On 24 Aug 2012 (Friday) about 3pm, I messaged a shemale who has posted her brief introduction in one of the product and services directories.  I asked whether she was keen on meeting me for crossdressing and other services.  I was thinking of having sex then.  She welcomed it and quoted her rate as $150 for two hours.  I thought of meeting her in one of the hotels in town.  Instead, she suggested that I went direct to meet her at her rented room.  We arranged to meet at 4.30pm.  I reached there on time.

She was waiting for me at the living hall with the main door not entirely closed.  I rang the door bell.  She opened the door.  I saw a gorgeous and slim lady, dressing in black corset and black panty with a pairs of 6 inches black boots heels.  With the heels, she was slightly taller than me.  She stared at me from head to toe till I was a bit uneasy.  Then, she held my hand and led me to her room. 

In the middle of the room, there was a queen size bed.  I looked around and saw many big and small soft toys, mostly bears.  She also had a television set and a laptop.  Both were turned on but I did not pay attention to the programmes running.  She lied down onto the bed and posed sexily.  I stood at the side of the bed and did not know what to do at first.  I requested her to guide me.  She told me to take off everything and stay naked.  Then, she suggested that I took a bath first.  She gave me a towel and led me to the attached bathroom in her room.  I bathed and cleaned myself up properly.

I was back to the room again.  She pointed to a mini skirt tube on the bed and told me to put it on.  I asked for her help.  She did so.  The tube had bra-padding.  When I finally put it on, she wowed and praised my body.  I told her that I should have brought along my breastforms and she agreed that I would look much better in it.  She took out two bra-paddings from her breasts area and inserted both of them into the tube to make me look more feminine. 

Then, she asked me to sit at the side of the bed and started doing the makeup for me.  She said that she was a trained makeup artist.  Indeed, she did a good job.  I looked very feminine even without putting on a wig. 

Subsequently, she removed her boots heels and told me to put it on.  I put it on. She instructed me to walk around in the room. I did so and paraded in front of her.  She told me to admire myself in front of the wall mirror in the bathroom.  I did so and found that I was quite attractive after her dressing me up.  When I walked near the side of the bed, she suddenly used her right leg to cuddle around my left thigh.  Suddenly she gave a hard pull and I found myself falling into the bed.  At this time, she removed her corset and black panty.  I saw her huge 7 inches penis.  I suddenly got the urge and used my right hand to hold it.  She told me to go slow and remove my tube and heels first.  She asked me when I had started my crossdressing fetish.  I told her that I always felt like a woman in my male body since age 11.  She replied that for her she knew that she was a transgender and a gay since age 5.  I made myself naked without hesitation.  Then, I used my tongue to lick around her penis and the two balls.  I moaned a bit while I was doing it.  I loved it.

Then, I asked whether I should fuck her or she should do it instead.  I said that this would be my first time I got fuck.  She said she would do it today and she put on a condom.  She told me to give an oral job for her first.  I started licking her penis and two balls again.  Then, I put her penis into my mouth and started moved it in and out of my mouth.  I did it very carefully so as not to hurt her.  But she wanted it hard and more.  I could feel that her penis was very hard.  I actually moaned and groaned when her penis was moving in and out of my mouth.  I always wondered why and how most women would moan and groan while performing oral jobs.  Now I could not stop myself doing the same thing.  I could not understand how it came about either.  It just came naturally.  And during a few occasion when her penis was completed inserted into my mouth, she held and pressed down my head closely to her groin area to stop me from moving her penis out of my mouth.  Strangely, I did not object to it though I could hardly breathe and felt erotic at that moment that I was being forced to give an oral job.  I also had great sensation because while I was doing the oral job, her right hand was holding and playing with my penis and her left hand was teasing my two nipples.  She caressed me very well.  While she was about to cum, she told me to stop.  She said that I did a very good job and could not tell that this was my first time doing this.  I said I learnt it from lots of porn movies.  She commented that I was a born in nature slut and prostitute.  I told her that if I was born in her country, I would become one like her.  She nodded her head and said that she could help me attain it if I did wish for it.

