July 2012

(This story is a dramatized version of a journal entry given to me by the man in the story, for the purposes of writing this story. It is true-ish, if he is to be believed.)

I lost my virginity on July 1, 2012. It was the beginning of a four-week adventure unlike anything else I've had since, and which I know I'm unlikely to experience again.

My family used to go to a lakeside resort for four weeks every summer, and there were a few other families that went to the same place for similar times. We and Margot's (name changed) family always went for the four full weeks in July, whenever those fell.

This would be the last time I planned to go to the resort, having turned 18 and graduated the previous month. I'd be off to college, and hopefully doing some things my own way shortly. But, I'd be along for this last time. There was, of course, Margot.

Margot and I had been friends, though only for the summer, since we were each about five years old. We didn't really stay in touch outside of the resort. She lived someplace else entirely, and although our parents stayed in touch via e-mail, we didn't really.

That said, I couldn't help but remember that on the last day we were at the lake the year before, she'd kissed me. In a way that had seemed like she really meant it. So, as we got closer to July, I gave it more and more thought. I wondered what our summer would look like.

The answer came that first night, when her family was over at our cottage getting reacquainted and catching up with everything from the past year. After about half an hour, Margot spoke up and asked if we could go for a walk down to the lakeside. Having secured the blessing of the parents, we left.

As we left the house, though, Margot quickly led me beside the cottage next door. "There's no one here this year," she said. "Something wrong with the wiring, Dad said, and so it's just closed up," she said as we crept along to the back door. She opened it up and led me inside.

"Which is convenient for us, especially if they leave the back door unlocked."

She took my hand and pulled me into the cottage, through the kitchen and into the living room. She sat me down on the couch and then sat beside me, her legs up under her body, and facing me. "So, what I want to know is: how far have you gotten since last year?"

I tipped my head sideways. "What do you mean? I graduated..."

"No. With girls. What base have you made?"

I opened my mouth to answer, but nothing came out. I hadn't really expected this particular conversation, and also wasn't sure how to answer it at all.

"You don't really know the bases, do you?" she asked. I shook my head, and she took both of my hands. "Okay. It's like this. Full-on sex is home base. Have you made it there?"

In that moment, I froze. Should I admit that I hadn't? Would she know if I lied? What was the solution, here?

"You haven't, then. Got it," she said, possibly disappointed. "I suppose you haven't made it to third base, either, then?"

I tried not to look puzzled, but I'm sure that, even in the dark room, she knew what my face said. She raised both of my hands a little, then lowered them again. "Okay. Before we left last year, that kiss was a first base kind of thing. At least, I hope it was. First base is kind of innocent stuff, but something that gets your motor going, you know? A kiss, some touching, but nothing too serious. But it gets you worked up. Have you done that since last year?"

Slowly, uncertainly, I shook my head. She sighed.

"Well, then," she said. "I guess we'd better start there again." With that, she placed my arms behind her back. She leaned forward until her face was up against mine, and she kissed me. Her lips were warm and soft, and her breath hard and hot. She opened her mouth against my lips, running her tongue over my lips until mine opened and she thrust her tongue into my mouth. With that, she grabbed the back of my head and held us close. I pressed my own tongue against hers, and she let it into her own mouth with a soft moan.

After several moments, she backed up a bit and we separated. She wiped her lips with the back of her hand, and smiled. "That was pretty good, for a guy who hasn't been practicing." She leaned forward again, and our second kiss of the evening was even more serious. If this was meant to, as she put it, "get my motor running," it certainly did. I could feel this intensity everywhere in my body.

"Now, let's talk about second base," she said. "Most people think of it as boobs." She paused to smile as my eyes flicked to the neckline of her tank top. "We'll get there," she grinned. "Technically, it's more like touching intimate places, but not genitals." She eased one of my hands down to her butt, and I offered no resistance. The denim shorts were softer than I'd expected, and her body felt incredible even through the material.

She moved my other hand to her chest as she leaned back. "That said, we both want you touching my boobs," she whispered. I ran my hand over the curve of her chest, trying hard to make it perfectly obvious that I'd never touched a girl's breasts before, even over her clothes. I slid my hand around from her back and brought it to the front, and cupped both of her breasts, circling the sides.

