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  #1  
Old 02-15-2011
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jamielily73 jamielily73 is offline
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Default ANY type First time stories! =)

Hi, one of my favorite things to do on here is to read the Amazing true life "1st time stories" of people on here!!! I would LOVE if yall would like to volunteer yall's 1st time stories here: First time crossdressing, First time giving a bj or j/o to a (cousin, relative, friend,etc), sneaking around your parents house to have sex, the 1st time going in femme, sexxy experimentation w/ masturbation, WHATEVER!!! The more sexxy details, the better!!! So come on, let's hear 'em!!!
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  #2  
Old 04-20-2011
hungweilo hungweilo is offline
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Default My first

I had my 1st T-girl experience last Nov (2010). It was awesome (she had just gotten new tits and I was the 1st to touch them!) I couldn't believe how tight her ass was. It felt incredible. She knew how to flex her ass just right.
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  #3  
Old 05-02-2011
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My first ladyboy experience was in 1996 in Bangkok. Me and a friend were on temporary duty there for an exercise.

I'd been stationed in Korea but I'd never seen anything like Bangkok. The sights and sounds of that city are amazing. Best of all for a young military guy was the night life. Patpong, Nana, Soi Cowboy...I'd never seen anything like it. So many go go bars with so many women. Hundreds of girls that wanted to go with us every night. It was amazing and for the first time I realized how backwards and closed minded my own country was. Why couldn't everywhere on the planet be like this?

We were on a 2 day binge already the night I'm about to tell you about. A binge of booze and pussy. I'm not sure how many girls I'd been with already but I'm guessing four. All were working girls but that is what we wanted anyway. Two young guys overseas in a town with no limits. We were alive!

Back then there were no ladyboy bars that I can recall in the red light areas of Bangkok. If there were any, we didn't see them. I'd heard there were some transvestites that prowled on drunken foreigners and I told myself if I ever saw one I'd run the other way. This was before the internet and I'd never seen a transvestite in person or in pictures and didn't yet know what a ladyboy was. I was green and naive.

We had one night left in Bangkok and hadn't yet hit Nana Plaza hard so that was our target for the night. Three floors of bars, about 30 of them if I recall correctly; probably about 2,000 women to choose from. Maybe more as that time was more lively than it is today.

We found ourselves in a smokey dark bar on the bottom floor. I don't recall the name. I only know we went in there because my wingman liked the door girl and wanted to chat her up. He was busy with her and I was just relaxing while he worked his magic. He didn't waste time and was soon back in the short time room with the door girl. The only thing I remember about her is she had purple hair. It was probably a wig.

After he took his girl for a short time, I was left at the table by myself. It wasn't long before a girl came up and asked if she could sit with me. This lady was stunning with a gorgeous body, long hair, cocoa brown skin and almond shaped eyes. She had the shortest mini-skirt I'd ever seen and fantastic tits that were falling out of her halter. I invited her to sit.

She wasn't a dancer in the bar, she was a guest relations officer which is a fancy term for working girl. Just what I was looking for. I bought her a ladies drink and we started talking the normal chit chat stuff. Much to my surprise, she was actually pretty funny, spoke good English and enjoyable to talk with.

Some more drinks for both of us and soon she had her hands on my crotch. I was fondling her smooth legs. Soon she got up and excused herself to the bathroom. This was when the waitress came up to me and said "That not lady". I wasn't really sure what she meant. The waitress wasn't getting her point across so a guy sitting nearby, I think an Aussie, helped to translate. He told me the girl I was sitting with wasn't a girl but a bloke with a cock.

I was stunned & couldn't believe it. She was not my impression of what a transvestite was. I guess I figured they were guys in a dress with a 5 o'clock shadow.

When she returned, I asked her directly if she was a guy. Not my most sensitive moment. Much to my surprise, she said she was a ladyboy not a guy. This was the first time I'd ever heard the term. She asked if I wanted her to leave. It would have been easy to say yes but I was still stunned and now curious about this mysterious creature I'd stumbled upon. I told her to stay and ordered us more drinks. This got me a hug and hands back on my crotch. I was too embarrassed for this so I kind of pushed her off me. I said she could stay but I wasn't interested in that. But she had a ladies drink so she stayed. My life would have been very different had she left then.

I was shy others would see me sitting with a ladyboy but it was very dark in there so I thought I'd be ok. Liquid courage helped too. To settle my nerves I had a couple tequila shots. Finally I began to relax again. My friend finally came back to the table saying his short time turned into a long time and he was tired, drunk, broke and heading back to the hotel for sleep. He asked if I was staying and my new friend said "Yes he is. Don't worry he's in good hands".

Very cool I thought. My wingman gave me a high five and said goodnight. I was now on my own in Bangkok half drunk with a gorgeous ladyboy for the first time in my life.

With my friend gone, I was able to relax more. Social pressure back then especially in the military was overwhelming. Had he known she was a ladyboy I probably would have left with him, but he didn't know. Soon I let my guard down a bit and she was back to rubbing my crotch. I realized my cock was getting hard in the bar. I reached up under her dress and felt her hard cock in her panties. Now my heart was pounding a mile a minute. For the first time in my life I was stroking a cock other than my own.

