This is an original story (M/M, anal sex) based on a real situation and real people from my past. Sadly, the sex is wishful thinking and pure fiction.
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Thanking the OG
I coached my son's soccer team for 12 years, all the way from pre-school until he graduated high school. I considered that I might resume if I ever had grandkids, but my son eventually let me know that kids were not in his plans.
When I walked my dog we would go by the high school team practice, and I liked to stop and watch. They had some talented players, but they didn't look very well organized. Thinking I could volunteer as a parttime assistant, I tried talking to the soccer coach. Looking overwhelmed and flustered, he just barked at me for interrupting practice.
I kept my distance after that. My help was clearly not wanted, and I was concerned that I would look like some old pervert, hanging out at the school and watching the kids.
So, the dog and I would watch the practice for a short while. Then we would head to the park. We are both seniors, so we walk for a bit and quickly get tired. I sit on the bench with my sketch pad, while he sacks out on the grass next to me.
This one time, we were both tired. So, while my dog snored next to me, my eyes closed and I was on the verge of joining him. I was jarred awake when someone plopped down on the other end of the bench. I looked over and saw it was one of the high school soccer players.
He realized he had startled me, and he quickly apologized. "Oh, hey! I am really sorry. I was running and needed a break. I didn't even think before I sat down."
I smiled. "No worry." Then I said, "You're on the soccer team, right? You play midfield."
He seemed pleased by the recognition. "Yeah! I'm Eddie," he said, shaking my hand. "Are you into soccer?"
I told him about my history with coaching and he seemed interested.
"I wonder if you knew my dad... That's about when he played."
"It could be. What's his name?" When he told me I was pleasantly surprised. "Justin? He was a terrific kid. I definitely remember him."
Justin was a beast, bigger than most, and very skilled. He was a holy terror on the field, but he was also the nicest kid you could ever meet.
"That's pretty cool. Too bad you're not coaching anymore," Eddie commented. "We're not very good. We could use some help."
"You've got good players," I offered. "I'm not too sure about your coaching though."
He nodded agreement. "Our coach is the PE teacher. He's a good dude but I think he got the job because no one else wanted it." Standing up he said, "I should get going."
A few days later, at the park, and I saw Eddie and an older man coming up the path. Eddie smiled when he saw me and it's about that time I realized he was with his dad, Justin, the player I had coached over 20 years earlier.
"Oh good! You are here!"
"Yeah. The dog and I have a reservation on this bench." I reached out my hand. "Justin? You've grown up!"
The man in front of me was clearly the same person I had known before, but now older and more filled out. He had the start of a bit of a dad bod, 20 years will do that to you, but he still looked fit.
"Hey coach! It's so cool to see you again. I love that you ran into Eddie. I just wish you were still coaching. His team needs the help."
"Dad told me you are the best coach he ever had."
"Well, thanks." I acknowledged. "You were definitely one of the best players I ever coached. "Did you play after leaving high school?"
"I tried in college, but I quit," Justin told me. "It just wasn't fun anymore."
"That's a shame... You were really good."
"I had good coaching," he countered. "I told Eddie he should ask if you were interested in coaching the high school team. I could even go to the school board and make a recommendation. I have some pull there."
I laughed and admitted, "I don't think I have it in me. I definitely don't have the energy for it. Walking to the park is about all I can handle anymore."
I could see they were both disappointed.
"But, you know what? I could draw up some drills. You can share them with your coach... or the players can just do them on their own. They're really simple."
"That would be so cool! Thanks!" Eddie crowed.
I diagrammed some grid drills that I knew would help them with their spacing and passing lanes. I tore the pages out of my binder and gave them to Eddie.
"Thanks coach!" He said.
"You already have a coach," I tried to correct, but he shook his head.
"Nope. That's Mr. Benson. He makes us call him that." Then looking at Justin, "Besides, Dad said I have to start calling you coach from now on."
"Well, okay." I agreed. "Let me know how the drills work for you."
After a few days I stopped by the practice and I could already see that they were better spaced and they were shifting to open field, which were the skills covered in the drills.
Eddie spotted me and quickly ran over. "Hey Coach! How are we looking?"
"Not bad," I confirmed. "With a few set plays, you guys could be pretty good. I can work on those and get them to you those next time I see you."
"Thanks coach. That would be awesome!" Looking back to the field, "I better get back. I'll see you later."
As he ran off, I hollered. "Tell your dad I said hi!"
