Tony to Tanya

My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. My ass isn't half-bad either.

I'm an open-minded person when it comes to sex. I'm also adventurous. I'll try almost anything at least once, and if I like it, I'll do it again.

I'm currently dating a girl called Sarah who's really into being the dominant one in the bedroom. And like I said, I'll try anything, so I'm all for it. She'd only had me do "normal" things like licking her pussy and role-play, which I'd do anyway.

My sex-life was about to change dramatically.

I was just leaving college one day, when my phone rang.

"Hello?" I said as I answered it.

"Hey, Tony." Sarah said with a cute voice.

"Sarah, how are you?" I asked.

"Fine." She answered. "I was wondering if you'd come over to mine tonight. I've got nothing to do, and my parents are out, so I thought we could have some kinky fun. Are you free?"

"Sure. I've got a few things to do, first, but I'll be over later." I told her.

"Great. What have you got to do, anyway?" she enquired. "Oh, I gotta send an email to Paul." I answered. Paul was in the army and was currently stationed in Afghanistan. "Then I'll eat, shower and come over." I finished.

"Alright. Give Paul my best." She said.

"I will. Love you."

"Love you, too." She hung up.

Half an hour later, I walked through the front door. I had a little chat with my parents about my plans for the evening, and went to my room to send my email.

When I'd finished, I went back downstairs and made a bacon sandwich. I ate it while watching a comedy quiz show and went for a shower.

In the shower, I could hear my sister, who was 20 and home for the summer, listening to some of my music, and I sang along to it quietly.

When I got out of the shower I dressed in my Guns 'N' Roses T-shirt and jeans and headed back downstairs to finish watching my show.

When it had finished and I'd finally managed to stop myself laughing, I put my shoes on and left the house to catch the bus to Sarah's. I spent the bus ride wondering what kinky things Sarah would do with me.

When I arrived at Sarah's, I knocked on the door and she answered it quickly. I'm always stunned by her beauty, but today she was dressed very sexily.

Sarah is 5 foot 5 inches tall, with long, curly, blond hair, and an amazing body, including 34C boobs and a lovely heart-shaped ass. But instead of her normal sleeveless top and jeans, she was wearing a top that revealed her flat and toned stomach, and showed that she had no bra on. She was also wearing the shortest mini-skirt I'd ever seen.

"Hey sexy, come on in" she said with a radiant smile.

I walked through the door and closed it behind me and my surprise must have shown on my face because her smile became even more radiant.

"Cat got your tongue?" she asked.

"You are the sexiest girl I've ever seen." Was all I could say. I pulled her towards me and kissed her passionately.

After a minute she broke the kiss and took my hand.

"Come on, lets go to my room. I have a present for you up there. Besides me, that is."

I let her lead me to her bedroom and I sat in the chair at her desk while she closed the door. She came over and straddled my lap, kissing me fiercely. She broke the kiss and climbed off me and went to the drawers she kept her clothes in.

"Close your eyes." She ordered.

I did as I was told and I heard her rummaging in one of the drawers for something.

"OK, you can open them."

I opened my eyes and saw that she was holding her school uniform from the year before: white blouse, green skirt that would reach about halfway down her thighs. She even had the knee-length socks and the shoes.

"I thought you were already dressed up for me." I said, slightly confused.

"I am. These are for you." She clarified.

It dawned on me what she wanted me to do. I have no real negative views of dressing up as a girl, I just never thought I'd do it before. And I never knew that Sarah would want me to do it. I was shocked to have it being sprung on me so suddenly.

"You want me to-" I started.

"Dress in my old school uniform? Yes" she finished for me. "You don't mind do you? You said you'd try almost anything and this isn't one of those 'extreme' things that you ruled out of trying."

"True." I thought it over. "Since it's just between you and me, I'll do it but it's not something I'd ever thought of before."

"It'll be easy. This'll fit since we're the same size." She told me.

She wasn't wrong. I don't have the same figure as her, but I'm not muscular or anything. My body's toned and slim. Her old uniform would fit.

"I don't quite see where this is going." I said.

"You will." She assured me. "Let's do your make-up and then you can change in the bathroom while I prepare everything else. Wear this, as well." She finished, throwing me a black lace thong.

She did my make-up: a bit of eye-shadow, a small amount of blush and some pink lipstick. She brushed my hair as well, making me look like a very pretty girl when it was all done. I set off to the bathroom to change.

I stripped to my boxers, put the blouse on and buttoned it up. I couldn't believe I was going through with this. I then took my boxers off and pulled the thong on, I had to rearrange myself so I was comfy. I pulled the skirt and socks on with no difficulty and my nervousness was starting to disappear.

When I had the shoes on I stood up and looked in the full-length mirror. I was astounded. I looked immensely cute and shy, like the new girl in school. It was as if I wasn't looking at myself.

My cock started to push against the material of the thong. I was really starting to get into this idea, but I still didn't have the full picture of what we were going to do. I went back to Sarah's room.

"You look cute, sweety." Sarah said as I walked in. "You need a girl's name to finish with and I thought of one: Tanya."

"Tanya." I repeated. "Sure."

"I need to ask you something. Do you have anything against receiving anal?" Sarah asked.

"No." I said. "I've experimented."

My sister went to a college in another town, so she was only ever home for the holidays. She had a lot of toys of different shapes and sizes. When she was either at college or out, I experimented with them: dildos, anal beads, vibrators and butt plugs. I even went to school with a butt plug in, once. I enjoyed anal more than I thought I would when I first tried it.

