A Cuckold’s Journey

A Month in Lockup

December 3, 2008 · 1 Comment

So I began my first month in lockup.  Going for a week at a time without an orgasm had been rough, so I had no idea how I was going to survive a month!  But I was intrigued by the idea, I have to admit.  The first week was a breeze – much to my surprise.  Before, a week seemed like an eternity, but now, facing an entire month in chastity, a mere week was child’s play.

My Fair Lady was pleased with my behaviour after a week and decided to reward me.  Not with an orgasm, of course, but the Sunday evening of my eighth day in lockup she cuffed my hands behind my back and removed my device for a few hours of freedom.  Relatively speaking, that is.

Even though I was in chastity, every night I spent about an hour pleasing MFL orally.  At first, I thought this practice to be cruel and unusual.  But I was starting to get a thrill from it.  She was very impressed with my submission to her and we made it though the second week without incident.

That weekend, MFL announced that although my oral skills had drastically improved over the past few weeks, she needed to feel penetration.  She didn’t think it was appropriate to give me another chance to penetrate her without cumming, so she took me to an adult toy store to find a suitable dildo.  It was both humiliating and exciting to help her choose one.  She told the clerk all about my situation.  He didn’t seem too surprised.  Must get a lot of couples like us in there.

We finally decided on one, made our purchase and then headed home.  MFL could barely contain her excitement!  She fondled her new toy all the way home, teasing me as she carressed and licked it, reminding me that I still had two more weeks to go.

That evening was quite a thrill for the both of us.  MFL directed me on exactly how she wanted me to use her new toy on her.  She had me alternate between pleasing her orally and using her new toy.  She pointed out how much bigger it was than my own, pathetic, caged cock.  As I licked and dildoed her to orgasm after exhilarating orgasm, she wondered aloud if she even needed my cock anymore.

This really did a number on my psyche, I have to admit.

Nevertheless, I eventually made it.  One full month in chastity.  No orgasms, only a weekly 2-3 hour release while my device was being cleaned (my hands stayed cuffed behind my back the entire time I was “free”).  I tried to mentally prepare myself for what was going to be an orgasm like I’d never experienced before.  I could only imagine!

That night, MFL brought out the cuffs and asked me if I was ready.  “Yes Ma’am!” I enthusiastically responded.  She dressed in her finest lingerie and cuffed me to our bed.  The anticipation was about to kill me!  She wore the key to my device around her neck, which she then took in her hands and began to fumble with the lock on my CB 3000.  Then a puzzled look came across her face.

“Wait a minute,” she said.  Her face wore the expression of someone doing math in their head.  “Tell me,” she started, “What did I say would be your punishment for cumming during our last experiment?”  Was this a trick question?

“One month in chastity, Mistress,” I polietly resonded.  “Yes,” she replied.  “And how long has it been since that failed experiment?”  Again, the answer seemed obvious, but I treaded lightly.  “It has been one month, 30 days to be exact,” I answered.  “Yes,” she continued.  “But didn’t you have a week left in chastity at the time?  The one month sentence was IN ADDITION to the time you ALREADY had left in chastity.  Isn’t that right?”

My heart sank.  I proceeded cautiously, not wanting to be accused of arguing and getting more time added.  “Well, I thought you meant one month total.  We even marked it on the calendar, see?” I gestured with me head to the calendar on the wall with today’s date circled in red.  “Yes, my dear.  I see the calendar, but I’m afraid I’ve made a mistake.  You will have to wait one more week and serve out your full sentence.  We wouldn’t want to cut any corners in your training, now would we?”

“Of course not, Misstress,” I responded.  If I had learned anything so far, it was to never question the judgement of the woman who is holding the key to your cock.

One more week to go…

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In the Beginning… part 3

November 25, 2008 · Leave a Comment

On the evening of Day 7, My Fair Lady had me strip and sit in a chair placed in the center of the living room.  I sat in the chair, wearing nothing but my CB 3000 as she cuffed my wrists behind my back, attaching them to the chair.  My ankles were secured to the legs of the chair with silk scarves, and a belt around my hips kept my lower bodied firmly bound to the back of the chair.

Then MFL brought out a new purchase, a rubber ballgag.  She placed it in my mouth and secured it tightly around the back of my head.  Now I was totally helpless and vulnerable to her, even robbed of the ability to protest!  To my surprise, she took the key from her necklace and removed my chastity device.  She explained to me that she had been looking forward to this night and was angry that my begging a few days before had ruined it.

