My First Time with a Cougar [30] [f] who Pried Me [m] [21] Out of My Bartending Shift

This story takes place a few years back. I was twenty one, in college and worked as a bartender at a sports bar just outside of downtown.

Although I lost my virginity in High School, and had a pretty consistent and solid sex life, I had always been girlfriends both in HS and College.

I had recently broken up with my girlfriend and just started to hook up with some of the girls at school who I knew and hung around with frequently.

That said, I’d never had a one night stand, nor had a hooked up with a customer from the bar and I had never been with an older woman.

Soon enough this would all change. Looking back on it, I was pretty naive about a lot of sexual things, but I digress.

The bar. It was a cool place. Private owner (non-corporate), great clientele, a handful of regulars and a solid staff. Most of us were in college or had recently graduated, it was very much the fun, vibrant grab-assy type of staff that I’m sure many of you who have bartended or worked in restaurants can relate to.

We were all super young except for the head bartender, the madam, mamma-san.

Her name was Jillian.

She was pretty, long blonde hair, blue eyes and wore a set of black hipster glasses. She could be fun, but for the most part, she was the boss, she was the warden that kept all of us idiots in-line and everybody knew it.

At any rate, one crowded Saturday, Jillian posted up at the bar with a friend of hers. This was rare to see Jillian bring friends to the bar.

“Johnny!” I heard Jillian call out as she summoned down to the other side of the bar. She and her friend were posted up at the right corner of the bar.

Her friend also very attractive for an older woman, I’m guessing she was in her early 30s, she had long auburn hair, brown eyes, slightly puffy glossed lips, perfect teeth and a warm yet flirtatious smile.

More cute than sexy, but an adventurous glimmer in her eye that made one want to know more.

As I made my way to their corner, I could tell Jillian was a little buzzed. She said, “This is my friend Kiara, Kiara this is Johnny.”

At least I think her name was Kiara. It must have the booze talking, but she put the emphasis on ‘my friend’ when she introduced her.

“Nice to meet you Jillian’s Friend,” I smirked.

Jillians friend was taken slightly a back I saw her mouth pull back slightly, but without missing a beat, she cocked her head and said “well, nice to meet you, college boy.”

Although I’m pretty sure her name was Kiara, I can’t be positive because I spent the rest of the night addressing her as “Jillian’s friend” in a playful, flirtatious way.

It was a busy Saturday, for the most part it was business as usual. I would check-in on the girls.

Always addressing her as “Jillian’s Friend”. Never my her actual name.

We would talk a bit in between busy rushes. She knew I was going to school for Business Marketing. She was a Mortgage Broker or did someone with Real Estate. There was some chemistry in our short interactions.

Throughout the day, occasionally our eyes would meet. A quick glance that only the two of us would share. Pretty innocent flirting and just good customer service in my mind.

As the night went on they started to get a little more loose. Shots. Sex talk. Would you Rathers and Never Have I Evers. All pretty normal Saturday night shenanigans.

Normal until Jillian motioned me to come down to the bar by summoning me with her index finger.

“Your not closing tonight are you?” She asked. Even through she knew the answer was no.

“Nah, not tonight. I’ll probably get cut in a hour or so.” I responded.

“Yep, that’s what I thought. Will you do us a favor?”

I nodded.

Kiara jumped in before Jillian could even ask and said, “So… Jillian has got to leave. But I want to stay, this place is super fun.”

“Great. Your in good hands” I responded. As I held up my hands.

“It’s not only that” she smiled shyly. “I’m a bit buzzed and shouldn’t drive. Jillian mentioned you live over by campus.”

I nodded yes.

“Cool, so I live in between, how bout I buy you a shot now and you drop me off on your way home?” She flashed her adventurous smile.

“Good by me.” I responded. “And the shot?” I asked.

“Two dirty Girl Scouts” she said with that same smile.

Fast forward 1 hr or so, I am driving her home in my Jeep.

Real talk. At this point I had zero intention or inclination of hooking up. We were flirty yes, but that was also my role as a bartender.

Plus she was Jillian’s friend. She was definitely attractive. But she was also order, although I knew it wasn’t out of the realm of possibilities it wasn’t the first thing on my mind.

