Son Needs Special Underwear Pt. 01

Growing up in a conservative household, I didn't receive much sexual education beyond the old "abstinence only" method. In fact, my parents didn't often discuss anything intimate or sexual with me, including how to be in a healthy relationship. As such, I got married at 19 to my high school "sweetheart," and less than a year after the wedding had already given birth to my daughter, Charlotte. A year after that, I gave birth to my son, Ben. My husband simply couldn't handle the trials and tribulations of parenthood, and left us soon after.

My husband leaving finally jolted me awake as to how I wanted to have a far more open and honest relationship with my children than my parents had with me. Raising a son on my own had its difficulties, but I always took great efforts to relate to Ben as he went through the ups and downs of boyhood, and teach him how to become a man. Despite the hardship, raising them has been the greatest joy of my life, and in a certain sense I wouldn't have it any other way.

Being 39 now, I have just one year left before I'm an empty nester. Charlotte is beginning her freshman year of college just as Ben is beginning his last year of high school. She had always been the brash, bold, outgoing one of the pair, while he was more shy and quiet. I had tried to get him into sports or hobbies that might attract more girls to him, but he generally seemed more content to spend time on schoolwork, or otherwise on his own. It didn't worry me too much, but now that he was 18 I was a little concerned that he hadn't ever had a girlfriend yet.

I will obviously miss Ben once he leaves, but I was enjoying having more free time without having to do much for Charlotte, save for the regular phone calls. I always kept pretty fit, but I was able to really up my workout routine and spend more time at the gym. Despite pushing 40, my tits were still nice and perky, and they never seemed to get smaller after having kids. At a D cup, they fit nicely on my slender frame. My real ASSet though is, well... I don't want to brag, but I'm constantly catching guys - even guys who are out with their woman! - checking my ass out. It's perfectly round and supple, and now with my workouts was staying nice and perky. It's a good few handfuls, not too big nor too small.

One day, Ben surprised me by saying that he wanted to start working out and getting into shape too. Dropping Charlotte off at college seemed to spark something in him, and seeing me workout probably helped inspire him too.

"Mom, do you think we could go shopping for some workout clothes? I don't really have any shorts or shoes that would work," he said one Saturday morning.

"Of course hun!" I replied. "Are you thinking of joining a gym or a sports league or something?"

"I'm not sure yet, but I just want to be in better shape once I start college next year. Figure it'd be easier to get in the habit now y'know."

"Oh well that's great! We can go right now if you'd like."

We hopped in the car and were off to a sporting goods store. I was honestly just happy that he was trying something new, and pondering if he would start trying to be more outgoing too. But I didn't broach the subject now as I didn't want him to feel embarrassed or self-conscious at all.

At the store, we picked out some nice running shoes that fit his size, then went to get some shorts as well. He took a while to try them on, and I was wondering if he felt self-conscious about how he looked in them. He was pretty skinny and usually just wore standard pants all the time, and baggy shorts in the summer. He wasn't really an athlete and I couldn't even remember the last time I'd seen him swimming.

Just as I was about to ask if everything was ok in there, he came out with a somewhat confused expression I couldn't quite place.

"Did they fit ok?"

"Um, yeah I think so. Do you think we could also look at leggings or something to wear under them? They're kind of short and it's going to get colder once Fall is here and everything."

"Oh of course! I think I saw them over there," I motioned towards an aisle that displayed the kind of underwear he was describing. I chuckled a bit at my correct guess - he probably just didn't want people to see his skinny legs.

Once we picked some out, we headed back to the fitting rooms. Once again, he seemed to be taking a bit longer than normal.

"Everything ok in there?" I asked after a good few minutes passed.

"Y-yeah, just making sure everything fits right!" He sounded unsure, and I was worried he was having second thoughts about getting into shape.

"Do you want me to have a look-"

"NO, I mean, no mom it's ok." He cut me off firmly. I started wondering if having a father who knew about menswear would help at a time like this.

I was getting a bit impatient though. "Honey, I know a lot about athletic clothes, if there's something wrong maybe I could help!"

