My Gay Crossdressing Vacation

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night.

I remembered that I had told Stacey that I would meet her for lunch at the resort bar. My plans went from there to a day by the pool and then meeting Timminii around 6:30 to do our makeup and get dressed for the evening.

After washing and shaving everywhere, I sat down to get dressed for the day. I was quite used now to reapplying my breast forms and to dry the adhesive put a bra on while I did my makeup. I used the tape and concealer to hide my wrinkles and applied some soft daytime makeup. I decided on my short wig as I was going to spend the day by the pool after lunch. I put on my red and black panties and decided to wear the red bra under a tight cut crop T-shirt. I wore jeans and sandals and headed for the bar.

Stacey was there, wearing a very tight pair of jean shorts, a white t-shirt and no bra. Her perky round breast and nipples were quite visible and my mouth was watering. If I did not know that she was gay I may have wanted to be straight. She walked up to me gave me a hug pressing those to-die-for breasts against me and gave me a big kiss full of tongue and promise. She brought me a glass of orange juice, a piece of French toast with a slice of bacon. Enough to keep me going but not enough to make me look fat.

We discussed last night and my plans for the day and evening. It turned out that Stacey and Terri knew Paul, John and Zack and knew of Daddy and Timminii. I told her that I was going to hang out at the pool and meet Timminii at 6:30 to do our makeup and get dressed for the evening. She asked if she could join us at 6:30. I thought that was a great idea and agreed. I finished my food and went back to my room.

For the pool, I put on my white crop top over my bare breasts and my pink bikini bottoms. The bikini was quite small with gold loops on the side so it just covered my front and back and except for loops my shaved legs were bare. I walked out to the pool, picked up a towel and chose a chair on the grass under a tree partly in the shade as the sun as very hot. Most of the guys at the pool were naked and there were some fantastic cocks that I could look at and dream about as I relaxed.

I imagine, I could have hooked up and had sex with any number of guys that afternoon but really wanted to rest for the evening. As the afternoon wore on I noticed 5 or 6 other crossdressers arriving at the resort, verifying what daddy and Timminii told me about a crossdresser party that evening. I had a diet coke around 6 pm and went back to my room to wait for Timminii and Stacey.

Stacey showed up first still in her tight cut offs and crop top, towing a bag with clothes and makeup for the evening. She came in and we kissed. She turned around and rubbed her beautiful ass against my crotch as I reached around her and ran my hands over her stomach, under her t-shirt and cupped those perk, round and firm breasts.

As I slowly cupped her beasts and pinched her nipples, she worked at getting her shorts and thong panties off. When they were off she got rid of her t-shirt and jumped on the bed with her legs spread. Without hesitation, I got on my knees at the end of the bed and stuck my tongue as far into her cute pussy as I could. I was enjoying my feast and her moans when Timminii walked in. She was wearing a tight pink top and a pair of silk shorts and also towing a bag of clothes.

Timminii lost her clothes faster that I thought possible her small breasts and little cock ready to be worshipped. Timminii walked over to the dresser and picked up a jar of lube and a bottle of poppers. She put her arms around me from behind kissed the back of my neck and used her small delicate fingers to help my tongue in Stacey's pussy. She then put the bottle of poppers to my nose and started to apply lube to my pussy. I took a good hit of poppers as I had a good idea what was coming next.

Timminii's fingers went into me her fingers and hand were small. First two fingers darting in and out searching for my prostate. As I started to moan, she got the poppers by my nose again and held the bottle there for a long period. As my head started to spin, she put the top back on the poppers and her hand started to move slowly into me. I felt her hand move past my sphincter and open up. As this was happening, I was driving my tongue into Stacey's pussy like a mad man. It seemed as if I was trying to get my whole head inside.

Timminii's and started moving further her delicate fingers were working further into me and teasing my second sphincter. As she moved past that spot, I was going crazy with delight, ecstasy and passion. Stacey managed to get turned around so that I was still eating her pussy but she was able to get my cock into her mouth. It took me about 10 seconds to cum in her mouth and as I did she had a massive orgasm, filling my mouth with girl cum. Timminii pulled out of me and joined with Stacey and I kissing each other passing cum back and forth.

