The Longest Night - His First Cuckhold Exprience

The Longest Night – His First Cuckold Experience

My Mistress with the keyI was in the shower when she arrived. From the bathroom, I heard the excited chatter of old friends catching up for the first time in a while. I stood beneath the hot water spray, trying to slow my beating heart and make sense of my emotions. She was here to have sex with you – my woman, my Mistress. Imagining the two of you together caused my chastity device to grow uncomfortably tight. It was a torturous reminder of the part I would play this evening.

You’d locked me up that morning. As you clicked the padlock shut, you described in tantalising detail what you planned on doing with her later. You slipped the small key onto a silver chain around your neck and with a sadistic smile, told me I wouldn’t be set free until tomorrow. We’d talked about cuckolding before; suggestive fantasies and playful threats. Her arrival confirmed that tonight, you intended on bringing those imaginings to life. My hand trembled as I reached for my towel.

I joined you both downstairs. The conversation (and the wine) flowed, but I found it difficult to keep up. I couldn’t help but imagine the things you might do to each other later. Would it be fast and passionate, or slow and intimate? As the conversation moved from family to work, I stole glances at the feminine hands that would soon explore your body; the lips and tongue that would taste you. Aroused and embarrassed by these recurring thoughts, I felt my cheeks start to flush. I attempted to distract myself by serving drinks and snacks. Little did I know, the true torment was yet to come.

You had booked us a table at a nearby restaurant and as evening approached, you hurried off to the bedroom to get ready. With your friend doing the same in the bathroom, I took what I knew would be my last opportunity to be alone with you. Parading around in your underwear, trying to decide what to wear, your body taunted me. You were close enough that I could reach out and touch you, yet completely off-limits tonight. Finally, mercifully, you wriggled into a little black dress. It hugged your curves in a way I wished I could. You looked beautiful; more so perhaps knowing that tonight, you were somebody else’s gift to unwrap.

The-Longest-Night-Featured-1We jumped in the car and headed out to the restaurant. Relegated to the back seat, she took my usual spot beside you. I understood; you were letting me know my place for the evening. At the restaurant, we were greeted by a bubbly waitress, who escorted the three of us to our table. There was an awkward moment as we allocated seating positions; the two of us wanting to sit beside you. After losing my seat in the car, I was all the more determined to win that seat. I had a selfish desire to grab your attention and keep it all for myself. We soon reached the most logical solution. A quick shuffle of chairs and we took a place at either side of you.

Waiting for our food to arrive, I watched as you exchange flirty looks. It turned me on to see you look at another woman that way. That look was usually reserved for me. I wondered if anyone else at the restaurant knew what you were up to. It was impossible to miss the stunning brunettes at the next table, but if anyone was unsure, the giggling and groping would give it away. I don’t think I blinked through the entire meal, too afraid that I’d miss something.

Arriving back home, you decided to settle down and watch a movie in bed. You invited me to watch the film with you, so I took a seat in the corner of the room and began to stare blankly at the screen. For the next hour, I had to make a conscious effort not to glance over at the bed, where the two of you lay together. Seeing you snuggle up to a woman on our bed, while I sat chaste in the corner, was incredibly exciting and my cage made its presence felt yet again. At the same time, I realised I was missing your hugs and watching you give them to somebody else made that yearning all the more intense.

Unable to follow the movie plot, I listened to your quiet murmurs and nervous giggles instead. I began to feel a little awkward; I didn’t want to impose on you, but I didn’t want to miss a thing either. Should I leave? If you wanted me to go, you would surely tell me. You are my Mistress after all. As I ponder this, I hear what sounds like kissing. My resolve crumbled. Do you know how difficult it is not to look? A quick glance to my left and I see your lips locking with hers, tongues exploring softly. The sight makes my cock throb painfully inside the cage. Seconds later, you break from your embrace and escort me to the spare bedroom.

