I had sex with a bi-curious boy on vacation with family

(All parties are 18+)

I caught him looking at me. It was just a quick glance, starting from the outline of my cock inside my sweatpants, then up to my face before quickly darting away. I smiled, watching him pretend to be focused with the conversation going on at his table. I continued walking past him, the server leading me to a table further away than I wished. I took a seat, one that gave me a good view of his profile.

He was pretty. Soft lips, intensely dark eyes. Light brown hair that was clearly brighter from being in the sun this summer. It fell over his ears and was feathered around his narrow face. He was dressed like a preppy Ralph Lauren model with his ruffled Oxford shirt and lean fitted chinos. I think I spotted a small gold necklace underneath the open collar. Looking like a prince. That’s when he risked another glance, right into my stare.

Dammit. Too much. He spent the rest of the meal avoiding looking my way even slightly. Maybe I misread something. But now it seemed purposefully not looking around. Oh well, leave him be, I thought. Looks like he’s with his family. Probably the bi-curious college boy who’s secret no one knows yet. I smiled, over-romanticizing the playful moment while choosing my dinner from the menu. When I went to wash my hands before the food came, he was gone. Empty table. I shook my head. Goodnight prince.

I had turned 35 this summer, and was visiting the east coast for work. It was a nice hotel, catered the business conference crowd and the vacationing resort set. I hit floor 22 and felt the elevator rushing up to the higher levels and dug out my room card. Rounding the corner I could hear the vending machine being used, and just as I passed by, he stepped into the hall.

This was one of those moments in life where I had to really try hard to keep cool and hide my shock. I wonder if I was failing as much as he was. I gave a nod, half a smile. “Hey, how’s it going.”

“I’m doing well, thank you, how is your evening?” He rambled it off at twice the speed either of us probably expected. He ended with an awkward gulp you could honestly hear, starting to flush and looking flustered. God. Too cute.

“Best dinner in awhile,” I said, casually. “How was yours, you were in the restaurant earlier, weren’t you?” He walked along with me, a few steps behind.

“Yeah, it was good.” He said excitedly, then nothing. We walked in silence a few steps and I looked back at him.

“Vacation?”

“Looking at colleges.” My turn to look flustered. Oh god, how old was this boy? What were you thinking? He’s still in high-

“I took a gap year, but I start next semester.”

“Awesome,” I said, feeling relieved, slightly better, and reaching my door, 2203. He continued past.

“Goodnight,” he said, suddenly stopping at the door directly next to mine, 2205. I stared. What were the impossible fucking odds… He smiled, white teeth almost too big for his face as he took out his room key.

I opened my door, then mustered up some charm. “I won’t play the tv too loudly, no fear of keeping you awake all night. You can reassure the family.” He paused a moment, and then pointed opposite the hallway behind him.

“Oh they’re in that one.” His finger aimed at 2204. He held his look at me, the exact opposite of his avoidance at dinner, and I took in that pretty face for a long moment. No, no misreading that.

“Maybe I will keep you up all night.” I stepped inside my room and let the door close. I threw the key to the counter and ran my fingers through my hair. Holy shit. Now what? I was here for 2 nights. How long was he going to be right there, this close? Do I try to take this further now? Or wait? Was he thinking these things too, right next door…

My thoughts faded as I stared at it in realization. We shared a connecting door. Fuck. Locked from both our sides, yes, but how easy it would be to leave mine… I undid the lock, my fingers reaching for the handle… No. Much too soon. I heard the lock on his side unlatch, followed by the sound of his connecting door opening.

I froze up. So this was happening. I looked around, making sure things were in order if I was going to be having company. Then quickly went to brush my teeth in record time. As I was rinsing with water, the sound of a tv began to grow increasingly loud. From next door. I frowned. Purposefully loud. I smirked. Boy had a sense of humor too.

I waited a few more seconds, committing to the bold choice I was about to make, then reached over and opened my side of the connected door, leaving nothing between our room but an open doorway.

He was standing in front of the blaring tv screen, wearing a pair of red Tommy Hilfiger boxer briefs that hugged his narrow hips and nothing else, his messy hair a result of scrambling to undress, his clothes tossed around the room in a hurry. His lean tan body was toned, smooth except for a light trail below his navel, between his tight abs. He stared at me, shrugging. “Too loud?” My smirk turned into a smile. I stepped into his room.

(Continued in Part 2)



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