We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469.
“This isn’t the dining room,” I objected.
“No, this isn’t,” she replied as she knocked on the door.
“Who’s room is this.” I asked.
Before she could answer, the door swung open and there stood the beautiful Tish. She was wearing a black latex out fit with an open bra top upon with her breasts rested, hot pants, full length gloves and a pair of stiletto heeled boots that came to mid thigh. In her gloved hand she held a long black whip.
I was stunned by how hot she looked. Sue walked up to her and embraced her and gave her a full open mouthed kiss in the lips complete with some tongue action. Tish responded by slipping a hand under Sue’s skirt and groping her pussy.
“Nice wet panties Sue, I take it that you had her eat you before you came over?”
“Yes,” she said pointing at me,"Vicki did a great job making me cum.”
We walked into the room and found Jess standing in the middle of the room wearing a pale pink dress similar in style to the one I was wearing, matching hose and a pair of high pink pumps. She looked shyly at me and grinned. I noticed with surprise that she was a big girl up close, she was virtually as tall as I was and just as large around, but she was much better proportioned with nice hips and a fantastic set of breasts whose ample curves showed through her dress. There was a table set behind her with place settings for four and food sitting under covered dishes on a rolling tray next to the table.
Tish looked at me queerly and commanded, “Sit down in that arm chair over there.”
When I did not move immediately, she gave the whip in her hand a flick and sent the tail of it stinging across the backside of my dress. I jumped and quickly sat down smoothing my dress across my stockinged legs. I felt fear and a strange mix of excitement and anticipation.
She moved before me as I sat there and pulled the down the latex hot pants and ordered me to eat her. I looked over to Sue to see what she thought but she was already lying back on the bed with her mini skirt bunched around her hips with Jess head down between her thighs. I shrugged and turned back to Tish’s puss. I knelt down between her legs and put my face to her musky puss. I started to lick her and smelled the distinctive scent of male cum. As I lapped her pussy, I found that she was full to the brim with someone’s cum! Licking her for all I was worth caused her juices to run and soon my face was drenched with the cum soup that dripped out of her pussy. My cock was straining against the tight satin panties, I was so horny and I could feel the back of the panties stretched tight across my ass. After she ground her snatch against my face for about the fifteenth time, she pushed me off her and slid her hot pants up over her soggy snatch.
Standing up my cock tented my dress at a lewd and very unlady like angle. Tish noticed and order Jess to stop pleasuring Sue. “Get over here Jess!” she commanded.
She had Jess tie me to the bed with my arms and legs spread. Sue sat and watched me with a smirk on her face. When Jess was sure that I could not move she lubed up a large butt plug and pulled my panties to one side and started to work it up my ass. The head of it slid in easily, penetrating my anal passage and filling it as it slid up my greased ass. Part way in though it started to hurt and I groaned. She stopped and waited for me to relax again before firmly pushing it all the way in. It hurt like crazy for a moment as the fat part of the plug stretched my ass to its maximum, then relief as the plug narrowed and my sphincter snapped the rest of it in against my ass. I could not believe how excited I felt lying there like a total slut before these three women, my mouth tasting of pussy juice and cum, my cock straining against my bikini panties, my ass filled with a butt plug, my legs gripped by the tight nylon stockings and my feet encased in the stiletto heels.
Then Tish told Jess to lick the cum from my face. Jess leaned over and I could feel her dress trailing across my legs as she got on all fours and began lightly licking my throat and face clean of the cum that saturated it. I could feel her smooth nylon clad legs slipping against mine and see the tops of her magnificent breast peeking out from the top of her dress. Her tongue was hot and wet and felt incredible as it moved across my skin. Soon, Tish told her to move down and suck my nipples. She reached down and unfastened the front of my dress and pulled my bra down so she could suck and nip and tongue my nipples. I could not believe how sensitive they were as she worked on them. My hips started to twitch involuntarily as I became more and more aroused. Tish handed her a pair of nipple clips and instructed her to attach them to my nipples. Jess pinched my virgin nipples erect and applied the first clip. When she let go pain surged through my nipple and I thought I might pass out, but soon it ebbed and as it did my cock surged against its panty prison and my sphincter gripped the butt plug tight. Then she did the same to the other nipple and the process repeated itself. Then Jess snapped my bra back into place causing another surge of pain/pleasure through my throbbing nipples. It felt to me as though I had actually grown breasts, I was so aware of my nipples and they felt so big from the thobbing achy sensations in them.
