Handling a “Karen” at a wedding. [MF]

I have a dear friend who runs a wedding catering business. Before the pandemic I would help him out on busy weekends. I would bartend and handle small jobs on the day of the wedding. I enjoyed the job immensely, made good money and met some great people.

The wedding in particular was over fourth of July weekend a few years back. I was bartending for a rather large gathering, 250 people for the wedding and 350 for the reception. The family paying for the wedding was your typical rich family in the area, no expenses spared for the bride. 

The wedding was held at a restaurant/hotel resort on a local popular lake. The day was gorgeous as the skies were blue and the sun was shining. The temperature was in the high eighties which made for some more provocative wedding guest attire. The resort was breathtaking and the hotel on site was one I could never afford to stay at.

The wedding itself was at 3 and the reception started 4:30. Immediately once the bar was open, the guests flooded the bar for refreshments. Everyone was hot and sweaty from sitting outside for the wedding. The women were all gorgeous and refreshing to the eyes, most had arrogant looking men attached to them at the hip. From sun dresses to one pieces, to conservative and very revealing. It was early on in the evening when I met her, I never actually found out her real name but I will refer to her as Karen. You know, “Karen” the name given to any white woman acting a fool or making a scene. They have a bad reputation, but some sure can fuck.

When Karen was sober she was a bitch, when she was drunk she was a cunt. Karen approached me at the bar asking me to make some random ass drink she probably knew we would not have. Of course this was unprofessional and quite the ordeal for her. How dare we my bend over backwards for her. Karen was someone’s aunt in a rich family, who was probably invited out of politeness. However, she also was a slender mid forties woman with a tight blue sundress, large breasts and the bluest eyes I had ever seen. Her dress was form fitting and hugged her body well. My imagination was curious as to what was under the dress. Her legs were toned and her calves fit. She wore respectful heels that matched and tied her look together. Her voice was pleasant when my cock was fucking her, but anytime else it made me insane. 

Karen settled on some tonic vodkas since we didn’t carry her rich ass tequila. I would make her a drink and she would dissapeare for a half hour. Karen would always return for more drinks, and more complaining. Some drinks were to strong, others too light. She made jokes she would laugh at before anyone could laugh, if they were funny. After her fifth drink in a hour and a half, Karen was getting pretty intoxicated. I also started getting more confidence and firing back at her quick bullshit complaint. I was basically playing the flirtatious asshole rather than be a huge asshole like I would normally be if I was not working for a dear friend. Karen at first was struck that anyone would talk back to her, but I could tell she liked it. There were 3 other male bartender’s and she sought me out each time. If she really didn’t like my tone, she could go elsewhere.

The more she drank, the more she flirted. She made it very evident she was divorced and staying at the hotel on site, so I didn’t have to worry about over serving her. As it got close to 7pm Karen arrived for another drink.

“Do you get breaks? You look tired.” She said to me slurred.

“Not really, we work till end of night.” I said to her handing her a drink. Wondering how fucking wasted she was. She was still standing and talking so that’s good.

” I think I’m gonna go take a break, in my room.” She told me. Karen reached in her matching purse that was probably bought just for when she wore her sun dress. She pulled out a pen and found a napkin on the bar. She skribbled on it and left it face down in front of me. Our eyes locked briefly, then she showed a half smile. She walked away with her drink and left the napkin for me. I stood a moment wondering what had transpired, and picked up the napkin. It read,

“Here’s my cell number. I’ll be taking a break in my room, maybe you can bring me another drink?”

The note was barely legible, but I understood it. I watched as Karen walked away to her table to grab something, then up the steps to the hotel area.

Another bartender named Anna walked up to me smiling, she had saw the entire thing. 

“That bitch leave that for you? She has been so loud and obnoxious all night.” Anna said laughing. 

Yeah she did, she’s been all right.” I replied back.

If we were being totally honest she was being the cunt of the wedding, but she was also really damn sexy. She had a look that made me want to peel off that dress and kiss her from head to toe  I was kinda into her and when she left me that note, I knew what she wanted. I found my buddy working in the food area. It was close to 7:30, and the dinner rush had just finished. Now was time for the boring wedding talk and bullshit. I told Dylan exactly what was going on and what I wanted to do. Like a good friend, he was totally on board as long as I didn’t cause any drama. So with my buddy’s blessing, I pulled my phone out and asked Karen what kind of drink she wanted. 

“Vodka Tonic, room 212.” Karen messaged me.

Like the good employee I was, I made the drink as requested and graciously brought it to Karen’s room. Two knocks on the door and she opens it. Her blue dress still fully snug on her slender figure. I hand her the drink. She takes it with a smile and invites me in.

“Good food, good drinks and room service.” she said with a smile. Her voice didn’t seem so slurred as before.

As I walked into the room, it smelled of alcohol. On her dresser I saw the expensive tequila we did not carry, opened and half gone. Karen was either a respectable functioning alcoholic, or she was about to pass out any second.

“Would you like a drink?” she offered to me. The first nice gesture from her I could remember.

