Getting Down at Brown

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Their first time.
9.6k words
4.71
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Part 1 of the 4 part series

Updated 06/08/2023
Created 05/08/2017
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I had just gotten my pants back up when Jeff and his girlfriend, MaryEllen, walked into the dorm room Jeff and I shared. Jeff went straight in to the bathroom, when MaryEllen smirked at me and said, "If you're going to jack off in this room, maybe you at least ought to do it in the bathroom."

I was busted. I didn't realize it for a second, but a deep breath was enough to tell me how she knew: I could smell my sperm, wrapped up in some toilet paper, in the trashcan, where I'd hurriedly thrown it when I heard Jeff's key in the lock.

Jeff was still in the head when she came closer and sort-of whispered to me, "You know, masturbation isn't good for guys. When you beat off, you're training yourself to get off quickly, but when you're with an actual woman, you want to hold back until she gets off. Think about that, next time."

Jeff came out of the bathroom a minute later, and announced that they were heading down to the cafeteria for supper. At least his girlfriend didn't say anything to him while they were still in the room, but who knows what she'll tell him once they're out of my earshot.

Yeah, guys masturbate: everyone knows that. Still, it's damned embarrassing to get caught at it. Thing is, MaryEllen's 'advice' was probably good, and I kept thinking about it. The problem with that is that I didn't have a girlfriend, never had a girlfriend, and here I was, a 20-year-old junior, and still a virgin.

Why? I'm not the greatest looking guy in the world, but I'm not ugly, either; I'm about as average as average gets. My name is Max, which ought to be a great name for a guy, but I just don't get noticed very much. In a college environment where the 'alpha-males' grab up the good-looking girls, well, nobody every called me an alpha.

Oh, I wanted to be one, wanted to have the confidence to just take what I wanted, and kept playing through my mind how I should have responded to opportunities, how I should have approached the girls I wanted to talk to, but playing them through my mind was as far as I ever got. When I saw the girl of my dreams, dreaming was all that I could do, trying desperately to think of an opening line, and never coming up with one before the opportunity was lost. Even a simple, "Hi," in the cafeteria line, was tough for me, and the couple of times I worked up the nerve to try it, all I got was a "Hi" back, and then the girl would head over to a table with other people.

I was going to go all the way through college, and graduate a virgin. I was going to go through forty years of my career, and retire a virgin.

I'm a math major at Brown University, an Ivy League school in Providence, Rhode Island, one of the most progressive areas in the country. Brown has "gender-neutral" housing - if you volunteer for it - which appealed to me, hoping that I'd get assigned a girl for a roommate, but that wasn't really how it worked. If I had a female roommate, who knows, maybe I'd have gotten lucky. Instead, I got stuck with Jeff, who wasn't all that alpha, but he seemed to have an easy enough time around girls, and he hooked up with MaryEllen the first day in our dorm hall. At least, I guessed that he hooked up with her that first day, but even if it took him a day or three, they've been together ever since, and more than once he told me stories about how awesome she was in the sack.

The weeks passed, and I took MaryEllen's advice: when I beat off - I never quit doing that! - I'd try to bring myself close, and then back off. Training, she called it, and maybe it was, but one thing was certain: if I ever did get a chance to bed down with a girl, I needed to make the most of the opportunity, because who knows when I'd get another chance if I didn't perform well the first time. I stopped looking at pure porn, and started checking out advice sites, trying to study what I really needed to do. I really thought that I was getting better, or at least getting prepared, but I was still getting no opportunities.

November came, and fall can be a miserable time in Rhode Island. The days are windy and raw, the leaves long gone from the trees, and even a beautiful Ivy League campus like Brown's was stuck in autumn dreariness. Then, everything changed!

Jeff asked me, trying to sound casual but with a serious undertone in his voice, how I'd feel about a roommate switch. MaryEllen had talked to Sheila, her roommate, and she was OK with the idea of MaryEllen moving into Jeff's room, and me moving in with Sheila. The dorm was gender-neutral, so there wouldn't be any problems with Student Housing, and the only issue was my consent. One thing Sheila had insisted on: she was willing to share the room with me, but she didn't want to have to pack up, and I had to move in with her, not her in with me.

Me, I barely knew Sheila. I'd seen her in the halls, but that was about it. She was about as far from the gregarious MaryEllen as a girl could be, and I knew nothing about her.

