So, we go out to dinner. Nothing too exciting, but we do pick up her birthday present, a Bluetooth mouse for her tablet. She gave me mine yesterday, a paid trip to a local gaming convention, hotel and everything included. Also, one book of my choice, since when she went to go look, the ones I wanted were sold out.

Anyway, when we get back, as soon as the door is closed she’s stripping, like a good little Slut. She then gets up on the bed on all fours, presenting her ass for her spanking. New rule implemented starting this weekend, and one she loves. So, I take care of a couple things while she’s waiting, and then get onto the bed behind her and start administering her spanking, light slaps, nothing hard, but they do come fairly fast. It takes a couple minutes before her ass is red, but it does happen. As I’m doing this, I look over and see her hairbrush nearby. I reach over and grab it and slide it into her wet cunt (you can smell it, from her excitement about being spanked) and resume my spanking. She moans like a good little Slut.

I give her a few more spankings, then reach down and start manipulating the brush in her cunt, sliding it in and out, turning it, wiggling it side to side and up and down, just driving her crazy. Soon she’s begging to cum. I let her, with her countdown starting at 15. As she’s counting down, my hands are wiggling that brush side to side, and you can see her jiggling, and hear the trouble she’s already having with numbers.  My hand needs a couple seconds break, and she rushes through as many numbers as she can. Probably wouldn’t have made it if I didn’t need a break. Seems those hours of popping a counter 3 times a second helped out. ;)

After she cums I have her roll over onto her back, leaving the brush inside. She spreads her legs for me, and I continue with fucking her cunt. I keep up the same things, eliciting a different feel due to the position change. Pretty soon she’s asking to cum again, and without hesitation I tell her to go. She has a good orgasm. As she’s coming down off of it, I slide her brush out and tell her to clean it. The little hole in the handle is filled with her goo, nice, white, and creamy. She opens her mouth and in it goes. I leave her there as I go to the toy drawer, thinking about what I want to use.

I come back and first cuff her hands, and then secure them above her head (while putting on the cuffs, some of the cold metal touches her skin, and she gives a little shiver. Delicious to watch). Next comes the blindfold. I make sure it’s in place correctly, and then go to get the rest. I put a couple more cuffs around her ankles, and then tie a couple of short ropes around the runners on the top of the bed. Next I snag her little red vibrator, turning it on and slide it into her still wet hole. She moans in satisfaction as two of her three holes are now filled. I then thread the rope through the rings on her ankle cuffs, and secure them in place, pulling her legs up and out. With both like that, her cunt is nice and exposed.

I point this out to her just as the little leather strands from her flogger find her cunt and clit. The reaction is sublime, as she tries to shy away, but with her legs as they are, she isn’t very effective. I’m using the small end, which is thinner and has more strands, and faster. She squirms as I continue the assault, the vibrator going about half speed. I continue this for a couple minutes, varying the tempo and placement of the strikes to keep her guessing.

As I ease up with the flogger I reach down and start work with that vibrator, which has her going all over again in no time, begging to cum. Tonight I’m in an obliging mood. She only has to count down from five this time. With a vibrator in her cunt and a brush in her mouth. It takes longer than normal, but she holds out until she’s allowed to cum, and then watching that back arch and that body spasm is great. I smile to myself as I catch it on video.

I toy with her feet a bit, watching her jump away from my hands as they slide along the soles, unable to go too far, being held in place by the ropes. Then, I turn her vibrator off (it shouldn’t be on for more than 15 minutes, and it’s been about that long since I broke it out) and pull it our of her, with an audible pop. Reaching up, I remove her brush, which she gladly relinquishes, leaving her mouth open, her tongue seeking for what’s coming next. The vibe goes in, and her mouth closes around it hungrily, tongue already working on licking those juices off. Not wanting to leave the brush alone, I pop it against her clit a couple times, getting a good jump from her, and then slide the handle back inside of her.

