Sexploits: My First Cougar

cougar2

On a summer, Friday night on the little coastal island named Tybee, about 12 miles south of Savannah, I was working at a bar on the beach.  It was great: warm weather all day, a plethora of women drinking all over the place, and to top it off, I was a bartender, so meeting girls was very easy for me.

This particular evening I met my angel…my trophy…my…Sophie.

At around 8:00PM, a group of about 7 women  all roughly 35+, came into the bar and sat down to order some food and get some drinks. They already seem to have some alcoholic fluids running through their system and I could tell this was going to be a fun evening.

A couple of the ladies were “OK” looking, one was haggard, and then there was Sophie.

Shoulder length blonde hair, tan skin, the body of a high school Gymnast, and big fake mammories. This lady was genuinely gorgeous, a total knock out.

Me - “Hello Ladies, what can I get you guys this evening?”

Girls –  “Mich Ultra, Vodka Cran, Tequila Sunrise….yada yada…” Girl drinks…

Me“Something to eat?”

At this moment I tend to notice that it seems Sophie is also the most prude of them all…damnit.

Sophie –  “I’ll have a small salad with light dressing and a Vodka Soda.”

Well, there goes my chance. Being behind a bar for a while, you can start to read how people are by the orders they make…maybe a burger and a beer and I might be able to get into this ladies pants, but after an order like that? Who wants to fuck this 21 year old bartender? Not someone that orders a small salad with light dressing!

I couldn’t! How dare I! This woman gave herself to me, she’s married, and she’s got money. I’m a broke bartender kid, I’m going to give this bitch the ride of her life.

My penis already accepted it and decided to move on for the evening.

They stayed for about an hour and a half, had numerous drinks, and eventually started taking shots. During the course of their stay and during the “Chit-chat” they tell me that they come to the island once a year, rent the same house for the weekend, and escape from their husbands.  Maybe this will turn out better than I expected?

When I deliver the bill, Sophie decides to grab it and pay for the party. I inform the ladies I have to tinkle and will be back after I relieve myself.

As I come walking back to behind the bar, I notice the girls chatting like a bunch of yentas, kind of like a group of school girls at the cafeteria table plotting something.

Me - “Well ladies, you all ready?”

Sophie gave me a look of a horny angel.

Sophie“Want a tip?”

Trying to be sly and cool…which never really works and probably makes me look like a complete tool:

Me“Well it is not required but it would greatly be appreciated”

…see… I’m a tool.

Sophie“Well come get it”

She opens up her blouse a little bit and reveals a fifty dollar bill tucked in between her gorgeous orbs of breasts. I was going to have to make this good and worth her $50.

I calmly walk around to the other side of the bar where the girls are sitting and I hear them saying things such as “Sophie, what’s he doing?”, “Are you serious? We agreed no guys for the weekend”.

Fuck that.

I get behind her and take put my face in-between her neck and shoulder, pull her back, and lick her all the way down to the middle of her breasts and grab the fifty with my mouth…she was squeezing my arms and back of my head the whole time. I think she got excited.

Before I could say another word, she pulled me forward and slid her hands to the top of my head (noticing the big boulder of a ring on her finger make it past my eyes) and pulled me down to her naughty places.

The bar erupted in screams and claps, I was the center of attention and Sophie loved every second of it. Flash photography from her friends and other spectators at the bar almost blind me from actually getting a good look at those breasts from up close.

The ladies leave the bar, but I know they will be around because it’s a very small island (2 miles X 3 miles) and on top of that I know where the beach house is they are staying at. I am not a stalker.

Me and the other bartender Brian, decide to close shop early so we can get in some drinking because the evening seemed fun, and our bar was slow so we said “Fuck it, lets bar hop.”

We go to a bar called “The Sand Bar” because Brian’s girlfriend works there and hooks us up.

Guess what group of ladies were there, completely shit housed?

It wasn’t the Golden Girls…It was my Sophie and her minions.

As they see me enter the door, they go apeshit.

