My name is Jackson, and now at the age of forty-eight, I’m the vice president of sales for a plastic products manufacturing company in the Charleston, South Carolina area. My wife, Margaret, and I have had a great marriage, but now that our children are grown and living near Atlanta with their own families, I’ve had more time on my hands and a wandering eye for voluptuous women.
I’ll admit to having several one-night affairs with married women I met in bars while traveling for my job, but they were just for sexual relief, since Margaret was becoming less interested in sex, and none of them meant anything to me emotionally. I learned about cuckold relationships from those married women I had been fucking who told me their husbands were not only aware of their promiscuity but encouraged it and enjoyed being submissive to their lovers when they had the opportunity.
Some people likely won’t agree with my perspective on this, but I get a lot more pleasure fucking married women than single women, especially knowing their submissive, little-dicked husbands can’t please them the way I can, and I was sorry that I never got to fuck them in front of their husbands. Married women on the hunt for cock are easier to handle and hornier, with no games, and there isn’t much concern about them wanting to start a relationship. Just two horny adults doing what comes naturally.
I was hoping to find a married woman in a cuckold relationship close to home that I could develop a longer-term sexual relationship with, and even get her husband involved so we wouldn’t have to sneak around. It would be less risky for me to avoid being seen in public with another woman, by going to the cuckold couple’s home for sex.
Even though I previously followed the adage of ‘don’t shit where you eat,’ I was attracted to Erin, the twenty-six-year-old wife of David, a twenty-seven-year-old sales manager who works in my department. My attraction to her became stronger over several years, and I was hoping to work my way into David's and Erin’s lives and convince him to be a cuckold to her.
But this story begins a year ago after David had been working for the company for two years, and he had just gotten married to Erin, after dating her for a year since she graduated from college. He was still a salesman, and I was a director, close to being promoted to vice president. I can still remember the first time we met at a company Fourth of July picnic at the CEO's beach house, and I was smitten with Erin’s beauty.
Erin is petite, and at five feet and three inches tall, weighing about one hundred and twenty-five pounds at that time, and with blonde hair and brown eyes, she looks amazingly like the singer/actress, Jessica Simpson. She even has full and round, melon-sized, 34DD breasts like the actress, and she wasn’t bashful about dressing to show off her substantial assets.
I was attracted to her then but was still being sexually satisfied by Margaret at home, and I hadn’t yet started cheating on her when I traveled. I made sure to spend time with Erin and David at the various company events over the next couple of years, and I tried to be friendly without being too obvious that I was attracted to her, for fear of seeming like a dirty old man.
Learning About Cuckolds
By the time I was forty-seven and David was twenty-six, he was being considered for a promotion to manager, I was a vice president, and I had begun fucking other men’s wives out of town and was becoming aware of the concept of women cuckolding their husbands. I naturally started thinking of David and Erin as an attractive couple to satisfy my growing sexual hunger for her, and I started reading cuckold stories online to get a sense of how I could approach them.
Over the next few weeks, I read hundreds of cuckold stories and learned that some husbands who were masculine and aggressive in most other aspects of their lives can have a subconscious desire to see their wives fucked by other men, and it just takes the right situation or trigger to make them aware of their hidden cravings, even to suck cocks.
I also learned that many of the cuckold husbands have smaller dicks, which fuels their desire to be submissive and humble themselves to other, well-hung men. Some of the stories even talked about cuckold desires related to ancient, biologically-driven sperm competition. That somehow, in a twisted logic, causes the cuckold to enjoy immense sexual pleasure through the humiliation of another man inseminating his wife, and the inherent risk of him impregnating her.
Then, of course, there are some cuckolds who are strongly bisexual, to begin with, and they can suck the cocks of their wives’ lovers, giving them cover for their innate desire to suck cocks. And they don’t have to worry about being exposed by the men they’re sucking, since the wives are enjoying being fucked regularly by big-cocked men. The husbands’ cock sucking becomes inconsequential, or even a source of amusement for them.
There are also men, who for whatever reason, have the need to be submissive to and controlled by others, and they get enjoyment out of their wives taking charge in their lives and then submitting to her, and to her lovers. The humiliation and degradation become bitter-sweet, and they love being used that way.
I learned all I could by reading those stories and I did other research that revealed that only about one to two percent of couples have cuckold relationships. I realized that the likelihood of David and Erin being convinced to enter that lifestyle was slight, at best, and the key would be for me to get into David’s head, to see if he had those hidden desires, and hopefully even a small dick.
Working More Closely with David
No one was aware of my deception when I started a mentoring program for the sales department and selected David as my mentee, just for the purpose of spending more time with him. He and several other sales staff were being considered for the open manager’s position. I got the credit for making the assignment from David and Erin, by making them aware of it together at a company function, where I had them assigned to sit at my table. I wanted them to see me as a benevolent boss who was looking out for their best interests.
That was good timing since Erin had given birth to their son three months earlier, and not only was she breastfeeding him, which made her breasts even bigger and fuller 34Fs, but David would be a little on edge from lack of sex since he was likely almost at the end of the abstinence period.
I danced a few dances with Erin that night, as David danced with Margaret, and I behaved myself by not holding her too tightly and had a good conversation with her about how well David was doing in the company.
