My First TS Experience....

My First Transsexual Experience

This is going to be quite lengthy, as I am basically adding my entire history of interest in transsexuals. About 8 years ago, I was online looking at some pictures, when I came across a word that I wasn't familiar with. The word was "T-Girls". It said something like "T-Girls are back and I don't want to hear it. If you don't like t-girls, don't look at them". So, I could tell by the title that they weren't girls of the regular type. My curiosity was arroused, so I clicked on it. Right away, I knew these ladies were born as men. These particular girls were not so hot. They mostly looked like men in wigs with breast implants. None of them were really passable, with the exception of Lisa Lawer, who ironically lives as a man now. When I saw her face, I remember saying, "this one actually looks like a woman". Still though, it didn't hit me. I exited out with no real intention of coming back.

Some time later, I was lying in a tanning bed and started remembering some of those ladies that I had seen and how their breasts were really nice. All of a sudden, I got a major hard-on! I mean an erection that would pierce through a brick wall. I was so turned on that I had a chill in my body. I was surprised as I had no real attraction to them when I saw their pictures. So, I thought to myself, "when I get home, I am going to look up some more of these "t-girls", but ones that I am attracted to". I couldn't wait to get home. I went straight to the computer and began my search. The more I searched, the more beautiful these ladies were. I was stunned by their beauty. I kept saying to myself, "No way! There is no way this girl was born as a male". I couldn't believe it. I had never had an attraction to a man and still haven't to this day. But, a beautiful woman with a penis? Well, I have a penis. It's not like it is some alien body part from outer space. When I saw these beautiful ladies with dicks, I wanted to please their sexual part just as I had always wanted to please a woman's vagina that I was attracted to. So, the penis thing was no big deal and that too surprised me. It's amazing what you can find out about yourself surfing the net. LOL!

So, for the last 8 years, having sex with a shemale was nothing more than a fantasy for me. For a while, I wasn't sure if I would ever do it. I knew that I was attracted to them, but there aren't really many TS's where I live. Well, there probably is, but I don't hang out in clubs of any kind and don't know any transsexuals. I am not bragging here, but GG's have pretty much always come easy for me. Any decent looking guy who displays confidence, but not arrogance, can get a girlfriend. There are a lot of young women and men out there looking for love. I always said, "I would never pay for sex!" and "Why should I pay her? Chances are, she will get off more than me". Yeah, I was a real cocky prick. But, I decided to go back on the whole "not paying for sex" thing, at least for this once, only because it was to be a special occasion and I wanted this lady to be attractive and not just some guy in a wig. Eww!

So, I finally did it. I came across some adds for TS escorts, not far from where I live. My preference in GG's and TG's is black and I was in luck because this particular area in which I was searching was predominantly black. I texted the one with the sexiest photos, which in this case, looked suspiciously fake. I asked her to send me a picture and she agreed. And...I was right. The pictures were fake, haha! But, I didn't even mention it to her as the picture she sent me was very nice and her voice sounded great over the phone. I met up with this hot, black tranny, who answered the door in her bra and panties. She stood about 5'8'', had a nice face, dark skin and a great ass! She complimented me on my attire and then lead me straight to the bedroom. She collected the donation and asked me what I was looking to get into. I told her I wanted to do a little bit of everything. I told her I wanted to prolong the experience and that I wanted both of us to cum. I was hoping that I wouldn't cum too fast, since I really wanted this. I was prepared to do everything in short spurts, if that's what it took. I usually have good-to-great stamina, but this was a whole new experience for me. I was actually surprised at how calm I was. Even on the ride over, I wasn't really nervous like I thought I would be. Looking at her great ass just made me want to enter it, so there was no room for nerves at this point. I was like a hunter who had spotted his prey.

She dropped her panties and revealed her nice, cut, chocolate dick. As I undressed, she walked over and put a condom on my still flaccid cock and immediately began sucking it. She could suck some dick, though she was a little aggressive with the upper teeth. I didn't say anything, as it still felt kind of good. She kept sucking and then I pulled her up. "Do you wanna fuck me now?", she asked. I gently moved her to the bed with the intention of entering her beautiful body when I noticed her cock just screaming for me to suck it. The sight of her lying there with her legs wide open was irresistible. I wrapped my mouth around her cock like a professional. I began sucking her and she immediately started moaning in pleasure. Her cock got hard and I began pushing it down my throat. I rubbed my tongue all over her balls and then made my way back up her shaft. I was really enjoying this. That warm, hard cock in my mouth was a major turn on.
I then stood up and she applied some lub on her tight ass and my fuck stick. I slid my cock inside her and it felt GREAT! I was in a standing position while she was lying on the bed. I held her tight while thrusting my cock inside her. We then moved to the floor where there was a nice, comfy blanket waiting for us. I got on top of her and began fucking her again. She started talking in my ear. "Oh yeah, I feel your hard dick inside me.", she said. Surprisingly, I didn't even feel like I had to cum. I had worried that I might cum too fast, but once the action began I knew my stamina was the same as usual, even though I was SO turned on. I put her legs over my shoulders and really started fucking that tight, sexy ass. She complained that it hurt some, which surprised me because I knew this wasn't her first rodeo. She asked me how long it was going to take for me to cum and I answered her the best way I could and simply replied, "I don't know".