"Yeah, but like, wouldn't you only know about women's clothes?" That stung just a little bit, as I'd always made sure to keep up with boys' fashion and styles and whatnot, and helped him buy all of his clothes (as plain as he liked to keep his wardrobe).

"Oh c'mon, we just wear shorts and leggings too! Let me in and I can tell you if they look ok."

"I dunno mom..." I could tell he was struggling a bit, and I sincerely thought I could give him some confidence if I told him how nice they fit (as I couldn't imagine his legs were THAT unsightly).

"Is it unlocked? It'll just take two seconds if you let me come in."

"Fiiiiine." I heard him click the lock to unlock it.

Upon entering the dressing room, at first I thought it all looked fine. The shorts were the same waistline as all his other pants so they fit fine, and he had on some white leggings that looked like what many other guys wear to the gym.

Then I saw the problem. And I saw how my son was, in fact, unlike any other guy.

There was a large and noticeable bulge running down the right side of his shorts. It looked profoundly uncomfortable, and like it defied physics. There were also two round bulges that must have been his balls right in the middle of his shorts. As I was taking in what I was seeing, I realized that the bulge went beyond just the shorts, and the head of his cock - er, penis, my son has a penis not a cock - was bulging under the white leggings. I couldn't even begin to guess how big it was exactly, or what was more impressive - how long it snaked down his leg, or how thick it was to create such a big bulge.

"See? I just can't seem to figure out how to make it look, like, normal." He was clearly pretty upset.

While I was open with discussing sex with my kids, the fact Ben had never had a girlfriend meant I never really thought about him having sex beyond just making sure he knew to use protection and to treat girls with respect. It had never occurred to me that there could be an issue with his penis.

"Oh sweetie it's ok, I totally see why you're having some issues with it. But y'know, it's not like you'll normally be going to the gym with an erection, so take your time to let it go down and I'm sure they'll look great." I was praying he was just a grower, not a shower. Given how big it was, even flaccid it might still make a little bulge, though that's not always the worst thing, especially if he's trying to get girls.

"Huh? Mom, I'm... I don't have an erection, like at all."

I was speechless. Here was my son, standing with a penis- no, I had to admit to myself, with a COCK that would put most pornstars to shame. And it wasn't even hard yet.

I had seen my fair share of penises since I had never remarried, and while some were pretty up there size wise, none of them were this big when flaccid. I was wondering if any were even that big when erect. I can't believe I had never noticed, and realized that that must be why he always opted for baggier shorts and pants than most boys.

"Um.. I mean, that's ok!" I was trying to keep my composure. "But yes, I don't think it would be wise to go to the gym like that. Ummm.. were there any tighter leggings, or looser shorts?" I couldn't keep my eyes off of it. The head looked so fat, and it was straining the material so much I could see some of the pink skin of his cock seeping through the white fabric.

"No, I specifically made sure to get the loosest shorts."

Ben couldn't be the first person to be too big for running shorts, right? As I was brainstorming, I realized that there was a solution that might work.

"Ok, why don't I go and grab some basketball shorts then, since those are usually looser and longer too. You can wait righ-"

"Forget it." He cut me off again, which wasn't typical as he was usually very respectful. "Let's just go home, this was a bad idea to start with."

"Oh honey it wouldn't be any trouble!" I was keeping my voice as peppy and clear as I could as I struggled to maintain eye contact.

"No, can we please just go home." I didn't want to upset him further, so I exited the fitting room so he could put his pants back on.

As we were leaving, I tried to sneak a peek at his pants to see if I could notice any bulge. While not too obvious, about midway down his thigh you could see the head of his penis bulge out a bit. It must have been swinging with his walk, because you couldn't really see it once he sat down in the car. I couldn't imagine how uncomfortable it'd be to walk around with such a large dick bouncing off your leg.

We drove home in silence, and I began brainstorming ways I could help. I was determined, as even though I didn't have a penis myself, that had never stopped me from helping him with all of his masculine issues. I then remembered something I hadn't thought about in years.

