My Gay Crossdressing Vacation

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February.

A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ago, I was a full on crossdresser and close enough to passable that I was comfortable going out at night.

My plan developed into a gay crossdressing vacation adventure. I called and emailed around looking for gay resorts in Palm springs that also encouraged or did not discourage crossdressing. I got some disappointing responses, some mediocre and one very encouraging response for a gay clothing optional resort that sounded fabulous. I made reservations for a Thursday through Sunday visit.

I had a few pairs of panties and a bit of other stuff but definitely not what I needed. So I located a crossdressing shop in a large town nearby, went on their website, made a list and ordered everything that I needed for the trip and placed an order to hold it for me until I could pick it up on the Wednesday before my flight to Palm Springs.

I bought 2 wigs, one flowing very feminine and a short one to wear during the day. I decided on breast forms that would give me a 40 D bust and adhesive to hold them on so I could wear them braless. I bought a couple of nice bras that were sheer so the breasts would show through, one red and one black. I filled the list with panties, nylons a nice skirt and tops as well as a sheer red dressing gown and baby dolls as well as all the makeup I could use and other items that I thought I would need. I had some toys and a nice pink bathing suit bottom as well.

I packed everything up and the next morning got on my flight to Palm Springs. When we landed, I picked up a car that I had reserved and drove to the resort stopping for some poppers and at a marijuana outlet for some pot.

I arrived at the resort around 1 pm almost shivering with anticipation and checked in. I was given room 43 and to get there walked right next to the pool lined with men of all ages wearing nothing or almost nothing. I was sooo horny I could have fallen to my knees and sucked every cock there.

However, I had a plan and managed to stick to it. My plan was to clean up and clean out dress up and go out to a nearby gay bar that advertised drag shows. So I showered, douched, shaved my body and attached my breast forms. I started to work on my makeup. My face is a bit weathered and needed face lift tape to get a smooth and fem look.

It was about 6pm, I had decided to wear jeans and a cute tight white top over the red bra and a pair of wedge sandals as I was going to walk the 10 minutes to the gay bar. As I walked out of the room by the pool I got a lot of stares most encouraging but one or two a bit disrespectful, no big deal. As I went into the lobby and by the desk, I stopped to talk to be sure that they knew who I was for my return. One of the guys behind the desk, walked up behind me reached around and caressed my breasts and gave me a big kiss. This made me feel real good.

The 10 minute walk to the bar was uneventful, A few people passed some looked but no reaction at all. I walked into the club, sat at the bar and ordered a white wine. It was about 7pm and there were 10 or 12 guys there. One guy about 65, slim sort hair and a goatee was checking me out and I liked what I saw so I smiled back. He got up and came over and bought me another wine. Two drinks in a short time had me a bit tipsy and I leaned over close to him and put my hand on his leg for support. He put his hand behind my neck and pulled me in for a big kiss.

What a welcome surprise, as our tongues twisted round each other, my hand slid up his thigh and covered a growing cock that was of real interest to me. He cupped my breast and whispered in my ear that he had a car and lived not too far from the bar. I agreed to go with him. His hand was on my back playing with my bra strap as we left the bar. As we got into the car, he opened his pants and took out his cock to play with. It was cut nice and hard and about 8" long we kissed again and as he put his car into gear pushed my head to his lap and my mouth to his cock.

I had been dreaming about this for over a month and did not hesitate for an instant. I slowly licked and sucked the hard pink head and as he started to drive away, I worked my way as far down the shaft as I could. The seats and the gear shift were a bit I the way. He was on his hands free phone about 2 minutes into the drive telling his partner that he was bringing a fem cocksucker home. That was surprise to me but the deep baritone voice on the other end of the phone had my imagination going wild. As we turned into a side street, I sat up and used the mirror to redo my lipstick.

We parked in front of a town house and he said to me not to worry as his neighbors knew he was gay and did not mind. I however, was not at all worried and like to be seen. We walked in the door and there in a white silk gown was a big black man saying hello and checking me out. Again my imagination started, you know what they say about black guys and cock size, I was dreaming.

