Here is how I got to mess around with two of my friends during our senior year of college. Names have been changed to protect identities. I will also warn you - this will probably end up long.

SO I knew Ashley and Sara since our freshman year. They had been roommates since the first semester, and we all had History together. We had been the best of friends throughout college, although none of us had done anything sexual together. My parents lived not too far from college, and they decided to take a winter vacation to a tropical The house was empty, which meant a perfect studying place for exams. I invited Ashley and Sara to join, since I knew all of us liked studying together, even if it was for different classes.

I should take a moment to describe Ashley and Sara. They are really polar opposites of each other. Sara is tall and slender, white complexion, with (I would estimate) B cups, a flat ass, and blonde hair. Ashley is 6'2", a little chunkier, is a little darker (basically looks like she has a natural tan), has huge tits (they look like fucking watermelons), a huge ass, and brown hair.

We ate dinner at college first then drove to my parents house. We decided that it was a little late to start studying, so we decided to drink in my parents half finished basement (half finished as in my dad started to finish it, but got distracted and never completed the project). We had an old couch and a bean-bag like chair with a mini-fridge stocked with some of my dads beer. We broke out the beer and start drinking while talking about random topics. Ashley and Sara were on the couch and I was on the chair. Ashley and I were three beers in, Sara was still milking her second. This was on-pace for us, and based on past experiences, I knew we were all buzzed. I got up and went upstairs to pee. As I got to the top of the stairs, I heard Sara say that she was going to go pee too.

Now, my parents house has two bathrooms somewhat close to each other on the first floor. I figured I would be polite and went to the further bathroom, leaving the closer one for Sara. I partially close the bathroom door and pulled out my dick when I hear the door open and Sara say "OH MY GOD." I look over, and she is staring at my dick. I close the door in her face and finish peeing. After I finished, I opened the door and she was still standing there. She said "I AM SO SORRY. I thought you were in the other one, that door was closed. And holy shit you have a big dick."

Let me stop again and explain. I hate to brag, but I will anyway. Yes, girls are routinely impressed by my dick. That is because it is huge and long while soft, but does not get that much longer hard. It mostly just gets thicker.

Anyway, I didnt say anything and went back downstairs. Sara came running down a minute later saying "Oh my god Ash, you have to see his dick. It is huge." Ashley smiled and said that she has seen plenty of huge dicks. Sara said "Yeah I know. I mean, not to sound like a slut but I have seen a ton of dicks too, but it was really big even soft".

So they start talking about guys and their dicks for a while. I was starting to think they forgot about me when Ashley turned to me and said "well, now I am curious. You willing to show me?"

Ok, sorry for the interruption again. There really was no good time to mention this before. Sara and Ashley had both been single for a couple of months, and I had been single for about 5. I was pretty certain neither of them had gotten laid in that time span, since I would usually hear about it.

I laughed and said that I would feel a little uncomfortable just randomly taking it out, and that Sara only saw it because she accidently walked in on me peeing. Ashley said "So what, I have to wait until you have to pee again?" It sounded like she was waiting for an answer, so I said "yeah, I guess." She countered with "What if I showed you my boobs?"

Well that took me by surprise. And I think Sara was surprised by it too. I thought Ashley was talking out of her ass and would never flash, so I said "sure, why not." In one move she sat up and grabbed her shirt and lifted it up, showing her bra. Then she lifted her bra up and her boobs flopped out. Holy shit, they were big and perfect. I should point out that the couch and chair were only a few inches apart..we were sitting really close to each other. So they were almost in my face. She shook her shoulders and her tits swayed back and forth, then she pulled her bra back down, fixed her boobs, and pulled her shirt back down. Sara looked shocked (almost a little horrified).

Ashley looked at me and said "Ok, it's your turn." I really didnt want to, but I pulled my dick out of my pants. By this point, the conversation and staring at her tits had made my dick semi hard. I shook it a brief second, and Ashley said "that doesn't count, it is hard!"

I laughed and said "Well yeah, boobs will do that." Ashley said that she wanted to see it soft, so I told them to change the subject. So Ashley turned to Sara and started talking to her about some on-campus event later that week. All while I sat there on the chair with my dick out. And it only took a minute until it was soft. I saw Sara glancing at it out of the corner of her eye, and she turned and said "oh, it is probably soft again."

I looked down and confirmed that yes, it was soft. Ashley said "bullshit" and leaned over and grabbed my dick with her hand. I heard Sara yell "ASH, WHAT ARE YOU DOING??" and Ashley laughed and said "oh man, that is large and soft. Jeez, how big does it get?" She then started stroking it.

I kinda gripped the sides of the chair, not too sure what to do. It got hard almost instantly, and Ashley said "oh, not that much longer, but pretty thick." She didnt stop stroking though, and only a few strokes after she said "Uhm, I dont know where I am going with this..." and then she laughed. I said "yeah, what are you doing?" and Sara yelled "ASH STOP THAT!!"

From someone standing in the room, it was probably a funny scene: Sara staring (with a horrified and uncomfortable look on her face) at Ashley's hand stroking my dick, Ashley staring at her hand stroking my dick, and me looking at my dick, then at Ashley, then at Sara, and then back at my dick, all in a loop.

Ashley then looked at Sara and said "here, feel this." Sara yelled "NO! It's Mark...I wont touch his dick! And you shouldn't be either." Ashley said "Shut up, just touch it." They bickered back and forth for a minute before Ashley grabbed Sara's hand and forced it on my dick. Either Sara was not expecting it and didnt have a chance to fight back, or she just didn't fight back at all.

So Sara's hand was on my dick. She squeezed it and the look on her face went from horrified to amazement. "Wow, that IS thick..." She then picked it up and gently started stroking. She took both hands and gently stroked with both hands for a few seconds, before going back to one hand. Meanwhile, Ashley was still staring at my dick. She pushed her hair to the side, and then leaned over and put her mouth around the top of my dick.

Sara pulled her hand back and said "Ash, what are you doing now???" Ashley took my dick out of her mouth and said "Shh, I am just doing this for a few seconds." She then proceeded to take my dick back in her mouth and bobbed her head up and down my shaft. She actually got it pretty far down her throat. She held her finger to the side of my dick to show how far it went. She turned to Sara and said "Ha, beat that."

