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It's not always that the first experience that guys have with shemales is a bliss and a dream come true, there can be unlucky exceptions too. Our reader, who calls himself John Doe, was hooked on shemale porn for a long time and finally decided to turn his fantasies into reality. What a big disappointment it was for him.

I was stationed in the middle east, and everything was ok, until a few months later when we got the internet in our rooms. That was the best thing that ever happened. Being so horny all the time, and being in such a shithole place, I started to experiment with all sorts of different porn genres. Finally I was exposed to shemale porn, and I got hooked like a fish on a fishing hook.

I consider myself straight, and have always been sexually attracted to genetic females, and have always had sex with genetic females only...UNTIL

The urge kept going higher and higher, and when I returned home, I started browsing craigslist for transgenders for sex. Finally I got an invite at a hotel room, and I went on with the date. The kissing part was extremley unbearable, I kept on thinking please please don't kiss me... arrrrrgggghhh, I still feel like puking when I think about it.

After I received a good blowjob, I returned the favor...yuck... I didn't like it, I actually hated it, I was cursing myself for going along with this plan, and then the disaster struck. After her keen insist on fucking my ass, and the unknown feeling of some obligation (maybe because I didn't pay for the hotel or anything), I surrendered; big mistake. Not even 2 minutes into anal sex, I experienced severe pain, it shot up from my anus to my stomach. I couldn't take it anymore, and told her to stop. My ass was bleeding. It wasn't due to her size at all, she was below average. After cleaning up, I walked out, and that was the end of the date.

I was cured after a few weeks, it seemed like a tear in the anal fissure.

A fantasy is called a fantasy because it is not suppose to be fulfilled. I learned that the hard way. Sometimes I get mad at myself for putting myself into such a position, and going along with it, and sometimes I am glad that I did it, because it gave me a much clearer understanding of my own sexuality, and taught me a lesson for thinking from the other head.

I still watch shemale porn, but no more live shows for me, thank you very much.

Tags for this post Post tags: anal, blowjob, fucking, reality, sex, shemale, tgirl, tranny
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12 Responses to “My first shemale experience was a disaster”

  1. Curious says:

    Although your experience went poorly, I wouldn't go as far to say fantasies shouldn't be fulfilled. I was once curious, and I experimented, and it went really well.

    Perhaps your experience went poorly due to the way you approached it. You went out a met a complete stranger off the internet, which to begin with is a little uncomfortable. You didn't have any trust with the girl, as you said you felt obligated to let her penetrate you. There are better ways to meet a T-girl, and plenty of attractive ones who can kiss and have a nice, clean cock.

    Reply
  2. Emli06 says:

    I myself have no experience with lady-boys.
    What I can tell from the many photos on internet is that the Asian girls look often very feminine , delicate and very attractive and somehow the fact that they often kept their genitals really contributes to their attraction , as if they combine two good things from both worlds , the feminine one and the male one.
    So you understand my position in this: these lady boys look great!

    But this appreciation makes a bit of healthy thinking all the more necessary.

    Let us , just for one moment , assume that all the lady boys that we see once started their lives as boys , who developed the growing insight that they were actually women caught in male bodies.

    Let us assume that -by their own free will- they chose to become women with help of hormones and ,possibly, operations.

    If that is not the real situation ,though, for instance, in some or maybe many cases boys were forced into becoming she-males in order to play a role in the sex industry , then we are dealing with a major violation of human rights and the boys must be seen is mere victims.Everyone who would "use" these victims for sexual reasons would victimize them in more than one way.

    Let us point out things very clear here :

    Everyone who wants to meet a she-male for sexual gratification only may then rightfully be considered a serious sexual offender.

    But let us suppose that we are dealing with case one: boys met with their destiny and became attractive women , just the way they wanted.

    In that case they would be honoured most if they were treated any woman or girl would like to be treated : with love and respect.

    That sharing a mutual love may be the outcome of a positive emotional encounter , well , who can be against it?

    If we are talking about "love" here, please let us -adults- not fool ourselves by mixing up love and lust..

    I think that the best that could happen to these beautiful persons would be that they would meet partners that madly fell in love with them and would (like to) marry them, so that they could live complete and rewarding lives, instead of being seen as objects only..

