Our Dark Secret: A Modern Cuckold Memoir

One evening, weeks later, I was pushing my cock into Janet’s tightness and she was moaning with pleasure. I could feel her walls gripping my small member. We became one, a perfect fit. She would explode in orgasm soon enough, and afterward we would snuggle side by side.
Janet kissed me softly and our eyes met. “I have been thinking about what you said at the beach, honey,” she said, “and I guess, if it means a lot to you, we can try it out.” I was nervous, not wanting her to freak out on it all, yet very excited by her words.
The next day I made my way to the porn shop and bought a Swingers Magazine. I spotted a new one, a local publication. I went to the counter, a little embarrassed yet intent on the purchase. The booklet was in black and white, not the big full-color format like some of the larger national magazines. However, it would do, and I left the shop with what was to become my intro the swinging lifestyle.
That evening Janet sucked my cock. She loved to suck cock. As usual, when we were ready enough to fuck, we used lubrication and that led to great sex. I kept thinking of the possibility that another guy might join us. How he would love her tight little body. What a gift she would be to an older gentlemen—a young, tight, sexy girl he could cherish. I was hard again in seconds after my own first climax. During our second joining we talked about placing an ad, and she came quickly again. God I loved a girl who could get off through just the screwing itself!
The booklet had space for placing an ad. I tore it out and filled in words. They read like this, “Tiny tight-bodied young girlfriend seeks an older lover. She is very attractive, toned and tanned. Boyfriend may watch or join in.” We placed the ad, bought a post office box for replies and waited anxiously for good letters. This was all new to me. In those days there was no Internet, no way to meet anyone other than through these magazines. I also had the option to post a note on the adult bookstore wall. I worried someone we knew would answer the ad but decided to try it anyway.
The anticipation of attracting a respondent was wild. Janet and I had a good relationship. She was a good girl and I was the ring leader. I would never have thought of myself as a cuckold at this time in my life. I pretty much called the shots. We received a few replies in the coming months, but most were weird or from men who were overweight, too old, or wanted me— the male—to participate in full. I was by no means interested in going there. Eventually, though, one reply stood out that was worth pursuing.
William was his name. He was in his late forties, in decent shape, and seemed classy enough. The following weekend we made plans. I was to meet him in a nearby hotel parking lot, a place easy to find off the interstate. Janet would be home waiting for us. She would wear a sexy blue cami and matching string bikini panty. She would wait on our bed. Our plan was, if I liked the guy, he would come to our home and massage her. Where things would go from there, we had no clue. Thinking back, I can’t imagine inviting a strange man to my now home. Sara would forbid it. Plus, it’s downright dangerous. A hotel was the way to go. Yet, as a young foolish guy, I knew no better, had no funds for travel and nice hotel lodgings, and did not even know if this stuff would be right for me and my girl more than just this one time.
William and I hooked up; I saw his red car and drove up and got in. The parking lot was quiet, and we sat and talked. Here I was, speaking with a random stranger about coming to fondle and possibly fuck my young girlfriend. Man was I crazy, yet fully aroused.
He seemed nice, relaxed and easy going enough, so I had him follow me home.
When we got back, Janet was right where we planned, lying on the bed, face down. She looked awesome—so small yet firm, tan and sexy. He was very pleased. He sat and prodded her body, touching and massaging her completely. Few words were spoken.
Janet then turned over, more relaxed now. William slid his hands to her small perky breasts, a nice rounded upright 34B cup. He fondled her and touched her as I looked on. I joined in, and her excitement began to build. The idea of four hands on her body was intoxicating to me, and I was amazed to see it become a reality.
He slid a hand in her panties, and she was enjoying it. Soon enough we had her out of her outfit and fully nude on the bed. William, too, got undressed. This would be my first time seeing another in-the-flesh male naked in front of me and my lover, yet he would be one of many to come. He was decently in shape, but my eyes went right to his thick, uncut penis. He was hung well, and his foreskin covered what appeared to be a nice cock head. Janet had unzipped my pants and was sucking me already. William exposed her inner thighs and dropped down to lick her now-ready pussy. Janet had no outer pussy lips, just an opening—an opening so tight that even my smallish penis couldn’t enter without lube. His saliva dashed about her and she groaned in pleasure.
This guy was in heaven. He was a near-fifty-year-old guy tasting a young twenty-three-year-old who was a looker. He had hit the jackpot. I loved having a fellow partner help me satisfy Janet. It was it easy to put her into sky-rocketing orbit. The stranger took no time between her legs; he grabbed her and made her kneel. He positioned himself behind her and wanted to enter immediately. She sucked me still and I watched as he mounted her backside, her tiny butt sticking up ready to receive him. I got a glimpse of his hard-on; he was big and rock stiff. She would take him deep and she looked right at me as he pushed in. I will never forget her face. She was like a deer in headlights; this large dong was one she had never experienced. His size opened her, and she looked at me with shock; yet her eyes began to glaze over once he was fully in. “Oh lord,” she blurted out. “He’s so big.”
I looked at this stranger who now had my foxy girlfriend in a frenzy. Then it happened way too fast; he could not hold off, and he pulled out, spurting his white goo all over her ass. She was too tight for him, too fresh, too young. This very pretty girl had made him cum in less that one minute. In those days I would take over, fuck my girl and make her cum. This was just the beginning, however. In time, when my bride Sara and I took to this lifestyle, things would be very different.
Janet and I planned a few more events in the coming months. We tried a couple in which the female half was a hottie. The girls pranced about for us guys, drinking margaritas and modeling various outfits. The guy in the couple was a good-looking, younger body-builder type. As the night progressed we all joined in on the floor for some fun. I was turned on by him being with Janet, but his girl wanted me. This was my first lesson in what I truly desired, and it was not another woman. I could not get hard. She commented on me being small in size, and Janet was over there sucking her guy hard and wanting more. I just wanted to watch my little sexpot go at it.
Those two encounters had set me off. Normal sex would not do anymore. I wanted my girl to have it all—meaning more men, multiple men if need be. We really did not need couples or women; I wanted men for her. Our sex life had taken a dive, so generic it had become. I found myself wanting more. It had taken a toll on us. But we still were doing fine and decided a year later to get engaged. Janet was my girl, a small-town poor kid who followed my lead. She was good looking, and men turned their heads when she passed by. I was happy and we made plans for our future.
I made it a point to update the ad we had placed, this time with a picture. Who could resist this tiny woman with perky breasts and abs of steel? With such a picture we got many replies. In today’s swinging world, the online aspect is truly awesome. These paper ads and letters via regular mail were a major pain. The quality of people seeing a porn store booklet ad sucked. However, we carried on.