Summer Reunion

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An encounter with an old classmate takes an unexpected turn.
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James19999
James19999
342 Followers

"That'll be $74.86." I said, fighting back boredom. The middle-aged man in front of me was already reaching for his credit card and inserting it into the chip reader. I watched the credit card approved message pop up on my screen before saying "have a nice day" for what must have been the twentieth time that day.

The routine was so familiar it ached. It was my first summer back from college, and I was working as a cashier at the same grocery store I had worked in through high school. My parents had insisted I do something over the summer, and in any case, I figured my next year would be a lot more enjoyable if I had some spending money, even if the $12 per hour I was making would get me anything too extravagant.

The man had hardly walked off before I started scanning the next customer's items. Some lettuce, some chicken, a few bottles of wine. My reaction to the wine was automatic.

"ID?" I asked, looking up from the conveyor belt for the first time. The customer was a woman who couldn't be too much older than me, tan with blonde hair that only just came down to the bottom of her head. Something about her seemed familiar.

"Hayden?" she asked, a hint of surprise and embarrassment in her voice. Now I recognized her: Emily Smith. We were high school classmates who had graduated the same year, although we'd never been especially close. Her hair was shorter than I remembered it, which was probably why I didn't immediately recognize her.

That meant she wasn't old enough to buy alcohol. Like me, she was only 19. This was a little awkward.

"Emily, right? I don't think I've seen you since graduation." I replied.

"Yeah, it's been a while." she said, blushing. She leaned in a bit closer. "Do you mind bending the rules for me just this once?"

"I don't know, I could lose my job over this."

"Please, no one has to know," she said, her blue eyes looking up at me earnestly. Then, they took on a hint of mischief. "How about I share some of it with you tonight?" she added, a smile forming on her lips as she leaned toward me.

I could feel my heartbeat speed up. That was an awfully tempting offer. I'd always thought Emily was cute. I looked her up and down, seeing that the last year had been kind to her. She was wearing short jean shorts that showed off tanned, muscular legs and a white tank top that left her toned arms exposed. If I recalled correctly, she was a soccer player. Between her tan, her fitness, and her short haircut, she had a very appealing tomboy look.

"Alright." I said. She gave me a conspiratorial smile as she handed me a driver's license. It was a pretty good fake. If I hadn't known who she was, it would have fooled me. I handed it back and finished scanning the rest of her items.

"That'll be $38.60, Ms. Piscatelli." I said, emphasizing the last name on the fake.

"Thank you very much." she replied, inserting her credit card. "Write your number on the receipt and I'll text you later."

Reaching for a pen, I eagerly wrote my number on the receipt and handed it to her. Emily smiled enticingly as she put the receipt in the bag with her groceries and walked off. My eyes followed her as she walked away, enjoying how the tight shorts hugged her small but pleasantly round ass. She looked over her shoulder and waved as she walked out the door.

My pulse gradually returned to normal as I scanned the next customer's items, and the next. The last three hours of my shift went agonizingly slowly as I replayed the encounter with Emily in my mind, awaiting her message and fantasizing about tonight. I found myself thinking back on our handful of interactions in high school, trying to figure out if she'd been flirting with me back then.

When my shift finally ended, I was more than a little disappointed that there was still no text from Emily. My phone remained disappointingly free of notifications for hours. I checked before I got in my car to drive home and then after, and still nothing. Had she played me? Was she just flirting so that I would let her buy the wine? Did she tear up the receipt with my number as soon as she walked out of the store?

I'd never been good with women. I've always been shy. When I liked a girl, I could never bring myself to tell her for fear of rejection. I was normally well-spoken with my friends or teachers or coworkers, but for some reason, words always failed me when I was trying to talk to a girl I like. Honestly, I was surprised Emily recognized me at all. We had hardly spoken in high school; after all, she was a pretty girl, and I was me.

My looks had never made up for my shyness either. I didn't have an athletic build or a chiseled jaw; I was short and thin. The only girls who had ever thought I was cute were the ones I wasn't interested in. I certainly didn't normally draw the eye of girls like Emily.

Examining all that evidence, I came to the conclusion that she really had just used me. Kicking myself for my naivete, I sullenly sat through dinner with my parents. I didn't talk much, and they pretty quickly realized I didn't feel like talking. After clearing my plate, I was walking up the stairs to my bedroom when I felt a buzz in my pocket. My heart skipped a beat as I pulled out my phone.

