Introducing Tony to Crossdressing

For as long as I can remember, I have always loved to try on women's clothes.

It started with my sisters knickers and bra's. Or my mother's tights. Or even all together. My mother's skirts dresses and blouses were too big. Sis's things never felt right.

I carried this kink, all alone. Even when I got married.

Eventually I did come out to my wife, after about five or six years.

Initially she was shocked. But not repulsed.

After a while she even accepted it, sometimes encouraged it. She helped select my first wig. Bought me my first cosmetics, to save her own. And showed me how to apply my make up.

We were similar sizes, and I was allowed to 'borrow' her clothes. Or if I needed it she would go to the shop and buy me what I wanted. There was always online shopping too.

Most of the time I was dressed up just for me. I felt more relaxed and happier wearing women's clothes. Not that I wanted to be a full time woman. (too tall for that) I simply enjoyed doing that maybe once a week. I could roam the house freely if she was at home.

On the odd occasion she would want me dressed up, so she could fuck me. Life was good.

Sadly we got divorced. Nothing to do with my dressing up.

I found myself a house of my dreams, detached, not overlooked mostly in a nice and quiet cul-de-sac.

The house next door, by my reckoning could see part of my garden from their upstairs window. So I installed a screen of sorts, allowing me to venture into my garden. Well onto the patio. There I could sit in the sun wearing whatever I liked.

My neighbours were hardly ever in anyway. He worked away abroad most of the time. She helped out in a shop. I knew her hours. They had a son, who was away at uni. I felt lucky to have such nice neighbours.

I had dated quite a few women, could never find the right one, so far.

There was also a crossdressing website, I frequently used. There were lots of friendly tips on how to apply new to me, make up. You could upload photos, so my crossdressing side was never alone. Although I would have liked some C.D company, most that I spoke to were only after one thing. I wouldn't have minded but they were not exactly what I would have been tempted to try.

Overall I was really happy with my lot.

From the window on my landing I could look onto next doors, back door, and the aisle that we shared. I had only opened the blinds.

Tony, the son from next door was back home. Must be yet another holiday. He was at their back door, with only his head peering around. Had no idea what he was looking for. Then the door swung open. There was Tony, stood there wearing white satin knickers, tights and a bra. I could see that he was aroused too. With another peer around he stepped out of the house.

Watching him and what he wore, had me wondering if it was his own things he had on. His mother was a lot shorter than him, and far too slim for the bra to fit, although she had a rather large pair of tits. But with my limited experience I was positive he was not wearing his mammy's underwear.

Now certain of him being alone outside. Tony rested against the wall, closed his eyes and began to touch himself. Feeling his bra, massaging his tits through his bra, eventually moving his hand lower down to feel the bulge in his panties.

It wasn't long until he freed his cock, it was impressive. About maybe seven inches and quite thick.

There he began to slowly stroke it, he pulled his foreskin all the way back, then brought it over his helmet, and wanked himself only moving his foreskin over his helmet. I could see on his face he was enjoying himself. Then he took longer strokes, all of his impressive shaft. He must have been close to cumming. He leant forwards, put his other hand in front of his cock and cum into his cupped hand. He tried to drain every last drop of sperm out of it. Then he licked all of it off his hand, licking his lips when he was done. Then he ran his finger over the tip, and took any drips up before sucking that clean too.

Once he was done he tucked himself back into his panties, went indoors and closed the door.

I was so hard after watching Tony relieve himself like that I had to do the same. There and then. Still hiding in the cover of the blinds I began to wank myself, all the while thinking about what I had just seen. It didn't take too long for me to start to cum. I cupped my hand and shot my load into it. At first I was unsure whether to lap up my cum, but if Tony could do it then so could I. It had been a good few years since I had last tasted my cum, and it tasted the same as I remembered. By the time I was sure the palm of my hand was clean, I began to enjoy the taste.

I had no intentions of getting dressed that day, but watching Tony and what he had done. I was having a shave and a shower, already planning what to wear.

When I was done I thought that I looked quite sexy, one of my best applications of make up, my wig didn't need much brushing. For a change I didn't teeter about in my high heels either.

