I knew what Island House was going to be, sort of a clothing optional resort with a little bathhouse element to it. For my first vacation by myself I thought I would give it a shot and see if I would be brave enough to participate in the possible goings on. I arrived on Saturday December 13th and got a quick tour and went to my room. I spent a few days wanting to get naked and wander around to see what would happen, especially in the "video room" with 24-hour porn and a sling table! I hoped that I could cut loose and have a little fun I do not have in Dallas. I am 43, 5'8", 210lbs; a pretty average white guy but I have very nice muscular legs and butt though it seems a toss up which men recall more, my muscled lower body or my long hair.
This happened on day two of my eight-day trip on a Sunday night.
I had a cheap room; the cheapest one could get with a private bathroom. I am a bottom and sharing a bathroom and cleaning out for fucking was not going to happen! It was good because I was right on the main path of traffic between the main entrance and the pool/bar area. Everyone would need to walk past my room and I might see something I like. I had spent the day being good and sightseeing around Key West but I came back to my room, cleaned up and was ready to get fucked. Lying naked across my bed watching a movie on my MacBook and "forgetting" to close my blinds got me some attention but not any offers unfortunately. Late in the evening I was ready to call it a night and then I heard a tap on my window....
In his fifties, six feet tall, athletic, British transplant to Key West and looking to get off, I knew all this in the first minute I met him at my door and invited him in. He was rough, really rough, with me. He pulled his cock out and told me to suck it. He pulled my hair tight to get a good grip on me as he forced me to take him to the base. I would gag and slobber all over his balls and my chest. He would yank my head back and ask me if I wanted his cock. I had to beg for it. He would hammer the back of my throat and yank me off and slap me with it. I have never been able to shake my gag reflex and a nine-inch cock was doing me no favors in that respect. He loved to make me gag hard and slobber all over myself.
He pulled my hair roughly and asked me if I had a condom. I barely gave it to him and he was already had me face down on the bed and balls-deep in my ass hammering me hard. It hurt. My hair pulled back, this cock hitting my insides hard with no regard for my pleasure, and him slapping my ass... I loved it! He yanked me up and twisted me around and threw me down on my back, I barely got my legs up and he was pounding me hard again. The pain was intense but the sleazy way he was using me had me hard. Then the nipple torture began.
While he was fucking me with all his might on my back, he started pinching my nipples with the force of a vice grip. Already moaning like a bitch in heat he had me yowling in pain as well. He took special pleasure in this. He crawled onto the bed to keep his cock in me while his mouth, or should I say his teeth, went to work on my nipples. I was protesting and trying to shake him off me as the pain in my nipples had me all but forget he was still fucking me. He held my arms over my head and laughed at my pain. He stopped fucking me and because the marathon of nipple torture the likes I have never endured in my life. By the time I finally got him to stop, my nipples were erect, swollen, red, burning, and in excruciating pain. It hurt just to feel his body heat close to them, even when not actually touching them. We had been at it for over five hours, loudly so I know the whole resort knew, and it was nearly 7am. He had to get back home.
He gave me his number and I gave him mine but we never met again while I was there.