Sure enough, there was a text from a number that wasn't saved in my contacts. I hurriedly opened the message.

"Hey, it's Emily" read the text. I grinned to myself, relief washing over me.

"How's it going?" I replied, probably a bit too fast. I hoped it didn't seem desperate.

"Could use a bit of company ;)" came the response a few minutes later.

"You did promise me some of that wine" I sent back, hoping it sounded flirty and not like I was scolding her.

"My parents are out of town until Monday. You should come over"

"I'll be there in ten minutes" I replied, then turned off the screen and thrust the phone into my pocket.

My heart was pounding in my chest. I started to shake with excitement. She was actually serious. I was about to be alone with Emily Smith and two bottles of wine.

She texted me her address. It was only a few minutes' drive away. Not wanting to tell my parents the truth, I told my mom that I was going over to my friend Paul's house. She smiled back and told me to have a good time, glad that I was getting at least some social interaction.

I pulled up at Emily's house a little after 8:00 PM and hurriedly looked myself over in my car's rearview mirror. After straightening out my hair, I took a deep breath. I didn't want to seem jittery or desperate to her. I had to play it cool. I took a minute to compose myself, got out of the car, and knocked on the front door.

Emily answered, dressed in the same short shorts and tank top she had worn to the grocery store. She smiled when she saw me, and my heart fluttered. She hadn't just invited me over out of a sense of obligation; she was actually glad to see me.

"Hayden, glad you could make it." she said, stepping out of the doorway so I could come in. I stepped up into the foyer and took a look around. In typical suburban fashion, it was basically the same model as my own house.

"Thanks, I'm glad you invited me." I replied after a moment. Looking down, I saw her shoes by the door, so I took mine off too.

"Come on, have a drink with me." She motioned toward the living room and started walking back into it. I followed her, once again enjoying the display of her shapely legs and round ass in her tight shorts. In the living room, I saw a glass coffee table surrounded by a couch and two armchairs. There was an open bottle of wine on the coffee table and a full glass next to it.

"Have a seat. I'll get you a glass." said Emily, walking off to the kitchen. I sat down on the couch, forcing myself not to stare at her. Play it cool, don't seem desperate or creepy. I'd heard nothing scares women off like seeming desperate or creepy. Maybe that's why I never had any luck.

Emily returned about thirty seconds later with an empty glass. She picked up the bottle, poured some red wine into it, and handed it to me.

"Thanks," I said, taking it from her and watching as she sat down on the armchair across the table from me. I took a sip and tried not to show any reaction as I felt the warmth of the alcohol fill my mouth. I was one of the rare college students who never drank, and I didn't want Emily to think I was a dork for that.

"I don't think we've talked since graduation!" she said. "How have you been?"

She was right about that, and even at graduation we had just exchanged pleasantries. We had never really been close. But hopefully that would change.

"I've been good. I'm really liking college so far. It's nice to get away from this town."

"Ugh, I know! It's a little weird to be back, honestly."

I took another sip of wine and felt myself flushing with warmth.

"You went to Tennessee on a soccer scholarship, right?" I asked.

"Yeah, Knoxville is great. Where did you end up again?"

"You haven't picked up a southern accent yet." I joked. Her laugh was pleasant and melodious, and it filled me with a bit of confidence that I wasn't making a total fool of myself. "I'm studying computer science at Temple. I like it, but it's cold."

We settled into a rhythm of conversation, reminiscing about high school, swapping stories about college. I could feel my nerves and inhibitions slipping away, probably thanks to the wine. We were going through it at a good pace, and before I knew it, the first bottle was gone.

"Let me go grab the other one." said Emily as she tried to pour herself a new glass and saw nothing come out of the bottle. She set the empty bottle down and got up. This time, with a little alcohol in my system, I didn't bother to avoid staring. I enjoyed watching her reach up into the cabinet for the bottle, her calf muscles taut as she stood up on her toes, and the bottom of the tank top riding up as she reached, showing me a tantalizing hint of her lower back.

She uncorked the bottle and walked back to the room, her hand on the neck of the bottle. I did remember to look away before she caught me staring.