Staring on Monday at work, I called David into my office, and since I was aware that he worked out at home to keep himself fit, I said, “This mentoring program is a good opportunity for you, David, and we’re going to be spending a lot of time together. We can’t do all the mentoring during the workday, so I’m giving you a temporary membership to the gym that the company subsidizes for manager level and above, and we can talk there. You’ll also be traveling with me, and that will give us a lot of time together while on the road and in hotels at night.”
He was curious and asked, “What is involved in the mentoring?”
I answered, “Some of it will be to impart management techniques, for if you get the promotion, and you’ll also get the benefit of my experience on our products, at handling sales calls, and especially closing sales. I work out three nights a week at the gym when I’m in town, and if that‘s convenient for you, you can join me tonight after work. You’ll have time to go home to get your clothes. They’ve got towels available there, and you’ll have a locker, so we can shower afterward.”
We met at the gym at 7:00 pm, and after jogging around the track for a few minutes, we went to use the machines. We had a chance to talk about business before moving to the free weights, and I was impressed with his fitness. He was also impressed with me, and said, “My goodness, Jackson, you’re over twenty years older than me, almost old enough to be my father, and I’m having a hard time keeping up with you.”
I was looking forward to hitting the showers with David afterward, and I knew he’d be impressed with my package. My cock is uncircumcised, thick, and seven inches long on soft, and it hangs heavily over my low-hanging, lemon-sized balls. I’ve been told by the married women I’ve fucked that my genitals are attractive swinging between my legs, and they loved sucking my cock and balls as much as fucking me.
The gym is a good, but older, facility and they have an open, group shower with multiple shower heads, instead of individual stalls. David seemed a little shy about taking off his towel, and when we got in the shower, he tried to hide that he was staring at my cock. I was happy to see that he has an average dick, less than three inches long on soft and of medium thickness, with a tight nut sack. It was a good sign that he was attracted to my cock, or at least curious about it.
I did everything I could to give him a good look at my genitals, by turning his way and closing my eyes as I washed and rinsed my face in the spray, but I was able to squint and saw him looking at my meat. We worked out two more times that week, and I was more revealing by soaping up my cock and balls for him to see, and even turning my back and leaning down to wash my lower legs, so he could see from behind my cock and balls hanging between my legs.
On the way out of the gym on Friday, I said, “We’re going to hit the road for a few days next week, David, going by car to visit customers in a three-state area. I’ll drive, and we’ll leave the office about noon on Monday, stay in hotels along the way for three nights, and return to the office about noon on Thursday. That should give us a lot of quality time to talk in the car. And since the CEO has been on a cost-cutting binge recently, we’ll be sharing the hotel room, with separate beds, of course.”
We talked mostly about work in the car on Monday afternoon, in between three customer stops along the way, and then we arrived at our hotel for the night. We had dinner in the hotel restaurant and ordered mixed drinks with our meal. I wanted to see if he was the least bit willing to talk about Erin.
After a couple of drinks, when we were both mellowed out, I said, “Tell me if I’m out of line saying this, David, but you must have to beat men off Erin with a stick. She’s just about the prettiest lady I’ve seen in a long time.”
I was pleasantly surprised when he responded favorably to the compliment, saying, ‘Yeah, thanks, Jackson, but you don’t know the half of it. We started dating seriously in college when I was a senior and she was a junior, and that year without her after I graduated and started working for the company was stressful for me.”
That sounded like a good way to delve into their personal lives, and since I knew from his personnel file that he went to college at USC in Columbia, I asked, “Why was that so bad? I think it’s a little less than a two-hour drive from Charleston to Columbia, and you should have been able to get together.”
He replied, “Yeah, it’s not that far, but with me starting a new job and traveling, and her with a heavy course load, we only got to see each other about every third weekend.”
I made another leading comment, saying, “I know that you had to be missing a beautiful lady like Erin, for a lot of reasons, but after you said, ‘you don’t know the half of it,’ I’m guessing there’s more to it.”
That wasn’t really a question, but a comment that he could reply to or not, and I was pleased when he said, “Well, you said yourself how beautiful Erin is, and she dated a lot of boys there before we met. I mean, we didn’t make a pledge of chastity or agree to not date other people or anything, but while I made the commitment on my own not to date others, I’m quite sure that she was partying over there.”
I wanted to be sympathetic, and said, “Wow, David, I can see how that would be upsetting. But why didn’t you two just agree not to date others?”
We were starting on our third drinks, when David answered, “I was willing to make that commitment, and even did it on my own, but I didn’t think Erin would have honored it, even if she promised. I didn’t want to put her in a position of feeling like she was cheating on me, and then having to lie to me about it.”
I was getting more information than I could have hoped for, likely because I had struck a nerve by asking about them being separated that way, and I took the risk to probe a little more. I asked, “If you two were close enough that you got married only one year after she graduated, why do you think she wouldn’t have been loyal to you when you were separated like that?”
He let me know that he had gone as far as he was going to in explaining her situation, at least for the time being, saying, “If it’s okay with you, Jackson, I’d rather not get into that right now.”
I said, “Okay, no problem for me, and I’m sorry if I got too nosy.”
