Chapter 1
It was Thanksgiving break which meant I was back home from college for the week. My sister and I were staying at my dad’s on account of him heading to Hawaii for Christmas and he wanted to spend the week with us before he left. The night before Thanksgiving I went downtown to bar hop with a few friends and we ended up at what would be considered the “Cougar bar” of the city. I’ve always had a thing for older women so suffice to say I was all for going there.
And it did not disappoint in the slightest. The room was packed with older women in skin tight dresses. Fake boobs, tan skin, gray hair, a slightly wrinkled chest, the occasional collagen lips. I was in heaven, and it continued to get better as the bar filled up through the night until around 10, this group of four women walk in. It was my mother and her friends.
Quick exposition: Mom is pretty tall(I’m 6’5″ so I guess I got it from her) so it’s easy for her to stand out. She has brown hair and is in great shape from being an avid cyclist. She has freckles on her face, shoulders, and chest. Despite my love for older women, I’d never really classify her as beautiful or sexy because I just kinda saw her as my mom, but as I watched her walk in with this long black dress that was cut just low enough to show just a small amount of cleavage, I thought she was the sexiest woman in there.
All in all, she was actually dressed fairly modestly compared to some of the other women in there, but that didn’t mater. It was my boring mom dolled up for a night out, and it made me so incredibly horny. I wasn’t embarrassed to see her there. Nor was I panicked. I was horny. This lasted for about five seconds, and then I came to my senses and started to panic. I mean, I was standing in the middle of a bar lustily looking at my mom.
I went to my friends and told them we had to go because my mom showed up. After they got done with laughing and had me point her out, they finally agreed and we closed our tab and headed to the exit.
As we walked out, I heard, “Jeremy! Is that you!?”
I stopped dead in my tracks and turn around. It was one of my mom’s friends. Dead to rights, I felt my face go red as I made my way over to them.
“Jeremy!” My mom said,”Are you guys just leaving?”
“Hey! Yeah, we… uhhh… we’re just bar hopping.”
Just then my friend Nick piped up. “But we can stay for one more!”
I could feel my friends holding in their laughter.
“Yes!” My mom’s friend shouted. “It’s our first time here! Come tell us what’s good to order?”
We made our way to the bar and it was probably the most polite conversation a group of college students and a group of mature women had in that bar.
As we drank our martinis, the two groups eventually separated except my mom and myself who continued to talk side by side at the bar. It was normal stuff until we got to the bottom of our drinks.
“That was really good!” My mom said and put it down. “I should come here more often for those. I used to love martinis.”
“Me too. All the bars around school focus on beer. I like this stuff much more.”
She smiled, “Look at my son! The distinguished gentleman.”
“Hah, I don’t know about that much.”
“Oh you absolutely are! I mean for one you’re the tallest guy in here. Tall, dark, and handsome! I’m surprised there wasn’t a flock of girls with you tonight.”
I finished off my martini and begin to feel pretty tipsy. It likely had to do with my head spinning over the course of the previous 20 minutes from looking at my mom as mom to looking at her as this sexy milf.
“Eh, easier said than done.”
The bartender came over and asked me, “Would you and your date like another martini?”
“Oh this is my son!” My mom said and put her arm on my shoulder. I remember getting a whiff of perfume. This high end floral stuff. It was so good.
The bartender apologized and I looked over at my friends who were currently chatting up with some girls our age. A rare sight in that bar. I looked at my mom and my eyes darted down slightly to catch that little bit of cleavage. I wanted to lick in between them and then move up to her mouth. Sweat began to form as I imagined french kissing my mom right at that bar.
“Let’s do one more!” I shouted.
“Fine by me! I like this!” She said.
“Me too.”
“Can you believe that bartender thought we were dating!?”
I shrugged my shoulders and tried to act nonchalant, despite wanting to scream out that I’d love to date her. “I don’t think it’s too crazy. Especially in this bar. You’re like the best looking woman here.”
Blaming that last sentence on the martini. So I explained to her that it was a cougar bar, albeit not in those exact words. She laughed at what she said earlier about coming back there alone for those martinis and that’s when I just put it out there.
“This isn’t that far from school. I could meet you here sometime for a martini. I like it too.”
“Hmm,” She said and pursed her red lips. “I’ll need to think about it, but it would be a big boost to my ego to have a martini with a tall, dark, and handsome man every once in awhile. Just gotta pretend you’re not my son. Oh, and no cougar bar!”
“Fine fine! I’ll find somewhere else.”
She began to laugh and leaned forward to playfully grab my arm.
