First Time Bottoming

[ChasingCouple]

Hi, everyone. This is my first post. I've been writing these stories for myself for sometime and some reason it just occurred to me that they may be welcome here. I'll share one and see how it goes. Thanks for having me!

Larizza is a special memory for me. She was my first T-girl experience that actually worked out. I had been with two t-girls before Larizza, but things didn't quite live up to my fantasies. With the first one I chickened out and didn't do very much (maybe I'll tell you about that one, one day). With the second... I was in an area with very few TS escorts and the provider was a total turn-off. That experience was terrible for a bunch of reasons including being rushed, the motel room being filthy, etc.

Determined not to get burned again I did a ton of research for the Boston area. I went there occasionally for work and decided to use my next opportunity to fulfill this fantasy and do it right. I spent hours pouring over TER reviews and Larizza was one of the most highly-reviewed TSs in the city (she was in close competition with another one I might talk about on another day, TS Lavinia)(if you remember those two in Boston you can probably get a rough idea of the time frame). I followed her for a long time before I finally made a move. As soon as my trip was confirmed I called her and scheduled and incall (her place) visit.

I contacted Larizza and planned a meetup for my first night in town so if something came up I could always reschedule for the next night, or schedule with the other top girl in Boston. Turns out none of that was needed - I met up with her as planned and I couldn't have found a better introduction to this world. I spent a good two hours getting ready for our appointment - I wanted to make sure I was completely clean and comfortable to let whatever was going to happen happen.

I left early to get to her area and was there way early. I killed a little time before calling her. When I did she gave me instructions on how to get to her apartment. It involved a gate, a code, and a quiet knock on the door. She immediately opened the door and hustled me in, presumably so the neighbors wouldn't see me. She had a beautiful face, lovely brown eyes, and long black hair. She was absolutely gorgeous. After a big hug she stood back, turned, and led me to the bedroom. Her apartment was immaculate - a very clean, modern two-bedroom unit. The bedroom itself featured a big king bed that had been freshly made. So far so good.

She was dressed casually - jeans and a cute little t-shirt. We sat down on the edge of the bed. She asked me if I'd ever done this kind of thing and, "have you ever been with a girl like me?" I told her I hadn't. She asked me what I wanted to have happen. I was very shy about saying it out loud but told her what I wanted.

Finally I forced it out and I remember being very specific: "I want you to fuck me, facing me."

"Why do you want me facing you?"

"So I can see you," I said. "You're so pretty I want to see you." As cheesy as that sounded it was true; I was very into how beautiful she was. If I'm being honest with myself I was also probably somewhat insecure and needing to see that I was with a woman while I was being penetrated. I think we probably handled the donation at that point, too. She said she'd be right back, told me to get comfortable, and left the room.

I stripped down to boxer briefs. It was that awkward moment of waiting, trying to be comfortable, but being very anxious - that weird, awesome combination of nervous excitement that I sometimes miss. When she came back she was wearing the t-shirt and a red thong. Though the t-shirt was still on I could tell she had taken her bra off.

She was so attractive and feminine - I even looked for a bulge in her panties but didn't see one - that I literally remember thinking, "did I book a 'regular' girl by mistake?" She straddled me and leaned over for some light French kissing. I pushed my hips up to grind my cock on...whatever was between her legs. She sat back on me and pulled her shirt off to reveal these amazing, beautiful tits.

Finally she moved up, still straddling me, with the crotch of her red thong right in my face. She pulled the it aside and there it was - a limp dick and a big set of balls, all silky smooth. I distinctly remember this brief panic moment, then thinking, “well, it’s what I’m here for.” I reached up and grabbed her soft cock, held it straight out, and moved my mouth toward it. I remember crossing that line, but I honestly don’t remember too much about the first time I put her cock in my mouth.

I was so nervous/anxious/excited and I was totally turned on... but also slightly grossed out. My eyes were closed and I doubt I did a very good job. After a couple minutes, though, she pushed my head back onto the pillow and her cock sprang out of my mouth, rock hard, big, and with a slight upward curve. It was glistening with my saliva and I remember this moment of excitement thinking, “holy shit! She got hard in my mouth! I got her hard!” I was really getting into it now.

