A Complicated Relationship

It was as if I had a balloon inside me, and every day my emotions pumped it up further, making me feel as If I were going to explode. The pressure built; I lusted after her in both perverse ways; I hated myself more; and the pressure built more, day by day, hour by hour, minute by minute. Trouble was, even if I got my courage up to make a move on her, why on earth would she choose a nerd like me, when she could, and clearly already had had her pick of more outgoing, stylish men. And women.

I've got no idea how I managed to survive without bursting apart, but somehow I managed to get to Vegas. The flight was delayed, though, so I was late getting to the hotel, and the event had just started when I arrived.

I was still in time for the launch, luckily, as it was the first of the big set pieces, and I joined the team in the wings.

"Oh, hi, Jack. I didn't think you were going to make it, as you were too busy jacking off," Diane said, smiling, but what she said was close enough to the truth not to be funny.

"Um ... yeah," was all I could manage to reply, not just from her comments, but her appearance as well.

I guess I should have known that she'd do the demo herself, rather than hiring a professional model. She was dressed just in a sheer white lacy bra and panties, which showed her nipples and pubes even more clearly than during the tests. I'd obsessed about as much of her tits and pussy as I got to see over the previous weeks. Now the extra detail in sight added to the pressure inside me, and I knew my cock was starting to stiffen.

It got worse, though, because Wesley, one of the guys I was certain had fucked her, walked over to her.

"Only a minute or two to go, Di. You've just got one nipple a bit twisted - let me sort it for you."

He slipped his hand into one of her bra cups, pulled the cup out with the other, and jiggled her breast until he was happy that this nipple wasn't caught up. Oh God, I thought I was going to pass out, as the pressure rocketed up inside me, and I felt my cock pushing hard against my pants. I must have missed it, but the presentation must have been announced, because Diane turned to walk onto the stage, and Wesley slapped her gently on her ass.

"Knock 'em dead, Di."

She ran through the demo, which worked every bit as well as the rehearsals, but of course, everyone knew it was pre-planned, so it absolutely should have. What I hadn't expected was that she then chose a woman in the audience, and brought her up on stage. Diane had chosen well, because the woman was in a body-hugging dress, so the measurements were good.

They must have brought a good range of sizes in the dress they were using in the demonstration, because Diane sent the woman off stage, and when she came back in the dress of the size predicted, it fitted perfectly, and the whole audience erupted.

It all got too much for me, though, when the demo was over, and Diane walked back into the wings.

"That was fabulous, Di," Wesley said, hugging her to him.

I felt as if I'd been struck by lightning, as I noticed his hands were down inside her panties, cupping her ass cheeks, then Diane turned to look over to me, and I realised she knew exactly what this was doing to me. I turned and headed straight back to my room.

I linked back to the office on my laptop, and started doing some difficult, low-level programming, which I probably didn't need to do then, but it just worked in stopping me doing what my body wanted me to do: to jack off, picturing Wesley fucking Diane. I only stopped, when there was a knock at the door, and a uniformed man handed me a note in a sealed envelope.

Jack,

Please come to Suite 1316 as soon as you get this. I have a new business idea for you, that I would like to discuss.

Diane

This just made the torment in my brain worse. A business proposition? I was certainly interested, given that the app that Diane had just demonstrated looked sure to put my Company into a completely different league. God, I wanted to see her, but how much more would I hate her and myself if she flirted, or worse, with anyone else in the team.

I had to go, though, even if the pressure inside me felt way beyond what I could cope with. I took the elevator to her floor, then walked along the corridor to her suite, full of anticipation and fear.

When I knocked on the door, she opened it herself. She was in just a bra, which seemed even more transparent than the previous one, barely hiding any detail of her nipples, with the only other thing she was wearing being a thong. Oh God, her ass was bare, and I might have let out a little groan as I tried to get my emotions under control.

"I thought you said this was about business, Diane? You hardly looked dressed for it."

"Oh, Jack, don't you like it," she asked, closing the door, then doing a twirl round so I could see her naked butt. "But yes, it is business."

I followed her into the lounge area of the suite. The doorway to the bedroom was open; I could see the king-sized bed, with filmy underclothes scattered over it, and I felt my blood pressure rise even further.

