A Complicated Relationship

"Don't worry, I'll get that tucked away somewhere nice soon," she replied, smiling, and 'accidentally' brushing her tits across his hand holding the bag, as she turned to look at me.

"You enjoyed that, Diane, didn't you? Not just letting him see you naked, but getting a view right up your cunt and asshole," I asked, after I'd ditched the robe, and we both ate, naked.

"I thought you didn't like the way I flirted in the office, or when Julie and I stripped down to our undies? I had you pegged as a bit of a prude, Jack. So how come you encouraged me to go to the door naked? You're right, I enjoyed it, but the funny thing was it was so much more enjoyable having you there watching me do it."

That was the question. It was one I couldn't find an answer to, even for myself. I'd now fucked her myself, if not very well, but rather than making me possessive, or disapproving of her slutty behaviour, somehow it just made me want her more.

"I don't know, Diane. Maybe I'm just some sort of pervert ..."

"... like me, you mean, Jack? Because that's what I know I am, but I've never found anyone who accepts me enough to let me give full rein to my twisted fantasies."

"To perverts, then," I said, raising my glass, and Diane copied me, chinking the glasses together.

"But you're still just a learner, Jack, and as soon as we've finished dinner, I'm going to teach you how to make me come."

It was strange, because it felt perfectly natural now to be bare with such a beautiful naked woman next to me, my cock softening a bit, then hardening again as I saw something new in the way her tits or her pussy were exposed. Nor did I feel embarrassed about being so ignorant, but I was just longing for Diane to teach me everything about sex and her body.

After dinner, Diane grabbed my hand, and led me into the bedroom.

"Pull up that chair, Jack, so you can get a good view," she said, laying on the bed on her back, knees bent, legs wide, and her cunt pulled wide open. "This is what you need to know about, Jack. It's my clit, a bit like a miniature cock. It's what you need to play with to get me to come."

I could see what she meant, as she started massaging an almost half-inch long nub of flesh at the front of her slit, which bent and turned, making her groan each time. I'd always thought of a cunt as just a hole that let sperm in and babies out, but I discovered that the reality was so much more complicated, with holes inside holes, and now little cocks, let alone the complex flaps of flesh that she was holding open.

"No, Jack, no jacking off," she said, as she noticed what I was doing. "You just watch, then you can fuck me again, but this time you've got to get me to come, else I'll get you thrown out of my room as an intruder."

That was hard, but what was fascinating was the way whiteish, translucent fluid had started oozing out of her hole as she was touching herself, and she used her fingers to gather it up, and rub it over her clit.

"What you can't see, Jack, is that the clitoris goes right along either side of my slit, inside my vagina. Some people talk about a magic G-spot which makes a woman come almost at once, but neither I nor scientists have found it. Personally, I think it's just a male invention, so that when the woman doesn't come, they can blame it on her vagina rather than their lack of technique. No, it's rare that I can come without my clit being played with, but if you do it right, I can guarantee I will. So just watch and learn."

I could smell her scent strongly, and now hear the squishing noises her fingers were making as she rubbed her clit, then drove her fingers inside her, before returning to her clit. I decided to be a bit more than just a spectator in her amazing display.

"You'd have let the room service guy fuck you, if I'd not been there, wouldn't you, Diane?"

"Oh God, Jack, do you really want to go down this path? I don't want to upset you."

"You would have fucked him, though, wouldn't you? Tell me what you'd have done."

"God, Jack, alright, if you're certain. Well, I'd have bent over the chair to show him my cunt and asshole ..."

"... the way you did in front of me ..."

"... yeah, but when I got up, I'd have suggested he might like his tip in something other than money."

"He wouldn't have believed you at first, though, surely?"

"Well, given I'm naked, and I've just shown him both my holes, I think he might have. Still, I'd have grabbed one of his hands, and forced him to touch one of my tits ..."

"... and I bet you'd have started undoing his pants, and taking his cock out, wouldn't you?"

"Of course, Jack, and then I'd have dropped to my knees and taken his dick into my mouth ..."

"... tasting the thread of pre-cum that was leaking out of it ..."