David would have been within his rights to nicely tell me fuck off and stay out of his business, but instead, he showed me deference as his big boss, and maybe even a little weakness, since he didn’t really say anything out of line, to begin with, as he said, “No, it’s okay Jackson, I didn’t mean to sound like that. Maybe we can talk more about that tomorrow when I have a clear head.”
We went up to our room after that discussion ended, and I gave Margaret a call while David used the bathroom to get ready for bed. Then he called Erin while I used the bathroom, and I decided to give him another good look at my genitals. I lied when I came out naked and said, “Sorry if this makes you uncomfortable, David, but I’m used to sleeping in the buff.”
There were two, queen-sized beds in our room, separated only a couple of feet by the nightstand between them, and I slowly walked between the beds and sat down facing David, instead of getting in on the other side. I loved the blushed, flustered, and focused expression on his face as he watched my cock and balls hanging over the edge of the bed. He periodically glanced at my cock as I sat there like it was no big deal for me, still facing him, as I talked for about ten minutes about our plans for Tuesday and gave him insights into the customers we’d be meeting with.
When I finally got into bed, I looked away from him and turned in such a way that I spread my legs giving him a full view of my ass, crotch area, and cock and balls swinging between my legs from the rear, and I could almost feel his stare. I turned off the light after getting under the covers, and during the few minutes it took me to drift off to sleep, I was almost certain that I heard the faint rustling of his sheets, like maybe he was stroking his cock.
Becoming Closer on Tuesday
We had a full day of driving and five customer visits on Tuesday, and I kept our conversations strictly to business. We stopped for the night in a town that I was familiar with, and after checking into our hotel, I took David to dinner at a country and western bar with a great barbeque, that I had frequented in the past, and it was close enough that we walked there.
I thought my attempts to get David interested in my cock the previous week at the gym, and on Monday night in our hotel room had been successful. It would have been reasonable to expect someone to call me out on sitting around naked like that if they were offended. I had even been able to get a little insight into his relationship with Erin before they were married. The bar I took him to on Tuesday night is one where I had luck in the past picking up married women to fuck.
It was my plan to reveal a little about me being horny and fucking married women when I travel, to get him thinking about the reality of married women fucking other, well-hung men. I hoped that if he were the least bit inclined to want to see Erin with other men, even subconsciously, that could get him thinking about the possibilities, as well as wondering how else I might satisfy my horniness.
I was planning on us getting inebriated, and if he showed interest in the conversation about adulterous wives, then I hoped to resume where we left off on Monday night in our conversation about Erin, and whether she was loyal to him after he moved to Charleston. It would be helpful if I could get him to conflate my experiences with married women in bars, to how Erin might have been behaving in his absence.
We sat in a booth in a relatively quiet corner of the bar, but still within view of the bar area and dance floor and were starting our third beers before ordering dinner. We first talked a little about our day at work, and then I started pointing out the hot women on the dance floor and at the bar, being careful to select those that looked a little like Erin in some respects. I especially praised the women with big breasts like Erin’s, saying how much I liked women with big breasts.
After dinner, we were starting on our fourth beers and were both pleasantly inebriated. I said, “I’m probably sharing more than I should, David, but I really get horny traveling like this, and I’ve had good luck finding women to fuck in this and other bars. I like the married women who are on the prowl for cock the most. That sure beats taking care of business by hand back in my room.”
David looked stunned that I would come out with something like that, but I was glad when he quickly regained his composure, and said, “Uh, yes, wow, Jackson, that really is probably more than I needed to know. But, uh, why the focus on married women, when there are probably a lot of single ladies around in these places? And aren’t you worried about their husbands being around and trying to kick your ass?”
It was a good sign that he didn’t change the subject, and I answered, “Married women on the hunt for cock aren’t as likely to play games as single ladies, and they aren’t looking for anything from me besides a little companionship and a good fuck. They also have the experience to know what they want and how to please a man. I even learned that many of them are in the cuckold lifestyle, and their husbands not only know they are out with other men but even encourage it.”
He really was naïve and said, “I’ve heard the term ‘cuckold’ before, but I guess I never knew much about it. Are you saying that those husbands urge their wives to fuck other men, and they’re okay with it?”
I replied, “Well, I have done some reading about it, and it goes much further than that. Many of the men in those cuckold relationships have smaller dicks, and they get off on watching well-hung men fuck their wives, cleaning their pussies with their mouths, and even sucking the men’s cocks. There are all kinds of studies that try to explain why men would be into that, but those are powerful emotions, and the idea of sharing their wives is immensely arousing to them.”
David was leaning forward in his chair, listening to every word, and asked, “This might be a silly question, but does Margaret know about your, uh, your activities on these trips, and with her being such a pretty lady, why would you feel the need to do it?”
I responded, “You’ll find out women can lose interest in sex later in life, and Margaret hasn’t been taking care of my needs for a few years now. And fuck no, she doesn’t know about my cheating, and will hopefully never know. You’re the only person I’ve ever told about it.”
Then he asked, “How does something like that even get started in a marriage?”
