The Terror of Option

Summary: 18-year-old helps a GILF and gets a special Christmas present.

-x-X-x-

"Derek, are you busy right now?" Mom asked as she walked into my room in the basement.

I was playing basketball online, which meant I was. It also meant Mom would think I was too, fortunately. "In the middle of a game," I said.

"How long until you're done?"

"Ten minutes," I said, watching the other team score an easy layup on me.

"Come see me when your game is over."

"Okay." I nodded, taking the ball up the court.

She left.

Me and my anonymous teammate won by three and I headed upstairs a few minutes later.

Mom was decorating Christmas sugar cookies, my favourite.

"I need a favour," she said, without looking up from the delicate work of making a Santa cookie.

"To eat these?" I asked, taking one and biting into it.

"Hey, I just made that!"

"And I just ate it." I shrugged and swallowed the rest. Nothing better than a warm cookie.

"Fine," she sighed, "I made them for you anyways."

"It's why you're the best mom ever."

"Is that the only reason?"

"Well, one of three," I joked.

"You're such a brat."

"So, what did you call me up for?" I asked. "Besides these delicious cookies."

"I need you to go pick up Mrs. Barnes and drive her out to get a Christmas tree," Mom said. "Then take it back to her house and help put it up for her."

"Oh." That was not what I was expecting. Mrs. Barnes lived across the street. She was a sweet old lady in her early sixties, who used to babysit me when I was young.

"With the snowstorm out East, Gwen and Hannah won't be here for at least a couple of days. She's upset about not having a tree up yet."

"Okay." I nodded. "I think I can fit it into my busy schedule."

"Can you go now?"

"After one more of these," I said, snapping up the cookie she'd not even finished decorating.

"Hey!" she called after me as I walked away. "I wasn't done with that!"

I changed out of the shorts that I always wore when Mom was cooking and the house was hot. Instead, I pulled on sweats and a long-sleeved shirt, grabbed my toque, mitts and jacket and headed out.

I drove the truck across the street and went to get Mrs. Barnes. It hit me that she must be pretty lonely living all by herself since her husband died a couple of years ago.

"You are such a sweet boy," she said as I led her to the truck.

"It's the least I can do," I said. "You put up with me in my terrible twos."

"You were a terror," she said with a smile and a soft laugh as I opened the door and assisted her in. She was a bigger woman. I imagined she was a stunner when she was younger, and she was still very pretty even at sixty. Plus, her daughter and granddaughter were absolute knockouts.

I'd had a couple of jerkoff sessions thinking about her granddaughter Hannah, who was a year older than me, and plenty thinking about Gwen - yes, I have a thing for older women. Truth be told, I'd had a few inappropriate fantasies about Mrs. Barnes as well.

"Well, I've kind of grown up," I joked.

"You've turned into a very handsome young man." She was always so sweet.

"Thanks," I smiled, knowing that it wasn't really true. I wasn't very popular at school, and at eighteen I was still a virgin. I mean, I wasn't a troll or anything, but a solid six, outside seven. I'd been working out the past couple of months to balance my academics. "I just have to get the girls at school to think that."

I closed the door, walked around to the driver's side and climbed in. It would be a short ride: the tree lot was only a few minutes away.

As we drove off, she said, "High school girls are brainless if they don't see what a great catch you are."

"Well, I guess they must be pretty dumb." I smiled again.

"Then they don't deserve you," she said, placing her hand on my leg and patting it twice.

"Thanks." I remembered that Mrs. Barnes was always very touchy-feely. "I'm planning to go away to college in the fall. So I don't really want a girlfriend anyways."

"Oh, just a friend with benefits?" she asked.

Caught off guard, I coughed. "Wh-wh-what?" I stammered.

"I'm up with all your teenage lingo," she said. "I was young once, too, and had one or two friends with benefits of my own."

I'd barely managed to get my previous coughing fit under control, and now this! "Mrs. Barnes!" I said when I could breathe again. Still, I managed to inject a playful tone. Her words surprised me, and yet they intrigued me as well.

"Call me Mary. 'Mrs. Barnes' makes me feel a hundred years old."

"Okay," I agreed. "Mary it is.".

"Also," she continued with a slight sigh, "I might not look like it now, but I was quite a looker in my time."

"You're still very pretty, Mrs. Barnes - I mean Mary." I meant it. She had a great smile and intoxicating blue eyes, and her full body showcased all her curves even at sixty.

Not that I was about to let her know I'd had a few jerk-off sessions about her full-figured body. I mean, I only watched MILF porn, and occasionally GILF porn, and I liked a woman with some meat on her bones. I couldn't stand the anorexic look of so many of my classmates.

"You're sweet, but I'm nothing like I used to be," she said with what sounded like a sigh of reminiscence.

"Mary, you're a beautiful woman," I said as we rolled up to a red light. "And your body is healthy and one of a good life lived."

"Oh, Derek, that is the sweetest way to describe me. You really are a sweet boy." She smiled, again resting her hand on my leg. This time she gave it a squeeze and a brief caress before removing it.

I was sure it was just her being sweet. Like I said, she'd always been a touchy-feely woman, like the hug she'd given me a few minutes earlier at her front door. Even so, the brief caress woke up my dick. It was rare that I was ever touched by any girl or woman I wasn't related to.

