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The Vacation Boyfriend

It has been quite awhile since I have had the chance to sit down at my laptop and write a blog post. It is not that I have not been writing, I have, just not the stuff you want to read… unless you are really into press releases.

If you follow me on Twitter you may remember I was recently in the Carribean. Jane and I were at an event in April and she won a trip for two to St. Thomas. We were ecstatic, I already had accrued vacation time and the rumor around the office was that I had better use it soon, as we were probably all getting canned anyway.

Janey and I flew from Chicago to Miami, then on to the island. We couldn’t wait, 5 days, 4 nights in paradise. We had no plans except relax in the sun, maybe snorkel or take some boat excursion and eat and drink. Perfect vacation.

It was on our second night that I met Tom, but later I would found out that he saw me the first night I was there… I’ll get to that at the end. Jane and I had purchased some rum to drink in our room, but we needed mixers. I went down to the closest restaurant just to purchase a Diet Coke. Tip: Marriott only has Pepsi in their vending machines, but they keep Coke at the bar for rum and diets, I assume.

It was on my elevator ride back up where we first, kind of, met. He was with two of his friends and truthfully, I did not pay much attention to them. My hair was wet, as I was half ready for going out, I was just wearing yoga pants and a tank, nothing special. I was not in meeting boy mode for some reason, which is odd, because… well, you know me. His friend asked me which bar is the best bar to go to, I said we just got here, I did not know yet. Then Tom and one friend got off one a floor below mine, the third friend was staying on my floor. He mentioned it was his birthday, that is why they were celebrating and I should come out. I blew him off.

Fast forward a few hours, Jane and I were sufficiently buzzed and it was time to go out. We went to the concierge and ask him where we should go, what should we do, etc. We wanted to get off the resort and visit a local bar, but one that was still safe for tourists. He directed us to one, and called a cab for us.

Jane and I go to this local bar, it was pretty touristy but still fun. We are drinking, we are talking, flirting, just having a good time. All of a sudden, I see the guy from the elevator who said it was his birthday. So, I gave him a hug, said happy birthday, then asked if he wanted a birthday shot. Then Tom comes up and says he wants in on the shot, too, and that he wants a hug. I was pretty flirty, replied that it was not his birthday, but I would make an exception this time.

We start flirting like crazy, just talking, hanging out and after I mentioned I live in Chicago, he mentions that he is starting a rotation (med student) there in the end of July. Wow, OK. So it gets fuzzy from here. I remember at one point he kissed my cheek, kind of near the corner of my mouth and then I just grabbed his face and kissed him, hard. I was pretty drunk but it was one of those movie-like kisses, the I have to have you, I do not care who is looking type of kisses.

We made out all night. I never make out in the bar. I was pretty drunk and since I have cut down immensely on the alcohol, I get pretty drunk easily. Also, we were holding hands, dancing, just being ridiculous – like you are supposed to be. I was happy; I had found a vacation boyfriend.

Jane was being a good wing woman, too. Oh, did I tell you she has a boyfriend now? Yeah, it is lame. Not the boyfriend part, but the guy. That is for another post. But anyway, I knew she was tired but she was a trooper and closed the bar with me so I could hang out with Tom a bit longer.

We left the bar about 1:30am and the boys walked Jane and me to our room. Birthday boy (I seriously cannot remember his name right now) was trying to get on Jane so hard. I went into the room and told Tom to wait outside for a minute. We must have discussed that I was sleeping in his room, or maybe it was just assumed, who knows?

I wanted to talk to Jane and make sure she was not weird about me sleeping in another guys room. Also, I wanted her to know his room number as a safety precaution, just so she knew where to find me. I also freshened up and grabbed a few condoms to throw in my bag.

I exit my room and there is Tom, but also birthday boy. Birthday boy was smashed and kept asking me to let him in our room so he could get it on with Jane. Wow. Tom was far less drunk and we walked birthday boy to his room to sleep alone.

This is all still hazy, but I know more details after talking to Tom. We went to his room and I immediately said lets wash our hands. Good to know my OCD even kicks in when I am wasted. After that, I pushed him down on the bed. I got on top of him and we were crazy making out again. It was semi-rough but the kisses were still soft. At that moment, it felt as if two people have never had to have one another more.

That went on for a bit. I remember saying, “I am not sleeping with you tonight.” He said, “Good, because I was not planning on sleeping with you either.” I laughed, fully knowing that if I wanted it to happen, it would have. I did follow up with, “But you can still go down on me if you would like.”

Wow, I have such a smart little mouth when I have been drinking, but at least I know what I want, right?

He takes my pants off, but I am fully dressed otherwise. He starts giving me little kisses in between my thighs and then comes back up to my neck and nibbles gently. I remember it being so soft, his nibbles, and they were driving me mad. He then pulled my tank top down a bit and my left breast was revealed. He flicked his tongue across my nipple and it instantly got hard. Then put his lips around it and sucked for a second, finished off with a little bite. I was running my fingers through his hair, he was switching between kissing my neck and then nibbling on my nipple. His fingers found my right nipple and he was pinching it in the same fashion in which he was biting the left.

He lifted up my tank top a bit and gave my belly kisses. When he got to my hip bone I was so ticklish and so turned on at this point. I asked him to feel how wet I was and he complied by moving my panties to the side and inserting a finger. He did not insert all the way, just the tip and then pulled it back out to taste me. That was hot.

He then kept my panties to the side and started my thigh, above my pussy, then eventually his tongue was on my clit. I remember him being very impressed that I was smooth down there. He just kept kissing and licking and mentioning how smooth I was.

Here is where it gets weird. The next thing I remember was waking up to someone walking in the room, it was his other friend. For a moment I forgot I was not in my own room (I did remember I was with the boy, though.) There I find myself, at 4am, wrapped in the boys arms. I was wearing my panties and tank top. He felt me move around and woke up for a moment, too. He asked if I was OK, and he handed me water.

I took a sip and then said, “I feel like I may have fallen asleep when you were going down on me.” He said, “Yes, you most definitely did.” I replied, “Yeah, I’ve been known to do that. Sorry.”

He then hugged me tighter, kissed my ear and said go back to sleep. I did.

I woke up the next morning to the alarm. They were going on a boat that day and had to be up early. He told me to sleep in the room as long as I wanted but asked for my cell phone, so he could call his with my number. Before he left, he gave me a few kisses, two on my forehead, one on my ear, one on my lips. Then he says to me, “I have to see you again.”

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