Ian's First Night

This is my first story so I apologize in advance for any mistakes as I also didn't have too much time to proof read. Any and all feedback is welcome. I hope you enjoy!

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It's 6pm and I'm standing in the shower, my toned upper body glistening in the artificial light as the water beats down on me from above. I've been standing there, anxious about the night ahead, for so long the water turns cold making my nipples go hard. The thought of what I've risked for tonight, scaring me more and more the closer it gets.

This is my first night.

It's now 7pm, and as I walk through the door of the bar I'm meeting her at, my hands are sweaty and I can feel myself scanning the room looking for a red bow. That's what she said she'd wear. There must have been dozens of women there that night. All seemed to be waiting for someone but none of them had a red bow on. I decided to take this opportunity to order myself a scotch to relax a bit. I couldn't believe how nervous I was. I'd been to bars to meet women for sex before but never quite like this. I hadn't even seen a picture of this woman before; we had only spoken on the phone and by text.

A few minutes went by and I began to wonder if maybe she'd gotten cold feet and decided not to come. I looked at my phone to see if she had tried to call or text. No call. No text.

As I put my phone back in to my pocket and went to order another drink I noticed a flash of red go past the door. My heart jumped and I could feel the adrenaline begin to pump through my blood as I anticipated this woman.

As soon as she entered my eyes were fixed on the red bow in her hair. It was a bold, bright, sexy red that matched her lipstick. Her small face was framed by long, flowing, wavy auburn hair that stopped just above her ample bosom that was sexily yet elegantly flaunted by her tight black knee length dress. She had a coat on, but it was open so I could see, even from the bar, that she had curves in the right places. She was breathtakingly sexy. At that instant all the thoughts I had had only moments ago of leaving washed away. She approached the bar; catching my eye as she went past and she stopped beside and ordered her drink. Vodka and cranberry juice. As she was paying I took what I thought would be a sneaky look at her arse. It was big, round and looked very tight. An arse to be proud of I thought as I admired.

Her name was Jane. I knew this from our conversations before tonight.

"Hi, Jane is it? I'm Ian"

Looking a bit shocked that someone she'd never seen before knew her name, she responded "Erm.. Yeah, my name's Jane. Hello Ian. Have we met before?"

Shit, I thought. She's here and she's not playing ball.

"No we haven't. Are you here to meet someone?"

"Oh, Ian! Sorry," She laughed as she finally realised who I was, "I was in a complete world of my own there! Oh do forgive me. And my apologies for being a bit late, too." She had such a full lips that drew my attention completely as she began to talk.

"Oh, don't worry," I chuckled, "Though I was beginning to think you weren't coming."

"Well, I must confess. I was having second thoughts earlier." She leaned in, looking around to see if anyone was listening and whispered, "I've never had a male escort before."

"Ah, well that makes two of us then."

The next 30 minutes seemed to fly by. We began talking about what she'd like to do with her time at one of the tables in the corner of the bar. Luckily for me that area was dimly lit so she couldn't see that just her telling me what she wanted to do to me got me hard.

When I decided to become a male escort I told myself that I would spend about half an hour with a woman, if she wanted to, before our little meetings 'off the clock' as a way to get to know each other a bit and to set some ground rules before we got started.

We had decided to go to a hotel room for this meeting, so we'd met at a bar right next to the one I had booked. We gathered ourselves and went next door to go to the room where we'd be spending our time. She had booked the whole night with me so a hotel seemed like a good idea. I had checked in before I went to the bar so we didn't have to wait around in the lobby after meeting.

"Good idea! I wouldn't have thought of that."

The room was spacious and modern with a king size bed, office desk and chair and a balcony with a view of the park. Its bathroom had a large tub and a separate shower.

As she walked in to the room, a sexy grin spread across her face. I could see she approved. I followed her in and locked the door behind me. As I went to turn around she pushed her body hard against mine, forcing my back on to the door. Before I got a chance to stable myself she was kissing me, those full, red lips on mine and her tongue in my mouth stroking mine. I could feel her large breasts pushing against my chest and her hips moving in time with her lips as she wrapped one leg around mine. I knew she could feel my semi erect cock against her because she pulled her chest and lips away while keeping her lower body writhing against mine while she slid her coat off and threw it across the room behind her.

