Tag: Anal

[MF] The Free Use girl

During a chance encounter on POF I messaged this girl because none of her pics were of her face. I got curious from her standoffish nature and after some texting we found out we’ve passed by each other constantly. She was 5’10” and built like a fat amazon. I just had to have her over just because I needed to cum and I was tired of jerking off. Her husband wasn’t giving her what she wanted so of course she was ready and willing with a little coaxing.

She brought little bottles of alcohol to do shots to work up the nerve but I soon had her in my bed and spread open. On the first slide in I realized that she was so super tight and gripped my cock like a vice. I enjoyed giving her what her husband didn’t selfishly. She stopped in the middle to cry from whatever stresses she had going on in her life. After a little year drying she pushed me on my back and mounted my cock and with a ferocity I didn’t expect she bounced and rode my cock like her life depended on it. I warned her I was about to cum and she just pushed my shoulders down to just ride me even harder and I felt myself explode deep inside her while she gasped and exhaled softly. We kissed after she got dressed and I didn’t hear from her for about a week until she randomly texted me. Read more »

[FM] I was an exhibitionist sort of by accident

I became good friends with an escort. I saw her as a paying client and other times we would just hang out and it turned into dirty fun.

Usually, if I called her it was a paying date. If she called me, it was a favor or just a chat or sometimes she was horny. It was a little bizarre.

She texts me and says “I need you. Can you come over at lunch.” I didn’t text her back immediately and a few minutes later she calls. She is a little panicky. I asked her what “I need you meant.” I was trying to figure out if this was a date or she was horny or something else.

After talking and not getting much information, I agree to meet her. She was really specific about the time.

I arrive at her place and she is walking out to my car before I even get there. She says, “Don’t be mad.” That sets off alarm bells. I wondering what’s up. She tells me she has a longtime customer that is old. He can’t get it up anymore but he really loves to see her get fucked. She wants me to fuck her while this dude watches. Read more »

My Roommate

She didn’t know I was there. Or maybe she did, and just didn’t care. It was 1:30am on a Wednesday. Late by my standards. I realize I wasn’t the typical college freshman, but I had shit to do the next day. Didn’t we all? I guess some people cared about responsibility more than others. Oh well. This is why I was in bed. I like sleep.

My roommate, Riley, had her boyfriend Andy over. He was always over. I guess they were high school sweethearts, or whatever. He didn’t go to college, he finished high school and went right to work at his dad’s landscaping company. The money was good, and hell, if he was just going to inherit a successful business someday, why bother going to college. I asked Riley what happens when winter comes and there’s no land to scape, and she said, duh there’s plowing. Ok. I still don’t understand how there’s so much money in that.

Well it was definitely winter now, because Riley was getting plowed a lot.

Riley and Andy must have been out drinking somewhere because they stumbled into the dorm, and basically just crashed onto the bunk below me. This is partly why I wanted the top bunk. As little disturbance as possible. Read more »

[FM] I faked it with an escort, but she caught me. A little Long story

had a period in my life where I was trying to figure things out. I was having problems at home. My solution back then was escorts. I can’t say it was a good idea. I spent so much money and time. I’m sure I was going through my mid life crisis a little early. Here’s one of the times I saw an escort.

I hope it is a funny and sexy story. All of my stories are true.

A friend of mine told me about an escort that could deepthroat anything. He said she was a nurse on the weekends but was fairly new and made extra money escorting. I was very interested in any woman who loved to deepthroat. I also have a nurse fetish that I still have not really explored or figured out.

So, I get a referral from my friend and Grace (not her real name) is satisfied after just a couple verification questions. She tells me she is ready on short notice for special friends. We meet a few days later. Read more »

[MF] A FWB for the books

After my separation from my wife and a string of one nighters I wanted to get a steady FWB. Sexy, dependable, and ready for bareback action that I craved. Whisper was locked and loaded and I posted on and off for a week until she replied in a direct message. A couple face shots and we moved it to Kik.

She was shorter, white, a bit of a stomach, and had some nice big hanging tits and a curvy ass. And she lived just right down the street from me, the best of luck!

It didn’t take much coaxing for her to drop by. We instantly connected physically and she was naturally submissive. She was forward that she wasn’t on any kind of birth control…..sigh…..grabbed a condom and went straight in. She was kind of bratty in that cute way, making me slide out to prolong the sexytime. But oh god when I had to slide back in her velvety pussy gripped hard. She loved nipple play and choking and loved every position. I fucked her hard and deep and she loved uttering sweet nothings in my ear and naturally wanted me to be pleased in the fullest and enjoyed being used like a sex toy. After I came hard and deep and disposed of the condom I just laid with her on my bed until I was hard again and went straight into using another condom with her. After she left I needed her again. Sex with her was like a drug. Read more »

[M]38 fucking a F[21] student

This happened so unexpectedly and it happened few months ago. I’ve signed up for some evening classes and it was a pretty small group. It was just the 8 of us and it was a split, 4 guys and 4 women. I really didn’t go there to meet women and at first I wasn’t interested in any. The youngest and the one I will fuck later was this artsy student, she is a small thing, 4’9, no tits but a nice ass, slim body and nice curly hair. And I was sure that she was wearing no bra the whole time as her tits are non existent. I usually am a tits guy but I did make an exception in her case apparently.

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We didn’t usually sit close so the most of our interaction were maybe few minutes chit chat before classes as we were gathering.

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This all changed as we moved to a new classroom and she sat next to me. During the class while we were working I looked at her and realized she is looking at me with the look on her face that made me melt on the spot. None of my ex girlfriends has ever looked at me like that. Not even my current one. Read more »

Regret [MF][submission][oral]

Here’s another story from long ago. Imagined meeting between an old friend and I

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The last time we talked, I talked you into our old bad habits. Into being bad again for the sake of pleasure. I know were miles away, and I know it’s just text, but being bad is addicting. And when you caved I knew we were going to have fun, and text each other to an orgasm or two apiece. But something always comes up, and you told me you were going to take your toy for a joyride.

I wanted so bad to hear from you again, while you fucked yourself. To read your messages as you imagined what I would say. What I would do to you. I know I was in a compromising situation, but that’s what makes it fun. I wanted to send you a message about what I was imagining, about what I wanted to be doing. But you stopped responding as I imagine you were watching a video and cumming with your toy buried inside you.

So here’s what I am thinking about now. Read more »

Trivia Night With Steph (Part 2) [MMFF, ATM, Incest]

…..continued

I sat there, taking in the view of this tiny tan skinned beauty facing us while straddling the head of her husband, as he lapped my cum from her pussy. She was standing on her knees at the far end of the ottoman. Her gorgeous breasts stood at full attention, filling her narrow chest, her brown nipples pointed up slightly. Her flat stomach lead down to her bare pussy that she was grinding forward and back on her husband’s face. One arm was above her head, holding her hair up in a mess at the top of her head. Her mascara was smudged and dried onto her face in the tears of the almost painful orgasm I gave her. Her eyes closed, with her mouth open as she breathed, the corners of her mouth turned up into a smile. Read more »

Spying On My Sister

The noise woke me up. I looked at my phone and it said the time was just after 2am. Laughter. The laugher was coming from the basement. My sister’s bedroom was down there and I knew she had her boyfriend, James, over.

My room was upstairs, two floors away, so it was weird that I heard anything. Jenna was 21, two years older than me, and she was home from college on summer break, and it seemed like James never left her side that summer. He was the same age as her, but that seemed to be about the only thing they had in common.

James is a cute guy. Slim build, toned. The slightest of facial hair stubble. At that point, he had been with Jenna for about five years. I think she lost her virginity to him. She always thought he was the nicest guy and the most chivalrous of men. And he was. He treated her great. They had fun. He made her laugh, obviously, because they just wouldn’t shut up that night. Read more »

Begging to Make a Movie [MF]

I was seeing Misty on and off for about 2 years.
Really it was purely just a hookup/booty call but we had fun and were very sexually compatible.
She was really a pioneer of using phone cameras to take naughty pics in the early 2000’s lol.
We have had some really good adventures in that time. She was a small girl, about 5’3, petite, very tight frame with a nice little bubble butt that I used to love.

One night I was at her apartment and we were drinking some tequilla and she was getting loopy and she was pestering me about making a movie/porn together. It wasn’t really my thing but I was game.
She really wanted to, she says she loves being in front of the camera.

I asked her what she would do with it?
“I would keep it and masturbate to it” she laughs.
I ask her if she has any she uses?

She slyly smiles and says she has one she uses all the time. I ask her to put on the VCR (yes we are going that way back), she is a bit embarrassed and says she isn’t sure.
I tell her I would make a deal, if she lets me watch it I would be game to film one with us. Read more »