Tranny
- 1 year ago
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First Time With A Tranny. free porn video
Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people.
People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He still found women attractive and some men. The thought or even the sight of a transvestite mad him very nervous. That was probably fueled by growing up in the sixties and seventies. There was a great ‘no go area’ when it came to trannies. Society made one think that these types of people were in some way sick and perverts.
Stevie had found the odd cross dresser desirable. He felt shame that he could experience this. The feeling did not go away. There were many sites for him to look at transvestites and see them having sex. It started to get better and he really enjoyed it. If only he had the courage to find someone that he could have fun with.
Then, one day, out of the blue a breakthrough came. Stevie was watching the news and on came this report about a catastrophe at a gay club. As some of the party goers were being interviewed he watched with interest. They were just normal gay guys, then suddenly this Transvestite came on the screen. She looked amazing and as she spoke Stevie felt his cock getting hard. That clinched it, his mind was made up. You didn’t get a hard on looking at a tranny unless you really fancied them. He had to get laid by a tranny.
Trying to avoid going to a gay club or bar, he eventually found a dating site where people who were nervous could meet safely. He was on the site for weeks and then one day met a great looking tranny called ‘Daisy.’ She was everything he wanted and was also quite inexperienced. They could both have fun and fumble about without worrying about anything.
So, after a few nights out having some drinks and a meal, the night came. Stevie didn’t mind going out with Daisy because she looked like a woman, and a very attractive one at that. They went back to Daisy’s place and both got themselves ready, washing, changing, and getting relaxed.
Stevie just washed and sat in the lounge waiting in anticipation, his bulge in his trousers said it all. Daisy decided to make herself look really sexy for him, and it worked. She washed and slipped on a dark blue basque and seamed fish net stockings with big lace tops. Then this very short black, wet-look dress, which just about stopped at the height of her stocking tops. A new pair of silky panties and re-did her make up. A quick spray of her Channel No 5 and she was ready.
Daisy walked into the lounge and smiled at Stevie.
“Hi, babe. Will I do?”
“Wow, you look divine darling. Really amazing.”
Stevie stood up and walked over to her, putting one arm around her back and the other on her bum. They looked into each other’s eyes and slowly came together and kissed passionately. Stevie pulled her towards him, she didn’t resist, and pushed his hard on up against her. He could feel her manhood too. The kissed for what seemed like ages and then sat down on the sofa.
Daisy’s skirt was so short when she was standing, but when sitting down it hid nothing. Stevie looked down at her stockings and the skin in between them and her colourful panties. In his minds eye, she couldn’t have looked any better.
“My god, Daisy, you look sublime. I cannot tell you how much I want you. You are the most sexy woman ever.”
“I love being called a woman. I am so happy you like my outfit. I wanted to be as sexy as I could for you.”
She lent forward and kissed him. Her hand then slid up his thigh until she was stroking his crutch. His cock was so hard it was almost splitting open his tight jeans. He was more turned on than he had ever been. They had gone past the point of no return, it was about to start and Stevie couldn’t wait.
Daisy stroked his trousers and looked at him, smiling.
“Wow, that feels nice. Is that for me, babe.”
She kissed him and undid the button. Then the zip went down and she slide her hand inside. He wasn’t wearing any shorts. She liked that a lot. Taking his cock in her hand she moved it up and down.
“Mmm, I bet that tastes nice. Do you mind if I give it a try?” The wasn’t any thought of doubt but she wanted to ask anyway. It made her feel really horny.
“Well, if you must. Ha-ha. Please take me in your mouth. I need that so much.”
Daisy pulled his jeans apart and moved her head down onto his throbbing member. It was about seven inches long and was cut. The purple helmet slid inside and she licked and gently sucked. She had not sucked a cock for about two years and wanted it as much as Stevie wanted her to do it. He pulled his trousers off and leant back opening his legs really wide. Daisy just got more passionate. She whined, groaned and he could hear her slurping. The best sound.
After about five minute of this she stopped and looked up at him. She put her lips on his, their mouths opened and their tongues played with each other.
Then Stevie moved around so he was kneeling next to her head.