Sara said "I probably could, but we shouldnt and your mouth was just all over his dick." Ashley said "who cares..bet you cant do it anyway." Sara looked at my dick for a few seconds, then leaned in and put her mouth around the head and slowly it went down her throat. And it went further than Ashley...it didnt seem like it wasnt even that difficult to her.

She pulled up, then sucked a few seconds, bobbing up and down, then took it out of her mouth and turned to Ashley and said "see, told ya."

Sara and I then realized that Ashley's hand was down her pants, playing with her pussy. Sara yelled "ASH! Really? Right here in front of us??" Ashley said "oh shut up, its not like we have not masturbated before when sharing a room." Sara said "YEAH, but we were each in our own beds, with the lights off." Meanwhile, without thinking, I was slowly stroking my dick. Sara sees me and says "MARK! Come on, we aren't supposed to be doing this stuff together.." I shrugged and said "Ash started it."

Ashley stood up and started to take off her pants. Sara started to say something, but Ashley said "Come on, we are all good friends, let's each just have a little fun." She took off all her clothes and sat back on the couch naked, with her finger in her pussy. Ashley could see that Sara looked uncomfortable, so Ashley said "It's not like we haven't seen each other naked. You can just close your eyes if you want." Ashley then fixated her eyes on my dick and continued to stroke her pussy. I stared at her pussy and tits, and glanced over to Sara from time to time. Sara sat on the couch, looking around the room and , from time to time, at Ashley and back over to me.

I saw she was looking at my dick a little longer, and slowly started to reach her hand down her pants. Ashley saw too, and said "you know Sara, it isnt really fair that you are still clothed."

Sara thought for a minute, then stood up and slid off her pants, but stopped and said "this stays a secret..." then continued to take off her underwear, shirt, and bra.

I should take a break here and say that this all happened within a few minutes, but it really seemed like much longer.

Anyway, Ashley is slouched spread eagle on the couch while Sara's legs are conservatively spread. Both are looking at my dick, but Ashley is also glancing over at Sara. I think Ashley was getting bored, because she whispered "you have a condom?" Sara's hands stopped moving, and she just stared at Ashley. I said "yeah, probably in my bag," and I reached over and looked through the front pocket. I had a few, and pulled one out. Ashley got up, snatched it from my hand and ripped the packaging open. Before I could even move, Ashley had the condom on my dick and she was standing over me, rubbing my dick on her pussy lips.

Sara started to get up and said "I should probably leave you guys down here..." Ashley said "No, just stay. I dont care," and I just shrugged my shoulders. Ashley's tits were swinging in my face, and I grabbed her boobs and sucked on her nipples. I looked up, and she started making out with me. I could see Sara out of the corner of my eye, and she was looking at us and masturbating slowly.

She got up off me, and I thought the fucking was over. But she turned around and sat on my dick backwards, facing the couch. I reached around and grabbed her tits as they bounced. She grabbed Sara's leg and pulled her closer. Before Sara could say anything, Ashley was bent over and her tongue was between Sara's legs. Sara's eyes closed, her mouth opened, and for once she looked like she was enjoying herself.

Holy fuck, this seems much longer written out. My fingers legit hurt. I will come back later to finish. If you have reached this far, CONGRATS. I doubt many will actually make it this far though.

With the house all to myself from Thursday through Sunday night, I suggested to Robby (our gang bang guru) that it would be great for him to arrange a fuck session where we could take advantage of an empty house for a change, rather than renting a hotel room for our activities. He came through within the first couple of hours, which just shows what an amazing track record he has of snagging seriously fuckable women.

He'd connected with Jamie via a Craigslist ad. She's 30, 5-5 120, with blonde-highlighted light brown hair and 32B tits. The photo posted here is the one she sent along with her request to meet. Because it was midday Thursday, Robby was only able to arrange a threesome, since the rest of the guys in our over-50 GB group couldn't make it on such short notice. Jamie was apparently OK with that, though, since this was to be her first multi-guy sex encounter and she wasn't too sure how overwhelmed she might be with more participants. And if her claims could be believed, it would prove the first time in more than a month that she'd had any kind of sex at all.

While waiting for them to show up, I gave Robby some shit via text because, after picking Jamie up from her place in North Denver, he had trouble finding my house on the southeast side. He claimed his GPS was all fucked up, but I was more certain it was operator error. Also on the way over, he "warned" me that Jamie was a bit on the skanky side, but I replied that, given our plans for the afternoon, that was a benefit rather than a flaw.

They showed up at my place just before 1:00 p.m., around 20 minutes late. I'd prepared our guest room in advance by stripping the queen-size bed and putting on a new bottom sheet plus clean pillow cases, setting out a brand-new tube of lube, and adjusting the shades so the room wouldn't be quite so bright. Meeting them at the front door, I saw that Jamie was dressed in a pleasantly slutty outfit: Short green cloth jacket over a black lace sleeveless top with a purple bra showing underneath, a denim micro-mini skirt that barely covered her ass, and over-the-knee high-heeled leather boots. She had her hair tied back in a ponytail and spun around after coming through the door so I could apply the green silk scarf I was using as a blindfold. She'd asked for this as one of the conditions of the afternoon's activities, and I was happy to oblige.

Given the lateness of their arrival and the fact Robby had to leave in an hour to pick up his kids from school, we immediately headed upstairs and got down to business. I helped Jamie off with her jacket and unzipped her skirt so she could slip it off. She quickly removed her lacy top and I unhooked her bra. We all agreed she could leave her boots on for the duration. Meanwhile, Robby was stripping down to bare skin, tossing his clothes haphazardly onto the floor in his haste to start in on Jamie. She asked us to leave her undershorts on -- they were leopard-print boy-shorts -- which was fine because they'd been altered by having two carefully placed holes cut out of the crotch. One showed off her smoothly shaved pussy while the other exposed her tight little asshole. I ran my hand down over her buttocks and slipped my middle finger into her tight, wet pussy while removing my clothes at a pace considerably slower than Robby had achieved. He put his hands on her small, firm tits and began to suck on her nipples, which stood up nicely to the attention. She used one of her hands to tug on his fully erect cock - it was hard even before he took off his trousers -- and meanwhile I disengaged so I could remove the rest of my clothes as well.

