First Is the Worst
Tem 16, 2022 // By:analsex // No Comment
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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, the one 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 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 my sisters, but I just couldn’t objectify women the way so many of my peers did. 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 frumpy, sad-looking coed, at the behest of this one skeevy preppy dude they’d begun hanging out with who had clearly also had 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 very 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 female 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 1990. 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. (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 the other caustic female comedians of the day. She 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.
It was 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 thought I might treat 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 bonus veren siteler 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 her roommate 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.”
“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?”
“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, Steve,” 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, 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 bedava bahis her way down from my bulbous head, circling my circumcision scar with curiosity, running a finger along my main vein along 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?”
“Haha, yeah. Be careful with them. The berries are much easier to hurt than the twig.”
“Twig, eh? I’d say it’s more like a nice thick branch,” Kris replied, making me feel proud of my average-sized endowment. She rubbed my head, eyes opening wide with surprise when precome emerged from my slit. She played with the substance, intrigued by the fact that it was both slippery and sticky, the way it stretched an inch or so between her finger and my cock before snapping. “An interesting, interesting branch.” I laid back, eyes closed, as she rubbed my fluid into my cockhead.
I was momentarily disappointed when her hand went away, then shocked when I felt something warmer and wetter replace it. I opened my eyes, saw that Kris had decided to take me in her mouth. “Oh my God Kris, I didn’t expect this,” I moaned as she engulfed my head and ran her tongue along the underside of it. “That feels amazing.”
“It tastes and feels…weird,” she finally said as her mouth slid off of me. “How do people do this?”
“It’s only skin?” I joked in reply, echoing a line a high school friend of mine had unsuccessfully thrown at his girlfriend a few years ago.
“There seems to be hair, too,” she replied, giving my balls a tentative lick that felt wonderful before sitting up. “I don’t think I can do this. I’m sorry.”
“It’s okay,” I replied, disappointed but understanding. “Can I…can I touch you?”
“I thought you’d never ask. We might as well get naked, right?” We rolled off the bed, and I pulled my tee shirt over my head, then sat down to remove my shoes, socks, boxers and sweatpants. She too removed her socks and shorts, stood in front of me in cotton-print underwear with our university logo on it. She sat back on the edge of the twin bed, legs spread, looking downright seductive, surprisingly hot bereft of the baggy clothing she typically wore. “Care to do the honors?” she asked with a lusty smile, pointing down between her legs.
I kneeled before Kris without a second thought and laid a tongue-filled kiss on her left knee, then proceeded to slowly kiss and lick my way up her inner thigh. Her skin felt and tasted delectable; a soft floral scent from whatever product she used for washing or moisturizing lingered beneath a slight saltiness. The little sounds she made as I did so were like music to my ears, encouraging me upward until my tongue was confronted by her moist cotton garment and my nose was filled with a wonderfully clean, fresh feminine scent I hadn’t enjoyed in more than a year. I used a finger to pull slightly on her panties, then clamped my teeth on them and pulled slowly, playfully, inching them slowly down her thighs before I impatiently hooked both thumbs into them and pulled them all the way off, leaving her wondrous womanhood fully exposed to my hungry eyes, my curious fingers, my yearning mouth.
I tried to remember what I’d clandestinely read about cunnilingus a few years ago in one of my mother’s *Cosmopolitan* magazines, which advised going slowly and paying attention to the clitoris and her reactions. I started by rubbing a thumb along her slit, feeling through her short curly brown hair, gently applying pressure to part her inner lips. Encouraged by her wetness, I slid a finger into her up to the first knuckle, then placed my thumb above her opening and circled around until I felt a small bump of sorts. I concentrated my efforts on that bump while sliding my finger in deeper, ultimately turning my hand over so that my finger made a sort of hook with which I tried to touch my circling thumb. Kris’s gasps told me I was onto a good thing. I reflexively began humping the mattress in time with my slow motions, my shaft maintaining its youthful hardness.
I removed my hand and pushed Kris’s legs further apart as she slid back to the head of the small twin bed, propped up by her pillows and sitting partly up on her elbows. I advanced, placing my mouth over her mound and giving it a single long lick from the bottom of her opening up to her clitoris. I rubbed my face over her, my face growing slick with her juices as I inhaled the uniquely sweet scent of a young, aroused woman while my hands caressed her breasts. I stabbed at her with my tongue, then returned to licking, noting that she didn’t seem deneme bonus to be as turned on by my mouth as she was by my hand.
