I (25M) had sex with a much older cougar (66F) and it was mind-blowing!
I'm a nerdy 25 year old guy who's pretty inexperienced when it comes to sex. Before this encounter I'd only had sex twice before when I was 21 (to a 24 year old girl I met on a night out at uni).
I've always had a fantasy of being with a *much* older woman…and realised I didn't have long left to hook up with one before I started getting older myself. I wanted to still be able to play up the younger guy niche, and look the part aswell. This fantasy turned me on so much that I seriously considered applying for some porn studios just to land an older/younger shoot role.
Until finally, I got messaging with a 66 year old cougar on a swinging website. She lived around an hour away from me in a pretty rural area. We arranged a day for me to come see her and I found the place.
When she answered the door she was wearing black high heels, tights and a low-cut blue top. She smiled and said, "Wow, 25, really?" I laughed and showed her my driver's licence. She seemed pretty surprised.
She took me to her bedroom and we had a brief conversation about ourselves before she noticed a bulge in my trousers.
"Alfie," she giggled, "You're throbbing."
"Hehe, can you blame me?" I asked.
She put her hand on my leg and it crept slowly up...
Her hand squeezed at my hardening bulge.
"Mmm," she said, "Getting big."
"I think it'll get bigger," I grinned.
She leaned in and kissed me. I kissed back, slow at first, then escalating. I put my hand on her face as our tongues danced in our mouths.
When our faces parted, I stared up at her chest. I'm not sure how real her breasts were, but they were absolutely huge. I asked if I could touch them, and she said of course. My fingers had a little play, and then she said:
"Let me take it off for you, darling."
She undid her top, sliding it off to reveal even more cleavage that had been hiding underneath. Then the bra came off. My mouth hung open. I couldn't fucking believe how big they were. She saw my expression and giggled.
"You look so young," she said.
"I've shown you my ID," I laughed, and she smiled.
"I guess you have."
I didn't suck them or touch them at all at first. I just buried my whole head in her chest, then shook my head all around. Her breasts were as big as my head and I fucking loved it.
"Mmm, Alfie!"
I came up for air and then dove back in, fitting one of her nipples in my mouth and sucking it. She moaned a little harder. Then I gently squeezed those enormous tits and she raised an eyebrow towards what was happening my side.
"I think you need some attention too, Alfie."
I lay on my back and said I think I know what's gonna happen next.
"I know how much you like young cock in your mouth," I said.
"You know what I like just as much?" she asked. "Teasing young cock."
She ran her tongue over my frenulum. Slow. Slow. Then with a dash more speed. I could feel the pressure mounting.
I groaned and told her how fucking desperate I was for her to suck on it.
Finally, she relented. She plunged my mid-20s dick all the way into her mouth and I felt an explosion of pleasure all over.
"OHH FUCK!" I cried out. I couldn't believe what was happening.
"OHHH YEAH! I'VE NEVER HAD MY DICK SUCKED LIKE THAT BEFORE!" and it was true. The blowjobs I'd got from the girl at uni were absolutely nothing on what this granny had.
"You've had so much practice," I laughed in-between deep breathing.
Then, she stopped, and my fear that I might prematurely finish vanquished. She said the words...
"Let's see how you fuck."
She reached into her drawer and pulled out a box of condoms.
"Regular or large?" she wondered aloud.
"Could go either way with me," I said, having not worn one since my uni days.
She smiled and said she'd go large for me to be safe. She wrapped it over me, squirting a dollop of lube over the top.
Then, she got on top of me. First, we tried cowgirl. She moaned and cried out how good I felt inside her. I was fucking mesmerised, but couldn't feel much. I suppose it was the lack of practice.
She suggested doggystyle instead, and I obliged. This time I put my cock inside her myself, without her needing to guide it. Then I thrust, and holy shit did it feel good now. I rode her older pussy, my young cock throbbing inside.
"AHHH!" we both cried.
My hands reached underneath and fondled those enormous titties.
"AHHH FUCK YEAH!"
I was getting close...quicker than I'd imagined, but it felt too fucking good to stop now.
"I'M ABOUT TO CUM!" I shouted.
"FUCKING CUM INSIDE ME, ALFIE!"
A string of white cum exploded from my cock, and my riding slowed down. I panted, each thrust becoming slower and slower, then finally stopped.
I pulled out, and she took a glance at the condom.
"Mmm," she laughed, "You weren't joking."
We walked bollock-naked out of the bedroom and each went into one of her respective bathrooms to clean up.
After getting dressed, I stayed for a good 20-30 minutes after and we chatted about our lives which in retrospect was quite sweet.
When it came time for me to go she gave me a hug and I said thank you for helping me fulfil my fantasy.
"You're very welcome," she smiled. "This was fun."