    I for one do not believe that any person who gets stuck in the framework of the sex industry will manage to keep his or her personal honour and integrity

    Reply
  3. MIKE says:

    Hey, I've been to Asia many times, visited Thailand, Laos, Cambodia, Vietnam, and China. First of all, there is no forced sex in this part of the world. The forced ever happened in this region was in Cambodia but that was 10 years ago, much has changed since the nineties. It seems rather dumb to invest 10000 dollars into forced sex change and gain a return of about 20 bucks a session, Ladyboys are not highly demanded in Thailand. If any of you have left the country at least once in a lifetime you'll find out that homosexuals are very much tolerated in Asia, and sex reassignment is cheaper than in the developed countries. Unlike rest of asia, Thailand has a major problem with this as there are way too many homosexuals and transvestites, I'd say about 1/3 of all Thai men are gay, not sure what's the reason.

    Reply
  4. tranny says:

    dears,
    i love shemale with huge cock.
    i love female bodybuilders too much,because they r the real MALE women with natural vagina & unnatural male physique..

    Reply
  5. GARY C says:

    WILL YOU LET ME SUCK YOUR BALLS AND THEN SUCK THE CUM FROM YOUR DICK

    Reply
  6. She male lover says:

    Sex with a she male can be nice. I met such a boy/girl in Birmingham, England. She had a stunning body and terrific legs. Tiny tits with big nipples. She dressed in a bra suspender belt stocking and a dress with a wig and full make up. She had a huge cock which I suck, but I like to penetrate her anus. The first time was over in a minute, but now with loads of lube I can make it last a long time. I like to do it face to face with deep kissing. It is wondeful

    Reply
  7. ED says:

    i was forced into dressing as a woman and takeing cock.the man next door used me for a long time for sex.i did so because caught me in stockings playing with my self.and said he would tell on me if i didnot.i did not like it at first,but after a bit i really liked it.now i dress all the time.when i go out i always dress in stockings garder belt bra slip sheer top short skirt heele and wig full makeup lipstick nails.i love to suck cock and to get fucked.dressed as i am it does not take long before i am on my back with leggs in the air cock in my ass and a cock in my mouth.i am good for 4 to 6 cocks in a night.

    Reply
  8. Mike says:

    Ed, I'd love to fuck you and stick my cock in your mouth. I've never been with a tg before, and I definitely want that experience. email me takeme2thebnk @ yahoo .com

    Reply
  9. Doug says:

    I would like to talk to and meet a transexual.
    my mail is lookingfil@yahoo.com

    Reply
  10. yturieowpq says:

    Emli06 has a point.

    Let us not forget in our lust that these are fellow people. Love of the eye, and love of the heart, should not be confused and ideally, we should not toy with other people in this manner. But of course, this is not an ideal world.

    I half expect someone to take something I just said and make it sound sus.

    Reply
  11. Mauser says:

    I've been with two trannys before, one in late 05 and on last week. The first was this Mexican chick with a small weeny. The last was this black chick with a big weeny. Both times I started out saying to myself "man, it would be cool to bang a tranny in the ass, I'd totally work em over!!!"

    Both times I ended up slapping on a condom and sucking their cocks... without a BJ in return.

    Grrr... one of these days...

    Reply
  12. johnny says:

    my first exp with a thai ladyboy was a disaster her cock stayed soft,got a great blowjob of her.the next week i met one in a beerbar paid the bf 300 agreed 1200 for all night.told her was my first time and would she show me what to do.after showering we got into bed.kissed a bit played with her tits she was slowly wanking me.she took my hand and put it between her legs she had panties on told me when i was ready put my hand inside and take her cock out.i felt so relexed .her cock was getting hard now i was wanking it ,she then went down to give me a blowjob.stopped b4 ishot my load.my turn now ,first time to suck a cock.that night we sucked and wanked each others cocks all night ,she stayed with me for a few days,during this time she shagged me up the ass,which i enjoyed,ialso shagged her ,im not interested in men but sucking a ladyboys cock seems normal,nothing like a good looking thai ladyboy walking around your hotel room in only her panties with her cock bulging out of them .

    Reply
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