The Hidden Rendezvous: A Tale of a Secret Hotel Encounter
by Warlock Girl (u/Opening-Preference56) - Reddit
My first was short: My friend Stephen, who lived down the street when I still lived with my parents, spent the night once when we were younger and we shared a bed. He was an athletic guy with a shaved head and a great smile. During the night I felt him spooning me and his erect penis against me, so I rubbed my ass against it. He didn't fuck me, but he humped my ass through our clothes until he came, gripping my hips as he thrust against me and I squirmed. Then that was that. My "first" time, if that could count.
After that, I conspired how to get him alone for a serious encounter and a real chance to do as I pleased with his dick.
I was a freshman at a local community college and my girlfriend was 8 hours away attending a big name university. She was coming back for a visit and wanted me to get us a hotel room. I asked Stephen if he wanted to come hang out at the hotel since it was paid for for the day and she wasn't getting in until the evening. I told him we could walk to the beach or "whatever" and he told me that sounded fun.
When we got into the room I stood next to him next to the bed and pulled some condoms out of my pocket.
"I got these for Daphne, but umm I was thinking we could test them out first" I said nervously.
"Oh yeah?" he asked, "who would use it on who?"
I was a shameless ho even then, "I was thinking you could use one on me"
I carefully slid my hand against his growing penis and stroked it gently, tracing my fingers along the shaft and slowly rubbing it through the fabric. He started unbuckling his pants and I instinctually fell to my knees. I was face to face with his delicious looking cock and I purred subconsciously before I took him into my mouth. I gently swirled my tongue around the head before I kissed down his shaft. I opened my mouth and bobbed downward, taking as much into my mouth as I could. I continued and would have kept going but he interupted me so we could take our clothes off and get to the business at hand. He wanted to fuck me as much as I wanted to get fucked. I slid the condom on and ran my tongue up and down it, getting lots of spit on.
"How should we do it?" I asked, I really didn't know. I had already been fucking myself with toys for years at this point, but this this was my first time actually getting fucked by a man in the flesh.
"Lean over the bed" he told me.
I leaned over the bed, my dick was so hard in anticipation of what was happening. He got behind me and rubbed his dick against my crack, finally settling on my hole. I wiggled it in anticipation and he slowly thrust into me.
"You're too tight" he said, "it's not going in"
"Keep pushing," I told him. After fantasizing about this my whole life I wasn't ready to give up.
All at once his full 7 inches slid into me, and the mixture of pain and pleasure was immense. Once he was buried in me, he stopped.
"I need a second" I told him. His dick deep inside of me, I pushed forward and back working it in and stretching me out, "Ok, keep going"
He started fucking me, slowly at first and then passionately. Hooked together, I crawled all the way on the bed and leaned over on all fours, my face pushed against the mattress and he started fucking me again. After a few minutes of this, I started wanting to take full advantage of the situation.
"I want to try more positions, what else can we do?"
"I like to fuck my girlfriend on her side, lets try that"
I laid down and he spooned me, his dick quickly finding its way back home as I moaned in delight. He held my hips and thrust in and out, I kept trying to push against him and match the thrusts but he kept holding me still. We fucked like this for a few minutes when I told him I wanted to ride him.
Riding is my natural position, its how I've always fucked myself when I was masturbating and gave me the most control over the penetration. It's basically the easiest way to make me come is to have me on top. He laid down and I straddled him and lowered myself on. It felt just like I had always imagined and I was soon passionately riding him in earnest. I probably rode his cock for a good 5-10 minutes before he breathlessly asked
"Can I come inside of you?"
Still bouncing up and down, I told him yes and shortly after felt him tensing up. I laid down my chest against his and my ass wiggling on his dick as he thrust up into me. I felt him cum and we just laid and held each other for a little while.
We both showered (separately), put our clothes back on, watched TV and waited for my girlfriend's arrival.
I wonder if she noticed that we'd used one of the condoms.