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The Best Wingman
🕑 Added 2020-08-06 18:11:00 +0000 UTC
Scott and I were best friends growing up. We did everything together and had those sort of “friendly rivalries” that often happen between young boys. He was a little better at soccer, me at basketball. Science and math were more my thing where he received a scholarship based on his music skills and, eventually, became a published author (much later). I was pretty popular in school but Scott was well liked, if slightly more introverted. When I graduated Valedictorian and Scott finished third, he was happy for me partly because he really didn’t want to give a graduation speech.
Our families, however, could not be more different. Scott’s was fantastic. He had two little sisters who adored him and parents who showered him with love, affection and respect. His littlest sister had a rare nerve condition that made her go deaf at the age of eight. We all learned sign language so that she never felt left out. His family was awesome. Mine, on the other hand, were… well… they’re not super important to this story but suffice it to say that they were the opposite of that. Not quite “monsters” or anything. Nothing that horrid. But just generally unhappy, miserable, loveless people.
I spent as much time at Scott’s house as I could growing up. Partly because his family was wonderful. Partly because I didn’t want to be at home. Scott’s mom was even my first crush though I quickly discovered that unmarried girl’s my own age were much more accessible if you know what I mean. Scott and I dated a couple of the same girls but we agreed to never let girls come between us. In fact, Scott even set me up with one of his exes whom he’d broken up with. He was a good friend.
We drifted apart for a little while after high school but both found ourselves at UVA for post-graduate degrees. This was in a day and age before internet so you can imagine our surprise when, during orientation, we found ourselves sitting across the welcome center from each other.
“Brian?” he said as he approached me after the first session.
“Scott? What the hell are you doing here?”
“Same as you, man. Going to law school. What a small world!”
“Yeah… Holy shit. Small world indeed! This is awesome. It’s nice to have a friendly face.” We gave each other a quick high five before looking at each other. Both of us had kept in good shape. I’d played D2 basketball and he’d managed to walk on the soccer team at Washington State where he’d gone to undergrad. I looked around and leaned in, “I hadn’t expected the girls to be so hot here.”
Scott smiled tightly, “I’m not supposed to look. I’ve got a girlfriend…,” he paused for a moment and then whispered, “but yeah… damn right!” We laughed and made plans to meet the next night for drinks.
Charlottesville is a college town. No doubt about it. There’s plenty to do and the city caters to the college kids pretty overtly. It wasn’t hard to get a recommendation for a good bar and we met up around 9 at The Livery Stable. It was a nice little bar. Relatively quiet and low key. Perfect for two old friends to get reacquainted.
“So what have you been up to?” I asked.
“Graduated from Stanford. Double majored in Music and Literature. Trying to decide if I want to write for a living or become an IP lawyer. You?”
“Geezus. I don’t have it together at all compared to you,” I said with a laugh. I took a sip of my drink, careful to not consume too much. I’d learned my lesson about getting black out drunk in college. The frat pictures proved that. “Majored in Business and Finance. Coming to law school because it seemed like the logical next step, I guess. I’m not really sure.”
“You’ll figure it out. You’ve got three years to find out what you like,” he said reassuringly.
“I guess… I don’t know. You have things planned out pretty well AND you’ve got a girlfriend… she cute?” I asked with a laugh.
Scott snickered, “Oh yeah… way hotter than I deserve, man.”
“Got a picture?” I asked. He pulled out his wallet and pulled out two photos. He slid one out and flipped it around to show me. The girl was, indeed, quite cute. Pretty blonde, blue eyes, short. She looked like she was fun. “Yup… definitely too hot for you!”
Scott laughed again in response, “What about you? No girl?”
I shrugged, “I had some luck in undergrad but it’s been a bit of a dry spell. I knew I was coming here and didn’t want to start something back up.”
Scott, who’d already thrown back one beer, took another long pull of his second and held the empty glass up, “Well we need to get you a girl. No need for something serious, right?”
I shrugged, “I guess so. One night stands aren’t really my thing.”
Our waitress walked up just then and the sentiment died in my throat. A one night stand with her might not be so bad. She was a curvy little brunette with a great smile. Wide hips, narrow waist and an ample, but not giant, bosom made sure she ticked all my buttons. She was wearing a tight cutoff t-shirt and short jean shorts. Standard bar waitress attire in my experience. She grabbed Scott’s glass and set down another before walking away. And it was a nice walk away. Her perky little ass shook and I couldn’t stop eyeing it.
