Your first time with a tgirl

[tlover]

For you experienced guy's, how about telling us about your first sexual encounter with a tgirl and how it felt.
and how you felt after the experience.

[hankhavelock]

Check out the thread: How Did Your Love For Shemales Begin ?

i yearn for the day i can tell a story like this.... i must keep dreaming for now though.

a man can dream, can he not?

*cry*

it was about 6 years ago ( first seeing and interested about Ladyboys were 15 years ago i wait for 9 years for that day ) when i was chatting in the Mirc channel i saw a nickname trv..... and asked "who are you?" then she said a girl name and i understand she is a she-male and i started chatting with her. she was living very close to my home and asked her to go there and have some fun. she said "i am doing this for money and i won't charge you too much bec. i liked you." she said. and then we agree on that money and i went.

i was so nervous and very excited to see my first she-male in real. After knocking the door she opened the door and invite me inside. We went to the living room and there was a friend of her. two She-male was hot they have nice boobs, they have sexy dresses and nice faces. after talking for a while.she asked me "what about going to my bedroom ?" and we say bye with a blink, she said "bye and enjoy with a good smile" i couldn't say come with me, i was so nervous and excited. we went to bedroom and i start to undress and she too. and go to bathroom 1by1 to take shower. she had a g-string and she hide her precious and i didn't say i am active and passive. and we start kissing eachother and touch her boobs and suck that hard nipples. she grasped my cock and started sucking it.i was touching her body and beautiful ass. and i fell her cock. i started to touch it outside the string and she looked at me and said " are you interested ?" i said " yeahh, lets make 69" and i took that beautiful my first she-male cock in my mouth and start sucking a little after she was hard and i was sucking her so wild . i didnt want to stop sucking but she said "would you wanna be fucked ?" and i said "i want but please be polite " my ass was virgin :D it was my first she-male cock in my ass.

she lubricated herself and my asshole too. started fucking by her fingers first, to open. and that big cock came and go inside of me slowly . i felt some pain. it was not easy for me first but when all of it goes inside i felt better and enjoyed that moment she fucked me and came in my mouth. i came when she was inside of me with a really good cumshot.

that was the first time and was really excited at first time.

ohh i am wet now

[eliogabalo]

It was about 4 years ago. She was a prostitute and her name was Kelly. She was a white brazilian ladyboy and we became quickly lovers. She kissed me with the tongue for about an hour (!); then asked me to be fucked. I loved her long kisses, but i was not sexually satisfied because i love the passive role and she didn't fuck me. I found my perfect partner only 7 months ago.

One of my excited adventure,

a place where freelancers comes together and they wait for their clients. you go there with a car and find your partner and go somewhere.

i went and one of them was walking near the street. i stopped my car and asked her if she would com with me and she said ok. we went a desolate place and i parked the car. she said i don't want anal and just sucking. i said ok then she started to rub my cock and took it out, while she was licking my dick i start to rub her ass and her cock. and i said i want to touch your cock. she said ok and pull out her dick.
it was hard and thick not too big but nice one. i started to jerk off her and put it in my mouth, that was delicious and the place where we were excited me so much, we could be arrested or be seen by someonen the thought of it was excited. i said her "would you wanna fuck me ?" she said yes and i bend over my shoulders becouse we were in the car and she spitted to lubricate her cock and push it in to my asshole. she fucked me so slowly bec. i like it slowly and when she said i m coming i said take it out and come in my mouth and i swallow it. and i came in to her mouth too.

and i bring her back and go to my home with that pleasure......

[aventura]

Most of you guys are lucky I've hardly seen any shemales where I live at in cali.

I wish I had a TS girl friend


Great encounter translover

[Paul]

I've been with shemales for the last 5 years, they are without doubt the best lovers I've ever had. I'm currently in a relationship with a very passive T-Girl and shes recently moved in with me. Anyway, it was my birthday a couple of days ago and we both got very drunk. I'd mentioned in the past that I've always fancied being fucked but shes always been reluctant. Well, my birthday night was my lucky night! It hurt like hell but she was very gental with me. I was suprised how good having a dick inside me felt, the after sensation was like having a warm glow all round my body. I'd like to take it more often but she said it's only going to be a once a year birthday treat! Not fair

[Wanzerich]

i hope i will have my first sex like you translover, slowly and not so fast.

its hard to find a good looking shemale, but my hope never ends

[tlover]

