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  #1  
Old 03-23-2015
jimoshea jimoshea is offline
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Default Your first experience

I am 25 years old. The first time I met a transsexual I was very young. It was in Dundalk in a hotel. I paid 100 to meet her. I was so nervous I barely spoke. When I came to the room she stuck her tongue in my mouth and asked me for the money in a nice way. She told me to take off my clothes which I did. She wore a tong and a bra. Very sexy. She asked me to suck her cock which I lay down a did. I couldn't believe what I was doin. She started then sucking my cock. Minutes later she asked " can I fuck you" I said yes so she put lube on me and put a comdom on. She pushed her cock against me and then it slipped in. My mistake was for my 1st time I should have met someone with a smaller cock. The pain was very sore. But she started wanking me which made the paid become pleasure. I didn't last very long. I came all over myself. But she continued fucking me which became very sore again. She started getting very quick and banging hard against me until she came. I will never forget it. It was unreal. Anyone want to share there experience and how old were you?
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  #2  
Old 06-19-2015
red99 red99 is offline
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I have your same age, never have experience with ladyboy, but i hope to start soon, preferably in Asia.. Western ladyboys cock its too big for 1st time. And.. now im in Italy, the ladyboy here its too ugly and not feminine.
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  #3  
Old 06-20-2015
dblack dblack is offline
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My first time I was in my late 30's. I had always wanted to do this but never had a real opportunity. I found her on an internet escort service and arranged to meet her. I was nervous but looking forward to it. When she answered the door see was wearing a black babydoll and a pair of thong panties. I went inside and we talked for a little bit. Then she got up and walked to the other side of the room and stripped, with her back to me. She had a great ass! I remember thinking that this was it. She turned around and had the most beautiful black cock that I had ever seen. I spent the rest of the time with her cock in my mouth, in my ass and her sitting on my face until she exploded all over my chest. That was a great night.
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  #4  
Old 06-21-2015
jayxi jayxi is offline
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At that time I was looking for this information
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  #5  
Old 07-02-2015
Stewie7 Stewie7 is offline
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I am 40 years old. My first experience with transsexual lady was 5 years ago. Though I had a tons of shemale porn and have fantasied about being with shemale I never had a real chance. I live in Estonia so there just weren`t many beautiful T-girls available. One day I`ve noticed one ad. T-girl from Portugal, 23 yrs, slim, 8" cock, beautiful body etc. So I phoned her and we met. She was visitng Estonia. Well I was little bit nervous, my first time with T-girl. And I felt myself like a virgin again. Okey, there I was. She was very feminine, long hazel hair and eyes, soft kissable lips and very beautiful tanned body. She wore only black stockings and high heels. Altough she had fake tits, they were just perfect! She looked just a little bit like Patricia Sereira. She had very sexy low voice. Took my 65 and offrede me a juice. We started to smalltalk and she said that she likes Estonian boys! I asked why and she revealed, that we are tall, gentle and polite

I asked her if she could please fuck me first. She smiled and said that I then should suck her dick first. Well, it was first dick in my mouth and I was little bit nervous. This dick was beautiful, big and at last 8". I licked and sucked it until it was rock hard. She smiled and asked: "Are you sure that this is your first time, you sucked quite well!" Then she took some kind of cream and lubed my asshole and put her dick inside me. At first we did it on a missionary. She took my legs and what a view it was - beautiful lady fucking my ass gently. Her dick was bick but it did not hurt at all because I had practised with candles, dildos, vibes and butt-plugs for about 20 yrs Then we changed the position. I lied on my stomach and she fucked me from behind. Ouch, it was great! I felt that I almoust could reach hand free climax. Then we did it on the doggy-style. I asked if I could fuck her and she agreed. She lied on the back, I took a condom and sort of anal cream (for lube) and entered her. Her "pussy" were so tight and it was a surprise for me. I felt that I was almost done. So I took my dick out and asked her to suck me. She took the condom off and gave me one of the greatest blow-jobs in my life! It took at last ten minutes `till I shot my hot load to her mouth and she swallowed it all. Then she caressed my body while I just jerked her off. Afterwards we took a shower together and she washed me completely. I am very glad that my first time was perfect. Portugese girls are hot
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  #6  
Old 07-05-2015
lozlewis91 lozlewis91 is offline
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Default first transexual experience

my first time was in cardiff and that was the day i truely discovered what i liked. I'm only giver never taker but i prefer sex with ts girls than biological women is much more fun lol
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  #7  
Old 07-09-2015
deepgame123 deepgame123 is offline
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My first time was in Istanbul.

