A couple of weeks ago I was browsing a fetish social network and saw there was a new user in my area. A crossdresser calling herself Lara, 20 years old, slim, 5’9”. There were two pictures, one of her ass in a black thong, showing a nice muscular ass, not hugely feminine, but more androgynous. There was a second photo or her crotch from the front, in black satin panties with a slight bulge and just the smallest hint of her cock head. She said she had no experience with guys and was looking to try everything from kissing to anal, but lived with her parents so couldn’t host.
I messaged her right away and we began chatting. Over the course of the coming days I found she was “straight” – or as straight as you can be when she’s telling me she wants a man to fuck her in the ass while dressed in her sisters clothes. We chatted back and forth for a bit and built up a good rapport. Eventually I suggested we meet last Friday night. She was kind of cagey about meeting, but did agree that we would meet at a car park close to my home and chat, before going to my house after if she was comfortable.
To cut the story short, she flaked on Friday and didn’t log on to her account until Sunday. On Sunday she sent me a lengthy message apologising and saying she made the mistake of masturbating before coming to meet me and then she felt guilty. That old post-orgasm guilt! She said she still really wanted to meet, but was nervous and has never done anything like this before. She said she had her girlfriend to worry about finding out. I basically said take it or leave it – if she didn’t want to meet I didn’t want to pressure her.
She got back to me late on Sunday night and proposed meeting at 4pm on Monday. I agreed, but stated that she could not stay late as I was getting an early flight on Tuesday morning. I went to the car park at 4pm, and as agreed there was Lara’s car – a black Ford Fiesta – sitting there. I beckoned her to come over to my car and she was just as described, although with male clothes as a top layer. She told me she’d be wearing white lingerie, including white stockings with red bows under her clothes. Lara got into my car and we chatted for a few minutes, quickly admitting she felt fine and was keen to meet me. We agreed to go in my car the short distance of a couple of miles to my home. I rubbed my hand on her jeans in the car and could feel that tell tale sensation of rubbing the stockings underneath.
Once there we went straight to the bedroom and Lara took off her outer layer to leave her wearing a very simple white bra, white stretchy nylon panties and the white stockings with red bows. She reiterated to me that she had never done anything like this before with a guy but she was excited. I could tell, as her cock was straining against the elastic material of the panties. She had obviously folded her cock down to try to hide the bulge, but in its erect state it was pushing the material outwards with force. Her face was boyish – clean shaven, blue eyes, smooth skin, with a longer hair style she had pushed back with a hair band. She looked cute.
I was fully dressed when she joined me on the bed, hiding that my cock was also rock solid. I embraced Lara and pulled her in close, grasping my hand on her ass. We kissed, which she soon got into and I could feel her rocking her crotch back and forth into my own. I removed my clothes, right down until I was fully naked and I could see Lara absolutely transfixed on my cock. I lay down again and she didn’t touch my cock, but we resumed kissing. I could feel the silky material of her panty covered cock rubbing on my own cock as we thrust and rubbed against one another. After some time of enjoying the feeling, I reached down and exposed Lara’s cock. It was quite large, a good 6”, but rather slim, looking quite natural with her very small body. My cock was a bit longer than hers, but absolutely dwarfed her thickness, making them almost look like his and hers together. I proceeded to rub our cocks, placing the heads against each other and swirling them around one another. Lara was loving this and soon told me she was going to cum. I stopped touching her cock completely and placed it back in her panties, and told her to begin by stroking my dick. To this point she had barely touched me, obviously nervous.