"Just get on with it, then Diane," I gabbled, not sure how long I could keep myself under control.

"Your present app is about getting a perfect fit for top clothes, and being able to see exactly what they would look like on you before you buy. Yes? It's great, but actually, underwear is even harder to get right online. Take this bra: it's only fitted by chest and cup size, but women's breasts are far more varied than is captured by the A, B, C system of cups. See how my nipples are flattened?"

I didn't want to look, yet at the same time I did, and I saw she was right. Then I realised she was reaching round her, and unfastening the bra.

"I might be a C-cup, but my breasts are more pointed than round, aren't they? Just hold them underneath, and see how much further forward the nipples need to be, while they are slightly smaller around than the cups."

"Uh ... I can't ..."

"Don't be silly, Jack. You must have touched other girls' tits, and this is just business. Though it's what I really like about you. Most other men would have grabbed me as soon as I offered, and would have started kneading them around as if they were making bread."

Oh God, I'd wanted this so much, but now I was trembling like a little child, as Diane slipped a bra strap over one wrist, then grabbed mine, pulling my hands up so that they were gently cupping her breasts underneath.

"See, Jack? I'm right, aren't I?"

She was wrong, or course, I'd copped a quick feel of the girl I'd taken to the final Prom, but I'd never even seen a woman's naked breasts this close, let alone touched them, and her brown, wrinkled nipples seemed to be eyes looking at me, inviting me.

"If we changed the app to take naked pictures - yes, I know we'd need to work on security even more - surely you could calculate the size and shape in much more detail, and we could tailor a perfect fit? I know some specialist lingerie shops offer fitting, but it's expensive, and not all women enjoy strangers touching their tits, the way I do, Jack."

The last was said with a wicked smile, as I suddenly realised I was still holding them, and quickly pulled my hands back, holding them down at my sides.

"Um ... yes ... just business ..." I mumbled, trying to hide the fact that touching her breasts was probably the most exciting thing I'd ever done.

"It's not just bra's, though, Jack. Look at this thong. The back has ridden right up into my ass, and it's uncomfortable when I sit, let alone not even covering the essentials."

Oh God, I was going to die, I knew it, because as she spoke, Diane had turned around, bent right over, and pulled her ass cheeks apart. She was right. What seemed little more than a thread ran up to the waistband, and it covered almost none of her wrinkled, pale brown anal ring.

"That's not all, Jack," she said, standing back up, turning around, then sitting down on one of the chairs, with her legs apart. Look, it's worked it's way between my pussy lips."

My heart was racing like crazy, and I was struggling to keep my brain aware that this was reality, and not just another jack-off phantasy, although my cock was sure it was, and wanted me to deal with it. Now.

"It not only would leave me flashing more than I wanted if my skirt blew up, but it's uncomfortable, and the crotch panel just gets soaked. Here, see?"

I was still trying to deal with the sight of the wrinkled, pink-brown flesh poking out on one side of her panties, and to reconcile it with my severely limited picture of a woman's pussy, so when she pulled them off and threw them at me, they hit me right in the face.

I grabbed at them, managing only to hold them hard against my face, and I was almost overwhelmed by a powerful odour that I'd never come across before. I wrinkled my nose, as the musky, slightly acrid scent initially repelled me, but the more I inhaled, the more I discovered I liked it.

"Gosh, Jack, I didn't realise you'd be another one of those men who can't get enough of the smell of my cunt," Diane said, smiling, opening her legs wider.

I think it must have been not just the choice of word, but the emphatic way she said 'cunt' that seemed to ignite the fuel that had been burning inside me for weeks, and I knew that whether she wanted it or not, I was going to lose my virginity and fuck her before I left her suite.

"God, Diane, that's it. I can't take anymore. You're such a slut, but now it's my time to fuck you.," I snarled, undoing my pants, and letting my cock spring out towards her.

"Oh, Jack, thank goodness. I love you being such a gentleman, but I was beginning to think you'd never give in. Come on, shove that cock right up my cunt. Join the long list of other men that have been up there."

I didn't bother removing my clothes, but just launched myself at her. I'd never understood what people meant when they talked about a red mist descending over them, but I did now. All I could think of was Diane's cunt, getting up inside her, and filling her with my seed.

