Best Wingman Ch. 3

I continued fucking Malia off and on for most of the year. She seemed to get off on having Scott watch which, truthfully, I was starting to think Scott also got off on. I thought it was a little weird at first but Malia was such a hot fuck that I wasn’t going to complain. Some weekends, I thought she was going to wear my dick off for good.

The other thing that happened was that Scott and Caroline started dating. On the nights she would spend the night, Malia and I would fuck enthusiastically in my room. I tried to keep quiet but between the bed banging against the wall and Malia’s barely muted moans, I’m sure they knew what was happening. One morning, Malia had already left and I awoke to the glorious smell of bacon and cinnamon buns. I staggered out of my bedroom and saw Caroline was standing in the kitchen looking all cute with just one of Scott’s T-Shirts on.

“You guys seemed to have a good night,” she said with a wink.

“She wasn’t complaining,” I said.

“Oh… we heard. That DEFINITELY wasn’t complaining big guy,” she said, giving me a saucy little wink. Her flirting would have made me uncomfortable if she’d been anyone else, but that’s just the way she and I interacted. It had become pretty normal. What wasn’t normal was the gorgeous expanse of well tanned legs that she was showing me. I’ll admit, my eyes lingered longer than they probably should have. She kept working on breakfast, switching back and forth from foot to foot causing her hips to shake slowly to some silent tune she was listening to in her head.

Scott walked out, catching my stare before I could look away. He smiled at me and walked up to his girlfriend, wrapping his arm around her waist and kissing her. “Good morning, babe.”

She turned and gave him a kiss and opened her mouth to him. As I watched the two lovebirds make out, Scott’s hand grabbed her T-Shirt and he pulled it up, revealing her bare ass to me.

She realized exactly what he was doing and smacked his hand away as she abruptly broke the kiss, “Scott!” she said, yanking the t-shirt back down and blushing. She she looked over her shoulder at me and gave me a tight little smile.

“What, babe? I like showing off my girl. You’re sexy as hell,” he said, winking at me. “Brian, tell her she has a fine little ass.” He gestured at me imploringly.

“Uhmm… yeah… I mean,” I stammered, unsure exactly how much flirtiness I should engage in with my best friend’s girlfriend.

“Scott! Brian is a gentleman. Not like you,” she said, smacking him in the shoulder again.

“Did you not hear Malia last night. I don’t think he’s as much of a gentleman as you say he is,” he said. Caroline blushed again. I’m not sure who was redder though, her or me. “By the way, my cousin will be here tonight.”

“The Harvard professor or the trailer trash?” Caroline asked. She had a way of saying things in a much snarkier way than she actually meant. We’d gotten used to it so neither of us said anything.

“The South Carolina one… Teagan,” he said. Scott’s family was originally from South Carolina but most of them had moved away and largely looked down on the one branch that had stayed behind. I knew it was a bit of a sore subject with him. He’d mock them and rip on them but really hated it when other people piled on. “You’ll like her, Care. She looks a little like you,” he said, teasing his girlfriend.

She shot him a look and when he tried to kiss her to make amends she turned her cheek and said, “Uh-huh,” in a decidedly huffy tone.

I knew why she was annoyed. Based on the pictures I’d seen, the only resemblance between them was that they were blondes with nice figures. Beyond that, everything about them was different.

“I’ve got class later, can you pick her up Brian?”

“Yeah, no problem, which terminal?”

Scott laughed, nearly snorting orange juice through his nose. He rubbed his face and muttered, “Damn, Brian… that stung. No way do they have the money for a plane ticket. She’ll be at the Greyhound at 3:30,” he said.

---

I got to the Greyhound station at about 3:20 and waited. It was in a really rough part of town and I didn’t want Teagan to have to wait very long. Brain had shown me a picture of her so I knew what to look like. But even if I hadn’t, I’d have been able to pick her out easily. She stepped off the bus wearing a pair of white flip flops and short cut-off jean shorts. The tiny little tank top she was wearing was doing nothing to cover the black bra she was wearing. Her clothes all looked a size too small except for the tank top which was two sizes too large and practically dangling off of her. She was thick but in a good way. Big chest, strong legs, broad shoulders. She looked around casually, almost as if she was surveying the world for the first time. I honked the horn of my car and she turned to look at me before walking over with an exaggerated waggle to her hips. I swallowed hard. This girl was going to be trouble.

She leaned over the passenger window, peaking in and showing off her big tits. “You, Brian?” she asked, smacking her gum as she chewed. I was suddenly reminded of every movie scene where a prostitute propositions a John. Yup. Trouble.

“Yeah. Scott told you I was picking you up?”

“Yeah,” she said, flinging her small bag of clothes into the backseat and sliding in. “What do I owe you?”

“Uhmm… nothing?” I said, confused.

