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.

I parked on the street out front and there were many nice cars and it was a well lit neighborhood which is always a good sign. The house was a large modern house with a perfectly manicured lawn and a light on at the front door. She told me to text when I was there, and I complied. The door cracked open and in the dark shadows I saw a small framed, but cute blonde. I slipped in the door and she told me to be quiet – maybe she had roommates? I honestly didn’t care at this point. I followed her up a marble staircase and noticed unlike the first girl she was a little more boyish and less curvy, but had yoga pants and a zip up top on. We went to her room where she had candles and music on and she asked if I wanted to cuddle.

I hopped on her bed and she climbed in with me and assumed the little spoon position. I was a bit nervous since I’m sure she was going to feel my already hard cock pressing into her yoga pant covered ass. Well, she did feel it and she liked it because as we laid there talking she would slowly move her hips and rub her small ass up and down and further into my cock. Again, feeling much more confident I took this as a sign to make a move. I reached around and grabbed her head slowly turning it to meet my eyes and gave her a kiss. She let out a soft moan and kissed me back with her tongue going into my mouth. I love sloppy wet kisses and she was all for it. I gave her lip a bite and the moan got louder (maybe there aren’t roommates).

We continued to kiss and I rolled on top and she went for my ass immediately. Her hand was under my pants and boxer briefs pulling on each cheek and a finger grazed my tight hole. She also ran her hands under my shirt and in one motion pulled it over my head. I said that wasn’t fair and told her she needed to lose some clothes. She obliged and pulled her shirt off, but as I looked at her sitting over me in a bra I made a motion for her to lose that too. She popped it off to reveal small perky breasts with hard small nipples. I kissed her again deeply while pinching her nipples and noticed she loved the attention they got. So I went to licking and sucking them and she was dry humping any part of me she could. I pushed her into the bed and continued working her nipples and felt her hands frantically tugging my belt and fly open. She was cock hungry and flipped me on my back and pulled my pants and underwear down. She instantly was gagging and spitting on my rock hard cock and I was in heaven. After a few minutes I again reminded her that this wasn’t fair so she obeyed standing up and hooked her thumbs in her waistband revealing a little landing strip atop her rock hard 4.5” cut cock or “clit” she called it. I was on my knees on the wood floor sucking and licking her. While on my knees I put a hand between her legs and up to her ass and pushed it into my face taking her all. It was the perfect size for a beginner like me. I popped it out of my mouth and slowly stroked it looking up at her. She and I got back into the bed and she was on top and spit in her hand and slowly stroked our cocks together rubbing them and letting our precum lube each other up further. After 69ing for a bit she asked if I would fuck her pussy. She pulled out a condom, lube, and lube injector. She filled herself up as I put the condom on.

She then squatted over my cock and lowered herself onto it. It actually took a few minutes for her to get it in and another few to take it the whole way, but as she did she was oozing precum and I would tease her cock with my hand. She then bounced on my cock jamming it hard and deep into her and I knew what she liked. We switched positions a few times and she bent over the bed with her feet on the floor, pulled her ass apart, and told me to smash this pussy. I didn’t need to be asked twice and was plowing her as deep and hard as I could. I reached around and gave her…a…well…reach around while burying my cock deep inside. She got back on top and rode me for another 20 minutes while she continued to drip precum. She told me she wanted me to cum, and being a gentleman who loves to please I asked where and she said on her clit. I pulled out and pulled the condom off. The combination of the lube and the entire situation had me shooting ropes all over her cock and bush in seconds. She said good boy now watch this and used my cum as lube to finish herself off. She then took our cum in her hand and lifted it to her mouth savoring it, but before she swallowed I was kissing her deeply sharing one last taste of us.

After we cleaned up we cuddled and talked a little and she sent me on my way. I actually met up with her again but I didn’t ask her to fuck me yet and I think I’m going to next time because she’s the perfect size.

Source: reddit.com/r/gonewildstories/comments/fuou11/my_m_second_time_with_a_trans_woman_t