Friend With Benefits With My Mom

CHAPTER 1

Jack:

My mother is a stone-cold fox.

She looks like a taller version of the adult film star Ashley Fires.

My mom, no joke, is her doppelganger.

She's 5'9, blond, with blue eyes, and has high cheekbones, a slim body, hour glass figure, long legs, succulent thighs, perky little tits, and the sweetest round apple ass...

My mom has always featured in my jerk off fantasies, ever since I hit puberty...

Now in my 20s, I still think of banging her, I admit.

Sort of a shame, really, that she's my mom. We get along quite well...

Sometimes I wish I could be with her, be closer to her, be intimate...

Vivian:

My Jack is such a sweetheart. He's such a caring, loving son. Always visits and calls, holds the door for me, helps me with housework. Constantly doting on me.

And the way he looks at me, even more so these days... Well, if I wasn't his mom, I'd think he was sweet on me.

Besides being a gentleman, what a strapping young lad he's developed into.

Why any girl would be lucky to have him. At 6 feet tall, 190 pounds, he's beefy and muscular and has wavy black hair, a strong square chin and almond eyes.

What a catch!

I can't believe that hussy of a girlfriend he had, Crissy, broke his heart and ran back to her ex...

Guess I'm not alone in the Broken Hearts Club!

Jack:

Recently my mom and I have gotten much closer. Being 26 now I can have more "grown up" conversations with her.

She's quite well-read and is a news junkie like me, so we talk a lot about world events, politics, and all sorts of stuff.

Like me, she also went through a recent break-up, with my dad.

I love my pops, don't get me wrong. He's a great provider and gave us a fantastic, upper middle-class life, big house in the suburbs, helped me get through college, got me my first job.

But he and mom, I never saw any sparks there. He'd be gone for months at a time, on business or wherever.

Can't say it surprised me when it turned out he had another family in another state! It did, however, shock and deeply sadden my mom.

At least he wasn't a jerk in the divorce settlement and set my mom up nicely. After her initial anger, a whirlwind of broken dishes and screaming in the kitchen, they parted on amicable terms.

She's been quite lonely ever since. I think she's been lonely, actually, for a long time.

Vivian:

It's been tough, yeah. As a young woman, I competed in beauty pageants, modeled, and was a genuine debutante.

When I met my husband, I was a junior in college, 21, and he was a 27-year-old entrepreneur, climbing business ladders.

We weren't careful and, after a couple months, I got pregnant and couldn't bear to lose my baby, so we got hitched, and I left school, abandoned my dreams- to help him reach his... and to raise our son.

I was so busy with parenting, PTA duties, and maintaining my figure, looks, that I didn't feel too lonely until Jack went off to college.

Without him around, with my husband there less and less, things have been just so...

Jack:

It's been sad. Sad to see my parents split up, of course. But also sad seeing my mom becoming a hermit, cat lady type.

She certainly doesn't look the part, though. At 47, she looks 37, mature, beautiful... I liken her to a fine bottle of wine or whisky, as she seems to get sexier, prettier, with age.

She's so gentle, and girly too. Always pays meticulous attention to her looks, in the gym nearly every day, doing aerobics, yoga, the StairMaster, the treadmill.

Love all her fishnet stockings and tight blouses and miniskirts, and her makeup, heavy rouge on her cheeks, mascara, and dark blue eye shadow, cherry red lipstick. Almost never see her without makeup.

Her long nails, always done perfectly, manicured, painted all sorts of colors... I gotta say I've had increasing fantasies about her recently since I broke up with my girl.

Sometimes I feel angry in a way, that she's my mom. Because she's so relaxed, fun, enjoyable to be around. And so hot...

The age difference doesn't bother me. It's more the barrier of her being my mom that bothers me. Like here's this amazing mature woman I want to be with, really be with, but it's impossible...

I can still enjoy her companionship. And since we're both single, alone, I've been visiting her more often, and she'll make me dinner (she's such an awesome cook!) and we'll eat her Mediterranean style dishes and sip wine, watch the sunset from the window in the dining room and talk about everything and anything.

If she weren't my mom, oh yeah, I'd totally make a move on her...

Vivian:

As tough as it's been, the divorce, finding my husband had another wife and family, the one benefit it's brought has been getting closer with my son.

