[M]y first MTF trans hookup that opened Pandora’s box.

After creeping for a long time I’ve decided to start sharing some of my sexual escapades. For my first few posts I’ve decided to reminisce on my early experiences with MtF trans women.

For as long as I can remember, I’ve had a kink for trans women. Something about a beautiful woman with a good cock has always interested me. This interest never took on more than the occasional porn search or jerk off session when feeling extra horny and the regular stuff wasn’t doing it.

Fast forward a few years in my early 30’s, I found out I was moving to Hawaii and I was being warned that Hawaii had a very large transgendered population. After arrivingI jumped on dating sites, message boards, kik etc. and noticed a larger open population of trans women oin most of the apps and dating sites. Before long, my horninesss and curiosity got the better of me and my porn searches became reality;I specifically started chatting with and searching for trans women. After a few weeks of chatting, trading random pics, and trying to make a connection I got a promising direct message; she saw that I had mentioned I was new in town and was looking to meet up, but had never been with a trans woman before. We talked about what I wanted to explore what I was open and comfortable with. Things progressed and we eventually traded pictures. Holy shit she was smoking hot. Thin, Hawaiian, tan with a perfect round ass and perky tits. I couldn’t believe it, I hit the jackpot. Our chats quickly turned dirty,e flirted and exchanged videos and pictures over the next few weeks.

One day she told me she needed to confess something. I figured a deal breaking confession was coming. She told me she was married to a male and he didn’t know she was fooling around with other people. Fuck it, I thought, not my problem. We continued flirting and quickly decided to meet up in a public to make sure everything was cool. The day of the meeting she tells me she wants me to come over to her place instead which made me real nervous. This was happening. Up until now, all of my sexual experiences had been with women, but my fantasy was finally in my grasp.Even though it excited me I was hesitant. What if it’s a trap,someone looking for a mark to rob or beat up? I was reluctant, but ultimately agreed.
At this point I had some experience with prostate play. I had been edging and hadn’t cum for a few days in anticipation of our meeting, knowing it would heighten my pleasure. She gave me directions to her place and I head over. Luckily, I saw her on her balcony before walking in. She seemed like the same girl which helped to calm some of my nerves.I walked up to her apartment, she opened the door and quickly pulled me in. I saw she was dressed in nothing but a short, silk bathrobe with her cute thong clad ass peeking out. She took me to the bedroom and told me to sit down and get comfy, she’d be right back.

I’m nervously sitting and waiting, she’s every bit as sexy as her pics. When she came back into the bedroom she didn’t say anything, she just dropped her robe exposing her cute panties and cuter tits. She walkeds over, pushedes me down and starteds to kiss me deep and hard as she straddled my hips. I eagerly began to explore her ass and titis; my hands grabbed, pinched, kneaded, and fondled while she ground herself onto my cock. Now officially rock hard, I pushed her over and got on top to continue to peruse her body. I kissed and bit her tits while I ran my hands over her sides, up her thighs and around her tits. Meanwhile, she rubbed my cock and guided one of my hands down to her panties. For the first time my hand rested on another person’s raging hard on. I abandoned exploring the rest of her body and sat up to pull her panties aside and expose her short, hard cock. I wrapped my hand around it and began to stroke it up and down as I did I heard, “Do you want to suck my pussy?”. I told her yes.
I prepared myself to cross a line I had never thought I’d come close to and at the same time realized I had no real clue what to do other than the stuff I liked being done to me. Throughout this revelation I continued to stroke her as I moved my face between her legs. Fuck it. I opened my mouth and took her inside it, suking and licking between her legs as my hands moved to play with her tits. After awhile she pulls me up tells me to relax and says it’s her turn. She spreads my legs and starts sucking my balls while slowly stroking my cock. She moves from my balls down to my ass tonguing my ass like I’ve never had before. I’m in pure heaven feeling her tongue my ass and stroke my cock. At this point the edging and 5 day absence has made me sensitive and I already feel myself getting close to cumming. I tell her to slow down as I don’t want to cum to fast. She stops stroking me and solely focuses on my ass slowly starting to work a finger inside me.

I’m in complete sexual bliss having this beautiful woman between my legs tongue fucking my ass. As she works her finger in I’m desperate for more and blurt out “fuck me!” I couldn’t believe I said that and I think she couldn’t either as she instantly sat up with a big smile and asked me to say it again. This time I collected my thoughts and told her to quit teasing me put more fingers in my and finger my ass hard. She quickly slips two fingers in and finds my prostate right away. She starts finger fucking my ass and prostate like I’ve never felt before. She’s slowly sucking my cocking and relentlessly finger fucking me. I keep telling her to slow down as I want to ride this pleasure as long as possible before I cum. After what seemed like an hour I tell her I’m ready to cum. She picks up the pace of sucking, stroking and fingering and I feel my orgasm building. This is different though it’s not coming from my cock but deep inside me and the feeling is overwhelming. I’m moaning, bucking my hips and completely lost. I tell her “fuck I’m going to cum, I don’t know from where but fuck don’t stop it feels so good” she starts sucking faster as I start to cum with the most mind blowing intense orgasm I’ve ever had. I’m almost yelling I’m moaning so hard. Thrusting my cock forcing every drop of my cum into her mouth. I finished physically cuming but my orgasm continued as I couldn’t stop moaning and shaking as I continued cuming. Finally after a few minutes I finally stopped and she came up to kiss me. I felt like I was in the verge of passing out, my muscles randomly shook I had the most intense tingling feeling all over my body and felt weak like I couldn’t move. She got up and offered me some water as I Laid there recovering. She came over kissed me then grabbed my face and pulled it to her hard cock. I started sucking as she slowly fucked my mouth. It only lasted a minute or two as I still felt like I would pass out. I apologized and she laughed and said she understood. She got between my legs and started to suck me off again. Unfortunately after about 10 minutes I still could t get hard still could barely sit up.

We chatted for another 20 minutes as I slowly recovered. I told her that was the most intense mind blowing orgasm I had ever had and apologized for not being able to continue or finish her. She told me not to worry and asked me if she could cum and I would watch. I said yes. She got between my legs and started jerking her still hard cock. She rubbed her cock along mine, stroking with one hand and rubbing me with the other. She quickly came covering my dick in cum which she promptly got down and cleaned up sucking my cock and her cum up.

I got dressed and got ready to leave. We agreed to meet up again soon. Sadly she ghosted me and we didn’t get to meet up again. However this only fueled the fire and led to a few more encounters over the next few years.

Source: reddit.com/r/gonewildstories/comments/djr4nf/my_first_mtf_trans_hookup_that_opened_pandoras_box