I look up and see her toybox sitting open, and notice the nipple suction cups we’ve hardly used since buying. I grab them and apply to first one nipple, and then the other, and her voice goes up an octave. The little Slut likes this. Then it’s back to fucking her with her brush, which she actively participates in, fucking it back like a bitch in heat. I pull out all the way out a couple times, and once it slaps against the coverlet, leaving a gooey mess. Guess I’ll have to wash the bedding after this. Oh well, worth it, I think. It doesn’t take long before she’s begging to cum again, this time on video, unbeknownst to her. I let her, and give her a few seconds to recover before I tell her to cum again. She spasms even harder than the previous one as the orgasm racks her body. Such an obedient little Slut. I do love her trick of being able to cum on command. For fun I have her do it a third time, and that one must have been pretty intense for her, and she writhes around on the bed, lifting her ass into the air and pulling those legs every which way. I had to make sure the ropes were holding and the knots weren’t slipping, but everything was fine. She didn’t pull the bed down around our ears, not for lack of trying though.

I ease her brush out one more time, and it goes into her mouth, her vibrator being set off to the side. She’s recovering, but I can’t just leave her there, can I? I reach down, two fingers parting her folds while a third finds her clit. She goes wild as soon as I do, and within a minute is ready for another go. She starts at 10, as told, and does have some trouble getting there. She manages, and cums, legs clasping around my hand as much as they can. It’s a nice long orgasm. Must have enjoyed that one. :)

She is spent, so it’s time to get her released. The ropes and cuffs come off, the nipple cups go back into their box, and the brush and vibe are set off to the side for cleaning (she’ll take care of that and put away the ropes when she’s recovered enough). I get her a glass of water, which she accepts, before going back and just laying there for the next five minutes, unable to really think or move. I cuddle a bit, and she rolls onto her side, molding against me.

While we lay there, I lightly stroke her side and squeeze her shoulder. She’s still horny, the little Slut. You can hear it in her moans and see it in her movements. Yes, well trained. As soon as I tell her to get a hand busy on her cunt it‘s there, working that pussy. I concentrate on her shoulder, one of her weak spots, and let my other hand idly play with her nipples as she undulates against her hand. The action on her shoulder is what really gets her going, the nipple play is just a bonus. As I increase the pressure, she is asking to cum. I let her, and it’s a nice and easy one, she’s had time to cool down.

I stroke up and down her exposed side as her hand continues it’s ministrations (she hasn’t been told she can stop yet). I then stroke lower, over her ass and then into her wet pussy from behind. She moans louder as I begin to lightly pump in and out of her, every few strokes taking time to just rub up and down on those lips of hers. It’s constant attention, though, and with her hand still going she doesn’t last long. She cums, hard, with me inside her. I do love her doing as she’s told.

Then, to end the session like it began, I slide out and land a slap to that ass. The sounds she lets out is exquisite, and I continue, the slaps becoming harder and faster, but only on the one cheek that is not covered by me. She doesn’t seem to notice that only one side is getting the attention, or doesn’t care. She’s bucking against her hand in no time. And her request for permission to cum takes her 30 seconds to say, the words won’t come to her pleasure addled brain. I love that, too. Can’t even concentrate enough to say “Sir, may I cum?” She doesn’t get to cum until she’s finished her words. It’s difficult for her, but she perseveres and lets out one final orgasm for the night, before collapsing, as I tell her she can stop.

We cuddle for a few more minutes. As I get up to leave, I lean down and kiss her ear, whispering “Happy Birthday”. I’ll take the grunt that elicits from her to mean “Very happy indeed”. After I leave, it’s another 20 minutes before she can get up and move again without falling down. She does clean her toys and tries to put away the ropes. But she can’t remember how to wrap them just yet, so I show her one, and she does the other. Brain foggy and all that.

Anyway, that’s how our night went. Hope you enjoyed. :)

A couple weeks ago my step daughter had a gender reveal party. Among the people she invited was her mom (my ex) her aunt JoAnn and her cousin Amanda.