Stacey and I realized that Timminii had not cum so we both got down on our knees in from of her and sucked that cute little cock to completion. We finished up with a three-way kiss making sure that we all had a bit of each other. I was glad that I had cum because I intended to be all gurl that night and did not want an excited cock to get in my way. We decided to shower together and get on with makeup and dressing for the night.

All 3 of us were able to get in front of the mirror. Stacey in her black thong and bare breasts, Timminii in nothing with those cute newly forming breasts just asking to be sucked and me in a new red silk pair of panties and my red see through bra. I put on a pair of black stay up nylons and used some of the Breast form glue to make sure that they would stay up for the night.

I applied the face lift tape and then concealer to my face covering that with a neutral foundation Stacey was watching what I was doing and came over to show me a bit about contouring to feminize my face. It was incredibly hard to concentrate with her breasts rubbing my ears while she was working. My real thoughts were how could I ever get a real pair like that. Once she had finished the difference was incredible.

She let me work on my eyes and my lips but interrupted again to show me how to outline and accentuate my lips and make them seem more plump. I finished it all off with my long auburn wig with blond highlights. I dressed in my see through beige blouse and my black leather mini skirt. I began to put on my gold wedge sandals but Timminii stopped me and pulled out a pair of 5 inch pumps that Daddy had sent along for me to wear.

I am not very good at walking in very high heels but both Timminii and Stacey coached me and I started to feel quite comfortable and felt very sexy. Timminii had on a red thong under a tube top that she was using for a mini skirt and a very tight pink short sleeve top that showed off her small breasts and accentuated her nipples very clearly. Stacey had on a black below the knee skirt and a black see through top with no bra.

We were ready to go about 15 minutes early. We kissed fixed up each other lip stick and walked out to the parking lot. We could have been fucked and sucked as many cocks as we wanted to on the way out but managed to stay focused.

Daddy had not yet arrived at the parking lot so we walked out on to the street just to show off a bit. Daddy arrived and he had Terri on the car with him. Terri got out and put a collar and a leash on Stacey and we all piled into the car. We pulled into the parking lot of the Gay bar stopped the car and Daddy pulled out a couple of joints that we smoked before going into the bar.

As we were smoking, Terri was leaning back in the seat and had pushed Stacey's face into her pussy. Her eyes rolling back in her head as she was enjoying having her pussy eaten,

We climbed out of the car, I helped Stacey with her lipstick and we walked into the bar. I no sooner walked through the door that Zack walked up to me put his big hands under my skirt and gave my pussy cheeks a squeeze. His only words were RV lets go. I had no choice and frankly did not want any choice.

We walked back out of the bar and into his RV. He handed me a joint and told me to take off my blouse and skirt and pick up a bottle of poppers. He got naked in a hurry and there was that huge cock that I had been dreaming about. He came over to me and started with a soft sensuous kiss that got more and more aggressive and his tongue pushed and prodded.

As he kissed me his hand moved up to the top of my head and slowly pushed me to my knees. There it was right in front of my mouth not completely hard but very impressive. I took a hit of poppers and slowly took the head into my mouth. The head was big enough that I had to stretch my lips to get around it and then using my tongue slowly worked my way down the shaft. I got about 5 inches of it into my mouth and pulled off for another hit of poppers. My head spinning now, I licked the entire length of his cock right down to his balls and scratched between his legs with my red painted false nails.

Another hit of poppers as I worked my tongue back up to the head and again stretched my lips over that huge cock. Working to control my gag reflex I got the head right to the entrance to my throat but in that position could not get it past. He pulled me to my feet kissed me and said let's try another position. He turned me around got behind me and used his now very hard cock on my panties to push me towards the bed. As we were moving, he put his big arms around me and started caressing my breasts. That made me feel very feminine.

We got to the bed he picked me up and lay me down on the bed with my head hanging over the side. He held my head up and put the poppers to my nose and had me take 5 real big hits. Putting the poppers down, he stood above my head and pushed his cock into my now very eager mouth. Slowly but without stopping he pushed into me right to the entrance to my throat and then past.

