Girlfriend's Away Pt. 01

I graduated from a directional state university in Illinois in 1991 with a double major in accounting and finance. I went through on-campus interviewing and was lucky (or smart) enough to get a job in beautiful, exotic... Milwaukee. Okay, maybe Milwaukee isn't on par with San Francisco or Seattle or Miami, but at the time the economy was in the tank and I was happy to just get an offer. Plus, even though I'd grown up in a small city in central Illinois, I'd never been to Milwaukee. All my journeys north only went as far as Chicago, where my friends and I would get royally drunk and limp home with crushing hangovers.

The moving allowance I was given as part of my compensation was way more than I needed to move my meager belongings, so I asked my childhood friend Sean if he wanted to come along with me. Sean hadn't gone to college. He was plenty smart and was even enrolled in a different directional state university when we were in high school. But around Christmas of our senior year his dad got laid off from his job at the local factory, and Sean had to stick around and get a job to help his family make ends meet. So while I was off at college, Sean was back in the old hometown working construction and taking general education requirement classes at the community college. By the time I graduated, though, Sean's dad had gotten a new job that paid better than his old one, and Sean was eager to finally get out on his own.

We found an apartment in a pretty hip but still affordable part of town. It was a two-bedroom on the third floor of an older building. The floorplan was sort of unique in that one bedroom was way bigger than the other, and you had to walk through that bedroom to get to the both the bathroom and the second, smaller bedroom. (I have since learned that such a floorplan would not meet building code requirements in most modern structures.)

The smaller bedroom had no closet, but the larger bedroom had a huge walk-in closet with built-in shelving and was more than big enough to hold the clothes for both of us that would not fit in our respective second-hand dressers that we'd bought from a thrift store. I took the smaller bedroom because it offered more privacy and I was still seeing my college girlfriend Rachel, who had yet to graduate but made it up as often as she could in her old hand-me-down Buick.

Things went pretty well in those days. Rachel graduated a semester after I did and moved to Milwaukee with a friend and got an apartment just about ten blocks from Sean and me. Sean got a job at a local outdoors store that sold hiking/camping/biking/skiing gear, and in no time was promoted to assistant manager. He also started taking classes at one of the local universities, which is where he met his girlfriend Sara. They were both in the forestry (or something like that, it had a more technical name) program.

Sara was a couple years younger than us but was about as far along in college as Sean was. She was sort of an earthy, granola-eating, mountain-biking girl who was very down to earth but also seemed to have a mischievous streak. She had neck-length, light-brown hair, blue eyes, and a very friendly and engaging personality. I had a little bit of a crush on her, owing in large part to the fact that I saw her left breast once when she was still asleep, topless, with Sean early one morning when I walked into Sean's bedroom to get a work shirt out of the closet.

By the time we had been there for about two years, Sean and I only saw each other two or three times a week despite the fact that we were roommates. I was out of the apartment before he got up most mornings and in bed by eleven most nights, some of those at Rachel's apartment. Sean was usually studying at the library past midnight and, like I said, was still asleep when I left in the morning. Or, he was at Sara's.

Summer of that year, Rachel and her family decided to take a ten-day trip to Europe. It was actually closer to a two-week trip, because it involved driving to/from her hometown in southern Illinois on both ends. She invited me to come along, but I couldn't swing that much PTO. Plus, I loved Rachel, but I was NOT interested in spending that much time with her family. Hell, I don't know if I could even spend that much time alone with just her or ANYone without going nuts. So we kissed goodbye on a Tuesday morning and she vowed to send me postcards and bring me some souvenirs.

Thursday night of that week, Sean and Sara and I decided to go to a divey neighborhood bar that we liked and have a few beers. It was still the interim between the end of spring semester and the start of summer semester, so both Sean and Sara had more relaxed schedules than they would when summer semester started in about a week and a half.

Sara had just gotten back that afternoon from a week in Montana or Wyoming to some such place visiting her grandparents and she was eager to tell Sean, and whoever else was around, about her trip. We got a booth with those two on one side, Sean on the inside, Sara on the aisle to his right. I sat across from them. Not surprisingly, a few beers turned into a few pitchers. We rarely got to hang out together because of our conflicting schedules, so this was a fun opportunity to just talk about nothing.

