The Story Of "The Sluttiest Thing I've Ever Done"

[Gregshaw]

A while back someone posted a thread asking "what's the sluttiest thing you've done?" & I posted a quick reply with a promise to tell the full story later on.

Well, it's "Later on" time, so here it is. I've tried to be as accurate as possible, names have been changed & much time has passed so my memory is a little vague. First, I hope you enjoy it & second, Jeanie, you know who you are & I miss you terribly.

Part 1

Back when I was 19 I was tall & slim, I'd already had grown my hair out long & kept myself in shape with running, biking, swimming & lifting. I'd played around with some guys even though I was still mainly dating girls & one occasion I'd become friends with a girl who was a lot like me, tall, slim, sporting a narrow waist set above perfect pair of athletic legs & flowing blonde hair.

Her name was Jeanie & people thought we were twins, or at least brother & sister. Jeanie wasn't your usual kinda girl, she was crazily athletic, I don't think anyone beat her at sprints. She was gorgeous, from a distance, but close up the scars on her elbows, knees, chin etc etc became obvious, earned through many years of downhill mountain biking, rock climbing etc. She had endless energy & a sex drive to match.

We were out running one day when I heard a car approaching from behind & a guy shouted "Hey ladies! Need a ri..."

I turned around & saw a convertible with the top down, full of young guys. The driver's face was one of pure horror when he realized I was male. He turned blood red & sped off, the others in his car laughing & jeering at him as they disappeared down the road.

After we'd stopped laughing I said to Jeanie, "Do I look like a girl from behind?" she gave a slight laugh, shrugged & nodded, adding "Kinda." She must've seen the look on my face because she craned her head over to look at me from behind & added "And a pretty hot one, too."

Jeanie would know because she often swung both ways given a few drinks & a pretty face on a warm summer's night. She had a thing for the lady swimmers & tennis players & it was hot to see her dancing like a cobra as she slowly got hornier & began to wrap herself around some gorgeous chick. I learned a lot from Jeanie about how to drive a woman wild & made good use of her advice.

I'd never thought anything like it before, U was already enjoying other guys, but her words stuck in my head & slowly but surely I began to think about what it'd be like dressing up like a girl &, eventually, fantasizing about hooking up with a guy dressed up. Was I really as "Hot" as Jeanie claimed? I decided to find out.

[Gregshaw]

Part 2

Later that year I was doing the “Poor Student Thing” & Thrift Store shopping for clothes when I got the urge to nonchalantly browse the women's section. I chickened out of buying anything several times, but then I saw a bright red Cheerleader outfit & it just bored into the back of my mind.

I went back mid week when it was quiet. It was still there & I casually looked it over. It seemed to be about right size & I threw it over my arm & tossed a man's jacket over the top to hide it then went into the changing room.

The top didn't fit too well, a bit too tight here & too big there & I'd have to pad out the chest, naturally. But the skirt was fine, sitting so that a hint of my butt just showed beneath the hem. I took a look in the all around mirrors & thought to myself “ WOW! Nice ass.”

I screwed up the courage to take it & my other purchases to the counter all the while feeling like a huge, flashing neon sign was above my head saying “Crossdresser!” No one batted an eye.

Over the next month I scored underwear, a pair of Hi Top sneakers & the most difficult of all, a small bra stuffed with old socks that took forever to get anywhere near looking right so i sculpted some foam I found. Less padding stuffed in there was definitely “more” when it came to looking anywhere near right.

This was back when Craigslist had introduced personals so I logged in with my dial up modem & typed out an ad & then waited & waited & waited through the no-shows & flakes….Nothing for weeks on end.

In desperation I texted Jeanie & asked her what she thought. She sent back the picture I'd used showing me from knees to neck, that revealed my flat stomach & slim waist & she gave a one word reply “HOT!” She wanted to hear the erotic details of all my encounters & was stunned when I told I'd not had any, until finally she said “Maybe I can help.”

[Gregshaw]

Part 3

Kris was an older guy, mid 30s, kinda good looking, kinda easy to overlook, active & available after a messy divorce. Jeanie had a fling with him & could vouch for him as sane & trustworthy, so I wouldn't be letting a serial killer into my apartment. I was sent a picture, he looked decidedly ordinary & like an accountant. There were no nudes but Jeanie assured my he wasn't packing a baseball bat in his pants that'd rip me to shreds.

