My Gay Crossdressing Vacation

I woke up. My bra undone, panties covered in lube and my nylons pushed down my legs. I felt as if I had been used. As I became more aware, I realized that I had been used and really enjoyed it. On the first day at the gay resort after getting dressed, I had walked over to a gay bar and been picked up by a nice guy, named Paul, just a bit older than myself. He took me home to meet his gay partner and they used me as a sex toy and invited me out the next night.

When Paul dropped me off back at the resort, I met another crossdresser named Wendy. While Wendy gave me a great massage and then fisted me, two younger guys who were watching came in my mouth and on my face. Wow!

I rolled off the bed took off my bra, panties and nylons and hopped in the shower just to rinse off before going to sleep. I put on the baby dolls that I brought with me over my breast forms but instead of the thong bottoms that came with them I put on a fresh pair of red and black nylon panties as I liked them better. I crawled into bed. My breast forms were about the best that one could by and felt very real as I rolled over and went to sleep.

I woke up at about 10 am and started to think about what I would do for the day while I was waiting for 9:30 pm when Paul and John would pick me up for our date to visit some Palm Springs gay bars. I figured that I would have to start getting dressed and doing my makeup around 7:30

It was a beautiful morning and I had seen the great pool and all the naked men around the pool when I first arrived at the resort the day before. So I decided that I would spend some time around the pool and in the water. But how would I dress and how would I be accepted. I did not want to take off the breast forms but did not have a proper bikini top. So I decided to wear the pink bikini bottom that I had with me and cut off a T-shirt just below the breasts to wear as a top.

I took a shower and shaved everything that needed saving and sat down in a sheer red nylon dressing gown to do my makeup. I decided to wear the short wig that I had with me. It was a sort of brunette color with blond highlights. My makeup was not too severe and I painted my nails and toe nails but did not put on my false nails. I slipped into my bikini and crop top and with sandals on my feet walked out to the pool.

There were a few stares and a few interested stares but no disrespectful looks. I seemed to be well received by all the gay and Bi men around the pool and relaxed a lot. I chose a lounge chair close to the water put my towel down and enjoyed the sun. As it started to get a bit hotter, I decided to take a swim but knew that I would have to be careful of my wig and makeup. I walked into the pool chest deep and kept my face and hair out of the water. When I had cooled off, I climbed out of the pool and realized that the cut off t-shirt was glued to me and showed of my pair of beautiful 40 D breasts. There, however was nothing to do but lay back down and dry off in the sun.

As I lay there, I noticed a younger guy, mid-twenties, looking over at me. He was thin and supple with soft creamy skin and beautiful lips. His cock was small and soft. He walked over towards me and shyly asked me about my breast forms how soft and jiggly they were and how they stayed attached without a bra. As I was talking to him and got a closer look, I could see that he had more than average breasts with a chest that looked very feminine. It turned out that he, almost she, was undergoing hormone therapy and was at the resort on vacation with her sexual Daddy.

She made it clear to me however that she was free to play and explore and wanted to know more about breast forms, lingerie and makeup. This started to get my imagination going and asked her to sit with me. The sun was getting hot and we both needed sun tan lotion. She offered, and I happily accepted, to apply it all over me. Her hands were soft and gentle and I was loving it. When she was finished it was my turn. She was completely naked. I started with her on her stomach and did her back and worked down to her beautiful rounds pussy cheeks and then down her legs.

I was so tempted while I was at the entrance to her pussy but thought that the suntan lotion may burn a little so I managed to stay out for now. She rolled over on to her stomach and I worked up her legs around her darling little cock and up to her chest. I circled her breasts which turned out to be almost a full handful. As I cupped and caressed her breasts, she started to squirm and moan and was obviously quite excited. I worked my way back down to her cock and took it in my mouth with a sucking sound. It twitched a bit but did not seem to be getting any harder.

I then moved back to her perfect little breasts and leaned in for a soft kiss. The kiss became more and more passionate our tongues twisting and darting. We kissed and rubbed our slippery bodies for about 30 minutes when I decided to ask her back to my room. She asked me the room number and told me that she would ask daddy if she could go with me. She came back that beautiful body swinging and quivering as she walked and said she could come with me and that Daddy would join us in an hour or 2.

As we walked back to my room, she was leaning on me and my hands was rubbing all over those delicious pussy cheeks. They moved and jiggled in my hand and I was in danger of getting an erection. We got to my room, no sooner were we inside the door than she was on her knees in front of me sucking on my little cock. I caressed her curly long black hair and then pulled her up to me for another sensuous kiss.

