At one point in my life (I was 27) I was fucking a sexy little 18 year blonde, a 18 year old tiny black girl with big tits, & a 41 year old blonde milf with perky B tits who looked about 28. Not at 'the same time' during the same time period. 1 in the morning, 1 at night. 1 the next day...before all that started, I was trying to fuck a beautiful 21 year old 6'1" chick with Ds. We became best friends and eventually I started fucking her as well and slowly got ris of the other chicks. There was also a butterface that was maybe 24ish. Butt fucking ugly face but amazing body. Anyway the 6'1" chick ended up being a contestant on Americas Next Top Model. She didn't win or anything. We stayed friends for a long time and did crazy shit together. I've never been overly attentive but I looked decent. Blue eyes. Curly blonde hair. Only 5'8". I was slightly overweight. When I was even younger, I dated 2 of the most beautiful girls in my town. (One was home coming queen)

Now I'm in my 40s with very thin hair and a white (grey) beard and I'm fat as fuck (not extremely obese but a huge beer guy) and out of shape. I don't have any social life. Im not wealthy (mostly by choice in all honesty. I live on the ocean and have a nice life in a nice small house but I don't have much money bc I work only as much as I need to survive). I couldn't get any pussy if I tried. I should also mention i have a small dick. I can grow up to 6" but when it's limp, it's tiny. And only gets 6" in the right condition. Usually it's a thinner 5.5". I used to be fun & girls liked me & I've had some bitches you wouldn't believe a guy like me could ever pull. But I'm dreaming about the past. Tinder doesn't work. Combination of low year round population and me being a old fat fuck. And the truth is, I think most people (not just women) are interesting in things I'm not and vice versa. I don't fit into society. I think I'll probably die without ever fucking again. I don't live in a big enough town to find a hooker, plus, idk if is even pay a hooker what they charge when porn & jerking off is free. Online sites make you pay when there's 5 women from my area on the site & 1 has been active in the last year. It's not like my area is desolate. But there's very few ppl from my area on online sites. I've live in other areas for short periods of time & tinder & online sites are almost too easy to find a hooker fast. Not like that here. Never has been. Anyway. I'm just typing this bc I'm high & bored as fuck. Wishing I had a 19 year old (or 55 year old) sucking my cock right now. 

I'm a long time motherless supporter, this will be my first entry and judging by your responses it will hopefully not be my last.
So this is my confession, my mother married a man with two daughters who are completely different in every way. The first we shall call her Natasha (Tasha) she was blonde 18 and extremely beautiful blond tight young body perky tits tight tone ass and legs, big blue eyes and straight blonde hair and a over all perfect sister very quite, shy and not the type to be open up about anything sexual. Then we have Natalie my second new step sister she's is 20, blown haired. Big blue eyes same body as her sister she was they type of sister that had no problem talking to me about sex and people we've fucked in the past she actually seem to bring up the topic more then I did. I had drove to pick up Natalie from a abusive relationship and gave her comfort in staying at my house for a while. At first she didn't really open up to me. She would cook a meal then return to the room which I provided for her. I figured this is normal. One morning mid summer I started my Harley and came back inside quick to grab a new cd to listen to on my way to work. I opened my bedroom door to see Natalie standing in my room with only a towel on. I asked why she was in my room, Natalie replied I was looking to see if you were leaving. I thought nothing of it and replied yep enjoy your day sis ttyl. She smiled and said ok see ya later. That night I brought home a girl we sat and watched a movie Natalie joined us in the living room. The girl I brought home and Natalie seemed to hit it off and were giggling and enjoying the movie. I how ever was getting more and more in the mood for much more then a typical sit with my sister and watch a movie Friday night. I reached across my date and grabbed a blanket covered us so that I could hopefully reach down my dates pants and play with her pussy. I was met at her jeans button and was stopped. My half hard cock returned to its prior state and upon finishing the movie I walked my date out. I returned from walking her out to my sister in a sports bra, basketball shorts that hardly covered her butt cheeks. laying under my blanket. I walked to the kitchen and grabbed a drink and returned to seeing her shorts on the floor at the foot of the sofa. I gulped very hard and to my shock and surprise my new sister asked if I was still cold. At first I didn't even think about the fact of how she was seemingly asking me to cuddle with her under the blanket. I replied nah thats ok I can grab a blanket from the hall closet. She insisted she didn't want to fold up two blankets we could just share one. So I sat up on one side of the sofa and she laid across the rest. We started another movie and I shut off the lights thinking she would or I would end up asleep soon. We had both fallen asleep with in the credits or shortly into the movie. I woke up to the Dvd play / menu options and a song playing over and over. I blinked twice then noticed something odd, my sisters sports bra is now on the floor as well. I knew this maybe the only time I get this perfect chances to see my step sister naked as she slept. So I slowly stood up and slowly tugged the blanket down just to see her perfect perky tits. I wanted to see more so I slowly tugged again she started to move a little so I gave up and grabbed the remote and shut off the tv. I was about to walk into my room but though about it and figured I could rub one off while sharing the sofa with her. My cock began to get rock hard as I thought about stripping off the blanket and fucking my new sister. I had never had sisters or brothers growing up but this made me extremely horny. I sat back down and pulled my jeans down, then my underwear down... and she starts to move she grabs the blanket and pulls it back up over her tits. I sit there and pretend to still be sleeping when she sits up looks over threw the darkness towards me. She slowly feels around for the remote or possible her cell phone when all of the sudden I feel finger tips on my leg slowly moving upwards. She isn't looking for a remote or cell phone shes sitting up right and reaches across my leg and finds my rock hard cock. FUCK ! I am busted. Natalie slowly reaches her hand out and grasps my cock and I hear her mutter "Wow" then she lays back down still naked and now with out a blanket on her at all. I feel the sofa moving slightly and then realize Natalie is playing with her self right next to me.. I pause for a second and think should I "Wake up?" or should I just stay "asleep?" I let go for about 2-4 minutes then I start to move she quickly tries to cover up so I grab tight and yank the covers tight so she cant cover back up. I look over towards her and said something like "Natalie I thought you were going to watch this movie with me?" She replied "I passed out, sorry... restart it!" I reached over and flipped the tv on and the bright TV nearly blinded me, I than asked her, "are you going to stay awake this time?" She, giggled. I looked over and noticed she had her legs still uncovered and her little freshly shaved pussy was just sitting there exposed and waiting... I didn't know if this was her doing or just a accident so I started the movie and she said her back hurt so she moved her head onto my lap. Again I could feel my cock start to throb. She noticed my hard cock with out a doubt, but said nothing. I laid my arm over her body and my hand on her ass. More for a comfort thing than a sexual thing at this point. So were into the movie and I start to fall asleep again. When bam I wake up and notice my little step sister Natalie has my cock in her mouth. Shes sucking my cock so good I was about to cum rather quickly. I wake up and she looks me dead in the eyes and said to me I've been waiting for this since the first time I met you. I smiled and said me too. She went back down and let her mouth sallow my cock. I slowly started to pull the blanket she still had across her back off and noticed she was on all fours with her ass in the air and sucking my cock. So I reached down and started to play with her tits then reached all the way behind her and started to rub her pussy it was fresh shaved, tight as fuck, and wet very wet. She let out a small gasp when my finger went inside her young pussy first. Then I grabbed her hips and pulled her closer I was about to wear her pussy on my mouth for hours. I laid her down an slowly started to kiss her nipples and move downwards. I reached her beautiful pussy and stopped and then went face first into heaven. She put one hand on the back of my head and pulled my tongue inside her I ate her pussy for about 20-25 minutes when she stopped me and said the sexiest thing I've ever heard "We can't tell anyone, ever!" I agreed she continued to enjoy my lips kissing her and my tongue licking her. I have never ate so much pussy and didn't want to stop for anything. I paused and looked her in the eyes and asked her how far she wanted to take this. She said we should problem stop now. For now... I smiled and agreed my cock was still hard as fuck and I had to cum soon or my balls were going to turn blue and explode. We continued to sit on the sofa for a few move minutes until I couldn't stop myself I stood up and stepped in front of her and pulled her head towards my cock she smiled and said, "I thought you didn't like it that's why I wanted to stop, I figured I freaked you out." I laughed and replied with her putting my full cock back down her throat and gasping for air every time she pulled it out. Then again I pushed her backwards and lifted her young tan legs up in the air. This time I wasn't going to eat her pussy this time I was going for more.... If you liked this entry and would like to hear move make sure you comment and I will return. Thanks - FYI I have a few entries to submit including the good sister isn't so GOOD after all and how that happened. Also where we are now ;) Stay Continued !

Hi Motherless, this is my first post here ever, been a lurker for a long while now and haven't gotten into posting that much, as I don't think anything interesting ever happens to me

Anyway, I just came back home from a hook up. I traded my old phone for sex, it was awesome. The girl was 20 years old, very very tiny, like 150 cm tall and weighed less than 50 kilograms. I was able to lift her up and fuck her hard while holding her in the air, she also sucked my dick like no other girl ever. Something tells me that she had done it before.