“I want to look at your panties and stockings while you finish me off. I want to see that it is a guy dressed up sucking me. I need to cum knowing that I am indeed having gay sex with a tranny.”
Daisy, moved around so that her panties were in full view. She was hard too and wanted him to know. Stevie placed his hand on his cock and placed it into her mouth. He didn’t let go but started wanking into her mouth. She sucked and licked and put one hand between her legs. Stroking herself whilst sucking was making her feel perfect. Stevie felt the same. He was fore-filling a dream. He held her head and looked down at himself. She was a guy. She was dressed up like a girl and looks beautiful. He knew he was close and told her so.
“Darling, I am going to fill you mouth with my juice. I need you to swallow it all. Oh babe, babe, babe!”
At that moment the sensation welled up inside him. He saw this cross dresser sucking him and shot his load. He had never felt so horny in his life and this was by far the best blow job he had had.
Daisy pulled away and swallowed it all up, making sure he knew what she was doing. Then Stevie, moved down and kissed her full on the mouth. His tongue delving deeply inside. They passionately kissed for a couple of minutes. They held hands and looked into each others eyes.
“My turn, I think.”
With that Daisy positioned herself next to Stevie’s head and keeping her panties on, she moved them to one side and took out her cock. He hadn’t thought about this part of sex with a guy. 'Of course I have to suck her too, it would be rude not to.' He felt a little reticent at first but then very quickly started to like it, more than a little. He was sucking a hard cock and was feeling so at home and right within himself. The feeling that he was actually sucking a guys cock made him want more. This type of sex was what he’d been graving all these years. It was the best.
As Stevie sucked he suddenly started to think of Daisy cumming. He wasn’t sure about that and didn’t know if he could swallow himself. Then, almost on cue, she took her cock out of his mouth and leant down and kissed him.
“Babe. When I am alone, I always drink my own cum. I want to empty myself into your mouth but I want to swallow it myself. When I cum, can I kiss you and take it into mine and gulp it down.”
Stevie hadn’t expected that but loved the idea. Wow, how horny was that. Cumming in my mouth and then kissing it out and drinking. She really was the best.
“Of course you can my love. You can do that as much as you like. No problem.”
“I like it every time. I can be the sexy girl who swallows us both. It can be our little secret.”
She winked at him and got straight back to it. As Stevie had done, she started to wank into his mouth. He simply loved that and even the thought of it was unreal.
It didn’t take very long. Stevie was sucking and Daisy was wanking faster and faster. Then the moment arrived and Daisy’s cum shot into his mouth. It was quite a lot and he sat there with the cum almost spilling out of his mouth. As soon as she had finished, she moved, opening her mouth on his. Her tongue searching for her cum, she sucked it into her mouth and swallowed every drop. Then, as before, they kissed.
After a little rest, Stevie knew that the oral sex part was just the build up to having proper sex. Anal. He had never done that but always wanted to this was his chance. He wanted to fuck her and noticed on the table a bottle of lube. He asked to have it and she willingly gave it to him. Then she helped him rub it on. She quickly removed her silky panties and knelt on the floor. She looked over at him and then looked behind herself. That was the request he wanted.
Stevie positioned himself behind her and placed his rock hard, oily cock up against her hole. He squeezed her cheeks and then slide himself inside her. He gave her a hard, but affectionate slap. Her hole tightly gripped his prick. He pulled out and then in again. It was too wonderful for words. She wiggled her bum and he pumped her, pulling it right out and then right in. It was the best.
After a few minutes he told her to lay on her back on the sofa. Again he wanted to see himself fucking a gay tranny, and, oh boy, he did. The turn on was absolute. He couldn’t wait one more second. Stevie pulled out, hand on cock and wanked himself off over her stomach. He came with such a feeling of excitement and happiness that it almost overwhelmed him.
He looked down and saw that she was busy collecting up all his cum on her fingers, licking it off and swallowing. They were both in heaven. The best for both of them.
Over the next few hours they made passionate love to each other and decided that they should do this lots. So, both Stevie and Daisy started this night thinking that it would be a nice evening of horny sex, but ended up being the start of a wonderful friendship.
