“Friend with Benefits” with My Mom – {Mom and son set out “the rules” for their special friendship.}

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.

I always thought his compliments on my looks were him just being nice. I have to say I was rather flattered to find out he’d developed something of a crush on me and really thought of me as beautiful.

Jack:

I’ve watched a little MILF porn here and there, Ashley Fires, only, because, she’s like my mom’s identical twin, but the MILF thing has never been my thing… Except for my mom.

She’s practically perfect looking. And cool too. Since we’re both single now, and highly compatible, attracted to each other, grown-ups, why not date? She’d be an ideal girlfriend.

Vivian:

I felt weird about it at first, and still kind of do. It’s not normal, to be with your son, like that.

But I guess we never had a usual relationship anyway. I love him, feel at ease with him, and enjoy his company. And, honestly, I enjoy the male company.

He’s old enough to make his own decisions and if this is really what he decides…

Still, the idea of dating, being his “girlfriend”. I don’t know. I can’t wrap my head around it. It’s not like we could tell anyone.

Pretty much everywhere there’s laws about this thing. Isn’t there? I’m not sure. I would never tell my girlfriends or nosy neighbors about it. No matter how handsome they think Jack is.

Oh my word, if his grandparents found out!

Jack:

I’m jumping the gun again with “girlfriend” talk. Amazing to me that I’ve gotten this far.

She’s right, though, no one can know. We have to keep it quiet. That is rule number one.

Vivian:

I told him we could be friends. Couldn’t say the “benefits” part.

But we need to set parameters. Rules for this, I told him.

Besides not talking about it, there needs to be others.

It’s not like we’re getting married. And I’m still getting my period, so we must take precautions.

Did I just say that to him? Precautions… What am I thinking? Oh, my…

Jack:

When she told me we have to take “precautions” it was like a bolt of lightning shooting up my spine.

I knew. I knew what she meant. We were going to have sex. I was going to have sex with my mom. My 10/10 mom. The woman of all women I’d wanted to have sex with most. It was actually happening.

Vivian:

I couldn’t lie to myself. I’m sick of being alone and his touch and kisses last night were beyond incredible.

I don’t feel totally right about it, but I’m into the “friends with benefits” thing. He’s already my friend…So…Maybe… We can do… Some things… I’m not totally sure what yet…

Jack:

I’m gonna be friends with benefits with my mom. My mom who looks like a pornstar. I really hope I don’t cum too quick.

Will this really happen, though? I’ve talked her this far. Let’s see.

Vivian:

After we agreed to do the friends with benefits thing, he got up and approached me, with a look in his eye, like a lion after its prey!

Not so fast, young man, I said. Don’t think I’m that easy. That this is easy. I still have to think about all this… We still have to talk about this…

Jack:

I respect that. I respect her. I’m not gonna be pushy and mess it up.

I asked if I could take her out to somewhere nice.

Vivian:

Oh no, we’re not doing the dinner and movie. This isn’t dating. We already see each other every night, nearly. So we’ll lay out the rules first, agree to them, then we’ll proceed from there.

Jack:

Will these be written or oral rules, I queried. We both laughed when I said “oral”. I guess my mom isn’t as prudish as I thought. This was getting better and better.

Vivian:

These will be… Spoken… Spoken rules.

First one is we don’t talk about it. To anyone. It’s a secret we keep to ourselves. Forever.

Jack:

The second is we take… Precautions… Like you said before…

Vivian:

The third is that either of us can stop at any time. Either during, before or after anything.

The fourth is that we don’t go out together, no hand holding, PDA.

Jack:

My mom was really getting into these rules. I’d always been a good kid. Never got in trouble. Always did well in my studies, athletics.

My parents never had to ground me or discipline me, so this was the first time ever my mom was laying down the law. Gotta say I liked her assertiveness.

The more she talked about it, the realer it got…

Vivian:

Right as we were having this very, unusual, discussion, the doorbell rang. It was my ex-husband! He’d come by to pick up some documents he’d forgotten in his old office.

