After crossdressing for about a year and being part of a few orgies, I decided I should try my luck at making some money as an escort which would also really push the limits of my crossdressing.
I've always had a feminine body, slim but some female curves so I've been able to pull of being woman in public a few times already.
I started by placing an ad in the local erotic escort guide with some of my best pictures and immediately got replies from interested men. I decided to call one of them who wanted to bring a buddy and we set a date at a local hotel for 8 pm.
I wanted to look amazing for the first time so I started by shaving and making sure I had no body hair whatsoever. I put on my favorite black and red corset and inserted the breast forms and cinched up the mesh halter over my neck. Next came the fishnet stocking that attached to the garters of the corset. I was already feeling horny but the feel of the stockings started to make me hard so I knew I had to take care it. I placed a condom on my cock and, with only a few pumps, I spurted and flooded the tip. Since I love the taste and feel of cum in my mouth, I drank the rubber dry squeezing out every drop.
Back to dressing, I donned some new 5" stiletto heeled sandals I just bought. I knew they would really turn on the customer even though they are a little hard to drive in. I then slowly put my heels through some silky black panties and slipped them all the way up making sure to tuck my cock underneath. It was a warm night so I decided to wear a PVC mini skirt that showed the top of the fishnets but would be decent enough to get into the hotel. For a top I wore a black blouse that screamed whore.
After putting on foundation, I finished up with eyeliner and shiny red lipstick. I pinned on a gorgeous blond wig that really makes me look fem and put on a few rings and a necklace. After a few spurts of perfume on my neck and then on my cock, I was ready to go but since the customer might have a large cock, I lubed up an anal plug and pushed it in my hole to wear on the drive over there just to make sure I was stretched out in case things got rough.
At 7:30 I grabbed my purse and walked out to my car. On the way over, I stopped at a convenience store and bought some long cigarettes since I read that many men have a smoking fetish and I didn't want to disappoint. After parking at the hotel, I reached under my skirt and panties and pulled out the anal plug which had really opened me up. I would be able to take anything now.
I approached the hotel desk and asked if there there was a key waiting for Michelle and there was. The desk clerk checked me out. The sound of my heels on the marble floor was intoxicating.
After a short elevator ride, I knocked on room 2213.
They were better looking than I expected when the door opened.
I asked them to leave the money in an envelope by the door and then we could discuss what they wanted. Sure enough, one of them had a smoking fetish so I immediately lit up and smoked as sexually as I could.
I told him to take their clothes off and then I had them both sit on the couch. With one cock in my hand and one in my mouth, I started getting them hard. I loved it that my red lipstick came off on the cock. After a long time of alternating between sucking and jerking, it was obvious they were incredibly hard. I decided to smoke another cigarette and blow it on their cocks.
Both of the guys had obviously been with a crossdresser before but neither had sucked a man's cock, let alone a crossdressing man's cock. I could tell they wanted to so I offered. I told them to kneel on the floor and then I took my my skirt off and pulled my panties down revealing my tucked cock. Pulling it out, only a few seconds passed before I was rock hard and the guys were sharing my shaven cock and balls. I asked if they wanted to taste come and have me blow my load and only one said okay so we concentrated on him. Moving over to the couch, I settled in and let him go to work. At one point, he had my entire cock in his mouth and throat. After a few minutes, I let out a fem scream and semen started draining out of my balls into his mouth. I told him not to swallow it but to share it with a kiss. The cum tasted so good as our tongues mingled and my red lipstick covered lips kissing his.
I stood up, pulling up my panties and was about to have a cigarette when things got a little rough. One of the guys threw me on the bed ripped off my panties and then rammed his cock in my hole and pounded as hard as he could. It was incredible and I was so turned on I got dizzy as the other guy throat fucked me until I gagged. After the fucking slowed down, they switched placed and the guy I was sucking asked me how much extra it would be if he could throat fuck me so hard that I would throw up on his cock. I told him an extra $100 would be enough. He agreed and I knew I was in for some hurt because he rammed his cock down my throat while holding my nose. After only a minute or so, tears started to run from my eyes and I hurled all over his cock which made him shoot cum all over my face. It was very weird but very hot at the same time. The guy fucking me started to scream and shot a hot load in my hole and said that was the hottest thing he had ever seen.
We cleaned up and drank some bourbon while I smoked some more. The feeling of having semen dripping from my hole into my panties was overwhelming. I asked them if they wanted to do do anything else to which they both said yes but then said I would not want to do it. I said I'll try anything if the money is right. They said they wanted to both fuck me again and cum in my ass but then wanted me to do a creampie into one of their mouths. This was going to cost another $100 and they agreed. They also wanted their wives, who were down in the hotel bar, to come up and watch.
After finishing my cigarette, the ladies arrived and sat quietly on the couch. I went to the bathroom and reapplied my makeup so I would look good.
When I got out to the bedroom, both men were being serviced by their wives and were hard. I got on the floor and they alternated fucking my hole. Both had staying power and fucked me for at least 20 minutes. At one point, I looked over and noticed the wives making out. Both guys then shot their loads into my ass which was now very full of cum.
They decided one of the wives should drink the cum so she laid down on the carpet as I straddled her mouth. I started pushing and then all of a sudden a stream of my juice, lube and their cum shot into her mouth. She gulped part of it down and then shared the rest with the other wife.
The men paid me the extra money and told me to come back the next day.