People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He still found women attractive and some men. The thought or even the sight of a transvestite mad him very nervous. That was probably fueled by growing up in the sixties and seventies. There was a great ‘no go area’ when it came to trannies. Society made one think that these types of people were in some way sick and perverts.
Stevie had found the odd cross dresser desirable. He felt shame that he could experience this. The feeling did not go away. There were many sites for him to look at transvestites and see them having sex. It started to get better and he really enjoyed it. If only he had the courage to find someone that he could have fun with.
Then, one day, out of the blue a breakthrough came. Stevie was watching the news and on came this report about a catastrophe at a gay club. As some of the party goers were being interviewed he watched with interest. They were just normal gay guys, then suddenly this Transvestite came on the screen. She looked amazing and as she spoke Stevie felt his cock getting hard. That clinched it, his mind was made up. You didn’t get a hard on looking at a tranny unless you really fancied them. He had to get laid by a tranny.
Trying to avoid going to a gay club or bar, he eventually found a dating site where people who were nervous could meet safely. He was on the site for weeks and then one day met a great looking tranny called ‘Daisy.’ She was everything he wanted and was also quite inexperienced. They could both have fun and fumble about without worrying about anything.
So, after a few nights out having some drinks and a meal, the night came. Stevie didn’t mind going out with Daisy because she looked like a woman, and a very attractive one at that. They went back to Daisy’s place and both got themselves ready, washing, changing, and getting relaxed.
Stevie just washed and sat in the lounge waiting in anticipation, his bulge in his trousers said it all. Daisy decided to make herself look really sexy for him, and it worked. She washed and slipped on a dark blue basque and seamed fish net stockings with big lace tops. Then this very short black, wet-look dress, which just about stopped at the height of her stocking tops. A new pair of silky panties and re-did her make up. A quick spray of her Channel No 5 and she was ready.
Daisy walked into the lounge and smiled at Stevie.
“Hi, babe. Will I do?”
“Wow, you look divine darling. Really amazing.”
Stevie stood up and walked over to her, putting one arm around her back and the other on her bum. They looked into each other’s eyes and slowly came together and kissed passionately. Stevie pulled her towards him, she didn’t resist, and pushed his hard on up against her. He could feel her manhood too. The kissed for what seemed like ages and then sat down on the sofa.
Daisy’s skirt was so short when she was standing, but when sitting down it hid nothing. Stevie looked down at her stockings and the skin in between them and her colourful panties. In his minds eye, she couldn’t have looked any better.
“My god, Daisy, you look sublime. I cannot tell you how much I want you. You are the most sexy woman ever.”
“I love being called a woman. I am so happy you like my outfit. I wanted to be as sexy as I could for you.”
She lent forward and kissed him. Her hand then slid up his thigh until she was stroking his crutch. His cock was so hard it was almost splitting open his tight jeans. He was more turned on than he had ever been. They had gone past the point of no return, it was about to start and Stevie couldn’t wait.
Daisy stroked his trousers and looked at him, smiling.
“Wow, that feels nice. Is that for me, babe.”
She kissed him and undid the button. Then the zip went down and she slide her hand inside. He wasn’t wearing any shorts. She liked that a lot. Taking his cock in her hand she moved it up and down.
“Mmm, I bet that tastes nice. Do you mind if I give it a try?” The wasn’t any thought of doubt but she wanted to ask anyway. It made her feel really horny.
“Well, if you must. Ha-ha. Please take me in your mouth. I need that so much.”
Daisy pulled his jeans apart and moved her head down onto his throbbing member. It was about seven inches long and was cut. The purple helmet slid inside and she licked and gently sucked. She had not sucked a cock for about two years and wanted it as much as Stevie wanted her to do it. He pulled his trousers off and leant back opening his legs really wide. Daisy just got more passionate. She whined, groaned and he could hear her slurping. The best sound.
After about five minute of this she stopped and looked up at him. She put her lips on his, their mouths opened and their tongues played with each other.
Then Stevie moved around so he was kneeling next to her head.
“I want to look at your panties and stockings while you finish me off. I want to see that it is a guy dressed up sucking me. I need to cum knowing that I am indeed having gay sex with a tranny.”
