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Tony returns home

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I converted Tony to becoming a crossdresser.
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Lynda68
Lynda68
130 Followers

I had spied on my neighbours son, Tony. Wearing some women's underwear while pleasuring himself. I seduced him into full on crossdressing, and more. Only for him to go on a family holiday, and to go straight back to Uni.

It was sad that there would be no Toni, to play with. We had shown each other so much during our brief time. Still she would be back eventually, students always had plenty of holidays.

I had bought some new clothes for the both of us, and a few toys. Along with more cosmetics.

Buying myself skirts and dresses, almost started to get out of control. I had to buy some 'manly' clothes. Get out to the shops, instead of being online.

Even trying out online dating was not up to much for me.

Almost all the women just didn't do it for me. Crossdressing sites were either admirers, or worse still, weirdo's. Or I had set my aim too high.

When I had the time alone, I felt that I was getting better and better at being feminine. My new toys were bigger, and I accommodated them in me, after a little practice. My favorite one come with a suction cup, I never stopped looking for new places to find, and fuck it, while sucking on a slightly smaller dildo. I still couldn't manage to deepthroat it though.The only place that I never tried with it was on the patio during the day.

Being dressed with Toni, started to become a distant memory. I received the odd text from Tony. But I had said from the beginning that we should keep our girly side to only when we were together. He never mentioned that he had arrived back home.

It was a nice surprise when he knocked. Obviously his mother had gone off to work before hand.

Tony tried to get a kiss as soon as the door closed.

"I'm not into that. If you had your girly things on, that would be different."

"I can see no difference. I have missed you."

"No, you have missed me being dressed as a woman the same way I have missed Toni."

"Have we got the time to get changed then?"

"If we are quick, your mammy wont want to be away for too long from her little boy. Will she?"

Tony was taking his things off as I spoke.

I joined in by stripping off too. I tried to hide the fact that I was getting hard. Tony seemed to enjoy the fact that he was very hard already.

"You wont get any knickers on with that the way it is. Fuck it do you just want to put on a little make-up and just our lingerie?"

"Oh yes please."

We only used a little blusher, eye shadow, mascara and lippy.

Our undies were a mis-match. But we were ready in record time.

We stood there in front of each other, eyeing each other up.

Toni was the first to move, she held me before giving me a long deep kiss.

I could feel her body against mine, she was still smooth. Our hard cocks pressing together, false tits squeezing together. As we kissed, groped and fondled.

Without speaking we edged our way to the bed, lips still locked together, tongues in each others mouths.

Once we had fell onto the bed we could get a feel of the one thing that we had both missed the most.

For me having someone else to take my cock in their hand was a relief.

I did think that I may have become too excited. Once I had a hold of Toni's cock, everything calmed down. I became so relaxed.

Toni spun herself round, so we were facing each others cocks.

With her magnificent member right in front of my face, my mouth started to water.

Teasing myself as well as Toni, I began to wank her slowly, pulling back watching her foreskin roll back, and cover her glans.

Toni didn't wait, she had me in her mouth almost immediately.

I couldn't wait. I kissed the tip first. Then ran my tongue around her helmet, before sucking her. I still tried to deepthroat her. I didn't gag. But still couldn't swallow her.

The moans that Toni made, was telling me that I must be doing ok. I sped up with my sucking. Toni began to match my rhythm so she gently thrusted her cock in my mouth.

I wanted her to cum. I wanted her to do that so much. I was now desperate for her to blow her load in my mouth. I began to wank her as fast as I could.

Toni stopped sucking me just as she started to cum in my mouth. Her delicious sperm spurting on my tongue.

That was enough to set me off. As I cum in Toni's mouth, I was trying to squeeze the last drops out of her.

Not wanting to make it too uncomfortable for Toni, I left the head of her cock alone, instead I kept trying to take her softening cock all the way in my mouth.

By the time I managed to, her cock had gone down by an inch or two.

Toni began, "I really needed that, and I think that was better than the last time."

"I have been a good girl and practised, while you were away. I did hope that you would have fucked me though."

"I can do that every day for the next week and a half."

"Not tomorrow you can't, I'm working, miles away too. Why half a week?"

"One of the lads has dropped out or is going to. We have some interest for his room, so the rest of us are going to interview them."