I wanted to respond in a way to indirectly get him thinking about his own situation, and said, “I think it’s hard to define. Some men who are alpha males in most aspects of their lives might have a submissive trait when it comes to their wives, and it could start out with them becoming aroused when other men hit on their wives. That could stem from the husband feeling inadequate if he has a small dick, and when he sees other, well-hung men, he thinks about how much his wife would enjoy fucking them. I also read that some men are bisexual, to begin with, and watching and participating with their wives and other men gives them cover for their cock sucking urges.”
He was still listening intently after a brief pause, and I continued, “But the wives can start something like that too. If she was promiscuous before getting married, she might have a wandering eye, especially if her husband isn’t that well-hung. It could happen kind of naturally, I guess, when he notices her being attracted to other men, and then either of them could bring it up to discuss. I’m not an expert on this shit, I just know that I love that wet, married pussy.”
David thought for a few seconds and asked, “How do you manage to find these horny married ladies that are on the prowl.”
I answered, “For me, it’s just a matter of being friendly to married ladies, usually those with the biggest breasts, and it’s easy to tell because most of them wear their wedding rings. I buy them a drink or two, and if I can get them to dance with me, I usually end up fucking them. I hold them close on slow dances and let them feel my cock lump pressed into their bellies, and that sets the mood.”
He asked, “Well, why aren’t you pursuing any of the ladies tonight? You said you get horny when you travel.”
It was good that he was still talking with me about it, and I replied in a way to let him know I had a sense of kinship with him, saying, “Oh no, David, I’m on this trip with you and wouldn’t want to leave you out of anything or alone. There’s more than one way to satisfy my horniness. Besides, I’m enjoying talking with you about it.”
We sat quietly listening to the music for a few minutes, until I said, “I’m still interested in finishing the conversation we started last night. I think you said you didn’t want to push Erin to take a vow not to date others, because you were sure she’d party with other boys anyway, and you didn’t want to make her feel like she was cheating. Come on, David, I shared some intimate details with you. Tell me what was causing more than the normal stress of being apart.”
David took another sip of beer while he was thinking for a few seconds and then said, “I think part of the problem was that I found out after I started dating Erin that I knew three of the boys she had been dating before I even met her. I played in the intramural soccer league with them in college and had no idea those boys were dating Erin.”
“I had seen them dozens of times in the locker room and showers after our matches, so I knew that they are well-hung. This might sound strange, but that bothered me because I couldn’t help staring at them and thinking that their, uh, their genitals were attractive. Then when I started dating Erin and found out that she had been dating them, I couldn’t help feeling self-conscious, since as you’ve seen, I’m not well-hung. I found myself trying to envision what it was like when they were in bed together.”
“I even told Erin that I had seen them in the showers and tried to get her to tell me what it was like for her to fuck them. She diplomatically told me that I really shouldn’t delve into that and upset myself and that I satisfied her in bed, especially since I enjoy eating her out before and after we fuck. But shit, that’s all I could I think about from then on, and after I moved to Charleston, I just knew she was fucking those boys, and probably several others.”
He was being very forthcoming, and I asked, “Did you ever have any evidence that she was fucking them?”
David answered, “I drove over unannounced a few times to surprise her, and it’s not like I caught her in bed with anyone, but I did taste cum in her when I ate her out. So, she must have been with one of them only a little while earlier. I didn’t want to get into arguments and spoil my visits, so I didn’t bring it up to her.”
I asked, “Wow, David, what was that like when you sensed you were eating other boys’ cum? Did you stop, or continue?”
He replied, “I’m sure this will sound gross to you, but it tasted like my own, and I had eaten plenty from her, so I kept sucking just for the joy of tasting her pussy.”
That was my chance to relate his experiences to my earlier conversation, and I said, “No, I don’t think it’s gross if someone is inclined that way, and it’s probably no big deal. In fact, the married women I’ve fucked told me that their husbands love to eat them out when they get home, and even better if they can watch her being fucked and then eat her out when it’s fresh, and even suck her lover’s cock.”
Then I said, “I’m curious about something you said earlier, about finding those boys’ genitals attractive. Did you have any experiences with boys when you were younger that might have sensitized you to looking at them?”
He answered, “This is embarrassing to admit, Jackson, and I can hardly believe I’m telling you, but a couple of my friends and I experimented in our senior year of high school, or, it’s more like I was doing the experimenting. They were well-hung too and caught me staring at them in the showers. One thing led to another, and one night when we were drunk and our dates had left us with blue balls, they dared me to, uh, you know, uh, to suck them off. That was in the middle of our senior year, so I sucked them many times over the next few months. I guess that’s why I was so impressed with the boys in college.”
I asked, “What’s the thing that bothered you the most about thinking of Erin with other boys?”
David replied, “I know this will sound sick, although apparently not to those cuckold husbands, I couldn’t stop fantasizing about seeing her with those boys, and I hoped that I could catch her with them.”
He had given me the perfect opening to say, “I don’t mean any offense by this, David, but the way you were thinking isn’t any different than the feelings those cuckold husbands have. And if you’re still feeling the same way, especially with your bisexual experiences in high school, have you ever considered encouraging that to happen? Has Erin ever given you any reason to believe that she would be willing to help you live out your fantasy?”