Daisy, moved around so that her panties were in full view. She was hard too and wanted him to know. Stevie placed his hand on his cock and placed it into her mouth. He didn’t let go but started wanking into her mouth. She sucked and licked and put one hand between her legs. Stroking herself whilst sucking was making her feel perfect. Stevie felt the same. He was fore-filling a dream. He held her head and looked down at himself. She was a guy. She was dressed up like a girl and looks beautiful. He knew he was close and told her so.
“Darling, I am going to fill you mouth with my juice. I need you to swallow it all. Oh babe, babe, babe!”
At that moment the sensation welled up inside him. He saw this cross dresser sucking him and shot his load. He had never felt so horny in his life and this was by far the best blow job he had had.
Daisy pulled away and swallowed it all up, making sure he knew what she was doing. Then Stevie, moved down and kissed her full on the mouth. His tongue delving deeply inside. They passionately kissed for a couple of minutes. They held hands and looked into each others eyes.
“My turn, I think.”
With that Daisy positioned herself next to Stevie’s head and keeping her panties on, she moved them to one side and took out her cock. He hadn’t thought about this part of sex with a guy. 'Of course I have to suck her too, it would be rude not to.' He felt a little reticent at first but then very quickly started to like it, more than a little. He was sucking a hard cock and was feeling so at home and right within himself. The feeling that he was actually sucking a guys cock made him want more. This type of sex was what he’d been graving all these years. It was the best.
As Stevie sucked he suddenly started to think of Daisy cumming. He wasn’t sure about that and didn’t know if he could swallow himself. Then, almost on cue, she took her cock out of his mouth and leant down and kissed him.
“Babe. When I am alone, I always drink my own cum. I want to empty myself into your mouth but I want to swallow it myself. When I cum, can I kiss you and take it into mine and gulp it down.”
Stevie hadn’t expected that but loved the idea. Wow, how horny was that. Cumming in my mouth and then kissing it out and drinking. She really was the best.
“Of course you can my love. You can do that as much as you like. No problem.”
“I like it every time. I can be the sexy girl who swallows us both. It can be our little secret.”
She winked at him and got straight back to it. As Stevie had done, she started to wank into his mouth. He simply loved that and even the thought of it was unreal.
It didn’t take very long. Stevie was sucking and Daisy was wanking faster and faster. Then the moment arrived and Daisy’s cum shot into his mouth. It was quite a lot and he sat there with the cum almost spilling out of his mouth. As soon as she had finished, she moved, opening her mouth on his. Her tongue searching for her cum, she sucked it into her mouth and swallowed every drop. Then, as before, they kissed.
After a little rest, Stevie knew that the oral sex part was just the build up to having proper sex. Anal. He had never done that but always wanted to this was his chance. He wanted to fuck her and noticed on the table a bottle of lube. He asked to have it and she willingly gave it to him. Then she helped him rub it on. She quickly removed her silky panties and knelt on the floor. She looked over at him and then looked behind herself. That was the request he wanted.
Stevie positioned himself behind her and placed his rock hard, oily cock up against her hole. He squeezed her cheeks and then slide himself inside her. He gave her a hard, but affectionate slap. Her hole tightly gripped his prick. He pulled out and then in again. It was too wonderful for words. She wiggled her bum and he pumped her, pulling it right out and then right in. It was the best.
After a few minutes he told her to lay on her back on the sofa. Again he wanted to see himself fucking a gay tranny, and, oh boy, he did. The turn on was absolute. He couldn’t wait one more second. Stevie pulled out, hand on cock and wanked himself off over her stomach. He came with such a feeling of excitement and happiness that it almost overwhelmed him.
He looked down and saw that she was busy collecting up all his cum on her fingers, licking it off and swallowing. They were both in heaven. The best for both of them.
Over the next few hours they made passionate love to each other and decided that they should do this lots. So, both Stevie and Daisy started this night thinking that it would be a nice evening of horny sex, but ended up being the start of a wonderful friendship.
Becky
- 22.10.2020
- 61
- 0
- Category:
- Gay Male
