My Son's Big Cock

Summary: Widow helps son cross dress for Halloween, and....

Note 1: This is a Halloween 2020 Contest Story so please vote.

Note 2: Thanks to Tex Beethoven for editing this story.

My Son's Big Cock

"Mom, can I borrow a pair of pantyhose?" my son Mike asked me.

"Those are words I never thought I'd hear from you," I joked, as I looked up from reading my kindle, my ankles crossed on the coffee table.

"We've all decided to cross dress tonight for Halloween."

"We who?"

"Daryl, Eddie and I have."

"Pretty last minute," I pointed out, wondering if he had any clue his dad used to cross dress all the time when he was younger (although we never called it cross dressing)... even winning some drag queen competitions back in our wilder days in San Francisco. Unlike many people's stereotypes of drag queens, Barry had been straight, never involved in any sort of gay action at all. In fact many of the drag queens were straight, just loving the sensual experience and sensations of dressing like a woman... something he'd kept secret from everyone except me until his cancer overwhelmed his body. Well, he also told his parents, but the less said about that the better.

"I know," he nodded. "Which is why I'm asking you for them, instead of taking the time to go out and buy some."

"What are you wearing for a dress?" I asked, wondering if I should allow him into the back of the closet in my room, where I still had a trunk full of all his father's drag queen costumes, including the important accessories for under the dress.

"Well... I was wondering if I could borrow a dress, too," he admitted sheepishly.

"I don't know whether I should be amused or insulted that you think you could possibly fit into a dress that I wear," I said, as he was a starting football linebacker at his college, rather impressive for a freshman, and I was still at forty-eight years young, a petite woman... five foot four and 110 pounds, compared to his athletic six foot two and 190.

"Sorry, that was kind of dumb," he said, as I rose to my feet and looked way up at him to illustrate my point.

"But I do have something you can wear," I added.

"You do?" he asked, surprised.

"Yes, but if you're going to dress up like a woman tonight, we're going to do it right," I asserted, thinking it would be fun to relive the days of helping Barry to become Bárbara. I'd never had a daughter to do nails and so forth with, but maybe I could get my son into exploring his feminine side, and thus bond in a way most mothers never could with their sons.

I knew he loved nylons. I'd found cum stains on my pantyhose on more than one occasion, and every day I noticed him checking out my legs and feet in the always sheer and shiny hosiery I ordered from France... receiving a big discount for being a loyal customer for years, for myself and, of course, formerly for Barry.

"How so?" he asked, completely oblivious to the crazy idea spinning in my head.

"Do you trust me?"

"Well, I used to... up until the very moment you asked me that," he quipped, teasingly raising a suspicious eyebrow.

We'd been a family of two for the past two years, and fortunately we were as close as a mother and son could be. He'd told me about receiving his first blow job (I'd congratulated him and asked for all the juicy details, rather than freaking out), he'd asked my advice about going down on a girl (which also included all the juicy details, although I stopped short of Show & Tell), and we'd gotten moderately drunk together to celebrate, when he'd lost his virginity to a third-year college cheerleader, back when he was an eighteen-year-old high school senior. Maybe this makes me sound like a bad mother, but I wanted not only to remain his mother, but I also felt the need to try and be his worldly-wise father.

"Come with me," I said, walking upstairs to my bedroom.

"Okay," he said, clearly intrigued, but a bit confused by what was suddenly happening.

"I have a surprise for you," I said.

"You have me very, very curious," he said, as he followed me down the hallway.

"just very, very?" I smiled as we entered my bedroom. "Not very, very, very?"

"Well, now that you mention it," he laughed, stressing each 'very', "I am indeed very... very... very curious."

"You know your dad and I lived in San Francisco, right?" I asked, a dumb question because of course he knew that, since his grandparents still lived there, in the same house for the past three generations.

"What? No, really?" he mocked, as I walked into my walk-in closet.

"No one likes a smart ass," I tossed back over my shoulder, thinking not only how much he looked like his father, as he'd matured in the past year, now in college, and how sarcastic he was, also just like his father.

"You married one," he pointed out.

"Didn't mean I liked him," I called out insincerely from the closet.

I reached for the chest and realized it was really heavy. I called out, "Come help me with this."

