Comments very welcome. Send to todd.dunne at protonmail.com.
All characters are fictional; this is pure imagination. Disclaimer: If fictional sexual stories involving consensual sex between adult men and teenagers offend you or are illegal for you read because of your age or location, do not read. Do not read if sexual relations between family members offend you or are illegal to read about where you are. This story is the property of the author, and is published on Nifty under its standard non-exclusive license.
Remember that Nifty needs your donations to keep providing these stories.
I wasn't quite sure what to do with my son, Tom. Of the three kids in the Baker family, he'd always been pretty good. Not as bad as his older sister, Kelsey, nor as goody-goody as his younger brother, Peter. Tom had just turned 18 and also just started his senior year of high school. Up until his freshman year, he'd been my quiet, nerdy son. A shift started then, though, and now he seemed to have outpaced his sister, who was an absolute sex fiend.
Before that shift, his sister had been the only one to make me worry. We'd always been open and lenient with our children. My wife Kristen and I encouraged our kids to make their own decisions and not to be ashamed of their natural feelings or bodies. We had a pool in our backyard, and Kristen and I would often skinny dip. Neither of us was above walking around the house totally naked. All of our kids had run into me leaving the bedroom to go grab fruit for sex games with Kristen, and they had all seen me with an erection. We didn't invite our children in to watch us having sex, but each of kids at some point in time had seen Kristen and I fucking. When they stumbled into our bedroom, or the backyard, or the kitchen, wherever we were fucking, we assured our children that Daddy wasn't hurting Mommy, that Mommy liked it, and that they didn't need to stay but they didn't have to run out. That way, we hoped out children would not grow up with the unnaturally harsh beliefs about their bodies and the way sex was supposed to work. Kelsey had taken it to the extreme, however. Especially when it came to sex.
She was now 20, but we'd known she was sexually active since I caught her blowing my boss at a house party when she was 13. We were aghast, and threw him out, thinking that she'd been manipulated by my boss. In truth, she was manipulating him. After that first incident, she would show up at my work to fuck him, unbeknownst to me. A couple times, I walked into his office first thing in the morning, only to find him with his cock in my daughter's pussy. She was skipping early morning tennis practice to get screwed by my boss. My wife and I finally recognized that she was a serious nympho. We were worried that she'd get pregnant or a serious STD, but since we couldn't seem to stop her from sleeping with almost anyone, we set up a practical rule. She could fuck anyone she wanted--be it her latest boyfriend, the UPS man, or (at one family reunion) her cousin--so long as it was in our home, and as long as she was on birth control. That meant my boss showed up to our house frequently for a couple years. In fact, since she started having sex, we have been waking up to some man in our house who isn't in the family most mornings each weeks. These days, it's often the neighbor who happens to be her community college professor. He comes over a few nights a week, and that's how she gets reasonable grades in that class. Her boyfriend (not the professor) is also at our place a bunch.
Kelsey had class last night, so this morning I expected to see the neighbor. I sat at the table with Peter, who was 14. Since he was our good son, he came in dressed for school, wearing jeans and a polo. We were talking about how speech and debate club was going for him when my daughter came in. Unlike Peter, she was not dressed for school. Of course, taking community college classes and working a few hours a week at a coffee shop, she often would laze the whole day away fucking the professor (who most days off, since he taught at night), whatever delivery man she could find, or sitting out by the pool wearing nothing but working a vibrator up into her pussy. This morning, it seemed she probably had a free day, so she was barely dressed. She was wearing only a sheer black thong, so her breasts were fully on display. This wasn't unusual. Like I said, my wife and I encouraged our children to be themselves. On hitting puberty, Kelsey had taken this to the extreme. She would show up at breakfast nude, or wearing only a swimsuit, or wearing an open robe without any underwear on. Sometimes, she'll be having sex in the kitchen when the family starts to gather. She often asks me whether she needs to her pussy or whether I think her pubes are in good shape. Yesterday, when I came in to grab breakfast, she was splayed out on the dining table, absolutely naked, with her boyfriend fucking her. Of course she didn't stop until he came in her pussy. Why would she? I served myself cereal and ate it at the counter, watching her 19-year-old boyfriend ram his raw cock in her pussy. Peter came in and joined me in doing the same.
So, given how wild Kelsey was, I had been sure my boys would never be more a cause for concern than her. Boy, was I wrong. Now it was my son Tom I was worried about. You see, Kelsey may have been hyper sexual, but she kept it reasonably private. She would have sex with anyone in our home, any time, or in other private spaces, but I'd never caught her in public having sex. Sure, sometimes she seemed to like making other family members a little uncomfortable, but nothing too serious.
Tom, though, was a different story since he started coming with me to the gym when he hit his freshman year. That was on top of him going to the gym at school. Something flipped in him. He decided that he wanted to be muscular, and we were happy to encourage him in that, and his workouts started showing results pretty rapidly. There was a fateful incident about his penis that seemed to affect him a lot, though.
