"Friend with Benefits" with My Mom

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.