Robby suggested she lie on her back, which she did, and he stuck his face in between her thighs to taste some of that sweet, sweet pussy. I thought he might be down there a while, but after only about a minute of some serious licking he stood up, pulled her hips closer to the edge of the mattress, and jammed his seven-inch dick into her wet slit. She had her legs up in the air with Robby pressing his hands against the backs of her thighs to keep them there as he pounded her hard. I'd stroked myself from a semi-hard to a fully erect state and climbed onto the bed so she could take my dick in her mouth. By changing my angle of approach, I was able to slide my entire member into her mouth. Of course I'm less than six inches, so it's not a huge challenge, but I could still sense the tip of my cock hit the back of her throat with every downward thrust, which was a great feeling.

After a few minutes of fucking her while standing alongside the bed, Robby suggested it was my turn to squeeze my dick into that pussy. We helped flip her over -- her equilibrium was compromised somewhat by the blindfold -- and I entered her from behind, doggie-style. It had been a couple of months since I'd had sex, so this was a welcome opportunity and I made the most of it, thrusting enthusiastically as Jamie reached down with her right hand and rubbed it briskly across her clit. Meanwhile, Robby had opened up the small bottle of Astroglide he'd brought with him and suggested we DP the girl. She was definitely on board with that idea, so we maneuvered ourselves into position with me on my back and her on top, facing me. She reached down and re-inserted my cock into her pussy and leaned forward so I could suck on her tantalizingly erect nipples. I moved my legs together and Jamie did the same with hers, which allowed Robby to climb aboard and straddle the two of us. He squirted some lube onto his index finger and worked it into Jamie's rear hole, removed it quickly, and leaned forward while pressing his cock's head against her anus. She balanced on one hand above me while reaching back with her other hand and pulling her butt cheek aside to provide him greater access. A deep grunt from her, plus added pressure on my dick inside her pussy, told me he was in her ass. I lay still with my hands on Jamie's hips while Robby did all the work. He pounded her ass with enthusiasm and some deep penetration while she ground my pussy against my lower body. I saw Jamie's chest flushing red and moved my hands from her hips to her tits, tugging insistently on her nipples to match the rhythm the two of them were playing out above me. After a couple of minutes, Jamie let out a big groan and announced she was cumming.

By this point Robby was starting to run out of gas, so he pulled out of her ass and stepped across the hall into the bathroom so he could find a towel for wiping off his dick. Jamie rolled off me and onto her back, but she was clearly far from done. Neither was I -- so I climbed off at the foot of the bed and pulled Jamie toward the edge, pushed her legs up into the air and told her to hold them there (which she did by looping her arms around the backs of her knees), and then I sank my cock into her ass. It was the first time I'd done anal in probably 20 years, and it felt terrific. I was soon pounding her with balls-deep thrusts, and she let go of one leg so she could reach down and mash her fingers against her clit in a rapid-fire manner. Meanwhile, Robby crouched next to her face and stuck his newly cleaned-off dick into her mouth. She sucked him enthusiastically while I fucked her ass; then her butt muscles clenched and she was suddenly in the midst of her second orgasm.

Once it passed I withdrew, especially since my legs were shaky from all the thrusting that I was hardly used to anymore. Robby decided he wanted some more of Jamie's asshole, so we switched positions and he stood at the foot of the bed with his dick inserted all the way into her poop-chute. After about eight or ten thrusts he announced he was ready to cum, so he pulled out and shot a nice thick glob of white goo all over her pussy lips, with some coming to rest on her shorts. I was positioned behind her, with her head cradled in my lap, so I reached down and used two of my fingers to scoop up some of Robby's ejaculate. Then I popped my fingers into Jamie's mouth and she sucked them dry.

By now it was time for Robby to split, but I wasn't quite ready to call it quits and Jamie agreed to let me take her home. As Robby dug around on the floor for his discarded clothes and started to put them on, I finally pulled off Jamie's blindfold -- it was simply too much in the way after all this time -- and convinced her to get on top of me, 69-style. Robby said a quick goodbye, to which Jamie was only able to reply with a muffled grunt, since at that moment she had my entire cock in her mouth. I licked her pussy, sucked on her clit and slipped a finger into her ass, hoping to induce a third orgasm, but she came off my cock long enough to explain we'd made her pretty sore down there, so instead I pulled my face and hands away from her crotch and simply let her do her work. About three minutes into this latest activity I said, "OK, finish me off." Jamie took that as a cue to get me to cum, so she wrapped her hand around the base of my cock, sucked harder on the head, and shortly thereafter I was pumping my jizz down her throat.

She wanted to smoke a cigarette (Marlboro!), so she slipped on her black lace top and I led her toward the deck that's just outside our back door. She also wanted something alcoholic to drink, so I unscrewed the top off a tiny bottle of Barefoot Moscato and poured it into a juice glass. Classy presentation, eh? By now it was nearly 2:30, so rather than begin another fuck session -- we were both pretty sore at this point -- I suggested I drive her home. We got dressed and hit the road. On the way there, we enjoyed an interesting conversation about local politics, the police -- she was on probation for her 2nd DUI, thus a suspended drivers' license and the inability to drive -- and other non-sexual elements. As she exited my car she stuck her head back inside and gave me a warm kiss on the lips. "Tell Robby I'll be in touch again soon, OK? And next time, a couple additional guys would be all right." She'd obviously enjoyed herself!