"That's ok I can keep the mother happy. Let her show me off to her friends. Then she will leave me alone after that."

"We have a good weather forecast ahead, so we can be dressed up and have some fun together outside too."

I spun around to be face to face with Toni. "then we can do more of this too."

We kissed some more.

Between our kisses, Toni tried to find out what I was planning. All the while claiming that she had nothing planned or wanted to do.

"Looks like our time is up, back to being normal I suppose."

Toni was up first to the dressing table to remove her make-up. I dug around in my nail varnish bag. I handed a bottle of bright red varnish, and some clear coat to Tony who was now back, all make-up gone, no wig, false tits removed bra unclipped.

"What's this for?"

"When you get the chance, do your toe nails with this. Clear first, two of the red and another of the clear. Just make sure each layer is dry before the next. And have a window open, for the smell. It will save time."

"Will you be wearing some too?"

"As soon as I get home I will do both my toes and fingers. I might even be ready when you get here."

"I have to go, see you very soon."

"Bye."

I let Tony give me a little kiss on my cheek as he left.

A quick check around the house, to see if I would need anything.

Plenty of lube left, best buy some more condoms. Loads of cotton pads to remove our make-up and nail varnish.

On the night before, I managed to get home earlier than I thought. That gave me enough time to carefully do my nails, and a bit housework. I almost got changed to do that, but talked myself out of it in case I turned myself on too much and then I would have ended up wanking myself off, and wasting my juice for Toni.

Without doing it on purpose, I saw Tony's mother setting off in the morning.

By the time I got to the front door to unlock it, Tony was there already. With painted fingernails too.

"I'll get the make-up out for you, I'm going to have a quick shower. I was a bit slow off the mark this morning."

"Do you need a hand in there?"

"Nope definitely not. I can cum really fast in the shower, don't know why, always have."

In the shower, I made sure that my cock and my bum was nice and clean. I shaved again just to make sure there was no stubble.

A naked Tony was at the dressing table, almost transformed into Toni. "I still don't like putting on this eyeliner."

"Just take your time, and do your best. I found it the hardest thing to do as well. Pick what you want to wear out of the wardrobe, all the undies are in the second drawer down over there."

I dried myself and waited to see what Toni would choose to wear.

Applying my own make-up, I had to slow myself down, I didn't want to rush. After all we had plenty of time.

"What about this?"

Toni had picked out a pencil skirt and a white blouse.

"Do you want the sexy secretary look?"

"A bit. Do you think it will look good?"

"Anything would look good. We are not going anywhere. I think black underwear would look great, and stockings. Don't clip them on yourself, you might spoil your nail varnish."

I went for a skater skirt and a cami top, along with a white thong, bra and hold-ups. I had to tell Toni that she would have to wear high heels to complete the look. I chose flats again. I liked it when I had to get on my tiptoes to kiss Toni.

Once Toni's suspenders were fastened, we stood facing each other. "Lets start in the garden, on the patio. Take your time in them heels."

I stood by he patio doors, and watched Toni teeter over to me. Looking up to her, holding her hips. "Hi." I lifted up and kissed her.

As Toni kissed me back, she seemed more desperate than the other day. She pulled me tightly to her, little sighs from her as our tongues met. We ran a hand over each others hard cocks at the same time.

I broke away. "Sit there and let me see you play with yourself."

Toni tried her best to walk properly in those stiletto's, she looked at the seat and thought it best to hoist up her skirt before she sat down. Once seated she rubbed at her cock first, then fished herself out of her thong. Looking at me she stroked herself slowly.

I stood out of reach and began playing with myself.

Toni then started to rub herself as if she really had a clit, leaving her cock alone to hold back her sack, and rub at her imaginary clit.

I stood beside her and offered my cock to her mouth. She took me and sucked me, still rubbing herself. I had to tell her that she was a good girl, and that I had a present for her.

That stopped her sucking me and playing with herself. "What have you got?"

I had an old quilt hidden just inside the house. I brought it out and placed it in front of Toni.

"Bend over the table first and then I will show you in a minute or so."

Toni stretched herself over the table, still with her skirt pulled up. I got on my knees, and peeled her knickers down. With both hands I caressed her arse, before parting her cheeks and began to kiss her bum.

