(A pre-Covid extracurricular sextivity. Wear a mask and social distance, you animals.)
So I’ve always had a little bit of a fantasy about sleeping with an older man—silver(ish) fox, experienced, confident, etc. Your standard hot college professor daydream. Hardly a new one, I know. But it’s probably a result of all those years as a good little student (and some other issues I’ll choose to ignore for my own sanity). It’s still a good fantasy, I think.
A bit about me. 27. I’m tall, 5’9”, with fair skin and light brown hair. I have some decent, well-proportioned curves, probably courtesy of all the sports that I used to play. Recently, I moved to a new city and got back into the grad school grind. The standard mid-20s changes. I’ve been working hard and keeping my head down, but there’s only so much work without play that a girl can take, right?
I figured, I’m young. Miles away from home. Now is the time to live it up and do something crazy for once.
Well in a fit of boredom and sexual frustration (a dangerous combination), I hit up good old tinder. In swipes Tom. And he ticks all my little fantasy boxes. He’s easily 15+ years my senior. He’s got salt and pepper hair and just a little bit of grey scruff. Oof. I saw my chance, and I took it.
*Swipe right* *Match*
Tom was on a business trip to my city. He was well educated and well spoken. We hit it off right away. We were both busy with our own lives, but were down for drinks and some fun. Perfect.
Fast-forward to a few nights later, and I’m a confused mixture of nervous and turned on while I wait for Tom to arrive at my door. I mean, was I really about to fulfill a fantasy that started somewhere in high school? Eventually, I came to my senses and made a decision; this was my chance to lose myself in a fantasy, and I was going to embrace the hell out of it.
So Tom finally arrives at my door. He’s about 6’, medium build, rocking the salt and pepper hair, and sporting a pair of glasses that really spoke to the old crush I had on my English lit professor. We hug at the door, and that’s when I figure he first appreciated the leggings and t-shirt with no bra combination I was sporting. He was the older guy of my fantasy, so my thinking had been I might as well be the hot, younger woman of his.
Tom brought a bottle of wine to share, so I led him into my kitchen and broke out my best grad school budget mugs. We spent the next hour or so leaning against the counters in my kitchen, just drinking and talking. It was honestly pretty nice. Conversation flowed while we got progressively drunker on the bottle of *Any Alcohol Will Do 2019*. A good vintage for a slightly forbidden internet hookup.
Eventually Tom made a comment about how I was getting a little tipsy. (It was true.) So I figured that was my cue. I offered Tom the grand tour of my small, one-bedroom apartment that would inevitably end in my bedroom. Who would have guessed?
My room was darker, lit with just a small lamp. So when the tour ended at the foot of my bed, the mood was set and the inevitability of what was about to happen hovered between us. Tom took off his glasses and put them on my dresser, and then, somehow, we were all over each other.
Here I was in my bedroom, making out with this much older guy. His hands ran up and down my sides, thumbing at my breasts as he moved. My fingers tangled in the hair at the nape of his neck when I pulled him closer.
This is when things really start to get hazy. At some point, his shirt was gone and I ran my hands across his chest. I remember undoing his belt with more confidence than I actually had at the time. My clothes were easy to dispatch, and it wasn’t long before I was on the bed and Tom was between my legs, his tongue flicking over my clit while I pulled at his hair.
In between the kissing and cunnilingus, there was some dirty talk about what we were doing. A much older man fucking a younger woman. The whole forbidden age gap thing really worked for us. Not that I needed to be any more turned on at that point. Jesus. I was so ready for him. I hadn’t been fucked properly in months. And here was this hot guy who knew what he wanted, and it was me.
Before I knew it, Tom was on top of me. His mouth grazed my ear.
“How would you like me to fuck you?” he growled into my ear.
It was honestly one of the hottest things I had ever heard.
“Start slow.”
And with that, Tom was pushing inside of me.
His cock was probably a little above average length, and just the right thickness. I was so wet that the adjustment was easy. He started slowly, but before I knew it, my legs were wrapped around his back and he was picking up the pace. I was lost in the moment, but it was a fantastic moment.
Not wanting to forget my best-laid plans to enjoy my fantasy, I took back some of the control from Tom and changed our position. I had him lay behind me and hold up one of my legs as he fucked me. Let me tell you, that really hit the spot. The angle was delicious.
Occasionally, I reached back to grab his head for a kiss. Every so often he would murmur in my ear—how glad he was he had come over, how amazing I felt, how much he loved fucking me. It was so fucking sexy. And he had great access to my body with his hands. He’d explore and grab my breasts. Or hold onto my stomach when he picked up the pace. Sometimes one of his hands dipped down to rub my clit.
Eventually we ended up facing each other, one of my legs thrown over his hip as he slowly pumped in and out of me. He felt fantastic, and I lost all track of time. I still couldn’t tell you how long we went at it, but eventually his body stiffened and he grabbed me tightly as he came. I could feel his cock twitching inside of me.
As he slowly came back from his orgasm, I squeezed my muscles a few times, teasing his tired cock. Letting him know who was in charge here. We dozed for awhile, but eventually, real life called and Tom went back to his hotel.
He had a trip to a nearby city scheduled. The next day he texted a few times to ask me to come with him, said he’d leave me a ticket at the airport. Teased me with the idea of a weekend away filled with sex. It was tempting. Fucking Tom was fantastic. But the whole forbidden fantasy thing usually only works the first time.
Anyway, that’s how I fulfilled a lifelong fantasy and fucked an older man.
TL;DR Turns out the older, more experienced guy of my fantasy had a fantasy of burying himself inside a younger woman. 9/10 would live out a fantasy again.
Source: reddit.com/r/gonewildstories/comments/ilftp5/i_fulfilled_a_fantasy_and_fucked_an_older_man_mf
Never took him up on the plane tickets?