"I mean it," I said, hoping for more sweet acknowledgement. No matter how innocent, it would likely fuel my late-night self-pleasuring. "You have a woman's body, not like most of my skinny classmates."

"I was once a skinny classmate," she said as the light changed and I started driving again.

"I imagine you were just as beautiful then as you are now." I was doing my best to make her feel better while subtly trying to adjust my dick.

I was beginning to see Mary as a GILF. She was even wearing pantyhose, I realised, letting my eyes drop to the mocha nylons that covered her legs. Pantyhose were my fetish, though I had no idea why. I just found them sexy, and while almost no one my age wore them, many older women did - especially GILFs. So many GILF videos included nylons.

Apparently my attempts to adjust my now hard dick weren't quite as subtle as I hoped because Mrs. Barnes looked right at what I was doing. Her eyes widened a little, but she didn't say anything.

After a brief silence, she said, "I was a cheerleader, prom queen and all that high school drama."

"That makes you the first cheerleader I've ever had in my car," I joked.

She laughed just as we reached the tree lot.

I helped her out and put my arm around her waist to steady her on the uneven terrain. Snow began to fall during the twenty minutes we spent looking at trees. Once she'd picked one, I helped her back to the truck and got one of the workers there to assist me in loading the tree.

On the drive back, Mrs. Barnes said, "Thank you so much, Derek. You're such a gentleman." Again she placed her hand on my leg and gave it a squeeze. This time, she added a slightly longer caress.

"You're welcome," I said as she moved her hand away again, "I'll do anything for you, Mary."

"That's so kind of you.".

"I mean it," I said, trying to find the right words that would get her hand back on my leg. I was surprised by how good it felt, how much it turned me on.

Still, I was eighteen. A virgin. Kissed two girls. Went down on one. Had one hand job. It was only logical that such simple, probably innocent, touches excited me.

"Well," she replied, "I could use some help putting the tree up and decorating it, if you have the time."

"I'm free all day." Mom had already instructed me to help her anyway.

"You're just so sweet!" Her hand returned to my leg, this time just moving up and down for a few delightful seconds before she patted me and withdrew it again. "It will be nice to have some company. I've been quite lonely without Jack."

"I'm so sorry about his passing. He was a great man," I said, and I meant it.

"Yes, he was a wonderful husband and father," she said with a nod, and an air of sadness filled the truck.

"So, when are Gwen and Hannah coming home?" I asked to break the uncomfortable silence.

"In a couple of days, if the storm lets up," she said. "Although who knows, really? It's quite the storm."

"Yeah, they're calling it the storm of the century." I'd watched the news and seen over four feet get dumped on the Eastern states.

"I hope they can get here in time."

"I'm sure they will," I replied, trying to sound reassuring. Then, sure that Mom and Dad would be fine with the offer, I added, "And otherwise you can definitely spend Christmas at our house."

"You really are a sweet young man," she said again, and her hand once more went to my leg for a slightly longer tender caress before withdrawing. "It's really a shame no young lady has scooped you up yet."

"No, it's you who is sweet," I said, fighting the temptation to move my own hand to her leg.

"I mean it," she said. "You're a very handsome young man."

Once again her hand went to my leg, and this time it lingered. "You deserve a woman who knows how to take care of you."

"That's the dream," I joked as she gave my leg a firm squeeze before moving away again.

My dick was raging in my pants and I again had to adjust it. This time I was sure Mrs. Barnes noticed, and smiled.

Unfortunately, we reached her house then and it was the end of the surreal... flirtation? Was Mrs. Barnes flirting with me? I mean, I knew I had trouble reading girls, but I was sure there was something going on here... Yet I was equally sure I was misconstruing this.

She was over sixty years old, after all. I was eighteen.

So I helped her out of the truck, offered her my arm and led her into her home.

Once she was safely inside, I went and grabbed the tree and brought it indoors. Mrs. Barnes already had a tree stand out so all I had to do was put the tree in place.

"Thank you so much," she said as she looked at me and the tree.

"You're welcome," I said, glancing back at her. Now I really got a great look at her not dressed in winter attire. She was only maybe five foot four. She had very large breasts and thick hips, both things I liked in a woman. She'd taken off her boots, and through the beige nylons I saw to my surprise that her toenails were painted red. The splash of colour added to the sexiness of her feet, which were small and delicate. Somehow I'd never imagined her painting her nails. Looking at them now, though, I felt my dick hardening yet again after the brief reprieve while I set up the tree.

"What do I owe you?" she asked.

"Nothing," I replied, looking into her blue eyes.

"That's silly. Your time is worth something."

"I'm serious," I told her, "I'm having fun spending time with you."

"Really?" She was clearly surprised by my words.

"Yes, really," I said, noticing her vulnerable expression, the grey in her long black hair that somehow added to her faded beauty. "So, where are the ornaments and lights?"

"In the basement."

"Show me where and I'll bring them up and help you decorate." I glanced down again at her adorable cute manicured pantyhose-clad toes.

She led me down to the basement and pointed out the boxes. I grabbed the first and made two more trips. By the time I was done, she'd already started to decorate the tree.

Putting the last box down I asked, "What can I do?"

