When I'm striking out getting laid, or on the prowl on a business trip, I have an almost sure fire way to get off.
I'll shift my attention to bigger girls. I'm decent looking and have no trouble starting up convos.
If using a dating app, they soon realize I'm from out of town and skeptically ask if in just trying to hook up. My answer surprises them and kind of turns the situation around: "I'm not into random hookup sex, I'm just bored out of my mind and seeing who's out there."
I'll quickly follow up with, "but I'm still naughty."
So now they know I'm not just trying to fuck them, but they're also curious about the naughty thing. I'll joke around saying I horseplay by the pool or sometimes get parking tickets - just silly stuff. Now things are light hearted but they're still curious and ask again. I'll respond by saying, "I'm a respectful guy, but ya I still like to have naughty fun." They'll ask again to be specific (seriously, every time). Finally I say something like, "I'm a dude alone in a hotel, if I'm going to jerk off it would be better to have company."
That might scare off half the chicks, but the ones that keep chatting are down for something. I suggest (and I'm sincere) that we meet for drinks, no pressure, and see how it goes.
So maybe a bigger girl that doesn't get that much attention from guys thinks, ok hell it's just a drink. And it is, no expectation, just a possibility if we're having fun.
I'm well presented and polite and genuinely like people. So I proceed like we never talked about anything naughty. Just chit chat and get to know each other. With everything going well, maybe midway through the second drink I'll say something like, "we're so innocent, almost forgot about we talked about earlier!"
In a sense, I think they're relieved that I'm bringing it up. As not mentioning it might be taken as rejection after meeting in person.
I'll compliment her then ask if I can tell her something crazy. Then I say, "I'd really like to show you my cock."
Online I already told her I'd rather jerk off with company and that I don't have random hookup sex. So it's pretty limited and if I get this far they always giggle and say yes. While I'm not going to have sex with a hottie on this night, this does satisfy an exhibitionist streak. Even if I end up just jerking off in front of her it's a win.
Anticipation builds as we walk to my room, once inside I'll confirm consent and strip down. Just the scenario gets me super hard: me naked in front of a cute chubby chick.
I'll just stroke it in a chair opposite her, and they're always fascinated,staring intently. I do have a nice cock too :) after several minutes I'll offer to come closer for a better view, which they always agree to. I'll show her my bulging hard on up close, and if she remained sitting it's right in front of her face. After a giving her a good look, I'll start jerking it right there.
After stroking it at her face for a couple minutes I'll say, "you can touch it if you want." And every time she will. Sometimes just feeling it then back to watching, but usually a hand job and often a blow job. Once they take over I'm asking to see their tits. And the best thing about chubby chicks is their big soft boobs which I'll then slide my cock between.
Finally it's "face or tits?" for more cum than they could have expected.
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