[Captivated Caveman] A Journey into Chastity

[hope2lock]

Ditto on that ...you are a very good writer and erotically describe all of what is going on.

I did enjoy your first two posts but felt it would be odd for me to reply since I am a newbie at this forum. Thanks for sharing!

[CaptivatedCaveman]

Gonna post soon. Lots to share.

Kids going back to school this week. Been keeping me busy.

[CaptivatedCaveman]

The kids are back in school and I'm home with the whole house to myself. Finally some time to write.

I'm going to keep the dates a little vague as I don't want to specify my anniversary date. I feel like I'm walking a tightrope as far as how much personal information I share while still preserving my anonymity.

So jumping back to last month. I'm wearing the Jailbird constantly now. I'll probably start a thread in the Chastity Devices forum soon with a detailed evaluation of the Jailbird, but for now, suffice to say I've had no major problems.

It's evening. We lock our bedroom door to have some fun. My wife puts my laptop on her chest and watches some porn on xhamster while I go down on her. I'm lucky to have a spouse who really enjoys porn. A few minutes of viewing and she's always soaking wet. I'm relishing my feast. Pleasuring her orally continues to become a more intense and fulfilling activity for me. I've always enjoyed it, but of late it's become more satisfying to serve, to give pleasure rather than to receive it.

Soon she is quivering as her orgasm takes her. After a few minutes to cool down she puts the laptop aside and orders me to grab a desensitizing condom. She has me put it on and get on all fours in front of her, my head on the bed between her legs and my ass in the air in front of her. She pulls on a pair of latex gloves and reaches for lube. I had been asking her recently if we could make anal play a more regular part of our sex life and she happily agreed.

She spreads the lube around my asshole and slowly, gradually, eases a finger inside me. She strokes my cock lightly with her free hand as the desensitizing chemical slowly does its work. She works me over like this for a while. Gradually working up to two fingers and then to one of our smaller dildos. It's been years since we've done this sort of thing and I'm out of practice. I won't be able to take anything bigger tonight.

She fucks me steadily for a while. She continues teasing my cock with one hand when she's not using it to add more lube. She's keeping me hard but nowhere near orgasm. She just wants me ready for use soon. I'm lost in the sensation, kissing her feet and sucking on her toes as she thrusts the dildo in and out of me.

At some point she decides it's her turn again. She pulls out the dildo and a quick wipe with a towel assures us that I'm clean. Yay. No mess.

She lies back and spreads her legs. I enter her tenderly and begin thrusting. This time the condoms work perfectly. We took our time letting them numb me before penetration and now I have no problem building up to the kind of hard fucking she prefers. I settle into a rhythm and maintain it as we talk dirty to each other. Even though I highly doubt we will ever actually do it, we talk about how hot it would be for her to cuckold me. Imagine, I tell her, that several guys have already shot their loads inside her. Now I'm fucking her with their cum lubing my cock. She orgasms. Hard.

And just like that she's done. She orders me out and I withdraw, feeling deliciously used. Just another sex toy for her pleasure. It's not even a question at this point about me having an orgasm. It's all about her.

She doesn't even allow me to clean the desensitizing chemical off my cock after removing the condom. I go straight back into the Jailbird. She looks at me with a naughty expression on her face as she tightens the screw, turn by turn. I'm locked back in. I don't know it yet, but this is the last time I'll be freed until our anniversary.

Which isn't to say we didn't have a little more fun before that. Several days later we woke up a little on the early side. The kids were still asleep. We hugged and spooned under the covers.We talked about about how hot the cuckolding fantasy was. My cock tried to harden and strained against its cage with agonizing pleasure. I begged for permission to hump her thigh. She granted my request and I began grinding my caged cock against her leg.

We continued talking quietly as I ground against her. How hot it would be if she were fucking other men and all I got was to hump her leg like a dog as I was doing at that moment. I love when she talks dirty to me. It's one of the few things I wish she'd do more.

The eroticism of the images going through my head, coupled with the sensation I was experiencing through the cage, soon brought me to the edge of ejaculating. These caged ejaculations are not really orgasms, so we've started referring to them as "spurting" instead. I requested permission to spurt. Once again she granted my request and moments later my cum was dribbling down her thigh.