So, I am going through a rough time. Having a break up with my now x gf. We havent been dating for a long time but we have known each other for years, so the break up is going over rather poorly. Constantly fighting, always, about the same old shit over and over and over. WE cant move pass it, so i have kinda just given up. By doing so I have spent more time with my friends... One of my friends mothers has been curious about me for a while, i used to live with them and would sleep in her room, not with her but in the room. I would come in and find her play toy just laying on the bed, or find it when i tucked into bed. I loved it, so hot for me to come home to. We have talked a few times about doing stuff together but always boiled down to "youre not old enough, maybe when you can buy me a drink". though i have dranken plenty in my lifetime before hand let alone any other drugs. When i turned 21 i would hit on her when my friend was away, sometimes get drunk and come on SUPER thick with the interest. Eventually i moved away for a while, and came back. Start hanging out with friends a bunch again because i didnt have much friends where i moved to. Hung out with my friends and my friends mother again, my friends mother didnt seem too different, but one night she gave me a hug after a long day at work and a long day of screaming with the gf... It felt so amazing, her breasts held tightly against me. I held her a little uncomfortably long, she tried to stop real fast, like a fast friendly hug, but soon she started hugging me back and and rocking side to side. I eventually let go and told her sorry, but i needed that. And she said no problem, we stood there and talked for a while before she left. Then i texted her almost as soon as i got inside that her hugs were amazing and sorry if it were too long. Told her she was amzing for being there for me, because i havent had much for parents so my friends parents had typically been what i would refer to as my parents. Her reply was that she also enjoyed the hug very much, and that beyond our relationship with her child we had great chemestry. Then went on about not sure if shes a cougar or a milf but she hasnt been attracted to a younger male in a long time and that she doesnt want to make things awkward... but she wants that D. eventually the conversation leads to how she doesnt like to wear condoms and is recently off birth control, but we can have some fun... Idk what exactly that means due to me being rather vanilla and this would be the first older woman i would have ever had sexual relations with. ive had plenty of sex with younger women, but this is different... this is my friends mom, of which ive been attracted to for a while, and yet shes opening the gates for this.

When I was 19 years old and in college in Florida, I got really heavy into drugs. Mainly party drugs like coke and ecstasy, and of course plenty of weed, but on occasion other drugs as well. I was out of control and living one big party life on my parent's dime while they struggled mightily to pay for me to have the opportunity they never had and go to college. Looking back I feel like a total asshole about it now as they wanted nothing more than for me to be successful and not have to struggle...sorry, I digressed.

Anyway, since I had no money and wanted to keep up my partying lifestyle and since I was always very athletic, in shape and considered "good-looking", through one of the people I met in the party scene I ended up doing some modeling to make some extra money. Pretty low rent stuff, nothing glamorous, but a couple hundred bucks a week.

This quickly evolved into the opportunity to do some "videos". It started with just masturbation videos of me lying in bed, or on a couch or in the shower jerking off. I figured I was going to do it anyway so why not get paid for it and I was getting paid $100-200 per day that I did a shoot. I could sometimes do 3 or 4 scenes in a day. The guy running the operation said he was impressed by my "re-load" ability and also that I had just the right cock for it...I'm about 8 inches, decently thick and my dick looks perfectly formed from shaft to head and can blow pretty big loads even after only a little break in between. I knew that these were primarily for gay guys to watch but I didn't care. If someone gets off from seeing me, so fucking what. I did these for a while and then he asked one day if I'd want to do some full sex movies and photo shoots and showed me some of his portfolio and all things considered the chicks looked pretty hot and we were now talking more like $300-500 per day so I jumped right at the chance.

It was a crazy scene and pretty much everything you wanted was at your fingertips. Women and drugs galore. Parties every night after shooting. We were all in the 18-22 age bracket so it was just a no responsibility show. But as quickly as I made money it went back out the door on drugs and partying. Then one night when we were partying at the main house this director used for shooting videos, him and a couple of the other "big wigs" in their operation asked me if I would be willing to do some more hardcore shit. At first I was thinking they meant bondage, s&m type stuff, but they quickly made it clear they were talking gay action. I immediately said not a chance, I was straight and no way I could do it. They pushed the matter (and a coffee table with a big pile of blow on it) and said that all the actors in their gay shoots are straight guys because that is the look they wanted in their videos, strong masculine men, not femboys. The guys just do "gay for pay" and they also said I could make up to a $1000 per shoot depending on the circumstances. At that point my eyes lit up and I think they knew they had me. I asked them more questions and they said I could be strictly a top and receive blow jobs, that I didn't have to get fucked or suck or kiss anyone if I didn't want to. I could also do bi scenes where a female actress or two would be involved. I said, what the fuck, let's give it a try.

The next week they had scheduled me in for my first scene. I was shaking like a leaf prior to which was totally not like me. In the other stuff I had already done I was totally calm and had no issues getting naked, getting hard and fucking in front of other people. It was a one on one scene with me and another guy. I was going to be swimming naked in the pool and then get out and immediately go to the lounge chair next to the pool when the "pool guy" was going to show up to service the pool and eventually me who was masturbating while watching him clean the pool. I actually was having a difficult time getting hard which was totally not the norm for me, but he came over and began blowing me for a while and soon enough I did get fully hard. I had sunglasses on and just kept my eyes closed and picturing hot women. I put on a condom and ended up fucking him in a few different positions and then to my surprise he end up blowing his load on my chest as he was riding me, then slid off my cock, dropped back down and sucked me to completion taking my load all over his face.

I said afterward that it wasn't that bad, but I didn't think I wanted to do it again...until I got my next offer and more cash. It went on like this for a while and me just doing the fucking and getting sucked. I still was primarily doing straight shoots though. Then the director came to me with a proposal for a scene. It would be me and this girl I had done some straight scenes with and we would be a "married" couple and then another guy who was coming to our house to do some repairs. But he wanted it to be a scene where me and her completely serviced this guy. We all were going to suck and fuck each other, no holds barred type stuff. I was extremely hesitant but he offered up my biggest payday yet and it was a good chunk of money for 4-5 hours of total "work". I was so far gone into the scene at that time that I agreed and said let's do this.

The day came and again I was nervous. I did all my usual prep on my "manscaping" and where I normally do everything I can to keep myself fresh down below, this time I added the step of the diet one of the other male actors recommended and his full enema routine to completely clean me out. The worst thing on a porn set when anal is involved is having a shit accident. It came time for the scene and we were in the bedroom on a king size bed where I was fucking the girl for a while then the "repair" man came in, he joined in with me "thinking" he was just going to play jointly with my wife but then he starts licking my balls and ass and pulling out my cock from the wife's pussy and sucking on it. We go through some more motions and she is sucking him then she tells me she wants to see me suck him and this is it, the moment I took a cock in my mouth. I did what I had to do and then after he fucks her it was my turn to take his cock. I was laying on my back as she sat on my face and then he started fucking my ass. Hurt like hell but I had to put up a good front. He even made a comment that got into the video about how tight my ass was. Anyway, we finished the scene after everyone had been fucked and sucked and I went out that night with some of the other people from set and we got destroyed on drugs and booze. I was fucked up beyond belief and when I got home that night I said that was it, I was done. Absolutely no more of all of it. The drugs the porn, nothing. The next day I called up the director and said to pull me from the stuff he had me scheduled for the next week. He tried to convince me and told me what a fucking amazing job I had done the day before, but I told him I had to get out. I couldn't handle the life and really was regretting all of it. I pulled the plug that day and never looked back.