Emily sat down next to me on the couch. I could feel my heart rate pick up again as she sat less than a foot away from me. She leaned down over the table to pour herself another glass, and I couldn't resist taking a peek at her cleavage. Her breasts weren't big, but they were well-shaped and they fit her frame well.

"Do you have a girlfriend?" she asked. Now my heart was really pounding.

"Nope, still single. What about you?" The liquid courage let me get those words out without sounding like the stuttering mess I probably would have been sober.

"Nope, no girlfriend." she said with a giggle. Then the smile dropped off her face. "I had a boyfriend, at least until a couple weeks ago."

"Ouch. Sounds like it didn't end well."

"That's an understatement. He cheated on me with half a sorority house. I just found out."

"I'm sorry to hear that." I wasn't sorry to hear that at all, but I didn't want to sound like an opportunistic dick.

"To rebounds," she said with a glint in her eye and her lips turned up in a smile, reaching her glass toward me.

"To rebounds," I repeated, clinking my glass against hers. She pulled her glass back to take a sip, but tipped it too soon. A splash of the red wine fell onto her white tank top.

"Oh, shit." She looked down at the stain on her top for a moment, then reached down to the hem. I watched wide-eyed as she took it off over her head, revealing her fit, tight torso.

"Enjoying the view?" Emily asked, glancing over at me. I forced myself to look away from her body, the black bra the only thing stopping me from seeing her breasts. My cheeks were already flushed from the wine, but I could feel them burning even hotter.

"Sorry" I mumbled, staring at the wall, not daring to take another glance or even to look her in the eye.

"It's okay," she said with a giggle. "I like the attention." She stood up from the couch and stood just in front of me. The outlines of her tight abs were visible just inches from my face. She reached down and cupped my chin, drawing my eyes up her torso, past her cleavage, and toward her pretty face, now graced with a mischievous smile.

"Let's go upstairs." she said, grabbing my hand. I stood up, my heart pounding in my ears and the front of my jeans suddenly very tight. Holding my hand, she led me upstairs to her bedroom. My eyes were locked on her nearly naked back, admiring the muscular tone as she tugged on my hand. At the top of the stairs, she pulled me into her room and closed the door.

I stood there, staring at her, trembling with excitement. She stepped even closer, her body brushing up against mine. Emily was only half an inch shorter than me, so she didn't have to lean up far to plant a kiss on my lips. I closed my eyes and awkwardly kissed back, her soft lips pressed against mine.

After a moment, she pulled away, a wicked grin on her face. She stepped back, eyes still locked on mine, and walked backward to her bed. Motioning with one finger for me to follow, she lay down supine on the bed, spreading her legs.

I've never been great at reading women, but even in my tipsy state I couldn't miss her meaning. I eagerly climbed on top of her and between her legs, leaning down to kiss her. She eagerly leaned back up to kiss me and wrapped her legs around my waist, pulling my body up against hers. My whole body thrilled at the intimacy, my now fully erect dick separated from her only by our clothes.

Emily threw her arms around my neck again as I kissed her. I almost whimpered with pleasure, my waist sandwiched between those muscular thighs, my lips locked with hers. I could feel a tingling at my groin, and my eyes went wide. I tried to pull away, but her hold was too strong. There was that set of contractions all too familiar from masturbation, and before I knew it, I could feel a hot splash in my underwear as I orgasmed.

"Fuck." I muttered, angry with myself and thoroughly embarrassed. Here was my one shot with a girl way out of my league, and I had blown my load before my pants were even off.

Emily looked up at me, confused. She thought for a moment, and I saw recognition dawn on her face.

"Did you just cum?" I could see her stifling a laugh, and my cheeks somehow burned even hotter. Her legs relaxed and I pulled myself off her, standing up. I couldn't bear to look at her.

"Shit, I'm sorry." I said, looking down at the floor.

"It's okay, you were just excited. I'll take it as a compliment."

The hot mess in my pants had very quickly become a cold mess. I shifted, uncomfortable with the sticky moisture in my underwear. All the excitement of the last few minutes had been replaced with shame, disappointment, and discomfort.

"Where's the bathroom?" I forced myself to ask. I couldn't do anything about the embarrassment, but at least I could clean myself up.

"Across the hall."