David answered, “I’m sure you’ve noticed that Erin likes to dress revealingly, and I even encourage her to wear those tight leggings and yoga pants, and the tight or lowcut tops. We sometimes tease each other after events where so many of the men almost trip over themselves from gawking at her. Knowing how sexually active Erin had been before we were married, and even as I found out when we were dating and apart, I have little doubt that she would fuck other men if I encouraged it.”
I wanted to see how he would react to me making some vulgar comments, and I said, “It’s nice that a man like me can have hope of getting into her pants someday. Her melon-sized breasts are fantastic, especially now that she’s lactating, and that bulging camel toe and fine ass of hers makes me hungry. Now we just need for you to encourage her.”
It was amazing that he didn’t give me shit about those comments, and I pressed further, asking, “You saw me naked in the showers last week and in our room last night, David, and I’m wondering how you think I compare to those boys you played soccer with and your friends from high school?”
He looked down at the table and blushed, as he replied, “This is kind of embarrassing to admit, but your, uh, your genitals are bigger and more attractive than any of those boys, and I can’t help staring at them. I’ve even wondered how big that thing gets on hard.”
Things were falling nicely into place, and I revealed a little of my subterfuge, saying, “Thank you, David, that’s a nice compliment. I was hoping you’d be attracted to my cock.”
David looked puzzled, and asked, “Wait, Jackson, why were you hoping I’d be attracted to your cock?”
There had been enough said that I thought it was safe to reveal everything, and I answered, “Please don’t take offense, David, but from the first time I met Erin, and especially after Margaret started losing interest in sex, I’ve been thinking about the possibilities of sucking and fucking your wife. And then when I learned about the cuckold lifestyle from those women I’ve been fucking, I decided to test the waters with you, to see if you had any of those tendencies, even if subconsciously.”
I let that sink in for a few seconds, and continued, “Now that we’ve talked this through and bared our souls to each other, I’m feeling pretty good that we could get into a mutually beneficial arrangement, with Erin’s acceptance, of course, and I was especially happy to hear about your experiences with those boys in high school.”
He was a little stunned at first, and then asked, “Why are my high school experiences that relevant?”
I responded, “I mentioned earlier that there’s more than one way to satisfy my horniness, and if you’ll do for me what you did for your friends, that will sure help me out and probably be enjoyable for you too.”
David asked, “My goodness, Jackson, are you inviting me to, uh, to suck your cock? Do you think that would be such a good idea with us working together?”
I replied, “I agree, that’s it’s not usually a good idea to mix business with this kind of pleasure, but I’m in a position to help you advance in your career, and it would be helpful for both you and Erin to be receptive to me. Let’s get back to our room and you can experiment with me like you did with your friends, and then we can talk about me getting my cock into your wife.”
He was likely thinking that he would like to try sucking my cock, but was still embarrassed at admitting it, and he said, “Well, it’s late and we should be getting back to our room anyway, but I don’t know if I can do what you want after so many years.”
We got back to our room and got ready for bed again like the previous night. He watched me walking from the bathroom to my bed, and when I sat naked facing him, I said, “I’m not going to pressure you to do anything, David, and we’ll work together the same as before no matter what you decide. Maybe it’ll be easier if I just lie back on the bed, close my eyes, and you can decide whether you want to look, touch, explore, or do nothing.”
I was near the side of the bed mostly on my back, with my right leg, which was closest to him, pulled up a little and bent at the knee, which had me leaning slightly towards him. My soft cock was laying across my thigh, and my balls were hanging down on the bed, so he had a good view of my genitals.
David didn’t do anything for what seemed like a minute, and then I heard his bed creak as he moved to sit facing me, for a closer look. Then his bed creaked again, as he moved to his knees next to me. He gripped my cock, weighing it in his hand, and I heard a barely audible, “Oh my,” as he stroked it and fondled my balls with the other hand. I didn’t peek until I felt his breath on my cock, just before he took it into his mouth, and began sucking.
I moaned to encourage him and watched as he sucked my meat, moving up and down, and taking most of my shaft into his mouth and throat. I reached down and pulled his shoulders as I moved over, letting him know to lie on the bed, and I was soon partially rolled over on him, fucking his mouth, as he gripped my ass to hold on.
He sucked my cock for about five minutes and didn’t resist or try to pull away as I fucked his face and my cock throbbed and pulsed, filling his mouth with cum. He swallowed and kept sucking for more, before moving down to suck my balls. He really got into it, hugging my ass, and burying his face in my balls and crotch, but finally pulled away and sat on the side of my bed.
David sat next to me, staring at my spent cock, and said, “This is embarrassing, Jackson, but your cock is so huge, over nine inches long I’d guess, and it’s bigger than the boys’ cocks from college. I loved sucking it and eating your cum, and I know that Erin would enjoy it. But how could we ever make that happen?”
I answered, “I think you can start by telling Erin that you saw my cock on our trip and that it looks bigger than the boys you played soccer with that you’d tried to ask her about in college. Let her know that it excited you seeing me naked and remembering seeing those boys in the showers, knowing that she had fucked them. See how she reacts to that, hopefully wanting to hear more. But then comes the tricky part.”
“You’re going to need to muster the courage to share your fantasies of watching her fuck those boys and let her know that you’d be open to watching her with me. I know that will be tough and embarrassing to talk about, but you can take it slow, exposing your fantasies a little at a time, so you can easily back off if she isn’t receptive to it. You can even tell her that I’ve been making flattering comments about her, and you have no doubt that I’d want to fuck her.”
