Truth be told, my attitudes toward sex were pretty conservative in my formative years, leading me to graduate high school in 1990 as a virgin who'd only managed to finger-bang Linda, my girlfriend who'd given me a few hand jobs. (This after she remarked that she'd expected my penis to be bigger - thanks for the esteem boost, John Holmes and other stars of early VHS porn!)
Linda's hardcore Catholicism had contributed to my hang-ups about sex. She'd roped me into a Monday night Christian youth group that I attended with her mainly so we could make out and touch each other's sexy parts afterwards. She clearly enjoyed it - man, did she ever get wet! - but then she always told me about how she felt guilty afterwards. And the first time she got me to come she reacted as if I'd shot Satan's spit all over her hand and wrist! So that relationship didn't last all that long; we couldn't put the sexual genie back in the bottle once we'd started to touch each other below the equator but she didn't want to lose her virginity, either.
Beyond my own experience, I found myself repulsed by the way a lot of my peers talked about sex. Maybe it was because I was close with my mother and sister, but I just couldn't objectify women the way so many of my peers did. Like I found myself incredibly grossed out when I learned that two of my good friends lost their virginity within the space of a few weeks to the same girl, a very sad-eyed coed, at the behest of this annoying preppy dude they'd begun hanging out with who had clearly also been with her.
Then you add in the fact that I was a *huge* Smiths fan and took Morrissey's every lyric about how confusing and terrifying all things sexual were and...well, I just learned not to think with my little head. I was living under the mistakenly naïve notion that any act of sex was a crime against women and decided not to be a part of any of it, taking a very good friend to senior prom without sharing so much as a real kiss.
Flash forward to the first semester of my freshman year of college life on a coed dorm floor in 1988. Were there hookups? Oh yes. Did I have any? Hell no. Was I hoping to? Well, possibly. But my lack of "game" quickly got me pushed into the "friend zone" by most women I was interested in. I was described as cute enough, known for my sarcastic wit, appreciated for my smarts...but also shaping up to be the last virgin on the floor. (Well, except for the gamers and a few of the Christian youth group types.)
The female version of me on my dorm floor was Kris, a brunette who idolized Sandra Bernhard and a few other caustic woman comedians of the day. Kris was on the tall side, with a pretty-enough round face, brown permed hair that fell a few inches past her shoulders, big bright brown eyes, smallish breasts and a nicely rounded rear end that became a little more round each month as she fought the dreaded "freshman fifteen."
Kris and I would verbally spar whenever she was around, which she often was because she seemed to have a thing for my openly gay roommate. Looking back, I know that she and I were both insecure and tended to build walls of words around ourselves as a sort of coping or defense mechanism. At the time it just seemed the way to be in order to get by at a mediocre land-grant university.
So there I was on the weekend following Thanksgiving break, a cold and rainy Saturday night. I had a paper due in my composition class Monday morning that I was trying to get a head start on (versus kicking the whole thing out in a caffeine-and-nicotine-fueled binge on Sunday night), so I'd opted to stay in rather than walk the mile or so over to a kegger that a bunch of my floor mates had decided to hit.
I was making decent headway on my paper when I looked over at the clock and saw it was 10pm already. The two cans of Mountain Dew I'd used to jolt my brain into action were ready for their exit, so I made my way over to the men's bathroom. As I urinated I thought about how my roommate wouldn't be back from the kegger for a few more hours, so I pondered treating myself to a wank when I got back to my room.
As I walked back down the hallway I was surprised at how still things were with quiet hours not due to hit until midnight. I'd been playing music through my headphones while working on my paper to drown out the loud music and TVs that typically blared throughout the dorm on weekend nights. When I got to the room Kris shared with her roommate Erin, three doors down from my own, I saw that the door was partway open and decided to stop and see who else had decided to stay in for the evening.
I knocked twice, then popped my head in. "So, what loser beside me is staying in tonight?" I said by way of greeting before noticing Kris lying on her side on her twin bed, her face etched in sadness, listening to some female vocalist's music quietly. "Is something wrong?"
"Yes. No. I don't know."