Girls “Kevin!!!” “You off work?!?!” “Lets take some pictures”

I am a mannequin for these girls, they have me pose in different positions, grab my ass, make me put bra straps in my mouth…I didn’t mind one bit.

The bar closes down and we are told to leave. Brian and I decide to take a two minute walk to a bar that stays open a little bit later for the bartenders on the island.

As soon as I exit the bar, Sophie is standing outside inches away from my face, as if she was waiting for me.

Sophie – “Hey, what are you doing right now?”

Me“Umm…getting ready to go to have a drink and maybe call it quits, you?”

Sophie“I know I’m not supposed to do this but….”

At that moment she grabs me and starts making out with me…pretty hardcore. It was as if our tongues were having a boxing match. Sophie was no longer a prude.

As I’m showing her tongue how to wrestle, I hear her friends, some laughing, some in disgust, some cheering her on. I feel I must stop this make out because I noticed she had a fucking ring on her finger that looked like a rock from Stonehenge.  This lady was loaded…and married. If that is not the definition of a cougar, I don’t know what is.

This is also when I had feelings. I just got out of a 5 year relationship about 4 months prior and was not really used to just hooking up. So this was new to me. I felt bad for her husband.

I leave her and head to the bar. As I walk in there is my buddy Brian (6’3” 300lb rugby player) , Doug (big tattooed Irish bartender) and Larry the Karaoke guy (Fat motherfucker). Then there is me, the new guy to the island, 5’7 and 175lb. I’m like everyone’s little brother.

Sophie lays there with her covers all the way to her neck as if she had done something naughty.

Me – “Guys, I think I’m gay.”

Doug – “Well we all know this, but what makes you finally realize this? Hey you guys see that group of girls from Pooler, that blonde with them was fucking hot.”

Me“That is why I’m gay.”

Brian“Yeah, he just made out with her…and he’s here. I was expecting not to see you till tomorrow cause you seemed to have it in the bag.”

Doug“This New Castle is on me, homo”

I drink my sorrow away. Why did I leave? Why did I let my conscious get in the way? WHAT THE FUCK!!! GOD GAVE ME A CHANCE AND I THREW IT AWAY!!

Brian“Come on man…lets go, you can crash at my place.”

Me “Thanks man, can we drive by their house to see if they are still partying out on the patio or something, I really wanted to put my penis in her.”

Brian “Sure little buddy.”

We drive toward where they said they were staying and it’s actually on the way to Brian’s house with Larry the Karaoke guy following behind.  And what do you know; all of them are on the deck still drinking.

Me “Brian, stop the truck…that’s them! LOOK LOOK!!”

I was like a kid waking up Christmas morning.

Before the truck even stopped I threw open the door and almost ate shit getting out. I run to the driveway and scream “Ladies!!”

Girls “What the fuck..who is… KEVIN!!! Oh and Brian!!! Come up come up! Have a drink.”

SCORE!

All of us are sitting on the deck drinking: Me, Sophie, Brian, Larry the Karaoke guy, and the rest of the girls. The conversations were getting graphic. Some of the girls were talking about liking it in the ass, how their husbands were worthless, yadda yadda yadda. Sophie wasn’t saying a word, but just looking at me.

Sophie“Alright, well I am off to bed”

She walks passed me and gets right in my ear and says “Second bedroom on the left” and vanished into the house.

Brian noticed she whispered something to me but couldn’t quite make it out and Larry the Karaoke guy also noticed something had occurred…I sat there for a moment in shock.

Brian“God only gives you a few 2nd chances, whatever she said, you better do it”

Me “Could one of you girls please let me know where the restroom is?”

The coolest one out of the group eagerly jumps up and walks me into the house.

Girl “She is in this room”

Me“I really have to pee though”

Girl – Yeah right, go ahead”

Me “No I really have to piss”

Girl “…bathroom is right there.”

I ponder what I should do. Do I walk in and say, “Hey, how ya doing?” I had no idea! I was nervous as all hell, how could an older woman, a damn good looking one at that, want to screw me?

