Losing To Win VII
"The Loss, The Win"
By Joey E

Here is the long-awaited installment of Losing To Win, a gay high school series. I hope it lives up to the rest of the series. Thanks to all who have written to me to tell me to get my ass in gear and write another part. Though this one wasn't as fun to write, this is a VERY crucial chapter. If you are under 18, go away. If you don't like gay sex stories, go away.

On my way home, I thought about what my older brother had said to me. Be yourself, don't give a fuck about what anyone else thinks. All my life I had always been confident about who I was. This uncertainty was a new thing for me. I wasn't prepared for this. There was no way I could have been. Was I prepared to lose to win?

There was one thing I was sure of. I had to let Jill go. I loved her too much to put her through this. I had to be honest with her. It wouldn't have been right. Jill meant everything to me. I couldn't just push her to the side, leaving her out of what maybe the most life-changing decision that I would ever make.

I got home around ten and my parents were in the living room.

"Where were you?" my Dad asked.

"I went up to see Matt."

"On a school night?" my Mom asked.

"Yeah, I needed to talk to him," I said, sitting down on the couch next to my mom.

"Oh, anything wrong?" she asked.

"Nah, nothing I can't deal with."

My mom gave me one of those looks that told me she wasn't satisfied with my reply, but she left me alone.

"Well, honey get to bed. I'm not waking you up tomorrow morning," she said.

"Yeah, I'm beat," I said, yawning as I stretched. I went upstairs, got undressed, and headed straight for bed. I was beat. I didn't think of anything as I climbed into bed. I closed my eyes and just fell asleep.

It was Wednesday now. I woke up, surprisingly feeling refreshed, ready for the battlefield. I could almost feel my older bro's presence with me as I picked up Joe for school.

"Where were you man? I tried calling you last night, your parents said they didn't know where you were!" he said as he got in the car.

"Oh, I was up at the college, visiting Matt."

"How come?" he asked, as he slammed the door shut.

"Oh, I just had to talk to him about some things," I said, driving off.

"Ah, about Jill and Josh?" he asked. "You know I was thinking about your dilemma. Why couldn't you just have both of them at the same time? Do you know if Josh likes pussy?"

"WHAT?" I asked, laughing. "You're fuckin' nuts!"

"Well, it would solve all your problems. You'd have both of them."

"Well, I'm not sure Josh and Jill would be cool with that. Besides, I've made a decision."

"You're going to become a priest? I hear they get plenty of little boy dick," he joked.

"Man, you certainly got comfortable with me being gay fast."

"Hey, you're the same guy, man. It just gives me more to make fun of you," he said, looking at me.

"Thanks," I said softly. "No, it really means a lot for me to hear you say that."

"Aw, no problem, dude. Listen, whatever you decide, you have me behind you."

"I may hold you to that. But I am going to tell Jill what's going on after school today."

"Shit, you are?" Joe asked, surprised.

I turned to look at him for a brief second before focusing back on the road. "What, you don't think I should?"

"Well, I don't know man. You've got one of the hottest chicks in school, man. You sure you wanna give that up?"

"It's not a matter of wanting to, bro, it's a matter of being honest with her. I love her so much that I can't drag her along while I work my way through this shit, bro. I care about her too much."

"Shit," he muttered.

We pulled into my usual parking spot on the street and got out of the car.

"Well, whatever you decided to do," he said, getting out of the car, "I'll be there for you."

"Thanks, buddy, I know you are," I said, closing the door.

We walked on to school grounds. Jill was waiting for me at my locker as usual, and I smiled.

"Well, I'm glad to see you're still alive. I'm sorry about what I said last night," she said. "I tried calling you last night, but your parents said they didn't know where you were."

"Yeah, I went up for a visit with my bro, Matt," I said, opening my locker. I found it hard to look at her. I knew what I had to do today, and it wasn't going to be easy. It wasn't going to be easy at all.

We somehow made it through a formal conversation and then we parted, going to our respective homerooms. Everything was fine up until lunch. I used to find lunchtime enjoyable, but now as of late, it has been nothing but a stressful situation. Probably because I had to face the two sides head on. I sat down at my usual table with my usual jock friends and, of course, my best bud, Joe.

The lunch went smoothly today. I looked over at Josh on occasion, and even shot him a smile once or twice discreetly. However, Joe, who notices everything, caught on instantly.

He punched my lightly in the leg and said softly, "You really got it bad, don't you?"

I smiled back at him and nodded my head yes.

We talked our usual talks during lunch, nothing out of the ordinary. I found myself staring at Josh a couple of times. He was so fuckin' cute and adorable. I couldn't help being drawn to him.

The rest of the day passed by quickly as well. We were all busy because the end of the semester was coming. I had to go work out with my buds after school, but I made sure Jill was going to be around. I agreed to pick her up at her house around 7PM for dinner.