She got off of me, moving to my right side, sitting back on her knees on the bed, leaning back and propping herself on her arms. That was one of the most amazing sights I’ve seen, sexually. I have this realization that I'm in a room with an absolutely beautiful Brazilian woman with some of the best boobs I've ever seen, and she certainly seems to want me. Oh, and she has a cock. And it's so hard it's pointing straight up at the ceiling. And she's looking at me, waiting for me to do finish what I started.

Her cock wasn't huge - maybe 6 or 6.5" long, average thickness, with a slight upward curve. Though not massive it was still about the perfect size. It was the ideal size to start on - a little challenging but doable - and about the size I prefer now when I really want to get fucked long and hard. It had a uniform girth from the tip all the way back to the base, and everything was perfectly smooth. She was cut and had a very well-defined head.

I sat up and faced her. I kissed her briefly, then started at her boobs. I kissed them, sucked her nipples, and kissed my way back down to that dick. I was still a bit awkward about it but I was determined to get back down there and spend some time doing what I came here to do.

Being so inexperienced I kind of wanted to play around a bit. Just touching another person's dick was a very strange feeling. I stroked her a little, then lowered myself licked the underside of her shaft up and down several times. I licked around the head and pulled back several times just to look at it. Then I slid it back in my mouth. I know my head-game was nothing special but I did the best I could and loved running my tongue over her smooth, warm erection.

Finally she asked if I was ready. I was as ready as I was going to get. She told me to lie down. I lay on my back, and she bent down and sucked my cock for a minute. Then she got up, walked to the side of the bed, and pulled a condom out of the bedside table. I watched her roll the condom onto herself, apply a healthy dose of lube, then get back on the bed and come toward me with a bottle of lube in her hand.

She squirted some on her fingers and rubbed it on my asshole. This was one of the very few times another human being had touched my asshole to that point, and she wasn't being shy about it. It was a very strange feeling. When she was finally ready she pushed her cock down to a horizontal angle and aligned it with my ass. She rubbed the tip against me, up and down, getting me used to the sensation. Then I felt some pressure.

I felt it coming, I wanted it. It sort of popped in all at once - not the whole length, just the head - but holy shit it was painful. I asked her to stop, then to pull out. She was so patient with me. It was this intense burning sensation. I lay there a few minutes and pretty soon it completely went away. I had experienced this before with toys when I was getting ready for tonight. I knew this was just the result of going too fast. I told her I needed to go more slowly.

She told me to get on my hands and knees at the end of the bed. She stood at the edge of the bed and we started over. I felt that familiar pressure, but she went very, very slowly. It seemed to be taking long time and I couldn't tell what, if anything, was happening. I must've seemed curious because she said, "it's almost all the way in."

"Really?" I asked, genuinely surprised. It sure hadn't felt like it. But when I clenched my ass...yep, there was this thick, rigid foreign object. She just kept applying lube, and kept doing what she was doing until I felt her thighs against firmly against me. Then she held it there, leaned forward until I felt her tits on my back and asked how I was doing.

"Good!" I said,

"Are you ready?" she asked.

"I think so, just go slow."

"Oh I will, baby." And she did. I felt it start sliding out of me. Just moving her hips and nothing else - her chest firmly against my back. I tried not to clench, and just relax and let this happen. Then back in it came, slowly but assertively. Again. Again. Again. Each time just a little faster. Finally she stood back up and I felt her hands on my hips. I pushed myself up which naturally arched my back and suddenly her slow thrusts felt amazing.

"There we go," she said. Then she actually fucked me. Just a good steady rhythm, in and out. I didn't get pounded or anything like that...but she definitely fucked me. A steady in and out, in and out, in and out. It was still very foreign to me but I was starting to relax into it. Or "onto" it, as it were. She stopped and asked if I wanted to turn over. I did.

We got back on the bed as we had been before: me on my back, her on her knees between my legs. Again, she lubed me up. This time it slipped right in with very little resistance. I could feel it plunging into me. I finally hit a point where I was actually enjoying it and not merely tolerating it. It hit a certain point where it felt really, really good - like nothing else. As she was fucking me she was stroking my cock with her lubed hand. I had to stop her several times because I was very close to cumming and wasn't ready for this to end just yet. While on my back I reached down and felt her cock. I ran a finger around the ring of my stretched asshole, feeling her dick sliding in and out. I touched her cock, and even reached my hand under and lightly touched her balls. I could have stayed right there forever...but I told her I wanted to get on top of her.

