The Wingman

All characters in this story are 18 years of age or older. They are in or have completed their final year of high-school and are moving on to college.

Iowa has been the corn capital of the good old U.S. of A. for as long as anyone in my state can remember.

We have corn festival's, corn parties and I'm sure any other thing that you can imagine that is associated with the sacred yellow cob.

I come from a small place called Pleasantville. Yeah, just like the show. It's near Lake Red Rock and it was a great place to grow up.

Like the Keith Urban song says, it had, "Everything I needed, John Cougar, John Deere, John 3:16."

Music, farming and Jesus. What else could a boy ask for? Oh, I don't know, maybe a girl.

You see, all through high school I played the Invisible Man. Not intentionally, but because of my lack of status on any of the sports teams, I was usually just a ride along, or as my best friend once put it, I was the World's Best Wingman.

The handle was given to me early in my first year. Mark Robinson was a star at everything that he did, but basketball was his calling. He starred immediately in the early years of high school. All the pretty girls wanted to be by his side, and he refused to disappoint any of them.

Mark's biggest problem was that he came from a very religious family and he was never allowed to date unchaperoned, and that's where I came into the picture. The only time that Mark was able to get away was if he took his twin sister Macy and or me, along with him and his date. Turns out that it was also a community thing, strength in numbers when teenagers are out, I guess.

With only 200 students at our school it wasn't hard to know most of the students, so Macy was almost always friends with, or an acquaintance of Mark's dates.

Once, and only once, Mark referred to it as a double date. For his efforts he received an earful from his sister, and a threat to tell his parents about him having pre-marital sex in the backseat of their mother's SUV. Even if that sex was just a hand job.

Many a Saturday night, Macy and I would sit in the front seat together at the drive-in, sharing a tub of greasy, buttered popcorn and a pop, while her brother and one of her friends learned the facts of life in the backseat.

Macy was everything that you would want in a girl. She was beautiful with her dark hair and Eastern European, almost Russian looks. She was also very athletic and smart. I know what you're thinking, and yes, I tried to make a move. Both times it resulted in a slap and a punch.

The punch was from Macy, "I swear to fuck Brandon, you touch my tit one more time and I'll knock you out", and the slap came from Mark in the backseat of the car both times. "Fuck man, what are you doing? That's my sister."

It was hard to explain to my best friend that his sister wasn't ugly, and the sounds and smells of him playing with a pussy just over my shoulder had the same effect on me that would on most other guys my age.

So, after a couple of months of riding shotgun on dates, with a number of different girls, the nickname, "Wingman" stuck with me until graduation.

By the start of senior year, I was the guy that you hired if you needed someone to tag along so that your dates friend or ugly cousin was covered. And if your dates friend / cousin tried to cock block you, I could steer her clear. A true wingman.

"Hey Brandon, I'm taking Alysa to the Vallee on Saturday night, you feel like tagging along?"

Not only was I not that close of friends with the guy asking, I had always had a small crush on Alysa, so the idea of her getting fingered or worse, while I played nice with her friend had absolutely zero appeal to me.

"Sorry man, I saw the movies last weekend."

"Yeah, I know. Mark told me. Look, I'll pay for everything. I'll even buy dinner and I'll get my brother to pick up a six pack for us."

"Nah. It's not going to work for me. Thanks anyway."

I could tell what was coming next, Harry Bateman's parents had the biggest farm within 100 miles, and he wasn't afraid to flash their cash around.

"Come on man, she promised to blow me. Maybe you can hook up with her friend."

That wasn't likely. It had never happened so far. Most times when the girls at my school were going out and needed to bring a friend, they requested that I came along, because knew that I was the safe choice. Not too handsy, never forceful, and as a few had said, I even smelled good.

"Sorry, Harry. Not gonna happen."

"Fuck man, I'll give you fifty bucks and you can drive the Yukon. Look, I'll even put in a good word with Alysa, maybe she can talk her friend into blowing you too."

"In advance." I held my hand out and waited for him to peel off five $10 bills. It was a drop in the bucket for Harry and it would be a bit of extra cash for me.

Pocketing the Alexander Hamilton's, I made my way toward the gym. I could hear the sound of Mark's monstrous feet slapping the asphalt as he ran to catch up to me. From the speed of his approach, I could tell that it wasn't a good sign.

