The Strap-on pt. 5 “New Tricks”

I Learn about Cuckolding

[This series, of which this is Part 5, begins with a gift that is put to unexpected use. Ali keeps her boyfriend off balance, but he keeps coming back for more. He’s in a chastity cage as this part begins, and he’s been there for many days. Things have happened, and a new adventure is set to unfold.]

Over the next few days, although I practically begged Ali to uncage me, increasingly my fantasies had turned to pegging – I was just too embarrassed to say. She’d made some reference to my “boi pussy” (she told me how it was to be spelled, as if I would ever write the word!), and I didn’t like the connotations I drew from that and avoided the subject of pegging as much as possible. During this time, when I’d request for her to take the cage off, though, she loved to talk about how I had cum with it on and how much that turned her on.

“I never would have believed it,” she said. “I want to do it again where I can watch it!”

“But I didn’t cum, not really,” I explained. “I know you said it was real cum and not precum, and it must have been, but I didn’t really cum, or maybe I should say ‘orgasm.’ I didn’t orgasm, it all just leaked out of me.”

“You didn’t cum?” she asked as if she’d just heard it for the first time, and I was immensely relieved that she finally seemed to grasp what it had been like for me.

“No!” I said.

She seemed so disappointed by that!

“And I’ve just been gushing at the thought of it! Do you even think you could?”

She looked at me so skeptically that I felt challenged in some critical way, like it was a form of impotence or something. I can’t explain it, exactly. I just know I suddenly wanted to make that fantasy come true for Ali so much.

“I’ll bet I could,” I said.

“What do you think you’d need for it to happen?” she asked, and I had to admit I didn’t know.

“I wonder if gets more likely the longer you’re in the cage?”

“I’m sure that’s true,” I said, like a complete idiot, not realizing how much of an idiot I was just yet. But I did realize, even then, that it meant Ali would suggest leaving the cage on, whereas she’d practically promised to take it off pretty much at any time now.

She did make that suggestion, and I reluctantly agreed it would make sense.

“Is that really what you want?” she asked, not satisfied with my apparent reluctance.

“Oh yes,” I said. “It’s what I want.”

“But you’ll have to go without for who knows how much longer,” she said. “Can you stand that?”

“Well, we could try sometime soon,” I suggested in a spirit of compromise, and she agreed with that. And in fact the very next day we tried it, but it didn’t work.

“I don’t think you’re being kept excited enough anymore by just the cage,” Ali said.

“I’m pretty excited,” I protested. “You can’t tell, of course, because of this tiny cage, but if you let me out you’d know.”

“But you don’t want to be let out?” she asked.

“No, I guess not. It would spoil the experiment.”

“I think I know just the thing to keep you more excited without letting you out. Plus it might help me solve a certain craving I’ve been getting lately since you’ve been, um, indisposed.”

“You’re wanting me to use the other one on you, you’re saying?”

“No, but never mind. I don’t really think you’re ready for what I have in mind yet. Maybe we should just call it all off…”

She actually started reaching for the key on her necklace as she spoke, which I found alarming, to my surprise.

“No, no, I’m sure I can take whatever you’ve got in mind,” I assured her. “I want to do this for you!”

I don’t know if it was my desire to please her that was speaking, my desire for her not to be disappointed in me, or the challenge that she thought I couldn’t take what she had in mind that was speaking, but I assured her I could handle anything she might dream up. I talked us both into it over her obvious reluctance. I even felt a little guilty for pushing so hard, so I tried to make up for that by giving her especially good oral sex for the next half hour as she gradually overcame (so to speak) her concerns.

There was a strange man sitting in the living room when I arrived home the next night.

“Darling,” Ali said, “this is Travis. He’s agreed to help us with that thing we were discussing last night.”

I had no idea what she was talking about and said as much.

“He heard what you wanted to do and said he could help.”

“With what?” I asked, still baffled, and the more so by Ali’s apparent reluctance to be clear about it.

