Introducing Tony to Crossdressing

"When do you want to do this again?"

"To be honest I could do this every day. I feel great being like this."

"So you like being feminised then?"

"I have wondered about trying it, I want more now."

"When your alone, there are loads of tutorials on Y.T. and other sites."

"For make up?"

"For everything to do with being feminine. Don't follow any links away from there though."

"I'm not an oldie you know."

"Downstairs and have a cuppa eh?"

It wasn't long before Toni had to go back to being Tony. His mother would be back home shortly.

Tony asked. "Tomorrow?"

"Why not, you can come earlier I hope."

Tony made a move to give me a kiss goodbye.

"Sorry, I don't do men. Next time before you get changed?"

Tony looked at me as if I was mad.

With him away, I went straight upstairs and had a sort out of my clothes. Putting outfits together to see what Toni would look good in.

I hung them back in the wardrobe, for Toni to try for herself.

Then I realised Tony had a bit body hair.

If I used my epilator, that might hurt him.

I was never one for shaving it off.

There was nowhere near enough hair removal cream in. But I could go and buy a few tubes.

I needed condoms anyway. Things might progress, fingers crossed. Oh and lube.

Then I thought. What if his mother still sees him in his shorts or topless, would she notice? Or ask why?

I think that he would want to lose the body hair.

Right off to the cheap shops, two tubes in each of them, condoms in one shop, lube in the other. I couldn't be bothered with the glares off whoever was on the tills. Then get back here and shop for some nice and new undies. Perhaps the body that I was trying not to buy myself. Have a quick look for some jewelry too, there was barely enough for two.

Tony arrived minutes after his mother had gone. "Thought she would never leave." "What have you got planned for me today then?"

"Well there's allsorts." "Have you shaved this morning? Do you want to keep the hairy legs/chest? What about your pubes?

"I did have a shave. How would I do my legs and chest? My pubes are the longest they've been for a while, I usually trim them short."

"I bought some removal cream for your legs and chest." "I only use it for my pubes, I have an epilator for the rest." "I'll show you how to shave better, for smoother skin."

"I noticed that your bum was smooth too, will you be doing mine the same?"

"I can, but it will be a bit embarrassing for you."

"Oh really?"

"Well you will have to bend right over, so none of the cream gets onto your ring, it stings like fuck." "I hope you've been in the shower."

"I shower every morning, and I seen how to shave last night and I done it this morning too."

I brought out the removal cream. "You sure you want to be smooth?"

"I'll try anything once."

I placed a towel on the floor by the dressing table. "If you stand here then you will have something to lean against while we wait."

Tony stripped off, and stood on the towel. I knelt in front of him. I had never had a cock so close to my head before. Yesterday didn't count. I was dressed as a woman.

Spreading the cream all over his legs. "I forgot that I should have tested it before hand, it's not burning or anything?"

"Nope."

I had to hold his cock while I done his pubes, a strange feeling. And up and over his chest. I then told him to turn around, and bend over so I could do his arse cheeks.

"Right we will give it a few minutes and then rinse it off in the shower."

With Tony in the shower, I stripped off too. He rinsed off his bits, and I rubbed off the hairs. I must have touched him too many times, he started to get a semi. For the first time ever. I did think about taking it in my mouth.

When he was all rinsed and hairless, Tony washed himself down, and began to dry off.

"What do we do now?"

"Want to try and do your make up by yourself?" "I'll try and keep you right."

Tony applied the foundation, and blusher easily. I helped him with the eyeshadow and mascara. Toni was back once she done her lipstick.

She watched intently as I applied my cosmetics.

"It looked so easy for you."

"Keep trying on yourself, it gets easier. Would you paint my fingernails please."

"If you do mine as well."

"I won't go right to the edges of your nails, it will have to be took off soon, so I'll keep it simple."

She chose my favorite colour, a shocking pink for herself. I went to match my toenails, a deep red.

Waiting for the nail varnish to dry we lay on the bed and chatted about why we enjoyed being girly.

It was obvious that while we chatted, both of us looked at each others cocks, and by doing so we both ended up semi erect.

She asked if we should just satisfy ourselves then. I said that it would be better to tease ourselves, and I wanted to see her in a pair of high heels, these one's had more of a block heel so they should be easier to walk around with.

I showed her the things that I thought would look good.

We got dressed together. She chose a black miniskirt and a sparkly top, clip-on earrings and a bracelet. Always watching each other becoming women.