"What the fuck Bran, did you just pimp yourself out to Bateman over me?"

"If that's what you want to call it, then yes. And just so we are crystal clear, he pays me. Unlike my ungrateful, piece of shit friend. Also, he said that I might have a chance with the girl Alysa's bringing."

"Yeah, let me know how that works out for you."

"What's that mean?"

"You're too soft buddy. The girls at this school want a guy that's assertive. You know, someone that will take what they want. Anyway, now what the fuck am I gonna do on Saturday? I already told Cheryl and Macy that it was a go."

"Sorry buddy, but I'm trying to be more "assertive"." Putting my fingers in the air for quotations to mock him just pissed him off more.

"Fuck you Brandon. Next time I'll bring someone else."

"Oh yeah, I bet that there's a line-up of assholes dying to listen to you getting a hand job from Cheryl. The sound of latex gloves rubbing on your dry dick is a turn on for us all. Tell you what, I'll honk the horn when I drive Harry's Yukon past your house."

"Wow. You're such a cunt when who wanna be."

"Yeah, but I'm a cunt with $50 bucks in my pocket, the keys to Bateman's whip, and he, unlike you, is going to try and hook me up."

"Fuck you."

"Is that all you got Robinson? Don't play this game with me, you're just not any good at it."

I wish that I'd kept my mouth shut, because this basketball practice was harder than most. Coach had me trying to guard Mark, and he proved a point to me about just how good he was by punishing me on the court.

As planned, Harry's text came in around 3:00 in the afternoon. He picked me up and as agreed, I got behind the wheel and drove over to Alysa's house to pick up the girls.

They were standing near the end of the driveway as we pulled up. Alysa was waving and bouncing like a maniac while her friend had her back to us making a phone call. Alysa was dressed in her usual short skirt and low-cut blouse. She always liked to show off the goods. That, accompanied with her blonde hair, is why she is so popular around school.

I knew the other girl before she even turned around. Her shoulder length brown ponytail, with her small frame covered with tight Levi's, a school hoodie, and the ever-present plaid backpack that she called a purse, gave her identity away.

Harry jumped out of his truck and held open the back door like a gentleman. He and Alysa jumped in and buckled up while we waited for the friend.

The look on her face was enough to make me laugh when she saw who was behind the wheel of Harry's Yukon. She shook her head and climbed in.

"Brandon?"

"Mace."

"Mark couldn't talk you into going with him and Cheryl tonight?"

"Nope. Better options here. Plus, the last time we went out with Cheryl, I was seated in the splash zone. Ended up with a little something extra on my jacket if you remember?"

"Ew. That's gross. Thanks for reminding me."

"Oh shit, I forgot." I looked over at Mark's sister as she shot death rays at me through burning eyes.

"You say one fucking word, and I swear, I'll kill you right here."

"What?" Both Harry and Alysa asked from the backseat.

Macy was quick with a "nothing" and from her tone, neither of them had the nerve to continue the questioning.

It was the same night and the same time as the jacket incident. Cheryl had her hand wrapped around Mark so hard that he couldn't ejaculate. All of the sperm was being held in the shaft of his dick as Cheryl stroked him furiously. Mark was groaning in what was later determined to be agony. When she finally released her hold. Mark's cum flew everywhere. Some landed on the shoulder of my jacket, but the best was the huge glob that landed in his twin sister's hair.

Mark laid back against the seat. Cheryl tried her best to clean up all that had landed on her, and I laughed like a hyena. To this day, it is a sore spot with Macy.

"I'm not joking Brandon. Say anything, and you'll burn in hell."

I didn't say anything, but there was no way she could erase the smile that was curled up on my face.

The ride to the restaurant was quiet. The sounds of Harry and Alysa making out was drowned out by Harry's playlist belting out of the speakers while Macy kept herself busy, texting."

About 10 minutes away, Macy looked at me with a look of disgust on her face.

"Really?"

"Really, what?"

"Did you tell my brother that you were getting a blow job tonight?" Her tone wasn't much higher than whispering so that those in the backseat couldn't hear. So was mine.

