My first time as cd gurl

My first time as cd gurl
So. I’d been talking to a guy for a while, probably over six months. I’d gotten in touch with him through a website I’ve been a member of for ages, called He was forty at the time (this was 2013, so I was 23). We had talked a lot about sex, our fantasies, and I had shared my fears (fear of meeting someone who would treat me badly in a non-hot way, fear of meeting someone who wouldn’t think I was hot, fear of not being good enough at sex). He had made me feel comfortable about everything, and put me at ease. He was also as kinky as I am, and we had talked about all kinds of possibilities for the future…

So based on that, we started talking about meeting up. I’d never met up with a dude before, even though it had been a fantasy of mine since I was about 11. I had always wanted to meet an older man, and this guy was twice my age. So it all added up.

We decided on a day to meet up, but when that day came around it didn’t work out because of conflicting plans. Which was unfortunate, cause I was fucking ready that day. I was going away two days after, and when he proposed doing it the day before I went away I was a little weary (PS, through this entire process I was TERRIFIED, but I knew I wouldn’t regret it so I just kind of powered through). I had prepared my ass and dressed up and everything on the day that didn’t work out, and the short notice of the day after meant that I was a little less ready. More on that later.

We decided that he was gonna come by my place. A few hours before he came by I started getting ready, washed out my asspussy (but I had told him that I only wanted to suck that day), put on makeup, put on a dress and panties, and my thigh high socks (I was going to see my family in a warm place the week after, so I was only shaved from my knees up. Weirdly enough I had even shaved my arms, but couldn’t bring myself to do my shins and shit… oh well). Still fucking shaking from nervousness.

He was gonna text me when he got there, so I sat down on the couch to get ready mentally. I don’t drink or do d**gs, so that wasn’t an option… Instead I put on a bunch of sissy hypno and put my buttplug in my ass. My idea was that he would get turned on by the buttplug when I was sucking his dick, I wasn’t actually getting my ass ready for getting fucked (at least I didn’t think I was). I have absolutely no idea how long I watched that stuff, but it must have been a while. I was really trying to turn my brain into mush so I would be a good whore and not be so nervous about fucking up. My plan was that as soon as he would text I would get up and get on my knees in the middle of my living room floor, to greet him properly. My mind was a total mist at this point (unfortunately not from the hypno, but from nervousness. My legs were jelly and my body didn’t feel like my own).

I got the text. I don’t remember what it said. I got up right away, barely able to stand, holding my hand on my plug so it wouldn’t slide out (my plug sucks), and got on my knees on the floor. I arched my back to sit up straight, and put my hands in my lap. I wanted to get the submissive posture just right. I also looked at the ground a meter or two in front of me to keep my head down, as opposed to looking at the door when he came in. I wanted everything about my body language to say submissive, willing to please, and pretty.

The door opened, and I felt like I was dying. He came in, and I was looking at him from the corner of my eye, not compromising my posture. He took off his shoes and his jacket, all while looking at me and smiling. I don’t remember if he said anything right then. I heard him coming in and saw him closing in in the corner of my eye. He walked up to me and inspected me. He put his hand on the top of my head while he walked around me, it made me feel small and owned, and ready to hand myself over. He was telling me how pretty I looked, and that I was his pretty little sissy. The hand that wasn’t on my head reached around and lifted up my dress, and he saw my plug and panties. He was surprised (and clearly very happy about it), and told me so.

Then he got in front of me. He was wearing a button-down shirt and a pair of jeans. He was slightly shorter than me I think (but I was pretty much never standing up in his presence), bald, and with an athletically thin frame. Light stubble.

He put his hand on the back of my neck and pulled my face close to his bulge. I felt the heat through his jeans, and opened my mouth and made out with his crotch. It was turning me on so much, but I was still soft. Maybe the nervousness (but for hotness I’ll tell myself and you guys that it was because my body realized that I was just a pussy when I was around this man, who at that moment was my alpha).

He put his arms on his hips and told me to open his jeans. I unbuttoned his belt, and the top button of his jeans, and pulled his zipper down. That was my first time ever seeing a dick up close (that wasn’t my own, duh). He told me to take it out. It wasn’t hard, but about halfway there. That turned me on a lot. The idea of getting to suck a soft dick hard is amazingly hot to me. I reached my hand in and took it out. It was fucking beautiful, and how the warmth turned me on so much. When it got hard it was about 19 cm long, and average thickness I’d say. I wanted to suck it really bad, even though it scared the shit out of me.

I don’t remember if he told me to suck it, or if I decided to myself, but I remember having it in my mouth after that. I think one of the things that struck me is that sucking a dick is both dramatically different and surprisingly similar to putting a dildo in your mouth. The textures, smells and touch are so different. It was crazy. At the same time, the feeling of gagging and getting it deep in my throat was surprisingly similar to when I’ve practiced on dildos. I was so eager. I wanted to gag, I wanted to tear up, I wanted him to love it. I took it out and sucked his balls, the hair on them turned me on (he was shaved on his dick and everything, but I remember there being hair on his balls). I wanted to get messy.

I don’t remember how long I sucked it for. I know that the total meet lasted maybe a little more than an hour. He had shit to do afterwards so that was the time we had.

Anyway. I was going to town on his dick, trying to get it as deep as I could, and he was getting into it too. He was pushing his dick into my throat, I was tearing up and getting drooly. He slapped me now and then, and he was talking dirty the whole time, calling me a good sissy, and that I was his. I’ve never talked much during sex, so it was different from what I was used to, but I liked it in the situation. He told me he couldn’t believe this was my first time, and that I was great. I don’t know if it was true, but it made me feel so proud.

