My Very Brief Weekend Dating “Adventure”

Last Wednesday I received the sweetest note on FetLife. The subject was “Interested, so very interested”. The message that followed was so charming I checked out his profile.

He’s only 26. Not much there for a profile, but I don’t have much either. Just pictures, and only one kind of with my face.

He didn’t have any pics posted online, but he addressed that in his note:

The way I see it being loud is like cheer leading, lets me know I’m doing a good job, and you can break as much of my skin as you like 😉
Hi, I’m “RS” (short for Rock Star) and I’m hoping that we can get to know each other.
What kinds of things are you into (both vanilla and kink)
I don’t have any pictures on my profile right now, but if you’re interested I can send you some via email or KIK.

Note: Rock Star is not his name on FetLife

I responded. He sent pics. He was gorgeous. We emailed a couple more times and then exchanged numbers. He’s new at the kink thing and so am I. We had common interests in rope/bondage, wax play, switching and also similar personalities and interests outside of the bedroom.

After my Thursday evening dating snafu, I was looking forward to something a little different. He asked me out for late drinks on Friday. We met at a bar and 3 hours flew by as we talked. Conversation flowed smoothly. I only had a couple weak bar drinks so I was fairly sober, he had a couple beers…

I really, really liked him!!

He walked me to my car and sat with me while it warmed up. We talked for another minute or two and he leaned over to kiss me…

His kisses tangled tenderly with mine. His tongue gentle, but not invasive. His hands caressing my back…

I want to write this in a sexy story kind of way, but my weekend didn’t end quite like it started.

We had perfectly-timed, amazing front seat car sex! I say perfectly-timed because, as soon as I got my pants back on, someone got into the car next to us 😉

RS winked at me and said, “I kept checking to make sure that no one was coming our direction.” I giggled and looked around. There was a car in the row behind us with its parking lights on. I’m fairly confident whoever was in that car watched the entire thing. (Hahaha! Kinda kinky, right?)

What a great way to break in my new car!!! (I’ll tell you about the car later.)

We texted briefly Saturday and Sunday afternoon he asked if I wanted to spend that night with him. I had Monday off, car sex with him was fun, so I thought What the hell? Why not enjoy a youthful frolic with this young gentleman and see where it takes us.

Not very far, it turns out.

I dressed up in my fuck-me boots and some patterned thigh-highs, short skirt, low cut shirt, favorite bra… I looked and felt amazing!

When I got to the hotel, we sat and talked for a while. He told me he really liked my stockings and my boots. It was comfortable when we kissed. It was comfortable when he took off his clothes and stood naked and glorious in front of me.

It was comfortable when I sucked his dick and when he entered my pussy from the front and from the back. I came so many times I can’t even count. His cock thrust so deeply inside me.

Slow…. Then fast. His hand on my clit sometimes… He grabbed my ass-plug and tried to put it in without lube. I reminded him, after a screech…

He played with the ass-plug while he continued to thrust into me. He was like a bunny. My legs were almost complete jelly when he entered my ass. He’s only the second man to have that hole and it still makes me a little nervous. Alaska was so gentle and good to my asshole… RS thrust a little to quickly and completely at first, but slowed when I asked.

I came again and again until I couldn’t hold my legs up underneath us any longer. I said, “I don’t think I can…” and collapsed on the bed, still convulsing from the aftershock.

He pulled out and went directly to the bathroom where he spent a really long time cleaning himself off. So long, I started to wonder if I had “messed” him up and he didn’t know how to say so.

Eventually, he emerged and sat down next to me. He was awkwardly uncomfortable and stood up again to grab his underwear before he said, “I should put these on before I tell you this. I feel so stupid.”

“What’s up?” I asked. Honestly concerned that something had gone wrong. “Did I do something? What happened?”

“Oh, no no! It’s not you at all it’s me. I know it sounds corny, especially with what was just happening, but I can’t do it.”

“Is it the age thing? Seriously, I don’t have a problem if you tell me whatever’s wrong. I’m grown. I can take it.”

“It’s not that, Smitten. I feel so stupid thinking it or even saying it because I haven’t even met her yet, but I think I’m in love with another woman.”

Honestly, I had not ever anticipated this scenario. I was completely speechless.

“I’m sorry,” he said. “I was really a jerk to think I could do this, but I can’t.”

“I really liked you, RS,” I said as tears welled up in my eyes. I wanted to hold them back, but then I didn’t. What difference did it make that this guy saw that he made my cry.

“I like you too, Smitten. Friday night I completely lost track of time while we were together. When you told me how late it was, I was genuinely surprised. I was even looking forward to learning things from you and together with you, but it wouldn’t be fair and I just can’t do it.”

He was so sweet about it. We hugged a lot of times and talked more as I got dressed and then I partially dressed him. He cried with me; he saw my hurt…

I said that usually all I want to do was cuddle after brain-mangling sex like that, I didn’t know how to react to what he’d told me. But I thanked him for giving me the opportunity to learn something new and being completely honest with me.

I know he was young. I knew it couldn’t last.

I was just hoping for some kind of connection. Even if it was only temporary.

This was just Fate looking out for me long term, I’m sure…

When I got home at 10:30PM, I sat in my car and cried. It took everything in my power not to text Alaska.

Monday my willpower was not so strong…

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