[five hole]

Back in the late 90's I was in college and never really had much luck dating at the High School level. Truth be told I hated high school and it was the absolute worst four years of my life so far. Going to college was a great new experience and I made sure to go both where I wanted and far away from the people I went to high school with. I ended up dating a lot during my time there and found out that being the "good guy" during the hell years of high school would pay off in meeting a great girls.

One girl who I will never forget is Carrie. After my freshman year, I was debating whether or not to move out and get my own place, but financially it was not a good time. So I moved in with my future good friend Dan (who I would wind up renting a house with and three other girls, but that is a WHOLE other story). Dan and I planned to work our asses off, save and get a place. With busy first semesters, sports, and homework, we wanted to be able to do it right and not kill ourselves. So we started off living in one of the better student dorms (which was essentially an old hotel that overlooked the Atlantic Ocean in New England). The facility had several Resident Assistants who got their own room and were paid to work as an RA. Carrie was one of these RA's and we quickly became friends. Everyday I would see here when I came back from class working behind the front counter and I would get my mail from her. We would end up chatting for 15-30 minutes each day and got to know each other pretty well. In addition, I would ask her to go to dinner or lunch with me. Sometimes just us and sometimes with her friends, mine or a mix. Regardless we would walk there, eat, and hang-out and get into some kinda' fun trouble.

One weekend (our weekends started on Thursday night and we had off Friday, Saturday, and Sunday), I came to down to the front desk and saw she was really sad and there was usually no one around on the weekends unless you worked, lived too far away, or wanted to do school work. I asked her what was wrong and she started to cry. She leaned into my chest and I put my arms around her and I'm pretty sure although we playfully flirted with one another, it was our first time hugging or touching anyway other than being goofballs. She slowly told me what was wrong. It turns out there was some major mechanical problems with her car and she needed them fixed, but had no idea on how to fix it or who to go to. We both owned Volkswagon vehicles and I had just found a garage guy I trusted so I volunteered to take her there and see what he thought. Carrie followed me in her car and it "BARELY" made it there. The guy looked over the car and said he would get back to her on a price, but asked her if we were friends. I put my arm around her and said, "she's my girl Walt" to the owner. Carrie flinched a bit but smiled the whole time. Walt smiled and said something about giving her a discount since I brought her by with me. That made her smile bigger.

I drove her back to the dorm and she thanked me a lot for taking time out of my day to get her over there and the discount. It was not anything big for me as I just thought I was helping her out and she was a friend. So Friday comes around and Walt calls her and tells her that it will cost $1500 to repair everything and that is a discount for me since I regularly (my car sucked too) used him. Carrie was tears as she told me and I was blown away at the price. Holy shit that's almost as much as I had saved in three months of work... and then it hit me. She needed the car so she could drive to class, be and RA, and drive home every other weekend for work. I told her let's go talk to Walt and we did. She was so sad on the way there, but once we got there, I told her I'd pay if she could pay me back. At first I think she thought I was messing with her, but in a few seconds or a minute she realized that I wasn't. She hugged me and then she put her arms around my neck and kissed me right on the lips. I think we were both shocked that it happened, but I know we both looked at each other differently after that. There was an awkward moment of silence until Walt said something like, "You too need a room or you gonna' pay now?" We both giggled.

So repair work started on the car as we paid up front (well, I paid). I remember telling Dan what I did and he told me I was nuts. I believe he said, "You aren't even sleeping with her and you gave her $1500.00!!! What the fuck Matty, What the fuck!" I did question what I did and was nervous. That was a lot of money and well... that was a lot of money.

So in the coming days she started to pay me back and we started to slowly date too. I would take her out in my car as hers was fixed. On the night before her car was fixed, we went to a party several blocks away from the dorm and walked there. The idea was drink and not worry about being pulled over if the cops stopped us. We also decided to leave our IDs at home so as to prevent the cops from asking for IDs and seeing we were NOT 21. It was smart and worked one time for us (but not that night). It was cold out and we were walking back. I know I was intoxicated and judging by her idea to ride on my back piggyback style, I'd say she was too. So we get back to the door and we go to my room giggling and laughing. I decide to drop her on the bed, which was essentially me tossing her 5'03" body onto the bed. She rather enjoyed it and laughed.

At some point we started to make out and it got very heated quickly. The picture included was taken on that day as I said she looked hot. I am the guy in the picture I cut out, but I think you would rather see her than me. I was a full foot taller even though she said she was 5'3", I am 6'02" and that was definitely a stretch to kiss standing. Back in the 90's the overalls were popular for a bit and Carrie looked quite awesome in them. My hands were up that shirt and playfully teasing her hips as I dry-humped her through those overalls. Soon she couldn't handle it anymore and we were down to our underwear. My erection was all but popping out my boxers and during our kissing, I don't know what came over me, but I dropped down on her and pulled down her underwear (which I recall were thongs!). I then ended up licking her and touching her pussy. I had never done any of that and just tried to do what I thought was right. I think I did as she moaned and said my name in a soft yell as she arched her back and shivered after a few minutes. I brought her to that same feeling again this time as she lay nude. She was, however; quite loud and I hoped no one was next door listening. As she slowly calmed down I kissed her nipples, neck and lips and we continued to make out. Then she stopped kissing me and looked deeply into my eyes. I will never forget what those eyes looked like looking at me. They were a combination of want, thanks, desire, and dare I even say deep satisfaction.

"Stand up" she said quietly and I questioned her...but she repeated so I did.

She dropped my boxers and gently kissed around my thighs and "area" in general. She would look up at me from time to time with those eyes and that "LOOK". I enjoyed her kisses immensely and then she gently put her hand around my penis and started to stroke it. Her hand was dry and yet she was very gentle with it. Realizing the dryness, she wrapped her lips around it and started to suck on it. Then she'd let it slip out of her mouth so she could tug on it. I had never gone this far with a girl before, but I was very turned on. She repeated this stroking on me and sucking for a good 45 minutes because I know she asked if she was doing it wrong. I told her it felt amazing and she asked if she could go faster. I let her and soon I had that feeling that I was going to. She looked up and me and said, "are you?" and I nodded. I had never had an orgasm from anyone else other than me before and suddenly I shot. There must've been months and year of sexual frustration built up in there because my first shot flew out and hit her front teeth. The ricochet of it hitting her teeth flew back a little and dropped onto her lap and boobs. It wasn't that she was unhappy, but she looked like she suddenly didn't know what to do. She looked around as she continued to jerk and more came out. I don't know where it all went, but there was a good bit before some went into her hair and she finally just put her mouth over my cock and sucked the rest. I think BJs were new to her too, because I know she gagged at the amount I sent down her throat.

Pretty soon I was done, but she kept on sucking. She let my penis fall out of her mouth and I just laid beside her and held her. We fell asleep like that and the next day got her car. I know we dated the rest of the year with many more times of that, but she was definitely my first in that regard. And for the record, she paid me back everything she owed me monetarily!!! She also paid me back with BJs, but I won't ever forget that first one!

Oh and that my hand around her in the picture.