Toni's First Night Out

I stared at the woman in front of me, she was an absolute stunner. Her legs were, slim, long, smooth just like her arms. She had slightly tanned skin, long flowing black hair, pert but fake 36c tits and a perfectly rounded ass.

Standing before him in just a white corset with lace trim, matching thong and stockings with black stiletto shoes she looked like a supermodel. Her make-up was lightly applied, with just the right amount on, and looked like it had been done by a professional. We just stared at each other and then I turned away from the mirror.

I had been practicing putting on make-up for months. Night after night I would sit in front of the dressing table mirror and slowly, but deliberately, apply foundation, eyeliner, mascara and lipstick until it was perfect. Some nights I would be up until three or four in the morning making sure I looked as good as any woman out there. Then, once I was happy with the speed and skill I could make myself up, I began buying lingerie.

It began with just simple bras and panties, small items, but soon I was scouring the internet for all manner of erotic and fancy items. I owned everything from corsets to camisoles, chemise to teddies and body stockings to bra and panty sets in all different materials and colours, my favourite being red or black satin.

Taking one last look in the mirror, at Toni, in the mirror I went and lay down on my bed. Choosing the name of my alter-ego had been easy, my real name was Tony, so swapping the Y for an I seemed the easiest thing to do. Lying there I ran my hands down, over my fake tits, and into my thong. My cock was already rock hard, thanks to the feel of my underwear, and I gripped it softly and slowly started to wank myself, all the time thinking of my first night out as a woman and how it was going to go.

I closed my eyes as I began to wank faster, picturing the look on the face of the man I went home with when he saw my cock, and I soon felt my balls tightening and ready to explode. I rolled onto my side, freed my cock from my thong, and felt my cock start to twitch. Cupping my hand under the shiny purple end I released the first stream of cum, straight into my palm. Jet after jet shot out until all that was left were a couple of small drops on the end, hanging there, causing it to glisten in the light.

Quickly I cleaned myself up, making sure I didn't make a mess on my new underwear, and finished dressing. I had chosen a black skirt with white blouse and soon I was ready. After taking a last look in the mirror, to make sure I looked all woman, I turned and headed outside. I walked into town, enjoying the cool night air, and headed straight to the only club in town. As soon as I walked in I could sense people staring at me and, without looking around, I walked confidently to the bar.

"What can I get you miss?" The barman asked.

"White wine please," I replied and waited for my drink to arrive.

When it did I paid the barman and turned to look around the club. I had been in here loads of times, just never as a woman, and I could see loads of younger women on the dance floor, having a great time with friends. I felt a bit out of place alone so stayed at the bar and just watched.

While I was watching I didn't notice the man come and stand next to me. It was only when the bar man tapped me on the shoulder to tell me I had been bought a drink that I saw him. He was tall, at least six feet four and looked to have a very muscular physique.

"Hope you didn't mind me getting you the drink," he said and inched closer to me.

"No thank you it was very nice of you," I replied.

"I saw you here alone and I just couldn't leave you like that."

I stared at this man in front of me and felt my cock begin to twitch inside my thong.

"The name's Toni," I said.

"Mine's Paul pleased to meet you."

"So Paul do you often buy drinks for strangers?" I asked the throbbing from my cock getting worse.

"Only the good looking ones."

"Are you trying to chat me up Paul?"

"How am I doing if I was?" He asked.

"Well the night's young and we haven't talked much but so far not too bad."

Paul stayed at the bar with me for the next couple of hours, kept buying me drinks and continued in his efforts to get in my panties. If only he knew the truth he would get the shock of his life, but I was that horny that I was determined that I would at least suck his cock before the end of the night.

"Paul I'm beginning to feel too hot I think I need some fresh air."

"Okay let me come with you and make sure you're alright," he replied. "Can't be too careful nowadays."

I let him lead me through the crowd and into the cool night air.

"Would you like a cigarette while we are out here?" He asked offering me the packet he had took from his pocket.

"Thank you I could definitely do with one."

Paul gave me a light and I inhaled deeply. Ever since smoking in public buildings had been banned I had tried to give up, to no avail. As I inhaled again I saw that Paul was watching me closely.

"Is everything okay Paul?" I asked.

"Yes sorry for staring but there is something about a woman smoking that I find so hot," he replied.