"Anyway, dude, if you're cool with the idea, why don't you at least go talk to Sheila, and see if you'd be comfortable with it. She knows that you don't have a girlfriend, but she's not looking for a boyfriend."

"Yeah, well is she happy about MaryEllen moving out and her getting a male for a roommate?"

"She and MaryEllen got along OK, I suppose, even though they're like nothing alike. I don't know if she's happy MaryEllen is moving out, but she didn't object when MaryEllen made the suggestion to her."

"Is this Sheila waiting for me to talk to her or something?"

"I guess so. Let me call MaryEllen and see if Sheila is in the room." With that, Jeff called his girlfriend, and, sure enough, Sheila was there, and she did want to talk to me. I brushed my teeth quickly, headed down the hall, and knocked on the door.

"Hi," she said, kind of quietly, when she answered the door. "Come on in."

"Hi, I'm Max," I introduced myself. I was nervous, though not as badly as I thought I'd be. "I guess that this is kind of awkward."

"Yeah, it is." Sheila's voice was still quiet, almost too soft to hear.

"Just so you know, this wasn't my idea. If it bothers you too much, we can always tell them 'No.'"

"Well," she was talking slowly, "I guess that I can handle it if you can. I've never shared a room with a guy before."

"So, that just means we have to have solid ground rules, and respect each other's privacy as much as possible."

"Yeah." That was it, all she said.

"So, what's your major?" I asked, trying to get some sort of conversation started. "I'm majoring in math, and while it's not official, I'll wind up with enough coursework to declare a minor in physics."

"OK, that's cool. I'm studying education, hoping that I'll be teaching some day." Her answers were still kind of short.

Eventually I was able to draw out some more information from her, mostly by telling her about me; I guess that she figured she'd have to share the same kind of stuff with me. It took a while, but we started to get less nervous around each other.

Sheila was just about as awkward around guys as I am around girls, so in a strange way, we had that in common. If I was pretty much average for a guy, she was for a girl. Her hair was a kind of mousy brown, cut shoulder length, but with no particular style. Her figure seemed slight, but in a kind of bulky sweater - hey, it was November, after all - it was just sort of there, average again. She was shorter than me, somewhere around 5'3 or 5'4.

"Hey, Sheila, it's around dinnertime. Want to head down to the cafeteria, and we can keep talking about this?" Wow, that was almost like asking a girl out on a date, or as close as I had ever gotten to doing so, but I didn't even realize it until after I had said it.

"Sure, we could do that." With that, she pulled on a pair of sneakers and grabbed her wallet with her meal card.

"Let me stop at my room, so I can grab my meal card," I said, and we headed back up the hall.

Well, there were Jeff and MaryEllen, in my dorm room, and naturally, they wanted to know if Sheila and I had agreed to this. I hesitated for a second, and then Sheila beat me to the punch. "Yeah, we're going to try it. We're just heading down to dinner, to discuss the details."

I was kind of surprised. When Jeff asked the question, I was going to defer to Sheila anyway, but she stepped right in there and took charge. I noted that, once we got our meals and sat down in the cafeteria.

"Well," she said, "I'd already told MaryEllen I'd do it, as long as you were OK. I'd signed up for the gender-neutral dorm anyway, just to see what would happen. I grew up with brothers anyway, so I know how to share a bathroom with guys. My only real issue is that I'm kind of a neat freak, and I don't want to see a bunch of toothpaste or soap scum or other nastiness all over the bathroom. MaryEllen is nice enough, but she's a bit of a slob that way."

"OK, fine, I can do that, but that kind of needs to be a rule: if one of us does something that bothers the other, say something, and don't let it fester. Oh, by the way, I didn't have any sisters, or brothers, and had a bathroom to myself when I was growing up."

"I always changed my clothes in the bathroom anyway when MaryEllen was there, so that's nothing I have to change. If we have to get ready at the same time, you can change in the room while I use the BR."

"That's fair enough. I don't really take that much time in the bathroom in the morning; I just have to shower and shave, is all."

We pretty much got everything settled, and I moved in the next day. There were a few giggles from the other people in the hall, but I didn't have that much stuff to move; MaryEllen had more junk to move out than I had to move in. Naturally, as a math major, I had a pretty awesome computer set-up, a desktop as well as my laptop, but the whole dorm was set up with WiFi, so it was easy enough. The closet I got looked a lot less packed with my stuff in there than it did when MaryEllen's stuff was in it. Yeah, Jeff would be getting laid more, but I wasn't so sure that he was going to like having all of his girlfriend's stuff crammed in the room.