"... then I'd have pushed my head forward, and let his cock go way down my throat. But I'd also have one hand on my clit, because he couldn't reach it, even if he wanted to then. You are watching and learning, aren't you Jack? Just running my fingers around it, not too much pressure, then letting it recover as I slide them back along my slippery gash and into my vagina. See how wet I am now, Jack?"

"So, you'd just have given him a blow-job, then, Diane? Would you get him to come over your face or your tits?"

"Oh God, Jack, that would have been fun, but look how wet I am now. No, he's going to come right up inside my cunt ..."

"... the way I did earlier, Diane ..."

"...yeah, but I'm going to fucking come as well, get a level of pleasure you failed to give me."

"Teach me, then, Diane. Teach me to send you crazy when I fuck you."

"I'm undoing his pants while I let him fuck my mouth, letting him almost choke me, and saliva fall out of my mouth on to my tits, running down and dripping off my stiff nipples on to the floor. I pull back, help him take his shirt off, then I pull him into the bedroom ..."

"... and I bet you laid back on the bed with your legs open ..."

"... just like I am now ..."

"... holding yourself open, so he can see all of your cunt, from your clit to your slippery, gaping hole ..."

"... yeah, his cock is throbbing, it's so stiff ... fuck me, I'd beg ... fuck me till you fill me with your spunk ..."

"... so he rammed his dick up you, and started pumping away ..."

"... but he also put his hand down to my clit, and between us we rubbed and stroked, pinched and flicked it, just like this, Jack. Look."

I couldn't believe the violent way Diane seemed to be abusing the little nub at the front of her cunt, or the way she was ramming the fingers of the other hand into her vagina, mimicking the hotel guy, who in both our imaginations was now fucking her hard.

"Oh, fuck, Jack ... I can feel him in me ... and my pussy feels as if it going to explode ... oh ... he's rubbing my clit harder ... FUCK ... I'm coming myself, as I can feel him pumping his seed inside me ...aagghhh ..."

I watched Diane in amazement, as her back arched, lifting her ass right off the bed, and she slapped her legs together, her hand trapped in between them. Then she let herself fall back, her legs opening again, giving me another view of the glistening wetness of her cunt, as she rubbed her clit again, before the whole cycle was repeated.

Then she slowed down, groaning as the movement of her fingers slowed, then stopped. Eventually, she just lay on the bed, panting, her legs wide, her pussy a sticky wet mess of her cum.

"Now that, Jack, is how a woman comes, but God, I haven't come like that for - maybe ever. It was knowing you were watching, while I imagined being fucked by someone else. So, come and fuck me now, Jack. Fuck me while I've still got his sperm sloshing around inside me, and see if you can make me come again like that."

"Oh, I'll fuck you alright, Diane. You call me a jack-off, but what sort of whore jacks herself off in front of one man, while telling him how she's getting screwed by another?"

"Me ...uh," was all she managed to say, as I drove my cock up her slippery wet cunt.

I was determined she was going to find out just what a fast learner I was. I worked the hard, wet lump of her clit the way she'd shown me, but hard, like when she was close to coming. I felt her squirm under me, as I pulled almost out of her hole, then banged my cock back in her hard, making my balls hit her ass.

"Not to fast, Jack, else I'll ... you fucking bastard!" she said, as I stopped playing with her, but lowered my head and started sucking hard on one of her nipples, pulling it up as far as I dared. "For fuck's sake get back to my clit," she gasped, digging her nails into my ass, as I pounded in and out of her.

"I hadn't forgotten, you dirty cunt," I said as I dropped her tit out of my mouth, and started rubbing hard again between her legs.

"Aagghh," she groaned, as I felt her start to squirm and twist under me.

I had to slow down a bit myself, else I was going to explode inside her too soon, but I kept rubbing her clit as long as I dared, then I slid my fingers back and forced them into her hole, alongside my cock.

"There you are Diane. Now you've got me and the hotel guy up your cunt at the same time. How does that feel?" I asked, ramming my fingers in and out of her, out of time with my cock.

"Fuck, Jack ..." she gasped, as I twisted my arm to force my thumb to rub around her clit.

"Now we're both going to come up you together, Diane. Two cocks, each filling your cunt with spunk, and you're going to fucking come like you're never come before ... uh ... uh ..."