So, somehow through all of this I didn't flunk out of school. I ended up completing my degree and living out a pretty mundane, boring college life and working a bullshit part-time job in one of the offices on campus answering phones and shit. Really nobody in my "normal" life had any clue about what I had done. My parents were none the wiser about anything I did partying or whatever and were proud as could be the day they saw me get my degree. I started a job with a top consulting firm and in the decade plus since, have worked hard and progressed so much in my career that I look at the "crazy" money I was making from porn and laugh at how little it is compared to now. I am engaged to a very attractive and smart girl who is an attorney and makes plenty of money herself, but also has no clue about my prior life.

I guess my biggest fear is that one day I am going to come on here and see one of my videos front and center. I know they are out there in various places on the web, but they obviously weren't under my real name and the look I had back then was very different than it is now where I am clean cut hair, have a beard, and even back then in a bunch of the scenes I had bleached blonde hair for a while and a deep Floridian tan. I guess my real name and SSN is on file with the porn company somewhere so that could somehow get out, but generally speaking I got away free and clear without any repercussions. Crazy the journey our lives take.

I confess that over the summer I was on a double date with my buddy and his chick at the movies and we saw Paranormal Activity 3 I believe. We came back to his house and smoked a shitload of weed and got totally baked. It got late and both our girlfriends drove home. We were surfing around on the internet together and he eventually went to a porn site and browsed the genres. He got to some gay shit like he was trying to push it on me, which made me kinda horny. And so I wanted to conceal my arousal so I told him I was gonna go to bed in his guestroom so I could masturbate. Maybe 5 to 10 minutes later he knocks on the door and I tell him to come in. He mentions to me that he's gonna go to college after the summer is over and he's never done anything with a guy before and he kinda wants to try it before he goes away. I play it cool but on the inside I was so totally nervous and excited because I've always wanted to fuck around with him. I go to his room and we take off our pants. We grab each others' cocks and he goes down on me, but he does it kind of awkwardly and made it a little strange so I ask if it's ok if we stopped, because I was starting to feel weird about the whole situation. Embarrassed, he says that's fine and I go back to my room. A few minutes later I had a change of heart. I walked back into his room and without saying anything take his cock out and start sucking his dick like a fiend. I was so horny by that point and the feeling of his dick in my mouth turned me on so much like nothing that has ever happened before. Within minutes, he starts moaning loudly saying that he's gonna cum so I start sucking harder and faster while rubbing his balls. And he shoots a hot load of cum into my mouth and I swallowed it all. We smiled awkwardly after it was over and I headed back to my room to masturbate to what just happened. We have never said anything about it to each other or to our girlfriends since. But there is always an air of sexual tension whenever we hang out. And I get hard whenever I think about his thick cock in my mouth. Just wanted to get that off my chest.

I want to confess I've cheated on my wife a lot. It all happened after we had kids and in a 2 yr span. Before kids our sex life was pretty good. It was nothing crazy at all but we did it 3 or 4 times a week and we were happy. Before my wife I was a man whore and fucked anything that was at least a 6 and I was known to slay some 5's if need be. My wife knew this and still loved me. This is how it all started

After about the 5 month of preganancy my wife hated sex and it just wasn't happening.After we had our child she wasn't in the mood ever. At about 5 months after my son was born we had sex finally and it was really great but needless to say things didn't change. As things would have it we had sex once in almost a year and my wife got pregnant again. Between the baby and being pregnant sex went out the window. It was over a year before we had sex again.

During all this we had a couple we were friends that had a very flirtatious wife. She had stated plainly in front of my wife and her husband that I was her type much more then her husband was. She would text me randomly with a dirty joke or off the wall comment and was always very suggestive. Finally one day I was sick of being the one who was always uncomfortable so I told her she should come by one day when my wife was at work. She texted back "ANY TIME,ANY PLACE". I called bullshit and said "my place 15 mins". She texted back "have my kids with me,call me" I called and she was laughing. She told me I was the one who was full of shit. I said "yes I was just trying to make you uncomfortable like you make me". She responde "Can I be honest for a second?" "Totally" I replied. " I wish I was married to you instead of Rick" she blurted out. Silence on both ends. "Hello Jake are you there" "Uh yeah yeah I'm uhh here" I stuttered. " Are you OK?" she said. "Yea Melissa I'm fine, just caught off guard." "Jake it's true I've wanted to be with you since I was 13 and you were graduating high school but when you moved back to town dating Amy after college I knew it would never happen. I prayed everyday that y'all would break up and you could be mine. You don't know how many times I've thought about you when Rick and I where having sex. How manys I've masterbated to the thought of you. Seriously you were the first guy I ever thought about when I masterbated. I wanted you to be the one to take my virginity"." Are you fucking serious" I responded. " As serious as I can be Jake, I think I'm in love you I have been since I first saw you."

Now lets go back 15 yrs. The first time I saw Melissa she was a homeschooled kid whose dad wad pentecostal eveangelist, and lived in a Camper being pulled by a truck. She was nothing to look at even for 13. Dumpy clothes,out of style hair,and big ass nerd glasses. When I moved back 8 yrs later she was 21 and had comepletely changed. Long blonde hair,36 c tits,nice ass,and no more glasses. I told my dad one day if it wasn't for Amy I would be all over Melissa. If I was going to pick a woman to cheat on my wife with it was Melissa.

