When I was in high school, I was part of a circle of friends. We didn’t really have anything that defined us — we weren’t band geeks, although some of us played in the band; we weren’t jocks, although some of us played on the sports teams; we weren’t really ‘brains’ or ‘nerds’, although most of us got good grades; we weren’t the popular kids, or the kids who slept around. All we really had in common was that we liked each other, and enjoyed each other’s company.
When it came time to go to college, we all kind of scattered to the four winds. I was the only one of our circle who went to my school, but several others went to a couple schools that were within an hour’s drive of mine, so it wasn’t all that difficult for us to get together.
During the fall of my freshman year, before I’d really had much of a chance to make many new friends at college, a small group of my ‘circle friends’ from high school called me up, and we set up a weekend where I would go and spend the weekend with them at their school. Of course, that sounded like a lot of fun, so I bought a bus ticket and went to see them — Steve, Rose and Ellen.
When I got there, they had me stash my bags at Ellen’s place, since it was closest to the bus station. They took me on a walking tour of their campus, which was very nice. Then we went to a football game (their school won); after the game, we hung out and had dinner at one of the local ‘student hangout’ places. It was great to see my old friends again, and to see them adapting to their new environment, as I was doing at my school.
But among the four of us, it was almost like we’d never been apart. For a few hours amidst the insecurity of freshman year, it was nice to relax for a while with familiar friends.
As it got late, I sidled up to Steve, and asked him how we were going to get my bags from Ellen’s room to his, figuring that, since he was the only other guy in our group, I’d be staying with him.
“You’re not staying with me,” he told me. “There’s no space in my room — my roommate is having his brother stay with us this weekend. Ellen said that she was gonna set up your sleeping arrangements.”
When I asked Ellen about it, she assured me that it was all taken care of, and not to worry about it. So I didn’t.
When it got late enough that Steve and Rose had to get back to their respective dorms, I followed Ellen back to her room, where my bags were stashed. When we got there, I asked Ellen what she had set up, figuring that she had me bunking in with some guys in the men’s wing of her dorm. But that wasn’t what she had worked out.
Ellen sighed heavily. “Look, Jon,” she began, “I’m a little embarrassed by this, but I couldn’t set anything up for you. When Steve couldn’t take you, I was kinda stuck. But I didn’t want you not to come.
“Here’s the deal,” she continued. “My roommate is gone for the weekend. If you’re OK with it, you could sleep here in my room.”
Well, that was pretty completely unexpected, and at first, I was tempted to be a little upset with Ellen. It would be awkward, sharing a room with her for the night, and I didn’t relish the thought of getting up in the morning and emerging from her room, walking down the hall of the girls’ dorm, and all that might be inferred from that. But if I had better options, I sure didn’t know what they were. And I was only going to sleep in her room; it wasn’t like I was going to ‘sleep with’ her, right?
I had always liked Ellen; we had both been ‘good kids’ in all the years we’d known each other, growing up. In high school, we used to take long drives together, and stop to talk, and ‘solve the world’s problems’ for hours. I knew her as a serious, thoughtful girl, and I had really enjoyed our conversations. I figured we’d probably just stay up into the wee hours, sharing another of our deep conversations, like we had in high school.
“OK,” I said. “No problem.”
Ellen grinned, perhaps a little wider than I’d have expected. “I was hoping you’d say that,” she said. Pointing at one of the beds, she said, “You can sleep there.”
I tossed my gear onto the designated bunk, and flopped down onto it. “So which of the world’s problems do you want to solve first?” I asked, with a chuckle.
“I don’t know,” she answered. “I’m pretty tired, actually. Do you mind if I just change into my pajamas? Then we can see what comes up.”
Of course, I didn’t mind, but I was a little disappointed that she seemed not to be all that interested in talking. She ducked into the bathroom to change into her PJ’s, while I just stripped down to my underwear and slipped under the covers. I hadn’t brought any pajamas, figuring I’d be sleeping in a guy’s room. I kept my clothes nearby in case I had to get dressed under the covers in the morning.
After a few minutes, Ellen emerged from the bathroom, and my eyes about fell out of their sockets. Her ‘pajamas’ were a sheer nightgown, through which I could easily see her entire naked body. She wore no bra, and her breasts were easily visible through the sheer fabric. They were round and firm, and larger than I’d have expected, with dark circles surrounding her nipples. They jiggled and bounced in a most stimulating manner as she walked. A pair of red thong panties covered her pubes, but very little else. I felt my cock stirring at this totally unexpected visual feast of Ellen’s body, so alluringly displayed.