My ex is in between men so she dressed sexy to get my attention.  She is and has always been a slut. That's why we married but eventually divorced. She kept sleeping around while we were married. She came home with a pushy full of cum. I use to enjoy sloppy seconds and cleaning her shaved pushy but when got pregnant my a black guy I had enough.

Amanda is a year older than my daughter and were always close growing. JoAnn is a near mirror image of my ex except with larger (fake) tits.

My ex always fantasized about me fucking her sis while she watched. She even loved it when I'd moan her name into her ear as I emptied my balls into her 

The gender reveal was fine but mid way though I noticed how Amanda was paying a lot of attention to me.  Sitting next to me, finding reasons to touch my arm or back. I also noticed how pissed off my wife became. 

She was dressed to attract attention but I was enjoying Amanda much more who was wearing a simple sun dress.

As we were finishing cleaning up, Amanda took me aside . She asked me to lean down and she quietly confessed she had the hots for me and wanted to feel me inside of her while she was growing up. Then she gently kissed me. 

I was beyond turned on and told her i would be happy to make that happen then kissed gently on the lips and left

This past weekend I took my niece to a hotel and made love to her. We started the evening after she dropped her two children off to her moms so she would babysit them. We got dinner them walked along the river front park before heading to a nice suite hotel. 

We made love for several hours. Her body was my willing playboy. I made her cum 6 times before filling her body with my seed. It was when she started calling me Uncle Shawn that I couldn't take it any longer.

We lay cuddling each other afterwards and talked. She said  the 22 year old age difference didn't bother her and how it was worth the wait. She also told me JoAnn knew she had come to see me. I guess she told her daughter that she knew I had a big cock because her sister bragged about it to her.

All this talk just got me excited again and I throughly ravished her lithe body again. Pulling her on top of me at the end to empty my second load into her.

Afterwards she called her mother to see if the kids were  all right. I heard her mother saying they were fine and that she stay with me and just come home in the morning.

The next morning we woke and gently made love a third time. Afterwards we dressed and went down to get the continental breakfast. All the while we sat together she kept calling me her uncle so others could hear it. 

As we went back to the room  she wrapped her arm around me and asked me not soquietly of we could make love again. I said of course. One of the other guests heard us and looked very confused.

We have plans on seeing for lunch the week near the hospital she works at, the grabbing dinner and a movie saturday.

Last night I was thinking about a convo I once had with another guy about anal orgasms, I've never tried any kind of assplay and didn't want to start, but I was bored and a lil horny, but not hard, and something possessed me to go ahead and try something. So I went into the bathroom and tried getting a finger in, wasn't too tricky, didn't get too far before I ran into some shit, but I 2'd and tried some more, and then two fingers. I felt around in there, but wasn't sure what angle to look for so I kinda just felt around hoping something would feel right, but didn't feel much. I thought maybe it just wasn't reaching it. I kinda got carried away and decided to stick something up there, the only suitable thing was the handle of a toilet brush which I lubed with some vegitable oil and stuck between the mattress so it would hold itself, then got into kind of doggy and backed into it.it felt cold and weird, and I had to bend kinda funny to get it in smoothly, at one point like a dog lifting its leg. I didn't do too much back and forth action, just kinda tried to get used to it or find whatever spot I was looking for. didn't really get much out of it, but I wasn't even hard, I had already fapped that day so didn't have much to go on, that might have been where I went wrong in this experiment, I shoulda waited until I was really horny. But I did feel my dick when I was about to stop and I was dripping a lil bit of clear cum, so maybe I just had empty balls to start. anyhow, didn't get much out of it but was probably doing it wrong, and when I pulled it out again I was probably 7 inches deep, at least from where I held it as I pulled out, but I got worried when I saw a redness mixed in with some of the stains, thought I may have hit something, like a polyp or just ripped a lil. but I'm not too "butthurt" atm, maybe on the outside a lil, and I've been farting more today. idk, maybe I need something softer to practice with, and that led me to thinking about letting someone fuck my ass, but I'd have to get head or ass in return or it wouldn't be worth the effort. then I started thinking I've become exactly what I didn't want to be when I first had that convo. Now I'm kinda mixed up about what I wanna do.

