The Babysitter’s Dirty Little Secret

When I was in my teens, I babysat a lot to put aside money for college, and this one family I babysat for had a really hot dad, I was always flirting with him when we were alone and I thought he liked me too from the way he looked at me. He’d drive me home most of the nights I babysat, since he didn’t want me walking home in the dark even though I was only a few blocks away. One night before he got to my house, I placed my hand on his thigh and rubbed my hand over his crotch. I could feel him grow hard instantly. I kept rubbing and told him to pull over into an empty parking lot nearby. He did.

He reached over and kissed me and I slipped my hand into his pants and stroked his cock for a while, and then lowered my mouth down onto it, sucking on his hard cock. He was moaning a lot as I sucked him off. I could feel his fingers in my hair pushing my head down further onto his cock. I felt naughty sucking off a man over double my age, but it was fun and he was obviously enjoying it.

Nearly every time he drove me home we pulled over into this parking lot before we got to my house and we’d fuck and perform oral on each other, this went on for a few years and I loved every single time. His wife never seemed to have a clue about it, and it was our dirty little secret, but a very fun one and I learned a lot from him sexually. I had a thing for older men for years because he was my first, and I still think of our times together when I masturbate.

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Here, Let Me Do That

Lots of guys have fantasies about their mom catching them jerking off and then helping them. A caller of mine last night said he’d fantasized about just that scenario many times, that his mom came into his room, say to put away his laundry, and she hadn’t known he was in there and she walks in and sees him with his hand on his large, teenaged cock, stroking away, and then he gasps as she walks in and sees this. In his fantasy, she doesn’t tell him to stop, or shame him, she asks if she can help.

She tells him she notices his technique, and how she knows of a better positions to place his hand in and she offers to show him, and of course he lets her, and it’s far better than the way he’d been doing it. No one can touch you like mom can. Her soft, knowing, gentle hands, on her boys shaft, pumping it up and down, and she asks if maybe seeing her breasts while she touches him might make things even more arousing. Of course they would, so he undoes her blouse and takes her tits out from her bra as she continues to caress him.

He rubs her nipples and they get hard instantly. She asks if maybe laying his cock between those breasts might be something he’d enjoy, and of course he nods yes, so she grabs a breast in each hand and wraps them around his cock and starts sliding them up and down his dick, while kissing the head of that cock and driving him crazy, and of course soon she is sprayed with her son’s cum all over her full titties. Then she tells him they can start to do this every night, and he’s happy to hear about his new bedtime routine.

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Please Let Me Worship Your Cock

One caller this past week is quite well endowed, or so he claims. You never can tell when a caller is being truthful of course, many will send you pics of huge cocks they find online and say it’s them even though the pic is easily looked up online and you can tell them so. The best rule of thumb is to divide by three. “Hey baby, my cock is twelve inches long.” Uh huh, sure it is, it’s likely around four inches or even less.

So you play along and say what a grand cock they must have how happy they must make all their bed partners and how many likely cannot even accommodate such a monster cock. One guy this week is supposedly over ten inches and he likes me to “worship his cock” and say how I’d be so glad to touch it, what an honor it would be to give him a hand job, since then my hands could fully explore the greatness of his manhood. He’s not interested in talking about any mutual pleasure activities like fucking, just a hand job since you couldn’t take your eyes off of it and be in sheer awe of it.

How it would take two hands, and even then it would be a stretch to get them all the way around his man meat. Wouldn’t it just be glorious to see and touch it? Wouldn’t I be describing it in all it’s glory to all my girlfriends? How could I not want to share it, spread the good news so to speak about his glorious member? Hey, it’s his fantasy, that’s what they are paying for obviously.

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I Spy

When I was younger and still living at home, I masturbated a lot, I still do, but sometimes I wasn’t as careful as I should have been, and one time I hadn’t closed my door all the way and I saw out of the corner of my eye, my brother watching me at the crack in the nearly closed door. I knew he could see everything I was doing, but I didn’t call him out on it or look directly at him. I in fact opened my legs even wider to give him a better view of my cunt as I toyed with it and I couldn’t see his hand or body since it was nearly dark in the hall, but I just knew he’d be stroking his young cock to my pussy being masturbated.

Our parents were out, so I didn’t need to worry about them interruption g us, and I let out a moan and I’m sure it must have sent shivers up his spine when I did. I could just picture his cock in his hand, his hand moving quickly up and down his shaft as he pumped his dick and watched his sister masturbate.

I could if I listened really hard, hear him breathing really heavy as I stroked my clit and lift my legs up in the air. I moved my hand faster and faster until it was nearly a blur from all the fast motions stroking my stiff clit, and then I came, I arched my back and I’d bet anything he blew his load as well at the same moment. I did this several times when I knew we were alone and not going to be disturbed. My brother saw me stroke my pussy many times, and it always made me cum harder.

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Teach Me Naughty Things

I’m a teacher at a local high school and I know lots of the young men I teach find me attractive. It’s not hard to motivate some that need extra help to do well. I do tutoring on the side, often their parents will contact me and ask if their little darling can get some extra help on the evenings or weekends, and I’ve found some of the young men need a little “extra encouragement”, but once they have it, they will pass with flying colors. This one good looking young man just didn’t get math, so I flat out told him if he passed, I’d fuck him. I thought his eyes were going to pop out of his head!

His mom had promised me a sizable tip if I got him to pass his exam, and I wanted the money, so I knew that my pussy would be the motivating factor here. Obviously I didn’t share that with her, I don’t think she’d have approved of my tactics. He learned, oh how he learned! He passed with flying colors, and he came by my house after the exam was over and he said he’d come to collect on my promise, and I delivered. I rode his young cock and sucked his cock for hours. He left so happy he looked like he was in some sort of drug induced haze.

I usually didn’t see the same students more than after the first fucking, after all, fucking me was the reward for passing, not an ongoing thing. There were always new students coming up in the ranks that needed my “special help.” I was only too happy to help, I felt I was doing them a real service, teaching them proper motivational skills, that would help them go further in life. I’ve taught many young men, and will teach many more. I’m really helping them in so many wonderful ways.

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