I stopped by the next day and handed off a few pages with some plays for corner kicks and penalties, Eddie grabbed them as he ran past, still trying to cover his position during the scrimmage.
I was back at my bench the next time I saw him. "Hey Eddie!"
"Coach!" he gasped almost breathless after running hard. "Guess what... We won!"
"You did? That's great. Who were you playing?"
"Midtown," he crowed, and for good reason. Midtown had been solidly in the running for the division title. A win against them was a major accomplishment.
"That's outstanding! I'm really proud of you."
I could see how excited he was by the win. "We couldn't have done it without your help. Even Mr. Benson admitted that. I'd really like to thank you."
"Well, you're welcome," I answered.
"No," he interrupted. "I mean... I would really like to thank you." "Okay..." I responded, unsure what he meant. "How do you plan to do that?"
"Well... I really like you and... I was thinking... and don't get mad... but if you wanted to... I could maybe have sex with you."
A punch in the face wouldn't have hit me harder than that. "Eddie! You can't say stuff like that. I can get in trouble."
"No, you can't. You're not really my coach," he assured me, "and I'm 17, so that makes me legal. I looked it up."
"Why would you look that up?" I asked.
"I've been thinking about it for a while," he explained. "I just wanted to be sure."
"Damn Eddie! I mean, I'm old enough to be... your grandfather, for crying out loud."
"I don't care," he answered, matter-of-factly. "I really like you... and my dad was right about you. You're a great coach and you're cooler than most OGs."
"OGs?"
"Old guys," he explained. "That's not a bad thing. It's respect, man. I really like OGs."
"Well... look... I'm flattered. And I appreciate that you feel safe letting me know you're gay... but there's no way it can happen."
Eddie looked confused. "I'm not gay. Well... not exactly. I like girls, but I'm horny all the time and I know I don't want to get a girl pregnant. I don't need to worry about that with a guy. I just think, sex is sex. I don't really care if it's with a girl or a boy. I just think it would be hot."
"Then you should find someone your age you could get with."
"Girls and guys my age are idiots."
"No argument there," I laughed and accepted, "but I still can't do it with you."
With a look of concern, he asked, "Did your parts stop working?"
I barked a laugh. "No! The parts work just fine... At least those parts. The rest of me is probably past warranty... but those parts still work fine."
"Is it because I'm a guy?"
The answer to that was complicated.
Like Eddie, I could say with some confidence that I was not gay. But I was also not completely straight.
I had met my best friend about the same time I met my wife, and we were tighter than three coats of paint. He was even the best man at our wedding. But it was shortly after that he confessed to me that he was gay. I tried to act cool about it. But then he confessed that he had always been attracted to me and still was. He felt he had to tell me, but he wasn't trying to hurt my marriage.
The problem was, prior to getting married, I had been working through some questions about my own sexuality, so his revelation created a lot of tension between us and after a couple uncomfortable months of avoiding the topic, we gradually drifted apart.
I missed him and I still thought about him a lot. Over time I even came to comfortably accept that if I had not hooked up with my wife, I might very well have hooked up with him. I assumed that made me bisexual, but at the time I was happily married with a good sex life, and I figured I would never have to put it to the test.
Now, many... many years later, I was still happily married, only there was no longer any sex to speak of. We were still close, but we both seemed to have lost interest in having a physical relationship. But it wasn't like I had lost interest in sex.
Being an old fart I just accepted that masturbation was my outlet, and the last thing I expected was to have someone offering me sex, especially someone who was young enough to be my grandson.
"No, it's not because you're a guy... but it is complicated," I finally answered Eddie. "I am really flattered but, for I'm pretty sure your dad would hunt me down, especially if I hurt you."
"How would you hurt me?" He asked, looking confused.
"Well..." I nervously stuttered, "if we had sex... you know... like... anal sex... and I hurt you... I couldn't risk that."
Eddie laughed, confusing me even more. "I can't get hurt if I'm fucking you."
"Oh... I guess I just... I assumed..."
Eddie interrupted me. "I mean... I would let you if that's what you wanted. But I'm really hoping that you will let me fuck you. I know that's what I really want."
Not knowing how else to respond, I asked, "Why would you want to fuck an old goat like me?"
He shrugged his shoulders. "I told you. I'm a teenager and I'm always horny... I'm tired of fucking my fist... and I really do like OGs. I don't know why, but I do. But mostly, I really like you."
I was at a loss for words, but Eddie still had a few.