She reached her dainty hand with long fingers around my cock and began to stroke up and down while we kissed. It wasn’t great. Her technique was too gentle. I don’t require a death grip, but she was so timid with my cock that I could barely feel anything. I pushed her head down and asked her to “be a good girl” and take my cock into her mouth. She loved that. Lara was enjoying playing the role of being someone she was not, and I could tell that her “straight” façade was being eaten away by thoughts of sucking my cock. I was so fucking turned on. Turned on by the fact that I was lying on my bed with a virgin crossdresser just ready for my cock to enter her mouth. Turned on by the fact that I was lying on my bed with an outwardly apparent straight young man, with a girlfriend. I thought about her fucking her girlfriend and wondered what she’d do if she knew I was about to bury my cock into her lover’s mouth. I thought of her sister and wondered what she’d do if she knew her younger brother was making love to a man in her lingerie. I wondered what her sister had bought those stockings for – probably fancy dress. I thought about Lara furiously masturbating her slim cock on Friday night and bailing on me after she came. As you can imagine, I was so fucking solid my cock was almost hurting.
At that moment of these thoughts racing through my head, Lara tentatively placed her mouth around my cock and looked up at my as she moved ever so slightly up and down. She really wasn’t that great at sucking me, so I coaxed her to try different things, particularly involving her tongue, which she did pick up on.
After a bit of time she was going quite well, and I asked her if she wanted me to take her in my mouth. It’s not something I often do, but I felt in the mood to suck her cock. She was very keen and I lay her down on the bed and went to work licking her very cute little balls held tight against her body and very cold, with the panties pushed aside. I soon found myself putting her whole cock in my mouth and sliding my lips up and down her shaft. There are amazing things in life, and seeing a virgin crossdresser writhing in her sisters clothes beneath me was an amazing thing. I Rubbed my own cock up and down her stockinged leg as I did this and enjoyed the coarse yet smooth nylon rubbing on my head.
Within just a few minutes Lara went totally rigid and silent. Not a noise in the room, and within a couple of seconds she was flooding my mouth with a very liquidy cumshot. A good amount shot into my mouth and I hastily swallowed, personally not being a fan of the taste of cum. After she was spent I removed my mouth from her cock and started rubbing my own cock head on her rapidly softening but slippery glistening cum-covered cock. I pushed the softened head inside my own foreskin and enjoyed the lubrication from her cum on my shaft.
“I’m sorry, I don’t like this, I don’t think I can do it,” was the next thing I heard. The post-orgasm guilt was back. Lara was feeling guilty about the fact that a man had made her cum in his mouth (and she enjoyed it). I wondered what was going through her head. “I want you to cum,” she said. “I’ve always wanted to do this, and I want you to cum on me.” She put her cock away inside her panties and I began stroking my cock over her chest.
I let myself build up to the thoughts of this sexy young thing, conflicted about being there, about to take my cum on her body. I could smell the bleachy smell of her cum in the room, and I could see her lying there, eyes closed as she gently stroked the top of my leg. I felt the cum travelling from my balls, and momentarily stopped stroking as I waited for the point of no return to stroke myself to a well-deserved orgasm. I held, and held, before letting out a satisfied groan, felt Lara tense up, and I shot 3 huge ropes of thick cum from my cock, the first of which shot a good 2 feet up her body and landed on her cheek. The rest of my cum was on the cotton bra and spread across her chest. She recoiled and smiled slightly as she realised I had shot my load on her face.
I got up from the bed and got a couple of towels. I asked Lara how she felt. “Good, I enjoyed that but I think for me it’s a one off.” I told her it was a shame, but I knew she was conflicted all along. We chatted a bit in bed, fully clothed and then I drove Lara back. She remained fairly bubbly throughout, but I was in no doubt that it would be a one off for her. I took it that she was straight, had tried something new, it wasn’t for her but that it was an eye-opening experience.
Next day I arrived in Brussels on business and checked my account. Message from Lara. “Sorry I was a bit weird last night, I get really strange when I cum. I really enjoyed last night and came this morning thinking about it. Meet again soon? xx” Fine by me. We’re meeting next weekend, and her cock will be out of bounds. I want to pound that ass.
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.
I met with Poppy last week as well (from a previous story). She is superb. I wish I had time to write stories of every meet we’ve had.
Source: reddit.com/r/gonewildstories/comments/6llv7g/mutual_sucking_with_a_straight_virgin