[MT] My first experience with a trans woman

I had been browsing sites like CL, OKCupid, POF, etc. for years trying to strike up a conversation with a legitimate trans woman. Most would end up being either professionals, or bad CD’s in wigs (nothing wrong with CD’s it just wasn’t what I was attracted to). I am a straight guy in terms of my dating past and sexual experiences, but the thought of being with a woman who also posses a penis is something I have been drawn to. I am 5’9″, in shape with a decently defined 6 pack, and oblique muscles, clean, and a working professional so I thought finding someone through these sites would be easy and we could go on a date and feel each other out.

Unfortunately, this was not the case and for years I would message girls only to have things fall through at the last second. Sometimes this was my fault since I was new and nervous. I had no experience and would also end up worrying that I was going to be chopped up by some axe murdered via Craigslist. Years had gone by, and after a long term relationship ended I decided I was serious about exploring this new side of things. In reading online I noticed that a popular app seemed to be a good place for linking up and actually connecting. So I downloaded it, and spend a few weeks messaging and looking around to no real success.

Fast forward to about two months ago…I received a message from an older cougar type. I have actually dated a couple older women in my past and loved their confidence and dominance so this was a great first sign. We got to talking and exchanging pictures and we actually clicked and shared a mutual attraction, so she invited me over. She lived about 10 miles away (one of the conveniences of living in California) and I decided this would be the time for me to actually go through with things. Of course I was nervous, but I went ahead and showered, brushed teeth, and shaved (I am relatively hairless so this wasn’t too hard).

Upon arriving at her house I let her know I was there and waited nervously at the door. It cracked open, and then fully opened to reveal a gorgeous curvy cougar that we will call Veronica. (Name changed for anonymity) I know it’s cliche, but she looked even better than her pictures in person she was wearing a silk slip with very feminine curves, and nice breasts thanks to her reasonably sized implants. She was a bit taller than myself, but I didn’t mind that at all. She took me by the hand and invited me in and we sat on her sofa and talked for about 30 minutes. It turned out we had a lot in common and got along really well and that really helped me feel comfortable. After talking and laughing for a while, she looked into my eyes and said “well are you going to kiss me?” Now keep in mind this is the first time i’ve kissed anyone besides a CIS woman and I was probably trembling, but I went in for it and it was great. She had these very plump and full lips which I am sure were thanks to injections, but the were great. Within seconds our tongues were in and out of each other’s mouths and her hands were running up my back and under my shirt to feel my skin. She stoop up and led me to her bedroom and I knew where things were going and couldn’t have been more excited. I glanced down and admired the curves of her hips and ass as we walked down the hallway. Once inside her room she laid on the bed and patted it signaling for me to come lay down, but told me to undress first. I pulled my tshirt and socks off and slid my pants down, leaving my underwear on and climbed into bed.

She and I laid on our side continued making out while running our hands on each others bodies. I was following her lead and she slid her hands into my boxer briefs and grabbed my ass so I did the same. She commented on what a nice bubble butt I had and with a little smirk told me she was going to have fun with it. I ran my hands down her back and on her silky nightgown and to her ass and squeezed it firmly as we made out. She then rolled me onto my back and straddled me which gave me perfect access to her breasts. I pulled each strap over her shoulder and slid her dress down to reveal nice globes of flesh with semi hard nipples. My mouth instantly jumped at the opportunity to kiss, lick, and nibble on her as this was familiar territory and this is something I could tell she was enjoying by the moans she let out as my tongue circled each nipple. At this point my cock was throbbing and leaking precum in my boxer briefs and I was ready to make a move. Slowly I ran my hand down her breast and stomach and down the inside of her leg and she let out a big sigh of breath and I knew she was horny too. On my way back up her leg I lifted her dress and realized she had no panties on which made making my way to her cock even easier. I ran my hand up her leg and to her taint and then tight hairless balls and then let my fingers wrap around her hard cock. It didn’t feel weird and at this point I was so into it that my mind was no longer thinking straight (pun intended) with my fingers wrapped around the shaft I let my thumb play with the tip and spread out some precum she was leaking. I slowly stroked it and realized it was uncut, which is another first for me as I am cut myself. With her position being where it was she seized the opportunity to move on her knees higher and higher until her cock was inches from my face. She then reached behind herself and freed my throbbing cock from its boxer brief prison and stroked it slightly, this pushed me over the edge and I lifted my head enough to take the tip of her in my mouth. Her precum was essentially tasteless albeit a little sweet and I loved it. She proceeded to move her hips and gently fuck my mouth. I wanted more so I told her to get on her back and then assumed my position between her legs. I ran my tongue all over her balls and up her shaft then filled my mouth with saliva and proceeded to slowly and sloppily suck her maybe 5″ cock and take it as deep as I could for a first timer. After only a few minutes she told me to slow down because she was going to cum. Then she said it was her turn and took my 8.5″ cock in her mouth. Gagging on it like a pro and showing me how one really sucks cock was such a turn on. She let spit and saliva run down and slowly fingered my virgin hole priming it for her next move. I knew what she wanted and I wanted it too.

She pulled out a condom and lube and asked if I was ready to be hers. I nodded and she told me she would go slow. She lubed up her cock and my hole and slowly tried to push the tip in, but I was too tight. So she told me to straddle her and lower myself onto her. I obeyed and slowly pushed the tip of her into me and maybe the first inch and a half, but it hurt and was splitting me open. I backed off and reattempted, but it would pop out. My cock was oozing precum from the thought of being fucked by this woman and I wanted it, but after about 15 minutes of trying it just wasn’t working. Don’t worry she said, there will be plenty of time to try again. So we continued to stroke and makeout and then I wanted to 69. We 69’d for about 15 minutes and she was getting close so I flipped her on her back and sucked and stroked her until she shot cum all over her stomach and breasts. Then she told me she wanted me to cum all over her face so I kneeled beside her while she sucked me and right as I was about to cum I pushed her back and jacked off until I sprayed a huge load all over her face and plump lips. I collapsed next to her cum covered body and we cleaned each other up. We laid and cuddled and talked for another hour or so, but due to the time being so late we both needed to get sleep for the following workday.

After a long parting kiss, I headed home. On the drive home I was able to reflect on what just happened with a clear head, and I absolutely loved it and knew that this was something I would be excited to experience again. Since that day I have seen her again and she still wants to be the first to take my ass and I love that thought. Also, in the last couple weeks I have met up with another girl and will have to share that story as well.

Source: reddit.com/r/gonewildstories/comments/ft84wx/mt_my_first_experience_with_a_trans_woman