Chastity Confidence Booster Ch. 01

My wife was filling me in on the latest details of her best friend Ofélia's divorce. It sounded messy: he handled the finances and blew their shared income on a buddy's investment without telling her. The guy was so ashamed he wasn't putting up much of a fight, but there was a lot of stress. "Good thing there's no kids involved," I commented idly.

"You said it," replied Nora. I was leafing through instructions for installing a light fixture, keeping half an eye on my wife. She had dressed up for her latest fancy lunch date with Ofélia. She was in a wide leg pantsuit, which was flowy but showed off her best feature, those curvy hips. I felt myself getting a little hard, and was kind of grateful to be leaning over the kitchen counter where my dick wouldn't be so obvious.

"No kids but they have to divide stuff up anyways. He wants to keep the car."

"Uh-huh," I said.

"He works from home!" Nora said, outraged. "I can't believe he's making this kind of trouble for her, and in the middle of a campaign."

Getting hard, I started thinking about my wife and Ofélia's lunch date. You can call me a pervert, but when my wife says she's going out on a date with a girlfriend, it gets me going a little bit. I don't know why, I never thought there was any flirtation happening there, but... ah, what the hell, it was just getting to be too long since Nora and I had sex. We just didn't have time, and so I mostly took care of it myself, and my fantasies often drifted to my wife and other women. As it happened, I knew she'd had some of those experiences in the past, and that kept a couple of fantasies alive. Sometimes, if I'm being totally honest, my wife drifted out of the picture and it was just the other women.

A lot of people would have found Ofélia sexy, and I did too, but mostly in a scientific "yes, she is indeed" kind of way. She had a strong but cute face, she was petite but assertive, she dyed her hair white-blue which contrasted nicely with her olive complexion--but if you asked me, and Nora had, "would you have sex with her", I'd say no because the truth was that Ofélia was boring as hell.

She was a campaign manager in local politics, and she lived, ate, and slept local political campaigns. Maybe somewhere there's a city where the local politics are really interesting. If there is, I've never lived in it. Nora reported to me that Ofélia had a rich personal life, but all I'd ever heard her talk about was this bond issue or that gerrymandering or even worse, city council races.

You could call me an idiot for letting that get in the way, but I don't have a wandering eye and when she asked me--in bed, after sex, in an idly trailing-her-fingers-across-my-chest kind of way--Nora wanted the truth, and the truth was that I didn't want to have sex with Ofélia.

As it turned out, that was for the best.

"She just seems so stressed, babe," fretted Nora, going through our mail. "This comptroller thing is eating up all her time and she just doesn't have time to work through the divorce."


"What is a comptroller, anyway?"


"Like the accountant for the city."

Fascinating, I thought. An elected accountant. But I'm smarter than that, so what I said out loud was "Poor girl--woman. I hope she'll let us know if there's anything we can do to help."

Nora turned to face me with a curious look on her face. "Well, it's funny but she did mention something. It's kind of weird, though. Something we could do for her."

You don't stay married for as long as we are without picking up on the subtext. It was sexual. A little blush was creeping into Nora's creamy pale skin, and she was deliberately facing me with shoulders squared. I shifted a little. Still hard. I didn't necessarily want to do it but the thought of Ofélia and sex was still effective.

I'm a typical guy. My wife had asked me, after we had good sex, whether I'd fuck Ofélia. It took me a mere several months before I realized she was alluding to a threesome. But these days, we weren't even doing each other, much less bringing a third into bed. I wasn't going to bring it up again--honey, remember the time you implied you wanted to fuck your best friend--but hope springs eternal.

And here she was, my wife, alluding to it. The blood continued to keep my cock throbbing.

"What do you mean?" I asked, trying to waggle my eyebrows.

"It's like this-- she was telling me about a sex thing she's always wanted to try but she never could because Dave wasn't into it."

"Oh boy," I said.

"But just to be clear, it's not having sex with us!"

I blinked, genuinely confused. "Oh okay, because I just assumed, and like that would be, not the worst maybe."

I can be smooth, I swear to god.

"James," said my wife, "she doesn't want to have sex with you, I don't want you having sex with her, that's not it. It's a lot weirder!"

"Okay, well this I have to hear."

