All completely true.
I was horny, in my mid 20s, backpacking, single, and living in a big city with a famous red light district. Walking to the shops everyday one could see the trans sex workers in bars and going about their daily lives. A lot of the times one could tell who the m2f ladies were due to certain physical aspects, but that’s one of the main things that I found a turn on, the slight bulge, the slightly deeper but effeminate voice, the sluttiness of their outfit, their over-high heels. It drove me wild to see them every day.
One particular horny night, I had drank some beers with friends at the hostel and was totally unable to shake the thought of these sexy ladies. So I told my friends I was heading out to a bar to meet a “friend” whom I had recently met whilst working on a temporary job site. A total fabrication. I just wanted to go and talk to one of these ladies hanging outside the strip clubs and bars. Not even for sex particularly, just to speak to them face to face and admire their sexy bodies.
I did find some ladies at the entrance of a bar but wasn’t able to talk to them for long without actually entering the bar. Being a backpacker, living hand-to-mouth, I just didn’t have the money to go in to the club to just sit and talk and buy expensive drinks, with possibly no action at the end.
So I went to a bar. I checked out the local classified ads. My friends had told me about getting cheap blowjob’s from a woman on the website so I thought I’d check it out.
There were dozens of hot trans women advertising. I couldn’t believe the choice, All within literally walking distance from where I was staying.
I chose the lady whom I found most attractive, she listed herself as “The Bod”, she was Thai, her body was sensational, she advertised photos of herself wearing fishnet stockings, long smooth tanned legs, a g-string, high heels, a 7″ penis, long hair and was passably pretty and very feminine.
Being too nervous to call her, I texted and told her I was looking to hookup that night. She replied almost instantly telling me her address; a hotel about 15 min walk from me.
I had been attracted to the idea of Trans ladies and crossdressers for a number of years so this night was the culmination of years of lust and desire. I remember my heart pounding and trying to hide my obviously rock hard erection, during the entire walk there. Luckily the streets weren’t too busy it was around 1am.
I arrived at the hotel, the receptionist looked at me blankly and said hello out of politeness. I could tell that I was just one of many horny, anonymous people who must dip in and out of places like that hotel night in night out. It kind of dispelled my self consciousness knowing he’d seen this play out so many times before.
I punched the floor number she had told me into the elevator, and felt my heart thudding uncontrollably as the 9th floor bell pinged. I wasn’t unconfident, I was actually totally earnest in my desire to live out a long dreamt of fantasy. I knew exactly what I wanted to do.
I knocked on her door, she answered with a coy smile and a “hello baby” in greeting, and proceeded to leave the door ajar and walk back into her room letting me enter. This was all done very theatrically, her heels clicking off of the floor, her ass bouncing from side to side; the view of her g-string and fishnets and body stocking was so immensely erotic to me, I remember having blurred vision because I was so horny and turned on.
I remembered reading some thing about handing money over as soon as one arrived, so I did that promptly and she sat me down on her bed. The room smelled of perfume and incense, the lighting was very low. She told me to go and freshen up with a shower in her en-suite, and to come out naked – ready for my ‘body massage’, which I did unhesitatingly. I showered very quickly to not waste any of my 30mins, and came out unashamedly fully erect.
“Lie down on your stomach baby” she purred…..”I’ll massage your back” I knew this was just a precursor, and found it quite uncomfortable as i was nursing a full erection. I was laying with my head at the end of the bed resting my chin on the backs of my hands, she came and stood with her groin directly Infront of my eyes, while she was rubbing my shoulders. She had the bulge I was so obsessed with, I couldn’t believe this was happening. She lent right over to massage down my back and pressed her bulge into my face and after a very short while, I shifted with lustful, but polite, impatience, she must’ve know she was driving me wild.
“Do you want to play with my cock, baby?” She questioned, clicking back on her heels, flicking her hair back over her shoulders, standing there, eroticism personified. Wavy black hair half way down her back, black body stocking, no fake breasts (I hate them) skimpy G-string, black fishnets, red toenails and hot strappy heels. She had a beautiful flat stomach, long legs, honey coloured skin, and red lipstick.
“Yes, I really do” I replied. So she walked over to me, I rested on one elbow and started rubbing her bulge through her underwear. This was the first penis I’d ever felt aside from my own. I felt her growing harder. I felt the urge to just rub my face into her burgeoning bulge. So I did. Feeling her erect penis on my face was amazing. Knowing she was hard, I slipped her underwear to one side and out sprang her penis. It was amazing. I immediately sat up and positioned myself on the end of the bed and began playing with her penis, it was totally smooth and uncut. I loved gently jerking her, pulling her foreskin back and forth over the head of her penis. Sticky precum leaking.
One of the main things I wanted to do was to suck and lick her balls, then rim her ass hole. Her balls were big and dangling and smooth. I asked her if I could.
“Sure baby” she replied. So I lay back on the bed, head at the end of the bed looking at the ceiling. She slipped her g-string off, cocked one leg up, resting one heeled foot next to my left shoulder and presented her balls to my face. Basically she teabagged me. I kissed, licked and gently sucked her balls. So smooth and wonderfully erotic and taboo. I then got her on all fours on the bed and I rimmed her for a while too, this was just too incredible.
The pièce de résistance was sucking her penis.
“Your first time baby?” She asked, I replied in the affirmative.
“Ok, hot” she giggled. She slipped on a condom. I got onto my knees and took her into my mouth.
The feeling of a penis in one’s mouth for the first time is unforgettable. It felt absolutely incredible, slightly pulsing, growing harder and so smooth with the condom on. I asked her to slap me in the face and on my tongue with her penis, she happily obliged. I was obviously getting way too into it as she had to ask me to calm down; I just loved doing it.
The time must’ve been ticking as she then asked if I wanted to fuck her. Now, the actual act of sex wasn’t at the top of my list, the fondling and oral foreplay was my main interest, but I couldn’t deny the fact that I was packing a big load that was crying for prompt release.
So I asked to fuck her doggy-style, she nimbly slipped a condom on me and assumed the position on the bed.
I had performed anal sex on previous girlfriends and this felt exactly the same. Not quite as stimulating to the penis as vaginal sex, but still great, coupled with looking at her ass and thinking about all of my erotic desires that I’d taken care of that evening I knew it wouldn’t take me long before I exploded. I slowed down and slipped in and out of her ass slowly just to savour the view/memory/experience. She was still wearing her heels. So slutty and hot. I wished I could have made her cum on my face but couldn’t afford the extra.
I pulled out and whipped my condom off and came all over her back. She laughed and mentioned that the amount of cum felt like a lot. I cleaned her off with a towel. She said I could shower again if I liked. I thanked her for such a good time and had a short chat – she was 32 and studying in the City. I didn’t shower there. I felt like I had experienced a dream and left.
I walked back to the hostel, and showered in the early morning hours.
I have never told anyone about this experience. It was one of the most liberating and hot experiences of my life. And I think about it with veryfond memories.
Since this experience, I have had 2 more experiences with trans escorts.
Thanks for reading my story.
Source: reddit.com/r/sexystories/comments/n9ngfh/trans_escort_experience_m_26
I had a similar experience in thailand. It was my first experience with a ladyboy and sucking her nice smooth cock. I love reaching down and stroking her as I did the deed