She crossed the room, stopped, and slowly turned in a little circle, until she was facing me again. “Do you like what you see?” she asked me, with notes of hope and desire in her voice.
Of course, I liked what I saw, very much. But as I tried to form an answer in words, I couldn’t find any, and only stammered, “Uhhhhh-huhhhh.”
To be perfectly candid, it had never really occurred to me to think of Ellen in any kind of sexual way. In high school, I’d thought of her as being a little on the skinny side, and her facial features as being just a bit ‘angular’. But she was far from homely, and had her own unique, undeniable charm, even if she was no ‘classic beauty’.
I could see now, with my own eyes, that what I had taken for ‘skinny’ was really more like ‘lithe’. Her breasts were certainly not undersized, and her ass was pleasantly round. My brain was recalculating its appraisal of her beauty a thousand times a second.
Finally, I managed to form a few words with my mouth. “Ellen,” I stammered, “you look incredible.”
She didn’t answer immediately, but came over and sat next to me, on the edge of my bed. Looking directly into my eyes, she said, “You have no idea how many times I’ve dreamed of having you in my bed. And now, here you are.”
I was stunned. As far as I knew, I had never particularly been the object of any girl’s sexual fantasies. A couple had let me feel their boobs, but I’d never done anything more erotic than that in my life. But now, here was Ellen, telling me that she’d had fantasies of sleeping with me.
“Seriously?” I stammered. “You’ve wanted me?” I couldn’t help myself staring at her fulsome tits.
She nodded, smiling to herself as she followed my eyes. “More than you could know.”
I tried to respond with a lame joke. Pointing at the bed across the room, I said, “But technically, I’m not in your bed, am I? This is your roommate’s bed.”
But Ellen was two steps ahead of me. “No,” she explained, pointing across the room with a wink and a sly grin, “that’s my roommate’s bed, over there. You’re in my bed.”
“But. . . why ME?”
“I want to find out what sex is like,” she said, “and I want you to be my first. Do you mind? You’re perfect for me — you’re my closest, best guy-friend in the world, and I trust you. I’ve already been fantasizing about you for years, so I promise I won’t have any regrets. And you’ve probably had sex already, so you can show me how.”
“Ummmm,” I demurred, “not really. I don’t know what you’ve heard, or who you think I’ve done it with, but I promise you that I’m just as much of a virgin as you are.”
“Oh,” she replied. A look of consternation crossed her face. “Does that mean you don’t want to have sex with me?” She paused in thought for a few seconds, then her face brightened and she said, “But I could be your first, too! What do you think?”
My mind raced. I had always appreciated the way Ellen and I could talk about anything. I’d never thought of myself as anyone’s boyfriend, and most of the girls I’d known growing up had shared that opinion. But obviously, Ellen was willing to think of me in more-than-platonic terms, and I didn’t find that thought at all unpleasant. Here she was, offering me her virginity, and offering to take mine. It might be a long time before I had another opportunity like this. But it was all so sudden; having sex with anyone, to say nothing of Ellen herself, hadn’t been in my mind at all, until only a few minutes ago. But then. . .
What the hell am I thinking, I chided myself. She wants to have sex with me! She’s been fantasizing about me! She’s sitting here in front of me half a millimeter from naked! How thick do I need to be?
I smiled and looked into Ellen’s eyes. “Sure,” I said. “I’m game if you are. Let’s do it.”
She fairly leapt across the bed at me, pushing me onto my back, and throwing her body on top of mine. “I KNEW I could count on you!”
Instantly, she was covering my face with kisses. I gripped her head between my hands and eagerly returned her kisses. I parted my lips and traced along her lips with my tongue. In response, she opened her lips and plunged her tongue into my mouth, probing the far corners of my mouth, and passionately tangling her tongue with mine.
With my hands, I began to explore her body, stroking her back and sides through the fabric of her filmy negligee. As we rolled around, it rode up over her hips, and I was soon running my hands over her bare skin. She sat up, and peeled the gauzy nightie off over her head, leaving her bare breasts jutting out from her chest, directly at me.