"Okay," he said, entering the walk-in closet, then asking, "What is that?"

"It's a chest, silly," I replied, able to be just as sarcastic as my husband and son.

"What's in it, smart ass?" he said, as he hefted it up on his own.

"Don't you go calling your sainted mother a smart ass," I scolded playfully as I followed him out.

"I'm certainly not going to call you a dumb ass," he smiled.

"You bet your sweet ass you're not," I said, as he set the chest down on the bedroom floor.

"So, what is in it?"

"Okay, so there's something about your father we never told you," I preambled.

"You're scaring me," he said, looking concerned.

"It's not a bad thing," I said, "although some people judged him harshly for it, including your grandparents."

"And now you have me scared, confused, and concerned," he embellished.

"So..." I paused, reconsidering whether this was the right time to tell him.

"What, Mom?" He asked. "Just tell me. Nothing you can say will make me think any less of him."

"Your father liked to wear women's clothing, and even performed as a drag queen during most of his college years," I revealed, before adding, "and after we moved here, he did it monthly at Jake's, almost until the day he died."

My son was shocked.

Speechless.

I added, needing to clarify, "He wasn't gay or anything. He just liked to wear feminine undergarments and outfits to explore his feminine side."

"Oh," he said, his mind seeming to be spinning, as he tried to process this unsettling news... although his tone not revealing what he was thinking, good or bad.

"Don't judge him poorly for that," I urged, now worried I'd tarnished his father's image for his only son.

"No, it's not that," he said, looking like he wanted to say something more, but couldn't find the words.

"What is it?" I asked defensively. "He was very comfortable with his feminine side, and it made him a better man, a better husband, a better father, and even a better lover."

"It's just that..." he began and stopped. "Lover?"

"Yes. By exploring his feminine side, he was better able to understand my needs," I explained, thinking I might be giving him too much information; he probably never needed to know what we'd done in the bedroom.

"Oh," he said again, clearly still struggling with something.

"What is it?" I asked again, as he was looking insecure and vulnerable... the only time I'd seen that in him before was when he got dumped from his girlfriend of six months, by cheating on him with one of his teammates.

"I, um."

"Just spit it out," I said, now rather desperately. "You know you can tell me anything. I mean, just last month you told me about butt fucking that older woman."

"I was drunk when I told you that," he pointed out.

"Hey, no judging," I said, "I don't judge you for things, I know you don't judge me, but right now I'm hoping like hell you're not judging your dad," not disclosing that I too liked a dick in my ass, although that hole had cobwebs over it, not literally of course, after years of neglect. Other than a magic wand I bought at a sex party, my sex life had died when Barry had.

"It was my idea to cross dress tonight," he admitted nervously.

"Oooooh," I nodded, as I suddenly realized where he was coming from. I then smiled delightedly, "So you're saying like father, like son?"

He laughed awkwardly. "Maybe. So Dad really used to be a drag queen?"

I opened the chest and said, "See for yourself. I kept all his outfits, and some of the accessories that enhanced his sexy look."

"Sexy look?" he asked, as he knelt down and peered into the chest with me.

"He made a very sexy woman."

"Really?"

"I'm still worried. You're not judging him?"

"No," he said. "I'm absolutely not. If anything, my own curiosity and confusion are beginning to make a bit of sense."

"Would you like me to help you get all dolled up for tonight? Just like I used to do for your Dad?"

"Will you?" he asked, looking both excited and nervous.

"I helped him get dressed up nice and gorgeous lots of times. I bet you'll look just as cute!"

"I can't fathom."

"And... we had some of our hottest sex when he was all dolled up," I admitted, having never shared that with my son or anyone before... but recalling how feeling his legs in sheer nylons as I sucked his cock, sometimes through the special men's pantyhose we'd ordered, where he slid his cock into a special sheath for it... he'd even fucked me many times while wearing pantyhose... with some lube, it felt pretty damn amazing.

"Mom!" he gasped, as he pulled out an upper body piece that served as tits.

"What? Your dad and I had sex," I said, before adding, "a lot. It's kind of how you got here."

"Lol, fine," he said, as he examined the special 'male mammary' accessory.

"Your dad liked his tits big," I joked.

"Who wouldn't?"

