My name is Ryan, and my wife, Karen, and I moved to Charleston at the age of forty-four, after having lived in Atlanta since graduating from college. I have a degree in mechanical engineering and, after a long career working as an engineer, I moved to Charleston to begin my career as a manufacturer’s representative. Karen, with her degree in education and years of experience teaching, got a job in a high school here.
Our son, Jason, graduated from college and moved to Charleston to begin his career two years earlier, and we wanted to be near him and his young family. We bought a more-modest home than we could afford, on a cul-de-sac in a Charleston suburb, since we wanted to be able to save enough to one day buy or build a cottage on the seashore that both of our families could enjoy.
Karen and I had a good sex life, at least for our first twenty-one years of marriage. We fucked four times a week on average, and even though I have a decent-sized, uncircumcised, thick, seven-inch cock and really enjoy fucking, my favorite thing is to suck Karen’s thick-lipped, hairy pussy, both before and after we fuck.
I just can’t seem to get enough of her sweet-tasting pussy juices, and even enjoy the taste and texture of my own cum. I love tasting and swallowing her fluids so much that I tried to talk her into pissing in my mouth. She loves me eating her out but thinks I’m a sick fuck for wanting her to do that, and she would never do it for me.
The sex was good right up until about a year before our move. Maybe it was because of premenopausal issues, but her libido diminished, just as mine was increasing. We still fuck about twice a month, and luckily for me she somewhat reluctantly lets me eat her out almost any time I want to. The reason I’m explaining my situation upfront, is because my constant horniness is at least partially responsible for me becoming attracted to my neighbor MILF and her daughter.
My wife is a beautiful woman, with naturally blonde hair and sparkling blues eyes, and at five feet and six inches tall, and weighing one hundred and thirty pounds, she is fit and very sexy. Her breasts are 34Ds, about the size of a cantaloupe, if I may use a fruit comparison. So, you can imagine how her diminished sexual desires affected me.
A week after we moved into our home, we met our neighbors. I don’t mean to sound snooty or anything, but that’s when we realized that we should have picked a more affluent neighborhood. We eventually learned that the mother, Tara, was thirty-four years old, and had gotten pregnant when she was only sixteen years old. She was living there with her daughters; Savannah, sixteen years old, and Willow, seventeen.
The father, Cash, is an entertainer, living away from his family in Atlanta, while Tara’s boyfriend, Grady, lives intermittently with Tara and the girls. Cash apparently makes enough money to support his family, and Tara helps, as we eventually found out, since she works part-time at a gentlemen’s club as a ‘dancer’.
Tara is very fit, at five feet and six inches tall and weighing one hundred and twenty-five pounds. She’s very pretty, but wears too much makeup, and has long black hair and green eyes. I was especially attracted to her perfect ass and 34DD breasts.
Grady is a tatted-up redneck. He isn’t very friendly and seems to always be uptight when we see and hear him rumble up in his older, souped-up, black Camaro. It was apparent to us and some of the other neighbors that the main reason he stops by is to fuck Tara. We couldn’t help being concerned about those girls living in that unconventional and unwholesome environment.
I had never been attracted to trashy women, and prefer conservative, tasteful women like my wife. Tara is a special case, though, and very appealing to me. Her pretty face, flirty behavior, lovely smile, and cute Southern charm are just the beginning of my attractions to her. Her big breasts are an obvious lure, and her big, firm, shapely ass is amazing. I also like her prominent, thick labia which are plainly visible as a bulging camel toe when she wears tight, stretch pants or Lycra shorts, as she often does.
We tried to get to know Tara, but she’s always been a little standoffish, and I got the feeling that she isn’t very attracted to me. I never played sports, but I do exercise regularly, and at six feet and one inch tall, and weighing one hundred and eighty-five pounds, I think I’m very fit for my age, and not bad looking. The age difference must have been a turnoff for her, and we probably seem old-fashioned compared to her promiscuous lifestyle.
The girls have to fend for themselves much of the time when they aren’t in school, since Tara works a varied schedule, and Grady isn’t around that much unless Tara’s there. That gives the girls a lot of free time at home and is part of the reason I became closer to Savannah, who everyone calls by her nickname, Vanna.
I work from home as a manufacture’s rep, when I’m not traveling, and I have a lot of free time to spend in my nicely finished, unattached office/workshop behind our home, that the previous owners built. In addition to my desk, cushy leather couch, and work area, it has a bathroom and a small kitchenette. I’m out there a lot during the day and sometimes at night. I’ve got my laptop computer and a phone out there, so I can work on personal projects and hobbies while keeping up with my clients.
