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.
One of my more interesting calls this week was a man that had a fantasy about paying to be a cuckold. He wanted to rent an escort and have her fuck a black man in front of him while he watched. He knew his wife would never go for such a scenario, so he wanted to pay a woman to make this fantasy come true for him. When I mentioned this to another caller sort of into the same thing, he said he too had thought of the same scenario himself over the years. When you think of a man paying an escort, you obviously assume he’s paying to fuck her himself, but not always apparently.
He has a little cock himself, like many, but not all, cuckolds have. He loves the idea of a big, black, physically superior man taking control of the white woman in front of him as he strokes his undersized cock and gets aroused while watching her scream with ecstasy as that big, black cock stretches her open until she’s literally gaping and dripping that jungle jizz right out of her stretched out cunt. After he’s watched them fuck and the guy goes home, the one paying to be a cuckold licks the cum out of the escort he hired.
He adores the sense of degradation and being beneath the huge dicked black man. He’s just a little worm with a tiny cock, not much bigger than a peanut. So pitiful he has to pay to witness it in person, but no one’s going to do it for him for free, and having to pay degrades him even more in a way. So many pitiful men out there that want to be belittled and made fun of. He likes calling women up and having them laugh at him when he tells them all of his odd fantasies. It’s easy to laugh at others for sure.
There’s a large wooded area behind my house I go hiking in sometimes. It’s very private, several properties back onto it, but there’s usually no one around to be seen. I went for a walk last week out there and was looking at the leaves and little creatures scurrying about when I realized I had to go pee. I should have gone before I left the house but had forgotten to do so. It would have taken too long to get back, so I looked around and realized it would be just as easy to pull down my pants and go there in the woods.
As I was finished and about to pull them back up I realized there was a man watching me from around fifty feet. I was frozen. I could see him clearly and he was masturbating as he’d been watching me pee. He started to walk closer. All the while still stroking himself. I pulled up my pants and started to walk home. He came up to me and said it had really turned him on watching me and would I do him the honor of watching him finish himself off? I was a bit shocked, but was afraid he might get angry if I said no and try and hurt me, so I said sure, just finish up.
He pumped his dick, and it was a good size. I looked and saw the dripping precum at the tip. His balls looked large and swollen and filling with cum. I didn’t mind watching him, it was just a bit weird watching some stranger like this. I’d not seen him before and wondered who he was and what he was doing here, but didn’t ask. He sped up his motions until his hand was a blur and he shot his load all over the fallen leaves on the ground. He sighed with relief and zipped up and continued on his way. I went back home and wondered about him, it was an odd encounter to be sure.
Sometimes we do things we know we shouldn’t because it feels right at the time. Last week I had such a moment. I was going to a parent teacher meeting and I’d never met this teacher before of my son’s. I liked him immediately. We discussed my son’s progress and I was the last scheduled meeting he had for the evening. I had a feeling he liked me too. He complimented me on my dress and figure and before you know it, I was on his desk and we were fucking one another. It was hot, fast and very passionate.
He was divorced and I was as well, one kiss and he swept his arm across that desk sending papers flying and I was soon laid out on it, dress up to my waist, my panties removed by him to give him access to my dripping cunt. He licked pussy extremely well and I was soon cumming from that flickering tongue. He had a large and beautiful cock that was soon sliding in and out of that wet pussy. His cock rubbed against my clit with every thrust and I was soon clawing at his back as he made me cum again.
I sucked his cock still wet with my juices an that drove him wild. I swallowed his load and was then bent over the desk for round two. The fucking just did not stop. He knew all the right things to do and we both came and came and came some more. I have a feeling I will become addicted to his cock, but we don’t want my son to know about it. We have plans to meet at his place tomorrow night to further explore our mutual passions for each other. It’s been a while since I’ve been fucked this well. We are both deprived of sex and have found we are quite compatible in that department.