A Gentlemen's Agreement Ch. 05

On Monday, Grady and I were teamed up on an American History assignment. I suggested we research the subject individually, then meet up at my house on Friday afternoon to work on the finished project together.

"Maybe we could do a sleepover," I suggested, trying not to let on that I had ulterior motives in mind. Ever since I face fucked Grady, and experienced the most powerful climax of my life, I'd found myself reconsidering fucking him. I had yet to make up my mind on the idea, but it was pointless to take it off the table. It's not like Tyler has shown any interest in popping my cherry, and why should I wait for him?

"A sleepover? What are we, fourteen year olds?" Grady scoffed at the idea with a roll of his eyes.

"You could come over Friday, after school. We can do our homework and then knock out this project together. No point in you going home after, it could take hours to complete. We could hang out on Saturday, so maybe you could stay the weekend? You can go to church with us on Sunday and go home with your folks from there."

"Where would I sleep?" Grady asked, giving me one of his sly, crooked grins.

"Wade's away in college," I answered coyly, "You can sleep in his bed."

"Oh, I see," he said, sounding defeated.

"Hey, we can still fool around, and take our time about it. I just don't know how my grandmother would react if she came in to wake me and found us lying naked in bed together."

"Yeah, that could be awkward," he said, "Okay, let's do it. Have your grandmother call my mom, so she knows it's all right with her."

On Wednesday, we decided to hit the reference section of the public library. On Grady's suggestion, we discreetly meet up into the men's restroom by heading in one at a time. He realized that we had never performed mutual masturbation together, and wanted to give it a try. I hadn't busted a nut since face fucking Grady and was more than willing to take the chance of getting caught. We jacked off each other into the urinal, then lapped up the excess cum off each of our dicks before swapping and mingling it in a long, deep kiss. We were both still bulging in our jeans when we made our way back to the seclusion of the reference section.

Afterward, I had some difficulty concentrating on our project. I hadn't sought him out in the last few days because I realized I had a budding affection for him, which was a violation of our agreement. No strings, I kept telling myself. But it was no use. I was on the precipice of falling deeply in love with Grady. It was the main motivating me to have intercourse with him. Even if it all falls apart in the end, I wanted it to be Grady who took my virginity from me.

On Thursday, I decided to have lunch off campus and stopped by the local drugstore while I was out. I have to admit that buying condoms and lubricant was an embarrassing endeavor, but better to be embarrassed a little while now than regret it later. I didn't want to go through all the trouble of setting up this weekend only to have Grady insist on using condoms, and not have one. I stashed them in the glove compartment and went back to school.

By Friday I was ready to have a nervous breakdown. Grady noticed I was acting odd and asked me what was wrong. I brushed it off. After school, he threatened to go home and flunk American History if I didn't tell him what was up.

"I'm nervous is all." I told him, hoping my non-answer would be answer enough.

"About what, our messing around in your grandmother's house?"

"No- yes," I stuttered, then decided to come clean. We probably needed to talk about the condom situation before we got to my house anyway. "Open the glove compartment."

Grady opened the glove compartment and pulled out the white paper bag. He opened it, looked inside, then pulled out the bottle of lube and box of condoms. He stared at them a moment then stuffed them bag into the bag, and replaced the bag where he found it. He stared out of the window in silence. I could tell something was wrong.

"What's wrong, Grady?" I asked, "I thought you'd be delighted."

"Why would I be delighted? It's none of my business that you're finally going to get to fuck Tyler."

"Tyler?" I was dumbfounded. "I'm not spending the weekend with Tyler. I'm spending the weekend with you." It took a little while for what I said to sink in.

"So You're not going to fuck Tyler?" He asked. I could tell he was choosing his words like he was walking through snake infested high grass.

"No, Dumbass! I'm planning on fucking you. Tonight. If you want to." For a moment, Grady's face lit up, but then it faded into a look of confusion.

"Then what are the condoms for?"

"I didn't know if you wanted me to cum inside you or not, so I thought I better get them in case you preferred I wear one." He looked at the glove compartment for a while.

"I don't want you to wear a condom," he finally answered, looking at me a little sheepishly, "but I'll understand if you want me to."

"No condoms it is." I yelled out the window to the forest of trees lining the highway.

"Just promise me that you will wear one if you do get the chance to hook-up with Tyler." His face was dark, and his voice sounded sad.

"I promise." I smiled at him, and he smiled back. It was an easy promise to make. I realized a few days before I really wasn't interested in fucking Tyler anymore. I wanted Grady, and only Grady.

What I thought was going to be a torturous wait for the afternoon and evening to pass, turned out to be a pleasant evening spent with my best friend. We hit the books as soon as we got home, we did our homework then moved on to the project. After we finished and cleared away our mess, we watched television with Grandma. She retired to her room after the evening news, and we headed upstairs. We were stripping out of our clothes as soon as I closed the door.

I double checked that both Wade's and my doors were locked. Mine and Wade's bedrooms were the only rooms on the second floor, with my grandmother's bedroom on the ground floor, so I was fairly certain that as long as neither of us lost our minds and screamed, we wouldn't disturb her.

First, we headed into the bathroom and showered, taking our time in exploring one another's bodies. We toweled off and headed for the bed, retrieving the bottle of lube from the paper bag. We flipped a coin to see who would be first. Heads, for Grady.