Student - Professor - Instructor story

I just became an instructor at a university on the west coast. Before starting, my friends joked that students would hit on me but i vowed they'd be met with rejection. That was naive of me...

This beautiful freshman of mine (slender, toned, used to play soccer, minimal makeup, 20) started attending my online office hours for genuine reasons and we really got along. At the end of one online office meeting she mentioned how she'd come to my next in-person office hours (which was last week). Despite finding her very attractive, I kept telling myself to get a grip and to stop fantasizing. That was also naive of me...

True to her word, she attended my in-person office hours last week. While we still have to wear masks, and while I'd never met her in person, I could instantly tell it was her walking through my door. She was wearing a tiny pair of short shorts that failed to completely cover the bottom of her ass and a crop top. Despite students normally sitting opposite me, she sat down on the chair closest to me. We conversed, joked about where we both grew up/accents, and then she decided to show me a picture of her parents' house on her phone... As she scrolled through her pictures, she rested her phone against my leg and leaned forward. I immediately panicked at the idea of a colleague walking through the door and I quickly moved away. I then asked her to sit opposite me as "those were the rules" (they weren't really rules, I was just afraid). I instantly felt like an idiot, and i still kind of do. I'd have done anything to have her little hands under my pants.

She consumed 45 minutes of my office hour and as she stood up to leave, I noticed her left short had risen/folded up, revealing half of her tight ass cheek and better yet, part of her crotch. As she was flinging her bag onto her back and making her final comments, my heart stopped... The action of slinging her bag had revealed part of her pussy lip as a result of her left short being raised even further (I could literally see a tan line). As I starred, I quickly realized she was unfortunately wearing nude colored panties, and there wasn't quite as much lip showing as I first thought. Nevertheless, the thought of this tight bodied 20 year old being (seemingly) oblivious to what was on display to my older eyes sent my heart into overdrive. All of those fraternity boys who have probably flirted with her in hopes of seeing her tender pussy, and here I was effectively being paid to spend time with her and gawp at her body. I couldn't help but imagine what her parents would think about their girl being looked at like that while they're at home paying her tuition. Their beautiful smart daughter parading her tight ass around campus as students and faculty looked.

She emailed me yesterday about meeting in person after Thanksgiving break along with a comment about how she enjoyed our chat. I have no idea what to do... If I could do what I wanted and she consented, I'd bend her over my desk and spank her tight, athletic butt cheeks that she happily parades around campus. I cant help but fantasize about pushing my face into her crotch, sweaty from walking around campus all day... before sliding into her warm pussy that she seems to obliviously display. All i want to do is lick her (probably) tiny butthole.

It is worth risking my job? What if the 'phone on my leg' thing was totally innocent and she has no interest in me? What if she's just after a good grade? Obviously I wouldn't do anything without her consent, so surely I have to wait for her to initiate things? Did I scare her off by asking her to sit across from me instead of next to me? What if she's a completely innocent ditsy girl, oblivious to what she's displaying to the campus?

I hope to be able to update this post after Thanksgiving with developments.

I shall title this confession post:

When Your Hooker Has A Surprise For You (And It's Not a Penis)

I have made a post or two about a blonde MILF hooker (escort, technically) I've been seeing on occasion by the name of Savannah.

The last confession about her that I posted was after going to a strip club. I was drunk, horny and had her roleplay as a stripper that takes me into the vip. That night we sucked, we fucked and in the heat of the roleplay when I wanted to fill her up... she sank into her roll and told me that she wasn't on birth control and that if I wanted to cum in her I would have to fuck her in her ass (she's actually fixed).

She ended up riding me reverse cowgirl with my dick buried deep in her ass. I took in every moment, slowly climbing to a huge orgasm, filling her shitter with my seed. I didn't think I could cum as much as I did. I will never forget the feeling as I erupted deep in her, I wish I could properly describe it.