“Not an Ass, Grass or Cash sitch, huh?” she said. Her southern accent made her words slide out as one, horribly poorly enunciated, blur.

“Uhhmm… no… it’s fine… just happy to help a friend.”

“Suit yourself, stud,” she said then looked out the window and instantly started fiddling with a joint and a lighter.

“Uhmm… not in my car if that’s okay.”

“Whatever,” she said despondently but she slid the small joint back into the plastic bag she’d pulled it from and went back to staring vacantly out the window.

“What brings you to town?”

“Had to get away from that hellhole. Scott offered me a place to crash for a couple nights. Figure I’ll just hitchhike to LA. I’m gonna be a star, you know,” she said.

“Uhmm… movies or TV?” I asked, really not sure how to respond to that.

“Don’t matter… just so long as I’m rich,” she said. “I met a guy who runs a talent agency. Says I’ve got what it takes.”

“Teagan… I… A lot of those are scams,” I said.

Her head snapped around to me, “Dontcha think I already know that? I done did my research. This here’s a legit talent agent. Dockwell and Jenkins. They represent Scarlett Johansson… did you know that?”

“Uhmm… no… I didn’t,” I said, mentally reassessing the young woman. Her accent and grammar were poor but maybe they simply masked the mind behind it.

“He and I got to talking at a bar. He tried to sell me on being a triple threat… you know what that is?”

I shook my head as I stole a glance at her. Her tan legs looked shiny and inviting and I was, admittedly, a little distracted.

“Oh bless your heart, Brian,” she said, patting my knee, “It’s a bitch who can dance, sing, and act. But I gave him a sample of my singing and we agreed that wasn’t my strength, if you get my drift.”

“But at least you can dance?”

“He sure thought so…” she said as she let her words drift off. I imagined her dancing and found the image completely incompatible with what I knew about her, “But just my extra special kind of dancing… private dancing… you know?” Her voice got low and suddenly the image I had of her dancing had much less clothing and a big metal pole. Now that made more sense. I swallowed hard and nodded.

“How long are you staying?”

“Probably just one night… unless something gets me to stay a second… or someone,” she said with a smirk. It was hard to tell if she was flirting with me specifically or just randomly positing that she might hook up with someone. We rode along back to the apartment without speaking, me unable to get the image of her dancing erotically out of my mind, her humming some peppy little pop song and proving that she was, indeed, completely tone-deaf.

When Scott got home later, we had a nice dinner and a couple beers. Teagan flirted with me the whole time, leaving me embarrassed and uncomfortable.

“What’s the matter, Brian?” she asked, giving me a little wink as she brought a forkful of  salmon to her lips, then closed her eyes and ate it with an exaggerated “mmmm” of enjoyment.

“Nothing,” I said, shifting in my seat as Scott chuckled.

“Ohhh… am I making someone uncomfortable? Or something?” she snickered. She and Scott exchanged a glance of amusement. “Maybe there’s something I could do to help with that?”

“No… no… I’m fine,” I stammered.

“She really doesn’t mind helping out, Brian. She’s easy,” Scott said. I stared at him and then glanced at her. Her cousin had basically just called her a slut to her face, surely she’d be pissed off.

Instead, she simply looked at me and ate another bite of her fish, this time twirling her tongue around it with a blatantly sexual action. I swallowed hard, the thought of a different pink meat getting tasted by her tongue flitting through my mind. “Uhhmm… that’s your cousin, man…”

“So what?” she said, “I bet Scott wouldn’t even mind watching, would you cuz?” My friend simply shrugged and she continued, “I want to get laid… do you want to get laid, Brian?” she asked, leaning towards me and using her arms to squeeze her breasts together highlighting her large breasts.

"Uhh… maybe… I mean…"

"Good… cause I wanna get fucked… and not like some kinda romantic shit. In fact, don't even stick it in my cooch. Just grab a stick of butter and lube my ass up, stud?"

I couldn't think of anything to say. I'd never had someone so sexually aggressive and blunt before. Malia was eager and not shy about much of anything but this was like a whole other level.

"It's weird with Scott here."

She laughed and slid down on the floor, looking up at me with big eyes accented with copious makeup. "Scott's fine. He likes watching?" The way she said it left me with the distinct impression it wasn’t their first time doing this.

"Sure. Sometimes," he said. Those were his words but his smile, posture and the look in his eyes told me something different. He was getting off on this.

The realization gave me a little more comfort. I grabbed Teagan's hair in my hand and she murmured, "Mmm… yeah, stud."

"Show your cousin how good you can suck dick," I responded, fishing my cock out and presenting it to her. She dove forward, hoovering up my cock like it was a heroin laced popsicle. I leaned back, enjoying the work as I gently guided her up and down on my cock. I didn't watch Scott directly but I couldn't help glancing at him occasionally. He was just sitting there stroking his cock through his pants. "You sure you're good with this. It's your cousin, man."

