Losing to Win

Losing to Win 12

Losing To Win XII
"First Official Date"
By Joey E

Welcome to the newest chapter of "Losing To Win", a gay high school series about guys learning about life and love. I know it's been a while, but life gets in the way sometimes. As usual, if you are under 21 (or 18 in some areas), please leave. If you are not even remotely interested in the gay life, don't read on. This is a work of fiction. All rights reserved. No unauthorized reproduction in any form is permitted without the permission of the writer, Joey E.

"Really?" Josh asked, lifting his head off my chest and looking straight into my eyes.

"Yes," I said as I hugged him harder.

"Aw, Steve," he said, tearing up. "You don't know how good that sounds to me."

I felt a tear drip down on my chest. I kept holding him tight. I knew right then and there, this was for me. No turning back, no apologizing, nothing. This was it.

I looked over at his clock radio on the night stand next to the bed. The red LED display indicated 10PM.

"SHIT!" I exclaimed, jumping up. "I need to go home!"

Josh looked over at the clock. "Yeah you do," he said. "Wish you could stay the night."

"Hey, I tell you what. You know my Birthday is coming up this weekend...."

"Oh yeah that's right."

"Well, why don't we go out on our first official date Friday night? Just the two of us? Dinner and a movie?" I asked, desperately hoping he'd say yes.

"You serious?" he asked.

"Never more serious in my life," I replied.

He threw his arms around me and said, "Sure, baby."

Just then, we heard some movement downstairs which was Josh's mother getting home.

"Aw, shit," Josh said, jumping out of bed. We scampered to put our clothes on. Truth be told, if I was caught with Josh by any parent, I would want it to be Josh's mother. After all she already knew about Josh.

"Calm down dude. I'm dressed already," I said.

"That's easy for you to say, where the fuck is my t-shirt?" he asked, in a panic.

"Josh, here," I said, grabbing a t-shirt from the closet. I threw it at him. He stopped and smiled.

"Thanks."

Just then, there was a knock at the door.

"Josh, I'm home!" the voice said.

"Hey Mom," Josh said, getting up to open the door. I grabbed my backpack to make it look like I was just leaving.

"Hi Mom," Josh said, after he opened the door. They hugged each other.

"Oh Mom, this is my friend Steve. Steve this is my mom."

She gave me this look that I've only seen from my past girlfriends' parents. It was strangely similar but different as well.

"Hello, Mrs. O'Hara," I said, trying to remember my manners.

"Hi, Steve, nice to meet you," she said, smiling.

"Well, Steve was just leaving," he said, obviously trying to avoid any awkward moments that could arise.

"Yeah, I'll see you tomorrow. Pick you up at seven fifteen?" I asked.

"Sounds good," Josh said, grinning.

"Nice meeting you, Mrs. O'Hara," I said, as I walked through the bedroom door.

"Nice meeting you, too, Steve. Careful driving home," she said.

Josh walked me out to my car.

"That was close," he said.

"Buddy, I'd rather get caught by your mom than my parents," I said, opening the car door.

"Yeah I know what you mean. Mom knows about me, but she's never really seen me with a boyfriend before, if you know what I mean," he said.

I winced at the word boyfriend, but then thought about it. We were boyfriends. We were fuckin' boyfriends.

I grinned and winked at him. "We are boyfriends, aren't we?" I asked.

Josh smiled. "If you want to be."

"Dude, I just asked you out on a date! Of course I do."

He smiled even more. "Good. I'll see you tomorrow. And guess what I just remembered? My mom goes away this weekend. So, you know what that means...."

I laughed. "Guess we'll be staying at your place this weekend."

"You know it!"

"All right, little buddy, I gotta get back so I can do some homework before I hit the hay," I said.

Well, the week went past without much commotion. Ben still seemed to not like having Josh sit at our table. However, the other guys were mostly cool with it. Josh seemed to open up as time went on. He really was something, this guy. Man, I couldn't wait for Friday night. We got together for our study session, which we actually did study...and do other things as well. Thursday night was a prime example.

I was over at his house, studying for a big Physics test with him. We hit a snag and I just couldn't remember some terms and definitions. Frustrated, he suddenly grinned at me.

"Hey, Steve?" he asked.

"What's up?" I sighed, leaning back on his desk chair. He was seated on his bed.

"I think I know of a way to make this more fun..."

"Go ahead," I said, listening.

"Why don't I ask you a question, and if you get it right, then I take something off?"