"Do you like a woman that takes control?" She asked playfully, her lips now only centimetres from my own.

"When she's doing things like this, I love it," I replied. But when I was done I pushed myself away from the door, grabbing her hips tightly with my hands, turning her around and now pushing her to the door, "But this isn't about what I want. This night's about you."

I pressed my lips to hers again, more forceful than before. My hands moving down her body as I kissed her. Then in one powerful motion, I wrapped my hands round her thighs and picked her up, pushing her hard against the door again. She moaned as I playfully bit her neck, moving my mouth lower and lower each time until I was finally at her breasts. At that instant she grabbed my head, pulling my face up to look at her and landed a long soft kiss on my lips. My dick was now almost fully erect and with her legs wrapped around me I knew she could feel it through her panties.

I put her back on the floor and she pushed me backwards, not too far. Just enough so she could begin to undo my shirt, kissing down my chest as she did. As she got lower and lower her moans started to get slightly louder. When she had reached the last button she started to tug on my trousers and rubbing her hand slowly over my cock through them. I stopped her and stood her up. Her black dress had a strap over only her left shoulder. As I started kissing and biting her right shoulder my hands were slowly moving up her body, rubbing her thighs and meeting in the middle, over her pussy. I put one hand over her soaking wet panties rubbing her pussy slowly as my other hand carried on towards her shoulder strap. When it got there I pulled down her dress and it fell almost all the way to the floor stopped only by my hand still rubbing her through her panties. To my great surprise she wasn't wearing a bra. Her large yet perky, warm breasts were now pressed against my naked chest. I could feel her hard little nipples rubbing along my skin as we moved against one another.

We were kissing again, her hands moving over my body, both my hands now playing with her beautiful breasts.

"And how come...I'm the only one...in their underwear out of...the two of us?" She mumbled in between kisses.

I didn't need to be told twice so I moved back, letting her hands run down my chest and abs to undo my trousers. She skilfully undid the button and zipper in one swift move and my trousers dropped to the floor. She leaned against me, pushing us away from the door and in to the room, passionately kissing and touching all over each other's bodies.

Feeling my legs hit the edge of the bed I spun round pushing her on to it on her back as I quickly took off my shoes and finished taking my trousers off. As I went to crawl on to the bed over her she stopped me.

"Wait. Take your boxers off. Slowly."

I did as I was told and slowly pulled my boxers down, staring her in the eyes as she stared right back. When they had reached the floor I kicked them away and stood straight so she could see my now fully erect 7 inch cock. She glanced down at it and straight back to my eyes. The look in her eyes was playful and naughty. She then moved her eyes down my body slowly, seemingly to look at every well-toned muscle on the way. After she had finished, she ushered me to her on the bed. But as I went to crawl to the bed again she stopped me.

"Now. Take off my panties. However you wish." And she shuffled herself so her firm buttocks were just on the edge of the bed.

I knelt down between her now open legs and began by kissing her soft, smooth legs. Licking and kissing up her thighs, as I moved closer to her wet cunt. I kissed her pussy through her black thong, and licked at the sides of the fabric so her hot flesh could feel my tongue. Before she even realised I slid off her panties with my hands and buried my face into her dripping wet pussy. She let out a moan of pleasure as though she had just come. I played with her pussy lips with my tongue, occasionally flicking her clit with it, causing her to arch her back and writhe on the bed. My hands moved up her body to her tits now, playing with her rock hard nipples. Flicking them and pulling them sent her over the edge and within minutes she was already having her first orgasm of the night, coming all over my face as she wrapped her thighs tight around my neck. I carried on, licking, sucking and kissing her clit through her orgasm which seemed to last for minutes. When she finished, I moved one hand from her breast and began to finger her gently. One finger at first. Still with my mouth on her clit I slid another inside her, with every thrust she would moan, and her hips started to gyrate again. Still kneeling on the floor next to the bed, I was in a perfect position to hit her G-spot. I knew the instant I had found it because my whole hand was now soaked from her wet pussy literally dripping now and her fists grasping tightly to the bed cover. With her back arched again she now opened her legs even wider; allowing my fingers to go deeper and harder. Her pussy tightened once more around my fingers, almost pulling them inside her with me now licking her clit even harder and faster than before. She was on the verge of orgasm, I could tell, so I kept her there for as long as I could, teasing her until she finally came again, this time harder than the first.