"Can you help me wrap the lights around the tree please?"

For the next thirty minutes or so we decorated the tree. Mrs. Barnes put on some Christmas music, and we sang along to classic tunes.

When we were done she said, "Wait here," and headed into the kitchen.

She came back a few minutes later with cookies and hot chocolate. We sat down, she on the couch and me in an armchair opposite her, and she put her stocking-clad feet up on the coffee table.

Sitting across from her, I sipped on the hot chocolate and admired her silky soles all the time. Just like I couldn't explain my fascination with nylon-clad legs and silky sheer toes, I was also attracted to the silky soles of a woman's foot - yet somehow a woman's bare soles did absolutely nothing for me. I know, I'm a weirdo.

After a few moments of silence, she said, "I'm so thankful for your help."

"No problem," I replied, dragging my eyes away from her soles, "it was fun."

"It's been pleasant to have company," she said, moving one foot over the other.

"Well, I can't lie. It was a nice break from playing video games. I need to get out more."

"Me too," she sighed. "I don't get out nearly as much as I should."

"Me neither," I said, "I mean, when I'm not at school."

"So you really don't have a girlfriend?"

"No." I said, then added, "I've never really liked girls my age." I thought I'd at least try to plant the seed, even if I was sure it wouldn't go anywhere.

"Oh, no?" She wiggled her toes as if she could sense my distraction.

"I mean, I don't have any real experience with women of any age," I admitted, "but girls my age don't do much for me."

"You're not gay, are you?"

"No, no, no," I quickly stressed. "I like girls. I mean women."

"Women?" She readjusted her feet, putting one on top of the other and then changing them back.

"Well, I'm just attracted to older women."

"That's interesting," she murmured.

"I just find girls my age shallow and immature." It was the truth. Sure, I'd love to get a blow job or get to fuck one of the cheerleaders, but usually I masturbated to the teachers.

"I see," she said, seeming to ponder my words.

"Yeah, and truth be told, I am attracted to a woman who isn't going to blow away on a windy day," I added.

"Well, it would take a tornado to move me," she joked.

"Mary, you are an absolutely beautiful woman," I repeated. I realized I'd keep repeating it until she believed it herself.

"You're too kind," she said, rising. "Wait here. I have something to show you."

I adjusted my hard dick before she returned with a photo album in her hands. "Come sit beside me," she said, sitting back down on the couch.

"Okay," I said, getting up and joining her.

"This is me in high school," she explained, flipping open to a page of her in a cheerleader outfit.

"Wow!" She looked absolutely gorgeous.

"I know," she said, "I used to be quite the looker."

"Mary, that's enough." Her nylon-clad knee had been revealed as her dress rode up when she sat, and I placed my hand on it. "You're still a beautiful woman."

"Except twice the size." She didn't move my hand off of her leg.

"And just as beautiful."

"Do you really think so?" She looked completely vulnerable.

"Yes," I replied, my hand still on her leg. "You've aged gracefully."

"It's been a long time since I got a compliment," she whispered, her cheeks a little red.

"Well, here are some more," I said. "You have amazing blue eyes a man could drown in."

"Thanks."

"You have a beautiful full-figured body," I continued.

"Well, it's full-figured." She laughed awkwardly.

"And beautiful," I stressed, giving her knee a soft squeeze. "Plus, unlike girls today you wear nylons, which I have to confess make your legs and feet look super sexy."

"I thought I noticed you admiring my feet."

"If you were my woman I'd worship them," I said, my naughty fantasies leading the way.

"And what would worshipping my feet entail?"

I looked up, surprised at how far I'd dared to go. "Sorry, sorry!" I apologized, "I've been way too forward."

"No." She closed the photo album and placed it beside her. "Perhaps I haven't been forward enough."

She turned her body and swung her legs onto my lap. "Would you be a dear and massage my feet? They're a little sore."

"Sure," I breathed. Her nylon-clad heels were resting right on my hard dick as I moved my hands to her feet.

"Thank you," she said, letting out the softest of moans. "Jack used to always massage my feet."

"He was a lucky man," I said.

"Lucky?"

"Yes," I said, enjoying the soft silky sensation having wondered many times what feeling a woman's legs and feet in nylons would feel like. "Every woman deserves to be catered to."

"You're going to make some woman very happy," she smiled.

"Maybe one day."

"Trust me, once you get out of high school and the cesspool it is and join the real world, you'll be a great catch."

"I look forward to such a time," I said. I mean, I was an average-looking guy. Not ugly, not hot; not skinny and not fat. I just didn't fit into the cliques of popularity. I was too smart to be cool at a school that celebrated football championships, not academic bowls.

"You're going to turn into a handsome man," she continued.

"Thanks." I was flattered, but her words made me a little uncomfortable. I wasn't used to compliments.

"I mean it," she went on. "If I was forty years younger, I'd be all over you."

I laughed awkwardly and moved my hands to her toes, massaging each one individually. Finally, I replied, "And if I was a little older, I'd be all over you."

"Would you now?" she murmured.

"In a heartbeat," I said firmly as I finished her fifth toe on her right foot.

"Why?" She clearly meant it.

"You're a real woman, a beautiful woman." I switched to her other foot and began massaging her sole.