"Well if we are being honest Melissa I've thought about you many times since I moved back but I couldn't hurt Rick and I surely don't want to hurt my wife,' I responded. "I know" Melissa whispered and hung up. Needless to say my thoughts for Melissa were totally sexual and my cock was hard as rock after her confession. I jerked off got cleaned up but couldn't get her off my mind. "You ok?'" I texted her. "Yes,I just feel stupid" she replied. " Why" I replied. " I'm not a 13 yr old girl anymore Jake,hell I'm not even 21,I'm 28 and I have 3 kids, your wife is one of my best friends and I'm telling you I love you" "It's ok" I replied "I love you too" In hindsight that was maybe the shittiest thing I've ever said to someone. "DO YOU REALLY?" she asked." Yes why would I lie?" "To be nice so I don't feel like an idiot she answered. That was partly true but my ego needed to be fed and this was the only way I knew to do it. "Nope" I texted back " I'll call you later.

Later that night after the kids were in bed I told my wife bye and went to work out on the way I called Melissa. I told her how much I thought about her all day and that I wished I could just touch her. I threw out as much BS as I could so I would get what I wanted. " You know Melissa telling me you fanatsize about me got me so turned on honestly I'm hard right now just thinking about it." "oh Really" She replied "well guess what Rick is still working and the kids are asleep why don't you come over." "I can't tonight I told Amy I was just going to run on the treadmill and work out for a minute. What are you wearing?" I blurted out."T shirt and some boy shorts" she answered. " Send me a pic" I said. No response I waited a few minutes and started to get sick. The phone went dead. OH shit I fucked up " You Alive" I texted No response. I sat my phone and started to wonder if Rick walked in and found her phone. Finally my phone beeped and there she was laying on the bed no face but her smoking hot body. "Do you like it?" she said "Oh yes" I responded "less clothes more skin" I pushed. No response finally my phone beeps and she is there shirtless in her panties. Now honestly she wasn't as hot without clothes as I hoped but her tits where pretty good. They were sagging a little having had 3 kids in 5 yrs but her nipples were perfect and very suckable. Her stomach was ok. She had some stretch marks but I could work with it.I immediately called her back and said " My dick is so hard no way I can work out." " How big is it" she responded. "Want to see it?" I asked. " Since I was 13" I took a pic and texted it over and she responded "you think I can get it all the way down my throat. Your head is massive." Now by this time of my life I knew what I was working with.A slightly above avg 7in cock with a big thick dick head and good size thick shaft. I've had quite a few girls compliment me on my girth without being prompted. "I'm sure it will fit somewhere." I answered. " Jake make me cum" she said "tell me what you want to do to me spit in your hand and let me hear you stroke that cock." Rick had shitty job and worked shitty hours but he told me many time Melissa was a nympho and would call him while he was work and beg him to have phone sex. That he would get home 2 or 3 in the morning and he would fall asleep while she would ride his cock. So with this is mind I spit I moved my truck to the back of the parking lot and started stroking my cock for her. " Oh Jake I wish I was there to help you I'm so wet already," she cooed "stroke it hard and fast and tell me how much you want"."Oh Melisssa I want to fuck you so bad" I grunted."I know you do Jake" She took over "I've got my vibrator out on my clit too bad it's not your tongue. Tell me you want me" " I want you" I moaned " Tell me when you are ready to cum" she said sounding like she was almost there. "Now" I said Immediately and sprayed a thick rope all over chest and stomach. "OH Jake fuck me" she moaned out. After a few minutes she calmed down and said "I gotta go one of the kids is up call me tommorrow."

I'll finish the story if people want me too.

Craigslist Story #1

So I've been using craigslist for about 15 years and started using the hook up section about 13 years ago and I'm still going strong! Let me tell you about my first casual encounter.

I was browsing through the casual encounters like I had been doing for a while and finally decided to answer an ad looking to get their cock sucked. The pic in the ad was a nice looking average sized dick with a pretty straight forwardly written ad, he wanted his cock sucked by another dude. I was in the mood and sent him a response, almost immediately I had a new message in my inbox! He sent me his address and I told him I was on my way. I get up and grab my jacket and cellphone and run right out the door to my car. I hop in my car and hit the highway. He lived a city over up on the hill or at least that what was the address told me. I drove for about 15 minutes then hoped of the exit and up the windy roads until I reached the house.

I pulled into the driveway of this massive modern mansion built into the cliff, it was pretty fucking impressive. I turned the car off and pulled my phone out of my pocket and put my earpiece in, it was corded one that went in a single ear. I look down and dialed this chick I had met on AFF the month before, she a massive 375lb disgusting whore of a woman, I really miss her... Anyways the phone begins ringing and after only one ring she picks up the phone but before she even says hello or what's up instead she says... "Come fuck me". My response was just as classy... "Shut the fuck up and just listen", She asks "What?". What I MEANT WAS "I cant talk so just listen to what's about to happen". I explained myself better just as I was opening my car door and immediately she asks me "Are you going to suck some cock? Please tell me you're going to suck cock ( )". I tell her "Ssshhh, just listen", I step out my car and shut the door. As I look up there is a man standing at the gate staring at me, so I stuff my phone into my pocket and walk toward him. Just as I get in earshot of him he says "Nice car, you must do well for yourself", at the time I had a pretty swanky ride. I answered with "I do ok, you must do pretty good by the looks of this place.". The guy smiled and tells me he is just house sitting for a fiend. I follow him into the house and he shuts the door behind us...

As he leads me to the lower level of the home the chick is in my ear talking up a storm saying shit like "Oh my god ( ) you're going to suck some cock" and "Swallow all his cum", she was so turned on. As I get to the lowest level where I'm about to put this strangers cock in my mouth I look up and see the entire wall facing out toward the urban sprawl at the bottom of the hill is a giant panoramic window. I turn and walk up to the window and take in the view but when I turn back around I see him sitting on a couch facing me he has opened his robe and has his rock hard cock out. I walked right over and got on my knees without saying a word! I leaned in and slid his stiff cock into my watering mouth and he immediately let out a moan which the girl on the other end heard sending her overboard. She loses it and starts rambling aggressively "Suck that fucking cock! Take it all" that gets me salivating hard as I bob up and down on his cock deeper, wetter and faster. All this causes the guy to start gyrating his hips and trying to fuck my mouth as moans and says "Oh my god you have super head". That pushes me over the edge... I pull back a little and grab his cock with my hand then slide it out of my mouth so that the head is barely touching my lips, I'm staring him in the face but his head is leaned back.