I asked her if she wanted to come to my hotel with me & she said yes so I told her to go change and I'd pay the bar fine and my bill. The waitress looked like she'd eaten a lemon. She didn't approve but I didn't care. We left the bar and were back in my room in no time. It was a frenzy. Clothes flew off in all directions. Suddenly she was standing before me naked; this beautiful goddess with the most feminine body, gorgeous tits and a 5 inch hard cock. She guided me to the bed and I kissed her neck, shoulders and breasts. She moved my head down lower and I found myself sucking dick for the first time in my life. I didn't know how to do it but I tried doing like I'd prefer it; lots of lips & tongue & no teeth. I sucked her for awhile but she didn't cum. We switched positions and she started sucking me. Oh my god, it was fantastic and the best blowjob I'd had up to that time. I knew I wouldn't last much longer so I rolled her over and said I wanted to fuck her. She complied and showed me what to do. Luckily she had lube because I didn't. I did have condoms though which I made sure we used.

She lubed us up and guided me into her. At this point I didn't have much control and I cummed within a minute of being in her. I think this the first time I ever yelled out loud while having sex. The waves of sensation were staggering. Not just physical sensations, but mental as well. She actually cleaned me up a bit and I noticed she was still hard. This was when she scared me half to death. She told me now she wanted to fuck me. I didn't know what to do. She could tell I was nervous and told me not to worry that she would do everything and be gentle. She lubed us both up again, put me on my back, spread my legs and slowly, gently slid her cock in my ass. It hurt but it was a good hurt. An exciting hurt. My heart was racing again and much to my surprise my own cock got hard again. As she fucked me she started jerking me off. I'd neglected to do this for her when I was on top.

As I got more and more excited, so did she. Her pace on my cock and my ass quickened. I couldn't believe it but I was cumming again!!! When she saw me shoot my load she let go of my cock and hooked my legs over her shoulders. Now she was banging me hard. My knees were pinned back and hitting the head board of the bed. It hurt more but I was also experiencing only what I can describe as a mind orgasm.

I couldn't take much more though as she was fucking me now like a wild animal. Finally she cummed in my ass. I could feel her cock throbbing as she unleashed her juice in me. She gave a yell this time when she exploded.

We tumbled into each others arms smiling and laughing. I no longer felt any shame. I felt like I'd discovered something I was always meant to experience. There was no other person in the world I wanted to share my bed with that night. Only her. I drifted off into a semi-drunken blissful slumber with her massaging my back.

I woke up the next day and felt like I'd experienced an epiphany. My eyes were open now to this whole new world. We had another morning session of fucking and sucking. Then we took a shower together. I asked if she'd stay with me my last night in Bangkok and she said she would. I gave her some money for the night before and to pay her bar fine for my last night. She left and said she'd be back later. After she left I felt like an idiot as I gave her money for this day when I could have just went to the bar that night and paid it directly myself. I began to think she wouldn't return. I ate a room service lunch, watched some TV and snoozed. I began to write off the extra money I gave her when my phone rang. It was the front desk saying a Ms. Thongsook was downstairs and they were asking if she could come up. She had returned...My Angel.

We spent the next 24 hours doing everything you can imagine. Fucking, sucking, jerking each other, taking baths together, I even held her cock when she took a piss one time. After a few rounds I had to ask her to please not fuck me anymore as I was just too sore. She complied again and just jerked off on my chest. Around dinner time my hungover friend showed up at my room. I had her throw on her dress which was quite conservative compared to what she wears in the bar. She looked like a bank teller. My friend came in, saw her and gave me another high five. I told him I was staying in with her and he said "Good choice". Again, she fooled him and he had no idea she was a ladyboy but this time I wouldn't have cared if he did know.

That's the story of how I met my first ladyboy Thongsook. We kept in touch for awhile and I went back to see her again about 4 months later but we eventually lost touch. This was before email and neither of us was very good at writing snail mail. She changed my life and I'll never forget her.
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  #4  
Old 05-05-2011
RiverRatJimmy RiverRatJimmy is offline
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Great tale, you`d have got a high five from me!
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  #5  
Old 05-26-2011
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jamielily73 jamielily73 is offline
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GREAT Story PI!!!! would love to hear about any other experiences u had!!! ur gooood! =)
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  #6  
Old 05-27-2011
trannyluva trannyluva is offline
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wow! i cant wait for something like that to happen 2 me!
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  #7  
Old 05-27-2011
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Riovacation Riovacation is offline
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Well written, great story.
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  #8  
Old 06-01-2011
kkq kkq is offline
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I am in bed now with my Ladyboy. We have been together for a long time now but here is my story.

I have been in Thailand a long time; done my time with many angels an after the three day rule an then them wanting me to buy them a Condo the moment I started getting marginally close to them, I got very despondent in my thinking.Was I just a walking ATM?...another story of a sick water buffalo was going to make me leave Thailand. I had dated several very nice non-bar girls but the story was not much better an I never got to fuck them without them wanting more. You might call me greedy, but marrying a starfish would not be good fun.

