Taking the virginity of an athletic crossdressing student [MT] [M30,T19]

I haven’t been able to share a good story for quite a well. There haven’t been any to share. I was travelling on business almost constantly from August until the end of the 2017. During that time, I had sex with two women, but neither story is overly exciting. I do have a great experience from New Year but I’ll save that for another time. Instead, this is an experience that happened only just last weekend written up while it’s fresh in my mind and not embellished in any way.

I received a message last Monday afternoon on a fetish social network from someone listed as a man. “Jay” he called himself. I make it clear on my profile that I’m only interested in messages from crossdressers and transsexuals, but before I deleted the message (which I hadn’t even read at this point) I clicked through onto his page. There were no pictures of his face, but I could see that he was very well built and kept himself in good shape. He was 19 and looking for women and couples. This piqued my interest as I wondered why he would be messaging me when we have such incompatible interests. I went through to his message and read it.

“Hi. I’m a bit nervous messaging you, I’ve never done anything like this before. I have secretly been dressing in my roommate’s clothes for the past few months. I don’t know how or why it started, but I’ve got really into it. I love wearing her underwear and tights. Recently I’ve been having fantasies of being dominated by a man. I have no experience whatsoever with guys but want to try. I suppose I am curious, possibly bi. I know I’m maybe not what you’re looking for but if you’re interested I’ll be alone all weekend. Let me know!”

If you’ve read my other stories you’ll know I’m usually into effeminate, sissy types. This guy was anything but. He was – without seeing his face – clearly a very physically attractive man, and from the pictures of his cock he was not lacking in that area either. His profile had been verified as genuine by several women, so he clearly wasn’t stuck for sex. I was intrigued. We began messaging back and forth over the next 24 hours, and Jay sent me a couple of pictures of him stroking his cock in his roommate’s silk panties. I began to consider that I would like this. I felt I would enjoy the power of exploring unknown territory and – quite frankly – fucking a virgin crossdresser who otherwise presents as a confident, athletic, attractive student.

I usually prefer to meet at either a hotel or in my house, but Jay was very keen to meet at his flat. He lived with another guy and two girls. We talked on the phone on Thursday to make arrangements and to satisfy me that this was the real deal. On the phone Jay sounded normal, albeit extremely nervous. He told me he had almost chickened out of the phone call after he had cum thinking about our meeting. I told him to give me his address. He did. I arranged to go to his house at 7pm on Friday. It was the first time he would be totally alone for the weekend in the flat. The others left earlier in the day.

Friday felt like it took forever. As the week had gone on I’d become more and more convinced this was something I’d like to try. I’ve had sex with quite a lot of women and more than a few crossdressers over the past 10 or so years, but in all that time I’ve never been with anyone remotely masculine. The reality is that I consider myself reasonably straight, albeit with a twist. Jay was straying into a new territory for me. This felt more “gay”. He was clearly unconvincing as a woman, and had made it clear to me that he just enjoyed wearing Laura’s underwear. That was her name. I’d been told that two of the roommate’s were a couple and stayed in the same room. Strangely Jay wasn’t attracted to the underwear of the girl in the couple. Only Laura. He told me she is hot and that he has had drunken sex with her.

Anyway, on arrival to the block of apartments I pushed the intercom and Jay answered. He let me in and I went up two flights of stairs. At the top, Jay had opened the door and was awkwardly ushering me inside. I suppose the neighbours might wonder what a 30 year old in a business suit was doing in his student flat. Inside we went straight to Laura’s room. I could see from the pictures on the wall who I assumed to be Laura and she was a nice looking girl. Typical student room with magenta walls, a fake beech bedframe and quite messy. The duvet was flowery and pink and the room had scattered around it enough femininity that it definitely wasn’t a male’s room.

We both sat on the bed as we chatted. Talking was easy at this point as we had chatted on the phone at length the day before. Jay was attractive. He was a genuinely good looking guy. Tall, muscular with cropped brown hair. He had quite a distinctive jawline not unlike Daniel Craig. He wore a white fitted t-shirt and jeans.

He told me that he had dressed in his mother’s underwear years ago but felt that he had grown out of it. It was only when he came to university that he had began crossdressing again. He told me that he had lived in halls his first year and had bought some lingerie but had thrown it away when he moved. He then moved in to his current house and felt lucky that he had easy access to a girls things again. He told me he usually came into Laura’s room, grabbed something and returned to his own room, stroked his cock while wearing her clothes and then felt immense shame. He said it was only recently that he had started to wear her panties under his clothes and felt more comfortable even after he came. He told me he had worn her tights under his trousers to class that day and was very horny.