"How so?" She seemed to have forgotten the compliments I'd given her earlier.

"I don't want to objectify you," I protested.

"Please do. I haven't been objectified in a long, long, long time."

I laughed. "Truth?"

"Yes."

"Well, besides your intoxicating eyes that I already mentioned, and the fact you wear nylons, which are my fetish," I began, but halted as she bent her knee and moved her other foot to rest directly on my dick. Maybe it was on purpose, maybe by accident. Either way, it was distracting.

"Go on," she said in a slightly sensual tone.

Her entire sole was resting on my dick. I let my dick twitch against it. If she noticed, her face betrayed no reaction.

I swallowed and went on. "You have very pretty toes, and they're perfectly manicured." I glanced down at the foot resting on my aching dick.

"These toes?" She asked, wiggling them.

"Yes." I let out a small groan as her wiggle caused a slight wave movement along my cock.

"I painted them just yesterday, for the first time in months."

"Well, trust me, they look amazing!" I meant it. "Especially with this shade of nylon."

"I'm flattered," she said, and then asked, "Anything else?"

"You sure? I really don't want to offend you."

"I need this, Derek." Her tone made it clear she did.

Well, if that was what she wanted, I was very willing to give her all the compliments I could. "You have voluptuous breasts, wide sexy hips, and an amazing ass," I rattled off quickly before I could change my mind.

"Derek," she said, moving her foot slightly on my raging rod, "you have no idea how much I needed to hear those words."

"And I meant every word." I moved my hands to her toes. "You're a beautiful woman inside and out."

"You sure you don't have a harem of women wanting you?"

I laughed, and then not even sure why, I muttered, "I've never had sex."

"Never?" There was surprise in her voice, and perhaps a hint of concern.

"Never," I admitted, a little embarrassed after her shocked reaction.

"A blow job?" she asked. Her question almost took my breath away.

"No."

"A hand job?"

"Once," I replied sheepishly as I finished her final toe.

"Well," she said, her foot again sliding over my crotch, "good for you for waiting for the right person."

I laughed. "That's one way to look at it."

Her foot seemed to drag ever so slowly over my hard dick, before she swung her legs off and rose from the couch. "I'll be right back," she announced.

"Okay," I mumbled, embarrassed at revealing my virginity situation. More importantly, I was disappointed that I'd screwed up the thrill of massaging her feet and feeling her foot resting on my dick.

A few minutes passed before I heard her return. She didn't come into the living room, but instead stayed outside the door and said, "Derek, close your eyes and stand up."

"Uh, okay." I did as requested, even though I was worried that the bulge of my hard cock would be obvious. The sweats I was wearing weren't the best for covering up a raging erection.

A dozen seconds later, I heard her voice again, sounding closer now. "Open your eyes."

I did and gasped.

Mrs. Barnes was standing before me in all red lingerie, with panties and stockings that were held up by clasps. A Santa hat on her head completed the outfit.

"Merry Christmas, Derek❤," she said, covering the three feet that separated us and reaching out with her hand to my crotch. "Is this because of me?❤"

"Yeeeeeees," I moaned, astonished at this sudden turn of events.

"Is this my Christmas present, Derek?❤" she breathed, slowly rubbing my dick through my sweats. I loved how she repeated my name. It felt sensuous.

"S-s-sure," I stammered, bewildered by what was happening, even though it was literally a dream come true.

"I'm not being too forward, am I, Derek?" Her hand continued to glide slowly over my hard-on. "I don't want to be presumptuous and assume you want this."

"I do... I do want this!" I said and then added, "Very badly."

She smiled, then, leaning in, pressed her lips against mine.

I'd kissed girls before, two to be exact, Sandra and Jamie, but this just seemed more real. Raw. Intimate.

I kissed her back, feeling her hand slip inside my sweats and underwear to my throbbing dick.

She slowly stroked me and rolled her fingers over my cock head. Her touch was like magic; like nothing I'd ever experienced.

When she broke the kiss, she lowered herself before me, tugged my sweats and underwear down in one smooth pull. My six-and-a-half-inch dick (I knew its precise measurements) popped out.

"What a lovely dick❤," she purred, taking it in her left hand before leaning forward and wrapping her lips around it.

"Oh my God," I moaned. I watched wide-eyed as she slowly engulfed my dick. You can imagine what a blow job would feel like, but nothing can prepare you for the amazing sensations of actually getting one.

"Mmmmmmmm❤," she hummed, bobbing back and forth on my dick while I watched in complete disbelief.

Unfortunately, it probably wasn't even a couple of dozen bobs, with my entire length inside her mouth, before I knew I was going to come. I managed to croak, "I'm... going... to...."

She let me slip from between her lips and murmured, "Come in my mouth❤, baby. I need your cum so bad. It's been so long❤." Before I knew it, she was sucking my dick again.

She switched from long, slow sucks to fast devouring gulps, taking my whole dick in with each hungry movement. After only a dozen or so lip-wrapping strokes I couldn't hold back any longer, no matter how desperately I tried, and I grunted and shot my load in her mouth. It was easily the most intense and longest orgasm I'd ever experienced.

She didn't slow down. Instead, she swallowed every drop for a good minute longer before she pulled back. "Mmmmmm❤, I needed that❤."

