My Gay Crossdressing Vacation

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my breast forms and start from scratch. I showered and shaved making sure my bikini line was neat as well. A clean up inside as well as outside was in order due to the plans I was hoping for this evening.

I cleaned and changed the adhesive on my breast forms and carefully applied them to my chest. I then put on a bra to keep them in place as the adhesive cured. My wig skull cap was next and my red nylon dressing gown. I then sat down to do my makeup starting with the face lift tapes to smooth out the effects of weather on my face and then concealer and foundation. I really enjoy putting on makeup especially doing my eyes and lips. As I was working, I could see the gurl coming out and was thinking about how much I hoped that I would enjoy the coming night. My Makeup finished, I put on my longer flowing wig and took a look in the mirror enjoying what I saw. I put on a nice red and black pair of panties, changed my bra for a red see through one that would allow my breasts to jiggle as I moved.

My nylons were black thigh high stay ups but I decided to use some skin adhesive to make sure that they did stay up. I had decided on a cream colored sheer blouse and a leather mini skirt with a chrome zipper in front. I completed the outfit with a pair of cream colored wedge sandals with gold bling. They made my legs look longer but were not impossible to walk in. I had just finished when got a call from Paul that they were in the parking lot waiting. I was excited, I was about to go out enfemme with no back up and not really knowing where I was going or how I was going to get back.

I walked by the pool got a few cat calls, walked out through the lobby and saw Paul and John waiting. They were driving a black Lincoln Navigator. Paul was in the driver's seat and John, the big black guy got out to open the door for me. Wow that felt special. I was surprised when John got into the back seat beside me. As Paul drove off John moved over close to me, put one of his big fingers in my mouth and cupped my breasts. I was thinking oh boy this evening is starting off well as I ran my hand up his legs to cover that massive piece of meat in his pants.

I was wondering what John had in mind during the trip to the gay bars but never imagined what was about to happen. John slid over right beside me and pulled me across his knees and slapped my pussy cheeks. He ran his hands over my panty clad cheeks as he reached for a black box on the seat beside him. He pulled out a bottle of poppers and gave them to me and then pulling my panties aside started to lude up my pussy. This is going to be special, I thought. Out of the box came an object that looked like and egg but a little smaller on a stick about 12 inches long with a soft flexible cable running out of it and a small elastic loop on the end.

John started to push the egg into my pussy using the stick to push it in. I knew then what the poppers were for and took a big hit. The egg slipped in more easily past my sphincter and past the second as well. The stick was pulled out leaving the egg and the cable inside me. John pulled the cable between my legs and put the elastic loop around the base of my little cock and balls. I had no idea what this was all about but was ready to try just about anything. John then put more lube on my pussy and stared using his big fingers to open me up.

Then more, to my surprise, he pulled a big ass plug out of his box of pleasure and started to fuck me with it. It was really big and I was not sure that I would be able to take it but was sure that I was going to try. I took more poppers and enjoyed the plug being worked into me. I was surprised that it did not take long to get it all the way inside and my cheeks closed up around a very small loop that would be used to pull it out. John then pulled my panties back over my pussy and told me to sit up. As I sat up the feeling was incredible. I jiggled my ass around and felt the plug and the egg move inside me as If I was getting fucked. I asked about the egg and Paul laughed as he showed me a remote control and pushed a button. I nearly hit the roof as the egg started to jump round inside me, the feeling was intense.

As we pulled into a parking lot on Arenas Road, Paul and John told me that I was to leave the plug in place and that they were going to use the egg to control my movements as we toured 3 different gay establishments. They informed me that they would use the egg to let me know when to suck a guys cock and when to let them take out the plug and fuck me. I did not have to be told twice. We got out of the car and walked to the first bar. The plug was rolling around inside me and as we went through the door Paul activated the egg making me jump and squeal with delight.

Here I was all dressed up and waking into a public place, my breasts jiggling in a see through red bra that was completely visible through the very thin cream colored blouse. My legs clad in black nylon under a short leather mini skirt and I knew that my panties were close to being visible at my skirt line. We found a high table with bar chairs around it. As I sat down the plug pushed up inside me. Just as I was enjoying that feeling, Paul activated the egg and I jumped off the chair. After sitting down again, John went to the bar and got 2 beer for him and Paul and a wine for me.

I noticed a tall slim guy in jeans and a western style shirt with a handlebar mustache. He walked over to us, said hello to Paul and John and asked me to dance. I looked over at Paul, he leaned over and stuck his tongue in my ear saying this is Zack, he has a very big cock, enjoy yourself. It was a slow song and Zack put his arms around me and held me very close as we swayed to the music. His mustache was tickling my ear and his hands were up under the hem of my mini skirt playing with my panties. He started to grind against me but I was not sure what I should do until the egg was activated and my reaction ground my pelvis into him.