I lay down on my back and Grady lubed up my cock, then his ass. He climbed on top of me, lining up my hard cock with his lubed hole. On all fours, he leaned back, lining up his little butt hole with the head of my cock. I thrust my hips upward, pushing the head of my dick into him. I felt the head pop through the wall of his sphincter, which clinched down hard on the top of my shaft. It felt like his sphincter was trying to strangle my dick to death. I could see the sudden torrent of pain wash over his face and felt his legs tremble. He tried to pull off, but I held him in place.

"It hurts too bad. Take it out," he pleaded.

"If I do that, you'll have to do this all over again. Just wait a minute and the pain will go away." I hoped I was right about that. I knew there would be pain the first time. I just hoped the pleasure that followed was worth it, especially since I was up next.

We waited. The pain seemed to subside a little, and he relaxed as I felt the grip his sphincter had on me begin to subside. He shoved a little more of me into him before completely impaling himself on my shaft. A wave of relief washed over his face.

"You're going to pay for that," he said, smiling down at me.

He sat upright, my cock buried to the hilt, and I noticed he had lost his once proud erection. Grinding the base of my dick into his ass, he played with the new sensation of having a cock buried in his ass. Slowly, he began to slide his tight hole up and down, his cock slowly returning to its rigid form. I pulled him forward, our lips meeting in a kiss. Bracing my feet on the mattress, I started to slowly pump in and out of him while I continued to explore his mouth with my tongue.

"Yeah, that's it," Grady breathed into my lips, "Fuck!"

I rode him slowly, picking up my pace, trying to match my rhythm with the intensity of our kissing. With some difficulty, I rolled him onto his back and untwisted his legs, pulling them up to my shoulders. I drove into his now willing ass, fucking my cock into him. He started moaning in pleasure. His eyes glassed over and his face took on a dreamy expression. I lost myself to our rhythm.

"Oh Fuck, I'm going to cum." I was so close now, my orgasm mounting.

I buried my cock inside him, flooding his guts with cum. After collapsing into his embrace, I slowly collected my senses, before giving his ass a few more pumps. I withdrew reluctantly and lay next to him.

"What did you think?" I asked.

"It's great, once you get started." He was breathless. "It's your turn."

Grady sat up and positioned himself between my legs. He lubed my hole, then his cock, before positioning himself. With a thrust, he entered me. A sharp pain shot into my stomach, balls and legs, quickly replaced with a radiating pain that seemed unbearable.

"It's okay," he told me in a reassuring whisper, "Just breathe through it."

He remained perfectly still, but impatiently watched my face for a sign to proceed. Lying flat on my back, I didn't have the control he had. After what seemed like a longer time than it probably was, the pain subsided and I became aware of his girth inside me.

I nodded my consent and did my best to accept him inside as he pushed deeper and deeper. There was a sharp pain deep in my bowels, causing me to wince. Grady stopped moving, then pushed slowly deeper, exploratory, until he'd buried himself completely inside.

Immediately, he began slowly fucking me with short strokes. The feeling of his big cock moving inside me was incredible. He increased speed and stroke as he reached down to toy with my growing hard-on.

"Oh, God. Fuck me, Grady." I said breathlessly, barely aware I was even speaking.

He released my cock and mounted himself above me. He fucked me hard. He thrust himself deep and held himself there. He fucked me in slow, long strokes. He fucked me hard, thoroughly, completely. I was awash with ecstasy, his every stroke pulling me deeper into passion. Something stirred in my loins, increasing my pleasure. My cock throbbed as Grady dove me toward orgasm.

"Oh, my god, I'm cumming," I nearly screamed, surprised by the sudden certainty of an unplanned orgasm. The orgasm was intense, my cock erupting cum between our bodies, drenching my stomach and chest. Surprise flashed across Grady's face, quickly replaced with a look of total satisfaction. With just a few more strokes, he buried his seed in my ass, growling as his came.

He collapsed on top of me, breathing hard, then began to laugh.

"What's so funny?" I asked, his laughter becoming infectious.

"I made you cum," he said into the crook of my neck, then raised up to look at me, "and I know you didn't fake it." He pulled out of my ass, leaving me feeling strangely empty inside.

We snuggled together while Grady ran his hands over my sticky chest and stomach, spreading his achievement all over me. His eyes moved between the work of his hand to my face and back again.

"I love you," he finally said, his voice barely audible.

"That's just the afterglow talking," I countered with a smile.

"No, it isn't." he insisted, "I've been feeling this way for a long while now. I haven't even thought about fucking a girl since we've been messing around. All I think about is being with you, and not just for the sex, but just to spend time with you. Hanging out with you."

"I love you too," I whispered, tears beginning to well in my eyes. I was aware that my thoughts about Tyler were thoughts of letting go. I gave myself permission to be with Grady, to give myself to him, because the chances of being with Tyler were so unlikely. I came to understand that I was obsessed with the fantasy of Tyler, and not Tyler himself, while steadily falling in love with the reality of Grady.

"Being with you feels natural and easy. Sex with you is playful and fun. I don't want us to end. I'm committed to this, if you are. I want to be your boyfriend." I pulled him onto me, holding him in a welcoming hug.

"I would be honored to be your boyfriend," I told him, "but it has to just be the two of us. No more 'no strings attached' business. If we do this, we do it right."

"Absolutely."

Sleep came upon us quietly and swiftly, cuddled together in the dark of my room. When I woke up, I woke up with the realization that I was his now, and he was mine.