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This story that was posted at the forum today by our new member got me hard as hell. He writes about his first experience with a tgirl and i can't be more positive that most of us would like to experience this too. Enjoy reading...

I recently had my first experience with a shemale. Here's how it happened.

For the last few years I've being seeing escorts, and I search for them online. I noticed ads for shemales, and they looked pretty hot. Didn't think anything more about it, though, for a few months. One evening I was seeing a girl I'd seen a few times before. She was complaining business was down - was losing trade to shemales! It wasn't long before she lost another one: me.

I looked up available shemales in Toronto, and went to one next chance I got. Oh my god oh my god what an experience! I won't give her name here but will do so in a private message at the forum. She was about 5'8", blond, and very, very feminine. She took me into her bedroom, and had me lie down. I looked her over as she turned away for a minute. She was so beautiful - there was no way anyone could have known she had not been born a woman - that is, until she turned around, her dick exposed with a condom on it, and said to me, "suck my cock".

Now that is what I had come there for. I had been fantasizing about sucking cock, but the idea of doing it with a guy grossed me out - I had to do it with a girl. So here goes.

Now one problem I have is that my gag reflex is really strong - makes trips to the dentist kind of tough. So I couldn't take as much of her cock into my mouth as I wanted. But I tried my best. After a while, she took the rubber off when I asked, and I kept on going. What I really wanted was for her to cum in my mouth but she didn't want to cum (I found out that most of the time a shemale escort is not going to cum until they're on to their last customer of the day, for obvious reasons). She stayed standing by the side of the bed, holding my head with one hand while she fucked my mouth - a huge turn-on for me.

She she put another rubber on, and told me she was going to fuck me. This was not part of the plan - not something I'd been fantasizing about. But it was really interesting - she was very much the take charge type, and was running the show, so I thought I'd go along with things, and I let her move me around so I was lying on my back, my legs over the edge of the bed.

She had some lubricant, and worked it into my ass.

"You're really tight," says she in her cute east european accent.

"I've never done this before," I explained. That seemed to turn her on. "I'd better open you up a bit first." She got a dildo from a drawer, put a rubber on it, and started to gently work it inside me. After a while she was gently fucking me with it, while I squirmed underneath her, watch her beautiful breasts jiggle as she worked on me. After a while, she pulled out the dildo, and suddenly I felt her hardness pressed up against me. She was much bigger than the dildo, and had some trouble at first. She told me first to squeeze very tight, and then to relax. As I relaxed, she inserted the head of her cock in me. Then she told me to squeeze hard again, and then to relax, and pushed further in. Then she started short, quick strokes which seemed to open me up, and in no time, she was in me to the hilt.

Now I can say with total authority that being fucked up the ass is the most natural thing in the world. I absolutely loved it! I had never been so turned on in my life with the wonderful sensation of her hard cock sliding past my prostate over and over again, faster and faster. She talked to me as she fucked me:

"So you've never been fucked before? Want me to stop now?"

"No don't stop please don't stop keep fucking me oh godddddd"

"You're sure now? I don't want to hurt you!". She leaned forward closer, and held my shoulders while she fucked me harder. I pulled her face down to me and we kissed - a huge turn on with a cock up my ass.

She straightened up again and started to work on my cock while continuing to push in and out, her pace slowing a bit as she started to jerk me off. In no time I had such a powerful orgasm that my balls hurt, cum flying all over the place. She laughed as she watched me spray everywhere. When I was done, she pulled out, and off I went to the shower.

After goodbyes, I was in my car a few minutes later, already hard as a rock just thinking about what happened.

I still see women a lot more often than shemales, but I will never stop seeing a nice shemale now and again. There's no experience like it.

Tags for this post Post tags: anal, beautiful, blonde, blowjob, cum, dildo, domination, fucking, jerk off, reality, sex, sex toys, shemale, Shemale Stories, stories, tgirl, tranny
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25 Responses to “My first time with a shemale escort”

  1. jo says:

    Great story.

    Reply
  2. Charlie says:

    WOW! great story. I wish that I could expierience that. Huge fantasy of mine. I'm definitly jealous.

    Reply
  3. smally says:

    wow, i'm 58 and am going to try it out

    Reply
  4. jojo says:

    Sounds like a TS I've seen in EROS Toronto online? If it is I am thinking of checking her out! She looks and sounds unbelievable! I'm still straight too!

    Reply
  5. sarah says:

    I would love to experience a night like that! I would like to be shemale one day. Until I can do more than just dress up to resemble a tgirl, I would love to be with a real shemale.

    Reply
  6. sarah says:

    I want to meet ladyboysor shemelt . Im 29, Im BI. I like everything! I travel everywhere thisis my address sarahpolly1980@yahoo.com

    Reply
  7. jojo says:

    Always love reading this great story.When I get the courage I will try to experience too. For now I am going to a live shemale webcast and jerk off!

    Reply
  8. woody says:

    I would like to leave my jizz in a ladyboy's mouth while I enjoyed hers in mine.

    Reply
  9. woody says:

    I think a ladyboy with a eight inch cock would be ideal for a blow job because I would like the taste of it in my mouth while she enjoyed the succulent taste of mine. Oh boy!

    Reply
  10. t@$ty says:

    w0w h0t st0ry s0undz exciting like @ whol3 different feeling i"m @ girl n straight but th@t st0ry juz turn me 0n i 90tt@ experience @ shemale 1 0f these day

    Reply
  11. Jiggly says:

    I once took a $hitt in a shemales mouth , it was Pooh-tastic.

