The pushing of his boundaries started as a bet. We would bet on the smallest of things. If he lost the bet, I challenged him to do something small: a smoochy kiss, a back rub, a foot massage.
After a while, I started using bets to test his inhibitions. I quickly learned that he could overcome them when it was paying up on a lost bet.
The first serious broaching of his boundaries resulted from a football game. Neither of us follows football, but there was nothing else on the tellie one lazy afternoon, so we had a bet on this game. We each to took a team; if his team lost, I told him that he would have to masturbate in front of me. I immediately saw that the very idea of this made him nervous. In his mind, masturbation was supposed to be private, even secret… certainly not shared.
His team lost. He was obviously uncomfortable.
"Now?" he asked, clearly embarrassed.
"No, not now," I replied. "I'll call in the bet when it suits me!"
We were driving to my mother’s for dinner that night. As I stopped the car outside on the street, he moved to open the car door to get out, but I grabbed his wrist.
“No, don't get out yet," I said. "You lost the bet, remember. Now I want my payment.”
He was disbelieving, staring wide-eyed at me as he processed this. The he looked around, trying to judge whether there were people walking up or down the street and how close to the car they might come.
“Now!” I insisted.
He fiddled a little with the car door and shifted in his seat, as if gathering courage. And then he just started. Glancing down, I could see his erection already pushing at his pants. He unzipped his fly to release it, but was too shy to look at me. I'm sure he was blushing.
He slowly touched his cock with his right hand, still glancing furtively up and down the street. He stroked himself, then slid his other hand down to cup and squeeze his balls. It surprised me what he did with his cock and fingers; so different from how I played with him.
Soft, slow and tender, he continued to stroke his cock. Then, suddenly, faster and firmer, more rhythmical. His eyes were open, watching his hand moving and the tip of his cock swelling and reddening. Then his head tilted back, his eyes now tightly closed.
The car rocked slightly with his motion. Now it was me glancing around to see who might be walking past. My heart thumped as I watched. I felt as if I were a voyeur; watching something very personal in an exposed location, but not being part of it. He seemed vulnerable and that made me so hot. And wet!
I stopped him. I was finding it difficult to resist getting involved, to resist putting my hand around his shaft, or tweaking his nipples, or even bending down to put my mouth around him. Oh, I'd love to have him sliding into my mouth.
But I did resist.
“Wait! open your eyes," I ordered. "Turn and look at me. Look into my eyes. I want to see deep inside you as you come. I want to share your orgasm.”
He continued to rub up and down, looking into my eyes. Soon, he relaxed into the blend of sensations that were overcoming him. He started breathing heavily as the intensity grew. I watched how he sped up at the end, his hand moving so quickly that even if a pedestrian had drawn up beside us he could not have stopped.
When he came, his eyes drooped and almost glazed over. His pupils widened … such a vulnerable, intense, deep, sexy look. It made my clitoris swell and twitch. His cum spurted out over his hand and pants and made a beautiful mess, a slowly spreading stain on the fabric around his crotch.
When his breathing subsided, he finally spoke: “Do you have something?” He was looking for a napkin or tissue to wipe with.
I did, but I lied. “Nope.” “Pull your shirt tails out and it will hide the wet patch.” I wanted him to be nervous through dinner with my mother. A sticky, sweet reminder of his ongoing vulnerability and my role in it.
This football bet was just the start of it. It got me fantasizing about what I might do next, how I might craft my demands for payments into more vulnerable acts and nerve-wracking situations. The thought of how he might squirm at the whim of my creativity and the nervous anticipation of constant unpredictability gets me hot.
Sometimes he fusses a little, but I'm sure he is secretly stimulated by being ordered to do things he would not normally let himself do; even some things he claims he's never even thought about!
And there's been quite a few now: I’m sure he secretly wanted to be wrapped in cling-wrap and left helpless... apart from his cock. Maybe all men are turned on by the idea of being dressed as a woman, even to the knickers, bra and stockings – and lipstick! He certainly was. Though he denies it, I could see how much he got off on me watching him oiling his own nipples and playing with them. He almost came without assistance the time I tied him up and made him watch me having an orgasm with my vibrator, right up close to his face. And he was very turned on by me controlling the wireless vibrator in his pants, while we were out at dinner the other night with a group of friends. Almost repeated the experience of dinner with my mother!
I'm certain the "upcoming attraction" will have him dripping with nervousness and anticipation, because he'll be blindfolded while I film us having kinky sex, somewhere outdoors. Look out for us on a sultry summer's day in London!
Of course this is only half a story... I don't always win the bet.
Copyright © 2019 Crystal Knight. This is an original work. It may not be reproduced or distributed in any form without the written permission of the author.