Role Play - Alison Hendricks Page 0,8
my cock through my jeans, undoing my fly to get some relief.
Gaytor69: me 2
Gaytor69: show me ur hole
Gaytor69: pls
Gaytor69: im gonna nut
It sounded like he didn't really need my help for it, but I was just horned up enough to decide it wouldn't be the worst idea in the world to send a stranger a picture of my ass. Pulling off my jeans and boxers, I gave my hard cock a couple strokes, holding my hand around the base as I positioned my phone behind me to take a shot.
The picture wasn't bad, all things considered. I'd put one leg up on the couch and had leaned forward, so my cheeks were spread. The second time I'd even had the foresight to grab one of them and draw it away, so my hole was more visible.
I sent it, the picture appearing in our exchange. Then, I promptly realized just what I'd done. I'd sent an absolute stranger an actual pic of my asshole. What the fuck.
Mortified, I closed the app before I saw his response. What if he didn't like it? I hadn't bleached or anything. Was that something men were always supposed to do? What if it was shaped weird or too hairy or somehow screamed "I've never actually had a real dick in me"?
Worse, what if he liked it? He'd probably want to meet, and I wasn't ready for that. Getting railed by some random guy seemed fun in theory, but--
Oh, God. Okay. Maybe that was a bit too fast. Maybe I just needed to figure out what the logical progression was. I could ease into it, open up my mind and then show my ass to somebody else.
I searched for "how to talk to guys on Grindr" and found a ton of videos and articles. Tapping on several of them, I saw the same wholesome but ultimately unhelpful advice repeated: Just be yourself. The problem was, I didn't want to be myself. Myself was a nerdy thirty-something who'd never been with another person outside of his wife. Myself was someone who thought hookup apps were weird, and that sex should be an intimate experience between partners. That guy wasn't ever going to get laid by anyone on Grindr, and that was all I could handle right now.
As I scrolled down the results, trying to find something a little less heartwarming, I noticed an ad placed in between the site listings.
I Know What Guys Want
Foolproof advice on sex and relationships or your money back. Whether you want a hookup or a marriage proposal, Dear Lonely Guy will help you be the man you want to be.
Okay, my first reaction was that it sounded like one of those gross pickup artist scams, but for MLM. I was prepared to scroll right by, but something about the ad caught my eye. Dear Lonely Guy will help you be the man you want to be. As in they'd teach me how to perform; how to not be so uptight about sending an ass pic to some guy I might see once and then never again.
I tapped on the ad, finding a simple page with a little more information and a form at the bottom. Apparently it served as a private Dear Abby-type column. He had some letters published as examples, but only with the guys' permission.
The advice seemed... pretty good, actually. And, the guy wrote in complete, grammatically correct sentences, which was a plus. Eying the form, I tapped on the PayPal button, paid the fee, then entered my question.
I went into more detail than I'd intended, telling them this was my first time getting back on the scene since my wife died, that I'd never been with a man before, and I needed help being someone other than myself so I could get outside of my own head.
They wrote back less than an hour later.
Dear Lonely Guy,
I'm sorry to hear about your wife, but good for you in taking this step. It makes sense you wouldn't want to jump into a relationship right off the bat. A casual hookup could be just what you need, and I'd be happy to help you find one that's going to satisfy your curiosity and get you out of your comfort zone.
I need you to understand that I'm going to ask you to do some things and talk to people in ways you probably haven't before. If it ever makes you too uncomfortable, let me know, but a little discomfort is normal. You're trying