Zack whispered to me saying come with me I have an RV in the parking lot. I was not sure what to say or do until I saw Paul waving to me telling me to go. As we were walking out I realized that Paul was going to come with us. We climbed into the RV, Zack's hands were now completely under my skirt rubbing my backside through my panties. Zack turned me around pulled me to him and kissed me, his tongue probing and his hands on my back and on my breasts. He backed off and took off his shirt and his jeans and was completely naked underneath.

I saw his huge cock. And wondered if I should just get out of there. Huge was an understatement, you see the really big ones in gay porn and this was every bit as big as any I had seen there. As I was looking in in amazement, Paul activated the egg again and kept it going until I had to fall to my knees. There it was right in front of me and I knew what was expected of me and what I really wanted to do anyway. Thank god for Paul as he handed me a bottle of poppers. Two big hits and my lips were on the head of that massive tool. My mouth was stretched as wide as I could get it just to get the head in. I had to work hard at keeping my teeth away from the sensitive parts.

As I was struggling to get the head further into my mouth, Zac pulled back saying that I should take off my blouse and skirt so they would not get wrinkled. Sitting on a leather couch in my bra and panties, Zack brought out a joint and said lets smoke a bit before we try again. Every time I took a draw on the joint, Paul activated the egg again. Once the joint was finished, Zack took my hand and led me over to the bed. He had me lay down on my back, feet towards the pillow and my head off the end of the bed. He started to caress my breasts and work down my stomach and my panties. As his hands reached my panties his cock which, was now hard and massive was rubbing all over my face.

Paul put the poppers back into my hand saying to me you will want these. I moved my head enough to get the bottle to my nose and started breathing in as much as I could knowing what was about to happen. Zack, gently pushed the head of that weapon into my mouth. It was a bit easier this time as I was really high on pot and poppers. I was in heaven, his big cock in my mouth and hands all over me. Zack started pushing but slowed and pulled back as little as I gagged then back in again. I started to think that I may be able to get this thing all the way in. The next time Zack pulled back a bit, I pulled right off and in my most femme voice asked him to please put some lube on the head of his cock.

All lubed up now and more poppers for me, he started back in. My jaw was stretched but the head of his cock kept moving. At one point I felt him start to rub my neck and realized that he could see and feel his cock in my throat. I was gasping for air so he pulled out allowing me to take a few deep breaths before pushing all the way into my throat and got his balls on my nose and in my eyes. As I was wondering what was going to happen when he came, he pulled all the way out and kissed me with passion.

Paul help him turn me around on my stomach on the bed and took off my panties. They pulled out the plug and applied and generous amount of lube on and into my pussy. My only thought was how the hell was I going to take this? The head of his cock was probing around my pussy lips and he started to push in. I could feel the head stretching my sphincter, it almost felt like I was being fisted. When the head popped in I thought that I would feel some relief but the shaft of his cock was not much smaller than the head. Thank goodness, I had that plug in me for the past couple of hours. He slowly pushed in working back and forth realizing that if he hurt me we would have to stop. When I thought that he must be all the way in, reached back to feel his cock. I was surprised and a bit frightened that there was still 6 inches or so to go.

Another hit of poppers and he was able to get more into me but I felt him reach the egg. As he did, Paul with a big grin activated the egg again. I started to squirm and Zack vibrated a lot. He pushed all the way in and in doing so pushed the egg another couple of inches into me. This had the effect of tightening the cable around the base of my cock. The sensations were out of this world. Zack's cock was deep inside me and he was slowly pumping in and out.

He started to move a bit more quickly and tensed up just before he blew a huge load into me. He must have cum for 60 seconds or more just shooting more and more warm cream into my pussy. I was in heaven and was really disappointed when he pulled out with a little slap to my ass saying well done. Paul came over and put the plug back into me blocking the cum from being able to get out. I put my panties back on and found my blouse and skirt. I was allowed to use the bathroom to fix up my makeup and Paul walked with me back into the bar.

We went over to John and he told us that it was time to go to our next stop. Walking out Lincoln I could feel Zack's cum squishing around inside me kept in by the plug. We got in the car and drove to the next stop on our tour. This bar was not as busy and the lighting was very dim. We sat for 2 more beer and a glass of wine for me. There was not much going on and we were sitting in a half round booth, me between Paul and John.

John pulled a $10 bill out of his pocket and dropped it on the floor under the table. Paul told me to lean over to pick it up. When I did I saw John's big black cock out and hard. Paul pushed me towards it and John put his hand on the back of my head and pushed my mouth right down the length of that beautiful piece of meat. He did not have to push very hard as it was not hard to convince me that I wanted to suck his cock. It only took me about 5 minutes to get a big load of cum. Paul pulled me back up and to his lips. We kissed John's cum back a forth a bit until John said drink up time to move on. I sipped a bit more wine and we were off.

