Southern Belle Cuckold

by Derrin Hart

  I thought, hell yeah, but knew I’d be lost in that cave after a real man’s dong had drilled her so deeply.

  She pulled my tiny dong out and fondled it. “Gee, honey, you’re so small compared to Barry.”

  I looked her in the eyes and saw her grin. “You think so?” I said.

  She laughed and kissed my cheek. “Let me make it all better, baby,” she insisted and with that sucked my cock. She sucked it good and got me off. I was happy and glad for the milking.

  I asked Cat if she’d like to have Barry back in the morning for another fuck session, but she wasn’t interested. She was still sore from the earlier pounding. So in the morning we sat and ate a nice breakfast, leaving the room with our bags at close to ten in the morning. The second Mandingo party had certainly been an interesting one. I wondered if we were going to get a bill for the bed. We’d managed to prop it up but it hadn’t been a very comfortable night.

  As we were exiting the hotel, who should appear but Charles. Cat was of course excited to see him and ran over to give him a hug. He was tall and lean and his bald head was shining in the sunlight. Everything about him was sexy. She wanted him. I just knew it.

  They chatted and I made way over too. He said hello and as usual I was bowled over by his charm. He’d touch her as he talked and smile at all her words. “Do you guys know about the big gathering coming up in Jamaica?” he asked.

  This was the first I’d heard of it. Catherine was all ears.

  “ ‘Hedonism’ ” he explained, “is a big swingers’ party in the Caribbean. It’s held at a sexy resort with all trimmings. Just one big party and the memory of a lifetime.” He leaned in close to Cat’s ear and added, “I’d love to see you there.”

  She blushed and turned giddy. “I’m sure Michael can get us reservations; he’s good at stuff like that,” she said, looking at me with a great big smile.

  Chapter Ten

  The next few weeks were all about me getting us a trip to Jamaica. Work had never been busier but Cat kept asking if I had looked into it.

  Julie came to me one afternoon and asked for a truce, meaning she’d be nice to me if I helped her. She wanted to go on the pill and her mom was not sold on the idea. If I were to put in a good word, she would be ever so happy with me. I knew her secret and thought it was a good idea. I agreed and finally met with success a week later.

  The following week we bought a new giant fifty-four inch Samsung LED flat screen TV. Soon after, Sunday became movie night for the family. The thing featured amazing visuals and the surround-sound knocked us back with its awesome effects.

  I did my best to be a good dad to Cat’s girls. It was not easy, but I made strides. I also gave it my all with my own kids, even though Jayme my ex was a pain to deal with. To her I would always “the pervert,” which really pissed me off. I was no different from most men. I loved sexy women. I looked at them constantly, fantasizing about what I would do with them. I masturbated a lot. I have to admit, the chastity padlocked device had made a difference with Cat. It had kept me from jerking off and allowed me to focus more on her needs. Not wearing it anymore gave me way too much individual playtime.

  I had made the reservation for the Late August trip to Jamaica. I pulled many strings to get covered at work and find safe friends and family to watch the girls for the four days we’d be gone.

  We boarded the big plane Thursday morning. The flight was long at about five and a half hours, but we slept part of the flight, napping on and off. We made a connection flight in Miami and arrived in the Montego Bay region not too long after. We then took a ninety minute very adventurous countryside bus ride to our resort in Negril.

  The beach view was absolutely stunning—white sand, palm trees, blue skies. Catherine was excited, to say the least. She had bought an entire wardrobe of beach clothes for the trip, and man had she picked up some sweet items. Our exclusive resort and bungalow were perfect.

  We unpacked and looked around some. The local workers were very nice and we were shaking our heads at their accents and slang expressions. Our bell girl kept saying, “Beat dem bad,” as she helped us get settled and showed us various brochures. Once she was gone I asked Cat what she thought the girl meant.

  Catherine—in her white, pink, and yellow floral sundress and huge white wide rimmed sunglasses—ran to me, jumped into my arms, and kissed me. “I think she wants us to have a good time, Mike. We should walk around some.”