My hometown was an ultraconservative environment in which finding a ladyboy or shemale was IMPOSSIBLE.

Since my 18, I started to watch shemale porn. My sex drive toward them inevitably growed. I lost nearly half of my sexual apetite to girls. I started to find them very boring. First I searched in web. I found her webside. I watched her videos and her pictures. She was 21 years old when I was 25. Manytimes I tried to call her. Something inside me stopped me. I was looking her pictures and jerking. But I couldn't find enough courage to call her. I was always saying myself "I shouldn't do that, that is not good". I was in a big dilemma to call her or not.

One day, before I go for military service for god damn 6 months, one of my friend made me a suprise. He called a Russian prostitute for me. That girl was a drug addict and we enjoyed all night long with her. That night I confessed her that I wanna try a ladyboy. She said she had sex with one ladyboy and one guy once. She told the story, that made me very hard. I called my first ladyboy lover that night. She spoke very polite, she understood me very well. She gave me the courage I looked for.

After two days, that was a saturday night. I went her home. She was living alone in a very expensive residence. She was stunning. I remember her long blonde hair, small white ass, hormone titties and her tiny girl cock. Omg she was wonderful. And she was so expensive.

I wanted my first experience to be spotless. Thats why I paid for her full service for all night. First she asked me what to drink. She openned a red wine. We talked like half an hour and drank wine. Her words was oppening my hearth. When she spoke she was touching my hand, my chest and my leg. She started to kiss my neck. What I definetly like is a girl's touching or kissing my neck, but she started to lick it.

My first kiss, I can never forget that feeling. I can never forget her warm lips. No girl can kiss like her. I felt fire in all my body. My chest was burning when she kissed me. She stand up while she was holding my hand. She brought me her bedroom. She sit down on red satin bed sheet, spreaded her leg and pull me her self. She was wearing a white dress with mini skirt. I felt her cock on my cock. I never remember that I was that hard before. When I was kissing her I felt that she was already hard. I asked her if I could touch. She hold my leg again and put it on her panties. While I was touching her she looked my eyes gave me a little warm kiss again and touched my cock on my trousers. I was about to tear my pants

She oppened my zipper and started to stroke my bare cock. I couldn't stop to kiss her. My cock is a little bigger than 19 cm. She said me that she wanna suck me. She bent over on the bed and first kiss my cockhead and started to suck slowly. She was sucking with passion and moans. While she sucked she asked me to finger her ass. I pulled her mini white skirt and then her white g-string. When I was about to penetrate my finger she stopped my hand and sucked my finger. Then she brought my hand to her love hole. I asked her to allow me suck her cock and lick her hole. We made 69 and sucked each other. She dripped her cock juice in my mouth while she was getting hard. I swallow. She was saying that she loved my cock. She asked me to prepare her hole with my finger. I specially asked her to sit down on my face. I licked her hole while she was stroking me, she was dancing on my face. She putted the condom to my cock and pushed it with her lips.

Then she turned her face to me. Hold my cock, and slowly sit down. Her small cock was rock hard because I sucked her well. She rubbed my cock to her hole for a while. I was about to cum. I didn't wantted to cum and stopped myself. My cock slowly entered inside her. When she reached half of my cock she moved upward and sit down again. One, two three and she took all of it. Her boy pussy was tight for me. She started to stroke her cock while riding me. I wanted to see her cumming on me but I couldn't control myself and cum.

I fucked her all night long. When both of us cum we talked and drank. Till 5 o'clock in the morning I was with her. When I leaved she gave me a last kiss.

I slept with her 3 times more. She was my first love I cannot forget.

Last edited by deepgame123; 07-09-2015 at 12:45 PM.
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  #8  
Old 04-28-2017
jimoshea jimoshea is offline
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Any more stories for me
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