I Lost My Virginity Cheating on My Boyfriend

He was 24 & I was 18 (and so ready)

Photo by Alí Díaz on Unsplash

As this is Sexpressions’ first sexy post, what better way to celebrate that than with a story of how I lost my virginity?

I was 18 that summer and perhaps a little old as far as losing my virginity goes, but I wasn’t ready before then. I was in Quebec for the summer on a language exchange trip after finishing high school from my home on the west coast and was there to learn French.

Summers in Quebec are hot and steamy as the humid air from the Gulf of Mexico floods north. The area where I was staying was near Sherbrook in what they call the Western Townships. It wasn’t a bad place to be because there were many English speakers there, so it wasn’t too hard to get by. We were staying at the local university and taking classes by day and the town by night.

It helped that the drinking age in Quebec was 18.

The warm night air on the downtown patios was intoxicating. Starting there, we’d eat and drink on a Friday night before heading to the clubs. The dance bars stayed open until 3 a.m., and I’ve never danced again as much as I did that summer. It was exhilarating.

I happened into him one weekend near the end of July. Although I’d seen him around the campus, he wasn’t part of our group but took a summer session course in the same building we’d used, or so I’d thought. Before that night, I hadn’t paid much attention to him but recognized him enough to say hi.

I’m not sure what it was, but I wasn’t feeling it that night. I’d had supper and a glass of wine, and when the group began heading to the dance bar, I decided I wanted to head back to the dorms. No one else wanted to go back with me, so I said good night and turned back to campus.

Meeting Jacques

Jacques was waiting at the next crosswalk for the light to change. When I moved up beside him, I said hello, and said,

“Nous sommes aller au meme direction, n’est pas?” And giggled at my triumph over his language.

“I guess we are. Are you going back to the campus too?” He smiled at my attempt.

“Oui, monsieur, je vais chez-moi.”

“Well, then, would you mind if I walked with you? I’m going back to my room too.”

He was charming, 24, and a perfect gentleman. The walk was only 20 minutes, but by the time we reached my dorm, I’d wished it had been longer.

“A demain, mademoiselle.” He said, and he turned to walk away.

“Teresa. Je suis Teresa, et vous?”

“Jacques. Pleased to meet you Teresa, good night.” He smiled.

“Bon soiree Jacques.” And that was that.

Jacques had hazel eyes with flecks of green, light brown hair, and a light complexion. His teeth were straight, and he had thin red lips. Not much taller than I was, he had a little extra weight and didn’t look particularly athletic, but his soft face and features suggested a gentleness that attracted me.

Thoughts of him lingered as I lay in bed, and for the first time in a while, I went to sleep thinking of someone other than my boyfriend in British Columbia. Although I wasn’t willing to admit it then, we were finished by the time I’d stepped on the airplane. He’d wanted me, but I wasn’t ready, so said no. That led to a small spat in the days before I left, so we didn’t have a chance to make up, and we never did.

Jacques, I learned, was a graduate student who’d stuck around as a teaching assistant over the summer in the anthropology department.

Our first date

It was two weeks before Jacques asked me on our first date, but we’d often have lunch together in the cafeteria when we had the chance. Some of the girls were jealous of me because I was seeing an older guy while they chased around with the boys in our program. I didn’t care; Jacques was so much more mature than they were, and what he might not have had in looks, he more than made up for in charm.

Dinner and a movie was the plan, and by then, we conversed easily in English. He’d always let me torture him with my horrid French, but beyond the simple greetings and expressions, I was lost. So when I wanted to say something beyond that, it was English, which was fine for him. As a Montrealer, he was fully bilingual, although it didn’t do much for my French studies after hours.

It was a Thursday night, and after the movie, some Hollywood thing with French voice-overs and no subtitles, we went to a café for a drink and chat. I didn’t want to stay out late, and he knew that, but the drink was nice. I wasn’t in a complete rush, and it helped that I felt sophisticated beyond my 18 years, sitting there at the sidewalk table with a grown man hanging off my every word.

We walked back to campus, hand in hand, and on reaching my dorm, I turned to him to say goodnight, and he pulled me in and held me close. I’m not sure if it was him or the wine, but I melted into his arms and buried my head in his neck, breathing his scent, before I kissed his neck. Turning my face to his, he looked back at me and smiled before kissing me deeply. I didn’t want it to end, but it was just before eleven, and I had to go. It was one of those perfect moments I’ll never forget.