As you tucked me into bed, you patted the straining bulge at the front of my boxer shorts. Grinning devilishly, clearly amused by my suffering, you tell me to behave myself. With that, you turn tail and make your way back to the master (or should I say Mistresses) bedroom. I didn’t know it then, but this was going to be one of the longest and most intense nights of my life.

Lesbian Sex

Image by Santl Mollna

I was fiddling with my iPad, trying to find something interesting to watch as I drifted off to sleep when I heard the first whimper filter through the walls. OH MY GOD! There was a sudden, intense explosion of feelings, both mental and physical. I was so turned on, I felt like I was going to bust right out of my cage. For a moment, I considered snapping the damned thing off so that I could masturbate to the sounds of your pleasure. I would have been in so much trouble, but I could deal with the consequences later, right? I took a deep breath and came back to my senses.

More moans, getting louder and faster now. My stomach twisted with jealousy. What was she doing to you? Were her fingers buried deep inside your pussy, or was she expertly teasing your hard clit with her tongue. I hadn’t heard her moan yet, but I imagined she was busy taking you to new heights of pleasure; heights I hadn’t taken you to before. A sudden wave of paranoia hit; what if she was better than me? After all, she could touch and tease you like only a woman could.

Cannot Sleep

Image by Ivana Vasilj

I tossed from side to side, my body tingling with arousal and envy. As jealous as I felt, I desperately wanted to hear more. Soon enough, your moans gave way to gasps and I knew that you were close. Holding my breath, determined not to miss a single sigh, I listened as you exploded beneath her touch. I longed to be a fly on the wall, perving on your naughty antics.

Staring up at the ceiling, I heard your passionate cries give way to soft sighs. My boxers were soaked with pre-cum. I could feel it collecting at the base of my cage, occasionally trickling across my waist. I ached, desperate for release. I wondered if you would come to me. I wanted to hold you in my arms, inhale the sweet scent of your hair and stroke your soft, warm skin. If you came to me, I knew I would never let you go. I needed to fuck you; a fierce and frenzied fuck, I’d devour and reclaim every inch of your body. I felt closer to you than I have ever have, yet you seemed a million miles away.

I waited….

Sometime later, I heard the flick of the light switch and the house fell silent. I was left alone with my thoughts and fantasies.

It would be quite some time before I drifted off to sleep.

6 replies
  1. Jimmy
    Jimmy says:

    Interesting. My wife is bi and often had me watch her with women when they did not want a threesome. I never felt jealous though because she was with a woman, not a man. I merely got sexually aroused. When my wife did have sex with another guy, the first and the last, I still did not feel jealous or even aroused. Perhaps I feel very secure in my sexual abilities to feel jealous. After all, my wife did tell me that I was more than enough man for her so she was going to stick to women. She had her girlfriend move in with us and I watched them almost every night. I also was denied intercourse for the last 15 years. I was only allowed to masturbate. When the came out with the plastic Chastity device, I was locked up as much as my skin could take. From there I went with a custom decvice which I have worn for the last 3 years and I am still allowed to watch and still get aroused.

    • GrittyWoman
      GrittyWoman says:

      This goes to show how everyone is different. I personally think that some jealousy is natural and healthy. I see it as another form of passion; it highlights the love and desire we have for each other. For some people, feeling jealousy is part of their kink. Perhaps they enjoy the power-play or the sadistic/masochistic feelings it evokes. Outside of cuckolding, I know polyamorous couples who experience jealousy and believe it is natural; something to work through together, but not a threat to their relationship.

      Of course, it all depends on how you handle the jealousy. Some people avoid open relationships because they already know they would feel too jealous. Others might experience jealousy, but know they can work through it with good communication and respect. Then there are people, such as yourself, who don’t experience jealousy and that’s fine too. People are just too varied to follow a single path to happiness.

      It sounds like you and your wife are having an amazing experience with cuckolding/chastity! I especially like how you get to watch, but are ultimately denied any pleasure from the women…having to satisfy yourself when allowed. Very hot! 😀 Thanks for stopping by and commenting!


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