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.