He asked, “Even if I can do that, and she’s receptive to it, which is doubtful, then how and where could we get together?”
I answered, “The CEO lets executives use his beach house from time to time, and Margaret and I have been there before. Maybe I’ll see if I can borrow his beach house the weekend after next, when my wife will be out of town visiting her parents. You can tell Erin that you’ll be joining me and my wife at the beach for the weekend. You could bring the baby too, but it would be better if just you two came and she could pump and store some milk for the babysitter to feed the baby.”
“When you two arrive at the beach, I’ll say that Margaret was unexpectedly called away to visit her parents. Erin will have to realize the possibilities after you tell her about my cock, but I’ll be polite, like I’m unaware of the possibility of fucking her. We can let the weekend unfold naturally, with plenty of drinking, and I’ll find a way to ‘accidently’ expose myself to her, to see if that helps get things started.”
David said, “You’ve really thought this through, and it seems to be moving so quickly. I’ll try to start talking with Erin about this as soon as we get back, but I can’t promise she’ll be receptive to hearing about your cock or the boys from college, since it’s been a while since she quit that lifestyle.”
I laughed and said, “I know you’ll do your best, and even if you’re not successful, I’m betting that you’ll still want to take care of me with your mouth.”
After relaxing and talking for a while, David sucked me off a second time that night, and again in the morning before breakfast, before another long day on the road and visiting customers. We kept our conversations in the car mostly on business, but when we stopped for the night, we talked more about me fucking his wife. He not only sucked me off twice more on Wednesday night, but he also spent time casually sucking my cock and balls before and between my ejaculations.
By the time we got back to the office at mid-day on Thursday, David was happy to be my cock sucker, and he was getting more into it each time he sucked me. He loved sucking my balls and perineum too, and I knew it was just a matter of time before I convinced him to suck my ass.
I gave David his space and didn’t question him about his conversation with Erin on Friday, but Monday I took him to lunch, as part of my bullshit ‘mentoring’ program, to find out how it was going with them.
After talking business for a few minutes, to justify it as a business lunch, David said, “I was surprised that Erin was so interested when I described your cock and balls, but she also wanted to know how I got such a good look at you. I told her about the gym, and then us sharing a hotel room, and she thought it was kind of flaky for the company to make us share a room that way.”
“Then it was my turn to surprise her when I brought up the boys from college, comparing their cocks to yours, and then admitting that I had fantasies of her fucking those boys back then. She’s very perceptive, and before I could even bring up sharing her with you, she asked, ‘So, David, why are you bringing all of this up? Are you hoping I’ll fuck Jackson now?’”
“I admitted I had been fantasizing about it, and she said, ‘I don’t know about that, honey. I tried so hard back then to spare your feelings and shield you from the specifics of my being with those other boys, and now you’re excited about Jackson’s big cock, and bringing it all up again. You need to think long and hard about trying to get something like this started, and I’m not agreeing to any of it, at least not yet.’”
That sounded positive to me, and I said, “That’s a lot better outcome than I expected. Did you tell her about being invited to the beach house this weekend, and does she have any idea that we’ve discussed this?”
David replied, “She’s excited about spending the weekend at the beach, and even mentioned that having Margaret there would keep my perverted expectations in check. But I also let her know that I had discussed my fantasies with you.”
Getting to Know Erin Better at the Beach
The rest of the week passed slowly, waiting for Friday when we’d take the short drive to the beach. We took off a little early from work, and I arrived at the beach house at around 6:00 pm. It was 6:30 pm when David and Erin arrived, and I had already opened everything and made a pitcher of margaritas.
I welcomed them inside, and when I saw Erin glancing around for Margaret, I said, “Margaret had to go visit her parents in Atlanta at the last minute, to help with an emergency of some sort, so I’ll be the best host I can.”
Erin looked a little apprehensive, and then recovered, saying, “Oh, that’s too bad. I was looking forward to having another lady here to talk with. But just let me know if I can fill in and help with anything.”
The beach house has three bedrooms, two bathrooms, and a family room that opens to a large, veranda porch across the front looking out over the beach and ocean. There’s also an outdoor shower for rinsing off when coming up from the beach. All the windows have a solar-reflective film to help keep cut down on glare and to keep the house cooler. The master bedroom suite and one other bedroom are in the back of the house, and the third bedroom is in the front next to the family room, also opening onto the veranda.
I took the master bedroom and let David and Erin use the bedroom in front with an ocean view. After we got settled, and poured our first drinks, we took a stroll on the beach. Erin looked fantastic in a pair of tight yoga shorts and a tight t-shirt with our company logo, and it didn’t look like she was wearing panties or a bra.
We walked and talked for about an hour on the beach, and it was still light out when we came back for dinner since the sun sets at about 9:00 pm that time of year. I cooked steaks on the gas grill while Erin helped prepare baked potatoes and a salad, and we sat on the veranda eating dinner in the twilight.