"Promise you won't laugh?" asked my wife, sitting on the couch. I stayed where I was, erection hidden by counters. But I put the manual down. "So Ofélia says that she's always been really busy, too busy even to drop everything and have sex for an hour or two."

"Is that how they do it? In politics?"

"Yeah it's all hook-ups. Worse than the Olympics. But she doesn't work that way. The thing that works for her is being in control of a guy, even when they're not having sex."


 I frowned. "Like a dominatrix thing? How's that less time consuming?"

Some part of me--my penis--was still convinced this was going to end in me getting some, whether my wife, her friend, or both. But my brain was deeply confused. Ofélia liked to, what, tie guys up and whip them? It fit with her boss lady persona, but I didn't see how it made any sense with what Nora was saying.

"No," laughed my wife, red rising further in her cheeks. "Like a, they call it, chastity?"

"Chastity?!" I said. "She likes to lock up guys' dicks?"

"No, no, she's never done it before, remember? Dave always said no. She said it was a big thing in their relationship. She felt like it would be a thing she could think about all day, kind of a way of having sexual stuff going on without sex happening, you know?"

"And she's in control? What a surprise."

"She is a very in-control woman, yeah. It does make sense. She says it'll give her confidence."

"Okay, so let me get this straight--she wants to lock up my dick to help her through her divorce?"

Nora laughed again, a little bit too much. "No, silly--James, she wants me to lock up your dick for her."

I was, of course, still fully erect. Look, you probably think I was lying about not wanting to sleep with Ofélia but I swear to God, everything I said was true. I get along with her but I don't really like her all that much, and she's good looking enough but not really my cup of tea. Nonetheless, my theory of straight men is that if your wife is ever talking about doing something sexual to you, and there's another woman involved, you are going to have a crowbar in your pants until you can get away and start thinking about something else.

I also want to be clear: don't have sex with anybody for a little while, and your wife's friend who you don't really like all that much starts to seem very appealing.

So I'm going to admit that I did what I did for bad reasons. I said yes. Because, on some level, I thought it would end with my p inside a v.

I'd never done anything like this before--Nora and I never got past handcuffs (for me) and some spanking (of her) and while we used to have sex a lot, we never did a tenth of the stuff we talked about in the heat of the moment."Oh Jim I'm gonna tie you down and ride your fucking face all night long"? That's just pussy talk, and realistically, we both have to get some sleep.

Nora's proposal was specifically to slip a cock cage around my dick, take some pictures (without my face, the last shred of my superego said wisely) and send them to Ofélia so she could vicariously have a penis under her control during this difficult time. And it felt good. Nora was insistent that I would not have sex with Ofélia, which made me feel good because she phrased it as 'that dick is mine'. That's always a nice thing to hear.

Maybe there was some kind of voyeuristic impulse inside me. I wouldn't have said so, but this felt safe and I trusted Nora. She said you can look at all the pictures before I send them, and if you don't want to, you don't have to talk to Ofélia about it. For some reason that seemed even hotter. So after swearing Nora to secrecy, I agreed.

Nora had to go downtown that afternoon to sign some things, and I was jerking off to some ffm threesome clip when it suddenly occurred to me that if we did this, I wouldn't be in charge of my own orgasms. I came immediately. Even that post-nut clarity just left me thinking yeah, it's probably for the best if I can't keep doing this so much. I was very aware that I had a bit of the death grip developing.

I did a little research. A lot of chastity stuff out there is just stroke material. A ton of it is pretty obviously by guys who feel bad about self-pleasure, and they want a lady to stop them but sexily. Usually it takes some turn at the end where the wife forces the man to live as a woman, which felt like a dead giveaway for being porny fantasy--but a lot of it rang true, and it gave me some things to watch out for. Mostly, it warned, keep things clean.

I got freaked out by some of the more elaborate stuff, so freaked out I texted Nora. "So honey," I said, "O knows I don't have a piercing, right? And I'm not getting one."

"LOL," she texted back. "She knows. No expectation of body modification."

"Well except the obvious," I shot back.

"Except the mandatory one," she said with a winking emoji.

Through my wife, I had made a few guidelines. Nothing was going in my urethra, multiple keys were to be secreted in multiple locations, absolutely no identifiable photos were to be exchanged.