Jack and I both froze upon seeing him. Aside from business, he was never that shrewd, and asked us, innocently, if he was “interrupting” anything.

Jack:

That was crazy seeing my dad. Good thing I wasn’t behind my mom at the kitchen counter or something, plowing into her sweet pussy wildly or even just making out.

Definitely good he didn’t come by last night. Woulda given him a heart attack.

Vivian:

Seeing my ex-husband and thinking of him lying and betraying me all those years solidified my resolve.

I was going to have sex again. I was going all the way. I was going to have sex with Jack.

Jack:

I could see how my mom was still pissed at dad. With good reason too.

His “other” wife, I’d seen a picture of her, and she’s not nearly as hot as mom. Not sure what he was thinking. His loss, my gain, though.

Vivian:

With my ex-husband gone, I set out the last rule. Anything we did, it had to be with the lights off.

We would finish dinner. Afterwards, I’d go up to my bedroom, get ready, turn off the lights, and he’d come in, and we’d, do, whatever we did…

I still couldn’t say it directly to him.

Jack:

She was nervous and her voice cracked as she laid out the last rule. I was slightly nervous too, I must admit.

Vivian:

He left soon after we finished discussing the rules. I suggested he come back later for dinner. We usually hugged, but this time, when he left, we didn’t.

We just giggled a bit and I waved goodbye and scampered back up to my bedroom to get ready for the gym…

CHAPTER 3

Jack:

That whole day I could think of nothing but my mom. I was possibly gonna have sex with her tonight. Even if I didn’t fuck her, I’d at least make out with her. Again. How lucky was I?

I met some buddies for lunch. As the conversation turned to girls, one of my buddies ribbed me for being single so long and needing to get back in the “game.”

My buddies had always indirectly told me my mom was hot. I know they all wanna fuck her as much as I do, but they know I’d punch their teeth in if they said so.

I took their ribbing in stride. I wondered how they’d react if I told them about what happened last night…

Vivian:

At the gym I ran into a girlfriend who kept pestering me to get on this or that dating app. She was saying how I needed to just dive in to something, even a casual fling.

Little did she know…

Jack:

After lunch, I hit the gym, did weights. I bumped into my mom by the front counter and we said a passing hello, quickly, clumsily, but nothing else, and I caught a sneaky glimpse of her tight ass in her yoga pants.

Vivian:

I sort of knew he was looking at my behind.

He’d always had a way of watching me from behind me, especially when I dressed up or went to the gym. I’d always thought it was him being sweet, seeing me off.

But now I know what he was really thinking… And felt myself blush a bit…

Jack:

I got to the house around 7pm. It smelled so good in there. She’d made a roast chicken dish that was immaculate.

I’d worn a button-down dress shirt, designer slacks and wingtips. Even though it was Sunday evening and a casual setting, I wanted to dress to impress.

Vivian:

I knew that chicken I do has been his recent favorite.

I’d dressed casually, loose t-shirt and jeans, simple white cotton bra and panties underneath…

I like to show off my figure, I mean, I work so hard at it… But I didn’t want anything too revealing because I didn’t want this to be weird. Weirder than it already was.

And same as that morning, I didn’t hug him… Kept him at a safe distance…

Although he looked all handsome and GQ, I wished he’d looked plainer. It felt too much like a “date.”

Jack:

Even in her t-shirt and jeans, fuck, she was a dime! Her ass and thighs made those blue jeans talk.

Vivian:

We sat at far opposite ends of the long mahogany dining table. We usually were closer to one another and ate by candlelight. However, I didn’t want any candles and kept the chandelier on instead.

While eating, we didn’t talk much. We only talked about the weather. And we never talked about the weather. Our conversations were always more substantive.

Jack:

It was… Different. For the first time, we had nothing to say to each other.

Vivian:

I worried that we’d made a mistake. We shouldn’t be doing this. I told him so too.

Jack:

I told her she’s beautiful and that her hair looked better curly and parted to the side, the way she’d styled it tonight.

Vivian:

I wondered if he’d listened to anything I’d said.