Midway through our third pitcher, Sara asked why Rachel wasn't with us.

"She's on her way to Europe for about two weeks," I told her.

"Ooooo, gonna be a lot of cold showers in your life for a while," replied Sara with a grin.

"I'm sure I'll manage just fine," I assured her.

"I guess you do have the old manos to keep you satisfied. But you gotta admit it's not the same thing," she said, still grinning.

"I have no idea what you're talking about," I said, feigning ignorance.

Of course, I knew she was talking about masturbation, and I was certainly no stranger to that particular pastime. Even though my girlfriend lived ten blocks from me, I still masturbated a few times a week. I was in my early-20s. Guys are just that horny at that age. At least I was. But I had never admitted to anyone that I masturbated, and no one had ever admitted it to me, even though I was pretty sure that all guys did it. And I wasn't real comfortable talking about it. But Sara apparently was.

"Oh, don't be such a liar! Everyone does it!" Sara said indignantly.

"Everyone?" asked Sean, with his interest obviously piqued.

Sara turned her head to slowly to her left to look at Sean and said, "You're afraid to admit it too? Is this because of that Catholic high school you guys went to? You're not allowed to talk about masturbation?"

Sean opened his mouth, but no words came out.

At about that time, the beer I'd been drinking must have kicked in, because I decided I'd pursue this conversation further, but not in a lecherous way. Basically as a way to make this cute girl talk dirty to us.

"Okay, I admit it. I do it. Sometimes."

"You do what, Mike," Sara pressed, seemingly enjoying getting me to admit it.

"I masturbate. On rare occasions." I lied a little there.

"Okay, that's a start. And you, Sean?"

"I also masturbate," Sean replied obediently.

"Now was that so hard?" Sara asked jokingly.

This was fun, but I wanted more detail. So I asked, "How often do you guys do it?"

Sara looked directly at Sean, as if to inform him that he must answer first.

Sean shrugged and said "I guess two or three times per week? Depends on the week. And my schedule. And Sara's schedule."

"And you, Sara?" I asked.

"At least three times a week," was her prompt reply. "Usually more."

"Wow," I responded, "that's impressive."

"Look, it's a great stress reliever, and I have a lot of stressors in my life between work and school and balancing schedule and money and parental expectations," Sara explained. "Plus, it's damn fun!"

"Well I suppose it's easier for girls," I offered, "since you don't have the clean up to deal with."

"That's a fair point," conceded Sara, "but there are more important reasons for a girl to masturbate as well."

"Such as?" I asked.

"Well, for guys, cumming is easy. You have a cock, you get horny, your cock gets hard, you stroke it, or insert it in whatever - a vagina, a mouth, a watermelon -"

Sean and I looked at each other with puzzled expressions on our faces at that point.

" - and you cum. It's not difficult. It's usually harder for a guy to NOT cum than it is for him to cum. With girls it's different. Most girls have to learn HOW to cum. And it can be very different for different girls."

"Would you like to expound on that?" I asked, suddenly genuinely interested on a not solely titillating level.

"Gladly. Sophomore year, which was just last year, I spent the spring semester studying in Italy. We were four girls to a room, so we all became pretty good friends. One Thursday night towards the end of the semester, two of my roommates were out and I was studying in the room with my other roommate. She was an Irish girl. She was a senior so she was a couple years older than me. We were drinking wine because why not when the wine there was so good and so cheap."

"That doesn't sound like a very effective way to study," Sean interjected.

"We'd been studying for a long time so we were pretty much ready to wrap it up anyway. So my roommate and the wine she'd been drinking ask me out of the blue 'Have you had much sex?' I said 'Enough I guess, why?' And my roommate asked 'Do you like it?' I said 'Well yeah, of course, why wouldn't I?' She then went on to confide in me that she'd had sex with a few guys, including the guy she'd been dating most of the semester, and never really understood what the big deal about it was."

"Maybe she was lesbian," I offered, trying to sound worldly.

"She wasn't lesbian. We talked a little more and I asked her 'Have you ever had an orgasm?' and she said she wasn't sure. Of course, that meant that she hadn't, so I asked her if she ever masturbated and she said she didn't. So I told her 'Listen, you can't expect someone else to get you off if you don't know how to get yourself off.' Long story short, the next hour was pretty much me giving her a lesson in masturbation. And she did learn how to make herself cum, and the last two weeks of the semester she was hardly ever home at night because she was off having sex - actual good sex - with her boyfriend."