I decided to have a coffee on the patio. The only thing wrong with the day was no breeze, I had a skirt on that would have blown around a lot, perhaps blowing up to show my stockings and suspenders.

There was a knock at the front door, I nearly choked. Not to worry the door was locked. Do what I normally done if someone knocked- ignore them.

After a minute or two Tony shouted over the fence for me. I bolted back in to the house, my heart nearly stopped. It takes at least ten minutes to remove all my make up.

I decided to shout and stay hidden. "Yes?"

"I need a hand."

"Can it wait? I was just about to jump in the shower."

"Suppose so."

"Give me five minutes."

Fifteen minutes later. I called round to see what he wanted.

"Thanks, my mother asked me to get rid of these." Tony pointed to a load of black bags. "I don't know where to take them."

I tried to give him directions to the tip, it just wouldn't sink in where he had to go.

"Tell you what, put them in my car and I'll take you there."

"Will you, thanks I owe you one."

I drove him there and watched him unload my car. Thinking back to when I was spying on him. I thought he would look good dressed up properly.

"When are you due back at uni?"

"I have another three weeks here."

"What a hard life eh?"

"I'm supposed to be studying now, just can't get motivated."

"Anything wrong?"

"No just missing being away, that's all."

"I thought you would have been glad to get home."

"Oh I am, its...its complicated that's all."

When we returned. "Coffee?"

"Go on then please."

We talked about this and that, I tried to find out what was 'complicated' but Tony wouldn't say. Eventually going back home.

I considered trying to get dressed again, decided against it.

The next morning, I was hidden at the window, hoping that Tony would be at it again. I had been there about fifteen minutes, and was about to give up. Thinking he was probably in his bed, after all he was a student.

Then their back door opened. Tony having a good look around, making sure he was hidden, stepped out again. Today he was in black. Bra, a thong showing his bulge and black hold up stockings.

Like yesterday he came out and rested against the wall, closed his eyes and began to pleasure himself. Only today I noticed he had on lipstick, and eyeshadow too.

While he touched himself his cock, freed itself from his thong. His foreskin withdrew by itself as his purple/red helmet grew.

I never had any real feelings to do anything with another male before. The odd fantasy maybe, but that was if I watched transsexual porn really.

Should I go and see if he needed any help? If he did would it be to empty his balls, or would it be his make up? Would I have the courage to even touch his cock never mind wank it off.

The thought of doing that though made me harder. Watching him had me hard enough already.

Then the plan hit me. I would be made up, wearing my wig, underwear and an open dressing gown in the morning. If Tony crept out again, then I would open the little top window while the blinds were open. He should get an eyeful of what I had.

Back to spying on Tony. As before he cupped a hand and shot his load into it, and licked it up. Now I wanted to taste what his spunk tasted like. Me in my best lingerie, sucking Tony, wearing a basque.

I just stroked my cock. I could cum later.

The next morning I was up extra early. I made sure I shaved all my stubble off. My legs were extra silky smooth. With extra cups of coffee I could apply make up without my hands trembling. Looking at myself in the mirror, I thought that I looked stunning. Now time to wait for Tony.

The only problem that I failed to see was I had to open the blinds, which meant to stay hidden I had to stand a bit further back. It wouldn't have been a problem if I were not wearing high heels.

Sure enough Tony's head appeared again. Now wait till the right time, walk to the window, reach up and open it. Tony, if he didn't jump out of view would see me looking femme.

It seemed to take him an eternity to go outside. He wore the same things that he had on yesterday.

Seizing my chance, I walked up to my window, took a deep breath and made sure the window catch made a noise as I opened it, paused a second, walked away and hid.

There was no way of knowing if he saw me. I had to walk past the window again and go downstairs. Shoulders back, chest out. I coolly strolled past he window. Heart pounding.

I made myself a coffee and went back upstairs to change back. Passing the window again I looked out. No Tony. But I was sure I saw some movement in their landing window.

I stood there looking out, playing with my hair and feeling my cock growing in my knickers.

Out the corner of my eye, I saw Tony, he had moved their blinds so he could see me better. I turned and looked directly at him. He stood there, I could see that he still had his bra on. I waved to him and closed the blinds, not knowing if he waved back.

