After eating lunch at his favourite deli Stan was walking back home when he saw an astoundingly beautiful woman coming toward him. She had long, shimmering brown hair, the most innocent eyes he’d ever seen, a cute little button nose and a flawless body. Her tits were big and perky, her legs were long and thin and her waist was slim.
She looked like the woman he had always dreamed of being with and there she was coming right towards him. When they passed he offered her, hello and she smiled at him in return.
At that moment he was in love. He knew he’d have to be with this woman if it was the last thing he did.
To gather a little more information for his mission of love he turned around and followed her at a safe distance. She walked a few more blocks and then stepped into a gynaecological clinic where it turned out she was a doctor. He got a nice little surprise when she started changing where he could plainly see her.
She had a fabulously sexy body and under that skirt and top, she was wearing a very hot bra and panty set with a garter belt that made his dick stiff in his pants. How could he possibly get this girl to go out on a date with him or to just let him into her pants to give her a good fuck?
He couldn’t very well make an appointment at the gyno office so he turned back and started walking home again. His mind was racing with ideas for how to make this girl his but nothing was coming.
He could wait outside her office and ask her out when she finished the work day but he figured that would be too stalkerish. They needed some way to meet.
When he got back home he saw that some of his mother’s laundry was sitting in a basket next to the washer and that’s when his genius idea came: he would dress up like a woman and make an appointment with the doctor so she would have to see him!
It didn’t really occur to him that perhaps dressing as a woman would be even weirder than just asking her out when she finished her work day but this was a horny young man with an ingenious plan and nothing was going to derail him from it.
He was alone in the house so he took his time looking through his mother’s stuff to find something that would fit him well. She was a fairly stylish woman for her age and she had maintained a slim body so it wasn’t all that hard to find an outfit that he thought would be good-looking enough.
He ended up going with a pink bra and panty set, a short green dress and a pair of black stockings. The experience of putting everything on was far more arousing than he thought it would be.
He started with the bra and panties and they felt really good going over his skin, especially when the panties cupped his balls. He was puzzled at how aroused he was becoming while changing into a crossdresser. There was nothing wrong with being, even more, aroused going into her office though. That would only make whatever happened more fun.
He put on the green dress next and as it fell over his shoulders and down his body he felt a wave of femininity wash over him. It was really weird to feel like a woman for a brief second but there was something about it that he really liked too.
Maybe being a cross-dressing boy wasn’t all that bad. Maybe it was something he’d end up doing a lot more, especially if his plan worked out well. The stockings were the final piece of his outfit and they were the most arousing.
The nylon slid up his legs and caressed his soft skin so beautifully and sensually. He understood at that moment why so many guys were obsessed with nylons and why women seemed to like wearing them so much. If they felt that good there would be no reason not to wear them all the time.
He completed the outfit with a cute little hat that matched the green dress and then walked out the door with newfound and somewhat puzzling confidence.
Why did he feel better as a woman than he ever had as a man? He walked down the street with a sexy sway in his hips and even though he looked a little boyish he could tell that people actually thought he was a woman. When he arrived at the gynaecologist’s office and asked for a walk-in appointment they were happy to have him. As it turned out she had an opening in her schedule for that day and she would be able to give him all the time he needed.
Twenty minutes later the doctor appeared in the waiting room and beckoned him to the examination area. He looked at her ass as they walked down the hallway and he could feel a stirring in his pants at the sight of those tight cheeks. He was thinking about what it would be like to kiss them when she opened the exam room door and pointed him inside.
“I’ll need you to take off your panties and take a seat on the table there. I’ll be back in just a moment.”
She stepped outside to give him privacy for change and Stan tried to puzzle out what he should do. Should he just keep his clothes on and tell her that he had become a crossdresser as an excuse to see her? Should he pull off his panties and let her discover his throbbing cock? What would happen if she was mad at him for tricking her?
