The Wingman

Another blushing emoji.

I knew better than to send nudes of myself. Dick pics live forever on the internet once they are out there, but common sense had long gone to bed for the night when I pushed the send button. I knew it would be less than a second before Macy was looking at a picture of my semi hard cock pressing the material of my Joe Boxer's, on the screen of her phone.

"Fuck me" Her text was short and sweet, yet not very lady like.

"Is that a request or a statement?"

"Why do you have to ruin stuff Bran?"

At some point I drifted off into a restless night of sleep. This would be a night that I would relive more than once in my lifetime.

The sound of my phone ringing woke me. I wanted it to be Macy, but it was the exact opposite, it was Mark.

"Hey."

"Hey skid, we're heading to the lake to kayak in 45, I'll pick you up."

"Who's we?"

"Cheryl and me. You and Macy. Who the hell did you think "we" was?"

The Robinson Family SUV pulled up in front of my house and my options were limited so I hopped in the back with Macy. With a round of, "Hey. Hi. What's up?", we were on our way.

There was no uncomfortableness between Macy and I, the only thing that was out of the norm, was when she, tilted her head pursed her lips and looked down at my crotch.

Macy looked amazing in her cut-off jean shorts and grey t-shirt. For the entire trip she sat sideways, half looking at me, half looking out the window.

With everything loaded into the kayaks, we headed in different directions, only agreeing on a place and time to meet for lunch.

After a solid 2 hours of kayaking around the lake we made our way to the stone bluffs to swim and cool off.

My eyes were glued to Macy's ass as she shimmied her legs out of her jean shorts to reveal the white bikini that lay beneath, but when she pulled the t-shirt up over her head, I almost died. The real live boobs that I had a picture of on my phone were less than 10 feet away from me.

"What?" Macy was staring at me, staring at her.

"Oh, you know exactly what. I'll never be able to look at you the same again."

For the first time ever, Macy and I were alone on what some might just call a date. Laying on a blanket, soaking up the sun, we talked about everything from going away to college, to sex.

"Why do you think your brother does so good with the girls at school?"

"Definitely basketball."

"Do you think he'll do as good in college."

"Yeah, even if he doesn't start, he has good pick-up lines to fall back on." I couldn't help but laugh. Mark didn't have any lines that I could ever remember him using effectively.

"What? They all say that he's sweet. He charms them with his words. All the girls say that he has classic pick-up lines." I was still smiling but played along.

"Okay, so your friends with most of his dates. Enlighten me with the magic words that he uses, maybe I'll try them on you"

"Ha, you wish. Well he told Cheryl that she must have come from heaven, because she looked like an angel."

"Come on. That's sooooo cheesy. And you think that it's a good pick-up line?"

"I suppose that you could do better?"

"Easily." Macy cocked her eyebrow and called my bluff.

"Then let's hear it tough guy."

"Well, my personal favorite is, "Does this rag smell like chloroform?" It works for me every time."

Macy threw herself back on the blanket and screamed with laughter.

"Fuck Bran, you're truly a jerk."

"Really Mace? Then give me your best line."

"Okay, "You're so hot, even my pants are falling for you". She tried to cover her eyes in mock embarrassment, but we both knew that we were just having fun.

"So, you going to take it there? How about, "Your ankles are having a party, I think your panties should come down for a visit". Macy was instantly ready with her next one.

"I'm just not feeling like myself today, can I feel you instead?"

"I like it. It's good, but not nearly as good as, "You remind me of my baby toe. You're small and cute, and I'm probably going to end up banging you on the coffee table later tonight".

"Like hell you are. How about, "Legs are the word of the day, now let's spread the word"' It was my turn to laugh and scream.

"I'm still ahead on the score clock. This is also a good one, "I've played lots of Tetris in my day, let me see if I can make this fit" or "Hey, my dick needs a hug from your mouth". Macy stopped before she spoke, with her mouth just slightly open. Was she thinking of her next line or had I crossed a line to a game that she was no longer comfortable with?

"Sorry Mace, I was just playing."

"I know. It just gave me a flashback from last night. Maybe we should have stuck to ones that were less aggressive."

"Like, "Do you know what you'd look really beautiful in? My arms." Macy looked at me and though barely noticeable, she bit her bottom lip.