I told her I wanted it like it was an anonymous hook up, with an unlocked door & me already bent over, no small talk, just dim lights. The next night I got ready & awaited the message, “I gave him your number”.

After what seemed like an eternity I received my first text. We messaged back & forth, he was, as they say “Straight” but “Curious” & was enjoying his new found freedom. We thrashed out ground rules, he wanted no kissing, no face-to face & no talking. He agreed to being sucked but he wasn't going to do any reciprocation, which was fine by me.

“Ever done this before?” I asked. There was a long time before he replied.

“No.” and then. “When?”

As if in a dream I typed out. “Tonight?”

Minutes passed like centuries as I stared at the phone….DING!....”OK.”

[Gregshaw]

Part 4

My heart raced, my head spun, I cleaned out, pre-lubed myself, dressed up & turned down the lights. At the last moment I decided on a small amount of lipstick & then a blindfold. The thrill of being on my bed face down, ass up was enormous. I didn't have to wait long & yes, Kris knocked & even rang my goddam doorbell! Several times.

Just as I was beginning to think I'd have to get up & open the door I finally heard it swing open. Then nothing. I was confused but then I heard the door close & car keys softly clink. Was he taking his jacket off? He moved as quiet as a cat & I didn't turn around to look because I didn't want to show my face & ruin the illusion so it came as a surprise, therefore, when I felt his fingertips brush the curve of my ass under the skirt. For the first time he made a sound, a slight gasp & I felt a shiver in his touch.

I slowly wiggled my hips from side to side & now his full hand rolled over me. I heard belt buckle & zipper & soon the bed heaved as he knelt beside my head. Around the edges of my blindfold I saw a meaty hand dig into his underwear & rummage around, pulling his cock out. It curved away from his groin, the cut head resting on two hairy balls. I was intimidated by his size, but stroked him tentatively.

I heard him give a muffled “Umph!” sound, saw his cock twitch upwards & begin to stiffen. I lifted him up & opened my mouth, now he audibly gasped “Oh yeah! Mmmmm!” I felt his balls move & his cock harden in my mouth. I was relieved to find, when I took a moment to stop sucking & stroking his length, that he hadn't grown much fatter & longer. He was definitely a “Shower” not a “Grower”.

A hand was now gently but firmly pressing on the back of my head making it clear what he wanted & I eagerly took him in my mouth again. I felt so slutty & horny in a way I'd not experienced before. I wanted to tell him to fuck me, rather than squirt in my mouth, but his hand insistently kept my head bobbing back & forth.

I needn't have worried, I felt him shift slightly & then felt his hand go up my skirt & on my ass as he continued to let out contented moans. I wiggled my hips from side to side again & he pulled back slightly then slipped his fingers into my panties squeezing first one pert butt cheek then the other. “Dam!” he half whispered “Mmmm.”

First one finger, then two brushed over my pre lubed hole, circling it & sending shivers up my spine, then gently slipping in. I groaned deeply causing his cock to fall out of my mouth. This seemed to be the signal he needed & soon he was behind me on the bed as I dug under the pillows to pull out lube & condoms. When he'd rolled one on I reached back & liberally lubed his throbbing cock.

[Gregshaw]

Part 5

And so we reached the moment of truth, him holding my hips in both hands & me, in full cheerleader outfit, reaching back, guiding the tip of his cock towards my aching hole. Until now we'd hardly said a word, but I couldn't contain it any longer & found myself saying “Fuck me, I want you, fuck me!” I didn't have to make it any clearer as he gently, but firmly pressed forwards & speared my tingling spincter.

There was that moment of being penetrated, that feeling of being stretched open & invaded, then he was all the way in, resting on my back, his breath on my neck, he sighed “Oh god, you are SSOOO FUCKING TIGHT!”

“Fuck me! Cum in me!” I wanted to yell but managed only to whisper it. Kris didn't let me down soon he was thrusting, gently at first, but soon harder & harder until I could feel his groin slapping into my butt cheeks. He kept grunting, panting & going “Oh yeah” or “Oh you feel so good!” In fact everything I wanted to hear.

Soon his thrusting got harder, faster & he grabbed my hips again, roughly & harder this time. He was getting close & only confirmed it when he gasped “I'm gonna cum. You want me to cum inside you?” but barely had those words been uttered than he shuddered & spasmed, letting out a ragged “OH-Fuu-uuck!” as he exploded. My cock was so hard it felt like iron as I reached back & stroked off.

