Meeting Jack, The Second Try
The morning after the night I spent at Chris's place, we got up early since both of us had to teach. I was really aware of what he had said to me the night before, after we had traded cum, and I wanted to say something to him. I was afraid he was waiting for me to respond. Finally, after having a coffee and as we were just getting ready to leave, I said, “Chris...I was really touched by what you said last night...”
He looked uncomfortable, which was unusual for him. “No...don't worry about it. I was just talking...”
I put my hand on his shoulder. “No, you weren't just talking. You said something important. I just want to say how much I've enjoyed hanging with you. How much I like you. It's not just you.”
As I finished saying this, I realized it wasn't just me trying to make us both feel better. I actually did feel that way. I liked the guy. I really enjoyed spending time with him. I wanted to be around him. Why else was he the first person I called after yesterday?
Chris was beaming at me and he leaned in and gave me the nicest, softest, warmest kiss I've had since my girlfriend. Really. It was epic. I kissed him back and we held each other for a moment. I ran my hand through his pale blonde hair. It was like silk. But we had to go to work.
The rest of the day had nothing to distinguish it. Students. I worked out. I met with my trainer and I bashed away at my serve for a while. I had a match coming up in New Jersey – along with Brad - and I wanted to do a little better than last time. Chris was headed to one in Toronto at the same time.
I went home, tired and feeling a bit better. I was still stinging from the way that Jack had just walked out. Fuck him, I thought. The rest of the week I put my head down and worked. I taught and Brad and I traded serves as much as we could to get ready for the matches we had. I was glad we weren't playing each other. That was relief. Brad is way better than I am.
The night before the tournament, I got a text from Jack. I almost didn't read it because I was afraid it would take my focus. But I just had to, right?
Chris,
I'm sorry for the way I ran off the other day. That must have sucked. I'll be honest. You kind of freaked me out when you said you were bi.
I wonder if we can get together again. I mean, like try again. I promise not to run away.
Jack
I had to admit I felt relived. It wasn't me. It was him. I had done nothing wrong. A huge weight lifted off me and I realized I had been feeling like I had fucked up his life or something. But no. I texted him back and we arranged to meet the following weekend. This time he was coming to Boston which I thought was only fair.
I went to bed and slept really well. I woke up and drove to New Jersey and was the tennis player I wanted to be. I got to the semi's for fuck's sake. How awesome is that? My serve just came together for a few days and I beat some really good players. In the semi's I had to play this seventeen-year-old prodigy. Kind of like Jack had been, I think. He was amazing and he ran me off the court. I didn't lose terribly, but I lost. But I took him to five sets. I made him work for it. But in the last set he had worn me down and he won it six to one. Oh well.
I got some money and Brad seemed really excited for me. He lost in the second round which is really unusual for him, but he lost to the guy who eventually won the tournament. We went out to a diner near the tournament after my match, and the kid who beat me was there. We sat down with him and he really was a kid. Cute as fuck, but clearly straight and clearly not interested in anything but tennis. When he finally got up and left Brad said, “Sexy little fucker. You gave him a run for his money. I'm proud of you.”
That felt really nice. We ate our greasy lunch, then we went back to our hotel room. We decided that since we were more or less fuck buddies, we might as well take the opportunities as they came. And now that the tournament was done, we had a really nice opportunity.
We got in the bath and soaked for a while together. Brad's brown hair was plastered all over his head and his curls had disappeared. I sucked him off in the tub, enjoying his equally brown bush that he refused to trim, apparently, but he wouldn't let me take his cum because he wanted to give it to me in bed. We got out and I threw him down and feasted on his ass for a while, really driving my face in and exploring his hole with my tongue. He turned over and got on his knees and wiped his cock all over my face. I tried to grab it with with my mouth, but he kept pulling away and rubbing it on my cheeks and hair. It was getting all drippy, so he let me lick it off before sliding his pretty hairy balls into my mouth.
We were both a lot crazy after working so hard at the tournament. I sucked him a whole bunch, but he clearly had other ideas. “I want to fuck you, Mike”
I got on my back and he said, “No...I want you like a dog.”
Laughing, I got on my hands and knees and he lubed me up and slid his big prick deep. At this point I could take a cock without too much trouble, but this time he didn't hold back and I groaned with a little pain and a lot of pleasure. He said, “Oh...sorry...a little too much force?”
“Fuck no. You can drive that thing in me as hard as you want.”
He held my hips tightly and began to smoothly ream me. He fucked me hard and each time he thrust he smacked into me. I almost fell forward a few times, but I liked the way he was taking me. I liked the feel of the length of his cock going really deep. He used this lube that was way slippery and it seemed to allow him to go even deeper than usual. I fucking loved it, whatever it was.