She messaged me on toe messenger. We chatted a while until she told that her old phone was broken and needed a new one, I told her I could sell her a phone. She didn't have any money, and I asked what she could give in exchange for the phone. She said she'd fuck me, I was surprised, and honestly, though it was a joke at first. Then I asked her how she'd like to do it and it didn't matter to her.

We decided that I go to her place, even though it was late in the evening and I don't have a car I still could use the public transport to her place in under an hour, so it was no problem. She gave me the address and I was on my way, with the phone in my pocket, I still thought it was some kind of joke, but when I arrived, this tiny, very hot woman greeted me and she was super cool. Her place was nice studio apartment, cleaned up and cozy.

She wanted to do it in the bathroom, I was down for that. We started with me feeling her body, through clothes, and I could already feel that amazing butt of hers, oh my god. I took off her top, no bra, pretty small and perky tits, I liked them, could've been bit bigger.

I lick and suck her nipples and she starts to push her stomach against my penis through my jeans, keep in mind, this girl is very small, like a full head shorter than me. I opened my belt and lowered my pants to my knees and she grabbed it instantly, started to feel it as it grew bigger in her hands, she was biting her lip at this point.

I took my condoms out of my pocket and put one on, since I'm clean and want it to stay that way, I take off her jeans too and she had a little bit of hair down there, just enough for me, I liked it, I felt how she was starting to get wet already, I rubbed her while grabbing her amazing ass, I made sure she was wet enough for my cock, which was raging hard at this point, I just wanted to stick it right in. I made her sit on the sink with knees up, I took my 7 inch dick and put it straight in, she moaned, I couldn't tell if there was a little bit of agony in the moan since SHE WAS TINY DOWN THERE, i don't know how it fit there, but it did. It felt really nice, probably the best pussy I've fucked. After a while of letting her sit there, I suddenly lifted her up and kept her in the air while fucking her very hard and deep, she started moaning loud and bit my shoulder real hard. I loved it.

After a while I let her down and made her bent over the toilet and fucked her from behind, this position somehow felt so amazing with her that I couldn't hold my load for much longer, I came, she didn't, but I don't care, she got the phone, so win/win. I threw the condom in to the trash, wiped my penis with a wet wipe and washed my hands, put my clothes on while she asked if I smoked, I said no, but I stayed with her while she smoked a cigarette in her balcony, still naked. We talked a bit, about life and everything, she just broke up with her boyfriend of 5 years and never cheated on him, she said the sex with him was boring, and she liked me a lot. I'm probably going to talk to her in the future, maybe try to have more sex with her, since I really liked it and she did too.

I put my shoes on and left, smiling, like after a successful date, that ends in sex, but this time, I got to skip the date part, straight to sex. Awesome.

Thanks for reading, and sorry for any grammatical errors, since my English isn't my main language.

I'd like to hear your opinions and suggestions on what to do next, when to message her or do I ask her for a proper date? Wouldn't that be awesome?

I confess...I have a fetish for older women that has only gotten stronger as the years have passed. The reason for this is the best (actually the ONLY *really* good) sex story I have.

This was 8 years ago, the summer of 2005. I was 15 and it was the July 4th holiday. My parents had a little pool/barbecue party for the block. I was swimming for a little while. When the sun started to go down I decided that was enough so I went upstairs to change. I dried off and got into a pair of my gym shorts, just for the time being so I could hang my suit in the bathroom and get a shirt and some sandals.

I went to the bathroom and was waiting. I thought- weird, the only people I figured would be using the upstairs bathroom was my mom or dad or sisters but they were all outside. The door opened after a minute. It was Mrs. Batelli, who was my mom's friend from the block. When she came out, she was adjusting the top of her sundress- really nice dress, orange with a pretty good cut, and I'm sure you know exactly where my eyes went. She was probably about 41-44 and she was nicely proportioned, probably around 145 and 5'6" or 5'7". Shoulder length auburn hair. Had a good tan on by that point in the summer. Her name was kind of deceptive, she wasn't Italian at all, that was her husband's name. I think she was some kind of European little-bit-of-everything mutt, but the tan was pretty far from her natural skin color. And it looked good. She had the legs out, nice shape- not very long but hey. Her tits were very nice, very perky for her age. Not huge, probably a small C or large B. I was staring dead at those suckers because in adjusting herself she was really moving them around and hadn't noticed me. In fact, I think she was about 6 inches away from bumping into me before she realized I was there.

She just went "Ooh!" and stepped back, definitely startled.

I just stood there, probably with some idiotic look on my face because I just got to watch a solid 6 seconds of tits bouncing around.

I expected her to react adversely, but she put her hand on her chest and started laughing- actually quite hard, much harder than the situation probably warranted.

She was like "Shit!" and kept laughing. I had no clue what to say, just kept smiling like an ass.

So she takes two steps, stumbles right into me and gives me this big half hug with one arm so that those firm tits and pressed right into me and she goes "You scared the HELL out of me!" and just kept laughing. I had still not said anything!

This is when it dawned on me- how long she'd been here, since noon, I wasn't keeping track of her drinking but she was fairly petite- this lady was HAMMERED.

So I think I said something like "Glad to see to you too,"

She said, "You didn't talk to me all day!"

We exchanged bullshit for about two minutes, none of it is interesting. Finally she said, "Your house is nice. I'm staying here. I'm going to sleep over."

I was kind of chuckling at this point and I just wanted to humor her so I said "Cool!"

She goes "Let's have a sleepover party" and I answer "Sure, that sounds like fun."

And then out of nowhere, she goes "Do you trust me?" all serious all of a sudden and I answer "Of course," because I think she's going to tell me something weird or something.

But no, as soon as I say it, she comes right up, pulls me in and gives me this deep, fucking awesome tongue kiss. Let me tell you. I had NO clue what was happening. She was working her tongue all over my mouth and I got instantly hard. She tasted like spearmint and- I didn't know at the time, but now, unmistakably- rum. And lots of it. Captain Morgan and Doublemint. I'll never forget it.

After about twenty seconds, she pulls back and goes "Somebody's gonna see this" and I think "FUCK! Come on!" but I was very happily mistaken because she grabbed my hand and pulled me into the bathroom.

I threw my towel and suit into the tub. She locked the door and put on the lights and the fan (cover up noise? I dunno) and she pulls me into the sink, falling, so that we both hip-check the counter. More tongue kissing. Fucking awesome, none of that awkward high school bullshit.

Her tits were right up on me and after a minute I started feeling bold so I slowly raised my hand up the back her leg and felt on her thigh. She had damn good skin for a middle aged woman, must have lotioned up all the time. I was wary, and frankly, a little worried that a wrong move on my part would blow the whole thing and I'd kick myself forever. But I was also horny as fuck at this point and just wanted to touch all her bits. But, to my delight, as I felt on her thigh she pulled my hand and guided it right up the dress onto her nice, firm ass. She was wearing the high-cut bikini panties. Guess she hadn't embraced the thong yet. I didn't care. It wasn't a big ass, but the texture was fantastic. Firm, but soft. Not muscular but not flabby. I was throbbing at this point.

She must have known, because she grinding the top of her leg against my shorts. She had me salivating. I pulled my other hand up her dress and onto the other ass cheek. Fantastic.

Then she reached down and fondled me through my shorts and gave me a little squeal. It was a lovely little sound. She stopped to spin me so I was up against the counter then back away and pulled her dress over her head (with surprising grace) to show off her body. She had a nice figure, cut pretty well for her years. Her bra was white and strapless. She whipped it right off. I got my third really good look at some live tits. This was the epitome of awesome. I felt like a fucking champ. But it was only the beginning.

She sauntered over to me and smiled and said "Show me" in the hottest voice I'd ever heard. I immediately dropped my shorts. I'm not going to brag about my cock. I'm no mandingo, but I was hard as a motherfucker. She said "Nice" and dropped her panties.

Her pussy was beautiful, symmetrical. None of the curtains you might expect on an older mother of two. She was shaved smooth. I'm pretty sure I audibly said "Fuck"- as in "Fuck, I am going to wake up any second now."

She came up to me and put her lips back to mine, and as she did she cradled my balls and started carefully to appraise my cock. She was teasing me. My heart was beating like it was going to explode. Then she got up on her toes and slid her pussy over the top of my shaft. It was like heaven. I don't know how I didn't cum right then and there. She leans into me and I think she asked "Do you want to help me cum?" and I just nodded "Yes" even though I didn't hear her completely. Whatever, she could have asked me to to stand on my head.

So she grabs my head and moves me so I'm about eye level with her tits and pulls me into them and says "Kiss my nipple like I kissed you". I tried my ass off to be good. Who knows if I was. Soon, she was purring like a kitten. She dipped her hand down into her snatch and started playing with her clit. I could hear how wet she was. I told myself "Shit, good, I'm doing it right."

She took my hand and guided it to her pussy. Her slit was so wet. She used just my fingers at first, but soon she was using my whole palm- long strokes, she had me cup it hard and my whole palm was getting slick.