Then, she took up a bottle of liquid lubricant.  She poured some of it at her groin area and told me to massage evenly to her penis.  I did so willingly.  She continued to lie on the bed and told me to sit up and move my ass towards her penis.  She wanted me to sit on top.  We tried a couple of time but her penis just did not manage to get into my ass.  At one stage, I did it so hard and hurt her.  I felt so apologetic about it.  She wanted me to focus.

She suggested that we did a doggy style.  She told me to prone onto the bed and lifted my hips.  I did so but with my both legs closed together.  She told me to open wide and used her both hands to open my both legs wide abruptly.  I felt that my ass was completely exposed to her.  I requested her to go slow as this would be my first time getting fuck.  Though she agreed but I supposed she did not care and could not be bothered with me.  I felt that her both hands held my hips very strongly.  Suddenly, I felt a sharp pain in my ass and a hard object was trying to force itself into it as deep as possible.  I cried out loud and kept on shouting “pain”, “pain”, “please”, “please go slow”, “please”, “I beg you”, “I can’t take it”.  She did not bother at all.   She kept on thrusting her penis in and out and yelled that I was a cheap and low slut, that I was a prostitute and I was destined to be raped and fucked.  I actually felt that I was being raped.  Suddenly, I felt so helpless and tears started rolled down my cheek.  I struggled but could not get out of her grip.  I nearly fainted and my both hands just gave way and I dropped my whole body facing down onto the bed. 

She lied on top of me, moving her lips close to my right ear and mumbled and consoled me that she liked my tight ass very much and that she felt very great fucking me because she was the first person who took away my virginity.  She said that she enjoyed raping me.  My urge was aroused by her words again.  She did not let me rest long.  She told me to get up and wanted to try the position which I sat on top of her again.  She told me that now my ass would be readily opened for her penis if I sat on top of her because she had widened it while fucking and raping me doggy style earlier on.

She poured some lubricant again.   I gave her penis a good rub.  Then, I moved and sat on top of her body.  Truly, I managed to hold her penis and insert it into my ass with ease. It just slide in I did not feel any pain at all.  Indeed, I felt very good.  I felt one warm hard object, with some elasticity, inside my ass.  She instructed me to move my hips up and down.  I gladly did so.  I moaned and groaned and was getting hysterical.  At the same time, I imagined that I was just like any other women serving their sex partners.  I wanted to do this more and often.  I peeped at her and saw that she was enjoying my sex service too.  Then, she used her both hand to play with my penis which was exposed right in front of her.  After a while, I felt a sudden contraction in my ass area. I knew that I was getting orgasm soon.  I mumbled that I was cuming and she played with my penis harder and harder.  Yes, the contraction in my ass speeded up and I cum.  I cum all my white and thick load on her body.  She continued to use her hands to squeeze out every bit of my load.  She loved my load and collected most of them at her navel area.  She used some to rub around her both breasts.  I collapsed and lied down next to her.

After a while, she told me to get up and sit beside her and gave her a hand job to let her cum too.  I obeyed.  I patiently licked her penis first and gave her the hand job.  This took me quite a while, perhaps around 30 minutes before I made her cum her load in the condom she was wearing.  She removed the condom and poured her load onto her body.   I saw that her load was not lesser than mine but just a bit more transparent than mine.  

I enjoyed this sex encounter very much and mentioned to her that I would most probably come back again for her next week.  I also suggested that I would bring along my wig, breastforms, bra, and dresses.  She said that I should.  However, she reminded me to book her before 4 Sep 2012 because she would be going back to her country for a while.  I promised her that I would definitely do it.  I was a bit horny then when I was thinking of asking her whether she would be keen to partner me to serve clients together.  Worst, I was wondering whether she could recommend me to work as a prostitute.  I believed that I could do a fantastic job especially after I had done so for her earlier on.  Come to think about it carefully, I was providing sex services to her.  I was a prostitute and not her.  However, I did not say it out because I felt that this was just my first time and with her.  I should get to know her better first before I decided to plunge into this line.  I paid $160 to her and bid goodbye to her.