When she had finished, she pulled my head up to hers, kissing me tasting herself on my face. She took my hand and sucked my fingers that she had just come all over, moaning at the pleasure of tasting herself.

Then we began kissing again, our bodies moving against each other when she pushed and rolled me on to my back. This was a woman who clearly could take control should she wish. And that just what she was doing. She was straddling me, over my thighs and her hands moved down my body, playing with my nipples and scratching playfully on my skin until her delicate hands reached my cock. She teased me at first. Lightly brushing her hands along my shaft but not the tip. It felt like hours before she eventually grasped it fully with one hand. Her tiny hand made it look larger than it is as she rubbed, slowly, up my full length, staring in to my eyes as she did. Her grip was tight. She was in control. As she sped up, her grip loosened slightly but she was clearly a master at this. I very nearly came right there. She must have sensed how close I was because she moved down my body, so she was now kneeling on the floor, her head inches from my throbbing cock and she said, "Here, let me sort that out for you." With that, she licked slowly up my dick, from the base to the tip. When she got there she kissed it softly. She kept kissing, each time her kisses getting harder, wetter and her mouth getting wider until finally she had her lips around my whole girth and began moving up and down. I could feel her tongue excitedly licking my whole dick as it moved further in and then out of her mouth each time. Then she finished with the teasing. Her lips tightened around my cock and she was sucking it hard every time she took it in her mouth. I was moving my hips up every time too to get a bit deeper and she started moaning when I did. By my moans she could tell I was close. I grabbed her hair out of the way with one hand so I could watch her taking my full load as I told her I was about to come. I half expected her to stop when I said it but she kept going, getting faster even. It was like she was actually trying to suck the semen out of me. Seconds later I felt the orgasm building inside me, and I came hard in to her mouth. Shooting hot spurts of spunk at the back of her throat while she kept her lips wrapped tightly round my shaft. She slowed now, to savour the taste of my spunky cock, waiting for every last drop so she could swallow it all. When she took her lips from my cock, it was still twitching, as she licked it slowly, cleaning it with her tongue. She got back to her feet and straddled me again.

As she got comfy again, she planted her lips to mine again. I could taste my own cock and spunk mixed with the distinct taste of her pussy. This sent me crazy again straight away and I rolled her on to her back and stood up, leaving her on the bed. As my penis went flaccid I opened the drawer beside the table and pulled out a bottle of lube and put it on the side.

"You're not gonna need that. I'm still soaking wet." She grinned as she rubbed her fingers on her visibly wet pussy, put two inside and began to get herself off. I stood there amazed at the sight before me and my dick grew again instantly. I snapped out of the trance I was in from watching her and grabbed a condom from a packet and put it on. Watching me do this, Jane took her fingers from her snatch and licked them clean.

Within seconds I was on top of her, my body bearing down on hers so I could feel her breasts against me as she wrapped her thighs around my hips. Without any help my dick glided into her dripping pussy with ease. The sudden hot, tight feeling around my cock caused me to moan simultaneously with her as she felt my dick penetrate her. Slowly at first, I began thrusting. Going deeper slightly every few thrusts until I was in her right to the base of my cock. I could feel my balls getting wet from rubbing against her juices.

Then, she tightened her grip around my hips and with her hands grasping my bum pulled me hard and fast inside her. The feeling was sensational and she obviously felt the same because her body was moving faster and faster now. Without warning she loosens her legs and rolls me over so she's now in the cowgirl position. Her legs doing all the work, she jumps up and down on my dick, every time she comes down the slapping of our bodies gets louder. She starts moaning as I can feel her pussy tighten around my dick and I go as deep as I can. Then she stops and starts riding me back and forth. My cock buried in her right to the base, I feel it moving around inside her tight pussy until she lets me find the G-spot. She's in control now and brings herself to orgasm quickly. Even through the condom I can feel how wet she's getting and how tight her muscles are gripping me. She lets out a huge moan as she comes hard on my cock, I nearly come from the feeling of her tightening around me and she falls exhausted on my chest, kissing me softly yet hungrily again.

