My first time with a trans woman [MF]

So as the title says this is the story about my first sexual experience with a male to female transsexual, so if that isn’t your thing I’d recommend not reading this story. I’ll call her Megan. Also if I say anything that isn’t the correct term or you find offensive I apologise, I’m not 100% clued up on all of this, so just leave a comment or dm me if I say anything wrong. I’ll try and remember to refer to her penis as her clit, and her asshole as her pussy because that’s what she liked me to call them at the time.

I first met Megan on a dating app and instantly saw how gorgeous she was, she had shoulder length brown hair and piercing green eyes. Nice plump lips and a cute button nose. She was about 5’4 and very petite, her legs and bum were nice and toned from working out and her boobs were about 34C and looked very natural. Obviously I was very interested in her when I first seen her profile and had to message her. I honestly didn’t expect a reply as I thought she was way out of my league, but to my reply she messaged me back within 5 minutes. We chatted on the dating app before moving to WhatsApp.

Her first message to me on WhatsApp was to tell me that she is actually trans, it caught me off guard as there was nothing on her profile saying that and you’d never guess by looking at her. It took me a few more messages or her explaining everything but I decided that I enjoyed talking to her and I found her really attractive so I should keep talking to her. I won’t bore you with every little detail of our conversation but eventually things got dirty between us and we started sexting. I learned that she was actually a virgin as she was worried what people would think of her, I reassured her that she was gorgeous and she’d have a queue of men who would find her attractive. I also found out that she was pre surgery so she hadn’t had the operation on her genitals yet. I asked her what she liked to call her genitals and she said that she calls her penis a clit, and her asshole her pussy. So we spent that night with me telling her how to play with her clit and her pussy. We spent a few weeks of talking and making each other cum over the phone before she said that she wanted to meet me. I’d be lying if I said I wasn’t a little nervous.

We planned to meet on the Friday and I said she could stay at mine for the weekend as I have my own place. So Friday comes around and I get up early and tidy up and go get some food and drinks and wait around nervously. Eventually I get a call from Megan telling me she’s outside and I get up, dry my sweaty hands on my jeans and open the front door to be greeted by one of the best looking women I’ve ever seen. She looked even better in person and it took me slightly off guard, I composed myself and we greeted each other with a hug and I took her bag and led her into my house.

I’d be lying if I said the first few minutes weren’t a bit awkward, but after a bit of small talk we both calmed down and started laughing and joking with each other as we’d don’t countless times over the phone. I got us some drinks and we sat on the sofa and looked for a film to watch together, we ended up picking the shining as neither of us had seen it before. We spent the first 20 minutes just watching the film but Megan cuddled up to me and I wrapped my arm around her and held her tight. She felt so petite in my arms. She grabbed the blanket that was over the back of the sofa and threw it over us and rested her head on my shoulder as I planted a light kiss on the top of her head.

We sat like that watching the film for the next hour or so, before I felt her leg lightly rubbing up and down against my leg as I saw her out the corner of my eye look up at me. I looked back down at her and we held eye contact for a few seconds, before I leant down towards her and planted a soft kiss on her lips. Again we held eye contact as I leant down towards her again and kissed her again, holding the kiss for a few seconds this time. Her leg was rubbing against my dick through my jeans as I heard her breathe slightly heavier. I ran my hand up her leg until I reached her ass and gave it a firm squeeze, as Megan let out the cutest moan I’ve ever heard. This stirred me up slightly and I kissed her a third time, letting my mouth open as we kissed passionately while I squeezed and rubbed her ass. I pulled her up onto me so she was sat straddling my lap.

I squeezed her ass with both hands as she grinding slightly on my lap, letting out an occasional little moan. Again we held eye contact, ‘are you sure you want to do this?’ I asked as she bit her lip slightly and nodded. I pulled her towards me and me kissed passionately once more, our tongues wrestling as she grinded against my now rock hard dick. She had one hand on the side of my face and the other rubbing my chest as we kissed. She worked both her hands down to the bottom of my shirt and lifted up above my head as she pulled her lips off mine. I’d say I’m in fairly good shape but seeing her eyes light up at the site of my body definitely helped my ego, she ran her little hands over my chest and the down to my abs. I just watched her as her eyes followed her hand, seeing how much she enjoyed touching my body. She leant forward and planted soft kisses all over my chest before making her way to my nipple, I’ve never had my nipples licked and sucked but it felt surprisingly good. She kissed one softly, and then the other, before licking them softly, circling them with her tongue. She went back and forth between my nipples before looking back at me and smiling.

