My name is Jacob, and I always considered myself fortunate to grow up in Savannah in what I thought was a normal, stable home, with loving parents. My father, Randall, is a senior executive with a large paper company, and he has a good income that has allowed my mother, Jennifer, to stay home to raise my two older sisters and me. My sisters were away at college when the main events in this story began, as I had just turned sixteen, in the summer before my junior year of high school.
Dad entertained a lot due to his position in his company, and I remember all the great parties they had in our home when I was growing up, with guests mingling in our large family room, which opens up to the pool and patio area. I liked seeing everyone dressed up for the parties, and even as a boy in elementary and middle school, I had a sense of how pretty my mother was, when compared to the other ladies at the parties.
This might sound a little strange, but I remember how Dad was usually busy talking business with men at the parties, and although Mom socialized with some of the wives, she was usually drinking heavily, dancing with other men, and acting her normal, flirty self. I couldn’t understand why Dad wasn’t jealous of seeing her with those other men, but it all looked like innocent fun to me.
I’m nineteen and away at college now, but his story describes the amazing, life-changing experiences that began for me over three years ago, right after I turned sixteen.
Seeing Mom in a New Light
After I got my car that summer and began dating girls, I was starting to see Mom in a new light. I was fortunate to get to second and third base with my girlfriend and realized how much better-built Mom is than any of the girls in my class.
Mom’s five feet and six inches tall, weighs about one hundred and thirty pounds, and has brown hair and eyes. She has a light olive skin tone and looks a lot like the sultry actress, Rhona Mitra, who you might remember from the television shows, ‘Boston Legal’ and ‘The Last Ship’. Mom’s breasts appear to be even bigger 34DDs, though, and her ass is perfectly shaped and firm.
Seeing Mom around the pool that summer, I feel a little ashamed and guilty to admit that I started using her as my at-least-once-daily jacking material, and I was so happy when she bought her new bikini, with thong bottoms and a top that just barely covered her areolas and nipples. I couldn’t figure out why she would be wearing such a skimpy swimsuit in front of me, and even my best friend, David, but we both enjoyed it. David was also sixteen then, and he teased me about him using Mom for jacking material too.
David Makes a Discovery
I got my laptop computer that summer, and although I played a few games on it, it was primarily for my schoolwork, and I was too focused on enjoying the freedom of having a car, and hadn’t used my computer much. David got a laptop computer too that summer, and as you might expect for a horny teen boy with free time, he started going to porn sites in addition to playing games.
It was a Saturday morning in the middle of summer when David came over to visit me, and he was excited about something he wanted to show me. Mom was out by the pool, and I had been drooling over her before David arrived, and then we went to my bedroom. We sat on my bed together as I booted up my laptop, and David took control.
David entered a web address that he was familiar with, and it’s a site devoted to cuckold couples hooking up with men in the Savannah area. I didn’t even know what a cuckold was, until he explained, “The simple definition is a man with an unfaithful wife, but the stuff on here is about married couples with submissive husbands who help their wives date other men and even participate with her and her lovers. I know it sounds fucked up, but some men are into that shit.”
He started scrolling through the various sections of the site, and said, “It’s amazing to me that so many of these husbands, wives, and even couples post naked photos, as advertisements for themselves, and even explicit photos and videos of them with other men. They also have groups and forums where they can share ideas and experiences online, and email to chat privately to arrange hookups.”
I could hardly believe what I was seeing. I had never seen any other boys or men with hard cocks, and I had never seen such explicit pictures of naked women either. They spread their legs and even had photos and videos of them fucking the men.
We perused the site for a few minutes, looking at several profiles, before David said, “The reason I wanted to come over was to show you something special I discovered, but only if you promise not to get mad at me for being the messenger.”
I promised him, and he clicked on a profile that included a compound name, including ‘Jen’ and “MILF’, that I don’t want to fully identify. He started scrolling through some of the photos of the wife, with the faces blurred in all of them. The beautiful body on her looked somewhat familiar, with her smooth and tight, light olive skin tone, her breasts that were busting out of a bikini top, and a thong that displayed her bulging camel toe and a perfect ass, in the various shots.
He stopped on one photo of the lady standing by her pool, and David said, “Look at this picture very closely, and tell me what you see.”
I stared at the picture for a couple of minutes, before I recognized the patterns in the stamped concrete and tile trim around the pool, as well as the chaise lounge in the background. Then I focused more on the lady and realized that her body looked just like Mom’s that I was always drooling over.