The room had a nice couch that looked like it might pull out into a bed, it had few other leather chairs and a big TV playing gay porn. The best however was a table with some joints and about 5 bottles of poppers. I knew then that I was going to enjoy the evening. My friend from the bar was Paul his partner was John and I used my fem name Michelle.

As I was looking at John and wanting badly to see what was under that silk robe, Paul put his arms around me from behind pushing his now hard cock against my rear. He reached around and undid my jeans and pushed them to the floor. I was a bit off balance as I still had on my wedge sandals so I grabbed on to John as I took off the shoes and got rid of the jeans. John got my shirt up and over my head and as he did his robe fell open.

I gasped in surprise and delight, big did not do it justice, his cock was still soft and fucking huge. I won't guess as to dimensions but it would not take a back seat to two beer cans. Delighted and a bit scared, I stood there in my bra and panties and a pair of black stay-ups. Paul behind me had taken off all of his clothes and John took off his robe.

They suggested that we sit on the couch and smoke a joint. While we smoked, their hands were all over me and John was slowly fingering my mouth. Between pulls on the joint, I sucked on John's finger and squirmed a bit as Paul touched and prodded. When the joint was finished, John handed me a bottle of poppers and said you are going to need these.

He put his hand on the back of my head and pushed my mouth down onto his huge cock my lips were forced as wide as I could stretch them getting that head into my mouth. I was thinking my god how am I going to manage this. John opened the poppers, put a finger on one nostril and the poppers on the other one. I took about 10 deep pulls, relaxed and saw some stars but also loosened up and started to move down on the huge piece of man meat.

Meanwhile, Paul was under my panties with his fingers lubed up testing out my pussy, I liked his fingers but wanted his cock. Paul very nicely asked me if I wanted him to use a condom and I said hell no what I want is my mouth and pussy full of cum. Paul pulled my panties to one side and lifted me in to a doggy position with my head in John's lap and his very hard cock pushing into me. Damn I was in heaven. I had no trouble taking Paul all the way in but had to work on getting John's cock all the way in my mouth and down my throat.

I found the bottle of poppers and took another good strong hit. As Paul was using long slow thrusts to pleasure himself and me, I was slowly working my way down John's cock. I backed off until the head stretched my lips and then slowly pushed back down again until finally I felt his cock head hit the back of my throat. I was ecstatic until I realized that I still had about four more inches to go.

I slowly pulled right off and found the lube. I lubed up the head and took another hit of poppers. Determined to get all the way to the base of John's cock I started down that shaft again as the head hit the back of my throat, I supressed a gag and pushed the head into my throat. My nose hit his pubic hair and his belly,

As I was trying to use my tongue to lick his balls with his cock in my mouth, I heard "she did it lets switch". Both cocks were pulled from me leaving me feeling empty but not for long. They both lifted me up spun me around and as my mouth was pushed on the Paul's cock, John started into my pussy with that monster.

He pushed in and did not stop. I cried out in pain then moaned with pleasure. I have used some big toys so I was able to take it but I sure felt full. Paul's hands were on the back of my head as he fucked my face and John was moving in and out of me with care as he understood how big he was. I was able to get one more pull of poppers just as they both came inside of me amazingly both at almost the same time. Paul told me not to swallow and John milked more cum out of his cock with his finger and put it in my mouth. Now I had a mouth full of cum from both of them as they lifted my face up to kiss me both of them using tongues to push that cum down my throat.

Wow I was tired, I saw red lipstick marks at the base of two softening cocks which reminded me to fix up my lipstick. We talked for a few more minutes as I put my top and jeans back on. They told me that they had planned to go out to a drag bar the next night and asked if I wanted to join them. My answer was a swift yes. Paul drove me back to the resort where more fun was in store for my next installment of the Gay Vacation Adventure.