From Housewife to Cuckoldress

by Alex Hathaway

  “Yeah, we started doing that,” I said.

  “And yet, you didn’t take it all the way,” said Cheryl, “because you’re here, and he’s not. You have to claim your needs inside the relationship and see if he is ready to meet you halfway. From what I can see, he is.”

  I fell silent again. I had underestimated Cheryl, viewing her as a caution-to-the-wind hippie chick. That was still true. But there was more. It was like Cheryl understood my body, my conflicting needs, better than I did. Just like last time, I had a sudden urge to leave, to get out of that house and go back to whatever life I was trying to lead before, unspoiled by these experiences.

  Chapter 12: Sins of Summer

  And so I left. And I managed to forget. I put Cheryl and Eddie out of my head. I thought I would be so consumed by guilt that I would not be able to be around Dan without breaking down, but for whatever reason, that wasn’t the case. I didn’t want to make a habit of cheating on Dan, but the guilt was nowhere to be found. In some odd way, I felt defiant and justified.

  It wasn’t even a week before I had an incident. It was an incident in my own head.

  It happened at an odd time. I found myself looking up at Dan, watching as he pounded his cock into me. It dawned on me that my pussy was somewhat indifferent to what he was doing. It felt good, yes, but my pussy remembered something much more intense. Dan is not your sexual equal. What were the implications of that taboo thought? Can you be married to someone who is not your sexual equal?

  I probably could have found a way to sedate these thoughts, but change came along, this time in the form of a vacation. Dan’s division at work met a big milestone. Dan, as the project manager, was given two week’s vacation in the islands. We were off to an island called Turks and Caicos—a place recommended to Dan by his colleagues.

  We went in the summer, which is a hot time of year to visit, but we both needed to get away. I’m someone who likes the heat. The first week of our trip was spent largely in our own hotel room. We didn’t go out much, had some lovely talks, some tender but unspectacular sex, and plenty of room service. We also walked along the beach. One day, we decided to walk a bit longer. Eventually, the beach reached a point where it was blocked by a broken down peer. Someone had stacked a pile of rocks and hotel construction signs. You had to venture into the woods to walk around it, but we were feeling adventurous.

  On the other side was a sign: “nude beach: dress at your own discretion.” I smiled at Dan and we kept walking. There weren’t a lot of people on the beach, but one thing’s for sure: they were all butt naked. A few elderly couples, skin dried from years of sunny living, waved friendly greetings from their lounge chairs.

  I obeyed the urge to get naked. It felt good to have the sun on my breasts. I put my bikini in my bag. Dan seemed shy.

  “It’s okay,” I told him. “No one cares here. Try it—it feels good.”

  Dan took off his trunks and we kept walking, holding hands. Three college-age guys walked by, beer bottles in hand. When they got close, they took a hard look at me. I felt a tingling sensation between my legs, knowing I had their attention, knowing I still had that golden hip power, despite being a good fifteen years older than they were. My breasts, not as aggressively perky as they had once been, still arrested the male gaze. You have your pick of these men. I found myself glancing at their crotches as they walked by. They looked a lot like Dan down there, though one was definitely floppier and … uncircumcised. I looked at him the longest, trying not to stare.

  After we passed them, I turned to Dan and said something I wasn’t expecting to say: “See, honey, you don’t have anything to worry about.”

  My frankness prompted a new look on Dan’s face, one I would eventually come to recognize: surprise hiding some embarrassment and a flash of lust.

  But I had spoken too soon. The next two guys who walked by were older. Both wore straw hats but were totally naked otherwise. They had the flabby bellies of businessmen. I found myself smiling at them and sneaking glances downward. One of them had a tiny button of a dick, shriveled and shy. The other had a big soft cock. It was long and thin, dangling back and forth between his legs. I felt a primal tingle and stared at it too long. The man seemed to wink as I passed, both of them getting an eyeful of my tits.

  I was starting to feel very powerful. It was odd—here I was with my husband, yet I felt like the queen of the beach.

  “What a contrast in cocks!” I exclaimed to Dan. He laughed but seemed kind of shy about it, like he wanted to change the subject, like he wanted to be somewhere else.