"Really if I had known I would have come for one earlier," I said flirting even more than I meant to, before inhaling yet again. "Why don't we go for a walk?"

Paul was only too eager to walk with me and I led him down a couple of streets before we ended up standing outside the town park.

"Come on Paul," I said heading through the entrance.

Paul followed me through the gate and I led him to a secluded corner surrounded by trees.

"What are you playing at Toni?" He asked.

Instead of answering I dropped to my knees, quickly unzipped his trousers and took his rapidly stiffening cock out. He was bigger than me, about eight maybe even nine inches long and I could only just join my thumb and middle finger around the shaft.

"Very nice Paul," I said and began to stroke him slowly.

Paul leant back against a tree and closed his eyes. As soon as he was as hard as he could get, and with his eyes still closed, I bent my head forward and flicked my tongue over the swollen purple head of his cock. I could taste the pre-cum that had seeped out and, after cleaning it all up, I took Paul's cock into my mouth. My own cock was fighting to escape my thong, but I knew I couldn't release it yet.

I sucked his cock slowly, occasionally taking it out of my mouth to run my tongue along his shaft and suck his balls, before taking it back in again. I quickened my movements and Paul reached down and gripped my head in his strong hands.

"Fucking hell Toni I'm going to cum," he said panting hard.

I mumbled back at him and started to massage his balls while I continued to suck his cock. Soon I felt him tense his legs and then, without warning, his cock twitched in my mouth and unleashed a massive torrent of cum into the back of my throat. I swallowed as fast as I could but there was too much and some of his cum spilled out of my mouth and down my top. Paul kept hold of my head and started to move his hips back and forth, literally fucking my mouth, and he didn't stop until the last drop of cum had left his body.

"That was fucking amazing," Paul gasped.

Letting his softening cock fall from my mouth I looked up at him.

"Wait until we get back to mine," I said. "Then I'll blow your mind."

"Then what are we waiting for," Paul said stuffing his cock back inside his trousers.

I got off my knees and wiped my mouth, making sure there was no excess cum on my chin, and led him back out of the park.

"How far away do you live Toni?" Paul asked.

"It will take us about twenty minutes to walk there," I replied.

"We better hurry up then."

We started to walk and as we did Paul put his arm around my shoulder, as if we were a real couple. The speed Paul walked I found it hard to keep up with him, especially as my stilettos were beginning to hurt my feet, and we arrived at mine fifteen minutes later. As I got the door open Paul grabbed me roughly and pushed his tongue, hard, into my mouth. I responded, gripping the back of his head and copying his forcefulness.

Once we pulled apart I dragged him into the front room and pushed him back onto the sofa. As quick as I had in the park I got his cock out and began to give him a hand job, until it was fully hard. Once it was hard I went to begin sucking him again, only for him to stop me.

"Get your clothes off I need you badly," he said.

"I need you as well," I said. "You strip naked as well."

Paul jumped off the sofa and was soon standing in front of me totally naked. I looked his body up and down and was as impressed with his hard, muscular physique as I was with his hard cock, jutting out from his body like a sexual divining rod. His body was virtually hair free, all he had was a small patch of pubic hair which he had trimmed short and neat and his chest and abdomen were both well defined.

Slowly I took my blouse and skirt off and stood there in front of him.

"Fucking hell you are one hot chick," Paul said as he began to stroke his cock. "I want you to wear that while I fuck you."

"And I want you to fuck me now, in the ass," I said and dropped to all fours.

"Are you sure you want mein your ass?" Paul asked.

"Yes the lube is on the table." I told him.

Paul jumped up and went to fetch the lube, and I stared at his ass as he did so. That was just as firm and toned as the rest of his body and, if all went to plan, by the time he realized that I had a cock as well he would be that horny he would eagerly accept me into him.

"Come on Paul I need that hard cock in my ass now," I shouted to him.

"I'm coming," he called back.

"I hope you aren't," I said and started to laugh.

Paul came back and dropped to his knees behind me and I felt the first, cold, dollop of lube hit my ass. Paul started to massage it around my hole, evening slipping a couple of fingers inside me as he did so, before covering his cock as well. I lifted my ass a little higher and Paul gripped me with strong hands. I felt his cock as it started to poke at my tight little ass and, relaxing as much as I could, it eventually burst through and into me. I gasped, due to the size of him, but continued to push back until he was as far in me as he could go.