"I won't lie." There was mischievous look in his eyes. "Knowing that you knew my dad when he was my age... makes it even hotter."
"Eddie... I don't even know what to say..."
"Say yes!"
"This is... maybe too," I confessed. "You need to let me think on it."
"That's not a no."
I shook my head. "It's not a no. It probably will be... but for now it's not a no."
"Cool!" Eddie crowed, getting up to leave. "I don't know if it makes any difference, but just something for you to think about. I'm going to beat off when I get home... and I'll be thinking about fucking you."
"Good gawd kid... You really are killing me!" I sighed. "I'll be here tomorrow, and we can talk about it."
With that, he was off and running. My brain was running even faster. This was totally crazy, but mostly because of the age gap. Truth be told, if it weren't for that, I can't say I would have been so quick to resist. Eddie was a good-looking young man, and I wasn't opposed to the idea of having a man fuck me. I even had some idea of what it would be like.
I had tried my wife's vibrator, as an experiment. It was thin and only about 5 inches long, so it went inside me fairly easy. It was interesting and I did cum as a result. So, I had some idea that getting fucked could feel good, but I also knew the vibrator was a lot different than doing it for real.
The more I thought about it, the more I knew I couldn't go through with it. Eddie was just a high school kid and the son of a player I had coached back when he was just a kid. I didn't think there was any law against it, but it felt like it must be a violation of some unwritten code of conduct.
That night, I barely slept. My brain kept swinging back and forth between deciding how to tell Eddie it wasn't going to happen and then imagining what it would be like if it did. The next day, my head was still spinning as I sat on my bench and saw him approach, but I had finally decided on my excuses.
"Hey coach... What's the verdict?"
"Eddie, just so you know... I really did consider going through with it," I started, "But I know your dad, and I'd feel like I'm betraying his trust."
Eddie laughed.
"Why is that funny?"
"Mom and dad split a few years ago... They still liked each other but she was in love with her boss. Dad wasn't even mad. He admitted that he wasn't happy either." He paused to make sure it was sinking in. "The weird part is, Mom already had an idea about what was going on with Dad. So she asked him and he admitted that he thought he might be gay. He felt terrible about it and told her he'd been fighting it as far back as high school. She was really cool about it though, and they're still really good friends."
"Oh... wow," I acknowledged. "But... just because your dad is gay doesn't mean he would be okay with you and me..."
"But he is okay with it," Eddie interrupted and then explained. "He even admitted that he always had a crush on you. He said he wished he had let you know that, back when you were coaching him."
"I never knew, but... I was his coach. I wouldn't have been able to do anything."
Eddie nodded. "That's what he said too. But you're not his coach now... and you're not really my coach either."
"But that doesn't mean he would be okay with this," I said, referring to our present situation.
He chuckled. "I just told you. He is okay with it. I mean... I asked him."
"You told your dad we were talking about having sex?" I asked, mortified.
"Not exactly," he admitted, "but I talk to my dad about everything. I told him I wanted to ask you, and he told me I should."
That had been my best excuse for not going through with it, but I still had one card left.
"This is... crazy, but I still can't risk ever getting caught. My wife would not understand. We would need a place that's completely private and safe. We can't do it at my house, and I'm certainly not doing it at your house."
"That's no problem," he assured me again, to my surprise.
"How?" I questioned. "Do you have an apartment in town or something?" I was being sarcastic, but he was unphased.
"Not exactly, but I do have a private place." He could see I was skeptical. "Follow me. I can show you. It's not very far."
I followed him, half expecting he was taking me to a treehouse in the woods, but we headed toward the schoolyard, and he led me to an isolated shed that sat in a far corner. It almost disappeared against the wooded backdrop, and you wouldn't even notice it if you didn't know it was there or you weren't looking for it.
"What's this?" I asked.
"It's where we store all the old equipment," he explained. "When stuff gets busted or worn out, we put it here and then donate it or recycle it once we get a truckload."
"So, this is part of the school?" I offered, thinking that was too risky.
"Yeah, but I volunteered to be the equipment manager," and he continued, "I'm the only one who has a key."
"How did that happen?"
He shrugged. "Mr. Benson was just glad he didn't have to do it."
I looked around and there was no one who could see us, so I checked out the shed. It had no windows and just a single door that I could see. Eddie unlocked it and led me inside. My dog sniffed suspiciously at the door but then stepped through. Eddie closed the door behind us.