I quickly pulled her top up off over her head, exposing her beautiful perky tits to me, you’d never question if they were real or not. I grabbed both of her hands and held them together behind her back, causing her to push her tits out even more, gasping and then smiling as I done so. I leant forward and kissed one of her rock hard nipples softly and then looked up at her, she was watching me intently and biting her lip. I kissed her other nipple this time, letting my mouth wrap around it for a second. I went back and forth between her nipples, kissing them softly and teasing her a little. She was breathing heavier with every soft kiss, ‘suck on them, please’ I heard her breathily ask me. I looked up at her and smiled before wrapping my lips around her nipple and sucking on it as my hand squeezed her other boob. I felt her hand on the back of my head, pushing me slightly in her boob. I sucked a little harder before switching to the other nipple, I’m not even sure how long I spent sucking and licking her nipples, I just enjoyed her soft little moans. Megan spoke and broke me out of the trance I was in, ‘I want to suck you’ she said quietly, as if she was a little nervous. I pulled away from her nipples and looked at her, ‘are you sure?’ I asked running my fingers through her hair, she paused for a second before nodding and I pulled her in for another kiss.

Megan silently slid down my body until she was on her knees in front of me and I moved to the edge of the sofa for her. We held eye contact as she grabbed the bulge in my jeans as we both let out a moan. She rubbed and squeezed it through my jeans as her eyes now watched what she was doing. ‘Take it out’ she said a little bossy and I enjoyed her being confident enough to tell me what she wanted, I instantly unbuckled my jeans and pulled them and my boxers down as my rock hard cock sprung free.
‘Oh my god’ Megan said quietly as her eyes were glued to my dick, I’m not the biggest but Megan was so petite it made it look bigger. Her hands slowly started rubbing up and down my thighs as she looked up at me, as if she was teasing me slightly. I sat in anticipation for a minute or so as she ran her hands up and down my legs, getting close to my dick before moving back down, every stroke caused my dick to twitch. Eventually I felt her little hand wrap around it as she just held it for a second before she started stroking it slowly. With how horny I was pre cum had already started to run down my dick, and she used it to rub my dick faster. I sat there and watched her stroke my dick for a few minutes as her eyes never left my dick, when all of a sudden she leant forward and licked tip off my dick, catching me off guard and making me moan. Her eyes finally met mine as she smiled up at me, once again she leant forward but this time she wrapped her lips around the head of my cock, struggling to take me in at first.

Once she got adjusted to having my dick in her mouth she started bobbing up and down slightly, it honestly wasn’t the best blowjob I’ve ever got but her enthusiasm to please me and how hot she was still made it very enjoyable, and it was her first time giving one so I couldn’t expect too much. I held her hair out of her face as she looked up at me, seeing her eyes looking up at me as she sucked my dick almost made me cum. I pulled her off my dick and she giggled as she knew she almost made me cum, I laughed back as she kissed down my cock and then started kissing and sucking my balls. She was actually very good at sucking my balls and I stroked my dick as she sucked and licked them. After a minute of taking care of my balls she kept kissing down to my ass, I had never had my ass licked before but I wasn’t about to stop her.

I slid down the sofa a little more and lifted my legs up so she could reach my asshole better. She kissed and licked my taint slowly before I felt her tongue against my asshole. I wasn’t sure what to expect but if felt amazing, I let out a deep moan and swore as she started sticking her tongue in my asshole, fucking it slightly with her tongue. I just closed my eyes and rested my head on the back of the sofa as she grabbed my cock again and started stroking again as she tongue fucked my ass. I felt like I was in heaven. I knew I couldn’t take any more of this without cumming so I pushed her away from me, stood up and picked her up. Kissing her deeply as I carried her over to my bedroom.