They liked my margaritas, and I made two more pitchers of them as we talked and drank on the veranda until long past dark. I was more complimentary of Erin as we all became inebriated and I found that she wasn’t uncomfortable, but flattered, when I’d make comments, like, “My goodness, Erin, you’re just about the prettiest lady I’ve ever met. David is sure a lucky man to have a woman like you. You can probably feel the eyes on you at our company events.”
She teased me saying, “Thanks, Jackson, you’re a good-looking man too, especially for being old enough to be my father, and I’m feeling your eyes on me tonight too.”
I said, “Guilty as charged, but I appreciate beauty when I see it, and it’s hard not to stare at you.”
We finally got to bed at around 11:00 pm, after we all helped clean up the dinner dishes, and I said, “We’ve got a big day tomorrow in the sun on the beach and surf, so we’d probably better get some rest.”
With all the margaritas we had to drink, we slept in until about 9:30 am, when I prepared a nice brunch of omelets, bacon, hash browns, and orange juice. Then we took a cooler of beer and folding chairs with us down to the beach, where I set up a big umbrella that gave us some protection from the sun.
Erin showed that she wasn’t shy, wearing a skimpy, beige bikini, covering all the important parts, with the bottoms prominently displaying her fat-lipped camel toe, and the top covering little more than her areolas, leaving her big, lactating, 34F breasts spilling out all over. I couldn’t help saying, “Oh my, Erin, you’re breathtaking in that bikini, and you’ll be exciting a lot of men walking by today.”
We drank beer and walked on the beach for a while, before going into the surf, where I learned that her beige bikini becomes almost transparent when wet. I saw her thick nipples and even the little bumps on her tan, three-inch-wide areolas, as well as the hair on the bulging folds of her camel toe.
David smiled at me when Erin sensed me staring at her and she said, “David likes for me to wear this bikini, Jackson. I hope I’m not embarrassing you.”
I smiled and said, “You’re making this man, who as you said is old enough to be your father, very happy. The only way to improve on it would be to keep it wet the rest of the day or take it off.”
David and I took a short walk together after we went back to the umbrella and dried off, and I said, “Oh fuck, David, Erin’s driving me crazy with that body of hers, and she seems very comfortable with me. It might be time to show her what I’ve got too. When we go up for lunch later, you and Erin can go up first and rinse off in the outdoor shower and point out that you can’t see inside through the reflective material. I’ll hang back to gather the umbrella and other things. Then you two can go to your bedroom, and I’ll come up, rinse off, and put on a little show for her.”
We stayed on the beach for another hour, until I said, “It’s time for lunch, so you two should take the cooler and go up, rinse off the salt and sand in the outside shower, and then keep your swimsuits on. I’ll bring the rest and we can eat on the veranda, before going back to the beach after lunch.”
I waited a few minutes to give them time to get to their bedroom, and then went up with all our stuff. I turned on the shower, which is easy to see from their room, and first rinsed off my head and torso. Then I pushed my swimsuit to mid-thigh and moved around in the spray of water, facing their window, while I gripped and lifted my cock and balls, as if I were getting rid of a lot of sand. After that I stood in the shower, swaying side-to-side, so she could see my cock and balls swinging between my legs. I pulled up my swimsuit and dried off after that and went inside.
Erin was already in the kitchen getting the cold cuts, condiments, bread, and other supplies out for lunch, and I went in to help her make the sandwiches, and put them, along with chips, on our paper plates. She was quieter around me than she had been before, I hoped thinking about my big cock, and I acted like I was unaware of her seeing me.
We enjoyed the rest of the afternoon on the beach and came back inside to clean up at about 4:30 pm. After we were all showered, dressed, and drinking a fresh batch of margaritas, I said, “There’s a country and western bar near here that has delicious barbeque. I thought we could enjoy a few more drinks here, and then go there for dinner. They have a live band that starts at about 8:30 pm, and it should be a lot of fun.”
Dancing and then Back to the Beach House to Fuck
I didn’t warn them that we’d be going out, but Erin was prepared, wearing a pair of skintight, low-rise, hip-hugger jeans, and a tight, midriff-baring, Garth Brooks t-shirt, with no bra. She got a lot of attention from the other patrons as we ate dinner and had several more drinks, but not as much as when the band started, and she alternated dancing with David and me.
We were inebriated by around 9:30 pm, when she was mostly dancing with me, and I started holding her closer and sometimes ‘accidentally' rubbing her ass and the sides of her breasts. She was receptive to me and held me tightly, and the others had to wonder why an older man like me was dancing with such a sexy and beautiful woman, when the man who was obviously her husband was watching us.
A little later I felt comfortable enough to whisper in her ear, saying, “Erin, you look amazing in everything you wear. You look good enough to eat, especially in your bikini today, which leaves little to the imagination, and I’d love to feed from your beautiful, lactating breasts.”
She surprised me, as she squeezed my ass, pulling me more tightly against her, and said, “I haven’t been able to pump my breasts for a few hours, and they’re getting a little painful, so you’ll be able to drink your fill. But you didn’t leave anything to my imagination either, you bad boy. You had to know that we were in the bedroom when you took your outside shower today and let it all hang out for me to admire. Was that your intention, Jackson, to make me hungry for you too?”
I laughed and snuggled against her neck, saying, “I didn’t want you to think I was doing it on purpose; but yes, I was hoping you’d notice and maybe want a taste.”
