When I was in college, I started sleeping with this [much older guy for a while](https://www.reddit.com/r/gonewildstories/comments/k5abu9/i_23f_slept_with_this_guy_and_then_his_father/?utm_source=share&utm_medium=web2x&context=3) named Rudy. I saw him for the rest of my time in school and we still text every now and then. We had a really… special relationship. Part sugar daddy, part just Daddy. Like, he’d make me do my homework/write my paper for the next day, then take me upstairs at his place to fuck me. I miss him.
Rudy kinda pushed all my buttons in just the right way, and I would basically do anything for him. So once, when he asked me if I would go out with a friend of his who was coming into town and “show him a good time,” I said yes. It actually didn’t hit me until later that Rudy was kinda (okay, literally) pimping me out. But I went along with it, because I knew Rudy wouldn’t set me up with anyone weird.
His friend was “Vince,” and he was a couple of years older. (I didn’t find out how old until later.) He turned out to be super nice. He took me out to a nice restaurant in the city and we talked for a long time. (The waitress asked if I was his granddaughter, which 🤣🤣🤣….) He was funny and charming, and pretty handsome in a silver fox kinda way! I had just turned 21, so I could drink legally, which helped because I was also kinda nervous.
He took me back to his (very nice) hotel room after that. He asked if I would mind giving him a massage. I said sure. That turned into him taking off his clothes, and asking if I’d like to slip out of my dress. I massaged his back for a while, and then he turned around and, without asking, I started sucking his cock. (His cock was actually very nice, btw.) He let me do that for a while, and then he said he wanted to taste me. So I got fully naked and he went down on me for a while (and WOW he was very good at that). Then, he fucked me missionary. He didn’t last super long, but that was okay because I’d already cum twice.
We went to bed then – but in the middle of the night, he stirred awake, got up on me and started groping my breasts and hips again. He wanted to go again! So, sure – I let him fuck me again, from behind with me on my side. (Turns out, he’d taken a pill before we went out – I guess he still had some energy left, haha.) Before I left the next day, he slipped me an envelope with a thousand bucks in cash.
So honestly, it wasn’t like the best sexual encounter I’ve ever had, but it certainly wasn’t the worst! And I made a thousand bucks! I never actually did real escorting, but Vince was the closest I came. I don’t know if I’d feel as fine about it if he was gross or weird or something, but physically he was totally fine for a mature man, and he was actually really interesting and nice. And he kept saying I was “incredible.” So that was nice to hear. 🥰
Source: reddit.com/r/gonewildstories/comments/ocw03k/some_of_you_have_asked_so_here_it_is_the_oldest
Its always good when you enjoy it even without the cash, loved the story. Very hot
Such a wonderful person you are to share the love :) Sounds like Vince loved it
Whew! Looks like you met a couple of nice guys!
Nice story…. So is that how you paid for college? 😂.
Speaking as an older gentleman, I think this was an absolutely beautiful story. You’ve done good service, and I’m glad you were well compensated. ;)
Lol at telling a girl her pussy feels incredible
One of the precious few stories I’ve read recently which sounds, theoretically, realistic.