First Time With A Hot Crossdresser

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I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. Thats saying a lot coming from me, for a 26-year-old straight guy. Ive never been bi-curious either.

Its been months Ive passed this regularity, I observe they way things worked there. Just out of general curiosity.
Cars/rickshaws/cabs stopped by, the crossdressers walked to the people trying to make a deal. Sometimes they are taken away. I googled them, found out on an online forum that they are usually working on bargainable and inexpensive rates.
Each time I passed, I usually found one or two of them attractive.

One night, as usual, I was late from work. By 1:30 am I took a rickshaw for home. I was kind of horny that night. I also had an off the next day cos of the rigorous schedule, I had decided to take a days break. I decided to stop the rickshaw at that spot and just talk to them. Just wanted to try something bold.

I opened my wallet, left 1200 bucks in it and took away my debit card and the rest of the cash and hid it away in my backpack. I didnt want to be ripped off.
I told the rickshaw driver to stop at the spot. 3 of them walked towards me.
One of them was around 5 feet 11 inches tall, slender in body type but the height was a turn-off. The other one was around 5 feet 5 inches tall, slightly chubby, but a very sweet and fair face, she almost passed off as a girl. The third one caught my attention the most. Around 5 feet 6 inches tall, slim. Unlike the rest, she didnt wear a wig. She had short hair around 4-5 inches long, nicely parted sideways. She was dressed in a black mini skirt which barely just made it below her crotch area. She wore stockings to cover entire legs and wore heels on her feet. Her top was a loose half sleeved t-shirt with a wide and low neck. I could see she wore a padded bra to give off the look. She really had done an amazing job with her make up too, not overdone like the rest.

All 3 of them were in front of me, trying to touch me. I looked at the third one and asked her name. The other 2 backed out now. I was left alone talking to her. I was still seated in the rickshaw. The driver grew restless.

“Sania”, she replied, “Kya plan hai”.

I didnt know how to respond.

“How much?”, I asked

She said, depends on what I wanted. She asked what I was looking for. I asked her what can she offer. She said handjob, blowjob, full sex.

I asked her the cost of a blowjob, she said 2000 rupees. I rejected the offer. She then asked me how much would I pay. I said I can give 1000 rupees for full sex. She said its too little. I said fine and leaned back on to my seat. She leaned more forward and asked where we plan to have sex.

I responded by saying that I have a place.
She went into thought for a while and asked if it was nearby. I said 20 minutes away by rickshaw.
She stepped in and sat next to me. I told the driver to move ahead.

We sat quietly for a while, stealing glances sideways. She was smiling when she saw me looking. She asked me if i had done this before, I told her it was my first time. I asked her if she did it often. She said sometimes, when she feels like, but not that often.

“But youre really hot”, I told her, “you have a nice figure.”
I also told her I am straight. She responded saying most of their clients are straight and not gays. And most clients only take blowjobs.

I told her I was nervous, she said to relax and kept her hand on my thigh close to my crotch.
“I would have started here itself, but the driver would get distracted and horny.” She said.

I laughed.

We reached my flat. I stayed alone in the flat. I asked her if she wanted water or soft drink or anything to eat. She said she wouldnt mind a soft drink. I poured 2 glasses of cola for us both.
She was seated on the bed, I offered her the drink. I then asked her what is full sex and how to do it.
She said shell show me. She asked me if we can start. I nervously said yes, she took both our glasses and kept it away. She asked me to kiss her. I leaned forward towards her, our lips met. I could taste a fruity lipstick. She opened her mouth and her tongue slipped into my mouth.
This made me really horny.

We started hugging and leaned on the bed and ended up lying down. I was lying down, with her leaning on top.
She unbuttoned my shirt and started passing her fingers over my nipples, she bit them and pinched them. My cock.had gotten harder. We then continued kissing, exchanging saliva. I couldnt believe I was kissing a guy, it felt like I was a woman. I tried to take her top off, she asked me if I was sure and that I might regret it. I took it off anyway. I found her in padded bra. I took off her skirt too. I too took off my pants. We were now only in our undergarments.

I saw that she was wearing a black Lacey womens lingerie. It didnt quite hide his cock, though, it was nicely shaved and clean. In fact, he had waxed his entire body. I then leaned towards him and we continued our kissing. This time holding each other, I was on top. Our crotches rubbed against each other, making us both hard. I remover my underwear and his too. And then again we hugged and kissed. This time our naked cocks rubbed against each other. It was such an amazing feeling.

Our cocks were playing hockey with each other. He then told me he would like to suck my cock. I accepted the offer.

I lay down on my back. He went down and grabbed my cock and started teasing me with his tongue. He then took it in his mouth, fondling my balls with his hands.

This guy was really good at sucking, I was impressed and moaning loudly. I had never got pleasured like this orally.

I grew restless, the heat surged through my entire body. I requested him to turn and offer me his cock as well in the notorious 69 position. He quickly came into position. And here I instantly took it inside my mouth, it was neat and shaven. I was sucking it in a manner from whatever I had seen in porn. We were in this position for a long time, neither of us came. I then asked him what next. He asked me in return if I had anything in mind. I reminded him I was new to this. He said I could demand anything from him. I asked him if I could fuck him in the ass. He asked me if I had any lubricant, I did have vaseline which I offered. He smeared it on his asshole, I wore a condom and-and entered him. He twitched a bit and then I went in completely. I fucked him in the ass for 7-8 minutes. He was moaning a bit till I came.

Then I asked him if I can give him a handjob. I did so till he came. We cleaned up and sat on the bed and relaxed. He then wore his clothes and said hell leave. I told him he can wait. I took out the cash and gave it to him. He said he wont wait, but hed love to meet again. I asked him if we could exchange numbers. He gave me his number. We then hugged and he left.

We did keep in touch and met up often too for sex. He also hooked me up with other hot crossdressers. We also had group sex with 3 other people. This event really opened me up to a world of fun sexual activities. More about them soon.

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