I was wondering back home one night an in a bar I saw the most stunning girl; she was just a straight 10. I almost wreaked my bike in fact when I saw her from the corner of my eye by hitting a parked car. Anyway, I got a park an walked into the bar.

I was like a cruise missle; straight to her an bought a drink an then we played pool for 2 hours. I use to shark in my teens an can play way above average. I have been known to clear the table on break. Well, my girl was par for me. We played game for game with whoever broke, winning the game always by one ball.

I asked to bar fine her; Gee is 5th 7", natural shape in breasts and the arse an body of a angel. Just like wow!

Gee told me she would not bar fine an worked only for drinks in this bar as a relative owned it. She said we could catch up the next night for drinks am pool. I could not wait.*

The next night we ended up going to a pool hall an played locals at the game. After a few hours the locals caught on to our playing skills an we left to go to a late night disco. We danced an drank until 6am an I ended up in bed myself very drunk.

Gee rang me an she told me she was going to her Uncles place to cook for three weeks. Ot had been planned a long time ago. She told me to ring an if I wanted, could see her in two weeks at the Uncles.

I texted Gee over 300 times an spoke daily to her for 3 weeks as I could not go to see her for my business was busy at this time.

I finally got to see her an after a 8 hour bus trip, she rang into my arms an we kissed for the first time. For the next 3 days we ate an drank together but never slept together. She was special to me an sex was not on my mind. I knew it would come, but would give it time.

Now came the bomb shell; I was to go back to Chiangmai, an as I left on the bus to come home she told me as I departed on the last step, with a look of worry on her face, "I wanted you to know me first; I am very bad but I Ladyboy"

I got home in shock. I had seen many ladyboys over the years but not ever fooled for so long. She was perfect in all ways an that should have been the show stopper. China angel perfect an just too good for the likes of me. Well it put a dent in my pride, but after 90 hours of pineing for her so badly an missing the way I was loved an treated, I rang Gee to come to me.*

The sex for me now is too special to post on this board. We have been together now for sometime an live a good life here in Thailand. This is super long term.

I have till this point only slept with girls but to those who are sitting on the fence, my Ladyboy simply put, blows everything pale into comparison. The only thing I miss of a woman, is the ease of sex; Gee (not her name) likes to be, very, very clean before we have sex. It is not the same as a woman when you wake up in the morning an feel horny, where you can just slip it in. Anal sex demands things to be clean for safety but this small downside of just having to wait for a little while in the morning, before slipping it in, is no deal breaker...
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  #9  
Old 06-12-2011
Sabrina Sabrina is offline
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Default my first time with a man

okay this is a fun story. this is the first time i tried to be with a man. i was really horny and looking all over craigslist for months and months until i finally decided to post an ad that said i was a crossdresser that was looking for a man to pop my anal cherry and treat me like a woman, provided that he hosted and brought me to his place and gave me some clothes to wearl. little did i know that i would find just that. he was not a really great looking man but he was willing to take me to his place, let me wear panties and a bra and a cami and have sex so needless to say i did it. i was really nervous at first but the nerves were killed by my horniness. i walked to the place that we agreed to meet at and met him at his car. i got in and he drove me to his place. when we got there he had the clothes that he wanted me to wear that night. i quickly went to the restroom and got dressed up in the clothes. it was a pair of black lacy panties, a black bra, and a blackk lacy cami. i was already hard as i put the panties on. i tried my best to tuck in my tiny little dick. once i was fully dressed i went outside to greet him. i gave him a bit of a tease and a bit of a lap dance. i grinded my ass on his thigh and his crothch. i could feel his hard dick on my soft virgin ass. i took his cock out of his pants and started to jerk him off. then i started to lick it and tease him untill he took of all his clothes. he started to suck my nipples through the cami and the bra. and he started to take off my clothes. i was there in only my panties and my bra. as he licked my nipples even more and then took off my bra. i was sitting there in only panties at this point and he was rock hard. my man then took out a dildo and told me to pull down my panties, which i promptly did. he lubed up the dildo and slowly slid it in me. then he slowly started to fuck me with it. and then left it in me when he told me to suck his dick again. and as i was sucking his dick he grabbed the back of my face and started to face fuck me. it kind of hurt but in a good way, i wanted to be abused a little bit. after a while of this he fucked me with the dildo again. it felt so good. but then he said he wanted to fuck me with his dick and i was more than willing. he took out the dildo put on a condom and told me to get in the position for doggy, which i promptly did. he then tried his hardest to get his dick in me but it just would not go in. after about ten minutes we decided it wasnt going to happen so he told me to just suck him off which i did. and he then jerked me off to orgasm. i came all over the place. unfortunately it was over and he drove me back and drove me home. then it was over.
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  #10  
Old 06-12-2011
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Sonder Sonder is offline
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I still haven't had my first time yet.
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