"Well, that's clear enough," I said, walking into the room, picking up the cheap vinyl-coated chair from Erin's desk. I placed it on the ground, sat backwards in it, facing Kris. "You're not your usual chipper self. What's going on?"
"I dunno. I don't want to talk about it."
"Okay," I replied, not wanting to be a pain in the ass. "Should I go?"
Kris was silent for several seconds, then finally said "No. It's okay. Can you close the door?"
"Sure," I said, getting up and swinging it shut. I walked the four steps back to the chair and began to straddle it again.
"No. Don't sit," Kris said. "Come here and lie down with me."
"Oooooh, gross," I replied with a laugh that I quickly swallowed as she began to cry.
"Thanks, asshole. That's just what I needed to hear tonight," she choked out.
"What? No. Don't cry. I'm sorry," I replied. "Move over, make a little room."
Kris rolled over, now facing the wall, and I lay down next to her. She flinched as I placed my hand on her shoulder, and I quickly took it away. "No, it's okay. I just didn't expect you to touch me. Will you hold me?" I wrapped my left arm over her waist, slid my right beneath her, joined my hands together and held her close in a spooning position. "Thank you. This is nice." It was. As much as I'd enjoyed touching my high school girlfriend above and below the waist, close contact may have been my favorite part of being with her.
"So what's wrong?" I asked again, talking into the curly ringlets that covered the back of her neck.
"Do you know that guy Dave who lives on 2C?"
"The wanna-be surfer guy?"
"Yeah, him."
"What about him?"
"Well, I thought he was into me. So I somehow got up the nerve to see if he wanted to go to see the movie at the student center tonight. And he said yes. But then today he called me and said he'd hooked up with a girl from his floor last night and plans to spend the weekend with her now."
"I'm sorry. That sucks."
"Yeah. I swear to God, I'm going to die a virgin."
"Me too," I answered unthinkingly.
"Wait, what?" Kris said, rolling over to face me, her wide eyes showing her surprise. "You mean you've never...but you're always hanging out with girls. And some of them are pretty hot."
"I know, but...I think I maybe overthink things? Or something?" The searching look in Kris's eyes suggested this was not a time to think, but to do. And so I did, closing the several inches between us and putting my mouth on hers. She reciprocated, slid her tongue into my mouth, against my teeth as mine joined hers in eager exploration. I ran my left hand around her right cheek, played with her ear a bit before sliding my hand lower, palmed her right breast, felt her nipple stiffen through the cotton of her sweatshirt as my cock stiffened in my sweatpants.
"Oh, Tony," Kris moaned as I kissed down her chin, down to her neck, teasingly sucking for a moment, alternating licks and sucks and nips on her sweet, soft flesh. "Yessssss," she whispered as I ran my hand beneath her sweatshirt, kneaded her breast, a wonderfully soft handful that perfectly filled the palm of my hand.
"Is this okay?" I asked as I began tugging at Kris's sweatshirt. She nodded yes and helped me pull the garment over her head, then rolled over on her back. I straddled her, continued to kiss all around her face and chest, paying special attention to her perfect, perky pink nipples and quarter-sized aureole. She pulled me back up to her face and we kissed again, bringing my erection into contact with her femininity. I reflexively thrust against her and felt her raise her hips in response. The contact felt amazing, and I hovered above her as she spread her legs. I thrust again, not entirely certain where I was contacting her, just luxuriating in the sensation as we began to dry-hump, both of us moaning and sighing.
"Let me see it," Kris suddenly said, pulling me out of the moment as she took my hardness in her hand through my pants. I rolled over onto my back, shimmied out of my sweats for what seemed like an agonizingly long time until they bunched up down by my knees. Her hand wrapped around my cock, which stood firm and proud through the gap in my boxer shorts, explored it. "It feels so...spongy," she said as she ran her thumb and forefinger around my head.
"That feels really nice. I'm way too used to my own hand," I joked. She chuckled as she continued to gently manipulate my cock, slowly tracing her way down from my bulbous head, circling my circumcision scar with curiosity, running a finger along my main vein across the top of my length until she got down to the root, then felt around my sack.
"I didn't expect your balls to feel so...weird," she said. "They just sort of float around inside there, eh?"