"Well Bran, I don't know if you were trying, but that was your best one so far."

"Not really. I have one that's better, but I'll save it for another time."

"Not a chance buddy. The damage has already been done. Let's hear it." I wished that I could have just sent her the blushing face emoji in advance, but that wasn't an option.

"Hey, I just realized that you look a lot like my first girlfriend."

"Boo. That one's not even that good Brandon, because I know you've never even had a girlfriend."

"Exactly."

Our mouths found each other for the second time in as many days. Rolling onto my back, I pulled Macy over onto me so that her upper torso was on me. Her fingers clawed at my curly hair as she ravaged my mouth with her tongue. What we lacked in experience in kissing, we more than made up with in enthusiasm.

For the first time in all of my 18 years, my hands roamed naked flesh that didn't belong to me. Although it was only her back and shoulders, it felt perfect.

Macy's leg moved so that it was just over my lap, in a position where if she moved a little more to her left, she would have mounted me. There was no possible way that she couldn't feel my erection pressing against it.

Bravely, I slid my right hand up her back, over her ribcage, and with my thumb just under the bottom, I cupped her breast. A moan and warm breath filled my mouth.

Macy's leg rubbed the hardness in my shorts to the point where I thought that I might explode. Our first time in each other's arms felt very natural.

The only thing that could have possibly ruined it for us, did. The sounds of Mark calling our names from the shoreline of the lake, accompanied by Cheryl's cackling had us scrambling.

Macy was safe, but there I was with a boner pointing skyward in my shorts. It was going to be hard to explain to Mark what I was doing with one, when it was only me and his twin sister.

Distracted by a fish or some stupid thing in the water, Macy took the opportunity to drag my sorry ass into the water and to safety.

"What the fuck are you two doing, I thought that we were having lunch, not swimming." Mark seemed a little irritated by us.

While the girls opened the cooler bags and took out the sandwiches, Mark told me why he was so upset.

"Fuck man, I thought that today was the day. We talked about it all week." I knew that Mark meant having sex. He always meant having sex.

"What happened?"

"Nature. She's got her period man."

"Shit luck buddy."

"Right? Mandy Townes ask me to hang out today. I know that I would have got something from her."

"Wow man, that's pretty shallow. Just because Cheryl's not down to fuck, doesn't mean that she won't blow you or something. Maybe, just maybe, you can treat it like a real date and try having some fun with her. She's pretty cool to hang with."

"Fuck you. What kind of bullshit have you been eating? Once you ever get to touch a pussy, you'll want it all the time. Wait and see."

He wasn't wrong. I had looked at a picture of his sister's perfect boobs 12 hours ago and I had a covered one in my hand less than 10 minutes ago, and it was all that I could think of.

The rest of the day was spent on the lake. We kayaked until darkness approached and we could no longer move our arms. Mark's pouting had dropped to a level that was acceptable for everyone and when we loaded up and headed out, he even treated for ice cream.

Cheryl rode with her body hanging over the console of Mark's mom's SUV. If we had to guess, he was getting a hand job, while driving. Sitting in the silence, Macy undid her seat belt and turned her back toward me and pushed closer.

"Rub my shoulders Brandon. They're sore from today." Her words caught her brother's attention and he looked at us in the rearview mirror.

"No way. I'm sore too. You rub mine."

"Don't be a goof Brandon, rub my sister's shoulders." And there it was, Mark's approval to touch his sister. Macy had wanted contact of any kind on the ride home and this was all that she could come up with.

I undid my own seatbelt, turned to my left and lifted my leg onto the seat so that Macy could slide back between my legs and I could rub her shoulders.

"Not like that. A little harder by the neck. Jesus, I should just get Cheryl to do it." The show was a good one. Mark looked back a couple of times and smiled at his twin giving me shit, but what he didn't noticed was her hand gently running her fingernails over the skin and hair on my thigh.

Shifting and moving until she had perfect placement, Macy reached back and untied the strings of her bikini top.

"Do it on my skin. The material of my t-shirt is going to give me a rash." It was the same as earlier. Me touching her bare skin, but this time someone else knew that I was doing it.

I was concerned about my best friend and what he might feel if he knew what was going on with his sister and I, but I didn't have to worry. Cheryl's handy work had him in a spell and it was all that he could do to focus on driving.