I sat down on the stairs, giddy at what I had just done. Should I change back into my normal clothes? Or stay like this, and perhaps paint my fingernails? There was a knock at the door.

This time I crept up to the door and had a look through the spyhole. It was Tony. It looked like he had a dressing gown on. Could he still have his things on?

I opened the door, Tony come straight in, without any invite. We looked up and down at each other. No wonder Tony come straight in, he had his little bit of make up on, and letting his gown fall open. He still wore his lingerie.

"I have some things upstairs that you might want to try on."

"What like?"

"Well, there's a couple of wigs you could try on, and I have some spare breast forms." I looked at his slippers. "My shoes might fit you too." "If you want."

"I only have a couple of pairs of undies, they're all I can get."

"Don't worry I can help you a little."

We went upstairs, into my bedroom. "Here take a seat." Pointing to the chair in front of my dressing table.

I brought two wigs from my wardrobe. Both around shoulder length, one blonde, the other slightly darker than the one I was wearing already.

I thought Tony suited the blonde look better, he was not so sure.

"Is it your make up or your mothers? She will notice if you use it too much."

"No it belongs to me now. I had a girlfriend and she left it at my place just before she dumped me." "I've some G-strings of hers back down at uni too."

I brought out a pair of court shoes for Tony to try. "Have you tried high heels?"

"No not yet, I cant find any in my size."

"Don't worry, lets get you dressed then I'll show you some sites where I get mine from." "I'll bring a pair down for you to try as well." "Have a look through here and see what you want to put on. I'll be downstairs."

Leaving Tony to put on some clothes, I went and made us some coffee.

Tony walked into the kitchen. He had on a maxi dress, when he walked it clung to him. I could already see that he was starting to get aroused.

He sat at the breakfast bar, I gave him his coffee.

I asked. "How long have you been dressing in women's clothes?"

"For a while now. Since I could fit into my mothers things, until they got too small." "I used to have a friend. His sister caught us playing with each other and she made us dress up in her things. Or she would have told on us."

"What did she catch you doing?"

"We were playing with each others cocks, naked."

"I thought you said that you had a girlfriend"

"I did, I like girls more but I can go with boys."

"What did she make you wear?"

"Her dirty knickers, crop tops, mini skirts tights, all sorts really."

"Did it turn you on wearing them for her?"

"Oh yes, it turned her on too. She used to make me wank into the knickers she was wearing. She sucked me off once."

"What about her brother what did he have to do?"

"He had to either pay her, like empty out his pockets and give her all of it. Or she made him suck me off."

"Did you never have to suck him for her?"

"She didn't want to see his cock 'cos he was her brother, it would have been weird."

"Did you ever suck him?"

"Yes we sucked and fucked for a month or so. I had to go to uni."

"Did you fuck his sister?"

"She wanted to be on the pill before she started fucking around. Problem is that she's allergic to it I think."

"Do you like wearing women's clothes?"

"This is my first time wearing all the clothes, the wig and that. It's a lot better than I thought it would be." "Having some proper make up on would make it even better."

"There's no rush is there? Try on these heels first."

With the high heels on Tony stood above me in my slip-ons. Looking at his face, the light changed I could see what make up I should use and where to put it.

"Come back upstairs with me and I'll do your make up."

Tony teetered after me.

"Just take them off till we come back down."

Back in my bedroom. Tony sat there facing me. I managed to take off what he had put on, and began finding out that I was pretty good as a make up artist.

"There I'm done stand up and let me have a proper look."

Tony was stunning. He had become a she. "You look beautiful, have you had a look?"

Tony looked in the mirror. "Wow it's brilliant how you've done that." "I wish that I could have took my photo. But I best not in case the picture gets in the wrong hands."

"You can have a photo. You can join a crossdresser website and use it. Nobody will recognise you. Nobody is going to say that they have seen you on a C.D site either are they?"

I logged onto the site and showed him my profile.

"Are you sure about this?"

"If I was unsure then I wouldn't have put my face on here."

"Okay then I'll join...It is free isn't it?"