I reached up and cupped them in my hands, and nearly came in my pants. Her breasts were utterly perfect — large, and firm and round. How I had ever failed to notice her magnificent mammaries before then? Ellen groaned from the sensation of my hands on her breasts, and ground them against my hands.
Ellen was sitting on top of me, straddled across my groin. I was stiffly erect, and I could feel the shaft of my cock, still wrapped in my cotton briefs, nestling into the cleft of her pussy. Instinctively, I began to grind my hips against her, groaning with arousal as I did.
Ellen noticed my erection between her legs, and began to grind her pussy, covered only with her thong, against it. With her hands, she gripped my upper chest, digging her fingers into my skin until it even hurt a little. She was already gasping and panting, and shortly after that, she shuddered and groaned, and then seemed to relax.
At that point, I didn’t know that she’d had an orgasm (looking back, I’m not sure she knew, either). But as she laid on top of me, I began stroking the bare cheeks of her ass.
Abruptly, Ellen sat up. “Come on,” she urged, “we’ve got to get naked!” She peeled my shirt off over my head before rolling off me and tugging on the elastic waistband of my briefs. My poor, stiff cock was standing up like a tent pole against my underwear, a damp circle of pre-cum growing around the tip. Slowly, she peeled my briefs off me. I lifted my ass up off the bed to make it easier for her, and that had the effect of emphasizing my erection even more.
Ellen was fascinated by her first glimpse of an erect cock. She gripped it lightly in her hands, and slowly stroked up and down along my shaft. “It’s amazing,” she said, to no-one in particular. When she explored the fluid leaking from the tip of my cock, she took special delight in its slipperiness, playfully spreading it all along the length of my shaft. “I like your penis,” she purred.
While she played with my cock, I wanted to explore her vagina, as well. I reached inside the waistband of her thong and peeled it off her, leaving us both completely naked, at last. The rich, musky aroma of her arousal inundated my nostrils. I reached down between Ellen’s legs, to the patch of curly hair on her groin. I smiled to myself with the thought that, as delightfully different as our bodies were (and thank God for that difference!), both of us had pubic hair, and I delighted to run my fingers through it, and explore the wonderfully unfamiliar body parts that it covered, while Ellen purred happily.
I found her vaginal lips, and ran my fingers along them, then tentatively poked a fingertip between her labia, to feel the slick warmth of the inside of her vagina. Slowly, I slid my finger in and out of Ellen’s tight, moist tunnel, reveling in the utterly new and unfamiliar sensations.
Ellen removed her hands from my cock long enough to put her hand on mine, and take control of its movements. She took my fingertip and rubbed it to the top of her slit. There was a hard little nubbin hiding between the folds of skin, and she seemed most interested in having me rub the little nubbin. As I did, she grew more and more aroused, and began twisting and writhing at the sensations she was drawing from my fingers.
At last, she sat up. “I want to feel you inside me,” she asserted. I want us to have sex. I want you to put it in me.”
I watched with wide-eyed wonder as she climbed on top of me. She took my cock in her hand, and, raising her hips up off me, she positioned my cockhead against her opening, and slowly lowered herself onto me. My head spun as I felt her warm, moist smoothness envelop first the head of my cock, then an inch of the shaft, and then two. At one point, she paused and grimaced while she wriggled her hips around, seemingly searching for the downward path of least resistance. Finally, she gathered herself and plunged completely onto me. Her pubic bone bumped against mine; my balls tickled her ass; her pubic hair intertangled with mine. For several minutes, the two of us simply savored all the sensations of my erect penis wrapped in her sultry vagina.
“My god!” Ellen exclaimed. “You feel so GOOD inside me! It’s like your penis is filling me up!”
“Nothing ever felt so good in my life,” I breathily agreed.
Slowly, she began to grind herself on my rod, moving up and down, back and forth, against my own thrusts up into her. I really had no idea what I was ‘supposed to’ be doing; but the in-and-out, up-and-down movements felt really good, and we kept doing that.
I wanted to keep grinding together with her like that forever, but in short order (far sooner than I wanted), I felt a sensation in my balls, one I somewhat recognized from when I would masturbate, when I was just about to come. But it was very different, and cosmically better, to feel it while I was inside a woman. Before I could do anything about it, or even remotely try to hold it off, my balls exploded, and I groaned as rivers of cum gushed forth from my cock, into Ellen.