    Reply
  12. Bobblehead says:

    I was just skimming through some sites on the trannys. I'm 58 and it seems that all my life I avoided what I knew, that I secretly wanted to have sex with a guy, but The idea of doing it with a guy just turned me off. So I was checking out the trannys and just looking at them makes me hot. I read the story about the escort and I have to admit that I really would like to meet a nice shemale lady, discreetly, and visit with her with some wine and if things work out I would be willing to learn about Her and how it feels. I can't believe I'm really saying this but,I would kiss and make out with her and when the heat is right I would be a willing pupil. I would suck her cock and try to swallow it whole. I would hope that she would take control and get me hot and fuck me for a long time and fill my anus with cum, and make me cum by fucking me in the butt. I've dreamed of it secretly for most of my life. I couldn't afford to pay for this service but maybe one of the ladies would like to teach me about it. I've never done anything like this before, so I guess I'm a virgin except for a small dildoe I have lately started using. I will try it if I can get a teacher.

    Reply
  13. Mrhawk60 says:

    This story raised more than my spirits lol, I am an older male who would love a brief erotic encounter with a beautiful shemale.
    Any interested shemales in Toronto (Scarborough), contact me at mrhawk60@gmail.com.

    Great Story
    Thanks
    Hawk

    Reply
  14. demonshez says:

    i just love shemale. i always wanted a shemale to fuck me harder and harder and harder and at the same time masturbate me ... its my fantasm
    unfortunately, in my country, no shemale - must only dream

    Reply
  15. Fabio says:

    I'm 24 have money and would like to see what it's all about

    Reply
  16. jesse-x says:

    The story about the escort did raise it up for me. I am an older man who has fantasised about, one time even called and talked to, a lovely person on the phone. (HE? SHE, was in another state however. She sent me a long letter telling me about some of her ADVENTURES I got off on that letter many, many times, Even shared it with my wife and we bothgot off. If we could find her we would invite her to come stay inthe Salt Lake area with us for a while. I would love to be persuaded to suck female cock, and my wife would love to see it too. We still have that letter somewhere. have it somewhere. 'by! Jesse-x

    Reply
  17. benstoval38@gmail.com says:

    Would like to experience

    Reply
  18. Jose Mario says:

    I wish I was in your place!

    Reply
  19. Josh Artlu says:

    I was lucky enough to have my first experience recently, I have not ever spoke of it before.
    Its something I had to do for a long time.So I wrote a note to myself. here it is-
    Well today, I took the plunge. I went to meet a real Tranny. After finally finding her place and after a quick chain smoke, the nerves set in. I waited outside the door. She let me in from the buzzer. I walked into a dim hallway. She popped her head around the door. There she was standing in high heels, bra and panties. She asked if I wanted to smoke. I tried not to but had a quick drag. I didn't know what to do at first, we were in a small room, mostly taken up by the bed. I stripped off, I felt her soft skin. And saw her cock between her legs, I touched it and rubbed it whilst she sucked mine. She asked what would I like to do next?I said can we do 69, it's always been a fantasy,the she stood over me and pumped it into my mouth. She didn't say a lot but she said do you want me to fuck you?I said can we fuck each other?she said lay down, she got her lube out, I guess I was shitting it. She went a little way in I could feel it a little. Then she stopped, It weren't happening,Then I was a bit floppy with nerves,second attempt. All good, I really enjoyed bareback whilst holding her cock mostly. It was a strange experience and would love to do it again with a shemalebut with big breasts next time.

    Reply
  20. mojo says:

    The first time I saw a trans lady, it was for "live porn" -- I thought I didn't want sex. But once I got there -- that candy stick begging to be touched and sucked -- what started off as a hesitant but curious kiss, became a full on feast! It felt so good flicking my tongue along her shaft, sliding the length of her penis along my tongue, mouth wide open and closing in when I had as much in as I could get in. I begged her to come, begged. When she gave in, the throbbing in my mouth gave me took me right over the edge with my own jerking. Gawd, I'm flaming hard just writing this and can't wait to relive this dream!

    Reply
  21. glen says:

    I can't wait until I find another tboy with a small dick and we are both dressed up.in mini's and high heels. Sitting in a bar full of people and teasing all the guys her playing with my dick and I playing with her under the table.whewn people are trying to peek.What a turn on

    Reply
  22. cant tell you says:

    that is my ultimate fantasy, I wanna suck some shemale cock then get fucked but i dont have the currage and I like girls so i'm kinda shy.

    Reply
  23. Steffi and Sivlon says:

    I was recently in Thailand on a business trip and as I had of course heard of the ladyboys in Thailand, I wanted to see if the fuss made about them was justified. I telephoned http://www.bangkokladyboys2go.com and booked Pai. The photos of her looked great and I thought perhaps that the pictures had been photoshopped. The booking was easy to do and very discreet. I was nervous about using Bangkok ladyboy escorts but I need not have been, she immediately made me feel at ease. Ladyboys in Thailand or as they are known in Bangkok Katoeys, are fully accepted and assimilated into Thai society. So it was very easy to sit in the restaurant that I had chosen for the evening without the feeling of prying eyes burning into the back of my head.

    Reply
  24. zzsy says:

    I'm curious what the cost was. I see adds on Eros that say such and such roses but is that the full amount? I want to have the same experience described above. Thanks for any and all info.

    Reply
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