Southern Belle Cuckold Read online

  Southern Belle Cuckold

  Derrin Hart

  Fanny Press

  PO Box 70515

  Seattle, WA 98127

  For more information, visit www.fannypress.com

  www.cuckoldtales.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. The names, characters, and incidents are products of the author’s imagination and are used fictitiously. Any resemblance to actual events or people, living or dead, is entirely coincidental.

  Cover design by Sabrina Sun

  Southern Belle Cuckold

  Copyright © 2014 by Derrin Hart

  ISBN: 978-1-60381-491-1 (Paper)

  ISBN: 978-1-60381-505-5 (eBook)

  Produced in the United States of America

  * * *

  Prologue

  When I first met Jayme I believed in the concept of love, and I was deeply in love with her. We married after knowing each other just two months and launched into our life together full of enthusiasm. An attractive brunette, Jayme had a curvy body and a zest for sports and other activities I too enjoyed. College field hockey had left her with the kind of hard body I found irresistible. I figured that one day—once the kids came—she’d become more heavy-set like her mother, but everything is a trade-off. Maybe I wouldn’t mind because by then I’d have a couple of nice kids to console me.

  In my job as a systems analyst, I’d sometimes work twelve-hour shifts. Jayme managed a ritzy clothing store in the main district of our quant New England town. In the early years of our marriage most of our rare leisure time was spent hosting large parties and cheering for the various Boston sports teams.

  Then we bought an old house in rural Vermont that took up all our spare time. Our sex life was all right at first, but as the years passed we made love less and less often. Our first child arrived with great anticipation, contributing to the infrequency of our sexual play. Jayme gained a lot of weight when she was pregnant with Jasmine, but was able to lose most of it over time. Then Danny arrived, and our little family was complete.

  Jayme was self-conscious about her body after the two babies. I did my best to reassure her she was still sexy, but her vagina had stretched with each pregnancy, and that didn’t help our sexual problems. We soldiered on, concentrating on raising the kids and never looking back. In time Jayme came to be okay with her new body. At 150 pounds she looked fine; I had no real problem with her weight. She was not fat, and her breasts were large and firm, her sense of style as sophisticated as any woman’s in the city. All I wanted was for her to be sexual again, to have fun, to be daring and adventurous. She was not interested.

  With the kids she developed a bossy streak. I was the fourth wheel. The kids came first, than her and lastly me. I made good money so she could care less how much time I spent on the road or at the office. I was simply the provider. Decisions involving the family and the house were hers. I went with the flow, but I was getting tired of it. I needed attention, too. I tried to touch her, to massage her, yet she paid no heed to my advances. With the kids growing up so fast, I came to realize that unless I started getting a little love in return or fantasy play, I was going to be one bored middle-aged guy. I urged Jayme to experiment with toys, and or to try dressing up. I bought her sexy lingerie and vibrators, but she didn’t care for any of it.

  On New Year’s Eve, we joined some of Jayme’s buddies in the retail industry and went out to a bar on the east end. The place was hopping and everybody was dancing and getting tipsy. Jayme was looser than usual and I was having a good time. I noticed her flirting with some random guy at the bar who had been watching her dance. Jayme was wearing this fabulous red dress, low cut and tight with narrow shoulder straps, and she’d let her naturally curly hair go wild, cascading down her back. I asked her, “Hey, what’s up with the guy at the bar over there?” Jayme just frowned at me and ignored the question. I kept at it while we danced and she admitted he was handsome. That was my cue. “I saw you watching my wife dance,” I said.

  “No,” he said. “I’m just minding my own business.” I understood what she saw in him. He was tall, maybe 6’3”, with a thick head of blond curls; a few fell into his eyes.

  “No, it’s okay,” I said. “I like you looking at her.”

  He was taken aback at first but we shared a little more small talk. Finally he grinned and said, “Yeah, she’s hot.”

  “I’d like you to fuck my wife tonight,” I blurted out.

  “But, does your wife want me to fuck her?”

  He had a point. I bought us both more drinks—we’d stopped counting how many we’d imbibed—and said, “I think she does.”

  The guy rose from his barstool and joined me as I walked back over to Jayme. I grabbed her arm and the three of us ended up on the dance floor. At first she struggled and pulled away, but I got her to dance with us. She seemed perplexed.

  “Honey,” I yelled as we danced. This is my new friend; he’s been watching you.” Jayme’s eyes shot daggers at me. “He thinks you’re smoking and would like to screw your brains out tonight.”

  Jayme gave each of us a pointed look and replied, “Oh really? Isn’t that cool. What exactly will you be doing when he has me on my back, legs spread, darling?”

  Then, all at once, her sarcasm turned into fury. “You know what? Fuck you both, friggin’ perverts!” She stormed off to her friends’ table, leaving me alone on the dance floor. The guy backed away and got lost him in the crowd.

  That was the first of a couple of episodes that labeled me as a pervert.

