I'd like to share how it really began for me.  Ever since I was very young I knew I was a little different, liked girly things, but I had to always suppress it, being that way just wasn't allowed, so I grew up the classic blue collar red neck country hick.  Then I enlisted, it was the thing to do, and of course anything sissy or gay would get you kicked out, or maybe killed.  But when I was 19 I was sent  to Thailand, my first experience out of country.  Being a support base for the war, everything, even the town of Udorn, was a 24 hour rotating operation, so I began to head off base a lot, started drinking too much, indulging in a lot of prostitutes.  I loved the small bodies and delicate features of the Asian women.  Then one evening, pretty drunk as usual, I unknowingly attached to a ladyboy, quite pretty as it seemed most of them were.  After awhile of partying, flirting, dancing, drinking, we went to her room to get serious.  We both were in a good mood, she undressed me, not unusual, and started the usual games of playing with me and sucking me, getting me horribly worked up as young men usually quickly do.  Then she stopped, got up and took off her panties, but still dressed in her blouse and skirt otherwise.  I expected her to mount me, but instead she straddled my body, leaned forward and began to kiss me, then gently holding my hands she began to slide up my body, bringing my hands over my head, her knees in my armpits.  I expected she was wanting some oral satisfaction herself, so I closed my eyes to avoid getting them poked by her skirt or anything, I was kind of held in a submissive posture, not natural for me but I enjoyed it, and then I felt the **** drag on my face as she leaned over me.  I was caught off guard and tensed, but I felt her grip on my hands tighten just a little as she softly cooed to do her like she did me.  She slowly moved her hips a little, rubbing her **** around my face, and for some reason, I wanted to please her, make her feel good, and I opened my mouth, taking in my first ****.  I found myself enjoying it, enjoying her moans of pleasure, enjoying the feeling of her getting bigger and harder, enjoying the pleasure I was providing her, enjoying her gentle dominance over me, and I was excited.  I wanted to grab myself but couldn't because she had my hands, she began gently pumping my mouth and came inside.  She stayed there for a few minutes, then slid down beside me.  I wanted release, but she said not yet, we rest now, told me how I was a #1 **** sucker, how I'd make a good ladyboy.  She fell asleep curled around behind me, I couldn't, my mind racing about what I had just done.  Did this make me gay, was I a ***, why did I enjoy this so much?  Eventually I did fall asleep, only to be awakened by Kim caressing me, her **** was hard again and pressing against me from behind.  She caressed me all over, pinching my nipples, stroking my hard ****, driving me crazy.  I could have very easily overpowered her and taken her, but I couldn't, I allowed her to do as she pleased, her delightful cooing and the happy sounds coming from her made me feel good.  She rolled me over on my back and I thought, what now, she has no *****, will she suck me so I finally get some relief.  But instead she got up, got a jar of Vaseline and came back.  She took some out on her fingers, took my hand and smeared it into my hand, then put my hand on her ****.  I had never *********** another **** before, but it was fun, and we lay there ************ each other.  She smeared Vaseline all over my balls, running her fingers lower and fingering my ***, and I would spread my legs and raise my hips a little to make it easier because I liked the feeling.  Once we were all loaded with Vaseline she rolled over on me, her legs between mine, and we rubbed together, kissing and holding each other.  It was fantastic, I thought I'd *** right then, but instead, before I could, she put her hands on my chest and pushed herself up on her knees between my legs.  As she put her hands behind my knees and begin to pull my legs up I knew what was going to happen, I said please don't, but she was smiling, telling me I was such a good sissy boy, how I was going to like it so much.  I was nervous and resisted, but you can only pinch so long, and as soon as I relaxed a little she pushed in.  It hurt, I yelled, she pushed forward on my knees shoving me harder on my back and pushed all the way in.  The she stopped as I gasped for air, deep inside me, and as I relaxed it began to feel nice, a fullness like I'd never felt before, and as she started to move in and out, slowly, only short strokes at first, telling me how good it felt to **** me, I found I was responding.  This time my hands were free and I could **********, it wasn't long before I was  moaning and bucking and shooting my *** all over myself, stimulating Kim to *** inside me.  I was exhausted, I thought I'd pass out, Kim let my legs down and laid on top of me again, my *** smeared all over us, and we went to sleep.  We got up a mess and went to wash up, splashing each other with bowls of cold water.  Few people have hot water there.  The cold will really draw things in, and Kim teased me about my tiny ****, sissy **** she said.  She ran to the bedroom first, I toweled off, freezing my butt off.  When I got to the bedroom I couldn't find my clothes, Kim had hidden them.  She said she wanted to dress me, I said fine, it going right over my head what she had in mind.  She got out a pair of panties, a mini skirt and a blouse and proceeded to dress me in them, she was laughing, giggling, so happy, then had me walk around the room while she told me what a pretty ladyboy I made and i wouldmake a good *****.  I loved it, it made me extremely excited, and this time I was dressed and Kim was naked, and I went over, bent her over the bed and proceeded to **** her silly.  But this was the dawn of a new me, the realization that I wasn't the *** hating country redneck I was living my life as, but I was actually a sissy who enjoyed dressing as a girl, sucking **** and being ******.  My live changed dramatically those few days, I hope to never forget a moment of them, and I will be forever grateful to Kim for setting the inner me free.   

SissyDenise SissyDenise
56-60, M
1 Response Feb 27, 2009

I got down to Pattaya for a week of R&R, since my security level prevented me from being allowed to leave the country. It's a shame you didn't have more time, it's such a beautiful area, which is why it was a French resort area for so long. The intermix between Thai and French has made for some incredibly beautiful women, some of the most beautiful in the world in my opinion, and the petite body structures make for some incredible lady boys, while the highly tolerant Thai culture allows them to very openly live their lives as they want. I attempted to extend my stay over there, hoping I could run out my enlistment there and just stay, but you know how the military was, they had other plans.