To start with he slowly pumped his cock into my ass before pulling back almost all the way and then ramming it home hard. His hand gripped my hair and he pulled it, bringing my head up as he continued to thrust forcefully into me. Suddenly he slapped my ass, causing me to yelp a little, and started to thrust faster and harder. Letting go of my hair I felt his hand start to go around to my front, and my excitement began to mount even more.

I felt him as he ran his hand over my stomach and, then it happened, he touched my cock. I thought I was going to cum right then. Paul stopped and pulled my head back again.

"You have a cock," Paul growled into my ear. "Are you one of those she males I've heard about?"

"No Paul I'm not," I answered calmly. "I am all male."

"You're a fucking sissy boy."

"Yes Paul I am and you're fucking me," I said. "Now finish fucking me, treat me like the sissy that I am."

For a couple of seconds I thought Paul was going to rip his cock out and give me a good hiding, but he didn't. He grabbed my hair again, harder now, and pulled my head back.

"Okay you dirty sissy whore you asked for it."

Paul pulled back as far as he could, without his cock coming out, and rammed it hard into me. Pain tore through me but I pushed back against cock.

"Harder Paul fuck me harder," I said and waited for the next thrust which came quicker and harder than the previous one.

Paul got into a rhythm very quickly and was soon pounding into my ass like a pneumatic drill pounds the pavement. I reached down and began to stroke my own cock as, time after time, Paul's cock drove as deep into me as he could.

"Fuck it I'm going to cum you little sissy." Paul shouted and rammed his cock into me again.

This time I felt the first stream of cum enter my ass and groaned loudly.

"That's it Paul fill my sissy ass with your cum," I said.

"Take it bitch," he said as jet after jet of cum continued to enter me, before he was completely drained.

As quick as a flash I pulled away from his cock, turned to face him and eagerly took it into my mouth, making sure that I cleaned his cock completely.

"Did you like fucking a little sissy Paul?" I asked him as he sat back on the carpet.

"Why did you let me think you were a woman?" He asked.

"Tonight Paul I am a woman," I said. "A woman who wants to fuck you now."

"What you can't be serious?"

"Yes Paul I want your tight little ass to take my cock," I said just like I took yours."

"But I can't I'm not gay."

"No-one will ever know Paul," I told him. "It's just between you and me."

I took hold of his hand as he sat there and slowly guided it to my cock. He flinched when he first touched it but soon he was wanking me, just as I had him.

"That feels so good Paul," I said. "Now suck my cock suck your sissy's cock."

Paul was obviously so turned on and too far gone to care, and he lowered his head, and began to suck my cock frantically.

"That's it Paul give me head," I gasped. "Get my cock all wet and ready for your ass."

I let him suck me for a few minutes before pushing against his head.

"Lay on your back Paul," I ordered him. "I want to see you face while I'm fucking you."

He did as I asked and, after covering his ass and my cock in lube, I lifted his legs to my shoulder and slowly eased my cock into his ass. He was so tight, it was obvious he was an anal virgin, and his tightness meant that I wouldn't be long until I came. Slowly I started to fuck him, before wrapping my hand around his hard cock and wanking him at the same time.

"Does it feel good Paul?" I asked. "Do you like the feel of a sissy cock in your ass?"

Paul just groaned as I fucked, and wanked him, and I soon shot my first load into his ass.

"Mmm yes Paul can you feel that?" I asked. "Can you feel my cum filling your tight virgin ass?"

As I continued to cum, more than I ever had before, Paul's cock twitched in my hand. I watched as he came all over his stomach, still thrusting into his ass as he did. Even though he had filled my ass he still had quite an impressive amount of cum to give me.

Finally, when we had both finished cumming, I bent my head down and started to lick all the cum from his stomach and the tip of his cock.

"You taste so good Paul," I said as I lifted my cum covered mouth up.

"I-I-I've got to go," Paul said gathering his clothes up and dressing as fast as he could.

"That's a shame we could have fucked all night," I said feigning upset.

Paul didn't answer he just bolted for the door, still putting his top on as he went. As soon as I heard the front door I reached into my thong and started to stroke my cock back to hardness. If nights were going to be like this when I went out as Toni I was definitely going to need more clothes, make-up and underwear.