Dating Mom

Chapter 9

The next morning, I awoke to a series of texts from mom.

"I was way over the line! I'm so sorry, Jeremy."

"I'm so embarrassed. I can't even leave the house now."

"Whatever you need. Therapy. A vacation. Just name it and I'll pay for it."

"Can you ever forgive me?"

They were sent one after the other. It was clear she was panicking by my lack of response, but the truth was I had been alternating between sleeping and jacking off at the thought of our previous night's date, especially the makeout session, and hadn't yet bothered to check my phone. Upon seeing the flurry of messages, I wrote back, "Sorry! I just woke up. You have nothing to be embarrassed about. No one found out, and I had a great time! Hell, I hope I can see Renee again!"

I received a response right away. "No, no more Renee the cougar. I've already scarred you enough for one lifetime."

I grabbed my dick again and started to play with myself. I thought about sending her a pic of the sight, but decided against it. To send a dick pic felt like going from 0 to 100 in a second, especially if she was having regret about the whole night. Instead, I responded, "No scarring at all! Well, maybe a fantasy or two, but I don't think there's anything wrong with that. I'm still keeping my online dating profile active and still looking for a girlfriend. Last night was just fun."

I didn't receive an immediate response that time. A few minutes passed and she finally texted back, "Good. I guess I'll keep my profile active then too. I had fun last night too, but that's gotta end now. Okay?"

"You sure?" I asked as I pumped my cock. "Even if it's just some roleplaying?"

She immediately wrote back, "You want me to roleplay as a cougar lusting after my young stud?"

Her phrasing sent me into overdrive, and I came so hard I completely annihilated the tissue that so far that morning had held up admirably.

As I tried to recover myself, another message of hers came in.

"We'll talk later. For now, stick with the dating site for your cougars."

Chapter 10

Later that night, I pulled up the dating app in hopes of finding some new cougar who I could use to replace my mother. I scrolled the first page of 40 and 50 year old women until the top result of the next page left my jaw on the floor and a tent in my pants. There she was, my mother. The algorithm gave us a match, and it only took me a second until I realized why she finally showed up for me.

My desired age range was always set at 22-60, but hers wasn't. Or at least it wasn't until now. Sure enough, underneath her name was her desired range, and it was even lower than mine. 18-60. Apparently, Renee the cougar lived on, although this time she was going by her real name.

Her profile picture was a bit more risque than I expected too. It was the same black dress she wore on our last date. Her freckled cleavage prominently displayed.

I wish I could say I thought long and hard about what to do, but at that point the only thing long and hard was my dick. I saved the pic of her in the dress and then shot her a "want to get to know you better" inquiry on the app.

That night, she sent me a text, "I can't believe the app matched us up!"

I joked back, "That was you? Judging from the new profile picture and the age range, I thought I was reaching out to Renee?"

"Ha ha, I thought maybe if I expanded my search, I might have better luck with men. And is the new profile pic alright? You don't think I seem too desperate in it?

I wanted to tell her she should post something even more daring, but wasn't sure how she'd react if I overly flirted with her. So instead, I wrote, "I think you look absolutely beautiful in it. I'm sure you've been getting tons of inquiries from men since you posted that."

"I've definitely been getting more messages lately. I can't believe how many young men are looking for a cougar. And thanks for the compliment. You're too good. You know that?"

"I try ;)"

That night, I had a notification from the dating app. I had received a message from my mom, but she had changed her name to Renee. It was the next step in their 'get to know you' process where she sent over three pre-arranged questions that I was supposed to answer.

1. What's your perfect date?

2. Where do you like to go for vacation?

3. What is your relationship with your mother like?

When I read the last question, I laughed so loud, I thought the neighbors might hear me. I immediately began to type of responses.

1. A meetup for drinks followed by whatever we feel like. A movie, a meal, dancing, or anything else that strikes our fancy. I love it when a date turns spontaneous.

2. Back home to my mom's house. It's always a good break from being so busy with school.

3. If you couldn't tell by the last answer, our relationship is great. My mother is smart, funny, and absolutely drop dead gorgeous to the point where I'd describe her as sexy. I'm sorry if that sounds wrong, but she's like my ideal woman.