There was a single bulb hanging from the ceiling, but we didn't need it. The shed had a couple skylights, and as long as it was daytime, the inside was well lit.
I saw shelves with boxes that overflowed with torn goal netting, deflated soccer balls, and worn-out soccer shoes. Then I saw a full couch, a couple chairs, and a garbage can that was half filled with empty pop cans.
"It looks like somebody's clubhouse."
He laughed. "I guess it is... sort of. We sometimes hang out here after practice."
"But you have the only key?"
He held it up and waved it. "This is it."
I shook my head. The lack of a safe and private space had been my last good argument. I quickly ran through all the other excuses I could think of, and dismissed all of them.
"You win," I almost whispered. "We can try it."
"Really?" Eddies excitement was visible on his face. Without realizing I was doing it, my eyes had dropped, and his excitement was also visible in the leg if his shorts.
I didn't have to look to know that I was in a similar state. My brain may have still been screaming no, but my cock had already decided to join in.
"Yeah, really." I agreed. "Should we pick a time to meet up?"
He looked confused. "We're already here."
This was moving fast, but he was probably right. If we didn't do it now, I would just make up more excuses. The dog had curled up in a corner and was already snoring.
"Are you really sure you want to fuck an old fart like me?"
He shook his head. "Not just an old fart like you. I want to fuck you."
I couldn't remember the last time I felt in any way desired. It was an amazing feeling and so unexpected.
"How do you want to get started?" I asked, wanting him to take the lead.
"We have as much time as you want." He explained. "Maybe we can get naked and do it right."
"If you're sure."
I started peeling off clothing. This would be a moment of truth. If my aged, saggy, wrinkled body didn't scare him off, then something might actually happen.
As I undressed, I watched him do the same. In contrast to me, his body was fit, with the tight skin of youth that was almost hairless and smooth as satin. He really was a good-looking kid. I guess he was technically a man, but I still had a hard time not thinking of him as a kid... until he dropped his shorts.
I guess I had expected because of his age that he might be less developed down there, but Eddie had me beat by every measure and it was still inflating to full erection. I did a quick comparison to the vibrator I had used and knew that all my practice had done little to prepare me for this.
He saw me staring. "What is it?"
"I just... I just hope we can make this work."
"I'm not that big," he answered, looking down. "At least not yet. Dad is bigger... so maybe eventually. But I promise I will go easy until you get used to it. I want it to be good for you. I know you'll like it."
"I guess we'll find out," I offered as I dropped the last of my clothing.
This time it was Eddie staring at me.
"Is it that bad?"
"Not even close," he laughed. "I know you don't understand it, but you look hot."
Eddie grabbed a first aid bag from one of the shelves and pulled out a half-used jar of Vaseline. "I sometimes come here to whack off," he admitted as he approached me. Then handing me the jar he said, "Do you want to do the honors?"
I swallowed hard and opened the jar. Scooping out a generous glob of lube, I reached out with a shaky had and spread it over the length of his shaft.
Just the feel of it in my hand confirmed that his was thicker than mine, and the distance my hand traveled confirmed it was a bit longer. As my hand spread the thick grease over the knob of his cock, Eddie gasped, and his head lolled back.
"Ah jeez, coach!"
I think I could have continued stroking him like that and that would have been fine with me. But I knew he really wanted to fuck, and maybe for the first time, I knew that I really wanted to let him.
I sat back on the couch, with my legs spread and my ass perched on the edge. Eddie quickly climbed between my knees and inched closer.
"Thank you for letting me do this," He said, as his cock prodded and pressed against my tight pucker.
It's not a sure thing yet, I thought, but I didn't say it out loud. I could feel my asshole stretch and flex, as his cock knob slid around, only barely in its grip. He managed to hold back and not push right into me, which was better than I could manage. I kept lifting against him, feeling a sharp pang of pain that finally forced me to ease off.
It took a lot longer than my first time with the vibrator, and I was even getting a little worried that it wouldn't work, but time and pressure ultimately won out. I felt a soft flutter as my sphincter began to relax and ease open. Then, like reinserting a cork in a bottle, I felt his cock knob pop inside me.
I think I grunted. Not the sexy bedroom sound I had planned, but it was honest. There was no real pain to speak of, but the entry was abrupt, and it caused me to tense up again.
"Are you okay?" Eddie asked.
I appreciated his concern, but I could hear something else in his voice.
"I'm okay," I confirmed. "How about you? Are you doing okay?"
"It's just... I just..."