She was so willing. She immediately rolled over onto her back beside me. There she is, on her back, that cock sticking up from her body with a condom on it. I wanted to take an active part in this. Rather than laying back just getting fucked, I wanted to do it to know that I could do it and prove to myself that I actually wanted it. I straddled her. I reached behind me and took her cock in my hand. It was so slick with lube. I raised it up until I found my asshole...and just sat on it. It slid in all the way to the hilt.

The sensation this time was a little different, just becasue of the angle, but it still felt amazing. This awesome, full, warm feeling. There was no getting used to it this time, I already was used to it. I immediately tried to show her how enthusiastic I was to ride that dick.

It took me a second to get rhythm of riding her down - it slid out a couple times when I pulled up too far, but I eventually did. I slowed down, payed attention to the amazing feeling it was producing, and I rode her. But not for very long. She was still stroking me and I was getting close. It felt so good I just let it go. I shot a very big, thick, white load on her right boob. I came with her still inside me which is such a weird and different type of orgasm. It was actually a bit less intense because my brain didn't know which cock to focus on - mine or the one in my asshole.

Before I actually did this I kind of expected to be grossed out by the situation as soon as I busted. Often when watching porn there was some immediate self-loathing that followed directly on the heels of an orgasm. But I wasn't. She had been so amazing that I was sorry it ended. We sat there for just a couple of minutes, me straddling her, her sheathed cock inside me, before she told me where the bathroom was. I gently eased myself off of her.

When I came out of the bathroom she was lying on the bed, still naked. I sat down on the edge of the bed and we chatted. She told me she was going to go to a club. The way she lay back and lazily stretched her arms over her head made her tits look so amazing...I still wonder if she was horny and trying to catch my eye. I often fantasize about what would have happened if I'd complimented her tits or asked if she wanted to cum.

But I didn't. I got dressed and left and that was the last time I saw her. She was such a gem. I got so lucky. She was gorgeous, good at what she did and so patient. I'm sure she'd done this with a million clients, but during the whole thing she just kept smiling at me, asking how I was doing, asking how it felt, asking what I wanted. She was the ultimate transexual for a first-timer. I saw a couple other trans escorts in Boston, but never Larizza again. I don’t know why - I just followed the appeal for something new. Just about everyone else was a letdown and immediately made me wish I’d gone back to her.

[rhh33]

Hi, everyone. This is my first post. I've been writing these stories for myself for sometime and some reason it just occurred to me that they may be welcome here. I'll share one and see how it goes. Thanks for having me!

Larizza is a special memory for me. She was my first T-girl experience that actually worked out. I had been with two t-girls before Larizza, but things didn't quite live up to my fantasies. With the first one I chickened out and didn't do very much (maybe I'll tell you about that one, one day). With the second... I was in an area with very few TS escorts and the provider was a total turn-off. That experience was terrible for a bunch of reasons including being rushed, the motel room being filthy, etc.

Determined not to get burned again I did a ton of research for the Boston area. I went there occasionally for work and decided to use my next opportunity to fulfill this fantasy and do it right. I spent hours pouring over TER reviews and Larizza was one of the most highly-reviewed TSs in the city (she was in close competition with another one I might talk about on another day, TS Lavinia)(if you remember those two in Boston you can probably get a rough idea of the time frame). I followed her for a long time before I finally made a move. As soon as my trip was confirmed I called her and scheduled and incall (her place) visit.

I contacted Larizza and planned a meetup for my first night in town so if something came up I could always reschedule for the next night, or schedule with the other top girl in Boston. Turns out none of that was needed - I met up with her as planned and I couldn't have found a better introduction to this world. I spent a good two hours getting ready for our appointment - I wanted to make sure I was completely clean and comfortable to let whatever was going to happen happen.

I left early to get to her area and was there way early. I killed a little time before calling her. When I did she gave me instructions on how to get to her apartment. It involved a gate, a code, and a quiet knock on the door. She immediately opened the door and hustled me in, presumably so the neighbors wouldn't see me. She had a beautiful face, lovely brown eyes, and long black hair. She was absolutely gorgeous. After a big hug she stood back, turned, and led me to the bedroom. Her apartment was immaculate - a very clean, modern two-bedroom unit. The bedroom itself featured a big king bed that had been freshly made. So far so good.

She was dressed casually - jeans and a cute little t-shirt. We sat down on the edge of the bed. She asked me if I'd ever done this kind of thing and, "have you ever been with a girl like me?" I told her I hadn't. She asked me what I wanted to have happen. I was very shy about saying it out loud but told her what I wanted.