“Reconsidering that comment about one night stands?” Scott asked with a grin.
“Uhh… maybe a little,” I said.
“Let’s make it happen, man?”
I demured. All I needed was to have some sort of drunken harassment bar incident before I even started classes, “I’m good… it’s fine.”
“You think I’m too drunk to get her for you? I’m the world’s best fucking wingman!” he declared to the bar in general. A couple people looked at us and he took another swig of his beer. Two and a half beers in less than 30 minutes seemed excessive. But Scott rallied hard. He sat up straight and fixed his leather jacket, straightening his shirt and running his fingers through his hair. Then he said, without slurring a single syllable, “I’m getting you that girl.”
He stood up and took one staggered step before pausing and righting himself. Then he proceeded to walk over to the waitress. I didn’t hear what he said but they both returned after 30 seconds and she looked me up and down appraisingly. I felt momentarily like a piece of meat. She put her hand on her hip and said, “Okay… Your buddy dragged me over here to hear this ‘war story’... so let’s hear it?”
“I’m sorry… what?”
“Don’t be shy, man. Tell her about how we met!”
I looked at Scott. We’d met on the playground in elementary school when I put mud in Scott’s hair and he punched me. Our dad’s had to come to the office to pick us up. Scott’s dad lectured him. My dad smacked me. It wasn’t a day I particularly liked to talk about.
“Okay… here’s the deal… Audrey, right?”
“Aubrey,” the girl corrected indulgently. To her credit, she kept her smile. As gorgeous as she was, she probably got this all the time.
“Scott was in the 141st in Afghanistan and I was in the 103rd, right. Big rivals. Always trying to best each other during performance reviews.”
I couldn’t believe what I was hearing. I was worried about a bar incident tarnishing my law school experience. Apparently Scott was going for stolen valor.
“... but then one night at this bar…”
“In Afghanistan?” Aubrey asked.
“Yeah… that’s right… Afghanistan,” Scott said, continuing his impossible lame story. “Brian here sees me getting into a little trouble. This may surprise you, but sometimes I drink too much,” he said.
Aubrey looked at me and gave me a smile. I tried to return it in a way that silently said, “Thanks for indulging my drunk idiot friend.” I guess it worked as she brightened a little and turned back to Scott.
“So anyways.. These three… no… four guys… it was four guys, right Brian? Yeah… four guys come at me and start pushing me around. Talking about how the 167th are a bunch of pussies.”
“Why did you care… you were in the 103rd, right?”
Scott stopped and squinted at her, his mind trying to process the critique of his story. “Yeah… but we 103rd guys always stand up for the heroes of the 167th… so yeah… anyways… I tell them, ‘you and what army!’ and the one guy throws a punch. I mean… I ducked it of course but his five buddies… there were six of em you see… they come at me… And then suddenly, out of nowhere, Scott jumps in. Like a fucking ninja he was. He did some sort of crazy ninjitsu kungfu stuff like you’d see in movies and then… blam,” he said, smacking his hands together suddenly with a loud clap. It actually caused Aubrey and I to jump in surprise, “Suddenly three of em are down. Now there’s only… uhmm… four left… And Brian says… what did you say, Brian?”
“I don’t remember,” I said, still aghast at what was happening.
Scott looked in confusion and said, “Is that what you said?” he studied me for a second then looked back up at Aubrey, “Yeah… that’s right… I remember now… he says to them, ‘I don’t remember how many towel heads I’ve killed but I can add eight more tonight if you want’.”
I winced… racist stolen valor. Excellent.
Aubrey looked at me with more compassion than I would have thought. Then she said, “Well that’s very impressive. It’s a good thing that Brian is such a good friend. You seem like you need it.”
“I do… I do…,” Scott said and slumped back in his chair. He folded his arms and smiled proudly. As if he’d succeeded.
“I think maybe you’ve had enough though. Don’t you think?”
Scott started to say something but I cut him off, “Yeah. We should get going. Thanks for the beers,” I said apologetically. “I hope your night improves.”
“I had the early shift and you’re my last table. So it probably will get better now,” she said with a smile. Scott paid the tab and stood up before stumbling to the floor. Aubrey and I rushed to pick him up, “I’ll help you guys out,” she said. She helped me pick Scott’s drunk ass off the ground and walk him the couple blocks to my car. “You really are a good friend, Brian,” she said as I slid him into the front seat and closed the door.