I kissed her all over there, before moving in and concentrated on her ring. I kissed licked and sucked away at her little ass hole.

"I wanted to do this the other way round but I couldn't resist doing it to you first, that's if you want to..."

"Do what?"

I produced my dildo with the sucker cup.

"What do you plan on doing with that?"

"It's going to get stuck on that doorframe, and either you or me will slide onto it while sucking on a cock."

"Well you will have to try it first, I've already done it with the real thing at Uni."

"I thought about that, it's why you were bent over there. You could lick me while fucking that first. Lube and condoms behind the door."

Toni slid a condom onto the dildo and lubed it up.

"Can I watch it while it goes in you?"

"Really?"

"All I have ever seen was me with it in a mirror, I have recorded it and on porn films."

"You said that you were married."

"Oh I have seen her putting it up her cunt, she wouldn't put it up her arse though. Even though she enjoyed anal."

"Did she not fuck you with it?"

"No, we never had one like this. I bought that. She did peg me, once or twice."

Toni had positioned herself on the duvet, dildo stuck to the doorframe, her hole ready to be penetrated.

She wriggled her arse until the dildo was tight against her hole. Then she pushed back onto it. Her anus opened willingly to take the dildo. She slid it in about halfway, before sliding almost right off it before pushing herself all the way along the plastic cock. After catching her breath she began to fuck the dildo with long steady thrusts.

"Are you ready for me?"

Toni gasped that she was ready.

I got onto all fours in front of Toni. She placed the hem of my skirt on my back, and slipped my thong down. Just like I had done to her.

I felt her tongue start lapping away at my hole. I thought that she would have gave my arse a kiss or two before diving in.

Then it felt as though she was trying to fuck me with her tongue as she fucked herself on that dildo.

"I think that will do for now. It's your turn to be fucked."

I looked over my shoulder to see Toni already turned around to take off the condom.

She stood up and adjusted her knickers, then bent over and rolled another condom onto the dildo before lubing that up ready for me.

"There you go. Can you take that? It is a bit big but very filling."

"How do you think I enjoyed myself while you have been away? Now all I want is to suck you as I fuck that thing."

I had to lube my hole first. Just in case I struggled with getting it in me. I needed not to worry though, the thing slid almost all the way up me in one go. I must have trained myself a bit too much.

The feeling of having Toni watching me and the fresh air on my barely covered body was a turn on that I had never considered.

Then Toni presented her cock before me.

As I sucked on her, I fucked that dildo hard.

It was as brilliant as I had imagined. There was a tiny problem though. I was loving it that much I started to think about having a threesome, so I could have a real cock at both ends to spit-roast me. I might ask Toni about that later maybe. But now just concentrate on the pleasure that I was having right there on my patio.

"Is this what we are going to do, till you get me to cum? Or can we go upstairs so I can fuck you.?"

"Come on then, lets go upstairs."

After I had pulled my thong back up, and managed to get the dildo off. I followed Toni upstairs.

In my room Toni stopped, leant over and kissed me. "Get on the bed assume the position and get ready to be fucked really hard. I have waited so fucking long to do this."

As I got myself comfortable Toni put on another condom, and lubed that up.

I felt my knickers being pulled down again. And then Toni sticking her cock all the way up me. She made sure she was balanced right, then she held my hips and began to give me the fuck of my life.

When she cum, she nearly pushed me flat, with the way she was thrusting into my arse. I could feel her twitching trying to squeeze every drop of cum out.

As she slid out of me I felt her take hold of my cheeks. "That would have been a lovely picture."

"What would?"

"Your arse hole being held wide open."

"Really? Perhaps I might do that to you."

"Would you? Really take a picture of my gaping hole?"

"When your phone is downstairs. Next time I will. Can I do you without a condom?"

"Bareback now? I'm willing to try."

Toni took off her panties as I lubed my cock.

When she was in position, I penetrated her, and began a good steady rhythm.

Even though she had just cum. Toni was loving it. I had to take a moment.

Now it was my turn to have a look at her gaping hole. Then I understood why she would want to see that. I wanted a photo took of my hole like that too.

"Have you had a good look? I need your cum in me. Fuck me hard and fast, try and push your dick out of my mouth when you cum."