Then she asked, "Do you have a condom?"

- FUCK -

I mean of course I didn't. I wasn't sexually active. My heart sank. I was abut to lose my virginity and I didn't have a fucking rubber.

I said, "No". She said, "It's okay."

My cock was denied entrance, but she balled up my hand and slid my index and middle fingers inside her and fucked away, vigorously. I went back to licking her nipples, harder and faster with the rhythm of her body. She came, I felt her snatch tighten as she squeezed and she threw her head back.

It was something to behold, indeed, but fuck man, did I regret not having a condom.

"Thank you," she said, with kind of a giggle.

"Now-" she said, and dropped down to her knees. I put my palms flat against the counter. She pulled my hips forward, grabbed my butt a little, and then slid her lips over my cock. I'm a little biased, but it's still the best head I ever got. Her skilled tongue lapped over my head and shaft and she gently caressed my balls. It was like waves of electric everytime she bobbed. She took the whole thing. I only lasted two minutes, having been dying for release for so long by this point. I came buckets and she moved down even deeper as I did so that it ran down her throat. She swallowed every last drop and cleaned me off with her tongue as she pulled back.

The whole encounter lasted less than twenty minutes. After I came, she started to dress herself again and said "Don't tell anybody, ok?" I nodded, lightheaded.

She left, and I laid in my bed for a few minutes to recuperate. When I went back downstairs, she was gone. Her husband was too, so I guess he decided they'd had enough and they were going home. I have a lot of theories- the husband was some kind of professional, like a lawyer or something. I first thought she was neglected but later I found out that he was most likely cheating on her. I never found out, but what does it matter?

Naturally, I kicked myself for not having a condom. It was about nine months later when I finally lost my V-Card.

After the encounter, I saw her less. I always wanted to try to see if she would ever be alone so I could ask her about it, but the opportunity never presented itself. Later, I thought about maybe trying to blackmail her, but I had a pang of consciousness and thought it would be shitty of me to do that to the lady who gave me my first great sexual experience out of the blue with no strings. I still have mixed feelings. I wish I would have hit it.

Eventually, she divorced the husband and moved away, out of the state and remarried. I haven't talked to her.

I took a few things away from this- first and foremost ALWAYS HAVE A RUBBER. you never know when your mom's friend will suddenly and for no reason decide to get frisky with you. Secondly, I still love the older ladies. I've only had a couple of other experiences after, but the first one was the best and most special. I still frequently knock one out thinking about that blowjob and fantasizing about what could have been.

Oh well, the inexperience of youth, etc.

That's it. This story is 100% true and I hoped you enjoyed it.

I'd like to share a story from last night, about a recently divorced MILF I met on Tinder (let's call her Jess); I'm in my early 30s, and Jess is a few years older. Jess was tall, in good shape, with a cute face and a really cute little butt. We matched Thursday and spent a good part of the day messaging back and forth. I could tell she was interested, but she was also playing hard to get. I asked for her number so we could discuss getting drinks, and she said maybe she would give it to me in the future. I persisted, we kept talking, and by 5 PM she had given me her number and told me she was going out for a few drinks later. I told her a friend was coming over to drink a bit too, and the conversation died down a bit.

By around 9 we were talking again, and I could tell Jess was interested in some dick. She started to get real flirty, and by 10 she was asking me when we could meet. I told her that I'd be free tomorrow, and she sent me back a sad face emoji, telling me her kid would only be gone for the night. My friend understood the situation and left, and by 11 Jess and I were talking about meeting up. She was a bit drunk, and had been smoking a bunch of weed, said she wanted me to come over, but was nervous. I told her we could wait, that I didn't want to take advantage of her while she was drunk; that was all she needed for that last bit of trust. She sent me her address, and told me to bring condoms unless I was certain I was clean.

I drove to her house, we talked for about 5 minutes, and then she came over to me and kissed me. She was wearing this low-cut short dress, and I was were making out in her living room I could tell she wasn't wearing any panties. She tried to grab my dick a couple times as we were making out, but I kept pushing her hand away. After making out for about 20 minutes, I asked her if she had someplace we could go, and we went up to her bedroom; I got a great view up her skirt as she led me up the steps.

Once we were in her room, I pushed her on the bed and got on top of her. We made out for a few minutes more, and I pulled her dress down to suck on her tits. They aren't the biggest, but they're beautifully shaped and she has cute, perky nipples. She was getting really turned on, and told me to get on my back. She took my pants off, and slowly went down on me. She started by gently licking my balls until I got hard, then put them in her mouth and went to town. She sucked my cock the same way...started with a few, delicate licks up and down, then put the tip in, and slowly worked her way up until she was gagging. I started to wrap my legs around her and hold her head down, and I could tell she was really digging it. She was moaning as she was sucking my cock, and I could see one hand of hers was fingering herself.

After a few minutes of a mind-blowing blowjob, she asked me if I was sure I was clean; when I said yes, she got on top of me and sat down on my cock raw. She was soaking wet and her pussy felt incredible; I let her pump up and down a few times and then told her to get off. When she started to ask why, I rolled her onto the bed, on to her back, and buried my face in her pussy. It was gorgeous, and probably one of the top 10 pussies I've tasted. I slowly licked around her pussy, getting the sides of her thighs and lips drenched in spit and juice from her. When she got into a good rhythm of moans, I put one finger in her and started to lick closer to her clit. She got wetter and wetter, and started saying things like "oh fuck" and "shit". When her hips started to thrust a bit, I pulled my finger out, licked a second, and put both back into her. She let out a loud gasp, and I started sucking on her clit as hard as I could. At one point she yelled "Jesus fuck you're good" as she thrust her pussy into my face. As she started to cum, she tried to get away, but I wrapped my arms around her waste and held her on me.She started screaming, almost having a seizure, and came all over my face; she didn't squirt, but it was pretty close.

I was rock hard as this point, so I got up, laid down on top of her, held her hands above her head, and started to pound into her. I won't even lie, between the blowjob, the excitement of her cumming, and a soaked pussy, I didn't last long. But after cumming that hard, she couldn't handle it either way. She was letting out this huge moan every time I thrust into her, and was barely coherent as I fucked her. When I told her I was getting close, she gave me the surprise of the night: she said I could cum IN her ass if I wanted. She rolled over, got on all 4s, and then backed her pussy up on to my cock. She slammed herself into a few times to get my nice and wet, then pulled forward a bit, grabbed my cock, and slowly guided it into her ass. She cringed as it went in, let out a little squeal, and then told me to do what I wanted. I swear to God, after she said that, I lasted 10 pumps. I fucked her ass as hard as I could, forcing her onto her stomach and making her go "ugggghhh" every thrust. Within seconds I was cumming, and I held her down as I filled her ass up with a huge load.

After we got done, she wrapped my arms around her, pulled me in close, and let the cum sit in her ass for a while. She told me that she almost never cums herself, and that it was some of the best head she's ever had. When I admitted I came a bit fast, she laughed and told me she felt honored I was that excited around her. We both agreed that there's nothing wrong with a guy cumming fast, as long as he takes care of his partner first.

When we said goodbye, she started to pull me in close to kiss her neck. I told her that if she started this again, it was going to be a much later night. We agreed to save it for another night, I left, and drove home.

Overall, it was one of my most memorable and fastest Tinder hookups. I'm going to give her some time to see if she texts me first; I've got some kinky shit I want to do, and want the green light to get a bit weird.

And guys, I'm only a 6-7/10 that takes terrible pictures that make me look like a 4-5/10. This girl was easily an 8, possibly a 9 if I didn't see her half trashed after the bar. If you take the most flattering pictures of yourself, have a good bio, and almost never talk about sex, you'll be surprised how easy you'll get it. Most women on Tinder want dick, they just also want to pretend like it doesn't happen often.

I must confess, I am an asshole. I grew up as a morbidly obese kid, and as a result had no success with girls. I finally decided enough was enough, and after a year of Atkins, I was slim and brimming with new found confidence. And a desire to repay women for years of rejection. This will be a bit long, but I figure the background will offer a better connection to what happened.

I first met Kayla when I was 16 and she was 13. My parents, along with their car club, including Kayla's grandparents, went out of town for a weekend of river boating and to attend a classic car show. We were the only kids along for the trip, so we pretty much had to rely on each other for entertainment, which wasn't too bad considering she was really cute. After 2 days of swimming, wrestling, and staying up late together, it was time to head home. Kayla's grandparents offered me a ride back so that Kayla and I could keep each other company on the long ride home, and I eagerly accepted. For whatever reason, I was nervous and things were ridiculously awkward on the way back. I ended up spending nearly the whole trip staring out the window, wishing I had the balls to make some kind of a move. Finally, as we were nearing the end of the trip, I had enough of my bleeding vagina, reached over and grabbed Kayla's hand, and leaned in and kissed her, with her grandparents mere inches away in the front seat. She looked at me, shocked, and a few minutes later we pulled into my drive way. As I was getting out of the car, Kayla's grandmother mentioned that her and Kayla were going on a church white water rafting trip the following weekend, and invited me along. Sensing opportunity, I smiled at Kayla and told her grandmother that I'd love to come.