When his orgasm had faded & his cock shrunk until it flopped out he patted my ass & got up but not before pulling my underwear up & putting my skirt back in place. He mumbled something like “Thanks, that felt really good.” Soon after that I heard him close the door behind him.

I’d got what I wanted. But I wasn't finished yet.

I leapt up & dived into my box of sex toys, found my fave anal dildo & got back on the bed. I worked that dildo while all the time thinking of Kris fucking me & I gave vent to all the slutty things I'd wanted to say while he fucked me. Eventually I stroked myself off, pushing my dildo in as far as i could as I came & collapsed exhausted. As I lay there, face down, I fantasized about him coming back & riding my ass again.

“SLUT!” I thought & I loved it.

I never got to know much about him & that's how I wanted it, as anonymous as possible. He did pay me several such visits & it got to the point where I felt comfortable speaking up & telling him how much I wanted him to cum in my ass. I sucked & swallowed him a few times too. He had me in the bed, over a table, up against the wall, flat on the floor, bent over in the kitchen & so on. Never face to face even though I really wanted him missionary style so I could grab his ass as he pumped his cock into me.

After about 8 months I saw him less & less, hed started dating a girl. I'd continue placing adverts & have others come & find me in my outfit, fuck me stupid & then go on their way over the next few years, but that's another story.

[jjourneyman]

Part 5

And so we reached the moment of truth, him holding my hips in both hands & me, in full cheerleader outfit, reaching back, guiding the tip of his cock towards my aching hole. Until now we'd hardly said a word, but I couldn't contain it any longer & found myself saying “Fuck me, I want you, fuck me!” I didn't have to make it any clearer as he gently, but firmly pressed forwards & speared my tingling spincter.

There was that moment of being penetrated, that feeling of being stretched open & invaded, then he was all the way in, resting on my back, his breath on my neck, he sighed “Oh god, you are SSOOO FUCKING TIGHT!”

“Fuck me! Cum in me!” I wanted to yell but managed only to whisper it. Kris didn't let me down soon he was thrusting, gently at first, but soon harder & harder until I could feel his groin slapping into my butt cheeks. He kept grunting, panting & going “Oh yeah” or “Oh you feel so good!” In fact everything I wanted to hear.

Soon his thrusting got harder, faster & he grabbed my hips again, roughly & harder this time. He was getting close & only confirmed it when he gasped “I'm gonna cum. You want me to cum inside you?” but barely had those words been uttered than he shuddered & spasmed, letting out a ragged “OH-Fuu-uuck!” as he exploded. My cock was so hard it felt like iron as I reached back & stroked off.

When his orgasm had faded & his cock shrunk until it flopped out he patted my ass & got up but not before pulling my underwear up & putting my skirt back in place. He mumbled something like “Thanks, that felt really good.” Soon after that I heard him close the door behind him.

I’d got what I wanted. But I wasn't finished yet.

I leapt up & dived into my box of sex toys, found my fave anal dildo & got back on the bed. I worked that dildo while all the time thinking of Kris fucking me & I gave vent to all the slutty things I'd wanted to say while he fucked me. Eventually I stroked myself off, pushing my dildo in as far as i could as I came & collapsed exhausted. As I lay there, face down, I fantasized about him coming back & riding my ass again.

“SLUT!” I thought & I loved it.

I never got to know much about him & that's how I wanted it, as anonymous as possible. He did pay me several such visits & it got to the point where I felt comfortable speaking up & telling him how much I wanted him to cum in my ass. I sucked & swallowed him a few times too. He had me in the bed, over a table, up against the wall, flat on the floor, bent over in the kitchen & so on. Never face to face even though I really wanted him missionary style so I could grab his ass as he pumped his cock into me.

After about 8 months I saw him less & less, hed started dating a girl. I'd continue placing adverts & have others come & find me in my outfit, fuck me stupid & then go on their way over the next few years, but that's another story.

Wow Gregshaw! That's quite the story!

I had a similar experience, although mine took place at an ABS. I had been there a few times, but on that particular morning, I stuffed one of my sexiest outfits (wig and high-heels) into a small backpack, bought a large handful of tokens and proceeded to one of the booths in the back. I scarcely had time to get re-dressed when the first cock came through the glory hole.

I was on spring break at the time, and didn't have to be to work until 8 that evening, so I thought I would make an afternoon of it. My first "patron" wasn't very big, but he definitely left happy (having cum in about three minutes). The booth was rather small, only about a 4'X4' with two holes on each side. My second patron was much more well endowed, and after he got his happy ending, he even slipped me a $20 through the hole.