  “Let’s lie down for a bit,” I said. “I want to get some tan on my boobs.” We made our way toward the edge of the beach, leading into the woods. Dan loosened up a bit, more so when I asked him to rub lotion on my breasts. But then he started to get an erection, and I told him to get off me. “I don’t think we’re supposed to have sexy time at the nude beach,” I snapped.

  Naptime. Dan read his book, John Steinbeck from the airport classics rack. I slept. I turned over from time to time, worried I would get a sunburn on my back. While I had napped, it had gotten late. The sun was still out, but it was on the downward slope. The nude beachers had left—tourists tended to be early risers here, looking to get on fishing boats and snorkeling trips.

  “Excuse me, do you have the time?” a booming voice startled me.

  I looked up from my nap to see a big smiling man, a black man, his skin as dark as most locals. He was not your typical island boat worker—younger guys who were in good shape from working on fishing boats. He had a pretty big belly, an older guy’s body, but I forgot about his belly as soon as my eyes took in his cock. Almost half erect, it hung down obscenely, protruding like a big fat snake. I couldn’t believe this man was willing to stand in front of me with a half-erection, obviously inspired by my own nudity. It was the most monstrous cock I had ever seen. It wasn’t beautiful, but it commanded attention. The weirdest thing: he was wearing a fanny pack around his waist. No other clothes. He looked distracting, ridiculous.

  I dug for my watch, buried in my beach bag, knowing Dan had forgotten his.

  “It’s uh … six o’clock,” I stammered.

  “Thank you!” The man boomed out, louder than necessary. “My better half expects me home at nine o’clock. I have three hours to get her to give me three more hours,” he chuckled, a dumb joke that made me smile somehow. He had a disarming way about him. His tone was better than his material.

  “I’m sorry; it was rude of me not to introduce myself. I am Benedict. My friends call me Benny.”

  Benny reached down, shook Dan’s hand. Then he came over, shook my hand. It seemed as if he made an effort to get nearer than he needed to. His dick was close enough to whack me in the face. I stared compulsively at his massive penis, but at the same time, I was annoyed at Benny and wanted him to leave.

  “Well, I guess I should be going,” Benny said, and started to walk away from us. Once he started to go, I wished he hadn’t.

  “Benny, sure you don’t want to hang out for a while?” I called out to him. “After all, you have three hours to kill.”

  Benny chuckled ….

  “We could use some tips from a local, too!” I called out. Benny turned and walked back toward us, his cock swaying all around.

  Benny borrowed a towel, took off his fanny pack, and lay down.

  “I’m surrounded by men,” I said to ease the tension, but it was surprisingly natural lying between them.

  We all laughed about Benny’s fanny pack and how funny it looked on a man when that was the only thing he was wearing. Then we made small talk about the island; Benny told us the fun spots we should check out. During the small talk, I savored the moment. Something was about to happen. My pussy was throbbing like crazy, getting wetter by the minute. And I was going to make it happen.

  “Benny, I couldn’t help but notice … you have a really magnificent penis.”

  “Oh thank you,” Benny said. “I do get a lot of co
mpliments … would you … like to touch it? I mean, if it’s okay with Dan.”

  Benny and I both laughed when he said that. What Dan wanted didn’t seem relevant.

  “Yes I would.”

  With that, I reached over and grabbed his penis with my right hand.

  “Wow, Benny … it feels so thick and meaty.”

  “That’s it, Linda,” Benny encouraged me. “I like how you work it.”

  “Benny, look how big it’s getting.”

  Benny’s cock continued to swell to life in my hand. It was still bent, but getting harder.

  “It’s already much bigger than Dan’s, and it’s not nearly hard yet,” I said admiringly.

  Benny laughed, enjoying his moment.

  With that, I got up and moved to the other side of Benny.

  “I want Dan to get a better view of this, Benny,” I said. “As you can see, Dan has a small penis, so he doesn’t know what it’s like to get stroked like this, and I want him to see.” Benny chuckled; he seemed to understand this sexual dynamic. I placed both hands on Benny’s cock and worked it. Even with both hands, his head stuck way out the top of them.