Finally I forced it out and I remember being very specific: "I want you to fuck me, facing me."

"Why do you want me facing you?"

"So I can see you," I said. "You're so pretty I want to see you." As cheesy as that sounded it was true; I was very into how beautiful she was. If I'm being honest with myself I was also probably somewhat insecure and needing to see that I was with a woman while I was being penetrated. I think we probably handled the donation at that point, too. She said she'd be right back, told me to get comfortable, and left the room.

I stripped down to boxer briefs. It was that awkward moment of waiting, trying to be comfortable, but being very anxious - that weird, awesome combination of nervous excitement that I sometimes miss. When she came back she was wearing the t-shirt and a red thong. Though the t-shirt was still on I could tell she had taken her bra off.

She was so attractive and feminine - I even looked for a bulge in her panties but didn't see one - that I literally remember thinking, "did I book a 'regular' girl by mistake?" She straddled me and leaned over for some light French kissing. I pushed my hips up to grind my cock on...whatever was between her legs. She sat back on me and pulled her shirt off to reveal these amazing, beautiful tits.

Finally she moved up, still straddling me, with the crotch of her red thong right in my face. She pulled the it aside and there it was - a limp dick and a big set of balls, all silky smooth. I distinctly remember this brief panic moment, then thinking, “well, it’s what I’m here for.” I reached up and grabbed her soft cock, held it straight out, and moved my mouth toward it. I remember crossing that line, but I honestly don’t remember too much about the first time I put her cock in my mouth.

I was so nervous/anxious/excited and I was totally turned on... but also slightly grossed out. My eyes were closed and I doubt I did a very good job. After a couple minutes, though, she pushed my head back onto the pillow and her cock sprang out of my mouth, rock hard, big, and with a slight upward curve. It was glistening with my saliva and I remember this moment of excitement thinking, “holy shit! She got hard in my mouth! I got her hard!” I was really getting into it now.

She got off of me, moving to my right side, sitting back on her knees on the bed, leaning back and propping herself on her arms. That was one of the most amazing sights I’ve seen, sexually. I have this realization that I'm in a room with an absolutely beautiful Brazilian woman with some of the best boobs I've ever seen, and she certainly seems to want me. Oh, and she has a cock. And it's so hard it's pointing straight up at the ceiling. And she's looking at me, waiting for me to do finish what I started.

Her cock wasn't huge - maybe 6 or 6.5" long, average thickness, with a slight upward curve. Though not massive it was still about the perfect size. It was the ideal size to start on - a little challenging but doable - and about the size I prefer now when I really want to get fucked long and hard. It had a uniform girth from the tip all the way back to the base, and everything was perfectly smooth. She was cut and had a very well-defined head.

I sat up and faced her. I kissed her briefly, then started at her boobs. I kissed them, sucked her nipples, and kissed my way back down to that dick. I was still a bit awkward about it but I was determined to get back down there and spend some time doing what I came here to do.

Being so inexperienced I kind of wanted to play around a bit. Just touching another person's dick was a very strange feeling. I stroked her a little, then lowered myself licked the underside of her shaft up and down several times. I licked around the head and pulled back several times just to look at it. Then I slid it back in my mouth. I know my head-game was nothing special but I did the best I could and loved running my tongue over her smooth, warm erection.

Finally she asked if I was ready. I was as ready as I was going to get. She told me to lie down. I lay on my back, and she bent down and sucked my cock for a minute. Then she got up, walked to the side of the bed, and pulled a condom out of the bedside table. I watched her roll the condom onto herself, apply a healthy dose of lube, then get back on the bed and come toward me with a bottle of lube in her hand.

She squirted some on her fingers and rubbed it on my asshole. This was one of the very few times another human being had touched my asshole to that point, and she wasn't being shy about it. It was a very strange feeling. When she was finally ready she pushed her cock down to a horizontal angle and aligned it with my ass. She rubbed the tip against me, up and down, getting me used to the sensation. Then I felt some pressure.

I felt it coming, I wanted it. It sort of popped in all at once - not the whole length, just the head - but holy shit it was painful. I asked her to stop, then to pull out. She was so patient with me. It was this intense burning sensation. I lay there a few minutes and pretty soon it completely went away. I had experienced this before with toys when I was getting ready for tonight. I knew this was just the result of going too fast. I told her I needed to go more slowly.