I told him to stand and take off his clothes. He removed his top and trousers, standing before me in nothing but socks and boxers. I told him to keep going, and though he was shy, when he pulled down his underwear I could see that his cock was already stirring. It was at least partially hard. I asked him what he wanted to wear for me and he was able to expertly locate exactly what he wanted.

He showed me the bra. It was nothing overly fancy, but it was made of a very soft and stretchy material. “Calvin Klein” was printed across the front. He showed me matching panties – again made of the same material. His hand was shaking. I asked him to put them on. He hesitated, but he wasn’t quite as nervous as I expected. He put the bra on across his muscular chest and pulled the panties up. Their bikini cut barely covered his clearly hard cock and the stretchy material just about allowed his cock to remain within.

Jay said that Laura had some stockings but they are gone. He thinks she has left them at her boyfriend’s house. I told him that was ok and to come and sit beside me. I gently touched his leg and although he flinched he did not recoil. I told him I thought he looked hot – in actuality I was slightly unsure myself as he was quite a bit more muscular than myself. I rubbed my hand gently up his thigh and ran it over the panties. By this point, having spoken the day before it was clear that Jay was into being verbally degraded.

“How do you feel dressed like a slut for me?”

“Do you like this? Feeling a man rub his hands over your sissy body?”

“Are you nervous? You’ve been waiting for this. Tonight you’re going to have my cock inside you.”

He squealed in delight with each comment I made. I gently stroked his cock through the panties. There was a little spot of precum had made its way through the synthetic material.

“You’re going to take my cock in your mouth. Your first ever cock. Put your hand on it.” He put his hand on the outside of my trousers and could feel my hard cock straining. I lay back on the bed and undid my trousers. I pulled them down and my cock was staring directly at Jay. He put his hand around the base and gently stroked it, all the while staring intently. This went on for at least a minute before I said, “what are you waiting for you little bitch, get your lips wrapped round my cock.” He did as he was told and within seconds his lips were around the tip. He gently bobbed up and down. “Deeper, slut. Rub your tongue on my head.” Again, he did as he was told. He looked up at me and said, “this is so fucking hot.”

At that moment, with this athletic man masquerading as a sissy I looked around the room. I was in a young woman’s bedroom. Unmistakable – the scent of feminine deodorant and perfume, the various creams, the dresses and clothes strewn around the furniture. The half-closed drawer with lingerie spilling over the top. Directly beside me I could see a picture of who I assumed to be Laura and her boyfriend. I looked at Laura and I imagined what she was doing at that moment. What she had absolutely no idea about was that a man – a stranger – was lying on her flowery sheets having his dick sucked by his strong, athletic roommate. A roommate who at this moment was wearing her Calvin Klein underwear. Underwear she will probably be wearing at university this week.

I groaned and said, “how does a dick feel in your mouth?” Jay mumbled “good” through his sucking. I told him that it was his place in the world to suck cock and could he imagine ever getting another girl if they knew he was a crossdressing cocksucker. He moaned while I ran my fingers over his nipple inside the bra.

I brought Jay up so he was sucking my cock side on. I began to gently stroke him through the panties. “How would you feel if this never went inside a girl again?” “How would you feel if the only way you ever got off was to wank yourself while you get fucked?” Jay was absolutely loving this. He was becoming more adventurous with his technique and it was beginning to feel difficult to hold back on cumming. I had Jay lay back on the bed and I took out lube and condoms from my pocket. I took my clothes right off and lay beside him. I told Jay to close his eyes. I put lube on my hand and asked him if he wanted my hand on his cock. He said he did. I told him he wasn’t getting it and instead and put my hand between his legs and lifted the panties to the side. I began circling my finger around the outside of his asshole. He took his hand down to stroke his cock and I made him take it back. “Don’t touch yourself. Enjoy the feeling of being a woman.”

I gently pressed on finger, and then after some time two past his tight rectum and into his hole. I pushed in and out. Jay clearly found this uncomfortable, but he was enjoying it all the same. His cock remained hard as a rock. Around 6 inches, cut and veiny. Stretching the panties right out. He moaned each time I thrust my fingers into his ass.