“Aren’t you even glad he wants to help?” she pouted, but it was a fake pout, and even with the cage on and in my desperate condition I was beginning to lose patience.

“I’m sure I’ll be glad if he can help, but what’s he going to help with?”

“Oh, never mind,” she said to me with a sigh. “Travis, you might as well leave after all.”

Travis stood up. He was a little taller than me, younger than me and not dressed in any way that made his business obvious. He could have been a mid-level manager somewhere or a grocery clerk for all I could tell. He seemed a decent enough guy, nothing special. It made me worried I was being rude.

“No,” I said. “I’m sorry. There’s no need to rush off. I’d just like to know what you’re here to help with,” I said to Travis.

He shrugged and sat back down.

Ali was still trying to choose her words carefully.

“That thing you said last night you wanted to do, for me, you know…?”

“No, I don’t know. Just tell me Ali.”

“Okay if you just want me to say it. You said you wanted to cum, really orgasm, with the cage on and wanted to keep the cage on till we could make that happen, right? But that we needed to find a way to keep you excited?”

I guess I shouldn’t have been shocked by that, but despite her avoidance of plain talk I just hadn’t been thinking along those lines at all, and the fact that she’d told someone else about what we’d been discussing hit me hard. I should have called it all off right then, no doubt, but I was just so embarrassed! So I just stammered out some nonsense about our intimate secrets and blah blah blah. It was lame.

Ali was so apologetic. She said she was sorry but had tried to speak in code to make it less embarrassing, but that there was nothing to be embarrassed about at all, my wanting to make her happy… She said that after last night when I told her I wanted to do anything that would help she’d thought I knew what she meant, and that she thought it was clear I meant she should bring another man in to take care of her needs while keeping me on edge.

It had been anything but clear, but I guess I could see her point, and god help me, my cock was throbbing in its cage at the idea of watching her have sex with another man, now that I thought about it. I guess it’s obvious to most people, but it didn’t occur to me till much later that Ali had set the whole thing up. At the time I thought she was just trying to figure things out, the same way I was, that it was all new to me.

Anyway, it wasn’t long before I’d agreed to go forward with things, and we all had a drink and settled into a somewhat uncomfortable social interaction. My questions to Travis were guarded, I guess you could say, but I did want to know how he and Ali had met and other basic things, and it turned out he’d been a somewhat distant acquaintance of hers from some time in the past. That did raise questions in my mind, but in politeness I didn’t pursue them. I found out some other basic stuff about him, but nothing worth reporting on. He was just a guy as far as I could tell.

As we started, I was seated in a comfortable, deep sort of chair, and Ali had been in another one beside me, while Travis had somehow ended up at one end of the couch. After a while, Ali replenished our drinks and sat beside Travis on the couch, her hand casually landing on his thigh, which I guess started it all in a new direction. Not completely comfortable for me.

“Craig is obsessed with cumming from being pegged,” she told Travis. “You should see the way he takes it,” she giggled.

I blushed furiously at that, but Travis took it in stride. He just nodded as if he’d heard it all before, and he also took Ali’s hand on his thigh equally in stride, although I was beginning to see signs that he liked having it there – there was a noticeable bulge.

Despite my embarrassment at Ali’s revelation about me, my cock was throbbing intensely, and I was so horny I could barely contain myself. I couldn’t peel my eyes away from Ali’s hand, which soon moved up and onto Travis’ bulging cock.

We all pretended none of that was happening, though, and Ali just left her hand there for a few minutes while we continued to make small talk. I forget what any of it was about. I don’t think any of us were paying attention to it at the time. For me it was just… Ali’s hand. And yes, I wished it could be on my cock and it could be my bulge, but I’d be lying if I didn’t admit it excited me where it was.

Ali knew my thoughts, and when the time was right she moved her hand slightly, and slowly, looking me straight in the eye as she did, pulled the zipper down.