"Good," She said, "Because today, I'm going to fuck your ass. Do you need lube or anything?" she gave me a smile. She was clearly being careful with this experience.

"I don't need any lube." I said, returning her smile.

"I can tell you're excited, so lets start with the foreplay, shall we, babe?" she asked.

I nodded and she motioned for me to lie on the bed. I did as she wanted and she straddled me, rubbing the crack of her ass against my cock as she kissed me. I opened my lips when her tongue brushed against them and our tongues started exploring each others' mouths.

After a couple of minutes, Sarah broke the kiss and stopped grinding on my cock. She moved up to my head and took her panties off, she then straddled my face while facing my feet. She spread her ass cheeks and lowered herself.

"Lick my asshole." She ordered. Something else I'd never done until then.

I extended my tongue to that tight, rose-pink bud and licked around it. She moaned with pleasure and ground herself into my face. I licked around once again and then pushed my tongue into the tight hole. Doing this made her scream with pleasure and lust.

"Get on all-fours." Sarah told me, climbing off of my face.

I did as I was told. She got on her knees behind me and spread my cheeks, moving the thong to one side, which made me tense with excitement and nervousness. She spat on my asshole and started to lick, working her saliva into it.

The sensation was amazing. It was one of the most erotic experiences I had ever experienced. I groaned in pleasure and happiness as she slowly pushed her tongue into me. I was starting to hope the sensation would never end. She stopped licking and spat on my asshole again.

She sat up and rubbed her saliva in, before slowly pushing two fingers into my ass as deep as they could go. As I was reaching new heights of pleasure, she doubled them by slowly pumping her fingers in and out of me. After a while of doing this, she added a third finger and carried on fingering my ass. My cock was straining against the thong she'd given me.

"Turn around and close your eyes, but stay on all-fours." She told me, removing her fingers.

I positioned myself as I was told, while she reached under her bed. I closed my eyes while she was searching. I heard her fiddling with something and I began getting a little more excited.

"You can open your eyes now." She told me. I did so.

There she stood, wearing a strap-on dildo. It was purple and fairly big at 10 inches long. It also looked very thick. She stood in front of me, looking at me with lust.

"Suck my 'cock', you little slut." She commanded of me.

I was happy to oblige. I leaned forward, grabbing the shaft of that huge fuck-stick and licked the end, before I slid it in my mouth. I bobbed my head, while swirling my tongue, sucking the strap-on how I liked my cock sucked.

"That's right you little bitch. Suck my big cock like you mean it." She encouraged. "Suck it as deeply as you can."

I slid it as far into my mouth as I could manage without choking which was about 7 inches. I was really into this, now.

Sarah started thrusting in my mouth, getting just a bit of the dildo down my throat.

She pushed my head away and turned me around.

"I'm going to tie you to the bed, now, slave." She said forcefully, tying one arm to one of the bedposts at the head of the bed. She than tied the other arm to the other bedpost, giving me just enough slack to lay my head on the pillow comfortably.

Once again, she moved my thong (as I began to think of it) aside and spat on my asshole. This time she rubbed it in with the strap-on, mixing her saliva and mine.

She grabbed my hips and positioned the head of the dildo at the entrance to my ass. After a bit of prodding me, she pushed the large, thick 'cock' into me.

I winced from the small amount of pain and the sudden intrusion, but within a few seconds, both sensations had dissipated. Sarah was letting me have a bit of time to get used to having something so large in my ass.

Slowly and gradually, she began pulling out of me. When she'd pulled out to the tip of the dildo, she reversed direction, pushing it back in a little more gently than when she first entered my ass.

After the first thrust, she set a slow steady pace of thrusting. It felt amazing. I could feel my ass squeezing the dildo gently, as if it was trying to keep it inside me. My cock was straining more than ever against the thong I was wearing, as if it was trying to get loose by breaking it.

Sarah started thrusting faster as she reached around towards my stomach to slowly pump my cock with her hand, after moving the front of the thong aside.

She rubbed her finger into some of my pre-cum and put it to my lips for me to taste. I stuck my tongue out and licked her finger. It was quite a nice taste: slightly salty and a little sweet.

I was really getting into having my ass pounded like a little slut. When Sarah picked up the pace again, I began to meet her strokes, making the dildo go into me as deep as I could accommodate.

I started feeling my balls tighten, ready to release a massive load all over Sarah's bed. I didn't want to cum so quickly, I was having too much fun, so I fought with the feeling.

I couldn't fight it off longer than a couple of minutes. As I was just reaching my boiling point, I let out a groan.

"Sarah, I'm cumming!" I yelled.

"Yes! Cum for me. Cum from having your ass fucked." She said in response.

Long, thick strings of cum flew from my cock, covering her bed and hand. She once again put her hand to my lips and I lapped my cum up without letting a single drop fall from her fingers. It had a stronger taste than my pre-cum, and it was thick and rather difficult to swallow, but it tasted great. I was surprised I was doing it, but had no misgivings about it.

Sarah kept pounding my ass until the friction of the strap-on against her clit caused her to cum with a squeal of bliss.

She collapsed onto my back and I fell onto my front in the pool of cum on her bed sheets. The dildo was still in my ass and I was content to leave it there for a while longer.

"Did you enjoy that, babe?" Sarah asked me.

"I loved it." I told her.

"Did you enjoy dressing up and do you think you'll do it again?"

"Yes and yes." I answered.

"I think we may need to go shopping, then." She said and kissed my ear-lobe.