"Sometimes I thought he liked his own tits better than mine," I said, as I stood up and ordered, "Get undressed."

"Here?"

"No, outside in the street while the neighbours take pictures," I adlibbed. "Of course, here."

"Really?"

"I've seen you naked lots of times, and I've laundered your stained underwear," I pointed out.

"That was years ago, and those stains were after my marathon sessions with hotties," he denied.

"I know you still jerk off," I said and then added, enjoying this frank conversation, "I can hear you when you jerk off."

"Oh, God!" he said, standing up himself.

"You often moan that," I teased, "presumably when you come. I'm not complaining, mind you."

"This is surreal!"

"No, it's really real," I corrected, as I went to him and pulled his t-shirt over his head. Fuck, he had a muscular chest. If he weren't my son....

He laughed, "so it is."

I then added, enjoying this frank conversation, that went deeper than our usual frank conversations, which were... well... pretty frank, "I also know you sometimes wear my pantyhose when you touch yourself."

"Oh my God, you do?" he gasped.

"Yeah, cum leaves stains when it dries, especially in black pantyhose," I pointed out.

"Shit, duh," he said, shaking his head. "I'm sorry, I've just always liked the feeling of nylons."

"Not to worry, I'm not judging you. 'Like father, like son'," I repeated, before ordering, "Take off your pants."

"What?"

"You heard me," I said, actually dropping down before him and yanking down his rather convenient sweats. "You'll need my help getting dressed from scratch, if you're going to pull this off."

I then gasped at the following observations:

1. He wasn't wearing any underwear.

2. His penis was hard as a rock and pointing right at me.

3. His cock was huge... easily eight inches.

"Oh my," I said, unable to hide my surprise before he attempted to cover his cock with both hands... his big... hard... thick... cock. And his large hands, perfectly suitable for snagging a football out of the air way down field, were totally inadequate for this purpose.

"Mom, I... um..." he said, his sweats at his ankles, and his hands (as I said, inadequately) hiding his cock, as he looked completely embarrassed.

"Oh, honey, I've seen your penis before," I said, trying to calm him down. Acting casual, like I wasn't at all startled to discover my son was very well hung, "Step out of the sweats."

"This is weird, Mom," he said, clearly uncomfortable at being naked in front of me.

"It's just a penis, honey," I said, as I grabbed a pair of 'mantyhose' and added, I don't know why, "Although it's a lot bigger than I recall."

"Mom," he said, still covering his penis.

"I'm sure the ladies love that thing," I said, before again adding, clearly my lengthy dry spell leaving me not thinking straight, "you're even bigger than your father was."

"Mom," he repeated, stunned by the direction this conversation was taking.

"Honey," I sighed, as I rolled up a leg on his brosiery, "look, just pretend I'm your Dad. This is a conversation you'd have with him if he was still here."

"It's just so weird," he said, as he finally stepped completely out of his sweats.

"Socks too," I added, as I dropped back down in front of him, unable not to take another furtive look at his impressive cock... and at his thick cock head, and at the slight upward curve to his cock. It was indeed a very impressive member, and if Mike weren't my son I'd already have it in my mouth.

"Are you actually going to put this pantyhose on me?"

"Actually," I parroted back, including his emphasis, then standing back up and setting the 'guylons' down on the bed. "If we're going to do this, we have to do it right."

"What does that mean?" he worried as he stood there completely naked, his cock still hard I noticed... clearly his discomfort and awkwardness in this situation wasn't deflating his inner excitement.

"Sit down on the edge of my bed," I instructed, feeling a bit of rejuvenation as I got the chance to do something I used to do all the time... feminize my man. Or at least my son.

"Okay," he said, still clearly shocked, yet also secretly intrigued, since he was no longer protesting, and all of his protests had been weak in the first place... no more than words, without any supporting actions.

I went to my dresser and grabbed my reddest fingernail polish, and walked back to him. I knelt before him as he asked, even though it was obvious exactly what I was doing, "You're not painting my toenails, are you?"

I smiled as I said, shaking the bottle, "Cross your legs for me, and actually I'll be painting your fingernails, too."

"Isn't that too much?" He asked, even as he obeyed and crossed his legs, having to adjust his raging rod.

