Crossdressing Housesitter

There was a caller today that was a crossdresser, not an uncommon thing by any means. It’s astounding how many men enjoy dressing up in women’s clothing. This crossdresser though had a bit of an unusual story. His boss had asked him to housesit while they were away on vacation and he took that time to rummage through all her drawers and try on her lingerie and stockings and prance around in them. He never did get caught doing this, but it was his fantasy that she had come home early and caught him wearing her lingerie and what would she have done had she walked in on this little scenario.

He liked to imagine her being shocked, surprised, and horrified stumbling upon this unexpected scene in her own bedroom, and that she would turn him into her pussy worshiping sex slave for doing this. He’d have to lick her pussy on demand any time she wanted it done, and she’d also use a strap on, on him as well. Her stash of sex toys was one thing he;d found in her drawers he’d been rummaging through and he saw it in there and fantasized about her fucking him with it.

If she was very mad, she might even bring in one of her male friends to have him give blow jobs to and service sexually anyway they saw fit. He’d be serving all of them, and be grateful to do so. All the while dolled up in her lingerie and his cock as hard as a rock as she fucked him and he stroked himself. He found himself willing she would come home early from her trip and do these things to him. In all likelihood she wouldn’t have made him a sex slave, she’d likely have fired him and maybe called the cops, but hey, ones have their fantasies.

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Watch Me

I love to be watched. Watched having sex, masturbating. It’s kind of crazy all the high risk situations I’ve willingly put myself into where I could have gotten arrested just for the thrill of being watched. On a hotel balcony in broad daylight was one of my bolder , or maybe I should say dumber things I did. When online sex cams first came about, I thought this was a safe way of showing off without worries of being hauled off in handcuffs. So I would go online and find some cam chat room and masturbated for men. I’d wear a mask, I wasn’t stupid and didn’t want my career ruined, but I loved they could see every inch of me otherwise.

I would get so horny during the day and knew when I got home I could become my alter ego, complete with wig and mask. I would strip down and have dozens of men watching me, for free, I wasn’t even doing this as a cam girl or anything for money, just for the thrill of showing off. I’d finger my pussy, or use large toys on myself. Play with my breasts, and get myself so wet they could see my cunt glistening.

I new they were stroking their cocks to me as they watched me masturbate. I even convinced my boyfriend to join me once and we had sex on cam. He was a bit more stressed about it, I loved it, but he was a bit camera shy about it all and he didn’t want to again, but he thinks it’s hot I love other men to enjoy watching my body. He’s sort of a virtual cuckold I guess. I do love to show off and then when out in public I know no one would know it’s me. It’s fun and sex double life I’ve got going on.

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My Spying Neighbor

Most people would be upset if they found out their neighbor was spying on them having sex, they’d be furious and most likely even call the police about it. I’m not most people. I’m kind of an exhibitionist and like people watching me, that’s why I never draw the curtains in my house and walk around naked a lot of the time and don’t worry about having sex or masturbating when the window is open for anyone to see, and I live in a one story house. Ones at street level can and do glance in when walking by.

The new neighbor in the house next to me discovered my show off streak when he happened to glance in and saw me on all fours in the doggy position with my boyfriend fucking me. I saw him walk by his window, which is only around eight feet from mine, and then he did a second glance and stopped to watch. I glanced over and smiled at him, so he knew I could see him watching. My boyfriend was too into fucking me to notice we had an audience. I didn’t mind and even reached down to rub my pussy, get my fingers wet with my juices, then stick them in my mouth to taste them as he watched.

The next time I masturbated I saw him being a bit more bold and not even watching from inside his window, but he was outside of my window. I pretended I didn’t see him, but I am sure he knew I knew he was there and jerking off. I feel like kind of a slut getting off by doing things like this, but it really turns me on and I can’t help but put on a little show when I know I’m being watched like this.

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Slide It Inside

Most guys seem to love fucking a woman from behind. It’s about the number one position that guys give when I ask them what’s their favorite position to fuck in. I love getting it from behind as well, the feeling of it is incredible, and they can stimulate my clit or I can if they are too busy grabbing my tits or slapping my ass as they drill that dick into me. I will sometimes use my vibe when in that position, and then will put the vibe on their balls as we fuck and they seem to love it.

Guys can be more into vibes than we would think, and will seldom complain if you use one on them. Fucking from behind might not be the most intimate position, it’s the most animalistic one though and some guys love to get downright primal when it comes to sex and fucking. We are animals after all, and most animals fuck from behind as well. They like it primal too. Animals aren’t fucking face to face for intimacy, they are fucking to breed in the most efficient way possible, and that’s from behind. So if it’s good enough for the animals, it’s good enough for me.

My breasts love to be squeezed and caressed, the nipples teased, grabbing them from behind works perfectly to do all of that and more. I like my neck being bitten and even a good ass fucking once that cock has done its job in my pussy. Fucking from behind has all kinds of fun advantages. Is it your favorite position as well? Why not call one of our sexy operators and have a nice little chat about it and you can tell her all you love about taking that pussy and filling it up with your cum, we’re waiting.

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He Fucked His Mom

This caller had a fantastic story they were telling me, I’m not sure if it’s true or not, but it was pretty incredible regardless. He told me of how he was adopted as a baby and how when he became eighteen he went on a quest to find his birth mother. With the internet, what once would have not even been possible to track someone down can now be accomplished in minutes or hours. It didn’t take him long to find her and they set up a meeting for dinner. They met a few more times, catching up on their lives.

She’d been a young teen mother and ill equipped to raise a child, and he’d been given to a happy, loving family. Now after a few meetings, he found himself attracted to the woman that was his birth mother and she apparently felt it as well. There’s even a term for this more common than you’d think occurrence called “genetic sexual attraction”, where now reunited family members are suddenly drawn towards each other sexually. This is a known phenomenon. He knew it wasn’t right or natural, yet he couldn’t fight his feelings, and the next time they met, they went to bed.

He told me of the tenderness and intimacy he felt that he’d never felt with any of his girlfriends he’d had sex with before. He said they are continuing their sexual relationship and he’s moved into her home. He said it’s the best sex he’s ever had and they are very happy together. He feels they aren’t hurting anyone and they can keep it a secret, so why not continue on and fuck one another and live as a couple? He had to tell someone, he hasn’t told anyone in his life about this affair, if that’s even what you’d call it. It will be interesting to see how it turns out in a few years.

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