Thursday & Friday, April 1-2, 2010 

Several years ago, during a spring break trip to Pensacola, Florida, I found myself with five of my girlfriends in a Beer Pong tournament.  I had taken numerous shots and Margaritas to get to this point.  I had great beginner's luck and ended up in the finals against a gorgeous hunk named Bradley (not Brad mind you, Bradley).  I was quite taken with him and as alcohol gets me horny and sluttier than usual, I proposed a wager.  I don’t recall all the details, but the loser would be the winner’s slave for the next day, as well as do a striptease for the crowd. Bradley accepted immediately, and we began in front of thirty to forty drunken college kids.

Well, my beginner's luck held for a bit, but ultimately failed.  I was well lubricated and as someone in the crowd played stripper music on their smartphone I slowly took off my bikini. I walked over to Bradley and gave him a long deep French kiss, while everyone in the place hooted, shouted for various sexual acts, and shot video.  I quickly retreated, redressed, and asked Bradley where I should report tomorrow morning. 

We were going sailing.  I met Bradley and four of his friends, who had previously rented a thirty-two-foot sailboat for the day, at the Lanier Sailing Academy.  We got our safety talk and were off. I don’t recall much of the first hour, as I was suffering badly with a hangover.  Danny, one of Bradley’s friends, fixed me his instant hangover cure once we were underway and I was back to ninety percent in no time. 

Bradley asked me if I was still OK with the outcome of the bet, as that meant I had to do anything and everything he asked until we got back to the dock.  I hesitated a bit wondering if he was serious and I could actually back out.  But looking at the crew of five, all very nice-looking men who took care of their bodies, my craving for a wild time took over and I told him I was OK with anything he could think of.  He smiled and told me to strip and that I was to stay naked throughout the trip.  I didn’t hesitate for one second. 

Bradley then told me I had to protect myself from the sun and told me he would apply the sunscreen personally.  We went below and he emptied a bag onto one of the cots, it contained two bottles of sunscreen and two-dozen Trojan condoms.  He smiled and wondered out loud if he had brought enough, not saying which. 

I was covered with sunscreen by Bradley’s very gentle touch and so wet I think I was dripping down my inner thigh. Bradley, stripping off his swimsuit, then told me to apply sunscreen to the area where the sun doesn’t usually see as he would be exposed a bit on this trip.  While facing his quite erect cock I applied sunscreen randomly to his ass and soon I was sucking his cock - I couldn’t help myself.  He came quickly and I swallowed it all, then applied sunscreen to his package. Bradley had never told me to do anything other than apply sunscreen. 

Bradley then told me he’d send each of his friends down one by one and I should give each of them the same service … applying sunscreen.  They all came rather quickly.  Danny, who was last took me up on deck and showed me a lounge chair, and brought me a Margarita, quite strong. Bradley allowed me to enjoy my drink and then took me by the hand to the stern of the boat and showed me a makeshift “bed” made of boat cushions and beach towels.  He told me this was where I would “fuck everyone.”

More margaritas came as did the five friends.  Fortunately, they used condoms.  By noon I was totally wasted on margaritas and had lost track of how many times I had come or how many guys I had fucked.  I was served a very nice lunch, I think, and napped for a couple of hours. 

Mid-afternoon brought a big surprise.  Bradley’s boat rendezvoused with another bigger boat, and they anchored next to each other.  Suddenly I was tossed into the water and in the middle of nine new guys.  Bradley told me that for the next four hours I would do everything and anything Phil, his best friend, and captain of the bigger boat wanted.  He’d pick me up right here, he assured me. 

I was escorted, rather carried, into the boat’s bunkhouse and began a long afternoon.  I was subjected to every sexual practice I knew of and learned a few more: golden shower, what’s up with that?  Even though I’d classify most of it as rough sex, each time the guys asked me if I was OK with what they were going to do,  stupid, drunk, and a slave, I always smiled and said yes.  I must have come fifty times and my face covered in cum many times.  I had had anal sex once before but now could brag that I had been ass fucked a dozen times, at least, in one day. 

I was exhausted, to say the least.  When Bradley rescued me, I gave him a huge kiss and told him thank you for coming back. Then I said thank you for pimping me out and I really meant it.  I had been so free that afternoon and enjoyed the sex so much that I wanted more. Bradley led me to the shower and told me to wash up really well.  He then apologized that he had forgotten to give Phil the condoms. My mouth hung open as Bradley smiled and closed the bathroom door on me.  I used all the hot water on the boat and then enjoyed a swim in the ocean.  I was ready for more and I wanted more. 

I climbed the ladder at the stern of the boat and told them I wanted to be fucked hard and often for as long as they could get it up.  I grabbed Danny’s cock through his swimsuit and pulled him onto the cushions of the makeshift bed. Margaritas came and so did I.  it was great.  It turned out to be an overnight rental. I had several new experiences on that trip; I took three cocks at once, I had several double penetrations, I gagged trying to deep-throat, I rinsed myself off in the ocean several times and I got several facials.  I wore those guys out and they wore me out as well, and I fell asleep at about 2 AM.   

The next morning I found all the condoms were gone when I went to the forward cabin.  No surprise I guess.  Bradley surprised me poking his cock between my legs as I was bent over looking in the bag.  He apologized again telling me they ran out of condoms at about 10 PM.  I turned smiled and told him what the fuck and then took him in my mouth, and the sex continued until we returned to dock at about 11 AM. 

I asked Bradley if I could put on my bikini just as we arrived. He told me I hadn’t been his slave since Midnight.  As we parted ways, I told Bradley that it had been a fantastic experience but to never think that I would ever repeat it.