Growing up, my parents didn't seem to be very loving with each other, and I never heard them having sex or anything. We lived in a pretty rural area, and so my parents would often purchase certain necessities in bulk. One big trip to Costco was easier than going into town every time we ran out of this or that. I remember one time my mom said she needed to get my dad new clothes, and was picking out white t-shirts and socks and whatnot. Just the boring stuff.

Once we got to the underwear, I realized I didn't know much about men's underwear. Boxers, briefs, tighty whities... I started pondering what my dad might prefer.

"Should we get him underwear too?" I didn't think much of it, and was mostly just curious.

"Oh no no, we get those separately." My mom's tone made it clear I probably shouldn't outright ask what he wears.

A few days later, I noticed a package on the porch, which was pretty rare. Delivering stuff out to rural areas isn't always easy, so we tried to avoid ordering things to be delivered. The package was branded with "Dick's BD Underwear." I didn't know much about sex or penises, so I was curious as to why we needed to order these instead of just buying regular underwear. But I knew better than to ask my parents, so I just brought it inside and left it in their room.

The more I thought about it, the more I was curious as to what this "Dick's" underwear was and why it was so special. I didn't have my own computer, so late at night I snuck onto the family desktop and opened up an Incognito window. I typed "Dick's BD Underwear" and eagerly clicked enter. The website for the company was the first result, so naturally I clicked into it."

"Hung like a horse? Balls bigger than baseballs? Long shaft, thick head, you name it. If you are overly developed in any part of the male pubic region, then we have the right underwear for you."

I was shocked. I had never thought much about penises, though I knew some could be bigger or smaller I guess. I couldn't believe the range of underwear they had, with specific designs for different.. abnormalities. One for if you had large testicles, one for if you were super long; they would even specify the exact length/girth measurement suited for each product.

There was one called "The Daddy" that they advertised as their design with the biggest accommodation space.

"Some men are simply blessed. If you have a length above 10 inches, girth above 7, and huge balls to match, then The Daddy is the only underwear that can contain you."

I had to imagine that part of advertising it was that guys who wanted an ego boost might order it, even if they were underqualified, since I was pretty sure very few men would need such underwear. Once again, I was really curious as to what my dad needed exactly, and whether he wore The Daddy design.

But the story of my dad and I is for another day. Back in the present, I knew certainly that Ben would need something from Dick's BD Underwear, and might even need their biggest size...

I let Ben sit in his room for a few hours to calm down before I decided to bring the subject back up. Once I thought enough time passed, I gave a gentle knock at his door.

"Sweetie, do you have a second to chat?"

"Sure mom." He still didn't sound as chipper as normal, but clearly wasn't as high strung as before. I came into his room where he was sitting on his bed, reading. I sat next to him, resting my hand on his leg. I had to be conscious to make sure I didn't go above his knee, since who knew just where his long shaft ended.

"So, about earlier today..." I snuck a glance at his crotch, but couldn't see a defined bulge. "I really do want to support your efforts to get into shape, and I don't want you to be too... discouraged because of your... equipment." His expression was somewhat blank.

"I mean, I'm a freak mom, it's fine and I'm at peace with it. I'll just walk and bike more places and I'm sure that'll be enough." He clearly had been thinking about this all day.

"Son, you are not a freak. Yes, you are... on the bigger end of the spectrum, but that just means you are blessed! And, if part of why you want to get into shape is to get the attention of girls, then trust me, having a big one is only ever gonna help." I was trying to stay positive, and luckily he seemed receptive.

"I mean, yeah, I was thinking I should probably have some experience before college, but it's whatever." I could be wrong, but I thought I saw a little bulge halfway down his thigh pop up for just a second. I wondered if talking about his penis like this was getting him aroused. "But it's not like I can have it on display like that in public, so how would girls even find out?"

"I mean, it's ok to have a little bit of a bulge, and some girls - especially at the gym - look for when they can see a guy is packing a big one." I was proud of my ability to be frank with him despite the sensitive subject matter.

"Ok... but like, you saw how it looked, so how on earth could I make it not so... obscene?"