As I was driving to her house, I was having second thoughts. I liked having her around and not just because of the image thing. I really loved her. I really enjoyed being with her. It broke my heart to think I was about to break hers. I didn't want to do it. But it had to be done.

I picked her up and we were on our way to where we had our first date, the local Friendly's. It wasn't my idea, she wanted to go there. We made small talk on the way there, not much else was said. There was a difference between being with Jill and being with Josh. I was realizing that as we hung out. And to be honest, all I could think about was being with Josh instead of Jill. That's when I knew it was time to go my separate way.

We sat down at our tables.

"Steve," she said as she took my hand in hers. "You've been acting very weird the last week or so. I'm only trying to find out what's wrong because I'm worried, hun."

I shook my head in understanding and said, "I know, and I'm sorry to put you through this. I just am so confused and I don't know what I should be doing."

"Confused about what?"

I wasn't sure how to answer that at the moment, and we were saved by the server coming to take our orders. We ordered and it was time for the answer.

"Jill," I said, looking down at the table. "I am confused about what I like. A person came into my life and just turned it completely upside down. I just feel so fucked up."

I looked up at her briefly and then continued. "I don't know. I love you, Jill, you know that. And that's why I can't keep this from you anymore."

Jill looked at me with frightened eyes.

"Babe, I am sorry. I don't want to hurt you. I really don't. I can't...don't....I just can't go on like this anymore. I....I...I think I am in love with someone else."

She withdrew her hand from mine. "Who is it?" she flatly asked. "Is it that bitch who is in your Physics class that you can't keep your eyes off of?"

"Well, no, not exactly. It's not who you think, Jill."

"Who is it?"

I looked down at my hand on the table and said, "His name is Josh."

I looked back up her and her face went through various signs of emotion. It was first mad, then surprised, then mad again, and then confused.

"Huh?" was all she could say.

"I think I could like guys," I said softly. "I think I do."

She just sat there shocked. Tears came to my eyes. "I'm sorry, Jill. I just have to tell you that to be fair. I don't want to hurt you. I really don't. But I cannot just sit here and lie to you."

"You mean, you have a crush on that kid who's tutoring you?" she asked almost in a whisper. A tear fell from her eyes.

I nodded my head yes.

"I can't be here right now," she said, gathering up her jacket . "Take me home."

"Come on, Jill. Sit down. We just ordered!" I said.

"No, I want to leave now. Get the check, pay it, and take me home, Steve. I don't want to hear anymore."

I groaned and caught the attention of our server. I felt totally embarrassed when I asked for the check. I just discreetly rolled my eyes at Jill to the server. He laughed.

"Well, your food will only be another few minutes, would you like to take it with you?"

Without even asking Jill, I answered, "Yes, I'll wait."

I looked over at Jill when he left and said, "Look, I know you're excited and shocked about this whole situation. But please, just wait for the food. We'll take it, and then I will take you home and we can talk, okay?"

Jill gave me a cold stare, one I had only seen once before, and it was very unnerving. "Fine," was all she said.

There was so much on my mind that I wanted to share with my girlfriend of two years. We had so many good times together and I didn't want it to end. She was the first person I ever had sex with. I loved her very much. I didn't want us to just walk away and never speak again.

"Jill, please, I'm telling you this because I love you."

"Oh?" she snapped. "I hate to think what you'd do if you hated me."

"Come on, babe. I can't go on like this anymore. I needed to tell you. When did you want me to tell you this? When we were married?"

We sat in silence for the next three minutes. I could tell she was very upset and so was I. I just wanted that food to come so we could leave and talk in private. She just wanted to leave.

Finally our food came by, we got up, put our jackets on, and left the booth. I payed the bill and we were out the door to my car.

"You're an asshole, Steve," she said, getting in my car.

"Why? What did you want me to do?"

"I can understand you leaving me for another chick. But for a guy? How long has it been going on?"

"For about two weeks now. I wasn't sure of myself. I am not even sure who I am anymore. But I know what I want. I'm sorry, Jill. I wish I could just turn back time and go back to what I was, but I can't. And it was bound to come out sooner or later. I just couldn't hurt you anymore. I didn't want you to find out from someone else two months from now."

"So does this mean you're breaking up with me?" she asked, with tears in her eyes.

I took a hold of her hand and held it. She pulled it away. That hurt. My eyes started watering.

"Yes, I am. I don't want to string you along, babe. I can't drag you down with my problems."

"But, all those times we were together, were they nothing?"

"Of course not. It was real. It meant a lot to me. And it still means a lot to me. I don't know. After seeing Josh, though, I cannot say that I ever felt like that about anyone before."

"Including me?"

I shook my head yes. She let out a sob.

"Don't cry, Jill," I said, pulling over the car. I turned to her and wrapped my arms around her. She cried into my shoulder. I cried too. I was letting the best thing so far that has happened to me in my life go.