There was just one problem, of course. I'd never fucked anyone, and my knowledge of the detailed anatomy of her vulva was sketchy at best. I was holding myself over her on the arms of the chair, and my cock was banging against her, but try as I might, it kept being pushed back by something solid, not sliding into her the way I thought it should. I put my hand down between her legs, but my fingers just seemed to get tangled up in the folds of flesh I encountered.

"God, Jack, my hole is a lot further back. Surely I can't be the first woman you've fucked?"

I still get shudders when I think back on this experience. I knew I was blushing, feeling totally stupid and ignorant; part of me wanting to run back and hide in my room. At the same time, the massive pressure in my balls and my cock was now unbearable as I felt her against the tip of my cock, so there was no way I was going to leave until I'd come inside her.

"Let me help, then, darling," Diane said, and the look on her face, and the tone of her voice gave me some confidence to carry on. "Let me take your virginity, Jack."

I felt her hand hit against mine, and somehow, she seemed to push my cock down at the same time as she opened herself up. All of a sudden, the resistance disappeared, and my cock slammed into her, not stopping until my balls hit the ass that Wesley had been feeling up earlier.

I thought I knew what it would be like to actually have my cock inside a vagina, but I was wrong. It was as different from jacking off as a Model T Ford is to a Cadillac, Ferrari or Rolls Royce: they both moved you from A to B, but the sensations along the way were quite different.

I'd never felt anything like it before. Diane's cunt seeming to grip the whole length of my cock, but the grip was warm and wet, and allowed me to smoothly slide it in and out of her. When I pulled back, I looked down, and could hardly believe the wonderful sight of my dick pushing her lips apart, and disappearing up inside her.

"Just fuck me, Jack. Fuck my cunt hard, then fill me with your virgin spunk."

I really didn't have any choice. I certainly couldn't have stopped if she'd asked me to, because I seemed to have been taken over by some alien being, whose only mission was to drive my cock in and out of Diane's cunt as fast as I could.

I looked down at her, loving the way her tits were bouncing around with every thrust, and I could see she had a smile on her face. But I barely noticed, as my senses were overwhelmed by the intense, almost painful feelings coming from my cock as I pumped in and out of her hole, a hole that I knew had been filled by so many other cocks in the past.

When I was jacking off, I normally managed to make it last, but I could feel the pressure in my balls reaching bursting point, as the millions of sperm were fighting to get out and into Diane's womb. I wanted the feelings to last forever, but so much sooner than I wanted, I felt my cum burst up my cock, and jet after jet shot deep inside Diane's body.

"That was wonderful, Diane," I gasped, as I collapsed on top of her, utterly exhausted, my dick shrinking inside her.

"Well, Jack, I enjoyed it being your first time, but if you want to keep fucking me, I'm going to have to educate you, so next time I get to come as well."

"But ... what ... you mean girls come as well? How?"

"Oh, Jack, you're so innocent, which makes it sweet, else I'd never forgive anyone who didn't get me off as well. Still, I need a pee, and we ought to eat, so let's order room service then have a shower, After we've eaten I'll teach you how to get a woman to come, and we can do it not just once, but several times, so you'd better be a quick learner, Jack."

Once I'd gotten off her, Diane called room service, and ordered us salads and beef filet, with a bottle of red wine to go with it. I noticed as she was on the phone that a trail of my spunk was running down the inside of her leg.

"Um ... Diane ... you're leaking. Is that supposed to happen?" I asked as she headed towards the bathroom.

"What did you expect? That we had a little door that would keep everything inside? Now get out of my way, and let me pee. I'm bursting."

"Um ... I've always wondered ... but just where does a woman pee from?"

"Jack, Jack, Jack. Oh well, I'd better start your education there, then," she replied as she sat on the toilet pedestal.

She sat back, and used some tissue to wipe away the trickle of sperm, then she pulled her pussy open again, setting my cock twitching already. See here - get a bit closer, Jack - see just inside my hole, there is another, smaller one? Get closer so you can have a good look."

I bent over in front of her, and with my face only a couple of feet from her pussy, I could see a little, pink circle, in what I'd thought was just a hole, the start of her vagina. While you could move a cock around to point it in where you wanted, this just looked silly.

