Another Transsexual Massage

These are true stories, with the names changed.

I wrote a few months ago about a surprise I had when I went to a woman's apartment for a massage. It was entitled "Search for a Great Prostate Massage". You can read that first, if you want, I think the title of this story may be a spoiler alert...

I was let in to her apartment and she was decked out in a very sexy outfit that showed off her great body. Let me describe her from the top to the bottom. She was a very pretty hispanic woman, from Columbia South America. Pretty face with hair down below her shoulders. Her wrap around lingerie clung to her D+ tits perfectly, below that a slim waist and nice bubble butt ass.

She took my right hand and placed it on her left tit. I squeezed and kissed it for a minute. Then she slowly lowered my hand down her tight abs around to feel her ass a bit and then she brought it around to the front of her crotch. To my shock, she led my hand onto her huge hard cock!! I was here for a massage, and I guess I didn't read her ad close enough. I didn't realize what "TS" meant in her ad. I do now!

I was surprised, but intrigued. And I decided to go with it. I promised I would write about it if I ever attempted this again.

Well I did attempt it again, twice.

The first time I picked a 30ish woman from an online site. She looked pretty enough and she described herself as having an athletic build. I will call her "Linda". We communicated a few times over text, until we found time to get together. She texted me her address, and it seemed to be in a nice enough section of the city, so I went over after lunch one day.

When I got there she let me in, and immediately I saw that her photos must have not been recent. She actually had more of a masculine face than I expected, maybe it was just that she had less makeup on? But once you are there your committed.

She led me into her room, which was dominated by a large screen TV. On the TV was a transsexual porno, with a succession of guys getting dominated by attractive Transsexual women who were fucking them in their asses. I was interested as to how this anal would feel, so I played along. We stood there embracing each other for a minute or two, while we slowly stripped.

I took off her dress to find a nice set of B cup tits, and a decent ass covered by her boy shorts. It didn't seem like her tits were implants so I guessed they were the result of hormone injections. She stretched out on her bed, just wearing her panties while I sat on the bed, to take off my shoes and dress pants.

I then got in the bed with her so we were both in our underpants. She stroked me and got me hard very quickly. I let my hand explore her crotch, but she had a small flaccid cock, so I took my hand away, it just didn't feel right. I am new to this. In a few minutes it was clear that massage was just a pretense, and it wasn't going to happen. So I pulled her panties off, while she was continuing to stroke my cock through my underwear. She was still flaccid, so I didn't know where we were leading to. She grabbed her own cock stroked and stretched it a few times and referred to it as pathetic. She said she could occasionally get it hard. (but it didn't seem like this was one of those days.) At this point I guess I should have made the move to flip her over and fuck her ass, but honestly this was not all that tempting.

She took the initiative and started blowing me. At this point I layed back and played with her tits while she blew me and played with my balls. The blowjob was mediocre, so I took matters into my hands. Slowly I got up to my knees while she continued to alternate between a handjob and blow job. I then kept leaning forward so she layed back on her pillow.

I put my dick back in her mouth, and I was basically face fucking her. I never did this before, and it was a real turn on. She seemed fine with it, and just asked me not to cum in her mouth. At one point I extracted out of her mouth as a break, and she was complaining that I came in her mouth.

I pointed out that I didn't. My dick was still as hard as a rock, if I came it would have softened. I told her it was probably pre-cum and I reinserted it before she could complain more. I kept this up for two more minutes and just before I did cum, I took my dick out again and aimed it directly at her tits. There was no doubt that I came this time as I covered her cute little tits with a few blasts of cum.

I quickly dressed and split, While I was driving home, I questioned whether or not I ever wanted to do this again. When I got home I looked her back up and realized that she didn't state that she did not smoke ( As soon as you stepped into her appt. it was clear she was a big smoker) and she didn't list that she was versatile - so I guess I should not have expected her to get hard. Still learning the lingo.

I put this specific fetish out of my head for a month or so, and then I found myself contemplating it again. I only had two strikes, I figured I would try one more time. This time I found Karina.

She had a number of photos online. She was about 5'10, 135 lbs. Huge double D tits with a rock hard set of abs, and pretty nice legs. Her shots were very revealing and it was clear she had a great body. In addition I started following her online and saw little videos she posted.

From the videos she looked very feminine. I started texting her, and we struck out a few times trying to get together. Finally one Thursday afternoon she was available. If I left work early to head over to her appt. Her appt was thirty minutes towards the city from my office, and my home is an hour in the other direction.

