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A Son's Virginity: A Christmas Tale

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Summary: A mom gives her son the best Christmas present ever.

Note 1: This is a 2018 Holiday Season Contest story so please vote.

Note 2: Thanks to Tex Beethoven, Wayne and Robert for editing this story.

2018 had been a tough year for our family.

First, a small fire in our house led to our losing almost all our family photos, among other less significant items. Thankfully, the last couple of years were digital, but all of our wedding, baby and family photos from the past two decades were gone.

Second, our car's engine died three weeks after the warranty ended, and it was a major expense to replace.

Third, and the worst of the three by far, the other two rather trivial in the great scheme of things, my husband Ken went to bed one night and never woke up. Four months later and we still don't know what led to his unexpected and mysterious death at age forty-five.

Thus at forty-four, I was a single mother of three and about to be going through empty nest syndrome all by my lonesome. My oldest son Jeremy was twenty-three and in his last year of college on a basketball scholarship; my only daughter Beth, who graduated last spring from high school, was on a year-long exchange that she'd considered withdrawing from after her dad's untimely death in the summer, but I insisted she go and enjoy Germany and the rest of Europe; which left my youngest son and me alone together in a house that once had five of us living here.

My husband's death hit us all like a ton of bricks, but it was particularly hard on my youngest, Xander, because they were so similar. Jeremy took after his grandfather and his athletic ability, Samantha took after me with the travel bug and cheerleading, while Xander was the academic one, like his father. He was socially awkward and incredibly shy... also just like his father.

His father and I were an 'opposites attract' couple. I was a college cheerleader, he was an engineer. I originally hired him to help me with math and I ended up helping him lose his virginity. It was a pleasant surprise to us both that he was well hung. He was of course familiar with his own equipment, but because of his meek demeanour he'd never paid any attention to comparing it with other guys', so he didn't even know the power he was carrying around between his legs. It was a power I let him know about in the bedroom, even eventually coaxing him into dominating me whenever we had sex, which was often, but no other women ever found out about it. It was our own not-so-little secret.

Anyway, with Christmas coming and neither of my other children coming home until right before or even after Christmas (Jeremy on Christmas Eve and Beth the day after Christmas when flights didn't cost an arm, a leg and a first-born child), it was just the two of us doing the Christmas traditions that we used to do as a family.

Xander had always loved Christmas and I hoped this closeness with his mom might bring him out of his lengthy melancholy which still had its grip on him after his father's passing.

He came home from school one day and I had the tree and the ornaments out and said, "Come help me put up the tree."

"Already?" he asked. We'd always waited for when all five us were home. It was a tradition.

"Yes," I nodded. "We need to get into the Christmas spirit earlier this year."

"Okay," he nodded, and I was glad to see a little twinkle in his eye as he headed over to the DVD shelf. "Home Alone, the Santa Clause or Trapped in Paradise?"

"You choose?" I said, all three being Christmas movies we watched every year. Actually, truth be told, we watched the first four Home Alone movies at least once, as well as all three Santa Clause films even though the third one was brutally bad. And, for some reason Trapped in Paradise had become a family favourite, if only because my husband had loved Dana Carvey. Although Dana's best movie, besides his iconic role in Wayne's World, was the one no one remembers: Opportunity Knocks.

"Trapped in Paradise, for Dad," he said decisively.

"Great choice," I agreed, and the movie played in the background while we decorated the tree.

I hadn't ever noticed it before, but Xander kept gazing down at my legs and feet. I'm a secretary at a law firm, so I always wear a skirt or dress to work with nylons, as part of the expected dress code. I also always wore nylons at home, as that had been my husband Ken's fetish. I never really understood it, frankly, but he loved seeing nylons on my legs, especially the sandalfoot ones, which are clear at the toe. Years ago I'd tried to argue the reinforced toe ones were more practical financially as they didn't run as quickly, but the enthusiasm he showed me in the bedroom for the sandalfoot ones soon convinced me that this was one argument I was happy to lose. Oddly, my toes barefoot did nothing for him sexually. Like I said, I never understood it. I mean I understood how much he loved the feel of sheer, silk stockings, I did too, but the look of a foot and toes I never understood... it was just one of his quirks, of which he had many.

For the first time I wondered if Xander had inherited his father's fetish.

I should note I buy my nylons online. At first I thought a stocking fetish was weird, but eventually I got into it, as it was hot seeing how turned on Ken would get just by my wearing nylons. So I got into the habit of wearing them every day. I researched the best kind. I discovered the variety of styles one could buy and bought them all.

I had a couple dozen pairs of thigh high stockings in a variety of colours and a couple even with the old school seam down the back for the slightly sexier attire or my friskier evenings with Ken.

I had three garter-belts (two black, one white from my wedding) and a half dozen pairs of normal stockings which I wore once in a while.

