u/Dace66

Reading your stories turns me on so much. I thought it was my turn to return the favor and share mine… kind of…

Okay so preface… I guess this isn’t really a “first time” story but it kind of is. I’d been curious for a long time. Met a few trans women and gotten head or topped them. I did 69 with a couple of them and it was so hot.

Then progressed to meeting a few guys to JO and/or get head. One guy asked me to suck him, and I did but only for a few minutes then stopped. I had already cum and pnc set in and made me super anxious. I wonder what he’s doing out there… still live close and would be cool to link up with him again lol. But anyway…

So I’ve explored a bit here and there with penis owners, either trans women or other men. But nothing like this…

So a few months back I was horny and wanted a “massage”… well I found a local trans masseuse. I thought that would be amazing. I could explore more and while I wanted to cum I also wanted to enjoy another penis a bit lol.

So I go to get a “massage” and it starts off normal. I get there and she’s dressed super sexy and it’s clear that we both know what’s up even though our chat ahead of time had no mention of anything beyond a massage. She’s starts the massage and it’s great. I’m expecting that when she has me roll over the real fun would start… well before she gets there the fun starts (or maybe rushed into the fun starting? Idk…)

She’s massaging my back like normal then as she gets lower to do my legs she keeps kind of playing with my butt. Not just massaging but playing with it. Then stars to slide a finger (maybe more than one?..) down my crack. I instinctively spread my legs just a little bit it. And she started to rub my hole. I kind of pushed back on her hand but nothing crazy. The intent on my end was to adjust and flop my now hard cock out. Which I did… then she grabbed. When she grabbed it she told me to flip over.

While she was doing that she was standing on my side and close enough to the table and my hand that I could grab her. So I did. When I did rubbed her butt then slid my hand around and pulled her dick out of her panties. She was mostly hard, but not rock hard. But she was dripping precum. Like a geyser. It was so fucking sexy. It took everything I had in my not pull her over to the top of the table and lick it off. I have a major cum fetish. My own, hers, yours, the neighbors, it doesn’t matter lol

So I flipped over and she started rubbing my though and chest. Kind of rubbing my dick, but not jacking me off. She was kind of staring at it. She paused for a second and was just running her hand on my chest and says “you have a gorgeous cock. Can i suck it?”

I said “yes!!!!” And I asked her if I could suck her too. I could tell this was not a normal request for her and she said “you want to try and 69 on the table??” I said sure let’s try it…

I am a big oral pleaser. I love giving women head, 69 is one of my favorite things on the planet, but honestly I’d prefer a women just sitting or grinding on my face over 69 most days.

So we try it. She gets on top and we’re going it. It was not super comfortable for either of us squeezed on the small massage table. She had a chair in the room so we moved to the chair and sucked me off and I left. She didn’t cum and aside from me licking and sucking the precum off her I didn’t get to really taste her like I wanted.

I left and could not stop thinking about her. Like non-stop for a couple weeks. Thinking about fucking her and even thinking I could maybe bottom for her?!? Something I’d never ever considered with anyone else. She was not very big maybe slightly below average but not super small either. I thought maybe I could try it. And I could tell by how she was playing with my ass she wanted to fuck me.

I had never thought about getting ducked before. Never used a toy, never fingered myself, but a few people had slipped a single finger in while giving me a bj, but it was never something I looked forward to. But now I found myself hard and dripping thinking about this woman fucking me. Fantasizing about her fucking missionary and making me cum all over my own stomach and chest. I was soooo turned on for weeks.

Well I finally decided I needed to go back and see her and see how far I would be willing to go in the moment. So I did. I booked an appointment. Just like before, when I got there she was so sexy. I immediately undressed and laid down.

She rubbed my back for like 2 seconds before I basically grabbed her and pulled her dick out. I was salivating. I wanted it in my mouth so badly. So while she was rubbing my back I turned my head to the side and started sucking her.

She almost immediately slid her hands down to my ass. She was rubbing it, spreading my cheeks a little, and teasing my hole with her fingers. She got hard almost immediately and just like before her precum was flowing. It was delicious.