Ofélia said--or, I should say, Nora told me Ofélia said--that for her it was just about control. In some way she felt like she had a sex life even while she was sitting at rallies and in meetings, as long as somewhere, there was a man whose dick she controlled.

That night, Nora brought it up in bed, idly stroking my cock through my boxers. "I think you're doing her a huge favour, honey," she said, tracing a little circle on the tip, "and I know we haven't had time to get it on ourselves lately, but maybe this'll be just the spice we need."

"You know, Ofélia is nice and all," I said, "but honestly it's just very flattering that my cock can be of interest to anybody."

"It's very interesting to me," said Nora, wiggling down and giving it a little kiss through the boxers. She gasped happily when it bobbed a little. In a few minutes, we were fucking, my wife writhing on top of me while I drove up until she came and then I did. As I was drifting off to sleep, I told myself in another moment of clarity: don't get carried away, don't blow things with your wife, and whatever you do, don't make it weird. Just play along...

Every time I thought about it for the next few days, I started getting hard again. It was going to be fun. The only detail Nora let slip was that the cage was one that Ofélia had bought years ago wanting to use it on Dave, but she assured me he never even put it on. "We'll sterilize it anyways," she said.

The day after that, I was driving to work, and I realized I needed to talk to Ofélia about this, one on one. I'm a trusting man, and I love and trust my wife, but it's a very intimate thing. And the photo thing still bothered me a little. My job was secure but it was never good for anything sexual to become public. Buses had ads warning teens about revenge porn for a reason.

I told my wife I needed to see Ofélia alone. She understood, but wasn't sure Ofélia had the time. "If it's that important to her, she'll see me."

And so I had a friend date with a femdom. We met at my favorite place, a barcade with lots of loud noise and room for private conversation. Ofélia breezed in in a trench coat and power suit, light blue checks and khaki pants. She was carrying a clipboard as if to convince us all of her importance.

I saw her through new eyes. She had a strong chin, and her hair was cut to be blunt but cute. It was almost tomboyish. I stood up and, believe it or not, we sidehugged. She put her clipboard down on the table and made a clearing gesture. "Well," she said. Then she cracked and started laughing.

"I'm sorry Jim," she said, "I've been in so, so many meetings today."

I smiled. "Well, thanks for meeting with me."

"Are you kidding Jim? Listen: I am asking you for a huge favor, and believe me, I know it. Nobody has ever been willing to do this for me. In a way you're being nicer to me than anybody ever has."

"Oh stop," I said, shamming modesty.

"I'm very serious," she said. "So. What do you want to talk about?"

"I'm scared," I said. "I'm scared of you, to be honest."

"Jim," she said, looking me directly in the fact with achingly sincere eyes, "I do not leave a bruise, at least not on the first date."

"Ha... ha?"

"No, that was a joke. Dammit, sorry, again I don't know to shift tone. In seriousness, I don't blame you. I'm asking you for a, a... extraordinary intimacy for the partner of a friend. We don't have a sexual relationship, we've never negotiated this stuff or even really talked about anything that wasn't our jobs. I am an open book for you."

I took a drink.

"So you've always wanted to do this?"

"Yesss," she said. She did a little fist pump. "Always, it's so exciting for me."

"Okay, so... why? Like I'm struggling a little with the idea that making somebody not have sex can be your sex life."

"Well like you Jim, I do masturbate."

I choked on my drink. "Oh holy shit!"

"Oh sorry, that also wasn't a joke. No but your wife says you've been jacking off a lot lately, and frankly, so have I."

"Do you call it that?"

"I call it the taco handshake Jim, but that's not important right now," she said in a brisk, businesslike tone. "I can see that you're uncomfortable with that idea, so let me just emphasize that I don't expect to simply have you do something intimate for me while you hardly know me. I do masturbate... frequently. And now you know. So let me explain why I like the idea of having a man in chastity."

Ofélia was one for having theories, and for expounding those theories. In my experience, these were usually theories about voting blocs and local elections and roughly as fascinating as reading the tax code. But here she was, using the same tone to elucidate her specific theory of femdom.