He simply nodded dreamily, entranced by the sight of his cousin basically skull fucking herself on my cock. I shrugged, still not sure of the game we were playing but my arousal was overriding everything. I fucked her mouth harder and harder, holding her on my cock as she spluttered around me before letting her up and repeating the process. Her mascara was running and there was saliva all over her messy face but she didn’t complain. Hell, she looked as if complaining was the literal last thing she might do.

“Fuck… I need some pussy,” I said.

“I figured you’d want to take my ass, stud?” she said, flipping onto her hands and knees and spreading her ass cheek wide and inviting.

“You sure?” I asked, stroking my cock at the target before me.

She laughed, “It’s a little big but I’ll manage.” She sounded so matter of fact about it. Like she was challenging me. I’d never had anal before. Most girls were a little intimidated by the size. Teagan seemed to take it almost as an insult that I was worried.

“Shit… I need some lube,” I said.

“Butter works just fine… vegetable oil if you got it,” she said but Scott gave a little chuckle from across the room and tossed me a bottle of KY jelly. “Oooh… big spender gonna treat my little ass right, huh?”

I said nothing, just applied a liberal dose of lube to her ass, rubbing it in with my thumb while stroking even more on my cock. I knew from the few aborted attempts I’d had over the years that my only chance was to have it be really slippery and go slow. As I positioned my cock against her sphincter, I pushed slightly, watching it strain at first and then as she exhaled, it opened up for me and I slid in. “Fuck… me… Damn… fuck,” she said.

“You okay?”

“Uh-huh…” she managed. It sounded more like an affirmation than a denial but there was uncertainty in her voice. I eased another couple inches into her and she gave out a long moan, “Yess… geezus… cuz… fuck… fuck…,” she said. Scott just sat there silently. Watching with rapt attention.

I slipped the last couple inches in and bottomed out. Her reaction was to simply collapse forward, ass still high in the air with her overly manicured fingernails spreading her cheeks wide. There was a light sheen of sweat on her and as I pulled out and slammed back in she started moaning more and more enthusiastically. Each slide in was met with a sound of pleasure and a tightening of her sphincter that was so pleasurable it almost made me black out.

“Do it bastard… fuck my fat fucking ass!” she screamed.

“Yeah?” I said, feeling that boiling over of aggression that Malia has taught me to embrace.

“OHhh… yeah… shove that fucking meat stick in my butt baby!”

I shoved her hands down and smacked her ass, causing her nice bubble butt to ripple pleasantly before gripping the flesh and spreading her more fully. Now with a cheek in each hand, I grabbed tightly and started increasing my pace. She said nothing, just fucked me back even harder in return. We were panting and groaning. Rutting like wild animals. I knew I wasn’t going to last long. When Teagan wasn’t grunting obscenely, she was instead spilling filth that would have provided a first class education to even the most worldly of sailors. I don’t remember most of it. Some of it was barely english. I do remember, “Rape my ass like a Viking,” as it struck me, even in that moment, as being incongruously erudite. She also at one point begged me to “hurt her so bad she couldn’t sit for a month.” I just spanked her harder and kept pounding her ass since that’s what she seemed to want.

After several minutes of this, I finally had enough. I grabbed her hair, yanking her back hard and used that as leverage to fuck her with three or four more really violent strokes. All I could think of through the red haze of aggression was how I wanted to fuck her until she couldn’t talk anymore. When I came, I screamed out and shot several spurts in her before pulling out and finishing on her back. She didn’t say or do anything, just started madly frigging herself until not 5 seconds later she was coming, her whole body quaking as my cum landed on her back.

She lay there panting as I collapsed beside her. I looked over, Scott was gone and his bedroom door was closed. “Fuck,” I said.

“I’ll say, stud. That baby maker of yours is fucking to die for. No wonder Scott keeps you around…”

“What?” I said in confusion.

“He gets off on it. You hadn’t noticed?”

“I mean… I guess… thought he was just trying to be a good wingman or something.”

She laughed, “Guys really are stupid. You know that.”

“What do you mean?”

“Just fucking pay attention. Geezus. If a dumb redneck can figure it out. Surely a smart college boy like you can!”

She said nothing more after that, putting off my attempts to talk to her about it. Obviously Scott liked to watch. I figured he just enjoyed being a good friend and probably was a little bit of a voyeur. Fortunately, it only took  me a couple more months to figure out a little bit more of the puzzle that was my best friend.

Teagan left the next day and I never saw her again. She went to LA and last I knew, she had some minor success on some trashy reality shows and leveraged that into being a decently successful “influencer”. Given her ambition and hidden intelligence, I wasn’t surprised. Still, whenever someone mentions her in passing, I always have fond memories of that afternoon.