Now I won't titillate you too much and offer you guys some false hope that I ended up mounting Kayla on top of the church groups cross. The first night out, we found a quiet spot and she asked me why I had kissed her. I simply told her that I thought she was cute and liked her, which apparently is like Kryptonite to 13 year old girls, since we spent the next 4-5 hours making out. We got back to where my tent was later that night, but she told me she wasn't ready to go any further, and I didn't press the issue.

The next few weeks we called each other constantly and emailed, and went on a few dates. Unfortunately, her mother found out about our relationship and, being the frigid, bible-thumping bitch she was, forbid Kayla from seeing me anymore. I graduated a year later, and moved out of state, moving on with my life.

Fast forward a few years to when I was 22. I had just moved to a new state, where my parents were now living, and was staying with them until I could find some roommates I trusted in the area. A few months into living with my parents again, my mom told me that Kayla's grandmother was coming to visit for the weekend...and guess what? She was bringing Kayla along. I felt as if I had a chance for redemption. I was going to get a second chance.

The morning that Kayla and her grandmother flew in, I had to work until late afternoon. I rushed home from work, and met my mom in the kitchen, where she told me I should go change and get in the pool, as Kayla, her grandmother, and my step dad were swimming out back. Changing quickly, I hurried to the back gate and was greeted by what I can only describe as the most perfect 'Fast Times at Ridgemont High' moment, ever. Kayla was just walking up the steps out of the pool, dripping water and wearing a two piece black bathing suit that hugged her body in every right way possible. She was no longer the cute, 13 year old girl I had a crush on as a kid. Kayla was fucking hot. She was 5'3, short bleach blonde hair, brown eyes, with tan skin. I secretly thanked God for her not being an underdeveloped, magazine cover anorexic, as she had D sized breasts, a flat stomach, and a gorgeous, round ass. As my Hispanic buddy would say, "She was thicker than a Snickers".

I stood there, dumbfounded, and she turned from the pool and finally saw me. Letting out a small, shrill squeak, she ran at me and gave the most pleasantly wet hug a guy could get living in the hottest state in the union. All her wonderful curves clung to me, and I was on cloud nine. We walked over to her grandmother, who hugged me as well, and caught up on life. We chatted about surface things for a while, and then her grandmother dropped the bomb that my fragile heart had been so afraid to hear. Kayla had a boyfriend. Not just a casual one, a guy she had been dating for three years. Fuck me. Kayla's grandmother then mentioned how much her family disapproved of him, as he was a terrible influence on her, getting her into the party girl/drinking/smoking lifestyle, hence one reason Kayla had been invited to come along to visit us. Apparently her grandmother was under the impression that I was the same sweet, Christian boy that she had known when I was younger. Oh granny, how you have underestimated me.

We all got out of the pool to go to dinner and then to a local country music/theater production. Kayla and I continued to catch up and rebuild our old rapport, injecting some flirting and light touching into the night. We got back to my parents house, and my parents and Kayla's grandmother we're ready for bed after a long day out (they were all 55+, go figure). Kayla, however, was ready to go swimming again. I teased her about being part fish, but wasn't about to talk her out of getting half naked alone with me. We jumped in the pool and splashed, rough housed, and swam for a bit, all the while talking about our new lives. After a while I started to pry about her party lifestyle, and began teasing her that because she was a girl, she automatically was a light weight compared to me (you say stupid things to get a girl naked). She responded to my challenge by saying she could easily drink me under the table, and I told her "fat chance". We ran inside and I showed her my parents liquor cabinet, and she selected a bottle of Captain Morgan 100, and we went back outside and sat on the loungers by the pool.

We drank gulp for gulp, and I started questioning her about her boyfriend, who she was texting while we were drinking. To my surprise, he was in Vegas for the weekend for a buddies bachelor party. Aside from him having a gambling problem that she was worried about, she also suspected him of cheating on her in the past. Well, the Captain in me doesn't spit on opportunity when offered, and I began to harp on whether she was worried if her boyfriend was taking advantage of the weekend alone and banging everything on two legs; after all, it is Sin City. All the while that I was sewing the seeds of doubt into her mind about her boyfriend, I was watching her text her him from the corner of my eye, and to my absolute delight, she had elected not to tell him about who I was, let alone me even living there. She kept trying to reassure him that she was so bored there, all alone with no one her age, and I slowly stopped taking actual shots from the bottle and simply mimed each shot, letting her get drunker in the process.

I decided that all my pieces were lined up, and it was time to make my move. I slid over from sitting across from her on the opposite lounger, and sat next to her on hers. I began to rub her back slowly, to build up comfort with my touch, and gently trailed my finger down her back and over to her thigh. I turned and looked her in the eyes, and I could see the passion and desire building. Still maintaining eye contact, I slowly slid my hands under her bikini bottom and lightly began to rub her slit up and down, feeling her getting wetter by the second. I reached over with my other hand and pulled her in closer, kissing her deeply while still exploring her under her bikini. Her breathing intensified as I began to add more pressure on her young pussy, and she exhaled roughly as I sunk my fingers deep into her. As I continued to finger her, I decided it was time to let those glorious breasts breath, and with one swift tug of her bikini top string, let loose two of the most beautiful, round, perky breasts I had ever seen. I took her nipple into my mouth and pushed on her with my body to get her to lie down on the lounger. I suckled like a newborn until my shorts felt like they were ready to explode from pressure, and began kissing down her stomach to where I was still knuckle deep inside her. I undid one side of the bikini bottoms tie, and pulled them to the other side, exposing her glistening vagina. It was simply too much for me to see, and I immediately began to lick, kiss and suck on her pussy, not leaving a spot uncared for. Her hips bucked up and down as I teased her between her thighs, and she began to let out short, clipped moans of pleasure. Finally, she pushed my head back, flipped herself over, and pushed her ass back towards my hips, inviting me to partake in riding her. I ripped the velcro holding my shorts together, and pulled out my throbbing cock, ready to sink it into her. Unfortunately, I misjudged my position on the lounger, and with both of our weight on the left side of the chair, we flipped over onto the concrete and on our sides. I let out a little laugh, and she got back up on all fours and started to shuffle-crawl away. I grabbed her hips, but she turned and looked at me and started saying "No, no, no, this is wrong. I can't do this. I'm so sorry, I have a boyfriend."

Seriously, fuck me.

She had a bit of a drunken, emotional break down by the pool, and ended up swimming around, crying, while I tried to get her to calm down, reassuring her that nothing that bad had happened. She finally consented that I was right,and came out of the water, still naked as a jaybird, and I grabbed her a towel and told her to quiet down, I'd get her inside. I grabbed her bikini and started leading her inside, all the while the Captains grog started taking affect on me, making me a bit light-headed and loopy. We got to my room, where I told Kayla to hold her towel up and I would try to dress her. She went from being sad and hating herself, to giggly and flirty again about her being naked. I kept trying to fumble her clothes on, but my hands were no longer working right, and she broke into a case of the giggles, letting her towel drop and falling into me, thereby pushing us both on top of my bed. Her back was on my chest as she lay on top of me, with her butt lying spooned in my crotch, which stirred my arousal again. I started to push her up off of me and the bed, not wanting her to freak out again, but she felt my growing hardness under my shorts, and I shit you not, began to grind against my cock like she was competing in a twerking contest. I wasn't going to pass up a good thing, so I grabbed her, swung my hips out, and turned her onto the bed, so that I was on top. She reached down, undid my shorts, and wrapped her legs around me, pulling my cock into her. I looked down and kissed her lips, kissed her breasts, kissed everywhere I could reach and began to fuck her with the sexual tension that only six years of waiting can produce. I was fading in and out of sobriety as my blood pressure increased, but her hips rocked in motion with mine, keeping me in the game. I grabbed her shoulder with one hand and the back of her head with the other, tangling my fingers in her hair and began to fuck her harder and harder, letting every last bit of frustration out. Her breath was hot on my neck as I pumped faster and faster, and after a few minutes she began to pant in my ear "oh god, oh god" as her legs tightened like a vise around me and her nails dug down my back. Then, her whole body tensed and she let out one last strangled moan as I pumped one final time into her, pushing in as deep as I could, and cumming spurt after spurt into her little body.

We lay next to each other, rubbing each others backs and sides gently, until I looked over at the clock and realized it was 5:15 in the morning. I quickly got her dressed back in her bikini, and led her out of my room towards the guest room, only to feel my heart stop dead in my chest as I saw my step dad in the kitchen (which is right next to my room) pouring himself some coffee and getting ready for work. He looked up after hearing me walk in, glanced back at Kayla, and looked me straight in the eyes. Then he smirked, turned away, and walked out of the kitchen.