I was shaking in this in horny excitement, but that’s kinda where the night peaked sadly. After that, it was pretty much that for the night. Each of our respective groups came back and we soon said our goodbyes. I gave her a tight hug. Again that great perfume all over my face. Hopefully she didn’t feel my boner in my jeans. We did one more bar and then that was it. I came back to my dad’s place where I’ve managed to jack off every fifteen minutes at the thought of french kissing my fifty-two year old mom the next time we go out for drinks.
Chapter 2
I woke up the next morning with a raging hard-on thanks to the thought of my mom, her cleavage, and the sight of her dressed like an actual women out to find a guy. I knew I had to at least reach out to her because otherwise I’d spend the rest of my life jacking off at the thought of our one night at the bar. So with my phone in one hand and my dick in the other, I began to text.
Me: Hey! That was awesome to run into you last night. How’re you feeling today?
Mom: Jeremy! Feeling great! Got a tip about hangovers from Shelly last night. Coconut water prevents hangovers. Glad I always keep it stocked for after my cycling. And it was great to see you too! The bar was so much fun with you. What about you? Are you hungover at all?
Me: Just a little tired, but that might just be from staying up late. About to head back to school.
Mom: Safe drive! Text me when you get there. Can’t wait till you’re back for xmas.
Me: Me too! Don’t tell Dad this, but I always like the years when Christmas is at your place.
I waited about ten minutes, but another message didn’t come in so I jacked off quickly and then began the drive back to my apartment on campus.
As I drove back to school, a message came in from her.
Mom: Good! I like those years when you’re here too!
When this came in, my mind was racing with ways I could try and get another bar meetup with her. I didn’t text her until I arrived though. Safe driving and whatnot.
Me: Made it! That drive always goes by so quick.
Me: Oh, and I might stop back before Christmas. Gonna see some of the guys.
Mom: Glad you made it back to school! And let me know if you come over before xmas and want to see your old mom.
Me: Bah, there’s nothing old about you.
Mom: You flatter me too much!
Me: Hey, just realized, we could also go back to that bar if you want. It’s close enough to school that I can meet you there some weekend.
Mom: Hmm, I actually thought of this last night after you asked. Yes, but on 1 condition.
Mom: No cougar bar! I don’t want to be looked at as some sort of cougar out for younger men.
My dick immediately got hard at the thought of her dressed like one of those cougars in a skin tight dress that shows off her freckled chest.
Me: lol I wouldn’t call you a cougar.
Mom: Hahaha me and the girls cracked up last night about that. None of us knew it was a cougar bar!
Me: So you want me to find some other place?
Mom: Yes! A place where a mother and her son can grab a good martini and no one will confuse her for a cougar.
Mom: Sorry if I just weirded you out about your own mother.
My mind was racing. Weirded out was one way to put it. Almost painstakingly excitedly horny was another. I freaked out and went straight platonic and escaped.
Me: hahaha no. I’ll fine something for us.
Mom: Thanks!
And we sort of just left it there. I immediately jacked off, and the crazy thing was, I didn’t even fantasize about anything overtly sexual. Like I got off at the thought of making out with her. The image of my tongue and my 52 year old straight-laced mother’s tongue dancing together in this passionate kiss was almost overpowering in its eroticism.
One thing was for sure though. I needed to find a bar for us, and pronto.
Chapter 3
We texted on and off throughout the week about the usual stuff- school, friends, family, but also spliced in the occasional mention of meeting up. She seemed really excited about it and would comment about a specific drink or the bar I picked out. Meanwhile I could hardly contain my excitement and pretty much jacked off 24/7 at the thought of it.
It felt like an eternity until the weekend finally arrived. I put on the one sports coat I have, jeans, and collared shirt. Like proper enough to look nice, but not too overdone. I decided to take an Uber there for multiple reasons.
1. Because I didn’t want to drive drunk
2. In case Mom decided to drive me home.
3. You ever try to find decent affordable parking in a big city?
The bar was packed when I arrived and filled with people of all ages. Several women had on skin tight dresses and I immediately felt an erection at the thought of my mom wearing something similar. I sent a quick text of “I’m here!” and waited by the door for her.
Behind me, a hand touched my shoulder, and I heard in this sultry sexy voice “Why hello there?”
I spun around so fast I got dizzy and did this little stumble/wobble maneuver.
Mom began to crack up and she said in her normal voice, “hahaa oh Jeremy! I’m so sorry! It was supposed to be a joke. I didn’t mean to scare you.”
She had on a quilted black sweater and normal jeans. It was a quintessential mom look. So much for the skin tight dress fantasy.
“You didn’t scare me. The voice was just surprising, that’s all,” I said as we found two spots at the bar and ordered our drinks.
