The Longest Night – His First Cuckold Experience

When she arrived, I was in the shower. I could hear the enthusiastic chatter of old friends catching up for the first time in a long time from the bathroom. I stood under the hot water spray, attempting to calm my racing heart and make sense of my feelings. She came to have sex with you, Mistress – my woman. My chastity device tightened uncomfortably when I imagined the two of you together. It was a cruel reminder of the role I’d be playing later that night.

That morning, you’d locked me up. You outlined in tantalising detail what you planned to do with her later as you clicked the padlock shut. With a cruel smirk, you put the small key onto a silver chain around your neck and told me I wouldn’t be set free until tomorrow. We’d previously discussed cuckolding, including provocative fantasies and lighthearted threats. Her entrance proved that you planned to bring those fantasies to life tonight. As I reached for my towel, my hand trembled.

I went downstairs with you both. The discussion (and the wine) flowed freely, but I was having trouble keeping up. I couldn’t help but think about what you’d do to each other afterwards. Would it be frantic and intense, or private and slow? I snuck glimpses at the feminine hands that would soon explore your body; the lips and tongue that would taste you when the discussion shifted from family to work. My cheeks flushed as I was aroused and humiliated by these reoccurring thoughts. I tried to keep myself occupied by offering drinks and nibbles. I had no idea that the worst was still to come.

You had reserved a table for us at a local restaurant, and as the evening drew near, you raced to the bedroom to get ready. I took advantage of what I thought would be my last chance to be alone with you while your companion was doing the same in the bathroom. Your body mocked me as you walked around in your underpants, unsure of what to wear. You were close enough for me to reach out and touch you, yet tonight you were off-limits. Finally, you wriggled into a little black dress, which was a blessing. It hugged your curves in a way that I wish I could do myself. You looked stunning, perhaps even more so knowing that you were someone else’s gift to unwrap tonight.

We got in our car and drove to the restaurant. She took my normal position beside you in the rear seat, which she had been relegated to. I got it; you were letting me know where I’d be spending the evening. We were greeted by a lively waiter who walked the three of us to our table when we arrived at the restaurant. When we were assigning seating arrangements, there was an awkward moment when the two of us wanted to sit next to you. I was much more determined to win that seat after losing mine in the automobile. I had an egotistical wish to seize your attention and keep it all to myself. We quickly arrived at the most logical solution. We took a seat on each side of you after a short shuffling of seats.

While we waited for our dinner, I observed you exchanging amorous glances. Seeing you look at another woman in that way turned me on. Normally, that glance was reserved for me. I was curious if anyone else in the restaurant was aware of your activities. The lovely brunettes at the adjacent table were impossible to miss, but if anyone was in doubt, the giggling and touching would give it away. I don’t think I blinked once during the meal, for fear of missing something.

When you got home, you decided to curl up in bed and watch a movie. I took a seat in the corner of the room and stared blankly at the TV after you offered me to watch the movie with you. I had to make a conscious effort not to look over at the bed where the two of you were lying together for the next hour. It was thrilling to see you snuggle up to a lady on our bed as I sat chaste in the corner, and my cage made its presence known once more. At the same time, I realised how much I missed your embraces, and seeing you give them to someone else only added to my longing.

I listened to your hushed murmurs and frightened chuckles instead of watching the movie since I couldn’t follow the plot. I started to feel embarrassed; I didn’t want to bother you, but I also didn’t want to miss anything. Should I get out of here? You would have told me if you wanted me to go. After all, you are my Mistress. I’m thinking about this when I hear what sounds like kissing. My determination shattered. Do you realise how difficult it is to look away? A quick glance to my left reveals your lips locked against hers, tongues softly exploring. My cock throbs uncomfortably inside the cage at the sight. You break from from your embrace seconds later and lead me to the spare room.

You patted the bulging bulge at the front of my boxer shorts as you tucked me into bed. You tell me to behave myself, devilishly grin on your face, plainly amused by my misery. You make your way back to the master (or should I say Mistresses) bedroom after that. This was going to be one of the longest and most intense evenings of my life, I didn’t realise it at the time.

When I heard the first cry filter through the walls, I was playing with my iPad, trying to find anything entertaining to watch while I slipped off to sleep. OH MY GOD, OH MY GOD, OH MY GOD, There was an outpouring of emotions, both mental and physical, that came out of nowhere. I felt like I was about to burst out of my prison because I was so turned on. I debated snapping the wretched thing off so I could masturbate to the sounds of your enjoyment for a little minute. I’d be in a lot of trouble, but I’d be able to deal with the consequences later, right? I took a long breath and regained my composure.

More moans are being heard, and they are becoming louder and faster. Jealousy made my gut churn. What exactly did she do to you? Was her tongue skilfully teasing your firm clit, or were her fingers buried deep inside your pussy? I hadn’t heard her moan yet, but I assumed she was busy introducing you to new levels of pleasure that I hadn’t before introduced you to. A feeling of paranoia washed over me; what if she was better than me? She could, after all, touch and tease you in a way that only a woman could.

My body tingled with arousal and envy as I tossed from side to side. As envious as I was, I was desperate to hear more. Your groans soon gave place to gasps, and I knew you were getting near. I listened as you burst beneath her touch, holding my breath and determined not to miss a single moan. I wished I could be a fly on the wall, watching your dirty behaviour.

I heard your furious yells give way to calm sighs as I stared up at the ceiling. My boxers were completely wet in pre-cum. It was gathering at the base of my cage and periodically trickling across my waist. I ached with a need to be free. I was hoping you’d come to me. I longed to take you in my arms and brush your smooth, warm skin while inhaling the beautiful aroma of your hair. I knew I would never let you go if you came to me. I needed to fuck you; I’d consume and recapture every inch of your body like a passionate and frenzied fuck. I felt closer to you than I’d ever felt before, but you seemed a world away.

I patiently awaited….

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

It was going to be a long time before I fell asleep.