Along with my answers, I was able to send 3 questions back to her. I scrolled through the list and discovered I could write whatever I wanted rather than use the ones they suggested. That must have been how she included that 3rd question to me. At that point, I was drunk off horniness and decided to be a bit more bold than her in my questioning.

1. Do you prefer older or younger men?

2. What is something a man does that drives you wild?

3. How often do you like to have sex?

The mere thought of what she might answer caused me to jackoff right then and there. Now all that remained were her answers...

Chapter 11

I must have refresh the app every minute, just waiting for her response. It wasn't until two hours, and two jackoff sessions, that my questions were finally answered.

1. Up until recently, I preferred older men. Lately, however, I can't help but find myself drawn to the young ones. I guess that could make me a cougar ;)

Whew, I took a deep breath and continued to the next answer as my dick twitched to life.

2. I'm a sucker for a hand on the small of my back. The spot just high enough that their hand glances the top of my ass.

I made an immediate mental note to never forget that fact. I began to imagine sneaking touches to that small of her back the next time we had some large family gathering. Some innocuous act that had hidden sexual undertones.

3. Oh my, you are forward! I hope you don't speak to your mom this way ;) Like any warm blooded woman, I want it as much as possible. That was one reason why my marriage didn't work. I was just too horny all the time. That's probably why I'm looking for a younger man now. I want someone who's always up for the occasion ; )

At that point, I had my dick in my hand once again. Furiously I pumped as I wished at that moment I could satisfy my horny mom. Based on how much I had jacked off since our first meetup, it was clear I must have inherited her libido.

Her answers were followed by another question from her.

"Tell me what you like about cougars?"

Fueled by taboo driven lust, I cracked my knuckles and began to type.

"Remember what I answered about my mom being beautiful? ha, I'm just kidding... maybe.

For as long as I've found women attractive, I've always been drawn to them. I think it started with my freshman math teacher. She was mid-fifties, tan, blond hair, and definitely showing the effects of having two kids in her tits and ass. Every day, she'd wear these short, low-cut dresses and hell, I was a teen. I just couldn't help but stare and fantasize at her deep cleavage that had a bit more wrinkles than normal because of all the time she must have spent in the sun damage. She was so much more developed than the girls in the class that it made it hard to chase after them when my teacher offered so much more."

I thought about ending my response there, but I wanted to push the envelope further and show her exactly why I was drawn to cougars in the most explicit, yet truthful way I could.

"Since then, my infatuation toward older women morphed and evolved to where it is today. Apologies in advance if this is too many details, but I've been with a few women in their 40's and 50's, and every time there's this incessant lust in their actions when we hookup. They ask, or actually I should say, they demand that my young, strong body gives it to them over and over."

I ended the response with a final question back.

"Care for a date soon, Renee?"

No more than ten minutes later, I received a short response.

"Yes, I'd love that. I know a great little bar we can meet up this Friday at 9. Directions are below."

The bar was the original cougar bar where I accidentally ran into her all those months ago.

After that, I headed to the bathroom for another jackoff session about my upcoming date! She was going to roleplay as Renee! Judging by the bar selection and her messages, it seemed like she was really getting into going out with me.

I began to pump my dick at the thought of her showing up at the bar in some skin tight dress in a fabric so tight that her large nipples couldn't help but be displayed. I was getting closer to orgasm at the single thought of her flaunting around the bar with those pencil eraser nipples, but was brought back to reality at the sound of my phone going off.

Horny and hopeful for more flirting, I checked to see if it was from mom, but instead it was a number I didn't recognize. I open it up and found the message.

"You can never tell anyone, and I'll reserve the right to call the whole thing off whenever I want. In the meantime, I figured I'd pass along two different outfits for what I was thinking of wearing tomorrow. Tell me which one you like more, stud.

-Renee"

What followed next were the images of two dresses in what I recognized as my mom's bathroom. The first, a pink one had straps so thin they could barely be seen on the hanger. The chest was lace which seemed possibly transparent from the angle of the picture. Judging by the way it hung, it would have come halfway up her thigh. I was really curious how well her freckled and tan legs would look against the pink.

The second outfit was a red club dress. It's natural elasticity made it extra short on the hanger, and the top was cut to the point where it likely would end in the middle of her chest. The thought of her constantly trying to pull her dress down because it was so short played over and over in my mind as I pumped my dick once again.