"Oh yes. Just log me out and follow the instructions to join, I'll get my phone to take some pictures, you choose the best one then we'll delete them."

While taking the pictures they become more and more risque. I plainly see that Tony was getting turned on. I tried to hide the fact that I was too.

Then Tony had to ask the question. "Have you ever been with a man?"

"I fooled around with a mate at school, only touching." "Then me and the ex were going to have a threesome with a bloke but he seemed more interested in me, which put her off it." "So not really no."

"Would you want to try it with me?"

"Dressed like that then I think I would."

"What about if I was just me in normal men's clothes?"

"No, I don't fancy men." "What about you?"

"I want you so much, while your looking like that."

She moved in and kissed me. I could taste her lipstick, I kissed back.

I knew that in reality I was kissing a man. I couldn't care. She was gorgeous.

We wrapped our arms around each other and locked our lips together, mixing the colours of our lipstick. Pressing our fake tits into each others.

Tony began to move her hand towards my hard cock. So far so good, it felt as if I was with a woman. Tony freed my member from my panties, and began to stroke it. I had to stop her almost straight away. I couldn't believe how turned on I was. I felt that I could have cum then.

I let my hand find its way to her crotch. I put my hand onto the bulge in her knickers, and fumbled around the waistband. I went for it and took hold of her solid cock.

It had a similar feel to my own, although it was strange to be stoking it from a different angle to what I was used to. Even doing this I could feel that I could have cum. I had to take my mind off this. "Do you not think that we should get you set up on here first?"

"We could do that later."

"We could. But I'm so fucking nervous and turned on I keep thinking I'm gonna cum straight away, I really don't want to do that."

Tony smiled. "Okay I can wait a few minutes."

It only took a few minutes as well.

"Be gentle with me, this is truly my first time." I kissed her again.

Tony slid down the bed, and took my cock out of the flimsy material keeping it back and started sucking me.

The feeling come back instantly. "You'll have to stop. If I do the same to you then I might be ok."

"I think that you will cum once it's near your mouth. That's ok, you know it can happen." "Plus there's always the next time."

"I'm just afraid that once I cum then I might not want to do anything more, I want you to have the same pleasure"

"Right then lie on your side and we can suck each other."

I lay on my side in the middle of the bed and she moved so our mouths were by each others cocks.

Now I had her cock in my hand right in front of my face. I slowly stroked it, a few times before moving in and kissing the tip. It felt so soft on my lips. I ran my tongue all around her helmet and glans. Then opened wide and took it in my mouth.

I had thought and fantasised about this and thought that it would have come naturally to be able to suck it. Now I have discovered that it takes a lot of thought as well. Soon I was bobbing my head up and down her shaft, the same as she was doing to me. I tried to wank her as I went along but I struggled to co-ordinate the sucking and wanking. But I felt I was doing a good job. I stopped to have another look at her cock just to stroke it. Then I felt it. "I'm gonna cum."

"Tony managed to get her cock in my mouth. As I felt it between my lips, and thought about what I had there I started to spurt my cum in her mouth. Tony then managed to cum in my mouth.

When I was younger, like all youths I had tried to suck myself, and only managed to lick the very end. But I had also cum in my mouth quite often.

Having Tony shooting her load was nothing like what I was used to doing alone. But the taste and consistency was very similar. I did notice that we both tried not to thrust ourselves too much as we cum.

I lay on my back. My first experience of cock sucking. And I loved it. Especially as I was dressed as a woman. And so was she.

Tony had also laid back. There was a silence but this was not an uncomfortable silence.

Eventually Tony said. "I thought you said you hadn't done that before."

"Your my first, honest."

"Well if that was your first time then I cant wait to try again. Your really good at it."

"I will only ever do it when I'm dressed." "And with someone who is dressed too."

"You don't mind sharing your things do you?"

"Not with you I don't." "I'm glad I let you see me like this now."

"What does that mean?"

"Well, I had watched you wanking by your back door, how you licked up your cum. I copied you doing that. And how I thought you might be up for some dressing up. I did hope for this though."

"So you planned all of this?"

"Not really, I hoped that this would happen."

There was some small talk. I touched up Toni's make up.