He's been so sweet, coming over after work, for dinner, still dressed in his suit and tie. He looks so handsome!

So nice to have a man around the house to do things that need doing.

Speaking of that, well, it's not easy to talk about, but, I, well, miss, certain... Certain duties only a man can perform...

I've never been open about... sex. My husband was my first and the only man I've been with. When we were first together, the first time, it hurt like hell!

I wondered, why would people want to do this, sex thing? I'd always desired to do it, for some reason, then I did it, and it was soooo painful.

I almost didn't want to do it again, but I couldn't let such a catch go, so I let him have sex with me again.

And the second time, wow, was quite different. I loved it, feeling his...

How large and warm it felt, in and out of me, down there... His hot stuff all squirting in me, that second time, made me experience my first orgasm, something I'll never forget.

We took to doing it like rabbits after that. As soon as I got to his apartment, we'd be on the floor, the table, in the shower, the loveseat, bed, just going at it. He was wild, but gentle, patient, and taught me how to do everything he wanted.

I was sure he'd done it before, probably with multiple partners, given how handsome he was. But I never asked. Nor did I have the courage or awareness to tell him to stop and wear a condom...

I hope Jack is being safer than me... He's had a string of girlfriends but hasn't found the one. I wonder if he's looking...

Maybe he's not having any luck and that's why he's coming over to see me so much.

Maybe he's lonely too...

Jack:

I've been feeling lonely since I broke up with Crissy. Holy shit, she was fine! She looked like a Kardashian, seriously, Armenian, with an angelic face and big bubble butt.

We used to fuck, and I mean, FUCK, constantly.

She was the first girl I really could give it to hard and who'd do anything, deepthroat, anal, even a 3-way with her Finnish blond friend.

Fucking Crissy was like being with a pornstar.

Before her I'd dated several girls, but they were mostly spoiled, prudish types. Most wouldn't let me go all the way, and, if they did, they didn't like the sex, and complained about my dick being too big.

Not that I have a massive, Ron Jeremy dick, but I guess it's slightly above average, 7 inches, thick. I keep it manscaped, too, so it sorta looks big. I'm proud of it, I admit...

With Crissy sex was finally fun. We also got along well. Sounds kinda sick, I know, but Crissy's personality reminded me of my mom. Laidback, fun, knowledgeable, could talk about anything.

I was totally heartbroken when she got back together with her ex, this muscle-bound Greek guy, a former Olympic swimmer. But I've been using it as motivation. Hitting the gym more, trying to get into the best shape of my life so I can bag a superhot chick.

However, every time I think about what I want in a woman, and every time I beat off these days, I think of only one person, my mom.

Vivian:

It's so hard to find someone. Everybody is so narcissistic, always on their phone, social media, ignoring each other.

My girlfriends have been encouraging me to get on a dating site or app or Tinder or Snapface or whatever it's called, but I'm so out of the loop with all that.

I don't even know how I would date. So many guys my age don't take care of themselves physically or are recently divorced guys looking for younger women to have flings with.

It's been years, decades, since I went on an actual date. I guess Jack coming over for dinner is the closest I'm getting to male attention.

Isn't that awful to say, that I'm basically dating my son?

Look, it's not like we're doing anything wrong. We just have dinner, drink a little wine.

But when he comes over, he always gives me a hug, and when we hug, it's like I feel this electric shock. I get all tingly. I get goosebumps.

And it's like... when we hug... as if I don't want to let him go. I don't know what's coming over me. I shouldn't feel like this. It's so wrong. Isn't it?

He's a grown man, nearing 30. I... I don't view him as the little boy I used to... It's like he's something else now, entirely...

Last night, too, when he slept over, well, that shouldn't have happened...

Jack:

My visits to mom's house have increased a lot, to almost every night.

I live close enough that I can stop by on the way home from work and walk home if I've had too many glasses of wine.

My sales job is intense and requires me to work practically every day. Not helpful for the social life, but it certainly helps my bank account. Not too many guys my age making the cash I make.

But yeah, I've been getting tired of eating at restaurants and trying to cook, and my mom makes such healthy, delicious food so it's been quite a good thing going by there for dinner.

Not just the convenience and food, though, it's also about seeing her.