I laughed and said, "Bring it on! I love how your mind works, buddy!"

He stood up and asked the first question.

I answered correctly.

He unbuttoned his button-down shirt.

He asked the next question.

Another one answered correctly.

He took his shirt off. Man, look at that fuckin' torso. All lean and defined. I sighed.

Then he asked me a true or false question.

"False," I said, not sure.

He frowned and put his shirt back on.

"Aw, dude!" I exclaimed.

Next question was even harder.

"Uh..." I started to say.

"Think, Steve, think."

I gave him a half-assed answer but he accepted it anyway.

He took his shirt off again.

Before I knew it, he was standing there in his boxer shorts. I was completely hard and rubbing my cock through my sweats.

"Wow, I'm amazed. We really did accomplish something," he said, walking towards me.

It ended up the usual way, with us fooling around, finding where our pleasure spots were, and ended in a big pool of cum.

I kissed him and said, 'Thanks."

We both got dressed again and made out some more on his bed.

"I can't wait until tomorrow night," he said.

I kissed him on the lips. "Neither can I."

We cuddled a while longer and then it was time for me to leave. As I was leaving, he yelled, "Steve!"

I turned back around and smiled. "Yeah?"

He walked up to me on the sidewalk. "Don't forget the lube and condoms tomorrow night," he whispered.

I looked at him, shocked he would say such a thing.

"What? You don't want to get fucked?"

Now I was speechless. A grin crept across his face. An evil one at that. "Don't forget them," he said. He turned around and walked back in his house.

To be honest, I hadn't thought about taking it to another level. I had no idea about anal sex, never even really thought about it. Not even when I was with a chick. Of course, when I masturbated, I did enjoy playing with the area around my ass, but never stuck anything up it. And now, Josh wanted to fuck me? I wasn't quite sure about that. I drove home in a daze, strangely excited and yet unsure at the same time.

The next day, I woke up energized and ready to go. I did my paper route, got a shower, threw on an outfit, grabbed my bag, and walked out the door. I picked up Joe as usual.

"Hey fag," he said, as he opened his door.

I laughed and said, "Get in you fuckin' breeder!"

We surprisingly didn't have much to say on our way over to Josh's house. But as soon as Josh came in the car, Joe spoke up.

"So, I hear you guys have a date tonight," he said from the back seat. I looked at him in the rear-view mirror. He smiled at me. That little fucker.

"So, who fucks who?" Joe continued.

Josh looked at me and laughed. "I'll let you know that after tonight."

"BUDDY!" I exclaimed. "That's none of your fuckin' business, bro," I said to Joe.

"I'll take that as Josh rides your hershey highway," Joe said.

Josh laughed again. "Yeah, like the bottom he is!"

I was slightly offended. This was getting too gay, even for me. Josh noticed immediately.

"What's wrong?" he asked.

"It's just a little too gay for me, buddy," I said, truthfully.

"Oh man, lighten up," Joe yelled. "You're gay. Get over it!"

"Shut the fuck up," I said, not at all amused.

Josh grabbed my hand and held it. I looked over at him. So fuckin' cute. I smiled at him and tightened my grip. I knew everything would be all right with him by my side. Joe saw this and surprisingly kept his mouth shut the remainder of the ride.

We went into school, all three of us, separating to go to homeroom. All throughout the day, I could not get the thought of Josh and I going out on a date out of my head. I felt like jumping for joy. Evidently, I showed it too, as my buddy John spoke up at lunch.

"Well, you look happy," John said, sitting across the table from me. Joe and Josh were already seated at the table, each on one side of me. "Did you get laid or something?"

"Not yet," Joe remarked to no one. "Ask him that tomorrow."

I shot a look of death to Joe. Joe grinned at me.

Just when I thought everything was going right today, Ben walked over and sat down at the table as usual. He didn't even acknowledge me anymore, which was fine by me.

"Hey, Ben, what's new?" John asked.

"Nuttin'," Ben said, glancing over at me and Josh. It was obvious Ben really did not like to see Josh and I together.

But surprisingly, nothing more was said about it. The day continued on perfectly, though it seemed to drag. I was going to take my little man out for a date and a movie. Nothing was going to stop me from doing that.

When I got home, I was pleasantly surprised to find my big bro at home for a weekend visit.

"Little bro!" he yelled as I walked through the front door. "How's it going?"

He outstretched his arms and drew me in for a big brother hug.

"Hey, Matt! What are you doing here?"