As we sipped our first cocktails, we just talked normal stuff. School, friends, family. It was good, but my sexual energy kept rising as I found myself getting aroused as I replayed her touch and the “Why hello there” in my mind. It wasn’t apparent at first, but she was also wearing extra makeup. There was light red lipstick that accentuated the creases in her lips. Dark eye-shadow that had a slight wrinkle right below her eyebrows. Even darker mascara on her eye lashes. And there was even a fair amount of blush that dulled her freckles. She made have been dressed like a mom, but her makeup was like a cougar.
Despite the platonic conversation, I was about ready to explode by the time I finished my first drink. I excused myself and went straight for the bathroom as I replayed that sultry voice over and over, except “Why hello there” was replaced with lewder and lewder things.
“Stick your tongue in mommy’s mouth”
“Lick my nipple”
“Shove that cock up in me”
“Creampie my asshole”
And that’s when I exploded. Over and over I shot ropes into a piece of toilet paper. By the time I finished, my legs were shaking I was so weary.
Moments later, I returned to the bar to see some man talking to my mom. She was getting hit on! A little squat and balding, but he was most likely her age. Mom was easily out of his class, but I wasn’t sure if I should have interrupted or not. And then I saw her face and she saw me. She smiled and nodded at me, and the man turned around to see who she was smiling at only to see me smiling back. I walked over and the man said, “Sorry about that, man.” and gave me a hard pat on the shoulder. Looking back on it now, he was trying to provoke me. Guess I just wasn’t paying attention at the time.
I took my seat, and found I had a second drink waiting for me. At that point, I was slightly tipsy. Well, tipsy enough that I wasn’t so nervous at least. I started to laugh and asked, “Was that guy hitting on you!?”
“Yes!” My mom answered, apparently a little tipsy as well. “Is that what I’ve come to? Frumpy old men?”
“Nah, that’s like the second time this week people thought we were dating. And look at how old I am.”
“That doesn’t count, the first time was the cougar bar! And that guy was just drunk.”
“Fair enough, mom, but just sayin'”
“Haha are you’re drunk too? You should be offended these people think you’d be with a 52 year old woman.”
“Nope, I think you look beautiful, mom.”
“Oh, thank you, honey! It’s really good to hear that.” She smiled warmly. A few wrinkles shown in her eyes and lips, and I just found them so goddamn sexy. Like I could easily remember what she looked like without makeup, but at that point, the thought of this mature woman was insatiable. She finished off her drink and said, “I should probably stop after this one. I have to ride tomorrow and anything more than one drink will leave me hungover. This has been fun tonight! We should do it again! Let’s just try not to be mistaken as dating for once.”
I laughed and said, “Sounds good to me. ” And I handed the bartender my card as I gulped down my second drink.
“Oh honey, don’t you dare do that, I’m your-”
“You can get the next one.” I grinned.
She gave a little laugh and said, “Who would have thought my son is so smooth. You better not use this to take advantage of girls!”
I chuckled and held up my hands. “I promise.”
So I closed out my tab, and we left. Just as planned, she offered to take me home! So many different scenarios ran through my head about the ride home, and while we walked to her car, I heard “Jeremy! Jeremy!” from an uber and a few friends from college spilled out. They were going to a bar to watch the basketball game and shouted for me to go with them.
“You’re young! You should stay out!” Mom said as I realized my drive home was quickly evaporating.
“Do you want to come too?” I asked in some last ditch effort to salvage things.
“The ride tomorrow, remember? Go have fun! We can do this again another time. But don’t take advantage of girls!”
“Alright,” I said and met her for a hug. It was a good three second one as well. My jeans were hopefully thick enough that she didn’t feel my hard-on through them. “Text me when you get home so I know you’re safe.”
And from there, I left and met up with my friends. That was basically it. I returned back to school to gear up for finals. All the while trying to suppress that sultry “Hello” in order to study. I’ll be staying with her during the Christmas break, and goddamn I don’t know how I’m going to manage it. I want to go through her closet and see what dresses she might own. I want to see her bras. God, what if she has thongs?
Chapter 4
Usually Christmas breaks feel like an eternity to arrive because of exams, but for this particular year, the slowed down time was due to the fact I’d be staying at my mom’s for two whole weeks. The nervous horny excitement rose each day until finally I stepped through the front door, bags in hand, erection rock hard. The first few days were the typical normal family experience with my mom and sister. We talked about school, family, and friends over dinner and did our own thing at night with the end result being me jacking off at the thought of going through my mom’s closet. Finally, on the last Saturday before Christmas, my mom and sister went out for some last minute shopping which led to me being able to snoop around her room.
I shook in excitement as I walked through the house and into her room. My mind filled with all sorts of lewd objects I knew deep down she wouldn’t have, but still wanted to believe. Crotchless panties? Sure. Shirts so small they show underboob? Absolutely. Multiple dildos? And in multiple colors and sizes too? Nothing was off limits in my mind.
