Dating Mom

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.