"Well, I needed to come home to go to my friends' wedding this weekend."

"Oh that's right," I said.

"Are you free to hang out tonight?" he asked.

"Uh, I'm sort of busy why?"

"Well, being that it is your Birthday tomorrow, I figured you and I could go out and celebrate."

"Aw, shit, man, I wish I could. I have plans with Josh tonight."

"Aw....you sure?" he asked, almost pleading with me.

"Yeah, buddy, can you hang out tomorrow?"

"No, that's when the wedding is," he said. "But I'll be here on Sunday."

"Matt, Steve, dinner!" our Mom yelled from the kitchen.

I walked into the kitchen. "Mom, I thought I told you I wasn't going to be here for dinner."

"Why is that son?" my Dad asked.

"Don't you remember? I'm going....er hangin' out with Josh tonight?"

"I don't remember hearing that," my Dad, always the strict one, said.

"Aw, dad, cut him a break. He's gonna be eighteen tomorrow!" Matt said, sticking up for me as he usually did.

"I wish I had known," my Mom said. "When did you think you were going to tell us this?"

"I thought I told you earlier this week," I said, not believing this was happening.

"Well, all right, then, go...but tell us the next time," Mom said.

"Thanks," I said to both of them. I ran upstairs, dumped off my back pack, and ran back downstairs.

"Be back by midnight!" Dad boomed from the kitchen.

"All right," I said, opening the front door. "See you later!"

(The remainder will be told in third-person to more easily shift from one scene to the other).

Matt sat down at the kitchen table with his parents.

"Hey, Matt, what do you know about this Josh kid Steve's been hanging out with?" asked his Dad.

"Well, I've met him once. He's a cool kid," Matt said, hoping that would satisfy his father without having to go into anymore details.

"It's just funny that we've never heard of him before and all of a sudden, Steve's hanging out with him a lot. And Steve doesn't say much about him," said his Mom.

"Well, he is helping Steve in Physics I know that much," Matt said, trying to avoid his mom's eyes. "That's all I really know. I've been at school all semester. I don't know anything else..."

"Matt, Steve said he came out to visit you a couple of times in the last month. Is there anything wrong?"

"No, mom," Matt answered, nervously chuckling. "Why would you think that?"

"Nothing, except he seems different now," his Dad said.

"Different, how?" Matt asked.

"I don't know...he just seems...different," his Dad continued.

"I haven't noticed anything," Matt said. By this time, Matt knew his parents were drilling to find something. But he was determined not to let the cat out of the bag.

"Matt, does Steve like boys?" his Mom blurted out.

"WHAT?" Matt asked, dropping his fork.

His dad remained quiet.

"Calm down, Matt. We're only trying to understand," his mom said. .

"Where the hell did that come from?" he exclaimed. "How should I know that?"

"Because I think he'd tell you before he told either of us," his Mom explained.

"I think you should ask him that. How should I know? If he does, he hasn't said a word to me about it!"

His mom and dad exchanged glances. "We're just wondering," his mom said.

Matt took a deep breath. "Look, even if he was gay, don't you think you should wait for him to tell you that? You can't just corner him in a room and ask him questions. You'll scare him off."

"So, he is?" his Dad asked.

Matt was visibly getting angry. "I don't know Dad. What's so important about it anyway? If he's gay, he's gay!"

"Matt, I heard him talking on the phone last night to this kid Josh," his Dad said. "I don't think Josh is the type of guy Matt should be hanging out with."

Matt could not believe that he was hearing this from his own Father . "Why are you telling me all of this?"

"We just wanted to know if you heard of anything?"

"Mom and Dad, do you think if I had, I would tell you? I can tell you one thing though, Josh is not a bad influence. He's a good, cool guy. He's very good for Matt."

"Because he's a fag?" asked his Dad.

"Don't use that word, Dad. What difference does it make? He's helping him pass Physics so he can play baseball this year!" Matt said, not caring if his parents knew the truth or not. It was far better than telling the WHOLE truth, he thought.

"Yes, we knew about that," his Mom said.

"Well, then that's it. What's wrong with that?" Matt asked.

"Nothing, I guess," his Dad replied, not sounding convinced.

"Well, I guess time will tell," his Mom said, getting up to go into the kitchen.

Meanwhile, Steve arrived to pick up Josh. He had just pulled up to his house and Josh practically bolted out the front door with a huge smile on his face. Steve smiled back.

"Hey, Steve," Josh said as he opened the passenger's door.