  I could see Dan stroking his cock in the background, he was already rock hard, almost in a daze from the shock and pleasure of what was happening. Seeing Dan like that gave me the confidence to take it further.

  “Benny, what a beauty. You must have fucked a lot of tourist pussies with this,” I said, getting wet just thinking about it.

  “I guess I’ve had my share,” Benny said casually.

  “You’ve probably wrecked a lot of marriages,” I said to Benny as I stroked him.

  “I don’t know about that,” said Benny.

  “Benny, can I ask you something?”

  “Sure Linda, as long as you don’t stop stroking. That feels fantastic!”

  “Have you ever fucked a girl in front of her boyfriend?”

  “Funny you should ask that, Linda,” Benny said. “I used to avoid those kind of scenes, but in the last few years, I’ve realized how popular it can be.”

  “That’s good,” I said while I was stroking him. “Because I want you to fuck me in front of Dan.”

  “Really?” asked Benny. I felt his cock hardening as I straddled him to jack him off.

  “Yes. Dan’s penis can’t fill me up and I want to show him how good a big man like you can make my pussy feel. He needs to see it so he can squirt and watch me come hard! Isn’t that right, Dan?”

  Benny’s cock was now as hard as I figured a bloated monster like that could get, and Dan was jerking off feverishly—I saw him coming in hard fast spurts.

  “Oh Dan, you squirted already?” I looked over and asked.

  Dan smiled sheepishly.

  “Your little cock loves seeing me like this; you can’t help but come fast. But Benny, he’s not coming at all, is he? Not at all!”

  It was true, Benny wasn’t anywhere close to coming, but he was hard as he could get now, jutting up with a small bent toward his stomach.

  “Jeez Benny, how big is that cock?”

  “Well, it’s been measured as big as eleven inches, but to be honest with you, I think it’s more like ten,” Benny said, as if apologizing.

  “Well, it’s plenty damn big,” I said.

  “Guys, can you both stand up for me?” I asked them, looking around to see if anyone was watching. But the beach was deserted.

  They both stood up, obeying me.

  “Now stand next to each other.”

  They moved closer together.

  “Closer …” I said, moving them together with my arms.

  “Wow,” I said.

  “I was going to have a cock contest, but there’s not much of a contest, is there?”

  Benny laughed loudly, with a touch of cruelty—and so did I.

  It was pretty shocking to see the comparison. Dan’s cock was all shriveled up from coming hard, tiny and withdrawn. Benny’s cock stood almost straight out, bending from the weight of itself, ten thick inches from his body. It was as if they were different genders.

  “Dan, this isn’t fair, let’s at least get your tiny penis hard,” I said to him. That was the first time I had ever called Dan “tiny”; he twitched right to life as I said it, clearly liking the truth of my words.

  I stroked Benny’s shaft absently with my left hand, while working on Dan’s with my right. I felt it grow in my fingers.

  “Oh there it is!” I said. “Let’s get this cock hard!”

  Dan moaned and twitched in my hands. I was dripping quite a bit myself.

  Dan’s cock twitched to life … getting harder by the second. Soon it was stiff, slippery with his previous come.

  “Oh Dan, there you are! But look how much smaller you are! See that?”

  Dan said, “Yes.” How could he not? But he was moaning, too.

  “Dan, be honest with me. Do you like my body?”

  “Yes.”

  “Is it hot?” As I asked him that, I swayed my hips around so he could have a good look at me.

  “Oh God, yes.”

  “Do I look like I deserve to have my pussy fucked—fucked real good?”

  “Oh, yes!!”

  “And Dan, I want you to be honest, which cock do you think is made for filling up a beautiful pussy like mine?”

  “His.”

  “Do you want to see him fuck me, Dan?”

  “Oh Yes!!”

  “Do you want to see him give me what you can’t, what I need so badly?”

  “God, yes!” With that, Dan came again in my hand, not so much come this time.

  “Wow Dan that was fast—doesn’t take you long,” I said as I stared intently at Benny’s near-hard cock, nowhere near coming yet, despite my constant stroking.