Going by there, I'm always looking forward to her welcoming smile and big beautiful blue eyes lighting up when she sees me, feeling the warmth of her tight hugs, her soft body touching mine, coyly watching her as she walks away, to ready dinner...

Yeah, I get more out of it than just the food...

But last night, things took a, shall we say, different, turn...

I'd been working overtime so I got there later than usual. It was a Saturday night, and, for once, I wasn't working the whole weekend.

We finished dinner around 9pm and drank wine and talked until around 10pm.

I honestly can't remember who suggested it, since I was sorta buzzed, but we agreed I'd stay the night since it was late and I was tired.

I do remember we decided to watch a movie in the living room.

It was some scary movie about a doll. My mom and I both like scary movies, and find them more funny than anything, but this one, maybe because of the creepy doll, really freaked my mom out.

We were sitting on opposite ends of the u-shaped leather couch, but, upon watching a scene where the doll suddenly appears in a closet holding a bloody knife, my mom screamed and slid over next to me, threw her arms around me and clutched me closely as we watched.

Oh fuck, the smell of her hair and feeling it on my cheek, was... indescribable. I put my arm around her and held her like I hadn't held a woman in a while.

Soon enough, maybe through instinct, perhaps due to the wine, I was caressing her arm and slowly worked my hand down, stroking her velvety, pantyhose covered thighs.

Vivian:

I have no idea how it started. Too much wine. But we were cuddling and he starts feeling me up. First my thighs, then he moved up to my stomach, and up to... my breasts...

Jack:

I was touching my mom's perfect little tits. I never thought I'd ever, ever do that or be able to say that.

I figured that if a situation arose in which I'd really touch them that it would be by accident or that she'd stop me immediately.

But here I was, feeling her up... And she wasn't stopping me...

Vivian:

It'd been years since a man had touched me like that. My husband and I hadn't been intimate in... forever... And here I was, with my son.

I should have stopped him before it went further. That was of course my first thought, even though I was tipsy.

But it felt... So good. I could feel myself getting wet. Down there.

While he was touching me, I held onto him. I didn't move my arms. At first. But then I also felt around his chest too. Felt his rock hard... Pecs...

We both stared directly at the movie and didn't make eye contact as any of this happened.

But as I adjusted my position a bit, my elbow brushed up against something quite... firm... that wasn't his pecs...

Jack:

Of course I got excited quickly. Here I was, with my smoking hot mom, who I've been beating off to for years, feeling on her legs and tits. And she was letting me do it.

Not only that, she was breathing deeply, making these cute, slight whimpers as I touched her.

I always wondered what she'd sound like when getting fucked. Now I realistically had an idea. And it made me hard. So hard. My cock was throbbing like never before.

But I couldn't help feeling indecisive. If this was any other female, I'd have taken it further right then and there. But it was my mom! On the one hand, she was letting me feel her up, on the other, we were slightly intoxicated.

Should I go in for a kiss? What if she flipped out? What if she #MeToo-ed me? How fucked up would that be? Getting #MeToo-ed by your mom?! I mean, of course I'd have stopped if she told me to, but she wasn't telling me to.

Instead, she took it further. She looked down at my dick, grabbed it and started rubbing it over my pants...

Vivian:

His, you know, was so big and... I... I didn't know what was happening... It was like... Suddenly... I was touching it. Touching him.

Then he did it. He lifted his face up to mine. We looked into each other's eyes. We knew exactly what the other was thinking, what we both wanted. What we both needed.

This part, I do remember. I so remember... Him leaning in, but me pulling back.

He then leaned in more aggressively. I could have pushed him away. Gotten up and left right then and there.

But I didn't. And it happened.

Jack:

It was one of those situations where nature takes over. Biology.

I'm with this gorgeous, mature woman in a tight black blouse and matching miniskirt. I'd been feeling her up. Her hand was on my cock. Of course I would kiss her.

I leaned in and she was reluctant. I don't know if it was because I was her son or just that she'd not done anything like this, anything sexual, in years.

But once her guard fell, damn, did it fall.

I lightly pressed my lips to hers. Her lips were moist and I could feel the humidity of her breath.

I pushed my tongue into her mouth. At first hers didn't meet mine. So I pulled my tongue out and kissed her lips gently a couple times, then I slipped my tongue in again.

This time our tongues met and we French-kissed for about a minute or so.