I asked her if she wanted to fuck. And she said “Yes!!” I could tell she wanted me and she could tell I really wanted her. She enjoyed playing with my ass and I could tell she liked my dick. (My dick is nice… very pretty slightly above average length and thick)

She asked me if I wanted to bend over the chair. I said “no, what if you fuck me while I’m on the table and you’re standing there” she said “wait really?” And I said “yes! I’ve been fantasizing about you fucking me ever since I saw you last.” She kind of chuckled and said something about me having a nice ass and her wanting it.

She put a condom on and lubed it up. I turned to the side and let her grab my legs. She basically put them over her shoulders. I felt completely powerless, but I a good way. (I don’t know if that makes any sense?..)

Well she slid it in very slowly but firmly. It hurt. Like a lot. My erection was gone in 1 second and I was flaccid. I asked her to stop, and she did. Just stood there. I kind of calmed down and came back to earth mentally. Then she started fucking me. At first slowly then speeding up as I got more comfortable. It wasn’t the biggest turn on ever in the moment but it was very hot.

I was not getting hard again, felt like it was not going to make me cum at all, and then it started hurting more and more as she was basically pounding away. Once she got comfortable with it and I kind of gave her the green light she was really fucking me. It hurt…

So I told her to stop and asked her if I could fuck her. She was all for it but I needed to get hard again. I wanted to take her condom off and suck her but I didn’t. Mostly because the condom wasn’t exactly clean coming out and I was immediately turned off by it…. (Sorry I’m sure that’s a bit of TMI…)

Well it was so weird…. I was still in pain and I was very much turned off… but as soon as she stated sucking me I basically exploded. One of the hardest and longest orgasms of my life. It felt like a ton of bricks when I came and it felt like the orgasm listed a year. It was incredible. I kind of wanted to try letting her fuck me again or sucking her but then pnc hit me hard and I basically ran away lol.

Well it’s been about a month now. And I’ve now been day dreaming about her fucking me again. This time I want to take it until she cums. I need it. I’m going to book the appointment. Maybe I’ll update you guys later lol.

Reading your stories turns me on so much. I thought it was my turn to return the favor and share mine… kind of…

Okay so preface… I guess this isn’t really a “first time” story but it kind of is. I’d been curious for a long time. Met a few trans women and gotten head or topped them. I did 69 with a couple of them and it was so hot.

Then progressed to meeting a few guys to JO and/or get head. One guy asked me to suck him, and I did but only for a few minutes then stopped. I had already cum and pnc set in and made me super anxious. I wonder what he’s doing out there… still live close and would be cool to link up with him again lol. But anyway…

So I’ve explored a bit here and there with penis owners, either trans women or other men. But nothing like this…

So a few months back I was horny and wanted a “massage”… well I found a local trans masseuse. I thought that would be amazing. I could explore more and while I wanted to cum I also wanted to enjoy another penis a bit lol.

So I go to get a “massage” and it starts off normal. I get there and she’s dressed super sexy and it’s clear that we both know what’s up even though our chat ahead of time had no mention of anything beyond a massage. She’s starts the massage and it’s great. I’m expecting that when she has me roll over the real fun would start… well before she gets there the fun starts (or maybe rushed into the fun starting? Idk…)

She’s massaging my back like normal then as she gets lower to do my legs she keeps kind of playing with my butt. Not just massaging but playing with it. Then stars to slide a finger (maybe more than one?..) down my crack. I instinctively spread my legs just a little bit it. And she started to rub my hole. I kind of pushed back on her hand but nothing crazy. The intent on my end was to adjust and flop my now hard cock out. Which I did… then she grabbed. When she grabbed it she told me to flip over.

While she was doing that she was standing on my side and close enough to the table and my hand that I could grab her. So I did. When I did rubbed her butt then slid my hand around and pulled her dick out of her panties. She was mostly hard, but not rock hard. But she was dripping precum. Like a geyser. It was so fucking sexy. It took everything I had in my not pull her over to the top of the table and lick it off. I have a major cum fetish. My own, hers, yours, the neighbors, it doesn’t matter lol

So I flipped over and she started rubbing my though and chest. Kind of rubbing my dick, but not jacking me off. She was kind of staring at it. She paused for a second and was just running her hand on my chest and says “you have a gorgeous cock. Can i suck it?”