She told me to get on my hands and knees at the end of the bed. She stood at the edge of the bed and we started over. I felt that familiar pressure, but she went very, very slowly. It seemed to be taking long time and I couldn't tell what, if anything, was happening. I must've seemed curious because she said, "it's almost all the way in."

"Really?" I asked, genuinely surprised. It sure hadn't felt like it. But when I clenched my ass...yep, there was this thick, rigid foreign object. She just kept applying lube, and kept doing what she was doing until I felt her thighs against firmly against me. Then she held it there, leaned forward until I felt her tits on my back and asked how I was doing.

"Good!" I said,

"Are you ready?" she asked.

"I think so, just go slow."

"Oh I will, baby." And she did. I felt it start sliding out of me. Just moving her hips and nothing else - her chest firmly against my back. I tried not to clench, and just relax and let this happen. Then back in it came, slowly but assertively. Again. Again. Again. Each time just a little faster. Finally she stood back up and I felt her hands on my hips. I pushed myself up which naturally arched my back and suddenly her slow thrusts felt amazing.

"There we go," she said. Then she actually fucked me. Just a good steady rhythm, in and out. I didn't get pounded or anything like that...but she definitely fucked me. A steady in and out, in and out, in and out. It was still very foreign to me but I was starting to relax into it. Or "onto" it, as it were. She stopped and asked if I wanted to turn over. I did.

We got back on the bed as we had been before: me on my back, her on her knees between my legs. Again, she lubed me up. This time it slipped right in with very little resistance. I could feel it plunging into me. I finally hit a point where I was actually enjoying it and not merely tolerating it. It hit a certain point where it felt really, really good - like nothing else. As she was fucking me she was stroking my cock with her lubed hand. I had to stop her several times because I was very close to cumming and wasn't ready for this to end just yet. While on my back I reached down and felt her cock. I ran a finger around the ring of my stretched asshole, feeling her dick sliding in and out. I touched her cock, and even reached my hand under and lightly touched her balls. I could have stayed right there forever...but I told her I wanted to get on top of her.

She was so willing. She immediately rolled over onto her back beside me. There she is, on her back, that cock sticking up from her body with a condom on it. I wanted to take an active part in this. Rather than laying back just getting fucked, I wanted to do it to know that I could do it and prove to myself that I actually wanted it. I straddled her. I reached behind me and took her cock in my hand. It was so slick with lube. I raised it up until I found my asshole...and just sat on it. It slid in all the way to the hilt.

The sensation this time was a little different, just becasue of the angle, but it still felt amazing. This awesome, full, warm feeling. There was no getting used to it this time, I already was used to it. I immediately tried to show her how enthusiastic I was to ride that dick.

It took me a second to get rhythm of riding her down - it slid out a couple times when I pulled up too far, but I eventually did. I slowed down, payed attention to the amazing feeling it was producing, and I rode her. But not for very long. She was still stroking me and I was getting close. It felt so good I just let it go. I shot a very big, thick, white load on her right boob. I came with her still inside me which is such a weird and different type of orgasm. It was actually a bit less intense because my brain didn't know which cock to focus on - mine or the one in my asshole.

Before I actually did this I kind of expected to be grossed out by the situation as soon as I busted. Often when watching porn there was some immediate self-loathing that followed directly on the heels of an orgasm. But I wasn't. She had been so amazing that I was sorry it ended. We sat there for just a couple of minutes, me straddling her, her sheathed cock inside me, before she told me where the bathroom was. I gently eased myself off of her.

When I came out of the bathroom she was lying on the bed, still naked. I sat down on the edge of the bed and we chatted. She told me she was going to go to a club. The way she lay back and lazily stretched her arms over her head made her tits look so amazing...I still wonder if she was horny and trying to catch my eye. I often fantasize about what would have happened if I'd complimented her tits or asked if she wanted to cum.

But I didn't. I got dressed and left and that was the last time I saw her. She was such a gem. I got so lucky. She was gorgeous, good at what she did and so patient. I'm sure she'd done this with a million clients, but during the whole thing she just kept smiling at me, asking how I was doing, asking how it felt, asking what I wanted. She was the ultimate transexual for a first-timer. I saw a couple other trans escorts in Boston, but never Larizza again. I don’t know why - I just followed the appeal for something new. Just about everyone else was a letdown and immediately made me wish I’d gone back to her.

We always remember the good ones! Thanks for sharing.