When I started to cum Toni was already face down, her tits squashed on the bed. As my cum spurted into her I kept thrusting and pushing my cock in her as far as I could.

I took my time pulling my wilting cock from her.

We had a little kiss, but Toni had to go to the bathroom and let my cum drain out of her.

I took the opportunity to clean my cock.

Toni was still sat there, when I was done. Just as I reached for a towel, she insisted on inspecting me. Taking hold of my soft cock, she looked all around it, before taking all of me in her mouth.

At first it was slightly uncomfortable, seeing as I had cum a few minutes ago. But Toni's mouth changed all that, and I began to get hard. She took my cock from her mouth. "Give me a few minutes to clean up, and I will see you on the bed. Kiss first."

I was torn between long sloppy kisses, or a quicker kiss so she would be ready sooner. I thought that if it was quick then I could adjust my make-up while I waited.

In my bedroom, I changed my panties, to a G-string, and touched up the make-up and lippy.

Laying on the bed ready for her, I changed my mind. I took off the skirt and top. Making myself comfortable in my lingerie.

Toni had taken off her heels, she carried them in. "By someone has been busy."

"I was just making sure that I looked my best for you."

"Oh you do. You look good enough to eat."

"Was that not what you were doing just before?"

Toni took off her things, leaving herself in her lingerie.

She climbed onto the bed beside me.

We had our arms wrapped around each other as we kissed with so much passion. I gave in first and had my hand in her panties first. She was almost hard when I took hold of her. With some gentle wanking she became hard again.

Then I had an idea. "Why don't we go back outside and have some more fun there? I'll wear those heels and you can put the other pair on."

"I need my make-up done first, I can't go out like this."

I waited by the door as she touched up her make-up.

Once done we made our way to the patio doors, stopping to put on our heels.

I was out first. I stood so the screen was behind me. Toni walked up to me and we began to kiss.

Now the sun had moved, so it was nice and bright and warm where we stood holding each other.

I was so hard, instead of breaking free from my tiny G-string, my cock had caught the elastic, and stretched the material out. Toni had noticed that, and went to suck me.

"Why don't we sit and watch each other playing with ourselves first. No touching each other just yet."

"I want you in my mouth though."

"Just wait a little. I want to see you in this beautiful light. I really want to suck you too."

We sat opposite each other. Toni had the sun directly on her, she looked gorgeous sat there with her eyes closed as she touched herself.

I settled back and stroked my hard cock as I watched her.

She asked. "Do you like the taste of your own cum?"

"Yes although I don't lick it up all the time. If I have a wank then I usually cum in a tissue or some kitchen roll. I know you like your own. Why do you ask?"

"Because I want you to cum in my mouth, and we can have a spunky kiss."

"Only if I can do it to you after."

She knelt in front of me. "Make yourself cum. Cum for me. In my mouth."

I began to beat my cock. Toni at the ready in front of me, with her mouth open already for my load. She looked like a porn star.

I felt my cum begin to rise. "Here." With her mouth still wide open, I started to spurt my cum in her mouth. It pooled on her tongue.

Once she felt that I was spent. She was up. Her lips on mine.

Soon as I opened my lips she let my cum dribble from her mouth into mine.

When there was no more she knelt lower so I could do the same to her.

Then we were level, we swapped my cum with our tongues.

In no time we had swallowed my load.

Now it was my turn.

I got on my knees, ready for Toni to spurt her load in my mouth.

I don't know if it was having my mouth wide open and ready. But it felt that she shot more cum than she had done when I had sucked her off before.

Soon it was now dribbling into her waiting mouth.

Once we had cleaned ourselves, and changed back to 'normal' clothes. Tony made his way back home.

I had other commitments for the next few days. One thing preyed on my mind most of the time. Why wouldn't I kiss Tony, yet when he became Toni, I was all over her? I loved to kiss her and go down on her. Let her suck and fuck me. But only as she.

Tony was a handsome man. If he tried it on again, then I would have to try it out with him. It would save time and make-up. I supposed. But getting dressed up was also part of the allure.

I found myself, when out and about driving. If a man crossed the road in front of me, no matter what age he was, I wondered if I would have sex with him as he was, and imagined what he would look like as a crossdresser.

Lynda68
Lynda68
130 Followers
12


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