"Second base is pretty extensive," she said after what might have been a minute or a week. "It's still second base, whether you're touching clothes or skin," she backed up a bit, then reached down and lifted her tank top over her head. She revealed a pink demi-bra as she dropped the shirt on the floor and lay back on the couch. "But skin is a lot more fun, isn't it?"

I moved to the floor and knelt beside her, now kissing her neck and face, my right hand stroking her breasts. Then, I moved my kisses to her chin, and she threw her neck back. I kissed it, then journeyed down her neck to her cleavage, kissing between the cups of her bra even as she sat up a little, reached behind her back, and unhooked it.

She tossed the bra onto the floor with her tank top as I reveled in my first real sight of a woman's breasts in their glory. I'm sure that my attempts to kiss, lick, and suck her nipples and the flesh were clumsy and amateurish, but I tried to make it a celebration of her body as I explored this new territory. After a while, she lifted my own t-shirt and dropped it onto the pile of her clothes. She beckoned me to join her on the couch, and we clung to each other, her breasts pressed against my chest.

She ran a hand down to the seat of my pants and cupped my ass, then moved it back up my chest. "So, that brings us past second base," she said. "On the way to third, we have an interesting little place called short stop, and there's a lot of debate about what that means, it turns out," she said. She ran her hand down to the front of my pants this time, pressing against the bulge that I was trying not to make too obvious.

"Third base means touching genitals, but not with each other's genitals," she said. "But exactly what makes the difference between stopping short and third base isn't universally agreed upon. Some say, it's touching through clothes," she curled her fingers around my erection, through the khakis. "Some people think it's if only one of us is touching the other." With her other hand, she took my left hand and placed it on the front of her shorts. She moved my hand down until it was between her legs. "Move in small circles until I let you know it's right," she whispered in my ear. I did, and she gasped when it was right. I felt myself getting harder when I realized what was happening with her, and her hand on my dick moved more eagerly, too, sometimes stroking and sometimes squeezing.

She grabbed my hand to make me stop, and panted at me, "Undo the buttons," she said, lying on her back. Using both hands, I undid the four buttons on her shirts as gently but smoothly as I could, which was pretty clumsy. I spread the shorts open, revealing her pale panties. In the dim light, I wasn't sure if they were pink or white. I didn't really care at that point. I eased her shorts down her legs as she lifted her hips for me, and I again put my hand between her legs. The warm wetness was easier to find than with her shorts on, and I soon had her panting. She unbuttoned my pants at some point, but had moved her hands back to herself as she began to get more and more excited. "Do this," she panted, drumming her fingers on my arm. My hand on her panties copied the move, and she rocked against me harder.

She moaned and thrust her hips to my hand, and I kept on stroking. "Put your thumb on my clit!" she gasped. "Up a little. To the left," with a few more directions, I got my thumb where she wanted it, and I felt the raised nub of flesh. "Right there!" she panted. And then, in a moment, "Oh, God! I'm coming!" She bucked against me a few more times, gasping and panting. She rolled to her side and opened up my pants, pushing them to the floor. She then barely took a moment before tugging down my boxers.

My hard-on pointed straight in front of me, straight at Margot, as the cloth left it free. Margot reached out with her right hand and began to run it up and down my shaft. I felt my eyes roll back as she touched me. Then, she leaned forward and kissed the tip. The second kiss nearly drove me wild, and when she wrapped her hand around the base and took the tip into her mouth, I threw my head back and moaned.

She moved herself off of the couch and knelt on the floor in front of me, and proceed to blow my mind. Her hand and mouth moved along me, and I could do little but grab the back of her head. With a loud slurp, she pulled herself back and looked up at me. "Tell me before you come," she said. "I don't want to swallow tonight."

I nodded, willing to promise her just about anything to get that sensation back. It took a moment to register that she had just said she was going to make me come. She took me back into her mouth, and I practically growled with desire. I didn't last long before I grunted out, "Now!" and she slid her head back, then sat up more and continued jerking my penis, aiming the tip at her breasts. Four or five more strokes, and I felt myself erupt, spewing semen onto her chest. She kept me going until I fell limp in her hand, and she slid back up onto the couch. She grabbed a towel from beside the table, then handed another to me.