I had him flip over. He watched my as a quickly covered my cock with a condom and rubbed lube all over. “Are you ready to get fucked?” “You told me you’ve only wanted this recently, but I know you’ve always been gay.” He moaned as he touched and squeezed his own nipples while laying almost flat on the bed. I positioned myself between his ass cheeks and pushed.

My cock reached the edge of his hole and I whispered in his ear, “do you want me cock?” I received a whispered, urgent reply of “yes.” I pushed and heard a sharp intake of breath. I not made any progress. I spread open his hole with my fingers. It was virtually hairless and very much puckered. I asked him to gently push out while I put my cock inside him. Eventually after quite a bit of manoeuvring I got the head of my cock beyond his rectum. I added more lube and continued my entry into this virgin ass. I began to slightly retract and thrust back inside. I asked Jay if he liked being fucked. “I love it. Please keep going.” This was, honestly, hard to believe, because of his moans of discomfort, but I suppose the mental thought of a cock inside him was more than enough to outweigh the physical pain.

As he became more accustomed to the feeling I began to thrust out and in more aggressively and more deeply. Jay was properly being fucked. I couldn’t get more than about 4 or 4.5 inches inside, but I was enjoying the tightness. Pulling right out to his rectum is my favourite bit of any anal sex. For those who haven’t tried anal there is a very different sensation to a vagina. With a vagina there is an almost uniform tightness once inside. Anal sex has an initial tight ring and then sort of nothing inside. That is what I enjoy about anal – the tightness of the rectum stretched to accommodate my dick.

I was properly fucking Jay by this stage – he was fully moaning as I thrust deep inside his ass. He hadn’t touched his cock since I made him lie on his front, so I flipped him over and told him he could stroke it. “Stroke your cock thinking about what is happening to you.” “You are a fucking sissy slut taking a dick. My whole dick is inside you.” He was loving it. He stroked his cock viciously as I fucked him missionary.

“I’m going to cum.” I pulled his hand off his cock and watched it twitch. He moaned as I pulled him back from the edge. He had a mini-orgasm – I could feel his rectum twitch on my cock, but he hadn’t cum. I told him I would make him cum like a girl. I gently fucked him as I lubed his cock and began running my index finger in circles around the tip of his frenulum. He was moaning. “Please stroke it, please make me cum.” No, I was going to make him cum from rubbing alone. Eventually he told me he was cumming. I dropped his cock and it jerked gently before staying just above his belly. I grabbed the shaft and quickly stroked up and down. A few seconds later Jay shouted, “fuuuuuuck” as a huge, thick stream of cum shot out and landed on his neck. A couple more smaller streams came out as I continued to gently fuck his asshole.

“Ok can you stop now. Sorry. I’m sorry it feels weird.” I took my cock from his ass and removed the condom. He sort of stroked my cock but I could feel that the moment was gone. He clearly felt guilty for the whole thing after cumming. Beneath me I could see this athletic, attractive 19 year old, freshly fucked on his roommate’s bed, wearing her underwear and with his chest absolutely covered in his own cum. I stroked my cock. He watched my intently. I was close to cumming anyway, so I pushed my cock up to his lips and asked him to lick. He did. Clearly he wasn’t as into it as before he had cum, but watching this sissy lie beneath me as I stroked over him sent me over the edge. I was side on at this stage and grunted as I shot my cum across his chest. A stream landed on his cheek and pooled in his neck. A stream landed across the bra cup. He looked in awe as my cum shot out. I was spent. I looked down and saw Jay also lying in a daze. Fantastic.

Immediately after this, Jay got up, stripped off the bra and panties and went out of the room. He came in a couple of minutes later cleaned up and wearing a tracksuit. I got myself cleaned up and got dressed. I left in a sort of awkward silence that I wasn’t sure what Jay was thinking. At that time, I’m sure he was thinking I just want this man out of my house.

“That was amazing. I’m so sorry it was a bit weird at the end but I just needed to process what happened. I hope you don’t mind. I’d like to do it again some time.”

Would I go there again? Maybe. I enjoyed the experience, but I’m more into passable or very effeminate crossdressers. What a night to remember though.

Please leave any feedback or comments. I enjoy reading them. Check my other submissions for some other experiences I’ve had with crossdressers over the years and one or two with women.

Source: reddit.com/r/gonewildstories/comments/82p43y/taking_the_virginity_of_an_athletic_crossdressing