One morning, early in Tom's freshman year, he came into the kitchen in the morning wearing a wife-beater t-shirt and nothing else. It had been a while since I'd seen his junk, so this was something of a surprise. It was more than I was expecting, by a lot. 9 inches or so, I'd guess. Bigger than mine. Tom had gotten a growth spurt starting about 6 months ago, and he'd grown nearly 6 inches in that time. He was as tall as I was, 5 foot 11 inches, and I had to expect he'd be taller than me too in a few short months. In a matter of months, he'd gone from looking his age to looking about 18 or 20. He was still very much an early teenager, though.
Since our family was open, his entering the kitchen in less than a complete set of clothing wasn't out of the question, Kelsey had been doing it for years already, but for Tom this was new. He saw me notice his penis hanging out, and he explained, "My underwear just felt too tight. The only way this to be comfortable if I'm wearing underwear is to let this part go out the leg or up through the top if I'm hard." He was standard in front of me, and demonstrated his shaft in those two positions. "I think I need new underwear. None of mine fit."
"Of course, son. We'll do that tonight after school." When the time came, I picked Tom up from school and took him to a department store. We quickly found a 20-ish, obviously gay salesman who clearly was both gay and went to the gym several times a week. He tried on a range of items, but most of them didn't work. I kept coming into the changing room to see, and it was getting crowded with dozens of unsatisfactory items. After a couple of annoying hours, we still weren't having any luck. The salesman noted that it was relatively late and the store wasn't busy, so we could just do the changing on the sales floor. Tom looked at me, and I agreed that it would be okay to change on the sales floor. At that, the salesman came into the changing room, pulled the underwear that Tom was trying on off of him in a quick motion, then grabbed Tom's clothes from the hook, and walked out saying "Follow me." The salesman was so prompt and officious about it that we just followed along. "Wait here in the accessories section. I've got a few more ideas, I'll go grab them. I'll leave your clothes at the checkout desk." With that, he disappeared.
I look at my 14-year-old son, nude, in the middle of the store. The underwear options we'd seen so far were either too tight in the front area if they fit at the waist, or too loose at the waist if they accommodated his substantial package. He was frustrated by the lack of success. "Who would have thought finding underwear that fit would be so hard?," I said. "I'm sorry, Tom."
"It's okay," he replied unconvincingly. A couple of straggler patrons in the store walked by us as we were talking. Tom seemed not to be sure whether to hide himself or just hang out where he was. I tried to make him feel comfortable by looking him straight in the eye.
When I felt that wasn't working, I said, "Tom, what you're packing right there is nothing that everybody here hasn't seen before. You don't have any reason to be ashamed." I patted him on his shoulder.
"Thanks, Dad," he said, hugging me. In the hug, I couldn't be sure, but I thought I felt his cock growing slightly.
The salesman returned with a few boxes while we were hugging and said "I have a partial solution for now." He explained that Tom's cock was just very large for a boy or man his size. "Most of what we carry just isn't designed for--," he gestured at my son's cock, his hand just an inch away, "this amount of penis." He looked a little flabbergasted at this gargantuan member in front of him. "What we need to do is--may I?" The salesman knelt down in front of my son, about to touch his penis, asking for his and my permission to touch it. We both nodded, and he gingerly grasped my son's mushroom with one set of fingers, and gracefully cradled his substantial testes with with other set. "We need something with substantially more volume to allow this to sit comfortably in a pouch." He then reached around Tom and grasped each of his ass cheeks. "We also have to make sure there's enough to accommodate this ass, which is also bigger than most of our clients." I looked behind Tom, seeing where the salesman had put his hands. He was squeezing my son's ass repeatedly.
"Okay," I said, "so what's your solution?"
"Like I said, this is a limited time solution." He explained, demonstrating while touching various parts of my son's penis, balls, and ass, that the store had all of 3 things that would work for Tom right now. "Two jockstraps and a thong."
He opened the first package and explained that jockstraps, since they didn't have restricting material in back, could accommodate Tom's dick, so long as the pouch is stretchy enough. He slid the jockstrap on Tom, and demonstrated how the pouch could fit his enormous cock by squeezing it. "And look, totally free in the ass." He squeezed my son's ass. I noticed that the dick was definitely responding the salesman's attention, starting to thicken and stick out substantially. It was absolutely easy to see Tom's dick in this jockstrap, because the pouch was black mesh. "See?" the salesman invited me to squeeze my son's cock, so I did.
"Yeah, that fits better, how does that feel, Tom?" My hand was still squeezing his cock.
He looked me in the eye. "Much better." Then the salesman pulled down this jock, and pulled up a second one. This was exactly the same style, but white mesh. He explained that he was sorry, but that while these mesh, see-through jocks were very stretchy and allowed my son's cock room to breathe, the others in the store were more designed to restrict. These were designer jocks, but they would work for Tom. Again, the whole time, the salesman was squeezing my son's cock, which was more and more sticking out.