She kissed me almost too enthusiastically, her tongue jabbing forcefully into mine. But as I tenderly twirled my tongue to hers, we found our rhythm.

My hands had been massaging her body from her thighs to stomach to breasts and neck, but perhaps I jumped the gun and went up her skirt, feeling my way to her lace panties, then down to her pussy...

Vivian:

As soon as my son touched me there, I came to my senses.

I couldn't go any further. I suddenly realized it was my son I was making out with. His... was in my hand. And now his hand was up inside my skirt!

His handsome looks, the wine, and loneliness had taken over me, and, if I didn't get the situation under control, we would be having..., probably unprotected, on the living room couch!

I pushed him off me. Got up and told him that this was a mistake, or something like that, I can't remember really...

Then I darted out of the room and ran up to my bedroom. I was hyperventilating and had to take a Xanax to calm down. Shortly after that, I passed out.

Jack:

Yeah, my mom kinda freaked out. I felt bad about it. I guess I took things too far. Probably should never have touched her like that. Or kissed her.

She's a lonely, older divorced lady, and slightly drunk. How much of an asshole am I? Was I gonna really fuck her?

Yeah, I probably was, I thought to myself, as I sat alone on the couch, the movie's ending credits flickering to spooky orchestral music.

I'm not an asshole, I thought. It's not my fault my mom is so hot!

She'd told me to stop and I did. I wasn't a creep.

I mean, hey, she'd grabbed my dick! Where is her responsibility in this? What type of woman goes around grabbing dicks and thinks that's just the end of it...

Whatever it was, I had just made out and felt up my mom. My superhot mom. I had touched her pussy. She was rubbing my dick.

My dick was still erect, so I went into the bathroom, lowered my pants, took a handful of body lotion and began to beat off, thinking of hiking up my mom's miniskirt, ripping open her panties and stabbing her hot pussy. The pussy I'd just touched.

I thought back on those little whimpering sounds she'd made as I'd felt her body. How perky her tits were. The heat of her pussy. How her vanilla shampoo smelled. When I came into a wad of toilet paper, I wished that the next time I came, it could be into her...

CHAPTER 2

Vivian:

The next morning when I woke up, my head hurt a little from all the wine, but not too bad. I've never been one to get serious hangovers.

I did feel quite guilty about what had happened, though. At first I was hoping it was a dream. Given how difficult it was when I saw Jack in the kitchen for breakfast, I knew otherwise.

Jack:

That was weird. I've always been a steady girlfriend guy. Even in college, I always had a girlfriend, and didn't do the whole drunken hook-up thing.

I'd heard from buddies how it can be waking up next to someone you probably shouldn't have been with. Now it was happening to me. With my mom!

Vivian:

Neither of us knew what to say. We just looked at each other for a second, didn't say anything, not even "good morning" and we were quiet for a few minutes, not making eye contact at all.

Jack:

I sat down to the kitchen table and we were both completely silent for a few minutes.

She brought me a plate of buttermilk pancakes and bacon. I looked at it and then up at her.

Then, nearly simultaneously, we broke into mutual laughter.

Vivian:

I don't know what it was. Maybe it was that my pancakes were mangled. I usually make such perfectly circular ones. Being so flustered that morning, I'd messed them up...

Whatever happened, the hideous pancakes or otherwise, then and there, as we laughed, all the awkwardness vanished.

Jack:

I told her it was cool.

Vivian:

I told him it was no big deal. Boys will be boys.

Jack:

I told her I'd had fun...

And I suddenly felt emboldened. Us laughing about it had set me at ease.

I wanted her. More than any other woman. Ever. I wanted more, to go farther. Now that it was in the open, I wasn't shy to admit it.

I told her that I wanted to do it again. That we could date or at least be "friends with benefits."

Vivian:

I was quite surprised. He's such a handsome young man, not to mention, my son. What would he want with me?

I mean, I know I look good for my age, I think, not trying to be arrogant, but I work at it and take pride in it...

Jack:

I had to explain to her what a MILF and cougar is.

Vivian:

I'd never heard of a MILF or cougar. Honestly, I can appreciate a well-put together young man, but I never thought of being with one. I'm usually more attracted to guys around my age.

It could be that my son reminds me of my husband, when he was young and courting me. I don't know. He's such a gentleman, my Jack, and so sweet to me.