She’d been reading on various femdom websites about women who let their husband penetrate them but do not allow them to cum.  Since she wanted penetration but I still had another week to go before I was allowed an orgasm, she said this was a perfect time to start my training.  I was warned repeatedly that I was not to cum.  If I did, she said she would add an extra MONTH to my time in lockup.

I desperately wanted to please her, but was also unsure of my ability to hold off cumming from penetration.  After all, it had been a full week since my last orgasm, and I needed one badly!  I began to muffle this through my ballgag and she shushed me, telling me she knew what I was thinking, that I didn’t know if I could hold out for her.

MFL had a plan to help me on this front.  She went to the back and returned moments later with a condom which she promptly rolled over my hardon.  This was somewhat humiliating, in that I had never worn a condom with MFL.  Then she removed one of her stockings and rolled it down over my condomed cock.  Then she did the same with her other stocking, before rolling a second condom over the whole package.  She then blindfolded me, telling me that this would add to the sensory deprivation and help with my training.

Moments later I felt her straddling my lap.  Then I felt her hand on my penis as she guided herself down on it.  As my wife slowly slid herself down on my cock, I began to panic.  Even with two condoms and two stockings to desensitize me, I felt like I wouldn’t last two minutes after a week of denial.  Sensing this, MFL told me to try and meditate – take my mind elsewhere as she enjoyed herself.  I was not to move a muscle; the belt around my hips prevented my urge to thrust inside her.

She sat on my cock for several minutes, giving me a chance to try and adjust, before she began to slowly ride me.  I tried to clear my mind, and for the first 10 minutes or so it worked.  But as she began riding me harder, I felt an orgasm approaching.  I whined through my ballgag, attempting to signal her to slow down or she was going to make me cum.  “Don’t you DARE cum!” she screamed at me, riding me even harder.

I was a goner.  It was out of my control.  Within another 30 seconds, I began having what was probably the most powerful orgasm of my life!  I tried to fight it, but it was just too much.  “You BASTARD!” she screamed, still riding me hard, as I exploded inside her.

MFL was not a happy camper.  “Well, you’ve just earned yourself an extra month in lockup!”  I felt her remove the outer condom, then the stockings, then the inner condom.  Then she removed my ballgag.  “I’m sorry!  I tried, I really did but it was just…” I tried to explain.  “Silence!” she retorted.

I sat there blindfolded, awaiting my punishment.  “Open your mouth,” she commanded.  “Now stick out your tongue.”  I obeyed and then felt her emptying the contents of my used condom into my mouth.  Once she had poured it all in, she commanded me to swallow.  I did so without hesitation, swallowing my own jism.

After doing so, I heard her retreat to the bathroom.  A few minutes later she returned.  She removed my blindfold and I saw her standing there, holding a wine glass filled with her own urine.  “Did you try your hardest to not orgasm as you were commanded?” she inquired.  “Yes Mistress, I did,” I assured her.

“Would you do anything asked of you by your Mistress?”  she asked.  I told her that I would.  She smiled and held the glass to my lips, telling me to take a sip.   I took a small sip, trying my best not to gag.  She made me take a bigger sip, then another, and so on until I had drank the entire glass.

Afterward, we showered together.  We washed each other from head to toe and talked openly about the past week.  I admitted that her new found Domme side was very exciting for me, but she had to understand that certain physical limits took time to break.  She said she did understand, but I still had to be punished for disobeying her.

After our shower, I cleaned my device as she dried her hair.  When it was time for bed, I asked if she was going to put the device back on me.  “How about if we start your month-long lockup in the morning?” she asked, coyly.  That night I made love to my wife over and over, going down on her in between sessions to lick up my own cum.  It was the best sex we’d had all year long!  The next morning she locked me back up to begin my one month sentence.

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In the Beginning…part 2

November 25, 2008 · Leave a Comment

So, with my penis locked firmly under My Fair Lady’s control, I began my first week of orgasm denial.  I hadn’t gone a week without and orgasm in longer than I could remember.  I was excited.  Besides, a week didn’t seem like such a long time.