“You know that whole story is bullshit, right?”
“What, the story about two 23 year old law students who ALSO were in the army and the four to ten men you killed in an Afghanistan bar? I had a hunch.”
I smiled, “I’m really sorry. He’s my best friend from high school. I guess he’s become a bit of a lush....” I paused for a second and then realized something, “Shit… I don’t even know where he lives.” I reached in the car and flung Scott forward. He was almost unconscious as I manhandled him trying to find his wallet. Finally I found it in his jacket and rifled through it only to realize his license still had his California address. “I guess he’s sleeping on my couch,” I said.
Aubrey frowned and then looked at me, “No worries,” she said. “Tell you what. I’ve got no plans for the night. How about we take him back to your place and I’ll help you get him all tucked in. Then you can tell me some real stories about you. You do seem like a nice guy,” she said.
I perked up immediately, “Really?”
“Guilt by association isn’t something I support,” she said as she climbed into the back. I watched her smooth toned legs disappear into the car as I wrenched my eyes back to her face. She caught me looking and gave me a knowing smile, “Just don’t be like your friend and get passed out drunk, okay?”
“No, ma’am,” I said and gave her a mock, formal salute. That broke a lot of the tension and we laughed.
We got Scott up to my new apartment and dumped him on the bed. It was a small studio apartment. The best I could afford at the moment. It wasn’t too bad but it wasn’t particularly nice either. Aubrey didn’t seem to mind. We sat across the room on the cheap leather couch I’d bought. “So tell me about yourself,” Aubrey said.
“So I enlisted at 17 and fought in the great war…” I said with a smile.
Aubrey gave me a playful slap, “Seriously, Brian.”
“Pretty generic story, really. Went to high school. Graduated. Went to Undergrad. Graduated. Going to law school… hope to add graduated to that too. What about you?”
“I’m going to UVA for pre-med. Trying to be a doctor someday.”
“Yeah? That’s awesome,” I said.
We hit it off surprisingly well. Aubrey seemed very cool and genuine and we talked until almost 2am. We shared stories of our families. Hers was almost as fucked up as mine. I told some of the good Scott stories, hoping to redeem my friend’s image a bit. Eventually, she looked at her phone and said, “Look, Brian. It’s getting pretty late…”
I frowned but understood, “I get it. You want me to give you a lift home?”
“No… I want you to kiss me finally,” she said looking at me.
“What?”
“God you’re an idiot,” she said and leaned forward. Her soft pink lips landed on mine and suddenly she was kissing me and I, dumb as I am sometimes, kissed her back. Our tongues danced together. We started making out in that hot and heavy way that young twenty somethings do. She moaned into my mouth as my hands, emboldened by her own boldness, wandered over her hips and ass. She responded in turn by grinding herself into me, breaking our kiss to smile at me as she bit her lip. “I see you finally figure it out,” she said, rotating her hips on my hard cock to emphasize her point.
“Yeah… I guess I did,’ I said and descended my lips to her neck. She moaned out loudly. I snapped my eyes up, concerned that Scott might have woken up. Turns out, he was already awake. He was watching us with a weird kind of intensity I hadn’t ever seen. I started to say something but he made a gesture with his hand cutting me off and then gave me an enthusiastic thumbs up before spinning his finger in the universal gesture for me to continue.
I didn’t really need to be told to continue at that point. I ignored my friend and focused on the bubbly, vivacious woman that was fumbling with my pants. “God it’s been so long since I’ve been fucked. You are going to FUCK me, right?”
“I mean… yeah?” I said unconvincingly.
“I mean it, Brian. Don’t make love to me… FUCK me… okay? I’ve had like an 18 month dry spell and I NEED it.”
“Fine by me,” I said and I yanked her shirt off and pulled her perfect tit out of the cup of her bra, attaching my mouth to the nipple as I licked and nibbled at it, trying to figure out what she liked.