Common thought would be that I would escalate the snooping from her dresses to bras to panties, but nope, I went straight to her dresser to look at her panties. I pulled open her drawer and saw mostly the sheer cotton types. Like the standard fit I think most women wear from day to day, but as I continued to shuffle around her drawer, I stumbled upon thongs! They were cotton as well and in solid colors like blue, black, red, but she had quite a few of them and I couldn’t help but whip my dick out and start playing with it at the thought of these strings running up her 52 year old ass crack. From there I went in reverse to the bras, nothing usual there, but for image-sake, I learned she’s a C cup. Like I said before, she’s a hobby level cyclist so she has a lean body, but it was hot to know she has some decent sized tits as well. Finally, I made it to her dresses, and yeah, nothing too scintillating except for the one she wore the night at the cougar bar. I went back to her thongs one more time and got myself off. Luckily, I shot it all in my hand. A small bit dripped onto the carpet, but I wiped it up and was likely too small to notice anyway.
Then just for shits and giggles, I went to her nightstand. Pulled it out and this little lipstick sized item was in there. I pulled it out, and it twisted and began to vibrate. My mom had a vibrator. Holy fuck I instantly became hard once again as I brought it up to my face. I smelled it and it felt like I crossed some sort of taboo threshold and began to shake once more as my dick grew hard. It smelled like a pussy, but the fact that it was my mom’s pussy made it all the hotter. And then I put it in my mouth and tasted. It was a little pungent, but I didn’t care because I was so horny about the whole thing. I ended up getting off once again with my mom’s vibrator in my mouth. Her aged pussy juice slurped up by my tongue.
And that’s how the first week of being back went. In addition to that, I found out a short story I wrote was picked up for an anthology affiliated with my university’s MFA program and as such I’ve been invited to give a reading at this bookstore after the new year. In other words, it was an opening to ask her out again and suggest that we treat it like a date since it would help my cache with some of the other authors of the city to see me with this beautiful older woman(I’ll likely use some other line than that, but that’s the gist).
Oh and I went back into her room and got myself off by licking her vibrator several more times. If only the pussy juice on it was fresh.
Chapter 5
Every chance I got over that final week at home was spent going through her thongs or jacking off to her vibrator. It got to the point where I eventually became worried she would notice my saliva on her vibrator since I was licking it so much, but this worry was dulled by the thought of her sticking a vibrator full of my spit up her pussy or on her clit was euphoric.
The day before Christmas break was set to end and with it me going back to school, I ended up getting the courage to ask her to come to my reading event as my date. I was sitting at the bar of our kitchen eating some lunch when she came in fresh from a bike ride. Her tan skin had a tinge of red to it from sweat and exertion from her ride. Her brown hair was pulled back in a ponytail and she had on a two piece spandex bike outfit. White top. Red shorts that stopped just above her knee.
“Hey mom I got something to ask you,” I said as I she passed me by and went for the fridge and proceeded to bend over. Her ass wasn’t facing me, but from the side, no panty line was visible. Was she wearing one of her thongs? Was she wearing anything under that spandex?
“Oh yeah, what’s that?” She asked as she pulled out a big liter bottle of coconut water.
“I…” My mind went blank. Her nipples were hard to the point where I could make out each nub perfectly. They looked two eraser tips protruding from her chest, almost to the point where they were comically long. I looked down at my lunch to focus on what I was trying to say. “Umm, so one of my stories got picked for this anthology and I’m supposed to give a reading for it next week.”
“That’s incredible! Congratulations!” She said as I looked up. I tried to look into her eyes, but her nipples were just too long. I wanted to pinch them. Suck them. Cum all over those fleshy nubs. “You’re such a great writer! But what do you need to ask me?”
“Ah, this is kind of awkward. So I’ve been to a few of these things, and when it comes to this stuff, being able to impress publishers and agents is bigger than just your story. Like they want you to look and act a certain way.”
“Hmmm, so do you need some fancy clothes are something? You should wear the same thing you wore when we went out for drinks. You looked so handsome.”
“I’m alright with clothes, but this is something else you can help me with. So these publishers and agents consider at author’s personal appeal, and because of that I was hoping you would pretend to be my date for it.”
Mom started to laugh and she said, “Oh Jeremy! There’s no way anyone would believe that!”
“They totally will! I mean, it already happened to us twice.”
Mom squinted her eyes like she was thinking it through. It took every ounce of my energy to look her in the face and not her extra long nipples. I added, “It’ll just be for show and I think these people will really be impressed. None of them know who you are and we could give you a fake name and backstory and stuff.”
