Friday, August 11, 2017

Simon/Joy: Crossing the Line

When Teddy revealed to me the secret bet between four of the guys at work to see who could screw me first, I went through a bunch of emotions: hurt, offended, annoyed, before settling on flattered. It was especially flattering that Teddy was making a concerted effort not to pursue me, not just because Stretch was in the "lead" but because he didn't want any part of the actual bet - even though he and I had a better connection than Stretch and I ever did.

So my first act after a bit of contemplation was to text Teddy and ask if he wanted to win a bet.

He was reluctant. Ever the gentleman, I've got to give him that. After a few weeks of hinting that I was eager to throw down with him, he still protested: why did there have to be a winner, he asked? And the answer was, because I wanted there to be one. Not only did I not want them to keep secretly plotting to get in my panties (to win a cool grand) but I also happened to want Teddy in said panties. I caught a bad case of thirst for him.

At first I thought I was too good to chase anyone - after all, at any random bar I walk into I can have my pick of dudes. But the results I was getting were starting to feel very bland, interchangeable and meh. As I've already said, anonymous guys don't really care to put much effort in. So while I was enjoying myself, I was really plateauing when I should be finding new peaks.

A rule that I have more important than "Don't chase" is "Always get what you want." I set my sights on Teddy and I was going to have him Even if just once (and something told me if I could get him once he would be mine as long as I wanted him.) So I formulated an ingenious plan. Step one: Invite myself over to his place under the pretext of work. Step two: Have a few drinks. Step three: Well, that's pretty much all I thought I would need.

So the next week, I found myself at his house, and we were going over some arcane real estate bylaws over a bottle of Merlot that I brought when my hand innocently grazed his. Our eyes met with that tempting flicker that I knew would cause him to wonder if it meant something.

I worked my body language. Pointed my knees toward him, Played with my hair. Put a sweet singsong in my voice. "You know... I really love your place. I'd like to see more of it." Hint, the bedroom.

He played dumb, going on about the square footage and the maintenance. I encountered a new problem... I've never had to work for it with a guy before. How do I go from playful flirtation to bumping uglies if he won't play ball? The wine wasn't working. I briefly considered just stripping down to my bra and panties to see how he'd react, but it's better to play the game. I made sure to touch his knee three times as we conversed.

Finally, he called me out on it. "Joy, I've told you before... I can't."

I pouted, "You don't find me attractive?"

"I... you're very attractive. But the bet... It taints the whole thing."

"Well, if that's the case," I said, fiddling with the buttons on my top, "Nobody needs to know."

"What are you suggesting?"

"A private fling," I said. "Our little secret. No bet. Just two adults having a good time."

His face went stony. "You... really want this?"

"More than I've ever wanted anything," I said, as sultry as I could.

He still seemed iffy. "There's just something about you... you seem to know exactly what a guy wants a woman to be."

I smirked, "Is that a problem?"

I guided his hand to my thigh. I felt the thrill of victory closing in as we neared the endgame.

"Not at all, I just... I've never had a woman throw herself at me this way. I can't believe it."

"Believe it," I said, leaning in to kiss him, caressing the stiffening rod between his legs over his slacks.

Before we knew it, I was on top of him, he was pawing at me, trying to get my bra unfastened. I moaned in pleasure as he teased my nipples with his tongue, as I knew all along he was fantasizing about doing. Our hot breath on each other's tongues, his fingers finding their way into my private crevices. I goaded him on with moans of pleasure, finding the more I played it up, the bolder he would get.


By the end of the night we had done it three times, and I had climaxed multiples of that.


The next day, he asked me out to lunch. I didn't see any reason to discuss what we had done, except to confirm that we would both want to do it again, preferably on a regular basis.


It turned out that wasn't the case.


"So, that can't happen again," he said with a stony face.


My eyes bulged out. "Uh, did you not have fun? Because it seemed like you enjoyed yourself."


He sighed. "I'm just not the casual type. I'm past that, I want something more real. If you want to try having a relationship, that's something we could consider, but... I feel like that was why you didn't keep going out with Stretch, so unless you feel differently for me..."


I rolled my eyes, "Sorry, I don't."


"I didn't think so."


Where was all this coming from? Isn't he supposed to be a guy? I thought he'd be thrilled at the prospect of no-strings-attached sex with a chick who looks like I do.


Whatever, I thought. I don't need this. I'm gonna be a guy again in a few months and this will all be behind me. I should probably cut myself off from my crazy sex life now so I don't get addicted.


Once I got "over" Teddy basically dumping me, I had an epiphany. Shayla, my hot friend, is totally into the relationship thing. I thought she would like a sophisticated older guy like Teddy. So I introduced them and they hit it off, and now they're dating. Which is awesome, because they're both super hot. Teddy's been a little coy on the details but I think they've been sleeping together for a few weeks. I've got to admit, I'm pretty jealous... I had halfway thought that when I got my body back I could get the new Joy to "introduce" me to Shayla. But there's plenty of fish in the sea.

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