Tonight was my 8th time going to see her (I believe). I wanted to cum in her ass again, so I told her I wanted that same roleplay.

After seeing her many times I've come to accept that she is always "running late". She leaves me sitting in the driveway while she is preparing for our time. She actually cares about what I want and I have no problem waiting for her to put on outfits, makeup... whatever. I've come to expect the wait.

Same thing this time, no surprise. As per usual she told me that she was getting ready and it was worth the wait.

Then she tells me that she was ready and I went to her door.

I walk in to find her and another, younger hooker dressed up like strippers with a chair in her living room for me to sit in. I'm in shock as I realize that she was setting me up with this girl as well. I didn't bring enough to pay both, but then I gathered that they expecting nothing additional in return. I was in awe of this young, skinny, sexy brunette who keeps starring at me up and down. She seems excited, but I was the one in heaven.

They gave me a hot double lapdance and made out with each other. The young hooker started kissing on me. As things heated up Savannah, taking to her character, says we need to go in vip if we want to keep the fun going because they will get in trouble on the floor. Before long they both have me by a hand and are dragging me into the vip (bedroom). They undress me before Savannah gets down and sucks my cock while the younger girl made out with me and rubbed my balls. After while she joined Savannah and they took turns sucking me taking little breaks to make out.

I laid down on the bed and my [new] favorite hooker jumped straight to sucking me off. She gave a much better blowjob than Savannah. A lot more tasteful use of suction and tongue.

As she did so, Savannah played with and nibbled on my nipples before looking me in the eye and told me that I need to pick one of them to fuck from behind.

I thought about it and had to clarify... pick one to fuck "first". I was correct, they both wanted to fuck. I was getting ready to fuck Savannah when she stops me me. "One thing different this time..." she reached for a condom and told me we were going to be using rubbers.

Savannah and I had not used a condom since our second time together. By the third meet I was exploding deep in any hole I wanted... down her throat, in her pussy, and in her ass. I wasn't excited about using one but I agreed.

Two naked whores in front of you, you don't complain.

The brunette put the condom on with her mouth and I was staring down Savannah who knew I wanted her. Before I could fuck Savannah the younger one was already telling me that she wanted to go first. She hadn't got the vibe that I was ready to fuck savannah first, but I liked that she was eager to fuck me. I looked at savannah as the brunette took position bent over with her ass in the air, face in Savannah's pussy. She liked to keep her legs together for doggy style, so I slid between her skinny thighs and started fucking her pussy from behind.

It was a beautiful sight, as I'm sure you're imagining right now.

But the rubber was having negative consequences. After a little while I was having a bit of difficulty staying fully erect due to not being able to feel her pussy around my cock. Savannah knows this is not normal and she looks up at me saying "your dick just doesn't like condoms, does it?".

No, no it doesn't.

Savannah tells me that I can take it off and she would fuck me. Apparently the condoms were just for the younger girl.

I get ready to pull it off when I hear the younger one talking to Savannah saying that it was okay and that she wanted to take it too. I could see Savannah giving her a serious look as she says "are you sure...? I guess if you want to, you're the one who knows your cycle." I hear this and before I even have confirmed that was fucking her raw also I had the rubber off, was at full erection and positioning to fuck her, completely ready and go.

This sexy skinny brunette with a beautiful tight ass looks back at me as I line up to enter her bareback. With the look of approval, I slide in and feel everything. She was way tighter than Savannah and I truly loved the way her pussy gripped my hard cock as it began to get more and more wet.

After while I had her pushed down flat on her stomach as I pounded away, making her squirm under me as she came. Her pussy overflowed , contracting in all different ways. I pushed myself to the edge a few times. I began pulling out to where just my head rested inside of her opening, in order to control my orgasm.

There were definitely a few times that cum was leaking out of my overe-stimulated dick into her pussy. After pulling out to my head a few times I remark at how badly her pussy makes me want to cum. Savannah tells me to make sure that I don't and tells me to save it for her.

