First Time A Cross Dresser Gets Laid - Pt 1 free porn video
Mark was a shy guy who had always found it difficult chatting up girls. There was always some reason. He didn’t like their hair, or their body, or their look, or their personality, or his family would not approve. His upbringing was very conservative, old fashioned and his stoically minded, overbearing, controlling parents, forced their ideology on him. This had left its mark on him and he was a nervous, timid person. Any idea of an alternative life style was just not something he could do or even contemplate doing. The thought had crossed his mind from time to time but he always quickly banished it.
When he was in his mid-twenties, after an uneventful university stint, and still a virgin, he moved out and got his own place. He managed to find himself a reasonable job and usually worked half the time at home on his computer. He did find his life lonely but the solitude suited him. He wanted sex but couldn’t stand the idea of hiring a hooker. His only sexual pleasure was masturbation, a subject that his father had emphatically insisted was only for perverts and sick individuals. Mark used to loose himself in his own little world, feeling pensive but also slightly rebellious.
As time went by he became entrenched in his private existence. He spent most evenings visiting many porn sites, feeling quite naughty knowing that his parents would have been horrified. Mark found that he felt quite content, a feeling he had not experienced in his life before. He stopped feeling so guilty about masturbating.
One day, quite by accident, he clicked on a link and found himself on a porn site for trans people and cross dressers. He looked at the page and felt a sudden panic attack. Quickly he clicked to get off the site and it went to another trans page. Then he shut down his computer and sat there for a few moments breathing heavily. His mind was suddenly awash with thoughts that he could be found out, even though it was just a few seconds. His father would almost certainly kill him, (metaphorically speaking of course) bringing much shame to his family, that he could do such a thing.
He turned his computer back on and deleted his search history and then went to bed trying to clear his mind of this. But one thing happened, that he did not expect. He remembered one image and it kept coming back into his head. He eventually went to sleep and had a very restless night.
The next day he had to go into the office and felt uneasy, self conscious, guilty, nervous and almost felt like everybody knew that he had looked at a porn site with cross dressers and trans people on it. Of course no one knew and a couple of his colleagues even asked if he was okay.
On his journey home he couldn’t stop thinking of the image of the cross dresser. Then after he had eaten super he went on line and suddenly found himself clicking onto the trans porn site, without even being aware of it. It popped up and he suddenly saw this picture again and clicked on it. She was a cross dresser who was playing with a dildo and jerking off. Mark looked on in awe and realised that he had a hard on. He quickly opened his trousers put his hand on his cock and started jerking off like mad and came in less than thirty seconds.
‘Oh my god, that was amazing. Maybe I am gay, or a transvestite fancier. That was so good,’ he thought to himself.
He left the computer on and went to sit on the sofa. His mind was reeling with enjoyment and also fear of what his parents would have thought if they knew what he had just done. His whole life he had constantly sort recognition for anything he did or affection or love but had spent the entire time feeling unworthy and inadequate.
He sat for about ten minutes just thinking and then he went straight back to the computer again and restarted the video of this tranny. He quickly ripped all his clothes off and started jerking off again. Very soon he came. He looked down at his cock and saw it covered in cum but just kept wanking. The video ended and another one started with a different cross dresser, basically doing the same thing. He couldn’t stop himself and within about five minutes was shooting again.
That night he slept better than he’d slept in years. He almost felt like he was defying his parents and being himself for once. Knowing his father would be disgusted bought on a sense of pride that he’d never felt before. The next morning, before he went to work, he sat at the computer went straight to the site and got hard immediately and wanked off again. Mark spent the day feeling euphoric and couldn’t wait to get home.
Over the next few weeks, he couldn’t stop himself watching more and more videos on the site and orgasmed four or five times a day. This really was his true calling, he realised. In fact, he decided that he wanted to dress up and before he knew it he was frantically ordering lingerie and makeup on line. The weeks passed and he had inadvertently turned himself into a part-time cross dresser.