  The trees were so beautiful here on the island and the walkways decorated with huge colorful flowers and interesting stonework. We strolled to the main resort building, spotting other smiling couples as we went. A big buffet was available three times a day in the main hall and man, the food was delicious—lots of exotic fruit and meat with spices we couldn’t identify. Bars were set up on the oceanfront; one was even a swim-up style beach bar.

  “This place is crazy,” I told Cat as we walked about.

  A local Jamaican man with long dreads rolled up to us in a golf cart. He stopped and said, “Hi dere nice people. You do outing here eh? Have fun time.” Then he handed us various flyers about activities offered in the region.

  We passed a miniature golf course; tennis courts, shops with all sorts of neat souvenirs, and even open-sky massage buildings.

  Catherine wanted to see and touch the beach, so we headed that way. Down closer we saw outdoor showers and a gorgeous ocean of aquamarine. Already people were on the beach frolicking about. The brochures called the main beach the prude beach, as opposed to the nude beach on the other end. We’d have to check that out for sure. I knew Catherine was hoping to find Charles in all of this, so we looked on. We could not spot him but ran into many couples here for fun and sun.

  We purchased cocktails at an outside bar and people-watched for nearly an hour. A young fellow approached us, offering to be our tour guide. He was no more than twenty, with a lean young body and big smiling face. His hair was cut very close to his head with a little black tuft sticking out on top.

  He came up to me and shook my hand. “Hello budda,” he said with a wide grin. “Me tell you, dis place have plenty to do.” We heard him out and decided he was a cheap ticket to all the area. It would be worth the fee to have Jayjune take us about.

  He told us all about the area, the nude beach down yonder, and the best activities to sign up for. He mentioned the buffet—open most of the day—the scuba diving, the massages, and the fitness center.

  He also was upfront in saying that Catherine was a sexy woman and he liked her look. His exact words were, “Rent-a-dreads okay man, eh? Me know many to service your milk bottle.” We were like, what? He smiled and we kept walking, stopping next at the glass bottom boats. We were very impressed. He kept talking about Cat, adding, “Dese mon no want the kitten man, dey want da cat.”

  Our guide Jayjune took us to all the local hotspots. He gave us a good idea of the resort and surrounding grounds. The rest of the day we relaxed and watched as many of the vacationing couples showed up. This was a big weekend for swinging and fun times.

  The next day we took a glass bottomed boat ride to the coral reefs and saw the most incredible sights. The colors and the sea life were amazing. Later, in the early part of the afternoon, we spotted Charles in the swim bar, wearing just a bathing suit. He waved us down, giving us a good view of his lean muscular body. His bald head sparkled in the hot sun and his bare chest was bulging with nice pecs.

  As soon as she saw Charles, Catherine broke into a run. She surprised me by practically tearing off her sundress to reveal her white bikini; then she headed straight for the water. They embraced as if they knew each other all too well.

  So the rest of the afternoon we hung out with Charles. I was the third wheel, but Charles treated me with respect and that kept me happy. We sipped margaritas, and tried all sorts of creative drinks together. It was cool to be able to swim up to the bar to get drinks and food. I enjoyed a massive shrimp cocktail and Catherine and Charles shared a big lobster tail. We made wa
y to the ocean a bit later and sat along the shore. Charles wore a black jockey type swimsuit, sort of like a thong but still with some backside to it. His bulge in front was impressive. Catherine noticed too, and I followed her eyes most of the afternoon as she took look after admiring look at him. We laughed and drank and had a good old time.

  The beach was very busy, perfect for people-watching. A walk along the water’s edge and a dip to cool off followed. Meanwhile Catherine and Charles took the time to be close, holding hands and even embracing in the water. I wondered if Charles was meeting friends here at the convention or if he was alone.

  Dinner plans were made, and yes with Charles. Back at our bungalow Catherine and I discussed the evening’s activities. Drying her hair with a towel as she exited the shower, my wife said, “Charles thinks we should try the reggae dance class tonight, honey. It’s supposed to be a lot of fun. We can hit the buffet first. Are you good with that?”

  I nodded my head agreeing to everything as my hot wife pranced about naked in our cabin.

  She slipped into a tight pair of Capri lime green pants and a stomach-revealing white halter-top. She wore sandals with medium heels and jewels on top, strapped to her feet with crossed rope laces. I slipped into some khaki shorts and a button-down blue shirt.

