The Wingman

My cock was so hard that I thought I would burst. I couldn't resist the urge to jerk off to the pictures.

"Fuck Mace, you're killin me"

The next text was a short video. It was the same pussy, but I could hear her breathing, as I watched a finger gently slide downward and part the wet lips and slide in to the first knuckle on her small finger.

I couldn't let this go without sending something back to her. Hitting the video on my phone's camera, I was getting closer and closer to cumming, so I gave my dick a few more tugs until it shot cum up and over my stomach. I hit the send button and waited.

"Was that cum?"

"Yes"

"From the pictures and video, I sent you?"

"Mace, you're so fuckin hot. What did you expect?"

"You came so hard, is there any on your shoulder?" There was a laughing / crying face emoji also attached.

"Close but no"

"Bet some of that would have landed in my hair" Same emoji as before.

"I wish"

"You wish it landed in my hair?"

"No. I wish that you were here" Here was nothing for a while after that, so I started.

"Hey Mace, why me?"

"???"

"You could have any guy at school. You've almost beat me up for trying to touch your boob and now... well you know" Again it was quiet for a bit.

"Your Mark's best friend. I couldn't just tell you what I thought, we've known each other forever, but now with us moving away it's different"

Different in what way? The rest of the night and the next day at school, it was all that I could do to not stare at the pictures and video of Macy on my phone. When the day was over Mark was waiting for me outside.

Mark had a proposal, that of course would work in his favor. He wanted me to be his wingman on Saturday, but only for a short time. He wanted his parents and Cheryl's parents to believe that the four of us were all going to hang out and the only way he could have the car, was to bring Macy along. Then after we were all together, he would drop his sister and I off so that he and Cheryl could be alone.

It was a great plan, but he didn't want Macy to know until the last minute, nor did he realize that it would be beneficial for me also.

"Bran, you have to do me this solid. Figure out what to do with Mace for a couple of hours and I'll owe you forever."

"You already owe me more than you'll ever be able to pay back."

Mark dropped me off at my place and told me that he would send details later. It felt good to be in my vacant house. My parents had left $50 emergency money and instructions on how to heat up a frozen pizza on the counter. Setting the temp at 350 and the timer at the required setting, I opened a pop and turned on the game.

The pizza wasn't nearly as bad as I thought it would be, but the game was. By the seventh inning I said fuck it and changed the channel.

When my phone rang, I assumed it was Mark, but for the hundredth time that day, I was wrong.

Harry Bateman was again in the need of my services. He needed a wingman for another night Alysa. When I told him no, he immediately came back with the usual $50 offer, but once again I turned him down.

"Come on Brando, I need this. Same deal as last time and I'll give you $100 cash." I thought it over in my head and came to the conclusion that we could make it work. Mark work drop Mace and I off at my place, Mace could walk over to Alysa's place, and Harry and I would pick them up there.

"Done." And then I told him the details.

"Sorry man, Macy's not coming."

"What, why?"

"Alysa's all freaked out. Said that Macy was watching and perving on us screwing last time. Said it felt like her grandma was staring at us doing it."

"I'm not third wheeling it man."

"You're not. Her cousin is in town for a couple weeks. She saw your yearbook pic and she's down. Buddy, you're getting a free meal, a couple of beers, a hundred bucks, and you're losing your cherry all in the same night."

In any other universe, at any other time, this would have been the best news that I had ever heard, but tonight it broke my heart.

"Sorry Harry, count me out. I can't do it", and I hung up. No sense even thinking about it any longer.

The sound of my phone ringing didn't surprise me. I knew Harry would try again. He'd sweeten the offer somehow. Guys like him aren't used to being told no. Without looking, I answered.

"Yeah."

"What the fuck Bran?" I wasn't Harry after all.

"Hey Mace."

"Did you just turn down Harry, a night out, a hundred bucks and a sure thing?"

"Ah, yeah."

"Did you tell him you'd go if I went?"

"No."

"Well Alysa's in my face about it. Said that you said you wouldn't go unless I tagged along."

"Never said that. Said I wanted you to come, and then said I wasn't going with Alysa's cousin. No more, no less."

The tone and mood changed with those words. Everyone knew that Macy was my best friend's sister and they would have never expected anything to be going on between us.