Once my stuff was in the new room, it looked a lot better than it had. MaryEllen was a mess anyway, and she had so much crap, not just clothes, that the room had looked like a tornado had hit it; with my stuff replacing hers, the room looked, if not Spartan, at least neat and organized.

I've got to admit: my first night sharing a room with Sheila was just plain nerve-wracking! She wore full pajamas, with long pants and a long-sleeved top, which was kind of disappointing but really a relief as well. I had mental pictures of her in a short baby-doll night gown, but if she has one, that wasn't what she wore that first night.

Or the night after that.

Or the night after that.

Actually, we settled into a quiet, respectful routine. Hey, I'm a guy, and I wanted to catch a glimpse of her undressed, but that never happened. As she said, she changed in the bathroom, the door always closed. We both had 8:00 AM classes, but she arose first, and went in the bathroom to shower and stuff, and always emerged fully dressed for the day. Me? While she was taking care of her bathroom stuff, I stripped out of the pajama bottoms (sometimes gym shorts) and t-shirt in which I slept, and had a new t-shirt and jeans on by the time she was done. My hair is short enough that I don't have to dry, or even comb, my hair, and that meant I took far less time in the bathroom. Sometimes we left for breakfast together, and sometimes we didn't.

Thanksgiving break came and went, as classes moved into December, meaning that exams were coming up. We both had to confirm our dorms for the spring semester, and Sheila and I were now both comfortable with each other, and made the switch to being roommates official.

 

The best thing that came out of this was that now I could talk to girls, or at least to one girl, casually, without being a nervous wreck, and, a week before exams, Sheila finally started opening up about her life. She came from a well-off enough family - hey, we were both in an Ivy League school! - but she was just really, really shy, always had been. Her parents were both outgoing, as were her brothers, but she was the family wallflower - her word, not mine - and just didn't meet people or make friends easily. She'd had one date in her life, one, and that was her senior prom, asked out by a guy as socially awkward as she was. He thought he could fumble around and get her dress off, but that didn't happen. She didn't say so, directly, but she sure implied that she was a virgin.

That was great, as far as I was concerned, and led me to 'fess up about my own virginity. I was specific, where Sheila never was, but she didn't seem the least offended that I assumed, from what she said, concerning her virginity. It kind of brought us closer, in a way I hadn't guessed it would.

Still, if Sheila was thinking of me as perhaps being a boyfriend, she never let on. Me? I was messed up in the head, still focusing on the hot babes all over campus, while I was roommates with a nice but hardly impressive girl. I could tell a little more about her figure now, since I saw her in her pajamas every evening, but it was nothing that set me off. She had boobs, maybe a B cup pushing out the top of her PJs, but then the top hung straight down past her waist, not defining her figure at all. He pajama bottoms hung loose on her, not giving me any clue as to whether she had nice legs, though I figured that they were at least decent from seeing her in jeans.

Her jeans weren't skinny jeans by any means, but like most girls, they fit fairly tightly. She looked decent, but nothing spectacular.

And the truth was that I was getting more attached to Sheila. I don't know if she realized it, because our relationship was about as brother-and-sister as it could be. I helped her with some problems she had in calculus, and she edited a couple of papers I wrote, telling me that it was a good thing I was a math major, because my English grammar sucked. "How the heck did you ever get into an Ivy League college?" she teased me, with a play punch on my shoulder, after fixing some fairly atrocious sentences in one of my papers.

Really, that meant two things. First of all, it showed just how comfortable we were around each other, because we'd never have joked like that before. But more, it was the first time she deliberately touched me, in any way, and it set my mind roiling.

It was the last day of exams, and Sheila would be leaving for Christmas break; her parents would be by around 3:30 to pick her up. We were busy packing, and - I even planned out the time - at 2:30, I handed her a small, gift-wrapped box, with a card addressed to the Best Roommate Ever.

"Max, I didn't get you anything," she protested, but I didn't care. As hard a time as I have shopping for presents, I assumed that other people did as well. I'd never seen my roomie wear any kind of jewelry at all, so I had gotten her an inexpensive, but still understatedly pretty necklace. I'd thought long and hard about what to get her, something that wasn't somehow too much, but one which could be interpreted as either just friends nice or hey, I kind of like you.