I double checked with her about two hours before my visit, and we were still on. I went to my health club so I could take a shower in advance. Unfortunately while I was driving to see her, she texted me, and I did not respond. When I got to her place she did not answer her door. I called her, and she said that since I did not respond to her text she was not home and would not be for an hour or two. This seemed crazy to me, so I left. I decided to go to one of my favorite full service massage parlors and I had a decent massage from an unbelievably hot Chinese girl who I got to fuck. But that is a story for another day.

After I left this parlor Karina texted me again and asked me to forgive her and rebook the next day. I told her I would think about it. The text was a photo of her nude, and kneeling down. Her great tits were visible (on the website they do not allow actual nudity, so I never saw her tits uncovered). Her knees were spread open, but her forearm covered the view of her cock.

Then she sent me a second photo, standing, topless wearing a thong. Boy did she have a great body. Tall lean and big tits that looked great.

I responded that she was not showing me the part I was intrigued about. 10 seconds later I have a nude photo of her holding her 9 inch very thick erection. We set an appointment time for the next day.

I showed up at the appointed time, and she didn't answer her door. I went back to the car and sent texts and left voicemails. Now I am thinking she is playing games.

To make a long story short, I started driving away when she called me. This repeated itself a few times until she promised she wasn't playing games, and if I went back to her apartment she was freshly showered and dressed sexily for me.

I figured I would give it one more try. I drove back and parked in front of her appt. I locked my car and approached her door, and opened it myself, instead of knocking - this was her last instruction.

When I opened it, she was standing about 10 feet from me, wearing just her small designer pink panties. She was a sight to behold. She looked exactly like her photos She embraced me and actually started kissing.

She took my hand and put it on one tit, while she guided my mouth to her other tit. She was pretty aggressive with shoving her tits in my face. She seemed like she was having fun and appreciated how obvious I was in adoring her body. I found myself saying "you are even more beautiful than your photos". She was. I was marveling at how rock hard her abs and ass were, but I rarely let go of her chest. While I was feeling her up and she was intermittently kissing me, she was also feeling up my cock, through my dress pants. It didn't take much to get me hard. This woman was just so beautiful and energetic.

I allowed one of my hands to go down and attempt to stroke her cock, but it was not erect, and honestly that didn't seem right to me. As I said, I am still getting used to beautiful women with cocks.

After a few minutes of this she broke our embrace, took my hand, and guided me upstairs to her bedroom. Overall it was a nice two story townhouse in a decent part of town. The place was clean, with a lot of christian items on the wall, and a 3 foot tall virgin mary statue at the bottom of the stairs. That seemed out of place.

When we got ot her room, I would still say it was clean, but not tidy. Her bed was not made, and it was covered with clothes and clean laundry. I was glad that it obviously wouldn't still be warm from her last customer.

She guided me to a chair in the corner of the room, where we embraced and felt each other up for another minute. Then she instructed me to strip and leave my clothes there. She quickly cleaned off her bed and stripped it down so it just had the sheet and pillow.

When I was naked, I met her at the foot of the bed. She surprised me by immediately dropping to her knees to start giving me a blowjob. It was great! She was going nice and slow with her lips and her left hand. Her right hand was fingering my asshole. After a few minutes I needed to stop her, I didn't want to cum in the first ten minutes. She slowly stood up, and guided me to my knees so I could reciprocate.

She still had her pink panties on, so I had to remove them. When they were a few inches down her cock came flopping out. I don't know how they hide then so well in these small panties. It was a strange experience to pull down panties and get hit in the face with a cock.

This was really a first for me. My first time with a trans she kneeled next to my head a minute or so after we got on the bed, and thrust her cock in my mouth. I barely got the words out "Oh- OK, we are doing this now?", when her huge cock started banging against my tonsils. This led to a minute or two of the roughest face fucking I ever witnessed. I never even was one third this forceful - ever.

This time was different. She was large, but not as large as the last woman. She was about three quarter hard when I started. It felt better to me since she was mostly hard, instead of starting on a flaccid penis. The best part was that she allowed me to set the pace. It was both wired and exhilarating for me. I have to admit, I wasn't that good at giving head.

She got hard pretty quickly. It is hard to explain how that happened, it wasn't my technique. She was able to put her hand by the base of her cock, and it would spring to attention. Was it a pump? Did she know where the vein is to hold the blood back like a cockring? I never figured it out, but a few times she put her hand to her cock, and it was immediately long and hard.

She allowed me to experiment for a couple of minutes before we got on the bed. She crawled up to the top of the bed and offered her cock to me again. This time she took control and was fucking my mouth. I was just glad that she wasn't as rough as my first time.