This was an earth-shattering revelation for me. I knew I masturbated and assumed all other guys did to and I basically knew what that looked like from doing it myself. But I'd never really thought about girls masturbating before. I'd seen a couple porn movies in my time (this was pre-internet days) and they, of course, involved scenes of girls sticking dildoes in their pussies. But those were porn actresses performing for the benefit of us horny, slovenly guys. This new idea of regular, cute girls making themselves cum with their own hand was the most erotic thing I'd ever heard of. Hearing Sara tell about it had made me about 75% hard and I knew I would be masturbating when I got home. Based on Sean's adjusting of his position in the booth, he was in a similar situation.

"What was the attire for this so-called masturbation lesson?" asked Sean, right before I could pose a similar question.

"Suffice to say less than full," was Sara's teasing response.

"So, did you actually see your roommate have an orgasm?" I asked.

"Most definitely. And the best part was the look on her face afterwards. It was like she'd seen the heavenly hosts and they'd showed her the promised land."

"Did you also cum as part of the lesson?" Sean asked.

Sara got a kind of "well duh" look on her face before saying "What sort of teacher would I be if I didn't?"

Sean and I both took drinks of our beers, and Sara followed suit.

"Wow," I said, "Consider me enlightened."

"Have you never seen another person masturbate?" asked Sara.

"I have not," I replied. "Well I guess the closest I've come is the couple porn movies I've seen, which had scenes where a guy pulls his cock out of the girl right before he cums and strokes his cock a couple times before cumming on the girl's torso."

"Umm, yeah," said Sara, "That's not necessarily a bad thing to do, but it is not the same as watching someone masturbate. Watching someone masturbate is much more intimate and much hotter."

"Have you ever watched a guy masturbate?" asked Sean.

"No. That one 'lesson' in Italy is my only experience in watching someone else masturbate. Unless..."

"Unless what?" I asked.

"Are you interested in exploring this further?" was her response.

"I am," said Sean.

"Me too," I added.

"Well then, I'd be interested in seeing a guy masturbate. Not just any guy. I'm not interested in anonymous sex. It would have to be a guy I know and trust and like. Like, for instance, you two."

My cock felt like it was going to burst through the front of my shorts based on where I thought she was headed with this. She continued.

"So, if I can watch one or both of you masturbate, then I'll let you watch me as well."

I desperately did not want to let this opportunity get away, but I was in a bit of a bind because Sara was Sean's girlfriend so it wasn't really my place to agree to her proposition unless Sean did so first AND consented to me taking part. Then Sean said something truly heroic. He said, "Let's do it. If for no other reason, than for the sake of our own education." The smile in my mind was way bigger than the smile on my face.

Sean had driven us to the bar, so we went out to the parking lot and I went to the back, driver's side door. Sara stayed by Sean's side as he unlocked the door and hit the switch to unlock the other three doors. Sara gave Sean a soft, sexual kiss and I saw her run her hand discreetly over his noticeably bulging crotch before she went and got in the passenger door.

The drive back to Sean's and my apartment was a blur, and when we got in the door we were all briefly struck with an "okay, what happens now?" moment. Sara broke the ice.

"Okay, boys, we've come too far to back out. How shall we proceed?"

I decided to talk because I'm more of a talker than Sean. "Well, it seems to me that just having one person undress and start to masturbate while the other two watched would be a little lecherous and not in keeping with the spirit of what we discussed at the bar. At least not as I understood it. The way I see it, masturbating WITH someone is much more intimate and respectful than masturbating FOR someone. If you do it WITH someone, it's more of a shared intimate experience than a mere sexual thing."

"I agree," said Sara, "but that doesn't tell us how to proceed."

"Well, let's think about HOW we usually masturbate, and then recreate that as close as possible."

"USUALLY I just lower my pants, put a sock on my cock, and do it," said Sean.

"That's interesting, baby, not really inclusive," Sara responded to him.

"And sometimes I do it in the shower," Sean added.

"Shhhhh, baby," Sara told him. "What about you, Mike?"

