I Accidentally Took Someone’s Virginity

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Every winter, our company sends a select few upstate for this mid-year conference. I was making my fourth consecutive trip for our outlet, mostly because I’m usually one of a handful of people who actually volunteers for the trip.

Saturday morning, they stuck us all in a room and went over the new “business plan” for the year, which translates to, “this is what we’re trying this time around.” They paired us with the person to our left to go out to various businesses around town and try to find ways we can incorporate something they were doing into our own business structure.

When the meeting broke, I introduced myself to my partner for the day. “Hey, I’m Zach,” I said. “Lauren,” she said, chuckling. “You ready to get started?” she asked. “Lead the way,” I said, extending my arm to the door.

She was a pretty cool chick; I’m not going to lie. She was a short little thing — maybe 5-foot-1, 5-foot-3, tops — and she was a crazy Michigan football fan. She worked up there, so she knew the town pretty well. She also knew which businesses were successful, which made our job pretty easy.

Maybe a little too easy.

“Look, I know this town like the back of my hand; you want to just hang out? I’ll have plenty of stuff to go over at the meeting,” she said. I liked the confidence, and I really wasn’t too keen about taking notes on other businesses. “Sure, what did you have in mind?”

We really didn’t have a whole lot of time to do anything, so we just stopped at a nearby pizza joint and talked for a bit. I found out that she was living alone here, and that the rest of her family lived back in Detroit. She mentioned that she loved wine, but that she “wouldn’t be caught dead” drinking white wine.

As we were finishing up and about to head to the office, I asked her about the nightlife around town.

“So, since you know this place like the back of your hand, what the hell do y’all do for fun?” I asked. “There’s a really good bar about two miles from the hotel. They play live music there every Saturday, although the performances are usually hit or miss,” she said.

“Fuck it, I’m down. What do you say we exchange numbers and meet up tonight?” I said nonchalantly. She chuckled again, just like when we introduced ourselves. “Sure,” she said, still chuckling.

“I’m at 9—,” I began, before my phone started ringing. I didn’t recognize the number, so I asked to take it. “No, go ahead,” she said, waiting for me to give the other nine digits.

“Hello?” I asked, turning around.

“You really don’t remember me, do you?”

I turned back around. There was Lauren, holding her phone in the air with the screen faced towards me and “Zach Armstrong” written across the top. Apparently we met last year, and apparently I gave her my number, even though I had no recollection of either.

“I thought you were just fucking with me this whole time,” she said, smirking. “But wow, you really don’t remember.” I felt like an asshole. I knew that nothing happened between us because, well, I would’ve remembered that. I must’ve given her my number at some point, but I don’t know why I didn’t have hers.

“We were hanging out at the hotel bar last year with some other people and you lost your phone,” she said, “so you asked if I could call it for you. It was in your jacket pocket.”

I remembered being in the hotel bar, but I couldn’t recall who was there or what happened. I wasn’t drunk or anything; I just have a shitty memory.

“I’m an idiot, I’m sorry,” I said, now embarrassed. “Were you still interested in going tonight?”

“If you don’t forget,” she quipped.

The meeting ended sometime around 5 p.m., so we went to our rooms to rest up a bit and get ready. Around 8 p.m., we headed out. There was no wind; just a brisk chill in the air.

We got to the bar and some indie band was playing, which was good for conversation. I wasn’t a big drinker, but she was putting them away. She had four glasses of wine before I finished my second Twisted Tea. It looked to be more nervous drinking than “I have a problem” drinking. She was open; intelligent; and yeah, cute.

When the hard rock band took to the stage, we took it as our cue to head out. She said that there was a bar across the street that was much quieter, so we left. I left my phone in the car accidentally, so I asked if she wouldn’t mind taking the detour to get it.

As I grabbed it from the front seat and closed the door, I asked if she was ready.

“Wait,” she said, walking towards me. She put her arms around me and kissed me against my door. We made out in the parking lot for probably 10 minutes before both of our lips started getting chapped. “You want to head back and warm up?” I asked, softly.

She bit her lip, then nodded.

We hit all four red lights on the way back. When we got to the third, she started massaging my dick, which was rock hard and pressed against my thigh.

When we got to the fourth, probably about a hundred feet from the hotel, I unbuckled my seatbelt and reached over to kiss her. I grabbed a handful of her hair while keeping the other on the steering wheel. I felt the glare of the lights change on my closed eyelids, so I opened them up and drove the rest of the way.