Well he must have felt me looking at him because he looks down and our eyes lock. I get so turned on that I grit my teeth and tighten my lips as I let out the most nasty, disgusting, filthy growl just before I lower my lips and start licking and sucking on his balls. Without breaking eye contact I move back up to the head of his cock while I still have his shaft in my tight grip. I clench my mouth tight again and slap myself on the lips with his stiff piece of meat a few times. He moans and I let out a deep breath then slide it back into my mouth almost taking it all down. At this point my friend sounds like a cheerleader at a high school football game, she is going crazy and can't stop cheering me on but in a disgusting sexual manner... Which gets me going harder. I must have been bobbing up and down on his hard cock for five minutes straight when he begins wiggle and thrust his hips, just then in a loud moaning voice he spits out "Oh, I'm going to fucking cum.

She hears that and her voice drops real deep and she talks through her gritted teeth... "You better swallow all that cum! Don't waste a single fucking drop" Just as she says that he grunts and I feel the first warm spurt in my mouth and I let out the loudest, deepest groan that I possibly could with a cock in my mouth! I grab his wet slippery cock with my hand and slide my mouth up to the head as I start jerking him while I suck the his hot cum right out the split in the head of his dick. I drink down his hot, salty jizz while my friend listens in bliss on the other end of the phone. I suck out every last drip then pull my mouth of the head of his cock and squeeze the tip getting a small drips worth off cum to surface... I lick it up and say thanks as I stand up to leave. He looks at me and says "that was amazing". I make my way to the stairs and he hops up closing his robe following me up the stairs. As we reach the door I open it and he grabs it by the wood holding it, I turn toward him and all in one motion I reach into the robe and grab his semi erect cock giving it one last stroke as I say "Thanks" then turn and walk out.

I go up the driveway and get in my car its so quiet I forget I'm still on the phone with my friend. She blurts out "That was hot!" and I say "You're welcome" jokingly. I start the car and back out the driveway then head down the hill. Before I reach the bottom of the hill I tell her to jerk off so I can listen, without a single word spoken I can hear her breathing heavy and moaning. When I get to the bottom of the hill at the stop sign I immediately get my pants down enough to get my big hard cock out and without letting her know begging jerking off. As I head toward the freeway I'm stroking myself slowly but once I get on the highway I start stroking hard and fast as I fly down the road. It's about 2 am on a weekday so nobody but me is on the highway and I'm zoned out listen to her jerk off and trying to drop a load myself. She is moaning like crazy and I'm getting close myself. I feel it coming so I start stroking like mad and out of nowhere she say says "Fuck yeah! Come for me ( )", she knew I was jerking off. I'm on the verge of squirting a huge load so my focus is only on my dick and the road in front of me. My cock is tingling and I feel the cum rising into my shaft ready to spray everywhere. I can feel that there is a car next to me at this point and they are keeping pace, I feel there eyes on me but I don't give a fuck because I'm ready to cum. Just then the tingle hits the head of my cock, I let out a growl and yell at the top of my lung "I gonna' fucking cum" and the first spurt of hot seed sprays out...

It is a huge thick stream that comes right at my face! I spray myself right in the face and over my head. The second is another fat rope and straight in my face again. I feel the third come out like a puddle of water all over my hand... The wetness does it and I let go and start licking the cum off my hand like the sexual deviant I am! I can feel the eyes of the person in the car next to me and I smile knowing I gave them a hot show. I mumble "Fuck yes" and my friend says "That was hot", I say back to her "You know what's hotter?", "What" she says... "The person in the car next to me just watched my cum all over myself", "Really?" she says. "Fuck yes" and I turn to look at the person driving the car and its a fucking ******* patrol... I turn white as a ghost and he slows down then gets behind me and hits his lights. I say "oh shit" out loud which gets my friends attention. She ask what's wrong and I tell her it was *** watching me and he's pulling me over now. The first thing out of her mouth is "Tell him you'll suck his cock", I tell her to shut the fuck up because its not funny, I'm going to go to jail. I throw my blinker over and cross the lane to my right to pull on the shoulder. He comes on the speaker and says...

"No! Pull off the exit up ahead"

To Be Continued...

my confession: I recently agreed to do a three way with my neighbors there in there late 60's and she is kinda chubby but always wanted to fuck a older woman so I agreed well I show up and they have a couple party favors and I have a couple drinks and partake in the party favors and feeling pretty good she excuses herself and comes back naked and she has some nice tiities and a nice shaved pussy and says today I went and had both my holes waxed for you and bends over and those holes were nice and smooth she walks over and starts rubbing my now hard cock I am about 8inches and pretty thick and she unzips my pants and it flips right out and she says omg I hope that fits and proceeds to start licking it and tries to deep throat me and starts to gag a little and then says I want you to cum on my face and she continues and I look down and on the floor is a wet spot I said your really dripping that much and she says I been want this cock bad I saw you by your pool and knew it was big and she continues and I tell her I am about to cum and she pulls back and I shoot streams on her face and tits and then her husband comes over and starts licking her clean I did not expect that at all and she says lets take this to the bedroom and she lays on the bed ass up face down and says eat my nice shaved holes and I go down on her and she is soaked and I start getting hard again and her husband who is now naked and playing with his cock steps in and starts playing with my cock and starts eating my ass and I am like omg this is crazy shit and it feels really good and I stand up and start fucking her pussy and I slide in balls deep and she lets out a omg that shit is huge and I start to fuck her nice and slow and pick up the pace and I can feel her pussy gripping my cock and she lets out a loud ass moan and starts yelling I am cumming omg I am cumming fuck my pussy fuck it and she came so much it was running down her thighs and I back out and start rubbing my cock on her asshole and she says please be gentle and I start to push it in and her husband gets uner her and starts licking her pussy and I push the head in and she grunts and then a little more and she grunts and then it just slid in and she says yes oh yes and I am just fucking her at a nice pace and she is moaning and pushing back and I can feel my cock swelling and I am about to cum and she says do it cum in my ass fill my ass with your cum and I just let loose and I filled that ass and I pull out and her husband grabs my cock and starts to suck my cock clean and again never expected this crazy shit and I am just sitting on the edge of the bed with her husband between my legs sucking my cock and I grab his head and start pushing it up and down and he is jerking off the whole and says please let me cum on your big cock and said ok and he satnds up and shoots a load all over my cock and balls and says now fuck that whore and I turn around and start fucking his wife with his cum and again he has his tongue in my ass and then I feel him penetrating trim and he has a finger in my ass and a bottle of lube and then he puts two fingers in my ass and says bend over and it her ass and I bend over and start eating that pink tight asshole and then I feel him rubbing his cock on my ole and then he pushes it in and pain just shot through me but it kinda felt good and my cock shot the fuck up and he starts to fuck me and it felt really good and I feel my cock dripping cum and he lets out a groan and I can feel his hot cum filling my now gaped asshole and he says are you ok and I say yes grab him put him over the bed and said your turn and he says oh no i just suck cock and I said not tonight and his wife says fucking that faggots ass I always wanted to see his ass with cock in it and I lube up and push my cock in his ass and he was crying omg it hurts please it hurts and I did not care and I fucked him and filled his ass with cum and then made him clean it off and now his wife comes over once or twice a week for her holes to be filled