I sensed in her that she wasn't yet finished. I was right. Almost straight away, her kisses became more passionate again, her body moving against mine again.

We started again how we had finished. She took it slower this time, not as deep. Her body was moving so fast and her pussy had felt so good before that I had hardly had time to admire her sexy, large tits. So as she rode me again, her bouncing causing her breasts to do the same I began to play with them. Her nipples were only half hard, and as I began to knead her boobs in my hand I could see them getting harder and harder. Making circular motions with my fingers I toyed with them, rubbing and flicking them. After a few minutes I sat up a bit, my strong arms around Jane's back and I took her breasts in my mouth, one at a time. I was sucking and licking her nipples when I accidentally nibbled one. This made Jane shiver and as I got ready to apologise she let out a soft moan of approval. So I carried on playfully nibbling every now and then.

After a while, she stopped me, stood up and walked slowly over to the desk, shaking her hips slowly, seductively as she went, and leant over it, resting her arms on the hotel welcome pack. She gave a perfect view of her pussy and arse from behind. I started to walk over but she stopped me before I moved a couple of feet, "On second thoughts, you might need that lube... I want you to fuck me in my arse."

I grabbed the lube and rushed over to her bent over.

"Fuck my pussy a bit more first, then put it in my arse."

"You got it. Have you done anal before?"

"Yeah, I did it a couple of weeks ago and I loved it!"

With that I rubbed her still wet pussy with the tip of my cock and slid it in her hard, forcing her to gasp at the shock. She turned her head to face me and had that sexy grin on her face again. As I fucked her pussy hard, I began lubing her arsehole. And sliding a finger in and out. As I slid two fingers in she let out a gasp again and a satisfied squeal of enjoyment. I could feel my dick with my fingers, both inside her and the sensation was better than anything I'd ever felt before.

She told me to stop and stick it in her arse now, so I quickly pulled out, put some lube on my dick and slid it slowly in to her arse. I slid in with surprising ease and began to slowly thrust in and out. Long, slow thrusts going as deep as I could. Her hips started to move in motion with mine and I could feel her rocking back and forth on to mu cock, trying to get it as far in as possible. I leant down over her and wrapped one arm around her, using it to pull her body backwards quickly and fast as I pushed my cock in to her. With my other hand I played with her tits, tweaking and pulling her nipples in turn. Then I moved it down to play with her pussy. It was still wet and hot as I rubbed it, separating her pussy lips with two fingers as a third slid inside her causing her to let out yet more moans of pleasure. As we got faster, and our bodies began to glisten with sweat I could feel my balls slamming against her pussy, stimulating her clit with every thrust. Still leaning against the desk she bent down further, letting my balls slap against her harder as she opened her legs too. I took my hands from her pussy and stomach and grabbed her hips. Using my hips and arms I fucked her as hard as she had wanted. She was screaming now. Looking back at me, begging me to go harder.

"Ohh.. Yeahh... Fuck...Mee... Harder!!"

I did as told and used up all the energy I could find.

It was definitely working. She carried on screaming, but instead of pleas for more, telling me she was coming. She came so hard her legs began to give out, but with me holding her hips I supported her while still fucking her tight arsehole. She suddenly stopped, turned around and pulled my face to hers kissing me harder, hungrier than before. I could feel her hands on my cock now; she had taken the condom off and was rubbing it hard and fast with that tight grip of hers. Before I knew it she was sucking my dick again. On her knees, her hands holding my bum to pull me further down her throat each time. I started thrusting, fucking her mouth with the same vigour that I had fucked her arse with. She was bringing me to orgasm and she knew it. I could feel all the muscles in my body tighten as it grew inside me. She knew it too and just as I came again she moved her mouth and pointed my hot shoots of spunk all over her beautiful tits. Exhausted, covered in sweat and panting for breath, we slumped to the floor in a pile.