"Yes, but how do you make sure that it comes out in the right direction, then?"

"Just get a bit closer, Jack, and I'll show you. You have to be really close to see it."

I was just starting to get closer, wondering if in some magical way the tube would pop out, when a powerful jet of pee hit me right in the face.

"Stop ..." I started to yell, only to find my mouth filling with pee.

Diane was laughing outrageously as I tried to pull back, and nor did she even attempt to stop, but just moved her hips a little, so I ended up dripping with her pee from head to toe.

"Oh Jack, the look on your face was just beautiful - this is one lesson I don't think you'll forget, will you?"

"You fucking dirty bitch ..." I started to say angrily, then I started to see not just the amusing side of it, and realised that somehow this marked a complete transformation in my sexual journey: I mean, I'm sure the must be many couples who didn't have enough trust and intimacy for such a thing to happen. I started laughing, as I tried to shake the pee off me.

"Don't bother with that, Jack. Just take everything off, and we'll put it in the laundry. Of course, it will mean you'll have to stay in my room tonight, until your clothes come back. Could you cope with that, Jack?" she said, pressing her body against my wet clothes, and kissing my pee-covered lips.

She looked so beautiful, so alluring and so sexy as she stood in front of me, looking at me like a young girl who'd asked for something, and was afraid the answer would be 'no'. God, I wanted her again, after she'd taught me how to give her pleasure as well, but I felt some other emotion growing inside me that I had never experienced before. Of course, I took my wet clothes off, and joined her in the shower.

"Wash me all over, Jack. I want to feel your hands all over me, and I'll wash you."

I put shower gel on my hands, and started with her breasts, which had water dripping off the nipples. They felt so smooth: firm, yet soft and giving, and the feel of the shape of them in my palms started to make my cock stiff again. Diane started washing me the same way, and we kissed under the water, as our hands soaped all over each other's bodies.

"Don't forget my ass, Jack. Right around my asshole. You do know where my ass is, don't you?"

I showed her I did, as if I could forget it, pulling her cheeks open, and soaping around the tight opening of her anus that I'd seen earlier, adding another first to my experiences that day. I pulled her to me, pushing my cock between her legs, hoping to get it back inside her.

"Oh no, Jack. No fucking until I've taught you to do it properly," she said, pushing me away. "Anyway, the food should come soon, so we should dry ourselves off, bag your clothes, and you can wear the other one of the lovely soft robes the hotel provides."

As it happened, we had only just dried ourselves off, when there was a knock at the door, followed by the familiar cry of 'Room Service'. I had my robe on, but Diane was just trying to find the arm of hers, when I had a brainwave.

"No, Diane. Leave it off. Answer the door naked. You'd like that, wouldn't you? I'd like to see the look of lust on his face, and the realisation that I was the lucky guy that had got to fuck you, so he was out of it."

"Fucking hell, Jack, you keep surprising me. Perhaps we've got more in common than I realised. Fine; sit down and watch."

I wrapped the robe around me and sat in one of the chairs, while Diane walked naked to the door, and opened it.

"Please come in," she said, and I guessed she was smiling, though all I could see was the look of shock on the guy's face.

Still, it was Vegas, and I doubted it was the first time he'd come across a naked woman in one of the rooms. He put a neutral expression on his face, and wheeled the trolley inside, laid a cloth on the table, then set everything on it.

"Now, where's my purse?" Diane said to herself, as she took the check to sign.

"I've got a pen ... " he started to say, but he broke off suddenly, as he realised that Diane was now bent over the arm of the chair, one leg off the ground, reaching for her purse, her back to him, which must have been giving him a perfect view of her asshole and her cunt.

I didn't have as good a view as him, but what Icould see was that she'd already found her pen, but was pretending she hadn't to give him a longer view. Eventually she stood up, and signed the check.

"I've given you a really big tip," she said, standing next to him so he could inspect her tits close up, "because I need you to take these dirty clothes to the laundry. I'm afraid my boyfriend had a bit of an accident, and pissed himself."

"You really need to do something about him," he said, taking the bag, but pointing to me, and I realised that seeing Diane showing him her pussy had got my cock stiff, and it was now poking through the gap in my robe.