  The second was at a football party for the New England Patriots Super Bowl run. That Sunday afternoon I had drunk a few before encountering a minor altercation in the hallway leading to our kitchen. Jayme had bumped into a guy who was a friend of a friend and they were going at it. The guy appeared to be apologizing for bumping into her, yet he was flirting at the same time. She was pissed at him and his lame explanation did little to help matters.

  “I said I was sorry,” he said.

  She was literally shaking her fist at him. “I just don’t appreciate that you did it on purpose.”

  The guy—his name was Pete, I discovered later—made her even more upset by stating, “Well, I guess you felt my hard-on press against those big knockers, huh?”

  That made Jayme furious. I hustled in to break it up.

  “Hey,” I said, “let’s go,” and dragged her down the hallway.

  Later that night Jayme wanted nothing to do with sex. Frustrated and still a little buzzed, I said, “I bet you’d like Pete’s fat cock instead.”

  That did it. “You’re a sick man, Michael,” she said.

  Over the next few years I never heard the end of it: I was perverted, sick, deranged, sex mad. She became a world-class nag, and I could no longer fool myself that she felt anything for me, let alone love. I was willing to put up with a lot for the sake of the kids and to keep the family together, but I needed something in return.

  We were divorced the following September.

  Chapter One

  I saw her for the first time at my gym late one Saturday afternoon. She must have been in her forties, yet had the body of a thirty-year-old. Her hair was sandy brown and medium-long and pulled back into a ponytail. I loved the way she strutted about as if starring in her own exercise video. She could not have been more than 110 pounds, compact, petite—my favorite type. She had tiny breasts but her spandex-clad ass was firm, pouty and proud. A mature baby doll with a butt.

  The
n I heard the subtle lilt in her voice and fell even harder. A classic southern belle.

  I mounted the treadmill next to hers and listened in as she spoke to the woman treading at slow speed on the other side.

  They were both watching the TV monitors, and she said how much she enjoyed Fox News. I thought, Oh great, not only a southern gal but a conservative one at that! I was even more interested.

  As a recently divorced father of two, I was badly in need of distraction. I’d been pushed around long enough and had finally made my stand. Now I was alone and it wasn’t so bad. I never minded the pushing around part as long as there was something in it for me. My prudish ex-wife offered little in return. She hated sex and disapproved of my mildest fantasies.

  I’m no loser, I thought. I have a great job and two young sons I adore. I’m also not bad-looking either for a guy in his forties.

  As I surreptitiously admired little Miss Southern Belle, I had no idea how my life was about to change. Of course I was a tad reserved when it came to attractive women. It wasn’t surprising that I felt intimidated.

  You see, I have a very small penis. That has always been a big issue in my life.

  This lass was very appealing. She worked out regularly at the same time I did, and during the next several gym sessions that coincided with mine, I heard her talk about her children. That fact reassured me. She wasn’t some intimidating single gal; she was a mother.

  One Wednesday evening I overheard her again talking with a friendly person in the free weight section, and her words were music to me ears: “I’ve been divorced for over two years,” she said.

  I was like, Wow, this milf is available. I had to make something happen. Or at least try to meet her.

  Over the next several weeks, I made no moves. She came to the gym at right about the same time I did. She always wore tight black spandex shorts and a loose t-shirt and usually tied back her hair. This outfit hid her beauty well— except for her round butt. She had quite an ass for someone so slim. She listened to her mp3 player and hardly spoke to anyone.

  One day I ran into her at the grocery store. She was with two small girls who looked like miniatures of her; they had to be her daughters. Her everyday clothing—snug jeans and a work shirt—gave her the look of a hip forty-something-year-old. Slim and fit and effortlessly lovely.

  Monday afternoon at the gym I made it a point to talk to her. I made my way over to the treadmill section and climbed onto the machine next to hers. She actually smiled.

  “I see you’re working hard, as usual,” I said.

  “Always!” she said, her smile even wider.

  I was at a loss for words. I pretended to be preoccupied with walking then running on the machine. Meanwhile I debated what to say next. Not much came to mind. “I’m Michael, by the way.”

  She glanced at me and smiled again, a heart-melting grin that showed off her perfect white teeth. “Catherine,” she replied.

  I finally knew her name. I was making progress at least. “Are you from this area?” I tried to give the impression that my workout was important but that didn’t prevent me from being friendly.

  She replied, “Oh no, I’m a Texas girl.”

  I tried not to reveal my excitement; my fantasies had labeled her a Southern Belle, and so she was! I asked her about Texas, and we talked about the heat and the dryness. I didn’t learn much but when I finished up my treadmill experience, I was satisfied with its successful outcome. I did not want to appear to be trying too hard.

  In the days that followed our eyes met a few times, and we exchanged casual hellos. I wanted to ask her out, of course. I was not only afraid of being turned down but also of losing my chance with her. She was new to the area and recently divorced, so I’d concluded she was available; others must have noticed her, too.

  I heard a woman comment on how she’d never seen Catherine with her hair down. I, too, wondered what she would look like.