"Well, I know of a specialty brand of underwear made for well-endowed men, and well, you would seem to be a well-endowed man! I've done some research, and I think it's a combination of having a pouch area for your genitals, but keeping it tight so that there's no huge bulge. It's like... the best of both worlds, you have some room down there but you're still... presentable!"

"Ok... so were you gonna just order those and we could see if they fit? I would be willing to try that if we got some of the looser basketball shorts." I was so thrilled that he was open to trying them out!

"Awesome, of course sweetie! The only thing is, we need to get a measurement of your co-, er, penis, both flaccid and erect, to make sure we get the right size for you. Have you measured yourself before?"

"I mean yeah- or, well, only when erect. But I can do all that and then just order them myself... I'm not sure I should be like telling you the exact size, y'know?"

"Oh hon, it might look a bit different now, but I've seen it like a million times! Unfortunately, the underwear is quite expensive since it's so custom designed, and with your sister's tuition you know money is a bit tight. I'm totally willing to buy you these underwear, but we would need to make sure you got the exact measurements correct. It would be a shame if we ordered them and they were the wrong size, and we had to order more."

"That's fine but like, you know you can trust me right? It's not like I'd lie to you or anything," he said with a chuckle. He was such a sweet kid and I wasn't worried he was lying, and for a second I considered it. However, the single woman in me had to admit... I kind of wanted to see it. I wanted to see just how big it was flaccid, and then how much bigger it got when erect. In my experiences with guys I always had preferred the bigger ones, and wanted to see if I'd had any bigger than my Ben.

"Honey... I do trust you, but money is tight and it can be hard to measure on your own. You know I've always been open with you kids and you have nothing to be embarrassed about, but I think I'm going to need to measure you myself, just to be sure." I was hoping he would just acquiesce, because I knew that my REAL reason wasn't something I could share with him.

"I'm not sure mom... I mean, would you be uncomfortable with it?" Such a gentleman, just how I raised him.

"Don't be silly, of course not! You're my son, not some random guy." Even if he was, if I knew any random guy had something like what Ben had, I would be willing to get on my knees and measure it.

"Hmm... ok, that's fine then. I think I have a measuring tape in my desk." As he got up to get it, I could see that huge dick, except this time it wasn't as bouncy as before, and instead presented a straighter bulge that almost reached his knee. I just about fainted, but I was so thrilled that he seemed to be getting aroused.

"Ok honey, just stand right here in front of me and I can measure it flaccid." He stood in front of me, and before he even began to take his pants off, I reached for his belt to undo it. I was almost surprised at myself at how badly I wanted to see this cock! I knew it was wrong, but I was just going to be seeing it, though I hadn't fully thought out how we were going to get it erect...

"Whoa, so like, should I just stand here?" He was a bit startled by my zeal.

"Yeah if that's ok, I can just handle it all. If you want to look away that's ok too, so you forget that it's your mother touching you down there." I sincerely was concerned with his comfort, but I wondered if I would want him to be watching, knowing that his mother was touching his huge cock.

"Uh, sure, thanks. I think it's fine though," he said as I continued to undo his pants.

As I began pulling them down, I slowed myself a bit to really drink in the moment. I may never see this cock again, I thought to myself. I have to make it count without being too deliberate. Slowly, I started moving his pants and boxers down at the same time. I was still so eager I just had to do them both at once.

His pubic region looked like it'd maybe been trimmed, though since he was so slender, it tracked that he also didn't have much or very thick pubic hair. I then started to see the shaft, and was amazed at how thick it was at the base. Definitely thicker than my wrist, and I immediately wondered if I could wrap my small hand around it!

As I kept going, so did his cock - it just never seemed to run out of thick shaft. Finally, once his pants were almost to his knees, I saw his flared cock head come into view. It was massive, and mushroomed out beautifully, a bit thicker than part of his shaft, maybe the same thickness as the base.

"Wow..." I said without thinking. That was all I could think. Unless this cock literally didn't get any bigger when erect, then I was absolutely looking at the biggest penis I had ever seen, including in porn. Despite being so thick, I could see his massive balls were also visible, and hung down almost as low as his penis. I could tell just by looking that it all must weigh a ton.