She used to believe that sex was about the positive act of sex; that is, if you weren't having sex, nothing sexual was taking place. As she learned more about the world she realized how flawed this was: many things that weren't inherently sexual could be sexually arousing or satisfying, leading her to the idea that the ultimate fetish would be not having sex. After all, she said, rising to the level of political speech, most of our lives are spent with sex as an interruption to not having sex. So the only way for something to be sexual constantly while also being a normal person and contributing member of society was to make "not having sex" sexual. For her, busy as she was, it made her feel sexually important without her having to rub anything or suck anything.

"Why don't you just not have sex?" I blurted out. "Why not put yourself in chastity?"

Ofélia leaned forward. "Because the truth is, Jim, my orgasms are too good. I like them too much to ever give them up. I've tried, and it just doesn't work. I can't give someone else control of my sex life. I'm just not that kind of person," she stabbed the table with her finger as she said this last part.

I paused, and frowned. "What makes you think I'm that kind of person?"

Ofélia smiled, the most dazzling smile I'd ever seen her unleash. It was a politician's smile, broad and all-encompassing, radiating warmth and embrace. She leaned closer and I followed, putting my ear next to her mouth.

"Well Jim," she said breathily, tickling my ear with her words, "you tell me: was I wrong?"

The rest of the conversation was about the photos--Ofélia proposed that she simply inspect my imprisoned dick in person, but she warned that her tough schedule stopped her from being able to do that often, and she suggested that would simply be more infuriating for me. "I want to be clear," she said, slipping back into politician mode, "right now your wife is keeping you in chastity at my behest, but if I am the one inspecting that penis, you will not have orgasms unless I am satisfied that you are obeying me."

It also freaked me out a bit, to be honest. It suggested that this was a deal with Ofélia and not with my wife, and that worried me on a lot of levels. I said I preferred to think of my dick as the dick to which my wife had access (the politician speak was catching) and that my wife's friend desired pictures of a dick in a certain situation and this dick was, simply incidentally, my dick. So my wife would domme me for her friend. Hands were shaken (Ofélia had an excellent handshake).

"Hey," said as I was paying, "how do you find time for the, you know, taco handshake? If you're so dang busy?"

Ofélia looked at me and smiled again, brushing her dyed bang out of her glasses. "Jim, you can always find a way to rub one out. It's just a matter of ingenuity and shamelessness."

Her phone rang, and she had to tell some alderperson about needing to wait for election day to find out. Don't trust the polls, she said, trying to encourage her client to keep knocking on doors.

It was then, paying the most attention to Ofélia that I ever had in my life, that the last piece fell into place: she was a success, a type-A boss, but her whole business was trying to wrangle the public, which ultimately was out of her control. I had liked talking to her, and now I even had a little sympathy for her. So we were agreed. I would help her out. Using my penis.

In the end, Ofélia passed the device off to Nora at one of their lunch dates. They usually met at a terrace cafe near Ofélia's office, and I kind of loved the thought of being sexually present on one of their dates.

Nora came in excited with a little brown paper bag and a white box that she carefully opened in front of me. And there it was, the favor I was doing for my wife's best friend.

It was a metal tube, with two long windows on either side, that clicked neatly into a little loop with a tiny lock. On the shaft of the tube, facing up so I could read it, were the words "You Wanted This" in elegant cursive writing--a nice touch, I thought, and a little glimpse into a side of Ofélia I didn't get to see.

The first problem was that just thinking about this stuff got me so hard the cage wouldn't fit on. The whole idea was that it would keep my dick at best semi-hard, and pointing down to avoid detection. Not the most comfortable position.

When Nora was taking it out of the box, I was hard. When she was turning it over in her hands, I was hard.

"Babe, how about this," she suggesting laughingly, "I'll just keep it around and we'll watch TV and then when you least suspect it I'll just pants you and slap it on!"

"There is absolutely no way that you're fast enough. You yanking my pants down will make me rock-hard instantaneously."

"Instantaneously!" chortled Nora.

This led us into a conversation about what the least sexy TV show of all time would me, something that would keep me soft even with my wife manipulating my pants. My wife suggested the news, I playfully said I'd always wanted to fuck Maria Bartiromo.

"What about old news? Like, the invasion of Grenada? Does that turn your crank, you sick freak? Are you or are you not sexually aroused by the invasion of Grenada?"