Sometimes some of the things callers confess to us can shock us, are they telling the truth, or is this all made up in their minds? Sometimes it can be one or the other and you never quite know what’s real, so you take everything with a grain of salt. One caller a few weeks ago was interesting to talk to and the details he provided made me think it was real, it’s odd they would be calling a phone sex operator rather than confess this to a therapist or a friend, but who knows why they choose to tell the people they do about their misadventures.
This young man, well he was late twenties, so not a kid by any means, he told me how he’s a male escort for other males and travels around the country from big city to big city, and posts ads on classifieds sites looking for appointments and he stays in that city for as long as he’s booked up, could be three days, could be three weeks, and he has several well heeled regulars he goes to see as well for a few days here and there, his sugar daddies as he calls them. He bragged how he was on that drug one can take to prevent HIV so he can have unprotected sex with some of the clients for more money.
It seemed a weird, nomadic and dangerous lifestyle, and he said he’d been doing this for nearly fifteen years, he’d started in his mid teens. I cannot even begin to relate to such a lifestyle, but you do get to talk to people in all walks of life when you are a phone sex operator. He genuinely likes servicing the older men, and said he plans to do this another good ten years, then feels he will have enough to retire with. Very odd the things some people do to get by on, I’m sure many would think doing phone sex for a living is also weird, but different strokes for different folks.
Recently I cheated on my boyfriend, and I’m a little surprised I didn’t feel the least bit of guilt about it whatsoever. I’m happy with my boyfriend, but recently I met this man and was really attracted to him, he asked for my number and I gave it to him, and then the suggestive texts began and secret lunches, which turned into dinners at his house and then we fucked. His cock is so much better than my boyfriend’s, and he just has incredible sexual stamina that far surpasses my boyfriend’s. I like them both, so I will keep up with them both.
Last night I had ten orgasms, I didn’t think it would be physically possible, but I did. I was such a slut. I was with the one I’m seeing on the side all afternoon and he gave me seven, then a few hours later I went to my boyfriend’s for dinner and he wanted to fuck all night and I had three more with him. At least I had a break of a few hours in between them to recover a bit.
I really am a slut, I guess, but my pussy was sure pushed tot he limits of her endurance yesterday, that’s for sure. I don’t think my libido can keep up with the two of them, but until I tire of one of them, I will be seeing them both, and neither knows about the other. My boyfriend is better at oral sex, since he doesn’t have a huge cock, so he can make me cum with that tongue of his anytime easily, and the new man can fuck like there’s no tomorrow, so I’ve been getting more than my fair share of attention, and I’m not really complaining. I just worry if they find out about one another, I may be the one that loses out, I will just have to see how it all plays out.
Recently I went to the theater with my boyfriend. His boss had given him tickets to some local symphony performance and they were lovely box seats in their own separate area. We settled in and had a lot of privacy, the music was lovely and then my boyfriend started to get a bit “friendly” and had his hands all over me. It wasn’t like we were in the main part of the theater, but I wondered if some usher walking by the back of the box might look in and see us.
I was a bit horny, so needless to say I didn’t stop him and he was soon kneeling on the floor in front of me and hiking my skirt up and pulling my panties off to the side and slipping his tongue between my pussy lips, all the while the symphony played and people down below had no clue what was going on in the box above them. I was squirming in my chair as I felt him tickle and tease my clit, obviously I had to be quiet and not make too many movements, as I didn’t want to catch the eye of anyone that happened to be glancing around.
I just sat back and spread my legs wide and let him do his work as I bit my lip and enjoyed it. I did soon cum and he licked my pussy clean before placing my panties back in their original position and then tugging my skirt down. I didn’t want to risk having sex and getting caught, he was fairly concealed in the darkness and in front of my chair, but he was going to get me when we got home! The next day his boss asked him how he liked the show and he said it was just fantastic. How much of that was due to the music and how much was due to my pussy, his boss will never know!
It’s almost Thanksgiving again, I hope I will get to see the sexy young man again this year that I got to know very well last year. I went to a new friend of mine’s home, she knew I was single and alone, and her son had come home from college fort he break, and as she was busy making the meal, he and I snuck off and had some naughty cougar and cub fun. He’d just turned eighteen, and was as handsome as they come, and he said while his mom was cooking, he could give me a tour around their farm and we went off walking.
As soon as we had some privacy, we were in one of the outer buildings fucking our brains out. His mom was entertaining a full house and she insisted she didn’t want any help from a guest, so we had plenty of privacy. His young cock was so hard, I hadn’t had one like that in many years and I loved it. He said he’d always fantasized about an older woman and I was certainly more than willing to play along with him. Even though he was young, he was a good fuck and knew how to use his cock very well.
I loved sucking on it and the sounds he made as I was sucking his cock turned me on so much, he just drove me crazy and he loved to call me a slut and a whore, which I also loved. We were gone for a few hours, and no one even seemed to notice us gone. I didn’t get to see him at Christmas, but I am very much hoping he will be back again and we can pick up where we left off. I won’t even masturbate until I see if he’s there, I want to be as horny as possible in case he is and I get to play with him.
One thing callers ask about frequently is breastmilk. Have I ever breastfed a partner, would I do I think it’s normal that they want to. Especially women with very large breasts make men think of this. Breasts have always been popular, obviously. Squeezing them, a titty fuck, sucking on them, but breastmilk is its own little niche that lots of men are curious about.
One called last night that said he was walking in his neighborhood and came across a woman with the largest pair of tits he’d seen in person and he couldn’t stop staring at them and of course she noticed and invited him back home, (this was likely pure fantasy I realize, since most women wouldn’t be inviting some creep staring at their tits to come home with them.) So he supposedly walks back to her place and laid on the sofa with her and she encouraged him to lay in her lap, his head in her lap, and she took out her supposedly H cup sized tit out and asked him to suck on it.
He was in heaven, and then he felt milk coming into his mouth, he hadn’t expected that, and while it was a shock, it was a welcome one, and he loved it and nursed hungrily upon her and said he’s not been able to stop thinking about it and he’s been hoping to run into her again in the neighborhood, but has not, and each time he’s passed her home, her husband has been parked in the driveway, so he knows not to approach her if that vehicle is there. He is now craving more erotic lactation and wanted t know where to find nursing women, I said just to keep trying for the one he knows about. So what one had never even thought of, can quickly become an obsession once you experience it.