At that moment the bedroom door swung open and one of our kids came in. We had neglected to lock the door. Fortunately we were under the blanket so our child didn't see what was going on. My wife slipped out of bed, surreptitiously wiping her thigh clean with the blanket as she rose. I was left alone in the bed, on my side under the covers with my cupped hand catching the remainder of my ejaculation as it continued to dribble out. Definitely washing the bedding today. No question.

When we talked later my wife expressed some surprise that I was actually able to ejaculate that way. She had given permission without actually believing I would be able to achieve any sort of release. Oh how badly did she underestimate the power of male sexual frustration.

And that, dear readers, would be the last sexual encounter we would have until our anniversary.

Coming soon to a forum near you.

[Tom Allen]

When we talked later my wife expressed some surprise that I was actually able to ejaculate that way. She had given permission without actually believing I would be able to achieve any sort of release. Oh how badly did she underestimate the power of male sexual frustration.

Be careful with this! Back when we started, we both were surprised when this happened. Over time, we learned that this would happen every once in a while, depending upon how, er, aroused or excited I was, but it seemed to be once a month or so. Like you, I was required to ask permission, and if I felt it getting close, I had to warn her so she would have the option of letting it continue or not.

Eventually, she started *trying* to to make me "release" (our word for it) this way, each time using it as an excuse to keep me locked up for longer periods. "Oh, you don't need to get out now, you just had a release a few weeks ago." After a while, the idea of *only* allowing me a release in that fashion became her own turn-on, and things just went downhill from there.

[TwistedMister]

we talk about how hot it would be for her to cuckold me. Imagine, I tell her, that several guys have already shot their loads inside her. Now I'm fucking her with their cum lubing my cock. She orgasms. Hard.

Damn you. Now I've got a chubby and can't do anything with it.

[CaptivatedCaveman]

Damn you. Now I've got a chubby and can't do anything with it.

All part of the fiendish plan. Bwwa-Ha-ha-ha!

[CaptivatedCaveman]

When we talked later my wife expressed some surprise that I was actually able to ejaculate that way. She had given permission without actually believing I would be able to achieve any sort of release. Oh how badly did she underestimate the power of male sexual frustration.

Be careful with this! Back when we started, we both were surprised when this happened. Over time, we learned that this would happen every once in a while, depending upon how, er, aroused or excited I was, but it seemed to be once a month or so. Like you, I was required to ask permission, and if I felt it getting close, I had to warn her so she would have the option of letting it continue or not.

Eventually, she started *trying* to to make me "release" (our word for it) this way, each time using it as an excuse to keep me locked up for longer periods. "Oh, you don't need to get out now, you just had a release a few weeks ago." After a while, the idea of *only* allowing me a release in that fashion became her own turn-on, and things just went downhill from there.

And this is a bad thing why?

Seriously, even though we used the removable Locktite on the security screw recently, I've been having some very intense fantasies about using the permanent one. In spite of all the concerns I raised before. But I'm getting ahead of myself.

My ex-wife put me through some serious hell recently, prompting our friends to give us a gift card to a fancy restaurant and an offer to babysit the kids overnight. This allowed my wife and I to turn our anniversary into the first real vacation we've had alone since...damn, maybe in nearly a decade.

We made reservations at a hotel in the city and at the restaurant for dinner. A day or two before the trip my wife turned to me and said, "I think my period is coming."

These are never words you want to hear at times like this.

"Don't worry," she reassured me, "if it comes we'll still have fun." I nodded. I felt a little disappointed at the inconvenient timing but knew she was right. We would still have fun.

The big day arrived. My wife came home from work early and one of our friends arrived for the first babysitting shift. We said our goodbyes and got into the car, giddy as teenagers. We chatted playfully with each other as we drove, making the ride pass quickly.

Soon we were checked in and settling into our room. I pulled out her anniversary gift. A gold anklet to complement the toe ring she wears. She loved it and thanked me with a deep kiss. My gift, she said, was the chastity device I had spent so much money on.

We both stripped off our clothing, climbed into bed and began kissing. The long, slow, deep kisses of a couple in love. The kind that make you lose track of time. When we finally came up for air my wife removed the Jailbird. It felt strange having my cock free of its cage. I'd gotten so used to it.

She lay down at the foot of the bed and I gave her a massage. She idly teased my cock a little as I worked on her. Something in her neck was bothering her so I gave it some extra work until things popped back into place. She stretched luxuriously and scooted up to the head of the bed, motioning me to follow.