"Jill, I love you," I said softly as I held her.

"What should I tell every one?" she asked.

Oh shit. Good question. "Good question," I answered, kissing her on her forehead. "Make me look like the bad guy all right? I won't say anything against you."

"Like I caught you cheating on me?"

"Yeah, which wouldn't be that far off," I said. "But don't tell them who it was with..."

She laughed through her tears. "You sure this isn't a phase you're going through?"

"If it is, shouldn't I have gone through it five years ago?" I asked.

"Maybe your time with me was your phase," she said softly.

"Yeah, true," I said.

"I don't know what to do, Steve. You've been a part of my life for two years now," she said, starting to cry again . "I don't know what I'm going to do."

"Hey, hey," I said, tenderly. "I'll still be here. And I'm sure there's many of other guys out there who want to date you."

"But none of them will be like you," she answered.

"No, that's true. No one could be like me," I said, smiling.

She punched me in the arm. "Shut up. Take me home," she said, smiling.

"I'll be here for you whenever you need me, all right? Just because I am not still dating you doesn't mean I won't look after you. I will always make sure you're okay," I promised. I knew that I would in any possible way.

We said a teary goodbye and I felt finally free of anything from my old life. I was ready to start over, and start over with the one I was really after. I stopped by Joe's house to tell him the news.

"Joe," I said, as I saw him come to the front door.

"What's up? You look like hell, but yet, you look happy too," he said.

"Yeah, I just broke up with Jill," I replied.

"Aw, shit, dude. I'm sorry."

"No, it was for the best. I am doing it for one reason."

"I know who that reason is too," Joe said ,smiling up at me.

I smiled back at him.

"Go get him," Joe said, softly but firmly.

"I intend to!" I said, giving him a high five.

I raced over to Josh's house and was there in three minutes. Please be home, Josh, please be home. I ran to the front door and knocked. A woman answered the door who looked to be in her late thirties. When I got a better look at her, I realized Josh had her eyes. I smiled at her.

"Mrs. O'Hara?" I asked.

"Yes," she answered.

"Is Josh home?"

"Sure, come on in," she said, opening the door wide.

I stepped in as she walked towards the steps.

"JOSH!" she yelled. "Someone's here to see you!"

"Okay!" I heard a voice yell from upstairs.

He came galloping down the steps, looked at me, and smiled.

"Hey Steve," he said, his voice showing his excitement.

"Yo," I said to him, trying to remain cool.

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

We shook hands.

"Are you doing anything right now?" I asked him.

"Just homework," he answered. "Nothing important. Why did you want to go out?"

I nodded my head yes.

"Uh just a minute, young man," his mom said. I grinned. Josh rolled his eyes.

"Yes, mother?" he asked.

"Don't you need to finish your homework?"

He sighed. "Mom I can do it when I get back. Besides, it's next week's assignment!"

His mom gave him a stare and then smiled. "All right, be home at a reasonable time though," she said.

"Okay, midnight," he said quickly as he walked towards the door.

"Eleven!" his mom said. I looked at her and smiled.

"Make sure he's in at eleven," she said.

I extended my hand to her and said, "Well, it was nice to meet you Mrs. O'hara. And I'll make sure the little runt is home on time."

"Hey!" Josh exclaimed, smiling back at us.

I walked towards the door and smiled at him. We both walked out and got into my car. I took his hand in mine and we were off to my house. I knew my parents were home, but I didn't care. I had to tell Josh the news.

Luckily, they were upstairs at the time and we quickly headed down to the basement. Once there, Josh and I sat down on the couch together.

"What did you do now?" Josh asked.

"Well, I don't know if you're going to like this or not...I did something today after carefully thinking about it... and..."

Josh looked disappointed. He looked so cute with the pout on his face. I stopped talking.

"And?" he asked, not seeming to want to hear the rest.

"And....after careful consideration..."

"Cut the crap, Steve, what did you do?"

"Well, like I said, I don't know if you're going to like hearing this or not...but I let Jill go today."

Josh gave me a look of disappointment, being that he was prepared for the worst already. He then gave a look of surprise and finally happiness.

"You what?" he asked, grinning.

"I'm all yours, babe," I said, smiling.

"I don't believe it," he said.

I wrapped my arms around him and whispered in his ear, "Believe it, Josh. I'm all yours."

He kissed me on the lips and soon we were involved in a full-fledged french kiss. His lips opening up, letting his tongue out and invading my own mouth. It was the most passionate kiss I had ever had in my life. He eventually pushed me down on my back and was now grinding on top of me as we kissed.

Suddenly, we heard footsteps walking down the steps above. I was brought back to reality and so was he. We separated and sat back up next to each other.

"Are you serious?" he asked again.

"Yes. If you still want me," I said.

"I do, Steve, I do."

Hope you enjoyed this chapter. Please send all comments to NEPhillyBoy76@aol.com Thanks!