Great experience with a trans woman and made a new friend...

jasondub

Experienced
Joined
Aug 6, 2010
Posts
78
I travel regularly, mostly up and down the west coast. I occasionally try to meet up with interesting people during my travels and had a great experience recently that I felt compelled to share. Feedback/discussion welcome...


We had been chatting on and off over a few months and when I got into town started chatting again. We exchanged a few pics and were definitely into each other, she is kind, sweet, sane, funny. She particularly liked that I was tall, masculine and open to bottoming. I was only staying 1 night but the timing wasn't great, she already had plans for dinner with friends. I told her I'd just be out having a drink and if she got done with her dinner to let me know, it would be great to meet up.

Fast forward a couple of hours, she texted me and we discussed getting together for just a drink - no expectations. After we agreed on the ground rules she invited me over - I showered, bought some bourbon (her favorite drink) and uber'd over.

When she opened the door I was immediately put at ease - she was pretty and was exactly who she presented herself to be - about 5'8, 120lbs, asian, non-op, very feminine. We went up to her 3rd floor walk-up above a bar.

She lives in a little studio apartment so we sat at the small table in the kitchen area sipping bourbon getting to know each other better. She offered some weed and we smoked a little. We got a little flirty and started kissing. After a bit she invited me to sit on her bed with her and we started kissing.

I unbuttoned her blouse and sucked on her little nipples which she definitely liked. I then made my way down her tummy to her pants and could tell she was turned on but then she stood up. I thought she was going to tell me we needed to stop. However, she started unbuttoning her jeans, pulled them down a bit, then sat down back on the bed and asked me to pull them off for her.

Once her pants were off I saw her pretty, delicate black lacy panties only sightly hiding her erect 5". She told me to pull them down, which I gladly did and started licking her clit/cock - she moaned in response. She was very directive on what she wanted/liked, and I eagerly pleased her. I sucked her while she laid down, on my knees while she stood and then she positioned us 69 and ate my ass while I continued to suck her. Then she repositioned me on my back, put herself between my legs and stroked both our cocks at the same time. All the while talking dirty to me. Super hot!

We were both really turned on but she asked me to wait for a minute and left the room - she returned with a condom and lube. She put on the condom, lubed it up and then lubed me up as well. I put myself on all 4's and she was behind me beginning to enter me. I don't have a lot of experience so I really tried to relax. I asked her to use more lube and then she started to enter me slowly, taking her time. She pushed a little into me, and I pushed back a little adjusting the angle of my hips to make it more comfortable. Once she was in it felt incredible.

She was gentle at first and then started picking up momentum. Surprisingly it didn't hurt at all, it helped that she wasn't that big. She had me ride her and then had me on my back. As she fucked me I was stroking my cock. She was going faster and faster so I picked up the pace myself.

We were both really loud, the noise from the bar below helped to drown out the noise we were making. She came first and then I did. She slowly pulled out, pulled off her condom and threw it in the trash. I excused myself to clean up a bit and then returned to the bed to cuddle with her a bit. After about 20 minutes of talking and kissing I told her I needed to go. We kissed goodbye and promised to get together the next time I was in town.

I went back to my hotel, showered and went to bed - I slept great! We have continued to exchange text messages and looking forward to my next trip.
 
A fantasy of mine

Very hot. This has long been a fantasy of mine. I would love to experience such an event.
 
I travel regularly, mostly up and down the west coast. I occasionally try to meet up with interesting people during my travels and had a great experience recently that I felt compelled to share. Feedback/discussion welcome...


We had been chatting on and off over a few months and when I got into town started chatting again. We exchanged a few pics and were definitely into each other, she is kind, sweet, sane, funny. She particularly liked that I was tall, masculine and open to bottoming. I was only staying 1 night but the timing wasn't great, she already had plans for dinner with friends. I told her I'd just be out having a drink and if she got done with her dinner to let me know, it would be great to meet up.

Fast forward a couple of hours, she texted me and we discussed getting together for just a drink - no expectations. After we agreed on the ground rules she invited me over - I showered, bought some bourbon (her favorite drink) and uber'd over.

When she opened the door I was immediately put at ease - she was pretty and was exactly who she presented herself to be - about 5'8, 120lbs, asian, non-op, very feminine. We went up to her 3rd floor walk-up above a bar.

She lives in a little studio apartment so we sat at the small table in the kitchen area sipping bourbon getting to know each other better. She offered some weed and we smoked a little. We got a little flirty and started kissing. After a bit she invited me to sit on her bed with her and we started kissing.

I unbuttoned her blouse and sucked on her little nipples which she definitely liked. I then made my way down her tummy to her pants and could tell she was turned on but then she stood up. I thought she was going to tell me we needed to stop. However, she started unbuttoning her jeans, pulled them down a bit, then sat down back on the bed and asked me to pull them off for her.

Once her pants were off I saw her pretty, delicate black lacy panties only sightly hiding her erect 5". She told me to pull them down, which I gladly did and started licking her clit/cock - she moaned in response. She was very directive on what she wanted/liked, and I eagerly pleased her. I sucked her while she laid down, on my knees while she stood and then she positioned us 69 and ate my ass while I continued to suck her. Then she repositioned me on my back, put herself between my legs and stroked both our cocks at the same time. All the while talking dirty to me. Super hot!

We were both really turned on but she asked me to wait for a minute and left the room - she returned with a condom and lube. She put on the condom, lubed it up and then lubed me up as well. I put myself on all 4's and she was behind me beginning to enter me. I don't have a lot of experience so I really tried to relax. I asked her to use more lube and then she started to enter me slowly, taking her time. She pushed a little into me, and I pushed back a little adjusting the angle of my hips to make it more comfortable. Once she was in it felt incredible.

She was gentle at first and then started picking up momentum. Surprisingly it didn't hurt at all, it helped that she wasn't that big. She had me ride her and then had me on my back. As she fucked me I was stroking my cock. She was going faster and faster so I picked up the pace myself.

We were both really loud, the noise from the bar below helped to drown out the noise we were making. She came first and then I did. She slowly pulled out, pulled off her condom and threw it in the trash. I excused myself to clean up a bit and then returned to the bed to cuddle with her a bit. After about 20 minutes of talking and kissing I told her I needed to go. We kissed goodbye and promised to get together the next time I was in town.

I went back to my hotel, showered and went to bed - I slept great! We have continued to exchange text messages and looking forward to my next trip.
What a wonderful encounter. So happy for you!
 
I think many guys fantasize about that sort of thing. Lucky for you that you were able to live it out - and enjoyed it.
 
Yep, that's super-hot and would be a dream situation for me. Especially the fact that she was very feminine, but took the lead and wanted to fuck you.
 
Back to SF next week...

Looking forward to meeting up with my new friend again ;-).
 
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