I had to break off, because not only was my spunk shooting out of my cock into her like a rocket's thrust, but I needed all my concentration to avoid being thrown off Diane's body, even the entire bed, because she was bucking and jerking so violently. We must have lain together for ages, panting, savouring the sensations as they passed away, my cock slipping out of her.

"Fuck, Jack, you nerds are good learners, aren't you?"

"Only because you're such a good teacher, Diane."

"I've got plenty more to teach you, Jack."

*********************

Fortunately, my clothes came back first thing in the morning, because the next day was intense. We had lots of interest from potential customers about the app, often coming with ideas for improvements or specific requirements. However, I still managed to find a bit of time for some gambling.

The sequence of spins in electronic fruit machines is supposedly random, but like almost all computer-generated random events, they are actually part of a very long sequence which eventually repeats. If you can identify where you are in the sequence, you can then work out when it will hit the next jackpot.

That was the advantage of being a nerd. I'd identified the best machines, and with a bit of reconnaissance, I located a few machines which hadn't paid out for a while. Casinos obviously don't like what they call 'counters', but I'd written an app, and with a tiny hidden microphone, I could record the sequences of a couple of adjacent machines, as I slowly played on one myself.

Jackpot! $10,000, but I could only do it once without people getting suspicious, so I went back to watch Diane flirting with customers, hotel staff and her team. That night, Diane started teaching me everything she could about a woman's body, and how it could be used for pleasure.

She gave me my first blow job, taking me right down her throat, in a way that I couldn't believe was possible, as I told her stories about how I'd like to watch her giving blow jobs to her team, and getting fucked by a customer.

Then she taught me how to eat her out, making her come with my tongue on her clit, as she described the cunts of the women she had fucked, and how they tasted so different. At first, I wasn't sure I was going to like the tangy, musky taste of the sticky fluid oozing out of her vagina, but by the time I'd got her twice, I was totally addicted.

Finally, she did me the honour of letting me fuck her asshole, even though I wasn't gay, and I was determined to reward her for it. I paced myself carefully, slowly sliding in and out of her tight anus, while we both used our fingers in her cunt, and on her clit. I took her right to the edge, then stopped, and if she carried on, I clamped her hand against her with mine. The two of us stayed close to the edge for ages, kissing, and talking about other men she let in her asshole, and, it turned out, women with strapons.

Eventually, we could hold on no longer, and as I injected my cum deep in her anus, she came, twisting and twitching against my cock, both of us yelling at the top of our voices.

"Oh God, Jack, I thought you were just a dork, but you're fuck amazingly, and I think I might be falling in love with you."

All I could manage to get out was a muffled "me too," as I found my eyes starting to fill with water, and an emotion I'd never experienced before in my life, swallowed me up. If this was love, then I wanted more of it.

I lay in bed after Diane had gone to sleep, thoughts ricocheting around in my brain, until eventually a crazy plan crystallised out.

The next day, I made my excuses to Diane and the team, and headed onto the Strip. First, I took the risk of taking a smaller pay out on a machine in a different casino, then I spent it all on the rother part of the plan, the cheapest component just being $77, but the rest a great deal more.

I managed to get back to the fashion event in time to join the day's sweep-up meeting, collecting feedback and specific requirements for the app from potential customers, then watching Diane hug and flirt even more than usual. At least, that was how it seemed to me, as I was itching to set my plan in motion.

"I've ordered room service again, Diane. I wanted to celebrate the success of the app, and I've a special present I want to give you afterwards. I just hope you like it."

"God, Jack, I love surprises, but do I really have to wait? It is a proper surprise? Not just your cock in me again? Though that would be fun."

"No, it's a real surprise, Diane. Still there's not long before the dinner should arrive, so you can start to get ready for it: take all your clothes off. This time, when the food is delivered, I want you not just to be naked, but let the guy touch you as part of his tip."

"Jack! Are you sure?"

"Oh yes, Diane. I know you'll enjoy it, won't you? You never seem to worry about your team touching you."

"Yes, but with a stranger, and with you watching ..." she said, taking her dress off, and the look on her face telling me that she was starting to get excited just thinking about it.

