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.