Willow, being a senior in high school and involved with friends, never seems to be outside much or spending time with Vanna. There aren’t many other kids in our cul-de-sac or adjacent streets to play with either, so Savannah often comes over to my office when she gets home from her junior classes and on weekends.
Vanna and I get along very well, and I noticed that she is a very mature and precocious for her age. She can hold her own in conversations with me, even though she sometimes shows the silliness that you would expect in a teen girl. We talk about just about everything, and I got the feeling that she genuinely likes me.
I was becoming attracted to her as an interesting girl, but also in a slightly sexual way. I had never had any attraction to teenagers as an adult, other than in a fatherly way, and I struggled with myself at having such a fascination with a girl only sixteen years old.
Whenever we’re together, I can’t help admiring her tight, shapely body, with the curves of an older girl. I’m also drawn to her pretty face, with those big, wide-set eyes, toothy smile, and big lips, that gives her a kind of pixie appearance. And just like her mother, her looks remind me a lot of the actress, Liv Tyler.
The thought that she was a teenager was concerning to me, although the age of consent is sixteen years old in South Carolina and I’m not in a position of trust with her. I know that society frowns upon contact by men my age with teens her age, if acted on, and I personally find it abhorrent.
Karen sometimes mentioned to me what a cute figure Vanna has for a teen girl, and I acknowledge her comments while still trying to act disinterested. Our son wasn’t nearly as mature acting at her age, so the contrast in their levels of maturity was striking.
Vanna had been coming over almost every day for a couple of months since we moved in. We were becoming close as friends, and she started calling me by my first name without me even giving her permission to do so.
I sometimes forgot her age, looking at her pretty face, those nice full breasts, and her shapely ass. She’s about five feet tall and weighs one hundred pounds. Her breasts look to be D cups, or about the size of cantaloupes, and she doesn’t wear a bra under her tight t-shirts. She sometimes wears tight shorts too, and I can hardly believe the size of her camel toe, with those thick labia pushing out.
It certainly wasn’t healthy for a girl her age to be identifying with me, a man in my forties, as probably her best friend, and I sometimes expressed concern about it. One day we were sitting on the couch together and I asked, “Does your mother know that you’re spending so much time over here with me, Vanna? I mean, I really enjoy your company, but I’m afraid that she might not be comfortable with it.”
She smiled that cute smile of hers and answered, “Yes, Ryan, she is aware, and I don’t think she really gives a shit. Willow is gone a lot with her friends, and with me out of the house, she likes spending time with Grady in the bedroom. But sometimes I get to join them in there too. I enjoy coming over here and talking with you, since so many of the boys my age are so silly, and you’re always so nice to me.”
Vanna had so casually mentioned joining her mother and Grady in their bedroom, that it didn’t sound like a big deal to her. I had been careful not to pry into their home life or make any disparaging remarks about her mother’s lifestyle, but I couldn’t resist asking about that, just in case she was really having sex with him.
I tried to be careful asking her about it, and I stumbled over myself as I asked, “My goodness, Vanna, did you say that you sometimes go into the bedroom with them? What, I mean, uh, uh, what do you, uh, what do in there with them?”
She didn’t even seem embarrassed when she replied, “Well, it was about two months ago, when I turned sixteen that Grady started paying a lot of attention to me. A week later, I overheard Mom telling Grady about how mature she thinks I am for my age. He made a remark like, ‘Damn, baby, she’s old enough to breed now, and maybe I can get her interested in me’."
"They might not have thought I knew what they were doing in there, but I knew that some of my friends from school were already fucking, and I was horny enough that I wanted to experience it too. It was only a week later when I surprised them by walking in and asking them to teach me.”
I sat there stunned with my mouth open looking at her, until I had the presence of mind to ask, “You mean that he, is fuc…, that he is having sex with you? Holy fucking shit, if that’s true, are you on any kind of birth control?”
She giggled when I cursed, and then answered, “Yes, Ryan, he did try to fuck me that first time, but we didn’t get very far. His cock is so big, and my pussy is so tight, that it hurts a little when he tries to push it in me. We have tried it a few other times and he’s getting more into me now, but mostly he sucks my tits and fingers my pussy, while I suck him off. Mom got me started on birth control soon after he tried to fuck me that first time, because she didn’t want me to get pregnant in my teens like she did.”
I said, “Yeah, I think I heard that Tara was sixteen when she got pregnant. Shit, Vanna, you’re only sixteen years old and you're asking him to fuck you!”
My mind was in overdrive, and my cock was getting hard, so I didn’t know whether to call child services or lean over and kiss her. But I wanted to learn more and asked, “Would you mind telling me about your first time?”