He removed the second set of underwear, and lifted up the third option, a thong. This one, he explained, could also accommodate Tom, because like the jocks, there wasn't much fabric in the back to restrict "this." At "this," he grabbed my son's bare shaft, which was sticking out above the thong's top. Then he opened the pouch, put the shaft inside (it did strain a fair bit). Again, I could see my son's cock easily, because this thong, though red, was utterly sheer. Rubbing his hand along my son's shaft, the salesman asked "What do you think?" to me, inviting me to feel the fit. I grasped my son's shaft, and squeezed it through the thong to test the feel. The salesman noted that his balls still had plenty of room, grasping them and inviting me to do so, and then that the ass had plenty of room to breath, again inviting me to squeeze my son's ass.
"Yeah," I agreed. "What do you think, Tom?"
"I like it, if you think it looks okay." I assured him that it looked great. "But will this be enough? I feel like I'm still growing. And these are only three pair."
The salesman explained that, unfortunately, only those three were currently in stock, but we could order extra sets for home delivery, and we could also go to either athletic specialty stores to find jocks more designed for Tom's cock, or go to gay clothing stores in person or online, since they had a better selection. As to whether this would be enough for future growth, the salesman asked how big my cock was, for comparison, and motioned to my waistband, asking for permission to pull it out.
I nodded to him, indicating he could fish my dick out. "Tom's already got me beat, at 14!" I smiled and looked at Tom. The salesman unbuckled my belt with remarkable speed and pulled my pants all the way down. My briefs, which were straining and the hard-on I'd developed from all the penis talk, came down just as quickly. Instinctively, I lifted my t-shirt and removed it, so that I was nude, for all practical purposes. My cock stood out before me. I'd always been impressed by it, but Tom was making me reconsider that.
"Wow, pretty big," the salesman said, grabbing my cock and pulling me over to face my son directly. He pulled the red thong off Tom, then held both our cocks against each other. I felt Tom's cockhead pressing into me. "Still, you've already got your father beat, kid, and you're still growing, so I'd bet you have at least a another inch or two to grow." He pulled my hand down so that I was grabbing my son's and my cock, next to each other. I agreed with the salesman's assessment. I though Tom still seemed a little nervous, and I thought of how I might assuage his nerves. These underwear were very different than what I normally wore around the house, so he might be feeling weird about that. I asked the salesman if he had of these jocks or thongs in my size. He did, and ran to go get them.
While he was gone, I was still holding our cocks together, and I noted that Tom seemed to be precumming a touch. I thought I might be, too. I assured Tom that this was all perfectly fine, and while we stood there another store employee, apparently the manager, walked up to us with a quizzical look. I released my son's and my cock, and turned toward the manager, starting to explain the situation. The salesman returned in the meantime, assured his manager that there were almost no other people in the store, and that no one would mind a wholesome father-son outing to fit underwear for a gargantuan cock, and at this he squeezed my son's cock again. He then asked me to completely remove my clothes, so he could fit me with the jocks and thong, and he gave my clothes to the manager and asked him to take them to the register. The manager did, and the salesman deftly pulled up each of the three pairs, wrangling them over my hard cock. Each time, he squeezed my cock, balls and shaft, and ass to emphasize how the design fit my package, "which is really quick large, something to be proud of." He also invited my son to do the same, and he did, feeling the parts that made him, slightly stroking my shaft each time.
"Great, are we set? Do you want to order extra sets of home delivery?" I said that we did, and the salesman removed the underwear. My son and I were now naked, barefoot, and hard in the middle of this store. Another shopper walked by, this time a woman with her teenage daughter. I thought I recognized her as a neighbor. She shielded her daughter's eyes but stared obviously at my cock briefly, and longer at my son's. He noticed, and blushed. The salesman was walking toward the cash register, and I put my hand on Tom's shoulder and moved us to follow him. We arrived at the cash register, where the manager and yet a third employee, this one female, were waiting. There weren't any other customers, so these other staffers seemed to be there just to make sure our purchase processed correctly, or something like that.
As the salesman started ringing up the purchase, the manager piped up. "I understand we don't have as many options as we'd like to fit your son's cock. I know you're going to order some more, but to make up for your trouble, we'd like to offer you these items free, plus an additional two free pair delivered, for each of you, as long as you order five more pairs each." I thought that sounded generous, and agreed. Tom picked out the colors for his underwear, and I chose the same for my sets. The female saleswoman handed me a black mesh jock, and handed one to Tom. "There. You can wear those out of the store if you like." We both nodded, and I started lowering the jock to step into it. "Oh, no," she said. "That's his, so you can help him put it on." She turned to Tom, "And that's your dad's, so you can help him." Somehow, after all of this, I still had the capacity to blush, and did. I knelt down in front of my son and helped him put his jock strap on. I had to grab his shaft to move it out of the way. Then, to make sure that everything was fitting properly, I ran my hands under his jock and gently massaged his balls. I reached around back and snapped the back of the jock.
"Perfect," I said.
"Now I'll help you," Tom said. He went through the same motions with me. As he briefly stroked my cock, he said, "I think it fits in there well. These are good for both of us, Dad." I agreed, then invited him to stand up. The saleswoman handed me our clothes, from which I grabbed my items then handed the remainder to Tom. I donned my clothing, and Tom put his on.
Read Todd Dunne's other stories here on Nifty, and remember that Nifty needs your donations to keep providing these stories: