John was nineteen years old. He had grown up on a large housing estate where there were plenty of other boys of his age to hang around with. He had been part of a gang of about twelve friends. One of the gang was a boyish-looking girl who always made sure that she was in on all of the games they played and the trouble that they got into from time to time. She always dressed in boy’s jeans and tee-shirts and although none of the boys in the gang had ever seen what she wore under her jeans, the consensus was that she wore boy’s underwear too. Her name was Ashley but the boys always simply called her Tom, which was short for tomboy.

John was pushing his bike up the street at eleven in the morning, intending to go home and have a bite to eat for lunch. Nobody else would be at home until this evening, and so he had planned to spend the afternoon having a long and slow masturbation session. He had never had a girlfriend and no sexual experience. All of his sexual relief so far had been by masturbating. He was already planning to get out his favourite pair of panties to put on. He had had his fetish for panties for years now. At first, he would wander around the estate where he lived, looking at women’s panties out on the washing lines to dry. He never dared to try stealing them, but would fantasize about what he had seen. He would imagine what they might feel like against his prick and what they would look like on a woman. Once he was back at home in the privacy of his bedroom, he would masturbate, continuing his fantasies.

A year or so back, his curiosity had got the better of him. He wanted to feel and touch the real thing, so he had taken the plunge and walked into a clothing shop and purchased six pairs of women’s panties. Now he could properly fulfill his fetish. His favourite way of pleasuring himself was to wear a pair of panties to masturbate in and when he reached his orgasm he loved to cum in them, feeling his juices soaking into the fabric. He was beginning to get hard already as he thought about the session he had planned in his mind for this afternoon and knew that his hard-on would remain until he dealt with it later.

As he passed a house a few doors down the street from his own house, John saw the tomboy girl. He hadn’t seen her for at least three years as he had been away from home working and living near the job. Her boyish looks were still the same as he remembered. He looked her up and down and observed that she still had a flat chest and narrow boy hips. She was dressed in jeans and a summer tee-shirt. She had her hair styled like a boy’s.

“Hi, John,” she called, waving to him. “Aren’t you going to stop for a chat?”

“Hi, Tom. Sorry, I mean, Ashley,” he replied as stopped and leaned his bike against her garden wall.

“I haven’t seen you around for years,” she said. Where have you been?

“It’s been three years to be precise,” he told her. “I’ve been away working.”

“It’s good to see you again. What are you up to now?” she enquired.

“What, now this afternoon you mean or now for the rest of my life?”

“I mean now for the rest of the day. Do you want to come indoors? We can have a bit of a catch-up on what’s been happening. There’s only me at home until my brother gets in. I don’t know when that will be.”

And so John followed her into her house and they stood in the kitchen. As they chatted about the past, he was aware of her glancing down at the lump in the front of his jeans. His hard-on was still there.

“Actually,” she said, nodding in the direction of John’s prick. “Judging by that, it looks like you’re very pleased to see me. I seem to remember that you were always pestering me for sex back in the day, but it never happened, did it?”

“No. It was all talk back then I suppose.”

“I bet you wanked when you went back home after we had been hanging about together though. Fantasized about fucking me I expect.”

“Well, what else could I do? I fancied you like mad but there was always the rest of the gang hanging around. Anyway, you were always avoiding me. Did you fuck any of the others in the gang? I bet you did.”

“No, I didn’t actually. I did give one or two of them a quick wank but that was all and they spent all the time trying to get a hand down my knickers, which I always managed to stop them from doing. I’ve never been fucked. Mind you, with that hard-on you’ve got there, it looks like I may be all change now. I suppose you will have had some experience by now. Living away from home, I suppose you would have had loads of girls. I should think that you could teach me a trick or two.”

“Sadly not. I’ve had the odd girl give me a hand job, and apart from seeing to myself, that’s about it.”

“And what about that panty thing?”

“What panty thing?”

“Well as I remember, you had a bit of a reputation of being a panty fancier. The boys used to say that you wandered around looking at knickers on washing lines.”

“Would that bother you if it was true?”

“No, not at all. In fact, it turns me on a bit thinking about it. So what do you do with them? Do you wear knickers instead of men’s underpants?”

“No, that’s not how it works. Look, I don’t know if I want to talk… Oh well, fuck it. I’ll tell you. I put them on to wank in them. They feel good. I like the feeling when I cum in them. There you go. My secret’s out. And if you have got any that you don’t want, I wouldn’t mind the odd pair.”

“I might have, but haven’t you got some already? You must have if you wank with them.”

“Well, I’ve got a few pairs. But sometimes it would be good to try some different ones.”

“I suppose you pinched them off washing lines.”

“No, I didn’t! I bought them actually.”

“Wow. As in bought from a shop? You mean you walked into a shop and bought women’s knickers? Actually, the whole idea of this panty thing is making me feel a bit turned on,” she admitted. “Let’s do something about it, shall we? I mean, you’re standing there with a flagpole in your jeans and I’m getting horny too.”

“What do you want to do? Go up to your bedroom?” John asked

“No, we can’t do that. I already told you, I don’t know what time my brother will be home. We could go for a bike ride together. Why don’t we go out down the lanes?”

“That sounds good.”

They decided that it would be good to take a bit of lunch with them and go out for the rest of the day.

Ashley prepared a few sandwiches and biscuits for them both and got a couple of fruit drinks out of a cupboard. She put everything in a backpack which she had retrieved from a kitchen cupboard, and then wrote a short note to her mother to tell her where she was going in case they got back late. She left the note on the kitchen table.

John couldn’t help noticing that under her thin tee-shirt she did not have a bra on. In fact really, from what he could see, she didn’t have anything that needed a bra. He was quite excited for some reason that all he could see were what amounted to just a couple of protruding nipples pressing against her tee-shirt with no swell of breasts that he would have expected her to have at nineteen years old. He had a sly look at her bum in her jeans while she had her back to him rinsing her hands at the sink, and had to admit to himself it was a nice bum although that also looked a bit boyish and her hips were quite narrow.

“I’m just going up to my room to get a couple of things and then we can go.”

“What things?”

“Well, some spare knickers for a start. There could be a bit of juice flowing, and anyway I want to see what you look like in a pair of them.”

“I can’t wait. And some condoms maybe?”

“No, we won’t need those. I’ll explain later. I will bring some lube though. I will be a bit tight.”

“So you really do want to go the whole way then?”

“Of course I do. And I guarantee that I will surprise you. By the way, I don’t suppose that you’re into pissing by any chance? It’s a bit of a thing of mine.”

“It’s not something I know anything about but I’ll give anything a go.”

“Well, that will be another surprise for you then. You may even enjoy it.”

She went off upstairs with the backpack and was back in a few minutes. The backpack looked to have quite a bit of stuff in it now.

Ashley got her bike out from the shed and they cycled off down the street and out into a country lane that was only five minutes from the edge of the housing estate. After almost half an hour of cycling down lanes, Ashley called to John to say that they should stop for a rest, so they pulled up on a narrow edge and she announced that she was feeling peckish.

There was a bit of a clearing in between some hedgerows before a farm fence prevented further exploration, so they sat down on the ground between a few bushes and she opened her backpack and took out the bag of sandwiches. It was somewhere around mid-day so pretty much time to eat.

“That’s a fair bit of stuff you’ve got in your bag. What else is in there?” John enquired.

“Well, there’s three pairs of knickers, the lube, a towel, some wipes, a couple of plastic bags, some tissues, and a roll of toilet paper.”

“What do you need all that stuff for?”

“You’ll see in a while. In fact, you’ll be glad I brought it.”

They sat on a flat soft piece of grass and had lunch, chatting while they ate. Lunch over, Ashley stood up and announced that she needed to pee, and said that she was quite full as she had been saving it. Then with her back to John, She immediately started to undo her jeans right there in front of him. This excited him and he asked her if she was going to go behind the bushes, although he really hoped that she wouldn’t. She didn’t. She continued to take down her jeans and her knickers were in full view. Then she took her jeans right off and stood for a few moments in her tee-shirt and knickers. She paused for a few moments as if to ensure that I was enjoying the show. Her knickers were full waist low cut white cotton. His favourite.

“I’m going to squat and piss in my knickers. It’s my fetish. It turns me on. I often do it before I masturbate. It won’t put you off will it?”

“No. Actually, it’s having the opposite effect just thinking about it. Are you going behind the bushes?”

“No, I’m going to do it right here so that you can watch.”

She squatted down and spread her legs with her back still facing John and began to pee. It poured out, soaking the knickers, and hitting the ground. She stopped peeing and told him to feel her through her knickers. As he reached down from behind and began to feel her she started to pee again onto his hand. And then he got a shock. Instead of what he expected to find, he felt that her pee was coming out of what felt very much to him like a small penis. A little bit more exploring and he found a tight little scrotum with a pair of tiny balls.

He began to get even more aroused. He took his hand away while she continued to pee. She finished and stood up. The knickers were soaked and as she turned around to face him, John could see a small erection sticking out, almost fully visible through the soaked cotton fabric of the knickers.

“Okay. So now my secret is out. I’m not female. What do you think? Are you completely put off?

“No. Just confused. I nearly came just then when I felt you.”

“Don’t do that. Not yet. We have plenty more to do.”

As she faced John and pulled the knickers down, he saw what he had been feeling. Sticking straight out in front of her was a small hard prick, only about three inches long. Below it, as John had suspected, was a tiny pair of balls which the tight scrotum held close to her prick. There was no pubic hair. John was fascinated.

“So. What do you think?” she said as she pulled the towel and other stuff from the rucksack and began to clean and dry herself. I’m a proper man.”

“Yes, I can see that. How have you managed to keep it a secret for all this time? I assume you’ve let other boys know.”

“No. You’re the first. Well, my parents know obviously. They treated me like a girl all the time I was growing up. I think they had rather hoped for a girl when they had me. There was some talk of seeing a specialist about it but that never happened. When I got older and in your gang, everyone assumed I was a girl, so I acted the tomboy. And now …”

“So what about now? What are we going to do? I mean, we are clearly not going to have sex are we.”

“There are things we can do. We can still have sex. Don’t worry. You will go home satisfied. I promise. Now put these on for a start.”

Ashley offered John a pair of black cotton knickers after extracting them from the backpack. John took off his jeans and underpants. As he did so, his prick stood straight out. It was a good seven inches long and very thick. His balls were also large and hung well. Ashley gasped quietly. As John put the knickers on, Ashley pulled another pair, pale blue cotton one, from the bag and put them on.

“Now, how shall we do this? There’s no way you are going to be able to get that in me. It’s huge."

“But I don’t see how I could fuck you anyway. I mean you haven’t got a… “

“You really are nieve. How do you suppose other men fuck men? Anyway, as I said, that may not be on the menu."

“So what is on the menu?”

“Well first of all, I’m going to fuck you. You don’t mind do you?”

“I’ve never done that before. Will it hurt me?”

“I haven’t done it either. But you’ve just seen what I’ve got. It’s not going to hurt you, is it? In fact, I doubt that you will even feel it. Now, get down on all fours with your bum sticking out and I will do the rest. One thing though. I may be tiny, but when I cum… Well, you’ll see for yourself. Or I should say you’ll feel it.”

John did as he was told. Ashley knelt down behind him and pulled John’s knickers halfway down his thighs. Then he did the same with his own.

“I’m just going to get this lube on my prick and then I’m going to go for it. Are you comfortable?”

“I’m fine. Do what you want to do. And you’re sure it won’t hurt me?”

“No, it won’t hurt you.”

A few moments later Ashley’s prick entered John. He winced and tightened at first, but then relaxed and he felt Ashley began to pump slowly in and out. He could hardly feel it. Ashley kept this up for about five minutes and then his body went rigid.

“Ah! … Ah! … That’s it, I’m going to cum! Oh, fuck! Here it comes!”

John felt the wet warmth of Ashley’s cum spurting up inside him. He was surprised at how much of it there was. It seemed to keep on gushing for what seemed like a couple of minutes, and as it did Ashley continued to move slowly in and out of John. As he withdrew, his cum trickled out and dripped onto the panties where they stretched across John’s thighs.

John’s erection was harder than ever. He needed to do something. They both stood up and as John looked at Ashley he saw that his little dick was now soft and only about an inch and a half long. Ashley pulled up his knickers. John took his right off as they were wet and sticky.

“That was fantastic," said Ashley. “Now what are we going to do with you?”

“What do you suggest? I really need to get rid of this hard-on. My balls are beginning to ache.”

“Well for a start, put this other pair of knickers on. I know you like that.”

He produced another pair of knickers, pink ones this time, and John put them on.

“Okay then. Panty job or blow job? Or even a bit of both if you like.”

“I wouldn’t mind trying a panty job. As I told you earlier, I’ve only ever cum in knickers wearing them myself. Are you going to kneel down like I did so that I can rub on you that way?”

“If that’s what you want to do.”

Ashley knelt down on all fours and pushed his panty-clad bum out. John eased his own panties down just enough to release his erection then knelt down behind Ashley. He pressed himself against Ashley’s panties and began to slowly slide up and down, rubbing himself against the soft cotton fabric covering Ashley’s bum.

“Fucking hell, that feels so good,” cried John. “I’m going to try to make it last.”

“Keep going for as long as you like. If you want to stop before you cum, I’ll give you that blow job to finish you off.”

“I really think I’d like to cum like this. Actually, can I put my prick inside your panties?”

“If you want to.”

John moved away a little, pulled Ashley’s panties slightly to one side, then pushed his prick in under the crutch of them. He started pumping back and forth again.

“Fuck! That feels even better. I think I’m nearly there.”

“Okay. Go for it. Spread some of the lube on me. It will feel really good, I promise. Go on. You can reach the tube. It’s just down on the ground beside you.”

John reached down, picked up the lube, and squirted some down inside Ashley’s panties and onto himself.

“Look, I know we agreed that I wouldn’t fuck you, but can I just put the end inside you?"

“Well oaky, but don’t shove it in any further.”

“Okay. Just the end.”

John adjusted his position so that he could insert the end of his prick into Ashley’s opening, and pushed it in. Ashley let out an audible gasp.

“Fuck. I like that,” cried Ashley. “And it didn’t hurt. Push it in some more.”

John slowly pushed little by little until his whole length was inside Ashley.

“Is that hurting you?”

“No. Just get on with it. I want to feel you pumping. I want you to fill me with your cum. Now! Put your hand around and wank me. I’m hard again.

John did as instructed. As he slid in and out of Ashley, he rubbed his tiny prick at the same time.

"Fuck! I’m cumming,” announced Ashley.

“Ah! Ah! Aah! So am I! Here it is!

As Ashley pumped his cum out into the front of his panties, onto John’s hand and onto the ground under him, John began to empty himself up inside Ashley in huge spurts. Before he completely finished, he pulled out and pumped the rest of his stuff into the fabric of Ashley’s panties.

“So what do think about all that then?” Ashley asked.

“Well, I don’t think I’ve felt this satisfied before. What’s next?”

“I think that going home is next. Then we can sort out another meeting.”

To be continued...