Since my wife's period had indeed arrived, my task was to bring her to orgasm with my fingers. Aside from resisting orgasm when we fuck, this is probably the trickiest way for me to get her off. Most of the time she really likes what I can do with my tongue.

I went to work. It took a while to get her there. First she was lying on her back as I stroked along the folds of her labia, building up to light, rapid flicks side to side across her clit. At some point she flipped onto her belly and I cupped her pubic mound with one hand as my thumb continued to tease her clit. I used my other hand to spread her labia apart and stroke up and down the lips.

One useful trick I find helpful to improve fingering technique is to close your eyes. It helps focus all your attention on what you are doing with your fingers. I noticed a change in my wife's arousal when I sacrificed the joy of looking at her and focused entirely on her pleasure. I savored the sounds she made when she finally came.

We hadn't had lunch and we were both hungry by this point so we dressed and went out to eat. We found some light, healthy fare to enjoy. Nothing too filling before our expensive dinner. Then my wife said she wanted to walk around. At first I thought we were sightseeing but it slowly became clear she had a specific destination in mind.

What could it be, I wondered. She had teased me on the ride in about a guy she used to fuck around here long before we met. I began to imagine she'd set something up with him. Since she had her period I fantasized that I was going to watch her suck him off.

Not that I thought this at all likely, but it was a hot fantasy. And we had been teasing each other about cuckolding a lot lately. But then I recognized what part of town we were in and realized where we were going. We were close to the dessert shop that had made our wedding cake. We went into the shop and had some small desserts. It was all very romantic and quite touching.

Is it weird that I find my fantasy scenario equally romantic? I guess I'm just strange that way.

We still had several hours before dinner. We went back to our hotel, stopped at the bar for some drinks and then went back to our room. She went into the bathroom to change. Back when we started exploring chastity a few months ago I had bought my wife two pieces of lingerie, a slutty one and a classy one (relatively speaking).

That first night she had worn the slutty one. This one:

http://www.wickedtemptations.com/plus-s ... 5-prd1.htm

This time she had put on the classy one:

http://www.wickedtemptations.com/plus-s ... 4-prd1.htm
(I guess it says something about me that I consider this classy. Go figure.)

My wife had me strip naked and get on all fours on the bed. She pulled out the lube, lube shooters, gloves and some very big dildos.

She placed a towel beneath my cock and began lubing up my ass. She stroked my cock with one hand as she worked her fingers into me. She commanded me to tell her what a slut I was as she finger-fucked me.

Then she switched to the big dildo. It's one I love but hadn't taken in a very long time. She pushed it into me gradually, allowing me to rock myself back and forth until it slowly slid in all the way to the base.

I picked up my pace. As I rocked back and forth she moved the dildo to match my motions, slamming it into me as I rocked back. Her other hand played lightly with my cock, bringing me close to the edge several times and then either letting go or roughly grinding the sensitive head against the rough fabric of the towel.

And then at some point she didn't stop. She kept stroking my cock as my moans grew louder. The dildo was pounding into my ass. As I passed the point of no return she let go of my cock and let my seed pour out onto the waiting towel. My thrusts slowed until I collapsed spent onto the bed, the rubber cock still buried in my ass.

When I could move again we kissed and then I waddled into the bathroom to remove the dildo and clean up. We got into the shower and bathed each other - another thing we rarely get to do at home.

We dried off and pulled out our dress clothes for dinner. But before we dressed there was something to do first. She had me pull the Jailbird back out. This was it. I was going in for a year.

I popped the cock ring back on with butterflies once again bouncing around in my stomach. It's a sensation I've come to relish. My wife worked the cage into position. Unlike every time thus far, this time she had a hard time lining up the holes for the security screw. She had to start and then unscrew it several times until the threads caught. And then she began tightening. It went fast. Before I knew it I was locked back in, my cock trapped in its restrictive little cage.

We dressed and walked to the restaurant, the familiar weight of the chastity device once again tugging gently on my genitals. We found the restaurant without difficulty. Once a house, it had been converted into an elegant little eatery focused on southern cuisine, and the menu changes regularly.

The dinner was fantastic. One of the finest meals I've ever had. Deviled eggs with pickled beets, horseradish and dill. Some amazing lamb appetizer with I-don't-remember-what. A rib-eye steak, also with stuff I can't recall but loved. Chicken with eggplant, farro, cherry tomato, natural jus. An amazing wine.