I had two pairs of crotchless pantyhose that I liked to wear to surprise him. He loved going down on me, and man was he good at it, so after he ripped a few at the crotch (wrecking expensive pantyhose) I thought ones with the crotch already missing was a good investment. Plus going commando was a fun naughty secret at work, at home or out and about. I was a natural redhead and I'd always kept my auburn pubes neatly trimmed for Ken, a practice I'd continued after his death, I guess just because it made me feel sexy.

It was also as we put up the Christmas tree that I noticed something else... my son looked a lot like my husband.

I mean I'd always acknowledged they looked similar, but now that he was eighteen, growing from a teenager into a young man, he really resembled his father.

Anyway, we decorated the tree, while Trapped in Paradise played, and then I made hot chocolate and we sat down to watch Home Alone.

We sat on the couch side by side, with my nylon-clad feet in full view for my son, who was clearly distracted by them. I don't know why this flattered me, but it did. I wiggled my toes every now and then; I moved one foot to rub the other.

I noticed him slyly adjust himself on more than one occasion. And perhaps it was the fact that I was unexpectedly single after more than two decades of marriage, but it felt nice to be noticed.

I do know I'm still attractive. I get hit on at work often; I still have a firm body from working out regularly, as I'm expected to look good for the clients in the office; I was a cheerleader in high school and college, so I'm very flexible with only mid-sized breasts, but great legs and ass.

When the movie was done, Xander said he was tired and was going to bed.

I suggested we take a picture together to send to his brother and sister. I set the phone up, pressed the timer and we posed.

I couldn't help but notice and feel the tent in his pants when he stood up. I also felt his cock flinch against my thigh as we posed together.

I wondered if he was going off to bed so he could jerk off.

I smiled, thinking he likely was, and I wondered if he'd masturbate about me. Then I shook my head at the inappropriate thought. Clearly having no sex in months was getting to me. Actually, truth be told, I hadn't had an orgasm since Ken's death. I hadn't wanted to. Yet, for the first time in months, my pussy was itching for some attention.

So while I was positive my son was jerking off, I thought I'd join him, kind of, and I went to my own bedroom, got undressed, except for my thigh highs, and pulled out my long-neglected vibrator. I cursed as the batteries were dead. I threw a robe on, went down the hall to my office to grab some fresh batteries, and on the way back, curious, I paused outside my son's closed door.

I heard a girl moaning. I knew there wasn't a girl in his room. He was obviously watching porn.

I smiled. Fortunately for him (and for me) I wasn't one of those mothers that thought sex was a bad thing, so long as nobody was taking foolish risks with their health or an unwanted pregnancy.

I was about to continue back to my room when I heard my son moan, "That's it, Mom, suck my big cock."

I gasped. Luckily his door was closed, and the porn was too loud for him to hear me.

But those words had me frozen in my tracks.

So although I knew it was wrong, I eavesdropped on my son as he listed a litany of sexual naughtiness, and all of it about me. "Take my whole cock in your mouth, Mom... Give me a nice nylon foot job, Mom... Bend over so I can fuck your tight cunt... Ride my cock, Mom... Spread those ass cheeks apart for my fat cock... I'm going to come all over your pretty face, Mom," and finally as he groaned, obviously coming while fantasizing about me, "That's right, take my load, Mom!"

Although I knew I'd gotten him all horny with my nylon clad legs and feet, hearing my sweet, nerdy son talk about me so sexually was shocking.

Equally shocking was the fact that my kitty was leaking down my leg.

I scurried quietly back to my room, closed and locked my door, tossed my robe carelessly on the floor, grabbed my long-forgotten suction cup dildo from my college days when I would fuck myself when I had no guy around, put it on the wall, backed up and furiously fucked myself to an orgasm in under two minutes, an orgasm that felt unlike any I could recall (although it had been a long time since I'd had one).

As I lay there in the afterglow of pleasure... a rush of guilt hit me.

I had teased my son.

I scolded myself and got ready to bed, knowing I had to be a much more proper woman and mother.

.....

The next morning, Xander having gone to school, I showered, and cleaned the house.

When I got to his room and made his bed (why could no kid ever make his own bed?), I noticed two things: a stain on his bedsheets that was obviously cum, and a pair of my soiled panties stashed under his pillow.

Last night came flashing back and before I knew it I was flipping open his laptop. He was so trusting that I'd never invade his privacy that he didn't even have a password.

I knew I shouldn't, but I did.

I searched his browser history to discover he went to quite a few porn sites. He also liked a story site called Literotica.

I then noticed he'd saved some scenes and had filed them in categories. He even had one section called "Top 10." Figuring this was his go to stroke material, I clicked on it and being somewhat of a pragmatic person, I started at ten and went to one.