Jack:

I told her we should finish that bottle of wine. Then I’d put the dishes in the dishwasher and would meet her in the bedroom when I was done.

I was pushing all my chips on the table. It was now or never. My cock swelled up.

Vivian:

Like most women, I like an alpha-man. Not only was he taking charge, he was gonna load the dishwasher for me. God, I loved my son.

And I’m sick of being alone.

Jack:

We tore through that bottle of pinot.

My mom really perked up and relaxed when I mentioned the dishes.

She finished before me, smiled sheepishly and went up to her bedroom. I gulped down a couple more glasses of liquid courage and loaded up the dishwasher.

I was so excited that I bumbled and nearly dropped a couple cups on the kitchen floor.

CHAPTER 4

Vivian:

When I got to the bedroom, I got naked, quickly, throwing all my clothes into the hamper…

I wasn’t planning on it. In fact, I didn’t really know what I’d do.

I hadn’t thought much through. Of course I wanted to have sex. Yes, with him, my son, as terrible as that may be.

But I also thought maybe we’d only cuddle, kiss again at most, keep it innocent enough. Friends with benefits.

Here I was, though. My instinct when I closed that bedroom door was to take off all my clothes. And I did. And I turned off the ceiling light, leaving only a nightlight on.

I got underneath the down feather quilt, sunk into my silk sheets and soft, memory foam mattress, and waited for him, taking long, drawn out breaths.

It was the most excitement I’d had since I can remember. My heart was beating out of my chest…

Jack:

I knew my mom was waiting for me up there. But I had no idea what to expect.

If the lights were off, I figured that would be a “go” sign. Anything was possible.

If the lights were on, I thought that’d mean we’d watch TV and cuddle or talk. I was cool and willing for anything.

Being a man, however, one can easily presume what I wanted most…

Vivian:

He came in and said hello. I told him not to speak. That’s a new rule. No talking.

Jack:

When I opened the door, and it was dark, my cock got so fucking hard. Instantly.

I didn’t know what I should say. Couldn’t bring myself to talk “dirty” to my mom.

So I just said hello. Then she told me not to talk. New rule.

I didn’t mind at all. At this point, no more talking was necessary.

Vivian:

He came in and was still dressed. Shows what a gentleman he was. A jerk would have been naked.

I whispered to him to come to the bed and get under the covers with me.

Jack:

I got under the covers and it was so cozy and warm in there. I could really smell her vanilla shampoo.

I inched up towards mom and went to touch her, I didn’t know where, anywhere I could. It was dark and I couldn’t see much. But, from what I could see, I could tell she was naked.

It was pretty surprising to find her naked.

Vivian:

He stretched out his arm and I took a hold of his hand and pulled him towards me. I took him in my arms, hugged his strong shoulders and he got on top of me, mounting me, resting between my open legs.

Jack:

We started kissing. This time it was way less awkward. It was like she and I both knew what to do. Like we’d been given instructions.

Her tongue was so gentle and she curled it around mine and lightly, playfully dabbed it onto mine. She was an excellent kisser. I think she was rusty that first time, but now had gotten her groove back.

Vivian:

God, he’s such a great kisser. So romantic. Took me back to college, those first kisses I had with his father. His father and one boy I dated in high school are the only people I’d ever kissed.

But of the three… he was the best.

Jack:

As we kissed, I played my fingers all over her body. Her skin was so smooth… Damn, the way her little tits, pointy nipples felt as I gently squeezed them in my hand…

As I ran my hand downwards, I combed it along her velvety inner thighs and then higher, closer to her pussy.

This time she didn’t protest.

I circled my pointer and index fingers on her mound and then drew them lower, over her wet lips.

She was shaven, which I prefer, and her lips were soaking… and so.. so very warm…

I dipped my right index and pointer fingers in between her outer labial lips, and pushed into them, up into her pussyhole and lightly fingerfucked her.

Vivian:

When his fingers went inside me, I broke our kiss and my whole body quivered. It’d been so long since anything had been… in there…

The way he moved his fingers, was… like he was an expert at this. He must have practiced this a lot with somebody.

