Our Dark Secret

by Derrin Hart

  Our Dark Secret

  A Modern Cuckold Memoir

  Derrin Hart

  * * * * *

  PUBLISHED BY:

  Fanny Press

  PO Box 70515

  Seattle, WA 98127

  For more information contact: www.Fannypress.com

  All rights reserved. No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher.

  This is a work of fiction. Names, characters, places, brands, media, and incidents are either the product of the author's imagination or are used fictitiously.

  Cover design by Sabrina Sun

  Our Dark Secret

  Copyright © 2010 by Derrin Hart

  ISBN: 978-1-60381-486-7 (ePub)

  Produced in the United States of America

  * * * * * *

  This is the true story of our “guilty pleasures.”

  Often the "guilt" involved is simply fear of others discovering one's doings, or otherwise embarrassing tastes, rather than actual moral guilt.

  Prologue

  One warm summer day my girlfriend Janet and I were relaxing on a beach blanket next to the Atlantic Ocean. The sun was shining and life was good. I had met Janet a few years earlier and we were planning on getting married one day. As young twenty-three year olds, life was ours for the taking. I was happy with my choices. Janet was a cute if not very sexy young woman. Today she had on a tiny yellow, orange and blue bikini. There was no denying that this little girl—a mere one hundred and five pounds—was a looker. She had frosted blond hair and a fabulous flat tummy. I, too, was not so bad. I was athletic and solid. Woman liked my looks and I was a manly man.

  Together we made a good couple and yes, we were in love.

  I—for some unexplained reason—enjoyed watching the guys on the beach look at Janet. It was a great turn-on to see them glance over and, when she walked over to the water, gawk and lick their lips. Like most men, I could be jealous, but this aspect of “all eyes on my tiny girlfriend” just got to me. I never much thought about having any sort of open marriage or swinging lifestyle with her. We were young and very compatible.

  Sexually we fit. For a couple years now we had made love a lot. Though in good shape and full of energy, I had a somewhat-small penis. However, Janet was a small thing and her vaginal opening was as tight as I had ever experienced in a woman. We connected well, the sex was good, and she was a “cummer”—orgasmic even with just straight intercourse. I loved it.

  This story, at least most of it, is about me and my wife. Janet is not my wife. But to learn how my cuckold ways came about, I must start at the beginning. I am currently married; my bride Sara’s long tale— Our Dark Secret— is yet to come. I was not a cuckold to begin with; I was a young, fun-seeking chap who just wanted to have a lot of sexual freedom. While visiting a local adult bookstore, I came across Swinger Magazine. These books got me thinking and the ads and pix made me wonder. I had never heard of such a thing, and with Janet I thought, wow, we could get into this stuff. I mean, after two years we needed some excitement; after all, I loved adventure.

  That day, while we sat on a blanket enjoying the wonderful ocean view, I told Janet, “Babe, I think we should try swinging and couple swapping. We could meet men for you to have fun with.”

  Janet stared at me with her big brown eyes and replied, “What on earth are you talking about?”

  Chapter One

  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 ha
d 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.

  Chapter Two

  One guy who we invited to our apartment arrived with Kentucky Fried Chicken buckets.

  Another appeared completely different from his picture. Both were way below Janet’s standards, which were not overly high as long as the guys were attractive and nice. These two were plainly average—if that. The balding second guy was aggressive, and when I was in the bathroom, he pushed Janet over and penetrated her before I was back in the room. I suddenly realized something: none of these people were using condoms.

  Months went by and we had our first big scare. Janet might be pregnant; she was late for her period. This took a toll on us—a big toll. Luckily she started again a week later. More replies to our ad came in and I found one most interesting. He was older, as everyone was compared to us.

  He looked attractive enough and claimed to have ten inches. I was starting to get into this whole size thing. All the men we met were bigger than me. Janet seemed to like it and I was really turned on by her taking a huge cock. This big guy was our next guest.

  I decided we’d have a little extra fun this time too. I bought a video camera and came up with a role-playing scenario, even though Janet was feeling overwhelmed by the idea of role-playing.

  Tim arrived on cue and the scene was set in motion. Janet wore a tiny black dress, thigh-high black stockings and heels. She wore no panties and no bra. He was a traveling insurance salesman who had arrived at our door. I had a good imagination. He entered while giving us his sales pitch.