The rest of the weekend was right back to Kayla being a sad sack wreck over cheating on her boyfriend, all while still trying to figure out what the fuck feelings she still had for me that made her do what she did. She went back home, I told her that she should keep it between us if she wanted to still have a boyfriend, but guilt got the best of her and she told him a gentler version of the story where we only saw each other naked and touched each other a bit. He was pissed and threatened to kill me, I only laughed and told him thanks for lending me his girlfriend for the weekend.

I'm not a good guy. This was the first time I stopped being an Average Frustrated Chump, and started being a dominant, successful male. I've slowly turned into more and more of an asshole, but this was the starting point of it all, although not the first instance of me being a dick. Do I regret the choices I've made?

Fuck no.

Ok, this is true, but I really don't care if you believe it or not. I'm just sick of reading the obviously fake shit on here.

I'm 39, married, average looking guy, little chunky with a thick but average cock. I'm married, and my wife and I have an open and polyamorous relationship. We're pretty social, and have friends all ages. Last year a couple invited us to a Christmas party.

They are in their mid 20s, with a kid. He owns a bicycle shop in a college town, she's a stay at home mom. Her name is Hailey, she's about 5'2, cute body, B-cup tits. She's constantly perky and always talking. She looks 16. She and her husband know about our lifestyle, but are strictly monogamous. She wants to have "the perfect little family". (eye roll)

She always themes her parties, so this one was Night at the Opera, or something. Everyone was supposed to dress up, but most of her hipster friends didn't. I, however, looked great in my suit, and she looked great in her tight, strapless formal with a slit all the way up the back.

I spent the evening drinking bad beer and cheap champagne, talking with a bunch of 20-something hipsters who couldn't believe I was in my late 30s, had a job, and was actually cool. My hopes of getting laid were dwindling. Suddenly the party vanished around 930 as some ukulele player was at a bar nearby. Hailey and I went to the living room and had a long conversation. She wasn't drunk, but pretty tipsy. She started flirting with me pretty hard. Her husband went to bed, and my wife was just drunk. I was tipsy, but in control. About this time Hailey's friend Kaitlin came over with her boyfriend, she had to work. Kaitlin was just cute, about 5'0, but a little chubby. She was a hipster, so stupid haircut, no makeup and bad glasses. Probably would be really cute if she fixed those. She was in a sparkly sweater, mini skirt and tights. Her boyfriend was a 6'2" black guy, educated hipster type, but an alpha male.

We were all hanging out on their big sectional talking and drinking, when Hailey tells Kaitlin that my wife and I were polyamorous. Instantly, Kaitlin's hand went to my thigh. Her boyfriend says nothing. Hailey then tells me that Kaitlin and her bf have an open relationship. He nods. Awesome! Things are looking up. Things have moved from cheap champagne to vodka. Hailey then insists we move to the chaise section of the sectional. I lean back, kick my shoes off, and stretch out on the chaise. Kaitlin sits right next to me, hand again on my thigh, and her skirt severely riding up. Hailey sits at the foot of the chaise, between my legs facing me. She pulls her dress way up so she can sit cross legged. She's wearing white lacy boy shorts. My wife is sitting on the couch buried in her phone. Kaitlin's boyfriend is sitting next to me not saying much.

Hailey and Kaitlin's conversation turns to sex. The normal girl stuff, nothing too interesting unless you're right there. Both are trying to impress me with their sexual exploits. Boyfriend goes out to smoke. Then Hailey tells me about the time the two of them took a shower together, and how hot that was. I ask if they went further, but Hailey says no. They'd never do anything like that, they're both super straight. She looks at Kaitlin and asks, "Right?". Kaitlin is hesitant. Clearly, she's bi and Hailey has no idea. I suggest they recreate the shower for me, Kaitlin seems eager, but Hailey shuts it down. He daughter's asleep upstairs, and her bedroom is next to the bathroom. Damn. Then, out of nowhere, Hailey gives Kaitlin a long, deep, passionate kiss.

"You've never kissed me like that before," said Kaitlin.

"Sure I have, I kiss you all the time," said Hailey.

"You've never used your tongue."

Hailey just giggles, turns to me and asks, "That was hot, wasn't it?" I readily agree.

My hand has drifted to Kaitlin's thigh at this point. Fucking tights are ruining skin on skin.

Hailey hops up and runs over to her iPhone and plays some dance song. She starts doing a burlesque number for us which then moves to a lap dance for my wife and I. She kisses my wife and grabs her boobs. My wife returns the favor. Then Hailey goes after me, while she doesn't kiss me, she does grab my cock. It's been mostly hard since all this started, and Hailey likes what she felt. When the song is over, she comes back over to sit again. I'm still in the same position, and assume she's going to sit cross legged facing me again. I was wrong. This time she pulls her dress up, climbs in my lap and sits directly on my cock. She even moved around to get it in the right spot. Right then, I wished I had my fly open. Through my pants I couldn't tell if it was her pussy or ass on my cock, but I think it was her pussy.

Kaitlin gets up to go pee and get more vodka. When she gets up her skirt is up all the way. I can see the thong she's wearing clearly through the tights stretched over her fat ass. I'm still on the chaise with Hailey sitting on my cock. We're cuddling, and I do some feeling of her tits, and kissing of her neck. She keeps talking about how wonderful Kaitlin is and how much Kaitlin likes me.

Kaitlin comes back, flashes her thong and tight covered pussy at me, and sits down in the same place. She switches to holding my hand now. Her black alpha male boyfriend comes back in, and surveys the site. Me with Hailey on my covered cock and Kaitlin, skirt up, holding my hand, my wife sitting next to me. He just stands there and talks to us. After a while he goes back out for a smoke, and Hailey goes out, too. My wife goes out for some fresh air, leaving me and Kaitlin alone on the chaise.

I decide this is the best time to make my move. I lean in to kiss Kaitlin, and she eagerly returns the favor. We begin making out heavily. Her hand goes to my cock, and mine goes to her thigh, then ass as she turns more towards me.

Hailey comes in at this moment, she loudly proclaims, "That is so hot!" and sits down to watch. Kaitlin and I continue making out for a bit, then Hailey kisses Kaitlin. Then she suggests we go upstairs.

The three of us go upstairs to the guest room. Hailey reminds us we need to be quiet so we don't wake her kid or her husband. Kaitlin quickly strips off. I mean in seconds, she's naked. She's short and chubby, but everything is firm. C cup tits, big ass, a tummy, but not bad at all. She's got a beautifully shaved pussy, too. Hailey is getting excited, but tell us to wait. She runs downstairs and a couple of minutes later brings up a bottle of vodka, my wife and Kaitlin's boyfriend. My wife kisses me and Kaitlin, tells me to enjoy, but she's too drunk to do anything and heads back downstairs. Hailey strips off her dress and panties, no bra, and starts kissing Kaitlin. She's got a youthful body, small B tits, fairly slender, nice ass, shaved pussy. Just a tummy and some stretch marks from having a baby.

The girls stop kissing and giggle. Then they start undressing me. I'm having the best night of my life! Kaitlin's black alpha boyfriend is just standing there, watching. They get me naked, and Kaitlin immediately drops to her knees and starts sucking my cock and I start sucking on Hailey's tits.

Kaitlin then stands up, kisses me, and tells me she wants me inside her. I tell her to get a condom out of my pants (always be prepared). She gets it, opens it and puts it on me. Hailey then yanks it off me, "No way! You need to cum in her! I want to see you cum in her pussy!" Normally, I don't fuck someone I just met without a condom, but Hailey has a definite plan for her own real life porno, and I'm not going to argue.

Kaitlin goes over to the bed and lays down, again Hailey has a better idea. She insists I fuck Kaitlin doggie so she can get a better view. She directs us into the proper position, and I slide my cock into Kaitlin's tight and extremely wet pussy. Hailey then lies on the bed and gets her face as close to the action as she can, while she plays with her own wet pussy. Kaitlin's boyfriend is still standing by the door, watching.

Honestly, I don't last long. Let's face it, I've been teased hard by these two girls for the past couple of hours and I was ready to blow. Hailey, I guess, can tell I'm about to cum (or she's just got good timing), and she reminds me she wants to see the cum in her pussy. So I back out so just the head is in Kaitlin's pussy and cum.

Hailey is so excited! I slide out all the way, and Hailey hops up and kneels down behind Kaitlin so she can see her cum filled pussy. She insists I kneel beside her so I can look, too. This honestly is my first look at Kaitlin's pussy. It's very soft pink, with tight lips, and now, my cum dripping out. Hailey then dives in, eating my cum out of Kaitlin's pussy. I tell Kaitlin what's happening and she let's out a loud moan.

I'm ready to go again, so I slide my cock, still covered in cum and Kaitlin's juices, into Hailey's pussy as she eats my cum out of Kaitlin. About now, I hear the door slam as Kaitlin's boyfriend leaves. Personally, I was hoping to see his cock come out and fuck the girls, as well.

Hailey continues eating Kaitlin to orgasm, as I fuck Hailey. I cum in Hailey the same way I did Kaitlin, and ask Kaitlin if she wants to eat my cum out of Hailey. She does. I move around and slide my cock in Haley's mouth, as she cleans it off and gets me hard again.

