So my dad (Sr.) plans a sailing trip for us. We have 5 guys on a 50ft cat in B.V.I. Lets get with protecting the innocent first, the 5 man crew includes me (jr), dad (sr), dad's best friend (Jack), dad's buddy (George), and the little bro (Trey). Well lets start with the first night. We all get to the boat but our checkout is the next morning. We are all sleeping on the boat in port the first night. I haven't slept in about 20 hours cause i don't sleep on planes very well.
There is a club on the boardwalk up from the boat that seems to be hopping so we go check it out. We walk in and everyone is kinda partnered up EXCEPT 1 girl at the bar. I immediately walk up to her and start talking to her. She is British and her accent is SEXY. Her name is Izzy and she is a pre-med student back in the UK. We talk and dance for a bit. I look up and the guys have disappeared. I ask Izzy where her friends went she has no clue. She is pretty drunk though so i suggest we go for a walk around the bay. She agrees and we walk for a bit. Talking and laughing she tells me that she is attracted to me and wants me to do what ever i want to her. I am caught a little off guard by this, but we start making out. She ask me to take her back to my boat I say ok. On our way back we make a few pit stops and make out. I basically have her dress off of her a few times. She has an amazing body and i tell her she does. It comes out that she is 21 and i figure out why her body is amazing. So we get back to the boat and go to my room. Get undressed and doing some 4 play, she starts convulsing and tells me that she has never big O from 4 play. She starts telling me that she is not as experienced as me. I ask her what that means to which her reply is i have only been with person. This is where shit goes sideways. She looks at me and says "I don't know your name", i am like JR. She basically starts crying and telling me that she has to go. I say ok and watch her get dressed and leave. Damn good way to start a vacation but could have been just a bit better. :)
So we set sail the next morning and do some sailing we end up in Norman Bay. We go to dinner, where i get a bit tipsy and somehow something comes out of my mouth about being a "Big Mother Fucker." This starts a running joke for the entire trip. After dinner we go to this bar on a barge called Willie T's there are people jumping off of the roof topless and naked. There are women giving body shots on the bar. There are women getting fake tattoos on intimate places. This place is crazy. We have a good time and go back to the boat and go to sleep.
The next morning we get up and sail away. We do some stopping here and there. Having a blast. I am learning to sail a huge fucking boat and love it. We pretty much stop by every island near us. Do some snorkeling or sight seeing. We make it to Virgin Gorda where the baths are. We get up the next morning and hike that area which is beautiful. After we get back to the boat we decide to sail around to a port on the other side of the island to get fresh water. One of the pumps had sprung a leak and the charter company came and fixed it. But we were low on fresh water. So we sail around the leverick bay. It should be noted that at some point before this i told Trey that i was going to toss him a soft ball at some point on this trip.
So Leverick bay is the sight of the most epic night of our trip. While the fresh water tanks are being filled George and i walk over and grab a drink at the bar. While we are there a group of young women walk past us. I say something along the lines of "hey ladies would you like to have a drink with us" The response i got was "No we are going to take showers." I say, "you ladies look fine to me you should have a drink instead." The leader looks at me and says "I know i am glistening." I let it go and then 4 more girls come up and sit at the bar. Immediately some little guy walks over to them and i hear them shut him down immediately. I play it cool and just say hey ladies where are you from. Their response is South Carolina. I don't say anything else just let it settle. Sit there a little longer then the first group of girls come back and sit with current girls. So 8 girls sitting at the bar next to me. I say "Hey glistening can i buy you that drink now?" She says let me finish this one then yes. About this time the rest of our crew shows up and sits beside George and i. So I bail off in the middle of these 8 girls. I am talking to all of them at once and i ask them if they are all Gamecocks? They say who said we were Gamecocks? I said well i was told you were from South Carolina. This is when i learn they are the Clemson female rowing team.
So glistening and myself move off and start talking alone. I tell the other girls to go flirt with my crew and they will get their drinks paid for. While talking glistening walks off and Anna comes up to me and tells me she is glistening's roommate. She then begins to inform me that Tatiana (glistening) has a nickname of Tits. She also tells me that Tits is a lesbian and that sometimes she brings home guys and they have 3somes. I am very interested in what Anna has to say at this point. We take some pics and do some dancing. Somehow i get on 1 knee and purpose to Tits. This night is getting crazy. Then someone gets the idea that we should go to our boat.
Our 50 foot boat is packed 8 girls and 5 dudes and it is great. We are drinking and parting. I am up on the trampolines hanging with tits and talking. We talk about her being bisexual not lesbian, i am good with both. We jump off the roof of the boat a bunch. It is a great night. Long story short Tits basically tells me that she wants to do this but we need to wait a bit.
At 1 point in the night one of the girls crawls into Treys bed and i throw him in there with her and shut the hatch. Those guys are in there for a bit. Not sure what happened but i can only imagine that my little bro owes me big. I told him soft ball i didn't realize i was going to put it on a T for him.
Then people start getting drunk and puking on our boat. Then Anna passes out, we are taking the drunk girls to their boat. It is totally a buzz kill and ends the night.
The next day we get up and sail to Anegada for a lobster dinner. We never see them again but what a night. Then we go to Jost Van Dyke for a couple of days. The only great thing that happens there is i flirt with a very hot chick. Turns out she is married though. Well that is my sailing trip.
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