"Come down to the kitchen, the light is a lot better there."

These heels were a lot better for her. As I walked behind I thought she had a very sexy figure.

I made her walk all around the kitchen, she was a natural.

With the urge growing, to get her in my mouth again, I suggested we should have a cuppa out on the patio.

Outside she was not as confident. "Don't worry, no-one can see us, I've done it loads of times."

"Are you sure?"

"Of course I am." "Am I going to get a taste of your lipstick now?"

Toni came to me, put her arms around my waist and we began kissing.

Using her tongue she enticed mine into her mouth and I could taste her lipstick, I had to copy her. Even though I demonstrated on how and where to put our dangly bits, while we kissed I could feel her bulge.

I had only sucked one cock, hers, I was desperate to have it in my mouth again.

"Will you fuck me today?" By she's forward I thought.

"Only if you do it to me first, and you will be my first." "Well my first real one."

"What does that mean?"

"I have a selection of toys upstairs. The ex had a strap-on for me too."

I had always been curious about finding things to fuck myself with. Then when we were together, and she started buying herself vibrators and dildo's, I tried them out when I was alone. Loved them so I suggested to her that we should use them on me too. Ending up with a strap-on and then a bigger one.

"Not yet though, take off your clothes."

"Why?"

"I want to see you in your bra and knickers."

"But we are still outside."

"I know, it makes it more exciting."

"You too then."

"But I've paraded myself out here loads of times."

"I never seen you though, if I'm in my undies then you should be too."

I began to loosen my skirt, then let it drop.

Toni slipped off her top. As she stood there I started to think that her bra and false tits did look good. I could never tell when I wore them. I could only see in the mirror or take photo's on my phone.

I pulled off my cami top. Her skirt fell to the floor.

Now in our bra and knickers, we could see that we were both hard.

Toni came closer. "Wait a second I want to know something."

She asked "What?"

I slipped my shoes off. Now Toni stood a good few inches taller.

"Now kiss me."

To reach her lips I now had to stand on my tip-toes. A few gentle kisses, and I started to feel for her cock.

Once I had it free, I dropped down on my knees and held her. Taking more time today, I stroked it right in front of my face, watching her foreskin move as I wanked her. The urge to cum like I had yesterday had gone.

I hoped that I still had some lipstick on, Taking her helmet gently between my lips, I ran my tongue around her glans.

Pausing for a look I had left a little ring of my lipstick on her bell end.

Then I started to suck as best as I could.

I had practised last night on a dildo, trying to deep throat it, but failed. I couldn't get it past the back of my mouth. But it made me determined to keep on trying.

"Are you sure you have never done this before?"

Looking up I said nope your my first, and gave her cock a little kiss.

"Are we going upstairs?

"Why?" Asked Toni, coyly.

"I want to feel you inside of me, instead of my toys." I reached up and gave her a kiss.

"Come on lets go I've never had a virgin before."

As I was going up the stairs, Toni stopped me, and pulled my knickers down.

"Lean over."

As I bent over I felt her pull my arse cheeks apart. Then felt her kissing all around my crack, before her tongue lapped away at my hole. The more desperate she got the more she pulled at my cheeks, she was trying to fuck me with her tongue! It was heaven. I wanted to be fucked even more now.

The rimming stopped. "You do have some lube, don't you?"

"Made sure of it when I got some condoms yesterday."

"Hurry up and get on your bed."

I lay on my bed wanting her to hold me and kiss me.

She pulled me down the bed so my bum was at the edge. Then my legs were high up and she started again, rimming my hole.

"Take me please, all you need is in that drawer." Pointing to my bedside cabinet.

She rattled about, and turned her back. I heard the wrapper tear.

I knew it wouldn't be long till I would get to be fucked for my first time.

"Turn over."

On all fours, I felt a little kiss on a cheek. Then the cold lube being spread around my anus. Then she had a finger in me, and another.

"Are you sure you want to do this?"

"Fuck me please."

The tip of her hard cock pressed against me, and into me so easily.

Feeling a real cock in me was so different to having plastic or latex imitations.

I then understood why the ex was not as keen on them. Preferring the real thing instead.

"You ok?"

Okay? I was in heaven. "Fuck me, fuck my girly ass."

Soon Toni was banging away, fucking me like the dirty slut that I was.

"I don't want to cum just yet, will you give me your cock now?"

She pulled her cock out of my hole. Then I thought about us sucking each other, later. She could dildo my hole as we sucked. Mmm delicious.