"Well I admit that I sometimes do with a sock like Sean described. Like if I'm in bed at night and hear you guys come in and have sex."

"You listen to us have sex?" asked Sara, raising her eyebrows in a not entirely disapproving way.

"But if I have time to myself," I continued, ignoring Sara's question, "then I like to make more of a full body experience of it."

"I think I like where this is going," said Sara, "Continue."

"Okay, most people when they have sex, including me, like to engage in some foreplay. Masturbating is having sex with yourself, so I like to engage in some self-foreplay."

"Such as?" prodded Sara.

"For starters, I like to be completely naked and in bed. I like the feel of the cool sheets on my body, and I like to be able to touch as much of my body as possible as part of the process. I also like to have enough lights on that I can see at least myself. So that there is a visual aspect as well."

"Don't take this wrong, Mike," said Sara, "but you sort of masturbate like a girl. Because that's how I like to do it. And pretty much every one of my girlfriends I've talked to about masturbation does the same thing."

"I certainly do not take offense at your comment," I assured Sara, "because based on what I've learned tonight I'm guessing that girls are much more eloquent masturbators than guys by and large."

"Perhaps we'll find out tonight," she replied. "So do you have any ideas for what happens next, right now, right here, with us three admitted masturbators?"

"Sure. I propose that we go into Sean's bedroom. Mostly because he's got a queen-sized bed and mine is only full sized. We turn down the blankets, all lie on the bed together, naked, and then masturbate, the way we would do so if we were alone, one at a time."

"I'm in," replied Sara immediately.

"Me too," added Sean.

"Great," I said.

But before anyone could make a move, Sara asked "But what order should we go in?'

We were all silent for a second, but then I had an idea.

"Hold on," I said, and went into the kitchen, where I pulled a piece of raw spaghetti out of a box in the pantry before returning to the living room.

"We'll draw for it," I said as I broke the spaghetti into three different sized pieces and held them out in my fist with just the top portions showing. "Short goes first, middle goes middle, long goes last."

Sean and Sara looked at each other, and then both reached for the spaghetti at the same time, leaving me with the last piece still in my hand. Then we all held our pieces of spaghetti in front of us.

"So then," said Sara, "Sean goes first, I go second, and you go last, Mike."

"Then let's," I said, and we all went into Sean's bedroom.

Sean had nightstands with reading lamps on both sides of his bed, and we turned both of those on and left the overhead light off. This left the room with light enough that we could easily see each other but still dim enough to offer some appropriate atmosphere.

I went to the far end of the bed and started turning the blankets down as Sean did the same from the side of the bed closest to the door. We then all began to undress. I didn't have any real qualms about being naked in front of them. I had (and still have) a pretty good physique. I was six feet tall, brown hair and brown eyes. I worked out regularly, and while I wasn't real muscular, I had a sort of angular leanness that more than one girl had complimented me on. And I had virtually no hair on my chest because, well, I just never did.

Sean was an inch shorter than me with sandy blonde hair and blue eyes. He was more muscular than I was but not in a bodybuilder way. He'd been a good basketball plyer in high school and had a basketball player's body (albeit a 5'11" basketball player).

I was eager to see Sara's naked body and was trying to discreetly watch her undress. But being discreet meant letting my eyes drift away from her instead of just ogling her, and when I let them drift I saw something that caught me completely off guard - Sean's hard cock was sticking out from a completely shaved pubic area.

Now Sean and I had been friends since high school, and I'd seen him naked in locker rooms on many occasions. I'd also lived with him for two years at that time and, while neither of us walked around naked, you can't help but catch a glimpse of your roommate naked from time to time. And every time I'd seen him naked before I'd seen a sandy-colored patch of thick pubic hair to match the sandy hair on his head.

I did not know what to make of it. I knew that Sean took advantage of all of the exercise facilities at the university and that included the swimming pool. And I knew that swimmers sometimes shaved their entire torsos and legs to cut down on drag. But I also knew that Sean wore the same baggy board trunks that he wore to the beach when he swam laps at the school pool, and the drag from those board trunks would more than defeat any benefit he derived from shaving his torso. Plus, he still had his usual amount of hair on his chest (which wasn't much) and legs. WTF?