"That was amazing," I breathed, basking in a daze of pleasure.

"I haven't had a cock in my mouth in a decade❤," she said. The look she gave me was surreal, a look of lust and satisfaction.

"Didn't Jack just die a couple of years ago?" I asked, then wished I hadn't. What kind of fool would want to wreck the mood of a once-in-a-lifetime experience by mentioning her dead husband?

"He had erectile dysfunction, and then came the cancer. Even with Viagra he couldn't get it up."

"I'm sorry," I said, looking down at her, still on her knees before me.

"It's alright." She shrugged and rose. "The past is the past."

Hoping that the experience wasn't over, desperate to make sure it continued, I moved my hands to her panties and rubbed her.

"You don't have to❤," she moaned. I felt the moistness seeping through her panties.

"Oh, but I very badly want to." I moved my hands to her hips and pulled her panties down, happy she was wearing them over the top of sexy seasonal garters.

Her entire body trembled slightly as I took them off and admired her hairy pussy. While I had limited experience with vaginas, I had a lot of experience admiring them in pictures and porn, and I'd always found a hairy pussy more visceral and visually appealing. The pussy almost wrapped up, I suppose like a Christmas present, in a forest of pubes.

I was tempted to lean forward and lick her right there, since she hadn't stopped me from sliding her panties down her nylon-clad thick legs. I wanted her to be comfortable, though, and rose again. "Sit down on the couch, Mary." It came out almost like an order.

"Very well❤" She sounded as if she was in a flustered daze too, not questioning me at all, though her cheeks were already blushing red.

She sat, and I slipped down before her. I grasped her nylon-clad legs and pushed them apart.

"I imagine you haven't had this for a long time either." I leaned forward and buried my face in her forested pussy region.

As I did, I discovered that her pubes were quite wet already, her scent unbelievably strong, exotic and captivating.

"Oh❤, Derek," she moaned, even before my tongue had parted the hairs and found her hidden peach.

"You smell absolutely heavenly." From my extensive online research, I knew that many women were insecure about their natural smell and taste.

"Oh❤, Derek," she moaned again. For an instant I simply briefly enjoyed being overwhelmed by her scent: so unique, so unlike anything else I had ever smelled. And much more present than the almost non-existent scent of the one girl I had orally pleasured. She had had very little hair on her pussy.

"Heavenly," I repeated.

"Please❤, Derek, lick me❤. I need it so bad❤." The desperation in her voice couldn't possibly be fake.

I wanted to make her happy, to give her pleasure she hadn't experienced in years. I wanted to return the favour of the amazing orgasm she'd just given me. Extending my tongue, I forced it through her forest and found her very wet pussy.

"Oooooooooh❤, yes❤!" she moaned the instant my tongue made contact. Her cry sent a rush of adrenaline through my body: not only was I eating the pussy of one of my fantasy MILFs, or rather GILFs, but what I was doing was working as well. That first moan had been louder than any sound Kate had made when I went down on her.

"Mmmmmmm," I responded and began to lick up and down between her pussy lips.

"That feels so good❤, Derek," she murmured, surprising me by raising her right leg over my shoulder.

"You're absolutely delicious, Mary." I wanted to assure her I was enjoying this as much as I assumed and hoped she was. I'd done plenty of research on women, on how to eat pussy, on how to best make a woman come, and I hoped my dogged efforts would overcome my limited experience to give her the orgasm she seemed to crave so much.

"Thank yooooou❤," she moaned, placing her other leg on my opposite shoulder. This gave me more comfortable access to her delicious pussy and let me go deeper with my tongue.

Following a tip I'd read in an erotic story somewhere, I began with the alphabet technique, simply recreating the alphabet between her lips. According to the story, the unpredictability of the movements created a wild pleasure that built up steadily.

It seemed to be working. By the time I was at ,she was moaning loudly, begging me, "Don't stop❤, Derek, don't stop!❤"

Of course I had no intention of stopping. I could have dined on this delicious delicacy all day and all night, wallowing in the amazing taste. The thrill of making a woman moan and gasp, especially Mrs. Barnes, had my dick hard again after only the briefest of rests.

At someime I felt her seize the back of my head. "Right there, right there..."

Figuring she was about to come, I didn't finish my alphabet routine. Instead I turned my attention upwards to her clit, sucking it into my mouth. The eruption this triggered was immediate.

Her ass lifted, her knees tightened against my head. A massive flood gushed from her onto my face and into my open mouth.

I lapped up her pussy juice like it was my last meal. I'd made this beautiful GILF come! A new rush of adrenaline coursed through me, rushing straight to my rock-hard cock.

"Fuck me❤, Derek," she pleaded, still gasping from her orgasm. The look she gave me was one of complete lust and arousal. "Do you want to fuck me?❤"

"I do." I nodded happily, looking up at her. I could see the desperation in her eyes. "I want it so badly."

She lifted her legs from my shoulders. "Fuck me from behind❤."

I rose, tearing off my shirt,

"Oh my❤," she murmured, "that's quite the chiselled chest❤." She stood as well and took my left nipple in her mouth.

