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Craigslist  

Soloweiner5 28M
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5/12/2020 5:23 am
Craigslist

I met a guy from Craigslist. This was years ago when they still had a personals section. We exchanged a view emails. He wanted to train someone how to bottom.

I eagerly agreed, showered, and started to make my way downtown to his apartment. I nervously knocked on the door in work out clothes with a gym bag. I walked in and it was clear I was nervous. He started caressing my butt when I noticed he had a station set up. That's where he would penetrate me, bent over his white leather couch. He had set up towels and a small bottle of lube with a few condoms.

We quickly undressed and I gingerly sucked his cock. I delicately licked his tip and made eye contact. He moaned "You're a natural. First time?" I nodded. He motioned for me to move to the couch.

I put myself ass out, face down doggie style using the couch to support my upper body. He grabbed both my cheeks and started tonguing my ass. He explored the crack and my tight hole for a few minutes. Satisfied I was comfortable, I heard a click. The lube was open.

He started slow with just a finger. Quickly graduating to 2. "Are you ready?" He asked as he broke open a condom. I begged for his cock. As he slowly entered me I gasped. "That doesn't hurt" I exclaimed. Proud that I had begun taking him, he began rocking back and forth. Making it balls deep inside me, he told me to flip over.

I got fully on the couch and laid face up, pulling my legs to my head and spreading my now trembling hole. He re-entered and began pumping. He started playing with my cock. First just caressing, then fully jerking it in time with his deepening<b> strokes.

</font></b>I involuntarily shuddered as I had the most explosive orgasm I've ever experienced. In that position, my own jizz slathered my face. I looked surprised. He giggled whispering "wow, didn't expect that to happen".

He showed me to the shower where I cleaned off and we made some small talk. I left and we haven't spoken since. To this day, my hole wishes to relive those moments.


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