They reposition and Hailey is on her back now as Kaitlin is eating her out. I decide I'm going to fuck Kaitlin's big ass. It's just begging for my cock. I slide it in her pussy a couple of times to lube it up, then I go for her asshole. I slip it in a little at a time, taking it easy. She's super tight and she's moaning and whimpering. It clearly hurts, but she's pushing towards me. Finally I'm in, and I hold it there, all the way in her ass. When I feel her relax, I start thrusting. Slowly in and out. I don't want to hurt her.

Hailey then realizes what's going on and she asks if I'm fucking Kaitlin's ass. I tell her yes, she says, "Awesome!", and runs out of the room naked. I keep fucking Kaitlin, and Hailey comes back a minute or two later. She hops on the bed and lays out 3 glass butt plugs and some lube. I like where this is headed! She takes one, lubes it up and slips it in her ass. It's a cute one with a blue jewel on the end. She takes another one, plain glass, lubes it up, gets behind me and slides it in. It's thick, but goes in without much pain. Feels great when it's in there. It doesn't take long and it pushes me over the edge and I cum in Kaitlin's ass. I'm as deep as possible this time. I pull out, my cock covered with shit and cum. Hailey quickly slips the other plug in Kaitlin's ass. Then they start kissing, and sucking each other's tits.

I go out to the bathroom to clean myself up. My wife comes in to see how I'm doing. Well, I've got a butt plug in my ass, shit on my cock and two naked girls 15 years younger than me in the other room.. pretty fucking good! She's sobered up and is ready to go home. We go back to the bedroom as the girls are still kissing and sucking. We tell Hailey my wife is ready to go home. She says my wife can crash on the sofa if she wants. She decides to go home instead. Hailey says I can stay and she'll drive me back in the morning.

So I stay, and I fuck Hailey one more time, cumming deep in her pussy. I'm pretty wiped out at this point, so I just hang back and watch the two girls fuck and suck each other. It's probably 4 am at this point, and we all pile up in the bed to sleep.

I wake up around noon, sun streaming in the window, and Kaitlin curled up with me. Hailey's not in the room. I start to get up, feeling a sharp pain in my ass. I fell asleep with the butt plug still in, oops. I lift the covers and see Kaitlin still has her's in, too. I slip the butt plug out, it hurts a little, but no damage. (Glass toys FTW) I stretch as Kaitlin wakes up. She turns over and smiles at me, the covers below her tits. She asks me if I want a blow job, and I tell her I need to pee first. She wants to come with me. She gets up and notices the butt plug, too. She slips it out, giggles, we get dressed in case Hailey's kid is around, and we go to the bathroom.

She tells me she wants to hold my cock while I piss, so I let her. I finish and she takes her turn to piss. She reaches for my cock and she suck me off as she pisses. I cum in her mouth and she swallows every drop. She licks her lips and smiles at me. "I never go to do that last night."

We clean up a bit, and head downstairs. Kaitlin lives across the street, so she kisses me and heads home. Hailey's in the kitchen and makes me breakfast. She's wearing a cute little dress, and as she moves around the kitchen I stare at her ass and legs.

He husband took their daughter out to the zoo for the day, so it's just the two of us. She brings me the food, and I slide my hand up the hem of her dress, and squeeze her panty covered ass. I then realize she's still got the butt plug in her ass. She sits in my lap as I eat. She even feeds me while my hand rests on her inner thigh. When I finish, I thank her for the breakfast, and kiss her. She asks me if Kaitlin and I fucked this morning. I tell her she just gave me head. She then takes me upstairs to the guest room again, and we fuck one more time. This is more gentle and loving. Very intimate. Still no condom. As we lay there cuddling, I ask about the butt plug. She says she usually has one in her ass. She started using one after a gay friend told her how much fun they made day to day activities.

We got dressed and she took me home. Hailey and I still fuck occasionally. Her husband doesn't care, and my wife sometimes joins us.

Kaitlin's boyfriend dumped her that day, then moved out of state. He couldn't stand the site of me in her pussy. Kaitlin and I fucked quite a bit for a few months, then she got a job across country. While Kaitlin was a great fuck, Hailey is the one I really wanted. She's got another Christmas party planned this year. I'm wondering who we're going to fuck this year.

I once got with my ex’s best friend, who was really only interested in me because my ex told her I liked to eat ass.This is a long story, in a far away time.I was living at Job Corps at the time, I was broke and fresh out of college and needed a place to stay. I entered college my junior year of high school, so I was still pretty young for a college graduate.

The ex would never let me do anal, sometimes she would let me finger it a little, but she loved having her ass eaten. After we broke up, her friend would sometimes tease me between class. Me and the ex weren’t super serious or anything, so we all pretty much stayed friends after we broke up, but by then the ex was already with another dude, so I didn’t really hang out with her much.

One day, Friend was like, “I hear you like to lick ass” and laughed, and I said, “Yeah, I do”. She was taken aback, like she expected me to deny it, I guess.
”Don’t you know that’s gay!?” she said, and I said “No, I don’t know that”, and continued on my way.

Later on she came up to me in the cafe and said, “Are you going off-res tonight?”, it was a Friday, and we were allowed to leave for weekends if you lived in the dorms. I hadn’t been planning to, but I asked, “Why?”, and she said, “You should go off-res and take me with you”.She didn’t have to ask twice, I was now planning on it. I wasn’t sure what she wanted, but I definitely had my hopes up!

Being broke at the time, most of my stuff was still with my parents, but they weren’t going to be home that weekend, which is partially why I wasn’t going home, I had no ride and I usually hated taking the bus.

But I now had a reason, and decided I’d be taking her home that weekend. I half expected her to be bluffing or messing with me, but nope, she showed up to the bus and got on with me.We didn’t talk much on the ride home, really, and I was still half-expecting a prank or for her to want something from me.

We then had to take a city bus to my house after the first bus dropped us off, and I expected her to balk or mock me, turn around and leave or something, but she just got on with me. I was at least decent enough to pay the fare for both of us, hey, two bucks, it was the least I could do. We chatted a little about nothing in particular this time, but my mind was racing a mile a minute. What did she want? Just to get off campus for a bit? Everyone knew I always had weed, maybe she just wanted to smoke?

We got home and I met a snag in my plan, because for some reason my younger sister was still there. She was supposed to have been gone, too, staying at her friend’s to go to some concert the next day or whatever.

Once she saw that I was there, and with somebody, she made it a point to be a huge pain. “What’s going on!? Why are you home!? Who is this!?”, wouldn’t leave us alone, kept asking annoying questions, kept hovering.

Friend and I were hanging out in my room and I could hear my sister hanging around outside my door, constantly walking back and forth for no reason, nosing around, it was infuriating, what would she think was going on, and why would she want to know if anything was, anyway. We were usually cool, too, so it was really bothering me that she was behaving this way.

My sister was supposed to leave that night, but she wound up staying the entire night, I’m pretty sure it was just to be annoying, just to fuck with me. I wound up staying on my couch and let Friend sleep in my bed just so my sister wouldn’t hassle us all night, not like she should have cared, it was really out of character for her, and again, infuriating. I kind of never forgave her for it, just for how uncalled for it all was. To this very day I harbor some small resentment over it, really. Gotta be honest.

I woke up the next day and took the world’s quickest shower because I was worried my sister would drive Friend crazy and I walk out to find she left or something. Eventually my sister did leave, but she dragged it on for as long as possible, just to mess with me, and again, for no reason, we were all adults, it was really odd. I was positive that Friend would be totally bothered and disgusted with me, too. If not just for my sister’s obnoxious behavior.

Once my sister left, Friend hopped in the shower and I sat on my couch seething with rage, expecting Friend to be planning her exit.

Friend came out of the bathroom in just a towel, and walked over to me.“I’ve never had my ass licked before”, she said. Well, that was unexpected. I stood up and started lowering her towel, and she let me.

Worried my sister might suddenly burst back into the house or something, I took Friend into my room, locked the door, and got her up on my bed on all fours. She had a small butt, but it was pert, and perky. Really nice, and looked especially good bent over. Perfectly pretty little butthole, too, very tight and pink.

I spread her cheeks and started eating her ass, making my way to her pussy as well, but focusing on her ass. Hey, it was why she was here!

After a while, I was good and worked up and quite ready to fuck her. I didn’t have any condoms so I had to rely on the honor system, “I’m clean, are you clean… !?”, I asked. She said yes and I was too horny to second guess her, almost as soon as she answered, I was inside her. Warm and tight, shaved, she had a nice innie pussy.