I placed her down onto my bed and continued to kiss her as my hands wandered her body. I slowly moved my hands down to her leggings and went to pull them down but she stopped me, looking at me a little nervously. ‘Can you close your eyes while I take them off?’ She asked, obviously nervous about showing me what was underneath. ‘Of course’ I replied before kissing her and closing my eyes. I waited as I heard her shuffle about and take them off before she gave me the all clear to open my eyes. I was greeted by the site of her bent over with her ass high in the air and her face against the bed, it was such a sexy sight. I grabbed the lube that was in my bedside drawer and stood up behind her, rubbing and squeezing her tight little ass. I put some lube on my fingers and started rubbing them against her asshole, I’ve never really been into anal but she had a very nice looking bumhole. I rubbed it for a couple of minutes as Megan let out the occasional moan, and then I slid the tip of my index finger into her ass, struggling to push it in as she was so tight. I spent a few minutes easing my finger inside her, making sure to take my time not to hurt her. Megan still had her face buried into my pillow as I finally got my finger fully inside her, I slowly started to fuck her tight little asshole with my finger, feeling it grip my finger. I fucked her a little faster as she opened up more for me, I decided to try and fit another finger in. This time her ass opened up and accepted the second finger, I was now two fingers deep inside her fucking her with my two finger, the noises she was making were some of the sexiest noises I’ve ever heard. Finally she looked back at me ‘spank me daddy’ she said out of the blue, she’d called me daddy over message before but this was the first time I’d heard her say it. Instantly I spanked her, not too hard at first, but she begged me to spank her harder, I wasn’t about to say no to that. I spanked one cheek and then the other, switching between each cheek as my spanks got progressively harder. She was moaning and squealing with each spank as I now finger fucked her deep and hard. I needed to fuck her.

I grabbed the lube again and covered my dick and then pressed it against her pussy and asked her if she was ready and she nodded. I slowly push my tip into her, taking a bit of effort to slide it in, once I was in we both moaned and I started thrusting ever so slightly into her, waiting for her to open up for me. It took a couple of minutes of easing in with small strokes before I was fully in and able to start fucking her. She now had her head buried in my bed as I fucked her tight pussy, with deep slow strokes, she was moaning and swearing into the pillow. I fucked her like that for a few minutes before I spanked her ass suddenly making her yelp slightly and then giggle as she looked back at me, I spanked her again as I fucked her slightly harder. I knew if I fucked her too quick I’d cum quickly. I decided I wanted her on her back looking up at me as I fucked her.

I told her I wanted her on her back and she looked a little nervous but agreed, I pulled out and she spun around onto her back and spread her legs for me. I’d say I’m completely straight but seeing her hard little clit was quite sexy, I told her that she was beautiful and kissed her again, easing her nerves. Again I pressed my dick up against her pussy but this time she opened up straight away for me and I slid deep inside her once again. I held her legs wide open and started fucking her harder, seeing her eyes roll back as I fucked her harder. I fucked her for a couple of minutes in that position as she rubbed and squeezed her boobs. I let go of her legs and looked down at her little clit to see it was dripping with pre cum, I wanted to make her feel good so I spat on my hand and wrapped my hand around her little clit.

Hearing her let out a sexy moan as I started stroking her as I fucked her made my dick that tiny bit harder. I stroked her clit and fucked her deep as I looked at her, she was squeezing her tits with one hand as she bit her fingers on the other hand, looking at me. I could tell she was close. ‘Are you gonna cum for me baby? I asked her, she nodded before letting out a big moan as she replied ‘yeah.’ It must’ve been about 30 seconds later and then I hear ‘I’m cumming’ quietly, I continue to stroke and fuck her as she starts cumming for me. Dribbling over her belly and my hand, I stroke her clit until I’ve completely drained her and she went soft in my hand and then I knew I was going to cum. She could tell I was gonna cum and I started breathing heavier and moaning, ‘cum in me daddy, cum in me’ she repeated over and over until I shot deep inside her, fucking her until every last drop was inside her. I eventually pulled out and went and got some tissues to clean us up before we jumped in the shower together.

Megan spent the weekend and we fucked a few more times and we ended up seeing each other for a few weeks until things eventually broke down. I’m still friendly with her and seen on social media that she’s in a relationship and I’m happy for her.

This post ended up being a lot longer than I thought it would be, as once I started writing it down every little detail came back to me. I’ve got a couple more stories that I’ll post eventually. The next one will probably be something that happened to me when I spent a few days in hospital. Hope whoever reads this enjoys it.

Source: reddit.com/r/gonewildstories/comments/oamzyu/my_first_time_with_a_trans_woman_mf