"I'm going to go in the bedroom, and just peek around the door, but I want you to make sure I can see everything. I want to see his hands on your tits, and his fingers parting your cunt. Who knows, if you do it well, maybe I'll fuck you again tonight," I said, ending up smiling, as Diane stood naked in front of me.

"Oh, if I do this, Jack, you won't have any choice as to whether you fuck me, darling," she said, pressing herself against me, rubbing her hand over the front of my pants, and kissing me.

My dick was throbbing in anticipation of watching her being touched by a stranger, but at the same time, my heart was fluttering, as I started to worry what she would think of the rest of my plan. I carried her clothes into the bedroom, undressed myself, then worked out how far open I dared leave the door, as Diane moved around checking where she needed to stand.

She'd repositioned one of the chairs and the little table next to it that held her purse, and only moments after she had finished, the knock came at the door of the suite. I watched as her gorgeous ass wiggled across the room. She opened the door, making my cock springing fully to attention, as I realised the front of her naked body was inches from the hotel guy, the same one as the previous evening, and exposed to anyone who was walking along the corridor.

"Come in," she said, letting the door close, and standing so that both the waiter and I could see her tits and pussy.

When the food was laid out on the table, she repeated the trick of the previous day, bending right over in front of him to get the pen from her purse. I could see the wet glint of her cum along her gash, which was gaping enough for her dark hole to be visible. From his closer position, the waiter must have had an even better view. And from his face and eyes, I could see exactly how intently he was staring at Diane's cunt.

She stood up, looking as if she was going to sign the tab, but then she paused.

"You seem to like my body, so maybe you'd prefer to take your tip a different way?", she asked, looking coyly at him as she pushed her tits towards him.

"But ... you boyfriend ..."

"That jerk! All he wants to do is gamble, and he hardly seems to notice that I'm like this," she said, doing a slow twirl in front of him. "I daren't let you fuck me, but wouldn't you like a good feel?"

As she spoke, she put the room service check down, then pulled one of the waiter's hands to one of her breasts.

"Do you like the feel of my tits?" she asked, and the fact that his free hand cupped the other one was a clearer answer than his grunt. "You can pull my nipples."

He squeezed and pulled, but then must have started to worry he'd gone to far, as he heard Diane gasp as her nipples were stretched out.

"No, don't go yet, I've got even better places for you to explore."

She bent herself over the chair, and pulled her ass cheeks wide. Once again, both the waiter and I could see the tight ring of her asshole, and her cunt, now pulled wide open, sticky liquid clinging inside her slit.

"Finger my holes, darling, then tell me how stupid my boyfriend is being to turn me down."

The waiter gave a massive, nervous swallow, as lust for Diane's holes battled with his conscience.

His conscience lost, as I knew it would. He slowly reached out a hand, then slipped a finger inside Diane's vagina. God, I almost came as I watched her body being invaded by a stranger, only a few feet from me.

I saw his finger moving around inside her, before he pulled it out, covered in her cum. Then he used it as lubrication as he pushed it into her asshole, forcing open her anal sphincter. I'd never really imagined I'd get to see a woman's asshole, nor find a woman who I'd fucked several times, and certainly not that I'd then see her with a waiter's finger sticking in her shit hole.

I couldn't help touching myself, though I was determined not to risk coming, as I saw the waiter's other hand moving to Diane's twat. He pushed three fingers into her, stretching the opening of her hole in a way that sent shudders of excitement shooting through me. God, she was a dirty slut, and a bit of me was disgusted by the way she let a man, who she'd only seen once before, put his fingers inside her most private areas.

"God, that feels so good, but I think that's enough for a simple meal delivery tip, don't you?"

The look on his face said just the opposite, and he thought she should let him shove his cock up one or both of those holes his fingers had invaded, but he reluctantly pulled out of her.

"Thank you m'am," he said, picking up the check, then he licked her cum off the fingers that had been up her cunt. "I'm always at your service, and perhaps I could do something more for you, that would deserve an even bigger tip."

After the door had closed, Diane turned towards me as I came out of the bedroom, my stiff dick leading the way. She had one hand squeezing a tit, and the other visibly inside her slit, which I knew it would be rubbing her clit.

"That was fucking awesome. We really are alike, aren't we, but for God's sake fuck me, Jack, the meal can wait."

"No, Diane, I need to get this done, while I still have the courage."