Sheila opened it on the spot, got a big smile on her face, and I thought, but wasn't quite sure, a bit misty-eyed. My Christmas present from her was a hug, a genuinely appreciative hug, not something that felt the least bit forced, but one which could still be seen as a safe, between-friends hug.

When her parents arrived to pick her up for the holidays - her family was from Portland, Maine - they were perfectly polite to me; Sheila had already told them about the roommate switch, so they weren't surprised that her roommate was a guy. I did hear, when I stepped into the bathroom, a hushed question from her mother, asking if I was her boyfriend. "No, of course not, mom," was the answer I heard, before walking back out. I offered to help carry down anything she needed to take with her, but other than some clothes and her laptop, she was leaving her stuff here.

 

The Christmas holidays just dragged by. The holidays themselves were fine, but we had two and a half weeks between the end of Christmas and returning to the dorms. I found myself missing Sheila, a lot, as she was really the closest friend I ever had.

New Year's Eve was party night, and as I was still not 21, that meant no nightclubs or anything. Some high school friends of mine were having a New Year's Eve party, and I actually got invited, something I didn't expect. Here I was, middle of my junior year in college, and I hadn't been to any real parties, and maybe I should have known how to act, but really, I didn't. The guys there, both better looking than me and some worse, were all managing to chat up the girls, the pretty girls and average girls. Somehow, the not-so-cute girls had not gotten invitations; imagine that. Trouble was, there were more guys there than girls, so I was shut out of the action, talking only to a couple guys who were about as successful with girls as I was.

The most 'fame' I got was when it was divulged, not by me, that I had a female roommate. I kind of wanted to brag about it, and make it sound like it was a lot hotter than it was, but the truth is, I couldn't: that would be disrespecting Sheila. Yeah, she'd almost certainly never know about it, but my conscience wouldn't let me do it, and I told the truth. Of course, the guys all assumed that I wasn't telling the truth when I said that no, I never saw her naked or changing, because their fevered imaginations just wouldn't accept that. One girl, Shannon, one of the more popular girls when we were in high school, pulled me aside later on, and thanked me for being so respectful of my roommate, but then she headed back to the other guys. Here I had thought that tonight, maybe tonight, I might lose my V-card, but I discovered the truth pretty quickly: the ease that I now had talking to Sheila was ease in talking to one girl, not girls in general.

A week later, and I actually had a chance to lose that V-card. We lived in Stowe, Vermont, a small town, and I was the only guy there going to an Ivy League school. It was just assumed that I had a bright future ahead of me, and Madelyn, a girl a year younger than me, working as a waitress, started flirting. I was so dumbfounded, because no girl had ever flirted with me before, and Madelyn had paid exactly zero attention to me when we were in high school.

Madelyn wasn't exceptionally pretty, but she was cute, cuter than Sheila if I were to tell the truth, and she brushed aside my ineptness in talking to girls. She was as close to direct as could be without saying explicitly that we should go out, but somehow, what would have astounded and delighted me a few months ago just didn't seem right. She was better looking than Sheila, she was certainly more flirtatious and sexually open, but you know what? She just couldn't compare to the one girl I could talk to, the one girl who had never given me the first hint of wanting to be more than friends, the one girl who was like a sister to me, rather than a girlfriend.

I left Madelyn disappointed, and I was trying to kick my own ass mentally for turning down such an opportunity, but I just couldn't get all that mad at myself.

 

Finally, finally! winter break ended, and it was back to school. It's kind of a long drive from Stowe back to Providence, and my folks were late dropping me off, but I still got back to the dorm room before Sheila did. I hooked my computer back up - I'd disconnected all of my electronics for vacation - put away my clean clothes, and stowed all of my new toiletries. I was sitting on my bed, reading Exodus on my Kindle, when Sheila finally got 'home.' It was 11:15 at night, and her parents had a long drive back to Maine, so they didn't hang around. Sheila and I chatted for a while, telling each other vacation stories - I didn't mention Madelyn - and then finally she got up to go into the bathroom to change into her pajamas. I was already in my PJ bottoms and t-shirt, when I heard her say, "Well, crap!" in the bathroom. I wondered what I had done, when she came out, with her pajama bottoms on, but still wearing a new, kind of expensive-looking sweater. She stood, facing her bunk, her back to me, and then pulled off her sweater, and then her bra. All that I could see was her back, and I guess my jaw had probably dropped all the way to my waist, as she then put on her pajama top, back still to me, and then started buttoning it up.