  Charles met us at the buffet, where we feasted to our heart’s content. He had worn a pair of off-white pants rolled up at the ankles and a black tank top a stretchy material that clung to his chest muscles. The two of them flirted all the while, and Charles mentioned he was here to just have a good time, not meet anyone in particular.

  I had expected Dirk and Sether Cox to show up, but I guess that was not part of the plan. Later at the dance class we were taught to move with style from a very friendly Jamaican woman named Estella. She was personable and moved with flair. I got involved some, but mostly Charles and Cat danced together. After the dancing we followed the crowd to a bonfire by the ocean. By the evening’s end, we were all tipsy and stumbled away from the beach.

  There was no stopping Charles from coming back to our bungalow. He and Catherine stumbled into the bedroom and there began their wild rendezvous with a passionate kiss. I sank into an easy and watched. He kissed her neck and ran his hands all over my wife. Gently her top was lifted over her head and he kissed the soft spots around her neck down to her shoulders. She grabbed his ass and tilted her head back, enjoying it all to the fullest. They fell to the bed, tossing aside the canopy curtains and wrapping their bodies into one entity.

  So much kissing followed … Catherine moaned in pleasure for at least twenty minutes. I heard her cry out, “God, I want you. I want you so much!”

  He licked her all over, then gently lifted off her bra. Cat’s nipples were his Garden of Eden. Her breasts were small but her nipples thick and prominent. He savored her chest and made her moan even louder. She moved about the bed, latching onto his strong frame. Her legs intertwined with his, and she kissed him madly. They squeezed each other ever so tightly, and she wrapped her legs around his torso. He slid down her body and unbuckled her green Capri pants; then he slid them down her smooth hips to reveal her silky white bikini panties. As he eased her pants off, he tasted her belly button, causing her to raise her pelvis longingly toward him. She was on fire! He licked a trail from her stomach to her nipples, teasing at her panty line. Then he came back up to kiss her lips with exquisite delicacy.

  Tiny my little dick came to life. This was so sexy, so damn hot!

  He took her panties off finally and, after an hour of foreplay, dove into her sweet cunt. Marveling at her massive pussy lips, he peeled them apart. His darting, probing tongue sucked her clit and she cried out in joy. He had her on the edge in no time but had no intention of finishing her off. I noticed her foot playing about his loins, probing his manhood.

  Charles had Cat ready to climax but held off. He rose to meet her and they clasped each other’s bodies in a close embrace. She was ready for more. She grabbed at his pants now, shoving them down his legs and grabbing his underwear and tearing them down too. His cock sprang loose.

  “Oh God, baby, I need you,” Catherine cried out.

  His penis was a magnificent specimen, dark brown and thick. It was much longer than mine and had this gigantic mushroom head that was the true centerpiece. I had never seen such a large cock head.

  Catherine bobbed up and down, proudly sucking his dong. Undoing my pants, I joined in as best I could, fiddling with my own weenie. As she deep-throated him, his head grew even thicker and more pronounced, its ridges swelling.

  Wow, what a dick, I thought. The head was lighter than the shaft, and I watched in fascination as it worked its way in and out of Cat’s tiny mouth. His moans of pleasure increased, as did Catherine’s zestful enthusiasm for her task. Unable to wait any longer, he slid his body up and lowered her tent flaps onto his massive fat cock. She cried out, “That’s it. This is what I need. Oh God, Oh God, yes, yes, yes … so, so good!”

  My little penis exploded into my hand. Catherine, my wife, my southern bride, lowered her sexy butt onto his manhood and took every bit of him inside her. Then she went wild, bucking and pumping. This is how my nymph needed to be fucked, and it was happening before my very eyes. They moved from one position to the next, connecting sideways, doggie style, with her on top and facing his feet. I sat for hours watching the union of Charles and Catherine. It was so perfect, so fitting, so complete. These two were made for each other. He never did come; the man could last for hours. Catherine had four orgasms, her most ever. When it was finally over, she was exhausted, as was I, just from sitting there taking it all in.

  Charles finally left our cabin at three a.m.