I was jacking my cock the whole time and Brad said, “If you cum, save it for me. In your hand.”
I wondered what he had planned but I just said, “Sure.”
He increased his pace and was going deeper and I could hear him breathing hard. I hadn't really thought I would cum fast but suddenly I was there and I put my hand at the end of my cock and awkwardly jacked into my fist. My body was trembling and I felt the cum spurt into my hand. I manged to gasp, “Yeah, I got it. Or at least most of it.”
“Fuck yeah.” He pulled his cock out of me and said, “Give it to me.”
I turned and held out my hand which was coated in my cum. He leaned down and sucked it all up, licking the last drops. His dark scruff scraped my hand and I loved the feel of his tongue against my fingers. Then he kissed me. Wild, deep and complicated cum-filled kisses. Then he leaned down and spread my legs and fucked me even harder than before. I managed to say, “Fuck, Brad, tournaments turn you into a fucking demon!”
He laughed and continued at this breakneck speed, but I could tell he was close because he shut his eyes and had this look of concentration of his face. He squeezed his eyes shut really tight and I could tell he was bursting. He gasped, “Fuck, fuck, fuck!” Then he fell forward and slid out of my ass at the same time. I could feel cum oozing out of me and I was surprised he didn't lap it up, but he was clearly spent. I collected some of his cum with my hand and I licked it off and kissed him. I really liked all the cum sharing that was going on with the guys I was fucking. Really fucking fun.
We lay for a while, then I pulled the blanket over us and, seeing that he was already asleep, I shut the light off and wrapped my arms around him and joined him in unconsciousness.
--
I decided that I would meet Jack at a place I had never been. It felt symbolic. New territory, or something. It was called La Mancha. Spanish food, Spanish wine. I got there early and it was dark and comfy, not too fancy, but not shabby either. I ordered a bottle of big red Spanish wine and had a sip. Wow. They really know what they were doing in those Spanish vineyards.
Just as I took another sip, he came in. He was dressed almost exactly like he was the last time. His brown waves of hair were a little messy. He looked really good. Like model quality, good. Again, I asked myself: how had I never seen that before. Maybe I had but didn't know what to do about it.
I stood up and extended my hand, but he surprised me by giving me a quick hug. He smelled woodsy and his mahogany eyes were wide as if he was surprised to be there, as if he hadn't expected to put those muscular arms around me. I sat down and wasn't sure what to say.
He finally said, “Nice to see you,” and sat down across from me.
I decided I wasn't going to make this easy for him. “Really?”
He looked guilty. “I know. I get it. I'm really sorry. I'll explain. Give me some wine.”
I poured him a glass and he took a big gulp. Then he sighed. “So, like I said, I was freaked when you said you were bi. I guess...it made what we did that summer seem real. Or maybe I mean seem meaningful. Does that make sense?”
I thought for a moment. Did it? I said, “I suppose. It was real after all. At least it was for me.”
He nodded and said, “Yeah, it was. I'm sorry.”
“Stop apologizing. Keep explaining.”
He laughed and looked down at his hand. The one with the wedding ring, I couldn't help but notice.
He sighed again and I could tell he was working up to something. “Mike...I really did like what we did that summer. I mean, I really liked it.”
I smiled. “So did I, if that wasn't perfectly obvious.”
Then he surprised me. “Why didn't you want to do the same to me?”
I felt awkward, but at least I knew the answer now. Chris and Brad and Seamus had helped me to that one. “Because I was not ready to admit I was into guys as well. I can't tell you why, really. My shitty parents, I suppose. You know, entitled rich people who pay lip service to being liberal but when it comes to their children, only straight is acceptable. It was in the air when I was growing up. I couldn't have let myself even know that I wanted dick, much less suck yours.”
He seemed a bit shocked at my bluntness but I didn't care. It was time to let it all out. I took charge and said, “So what about you? You sucked my cock – and I assume I wasn't the only one – and then you married a woman. Are you bi?”
It was his turn to look really uncomfortable and I was afraid he would bolt again. Just then, the waiter came over and we ordered some food. I barely remember what. When the waiter left, he ran his hands through his hair and it flopped back as if it knew what to do. He said, “I'm not sure, but I don't think so. I mean...I think I'm more gay than anything else.”
“So...?”
I didn't even need to spell it out. “Yeah, so I got drunk at a frat party and fucked a woman. It wasn't the first time I had done it but that last time I forgot to use a condom. And that was that. She wasn't about to terminate and my parents forced me to marry her. My parents aren't much different than yours. Rich and always focused on what people might think. Right?”