More so, I didn’t want to get crushed at work for trying to make a move, or worse, to get turned down by Jillian’s friend in the event she legitimately just needed me to drive her home.

I digress.

We pull up to her house. It’s a small little bungalow.

I pull up by the mailbox and said something like, “good times tonight.”

She paused and asked, “do you like wine?”.

“I like all the alcohols.”

She motioned her hand with confidence, not even so much of a question, but a statement and said, “great, you’re coming inside.”

I put the car in park and started walking in with her.

She unlocks the door. Immediately puts some music on as we walk into the house and says, “let me give you the quick tour first.”

We start walking down her hall way, she is giving the abbreviated tour with hand motions, “Kitchen, living room, and follow me.”

As I walk behind her, I get the first real look at the perfect little bubble butt she is packing in her White Denim jeans. She is in good shape.

We walk towards her bedroom. “This is the master”. She says after a slight pause.

I am nodding, doing the usual motions when someone is giving you the house tour.

She clarifies. “This is my room.”

I am standing there, nodding. Clearly being naive, just nodding my head like an asshole and still thinking I am on a fucking tour of the house.

In the brief silence and while I am nodding and pretending to look around, she comes toward me and pushes her plush lips against mine.

I could taste the apple cherry lipgloss as her tongue gently guided into my open mouth and she started to push me further into her bedroom.

Instantly, I grabbed her hair and started to kiss her back. Hard.

She moaned and pulled me into her bathroom just off the bedroom.

“Your going to take a shower with me”, she demanded.

At this point, I’m starting to appreciate how an older girl knows what she wants and can take charge to be assertive.

She turned the water on and we continued to make out passionately in her bathroom. Clothes started coming off, I was still in disbelief that this was happening as we continued undressing one another.

It was one of those make out sessions that was just fucking hot.

She was older, I was younger. She was a customer and my bosses friend. So much wrong and it was feeling so right.

I knew one thing. That I fucking wanted her. Now.

I unbuttoned her white denim jeans and she helped pushed them to the floor as she went for my belt buckle and unbuttoned my jeans.

I picked her up by her hips and put her on the bathroom counter.

She pulled me in closer, I could feel her warm breath panting on my neck as her hands tugged at the back of my hair.

The counter was perfect size. She pulled my hips into hers and the only thing between us was the cotton from my boxers, now lined up perfectly to her pussy covered only by a satin red thong.

She was making me so fucking hard, as she continued to moan and breathe onto my ears and neck between each kiss.

It felt like my dick was going to literally rip through my boxers. I’ll I could think about was the small layers of fabric that stood between me getting inside of her.

She reached around and started to tug my boxers down from the back. I quickly helped her and pushed them down to my ankles.

She wrapped her legs around me and pulled me in closer with her legs pulling me by being wrapped around my ass.

My cock now throbbing against those red satin panties. The shower still running, but neither of us getting in.

She let out another gasp and reached down and pulled her panties to the side.

For the first time I could see her beautifully exposed and shaven pussy.

She ran her finger up her slit and put her glistening finger up to my mouth. I could smell her sex.

It was such a fucking turn on, she smelled so good. So primal. As if she had wanted this all day.

I took her finger in my mouth as I locked eyes with hers.

She tasted so good and her eyes were begging me to be inside inside of her.

I leaned in for a hard kiss making sure she could taste herself. I could feel her grab my cock and position it just in front of the entrance to her pussy.

At this point, a normal person would probably be thinking about a condom, but that was the furthest thing from my mind, I went in for another firm kiss and fully thrust my throbbing cock deep inside of her.

It was one of those perfect angles where her pussy was angled slightly lower than me.

She was perfectly wet, I slid in deep right from the beginning. She let out a gasp of relief and moaned in pleasure as if she had been wanting this her entire life.

I gave a couple of thrusts and pulled back to look at her.

She was panting at me with her brown eyes, the look that you can only see when you have your dick fully inside of someone.

I took a minute to savor this look and went back in for another kiss.

She continued to moan as we thrust together.

“My god” she let out as she grabbed the back of my neck.