After a while she asked if I had any lube. Fortunately, I had an old bottle in my top drawer. “Yeah, I do”.
“You can fuck me in the ass”, she whispered.
Her gorgeous ass was incredibly tight and I kept having to stop so I wouldn’t cum, I was very turned on by how quickly things had escalated.
As I pulled out and stopped, clenching my gut tightly so I didn’t bust, she turned around and started stroking me. “Wait, wait, stop” I stammered, not wanting to shoot just yet.
I laid her down on her back and fucked her ass missionary for a while, I wanted to suck her big tits while I fucked her. When I was kissing her she would lightly bite and suck my lips and tongue, it turned me on even more.
Eventually I was really close and pulled out saying, “I’m really close”.
She had these big, pouty lips and she just sat up, opened them and nodded, not saying anything but moaning in agreement.
”I’m going to cum in your mouth” I said, stroking myself to climax, “I’m going to come in your mouth”.
She puckered her sexy lips waiting for my throbbing member, I kept stroking it while resting the head on her soft bottom lip, she started pursing her lips, sucking and flicking her tongue around my cock saying, “Cum in my mouth, cum in my mouth”, and I couldn’t hold back any longer, pulling back a little and repeatedly shooting thick streams all over her pretty lips and face and into her gorgeous mouth, pushing my cock between her eager lips once I was drained, my post-orgasm shaft spasming inside her mouth. She kept sucking after I came and my whole body shook with pleasure and pain.

We fell back onto the bed and just kind of laid there holding each other and breathing heavily for a while before I eventually got up to get her a towel. While wiping herself off she said, “I’ve never had my ass licked before, all my boyfriends always said it was gross or gay… “. I was going to ask if she liked it, but that felt kinda corny, so I just left it at that. This was before ass eating was a huge mainstream thing, she kept calling it “licked”, instead of eaten, but I thought that was pretty sexy.

We took a shower together, I groped and played with her luscious, wet body, soaping up her tits and ass, rubbing her up and down. Somehow she looked even better, wet, I don’t know why that’s always the case, maybe it’s just a me thing.

Afterward, we hung around watching TV for the rest of the night. We made out and groped a little, at one point she put her hand down my pants and kept fondling my nuts, but we didn’t fuck again.
Later on out of nowhere she said, “My ex was huge. Like, really big. He liked anal and it hurt. It didn’t hurt as much, with you”.
Gee, thanks, I thought, but didn’t say anything.
We chatted randomly and cuddled, before she eventually fell asleep on top of me, later on I conked out, myself.

We had a normal Sunday morning and left for the bus stop that afternoon, luckily my sister didn’t come back home at any point. At that time I would have been happy to never have seen her again, I was still so angry.
We pretty much rode both buses in silence, got back to the center and went our separate ways. I wasn’t sure if she would tell anyone and suddenly everyone would be talking or gossiping or whatever, but as far as I ever found out, she only told my ex, who Friend claimed didn’t care, and who I don’t think cared to tell anyone else, really.

But a few weeks, maybe a month later, my Ex walked up to me in the hallway and said, “Just so you know, I only ever came when I was on top”, out of nowhere, for no reason. I’m not sure if it was out of some kind of spite or revenge for finding out, or if she just felt the need to throw that at me in the moment, but all I could think to say was, “At least you came at all!”, before walking off. It didn’t bother me much, especially since during our TV talk, one of the things Friend had told me was, “I was curious, since ‘Ex’ told me you were good in bed, and that liked to lick her ass”. Hey, thanks for the good word, Ex!

Me and Friend were still cordial, but we didn’t really hang out again after that, and we (unfortunately) never hooked up again, I’m not sure if it was because of the Ex, or if she had just, gotten me out of her system, or what. All the flirting had pretty much stopped, too, and I tried to convince myself it was just a thing that happened, she got what she wanted and was done with me, guys do it all the time for instance, but I can’t deny it was a bit of blow to my ego. The little flirting thing we had was a lot of fun, I was a little sad to see it end. And I couldn’t help but thinking that perhaps she had found my sexual abilities substandard. Not like I’ve had many complaints or anything, but hey, you can’t please everybody!
Her and my ex found a new group of weirdos to hang out with, and they weren’t too fond of me and my friends, so we all kind of drifted apart, entirely. I saw Friend in passing at a rave and didn’t know it would be the last time until it turned out it was. I saw the ex one more time, the day I was leaving the program, and she ran up to me and gave me a huge hug and said a very heartfelt goodbye out of nowhere, I hugged her back and we chatted for a bit, I eventually left, and that was the last time I ever saw her.

I have a confession.. my girlfriend is 5'4" and around 170 Lbs cute face perky butt and a bit on the big girl side.. her sister is 5'5" pushing 200 lbs cute face nice rack ( as far as i can tell through her low cut shirts.. wish i could see more) me and her sister are good friends and i would really love to rock her world.. yet noone knows of this...

I am a real mother fucker... for real.

Me: 25yrs
Her: 37yrs

We met online and had chatted for a bit. I told her that I was into older women, and she said that it really turned her on to have a younger man lusting after her. After a few chats she gave me her cell number so that we could chat a little more as our online encounters were not meshing with our schedules. We would text message each other regularly and eventually got together for a "date". It was just a casual dinner to feel each other out in person. She then went on to tell me that she is a divorced mother of 2 boys (one 10 the other 14). We went on a couple more dates until two nights ago. After the movie she said she wanted to get a hotel for the night and I obliged. After checking in we went to the elevator to go up to the 12th floor where our room was. As soon as the doors shut she was on me. Her tongue was all over my mouth and her hand trying to work it's way down my pants to my cock. With my right hand I grabbed her tits through her dress and used my left to pull up her dress and slide my fingers across her pussy. The elevator 'dinged' and we stopped and waited for the doors to open. We stepped out slowly and looked around to see if anyone was near, and then ran down to our room as if some one was fallowing us. By the time I shut the door and turned around, she had already taken her dress off and was on the bed working on her thong. I stood there for a minute and stared at her body. For a 37 year old, she was amazing. Smooth glowing skin, perky tits (I know right?) and such curves! I ran over and jumped on the bed making her bounce and giggle. She reached for my belt and I took me shirt off. She practically threw me down and tore my pants off. Grabbing hold of my cock with her right hand she shoved it in her mouth and began to give me the best blowjob I'd ever had. Her left hand was busy fingering herself. I played with her tits while she continued to blow me. I don't know how long I lasted, but I told her I was going to cum and she pushed her head down as far as she could without gagging on my cock.. I let out a moan and blew my load into the back of her throat. My eruption had her choking a little from the huge amount of cum. When I quit thrusting and riling around she pulled herself off of my cock, swallowed, smiled and the spun around presenting me with her pussy. She grabbed my cock and pushed it into her pussy while I was going limp. She said "let get this hard again, right now"... I couldn't agree with her more. She stuffed me inside of her and she sat back onto me. As soft as I was her pussy was tight, and extremely warm. Once positioned and settled she began to wriggle her his and flexing her pussy. It's like she was giving me a hand job with her vagina, and let me say that I got hard QUICK. Once she felt me hard she leaned forward and began fucking me. I started to trust a little and her moaning increased. I couldn't believe it. This WOMAN was fucking me! When I couldn't take it any more I told her I was going to cum and she rolled over and opened her mouth. I jumped up, spun around and stuck my cock right where she wanted it. I blew a small load and she ate it up just as the first, with a smile and a wink. She pulled her legs up and said "My turn, get down there." I love it when women are bossy. We continued to fuck eachother for as long as we could until we just passed out in bed.

We woke up late in the morning in eachothers arms. I said, "I think we need a shower"... she smiled and said "I'll wash your dick for you." Getting up she grabbed my cock and drug me to the bathroom and started the shower. She got down on her knees and began to suck me off. When we noticed the steam we climbed in and I stood behind her with my dick in my hand. She leaned forward and stuck her ass out at me and spread her butt cheeks and said "pick a hole". I said "Either one?" She said, "Yes, any one you want." So I took my dick and poked her anus with the tip and I heard her moan, "Thank god". I told her this would be my first anal experience and she squealed with excitement for me. I took my cock and pushed it hard into her tight anus. She moaned and let out a gasp, and then I pushed for home. I was in, all the way in, balls deep in. She was quivering and making all kinds of squeaks and coo's. I grabbed her hips and began to slowly trust. She took her left hand and started to rub her pussy. I asked if she was ok and she replied, "I'm in heaven! My ex never did this for me! I had to use my dildo if I wanted anything near my asshole." I stated to make my trusts longer and a little harder and she'd moan with each movement. I cannot tell you how tight her ass was wrapped around my dick. The harder I got, the more I thought she was going to break it off. Every time she panted, her ass would grasp me and I'd struggle to trust. After getting a rhythm she told me to, "Cum in me ass!" I speed up my thrusts, slamming my hips into her ass. Her moans and cries of pleasure got louder and louder. I said, "I'm cumming!" and she stood up and grabbed me with her arms to pull me closer to her. After I stopped convulsing she stepped away and my cock fell limp from her ass. She turned around and grabbed the soap and proceeded to wash my cock. She kissed me on the lips and said, "Thank you".

We finished our shower and got dried off and dressed. We sat on the edge of the bed chatting, me rubbing her leg and she twiddling my hair. We talked about our experience and how much fun we had. I told her I'd never though anything like this would ever happen to me and she said the same. Kissed and stood up and exited the room. We checked out at the lobby desk and went outside. We said our thank yous and kissed each other and parted ways. Not a minute later she texted me as I got into my car, it said, "Lets do this again real soon. ;)".