He was all the way into me his balls on my nose and he was caressing himself by rubbing on my throat. Just as I needed a breath, he pulled out let me take a breath and pushed right back in without stopping. For five or ten minutes he fucked my face giving me a needed hit of poppers a few times. Pumping in and out using me and I loved it sooo much that I was trying to use my tongue to lick his balls as they got close to me.

As I lay there I was thinking that I just never wanted this to stop. His cock fucking my face his hands on my breasts and working under my panties. I was in heaven. I soon realized that his hands were paying more and more attention to my panties and my boi pussy. Soon he pulled out of my mouth, flipped me around on the bed and pulled my panties to one side. His huge cock head at the entrance to my love canal he tried to push into me with no lube. It was just not going to work. I was too tight and not lubed at all. He handed me a bottle of lube and resented his cock to me. I surprised him by putting the lube into my mouth and using my mouth to lube his cock.

As he was moving behind me I managed to get some lube on my pussy as well. Good thing because when he got there he pulled my panties aside and pushed into me without stopping. His cock head pushed right in and just kept going. It seemed like two feet of it already into me. I was breathing a constant flow of poppers as his cock pushed past my inner sphincter and further. When he stopped his stomach and balls were right on my backside and his cock was so thick that there did not seem to be any spot inside me that was not full.

He pulled out and I squealed like a girl his hand rubbed my back as if to say don't worry you will get more. He grabbed on to my bra strap for leverage and pushed right back into me. I was loosening up and felt proud than I could take ten or eleven inches with pleasure and no pain. As he was pounding me, I looked up and here was Stacey looking me in the eyes and mouthing WoW. She had pulled up her skirt and was fingering herself. She must have seen the pleading look on my face and moved to a position where I could get my mouth onto her pussy.

As I was eating her I noticed that she was quite wet. I realized why when she said, can you taste Daddy's cum? As I realized that I was eating Daddies cum out of Stacey's pussy, I felt Zack tense up and start to shoot load after load into my pussy. Zack pulled out and Stacey moved around to kiss me.

As we were kissing, Zack pushed his cum covered cock between our engaged lips. Zack gave me a little pat on the back tweaked Stacey's breasts and told us to use his bathroom to clean up. Stacey and I worked on each other's makeup got ourselves back in shape and dressed to go back to the bar. On the way, we ran into Terri, John, Paul and Daddy who told us that we were on the way back to the resort for some more crossdressing action.

When we got to the resort, the parking lot was almost full. We had a bit of a walk from the car to the lobby and there were quite a few people around. Walking in those 5 inch heels, I was enjoying being seen. Through the lobby and into the resort, we saw Crossdressers of all kinds, some Drag Queens, One Latino Gurl who had breast implants that looked real and quite a few older Gurls of all shapes and sizes. Most of all however, were the huge crowd of naked men and beautiful cocks.

Stacey, Timminii and I decided to head back to my room to pee and redo our makeup. All the peeing done and the makeup perfect, we smoked a joint and walked back to the party. People were dancing and singing and there were a lot of the gurls on their knees sucking cocks. As I was looking for a contender to put his cock into my red painted mouth, Paul walked up behind me rubbed his hard cock against the back of my leather skirt ad reached around me to caress my breasts.

He whispered into my ear that he would like to go back to my room to smoke a joint. I could not say yes fast enough and off we went. On our way there we saw John who decided to join us. We got into my room found a couple of joints and I suggested that we sit just outside my room to smoke to obey resort policy. John, rubbed that big black cock and said sure but you are too dressed.

They helped me off with my blouse and skirt. So dressed in my red silk panties, my red see through bra, stay up nylons and my 5 inch heels I sat outside on John's knees as we smoked. Paul moved a second chair facing us and we smoked the two joints. We took turns taking a drag and kissing the smoke into each other's mouth.