She squealed in excitement at the suddenness of my gesture and then followed a low, soft moan of sheer contentment as I felt the nipple harden in my mouth. “OOOoohhh… yeah… that’s it, baby. Oh yeah,” she said. Her fingers ran through my hair as she gave little soft shudders whenever I hit the right spot. Her voice cooed appreciatively in my ear as we got increasingly aggressive with each other. She pulled my shirt off then slipped seductively down to her knees between my legs. She pulled on my shorts and I shimmied out of them, flinging them across the room. The naughty look in her eye as she gazed at my hard cock made it twitch, bumping against her face as it swung between us. She nuzzled it sensually and murmured softly before plunging her mouth onto the swollen head. I glanced over, noticing my friend was still watching from the bed. He gave me another double thumbs up but I tried to ignore him.
Instead I returned my attention to the gorgeous co-ed currently sucking my cock with an eagerness that more than made up for her lack of technique. She looked up at and smiled with her mouth wrapped hungrily around my cock. I let my fingers tangle in her hair, remembering what she’d told me she wanted. I pulled her up gently and she stood in front of me. My eyes must have been completely glazed over with lust. Aubrey smirked at me and hooked her thumbs into her shorts before slowly pulling them down. She shook her hips as she did, dipping a little bit then pulling them over her cute little bubble butt and letting them drop to the floor.
I gazed at her, weirdly afraid to reach out and touch her. She looked gorgeous. Her skin was smooth. The neatly trimmed little tuft of hair above her pussy looked incredibly inviting. “Please… fuck me,” she whispered. I reached up and stroked her soft skin, making her shiver as my fingers teased her bare, pink flesh. She stood there, eyes closed and head back, moaning softly as my fingers traced their way up her thighs. I pressed my hands into her sex and she gasped, shifting her weight to spread her legs just a little bit and allowing me access to the hot, wet core within.
I slid my finger insider her and said, “So you want to be fucked?”
“God yes,” she gasped.
“Good,” I said and rewarded her with a second finger.
“I’m on the pill,” she said, making an obvious offer.
“Even better,” I growled as I gripped her hip and spun her over the arm of the couch. She gave another girlish yelp and giggled but I put an end to that by quickly lining up my cock and sliding into her. She let out a low, lustful moan as I filled her up. She felt like she was on fire, heat radiating from her and enveloping my cock with fire.
“Yessss… God I needed this… fuckkk,” she said. Her head was hanging down over the edge as I plundered my new conquest. I looked up again and caught Scott’s eye, he was watching in rapt attention, his hand was gently rubbing at his own crotch as I hammered into Aubrey’s almost limp body. I gripped her hair, pulling her head back as I pummeled into her. She caught sight of Scott and gasped, “Oh, God!”
“Don’t worry about him… focus on me,” I whispered and rammed into her harder than before, taking her breath away.
“Yessssss,” she hissed and I knew she was past the point of caring who saw. I complied with her earlier request. I fucked her. I fucked the hell out of her. I fucked her brains out. Basically every euphemism that you can think of, I did. When she was done, we collapsed in exhaustion on the couch and cuddled and kissed. “That was so good, Brian. A little weird that your friend watched though.”
I looked over, Scott seemed to have passed out again at some point and he was now snoring on my bed. “Yeah…,” I told her, unsure what else to say.
“Is this like a thing you guys do?”
“What?” No!” I protested.
“It’s cool if it is… it was kind of hot getting fucked for an audience,” she whispered.
“I mean… I’m glad you liked it but this was a first for me.”
“Oh,” she said, I couldn’t tell if she was relieved or disappointed.
I gave her a little kiss and said, “I’d kind of like this not to be a one time thing though.”
She cocked her eyebrow, “Fucking me while a friend watches?”
“No… I didn’t mean… No… I just meant I’d like to see you again,” I said.
Her smirk turned into a genuine grin, “I’d like that.”
Aubrey and I dated for a bit and genuinely had a great time until she went off to med school. We never did fuck in front of Scott again though it did occasionally come up. Fortunately, a week after Aubrey left for Med School, Scott got a new roommate. A new female roommate. A very hot female roommate. But that’s a story for another time.
Comments
Thanks so much. I'm always uncomfortable when I write those things even when I know it's "right" for the story. I worry sometimes that it comes off as a "lecture" from the author but I usually can't help myself.
Reso
Interesting premise for a voyeur story. I really appreciate how you include and immediately address inappropriate behavior in your stories. An example is your handling of racist statements in your stories (Scott's drunken 'towel heads' comment, Max's misuse of "chink" to refer to Asians outside the context of consenting role play), with another character immediately rejecting that behavior as inappropriate.