Not daring to meet her gaze, I turned around, opened the bedroom door, and crossed the narrow hallway into the bathroom. Shutting the door behind me, I unzipped my jeans and slid them down, looking shamefully at the cum on the inside of my boxers. I grabbed a paper towel and ran it under the faucet and began dabbing at the mess. After a few moments, I heard a knock on the door.

"I brought you a change of clothes" came Emily's voice, muffled by the door. I heard the door open and hurriedly turned around. It was only open a few inches; Emily's hand came through and tossed a bundle onto the floor, then closed the door behind her.

"Thanks." I managed, still sounding deflated, but grateful she wasn't being mean about what had happened. I spent a little longer wiping down my boxers and myself, then stepped out of my boxers and jeans. I turned to the bundle Emily had thrown on the floor and took a look at the change of clothes. It didn't look like much. Maybe just clean underwear? Whose underwear was it anyway? I hadn't heard her moving down the hall to another room, now that I thought about it.

I picked up the bundle, and saw something fall out. Taking a closer look, I realized what I still had in my hand was a pair of black lace panties. Looking down, I saw a matching black lace bra and a short black miniskirt lying on the floor.

"Uh, Emily?" I asked.

"What?" came her voice through the door.

"The clothes you passed me..." I trailed off, not sure how to phrase it.

"What about them?"

"I don't think -" I paused, still not sure what to say. "They're girl's clothes."

"Try them on."

"Look, I don't think this is a good idea. I'm just going to put on my clothes."

"Please?" she asked in exactly the same tone as she had used in the grocery store. I could imagine that same pout on her face. "Come on, I think you'd look good in them."

Was this some kind of elaborate joke? Was she making fun of me somehow? I couldn't tell, but either way, I got the sense she wasn't going to let this drop. I saw myself blush bright red in the mirror and sighed. Reaching down, I pulled the lace panties on, then the miniskirt over them. The panties were incredibly soft and surprisingly comfortable, even if they were a little tight. A bit of a thrill ran through my body as I realized they were almost certainly Emily's, and now I was wearing them.

The bra was a bit more difficult. I had never worn one before, and it took a few moments of awkward twisting to get both straps over my shoulder and to get it clipped snugly at the back.

I looked myself over in the oval mirror over the sink, blushing bright red. Obviously, I was flat-chested, but the way the bra covered my chest and the way the straps ran over my thin shoulders really did give the impression it was hiding something. The miniskirt was so short that it barely covered my ass. My midriff was almost flat, but I didn't have anything like Emily's toned abs. My thighs were almost totally uncovered by the miniskirt, and they looked slender but soft. I had never a strong man, and in the skirt and bra, I looked downright girly.

Bracing myself, I opened the door. Emily stood in the doorway, still dressed in her short shorts and bra. We were actually almost the same size; she was about half an inch shorter than me, and our weights probably weren't that far apart. The difference was that she was sleek, toned, and tan, while I was soft and pale.

Emily smiled widely as she looked me up and down, then whistled. My cheeks were hot again, and my heart pounded. I couldn't bear to look her in the eyes. She stepped a little closer and grabbed my wrist tightly. Still stunned and not sure what to do, I followed her back into her bedroom.

She gave me a hard shove onto the bed. I fell onto it, looking up at her. She had an intense and hungry look in her eye as she climbed on top of me, straddling my waist. I felt her tight, compact body pressing me down onto the bed. She weighed more than I did; after all, muscle weighs more than fat. Her lips hungrily pressed against mine and her hands ran down my sides, pinching and squeezing my soft body. She pinched my side just inches above my hip, and I tried to bolt upright in shock, but she was holding me down tight.

She kissed my lips hard, then my cheek, then my chin, and then the underside of my chin, and then my neck. I tilted my head back as she kissed my exposed neck over and over. Her teeth nipped at my neck and her hands continued to stroke, pinch, and squeeze. I reached up and grabbed her forearms, but she kept going.

I yelped in shock as she reached under me and grabbed my ass with both hands. She disengaged her lips from my neck and looked up at me, eyes still intense and hungry. I could feel her shaking with excitement as she groped me.

"You're so fucking soft" she said, staring right into my eyes. I looked away, more than a little scared of her sudden ferocity. She squeezed my ass tighter and let out a sigh. I had no idea how to respond. I felt one of her hands let go of my ass. Soon, it was under my chin, forcing me to look back into those intense, predatory eyes.

James19999
James19999
342 Followers
12