He was clearly struggling for words, but then the reason became clear. His body tightened up and he was trembling. Then I felt the soft pulse of his orgasm.
He hadn't even been able to start fucking me before cumming. Being inside of me had been enough to make him cum. Knowing he was that excited made me feel good. I was even okay if that was the end of it, but Eddie wasn't.
"I'm sorry... I'm so sorry," he mumbled. "I couldn't help it."
"It's okay." I assured him. "We can always try again another time."
"Oh no... I'm not done yet," he corrected. "I just didn't expect the first one would happen so fast."
"The first one?"
He smiled again. "I was just really excited. I can cum more than once. I do it all the time. I just wish the first one lasted longer than that."
"Well... okay" I said, accepting that we might not be finished. "Whenever you're ready."
"I still can't believe you're letting me do this," he finally managed to explain.
I had to chuckle. "I still can't believe you want to."
"If you still don't believe it after that, I guess I need to prove it."
I was stretched back on the couch, feeling calmer than I would have expected. Especially with a stump plugged up my butt and sperm already pooling between my legs.
Eddie was holding still, regaining his composure, until I heard him take a deep breath. "Okay... let's do this."
Then his cock started to move deeper inside me. I held my breath, anticipating another pang, but it never came, and I was able to slowly let out my breath as his thighs pressed softly against the back of my legs.
"I'm all the way in," he gasped.
"Yes... you are," I sighed.
The vibrator had been enough to make me interested, but the real thing ended up being a totally different experience that was even better. As hard as he was, it still felt soft and pliable, and the way it moved inside me made me feel things that were only barely hinted at with the cold, plastic facsimile. Add to that, I was not controlling the movement.
I wasn't sure how I would feel about being the receiving partner, not being the one who was fucking, instead being fucked. There was no question. It was so much better. Who knew?
Everything that happened had an element of being unexpected and uncontrolled. As Eddie began to fuck me, there were times when I would have paused... or moved faster... but I could never predict what he would do next, and I was continuously surprised at how much I preferred his choices.
His cock sliced through me, sometimes slowly and sensuously, like a snake worming through the grass, and sometimes hard and fast, like a battering ram. I was pretty sure that one was my favorite until he switched to the next, and that quickly became my new favorite, until he switched again.
I clawed at his back, feeling his muscles bunch and clench as he rolled his hips to pump his shaft through me. It was a perfect chaos that had me on the verge of cumming almost from the start.
Looking up at Eddie, I could still see the youthful inexperience in his face, along with his wide-eyed excitement. I was discovering feelings I never knew existed, and it felt good to know he was getting as much out of this experience as I was.
I couldn't say how long we were at it. There were moments when I thought he was close to cumming, but he would abruptly stop and freeze in position until the urge had passed. Then he would gradually work back up to a full, body slamming fuck.
There finally came a point where, no matter what he did, I couldn't hold back any longer. He pounded into me, and my gut clenched and suddenly my cock spewed jets of spooge that spattered my belly and chest. It was the biggest load I had fired in years and the spasms of my orgasm seemed like they would continue just as long as he kept moving inside me.
I wasn't sure how I could survive that if he lasted much longer, but my orgasm had been the trigger he was waiting for, because it was only seconds later when I felt the soft pulse of his cock, flooding my ass with his second heavy load.
As his tremors began to let up he looked down at me and I could see a tear run down his cheek.
"Hey! Are you okay?" I asked.
"Thank you... thank you so much!" He gasped as he leaned in and rested against me, cum gluing us together chest to chest.
"You're very welcome," I answered, wrapping my arms around him, and holding him close. "You have no idea what you just did for me. How much it means to me."
We rested together until the cooling evening air began to chill our bodies. We peeled apart and Eddie grabbed a roll of paper towels and water bottle from one of the shelves. We used them to clean up enough to pull our clothes back on. Then checking to make sure we had everything pulled together, I woke up the dog and we headed out of the shed.
"I hope you'll let me do it again, I really want to." Eddie told me.
"I would really like that." Something he had said earlier suddenly occurred to me. "But please, don't tell your dad about this."
He frowned. "I have to. He told me I have to. He really wants to know."
"Why would he want to know that?"
Eddie's smile came back. "He wanted to know if you'd go along with it. I told you, he's really glad you're not his coach anymore..." I thought about what that meant, but Eddie clarified. "Don't be surprised when he shows up at the park... with my shed key."
Well, at least the dog can still get some rest.