  “Okay, Dan, I’m going to show you how I get what I need.”

  Benny laughed, and I did a little, too. It was just so clear that Dan was outmatched. Clearly it turned Benny on, just as it did me.

  “Good thing Benny’s cock is still hard and ready to fuck a pussy.”

  With that, I started jacking Benny off with both hands, licking the head.

  Between licks I said, “Look at this two–hander, Dan! It is so intense to jack a cock with two hands like this, getting him ready for me. I can jack you off with two fingers, but not Benny!” I couldn’t believe how mean I was being, but in some strange way, I also felt justified.

  “Oh, but there’s a problem,” I said. “I don’t have any condoms.”

  “That’s okay,” Benny said, “I’ve got you covered there.”

  Without notice, Benny pushed me back on the towel, a little bit roughly. Dan looked my way protectively. Benny stood up tall, took off his fanny pack, unzipped it, took out a condom. He rolled it over his huge cock, making it seem that much more engorged. The condom only fit over about two thirds of it, which was so erotic for me to see. I’d never seen a condom that didn’t slide easily on Dan’s cock. I masturbated while Benny put the condom on, spreading my legs wantonly.

  Then he was kneeling, placing that big cockhead up against my lips.

  “Don’t hurt me!” I cried out.

  “Oh, don’t worry baby, we’ll take it nice and slow,” he said with a comforting but cocky smile.

  He really knows what he’s doing, I thought to myself. Then I saw his big cockhead, or heard his big cockhead, plunk inside me. It was a mixture of pleasure and pain, a jolting sensation.

  “Ow!” I called out. He just left his cockhead in there for a minute, letting me get used to the feel of it. I saw the rest of his cock still outside my legs. I spread wider, wondering how he was going to fit that fatness inside me.

  “That’s right, you’re nice and wet for me,” he said as he pushed his cock a couple more inches inside.

  “Oh!” was all I could say to that. I felt totally stuffed, a bit uncomfortable. He pressed a little deeper, about five inches of his thick cock inside me. He was as far back as Dan can get, but it felt way different, and just like
with Eddie the first time, it didn’t feel all that good. I was half-hoping it would feel really bad from here on out, then I could somehow get this sluttiness out of my head, go back to being a loyal wife.

  “That’s all for now,” he said, a good half of his cock still outside me. “Time to work what we have in there ….”

  So he started, pulling his cock out just a couple of inches, then pushing it back inside me. It still hurt quite a bit, and I found myself biting my lip, bracing as he took his slow, steady strokes. I was up on my elbows, taking a careful look at my pussy under this assault. A couple more minutes of thrusting, and it did start to feel good.

  “That feels nice …” I said with my arms wrapped around him.

  “We’re just getting warmed up,” he said reassuringly. “Now are you ready for some real fucking?”

  “Oh please …” I said kind of helplessly, between a yes and a no.

  With that, he pressed my legs nice and wide and gave his cock a push!

  “Ahhh!” I cried out. Propped up on elbows again, I could see that a good portion of his cock was inside me.

  “That’s it,” he said, “That’s it.”

  “Don’t push any more inside me; that’s all I can take!!” I pleaded with him.

  “No problem,” Benny said, “Don’t you worry, I won’t go any deeper than this ….”

  And with that, he started stroking in and out, withdrawing a few inches then slowly pressing them back in, about seven inches inside me. In, and out, in, and out. My body was consumed by the sensations. But then he started picking up the pace. As he promised, Benny went no farther in. He withdrew all but the head and pushed it back inside me.

  “Ugh” was maybe what I said then. This was a different type of experience; I didn’t have the language for it yet.

  He started pounding me pretty good. I could feel his thickness dragging against my clit, pulling my pussy lips in and out, coating his cock with my juice. His belly flopped as he moved in and out of me, faster and faster.

  I could feel a strange itchy hot sensation building between my legs—and in just a few more thrusts, that itchy hotness was spreading up my body and I was wrapping my legs around his and calling out, “I’m coming!! Oh fuck I’m coming!!” Wave after wave of orgasms bucked through my body.