I said “yes!!!!” And I asked her if I could suck her too. I could tell this was not a normal request for her and she said “you want to try and 69 on the table??” I said sure let’s try it…

I am a big oral pleaser. I love giving women head, 69 is one of my favorite things on the planet, but honestly I’d prefer a women just sitting or grinding on my face over 69 most days.

So we try it. She gets on top and we’re going it. It was not super comfortable for either of us squeezed on the small massage table. She had a chair in the room so we moved to the chair and sucked me off and I left. She didn’t cum and aside from me licking and sucking the precum off her I didn’t get to really taste her like I wanted.

I left and could not stop thinking about her. Like non-stop for a couple weeks. Thinking about fucking her and even thinking I could maybe bottom for her?!? Something I’d never ever considered with anyone else. She was not very big maybe slightly below average but not super small either. I thought maybe I could try it. And I could tell by how she was playing with my ass she wanted to fuck me.

I had never thought about getting ducked before. Never used a toy, never fingered myself, but a few people had slipped a single finger in while giving me a bj, but it was never something I looked forward to. But now I found myself hard and dripping thinking about this woman fucking me. Fantasizing about her fucking missionary and making me cum all over my own stomach and chest. I was soooo turned on for weeks.

Well I finally decided I needed to go back and see her and see how far I would be willing to go in the moment. So I did. I booked an appointment. Just like before, when I got there she was so sexy. I immediately undressed and laid down.

She rubbed my back for like 2 seconds before I basically grabbed her and pulled her dick out. I was salivating. I wanted it in my mouth so badly. So while she was rubbing my back I turned my head to the side and started sucking her.

She almost immediately slid her hands down to my ass. She was rubbing it, spreading my cheeks a little, and teasing my hole with her fingers. She got hard almost immediately and just like before her precum was flowing. It was delicious.

I asked her if she wanted to fuck. And she said “Yes!!” I could tell she wanted me and she could tell I really wanted her. She enjoyed playing with my ass and I could tell she liked my dick. (My dick is nice… very pretty slightly above average length and thick)

She asked me if I wanted to bend over the chair. I said “no, what if you fuck me while I’m on the table and you’re standing there” she said “wait really?” And I said “yes! I’ve been fantasizing about you fucking me ever since I saw you last.” She kind of chuckled and said something about me having a nice ass and her wanting it.

She put a condom on and lubed it up. I turned to the side and let her grab my legs. She basically put them over her shoulders. I felt completely powerless, but I a good way. (I don’t know if that makes any sense?..)

Well she slid it in very slowly but firmly. It hurt. Like a lot. My erection was gone in 1 second and I was flaccid. I asked her to stop, and she did. Just stood there. I kind of calmed down and came back to earth mentally. Then she started fucking me. At first slowly then speeding up as I got more comfortable. It wasn’t the biggest turn on ever in the moment but it was very hot.

I was not getting hard again, felt like it was not going to make me cum at all, and then it started hurting more and more as she was basically pounding away. Once she got comfortable with it and I kind of gave her the green light she was really fucking me. It hurt…

So I told her to stop and asked her if I could fuck her. She was all for it but I needed to get hard again. I wanted to take her condom off and suck her but I didn’t. Mostly because the condom wasn’t exactly clean coming out and I was immediately turned off by it…. (Sorry I’m sure that’s a bit of TMI…)

Well it was so weird…. I was still in pain and I was very much turned off… but as soon as she stated sucking me I basically exploded. One of the hardest and longest orgasms of my life. It felt like a ton of bricks when I came and it felt like the orgasm listed a year. It was incredible. I kind of wanted to try letting her fuck me again or sucking her but then pnc hit me hard and I basically ran away lol.

Well it’s been about a month now. And I’ve now been day dreaming about her fucking me again. This time I want to take it until she cums. I need it. I’m going to book the appointment. Maybe I’ll update you guys later lol.