Ten:

This was a lesbian scene where two girls tried to convince a beauty pageant judge to pick them as the winner by turning her into a submissive DP slut.

I'd never been with a girl, but the scene was very hot and the nasty talk as the girls dominated the pageant judge did get me a bit wet. I could never explain it, but I liked it rough and I liked name calling. Ken and I had needed to tone things down considerably once we had kids in the house, but whenever we had the chance, we loved getting down and dirty while he spewed sexy abuse at me and treated me like the dirty slut I loved being for him.

I had also liked being called and even acting like a cum slut back in my wilder college days (I even served once as the canvas for a fifteen-guy bukkake back in college at a sorority slut challenge).

Also, the scene reminded me of the high-stakes reality of beauty pageants which I'd been involved in from age six until sixteen. And although I never blackmailed a judge, I did often wish I could put them in their place.

I ended up watching the entire scene, over twenty minutes, imagining my doing that to the judge who gave me low scores at the state finals which had resulted in my finishing second. I quit entering pageants after that.

Nine:

I wasn't surprised to see a porn scene with a medieval theme, even though I also noticed even this scene had nylons in it (obviously my son did have the same fetish his father had).

I only watched a little of it as it wasn't my thing. I then realized I hadn't known I even had a thing for porn.

Eight:

I discovered in the next couple of videos a couple of things: first that my son liked shemales; secondly that I too found shemale porn was kind of hot. This scene was about a cheerleader who's turned into a cock hungry slut for a nerd she bullied. Watching the nerd girl reveal her massive cock and the look on the cheerleader's face likely matched my own, since it was massive. I couldn't explain it, but I found seeing a cock on a female body incredibly attractive.

I'd never been with a girl, since I loved cock way too much and had never been intrigued by a vagina. I mean I was very fond of my own, and understood the complex pleasure it could receive, but I wasn't at all interested in tasting somebody else's.

On another hand, a female with a cock was a different idea. I loved the female body and I loved cock. It really was the best of both worlds... hypothetically, anyway.

Seven:

Another shemale scene. This one was just oral, as a sorority senior puts a freshman in her expected place all first year... on her knees with a shemale dick in her mouth. The idea of a shemale sorority with pledges whose purpose was to suck and get fucked was pretty hot. It's a sorority I definitely would have joined.

I watched this entire scene too. For one, I'd been a cheerleader in high school and college. For two, there'd been a freshman in my senior year who looked almost identical to the nerdy shemale in the scene. Shit, if I could have had a live-in cock in college, that would have been the ultimate dream. Boys were exhausting... but a soft, curvy freshman with a big cock to use whenever I had an itch, would have been amazing.

Six:

Another shemale scene. I was beginning to wonder if this was supposed to tell me something about Xander. Was he secretly gay? Or did he just like the taboo of it? This scene was one where a princess from another kingdom was sent to the queen as a gift where she services the shemale queen and her shemale subjects.

The scene was surprisingly hot with dialogue that was actually believable. I watched the entire scene as the queen was clearly in charge, yet she trained her new gift in a compassionate way. It really had me revved up. I had to use all my willpower not to pleasure myself as I kept watching the scenes that turned my son on.

Five:

The next favourite scene really intrigued me. The title was 'Anal Mommy-Slut in the Kitchen', which wasn't much of a title, but it clearly let me know what it was about. The dialogue was terrible, but the essence was the mom hadn't made supper, so the son decided to fuck her for punishment. There was no vaginal intercourse in this scene... just hard anal and a rather impressive cum shot where the guy shot almost half a dozen ropes onto his fake mother's cunt, blouse and face.

I know the scene should have been disturbing, but it too kind of turned me on. A son who just takes what he wants? A son who sees through his conservative mother and turns her into the cock slut she secretly craves to be? A son who has a huge cock and can give his mother pleasure like she didn't know existed? What's not to like, at least in fantasy?

Four:

Another incest scene with a mother being triple teamed by her three sons. In college I'd been tag teamed a few times, loving the rocking motion of a cock in both my pussy and my mouth. That said, I'd never been triple teamed. I had taken a cock in my ass a couple of times in college, both times while I was quite intoxicated, and really enjoyed it in my inebriated state but never had considered doing it while sober... until now. I found myself musing, Unfortunately, I only have two sons... well, I also have a daughter who could wear a strap-on!

Shit, what was happening to me? Clearly I needed a real cock soon if I was thinking about getting triple-teamed by my two sons and my daughter.

Of course the fact that last night I'd teased my son relentlessly with my nylons, then later masturbated while I imagined being his mommy-slut, and was right now poking through his smut collection, already had me crossing the line big time.

Followed by the epic bukkake ending where I flashed back to my own cum coated face all those years ago.

Three:

This one began as a simple scene of a female teacher hitting on a male student until a girl walked in and gasped: "Mom?"


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