“Yeah, that's about it. So you did the honourable thing. Now you have a kid and I get the feeling that's a good thing.”
He smiled and he literally pulled out his wallet and showed me a picture of his son. He looked like Jack: the same wavy hair, the same intense brownish eyes. Sweet looking kid. Jack was beaming.
“He looks great. But your marriage...?”
“Yeah, that. I've tried to make it work. Tried to be a good partner. And I think I have been. But we don't have sex. I think she knows the score by now.”
“So why are you still together?”
“Argh. The thought of divorce and all that shit. I'm not quite there yet.”
“Do you...how do I say this? Meet your needs somewhere else?”
“Sometimes. Nothing real. I fuck anonymous guys here and there. I'm totally busy all the time, so it's really hard to fit that in with everything else.”
I nodded. Our lives were so different. Even before I started sleeping with guys our lives were different. Then I remembered our last conversation. “So why did you try to convince me you were straight last time?”
He gulped. He really did. “I'm so sorry about that. That was fucked up. I was scared. I wasn't ready to say to you that what we did meant something to me. I wasn't ready to admit it. That I had feelings for you. Sure, I fuck the odd guy here and there, but I've never been with one long enough to have feelings for him. You were the first one, Mike. The only one.”
That totally floored me. I said, “Never? Since me?”
“No.”
I looked around the room trying to collect my thoughts. I turned back to him and said, “But I never returned the favour. I let you suck me off like the shit that I was and I never did anything for you. We never kissed...I just watched you jerk off a bunch of times. I'm the one who should be sorry, Jack!”
We stared at each other and it was clear neither one of us knew what to say. Finally the silence got to be too much. I said, “What are you thinking?”
He blinked at me a couple of times then said, “That I wish you had kissed me.”
That hurt, but I deserved it. “Yeah. I wish I had, too. I think about it all the time these days. Now that I've kissed guys I realized how stupid I was then. I mean yeah, I was sixteen, but come on. How hard was it for me? I just couldn't. I'm really sorry.”
I realized he looked almost relived. He said, “It's nice to hear you say that, Mike. It means it wasn't all in my head. Even knowing that you had wanted to on some level helps.”
It make sense and I was glad. “I get it.” I was having an idea, so I said, “Um, Jack. What if we go to my place. What if I do the things I couldn't do when I was sixteen. What do you say?”
He looked really surprised. I mean stunned. “Uh...I don't know...”
I realized I had to work a little harder. “Come on. Just for history's sake.” I reached under the table and ran my hand up his thigh. I leaned forward and my hand found his cock. I gripped it through his pants and said really quietly, “What if I suck you off in payment for all the times you did it for me.”
His eyes widened and I could tell he was torn. He took a really deep breath and said, “You mean...now?”
I gripped a little harder. I could feel his cock chubbing up a bit. “Yeah. Now.”
It was still my job to take charge, so I pulled my hand back and waved the waiter over. I paid the bill and stood up. “Coming?”
Wordlessly, he got up and put his coat on. I put mine on and walked outside, not checking to see if he was following. But he was. We got out to the street and I said, “It's just a few blocks from here.”
We walked in silence and I kept saying to myself: I hope he doesn't change his mind. But he didn't and we made it up the elevator and I got him inside my apartment. I went to the kitchen and poured us a scotch. He sat on the edge of the sofa and I handed him the glass. “Cheers. Here's to the past coming back.”
He laughed suddenly as if I had broken the ice. We clinked glasses and I took a big swig. Then I sat down beside him on the sofa. I put my hands on his broad shoulders and pulled him toward me. I kissed both his cheeks, then I stared into his eyes. I was surprised how dark his eyebrows were compared to his hair. His eyes were big and dark. I realized I had never really looked at them before. I leaned forward and did the thing that I hadn't done fifteen years ago. I kissed him. And not gently, but with lot of energy. I grabbed the back of his neck and pulled him closer, forcing his mouth open, and I felt a little jolt of surprise when I felt him respond. His arm went around my back and his lips were suddenly all over the place, his tongue pushing its way in.
I felt a little nuts and I pushed him on to his back and got on top of him, my cock was aching to get going but I paid no attention. We kissed a whole bunch and soon he was moaning into my mouth, humping up. I could feel how hard the bulge was in his pants and I wanted to fucking get in there.
I leaned back and looked at him, grinning. I said, “Take your fucking pants off, Jack. It's time for payback.”
He looked a bit startled, but he reached down and undid his jeans. He was going too slowly as he pulled his zipper down, so I helped him. I grabbed the waist and hauled them off, his underwear and all. I had to work to get them over his strong thighs and then I threw them across the room.