She laughed and said, “Sure, Ryan, if you really want to know. When I barged in on them that first time, they were both in bed, partially under the covers, Mom’s big breasts were exposed, and they looked huge, even compared to my nice D-cups. They moved apart and Mom said, 'Sorry, Vanna, I guess we've been a little noisy in here and you got curious. Would you like to join us?'"
"Then she said, ‘You’re beyond the age of consent now, Vanna, and if you'd like to learn about sex between a man and a woman, we'd be happy to teach you. Grady has been taking care of my needs in bed since Daddy moved to Atlanta, and I'm sure he’d want to teach you.’ I was nervous and scared but even helped when he pulled up my t-shirt and began to suck and rub my big breasts. They’re not quite as big as Mom’s, but Grady was extremely excited to suck them.”
She paused for a moment and noticed that I was rubbing my crotch, before continuing, “Mom just watched as he sucked my breasts and moved his hand down between my legs. He pushed my shorts down, and since I wasn’t wearing any panties, he started probing my pussy with his fingers. I have a nice bush of hair down there, and I didn’t understand at the time how Grady could be getting so excited just from sucking my tits and fingering my pussy, which was getting wetter and wetter, when he’s always fucking Mom.”
“He kept sucking and fingering me as Mom moved over to the other side of the bed, and started pulling down the covers from Grady, as she said, ‘Just relax, Vanna. Grady has gotten to know your body a little, and now you need to learn about his. You’ll see that he’s a big man between his legs, which is why I like him so much. But he’ll take it slow an easy with you. In fact, it’s probably best if he takes your cherry with his fingers, before he fucks you.’”
“I had never seen a cock or balls before, and his soft cock is very thick, uncircumcised, and almost seven inches long on soft. His balls are the size of eggs and hang down low in his nut sack. Mom said, ‘Go ahead and feel his cock, sweetie, and it will grow for you.’ His cock is so heavy, and I liked how thick and wet it was in my hand. I think they had fucked only a short time before, so it was still gooey with his cock juices. His cock grew hard as I stroked it, to what seems like over nine inches long.”
“Mom was watching everything as she said, ‘Turn around here, Vanna. Men like it when you take their cocks into your mouth, and I want you to taste Grady’s big cock. I'll get a towel to keep everything clean when he breaks your cherry with his fingers, while you’re sucking his cock.’ We were then side by side, with the towel under my hips, in what I learned is called the sixty-nine position, and I took his big cock into my mouth as he began probing my pussy more intently.”
She paused again and smiled when she saw that I was still rubbing my cock, and then said, “I loved the taste and feeling of his thick, slimy cock in my mouth, and as I felt his fingers pushing even harder against my hymen, Mom said, ‘Okay, get ready, he’s going to quickly push through into your pussy now. Just relax and it will only hurt for a few seconds.’ I didn’t know what to expect, but as I felt two of his fingers press into me, it did only hurt for a few seconds, as he stopped moving his fingers in me.”
“We stayed in that position for about fifteen minutes, and Grady pushed me away from his cock a few times because he was getting too close to cumming. During one of those breaks, I asked Mom why Grady didn’t suck my pussy like I was sucking his cock. She answered, ‘Some men like oral sex, sweetie, like your father, but other men just like to fuck. Your father has even eaten me out after Grady’s fucked me, but Grady isn’t into that. As you get older, you’ll find boys and men who’ll love to suck your pussy for you, and it will feel so good.’”
Grady let Mom know that he was ready to fuck me. I turned around on his belly facing him. Then he pushed me down until his big cock was pressing into my wet, virgin pussy. Mom was coaching me, saying, ‘Just press down on his cock, honey, until you feel it pushing into your pussy. Go at your own pace, very slowly, and see how much you can get inside of you.’”
“There was so much pressure as his big cock head separated my pussy lips, and I was so excited and aroused that I loved it when he leaned up to kiss me. He started almost imperceptibly flexing and thrusting his hips, until it felt like the head and another two inches were inside of me. We stopped pushing at that point as we had a deep, sloppy kiss, with our tongues intertwined.”
“The pressure from his thick cock was painful, and when he finally started moving inside me again, I asked him to stop. He started taking shorter strokes, just in those first few inches of my pussy, and I felt his cock begin to throb and pulse. His cum was flooding into me, just as I had my first ever orgasm on his big cock.”
“I squirmed above him, swiveling my pussy on his deflating cock, as we continued kissing. We finally broke our kiss, and he said, ‘Sorry that I came so fast, darlin’, but I just couldn’t last in that sweet, tight, teen cunt...