After a few moments her voice seemed to be a couple of octaves lower, when she asked, "Are you still coming tomorrow night?"

"You still want me to?"

"Yes", and that was it.

Right on time, the Robinson family vehicle came into view, but unlike every other time Mark was going on a date, I didn't get in. Instead, I opened the door so that Macy could get out. She looked at her brother, then to me, then back to her brother.

"Come on Mace, I'll explain it to you."

When I had finished giving her the general idea of why her brother had dumped us both she asked if my parents would be okay with her hanging out until Mark returned.

"I didn't tell Mark, and I don't want to freak you out, but they're gone for the weekend."

"To where?"

"Chicago."

"Why didn't you tell Mark?" That was a good question. I should have. It would have made things easier for him, but I was self-serving. I wanted to be alone with his sister and I told her so.

"What do you thinks going to happen Brandon?"

"Nothing. I just want to be alone with you."

Macy had been in my home before, but it had been years. The last time was probably my 10^th birthday party, so I showed her around and offered her something to drink. Diet Coke's and a bag of Cool Ranch Doritos was served up.

Putting on The Mandalorian, we sat beside each other on the sofa.

Frightened, yet aroused would be the only way that I could describe what I was feeling. I swear that I could feel Macy's pulse beating into the cushion where we sat.

Every chance I got, I inched closer, until the naked skin of our shorts covered legs touched. Macy jumped when she felt the hair of my leg, pressing onto her smooth, hairless leg, but she didn't move.

My hands were shaking so much I had to set down my can of pop. With a quick, direct move, I put my right arm around Macy's shoulder. She didn't object, and leaned into my body, which was a good sign, and when I looked down, I could see that her nipples were erect beneath her brasserie and t-shirt, which was an even better sign.

We continued sitting quietly until I couldn't take it anymore.

"Mace, would you be mad if I kissed you?"

"More like, mad if you didn't." There was a smile on her face, but I noticed that her can of pop was shaking even worse than mine had.

Five minutes into our kiss, I was half-laying on the sofa with my back leaning on the arm, and Macy was laying on top of me. Our lips explored every inch of the others mouth. Macy tasted sweet and tangy from the pop and chips, but I wouldn't have changed it.

As casual as possible, I moved my hand up to the side of her ribcage and gave her boob a gentle cupping from underneath. When there was no resistance, I cupped it until my hand was full and my thumb worked back and forth over the hardened nipple under her clothing.

Macy stopped and back up.

"Are you sure that your parents won't be back tonight?"

"Positive."

That was the key word. In one fluid motion Macy pulled her t-shirt and bra up over her head. Her chest was naked in front of me for the very first time. Only strands of her long dark hair gave her any sort of coverage.

"Up." Macy beckoned me forward until she was able to reach down and pull off my tee.

When she leaned back into me, her naked skin felt warm and soft against my chest. Our lips met and our hands roamed freely over the naked skin beneath them. I honestly would have been content do keep this up all night, but Macy's thigh grinding on my bulging crotch told me that things would continue to escalate.

Lifting my ass up off the cushion, Macy pulled my boxer briefs to my ankles and stood back. Without removing her eyes from my erection, she looped her tiny fingers into the sides of her delicate panties and eased them to the floor.

Naked. Macy Robinson was naked and beautiful, and she was in my home. I was so excited that precum had started oozing from the hole in my dick. If Macy sat down where she was before we started all of this, and her naked thigh touched my dick, I'm pretty sure that I would ejaculate on the spot.

I didn't. Macy sat on my lap with her knees on either side of my hips. The warmth and wetness of her pussy pressed on the underside of my shaft. Every move caused the tiny delicate hairs above her slit to tickle me. It was a feeling that I could easily get used to.

The small cheeks of her ass filled my hands as I squeezed them together. Macy arched her back, removing her chest from mine. Without asking, I sucked one of her hard nipples into my mouth and rolled it around with my tongue.

"Oh shit." Macy was very receptive to my actions. Her hands and fingers wrapped themselves into my short hair and pulled my face hard to her breast.

Her slim silky body slid down my legs and off of me. Her hand grabbed at my penis and tugged the shaft up and down. Macy's mouth was opened and not far form the tip. I knew what was coming and as happy as I was with it, I offered to be a gentleman.