I undid my own pants and pulled my dick out which was straining to get some air. Fuck, I was turned on. His dick was fucking big. Bigger than my three friends. Way bigger than mine. Thick. Uncut. How the hell had I never noticed that all those years ago when I had watched him jerk off? I had been totally clueless.
I leaned down and ran my nose across the taut surface. He smelled clean and a little spicy with some no doubt expensive product that lawyers buy. I licked it experimentally, running my tongue over the surface, feeling the bumps and veins, tasting a little sweat. His cock jumped at my touch and I could hear him grunt. I wanted to give him back something of what he had given me. But I also just wanted this cock. I kept licking and made my way up the the head which felt a little more complicated under my tongue than the cut cocks I had sucked. More skin, more taste.
I took the base in my hand and pulled his dick up, my mouth covering the head so I could explore its smooth surface, circle my tongue at the piss slit which was starting to drool precum, making everything taste even better.
I slid a bit more of his cock my mouth, massaging it with my tongue, slurping with a little suction, pushing down further until I had to stop. Fuck, it was big. My lips were stretched and my mouth was full and the head was pushing into my throat. I took a few deep breaths and pushed a little harder and I had to work hard not to gag. I wanted this fucking cock in me, I wanted to take it. Not just for him, but for me.
I felt his hand touch my head lightly as if he was afraid I would stop him, then he started to caress my scalp. I heard his voice say, “Fuck, Mike. That feels amazing.”
I wanted to grin, but my mouth was full. I pulled back a bit so I could breath. I gripped the base in my hand and moved my head up and down a few times, getting used to the amount of his hot flesh in me, relaxing my throat and jaw, feeling my lips stretch. I tried to imagine what my sixteen-year-old self would have done with this thing. Probably not very much. But now? I could totally do this.
I moved a little faster, moving my hand a bit, jacking him in short strokes while my mouth did the rest. I was hungry. I was hungry for his cum. I wanted it. Not just for the sake of the past, but for now. For me. I felt his hand start to push me head and encouraged, I moved a bit faster. My hand slid in longer strokes and every time I pushed down I let his cock go deeper, right into my throat. I gagged a couple of times, but I didn't stop. I wanted this done. Not because I was anxious for it to be over, but because I wanted to find out what I had missed.
Soon he had taken my head with both hands and I could hear him breathing more heavily, groaning and gasping. I think his cock got even harder and bigger, if that were fucking possible. This was a porn sized dick and it was making me crazy with out-and-out lust. My own dick was aching but I ignored it. This was all for him.
My mouth was getting sore but I wanted his cum. I pulled off him and started to really jack his cock. It was slick with my spit and his precum and I loved the feel of the girth of it, the fucking length of it. How had this guy been keeping this thing more or less hidden for so many years?
Jack was moaning, and not quietly. He managed to say, “Fuck, Mike...I'm so close...”
And he was, I could tell. His cock was getting harder and his balls were starting to pull up and then it just started to explode. Big, long, ropes of cum shot out of the end. I caught some of it in my mouth and then went down and let the rest pour into my mouth, but it was too much. I pulled my head back and watched long streams run down the length, over my hand, onto his pubes and the contrast of his white cum and his dark hair turned me on even more. I licked up what I could and then pushed that fucking rod into my mouth again, all the way down, so I gagged. I just waned more and more of it.
Finally the cum stopped and I pulled my mouth off him and swallowed. I looked up at him. His eyes were closed and he had a hand over his face as if the light was too bright.
I moved up and put my lips to his ear and said, “Jack, your cock is fucking amazing. I'm so sorry I didn't let you give it to me before.”
He moved his hand and turned and looked at me, grinning. “Thanks, Mike. Your mouth is very talented.”
I laughed and said, “I've had good teachers.”
He moved and lay his head on my chest, which felt really nice. I kissed his hair and ran my hand up and down his back a few times. I was struck again by how beautiful he was. His hair was finally messy and a little sweaty. He seemed to be watching his own fingers play with the light tan hair around my still-hard cock. I kissed the side of his face. Why had he kept himself closeted and hidden for so long?
We lay, not talking, for a while. But then he raised his head and looked at me. “Can I return the favour?”
Part of me hoped he would say this, but at the same time I felt guilty since he had done this to me so many times and I had done it exactly once. But I said, “How can I say no?
He turned and gripped my dick in his fist. It was red and sticky with my precum. It had been drooling the whole time, waiting. It was rigid and I was afraid I would fill his mouth in two seconds. That wouldn't be a bad thing, right?
He looked at it as if it were the promised fucking land. I said, “Are you sure?”
He laughed and licked the head then said, “Yeah. I'm as sure of this as anything.”
