So this happened back in my early twenties.
I had this bar that was located right under my apartment, and I would occasionally go down there for a late night drink whenever I felt like it. The place would be quite packed with college students from the nearby campus and I would find myself a hot chick or two to spend the night with, but I did have one issue; I had three roommates, and even though I had my own room, privacy wasn’t really a thing there, so at times I had to work around that. One time I fucked one chick behind a dumpster, in other words; I had to be creative, this time was no different.
I’m sitting at the bar sipping on my whiskey as I usually do on Sunday nights when I’m not working, when this gorgeous milf catches my eye from down the row. She has long curly black hair, plump lips and sparkling blue eyes that make it incredibly hard to look away from.
I glance over at her and she smiles at me, I smile back and finish my whiskey in three decisive gulps.
Before I walk over I make sure the bartender pours up two margaritas.
“One for me and one for the lady with the beautiful red dress.” I say as I come up next to her.
“Is margarita your go-to drink when initiating conversations with women at the bar?” She asks as she slowly reaches her hand out to grab it.
“It tends to get me where I want,” I reply, playfully.
“And where is that, exactly?”
I slouch over the bar next to her and seductively take a sip from my drink, while looking for an empty table.
“How about we take a seat at that table over there and see where we end up?”
“How old are you?” She asks nonchalantly.
“Old enough to buy you as many margaritas as you can drink I reply.
She nods and gets up, giving me a nice view of her clearly fake, but impressive breasts.
I lead the way to a small table by the wall, pulling the chair out for her before I take a seat myself.
“So, I’m Chucky by the way, but you can call me Chuck, like Chuck Norris, you know, from the movies.” I say and give her a flirty smile.
She smiles back and takes a gulp from her drink, “well, it’s nice to meet you Chuck, my name is Julia, like Julia Roberts, you know, from the movies.” She smiles back confidently knowing she hit the nail on the head.
Our conversation took off from there and was mostly flirting back and forth with the occasional dirty joke, which she seemed to enjoy.
“I really have to use the bathroom,” Julia said, “and don’t put something in my drink while I’m gone,” she jokingly added.
I laughed and got up to order some more drinks, but before I got anywhere she grabbed my arm as she passed me, “but if you do, make sure you get me good.” She whispered in my ear and walked over to the bathroom.
I couldn’t help but to stare back at her ass as she walked away in that red dress that perfectly hugged her body, and those red heals made her slim legs look even slimmer in the dimly lit room. That’s when I knew she was in a completely different league.
It didn’t take too long for her to return, and the second she sat down she chugged the little margarita she had left and began sipping on the other one I had just ordered immediately.
“Are you alright?” I asked, since she went from being very confident, to being a tad nervous.
She looked at my while she slowly ran her tongue across her upper lip.
“Come closer, I want to tell you something.”
I leaned over so that she could whisper whatever she wanted to tell me right in my ear.
“I’m not wearing any panties.” Was all she said before leaning back, spreading her legs, staring me dead in the eyes.
She wasn’t nervous, she was over-confident.
It caught me off guard, but I decided to play along. I pretended to drop my wallet, giving me an excuse to bend down and pick it up, whilst doing so I glanced under the table and saw her soaking wet pussy only inches away.
I sat back up again thinking about what I should do next. I took a sip from my drink and suggested that we should take a selfie together, to have something to remember our first “date” by.
She just smirked and nodded in response.
I got up and moved my chair over next to her, sat down, got my phone out, held it up in my left hand, while sneaking my right hand down under the table and up her thighs, all the way up to her glistening entrance.
I slowly ran my fingers all along the outskirts of her pussy, just massaging it ever so gently. She moaned quietly before catching herself, and I just said, “smile for camera darling,” as I snapped a photo of us innocently having drinks together.
Her moans were getting a bit too intense as I picked up the pace, and this wasn’t really the place for it, so I finished my second margarita and suggested that we’d finish this in the bathroom before someone noticed us. She agreed, got up and walked over to the bathroom as subtle as she could, but she was practically dripping at this point.
I stalled for a while before finally following after to the bathroom, which was right passed the bar. I tried to stay as subtle as I could walking passed the bar, but hiding a boner isn’t exactly an easy thing to do.
I walked into the toilet and locked the door immediately behind me. When I turned around I was faced with one of the most amazing things twenty year old me had ever seen, a milf’s pussy dripping onto the toilet seat, as she had pulled her dress up all the way to her waistline, leaning back on the toilet, holding her legs up in the air.
I could barely hinder myself from pulling my cock out right then and there, but slow and steady wins the race.
I slowly walked up to her and gestured for her to keep quiet, before getting on my knees and with the same finger that I gestured with I gently began sliding it in and out of her pussy before adding my middle finger. She was so wet that her pussy juices began running down the length of my arm, so I removed my shirt and continued, but now I used my tongue instead, eating her clean.
I could hear her breathing picking up in pace and I could feel her body getting tense. In this moment I felt like testing the waters, so I licked the juices of my index finger and made sure we had eye contact before I stuck it up her butthole, and then I did it again, and again, and again, faster and more rough for each time.
Until she was on the verge of screaming, but she held her hand over her mouth hindering any noise from coming out. I continued to finger her asshole and lick her pussy until I felt her entire body beginning to shiver. I got on my feat and began viciously rubbing her clit until she let out a loud, “OH MY GOD!” and squirted all over the bathroom floor.
She leaned back and let out a relaxed sigh and giggled.
“How loud was that?” She asked, now on the verge of laughing.
I simply shrugged my shoulders in response and looked at the mess we had created.
“I had no idea I could squirt like that.” She said.
“Where in the world did you learn to do that with the finger in the butt?”
“I might be young, but I know a thing or two. Trust me, there is a lot more where that came from.” I teased.
“Well, I would love to return the favour, but I really don’t think I have the time to do so since my kids are probably waiting for me to pick them up from my sister’s.”
I was a little disappointed to hear that, but understood.
“So.. same time next week?” I joked as I put my shirt back on.
“Hmm.. why wait? Give me your number and I’ll text you whenever I have time, because I would love to do this again, but next time we should probably pick a bigger toilet,” she laughed.
We exchanged numbers and headed out, nobody gave us any notice other than the bartender that gave us a slightly judgmental glare, not that I mind.
Source: reddit.com/r/gonewildstories/comments/lxwch8/my_hot_and_steamy_affair_with_a_married_woman_pt1