Originally Posted by translover

it was about 6 years ago ( first seeing and interested about Ladyboys were 15 years ago i wait for 9 years for that day ) when i was chatting in the Mirc channel i saw a nickname trv..... and asked "who are you?" then she said a girl name and i understand she is a she-male and i started chatting with her. she was living very close to my home and asked her to go there and have some fun. she said "i am doing this for money and i won't charge you too much bec. i liked you." she said. and then we agree on that money and i went.

i was so nervous and very excited to see my first she-male in real. After knocking the door she opened the door and invite me inside. We went to the living room and there was a friend of her. two She-male was hot they have nice boobs, they have sexy dresses and nice faces. after talking for a while.she asked me "what about going to my bedroom ?" and we say bye with a blink, she said "bye and enjoy with a good smile" i couldn't say come with me, i was so nervous and excited. we went to bedroom and i start to undress and she too. and go to bathroom 1by1 to take shower. she had a g-string and she hide her precious and i didn't say i am active and passive. and we start kissing eachother and touch her boobs and suck that hard nipples. she grasped my cock and started sucking it.i was touching her body and beautiful ass. and i fell her cock. i started to touch it outside the string and she looked at me and said " are you interested ?" i said " yeahh, lets make 69" and i took that beautiful my first she-male cock in my mouth and start sucking a little after she was hard and i was sucking her so wild . i didnt want to stop sucking but she said "would you wanna be fucked ?" and i said "i want but please be polite " my ass was virgin :D it was my first she-male cock in my ass.

she lubricated herself and my asshole too. started fucking by her fingers first, to open. and that big cock came and go inside of me slowly . i felt some pain. it was not easy for me first but when all of it goes inside i felt better and enjoyed that moment she fucked me and came in my mouth. i came when she was inside of me with a really good cumshot.

that was the first time and was really excited at first time.

ohh i am wet now

Great and horny story Tran's, thanks for taking the time and effort to everyone. really enjoying reading your story's.
Really Sorry you had to wait 9 years for your first tgirl experience trans, hope i don't have to wait that long ,i might go mad!

[gizmo]

Myfirst time was about 3 year's ago!
Went to visit a GG in brazil, she was my "gf"
She lived in Sao paolo, not a nice neighborhood!
We went out for a few night's, but she was working
so I decided to try my luck! First time out, met a beautiful
"girl" I did'nt have a clue!!! Got back to her room
and she told me to strip! 0k, no problem, I was hungry for the pussy!
But it did'nt work out like that. She had the biggest cock I'd ever seen
I thought "why not", so I fucked her, and to my surprise she fucked me!
Long story short, I loved it, and never looked back!

Originally Posted by gizmo

Myfirst time was about 3 year's ago!
Went to visit a GG in brazil, she was my "gf"
She lived in Sao paolo, not a nice neighborhood!
We went out for a few night's, but she was working
so I decided to try my luck! First time out, met a beautiful
"girl" I did'nt have a clue!!! Got back to her room
and she told me to strip! 0k, no problem, I was hungry for the pussy!
But it did'nt work out like that. She had the biggest cock I'd ever seen
I thought "why not", so I fucked her, and to my surprise she fucked me!
Long story short, I loved it, and never looked back!

that is my fantasy Gizmo
Meeting a girl, hope to suck and fuck some pussy !!
A beautiful face and body

And you go home and see the surprise for you

I think it would be my horniest time :D

Hi people, :D

Thanks, if you like my real life stories. i have a lot of

But i am very busy in these days and i will post them later when i feel myself good and really horny (i think i must read some LB-69 forum, )

I am sorry for my English, if i write something wrong but this is my best

C U

[kamsutra]

Originally Posted by tlover

For you experienced guy's, how about telling us about your first sexual encounter with a tgirl and how it felt.
and how you felt after the experience.

I am still waiting for my 1st experience at 26

sorry can not post my shemale-dreams ...

Originally Posted by translover

Hi people, :D

Thanks, if you like my real life stories. i have a lot of

But i am very busy in these days and i will post them later when i feel myself good and really horny (i think i must read some LB-69 forum, )

I am sorry for my English, if i write something wrong but this is my best

C U

ur a lucky bastard u know?

Originally Posted by guest

ur a lucky bastard u know?

Not yet my friend

First, i have to go to Thailand and meet with that BEAUTIES (My Dream Girls)

Then i will be lucky

[hankhavelock]

My first meet with a trans-girl DID IT for me - I've described it more in detail in another thread, so no need to repeat myself.