I'd never known that nipples were an erogenous zone for men. Now, with her tongue flicking at mine and her lips sucking my nipple and areola into her mouth, I could only gasp, "Oh, that feels so good."

Her nylon-clad knee rubbed my dick as she went back and forth, giving each nipple attention in turn.

Suddenly she pulled away and spun around. Placing her knees on the sofa, with her hands on the back, she looked back at me over her shoulder. "Now, Derek, please shove that big dick into me❤. I need it so bad❤."

But I paused to admire her big back end, bent over before me. "Such a beautiful ass," I whispered, stroking her soft skin.

"You like my big fat ass?❤"

I squeezed both her big cheeks. "I love it."

"That feels nice❤," she said, rocking back and forth against my hands. "But I need that big dick in me so badly❤."

I was astonished by my own restraint. Mrs. Barnes was offering to take my virginity, and here I was, dragging out the moment.

"Just slide it in me❤, Derek," she pleaded. "It's been so long since I've been fucked❤."

"Not as long as it has for me," I joked nervously.

She spread her legs wider as I positioned my dick at her wet pussy lips and then slid it in. "Yes❤, baby❤, let me take your virginity❤," she moaned as I filled her up. "Oh yes❤, fuck me❤, Derek. Give me all that dick❤!"

"Oh my God!" The sensation of being inside a vagina was as exhilarating as being in a mouth, and yet completely different.

I still could hardly believe it. Not only had I just had my first blow job, now I was losing my virginity as well. For half a minute or so, still adjusting to the surrealness of it all, I moved in and out of her pussy slowly.

"Harder❤" she moaned, "harder!❤"

I placed my hands on her hips and pulled her against me, slamming into her again and again, loving how it felt as my thighs slapped against hers.

"Yeeeeeees❤!" she wailed. "Pound me❤ Derek, pound my pussy❤!"

"Yesss," I moaned. Hearing this sweet older lady talk so nasty drove me wild.

"Harder❤," she begged, "slam your body into mine❤"

I thrust away at her, grunting and gasping, for what felt like a lifetime. It was probably only a minute or so, though, before she reached round and placed a hand on my chest. I slowed, disappointed, wondering if I was doing something wrong, cursing myself for whatever it was.

But she pulled herself off me and clambered off the couch. "Sit," she instructed, gesturing. "I want to ride you❤."

Relieved, I obeyed hastily. She barely waited for me to be seated before she straddled me, grasped my dick and lowered herself onto it. Then she leaned forward and began to slowly grind up and down.

Being fucked this way was a very different sensation from when I was doing the fucking. Much as I'd enjoyed the view of her ass, now her massive breasts hung right before my face. "May I suck on your nipples?" I whispered.

"Please do❤," she said, as she tugged her bra down to free her breasts.

Almost before she was done, with the bra bunched up around her waist, my hands were grasping them, cupping them, squeezing them. I took a moment to wonder at how heavy they were before leaning forward and sucking one large hard nipple into my mouth.

"Oh yes, suck on my tits❤!" The words came out in a moan as her big body rose and fell on my dick in a smooth rhythm.

"So big," I breathed. Her tits left me reeling as much as any of the other wild acts I had experienced today.

"Play with them❤," she urged, pressing forward.

"I could do this all day." My mouth went from one nipple to the other.

"Be careful," she moaned as I squeezed and sucked. "I might never let you leave❤."

"I wouldn't want to." I was in lust of these tits, this body, this experience.

Then the whole world was just me going back and forth, back and forth between those two large tits with their hard nipples. I sucked. I swirled my tongue around them. I even slithered my tongue around and buried my face between the voluptuous mounds of flesh.

All this time she slowly ground on my cock. I was just happy to let her do as she wanted, but then I noticed that she'd picked up the pace. One foot was on the floor and she was lifting herself further off my dick before falling back. Her big tits bounced in my face like balloons of temptation.

I leaned back and watched her ride me.

I watched her facial expression.

I watched her body bounce.

"I want you to come inside me❤, Derek," she moaned. Her orgasm seemed to be approaching. "Will you do that?❤ Will you come inside me?❤"

"Yes," I gasped, "but I want to fuck you first. Lie down on your back."

"Yes❤, baby❤, tell me what you want❤." She clambered off of me and lay down on the floor and spread her nylon-clad legs.

I quickly got off the sofa and positioned myself between her open legs and quickly slid inside her. From this position her huge tits somehow looked even larger.

"Oh yes❤, Derek," she moaned. "Fuck me❤, fuck me hard!❤ Give me all that dick❤!"

I was in control now, and I discovered that I could go deeper than when I'd fucked her from behind. "God, you're beautiful."

"Thank you❤." She smiled, then her face became more earnest. "Now fuck me❤, slam that big dick in my pussy!❤"

What else was I to do?

I fucked her as hard and as fast as I could. Fucking was quite the workout, I realized. I'd started going to a gym the past two months, luckily, and was just beginning to get into good shape.

I thrust away at her until she ordered, "Grab my ankles. Pull my legs together❤. Lean on them and piledrive me!❤"

I was a little worried about hurting her in that position, but I did as she instructed. A moment later I was leaning on her strong nylon-clad legs and pounding her from this new angle.

Apparently this angle worked well, because this sweet grandma became wickedly verbal. Hearing her talk dirty made my balls boil, but I was determined to make her come before I did.