She moved further down my body and I could feel her hot breath through my tight satin panties. Her smooth cheeks touched my skin above the tops of my stockings and I could feel her breasts rubbing against my legs through the thin material of her dress. My body stiffened with anticipation. Finally, her tongue flicked out and touched my balls. She licked them until the slick fabric was soaked. Then with agonizing slowness she slid up to lick the base of my cock through the tight panties. The anticipation, the teasing licks had been excruciatingly delightful. When her tongue touched my cock, I thought I was going to explode, I was so excited. My, arms and legs jerked against the restraints and my ass rocked against the butt plug as I waited for her tongue to reach the head of my cock. She was licking in small ever expanding circles working across the sensitive bottom of my cock. She was halfway up it, my hips were grinding against the air trying to get some relief. As she reached the head and sucked it into her mouth through the panties, I knew that I would explode within seconds. I could feel my sphincter spasming against the butt plug that filled my rear passage and my nipples felt on fire with desire.
That is when Tish stepped in. “Jess, stop. I am not ready for her to cum... yet.”
Sue laughed at my bucking hips and at the obvious frustration that was written all over my face and my cock halfway out and straining against the tiny black satin panties that imprisoned it with the large butt plug. Sue reached over and removed the nipple clips causing incredible pain as the blood surged back into my pinched nipples. Then she massaged them with the nylon of my brassiere causing tears to leak out of my eyes.
Tish spoke up. “Jess pull up your dress and let Vicki fuck you up your pert little ass. I think he would like that very much.”
Jess turned her back to me and pulled up the back of her dress to reveal a pretty pair of pink panties clinging to her sexy ass. She grabbed a tube of lubricant and massaged a handful up her ass and pulled her panties to one side to give my throbbing cock access to her rear passage. She had a lovely tan line from her bikini that emphasized the moonlike whiteness of her ass. My cock head slipped in easily and then it took her several moments of sliding up and down on my now super slick cock before she could take all of it up her ass. She finally slid home and I gasped as the cheeks of her ass hit my pubic hair for the first time. As she bounced up and down, riding me like a horse, I enjoyed the sight of her breasts bouncing up and down in rhythm.
All of the teasing and now having this beautiful slut letting me fuck her ass while I’m wearing women’s clothing and watching my girlfriend and another latex clad gal going at it while watching me was too much for this boy. I shoot my red hot jism up her tight rear passage. She groaned as the steaming cum shot into her and rode me until my cock deflated and slipped out of her cum filled ass.
Tish spoke up again and said, "Now, Jess, I think it is your turn, why don’t you have fun fucking Vicki up her ass!”
I gulped and could feel my pulse start to race. With all of the anal sex that I had had, I had never been fucked by a girl wearing a strap-on before. I was a little nervous as I was untied and turned over. My hands were bound in front of me with my ass turned up to the ceiling and my dress was pulled up exposing my pretty panties. Jess pulled my panties down just far enough to expose my ass but left enough on so that my cock was still trapped in the satin panties. She pulled the butt plug out with a lewd pop. I felt it replaced with a firm warm head. The head of her phallus slid past my sphincter and filled my ass making me feel like a complete woman. After the hard butt plug, it was warmer and much more life-like. I found myself getting aroused again. My cock gradually filled the front of my panties while her dildo slammed into my ass. I was now moaning with pleasure and I could feel her breasts pressing and rubbing against my back as she sawed in and out of my ass. I was loving every minute of being fucked by this beautiful girl and began to push back against her thrusts to get maximum penetration.
She fucked my slick ass for what seemed like 10 minutes and then I heard her groan and felt the “cock” pulse in my ass. For a moment I wondered how she had made it feel that way, and suddenly, her cock erupted in my ass filling it with her searing hot cum. My mind reeled. That was a real cock in my ass not a strap-on that was fucking me. Knowing that this was a beautiful transvestite that was fucking my ass with her large cock caused my own cock to stiffen with excitement and I came again in buckets filling the front of my panties with cum. And I seemed to cum for what seemed like ages. I could feel “her” jism filling my ass and dripping out around her deflating cock, while my own cum overflowed the front of my sodden panties. I felt like a total slut!
I was no longer a virgin in my ass and to think that my virginity had been taken by a transvestite or a transexual or something. My heart was pounding as her cock pulled out of my sloppy ass. She pulled up the back of my panties and patted the growing wet spot on my ass where her cum was draining out of my wide open sphincter. I collapsed onto my backside and Jess lapped up the cum from the front of my panties. She moved up and gave me a sexy French kiss jamming my own cum into my mouth. I loved it and reached down to feel her shrinking “clit”. It was a very nice cock and I could not wait to have it in me again. God what a feeling! I lay there luxuriating in the soaking wet cum, feeling the ache in my ass that was both pleasure wanting more action and pain from the recent stretching.
I could see Sue looking at me from behind a video camera that had obviously recorded my “deflowering” causing me to feel even more humiliated and excited at the same time as I lay exhausted in the pool of cum, but all I could do was to stare at Jess standing before me her firm breasts held up by her bra, garter belt and hose framing her cock dripping cum. I knew that my life would never again be the same.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/caribean-vacation-part-2.aspx">Caribean Vacation part 2</a>