Disclaimer: All of the characters are fictional and over the age of 18.
~~~~~
"Dammit, Kurt, we need to get you laid at least once before we graduate!" said my roommate Dave. Graduation was in about four weeks.
"Mister Tongue-Tied?" asked Tom. "Good luck with that. Have you ever thought about a prostitute? I'll chip in."
"So will I." said Jasper. "What do you think?"
I blushed, even though this wasn't the first time the subject had come up with my roommates. "C'mon, guys, I don't want my first time to be with some unknown woman I need to pay to have sex with me. I want it to at least be a girl who likes me, who I like back. But you're right, I get tongue-tied anytime I make that my goal. That's the real obstacle. Paying a prostitute isn't actually going to solve that, even if I managed to go through with it. If anything, it will just make me more convinced that I'm a failure at relationships."
It was nearly the end of my college life and I was still a virgin. Not because I really wanted to be or was saving myself for my future wife. No, I was one of those poor cases where my brain freezes up around women whenever I was thinking about trying to be romantic with them.
Study buddy? No problem. I was asked to do that a lot, maybe a dozen different girls over the past four years, and agreed because it helped my grades, too. These were usually pretty girls, used to getting guys to help them out. So long as I kept my focus on studying, I did just fine being around them. The fact that I didn't hit on them only brought more girls to my door.
I really wished, though, that I could turn that kind of relationship into something more, but whenever I thought of it, I couldn't speak. I just froze up, until I gave up on the idea. For whatever reason, none of the girls were making a move on me, either. I wasn't even getting close to the "I'm a virgin at 22" speech that I knew I'd have to reveal before changing that status.
To be honest, I had nearly given up hope of ever losing my virginity, finding that I could enjoy myself more at parties if I stopped worrying about trying to flirt or picking someone up, could study better if I was only thinking of a study buddy as a study buddy.
Until one day, about two and a half weeks before finals were going to start...
~~~~~
I was coming back from Friday classes to our first-floor on-campus apartment, when I heard a woman's voice shout, "You want us to do what?!?" from the apartment next to ours, through an open window I knew was one of the bedrooms.
These were student housing right on campus, cheaply furnished two-bedroom-one-bath apartments housing four students each, with a small kitchenette and a living room. As the best housing option on campus, they were picked by the upperclassmen first. As we were seniors and I had a high GPA to select our apartment for the group, we had picked one of the better locations, closest to where our classes were.
The shout came from the apartment next to ours, across the stairwell that led to the two floors above us. It was occupied by four women, Colleen, Dani (aka Danielle), Susan and Wendy. All of them had been regular study buddies of mine multiple times over the years. We'd even gotten to the point of selecting courses that we could take together, just to be able to study for them together. At least one of them was in every course I had that last semester. All four of them were gorgeous, in their own ways. I would argue that they were the best-looking foursome on campus, maybe even the four most beautiful women I knew.
I crept closer to the open window, when I heard, "We want to get Kurt laid." That was Jasper's voice. "And we think you four are all perfect candidates. You've been platonic friends of his for a long time, you even chose the apartment next to us just to make it easier to study with him. I know for a fact he thinks all of you are hot. He just has this thing where he can't make a move on you, because he can't speak straight when he tries."
It was Colleen who spoke next, saying, "So you're offering a $100 prize to whichever of the four of us gets him in bed first? What do you think we are, prostitutes?"
Tom answered, "No, of course not. He's opposed to going to a prostitute, anyway, wants it to be a girl he likes and who likes him, which fits all four of you. You ought to do it for him out of gratitude for all of the courses he's helped you out with over the years. We all know you each would not have your current GPAs if not for him. If the money is your only incentive, instead of an added one, don't bother. Do it because he's your friend, and he needs this. Consider the $100 a bet that you can actually get him to give in. He's not to know about the money whatsoever."
Well, that ship had already sailed. I backed away from the window, just as I heard Wendy say, "Okay, we'll do it."
So, what exactly could I do with knowing ahead of time that the girls were coming after me? I sure as shit wasn't going to play hard to get, unless my shyness itself got in my way, but an idea did occur to me. I turned back around, and headed to the center of campus to get my little plan started.
~~~~~
Our usual weekend activities unfolded, a lot of it spent with the girls as a group together with my roommates, and I never had an opportunity to be alone with one of them without the guys around.
I studied with Colleen and Susan in their apartment for the last history exam before finals that Sunday night, with nothing happening. There wasn't even a hint that they were thinking of seducing me. Or maybe I didn't see a sign that would have been more obvious to a more experienced guy.
It was the next night, when I was studying with Wendy for both of the classes we had together, with the first hints of finals preparation, that everything started. My roommates were conspicuously absent, so we were spread out on the sofa and coffee table in the living room, rather than trying to study on the ridiculously small kitchen table the college provided, or trying to fit at the one desk I shared with Jasper in our bedroom.
An hour in, she excused herself to go to the bathroom. I was beginning to wonder whether the girls had backed out of the agreement they made, when Wendy came back, her jeans and shoes gone, and it took little time to see that she'd also relieved herself of the bra she had on, as her big tits were wobbling all around underneath the remaining tshirt the whole walk back from the bathroom. The tshirt covered her privates, barely.
Wendy was about 5'7", three inches below my 5'10" height, although she often wore heels that put us eye to eye when standing. She had straight, sandy blond hair down to her shoulders. She was really smart, contrary to the cliche. She was my favorite study partner, because she helped me at least as much as I helped her. Because we were both pursuing the same double major with a minimal number of electives, we wound up in a lot of the same tough classes, and had started studying together Freshman year, when we were all in the dorms. Her roommates became my study pals because of her, Susan first, then Colleen and Dani, whenever we were all in the same courses, later without Wendy involved.
With a big bust and a curvy butt turned into an hourglass shape by a well-exercised abdomen and a narrow back, she was also the girl most likely to give me an erection during a study session, which I always hoped she wasn't noticing. She'd never said anything but you never know. She did not have a reputation as a tease but I would have made an easy target. If I had wished for any of these four girls to be my first, it was her. Although I hadn't admitted it even to myself, I was in love with her. I just didn't know what to do about how she made me feel. She was about to teach me.
