Vegas Sissy

So me and my girl friend Michelle split up, we'd been going out for 2 and a half years but the arguments just got too much for both of us. Unfortunately we'd booked a holiday together to go to Vegas, something we'd planned for a while. After compromising with other things I ended up getting the holiday to Vegas, I was still hurting from the split but I also thought about all the hot bikini clad women that were gonna be around the pool. I thought it would be great for me and one of my mates to go and try and pull some American women but I couldn't get anyone to go. I had a free ticket but no one could get time off work, there girlfriends wouldn't let them go, or some other poor excuse, I had a free ticket!

So I had to go alone which I wasn't very happy about but I knew I'd still enjoy myself. The first day I spent drinking round the pool, sunbathing and looking at all the gorgeous women. I tried chatting to some of them, they were friendly enough but because I was on my own I think it put them off a little so I didn't get very far.

I then saw this couple enter the pool, the guy was in his late 50's and she was in her early 20's. She was all over this guy, I knew he had to be really wealthy or she was an e****t. She was a slim brunette with a perfect ass and fake tits. There was no shortage of amazing women round the pool but she just blew me away, I couldn't believe she was with this old guy.

She caught me staring at her a few times and I had to stop looking but it was very hard, and so was my cock that night when I jerked off thinking about her.

The next day I saw the old guy eating breakfast on his own and there was no sign of the young woman. I was convinced I'd never see her again.

Later that night I had a big win playing poker, well big to me anyway, I won just over $1800. I was determined to go clubbing and start throwing my money around to get some much needed female attention.

I went to the nearest bar in the casino and ordered a beer, I turned around and the girl from the pool was behind me.

It was if she could smell the money and appeared out of nowhere. She said hi and and we ended up drinking a bottle of champagne. Her name was Tiffany, it was clear she was an e****t but I didn't care because I wanted her and I had the money.

I bought another bottle of champagne and we went upstairs we ended up fucking until daylight and it cost me a $1000 but it was worth every penny.

In the morning we talked about sexual fantasies and things we'd done in the past as she stroked my cock. She told me about how she'd once gone down on one of her friends at the request of a client. She then asked if I'd ever been with another man. At first I said no but she could tell I was lying. By squeezing my cock she managed to get it out of me about my cross-dressing days and how I'd pleasured men. To my surprise she was turned on and pumped my cock harder until I covered my stomach in cum. Tiffany swirled her finger in my cum and put it to my lips.

"Maybe you'd like to have this experience again again yes? Tiffany said with a big smile on her face.

I told her maybe but I had no clothes or make-up and it was nearly 10 years ago. She said for another $1000 she would buy my outfit and make my CD dreams come true again. I knew it would wipe out all my winnings and I'd have to put extra money to it but I thought fuck it! I gave her $500 up front and she said she would be round at 6:30pm that night.

I was excited all day but nervous and I thought she might've just taken the money and I wouldn't see her again but something told me she was as excited as me.

At 6 I took some drinks up to my room and got showered, I shaved my body in anticipation and resisted the urge to masturbate.

Just after 6:30 I got a knock on the door. I was relieved. Tiffany strolled in with a bag full of goodies.

I immediately got dressed and Tiffany did my make-up. I had a pink cotton corset, a denim min-skirt, silk pink panties, white knee length socks and a long black wig.

We drank cocktails and danced in my room like girlies that were out clubbing. There was a knock on the door at 8pm.

"That'll be our guest" Tiffany said. "Remember to do as I say and don't speak unless I tell you to."

"Yeah" I laughed.

She grabbed my chin and said "DO YOU UNDERSTAND SLUT?"

"Yes" I said sheepishly.

She opened the door and let the man inside. He was called Jason, he was a really good looking guy and looked about 30 years old. I was happily surprised. She pushed him gently against the door and kissed his neck as she unbuttoned his trousers. She pulled his semi-erect cock out and held it in her hand.

She looked over at me sat on the edge of the bed.

"Jason that's Candy, and Candy loves cock"

Jason smiled nervously.

"Crawl over for this cock Candy" Tiffany ordered.

I lowered myself to all fours and slowly crawled over to the hardest cock I have ever seen. I stopped at his shoes.

"On your knees slut and put your tongue out"

I did as Tiffany asked. She grabbed the back of my head and pulled me forward. She started bouncing his cock onto my tongue slowly. I could already taste pre-cum and I just wanted to take him all in. I didn't have to wait long as she slowly shoved my head further forward and I wrapped my red sissy lips around his cock.

Tiffany stood at the back of Jason and started thrusting against him, making him fuck my mouth.

I could hear Tiffany whispering in Jasons ear "Candy a good little cocksucker Jason? I bet you wanna fuck her tight little ass don't you?"

"Fuck yes" he moaned.

Tiffany moved us over onto the bed. Jason was naked now and lying on the bed with his knees up and spread apart. I had been ordered to lick his cock, balls and ass. As I was doing this I could feel my panties getting pulled down and Tiffany rubbed some cold lube into my ass. She then grabbed my shoulder and eased the head of the strap-on dildo she had put on into my ass. I moaned as she drilled me. Jason sat back and began stroking himself while watching us. After 10 minutes Jason couldn't watch anymore, he ushered Tiffany aside and pushed himself inside me. It was so much nicer than the strap-on. So thick and warm. Jason hammered me hard, I had to hold on to the headboard.

"I'm cumming" Jason Said. Just before he did he pulled out and shot all over my ass back. He then collapsed onto the bed. Tiffany used my silk pink panties as a cloth and wiped up all Jasons cum from me.

"Come here slut" she said "open your mouth"

I did as I was told then she shoved the cum-stained silk panties in my mouth.

"Now sit here until we get cleaned up" and she led Jason into the bathroom. They were in the bathroom for nearly an hour and they'd obviously been fucking. They came out and Tiffany told me to lie in the bath tub, she then tied my hands to the taps with a dressing gown belt. As the two of them got dressed.

I could hardly breathe with the panties still in my mouth and I'd sucked all the cum off them as I waited. Finally they came back in the bathroom. Jason got his wallet out and gave Tiffany a wad of cash, she pulled a few notes out screwed them up and threw them on me.

"Oh look" she said and she picked something up from the floor. It was the condom that they must have used earlier. "We can't let that go to waste can we?" she then emptied its contents on my head, it went in my wig, on my cheek and in my eye.

They both began laughing at me.

Tiffany whispered something in Jasons ear and he seemed reluctant.

"Don't worry, it's part of the service" she pulled his cock and aimed it towards me. He then began to piss all over me, over my legs, my face and Tiffany pulled my skirt up and he pissed all over my cock. Tiffany couldn't stop laughing. I didn't know what to think, I was humiliated beyond belief but my cock was still hard.

Tiffany undid the belt and then she left the room with Jason. I was dressed as a girl and covered in cum and piss and my cock was aching. I had no choice but to pleasure myself and I came so hard I nearly collapsed.


89% (13/1)
 
Categories: AnalFetishShemales
Posted by lolli27
11 months ago    Views: 2,609
Comments (4)
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Normal_Guy
retired
9 months ago
mmmm love to feminize the young stud in the story...
and make her MY candy...
10 months ago
wow fantastic story I would love to have happen to me
thanks
Jay
11 months ago
Love your story. I wish I was the one getting fucked! Xx
11 months ago
lovly story