I stayed for another hour, but only had two other cocks. Apparently, it was a slow day, but I got my thrill, got dressed in my street clothes and left.

[Robtiti]

What a great story,Gregshaw! Got me hard. lol

[remington12369]

Oh man! Awesome slutty story Gregshaw!

[jimkimball]

I had five girlfriends plus hooking up with a few guys a week and giving head .
I had a Catholic school teacher,a nurse ,two secretaries,and a factory worker I fucked at least once a week,the school teacher and nurse I fucked or got a BJ from three or four times a week ,then if I had time before work ,I worked second.
I would have a guy over when I first got up at least once every two weeks Steve stopped by be had a 12" cock ,I just sucked him off he didn't last long .
I've only had a few guys that last very long when I sucked their cocks everyone else cums in five minutes or less .
The Catholic school teacher and the secretary was the most fun out of the five.
The teacher ate ass and finger fucked me while she sucked my cock and I ate her shaved pussy ,found out later she was seeing five guys while we were seeing each other .
.
The secretary I found on CL went right to her house after work walked in and kissed her right boff the bat very passionate then I went up to her room she let me shower then we got in bed and went at it in a sixty nine for a few hours ,she ate my ass and finger fucked me while I ate her ass and pussy then I fucked her a few times before I came then I got dressed and left was a very good time.

[BackyardShaman]

I think probably the sluttiest thing I’ve ever done was to take anal in a booth in an adult video store from a guy with a real fat dick with a female stripper in the booth cheering us on. She was yelling out things like “take that big cock boy”, “fuck like a girl”, “get your butt up there high” “fuck him hard”. It didn’t take long for us to get an audience, it was a small booth and I was up against the wall sticking my butt out for him.

[marine20]

this might not seem too crazy , but for me it was pretty slutty. i was in an adult theater two years ago. one woman was in there , so i went up to her to see if we could do something. well the young man working there, beat me to it. she started sucking him off right next to me , very hot. he blew his load all over her tits. he then had to leave to get back to his job. she was going to use a napkin to clean her tits , but i stopped her . i started licking his cum off of her tits , then shared it with her in a filthy kiss . can you imagine , we had never seen each other before , and here we were exchanging another mans cum in a dirty filthy kiss. that was really hot and really slutty. after that , of course , we had regular sex in front of other people. i ate her asshole , and sucked her cunt , before i fucked her like a whore. good times !

[chongster]

this might not seem too crazy , but for me it was pretty slutty. i was in an adult theater two years ago. one woman was in there , so i went up to her to see if we could do something. well the young man working there, beat me to it. she started sucking him off right next to me , very hot. he blew his load all over her tits. he then had to leave to get back to his job. she was going to use a napkin to clean her tits , but i stopped her . i started licking his cum off of her tits , then shared it with her in a filthy kiss . can you imagine , we had never seen each other before , and here we were exchanging another mans cum in a dirty filthy kiss. that was really hot and really slutty. after that , of course , we had regular sex in front of other people. i ate her asshole , and sucked her cunt , before i fucked her like a whore. good times !
That sounds hot as fuck to me. I love to eat another guys cum from a woman. My first time I ate it from a fresh fucked pussy

[Timetotell]

I guess the sluttest thing I ever done. Was back in May. This year, I was naked in another man's backyard. It was a black gay couple. I was sucking his cock while his husband was fucking me. While this was going on. His neighbor who lived behind them. And older black lady was sitting on her back porch watching them

[RICKCASV]

The sluttiest thing I have ever done was the first time I let a man give me a blowjob. I was 26 years old and I was exploring my bisexual side. It was 1979 so HIV and AIDs were not a concern. I had already let a man, a total stranger, give me a HJ when I was 22. This occurred in straight porn theater in Hollywood. Three years later I had my first experience giving a man a BJ (I had him cum in my mouth and swallowed.) at a bathhouse in San Francisco ( I lived in LA at the time). Both of those experiences were very hot and I enjoyed them very much.


Before I let a man give me a BJ I wanted to make sure that I could reciprocate and that I would enjoy the experience of having a man suck my cock.. After receiving the HJ and giving a man a BJ I felt like I was ready to have a man go down on me.

