I [then 22F] fucked a 50-something on his boat [FM] [full story]

*This is the more detailed version of my slutty confession earlier today.*

———

Today I am thinking back to the summer day that I met up with a 50-something year old who responded to my ad on Craigslist. I had low expectations, but the chat was nice, and after dinner we walked along the piers.

“Would you like to go on a ride? I could take you to my boat.”

“You have a boat? I’d love to see it.”

Always an expert at first Craigslist date safety.

​

I know I post a lot of age gap stories, and it might come across as if I were perpetually chasing older dick, but I can say in retrospect it was a very legitimate date. I mean, I wasn’t doing *all* the thinking with my pussy. His Craigslist response was insightful and the conversation over dinner was great. He was excellent at flirting and I had fun dressing the part. Hair down, great face, a very flattering summer dress: purple, form-fitting, clinging onto the right curves. He was smart and quite the respectful gentleman. All this said, who am I trying to kid? I had posted the Craigslist equivalent of a RAOBJ.

When we went for a walk, the evening had gone so smooth and politely that I thought we’d end it with an innocent peck. You know, save the sloppy blowjobs for the third date. But his hand found mine, his arm pulled me towards him… the mood shifted. I went from arm candy to sexual property for the night.

I was horny and the boat was the closest venue.

Back to it…

“Would you like to go on a ride? I could take you to my boat.”

Needless to say, we got on the boat but we never went on the ride. Or at least he never did. It was late in the day and the surrounding boats seemed empty. But really, not long ago we had been just dining and being polite. The barrier finally broke when my sea legs took their time to arrive, and I lost my balance. His strong frame helped me into the boat, holding me close to him for a second too long, smiling.

Alone in public, frisky, thirsty — I kissed my polite date intensely, and I could feel him switch into sailor mode. His hands fondled my ass and breasts hard, as if he had been struggling to keep his hands off me throughout the entire date, and he whispered between kisses that he wanted to give me a boat tour.

“I have never had sex on a boat,” I confessed, emboldened by the wine and by my newfound seductress power.

He led me to the somewhat more private room, where clothes were promptly taken off and he pushed me on the bed. He moved between my legs and circled my clit with his fingers, teasing, a sailor’s smile on his face.

“You may have never fucked on a boat, but you’ve certainly been ready for it for a while.”

I spread my legs further for him, lifting my hips. He shoved his cock inside me and started fucking me raw. Something about the thrill of being with someone much older, of being seen, of doing something so risky, really — it all added to the kink. He had me moaning in his boat, begging him to fuck me harder.

After a while, we flipped and I started riding him — and I will admit that riding in a boat feels different. Personally, I don’t feel compelled to try it again. But at 22, playing slut in an older guy’s boat felt like the ultimate kink, and my pussy benefitted from this arrangement. Despite the motor challenges involved in fucking in a boat, my insides were building pleasure, and he was certainly enjoying the squeeze. “Squeeze me, princess,” he grunted with his hands on my hips, keeping me steady as I prepared to explode. He moaned louder than I did when I finally came around him.

He enjoyed fucking my raw, but he didn’t lose his mind completely, so after I came he said he wanted to come in my mouth. Good thing I am always orally fixated. I dropped to my knees while he sat on the edge of the bed and I stroked and serviced him until he flooded my mouth with his cum. I remember that what pushed him over the edge was my briefly stopping to beg for his cum.

“Cum for me, daddy…”

I worked his head with the back of my mouth and then withdrew.

“Please fill my mouth with your cum, daddy…”

I didn’t need to do much more. His body tensed up as I rubbed my lips over his flesh, and he released a very respectable load into my mouth. I swallowed all of it.

​

Maybe I’m not the most experienced in this one field, but fucking on boats can be kind of awkward. He gave me better fucks and orgasms on later dates, but this is the one I fapped to today. Still, and it probably goes without saying: it’s not a great idea to go to a Craigslist stranger’s boat on the first date. But, if you do, I hope you’ll live to tell your sexy story, too ;)

Source: reddit.com/r/gonewildstories/comments/w7bkdm/i_then_22f_fucked_a_50something_on_his_boat_fm