Now it was Toni's turn to be fucked. She took up her position on the bed. For the first time I could have a good look at her hole.

For somebody so young she had a big looking fuck hole, more abused than mine I suspected.

When I applied some lube to her, I slipped two fingers in without any resistance, not that it mattered. Toni began to moan with pleasure then.

With my condom on, I entered her, and began to fuck her hard. She moaned and groaned non stop. I carried on pounding at her hole, until she said that she wanted to taste my cum. To be fair I really wanted to have her cum in my mouth.

We took our places on the bed, and took each others cocks in our mouths.

Now that I was being sucked, as I sucked, that feeling had me spurting my load into Toni's mouth in no time. It was amazing that I could have fucked her for ages, yet when her cock was in my mouth I couldn't hold on for a couple of minutes.

Then it was her turn to give me her lovely load. As soon as I felt it being released, I kept her helmet just in my mouth, so I could feel her spurt every last drop. Mmm.

I wished that I kept her cum in my mouth, we could have had a spunky kiss afterwards. maybe the next time.

I wanted to stay where we lay. So I could watch her cock, shrivel back to softness.

As it shrank, I had a little play with it, nice and gently.

"As I began to do it to you, I noticed that it was pretty easy to get in you."

"That would be the second man I let fuck me, he had a massive thing. It took three separate times before he managed to get it up me." "Now I share a flat at uni, there's two other guys and a girl." "It started with me telling one of the lads that I was bi, and we started getting together." "Then the other one found out, and wanted to try it." "So then the three of us would all fuck, I could take the two of them in me at once." "Now even the girl knows, she sits back and watches whoever is fucking." "none of us has fucked her though."

"Wow it's a lot wilder since I went to uni." "And I did not lead a sheltered life there." "Ask her next time your both alone if she would do your make up." "You never know."

Then back to playing with her cock, now it was soft I could get it all in my mouth. Toni could get all of mine in hers too. It appeared that we wanted to get our cocks hard again for some more sucking.

"Get your things back on and you can suck me outside."

"Why outside?"

"Because time is getting on and your mother will be back soon, its a turn on thinking of what your doing while she is just next door, maybe even hanging out the washing."

"Are you really sure we cant be seen?"

"I've told you nobody can see a thing, you have to be on the other side of the screen."

"Come on then, lets do it."

With our things back on we went to the patio. I was first to get on my knees and start sucking. Toni soon forgot about where she was and become hard for me.

We swapped positions, Toni on her knees my skirt lifted up, cock in her mouth.

In a low voice. "That's a good girl, your so good at that." Toni must have enjoyed hearing that. She kept sucking, but now wanked away, so fast.

"No please don't do that, I want to taste you again first, swap back."

Back on my knees, I copied what she had done to me, She was holding on. I decided to try and lick her balls, and attempt to t-bag her.

Even though it was a bigger mouthful than I had thought, I still managed it.

We heard the back door opening at her house. Toni was terrified.

Once she had calmed down, she began to enjoy me sucking her off. I got my second load quickly.

"Put yourself back in your knickers, you rude girl."

"Sshh, She'll hear."

"Can you see her?"

"No"

"Then she cant see you can she?" "What do you want to do now?"

"I'll have to get dressed, I'm too nervous with her about."

"Come on then back inside."

I followed her again backup the stairs, looking up her skirt.

"I can see your knickers."

"Your gonna see more than that in a minute."

"What like?"

"Me with your dick in my mouth."

She made me stand looking out of the landing window, while she sucked me off. Now I was terrified of being seen. Yet I still managed to give her a second helping.

I decided to keep my things on. I watched Toni turn back into Tony.

"When can I come back around?"

"I'm too busy the next two days. So after that?"

There was a sigh. "In three days then."

"Don't worry time will fly by, and I'm sure you'll think of something you want to do." "I know what I want to do next already."

"What's that then?"

"Wait and see." "You all ready?"

"Yes."

"Give me a kiss then before you go."

For the rest of the day I stayed dressed up. I changed my clothes a couple of times. Trying to find a killer outfit for when Toni was back.

The next two days were really busy. I barely had any time to myself.

When I got up on the day Toni was meant to be here. There was a note through my door.

Tony's dad had paid for the two of them to fly out and meet him and Tony to spend the rest of his holiday out there.

His mother has asked if I could keep an eye out for their house, while she was gone.

And Tony would see me whenever he could get back home. With many thanks xxx