During the first few days, I behaved as a model husband.  I prepared her dinner each night, did all of the dishes afterwards, and took care of the various other household chores that needed attending to.  And of course, I serviced MFL orally each night for no less than an hour, making sure she was well taken care of.  The discomfort from my new CB 3000 was relatively minor, and I was learning how to sleep, go to the bathroom, and just live generally with it.

Around Day 4 I began to grow weary of it.  I was constantly turned on, an ironic byproduct of wearing a chastity device is that your penis is always on your mind.  That night I began hinting around at an “early release.”  She pretended not to pick up on my hints at first, then asked me point blank if there was something I would like to ask her.

“Actually,” I replied, “I was hoping that since I have been so good these last few days, maybe we could have a little fun tonight.”  When she asked me to clarify, I told her I wanted her to remove my device and let me please her with my penis inside her.  She told me to take off all of my clothes and kneel in the submissive position in the middle of the living room again.

She returned a few minutes later, again in her sexy new nightie, stockings and heels.  She approached me and slapped me hard across my face.  “How DARE you ask Mistress to be released early!” she yelled.  “You know the rules!  I told you when you would be released – you have NO RIGHT to beg for anything earlier!”  She lifted up her nightie and got into position over my face and continued to berate me as I licked her and apologized profusely.

As I licked away, she told me that in order to teach me a lesson about what it mean to be her sub, I would be given an extra week in lockup as my punishment.  So instead of being a mere 3 days away from the relief I so badly craved, I now found myself 10 days away.  “And if you feel the need to argue any more about it, I’ll make it a full month!  Is that understood?”  I told her I understoon and apologized again, then went back to pleasing her until she came.

Day 5 was tense because of my faux pas the night before.  I tried to do my chores extra-well and that night I spent over an hour between her thighs bringing her to multiple orgasms to make up for it.  Days 6 and 7 were more relaxed, though I felt like I was going insane because I needed to cum so badly!  And to make matters worse, I knew I had another week to go.

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In the Beginning…

November 23, 2008 · Leave a Comment

My wife recommended that I start this blog as a pet project.  I’ve never published a blog before, so this is very exciting.  For starters, I suppose I should begin by introducing ourselves.  I am a 35 year old man, married to a stunning 32 year old woman.  We’ve been married for 4 years now.

My Fair Lady was raised in a conservative household and wanted to wait until we got married for sex.  Not that she was a virgin, she had been with a couple of others before we met, but she said I was different.  After we got engaged, she told me that early on in our courtship she had a strong feeling that I was the one, which is why she insisted on waiting.

I guess this led to a lot of ribbing from her friends, as someone gave her a male chastity device as a joke at her bridal shower.  She hid it away and didn’t even show me until after our honeymoon.  I was amused by the gift, and when she said she wanted to have me try it on I didn’t mind.  I could tell she was getting a kick out of it, and I had never experienced anything like this.  So I agreed to leave it on for the weekend.

And this is how it went for the first year of our marriage.  It was a cheap generic plastic device that we’d break out on the weekends for some fun and games, light BDSM and so forth.  We both enjoyed it, and I have to admit, having her control my cock was very erotic for me.  My denial periods were never more than a couple of days at a time.

On our first anniversary, My Fair Lady presented me with a gift that she couldn’t wait for me to open.  It was a brand new CB 3000!  Her other gifts to me included handcuffs, blindfolds, and various other BDSM devices.  She told me that she liked our play and wanted to take it a step further, meaning longer times for me in lockup and a more dominating role for her.

I wasn’t completely surprised at this, since things had been moving in this direction anyways.  Her first goal for me was one week in lockup.  I accepted, asking if we could have sex that night and then start my week from the next day.  She had a different idea, however.  MFL was eager to start my denial, not to mention have me try out my new device.  So on our first anniversary, I was locked into my new chastity device with no sex.

After locking the padlock, she placed the key on a necklace I had just given her.  Then she changed into the very sexy nightie I had given her as an anniversary gift.  She also put on a pair of very sexy stockings and heels and then had me kneel in the middle of the living room in a submissive position.  I was completely naked, except for my new device.  She cuffed my hands behind my back and then added that key to her necklace.

MFL stood over me, lifting her nightie and commanding me to kiss her thighs.  I worked my way up both thighs with my mouth, then licked her to orgasm as she held onto my head for support.  She took me to bed after that, where I lay between her legs for over an hour pleasing my lovely bride on our first anniversary.  She said it was the best anniversary present I could have given her.

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