We didn’t know whom we would see in the lobby, so we walked casually to the elevator. Fortunately, my pea coat ran down just long enough to cover what was an irritating erection to walk with.

We made out for the couple of seconds in the elevator until we got to my floor. It didn’t hit me until we got through the door and kicked our shoes off that I didn’t have a condom.

“Do you?” I asked her. She shook her head. I thought about chancing it for a quick second, until I had a sudden moment of realization. I ran to my laptop bag and sifted through it.

There it was.

Beat up and recently expired, but a condom wrapper with some form of protection inside. Even if it had timed out a month ago, an expired condom was still significantly safer than going at it bareback.

I stood up after grabbing the condom, and she started kissing me while undoing my pants. I started to unbutton my shirt. When I undid the last button, I reached behind her to unzip her dress.

I pulled my shirt off as she slid off her dress. We continued to kiss as I unhooked her bra. As I stood there in my briefs and dress pants with her hand stroking my cock, I could feel her sliding down to blow me.

I’m usually one for foreplay, but I was in a no-fucking-around mood.

“No,” I said.

“Is everything OK?” she asked.

“Everything is fine,” I said, sternly. “I just want to fuck you right now and I don’t want to bullshit around it.”

I reached into her panties and felt her wet pussy on my fingertips.

“Looks like neither do you.”

I tossed her on the bed, then took off the remainder of my clothes with the condom wrapper in my mouth. She was getting out of her thong. Once everything was on the floor, I placed the condom on and crawled towards her on the bed.

I got the tip in fine, but about halfway in I felt a little pressure and saw her wincing. “You OK?” I asked. “Yeah, it just hurts a little.” I was on the thicker side and any lubricant that was on the condom had surely worn off a while ago, so I just went slower.

Once I was about four strokes in, she seemed to relax a little bit. After four more, she relaxed a little more. When I put myself all the way inside of her, her legs clenched against my hips and she grabbed the back of my arms.

“You can go a little faster,” she panted in my ear. I obliged.

I went a little faster. She grabbed a little tighter.

I went a little faster. She pressed her fingernails against my arms.

I went a little faster. She clawed her hands down my arms.

I couldn’t feel anything, except my cock sliding in and out of her tight pussy. I would see her wince every time I would start to go too fast, so I knew when to slow down. After a while, I decided to slow things down altogether.

I laid my right arm beside her head so that I could lean down to kiss her. I slowed my strokes down, but I was elongating them. Her hands moved to my back; every time I went to the base, she scratched a little harder.

My favorite thing about kissing a girl’s neck during sex is that you can hear her panting directly in your ear. If you’re lucky, like I was that night, you get a girl who occasionally tugs at your ear with her teeth.

She bit down pretty hard on one bite, which caused a reflex “Agh,” whisper out of me. With the top of my ear still gripped between her teeth, she ordered me to go harder.

“I want you,” she said, in a deep breath, “to take that fat cock of yours,” breathing harder, “and I want to fuck me like you mean it.” I released my ear from her mouth and glared at her.

“Well?” she said.

I leaned down to kiss her as I started to fuck her harder, but when I pulled away I bit down on her lip hard enough for her to take another deep breath. She grabbed my ass and dug her fingernails in as she continued to pant.

“There,” she sighed. “Don’t stop.”

I didn’t want to cum before she did, but it was getting harder to resist the urge.

“Zach,” she sighed, “I’m gonna cum.”

As she started to cum, she bit into my arm. Not a nibble; not putting her teeth against; but a full-on, digging-in chomp. Because I was starting to cum as she was finishing, I blocked out the pain.

Once I blew my load and rolled over to lie on my back, everything hurt.

The chill of the sheets against the scratches on my back was uncomfortable. My arms were covered in claw marks; she even drew a little blood on my left arm. We fell asleep soon after, mostly because I was in too much pain to do anything else.

I struggled to put my shirt on in the morning before saying goodbye to her.

“Fuck, this hurts,” I said jokingly, with an undertone of seriousness. She cringed a little. “Sorry about that; I got a little carried away.” I looked at her with a mix of awe, disbelief and laughter following the biggest understatement of the weekend.

“Hey, at least I won’t forget you now,” I joked. “I’ll probably have scars from these this time next year.” She just smirked at me, almost as if she was proud of the work she had done.

“Hopefully I did enough to you to make you remember me as more than just a name in your phone…”

“Zach, don’t be silly,” she said, kissing me from the hallway, just outside the door.

“A girl never forgets her first.” TC mark

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