Jack:

My mom was panting and softly moaning and letting out little yelps as I played her pussy, clit and massaged her g-spot.

Crissy had taught me the proper way to finger a girl. I was grateful for her tutelage.

It was paying off in spades as my mom squirmed and creamed into my hand.

Vivian:

He made me… He made me… Have a…

An orgasm. A huge one. An orgasm like I can’t remember. His father had never done anything like that.

Jack:

After making her cum, and feeling how warm, tight and small her pussyhole was, I wanted to put my dick in…

I pulled down my pants and slowly worked my cock into her dripping wet…

Vivian:

I was still gasping from his fingers when he’d suddenly started inserting himself… his… in me.

About half of it got in and I screamed “ah!” It was bigger than I thought…

Jack:

It freaked me out to hear her scream. I wasn’t sure if it was in pleasure or not. But I never heard that type of scream. So I pulled out. It’d felt so fantastic, like paradise inside her, but I couldn’t…

Vivian:

He asked me if I was okay. I started to cry. I didn’t know why. It all was happening so fast.

I hadn’t done this in so long. Now I was doing it with my son. He’d… entered me… He’d stuck his… in… me… well, halfway, but still…

Jack:

I told her not to worry. Remember the rules. We can stop anytime.

Vivian:

He was so sweet. I wanted to kiss him again. So I did. We started to French-kiss. I wanted to feel him. I wanted him in me again. All the way in. But I wanted it slow.

Jack:

Mom took hold of my cock and began to stroke it, jerk it off gently. Last night I’d been jerking it, thinking of her, now here she was with it in her tiny, soft hand.

Vivian:

Geez, it was pretty big. A bit bigger than his dad’s, though nearly the same size, if I remember correctly. It had been a while.

I used to love it when I was in college and his dad would have… sex with me. It was so passionate. He had this fancy Persian rug we used to do it on.

Now we were in his, our bed, and I was touching another man. Our son. I’m a terrible person, I thought. I was still crying.

Jack:

We broke our kiss. Don’t worry, it’s cool, I told her. Then I took off all my clothes.

We held hands and I pressed her arms to the bed. I got on top of her, in between her legs, and thrust my hips and poked my cock around at her slippery warm pussy lips.

Vivian:

Slowly. I told him. Slowly.

Jack:

I pushed it in slowly. This time all the way in. She gasped and squeaked… Fuck, it felt amazing, my cock all in her small pussy. Stretching it out…

Vivian:

I think I had another orgasm when he put it in. My entire body felt fuzzy and electric… Having him in me, running his hands over me, kissing me, sucking on my breasts.

God, he was so good at this…

Jack:

She seemed inexperienced or rusty and was mostly quiet except for deep breathing and some cute little squealing noises.

But I didn’t care. With her looks, and how nasty and perverted this all was, having hot sex with my mom, in my parents’ bedroom, all she really had to do was lay there.

I sort of like a cross between hard-fucking and slow, romantic style. But with my mom, I wanted it slow and I wanted to take it easy on her. Although she looks young, she’s near 50. I didn’t want to hurt her.

Vivian:

He was in me for a few minutes and I was loving every second of it. What a wonderful thing about being a woman, multiple orgasms…

I’d not had one in years and now, even though I was still shedding tears, I was coming again and again as he moved deep inside me…

Then I remembered something. Rule number two. Take precautions. In his haste, he’d been in me without a condom.

I stopped him and told him to put one on.

Jack:

I had totally spaced on bringing a condom with me into the bedroom. I always kept one in my wallet, but it was downstairs.

It dawned on me that I’d been having sex with her without one. I’d broken the rules. Fuck!

Vivian:

He told me he was sorry and that he could go get one. But… I didn’t want him to stop. To leave. He said he could pull out. I told him it was okay. Just don’t get any inside me.

Jack:

She’s so cool and laidback. I didn’t want to stop either. Plus it was so awesome being in her raw… So warm…

My favorite part of her, well, I mean, it’s hard to pick a favorite since she’s basically perfect looking, but her ass, it’s… from heaven.

