[MT] Picking up where we left off

After waiting for what felt like an eternity (10 months in pandemic time feels like 10 years) I was finally able to see my FWB again, and she did not disappoint.

As I approached her place and stepped towards the front door I had the same familiar butterflies I got each time we hung out. “What if she doesn’t like me the same as before?” She must have been waiting right near the door as there was nearly zero delay between my knock and the door opening.

“There’s my boy” she said in her strong, but feminine voice. We both stood there as if to take each other in and erase the anticipation of the last 10 months. As we stared into each other’s eyes we instantly locked lips, and our tongues were in each other’s mouths shortly after. She was only wearing a thin silk slip and as we stood there making out I pulled her against me to feel her already hard cock shielded by a thin layer of fabric pressing against me. We continued to makeout and moved towards the couch to sit down. I slowly kissed her neck and collarbone and bit the lobe of her ear. I slowly ran a finger from her knees up her inner thigh and to her waist. She let out a soft moan and slowly opened her knees.

My [M] second time with a trans woman [T]

This is a true story, and is a follow up to my first time with a different trans woman.

I couldn’t get the thoughts out of my head through the days and weeks following my first time. I wasn’t ashamed or turned off, and wanted to explore this new side of things again and further if possible.

With a newfound confidence in myself I reached out to someone I had liked on an app and we got to chatting. It wasn’t too late on a Friday evening so talk of the approaching weekend came up, and she actually didn’t want to beat around the bush and invited me over that evening. Now that I had gotten rid of the first time jitters I felt a little more comfortable and knew what to expect. I again showered, cleaned myself, brushed my teeth and got dressed. She sent me her address and said to come over around 11.

I checked the address she sent on google maps and it was a super nice house in a rather upscale neighborhood near me which again helped ease the pressure. On the drive over she send a pic of herself in black panties and a bra and said she hoped I didn’t mind if she wore “comfy” clothes. This again enticed me to not back out or feel afraid of what was to come.

[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.