Again walking was an incredible feeling, cum in my mouth now as well as in my pussy. They then told me that the next stop was going to be interesting and a surprise. We pulled into a parking lot and walked into a modern looking well lighted bar. It took me about 30 seconds to realize that there were no men in the bar and it dawned on me that it was a lesbian hangout. I looked quizzically at Paul who told me that they had a surprise for me. And what a surprise it was.

As we walked in the waitress from the restaurant at the resort came up to me dressed in a very soft and sheer red dress with a black collar around her neck and lease attached to it and a bigger female holding the leash. I did not get her name at the resort but she told me it was Stacey and that her mistress was Terri. Terri was dressed in a black leather bustier a very short skirt that showed off stocking held up by garters from the bustier. On her feet were high leather boots.

Paul and John told me that this was not a place for them to stay and said they were going to leave me with Terri and they left. There I was all dressed up and left in a lesbian bar with a dom mistress in charge. Stacey looked at me and smiled but kept her eyes looking down. Terri handed me the leash and told me to take Stacey to a table while she called a cab. As Terri turned away Stacey put a hand under my skirt and gently rubbed my panties as she put her tongue in my ear. She told me quietly that they knew Paul and John and had planned this earlier today. She also said that she hopped I was going to have fun.

Terri came back and said the car was waiting outside, took the leash and lead us out. She took my hand and told me to get into the back seat and went around to the other side with Stacey. She put Stacey in the middle and she got in beside her and we were on our way. Terri leaned over grabbed one of my breasts and pulled me in for a kiss. She then kissed Stacey and pushed Stacey's face to me for another kiss. When the kiss was over she ordered Stacey to pull up my skirt and suck my cock which she did with a very light touch. Terri looked at it and smiled saying that it was about the same size as her clitoris and that we were going to have a bit of fun.

We arrived at a nice house in a gated community, got out and walked inside. As soon as we were in the door Terri undid the zip on Stacey's dress and it fell to the floor. She had no bra and a tiny pair of panties and black stay up nylons like mine. Stacey's breasts were small, firm and round with protruding nipples. I would die to have a pair like that myself. Terri asked if I like Stacey's boobs, if I did I should suck on her nipples. Which I did with enthusiasm. I cupped both breasts and alternated between nipples.

Terri took off her skirt and was not wearing panties. She left us alone for a few minutes and we started kissing and feeling each other in a hot embrace. Terri came back with a big double ended dildo that was at least 18 inches long. She told Stacey to lay on the bed and that I should kneel with my knees on both sides of Stacey's chest offering my little cock to her mouth. Terri then put the dildo into her pussy and stood on the bed facing me and straddling Stacey's head. She held the other end of the dildo and told me to start sucking and using my throat to push it further into her pussy. As I pushed my cock pushed into Stacey's mouth.

The feeling of Stacy on my cock was enjoyable, however, I do enjoy men more. But sucking Terri's dildo cock was heavenly. As I worked, I could see female cum start to flow around the dildo. Terri pulled it out of her and turned it around putting the cum covered end my mouth and the other back into her. She asked me how I liked the taste of female cum. I could not answer however as I had the other end firmly in my mouth. As I was sucking, she reached down and started to rub my breasts telling me that they were very nice and asking if I would prefer real ones. I shook my head yes as definitely as I could.

Terri pulled out and told Stacey to lay up on the bed and spread her legs. She then told me that I was about to get a lesson in eating a woman's pussy. By now I was as horny as I had ever been and dove right in. I spread the lips with my fingers and put my tongue in that wet cavity as far as I could all the time wondering if I was going to be able to get hard enough to fuck that tight pussy. As I was sucking and licking, I felt the dildo pushing up against my butt plug. When Terri noticed it she was a bit surprised but took it out releasing Zack's cum. The cum was plenty of lube for her to fuck me with the dildo. Terri and Stacey both started to moan and soon both were having intense orgasms.

I was told to finish licking up Stacey's cum and then with the dildo pulled out Terri had me use my tongue to clean her up while Stacey finished my blow job. I finally erupted a nice load into Stacey's mouth and we were told to kiss ad mingle the cum. Stacey was a good kisser and we enjoyed the moment. Terri told Stacey to drive me back to the resort.

As we drove back Stacey lost her submissiveness and we had a good talk. She told me that she was going to be working lunch at the restaurant and that I should come in to see her. As we got there Stacey took my makeup case and told me to look at her so she could fix my makeup before I walked into the lobby.

That was the end of date night, as I walked back to my room, I was wondering what more could happen the next day. I took off my clothes and put on my pink baby dolls and started to fall asleep knowing that I was going to have sweat dreams. It was about 3 am and I did not realize that I had not closed my door all the way as I went to bed. Little did I know that my next dreams were not going to be in my sleep.

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