"Mace, I really want you to, but I'll be okay if you don't."

With not so much as a blink from her, she put me between her lips, and started bobbing her head. It didn't take long for her to be rewarded for her actions. The sensation of her tongue wetly caressing me, while her fingers cradled my balls was more than my virgin cock could take.

"Mace, I'm there."

The mushroom head of my penis exited her mouth with a popping sound. My first spray hit her just under the chin and my second and third splattered across her chest and boobs. I watched in amazement as the cum dripped down her neck, dripping and coating her hard nipples. I wasn't sure what to do next, but I couldn't resist kissing her as hard as I could.

A warm, damp towel cleaned Macy's chin and upper torso. She was giggling when she asked if I always came that much.

"I don't know Mace. I've never been that excited before in my life."

"Me either. I think I'm soaking your sofa."

She probably was, but I wanted to check for myself. Laying back against the arm, Macy spread her legs so that I was able to reciprocate her earlier actions.

Small strands of her juices looked like a tiny spider's web on the lips of her pussy. With one swipe of my tongue, they were erased from her. Macy was very wet. Her excitement leaked freely, and my mouth savored all of her rich flavors. With nothing else to compare it to, I still felt that if would never be any better than it was at that very second.

Pleasing her became my number one goal. Everything that I did at that point felt like it was for her, but there was no doubt that I was enjoying it as much, or more. Macy let me know what she liked and what she didn't. Trying to push my rolled-up tongue into her was met with a "No". Then, while gently sucking her clit, she brought her hand to my cheek, and a soft "Yes" escaped her.

We were learning on the fly.

Focused on what was making her happy, I sucked on her dark pinkish lips and nibbled at the little button of her clit. My intention was to never stop doing this for her, but after her body shook from what I believe was an orgasm, Macy had other ideas.

"Break. Break, I need to take a break."

Before she would kiss me, Macy wiped the stickiness off of my face, with the same damp towel that she had used to clean up my cum.

It was a big day. One that I would hopefully remember for the rest of my life. I was normally the proverbial good-boy son, but for tonight's special occasion, I risked the wrath of both my parents when I snuck a beer and a White claw out of the family beer fridge.

Macy sat facing me. We idly played with one another's previously untouched body parts. Kissing, caressing, stroking, enjoying.

"Bran." I answered with a "Uhm" as she lightly pulled her fingernails down the length of my still hard shaft.

"Can we move upstairs. I don't want my first time to be on your family's sofa."

My head bobbed like it was on a spring. Macy stood first, held out her hand, and lead the way up the stairs.

The hand me down queen size mattress that had once belonged to my parents was in the center of the room. Macy stood on one side of the bed and I stood on the other. My lips were dry, my mouth felt like it was made of cotton and my stomach churned into knots.

"Mace, there's a condom hidden in the drawer next to you. It's in the tin Altoids box." She just shook her head and whispered, "on the pill".

Visibly shaking, we climbed into the middle of the bed. Macy was sexy beyond her years. On her hands and knees, her perky boobs hung down away from her chest, while her back swayed, showing off her firm belly and sweet round ass.

Her warm frame draped itself over my body. She was silky smooth compared to the abrasiveness of my skin, yet we both seemed to be enjoying the feeling. Our kissing and fondling were what could be considered foreplay, but other than the sensation, it wasn't needed. Macy's hard nipples and moist vagina, along with my raging hardon was enough to let anyone know that we were both ready to go.

"How do you want to do it Mace?"

"You on top, so that I can look into your eyes."

On my knees, between her spread legs we had the alignment perfect. Macy rubbed the head of my penis around her opening. My precum mixed with her natural lubrication was more than we needed. With a nod of her head I moved forward.

Almost with a pop, the slick knob was inside of her. Macy and I stared at one another and moaned in unison. Slowly, I continued. There was no barrier to impede my progress, so a little by little, I sank into heaven.

The feel of her silky grip and wetness was epic. If I hadn't came earlier, it would have already been over for me. When my testicles came to rest the cheeks of her ass, I knew that we were no longer virgins.

A smile came to my face and a small chuckle escaped me. Macy had a quizzical look on her face.

"What?"