David was smiling from ear to ear, when I said, “Holy shit, David, that looks like Mom. And if she’s on this site, then that must mean Mom is cuckolding Dad. This is unfucking believable!”
Mom had asked David to call her Jennifer, so she wouldn’t feel so old, and he said, “I’m certain it’s Jennifer, and you should see the pictures and videos in some of the other folders.”
We went through most of the folders, and found pictures of Mom totally nude, with her legs spread and playing with her big breasts, as well as scenes of her fucking one or more men at the same time. I recognized some of the men from the parties at our home over the years. Mom’s face was always blurred, but I could easily identify some of the big-cocked men. And then David pointed out something that almost made me throw up.
Mom was on her back on the bed, with one man, who I recognized as Dad’s boss fucking her, while another man was on his knees by her head, as she sucked his cock. And then there was Dad, on his knees sucking the cock of one of our neighbors, who was likely waiting for his turn in Mom’s pussy.
David tried to gauge how upset I was before he said, “I’m sorry to be the one to show you this, Jacob, but it looks like your parents are living a pretty active cuckold lifestyle. No offense, but I’d sure like to get in on this. Maybe I should send Jen an email on the site and see if she wants some big, hard, teen cock, and maybe your dad would like some too.”
I was getting upset that he was being so caviler about me finding out that my mother was a fucking slut, and Dad was a wimpy ass cock sucker, and I said, “Fuck you, David, that’s my mother and father you’re talking about.”
As upset as I was, I still realized that seeing Mom like that was turning me on, and it was hard to be mad at my friend for being aroused too. I asked, “Fuck, David, what do I do now that I know this. I can’t just unsee something like this and forget about it.”
Then he got even more brazen, and said, “I don’t know about you, but I’m sure going to be watching Jennifer more closely when I’m over here swimming with you guys, and maybe look for an opportunity to cop a feel, or maybe even try to get her interested in me. And shit, man, you live with her, and should have a lot of opportunities to approach her.”
I said, “Fuck, David, she’s my mother. I’ll admit that I do use her for whacking material, but it would be a whole other thing to be intimate with her, wouldn’t it?”
He teased me, saying, “It sounds to me like you’re trying to find a way to justify it, and I know I damn sure would if she were my mother. Let me know and share the wealth if you find a way to get into that shit.”
Taking a Bold and Scary Step
After David left for home, I again pulled up the site on my laptop, and fully explored Mom’s profile. I read the biographical section, and part of it read, “Horny, mature MILF with voluptuous body has two kids in college and a son still in high school. The husband knows his place, is supportive, and fully participates to enhance our pleasure.”
Then another part got my full attention, saying, “Please email me to discuss the possibilities of us getting together, and send explicit photos to entice me. Must be of legal age in Georgia, with the age of consent being sixteen here, and you being hung is a definite plus.”
With Mom specifically stating that she would fuck teens as young as sixteen, I had to wonder if she had already fucked teens, and if I might know any of them. But just learning that she was into that, was getting me aroused.
I had planned on going out that night, to cruise the areas where teens hang out, and to see what was happening. Instead, I decided to stay at home to compose an email to Mom, to question her about fucking teenagers, and to find out more about her cuckolding Dad. I wasn’t really planning on trying to meet with her at that point, but it was exciting to think about communicating with her that way, while I was anonymous.
It was easy to join the site, with no payment needed, and I just had to lie about my age. The site requires members to be at least eighteen, but no one would know. I won’t give my real profile name, but for purposes of this story, I used ‘Hung_Teen”, and I referred to Mom as “Jen’.
Mom sometimes spends hours alone in the den on her laptop, and after learning about her porn profile, I realized that she was likely corresponding with horny men, while Dad was out watching television. I saw that she was in her den that night and wanted to send a message when I could get an immediate response.
It took forever to compose my first email, not knowing exactly how to talk with a mature woman about sexual matters, and I finally decided it would be easier to be as honest as possible. I wrote, “Hi Jen. I am an inexperienced, barely sixteen-year-old boy in Savannah, and I just came across your amazing profile. You’re the most beautiful and sexy woman I’ve ever seen, and I was wondering if a boy like me would have a chance being with you? Have you ever been with a boy my age?”