“Oh my god!” cried Ellen, as my semen surged into her. “I can feel it! I can feel you squirting inside me! It’s incredible! Oh, Jon, oh, baby, you’re coming — you’re coming inside me!”
It felt like I was coming for hours — every little movement that Ellen made provoked another orgasmic spasm from my cock.
Finally, Ellen fell on top of me, and with my softening cock still inside her, I instinctively caressed her all over — her back, sides, ass and legs — bonding with her in the afterglow of our lovemaking, trying to grip the significance of what we’d just done together.
“Thank you,” I murmured into her ear. “Thank you for wanting me. Nobody ever wanted me before.”
“Mmmmm,” she purred. “I did. I wanted you so many times. And I finally found a way to tell you.”
“I’m glad you did.”
My shrinking cock slipped out of her with a wet *plop*, and soon, we both drifted off into a deep, contented sleep.
In the middle of the night, I rolled over, and Ellen and I found each other’s naked bodies again. I lazily fondled her tits, and soon I was hard again, my erect cock pressing between her ass cheeks. Without saying a word, Ellen pulled me on top of herself, and groaned sensually as I slid my stiff cock into her again. The inside of her pussy was just as warm and moist the second time as it was the first, and I began slowly pumping in and out of her again, before filling her with my cum once more.
I awakened the following morning, to find Ellen propped up on one elbow, gazing at me. Her naked breasts jiggled alluringly as she shifted position on the bed. I already had a nice case of ‘morning wood’, and Ellen’s delightful nakedness was only making me harder.
“Good morning,” she chirped.
“Good morning yourself,” I drawled, still not fully awake.
“Well, I’ve decided,” she said.
“You’ve decided what?”
“I REALLY like sex!”
“Wow. . . who could have imagined? Me too!”
She shoved me playfully. “You wanna do it again?”
“Hmmmmm. . . let me think. . . lovely naked woman in my bed. . . hard cock. . . Sure, why not?”
Ellen giggled, and eagerly climbed on top of me. She ground her pussy along the length of my shaft for a few strokes, and I could feel that she was already wet with arousal. Quickly, she raised herself up, gripped my cock in her hands, and placed it against her ravenous opening. Then, with a sexy groan, she lowered herself onto me, taking me completely inside herself.
We mated slowly, sensually, savoring every sultry sensation arising from the moist friction between my cock and her cunt. Time seemed to stand still, and the universe shrank to our two bodies, joined together.
Ellen looked into my eyes. “Thank you for being my first,” she said. “It was even better than I’d imagined.”
“Thank you for being mine,” I replied. “I wouldn’t have done it, if not for you.”
I rolled my hips, driving my erection up into Ellen. My cock was aglow with a happy warm buzz that radiated out to every cell of my body. Ellen groaned with deep erotic ecstasy as we ground on and on. Finally, she rolled her head back, savoring every minute sensation from her pussy as they permeated her body. Gradually, she increased her tempo, until she was grinding on my cock at a rapid pace. Her jaw fell slackly open, and she began to gasp for breath. Soon, she began twisting and writhing, seeming to lose control of her body as her orgasm crashed over her. Her climax triggered mine in its turn, and soon my cum was surging into her womb once again.
We didn’t even leave her room that day. Steve and Rose called us, wondering if we were joining them for some planned activities that afternoon, but Ellen told them something else had ‘come up’, while I stifled my laughter at her bad pun.
We had sex twice more that day — we simply couldn’t get enough of sex, or of each other. Finally, though, we had to reluctantly put our clothes back on, so I could make my way back to the bus station, and my own school.
My head spun for weeks afterward, as I recalled how Ellen and I had initiated each other into the wonders of sex. We called each other almost daily, reliving every nuance of our coupling. A month or so later, my roommate went home for the weekend, and Ellen came to spend a weekend with me, so we could renew our sexual relationship, and learn a few new things. We went back and forth like that, roughly one weekend every month, for the rest of the school year. And the more we had sex, the better we got at it.
I’d like to tell you that that weekend of freshman year was the beginning of a long and happy partnership, that we got married and had a bunch of kids, and lived happily-ever-after. But it didn’t happen that way. In the fullness of time, Ellen and I both met other people, to whom we’ve been happily married for many years. But no-one else can ever be my first, or hers, and she will always have a special place in my heart for that. . .