"Hey, buddy, hop in!"

They immediately kissed as soon as Josh was in the car.

"Mmm...I need that!" Steve said, as he put the car into drive.

"So where are we off to?"

"Oh I don't know. I was thinking we could do something like Wendy's or McDonalds..." Steve said with a grin on his face.

"Oh..." Josh replied, sounding disappointed.

"Bud, I'm kiddin' you! I'm not taking my boyfriend to a fast food restaurant on our first date. What kind of guy do you think I am?"

Josh grinned as he looked forward.

"Actually, I was thinking we could hit up something like the Outback or Olive Garden. It'll be my treat," Steve said.

Josh grabbed a hold of Steve's hand. "Babe, it's for your Birthday. It'll be my treat."

"Aw, come on. I wanted to take my boy out tonight!"

"Well, fine, we'll just see who grabs the bill first."

"Okay, you're on, buddy," Steve said.

Back at the house, Matt was still having dinner with his parents and there was some tension left in the air.

"I can't believe it," his father muttered.

"What can't you believe?" Matt asked, already disappointed in the way his father was reacting to the whole situation.

"Matthew, " his Mom said to his husband. "What's the big deal? You've got a gay cousin. It's not like it's new to you."

"Yes, but this is different!"

"No it's not."

"Yes it is. This is Steven we're talking about!"

"Fine, Dad, talk to him. He is your son. He's so afraid of what you guys will say. Please. Think of him, Dad. Think of what he's going through."

The young new couple arrived at the Outback Steakhouse which was about twenty minutes away. Steve watched his boyfriend get out of his car and thought, damn, I'm a lucky dude. He got out of the car, locked the door, and looked at Josh across from him over the roof of the car. Josh flashed that grin of his that Steve had seen more and more of and fell in love with. He let out a loud sigh and said, "You're my man, Josh."

Josh, sort of startled by the fact that Steve would say something like that at that moment, looked surprised.

"What?" Steve asked.

"Nothing. Just a little surprised to hear you say that here and now."

Steve chuckled and said, "Come on, bud, let's go. I'm fuckin' starving!"

The little guy and the big guy step inside the restaurant and were seated immediately. They ordered and clowned around, having a good time, looking like two high school buddies hangin' out.

"So, have you decided on the movie yet?" Josh asked, setting down his fork to take a sip of his coke.

"Nope. Have you?" Steve answered.

"Nah," Josh said, rubbing his knee against Steve's leg underneath the table.

Steve glanced at Josh realizing it was his knee and Josh grinned. Steve quickly looked around to see if anyone could see what was going on under the table and was satisfied nobody would. He smiled at Josh, reached under the table, and grabbed Josh's knee. Josh giggled and grabbed Steve's hand away from his knee. They held hands for a few seconds until their server came by. They resumed there previous positions and controlled themselves for the time being.

Soon enough, the two boys were full and ready to go. They walked out together toward Steve's car. This time Steve was in front of Josh and Josh's eyes were glued on Steve's ass.

"Hey buddy, stop trying to undress me with your eyes," Steve said, rather loudly.

Josh was shocked that he would say a thing like that in a parking lot, but could hear the fun in Steve's voice.

"How'd you know I was?"

"I can feel them on my ass," Steve said, turning around.

"Well, I was just trying to see how wide it was..."

"WIDE?" Steve asked.

"Yeah, you are kind of fat, now that I look at you," Josh said, with a straight face.

"Why you little..." Steve started to say as he came towards Josh. Josh didn't blink an eye.

Steve just picked Josh up underneath his arms and held him up. "Okay, skinny boy. The only reason I look fat compared to you is because you're built like a girl scout!"

"Hey, I'm perfectly proportionate," Josh said. "And who blabbed that I wanted to be a girl scout?"

Steve froze for a moment, looking at Josh. Josh let a smile creep across his face and Steve started to laugh. He set Josh down and wrapped his arms around him.

"You are so fuckin' cute, buddy. So fuckin' cute."

Josh hugged him back and said, "So are you, man, so are you."

"So you wanna go to that movie?"

"Actually, you know what I wouldn't mind doing?" Josh asked.

"What's that?"

"Just staying in at my place, watching some movies and cuddling with you," he answered.

"Mmm....baby, that sounds good!" Steve said. :"Then at least I can touch you and hold you tight."

And that wraps up this installment of Losing To Win. More will come shortly, I promise. Any comments or questions? Please send them to NEPhillyBoy76@aol.com Thanks!