"NO! Well not exactly. I told him that Harry promised to try and hook me up tonight. But that's before I knew it was you." Her expressions changed before my very eyes, they were both pissed off looks, but for completely different reasons.

"What, I'm not good enough for you Brandon?"

"No. Yes. You know what I mean. Fuck, we've been out so many times. I mean come on Mace, I tried to touch your boob once and you almost killed me. Do you honestly think I'd try anything funny on you?"

"You're a piece of work Wingman. You think that just because Bateman tells his new girlfriend to ask, I should blow you?"

I whispered that she should blow me just for putting up with all of her shit for the past several years.

"What?"

"I said that I think you should blo...nothing. Never mind. Look why did you come anyway. You must have heard that it was me tagging along."

"As a matter of fact, I didn't, or I probably wouldn't have come. But free food and a movie, is never a bad thing."

"Yeah, and we've both had our fair share of those over the years, haven't we?"

Dinner was good, and with darkness just on the horizon, we headed to the drive-in. Parked away from the other cars, Harry got a small cooler out of the back and handed out a round of drinks.

The cold beer tasted good as we watched the movie.

I could hear zippers and buttons being undone, but I never once looked over my shoulder, and that's why I was the best wingman in Iowa. Both Harry and Alysa knew that they were safe with me. Unfortunately, the same could not be said for Macy.

Curiosity got the best of her. The sounds of our friends making out was more than enough to draw her stares. At one point I noticed a naked leg pushing on the headrest of Macy's seat and knew that tonight's party had escalated beyond a simple make-out session.

Macy's head bobbed just like Alysa's as she followed the movements of her friend's head as she sucked Harry, and her eyes widened when the main act started.

With a few grunts and some "Oh, oh, oh" noises, I would have guessed that Bateman was in, but I didn't need to.

Mace had her eyes glued on them, and when she noticed that I was looking at her, she made a circle with the finger and thumb on her left hand, and thrust the index finger of her right hand in and out of it.

We had been together many times when her brother ventured deeper and deeper into sexual exploration, but this was a first for either of us. Never had anyone ever had full on intercourse in front of or in this case, behind us.

Macy squirmed on her seat while Harry thrust into Alysa. The sounds of, "Harry, oh fuck, harder, faster, oh my fucking god", will always be etched into my memory. My crush on her was over forever.

As fast as it started, it had stopped. It was a 42 second rollercoaster ride for both of them. Harry came quietly and Alysa put her hand over the doom light as he dropped the used-up condom onto the gravel of the drive-in parking lot below us. The eighteen-year old's had just lost their virginity in the backseat and Macy had watched the whole thing.

Disheveled, would be the best word to describe the couple as they walked toward the concession stands. Macy and I laughed at the same time, and for the first time, I looked in the backseat. Everything was in order. No spare clothes, no splashed cum dripping down or condoms laying around, just a wool blanket to keep their naked skin off the cool leather seats.

I didn't hear Macy move, but I felt her breath on the side of my face. Turning to look at her, I was surprised to find her on her knees on the seat next to me. She was leaning over the console, inches away from my face. Her make-up bare, all-American beauty was right there in front of me.

"What?"

I was lost. I had no idea what was going through her head.

My best friends twin sister put her hand on my chin and closed the distance between us. Her lips were soft and warm against mine, and although my kissing experience was limited to a couple of games of spin the bottle, I did what came naturally. I could feel her soft breasts pushing against my arm as Macy moved her mouth and pressed her tongue against my lips. Our tongues darted back and forth over our teeth and lips. It was the best things that I had ever felt, by a long shot. If I wasn't mistaken, our kiss lasted way longer than Harry and Alysa's copulation.

"Holy shit Mace. That was incredible."

Her "shut up" came out just as Harry opened the door to his Yukon. The doom light brightened the vehicle. I looked at Macy sitting next to me and noticed how flushed her face looked.

She looked a little lower and noticed how my pants were tenting out.

"Really Brandon?"

"Holy fuck, can't you two get along for even 5 minutes?" Alysa was scolding her friend but had no idea why.

Logically it was me that got dropped off first. Harry took over the wheel and with a round of good-byes, we parted ways.

My parents were long in bed and that worked in my favor. Even though I had only had the one beer, my mother could smell beer a mile away, and I would have caught proper hell for it. And then there was also the fact that my boner still hadn't gone down.