"Oh yes❤, Derek, pile drive my pussy❤! Fuck me❤, fuck me❤, don't you dare stop❤. Give me all that big fat grandma fucking cock!❤ Oh yes❤, hammer me❤, drill me❤, pound me!❤"

Sweat was pouring off me in this wicked unorthodox workout. "Come for me, my sexy GILF," I growled as I hammered, drilled and pounded her pussy.

"GILF?" she gasped. Her orgasm was close.

"Grandma I'd like to fuck."

"Oh you dirty boy❤," she cried, "then fuck your GILF~❤, give me all that fat cock and cum inside me❤."

"You first, my full-time grandma cum dump," I grunted with a smirk. Clearly I'd been reading too much erotica.

"Oh yes❤, Derek," she moaned, "I'll be your granny slut~❤, your grandma cum dump and your GILF fuck toy❤."

Her implication that this could be more than a wild one-time thing sent a shiver through me and made my balls boil with the imminence of my explosion. "I'll cum in this granny pussy, you sexy thing," I assured. Holding back was taking every fibre of my being. "I'll cum inside my grandma slut as soon as she cums on my dick."

A few deep strokes later she gave a scream and her body shuddered against mine. "Oooooh~❤, yes❤, Derek, I'll be your sluuuuuuuut!❤❤"

Only seconds later, triggered by the noises coming from her mouth, her declaration of being my slut, my own orgasm was released and I unloaded deep inside her.

"Just... fill me up❤," she moaned loudly.

"So good," I grunted, shooting rope after rope into her.

"So good❤," she agreed in a weak voice.

Both spent from our climaxes, so close together, we collapsed in a gasping heap.

After a moment I pulled out and helped her to lower her legs. Then I bent down and kissed her.

Tender and sweet.

After a long kiss, I helped her up and we sat on the sofa, still trying to catch our breath.

At last she said, "I meant what I said, Derek. Anytime you want to come over and fuck me❤, you're welcome to❤."

"I plan to take you up on that offer often," I assured her.

"You'd better❤," she said with a smile. "Now that you've reawakened my neglected libido I'm going to need a lot of fucking❤."

"And I always need it."

"I haven't felt like a woman for a long time," she whispered, resting her head on my chest.

"You're all woman," I began, when a sudden sound of the doorbell startled us both.

"Drat, who could that be?" she said, as I rose and took a careful glance out the window.

"Shit, it's my Mom!"

"Quick!" Mrs. Barnes hissed. "You'd better get dressed."

I hastily began to retrieve my clothes from where they lay scattered on the floor. "Go to your room and put something on over that outfit," I suggested, "I'll get the door."

"I suppose I should," she said with a cute giggle. "Your cum is leaking down my leg❤."

"There's more where that came from," I growled at her as I slipped on my sweats and hid my underwear under the sofa cushion.

Just as I was pulling on my shirt the doorbell rang again and I dashed over to open it.

"What took you so long?" Mom asked, walking in.

"I was downstairs putting a box away."

"Where's Mrs. Barnes?"

"In the washroom, I think." It was quite possible that she actually was.

Mom glanced around. "I was worried about you."

"My truck is outside, in the driveway. Where did you think I'd be?"

"You haven't been answering your phone," she said.

"Oh, uhm, maybe it's in the truck." I wasn't actually sure where it was.

"Perhaps. Anyway, why don't you see if Mrs. Barnes would like to come over for dinner today?"

"I'll ask her," I replied with a nod.

"The tree looks nice, by the way." Mom said, taking it in.

Just then I noticed a small spot of cum on the floor. "Yeah," I muttered, trying to rub it away without drawing Mom's attention. "She picked a great tree."

"Your son is an absolute gentleman." Mary's voice behind us almost made me jump.

"He sure is," Mom agreed, as we both turned around.

Mary was in sweater, pants and slippers, not even a remote trace evidence of our recent transgressions visible.

"Mom is inviting you for dinner tonight," I said.

"That would be lovely," Mary smiled warmly. "Will you have some hot chocolate now, though?"

"I'd love to, but I need to get home," Mom said with a regretful smile. "The chicken is in the oven."

"Well, I'll bring dessert," Mary said. "No, I insist," she continued over Mom's protestations, before adding with the slightest smirk in my direction, "I make a delicious homemade pie. I already have one ready that just has to be baked in the oven."

-x-X-x-

"Well then, thank you. That would be great." Mom looking at the tree again. "The tree looks amazing."

"Your son has been very helpful," Mary replied with a smile at me.

"Feel free to keep him for as long as you need. Work him hard."

"Oh, I will!" Mary and I shared a smirk behind Mom's back. "If he's willing," Mary continued, "I'd love to have him come by and help me with a few things over the next few weeks."

"Use and abuse him," Mom joked, turning to face us again. "It's good for him to get off his computer."

I was struggling to keep a straight face at all this innuendo, and Mary was faring little better.

"I'll work him to the bone," she told Mom, and my dick twitched in my sweats. Without underwear I wouldn't be able to keep it concealed for long.

"Well, son, you stay here and help Mrs. Barnes with whatever she needs," Mom instructed. "Just make sure you're home at five."