yesterday on the way to work i was seriously contemplating suicide.
i feel like nobody loves me and also keep thinking why should they? then i think of how selfish and weak suicide is, which just makes me more depressed and hate myself even more.
i'm 18, male, and still a virgin, i hate my parents, i feel like i'm behind a thick sheet of glass when i'm with my friends. when i'm talking to someone i never articulate my words the way i want to in my head. i feel like i'm communicatively retarded, which is so fucking frustrating. then i don't wanna be around people because i'm depressed, but the lack of human interaction makes it even worse.
i feel like such a weak pussy for being like this, and that i'm better off just ending it. i'm such an egotistical cunt for even thinking that me killing myself would have an impact on other peoples lives. it made me feel like i was some way important when i imagined how people would react when they found out, but then i realized what i was doing, which made me feel like an even bigger piece of shit. i dont even know why i'm confessing this, as if people here would care, but i'd rather get it off my chest here than talk to my friends about it and have them really know how i feel. and i cant even talk to my parents, let alone talk to them about something like this. i get so angry and frustrated at them sometimes i just wanna end it.

im not the person i expect to be, so why go on being this person?

I fucked my 1st cousin's wife at a wedding in early August, didn't pull out of her and I just found out she's pregnant (5 months later).
Heather was already a bit tipsy when she got to the wedding reception. My cousin was arguing with her that she needed to "chill out," but she wasn't having it. I always thought Heather was a pretty girl, only 23 years old (I'm in my mid 40s), and she was always showing off her cleavage. Heather is slightly chubby, nice and thick and has some massive tits to be proud of and I always wondered what they looked like and how they felt. Well I got to find out.
During the reception, she kept stepping outside to have a cigarette, avoiding her husband since they were arguing. I haven't had a cigarette in years, but followed her outside and asked to bum one off her. It was a primal urge, just to get a nice glance at her sexy tits and have some conversation too.
"Sure, you need a light too?" She asked, looking right into my eyes. I glanced down at her beautiful tits.
"Yeah," I told her, and she lit my cigarette, and as she did she pressed her massive tits into the side of my body.
She giggled, "sorry, I'm a bit tipsy. I didn't mean to offend you by pushing my tits into you."
I blushed, "Oh not a problem at all!" I said laughing.
"Oh really?" she pushed them into me again, this time a bit harder. My cock was twitching, ready to spring into action.
“It’s like I’m in heat,” she whispered drunkenly.
"Yeah, really Heather, I'd never deny you pushing your tits on me!" I laughed.
She grabbed my hand, threw her cigarette down and said, "come with me."
I followed her, looking around to see if anyone else was watching us sneak off. Luckily no one else was outside with us, and it was nice and dark out.
She found her minivan in the parking lot and opened the door, and when she climbed into the back seats, she slid her panties off, revealing a pretty nice trimmed bush.
"I don't know if..."
"Shut the fuck up and get in here," she told me. Heather was drunk, and my morals were out the window.
I did, she pushed me down on the seat, unbuttoned my pants and pulled my hard cock out and started to suck on it. She went all the way down to my balls, making slurping and sucking noises. I could smell her perfume, and alcohol she consumed combined with cigarettes.
I reached under her dress and pulled out one of her massive tits, she had lovely nipples and large pink areolas. I saw her lifting her dress and start fingering her pussy as she sucked on my cock. I pinched one of her nipples softly as she moaned.
She pulled up for air, "damn this is a big dick, I miss big dick."
"It's not that big it's only 6 or 7 inches," I tried to tell her as she got on top of me and shoved my dick inside of her.
She started bucking and I pulled at the top of her dress and pulled her breasts completely out. I put them in my mouth, trying to pay attention to each one - I thought ironically, "this is the way I want to die, big ass titties in my face," as she kept bucking on my cock.
She twitched a little and told me she was coming, and moaned. She kissed my lips, and then started moving up and down on the shaft of my dick with her wet hot cunt.
"Your turn," she said, biting her lip.
And I did cum, I came a lot. I felt her moving faster and faster as her beautiful tits bounced in my face and I grabbed her ass and kissed her lips as my cum shot deep inside her. After I was done nutting in her, she got off, and pulled her panties up, straightened out her dress and hair.
"Oh, that was so fucking hot," she said taking a deep breath, "phew!"
Reality was setting in for me; I just fucked my cousin's wife.
"Um, this never happened ok? Shit."
"Oh don't worry silly, no one will ever know. Get back to the wedding, I'll be inside in a bit."
I put my cock away, zipped up my pants and got out of her van. That was the last time I actually saw her, as we really never get together for family get-togethers.
Now my family isn’t that close, and I really don’t talk to my cousins that much at all so it’s only rare occasions we get together.
The other day my mother called me with the news, "Oh, Uncle Bobby called, your cousin's wife Heather, she's pregnant! We just found out. She's due in May!"
I did some quick math. May is 9 months away from August. I’m 90% sure I bred my cousin’s wife.
If given the chance, I'd definitely fuck her again. My cousin is a lucky guy. Kinda wish I could see her big milkers filling up with milk.

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