I held my breath, hoping that Mom would respond right away, and I wasn’t disappointed. It only took about ten minutes before I received her response. She wrote, “Hi Hung_Teen, I’m so pleased that you wrote to me and am flattered by your comments. I have been with a boy your age, and sssh, don’t tell anybody, but it was one of my daughter’s boyfriends. He came by to visit my daughter, and she was out with friends. My husband and I were happy to help that horny boy out. Please tell me a little more about yourself and send some honest photos that justify your profile name.”
When responding, I wanted to get Mom talking more about her family and specifically to get her to talk about me, her sixteen-year-old son, so I could ask her more questions about her perception of and attraction to me as her son. I also took several cock and ball pics using my cell phone and transferred them to my laptop, being careful not to show any revealing background that might give me away.
My uncircumcised cock is a decent-sized, thick six inches on soft, and over eight inches on hard. I took several photos, some soft and in various stages of hardness, as well as highlighting my lemon-sized, low-hanging balls. It wasn’t hard to get it up for the hard-on pics either, while I was looking at Mom’s pictures on the site.
I attached several of my cock photos and wrote back, saying, “Hi Jen. One of the reasons I contacted you in the first place is because you remind me so much of my mother, and I have to admit to having indecent thoughts about her. And as much as I’d like to be with you someday, I was hoping you might be able to give me some pointers on how I could approach Mom or get her to notice me in a sexual way.”
“How old is your son, and if you don’t mind me asking, have you ever had sex with him? I hope you enjoy the pictures, and I’m looking forward to hearing from you again soon. Thanks, Hung_Teen.”
Mom must have been struggling to find what to say, because it took her twenty, agonizingly long minutes to respond that time, saying, “Oh my, Hung_Teen, your attraction to your mother and question about my son have stirred up some strong emotions. My son is sixteen, like you, and I’ve been having a hard time keeping my composure around him and his friend this summer.”
“I even bought a new, revealing bikini to get them to notice me, and they stare at me all the time when they think I’m not looking. And based on what I can see of their soft cocks and balls swinging around in their wet swimsuits, I think both are probably hung as well as you are.”
“Oh, I love the photos you sent, and your mother would be stupid to turn you down, if you ever find a way to approach her. It’s starting to sound like we might be able to help each other. What do you think is going through my son’s and his friend’s heads when they’re staring at me the way they do?”
I wrote back right away, to be sure I kept her interest, and said, “Hi Jen. If your son and his friend are anything like me, they’re probably rubbing their cocks raw whacking off to visions of you in that bikini. I know that I masturbate at least once a day fantasizing about Mom, and I don’t even feel that guilty about it anymore.”
“I’ve been thinking about how to get closer to her, and one way you might be able to entice your son is to get into some playful roughhousing in the pool, and maybe your top ‘accidentally’ comes off. You could act all embarrassed, but if your son really is looking for an opportunity to show his sexual attraction to you, he might seize the opportunity to make some suggestive comments. You might even want to notice and comment on his hard-on.”
“One other thing might be to walk in on him in the bathroom or make it convenient for him to walk in on you and catch each other fully nude. After the embarrassment, that could lead to some suggestive conversations. What do you think about my suggestions? Oh, and I was curious to find out if your husband sucked that teens cock, the way I see him sucking other men in your profile photos? Hope to talk again soon, Hung_Teen.”
Mom responded fairly quickly that time, saying, “Hi Hung_Teen. Those are some good suggestions, and I might try it tomorrow in the pool, because we usually hang out by the pool on Sundays, although my husband doesn’t always join us. Do you think I should tell my son not to invite his friend tomorrow, or let both see me lose my top?”
“And about my husband, yes, he was involved with my daughter’s boyfriend, and sucked his cock before and after I fucked him. I think he’s sucked the boy a few other times too when I’m not around. He really likes being sexually submissive to men, and I think it turned him on, even more, to demean himself and submit to a teenager. I have to wonder if he would even suck my son’s cock, if he had the opportunity? ”
“I’m so happy that you contacted me, Hung_Teen, because our conversations are getting my pussy wet and nipples hard thinking about the possibility of fucking my son and his friend. I hope this is getting you excited too, and helps you get the balls to let your mother know how attracted you are to her. Love and kisses, Jen”
I quickly responded, “Hi Jen. I love talking with you too, and you have my cock hard and dripping. I’m glad you’re thinking of exposing yourself to the boys tomorrow, and I’ll be thinking of you. I have to go for now, but hopefully you’ll be online again tomorrow night, so you can tell me how it…