"Your just so beautiful. I'm thinking about how lucky I am. Six months ago you punched me for trying to feel your boob, and now you're naked in my bed."

"Naked in your bed and you've done more than cop a feel of my tit, you're inside me."

Wrapping her arms around my neck, she pulled herself up, buried her tongue into my mouth, and started gyrating her hips.

Every nerve ending in my body was on high alert. Our timing was off, but we would work on it. Each thrust, each push, every nibble and bite, was added to our sexual experience resume.

At one point, Macy flopped her head back onto my pillow and closed her eyes. Closing my eyes was the last thing on my mind. I watched every movement of the female form below me. I watched as my shaft entered and exited. I watched as my dick pulled back the fleshy meat of her pink lips and pushed it back together. I watched the grip of skin that encompassed me. I watched the build up of her juices that coated me. I watched her hands tearing at my bedding beneath her as she came.

It was all too much for.

"Mace...sorry"

"Do it. Don't worry baby." She knew it. She knew that it was over for me. I had given all I could, and she had given me permission to finish.

"Fuuuuuuuuuuuck."

Entwined, body and soul, we drifted off to a place most 18 years old's, don't normally go this early, to sleep.

"What?" I jumped out of my skin. Macy was beside me, still asleep. No one was talking and the room was dark. Then it happened again. Within a split second of one another's, our phones rang again. Searching the darkness for the offending sound and noises, I found my phone on the coffee table downstairs.

"Yeah?'

"Fuck man, where the fuck have you been? Cheryl's been calling Mace, and this is the third time I called you."

"We're watching Netflix. We couldn't hear because it's so loud."

"We'll be there in ten. Cheryl's gotta get home."

"Okay."

Three stairs at a time I sprinted up to my room. Touching my naked lover to shake her awake, had me starting to get hard again.

"Mace, Mark called. They'll be here in ten minutes."

Like a stretching cat, she raised her arms over her head, yawned and semi screamed, "I feel so freakin great."

"Bran, call Mark back and tell him that I'm staying until your parents come home on Sunday."

"Think I won't? I'd do that in a heartbeat."

Begrudgingly, she got out of bed and went into my washroom. With the door open, I had another first in my life. Macy sat and peed in front of me. When she wiped and washed her hands, she took my toothbrush out of its holder, dabbed on some paste and started brushing. My look must have surprised her.

"What?"

"Nothing."

"Damn right nothing. Just remember where your mouth has been today. I think you're safe letting me use it." I nodded in agreement. Macy spit, rinsed, dabbed on more paste and handed the toothbrush to me to prove her point.

Standing inside the door of my parent's home, making out with my best friend's sister was surreal. Every single kiss felt as alive as the first time at the drive-in. Her lips owned me.

When the brightness from the lights of her mom's car could be seen coming down the street, it took everything in my power, to let her go.

"Mace...I love you."

"I know you do."

Stepping out on the porch, the plaid backpack flung over her shoulder, Macy jogged toward the SUV and jumped in the backseat. With a honk and a wave, I was alone in my house.

The shower felt good, but it didn't fill the void that I was feeling. I had told Macy that I loved her and got nothing in return. She had been gone for nearly 2 hours, no text, no call. I knew that I was reading too much into it, but I missed her.

Watching sports highlights, eating cold pizza and washing it down with a Dr Pepper took my mind off the events of day, if only for a second.

I grinned at my luck. I was no longer a virgin. I had lost that card to the hottest girl in town, and it was great, even if no one would ever know.

Even on a noisy night like tonight, when the wind blows the neighbors chimes like that of a percussion orchestra, I could hear the creaking wood on the porch as it gave away the secret of someone's presence. I knew that I wasn't alone even before I heard the light knocking.

Macy stood on the other side of the screen door. She was wearing different clothes than from earlier, her still wet hair was pulled back in the customary ponytail, and her backpack was stuffed to the brim.

No vehicle in sight. No one had dropped her off.

Opening the screen, she slid in between and door and the frame, dropped her bag and basically jumped into my arms.

"I love you too. I'm sorry that I didn't say it first."

There was no need to apologize, but I wondered how she was, and why she was here.

"Mace, what are you doing? Your parents are gonna murder you."

Murder might be a little strong, but they certainly would be pissed that their only daughter was out past her curfew, and in the company of a guy.