The next day at lunch, he saw me and waved me over. He was sitting with his students, and they were talking about their camping trip. The reason we’d gone out that Thursday was because Jacques and some of the students were going camping that weekend. They planned their trip in French as I ate lunch and tried to listen, catching every 20th word as they flew by in their sing-song style of their regional dialects, which was far different than the Parisian French we were learning.

The camping trip

As lunch was ending and his students began filtering back to class, Jacques turned to me and asked with a bit of a waver in his voice,

“Would you like to come?”

“Sure, umm. What…do I? I don’t have anything for camping. What do I need…?”

“Some good shoes or boots if you have them, a change of clothes for two nights, and your bathroom stuff. I’ll take care of everything else.”

“Ok. What time and where do I meet you?”

“Five o’clock, outside your dorm. We’ll come and get you.” I was a little nervous, but he was beaming. I’m not sure if he just thought of asking me then or couldn’t manage to ask before that, but I believe our kiss had made it easier for him. It had certainly made it easier to say yes, but there was just one little virginity problem.

I was on autopilot all afternoon as I wondered why I didn’t ask where I’d be sleeping. Both boys and girls were going, so it never occurred to me to ask, and I began to get nervous but told myself it’d be ok and pushed it out of my mind.

I was ready to go by five, and Jacques pulled up not long after. Loaded into the station wagon with five others, I sat in the middle of the back seat, with Jacques to one side and another girl. The campground was only 25 minutes out of town, but the ride was fun, and everyone chatted the whole time. It’s funny, but no matter how many French people there are, when there’s one English person, they usually all speak English, which kept my mind off the sleeping arrangements.

Jacques held my hand the whole ride as he laughed and joked with his friends, which made me feel special in a way I’d never felt with my boyfriend. What also became apparent was the four other people in our car were couples. I wasn’t sure about the other people going, but it seemed like Jacques, and I were the only singles, which was quickly confirmed when the tents started going up.

Our tent

The wine helped immensely to calm my nerves, and true to his word, Jacques had two sleeping bags and two air mattresses for “our” tent. All I remember saying to myself was that I was a big girl and everything would be ok, but I was freaking inside. The only thing I hadn’t worried about was birth control because I’d started it the year before to help clear my skin, and it worked so well, I never stopped.

We did all the camping things that night sitting around the fire as they sang their Quebecois songs and teased my French accent, which flowed more freely as the night wore on. By eleven, the park staff came by and told us to keep it down, so we called it a night. All the girls headed up to the bathrooms in a group, and we got ready for the night as we laughed and giggled from the wine.

Getting back to the tent, I found it empty. The boys had stayed back to put out the fire and clean up before heading to the bathroom, so Jacques was still up there when I climbed into the tent.

It had cooled down a bit, so I’d slipped on my PJs and crawled into my sleeping bag, and waited in the dark. My nervousness had turned to excitement over time, as Jacques had held my hand and caressed me all night as we sat by the fire. He got my drinks and snacks and did anything else I’d wanted. He really was a sweet man, and if he’d only been doing all that to get into my pants, there was no sign of it.

When the zipper rattled, I was ready for him. He climbed into the tent quietly without saying anything. Before he spoke, I could already smell his cologne gently waft in, filling the room with the scent I’d first smelled on his neck. He’d freshened up for me, I thought, regretting I’d only reapplied my deodorant.

We lay in the dark, holding hands as we listened to the sounds of the night for a while before he leaned in for another kiss — our second. As I lay back, he rolled toward me and held me in his arms as our lips and tongues vied for the best purchase.

The first move

Feeling his hand near my waistband, I lifted my tee-shirt and gave him access to my naked chest underneath. As he caressed me and tugged at my nipples, I was reminded that this was how far my boyfriend had gotten before I chickened out, but this time, I felt different. Jacques had put me at ease from the moment we’d met, and I still felt that way. And then his hand was once again at my waistband.

When his hand slipped under the elastic, I gasped. Jacques froze, and our kiss broke off. I knew there was no turning back if I let him go further. I also knew what happened when I’d stopped my boyfriend. But Jacques wasn’t my boyfriend, and in the instant that followed, my hand was on his giving him permission to go further.

His fingers then slid under my panties and across my light bush. While my hair is a more course deeper red, my pussy has always had a soft light coat of wispy red hairs, so sparse, it looks like I shave, though I rarely have. By the time his fingers reached my vulva, I was already soaked. While no man had been down there, my fingers and hairbrush had been on many occasions after I’d taught myself to orgasm not long after my 18th birthday earlier in the year.