Compared to the last woman, her dick very smooth. Almost too smooth. It is hard to explain but you barely felt the ridge of the glands, and there were no veines or other roughness on the shaft. It wasn't what I expected, but wasn't a bad experience. I was hoping to jerk her off to completion when we finished, if it was possible and she would allow it.

When she was done She laid down alongside me to talk. In a very Matter- of-Fact way she asked "So, what do you want to do?"

This was an improvement over the first time when the woman just started to try to ram her dick up my ass without any preparation.

I responded "I, I, I really want to fuck your ass".

She said "Great", and went across the room to get a condom.

When she came back I was sitting at the end of the bed and said, "But I was hoping you could fuck me also."

She seemed happy about that. She put the condom in her mouth and proceeded to give me a blowjob to get the condom on fully. Once complete she had me lay back on the bed and climbed on in the reverse cowgirl position.

With her ass facing me I was able to see it slip right in. It was amazing. She was tight and she was moving up and down like a crazy person. At this pace I would only last a few minutes.

I am sure she knew that I wouldn't last long, which is why her next move surprised me. Just before I finished, she stopped, and rotated her body 90 degrees to the right. Now her legs were straddling my right leg. My dick never left her ass, but I was glad she paused the motion. The view from this direction was great as I could see her tits bouncing in profile.

She started her vigours humping again and her tits and ass were bouncing like crazy. Just like the last time, she paused before I came, and rotated again. Now she was facing me. This was the best view of all, and I had my hands plastered on her tits as quickly as I could.

Once again she started humping. However as fast as she was going I wasn't nearing an orgasm. The angle didn't feel right.

After a few minutes she was getting tired of supporting herself, and I wasn't progressing. I had her stop, and said, "Let me get on top".

She agreed, so I grabbed her by the waist, held my cock buried deep in her,. I sat up, and forced myself to my knees. I then spun around and laid her down beneath me.

I was pretty impressed my cock stayed in her the entire time. I proceeded to put my arms behind her knees to support her legs, and tried to fuck her as hard as she fucked me. It worked, in a couple of minutes I finally came. It was exhilarating.

I rolled off onto my back and she quickly got tissues and disposed of the used condom. She joined me back in bed and with a smile on her face, she said "Do you want to cum again?"

I told her I would love to, but at my age it may take a while. She was up for the challenge, so she got off the bed and crossed the room to get another condom.

It was hard to take my eyes off her ass walking away from me. When she turned around, your eyes were drawn to her beautiful face, tits, and then the cock. It wasn't hard right now. I was only about half hard. It was difficult to see how I would be coming again. And which soft cock was going to get the condom?

She crossed back to me and got on the bed. I was laying on my back and she crawled between my legs while unwrapping the condom. Then she did her sleight of hand trick again and somehow her cock grew hard and long. I really need to learn how to do that.

Once she was hard, she slipped the condom on, and slipped it into my ass. It is amazing how sensitive your ass it. She stayed shallow, just an inch or two playing with the rim of my ass. Then she pushed farther and hit the prostate. That did the trick and I was immediately standing at full attention.

For the next five minutes she fucked my ass at a slow to medium pace Much slower than when my cock was in her. She stayed kneeling between me with one hand steading herself, and the other stroking my cock.

She was right I was going to cum again. It is hard to stimulate your prostate this much without a forceful orgasm. And that is exactly what I had.

I blew all over my belly. It was hard to believe there was that much volume since I just came 15 minutes ago.

She got off the bed to get some wet towels to clean us up with. I stayed on my back while she took care to wipe me down and dry me back up.

After that it was like a switch was thrown and much of her bubbly personality was gone. She was still nice, but she was more business like and made it clear that it was time for me to get dressed.

I took my time getting dressed, as I still had a lot of time left in my hour. But since I was making progress she would come over and hug me, or rub up against me, grab my cock etc, just to play.

Overall, it was a pleasant experience. I had two great orgasms, and I got to experiment a little. I think my only complaint is that these sessions are advertised as massages. In all honesty it is just a prostitution visit. I like to justify the situation as a massage going overboard, than just saying I want to visit a prostitute.

On a final note, I had to stop by and buy a large beer to drink on my way home. I wasn't trying to get the penis taste out of my mouth - honestly there was no objectionable taste, but I had to get rid of the feel of the slippery smooth penis shaft. It just hung on my lips. I am still deciding if I want to do this again. I think I would rather if this was an option at a massage parlor, instead of going to someone's residence.

I will report back if I try again...

Let me know if you like this. I always write in this style, because I am just detailing recent events. I have had a number of massages recently and have a few new stories to tell.