After a while, he asked me if he could fuck my pussy. I don’t remember how he asked, but I didn’t feel like I could say no at the time. I also didn’t want to, and I really like how persuasive he was. Without that I wouldn’t have gotten fucked that day, and I’m so glad I did.

He led me over to my couch, and put me over it. My knees were on the floor and my body and face were on the couch cushions. I felt him lift up my dress and pull my panties to the side. I don’t remember if my plug was still in my pussy or not at this point. He was behind me, and I heard him open a condom and put it on his dick. He also picked up a bottle of lube that he had with him, put some on his finger, and lubed up my pussy. He stuck one finger in and moved it around, and I was going crazy in my head. Not like, cause it felt so good, but because of like “HOLY FUCK THIS IS HAPPENING”. It was insane to me.

Then he lined up his body behind me, and put the tip of his dick to my hole. He pushed it in slowly, and I was completely dazed about the whole situation. I felt him getting deeper and deeper, and it felt like he was in my fucking stomach. He pushed in slowly, but it was still overwhelming. He grabbed on to my hips, fucking me slowly. I’ve fucked myself with my fingers and dildos a lot and stuff, but this was waaay different. He was so deep, and it was making me lose control. I was whimpering, trying to keep my voice sexy even though it was hard to focus. He smacked my ass and kept telling me that I was his sissy, and I was starting to push back even though I felt like I was going to break. I wanted to be a good slut, and I wanted to feel him as deep as possible.

After fucking me like this for a while, he pulled out. He told me to get on my knees and suck his dick. He took off the condom and I could see that I wasn’t as… clean as I had hoped. Since I wasn’t planning on getting fucked I hadn’t gotten as clean as I would have. Oh well, he didn’t seem bothered by it at all, and I was just happy and thankful to be deepthroating his dick with my ass feeling used. My ass was a little sore, but mostly it had a feeling of openness.

I sucked his dick, and he helped push it down my throat. It wasn’t a full on throat fuck (I wouldn’t have minded rougher treatment, but it was the first time after all so maybe it was for the best), but it was pushing me physically. Spit was coming up, I was gagging, my eyes were watering.. He slapped me every now and then, all the while telling me that I was a good little sissy.

Then he laid me on my back on the couch, with my legs in the air, and my pussy sticking out over the edge of the couch. He put another condom on, and stuck his cock in my pussy. This time he was less careful, and if I thought I was feeling it in doggy this was on another level. He took hold of my thighs and fucked me balls deep, hard. His dick was jabbing my stomach, and it was painful, but the loss of control turned me on so much. My body was making sounds that I had no control over, and I really felt like I was being made his bitch. Even though it hurt and I kind of wanted him to go shallower, my body was pushing against him hard to get his dick all the way in. Something that really struck me was how much I loved the feeling of his pelvis hitting me when he bottomed out, the feeling of submission and connectedness when he was all the way inside and the impact that shook my whole body with every thrust. He kept telling me that I was his pretty little sissy, and I felt like it. This was the best part of the fuck I think. It was a****l and raw, and the loss of control and surrender I felt were something I’ve never experienced.

That was amazing. The only downside for me at this point was that he was wearing a condom. Although I’m glad he did (I would never have made him or even asked him I don’t think), I wish I could have felt him raw, and especially I would have wanted him to cum inside me.

That fucking went on for a while. I was looking at him fuck me and I was turned on as fuck, but still hadn’t gotten even a little hard. Which was great. When he was getting close he pulled out. He pulled the condom off his dick, this time also it was dirty. Again, he didn’t seem to care, and I was so thankful. He told me to get over to him and suck him again. I was eager to take it deep and show him my dedication. Gagging away, all the while looking him in the eyes with my watering eyes. He was holding on to my head, challenging how long I could keep it down.

Then he said he was ready to cum, and asked me where I wanted it. I pointed at my mouth and smiled as cutely as I could. I think he liked that, cause he started jerking off. I licked his balls, the feeling of him jerking his cock over my face while I had my face covered in his balls and my drool was driving me crazy. I could tell he was getting close. He told me so, and pushed my head back, aiming his dick at my open mouth. I was so happy to finally be earning my first cum. I didn’t miss a drop! I swallowed everything without flinching, and cleaned his dick off with my mouth.

That was it, after I had cleaned up it was like the scene ended, and he came out of character. He was suddenly a different person, and it was actually great. After a little bit I stood up. He was telling me he thought it was a great time, and that he wanted to meet up again. Then we talked while he was getting dressed and stuff, about music and whatnot. Super relaxed, and I liked getting my first ever opportunity to be myself, but also be a girl. I could talk about the stuff I like, but as a girl, with someone who saw me as a girl and who used me as such. That was cool.

Then he left. I went straight into the shower and came three times. We kept in touch for a bit after that, but I for some reason was not ready to meet up with a man again for a long time, so long that I had time to meet my girlfriend and get involved in the relationship I’m in now, which has prevented me from pursuing it since we’re monogamous. He was great in so many ways, and I’m really thankful to him for making my first time so great. So many dudes could have made it so shitty.

So to other sissies: go for it! As long as you’re careful and make sure you meet someone who you trust you won’t regret it. And worst case you hate it and don’t have to do it again. Nothing to lose

My virginity story

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