Many guys appear to be scared shitless when they FINALLY summon up all their courage to finally take this from fantasy to reality. Don't be - chances are that it will be better than your dreams! Chances are she'll take you to the moon and back!

Just do it!

Peace!

Hank

[scotty1090]

i envy translover soooo much

hi again,

1 month ago i met with an another T-girl in internet. we talked and decided to meet, we said we meet and jerk off together while watching a transmovie and then suck eachothers. i went to her home but when i go there was a male friend of her, we went to her room while her friend waiting us we sucked eachother, i jerked her and fucked her. while fucking her i was jerking then she came and a little after i came and squirt my cum on her breasts. she was not beautiful but it was a nice fuck.

i ll never meet her again. my ladyboy searching continious. i like adventures much.

[foly]

Still dreaming about that day... i hope someday it happens..

[DEFENDER]

I found my first (and still my fave.) by checking out the Eros website. I was as nervous as fuck but she was SO nice to me and really understood my feelings......and I will NEVER forget that moment when I eased down her panties to reveal a nice stiff dick with a lovely bead of pre-cum on the tip......and taking it in my mouth seemed the most natural thing to do. It took a couple of sessions before we fucked (just mutual wanking and mouth fucks to start with) and when I first pushed my dick into her sweet bottom, I thought I was in heaven!
This was a couple of years ago and it just gets better!

[giancarlo]

It wasn't such a different experience so I could have a special spot in my memory for it...

[wendals]

I havent had an encounter with a t-girl yet but I cant wait for the day I do!

[humbolt77]

Originally Posted by tlover

For you experienced guy's, how about telling us about your first sexual encounter with a tgirl and how it felt.
and how you felt after the experience.

My first time was last summer, finally managed to get the courage to go through with my fantasy. Where I live there are no TS Girls as far as I know, particularly Asian, which for me is the only way to go. Spent a week in London and did plenty of research on the "right" escort. Eventually found her, her name is Venus, Thai, stunningly beautiful and 100% passable, please see for your self (I was dubious if she was going to be exaclty as her picture/profile made out, but I had nothing to worry about, she was absolutely stunning)
I went to her apartment, and knocked on the door, when she opened it I couldnt believe my eyes, never met a TS girl before, she was so beautiful, her voice, posture, body language was 100% woman. I was nervous as hell, like a teenager about to loose his viginity!! I wish I could rewind and do it over again this time with a little more confidence.
Anyway, we played and 69'd and I fucked her, dont fancy taking it to be honest, but im sure I would some day. I didnt perform as I should have, and didnt do half the things I wanted, although she made me feel at ease. This is probably because I had never been with an escort before. And I felt guilty too, but that another story....
Suffice to say it was the BEST ?150 ive ever spent in my whole life, and woould do it again in a hearbeat. The only thing spoiling the experiance was the whole HIV thing in the back of my mind.. I would have loved her to cum in my mouth... I wish it was the 70's again...!!

[maxpiazza]

My first time with a shemale was back in the late nineties in Milan, Italy.
it must have been 1998 or 1999, I remember watching a lot of porn back then. I was especially aroused by shemale scenes and there I started fantazising about fucking one of those beautiful creatures. My favourite scene was a very sexy brazilian shemale wearing a white navy officer hat being screwed by two studs on a sofa . Her name was Sabrina Hemolly and I really fancied her a lot. One summer night i was driving trhu a part of the city which at the time was well know for the presence of trannies walking the road. So i was looking around when i spotted a black Alfa Romeo parked along the road, the side door was opened and a pair of long sexy legs in black stokings were emerging from the car. I stopped my car near her and i looked inside: here there was the sexiest, hottest tranny i ever saw. She was Sabrina Hemolly indeed. I really can't believe my luck. I did'nt know she was in Milan but i always dreamed to found her somewhere someday because a lot of brazilian trannies were working as escorts in Milan at the time, and theer were always new girls coming over. When I called her by name and I told her taht i was "in love with her" because of her movies, she replied with a pleasant smile and told me it was time for me to stop wanking and "doing the real thing". So i followed her at her flat and had some of the best sex I ever had. I remember her rolling her eyes upwards like a demon while i was fucking her ass, like she often does in her movies, and that really made me crazy. From that night i had regular sex encounters with other beautiful shemales but i still remember her as my first "special" time.