Still hearing the water from the shower running and the lights fully on, I could see my dick glistening as I continued sliding in and out of her ravenously hungry pussy.

I started to slow down so I wouldn’t cum and was fixated on watching myself glide slowly in and out.

In. And. Out.

My piece was glistening in the light of the bathroom and amplified by the white
tile of the counter.

I was in a hypnotic rhythm when I heard her moan, “I want you to cum in mouth.”

I held her red panties to the side as I continued gliding in and out.

In and out.

I’m guessing I didn’t acknowledge I had heard her, because she said it again, louder. Only this time she moaned, “I fucking want you to cum in my mouth.”

I was so fucking turned on. I had definitely been with girls who swallowed before, that was pretty common. But I never had been with a girl asking, hell, demanding, to go directly from her pussy to her mouth so she could swallow my cum.

I grabbed a fistful of her auburn hair and told her, “you are going to cum on my Dick first”.

The combination of those words, the hair pull and my deep thrust must have sent her over the edge as I could feel her pussy start to clinch and spasm on my rock hard cock and she moaned in passion.

Her legs were shaking and she moaned like something I have never heard.

She needed this release.

As her legs stopped shaking, she lowered herself off of the counter and came down to her knees.

She put me into her mouth and was moaning on my dick. She was so fucking good at giving head.

Her mouth felt almost better than her pussy and it was a turn on watching her feverishly licking and sucking like she was on a sole mission to get all of the cum out of me.

Moaning onto me with each passing lick as she took took all of me into her mouth.

Her left hand came up and started to tickle my balls and I could hear the shower still running in the background.

At this point, I couldn’t help but think that the only reason she wanted to shower was to “freshen up” from sitting at my bar in those red satin panties all day.

But, now, here she was, on her knees in her own bathroom floor, licking up all of her pussy juice and her fresh cum of off some random ‘college boys’ dick.

It was fucking hot. That thought sent me over the edge.

I told her I was about to cum. She continued sucking, started moving her other hand around my shaft and moaned “mmm hmm”.

I held onto her head with both hands as I started unloaded rope after rope into her wanting mouth.

She swallowed every piece of it. With out missing a beat.

My knees shuttered, I nearly fell over after my balls unloaded every last rope into her mouth and she was still on the floor sucking every last drop.

My dick was still in her mouth when my tip became uber sensitive. That post blow job sensitivity that can make you shudder.

I backed up slightly letting me slowly fall out of her mouth.

She closed her mouth, took one last swallow and looked up at me.

“Fuck that was hot. I really needed that.” She said, still on her knees.

“Yes, you are amazing” I said.

As she started to put her pants back on, she said, “we probably shouldn’t tell Jillian about this either. Probably best if you just tell her you dropped me off. Make sense?”

“Totally agree.” I said.

“This was fucking awesome, but I really do have to get going.” I said.

“Ofcourse.” She said with a smile. I gave her a hug and saw myself out.

Now, the best part of this whole story is that I had a career fair to go to the following Tuesday.

As I’m walking through the booths, I turn the corner there is Jillian’s friend. At a booth with what looked like her boss.

I was a student visiting booths of potential employers, handing out resumes and such. She was an employer trying to recruit students.

Our eyes met, my heart sank. I could only imagine what she was feeling as I could see her face started to blush.

Both of us frozen in motion.

“Would you like to learn more about XYX Mortgage Company?” I heard the older more senior woman ask me.

It’s at this point, I fully realized I didn’t know her name, I had spent so much time calling her “Jillian’s friend” that I actually forgot her real name.

I politely waved ‘no thanks’ with my hand and could see “Kiara’s” eyes beam a ‘thank you’ to me.

Was it a ‘thank you’ for not stopping to talk with her and her boss at the booth or a ‘thank you’ for the other night, I can never be sure

I can only imagine her response when her boss asked her why she was blushing or if she knew me at all.

Back at the bar, I told Jillian that I dropped her off. She didn’t ask any questions.

I didn’t ever see “Kiara” in the bar again.

Source: reddit.com/r/gonewildstories/comments/lbmj5y/my_first_time_with_a_cougar_30_f_who_pried_me_m