"So," she said. "Third base, by any definition." She wiped up the stuff from her chest as I tried to be discreet about wiping my own crotch. "How do you feel?"

"That was amazing!" I said. "I've never,... I mean,... wow..."

She grinned. "Yeah, that's fun," she said. "And you were good with your hand just now. I think we're going to have a good time."

"What kinds of things do you want to do?" I asked, not really sure what I was asking, but sure I should say something.

Margot grinned and slid off of the couch again. "Well, for starters," she slid the towel out of my hand and dropped it onto the floor, beside but not on the pile of clothes. "I've got one more place to show you," she ran her finger up my thigh, between my legs, and around my scrotum. I tensed as she slipped up the sack and to the base of my penis itself, which was already tightening for another erection. "This has been foreplay," she said. She grabbed my hips and held me in front of her. I felt my penis rising again, and inhaled deeply.

"That's right," she said, running her tongue over my dick and bringing it fully erect again. "Get back up there." She eased me through a turn, then began to push me toward the floor. I lay down on my back, and she stood over me.

With her feet outside my legs, she stood over me for a moment, then nudged her foot inside my legs, moving them apart. I fought against touching my erection, which was demanding to be touched. I just felt like this was not the right time to touch myself. She slipped her fingers into the waistband of her panties, then slipped them down. I felt the fabric land on my leg as she stepped out of them, and then she knelt at about my knees.

She lay down on top of me, and I wrapped my arms around her. Our lips locked, our tongues moving in and out of each other's mouths. She slid a hand down my thigh, and I moved a hand up to clutch her breast. Our breathing became heavier and heavier, and I was very aware of my erect penis pressing against her belly, her leg, her thigh, sometimes a breast, or wherever else it hit.

After what might have been a few minutes, she sat up, lifting herself a little on her knees, and grabbed my penis in front of her. I gasped with the thrill of being touched again and threw my head back. "No, watch!" she whispered. I opened my eyes and watched as she bit and opened a condom wrapper (where had that been?), then rolled the condom onto me. Then she raised herself up, guiding me underneath, and then inside, her.

We both sighed as she slid herself over me, sheathing my body in her moist softness. I don't think we sat there more than a moment before moving, but it felt in the moment like everything and all time. Then, she moved her hips slightly. She looked down at me, grinning, and did it again. I reached to her and grabbed her hips, and she moved my hands to her breasts as she moved in circles, now, sliding up and down on my penis. I tried to make my movements gentle as I both thrust inside her and stroked her breasts, but I was so consumed with sensation and lust that I know it was more ham-handed than it should have been.

I have no idea how long it was before she leaned herself back, dropping my hands to her legs as they could no longer reach her chest. She rocked only a few more times before she yelped, and I felt her body tighten around my erection inside her. That was all that I could take, and I felt my own body erupt in pleasure. I groaned, then sighed. We kept thrusting against each other until she raised herself up, sliding back against the couch. I sat up and gracelessly removed the condom, and she tossed me the towel again.

"That was... amazing," I panted. She smiled at me, then nodded.

We got dressed, and briefly took a walk around the cottages, just to be able to say that we saw something if our parents asked. Then, we went back to my family's place.

Over the next four weeks, we had sex every day. At least once, sometimes more. In the empty cottage beside mine, in a car, on the lake, in a riding stable,... numerous places. Her bed, my bed, the roof of my family's cottage,... It was the most erotic month I've ever had, and I learned a tremendous amount. Margot taught me how to give oral sex, how to find the clitoris and G-spot, how to talk about positions and so many other things. Before the month was over, we'd used up her box of 30 condoms as we went through cowgirl, missionary, reverse cowgirl, doggie-style, crab, and lotus-type positions.

Neither of us went back to the lake the next year, and we've never really been in touch since. We were a resort fling, and while we were childhood friends who went out own separate ways with one hell of a bang, that's all it was. I think of Margot fondly, especially in those flattering moments when a woman asks something like, "Where did you learn that?" The honest answer, often, is by that New England lake the summer after I turned 18.