"I'll go and put the pie in," Mary said, heading for the kitchen. "See you soon."

I walked Mom to the door. Before she left, she turned to me and said, "Thanks for doing this. Mrs. Barnes really needs the help, and the company."

"It's been a blast," I said, still trying not to smirk.

"You're a sweet boy," she said, kissing my cheek and leaving. I headed for the kitchen.

Mary was already out of her pants, revealing the sexy lingerie underneath the quick outfit she'd pulled on to cover herself up. "Come get some homemade pie❤," she said in a throaty voice, sitting down on a kitchen chair and spreading her legs.

"Mmmmmmm." I knelt before her. "Is this you working me hard?"

"This is just the warm-up❤," she murmured with a smile as I began to lick a delayed cream pie from her pussy.

I got her off again with my tongue.

She blew me for a while.

I bent her over the kitchen counter and fucked her from behind, before coming inside her for a second time.

That night, at dinner, she spent the entire meal rubbing my dick under the table. When we'd finished eating, Mom insisted I walk Mary home. I was rewarded with another blowjob that ended with me shooting a load all over her face.

It was the best day and night of my life.

.....

Next day I took Mary for groceries, and then to a sex shop. We bought a couple of toys and some sexy costumes for her, including a slutty Wonder Woman outfit that she let me pick out for her.

When we got back to her house, as soon as we'd put the groceries away we fucked again, right there in the kitchen. She still had cum leaking out of her when there was a ring at the door.

"Who could it be this time?❤" she sighed as she grabbed her dress. We'd just been gearing up for round two. She hadn't worn any panties, but she was still in her bra and pantyhose - ripped from where I'd been eager to get to her pussy.

"I'll check," I said as I put my pants on. I was beginning to appreciate how convenient sweats were.

I went to the door, peeked through the keyhole, and felt my eyes go wide.

I darted back to the kitchen, "It's Gwen and Hannah," I urgently said.

"Oh dear," Mary said. "I suppose I'd better answer the door then. You take this box and go downstairs."

"Okay," I said, as the doorbell rang again.

"How do I look?"

"Hot." I groped at her and squeezed. "You always look hot."

"You're so sweet," she said with a wide smile and shooed me away.

I grabbed the box from yesterday and took it downstairs. When I returned a couple of minutes later, I tried to be casual as I greeted Mary's daughter and granddaughter.

"Derek?" Gwen asked.

"Derek has been helping me," Mary explained. "We did the Christmas tree yesterday, and today he's been doing some odd jobs around the house."

"She's kept me hopping," I added with a grin. I looked at Hannah and couldn't believe how much she looked like her grandma in the pictures from Mary's youth.

"Hi, Derek," she smiled, giving me a hug.

"H-h-hi," I stammered, taken aback by the sudden embrace by this hot girl who was a year older than me.

"Thank you for helping Mom," Gwen interjected as Hannah let go. "It was very kind of you."

"Oh, I'd do anything for Mary," I said, trying to sound offhand.

"Why don't you stay for supper tonight?" Gwen asked.

"Yeah," Hannah added. "I'd love to catch up."

I agreed, a little surprised that Hannah was so excited to see me. We'd been friends since we were very young, though not very close. I texted her on occasion to ask about Harvard; she went there, and I had the grades to perhaps get in too.

"Well, that's settled then," Mary said, smiling at us all.

-x-X-x-

[Epilogue]

Over the next week, I was at the Barnes place most of the time. I even managed to fuck Mary once, when Gwen and Hannah went out for some last-minute holiday shopping.

I spent a fair amount of time with Hannah too, and we connected in a way we never had before. We didn't have sex or anything, but we kissed. I felt bad about that, but didn't mention it to Mary until after Gwen and Hannah had flown back to Boston.

Mary smiled through my second load, which I'd shot onto her face after a marathon fuck session with her dressed as Wonder Woman which was wickedly hot.

She said with a soft sigh "I'm going to miss this."

"Me too."

"And this may sound crazy after all we have done, but I think you and my granddaughter would make a great couple."

"You'd be okay with that?" I asked, shivering. Her hand was stroking my dick. It was still hard, but definitely needed a moment to recover. Sure, it was a strange time to have a discussion about her granddaughter since she had my load all over her face and she was stroking my cock for one more round, yet this was just who she was caring and compassionate.

"Of course!" she said. "I'd love to have you eventually become an official member of the family."

Half an hour later, she gave me a stocking-clad foot job and I came all over her feet.

"She loves how you help me and she listens to me most of the time," Mary said, taking the stocking off and sucked the cum from it, "I'll be sure to put in a good word."

****

Five years later Hannah and I married.

Mary was in a wheelchair by that time, and I only saw her occasionally. We hadn't had sex since a marathon session during the summer, six months after the Christmas fortnight of seasonal joy. We fucked non-stop over a three-day weekend before I flew out to Boston. As a going-away present, she even invited me to take her in the ass.

We agreed not to let it go any further if Hannah and I hooked up.

Well, we did hook up. We fell in love. We got married.

Sadly, Mary passed two years later, just weeks before Hannah gave birth to our first child. It was a baby girl. Of course we named her Mary.

Love. It works in mysterious ways.

The end

-x-X-x-