Under the shroud of darkest, I risked death and dismemberment when I lowered my left hand off of Macy's shoulder and put it on her belly. Her palm instinctively covered it, pressing me against the clammy heat. I wasn't sure where to go from there, but if Mark happened to look back, he would still see my right hand on his sister's shoulder.

To my surprise, Macy lifted her hand and pulled the thin fabric that was covering her breasts, away from her skin. With a gentle push, she moved my hand up.

The smoothness shocked me. As did the idea that her breast was hard, yet soft, all at the same time. The hardness of her nipple was like a stone under my thumb. I could never imagine ever feeling another boob in my life that would feel any better than this.

A moan that was probably louder than she expected, escaped Macy's mouth.

"Is he loosening up the stiffness Mace?" Mark asked his sister.

She put her hand over my hard shaft and told him, "Not really. It's still really stiff, but we're working on it."

I focused on the back of Mark's head to see what he was doing, and when the coast was clear, I kissed Macy softly on the back of her salty, sweaty neck.

Brakes being applied snapped us both out of our trance. There I was, once again in a predicament. Having the time of my life with Macy but pulled up in front of my house with a raging boner.

Macy shuffled over to her side of the backseat and I grabbed my backpack and held it in front of me.

"Thanks for the day. Ladies, lunch was great, see you guys later."

"Hey Bran, drive-in next Saturday?" I tried to downplay my excitement, but I answered way too quickly.

"Yeah, sounds good."

I hadn't made it to the door of my house, when for the first time that day, my phone binged. A paired of over-exaggerated puckered red lips appeared on screen. It was from Macy.

Later in total darkness, the vibration of my phone awoke me. It was shortly after midnight, but I was immediately awake.

"You up?"

"That would depend on what you mean by up"

"Awake"

"Then yes. Wasn't, am now. Why aren't you sleeping?"

"Can't"

"Why?'

"What are you looking for?" Macy apparently felt like texting about things that I had no idea about.

"I was sleeping. Wasn't looking for anything"

"In a girlfriend. What are you looking for? What are your "Classic" rules?"

"Classic rules? Dirty in the mouth...don't go down south"

"WTF"

"it's 3:00am. I don't know"

"Come on. Tell me one of your rules.

"Common sense. A dirty mouth implies poor hygiene. I won't kiss a girl with a dirty mouth, so I guess that I won't go down south either. Everybody knows that"

"Remind me not to text you after bedtime anymore."

"What? You asked?"

"You have lots of experience in the "down south" department?"

"Honestly? Seen a few movies, but that's it"

"Sorry I'm bugging you"

"You kidding? Your texts are the best. You can text me anytime you want." The very next, was a face shot with a dog's snout and ears attached to it.

"Thanks for today Bran. It was a good time."

"Great time. You?"

"Me what?"

"Lots of experience south of the border?"

"Nope...same as you. But, Mark walks around here naked all the time, so I've seen "it" several times."

"Hey Mace"

"Yeah"

"You kiss soooo good, and your lips taste like strawberries" Another blushing face emoji and some puckered lips showed up on my screen.

"You're not so bad yourself Wingman"

"OUCH!!!"

I laughed to myself about Macy calling me a wingman. Laying there surrounded by the dark, I wonder where this was headed. Would we progress to the point where my buddy might want to do damage to me? If my concerns were unreasonable before, the messages that followed were enough to cause me fits.

Three consecutive pings told me that Mace had sent a few more messages to me, but I was wrong. The first was a picture of her mouth and teeth. They looked clean and perfect. The second was the same picture that she had sent the night before of her boobs, and the third was the game changer.

Macy had held her arm up as high as she could and took a picture of her naked body, laying on her bed. She was lean, tanned and sexy. With one of her hands on her stomach and one of her legs bent at the knee, I could see the sparse black hair that barely covered her mound. It was short and straight, with absolutely no curls. From the angle, there was only the slight view of her ass. Her beautiful face was missing from the shot, but it was overall the best thing that I had ever witnessed.

"Mace, you're absolutely beautiful. I would have told you that even without these pictures"

As suddenly as the text messages started, they stopped. As my Grandpa used to say, "Radio silence".