We ate until our plates were clear, sharing each others food. We skipped dessert and strolled back to the hotel. We returned to our room and spent the rest of the evening cuddling, talking and kissing. We drifted off to sleep...

[CaptivatedCaveman]

We awoke the next morning feeling great. No alarm clocks, no kids climbing into our bed asking for television. Just me and the wife rolling into an embrace and kissing each other good morning.

We went downstairs and had breakfast in the hotel restaurant. My wife's period was in full force and she wasn't in the mood for any more sex so we packed our bags and checked out. Our mood this morning was light and playful, like the early days of our dating. Both of us have recognized a rekindling of romance in our relationship since adding chastity to our lives.

We still had a few hours of babysitting coverage so what did we do? We went shopping. We bought some new curtains, pictures, a few decorative items and new tablecloths. We had moved into our house when my wife was pregnant and for years a number of home improvement projects have languished in limbo while we devoted all our energies to getting through the toddler years. But now we are past that and finally trying to spruce up the place.

We drove home happy and content to just be with each other. We pulled in the driveway and went inside. Amazingly everyone was still alive and getting along. A good thing too, because the next few weeks would be challenging.

My wife had a tough work week ahead of her. We were supposed to travel out of state the following weekend to visit my family for a wedding. The day after the wedding she was supposed to leave for a week-long business trip. This meant she had a huge amount of work to get done in the five workdays available to her.

Every day that week she left extremely early and got home between nine or ten at night. In the meantime I held down the fort at home. I'd learned by now that it wasn't enough to have the kids and home well taken care of. If I let the challenges of the daily routine wear me down and stress me out, my wife wouldn't be able to relax and focus on her work. So I made sure to stay organized and well rested. I got the kids back to school, thank goodness. The extra hours were a welcome boon. No time for idleness, though. I filled all that extra time getting things done, preparing both for the wedding and the business trip.

Toward the end of the week my wife called me from work. She was still snowed under and didn't think she'd be able to have everything done before her flight. Would it be okay if she missed...

Yes, I said. No problem. I'd take the kids to the wedding without her and she'd go back into the office over the weekend. She was worried that she was letting me down. I reassured her it was okay. I had this. The only thing I needed for her to do was deal with the kid's dresses and shoes. It's not really my forte. She agreed.

With the extra time now freed up, she was able to get home Friday night at a semi-reasonable time. A week after our little vacation we finally had the opportunity to make love again. I went down on her, something I had been unable to do on our vacation and missed terribly. After her orgasm she gave me another ass fucking, this time with me on my back and legs in the air. My cock stayed locked in the Jailbird as she gave me a good pounding.

She kept going until I was blissed out on sensation and then stopped abruptly. "That's it. You're done."

"Did I do something wrong?" I asked. She had ordered me not to move as she fucked me. Had I moved? Is that why she stopped?

"No. Nothing like that. You're just done."

The end of love-making is a lot more arbitrary when you don't have an orgasm to define it for you. I searched my psyche for any resentment or disappointment and didn't find any. Okay then. That was fun. Time for bed.

We slept soundly.

In the morning I awoke to the sensation of a hand stroking my balls. This felt both good and bad. Good because, well, a hand was stroking my balls. Bad because the morning is also the time they try to make like a turtle and retract into my body. With the Jailbird on this isn't possible. Instead I experience steadily escalating pain.

Under normal circumstances I'd pull them back into position and rub a little skin moisturizer around the base ring. But I couldn't do that now with interfering with what my wife was doing and I sure as hell didn't want to do that.

So I lay there as both my pain and arousal grew. I waited until her fingers slid up to the cage before grabbing the moisturizer. She worked a finger into the underside of the cage as I worked around her, making my scrotum more comfortable. Just in time too because her finger found that sensitive spot under the head and began teasing it. I clung to her and shuddered as increasingly powerful jolts of pleasure and pain coursed through me.

I felt my ejaculation approach. I asked permission and she assented. I closed my eyes and let my body move of it's own volition, spasming as my body vainly tried to orgasm and failed, leaking spurt after spurt of cum instead. My wife collected all of it in her waiting palm and fed it to me.

That was the high point of the day. It was all downhill from there.

Next time.