As I recovered from shooting loads all over those pictures, I typed back, "Red all the way. Panties optional."

Chapter 12

Just like the last time we had a "date" at that cougar bar, I showed up about ten minutes early in hopes of finding a cozy spot for us. It seemed, however, that Renee beat me to it.

As soon I as I entered, she was the first person in the room I noticed. It was the red dress. It was her freckled tits pushed up and on full prominent display. It was the deep red lipstick and red eye shadow she sported. It was the highlights in her hair. Strands of highlights in her hair! What a change that was.

She stood up and walked toward me with nothing more than a grin. One tan leg in front of the other. She held her arms out and said, "You made it, babe." and reached embraced me in a hug. I had planned for this, and moved my arm down to the small of her back. Gripping my mom in the way that she said she liked. To my surprise I felt her hands grip both of my shoulder-blades and pull me in closer. My ever growing hard-on pressed up against her crotch. She jumped back slightly, but immediately seem to catch herself and then she pressed herself forward once again. She leaned in close and whispered, "And it looks like you're happy to see me too."

Flabbergasted at the sight of my mom dressed like a sex-crazed cougar, all I could do was let out a "you got that right." She grabbed my hand and led me to the dark corner where we sat next to each other in a loveseat. We each ordered a drink, and seem to fumble for words.

That was until a woman walked in who seemed to be Queen Cougar. Bleach blond hair. Bright red lipstick placed over swollen lips from the collagen. Her face taunt from botox. She wore an all white dress and her bolt-on tits were nearly up to her neck.

My mom broke me out of my trance with, "Whoa, look at her."

On her arm was the guy I recognized as our redshirt freshman quarterback on our college football team. Fresh faced and just out of high school, he seemed punchdrunk at being at the bar with that mature woman as his date.

"So that must be what a real cougar looks like?" My mom asked.

In an attempt to flatter my mom, but also because it was true, I shrugged and responded, "I'd say you're just as much a cougar as she is. You might not have the work done like her, but you still look as sexy as they come."

"You know, I used to think about getting a boob job." She cupped one in each hand and said, "What do you think?"

The thought of my mom with some big blown up tits came rushing in my mind. Huge bolt-ons that she wouldn't even need to wear a bra in order to keep them up. She would parade around town and be unable to hide her massive silicone milkers. Maybe she would even go as far as to have some nipple piercings?

In lieu of telling her that, I answered, "I think yours are great. If anything, you don't show them off enough."

She brushed me away with an, "Ah, you're just saying that."

"No seriously. I mean don't get me wrong, you'd look hot with some implants like that woman, but I think yours are great as they are too."

She leaned forward, and a got a better look at her freckled cleavage. "Maybe you'll get to see a bit better view someday. Depending on how this date goes, of course."

Caught off guard, I stuttered, "you... you would show me?"

She grinned, "This whole cougar thing is still new to me, but I thought showing off your tits was part of the role. You know, something like her."

My dick was so hard, it pushed through my boxers as I answered, "Yeah, I'd love that."

"Good," Mom purred as something caught her eye across the room. "Oh my god!" she whispered. "That woman... shes sitting over there with legs spread open enough that shes flashing half the bar."

I slowly turned around to take a glance. Sure enough, the queen cougar was reclining back, her legs spread just enough that she was flashing her bare pussy.

"Like i said in the text last night," I said as I turned around and grinned. "Panties optional."

"What a slut," my mom said, but it's funny, she said it more as a curiosity rather than some sort of admonishment.

I gave another glance. As hard as it was to look up from her pussy, one glance at her eyes told me everything I needed.

"She's flashing her date. You can see it in her eyes. She's staring right at him..." I couldn't think of the word so I spit out the first thing that came to mind. "Lustily?"

"Lustily," My mom began to laugh as she stared up at the cougar's eyes. "Ah, I see it now. She's eye fucking him. Goddamn what a slut. And she's fully shaved. Is that in now?"

"Some men like it. Definitely not my thing though."

"Oh yeah?" She asked.

"Yeah, the more hair, the better. I love a big bush."

"How big are we talking here?" She asked. The question must have caught her by surprise since she turned and changed her focus to me.