She smiled. “Okay, but keep things reasonable! And don’t mention this to anyone. I mean it. It’s been so long since I was on a date, I don’t want people to think I corrupted my son because of it. And you should have no problem finding a girlfriend for next time!”
At that point, I was over the moon. I’m fairly certain my voice cracked with excitement when I answered “Okay, I promise!”
“Nice! Send me the details when you get them. I’m off to take a shower and relax. That ride kicked me ass.”
“Okay,” I said as I envisioned her nipples poking through a soapy chest. I watched as she walked into her bedroom. Each ass cheek inside her red spandex rising and falling independently. Yep, she definitely was wearing either a thong or nothing at all.
I quickly finished my lunch and went straight to the bathroom where I proceeded to cum my brains out at the memory of her nipples and the prospect of our upcoming pretend date.
In the week leading up to the event, mom wanted a backstory and alias to make it fun for her and so we settled on Renee, age 45, a divorce attorney (She learned enough from her divorce with my dad that she felt she could answer any questions that may come up). We met on a dating site and this was our third date. In the beginning, I had to repeatedly go after her since I was a little younger than she normally dates, but she had a good time for the first two dates which led into this one.
I met her outside of the reading event about ten minutes before it was set to start. She had on the dress from the first night. The low-cut(for her) one that showed off actual cleavage. Her lipstick was a darker shade of red than normal too. She looked like an actual mature woman out on a date which made me all the hornier for her. We made our way inside and I found the host. I held out a hand, “Hi I’m Jeremy blahblah and this is my date Renee.”
I looked over at my mom and she gave a hi and a nod to him. He gave us instructions for the drinks, food, reading event, etc. and we proceeded to walk side by side to a little wine table they had setup in the corner. I would’ve loved to hold her hand or put my arm around her, but having a first physical contact turned out to be much harder than just saying she was my date.
We took our seats as mom said, “There’s alot of people here. Aren’t you nervous?”
As I gulped down my wine, I thought my nervousness was apparent. I answered, “Yeah, I’d say so.”
To tell the truth, I was nervous. I haven’t done that many of them, but public readings made me fairly nervous. That combined with all the horniness I was feeling about roleplaying a date with my mom had distilled into this pure essence of shaky nervous energy. I finished off the glass of wine, even though I knew the effects wouldn’t be felt right away.
Mom touched my arm, “Your stories are great though. Everyone is gonna love it.”
Whenever I get really nervous, I try to joke my way out of reliving the situation. So I responded for melodramatically, “What’s important is that you love it, my darling Renee.”
She laughed and swatted me away.
Throughout the course of the first few readers, we sat side by side, not really saying much since the event was pretty much non-stop. I grabbed one more glass of wine for us and then it was my turn to speak. I read my story, and really crushed it. No slip-ups and the crowd gave a really good response, including my mom who stood up to applaud. Before I sat down, I said, “That one was for my beautiful date, Renee.” and then returned to my seat where my mom was smiling from ear to ear.
She hugged me when I returned and I pressed her in close. Her perfume left me feeling more intoxicated than the wine and I swear my hand felt a ripple in her dress by her hips. I had enough exposure to her panty drawer to know the exact thong she was wearing. Thoughts of cumming all over it and having her put it back on swirled in my head as she exclaimed, “That was amazing!”
I said, “Whew, glad that’s over.” as we broke from the hug. We took our seats again as I sat back in my chair, full of confidence and alcohol and horniness, and just went for it. I put my arm around her shoulder and she leaned in to me. The perfume ensconcing my body.
I looked over and then down involuntarily. The cleavage was right there. I could’ve counted the freckles and the gradual wrinkles where her tits met. We stayed like that till the end of the show where we stood up and began to head out. I grabbed her hand, and she interlocked her hand in mind.
Mom smirked: “What a romantic!”
Me: “Anything for a woman as gorgeous as yourself, Renee.”
She leaned over and whispered, “You’re so good at this! I keep forgetting I’m in character.”
“Jeremy!” A man yelled out at me while we were walking to the door. He was an editor with a small indie house and just wanted to say hi and give me his card. I let go of mom’s hand to get it, and when I returned I put my arm around her waist. I could feel the seam of that thong against my hand.
We walked out the door with my arm still around her waist. Once we got outside, we separated and began to walk back to our cars. The deal was only to pretend we were dating during the event so sadly it was over.
My mom said, “That was alot of fun! And you did so good! Next time though, find a date who isn’t your mother.”
Me: “Thanks, and what are you talking about? You were a great girlfriend!”
Mom: “Nope, not healthy. I want grandkids one day haha!”
As we walked, we passed by a wine bar and I asked, “Care for one more glass of wine?”