“Am I doing okay?”
“I’m not sure,” she replied with candor. “Maybe oral isn’t my thing altogether?”
“Should I stop?”
“Maybe there’s something else we can do?”
I almost gasped in response, my cock involuntarily twitching several times. “Do you mean…intercourse?” I finally said, trying not to sound crude, failing to make it sound romantic.
“I mean…let’s fuck. I’ve got condoms from our welcome pack in the top drawer there,” Kris said, point to her dresser. I got off of the bed, my hard cock bobbing as I walked the few steps across the small room and opened the drawer. I quickly found the pink cardboard box, opened it up and removed one of the Trojans. “Do you know how to put it on?” she asked.
“Of course. I’ve practiced for this moment and jerked off while wearing them.”
“Smart boy. You’ll make the freshman honor roll at this rate.”
“Ha,” I replied, standing next to the bed, tearing the foil packet open while Kris’s wide eyes watched. I stroked my cock a few times, then placed the latex sheath by my head and rolled it down to my root.
“That looks kind of funny,” Kris said. “Does it feel weird?”
“Only a little,” I said, lowering myself to the bed, moving my body over hers. Our eyes locked. “Are you sure you’re ready?”
“I am,” she said, reaching down and stroking me through the slick synthetic material. I felt her guiding me in while she raised her hips, her tight lips opening to accommodate me. We smiled at each other as my head filled her, but as I thrust forward her face gave a brief grimace of pain, causing me to stop with perhaps half of my length inside of her. “Shit, am I hurting you? I can stop.”
“No, it’s okay. It just…hurt a little bit. Virgin here, remember?” she chuckled, her sexy smile returning.
“Not anymore,” I laughed in reply, lowering my mouth to hers, kissing her deeply, our tongues circling and probing as I moved my hips around as best I could. “I just don’t want to hurt you. Because this feels pretty amazing to me.”
“I think I like it too,” Kris replied, moving her hips up to meet me as I slid forward. I felt myself completely inside her, my full six inches sheathed by her womanhood. “Oh my fucking God, I feel so full.”
I began to move again, taking care not to slide out of her, which proved somewhat challenging by the slippery nature of her natural wetness and the condom’s lubrication. While it should’ve seemed as easy as doing pushups, I found my first time being inside a woman in missionary position somewhat challenging; I was never all that loose in the hips back then and finding a rhythm was somewhat difficult.
And yet, despite the awkwardness…these amazing new sensations were quickly driving me to come just a few minutes into our union, and I wanted this to be memorable for Kris as well as me. “What’s wrong?” she asked as I noticeably slowed, concern on her face.
“I don’t want to come yet. But it feels so fucking good to be inside you.”
“It’s okay, Steve. I’ll take it as a compliment. My pussy’s just so amazing that…”
Kris gasped as I took her words to heart and decided to just go for it, full out, urgently thrusting hard, fast and deep into her. Her eyes widened, and I felt her hand near my stomach as she reached down to touch herself while we fucked. “Oh my God, Steve, that feels so good, just take me, shit, fuck…” she said as I stretched her tight little pussy with my frantic motions.
“Fuck, I can’t hold back any longer,” I announced, continuing to piston in and out of her, my come jetting forth and filling the condom’s reservoir tip every time I bottomed out inside of her wonderful womanhood, five, six, seven times. I collapsed onto Kris, kissed her full on the mouth again as she wrapped her hands around my head while my spent cock shrank inside her. I carefully removed myself from her, pulled the condom off, somewhat surprised that it wasn’t bright red from her blood, tied it shut and tossed it into the waste basket by her desk before collapsing onto her chest, listening to her pounding heart.
“I’m sorry I didn’t make you come,” I said, feeling slightly embarrassed that I’d only lasted for five minutes or so.
“Don’t be. That felt really good. I’m glad my first time was with a friend who cares about me and makes me laugh rather than some random guy I met at a kegger.”
“I know. I feel the same. I was just hoping you’d see shooting stars and fireworks and scream my name ’til I went deaf, or something. Isn’t that how it’s supposed to be?” I laughed.
“I don’t think that’s really how it works. I think we’ll get better at this with experience.”
“I’m game if you are.” We held each other until we fell asleep, my erect cock against her ass as we lie on our sides.
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