Monday mornings suck. It was the last week of school and I had to get used to work, because I always have to work at my summer job early on Monday's with no exceptions. My only saving grace is a quick, cold shower and the jog to school, to wake me up. Unfortunately, today's shower wouldn't help my condition. The thoughts of Macy laying naked had me rock hard and my dick was pointed skyward like a missile that was ready to launch.

Fuck it. I grabbed my phone, took three quick pictures, sent them off along with the caption "you did this to me" and opened up my last night's text.

Looking at the picture of the naked body on the screen, I wrapped my hand around my shaft and started to stroke. It didn't take long, before I was stuccoing the inside of the shower with a fresh batch of batter.

After 8 hours of listening to repetitive shit, I found myself back in the shower and once again rinsing my load down the drain. No texts, no pictures, no messages. Nothing. Macy's radio silence continued on until Thursday evening, when my phone rang.

"What?"

"Get ready numb nuts, we'll pick you up in ten."

"For what?"

"I'm taking Cheryl to the Dairy Shoppe for an ice cream."

"Why the fuck would I want to go with the two of you?"

"Like you've got anything fuckin better to do. Plus, tonight we're celebrating. I'll buy."

"Celebrating what?"

"I'll tell you later. See you in ten."

"No. I don't feel like being the third wheel."

"You've always been the third wheel Wingman." Click.

Sure enough, Macy was in the backseat and gave me the usual "Bran" greeting.

Finding a table under one of the umbrella's I asked Mark what we were celebrating.

"Buddy, I got the call. It's Boston College baby. Full ride. I'll be just down the street from you."

"What? Wait. Where are you going to school?" Macy asked.

In all the times we had been in the same vehicle, or at the same function, I had never spoke to Macy about "where" she planned on continuing her education after we graduated high school.

"MIT. Why?'

"Shit. I don't know. Maybe you could have said something considering I'll be next door at Harvard."

"Fuck. Really? That's cool. I forgot to mention it and it never came up." Mark chimed in when his sister finished speaking. "Yeah, the three of us will be in Mass. We're just down the road from each other."

"Four of us." We all turned our heads in Cheryl's direction. "I'm going to Tufts, and in case you didn't know, it's also in Mass."

"Look at that Wingman, you'll still have to hang out with Macy to keep her company even when we're in college."

"Fuck you Mark. Yeah, pretty tough job isn't it, Bran?" Macy's sarcasm wasn't lost on me.

Cheryl and Mark started talking about all of the potential hook-up possibilities once they were back in school. How maybe after first year they could get a place together to save on money. All the things that couples talk about. Macy on the other hand looked at me in a way that she hadn't in the past. Our only contact was when she touched my hand so that she could pick up my phone and play with it. The outing turned into a very quiet night.

Macy kept her distance and Mark dropped me off at my house without her kissing me like she had in the past two times that we'd been out.

Sitting around with my parents and little sister, they let me know that they would be leaving Friday night when my dad got home from work and wouldn't be back until late Sunday. They were heading to Chicago to my mom's side of the family. Apparently, they had a wedding on Saturday and some christening thing on Sunday.

I had completely forgotten about everything else. Weekend freedom was a very rare commodity in my family, and having it was great news. After watching a ball game with my father, I headed upstairs.

Tossing the dirty clothes off my bed, I picked up my phone and flopped down. One text from Mark, and a series of texts from Macy were waiting for me. Mark's was just bullshit guy stuff, but Macy had questions and she didn't seem to be impressed that hadn't answered her.

"Where are they?"

"Bran"

"Tell me"

"WTF Bran"

"Okay, I'm sorry for not texting you after you sent the pics"

"Brandon come on"

And so on, and so on. When I finally responded, she came back in a flash.

"Sorry Mace. Watched the Cubs with my dad. Didn't have my phone"

"Where are the pictures that I sent you?"

"Gone"

"Gone where?"

"Gone, gone. Deleted gone" It took a while for her to send anything back to me.

"What? Why?"

"It broke my heart, but you know your brother uses my phone all the time. Pretty sure that you wouldn't want him finding them" This time it took even longer for her to respond, but when she did, it was worth the wait.

"So responsible. You get a gold star for that, but next time we're together, I'll show you how to make a hidden file so that only you can open them" Following her words was a close-up picture of her vagina. Protruding from her puffy pinkish brown lips was a clit that looked like a pebble.