She would probably call the cops and he’d get arrested for something truly embarrassing. He didn’t even want to think about what would happen if he was taken down to the police station and put in jail wearing a dress and stockings.
He considered every option and decided the best option was to take his pants off, sit in the chair with his legs spread and let the beautiful gynaecologist discover the dick between his legs.
When she came back in a few minutes later she put on a pair of gloves and slid between his legs to begin her examination. Obviously, he didn’t have a vagina so it didn’t take her more than a cursory glance to figure out his ruse.
“Oh my God!” she said with genuine surprise in her voice, “You have a penis! You’re not a woman at all. What’s going on here?”
“I’m sorry, I can explain,” Stan stammered, “I saw you when I was walking home from lunch today and I thought you were the most beautiful woman in the world. You were so pretty and so sexy that I just had to see you again. I didn’t even want to wait until the end of the work day so I went home and put on something from my mom’s closet so I could be one of your patients, all of whom are the luckiest men in the world.”
He was telling the truth when he explained how he had become a crossdressing boy and he wasn’t sure how she would react. He was hoping that she would be so charmed and aroused that she would want to fuck him right there in the office, of course. Things were tenuous for a few seconds and then he saw a sweet smile cross her face and he knew that at the very least she wouldn’t be calling the police on him.
“You know, I think that’s one of the sweetest things a guy has ever done for me. It’s a little weird, sure, but I’m a little weird too so I don’t mind. My name is Sharon, by the way.”
“You can call me Stan,” he said, reaching out to shake her hand.
“Well Stan, since you made an appointment it seems like you should get a proper examination just like any other woman would.”
That caused Stan’s heart rate to increase because he had no idea what she meant. How could she examine him, he was a man. For some reason, he wasn’t thinking about his asshole. Of course, she could shove her fingers in there and give him the examination of a lifetime!
She dipped her gloved hands into the bucket of industrial strength lubricant she kept for her examinations and spoke, “This is going to feel a little uncomfortable my little crossdressing cutie. Don’t worry, it won’t hurt too badly and I’m certainly not doing any permanent damage.”
Stan was still a little tense but he forced his asshole to relax so she wouldn’t have to push too hard to get past his anal ring. As it turned out Sharon was something of an expert at fingering a man’s asshole.
Her knowledge of the human body enabled her to find his prostate almost immediately and when she started massaging him back there he could hardly keep it together. He was moaning and writhing around on the table and telling her how good it felt to have her fingers up there. When she started stroking his crossdresser dick while fingering him he was in heaven.
The cute gynaecologist wanted to get fucked by her new sissy lover and he was definitely willing to pound her hot pussy with his big cock.
They switched positions so she was the one sitting in the exam chair with her legs spread wide and his dick was soon balls-deep in her hot hole. It was the best sex he had ever had and he could only attribute it to her naughty behaviour with the fingering and his absolute love of his new cross-dressing behaviour. It was kinky crossdressing sex and it left him quivering with desire.
He fucked the beautiful babe missionary style and then she got onto her hands and knees and there was some doggy-style crossdresser fucking. His big cock felt so good in her warm pussy hole and his legs felt so good in the black stockings. Every time he thrust inside her he could feel them rubbing against the chair and against each other and he just kept getting more and more aroused.
When Stan was on the verge of cumming the sexy gyno doctor had him pull out and start feeding her mouth. She wanted to suck on his big boner and taste his cum. She even gave his balls some serious attention, licking and sucking at the hot sack to encourage his cum to shoot out. It wasn’t long before he was jerking his fuck meat and making it shoot all over her titties.
When he was finished he put his panties back on and his new gynaecologist told him that he would have to come back again for further treatment. He clearly had a problem with stiffness in his panties and she could take care of that with some intense therapy. That was the kind of offer he was sure to say yes to. When a beautiful girl wants to fondle your balls and let you fuck her you don’t say no. Stan was going to come back over and over again and he was always going to be a crossdressing boy when he did.
Check out – The honeymoon will never be the same
Back to Mistress Chat Line