Mom: “Hmm, I’d say we can do one more. No more Renee though.”
We went inside and took our seats at the bar and promptly ordered two more glasses. We talked about the reading, and worked on our glasses until somehow the topic of dating came up.
Mom: “Seriously now, when was your last date?”
Me: “Tonight.”
Mom: “Who wasn’t…” And this was the awesome part. She looked at the bartender who was right in front of us and said, “Who wasn’t twenty years older than you?”
She didn’t say ‘who wasn’t your mom’ and so I decided to have a little fun with this. “What are you talking about? You only have fifteen years on me, Renee. And I doubt anyone would even notice.” I spoke up to the bartender. “Hey, how big do you think our age difference is?”
He already was listening into our conversation so I trusted him to help me out.
He smiled, “Yep, I wouldn’t guess over ten.”
Mom smirked in my direction and said, “Fine, I guess it’s okay, but I have an important divorce case this week and need to get home soon.” She looked at the bartender and said, “We’ll close out after this one.”
The bartender nodded and walked away when she returned to me and said, “Smooth stuff, mister. Fine, we can play date for this place, but that’s it. We both need to date people our own age.” And she whispered, “And aren’t mother/son.”
I reached down and grabbed her hand and she reciprocated. She said, “Ten years difference. Hah! I’ll take it. You’re a really good date though. Seriously though, you’d be into an older woman?”
Me: “Oh yeah, definitely. I mean, I’d date girls my age too.”
Mom: “So that night in the cougar bar…”
I felt my face grow red. “Guilty as charged.”
Mom: “Have you had luck with that before?”
Me: “I don’t do it often. Only once or twice.”
Mom: “How old of a woman?”
I don’t know why, but this almost felt like a brag: “50.”
She audibly gasped.
Me: “When I was 19.”
In a hushed exclamation, Mom said, “She could have been your grandmother!”
Me: “Well, she didn’t look 50. Just like you don’t look 52,” The bartender walked back over and handed the check. “I mean, you’re fucking smoking, Renee.”
One more audible gasp.
Mom: “Fucking smoking, eh?” God it was so hot to hear her use that language, even if it was pretty tame by today’s standards. The bartender walked away and she said, “Well you’re quite the young stud too, you sexy motherfucker.”
Me: “Emphasis on the mother.”
She busted out laughing and quickly said, “Hahah annnddddd I think about closes us up for the night. Here, I’ll grab these drinks.”
She set her card down as I apologized for being so forward, but she said it was all in good fun.
As we walked out, she grabbed my hand and I reached up and kissed it.
Mom grinned and rubbed my thumb with hers. “And that’s the closest thing, you’ll get to a kiss.”
As soon as we got to our cars, mom said, “This week, I want you to make an online dating account and start meeting girls your age.”
Me: “What?”
Mom: “Whatever it the current thing popular service is, I want you to sign up for it and start having dates. One per week. I know full well you’re capable of that.”
Me: “Okay, you did me this favor tonight so I owe you(I already had one of those hookup app accounts so mission accomplished). So no more dates then?”
Mom: “We can still get drinks, but the roleplaying stuff isn’t helpful. For either of us. Do you know how long it’s been since I had a date?”
Me: “Tonight?”
She busted out laughing again.
I’m not sure why I suggested it, maybe because it was fresh in my mind. I said, “Why don’t you try online dating too? We can use the same app. Like moral support and stuff.”
Mom: “That’s not a bad idea at all.”
And so that’s where we left it. Later that night, I deleted my profile in the dating app and decided to start fresh as a fresh fantasy developed around matching with her and sending filthy messages that would lead to lewd pictures.
Chapter 7
A couple weeks had gone by since the reading and subsequent agreement to start finding people via a dating app. I set my age range to 22-55 on the hopes that I could maybe come across my mom, but so far there’s been no luck. She refused to show me her profile, even though I showed her mine with the prominent “age range 22-55” displayed on it. Besides that, the dating app experience went pretty well. I had a few dates and they all seemed pretty interesting, even though they paled in comparison to the erotic taboo of fantasizing about my mom.
It was a Saturday night, and I just getting ready to go out on one of those dates when a text from her arrived.
Mom: I’m done with this app! I just got back from my second date and it was a disaster. All these old men just lie about their age. 52 my ass! He showed up with a walker!
Me: Well I could give you the name of a cougar site haha
Mom: I bet you can!
Mom: Mr. 22 – 55 😉
Me: Well I’ve had a few good dates, haven’t I?
Me: 😉
Mom: Very funny, I guess we’ll have to see. I have another date tomorrow so hopefully this will be better than the last one.
Me: If not, I wouldn’t mind going out with Renee again
Mom: Hah! There’s no way that’s gonna happen again.