"As much as possible. Like I want a forest between her legs. I want a brown or blonde or gray-"

"Or gray!?"

"Yeah, that'd be hot. A big gray bush that covers her pussy."

"Interesting," she said and leaned forward in her chair. Her tan, wrinkled cleavage converging right above the cut in her dress. Her crows feet on the corners of her eyes and lips showing every year of her 53 years alive.

I added some more context to the question of my big bush infatuation. "Actually, just to be honest with you, I've never actually been with a woman who had a big bush. They've all been trimmed or fully shaven like that Queen Cougar. What are you?"

She paused for a moment before coyly saying, "Trimmed. I can't be poking out everywhere when I get in the gym sauna after working out."

"That'd be so hot!" I blurted out. I couldn't help it. The thought of my tan 53 year old mom walking around in a bikini bottom with her pubic hair poking out the sides. I imagined licking the furthest hair and working my way deeper and deeper until I was tongue deep up my mother's hairy hole.

"Hmm," was all I received for an answer. At that moment, a cocktail waitress stopped over to see if we needed another drink.

"Hi, can I get-" she started. Her phone began to ring and as she glanced down, she had a look of annoyance.

"I need to take this." she said and stood up to look for a nearby quiet place to take the call. She mouthed "Be right back" and turned to leave. As she left, I couldn't help but stare at each cheek of her ass as it rose and fell in her tight red dress. She gave it a quick pull down, but it immediately shot back up. Her ass was still in great, toned shape, but the dress was just too tight.

She wasn't gone long until she came back looking quite a bit flustered.

"You wouldn't believe this, but well, I might as well tell you now, I have a teenage daughter. She was supposed to go out with her boyfriend tonight, but apparently they just broke up. She's hysterical, I gotta go put out this fire."

I laughed and said, "It's alright! I totally get it. My sister is a similar way. You wouldn't believe how crazy she can get sometimes."

"Maybe that's why you like older women?" My mom asked as I rose up to meet her. She grinned. "Well, that and a full bush?"

I put my arm around her waist, essentially on her upper thigh, and to my surprise, she leaned into it. The cocktail waitress appeared once again, and my mom slid her a credit card before i got the chance to pay.

"Hopefully paying will make up for having to leave early." she said and tapped several times on her phone. "Looks like the uber is about twenty minutes away."

She then carefully, almost as if on accident, brushed her hand against my hard cock. She purred, "Care to wait with me?"

We ended up in such a hurry to leave, we briefly left my mother's credit card there. I raced back in to get it, and managed to catch one last look at the cougar queen's bald pussy, and arrived back outside to find my mom standing alone on the curb. Tight dress. Tight body. I had thoughts of her whoring herself out like that. Willing to stand in public wearing the bare minimum and letting any paying stranger have their way with her.

"My hero," she said as she stepped forward to receive her card. She touched my chest lightly and said, "So, I have an idea."

"Oh yeah?"

"The bookstore over there, I believe I recall that they have solo bathrooms. Care to check it out?"

I could barely nod I was so excited. She interlocked her hands in mine and led me into the busy nighttime bookstore. Far in the back, away from the crowds, stood two solo bathrooms. My mom stepped forward into one and led me in.

"No, no light," My mom said as I went for the switch. "Just fucking kiss me!"

In the dark, I grabbed her in an embrace and met her mouth openly. My tongue danced in and out with hers as my hands ran up and down her body. I did not penetrate the outer layer of her dress, but I grabbed, molded, and squeezed her ass. For being in her 50's it had a wonderful amount of tone to it, no doubt from all the cycling.

"Mmmph, this is what I've wanted all night!" she whispered in excitement and ran her hands up and down my chest. "Some hot young stud to ravage me."

It was then I made the decision to remove her top and reveal her tits. My fingers slipped inside the red fabric and pulled back to expose my mom's bare chest. The pitch black darkness of the room made it impossible to see them, but I pressed forth until both of my hands were met with the pointed tips of her nipples. I lightly grabbed those two nubs like I was holding a cigarette and stroked them down until I reached her areola. Far and away, my mother had the longest nipples of any woman I have ever seen. I knew they were large after that last time I saw her in her cycling outfit, but to experience the feeling of touch drove home just how long they really were.