My Gay Crossdressing Vacation

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some energy bars.

I walked into the store picked up what I needed and went to the cash, The guy behind the counter was looking at me with lust in his eyes, I knew that he wanted me to give him a blow job. However, he looked as if he had been there all day and was probably a bit stinky so I just smiled and left.

I walked back to the resort and the same guy was at the counter as when I left. His name was Troy. I remember his name because that is my Boi name too. He smiled and looked at me saying it looks like you had a good time.

Walking back to my room, I noticed another crossdresser sort of wandering around the grounds. She was a bit over weight and not really convincing, however each to their own. She saw me and came over to say hello. As she talked to me it was obvious that she was a bottom as well and was not going to do much for me. "I thought". She seemed quite nice however and sort of tagged along as I went back to my room.

I decided to ask her in to share a joint and talk about our experiences. When I got into the room, I looked in the mirror and saw why Troy had noticed that I had had a good time. My mascara and eye liner were really messy and it was quite obvious that I had been royally used by Paul and John.

It turns out that my new friend Wendy, was very good with makeup and offered to fix me up. That sounded quite nice. She turned around and asked me to unzip her dress which I did and it fell to the floor. I was presently surprised by her smooth clean skin and really nice lingerie. Her cock, however, visible through the sheer panties was really small. She undid my jeans and pushed them off and pulled my top over my head. We were now both in bra, panties and nylons, touching and caressing each other. I sat looking at the mirror and she started working on my mascara and eye liner and did a better job than I could do.

When she was finished, I stood up and we kissed, tongues pushing and twisting in our mouths. She had very nice lips and was a very good kisser. We parted and got a joint and went out on the patio to smoke it.

As we were smoking a few guys passed by and took lecherous looks at us. She leaned over, stuck her tongue in my ear and told me that she wanted to suck my cock. I am a total bottom and a cock slut but am not against having a blow job so we went inside, opened the curtains so others could get a good view. She pulled my panties aside and took my small cocklet into her mouth. It was really feeling good and I was even getting a bit hard.

As she was sucking, she put a finger in my pussy and I started to think oh yea this is starting to get interesting. I stated to squirm a bit and she could see the effect that her fingers had on me so got a bit more aggressive. Remember, that John had just fucked me about an hour ago and there was still a bit of cum in my pussy for lube.

As she was fingering me, a couple of younger guys, in their 30s, were looking in the window and stroking their cocks as they watched. I waved to them and invited them in. I was laying on my back on the bed close to one side. One of the guys stood beside the bed watching and stroking himself, the other guy, with a real nice cock knelt on the bed and pointed his cock at my mouth slowly stroking it and watching the action.

Wendy started to get more aggressive and was pushing In with three fingers. I did not have enough lube for that much so I asked the guy standing to reach on the dresser behind him for some lube and the poppers while he was there. Wendy took the lube and lubed up her fingers and the rest of her hand.

The young guy standing beside the bed took a hit of poppers, handed them to his friend on the bed who took a hit as well. He blocked off one of my nostrils and held the poppers for me on the other side. I took a few hits and lay back in submissive ecstasy. I was staring up at those two cocks and trying to lift my head enough to get one or both in my mouth.

Meanwhile Wendy had 4 fingers in me and I was squirming and writhing on the bed begging for more. She mover her thumb in with her fingers and slowly pulsed and twisted, it was obvious that she had fisting experience. As she started to work on my pussy, she bent over and took my cock into her mouth again. One of the guys beside me, helped me with the poppers and I took 3 or 4 big hits. As the sensation was pulsing through me Wendy gave one final push and her hand was all the way inside me.

The guy kneeling on the bed put his cock head between my lips and I gratefully opened up and took him as deep as I could, given the position. Wendy opened her hand and then balled it into a fist and started to pump inside me. I lost all sense then and started to cum. Not a normal male cum but like a girl the cum just kept flowing.

The guy kneeling beside me started moaning and shot a big load into my mouth and the guy standing beside the bed started to shoot his cum on my face and onto the other guys cock that was still pushing in and out of my mouth.

The two young guys left and Wendy pulled out of me and crawled up beside me. We started to kiss and passed my cum and the cum from the two guys back and forth until it just went down both of our throats.

I lay there exhausted but real happy. Wendy got up and turned me over on to my stomach. She undid my bra strap put some lube on my back and started with a nice massage. A few times during the massage she put her fist gently inside me again, I was so open and relaxed that she could fist fuck me with very little resistance.

Wendy stood up leaned over and kissed me, got dressed and closed the door as she left. I was laying on the bed, my panties pulled to one side, my bra undone and my 40D breast forms feeling very comfortable pressing down on the bed. I fell asleep with dreams of how well the first day went and excitement about what was in store for the next 2 days.

To be continued: