Hello!!!
I want to share my story here, my first time wth a Transwoman.
So here it goes…
Background – I was 21 and I was in college. I had been fantasizing about transwomen for quite some time back then, been watching porn and was too deep into it already. For some reason, I never found men or women quite as attractive as transwomen. I was getting desperate to meet one and felt like I was losing control of myself. I couldn’t sleep, eat, study, anything. I was just obsessed with them – every hour of the day, I used to think about nothing but them. I had been thinking about going to an escort but there aren’t any good ones in my city.
A short trip with friends – Finally I had an opportunity to go to another city where there are a lot of good escorts. The gang has decided to go on a trip and I had enough time to research the escorting scene there. My friends had no idea that I was into transwomen. I started doing my research about the hotels and escorts in the area. I had help from some nice people from an escorting forum and settled on one.
About her – She is breathtaking. She was a little skinny for my taste but oh boy is she good looking. Her lips are bright red, her hair is pitch black, boobs are perky. She looked soo simple and elegant and yet stunningly hot. It’s two days before we had to leave for the city and I was very nervous to call her up but gained some courage after looking at her pics for half a day. Finally, I pick up the phone and called her up. I said “Hello! Uhmm I got your number from a friend and my name is Max” (not my real name). She said, “Uhmm ok, what do you want?” (politely) and her voice was very good. It didn’t totally sound feminine but it was really good and I like it that way anyway. I said, “I am looking to spend some time with you uhmmm and I was wondering if you are free this weekend”. The conversation went on for some time, we discussed the place and the price. I booked a hotel and gave her the details of the time and place.
My first time – Fast forward two days and we are there. I couldn’t sleep with excitement this whole, I was worried about how I will perform. It’s three hours to meet her and I told my gang that I was going out for a couple of hours to meet family in the city. I booked a hotel 3 blocks away. I didn’t want to go empty-handed and was not sure what to get her. A bottle of wine would be too tacky and a beer sounded rubbish, so I decided not to get anything and look dumb rather than get something unrelated to the circumstances and look dumber. I went to the hotel and checked in and I was a little scared. The hotel is upscale and I wasn’t expecting any trouble but just couldn’t shake the thought of getting in trouble. Anyways, I spent about an hour and a half worried about a lot of things. Finally, the time comes. She called me about 10 minutes early and says “I am there at the hotel” and I say “Alright, I will be there at the entrance in about a minute”. I go down to meet her and she’s just standing there looking like an angel. I say my name and couldn’t resist touching her and gave her a handshake, which went awkwardly. I take her inside the hotel and we are both inside the room. I asked her if she wants water, she says “No thanks”. I said “alright, did you have any trouble getting here”, she said, “no, it was ok”. She puts her things down and I followed her. I mumbled “uhmm..”. She came to me and held my arm and asked: “Is this your first time?”. I said “yes”. She then leaned forward and said “it’s going to be ok” and then proceeded to kiss me. That was my first kiss with a transwoman and a memorable moment in my life. I couldn’t resist anymore and started kissing her heavily. Then I kissed her on the neck and touched her penis from above her clothes. I kept kissing her while groping her body and she stops me after a couple of seconds. She proceeds to insert her hand inside my pants and held my penis with a very firm grip. Again, I couldn’t resist and removed my pants fast and whipped it out. She gave me a handjob for a minute while kissing and started blowjob after that. The first time her cherry lips touched my penis is another memorable moment of my life. She didn’t fully suck it at the beginning but was just teasing with her lips and with the tip of her tongue. She then started taking it all in. She gave me such a sensual blowjob combine it with my anxiety and lack of control, I came. I came and she spits it out on my very own cock and gave me some more handjob. Then I asked her if I can suck her off for which she said: “of course”. She lied down on the bed and I touched her penis and it was kinda hard. I immediately put it in my mouth and started sucking off and again, this is one of the most memorable moments in my life. The first time you suck off a transwoman is always something that will stay with you. At the same time, I was trying to reach her butthole hoping to finger but couldn’t reach it as she was lying on the bed face up. I sucked her off for about 10 minutes and at that time I was pretty sure I swallowed some stuff. It wasn’t cum but pre-cum. I enjoyed sucking it though, it felt really good. I asked her to turn around and started reaching for her butthole. She turned around and sat in doggy style. It was perfect, finally, I could see her hole. So I started fingering her in the butthole, it was smooth and I loved doing it. For some weird reason, I felt like a baby at that time. Anyways, after fingering for a while I said I want to do it. I took out a condom and asked her to do the honors. She spits on my cock and sucked it and spit inside the condom and gently rolled up my penis. I thought it was a very nice touch. So I tried inserting my penis, it didn’t go. Her butthole was tight, very tight. After multiple attempts, I managed to insert it and oh god did it feel like heaven there. It was warm and me and God only knows how amazing it felt. I always had this fantasy to hold hair and do doggy and wanted to go for it. I was also afraid of what she might say, so I gently pull her hair back and held it in my hands for about 10 seconds before releasing it. I fucked her for about four minutes and came. I took my penis out and proceeded to the bathroom. I washed my dick off and cleaned my self. She went in after me. We lied down on the bed for five minutes and I told her for how long and how much I wanted to do this. I told her that I am really glad that I decided to go with her and for that, she did a gentle nod with a smile I simply can not forget in my life. Then we talked about how we can be in touch etc. etc. Then I paid her more than what we discussed initially including tip and everything. She took the money and her things and was going to leave. She gave me a gentle kiss on the lips and left after saying goodbye.
Thanks for reading, I hope you enjoyed it. It was a long time ago and this is all I could recollect. I will post my other stories here soon.
Source: reddit.com/r/gonewildstories/comments/fwl6up/my_first_time_with_a_transwoman