  A tall, well-muscled guy made his way over to her one Friday evening, making chitchat and giving her the onceover whenever her attention was elsewhere.

  I needed a plan.

  Twenty-five minutes later, when I was in the communal shower, the same guy walked in, and my heart skipped a beat. Not only was he built in body size, but he also had a very large, thick member. As he pranced about in the shower, I—with my tiny tool—was in awe. If he was genuinely interested in Catherine, I’d didn’t have a chance. The time had come to put it all on the line.

  I dressed quickly, headed back into the workout area and approached Catherine, who was stretching, making it clear just how flexible she was. She greeted me with a big smile. “Hello, Michael,” she said.

  I swallowed hard and made my move. “I was wondering … Since you’re a stranger to these parts, how would you like to go out Saturday night?”

  This time her smile was shy. “That would be fun, but I don’t have anyone to watch my daughters.”

  I hadn’t anticipated this answer, so I simply said, “Well, that’s a bummer.” I shook my head with regret.

  Then she actually reached out and touched my hand. “Thank you though for asking,” she said in all sincerity.

  Before walking off, I managed to reply, “You’re welcome.”

  I considered what had gone down. At least there was hope. Although she’d said no, perhaps she truly had no sitter. I was still up to bat in my thoughts and could only hope she paid attention the next time we crossed paths. If she ignored me, I would have to give up. I went home and masturbated to the very thought that she might one day say yes.

  My job was busy as usual. As a computer security analyst, I did it all. I traveled near and far analyzing companies’ systems. I made darn good money and could work eighteen hours a day if I so chose. I made it a point to see my son and daughter weekly, and the ex-wife and I were at least civil when it came to the kids. Danny, my ten-year-old son, was a pretty good basketball player. I’d catch his games then take him out for a burger. Jasmine, my daughter of twelve, was more of a stranger; yet I did my best to keep up with her interests. I was sure her mother had tried to sour Jaz against me. I hated that.

  My life was busy, yet all I could think of was Catherine.

  I saw her again at the gym Monday afternoon. She strode up and down on the Stairmaster, brandishing her well-toned bubble ass and staring back at me boldly as I walked into the room.

  Encouraged, I approached. She looked at me and smiled but did not speak. I had been hoping she’d initiate a conversation. I made my way to the water cooler, took a drink, and then passed her again. She looked up and said, “So Michael, how’s your Monday going?”

  I was thrilled and replied, “It’s off to a good start.” She smiled even more broadly, maintaining her brisk pace.

  How easily pleased I was! I went about my workout with renewed energy, happy that she had at least said hi.

  These casual, brief, and pleasant but frustrating encounters went on for several weeks. We said hello, we chatted briefly.

  Each time I worked out I looked forward to seeing her sexy little body, ever hopeful she would take it to the next level.

  Then one Friday around noon, Catherine approached me, saying she’s like to take me up on my offer from a while back. “As a matter of fact, I’m free this very evening,” she added, tilting her head and looking at me through her lashes. “We could get a drink and maybe a bite to eat.”

  “I’d love to,” I said simply. Under normal circumstances I’d have tried to act coy, as though I had something of a social life, but her directness has taken me by surprise. “You found a sitter?” I added.

  “Uh-huh,” she said, “another single mom. It’s more of a play date.”

  We made plans and exchanged cell numbers. My confidence soared. After all, I was decent looking and in good shape for a guy in his forties. I had a lot to offer. I finished my day with an extra skip in my step, and no challenge could stump my fabulous brain. The afternoon flew by.

  Later that evening we
found ourselves at a quaint little pub in the heart of the city.

  From the start, Catherine put me totally at ease. Perhaps it was the way she gave me her total attention, never bothering to glance at anyone else. When the waiter took our order, she did flirt with him, but in that offhand almost unconscious manner that is as natural to Southern women as breathing.

  I learned something very important about Catherine that evening—the reason for her divorce.

  “My husband was just crazy jealous,” she said. “We couldn’t even go to restaurants, because he was convinced I wanted to go home with every waiter. He didn’t even want to go to the restroom or let me go. I think he was convinced I was planning a quickie in the kitchen instead.” She laughed, but her laughter was full of regret. “Maybe he thought every guy was like him—a wham-bam type.”

  “Why do you think he was so jealous?” I said, thinking I already knew the reason. She was just so damn cute; she couldn’t help attracting everyone in the room. Her answer was even better.

  “I do love sex,” she confessed. “And he wasn’t always Quick Draw McGraw.” She giggled. “At first all that intensity was a turn-on. But it got old real fast.”

  I think we talked politics a bit, but after she mentioned sex, I had trouble concentrating.

  We had met in the parking lot of the restaurant. After I walked her to her car, she gave me a hug and said, “We should do this again sometime.”

  I was one lucky man. I had caught her interest and made my move soon after her arrival in Vermont. This quaint New England town was not a Mecca for energetic young men; it was more a place people came to retire. She’d come here because she’d always fantasized about this area—so green, so different from Texas. Far away from her husband.