The next night, her text arrived right on cue.
Mom: Yep, another total disaster.
Me: The date?
Mom: Self-absorbed asshole. I’m officially done with this and all dating.
Me: Nonsense! You’re too much of a catch, mom.
Mom: You’re too sweet!
Me: Again, I wouldn’t mind going out with Renee again 😉
Mom: Tough Luck!
From there, I let it be for a bit until this came in two hours later
Mom: Fine, we can roleplay dating this weekend. Nothing sexual though! I just want to have a good time out with a guy.
I went from nothing to an erection in what felt like record time.
Me: Seriously?!
Mom: Sure, but I’m warning you. Any sign that you’re getting corrupted and I’ll end it immediately! We can meet in the city again. How about that bar we went to a couple of weeks ago?
Me: That would be incredible!
And then I decided to test things out.
Me: What if you wore something like this?
I sent her a picture of a dark green club dress. The type that barely covers the ass and cuts the cleavage almost down to the navel.
Mom: You’re out of your mind! I couldn’t wear something like that in public.
Me: Of course you could! You have a killer body, mom.
Mom: I suppose I’ll go shopping for something new to wear, but it definitely will cover more than that!
After that, we set some ground rules. No kissing. Arm around shoulder or waist only. I can’t say anything to my sister since she’ll be seeing my mom leave the house for a date. Suffice to say, I was ecstatic. I spent the entire next day just jacking off the fantasy of what she would wear. I had a date with my mom.
Chapter 8
In the days ahead, we talked on and off about the upcoming date. She backed out several times, only to cave once again after showing proof that I was in fact going out on dates with other girls and would continue to do so and that our thing was just to have some fun. Our date wound up being the same bar we were at before for our last meet-up. I arrived a half-hour early in order to get us a good spot in the corner on this plush couch. Had a quick cocktail before she arrived because my nerves were through the roof. Despite that, when she walked through the door, holy shit.
Although the black dress she wore was more modest than the slutty club dress I sent her, this one was still smoking. It clung to her so tight and was cut low enough that her freckled tits were on prominent display. I was speechless as she grinned and walked over. I stood up from my seat and reached out my arms for a hug. It was weird for a moment when I had to remind myself not to give her a hug like she was my mom. She came close and once we were almost eye to eye, I realized she had on heels which probably put her around the 6’2 range.
She said my alias as I closed my arms around her and pressed her tight.
“oooh oooh” she was startled from the closeness. “I definitely need a drink!”
We ordered a round from the cocktail waitress and sat back in our couch. She leaned in to me a little and I was amazed my hardon was staying concealed.
For the first two drinks, we just talked about our normal life stuff, although it had this twist where we be telling it like we were dating. So instead of being like “School is going decent, mom” It was “School is going decent, babe.” It was minor, but goddamn was it hot when she called me a stud.
Around our third drink, another couple came over and sat across from us and we started up a conversation. They were mid 30’s somewhere between mine and my mom’s age. It was awesome to introduce her as my date renee and her eager to play along. We made up a story that we were a freelance pair of road bike and travel magazine magazine writers who were in town to report on the city. It was a pretty good lie on my part and gave mom alot to work with since she was so familiar with road biking and traveling. I think she really liked the “roleplaying while roleplaying” thing because that’s when her hand shifted onto my knee. I’m positive she had to notice my erection at that point but it didn’t seem to stop her from talking to the couple about the importance of a good derailer for a bike.
I was pretty tipsy by the time we left. Our hands were interlocked and she was close. “Ugh, it’s not fair. Why do you have to be my… ssssss” She began to hiss out and then started to laugh.
I busted out laughing too. “You’re saying?”
“You know,” My mom said and came close to me. “Our rules. You aren’t going to grow up with some sex disorder about your” she looked around and said quietly. “mom.”
As I thought about seeing her naked body, her firm tits, her pussy, even going so far as her asshole, all I could thing was that it was way too late to prevent some sex disorder toward my mom.
And here’s where it gets good.
We were walking around looking for a night cap when we came across this dance club. It was this college dance club where the average age was my age, 22. I wanted to try for it though so I asked her if she wanted to go dance there. She protested at first that she couldn’t dance, but after telling her that it would be great, I could lead, etc, she grinned and said, “Alright, but only for one song”
We went in to an incredible amount of noise and flashing lights. The dance floor was packed, but with my mom’s hand in mine, I led her to the bar, got two vodka sodas, and we proceeded onto the dance floor. I grabbed her waist and began to dance. The music was pretty clubby and definitely warranted some grinding, but mom maintained her distance even though her hands kept running up and down my chest. I was drunk, but I could swear a few other guys were checking out my mom while they danced with their girls. I felt validation in a sense that I wasn’t the only one who found her sexy.