Where no man had gone before.

His fingers gently parted my lips as he found the source of my wetness and began spreading it with his fingers. Finding my clit, he circled it and tugged at it under its hood. My breath quickened, and my breathing grew labored as he fingered and played with me.

Moving from my lips, he traced down my chest with his tongue until he reached a nipple, which licked and circled with his tongue in unison with his finger between my now parted lips.

Grasping at me with his teeth, he took my nipple into his mouth, and I felt a jolt of electricity shoot to my clit. I was writhing under his touch and felt the pressure building inside me, fighting to get out. My feelings of uncertainty had long since melted away under his fingers, and all I needed then was for him to fuck me.

Pushing him off of me abruptly, he again froze, afraid he’d gone too far. I tore open the zipper on my sleeping bag and sat up. By that time, he was well back and off of me. I’m sure he’d been quite scared by my sudden movements. Scared until I whipped off my shirt and threw it to my feet. I then lay back, lifted my ass, and pushed my pants and panties down in one swift move.

I had gotten used to playing with my pussy in bed at night, but since arriving in Quebec, I’d only been able to orgasm once the night Jacques had walked me home because my roommate was still downtown. Although I got by without masturbating that summer, Jacques’ touch was too much, and I didn’t have a hairbrush, so he’d have to do, I told myself.

I was ready

When he saw what I had done, he followed my lead. I’d never touched my boyfriend’s cock, although I had rubbed him through his jeans the night of our fight, but that was in the past. I reached out to Jacque, and grasped his cock in my hand, and tugged at him gently as I pulled him to me.

Letting him go, I reached for his neck and pulled him to me. He was still unsure and hesitated a little, but I released his neck, took his hand, and pulled him down onto me. Spreading my legs for him, he positioned himself over me, and while holding himself there, I took his cock into my hand once again and used it as I’d used my hairbrush. Running his head up and down my glistening slit.

I worked his tool over me as he moaned lustily. As I found my passage one last time, I guided him into me. Unlike my hairbrush, his cock was velvety smooth with soft edges, even though he was rock hard.

I fucked my pussy onto his shaft as I willed him into me. Letting go, I reached for his hips and pulled him in. God, I need him to fuck me. To fill me.

Taking my cue, he buried himself in me in a slow but determined stroke. When he’d fully seated inside me, he leaned in for a kiss as my body pulsed under him.

“Fuck me.” I pleaded, “fuck me.”

Beginning to ride me now, his fleshy piston filled me over and over again, in a way my brush never could. I clung to him and urged him on, holding his hips and pulling him into me harder and harder.

God, I wanted him to keep going, but it wasn’t to be. He drew a sharp breath, then held it. Pressing down on top of me so hard it felt like his whole body was trying to get into my pussy.

He grunted and exhaled in jets of air as his cum filled me. I could feel every pulse of his cock as he unloaded into me. I remember thinking, he’s no hairbrush, but Jesus does he feel good.

My turn

As he began to relax, I released him, and he rolled off of me. I hadn’t orgasmed, but my cunt had never felt so satisfied. Reaching down, I found my clit, then went beyond to lubricate my finger when I felt his warm cum draining from me.

Wetting my finger with his gooey mess, I fingered my clit until I came, in under a minute. Fuck, my pussy had been so ready for a quick release after his cock had worked me. I felt like I was in heaven.

I rolled on to him and snuggled in. We lay like that for a while, his cum draining from me still, until I once again felt some growth from between his legs.

The second time lasted longer than the first, and we fucked into the night. The other couples didn’t see much of us that weekend because if we weren’t fucking, we were sleeping.

My French never got that good because of him, but my pussy would never forget an inch of him. Looking back, my hairbrush probably popped my cherry, but Jacques gets all the credit.

I told him the next morning that he’d been my first which was good for another session as he congratulated himself on a job well done.

This was the second time I lost my virginity —Adultery & Losing My Second Virginity
My first naked playdate.medium.com

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Why I wrote a book on cheating.medium.com

© Teresa J. Conway, 2021

By Teresa J Conway on .

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Exported from Medium on July 29, 2021.

Author of How to Cheat: Field Notes from an Adulteress, several short stories, I'm active on Medium @teresajconway where I sometimes share my blog posts.

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