I cannot wait to see her again.

We have to check in and out of our building with security at work, and there’s this cute young black girl who started working as a security guard a few months back. She is light-skinned and pretty and just a tiny little thing. I don’t have any pictures of her, but the one above is her “type”, to give you an idea. We have joked around with each other a bit over the last few weeks. She always calls me “Mister [my last name]”, and I call her “Miss [her first name]”. On Friday afternoons, I have been telling her about how I’m so ready to go get a beer. “Where’s my beer?” she asks me. When it happened again last Friday, I said that we should go get one together. She told me that she is only 18 and not old enough to go to the bar. I felt bad and figured I’d be nice, so I went down the street to buy her a 6-pack. I brought it back and told her to put it in her purse for later. She laughed and thanked me, and I told her to let me know if she needed any help drinking them. That sounded fun, she said. For the hell of it, I asked her when she was getting off work. She said was getting off work soon, and I told her that I would just wait in my car in the parking lot while I finished up on some emails.

I honestly wasn’t hitting on her or anything. I just wanted someone to go have a beer with before I went home to the wife and kids. When she finally came out, I told her to get in my SUV and we drove to a nearby park. We walked from the parking lot to a secluded bench by the lake there and sat down next to each other. We both opened a beer and we shot the shit before she eventually started telling me about her life. She still lived with her mom, and there was no dad or boyfriend in the picture. She didn’t have many friends, and no real close ones. She had moved around a lot as a kid while going to mostly white schools, and it was always hard for her to meet new people. She told me that she is afraid to get close to people because either she leaves or they do. She said that she had been feeling isolated and lonely during all this COVID stuff, and that she had no idea what to do with her life. Most of her high school classmates had gone onto college and she just felt left behind. It was all pretty raw, and while I felt dirty about it, her vulnerability and overall awkwardness was starting to turn me on.


I changed the subject by telling her that she was pretty and that I was sure that the boys all liked her. She said she’d never even been on a date before. I was incredulous, and started asking her more questions about her sex life. She had only kissed a few boys before and nothing came of it. I asked her in a teasing way if she was still a virgin, and to my shock, she said that she was. I told her it was fine to be a late bloomer but joked that she must be burning through the vibrators. She said that she had never even used one before. We laughed a bit and I joked about how all these young guys were sleeping on the job. I told her I would be all over her if I were her age, and that you’d need a crowbar to get me off of her. She giggled and there was an awkward silence.


I noticed that we were both out of beer and so I opened another one foreach of us. I started telling her a little about my life, but nothing too intense. Just a few funny stories from my past to lighten the mood. She laughed and told me that I was crazy. We eventually finished our beers and it felt like things were wrapping up a bit. I told her she was a beautiful young woman and that all those young men out there were fools for not seeing that. She thanked me and there was more awkward silence.

I stood up from the bench and pulled her up by the hand. I went to give her a hug and she just fell into me with one hand on my chest. I wasn’t expecting it at all, but sparks were clearly flying between us. We just stood there holding each other without saying a word for the next few minutes. I put my hand on her face and she looked up at me. I kissed her softly for about 15 seconds and then stopped. We looked at each other without saying anything. My cock stiffened up and I am absolutely sure that she could feel it pressing into her stomach. It was such a hot moment and we were both breathless and unsure what do do next. An older married white man and a lonely young black teenager half his size. Even when flirting with her, this had never even dawned on me as an actual possibility.

I told her to come with me and took her by the hand. We grabbed the other two beers and walked back to the parking lot together. No one else was around. I put the rear seats down and we laid down in the back of my SUV together on top of a blanket and just cuddled each other for a bit in the dark. I soon started to move my hands all over her to feel her young body. She was nervous but didn’t stop me. It felt like I was back in high school. I couldn’t believe it was happening. We kissed some more and I eventually started taking our clothes off. Once I got her naked I was blown away. It had been so long since I had been with a young woman. She had a super tight body and it was sensitive to my every touch. Skinny and petite with a bubble butt and perky tits. She had tight abs and you could see her hip bones sticking out.

I started to suck on her rock hard nipples while she moaned and then asked her if anyone had ever licked her pussy before. She said no, and I slid down and started kissing her stomach and inner thighs. Her body trembled with each kiss. I then sucked on her clit for several minutes. Her young pussy was shaved and she was soaking wet. It tasted so good and fresh. She eventually shuddered and I knew that she had cum for me. I asked her if it felt good and she said that it had. I moved up to rub my cock on her clit and she shuddered again while I did. I just kept sliding my cock up and down on her clit and eventually, the tip of my cock slipped into her pussy. She didn’t say a word and I just kept putting it slowly in and out. I asked her if it felt good and she nodded. 



As an older married man, it felt wrong on several levels. I knew that I was exploiting a vulnerable teenager’s innocence for my sexual pleasure but I just didn’t care. At least she was 18. I thought of stopping for a minute but there was just no way that was going to happen, even without a condom available. She was so tight and fresh, and I was too turned on. I’m pretty thick and didn’t think I would fit inside of her tiny body. I slid into her slowly. It would only go half way in and I just kept sliding it in and out. I started going a little harder and she winced a bit. I told her she was doing ok and that I would try not to hurt her. Eventually, I broke through her hymen and was able to slide all the way inside of her. It was so hot all the way inside of her and I could feel her blood leaking out onto me. I asked her if she was ok and while she was clearly in some pain, she nodded. I kissed her passionately and she wrapped her arms around my back and held me tightly. I kept going slow and it was sensuous. She was gasping for breaths and letting out little whimpers right into my ear. I had never taken a woman’s virginity before. I was so tempted to just hammer her roughly, but I honestly just didn’t want to hurt her and felt like her first time shouldn’t be like that. I told her she was beautiful and just tried to make it nice for her somehow.

She was shaking beneath me and grabbed at me while I continued to fuck her gently. I have never been inside a woman that was anywhere near as tight. It was like her pussy was grabbing at me, and I could practically feel her heartbeat on my cock. With each thrust, I had to push and pull just to get in and out of her. I tried to last as long as I could, but I was so worked up after a while that I just blew inside of her as hard as I have ever cum before. I fell on top of her and we kissed for a minute. I tried to slide my cock out of her and it had gotten so tight it was like her pussy didn’t want to let go of me.

We got dressed and went to the restroom in the park. While I was wiping her blood off of my cock in one of the stalls, it started to dawn on me what I had done. I had just just blown one of the biggest loads of my life inside of a confused teenager less than half my age while taking her virginity. That was a problem. I started to panic a little and couldn’t believe how stupid I was. It could easily wreck my marriage and even my job if I impregnated her. When she got back to the SUV, I asked her if she was on any birth control, and she said that she was not. I immediately drove her to the pharmacy to pick up some Plan B. I made her take it right in front of me in the parking lot just to be sure, then dropped her off just down the street from her house. I kissed her goodnight and told her she was beautiful again as she walked off.

I thought about her all weekend. What had just happened? Was it a one-time thing? And if not, what was it exactly? When I saw her at work on Monday, a few of us were checking in at the same time. I could tell right away that she was nervous. So was I, and I could feel the butterflies in my chest. I let the others check in first, and once it was just us alone, I told her I just wanted her to know that I really enjoyed seeing her the other night and getting to know her better. She was shy but smiled at me. I told her that I would love to spend more time with her sometime and she said, “I’d like that.” I could tell right then that she was probably already falling pretty hard for me. She could barely even make eye contact. That feels a bit weird and surreal as a married older white man more than twice her age, but I guess I was her first, after all. I asked her if she would let me take her out to dinner on Friday night, and she smiled and nodded. I asked her if she had a dress to wear. She said that she did. I told her to bring it to work with her, and that she could go change before we went out for an early dinner.

I booked us an early reservation for tomorrow night at nice restaurant that is in a fancy hotel near work. What I didn’t tell her is that I have also reserved us a nice room upstairs for afterwards. I made up some story for my wife about having to cover for a coworker out of town at some function on Saturday morning and am ready to stay the night. I’ll have some champagne and wine and some sex toys ready for us, and plan on taking a handful of viagra and expanding her sexual horizons all night long if she will let me. I think she is probably already starting to develop strong feelings for me as she undergoes this awakening about sex and love. I’m not dumb enough to think it can go anywhere beyond a fling, but I really do like her. She’s such a sweet kid and it is already some of the hottest sex I have ever had. I feel like I’m just going to ride it out and help to teach her about what sex and love are all about before turning her over to whomever life has next for her. I think it will be good for the both of us, and am grateful for the opportunity to cherish her for however long it lasts. In the meantime, she’s basically a blank canvas that I think I am going to be able to do anything I want with. We will work up to the kinky and rougher stuff soon enough but I don’t expect that to be a problem. If all goes well, she’ll be submissive putty in my hands to teach and mold as I please.

I can't wait for tomorrow.