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robynrobinson Novice Jackinchatter

16 posts since 2017-01-12
40 year old
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is the experience worth it? it does sound like fun
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artist Amateur Jackinchatter

455 posts since 2015-07-14
57 year old from My little corner of earth.
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The closest I have come is a woman I knew online. Gorgeous milf! We chatted daily and would cam several times a week....Nude of course. We had many erotic chats and masturbation sessions. So erotic and so very hot. I would love to have another woman to chat with again.
I'm probably hard right now
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Feminine_MaleLesbian Professional Jackinchatter

1088 posts since 2015-04-17
56 year old heterosexual from Louisville, KY.
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I have, sort of. When I was married, I loved having phone sex and she knew about it and was fine with it, but didn't want me calling sex lines when money was tight. At one point she said I should talk to some of my female friends and see if they were into phone sex and see if they would be interested in doing that with me so it wouldn't cost me anything. At first I was like yeah, right. That would be nice and I thanked her for giving me permission to do this, but although I was pretty open with most of my female friends with talking about sexual things, I felt like if I started asking of they wanted to have phone sex with the that I would start getting looked at as a weird perv and they might start avoiding me. So for a little while I posted some ads in swingers magazines and on adult dating/chat lines and met a few girls that way that I didn't know in person but had some great phone sex with. (this was all before internet was a thing)
Soon after though, I got in some conversations with some of my female friends and was surprised when they brought up phone sex and asked if I had ever done it and if I was into it and if they could try it with me sometime, so that was the start of my phone sex buddies. Female friends I have never had sex with but had phone sex with and had a few while I was married with my wifes blessing.
She had even told me once that I could masturbate with any of these girls in person as long as we didn't have actual sex and didn't do it in our house. I decided not to tempt fate. I have never cheated and think I could control myself, but thought it better not to put myself in a position of too much temptation. On the phone or webcam you don't have to worry about anything going too far in the heat of the moment.
After my divorce though I have dated and had sex with girls I had been in relationships with, or friends with benefits, I have had my phone sex buddies and even had female masturbation buddies that we never had sex but masturbate together. Again, if I am in a relationship, then I don't get with my masturbation buddies in person, but still do phone sex and webcam with some of my friends.
Some girls I have been in a relationship with have been fine with the phone sex and also with my webcam activities since that has been a thing. Some girls may be okay with me doing phone sex and webcam with a service that I pay for where I will never meet the girl in person, while others say enjoy with my friends and don't waste the money on a service and then some girls didn't want me doing it at all with anyone and a few times I have stopped while I was in a relationship and I was good. But when you break up, trying to regroup with your friends to do those things when you're free to do it again, sometimes you loose touch, or they get in a relationship and won't do it or whatever, you you have to try to gain new female friends who will masturbate, have phone sex or webcam with you and it's not always easy to find them, especially as I said, without risking creeping some friends out that you don't want to lose.
Now days I just tell them up front this is what I do and I'm not going to physically cheat, but I am not going to give up my phone/webcam fun with my friends.
I have had some online mistresses from chat groups or Facebook, etc. that I chat with through messenger or whatever who I may or may not say anything about, but they are girls that I don't really know personally and who do not live anywhere near where we'd want to actually hook up, just all fun online. They may be a secret because I don't always think they are worth mentioning.
So never a mistress in person. I would never actually cheat physically.
Online, I guess you may call it that, but I personally wouldn't say they are mistresses that I chat with, have phone sex or webcam with since I don't keep that a secret and have permission of my wife/girlfriend to do those things with them.
If my ex wife were still alive and we were still together she'd be loving to see me enjoying other girls online and on webcam or sexting. She'd walk in on me having phone sex with one of my friends and either just do her thing or watch me, ask who I was talking to and tell me to tell them she said hello or lay with me and play or sucked me with me while I talked to them.
I could only imagine the fun we would have had if I was camming and she walked in. Or when one of my friends texts me a pic of their tits or pussy. I'd just laugh and say "Hey babe, look at the pic Debbie sent me of her boobs". She would have enjoyed looking at them with me. I really miss her. R.I.P.
Love stroking with the women in person, on the phone or on webcam.
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francesCD Skilled Jackinchatter

871 posts since 2016-03-29
from UK
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I have been calling the same phone sex girl for about 5 years so it seems like we're having an affair. I even feel slightly guilty when she's not online and I call another girl.
My wife knows I use sex lines (and so does she sometimes), but doesn't know I have a regular girl.
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weesteveni Novice Jackinchatter

77 posts since 2014-08-05
43 year old curious from belfast
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yeah i have an online mistress and i would highly recommend it, we always do sub/dom roleplay and cuckold play where she tells me shes going out to get fucked by another guy with a bigger cock, its all very exciting
you can beat an egg.. but you can't beat a wank
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thedogindc Novice Jackinchatter

34 posts since 2016-07-05
54 year old heterosexual from Washington DC
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Yes I fuck a married chick when I travel to Minnesota
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robynrobinson Novice Jackinchatter

16 posts since 2017-01-12
40 year old
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Somehow a couple of hundred $$$ a week just for a penpal seems a bit steep. unfortunately nothing for free
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