  Janet soon had him sit on the couch to discuss our buying options. She interrupted him, saying, “My boyfriend was supposed to be here. I’m sorry he’s running late. He’s always late. We had dinner plan after this and dancing … very disappointing.”

  Tim was on her side, of course. He said, “I find it hard to imagine any guy being late for you.

  I mean, you’re such a little darling if I may say so.”

  Janet blushed and they chatted more. He flirted with her and played up what he was selling, moving in closer and after a while massaging her shoulders. The role-playing proceeded on its own. I just watched and filmed.

  He offered to take her to the bedroom, and she agreed. In our room he undressed her and ate her pussy with reckless abandon. She was loving it and moaning louder each minute he indulged her. She said, “Oh please, fuck me. Please give it to me.” I was like, wow, she is really into this.

  Has she had too many wine coolers? She sat up, undid his pants, and the little cocksucker went to town. Tim was not hung. He had six inches, not ten. I was wholly disappointed. He had lied. He took my girl and fucked her. She loved it, but I was upset the entire time.

  We took a break after that sad meeting. It seemed like this whole setup had disappointment written all over it. These guys were porn-shop-booklet readers. I mean, what did we expect? In the future the Internet would change all this. But not before Janet and I tried more encounters. Things would soon come crashing down on our engagement.

  We invited another older guy to join us in the bedroom about six months later.

  Janet wore a sexy red dress and white stockings. She furiously sucked his smallish cock, which his letter had claimed was bigger. He was not hard throughout. He wasted no time stripping her down, sliding her panties off and eating her pussy. She was on fire, but he could not get hard.

  They tried everything with no luck. We invited another guy over months later. He was a heavy-set guy but carried a thick cock.

  Janet sucked him good. He was stiff and had a big mushroom cockhead.

  Before this meet-up we had discussed the aspect of condom-less sex. We could not keep taking chances. We bought some condoms, but they stayed in the drawer. She climbed her little butt on top of him, looked back at me with wanting eyes and mounted him. She rode his fat dick and loved it. The coming weeks we were scared as hell again about her being pregnant. It was killing us.

  Then another major obstacle came up. Janet became obsessed with the subject of sexually transmitted diseases. Here we were having her screw random men, condom-less, unprotected and bare. Not only was she in danger, but so was I. She decided we had to stop all swinging.

  At the time I was teaching at a nearby school. Out of the blue a new student walked in. She was a sixteen-year-old bushy-blond baby doll named Sara. Janet met her at a gathering and immediately did not like her. It was a jealousy thing. Anyway, life went on. Little did I know my future wife had just stepped into my world.

  Years past. We met a few other guys, no one special. We mostly dealt with one another and what life was sending our way.


  Things in my life were changing fast. The little girl I had loved as a high school junior was still my best pal and lover. However, the sex was getting stale, and our swinging was on hold. I was wary of diseases from the past encounters, and even got ill at one point. I thought I may have AIDS—the latest scare in the modern world of the nineties.

  I still wanted more wild sexy adventures, but none came about for quite a long time. Janet and I were facing typical relationship woes. Finances were low, our jobs not what we wanted, and she was constantly talking marriage and children. I was leery of a lot. I did not know where things were heading. I hated all this stuff. We needed a house, better jobs, more money—not to mention more exciting sex. We also had to deal with Janet’s family.

  Oh boy, what a messed up crew! She was the baby of eight kids. Most were alcoholics, and her closest-aged sister was the worst. We had a fight one night about all the above and Janet left.

  Her sister encouraged her to leave. But Janet came back crying into my arms and we made amends. Again money was tight. Janet wanted marriage and she wanted a child. Swinging was not on her list. I began fantasizing about other women, just to get by sexually. I was a young teacher and students were but a mere six to seven years my junior, so these lovely girls were great fodder for fantasy.

  I did not want a child yet, and marriage scared the hell out of me. I knew only one true girlfriend. Janet and I never had reason to imagine we would not be together forever.

  She wanted more and wanted it now. I asked that we swing more, perhaps meet some hot men—not the duds we had met before. The Internet was now an option and more possibilities were soon to come. Janet lost her job. We had little money, and we fought more and more. Her sister missed her, and she her sister. We split again, but she came running back into my arms. “I love you,” she insisted. “You and me are all I have.”