The Business Trip Cuckold

The topic of cuckolding is always popular on phone sex calls, though there are many different branches on the cuckold tree. Some like to watch, others just listen, some want to participate and fluff the men up and clean the lady up afterwards. One caller recently was sharing how his wife goes away on frequent business trips, usually twice a month, but only for one or two nights, and not terribly far from home. He said he knows she’s fucking other men when she goes out of town, since she told him she was and he told her it was ok. He said his dick is a bit smaller than average, and he knows her needs exceed what he’s able to provide her sexually.

He said sometimes when she’s away she takes pics of what she and the other man are doing, or even gives him a live feed of it by turning her cam on and he can watch in real time as it’s unfolding. He said she’s even handed her phone to the man she’s fucking and had him take POV shots of her sucking the man’s dick and then sending it to her husband. He has a folder of pics of his wife with other men’s cocks in her mouth and he looks at them when he masturbates and she’s out of town. He knows she’s fucking one every night she’s gone.

She tells him all about the gory details when she gets home, who she fucked, what they did, how much she enjoyed it. He’s many times going down on her as she’s relating her tales of debauchery she lived out while out of town. He gets incredibly hard thinking of his wife fucking these strange men and then getting pictures sent to him. He said he’d even be ok if she wanted to do this in their own city, but it would need to be in a hotel, since they have kids and can’t host such a get together at home. He might be able to go to the hotel and watch if they got a babysitter he said, he’s got it all planned out in case it’s a possibility.

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Finalizing the Sale

Years ago I used to work as a sales clerk in an upscale men’s shop. The commissions could be pretty great, and the men were mostly well off that were there buying, since it was a pricier store. This man came in and had picked out several expensive suits and I was helping him pick out shirts and ties to complete them. Then he started saying it was too much, he shouldn’t spend more that month. I really needed the sale to pay some bills that were coming up. I asked him if there was anything I could do to finalize the sale.

He said he was horny, so I said I’d give him a hand job. He said that would be fine. I got him undressed and started to stroke his already hard cock. It was going to be a great sale for me, so I really wanted to give him a great orgasm. I moved my hand teasingly up and down that hard shaft and spit in my hand to make it extra slick. He leaned back against the dressing room wall and looked at our reflection in the mirror as I stroked him. He wasn’t a bad looking man, so I didn’t mind too terribly.

I rubbed his balls and could feel them tightening up as he grew more and more aroused by my hand job. He moaned a bit, but wanted to keep quiet since other customers might hear us and I sure didn’t want to be found out and maybe get fired. I sped up my tugging on his cock and he bit his lip as his orgasm approached and I soon had a handful of his cum. I left him to get dressed and I went to wash my hands. We then met at the counter and I rung up my largest sale of the month. It had certainly been worth it, and no one seemed the wiser.

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Rummaging Through the Laundry

There’s more guys out there than you might think that are into satin. Lingerie is a big fetish, but some are exclusively drawn to the cool, slipperiness of satin. Last night I had a caller that said he’d been rummaging through things he shouldn’t have. He said he’s roommates with his sister. They share a condo together and when she goes out, he goes through the laundry hamper and takes out her dirty panties and masturbates with them. He said he’s done it since his teens, and part of the reason he agreed to be her roommate is so he’d still have access to her dirty underthings. She knows nothing about what he does when she goes out and sometimes even when she sleeps.

She wears a lot of high end satin and lace lingerie. He said her boyfriend is pretty well off and buys her lots of fancy clothes and lingerie, so he also gets to enjoy it, but of course they don’t know he does things to it. He likes when he gets the items fresh off of her before she turns in to go to bed, practically still warm from her body. He said he knows when’s she’s been out with him, since sometimes the crotches still have a bit of leaked sperm in them from coming home after her dates with him.

I think if the caller every gets married, he’s likely to be a cuckold, there’s a good chance of it from the behaviors he’s described to me, in any case. Last month he said he put a pair of her worn panties on and wore them under his clothes and she had no clue about it. He likes when she has her boyfriend over and he can hear them fuck on the other side of his wall and he will jerk off and listen to them. No woman of his own of course, he’s kind of a sad case, but hey, he takes his jollies where he can find them.

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He Watched Her


There’s no shortage of men who like to spy and watch others while they have no idea they are being watched. Callers admit this all the time, that they are watching or following women they like and spying on them. Sometimes it’s easy, if the women are roommates. They are literally in the same house or apartment, so it’s very easy for them, other times it’s an ex they are still hung up on and obsessed with some new guy she’s dating they are jealous of. One man that has a thing for his roommate, her room is right next to his and he said he listens to her masturbate and spies on her when she’s in the shower.

He sounds like a creep to be honest, but many callers are creepy, it’s just part of the job. So this woman he spies on has no clue he’s watching her in the shower daily. The bathroom door has a faulty door knob and won’t quite catch, so it’s always open around an inch, even when it’s pretty much closed, so he stands there when she gets in the shower and looks in that inch door gap and watches in the mirror the reflection of her in there and beats off.

It’s his daily thing and she has no idea he’s doing it. I worry about her sleeping and him maybe going in and crawling in next to her if he can’t control himself, but he said he’d never do that, he just likes to watch her and gets aroused by it. He listens, he watches, he’s also volunteered to do the laundry and I’m sure you can guess what he does with her worn panties before he washes them and returns them. He sniffs and licks them and rubs them on his cock. Maybe one day she’ll catch on to his antics.

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Down a Dark Alley

Sometimes you will share things with clients and it will give them an idea for a fantasy. One caller that’s into reluctance, ok, rape, not brutal but definitely non consensual, he wrote a story when I told him about something that happened to me recently. I’d come out of the theater at night after a show and was unable to get a cab, so decided just to walk home, even though it perhaps wasn’t the safest thing to do. I had to walk through this alley and it wasn’t that well lit. There could have been someone waiting in the shadows looking to grab some unsuspecting lady such as myself that was foolish enough to go through there after dark. I got home fine without anything happening, but the caller created a fantasy of what could have happened.

He liked the idea of a woman walking alone at night in an alley, taking an ill timed shortcut to where she was going, only in her case, she wasn’t as lucky as I was. He wanted to image her being grabbed from a dark door well and pulled into the shadows. A hand over her mouth and another making it’s way up under her skirt. Ripping her panties down, forcing her legs apart. She too terrified to scream or move or fight back in case he had a weapon. So he rapes her there in the darkened door well standing up.

His hard cock penetrating her, his grunts against her neck, no one to see. His hand covering her mouth to muffle any screams that might come out. He fucks and thrusts into this stranger that happened right on by and into his path, just waiting to pull her in. He cums quickly, she can feel the cum running down her legs, he dashes off and she collapses, having an orgasm from a stranger she never even saw the face of. Crying, bewildered, yet in the throes of a violent orgasm she never expected. Some indeed do have dark fantasies.

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