'What to do next?' he thought to himself and pondered the idea of meeting a gay cross dresser and loosing his virginity whilst dressed. He still couldn’t bring himself to telling anyone he knew for fear of it getting back to his parents. The notion of going out in public dressed was also a no go area. Mark considered all the possibilities and thought that meeting someone on line was his best chance, even though it could be dangerous. He had looked at many of the CD’s on various sites and had a few favourites.
There was one person called Lucy Lou and he fancied her like mad. He searched on line and found her on Twitter. To his amazement the message part was enabled and nervously he sent her a quick note. Not thinking for one second that she would answer he was stunned to suddenly get a notification from her. Mark tentatively wrote a reply and tried to be direct but polite.
The next few weeks was intriguing and he gradually got on to the subject of his recent transition to being a cross dresser himself. He found Lucy very friendly and supportive and approached the subject of actually meeting some one like her himself. Lucy did show a little reticence at first thinking that this was a scam or set up but he assured her that he was as scared as she was but he was genuine. Even though Lucy had posted many videos of herself having fun, she had done so on her own. She hadn’t appeared in porn movies and had not had a multitude of sexual partners. She was very open on sites but meeting a total stranger was somewhat nerve-racking.
It transpired that she didn’t live too far from him, which was an incredible coincidence. There was something about his manner that made Lucy trust him and they decided to meet at his apartment the following weekend.
When Saturday arrived Mark felt many different emotions all at the same time. He felt ambivalent, desperate, unsure, scared, horny, and he didn’t know whether he could go through with it. Lucy too was feeling unsure and hoped that this was not going to be a nightmare. Luckily it was the fall so by the time Lucy arrived it was dark and so no one could see that she was a CD. Mark was very insistent that she try to look as inconspicuous as possible and hope that her arrival would go unnoticed, as indeed it was.
She rang the bell and he clicked the intercom, telling her it was the second apartment on the left from the elevator on the third floor. She arrived at his door and with a sense of fear, excitement and dread he opened the door. Lucy entered the room and Mark politely took her coat. He was gracious and friendly and ushered her into the lounge.
Lucy was wearing a black thigh length dress and fishnet stockings and four inch heels. She had long brown hair and quite heavy makeup. Large earrings, bangles, and a pearl neckless. Her nails were painted red and she looked a bit like a classy tart. But very attractive. She had on a big overcoat that was very ‘A’ sexual and also had a large shoulder bag.
Mark was wearing a blue dress which was very short and black seamed stockings. He had grown his blond hair long and it cascaded over his shoulders and a third of the way down his back. He also had heavy makeup and had done a sterling job.
“Would you like a drink, Lucy?” He was trying to be a good host and wanted her to feel relaxed. The truth be known, he couldn’t believe that this was actually happening.
“Yes please, red wine would be nice,” Lucy said and sat back on the sofa feeling at ease. This was going to be okay. Mark was being delightful and she didn’t sense any malice or bad intent with him. It seemed real.
Mark came in the room with a bottle of French wine and two glasses and sat next to her and proceeded to pour two glasses. He then handed one to Lucy and took one for himself.
“So, here’s to a new friendship and a wonderful evening.” They touched glasses and both had a sip.
“Well, Mark, you do look very sexy but we really need to find you a girly name. If you are going to dress then you need to get one,” Lucy said and gave him a little wink.
“Oh yes, I see. I did think about that but couldn’t decide. What do you think?”
“Well, you are very polite, and somewhat old fashioned, in the nicest possible way, so let me think. An old classy name. I know, how about Juliette. That sounds good, what do you think?”
“Wow, Juliette, yes I like that. That name didn’t occur to me but I like it, a lot.” Mark looked at Lucy and smiled.
“Okay, Juliette it is then.” Lucy leant over and gave him a little kiss on the lips. “That’s what we will call you from now on. I must say, that I really love your outfit and makeup. You have done a terrific job, even though your skirt is very short, but I like that. It certainly doesn’t leave much for the imagination but very sexy. If I didn’t know better, I would think that your intent is to seduce me.”