She pushed her hand between us to rub my hard cock, and asked, “How do you think David would feel about having this big fucking thing pushed inside me?”
I squeezed her breast and responded, “David and I had a lot of time to talk on our trip the prior week, and let’s just say I got the feeling that he was impressed with my package and there’s a chance he wouldn’t mind seeing us together. I think we should go back to the beach house so I can relieve the pressure in these milk jugs of yours and see how things develop.”
We kissed for the first time before going back to the beach house, and while David and Erin went to their bedroom to change into shorts and t-shirts to be more comfortable, I made a pitcher of margaritas and then went to change into the same thing. When I came back out, they were sitting on the couch sipping the drinks I prepared. I filled my glass and sat on her left side, while David was on her right.
I waited for a few seconds to see if Erin would make the first move, and she finally said, “My breasts are feeling a lot of pressure now, Jackson, and David’s not into feeding from them. Would you help a lady out, so I don’t have to use the breast pump?”
David didn’t object, and when she lifted her t-shirt up and over her breasts and off over her head, her melon breasts swung heavily into place. Her three-inch-wide areolas and thumb-sized nipples looked so tasty, and I lay across her lap to her right breast and sucked the nipple and areola into my mouth while weighing and fondling and both breasts with my hands.
Her sweet mother’s milk began to flow, and I not only loved the taste and texture of her milk, but also the reality that I was feeding from her. She leaned down and kissed my forehead, as she reached out with her left hand to rub my crotch, before saying, “See, David, some men love feeding from lactating women. It’s so arousing having a man do this for me, and from what I’m feeling in Jackson’s pants, it’s arousing for him too.”
Erin waited a few minutes and pushed her hand under my shorts and rubbed my bare cock, which was already oozing precum, and said, “You were right, honey, his cock is massive, even bigger than those boys on your soccer team. Let’s go to Jackson’s bedroom with the king-size bed, where we’ll be more comfortable.”
I undressed as we walked to my bedroom, as Erin took off her shorts, and I loved the sight of her being totally naked, with her pendulous breasts swaying and jiggling, and her thick-lipped pussy, covered with neatly trimmed, blonde hair. David pushed down his shorts and sat by the side of the bed stroking his little dick, as Erin laid back on the bed and held out her arms for me to turn around next to her in a side-by-side sixty-nine.
She struggled to take my thick cock into her mouth, as I licked and sucked her wet vulva, and we sucked each other for a few minutes, until I was getting too close to cumming. I turned around and mounted Erin, and sucked her left breast to relieve the pressure, as I pressed my cock into her wet, receptive, married pussy.
David watched and stroked his dick as I got into a rhythm fucking his wife, as she thrashed her head and moaned, “Oh fuck, I haven’t felt a cock this big in so long, and I’ve already had one orgasm. Fuck me, Jackson, fuck me and breed my married pussy with your huge fucking cock.”
I surprisingly lasted in her sweet pussy for what seemed like five minutes, with the slapping of our bodies together and my balls slapping against her pussy, inner thighs, and ass, and I felt like I was melting into her luscious body. Then my cock erupted inside her, and I moaned out, “I’m cumming, Erin, I’m cumming deep inside you. I love breeding other men’s wives, and you seem to be hornier than I am for a good hard fuck.
She held me in place with her legs as I continued stroking her with my deflating cock, and the sounds of us squishing together and the aroma of my cum leaking out of her filled the room. I finally rolled off to the side, and David didn’t hesitate to dive between her legs and lick and suck the cum off her vulva and inner thighs, before sucking her to eat the cum that was freely oozing out of her pussy.
Erin looked down at him munching on her just-fucked pussy, and I think surprised David and me, saying, “Oh shit, honey, that is so fucking hot. I’m sorry now that you didn’t catch me fucking those other boys back in college, so you could’ve slurped their cum from me too. And now, I’d love to see you clean Jackson’s big cock for me. If it’s no problem eating his cum, it shouldn’t be a problem sucking his cock.”
David had never mentioned that Erin knew about him sucking cocks in high school, and she was so aroused that she encouraged him to suck me. David didn’t disappoint her and moved over to suck my cock and balls clean, as I alternated kissing her and sucking her lactating breasts.
We stayed in bed together that night, with Erin and me alternating between hugging, kissing, and me sucking her breasts as it came time for her to breastfeed. We drifted off to sleep for a while, and woke up to fuck again, before falling asleep until sunup, when I drained her tits again before we fucked.
I prepared breakfast for us before we went down to the beach, and the other beachgoers were staring and pointing when they saw Erin and me kissing and fondling each other, as David, who was obviously her husband, looked on rubbing his dick. Then we went back to the beach house for lunch, where I suckled and fucked her again, and then we cleaned up and packed up to go home.
It's been almost a year now since that first weekend at the beach, and I have since been a part of a cuckold lifestyle with Erin and David. I go to their home two nights a week, when my wife thinks I’m at the gym, and I even stay with her days at a time, when David is traveling, and my wife thinks I’m traveling too. I was happy to find the perfect married woman for a cuckold relationship close to home that I could develop into a long-term sexual relationship so we wouldn’t have to sneak around, and I intend to make it last as long as possible.
