I was not a fan of my new boss at all, he’d been made my superior a few months back and I thought he was a total asshole. One night as I was on my way home he told me to come into his office, so I went. He sat me down and told me he had to make some staff cutbacks and unless I wanted to be let go I’d give him my underwear right now. My jaw fell open. He said no one would believe me if I told them and I needed the job. And he knew it. I did as I was told and went home stunned.
The next week he asked me to stay again and he said he’d “put my underwear to good use” over the last week. I did not ask for further elaboration, I could well imagine how he’d violated it. He told me to get on my knees and suck his cock or else I’d be leaving with my final pay check. I did as I was told. I took his cock in my mouth and sucked him off. I figured he’d cum quickly and that would be the end of it. Wrong.
He said for me to get up and bend over the desk, that he’d be finishing in my pussy. I was nearly crying, but thought of all the bills I had and medical expenses, there was no way I could lose this job. He fucked me hard, shot his load in me and then pushed me out the door, discarding me like a used tissue. He said he’d be using me regularly, so to get used to it and keep quiet about it. I would start looking for another job, but knew I was to be his sex slave on demand as long as he commanded it.
A man called today and said when he was in his teens he found an old VHS videotape of his parents having sex when they were younger. He said his dad had always been a big one for taping everything with his video camera, and I guess their sex life was no exception. Most men are extremely visual and ones into photography and videotaping even more so. The hit movie Sex, Lies and Videotape was a huge hit in its day. Perhaps his parents were so inspired. He found the tape in a box in the attic and they likely had forgotten where it was, but he found it and watched it, over and over.
He said they still had a set up in the basement with a VCR hooked up to sometimes watch old tapes on and he made good use of it. He couldn’t believe how much better his mom’s tits used to look when she was younger, and how much thinner she was, and apparently what a wanton slut she was as well. He would stroke his cock watching his dad fuck his mom. The mom was more of the star of the videos and it was a combination of being on a tripod and recording both of them and his father holding the camera both for POV action like fucking her from behind, and recording the mom masturbating as well.
He said they’d be very angry if they knew he’d been watching such a private video, but he was a horny teenager, what was he to do? Horny teenage boys are not known for their restraint in sexual matters. It was a two hour tape and when he was alone for hours after school before they came home from work he’d stroke away watching it. He was so disappointed when he went back to the old box he found it in and there weren’t more. He even searched their room when they were out and didn’t find any there, either. So it might have been a one time experiment to tape themselves, but he sure got a lot of use out of that tape.
Sometimes you just get so horny you don’t care where you are. You just need to cum. I had a situation like this recently when I was outside in a semi public area. I’d volunteered to do some fall cleanup work at a local park and get it ready for the winter when I was all of a sudden overtaken by a wave of horniness. I couldn’t wait to drive back home, there were not many people left and they were in a different area of the park than I was in. So I decided to go for it. I just got down on all fours, lifted up my skirt and rubbed my pussy.
I was already sopping wet I was so horny. You really get to the point where you don’t even care if anyone might see, you just want to feel your body shiver with that sweet, orgasmic delight. I hadn’t cum in a few weeks, I’ve just been so busy. I was working away in the park garden and the sun was warm, the birds were singing and the day was just lovely. I knew it would be the last nice warm day like this before it got colder, and I’ve always enjoyed playing outside in my own backyard and having sex a few times with various boyfriends outdoors as well.
My cunt was slippery wet and my clit already stiff and erect. I toyed with it, rubbing my middle finger over that hardened little bud. Smearing my wetness all over it. I was soon bucking my hips as I did. Masturbating in that position of course makes your clit stick out even more than usual, so it’s extra pleasurable. I rubbed and I rubbed and I felt a mini explosion in my cunt as I came. I fell over in an exhausted heap, looking around to see if anyone had seen me and what I was doing. It seemed my naughty outdoor secret was safe. I caught my breath and then went on with my work before going home a while later. The outdoors can be so fun when we do things like this.
Some men that have a small penis call for small penis humiliation, it’s quite popular and one of the most common calls we operators deal with. Other men though aren’t calling to be humiliated, they just want a sympathetic woman to talk to. One such caller reached out last night with a three inch penis. He was in his mid fifties and had never married. He’d had a few girlfriends, but things never worked out for him long term. He knew the reason for this was the size of his cock.
He never told any of his male friends about his little shortcoming and he said for decades they all tried to pair him up with someone, and he always rebuffed them. He said it had been more work for him to stay out of pussy than get any. He was deathly afraid if he dated a woman referred to him by a friend that word would get around about his small cock to his circle of friends. He said once he reached his fifties they didn’t try to pair him up so much, they’d pretty much accepted he was ok with being alone, so they didn’t push it. All his friends were married or divorced, none never married like himself.
He’d wanted a normal family life, but his cock size had made that impossible. He’s in good company, I’ve heard similar tales from countless men about their cock size ruining their chances at a normal life. I feel badly for them. No fault of their own, just being shortchanged by mother nature. So masturbation is pretty much it for a lot of them. The few that have had girlfriends end up getting cheated on. I suggest a cuckold type of situation, but they can’t seem to convince the women to do it, not a very happy existence for a lot of them.
Oddly enough twice in the past week I’ve gotten calls from men that claimed to both just released from jail and prison. Literally that day. Now if one was in prison, would the first thing you would think to do once free would be call for phone sex?! Well, apparently it was for these two men. One was only in jail for two weeks for a DUI case, the other for six years for dealing drugs. I was kind of speechless that they were both so upfront about it. Not sure if they were seeking real life prospects in their own world and just didn’t have ladies waiting, but the phone was their first line of defense when it came to being horny.
I’d imagine it’s not easy to find privacy to masturbate in jail or prison. Any kind of sex would be horrible, against your will, so you really wouldn’t want that. Many would not have someone waiting on the outside to be there for them and welcome them home, so I guess if phone sex was a part of their masturbation routine before they were incarcerated, it’s something they would seek to resume when they were free.
The voice of a woman could be a very comforting thing for these men, they would likely have had very limited contact with women of any kind since going in, other than maybe a guard or some other kind of prison worker. It’s understandable they would find someone as soon as they get out, be it an escort or the safer route, a phone sex girl, to give them some female attention, even if only for the length of the call. Not sure how many go from jailhouse to phone sex within hours, but it is happening. We ladies are here to offer comfort in any capacity we can over the phone.