[brian621]

I was getting in my car after work which is downtown and this babe with a micro skirt walked. She was working and he big thighs and round bottom looked good. I agreed to go to her place and when sh got in the car and grabbed my stiff cock she told me she was transexual.I agreed to go with her. Her cock was small and she did not get hard even when I sucked.But was a good fuck and I enjoyed the session

[StellaDixxie]

Top black girl, hung, uncut, my place. Best sex of my life. We went at it for about 4 hours.

[BentOverBitch]

My first time was about 15 months ago. We had been dating for a bit & She was a dominant shemale & I was a single submissive. So losing my shemale virginity was spiced with some s&m.

We were listening to music at her place and with no warning, Miss Stephanie had me kneel before Her and to get Her cock out. I had never touched another cock before and my hand was shaking. Part nerves, part lust! Ma'am was incredibly hung which excited me to no end. Or rather to my end. An average cock could not give me that feeling of submission I need. Once I took Miss Stephanie into my mouth I knew that being a great dildosucker = being a great cocksucker! Of course, it was more exciting because the reactions were true. She directed my cock sucking and was in charge the whole way. Her moaning just wanted me to please Her more. When Ma'am was close to cumming She ordered me to finger Her ass. She told me when She came to leave it in my mouth while jerking Her off. When She said now, I was to pull it out and have the rest on my face. I did and Her cum was so much sweeter than mine! A lot more of it too. Miss Stephanie smiled and rubbed Her cum all over my face and I was told to leave it.

I was commanded to suck Her until She became hard again which was almost immediate! She had me kneel on the couch cushions with my arms on the back of the couch. I was expecting to feel Ma'am's cock but was shocked to feel the hard stroke of a cane across my ass. I yelped and Miss Stephanie laughed and asked if I was surprised. She then laid another dozen strokes rapidly across my ass in what seemed like 2 seconds. I was whimpering and moaning unashamedly. My ass had been totally untouched in two years and so in a way, it was like the first time again for me. She came around to and grabbed my hair to face Her. She barked, "Do you want to be My bitch?" I nodded, which was a huge mistake. She slapped me HARD. I quickly stammered, "Yes Ma'am, I want to be Your bitch." She put a couple of big time, major pain nipple clamps on me and I gasped. I'm used to heavy nipple torture and these clamps hurt as much as any I had experienced. She then lubed me generously but roughly, fingering me crudely. Miss Stephanie told me not to move and left.

Miss Stephanie returned in about five minutes. She lifted my head up and began squeezing my tits hard and twisting the clamps. I almost passed out yet still remained hard. She then walked behind me and I prepared myself to be reamed by my first cock. Once again I was surprised to feel the smack of what I later found out was a thick wooden paddle. Ma'am gave me thirty or forty hard strokes and I bawled like a bitch. She then faced me and asked if I wanted to be fucked. I said only if it pleased Ma'am. She smiled and said good answer. I looked at Her cock and it was harder than I'd yet seen it. It was purple with arousal and the mushroom shaped head appeared eager for my ass. Miss Stephanie said that She expected me to be a great fuck at all times. I'm NEVER to just take it like a lazy bitch regardless of my physical condition. I was expected to meet Her every thrust with equal force. I agreed. She got behind me and spread my cheeks by digging into them with Her long nails. She also scraped my beaten ass with Her nails causing me to moan loudly. I was expecting Ma'am to ram it up my ass with a single, brutal thrust. However, She again surprised me by fucking me slowly and with just the head of Her massive cock. She said She wanted me to get used to that massive head. It hurt like hell but I was determined to please Miss Stephanie. After a moment She buried it in me and the race was on! Ma'am is not into gentleness and I was fucked hard for at least 10 or 15 minutes. Often She would pull Her cock out all the way but didn't miss a beat so I was really, really getting hammered. I hadn't been in such sweet agony in years! She changed positions, having me lay on the floor up against the couch with my legs pulled back near my head. Miss Stephanie ordered me to suck my own cock while being fucked! Never had such a thought occurred to me. But I'm built in such a way that I could pull it off. Or rather suck it off! lol The sight made Her fuck me even harder (if that's possible) When Ma'am was about to cum, She growled for me to cum and not lose a drop. When Ma'am came in a groan, She pulled out, cumming on my asshole, then shoving it back inside of me with Her cock. That caused me to cum with the best orgasm I'd had in years!!

Miss Stephanie smiled at me and said I was well on my way to being Her permanent bitch, which I was for over a year.

[chinotheonly]

I am new to the scene and I have been looking around to have my first Trans girl experience. I know that I have always been interested but I never have a chance to meet one. All I know is that I am ready and still waiting for my first time.