Hot crossdressing stories!

bict23 · #1 14th February 2005, 10:45 PM

i know some of you gals out there have had some wild times...

let 'em rip. i looooove a hot CD story (pictures are even better!). =)

gigboy · #2 16th February 2005, 11:17 PM

At the risk of being accused self promotion, I have several stories of my recent experiences as a crossdresser in the "weblog" area of this site under gigboy.

Here a story of special fem moment when I first started dressing in public, full fem.

I've only been dressing for about a year. At first, I felt so full of sexual energy I became sort of a sluty gurl. Several men have contacted me for sex. Guys love my legs (now shaved) and cute man clit.

Anyway, this one week day evening, last summer, I went down to the beach at night. I wore a gater and nylons, a short skirt, and white fem tennis shoes, plus a wig and full make-up

I went to this beach cruising area and sat on a bench in a dark area. I sat there with my legs crossed like a gurl, rubbing my nylon covered thighs. I felt sexy. In a while, I saw this guy walking slowly down the path. He stopped, smoked cigarette checking things out. After awhile he looked towards me. He turned, looked back towards the beach. Pretty soon I thought I could see him rubbing his crotch with his left hand. I kept touching my legs, every once in a while fingering my flacid shaved cock and balls. This went on for a while.

After he finished smoking his cig, he turned and walked towards me. At first, I pulled back my hand from under my dress. I got a bit nervous. He moved closer, then stopped, acting like he didn't see me, but very aware I was about 10 yards from this man.

I slowly returned my hand to my thigh and shaved pussy, and began rubbing myself self, but not too obviously.

Little by little, he got closer. I got nervous and excited at the same time. As he got close enough to see me clearly, I removed my hand from under my skirt, but remained cross legged in a fem manner, showing my lovely long legs.

Eventually this dude walks past me. We don't make eye contract, but are aware of each other. He walked past me then stopped and turned around. He looked back towards me. I had started rubbing my legs, I could see he had reached in his pants touching himself. In a while, he moved closer watching me rubbing myself. Eventually, he sat on the other side of the bench looking at my legs and slightly exposed thigh. He smiled intensely, slid over towards me continuing to play with his cock under his pants. He sat close enough moving his right leg against my left leg. He unzipped pants and pulled out his cock and continued stroking in the open. It was over six inches, not huge, but above average. His cock had a mushroom type head. He slowly stroked his cock with his left hand while rubbing my thigh with his right hand, making his way up between my opened legs. He could tell I wasn't wearing my underwear and was totally shaved.

He told me to pull up my dress. I did so, just enough to show my thighs, exposed skin and top of my black thigh highs and black garter belt straps. I played with myself as he stoked his cock more intensely. I showed off just enough of my man clit, thighs, and nylons. I acted like a dirty little gurl who wanted to feel his hands on my legs. But I acted sort of cool. While fondling me, he fucking jerked off to completion, shooting cum across the sidewalk. His cock must of been at least 7 inches. He squeeze all the jiz from his cock, shaking it several times. I was finished and I didn't even ejaculate.

This guy said "thanks" and "that was sexy". Zipped up his pants and walked away saying, "good night."

For several days, I returned to the same place, at the same time, hoping to see him again for the same and, maybe more. He didn't show up

Throbbin_9 · #3 27th February 2005, 02:12 AM

it was in the early 90s, at a time before the internet got popular when i hooked up with my first cd. i was in my 20s and i connected with MariLynn through a swingers magazine. she lived in Massachusetts and we exchanged hot snail mail for a time. MariLynn, in her late 30s, had a hot body and sounded like quite a cockwhore. she wrote the hottest stuff and sent me some pictures of her in some of her silky outfits and high heels. she left her lip-sticked lips with a pucker at the beginning of her letters and a big wide opened "O" lip mark at the end of her letters. she was HOT and eventually we exchanged phone numbers as well.

after a few months, we decided to meet half way - i had some business in a city not too far from hers, and we met at night in a hotel a few miles from where my company had arranged for me to stay. we decided to meet in a bar in her hotel around midnight. i, of course, knew what she looked like and quickly spotted her as she entered the bar. she wore brunette wig that covered a good part of her face and neck, but she had "a come-get-me" tight black dress that really showed off a figure. we were standing at a little table and ordered drinks. standing hip-to-hip, i could feel Mari's smoldering heat. Mari touched my arm, shoulder, and hands as often as she could, knowing that it was getting me steamed . . . and, without further ado, she brought her head close to mine and whispered how much she wanted to suck my cock. as she talked, Mari put her hand on my shirt and felt my hardened nipple through my dress shirt and she knew her smutty talk got me instantly hard. we decided to leave and go up to her room.