  Chapter Eleven

  We spent the rest of the vacation mostly with Charles. The alternative was the chastity device; that’s what Cat told me the following morning. I must either accept this lifestyle or agree to be locked up again.

  For the first time in a while, I actually wondered which was better. Being locked in that cock cage made me horny all the time and unable to jerk off. It did give me a reason to try harder with Cat and it saved my mojo for our sex life. These meetings with other men took their toll in other ways. The mind games and the jealousy were terrible. Only for now, here in Jamaica, there was no point in second thoughts. I really had no choice but to accept the current arrangement.

  Cat and I hit the fitness center without Charles. She wanted to get her work-out in and so did I. We also tried scuba diving and made another trip to the coral reefs. Golf was fun and we got in some tennis.

  Saturday we joined Charles for massages and afterward made a visit to the nude beach.

  Catherine was the first to slip out of her clothes and Charles showed no hesitation, either. I was embarrassed but followed suit. The three us hit the ocean and the beach was gorgeous, with lots of people milling about.

  Here was my naked wife next to this black bull … and then there I was. His cock was a “shower” rather than a grower, a proud, thick, fatheaded penis. Mine was a shriveled mess. Catherine looked great nude; all the locals and visiting couples were checking her out.

  We strolled about until we found the perfect spot to spread our blanket. Later we hit the water, took walks along the edge and watched couples and a few singles stroll past. Catherine and her guy covered each other with suntan lotion and flirted.

  The last thing I wanted was for Catherine to fall head over heels with some dude and be all moon-eyed. I did my best to keep things light, fun and not so serious. Charles was pretty cool about it, always trying to include me in conversation and whatnot.

  A lot of the couples were with other couples. Unlike me, the guys were not offering their wives up to single men. These foursomes gave the men someone else’s wife to keep company with. The ones I talked to said it was just easier. Four people meant less drama; the extra person kept the marriage safe. I pondered my situation quite a bit. We had missed out on the toga parties and couples events, but Cat could have cared less
.

  On the walk back a local guy and his buddy made a funny comment about us—well, about me. He yelled out, “Hey, check out the little worm on that guy. Put it on a hook and toss it out to sea!”

  That night Charles again joined us at our bungalow. A three-hour session followed. This time Catherine was much more vocal, more relaxed, hornier and eager to let it all out. She said a lot of stuff like, “Fuck me like only a real man can, and give me that awesome cock. I love that cock!”

  This time I didn’t just watch. It took too long. I read brochures and took pictures and tidied up. Meanwhile I heard her say, “Oh, baby, this is how I like it, take me, and give me all you have, make me explode. MY HUSBAND CAN’T MEASURE UP TO THIS UNBELIEVABLE COCK OF YOURS.”

  I waited to masturbate until Charles was gone and Cat was sleeping. She had no intention of giving me a mercy fuck. In fact the plan was to have Charles back in the morning for another session. Catherine had demanded it.

  In the morning, right at 9 a.m., Charles knocked on our cabin door and Catherine, in a tiny pair of peach panties, ran to let him in. They got right down to business. She pulled his shorts down, took his hand and led him to our bed. I was still in it. They frolicked for a few minutes and then he was on top and inside her. She cried out in pleasure, “What a way to wake up in the morning, ummm, so sweet, ohhhhh, yessssss, give me that fucking tool.”

  They fucked hard, right next to me. He was pushing deep into my wife, and she welcomed every bit of him. She then took control, turning him over and mounting him. Smiling at me, she tossed back her hair and lowered her ass to impale her cunt with his majestic rod. She bounced on him and arched her back in sheer joy. This was too much for me. I went to get some orange juice from the fridge.

  Sunday was our last day on the island. Charles had to leave that morning so Cat and I were on our own. We had heard about a small, secluded island nearby that offered the most magnificent views and chartered a small private boat to take us there. A local Jamaican guy with dreads and a pretty good body drove the boat. For the entire ride, he kept his eyes on Catherine. The day before, my wife had bought a new bright pink bikini that left little to the imagination; it had a thong back and a tiny triangle in front. Dokku, our captain, eyed her with interest. After docking, we headed up a natural staircase to some magnificent cliffs. The surrounding landscape was awesome and we enjoyed a bottle of wine from our picnic basket.