This is the story of my first time being on the receiving end of a BJ from a man. Seven months after giving my first BJ in a bathhouse in SF I decided I was ready to have a man suck my cock, hopefully to completion. I knew there was a bathhouse on Melrose in West Hollywood so on a Saturday night I decided to go there with the intent of having a man suck me and make me cum.. I parked my car went in, paid my money at the front desk and was given a very small towel and a locker key. I went to the locker room and took off all of my clothes and put them in the locker. The towel they had given me was far too small to wrap around my 28 inch waist so I would be totally naked.. I had been to a nude beach four years before that was mostly made up of men who were obviously interested in only men and I enjoyed being on display for them and having them check me out as I went in an out of the ocean. . I had also been nude at the bathhouse in SF so I had no problem with the fact that I would be totally naked in front of a lot of gay men. .

I came out of the locker room and saw a stair way going up to the second floor and decided to check it out. At the top of the stairs was a very bright light. There was a group of young guys standing around and just beyond them, where the lighting was much dimmer, there was a mass of men going all the way to the back wall. This was a very large room, about 30 feet wide and 70 feet long. Part of this room just inside the entrance to the left was totally empty. No one was having sex there. That area was a very well lit up area and all of the sex was happening in the area that was dark about 15 feet away from the light at the entrance. It was obvious that the men having sex preferred to do it in the mass of bodies that were in the dark.

Nothing was happening in the well lit area so I decided to venture out into the mass of men in the dark area of the room and made my way carefully through the tangle of men on the carpeted floor having sex. There were all kinds of noises....sucking and fucking type noises. I didn't want to just want to plop down on the floor and join in on some activity that was already going on so I went back to the entrance where the light was.

I decided I wanted a one on one situation with no one else involved. There were more young men standing around now and more coming in. All of us were just standing around naked with our soft cocks hanging out, waiting for someone to approach us. I was far too horny at this point to just stand there so I decided to take matters into my hands and I began to touch my cock to see what would happen. I started pulling on my cock with my left hand (I had my little towel and my locker key in my right hand) and it did not take long for my cock to noticeably react to my touch. My cock started to get hard and this turned me on even more. All of the men standing there were watching me as my six inch cut cock grew from soft to hard. I had no idea what I was going to do when I became fully erect when one of the guys said "You have a nice cock. Can I touch it?" He was nice looking and had a good body so I said "Yes".

I then made my way over to the area that was pretty well lit up about fifteen feet away from the darkened area where all the sex was going on. I laid down with my head on my little folded towel up against the wall and I spread my legs. It was very obvious what I wanted and what I expected. I wanted very badly for the man who had approached me to take my hard cock into his mouth and suck me. He followed me and moved in between my legs on his knees, took my hard cock in his hand and began to suck me. It was amazing. I had received oral from lots of women but nothing could compare with what this man was doing to me. It felt really really really good. Suddenly he stopped sucking me and moved his body so that his ass was just over my cock which he was holding straight up. I wanted no part of fucking him so I told him I didn't want to do that and he went back to licking and sucking my cock and balls..

By now the room was very crowded in the area under the light where we were all by ourselves and everyone that came in could clearly see me getting sucked by this man. Little did they know that I was experiencing my very first blowjob from a man. It made me even more aroused to be on public display that way and I started whispering to the guy sucking me "Make me cum, make me cum...." over and over again as he sucked my cock. All these men were watching me get my first BJ from a man and now I wanted them to see and hear me cumming while this man finished sucking me off. I had wanted to put on a show for all the men just standing there in the light watching me being sucked and that included watching me orgasm Out of nowhere I suddenly felt myself cumming in his mouth.. It was very intense and I couldn't help raising my hips and cock up off the carpeted floor as I came (I was laying down). I usually can feel an orgasm coming on but I was so mesmerized by what he was doing to me (he was very skilled at sucking cock) that when I came it was almost a complete surprise to me even though I was totally hot from what he was doing to me.. He kept me in his mouth the whole time I was cumming and knew exactly when my cock was getting too sensitive. At that point he took his mouth off of me.
Unlike many men who lose interest in more sex when they cum I could not wait to reciprocate and suck his cock. His cock had gotten hard while he sucked me and I told him I wanted to suck his cock and have him cum in my mouth, that I wanted to taste his cum and swallow it.. He had a nice average sized cock that curved upwards and I took him into my mouth. The crowd of people that had watched me getting sucked now watched me suck this man's cock. I love sucking cock and it wasn't long before he came in my mouth and I tasted his load, savored it and swallowed it.