Mari led me through the lobby, looking like, i suppose, any other late night couple walking through a hotel lobby. however, in the elevator ride up to Mari's floor, she unhesitatingly found my cock through my suit pants and stroked it gently, gently cupping my cockhead. i grabbed Mari's shoulders and turned her around slightly and placed my throbbing uncoiling mansnake between her ass cheeks as she felt me get harder and harder. i was so stiff, it was difficult to walk out of the elevator.

once in her hotel room, Mari unbuckled my trouser and knelt before me, parted my brief and popped out my cock. Mari positioned us in front of the room's large mirror and i saw how stiff and engorged my cock had become. Mari tongued the head, but quickly consumed my meat - - eating, licking and devouring my cock, like no one before. without question, Mari was a gifted cockwhore. i looked at my cock and my face in the mirror and i was totally enjoying Mari's wonderfully slurping mouth. Mari deepthroated me, my cock sliding down her throat, without any effort. my cock shuddered in Mari's mouth, spastically throbbing, and i knew i had spasmed some pre-cum deep in her throat. Mari loved it, opening her mouth for me to see my now-foamy pre on her tongue.

Mari began to pump my meat into her mouth, faster. and my hips thrusted to the rhythm of her fist around my cock and her mouth slurps. with her hand still around my cock, Mari stood up and whispered that she wanted me to fuck her. now. moaning to her strokes, i could only nod in agreement. Mari quickly slide out of her dress and slip, and wearing a black and red garter, holding up her black hose, she bent over showing me her ass, spreading it to show me her twitching puckerhole. kicking off her high heels, Mari took a lubricated condom out of her purse and, after sucking me in long strokes again while fondling and pulling my sac, she put rolled it on my stiff, curved cock. Mari put some additional lube on my encased cockhead and fingered some lube in her tight hole. i could resist her invitation, i drew near and my condom-encased cock parted her pucker lips. holding my cock tight at the base, i effortlessly slide my meat in - - hearing Mari catching her breath as she felt my meat filling her honeypot. with my hands on Mari's hips, i slide in alll the way - and felt her love tunnel hold my cock and pulsate around it.

i couldn't last much longer and soon began to thrust and ram my rod harder in and out of her hole. soon, my balls were slapping Mari's moist ass and i was so ready to cum - - and did when i felt Mari's hands pulling me toward her, to pummel her ass, lifting her slightly off the floor. gawd, i still remember the torrents of hot jizz i shot - and her love tunnel never stopped sucking me in. mmmm. i remember us laughing because the spunk running down both our legs because i came so much and so hard, there was hot spillage from the rubber.

after a shower and a drink, i was ready to go, but as i was dressing up, Mari gave me a good-bye suck with me shooting my thick ropes on her face and her eating my jizz. wow. Mari WAS such a wonderful cockwhore.

gigboy · #4 6th October 2005, 06:42 PM

What a slut you are. I'm jealous. You must have felt like the sexiest piece of ass walking down the street to you car that night.

Im also chicken to let a bunch of strangers in dark theater do me. I recently went to a local gay porn theater in WeHo after a night of firting at a local tgirl club. I was stoned and felt very horny. I looked sexy and was femmed up. I walked in the theater and was surrounded and attracted so much attention. I had to fend guys off from reaching up my short skirt. I had to leave soon after since I couldn't feel at ease enough to feel sexy and slutty. So, I left after awhile. But, what a rush! I will definitely go back, but not looking so trampy.

Too bad they don't make TS porn movies like that. Now that's one I'd watch again, and again, and again ...

Ulyssesbigcock · #5 4th December 2022, 03:08 AM

I went with my pig bottom faggot Kirk who took me there. We went in the booth and got naked Kirk got down on his knees and started sucking my cock at first while it was soft and in seconds I got hard as a rock cause Kirk is a great cocksucker. I shot my load quickly and then he started chewing on my foreskin and my big fat balls. I got hard again in seconds. This time I lasted a lot longer. I have a big fat 8 inch cock and he made me cum again and once again he swallowed all of it. We went in the bathroom and I pissed in his mouth and he drank it all. We went back out and found another cocksucker and invited him back to Kirk's house which is 5min away. Well first we went outside in his yard while I sat down and both of them went down and started sucking my cock at the same time. One would suck my cock while the other one chewed on my balls. They would switch positions and at one time they were both nibbling and licking my cock one on each side until I couldn't hold back anymore and shot my load on their faces. I licked the cum of their faces and spit it down their throats. After a few more loads of cum they both laid down on the grass and I pissed on both of them. I can't wait to go back to the bookstore and do this again. I hope you enjoyed my story