She obviously didn't want her younger hooker friend to get knocked up.

I fucked her for another 5 or 10 minutes before telling Savannah that I wanted her to ride my dick.

I slid out from behind her young friend who was panting, covered in sweat (both her own and sweat i was dripping down onto her) and laid down on the bed. Savannah took position and slid onto me. I began thrusting upwards, pulling her down as I pounded up into her. I made her squirt on me and her friend remarks at how hot this was to watch. I fucked her into three squinting orgasms, completely soaking me. Her friend assumed position at some point during this to lick my balls. Next thing I know I feel my orgasm building... I smack her ass as I grow closer and closer, finally throwing my arms around her back, digging my nails in and flood her pussy with my jizz. I lay there with my pulsating dick buried in her as her friend cleans the leaking mess, remarking at how she was content and that was "the biggest dick she had all day". It being just before midnight, this gave me a nice boost. After 5 minutes or so Savannah climbs off.

We began to talk as I tried to get dressed. It turns out that she asked her friend to join us for two reasons: she loved my dick and told her friend how much she appreciated me for being cool, and having a dick that was "something special". I first heard those words come out of her mouth the first time we met and I made her cum over and over, nearly to the point of her passing out. Also, it wasn't a good day for her when it came to anal and she thought this might make up for it.

It did.

Savannah mentioned one thing that caught me off guard but really turned me on.

The first time we fucked bareback I tried to get her roleplay mom/son with me. She wasn't comfortable with it, but agreed to stepmom/stepson. After we got together for it, I didn't think she was that into it... but on this night she mentioned how much it turned her on and that she didn't expect it to.

I think it might be worth trying to convince her to do mom/son. Maybe mom/son/daughter, if that sexy young thing can get kinky with us.

What I do know is that I will at least definitely be filling my stepmom's ass with a nice big load very soon here. I really want to see if I can push her boundaries even more and go full mom/son.

i have a confession.

the passed few weeks have been hard on me, i will spare you the details and just say this to start:

i am conflicted in myself, it seems im waiting on something to make me snap, just so i can beat the fuck out of something then break down and cry.

i am a male, about 25 years old.

the love of my life, just so happens to be single again, and i come down with this "psychotic episode".

i've placed myself into the sidelines, just to make sure i knew that i SHOULDNT try. i love her, in no way would i purposefully hurt her.

but as i was saying, i am conflicted and on the verge of "fuck it".
But, she helps me. she is what i need for a calming effect.
i see her, i see a future, OUR future.
when i am with her, there is no thought of "when will i get my next toke of weed".
she IS my toke of weed, she is my blue dream, she is my candy kush.

but i sideline myself, and all i can chant to myself is "best i can do, is help her along and keep her happy, because all i can do, is enjoy her company"

i want her to find someone that wants to make her happy, the last guy didnt work out to well.

where was i going with this?

i forgot, but short story into a sentence:

i love her, i cant be with her because im too fucked in the head, but she still calms me while we're together, even while she doesnt do anything other than sit there.

she is, all in all, a beautiful woman and worth the world, and i just hope she can find someone that sees her, the way i do.

My all time favorite sex partner was a girl from high school. She had a brain tumor and it stunted her growth. It was like she never entered puberty. even at 18 she was well under 5ft tall weighed only like 50lbs. She was a grade below me, we started to seriously hanging out when I was in 10th grade, but I'd known her for years. It took me almost a full year to sleep with her, but well worth the wait. She couldn't get enough of it, every chance she got she was asking for more. We were never a couple, she wasn't interested in being my girlfriend, just friends with benefits. And because of her appearance no one thought twice about us, I normally treated her like a sister in public. In 12th grade I introduced her to the joys of other girls, which she took to just as much as sex.
The only bad thing about her was that she refused to let me video tape or photograph her, too self conscience. I still talk to her occasionally and meet up for coffee.