Naked in bed, I replayed every second of night. Normally, the thought of hearing someone having sex right behind would have been enough for the spank bank, but then Macy had to go and fuck it all up.

The bing sound of a text snapped me out of my trance. I picked up my phone and opened the text. The shy blushing face emoji was the only thing on the screen. I didn't recognize the number, but I knew that it was either Alysa or Macy. Alysa would have been the logical guess. How often is it that you fuck someone with two people sitting 2 feet away from you. It would be no wonder that she was blushing.

The second bing scared me enough that I dropped the phone on my chest.

It was still the same number, but this time there was a message. "Don't tell Mark." Again, it could have been either girl. Alysa had been out with Mark a number of times, so maybe she wanted to keep him on the back burner in case things didn't work out with Harry. On the other hand, it might be Macy getting nervous about me telling her brother and my best friend, that she kissed me. I was torn, but in the mood for some fun.

"What's in it for me?" The response was instantaneous.

"Fuck you Brandon."

"Is that what's in it for me or is that a veiled threat?"

"Not veiled at all. I will kick your ass." I still wasn't positive, but given my experience with both, I was leaning toward Macy.

"Too late. Texting him now."

"No. Don't do it Bran. I'll tell everyone about your boner."

Definitely Macy. Alysa never called me Bran. I put Macy's info into my phone.

"Every guy my age gets boners. Who do you think you're gonna shock with that revelation?"

I waited for over a minute for the text to arrive.

"I'll tell them it was because you were perving on Alysa and Harry."

"You don't get the rep of being the best Wingman in the state by perving, so no one, not even you would ever believe that. I'll tell them the truth. It was because you crammed your tongue down my throat."

"What's it going to cost?"

"Boob pic."

"Fuck you, asshole."

"Hey Mace, you have to reel in that crazy. You know that when I tell Mark, he'll hound you about it forever."

My phone fell into silent mode. The screen darkened because of lack of use and I figured it was the last I'd heard from her until Monday at school. Just when I was about to call it a night, in came a text alert.

"Bra shot. No skin!"

"Bare"

"Fuck you"

"Hey Mark, did I ever tell you about the time..."

"Fucker. Bra. Some cleavage."

It was probably the best that I would get, and it would be better than anything else I had ever received in the way of a naked picture.

"Agreed"

It took longer than I thought it would, but when the attachment arrived, I was shocked. Macy's face wasn't visible, but she was pulling down the front of her black lacy bra, giving me a really good look at her cleavage and her soft mounds. Macy's hair was swept over her shoulder almost as if she were trying to cover herself up.

Something inside of me changed forever just seeing that picture. My courage to reply took forever. The dry lump in my throat wouldn't permit me to swallow and almost stopped me from breathing.

"Absolutely beautiful Mace. I'm going to stare at it for 5 more minutes, then I'll delete it. I promise. Thanks for the kiss."

It broke my heart, but as promised, I deleted the picture. Although gone from my phone, it would live in my memory forever.

Over 30 minutes had passed and nothing. It appeared as though our texting was over for the night.

Lights out. Tucked in. It was going to be hard to sleep thinking about my first real kiss and my first semi-nude girl picture text.

The light and binging from an in-coming message alerted me again. I almost rolled over and avoided looking at it, but for some reason I was compelled to. Drawn to it like a bug to a porch light, I picked up the phone.

"Mace" appeared at the top of the screen. When I opened my message center, my heart definitely skipped a beat.

My best friend's sister had sent me another picture. No words were attached. No explanation why. She just sent it. There they were Macy's naked breasts.

No one could prove that it was her, but there she was. Her boobs, naked and on display for my viewing pleasure. They were spectacular. Perky and firm, with hard nipples and crinkled areolas. I hadn't asked for this picture, nor did I plan on deleting it in five minutes like the other one.

The flash of my phone filled the dark room. Seconds later, I was sending a picture back to Macy.

"Jerk" came back to me in a matter of moments. I guess my naked chest didn't do to her what hers had done for me.

"Really? Yours had a way more profound effect on me"

The smiley / blushing face emoji was back, along with "I was hoping for something south of your chest"

"Wow. Who's a perv now"