I mentioned to her how sweet her ass looked in those yoga pants and I grabbed a handful of it and squeezed on it as I fucked her.

It was the first bit of dirty talk I’d done. Here I was again breaking the rules… No talking!

Vivian:

No talking! I whispered to him sternly and shushed him as he pumped into me.

Jack:

I withdrew my cock and flipped her over. I tried to pull her up to her knees to do her doggystyle. She didn’t know how to arch her back and bend over properly. Not sure she’d done it like that.

Vivian:

I’d never done it like that… I was always underneath, standing, or on top. Never did it any other way.

Jack:

I guided her body into the proper position and marveled for second at her shapely ass. It looked so perfect and round as it pointed in the air.

All those years of aerobics and yoga. Definitely paying off. For her and me.

Vivian:

When he took me from behind… Wow… Made him feel even bigger. At first it was slightly painful, but as I got used to it, it was amazing and I came again after a couple minutes.

Jack:

Hitting her from behind, her squealing and panting got louder and drove me wild… hearing her, hearing her skin slap at mine…

It was sublime, her asscheeks bouncing off my pelvis, my hands on her hips, gripping her ass, my cock buried up her little pussy. I savored every minute of it as I fucked her slowly but surely.

Soon enough, my toes curled up and it was time to blow my load.

Vivian:

He pulled out and I felt him spray his … all over my back. It tickled, but I liked it.

Jack:

She rose to her knees and we kissed deeply, intensely for a minute or so. Then she rushed into the bathroom to take a shower.

Vivian:

I cried in the shower. I’d had sex… with my own son.

And had enjoyed it so much…

CHAPTER 5

Jack:

After she came back to the room covered in towels, I went and took a shower myself.

I felt ambivalent.

It was possibly the hottest and most satisfying sex I’d ever had. Probably the most I’d ever cum. Literally, string after string, all over my mom’s perfect apple ass.

But I also felt sort of gross. I’d just fucked my mom. Good, decent people don’t fuck their mom… What kind of person was I?

I got back into the room, wearing my dad’s leftover custom-made, puffy white gold-trimmed hotel-style bathrobe, with his initials on it, and my mom was in her matching, puffy white bathrobe.

She was underneath the covers, laying on her side, facing the wall.

Vivian:

I told him we weren’t supposed to do that.

Jack:

I told her I know.

Vivian:

He apologized and offered to leave. But I told him no. I wanted him to stay. I wanted him to hold me.

Jack:

I held her, and we went to sleep soon afterwards.

When I awoke she was curled up on me, her head nestled to my chest. She was already awake.

Vivian:

New rule. I told him. No sleeping over.

Jack:

I loved waking up next to her in the morning. It was bliss. Seeing her stunning face, big bright blue eyes illuminated by rays of wayward morning sunshine.

New rule, I said, all rules are made to be broken.

Vivian:

Waking up, cuddling with him… I’m okay with this, I thought. I’m okay with friends with benefits.

We kissed, opened our robes, and he mounted me and I spread my legs wide open, holding them in the air.

We had sex again.

It was quick, fast, and hard… But I still liked it… And I was fine afterward, relieved, happy, alive…

Jack:

We had a morning quickie. I finally got a better look at her naked body. How perfect it was. Her curves. Her ass. Her tits. She was still shy, though, before and after, covering herself so I couldn’t see…

We kissed pretty much the whole time we did it. I fucked her harder. She’d gotten more into it, too, doing a split, her long legs stretched high and wide, her body rocking and bouncing in sync with mine.

And she was louder, screamed a couple times…

I nearly came inside her, but fortunately pulled out and shot all over her washboard stomach…

I had to be faster than I would like because I had work. Then I took a shower and had to rush out. I was almost late to work, and I’m never late.

Vivian:

I told him to come over after work for dinner.

Jack:

I’m definitely coming by again for dinner tonight. Not just for the food and company, but for the benefits also…