When I exit the bathroom, I see the girl who walked me into the house peeking through Sophie’s bedroom door and I hear giggling. She notices me and shuts the door and stands at attention like I’m getting ready to walk into a meeting with Hitler. I can’t even say a word when she breaks character and shoves me into Sophie’s room and the door shuts, I look behind and realize there is no going back now.

Sophie lays there with her covers all the way to her neck as if she had done something naughty. I try to play the innocent card by saying, “I don’t know what I’m doing here, she ah…she um..pushed..me um…I can lea…”

under-the-sheets

She seductively slid to her knees on the bed revealing a totally nude, beautiful body…I’m getting erect right now just thinking about it. Tan all around, had a nice six pack, perky fake boobies. Totally shaved down south and very small labias. It was like the Greek Gods carved her out of stone.

Before I could say another word, she pulled me forward and slid her hands to the top of my head (noticing the big boulder of a ring on her finger make it past my eyes) and pulled me down to her naughty places.

It was amazing. I could have munched on that for days. And what was great, you could tell she has yet to have had any kids. I was in heaven. Here I am, 21 years old, going down south on a lady who I thought at the beginning of the evening I had no chance with, because she ordered a Vodka Soda and a small salad with light dressing.

I slip my shorts off and shirt and slam it home after about 25 minutes of enjoying the nectar of the gods. As I entered her, she let out a smooth soft moan. I was ready to bust my nut right then.

I couldn’t! How dare I! This woman gave herself to me, she’s married, and she’s got money. I’m a broke bartender kid, I’m going to give this bitch the ride of her life.

Now at this time, she is laying on the side of the bed and I am standing on the floor giving it to her. I pull out a little too far and when I come back in for the landing, I accidently hit her ass. As I am ready to apologize she lets out yet another moan with this following, “Oh yeah”

DING DING!!! We have a winner!

So what was I to do? I continued fucking her in the ass.

After about ten minutes she stops me.

Sophie “Jesus, what is wrong with you?”

Uhhh what…oh no, might as well back off and start leaving.

Sophie“There is no way you’re 21”

YES!!!

Sophie – “Get over here and finish me off, I want to taste you”

We continue to fuck for another 45 min it seems. When I’m ready to cum I let her know. She can’t wait for it.

I pull out and unload my clip all over her lower stomach, right above the goods. She takes her hand and wipes it up and starts licking her palms, over and over again, trying to savor every last drop like a lost man roaming the desert drinking the last 8 fluid ounces of his water. I find this so hot I pray to god to make me a woman at that moment so I may have multiple orgasms. My prayers are left unanswered.

She lay there out of breath.

She did get the energy to say, “You got me off harder than my husband ever has.” Awkward.

We get dressed so we can go back out on the deck and join the party. Before we exit the room she tells me to say we were talking about the meaning of life if anyone asks what we were doing. I oblige.

As we exit to the deck everyone is looking at us and knows what we have just done.

Me“…Oooh yeah. Rright, right. So that is the meaning of life. Brian lets go.”

I go to give Sophie a hug and when I do I just had to ask how old she was.

48 and fucking beautiful.

I never saw her again but she did call me to ask where I was because she was back on the island having a divorce party. I just moved back to Las Vegas so I missed out.

Thank you liver. You made my night.

6 Comments

  1. I actually laughed at the Greek Gods comment. And I also enjoyed the part where you said, “This was when I had feelings.” (Implying that you’ve learned that feelings are for pussies, so bravo)

    Also, I have to give myself props for adding that picture. I would do unforgivable things to hook up with that girl…

  2. Great picture Ace… maybe you need to read the description of Sophie again…

    “Shoulder length blonde hair, tan skin, the body of a high school Gymnast, and big fake mammories. This lady was genuinely gorgeous, a total knock out.”

    Great story! I think we need to have a cougar series…

  3. That’s my little man, I wanta be like him when I grow up… Just knocking the botton out of the good’s on a summer, Friday night on the little coastal island named Tybee, What more could you ask for,,,,

  4. a sophie sandwich…Mmmm

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