Since I felt no signs of cumming and she was in a bit of pain, I gave her bottom a little break and restarted my mouth-to-cock action. Sucking her dick was so nice! I began sucking with more pressure to increase her pleasure. We moved back on the bed and she got on top of me. As she was about to sit on my hard dick, I began stroking her cock. It was right in my face and I couldn't keep my hands off of it. She leaned forward so I could put it back in my mouth. I don't know who was getting more pleasure out of this, me or her. She seemed to like it. After sucking her for a few more seconds, she sat on my dick and let it slide inside her. She rode me nice and slow. At this point, I wanted to experiment a little further. I asked her if she wanted to fuck me. She said yes and put a condom on. My virgin ass was about to be gone forever. She told me to get up and lie over the bed on my stomach. This wasn't how I had imagined loosing my anal virginity, but I let her do what she wanted to. She said "you have a nice ass" and my reply was like that of a school boy, "you too", I said. I felt the tip of her cock touch my virgin ass and even that felt good. She slipped it inside me and for a split second it felt fine and then the pain set in. She pulled it out, for whatever reason and it still hurt. Ouch! I asked her if we could take it to the bed and she said yes. I lay on my back and she pulled me to get me towards the edge of the bed and then she slid her cock back in my ass. She started grinding inside me, fucking me nice and slow. It felt so damn good, no pain at all. She was standing and rubbing her cock in my ass in a circular motion. She was grinding so passionately. She then started stroking my cock. For the first time since we started, I felt like I could cum. "You feel my hard cock in you?", she asked. She kept doing her thing and I kept enjoying every second of it.

I decided it was time for a role reversal. We got up and I bent her over the bed and prepared to fuck her from behind. I noticed my cock wasn't quite as hard as before, due in part to her rubbing that nice, hard cock in my ass. It was still erect, so I applied a little more lub and put it back inside. I held her down and fucked her like a man possessed. I can't explain how good it felt, probing my cock in that beautiful ass. Smack, smack, smack! I was shoving it in as hard as I could at this point. I still felt no signs of cumming and could tell she was surprised by this. I think she thought she was just going to make this first timer cum real fast and that would be it. I am glad to say that wasn't the case at all and believe me, I had my doubts. We only had the condoms that we were wearing since I forgot mine at home and she only had those two, or so she said. I told her that I wanted to see her cum. She said "Once I cum, I can't get fucked anymore", so I knew once we took the condums off, that was it. "Do you just want to pull these things off and cum everywhere?", she asked. At that point, it sounded good to me. We pulled those pesky condums off and began stroking each other's cocks like there was no tomorrow. I got a nice little puddle of lub in my hand and really started stroking her cock. She said "Oh, I'm gonna come fast like that" and leaned back and enjoyed the ride. I stroked her cock the same way I would my own and she was loving it. She just lay there, trembling in pleasure. She asked me to press my cock against her as I stroked. I felt really good that I was making her feel so good. My dick was left on the back burner, but again, that was more than fine to me as I was about to make this sweet little honey blow her load. As I stroked harder and faster, she shook and then blew he love potion all over her stomach area and my hand. My hand was covered in jizz. She removed my hand quickly as I could imagine her cock was senstive after cumming so hard. I kept touching it, wanting to gently squeeze all of that cum out. I wanted so bad to lick my hand clean along with her cock, but I knew that wasn't a good idea. Being safe is important, so I smelled her love juice and then wiped it off.

Now it was my turn. She jacked my dick like she was skiing in the Winter Olympics, but I just could not cum. It wasn't her, I just couldn't cum. The first time I ever fucked a GG it took me longer to cum than I had expected. Maybe it's something about that first time. I have made myself out to be a picture of stamina here, but my next time, I'll probably be a two pump chump, haha. I hope not. So, I started stroking my own cock and placed her lubbed up hand on my balls. She rubbed my balls as I jacked my dick. I could feel it coming and then I exploded. I cummed so much! She immediately got up and brought me a wet rag. Of course, I wanted more, but I could tell this poor girl had had enough. So we talked a bit and then I washed my hands and got dressed. She told me to call her again and then walked me to the door.

Overall, it was a very nice and pleasurable experience. I wanted to hang out, maybe smoke a little herb and then go at it again, but I don't get pleasure out of putting someone else in pain. She was nice, but a bit typical, judging from the other stories I have read here on HungAngels. She wanted to charge extra for kissing and her cumming. If she had been down to continue, I would've given her a nice tip. That is, the tip of my hard cock in her ass again, mwahahaha!! Just kidding. Seriously though, if she had been down to go on, she would've received a tip, but once she cummed, that was pretty much it for her. This just happened yesterday and I am already wanting it again. I made a deal with myself that if I am going to do this, I need to limit it. Now that I see that I like sex with a t-girl as much or even more than I thought I would, I wouldn't mind meeting a nice TS girlfriend. I am not really into paying for sex, as I mentioned previously. I'm sorry this was so long, but it was my first experience and I couldn't wait to share it. It wasn't perfect, but it was very nice. I hope to have that experience again sometime real soon. Thanks for reading.