“You’re a good dancer!” She shouted as she put her arms around me and came close. “Everyone here is so young!”
“You are too!” I shouted back. “And just think of it as you being a cougar!”
My mom backed off for a minute and gave me a sideways look. I forgot that she didn’t want to be associated with anything cougar-like.
She stepped forward and shouted, “Would a cougar do this?” and then turned around and began to grind into me. Holy shit, it only lasted a second, long enough for me to grab her hips before she backed away. Yep, she definitely felt my boner.
“This is so fucked up,” Mom shouted. “You’ve had that this entire time!”
“It comes and it goes?” I joked. I had no idea how she felt. “What can I say? I’m 22. I’m dancing with a beautiful cougar. You have a better chance of stopping time than stopping this.”
“A beautiful cougar eh?” She was back to dancing again, although at a distance.
“Absolutely, you have any idea how many guys have been oggling you tonight?”
“No way”
“Here, try this. Go to the bar. I’m going to go over there. If you get hit on in five minutes, you have to do a dare of my choosing”
“And if I don’t get hit on?”
“Ummmm…. I’ll clean the garage?”
“It’s on!” she said and walked over to the bar. I went to the other end to try to view. She posted up and looked over at me, giving a wink. She leaned back and put both elbows on the bar to look playful in an attempt to jab me, but sure enough, these two young guys immediately walked up and began talking to her. It was an actual convo too. She was smiling and engaged and I wondered when I needed to step in. Not that I was jealous, but I was so incredibly horny from the entire date up to that point and it felt unbearable to be apart. As I watched up, she seized up for a second. It was almost too quick to notice, and then proceeded to turn around and race over to me.
She walked up, grabbed my hand and proceeded to walk out, “They’re 18!” She shouted as I began to laugh. “We have to get out of here!”
We made it outside and the cool air felt so good on my sweaty skin.
“18!” She shouted again. “They’re almost Kaitlyn’s age”.
“See, I was right! You are a beautiful cougar.”
She playfully smacked me. At that point, it was midnight and mom decided to call it a night. We held hands as we went to a place where the ubers usually are found, the whole time I was thinking of the dare I wanted to issue besides the obvious, a kiss. Nothing else popped up though so finally when we arrived, I said, “And for the dare, how about a kiss.”
“Fine,” She said as my knees buckle. “Close your eyes.”
I did and I felt both her hands grab my arms. It steadied my body as I was shaking with nervous excitement. Finally, I felt her lips. Those soft plush lips, on my cheek. She backed away and laughed. “You didn’t say where to kiss you!”
“Fair enough,” I said. She tricked me fair and square and at that point I was too drunk to think of a clever comeback.
Her uber turned a corner and was only a block away at the red light.
I grabbed her hands and said, “guess this is it. I had a really good time tonight! We should do this again soon.”
Mom: “I had a great time too! And as for another one, get a few more dates with other girls under your belt and we’ll talk”
“Deal.” I answered and pulled her close for a hug. She backed her head away while my hands were still on her hips and I just went for it. Slowly, I leaned my face forward as she softly said “Jeremy, don’t…”
Too late. I went for it. I slowly touched her lips with mine. There was no movement on her part for a moment until finally her lips shifted to match mine. “mmm” she said as her mouth opened more. Enough to the point where I slid my tongue in. It took more time than I was used to until finally her tongue met mine. And there it was, I was french kissing my mom just as the uber pulled up. We backed away slowly and I went for one last kiss, which she responded to vigorously. She hopped in the uber and I immediately called one as well because I had to come back and jack off at the date. She texted the whole way home as a process it all.
Mom: Oh my god, that was so wrong. We shouldn’t have done that.
Mom: Well you did have the erection too so the kiss was nothing compared to me grinding on you.
Me: I had a great time! I’ll still date other girls! (I kept sending variations of this over the course of the next few messages)
Mom: You better still date around! What would your sister say if she knew? Your father!?
Mom: Not saying this was the last date.
Mom: Kissing needs to be back against the rules.
Mom: And where did you learn how to kiss like that?
And finally, by the time I arrived home, this gem came in that almost made me burst right there.
Mom: Renee the cougar. I guess I could see the appeal.
This morning I woke to a flurry of more messages about how we could never do this again and how wrong it way. I kept responding back that I had a great time and that I’m not messed up by it because I’ll still date other girls, find a wife, grandchild, etc etc. I figured I’d put the ball in her court because I have another sexual ammunition to last a lifetime right now. I’ve spent all day just jacking off. Holy shit her tongue had some real force and passion behind it. And that brief moment when she grinded on me. My mom the cougar.