"Like I said, if we're going to do this, we'll do it right," I repeated, thinking how much fun it would be to take him to the club where his father had performed during the last few years of his life.

I began painting his toes as he asked, "So Dad was really a cross dresser?"

"Not a cross dresser, a drag queen," I corrected, the two terms quite different.

"What's the difference?" he asked, allowing me to paint his toes.

"Cross dressers usually dress in female underclothing beneath their male outer clothing. They often do it secretly, are very insecure about their sexuality, and from my experience, they're usually either cock suckers, or wannabe cock suckers," I explained... still being completely frank.

"I'm not into that," he said.

"Good," I said, not that I was homophobic, I just wanted grandchildren one day. I continued, "On the other hand, a drag queen is proud of exploring his, or sometimes her, depending on how they prefer being addressed, sexual identity, doesn't hide it at all whenever they're in full flaunt, and revels in the admiration of other people as they push back against the boundaries of a boring, judgmental society."

"Wow, you're really passionate about this," he said, as I completed the last toe of his first foot.

"I hated the stigma your father had to swim upstream against," I said. "As far as I'm concerned, anyone should be anything they want to be. Gay. Straight. Bisexual. Transgendered. Drag queen. Or anything else imaginable, so long as they aren't hurting anyone. Narrow-minded conservatives assuming he was a cock sucking faggot because he wore women's clothing and looked gorgeous, really pissed me off." I realized I was getting a little hot under the collar, as I'd had to defend Barry many times, and sometimes hadn't gotten very far with some blockheaded bigot.

"I'm definitely straight," he clarified, then added, "but I've always had a thing for ladies' panties and nylons."

"I've long known about the nylons," I smiled, as I tapped his leg, and he uncrossed and recrossed his legs, allowing me to snatch a quick glimpse at his cock (still hard), which had gotten me undeniably horny. I silently cursed myself for thinking of my son in such an inappropriate way.

"You have?" he asked, surprised.

"You don't hide your attraction to my legs and feet very well," I said, beginning on his second foot, and realizing what I was saying would embarrass him.

He surprised me as he said, "Well, it's your fault I have a nylon fetish."

"My fault?" I asked, a little surprised.

"During my entire life, you've walked around the house or lounged about wearing sexy nylons," he said. "Which has been driving me crazy ever since I was twelve."

"Like father, like son," I said again. "Your dad insisted I wear them day and night."

"I tried to insist that Kimberly wear them too," he said. "But she was pretty reluctant to, and she whined about how uncomfortable they were every time she did wear them... making her 'terrible sacrifice for my demanding boyfriend' very clear."

"Girls today put almost no effort into their appearance; they think their youthful beauty is all they need," I said, and added, "but that eventually fades."

"It hasn't faded at all for you, Mom," he said, looking down at me.

"That's so sweet of you to say," I said, really wishing he wasn't my son, because that big dick would have been in my mouth or my pussy half an hour ago. "It isn't true, but it's sweet."

"Mom, it's the truth that you're really hot," he insisted as I was finishing his last toenail. "All my friends talk about you, saying things I find super awkward."

"Really?" I asked, as it was my turn to be surprised.

"Trust me, you don't want to hear the things they say about you," he said.

"Well, following that warning, I definitely want to know now," I said, enjoying this frank conversation and our slow-burning, sexually charged, interaction. My wand could look forward to a really good workout tonight.

"They're pretty crude," he warned, as I stood up.

"How crude? For instance do they want to fuck me?" I asked bluntly, for some reason feeling the need to shock him right back.

"Mom!" he gasped, obediently shocked.

"I hope they aren't talking about spit-roasting me or gangbanging me," I added wickedly, enjoying making my son uncomfortable like this. I hadn't been spit-roasted or gangbanged since my college days, when I was rather wild. I also hadn't munched a pussy since then... truth be told, I would likely allow any of those to occur if the opportunity presented itself. And I was sure Barry would be very understanding if he happened to look down from wherever he was.

"I can't believe you're talking like this," he said, shaking his head in disbelief.

"I haven't been fucked since before your dad passed," I pointed out, before adding, "and just like my sexually active drag queen wannabe son, a woman does have her needs."

"Well," he said, shaking his head incredulously, "I know that James, Hank and Wally would all love to help you with them."