“Thank you, Lucy, that is very nice to hear. But if my intention was to seduce you would that be a bad thing? If it is then I would not dream of pushing you. You are just so amazing to me and…well…I…I mean what I am trying to say…is…”
“I was only teasing you, Juliette, you need to lighten up. I know exactly why I am here and I haven’t gone to all this effort just to sit here drinking wine and chatting, however pleasant that may be. To be perfectly honest with you, you found me on line and have seen me, how shall I put it, being a slut in front of a camera. If your intention wasn’t to have serious fun I would be very disappointed.”
Lucy looked at him, leant over, put one hand behind his head and kissed him. This time though it was a proper kiss. Juliette, put her arm around Lucy and pulled her close as the kissing got really intense. When they broke off Lucy looked down at Juliette’s panties and could very clearly see a very aroused bulging cock.
“My, oh my, Juliette. I think you are one very turned on girly. I will have to do what I can to relieve you of your frustration. What should I do? Oh, yes, I know, I have an idea.”
With that, Lucy got on her knees and pulled off Juliette’s panties. Running her hands up his thighs she bent her head down and kissed the top of his cock.
“Oh, yum, yum. Very nice. Do you mind if I have a little taste? Your cock looks divine.”
“Oh my god, yes please. Be my guest. Do whatever you want. I can’t believe this is happening.”
With that, Lucy got to it and immediately started sucking like mad. She put her hands on his cock and moved them up and down as she slurped and groaned. Juliette felt the most enormous feeling of pleasure and lust rising up in side him and could not hold back.
“Sorry, Lucy, but I can’t keep it in, oh, baby, baby…oh!”
Then, he shot his load straight into her mouth like an explosion. Lucy somehow expected it to be quick, but not that quick. This sexy virgin was obviously so turned on that he couldn’t wait to cum which she felt was lovely. She lapped the cum up and licked it around his cock. Then, she pulled out, opened her mouth to show him and swallowed it all down.
“Wow, that tasted very nice you horny bitch, Juliette. Very quick. I think in a little while I will have to do that again. But first, my dear, it’s my turn.” Lucy jumped up beside Juliette’s head, pulling up her dress and moving her panties to one side and got hold of her cock with one hand and Juliette’s head with the other. Lucy pulled his head towards her hard cock and slid it inside. She gently started rubbing her cock up and down and slowly fucking his mouth with sensual thrusts of her hips.
“You just suck this, okay? I will make sure you do it right. You are going to have a big load in your mouth soon. This is just the starter, the main course will follow. Mmmmmm suck it good, babe.”
Lucy was working herself up and she was going to cum quickly because, inside she knew how much Juliette needed this. This was his initiation into the world of cross dressing and tranny sex. Lucy was going to make sure it was the best night of Juliette’s life. She didn’t really have to try though because it was the best of the best of the best for him already. Juliette needed this so much and he was, sucking a tranny’s cock after having his own cock sucked. It couldn’t get any better.
Lucy worked her cock and Juliette sucked like a star. Lucy could come quickly if she wanted to and knew that this was such a time.
“Okay, Juliette, you horny, sexy, cock sucking, tranny slut you. Here is your first mouthful of cum. Oh, baby…oh...take it!”
With that she came and the cum just kept shooting and half-filled Juliette’s mouth. When she finished she pulled out and said,
“Okay, girl, open up and show me. I want to see you with a mouthful of cum before you swallow.”
Juliette opened up, showed Lucy, then swallowed it all down. It felt so invigorating, liberating and just so damn perfect he almost came again. Lucy got down and sat there and gave him a wonderful kiss. Then took a sip of wine, then announced.
“Right, where’s your bedroom? It's time to do some serious fucking. Come on girl, what are you waiting for. We’ve only just begun.”
Liesl
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