I suggested that we smoke a joint and she happily agreed. There was a small chair just outside my room. I sat in the chair and she sat on my knees as we smoked and kissed for about 10 minutes. When the joint was finished, we went back inside and lay on the bed. I was stroking her hair and cupping those nice breasts as we continued kissing. I gradually started to move my hands down her back and started to cup and play with her pussy cheeks. They were nice and bouncy, soft but firm.

One of my fingers started exploring around they sift entrance to her pussy and I noticed that she already had a little lube that was helping me get my finger inside her. As she got a bit looser, I added one and then another finger but noticed that she was going to need more lube. I put my hand back behind her head and gave her a big kiss and then got off the bed to get lube. There was a bottle of poppers next to the lube and I brought both the lube and poppers back to the bed. I took a hit of poppers and gave them to her and she took a huge hit. She looked and me with a very sexy look and almost begged me to fuck her. I told her that was not going to happen, that I was a total bottom but I would pleasure her.

I took another hit of the poppers and gave the bottle back to her. The poppers had me very lustful and the kiss we shared was incredible. I again started to caress her pussy cheeks and had her really squirming as my fingers were slowly penetrating into her warm hole. I pulled out, put a lot more lube on my fingers and hand right up to my wrist and started work my 4 fingers into that sweet honey pot. I slid her down on the bed, got between her legs and took her sweet little cock in to my mouth. It was not getting hard but she was starting to moan with pleasure.

I noticed that she was really into the poppers as I started to work my thumb in with my other 4 fingers. She was quite tight and I was really enjoying the feeling of warmth inside her. I had 4 fingers and the tip of my thumb right on the outside of her tender sphincter and was slowly working my fingers around to open her up all the while sucking on that cute little cock. I had the knuckles of my fingers right inside her but the thumb joint still would not fit. I took my mouth off her cock and told her to take another big hit of poppers.

As the poppers started to take, I felt her loosen up a bit more and worked my thumb joint in slow stages through her tight sphincter. One more little, gentle, push and I was inside. I balled up my fist and was slowly moving around inside her while I was still sucking her cock. When the tension on my wrist started to loosen up, I squeezed my hand back together and pulled part way out.

As my thumb was fully enveloped by her tightness, I pushed back in again and started working on her in sanctum of pleasure. She was quivering and almost convulsing with pleasure. I decided to pull out with my hand still balled into a fist. It was tighter getting out but in a very feminine voice she begged me to put it back in again. With a balled fist now, I was able to re-enter with not much difficulty and started to fist fuck her with a passion moving in and out.

Suddenly, I felt a hand on my back and fingers under my bikini bottoms. My first thought was how was she able to reach? I pulled off her cock and look around and there was daddy, all 6 foot of him with silver hair and a wonderful moustache. As I put her cock back in my mouth, he started working my bikini bottoms off and I had to move my feet to get rid of them. He reached around me and put his hands under the crop top that I was wearing and started to gently squeeze my breasts. Although my breasts were fake, they were glued on tightly to my chest including my nipples so that any movement caused a sensation in my nipples. To reach my breasts, he had to push his hard cock right up against my pussy entrance.

He kissed me on the back of my neck and reached on the bed for poppers and lube. He put a finger on my nose and the poppers on the other and told me to take some deep pulls. After putting the top back on the poppers, he spread lube on his cock and aimed right at my sweet spot. The head of his cock pushed inside me and he kept pushing. I seemed like his cock was 3 feet long as he kept going. I was in heaven, my hand inside his gurl and his cock in me bareback. He cupped my breasts and rubbed my back as he fucked me with long slow strokes.

There I was fist fucking his gurl and being fucked by daddy. When she started to twist and moan telling me that she was going to cum. I opened my hand and started to gently urge the cum out of her as I felt daddy tense up inside me. To my dismay he pulled out, climbed on the bed and shot his cum on her face and into her mouth. As his cum hit her face, she came in my mouth. Daddy told me not to swallow.

He picked me up by my breasts, my hand pulled out of her and he placed my face next to hers and said "kiss". We kissed her cum and daddies back and forth. He told both of us not to swallow and told her to see if she could get me to cum in her mouth. I lay back and in no longer than 30 seconds, she got a rare load from my little cock. Again came the command to kiss and we did and enjoyed passing 3 loads of cum between the two of us.

After swallowing, we rolled apart and talked for a few minutes. I told them about my date for the evening fully dressed with two guys going to a few different gay bars. They thought that was a good idea and told me that they would look for me.

It was about 2 pm, so I decided that I would go to the restaurant for a light meal and then get some rest before starting my makeup for the evening. I had to fix up my makeup a bit to go to the restaurant but that only took a few minutes. I wore my jeans, the red bra and a tight t-shirt and went over to get a little food.

The waitress was very nice, we talked a bit about makeup and things. She told me that she was gay and that she and her partner would be cruising around the same bars that I was going to be at and that I should say hello. So off to bed for a nap.