The joints finished, John moved me off his knees and push my head towards Paul's cock, I was pretty high by then and did not care that I was about to suck Paul's cock on my knees right outside the door to my room. I felt John pull my panties aside and try to fuck me but with no lube that was not going to work. He reached around me and put his fingers in my mouth alongside Paul's cock. Holding my breast in one hand and my lips in the other he picked me up and carried me inside.

Paul climbed up on the bed, his back on the pillows. John got the lube and the poppers and got in place behind me. As John was preparing to put that big cock into me, I slowly took Paul's cock into my mouth. I licked at the head and got a bit of precum before putting the head between my lips. I sucked slowly on the head and then as I was about to start down the shaft, John used a finger to shut one of my nostrils and put the open bottle of poppers to the other side. I was slowly sliding my mouth over Paul's hard cock and every breath that I took I got a hit of the Blue Boy poppers.

I was floating in a world of sensuality and submissiveness when John decided to drive his cock all the way into my pussy. Of course about an hour ago, I was being rammed by Zack and John although big, was not as huge as Zack. In he went and with each stroke, pushed my mouth up and down on Paul's cock. After a few minutes like that, John pulled out and pulled me off of Paul's cock. John lay down on the bed and told me to get on top of him. He was quite far down on the bed and I thought that I was in danger of falling off backwards.

I straddled him and leaning back, almost falling off the bed, I managed to get his cock back inside of me. He pulled my face down and we kissed. His cock was big and even leaning forward to kiss him it was still all the way inside. I thought that I was in heaven. He pulled his tongue out of my mouth and gave me the poppers, saying hold on your going to need these. I took a hit and felt Paul putting more lube on John's cock and on my pussy. His fingers working into me alongside Johns cock. That was starting to stretch me and make me feel full.

Paul reached around me to squeeze my breasts and pushed the poppers to my nose again. As he did that I could feel his cock trying to push in to me right beside John's. Now I knew why they had pushed to poppers on me so hard. I was about to be double penetrated for the first time. I could feel Paul's cock push against John's looking for a way in. Just as I thought it was not going to work, I felt John pull out a little bit and on its way back in Paul's was pulled in as well. I had John's big cock all the way inside me and Paul's head was inside with it.

It was not comfortable at first but as Paul slowly moved around, I could feel him getting further and further inside. I started to loosen up and the uncomfortable feeling gave way to pleasure and ecstasy. I was kissing John and being fucked by two cocks inside me at the same time when I noticed about 5 or 6 guys and gurls standing beside the bed watching.

That beautiful Latino gurl pulled up her dress and knelt on the bed beside us caressing her nice sized cock and presenting it to my mouth. I turned my head and took it in my mouth. The position was awkward but she was ready to cum. I was able to take some of the cum stream in my mouth but most of it landed on John' chest. An older guy took her place and just jerked off onto John's chest and a guy not to convincingly dressed was on my other side. His cum also landed on John's chest. John, put his finger into the 3 pools of cum, mixed them together and put his finger into my mouth.

I was in a place that I had never been before, Both John and Paul fucking me at the same time and John's fingers putting a mixture of 3 other loads into my mouth with his fingers. John surprised me in that once he had cleaned all the cum off of his chest and into my mouth, he pulled my lips to his and eagerly kissed me sucking my tongue and some of the cum into his mouth. Has he did that he tensed up a bit and blew a big load of cum into my boi pussy. Paul pulled out and came beside us, put his cock between our lips and added his cum to the 3 loads that we were snowballing.

With all the poppers and about 3 joints I was out of it. I fell off John and lay on the bed makeup messed up my panties pulled off to one side and my arms and legs askew. I felt a few others cum on my chest and face and fingers putting the cum into my mouth but I could not stay awake any longer.

I woke up around 9 am laying on the bed in bra, panties and the black nylons with cum in me and on me. I realized that I had a very good time but it was now time to wash up, pack up and get to the airport. My Crossdressing vacation was over but there would be another one in the not so far distant future.

On the way to the airport, was the first news that I heard about the COVID 19 pandemic, I got on the plane and got home but the stay at home orders were just starting and as I write this we are right into the mess.