I didn’t though, I could drink at the bar if I wanted. “I don’t have much time, my boss think’s I’m just delivering a drink.”

She gazed at me, shocked I turned down her nice tequila. “Well if you didn’t come for a drink, why did you come?” she asked me with a grin. She knew damn well why I had delivered her that drink. I was growing tired of her voice by the second, but she did look ravishing. She looked no more than 30, and as a 26 year old, I was more than ready to see how Karen’s experience faired with my youth.

“I think you know why I came up here.” I said to her as I took the drink from her hand and set it on the table next to the bed. I walked over to the overhead light switch and flicked it off, leaving just a single lamp lit in the room. The room was darker, more intimate. I walked back closer to Karen and placed my hands on her lower back and hips, embracing her. We were close and the smell of her rich perfume and alcohol was overwhelming. Without letting her speak yet again, I kissed her and she responded with her tongue in my mouth. I could taste every drink she had that night, but it was pleasant. She began to run her hand in my hair and on my back. Our kissing was passionate and the momentum had us moving to the bed, entangled in one another. 

I fell to my back and Karen landed on top of me in the bed. Now my hand was finding that sweet spot of her lower butt and dress area, reaching under her dress I grabbed hold of her ass hard. Karen responded by biting my lip, which made y dick twitch. We paused momentarily, kissing, paused and looking at each other. I think we were both wanting that moment, but just making sure ourselves. As we kissed, she grinded herself on me. By sheer luck my cock was facing upward toward my belly button, she had found it and was grinding herself on my hard shaft. I could tell she was enjoying it. I helped her out by placing both of my hands on her ass and moving her petite body.

Without a word Karen gets to her knees and places her blonde hair in a ponytail, she shifts down the bed to the floor and stays on her knees. Karen in her drunkenness struggled to get my belt undone, which i helped with. She pulled my pants to my ankles and removed them. I slid my boxers off and exposed myself to her, right there. She took my cock in her mouth, it was warm and well fitting. She began to lick my head with her tongue as we locked eyes, carefully timing when she took my cock in her mouth and she sucked me to the base. I took a handful of her hair and began to force her to suck me faster, quicker, and go deeper. Karen seemed to like me taking control, and always adjusted herself well as she pleasured me.

I enjoyed the view and the silence. The only noise in the room was the AC unit and her slobbering and gagging. Music to my fucking ears at that time. Karen was good at what she did and if I would of let her continue she would have made me cum, which would of been fine with me normally. Looking back I wish I would have shot a load down her throat. However, I felt the longing and urge to fuck Karen that night. I wanted to rage fuck her for all the shit she had put me and the staff through. Maybe her attitude came from a lack of pleasure in life 

With my hand still tied in her hair, I lifted her head off my cock, drool and saliva all over her chin glistening from the single lit lamp. She showed me this smile that let me know I was dealing with a dirty woman. She was happy in her place and enjoying herself. I stood up and helped Karen to her feet. I helped her lay down on the bed, practically switching roles. She lay at the end of the bed, me on my knees on the floor. From my knees I could see her panties covering her labia, a slight wet spot on her white thong panties from where we dry humped. Karen pulled her dress up higher and I buried my face directly into her crotch, smelling Karen’s most intimate area and her panties. Her natural aroma had me aroused even more,  I could smell the pent up sexless life she had been leading, tonight would be different.

Using both hands I pulled off her panties completely, revealing the most beautiful pussy I had ever seen. Her labia lips were tightly together with bits of wetness making their way outside her lips. It was a visually appealing vagina and I wasted no time. Karen was flexible and showed it, she spread her legs far apart and I was able to bury my face into her. I licked her clit gently and placed a finger inside of her, she was wet and accepted it easily. I would run my tongue from her clit down to her opening, where I would bury my tongue as deep as I could go, licking her thick juices from within. The good thick pussy grool that milks cock’s faster than anything. 

“Get on your knees.” I ordered karen.

As she stood up to readjust herself, I hugged her from behind, kissing her neck. I helped her slip out of her dress to reveal her nude body. Her breasts were fake, but perky. They looked great. I had Karen get on her knees and I nealt down once more behind her. This time I was able to lick her from behind. My tongue found the familiar spots, but also I began to rim Karen. Her tight pink hole tasted fresh and my tongue was soon penetrating her ass a bit. Karen was moaning as I licked her and reached around to grab hold of my hair, to force me where to go. As I tried to lick lower, she redirected me to her ass time and time again, she was enjoying her rimming.

My cock had been hard the entire time and I knew I needed to bust. I had been up at the room close to thirty minutes. I rose up and undressed. I walked to the side of the bed and jumped on, laying on my back and resting my head on a pillow. I used a finger to motion Karen to join me up top. She crawled on the bed and positioned herself on me. My cock slid into her wet pussy with no issues, right to the base. Karen let out a moan as if the air from her lungs had been forcefully removed. She lowered her head to me, our nose’s touching.

“Are you supposed to fuck wedding guests?” she asked as she took my cock completely out of her pussy only to forcefully sit right back down.

“I wouldn’t say it’s recommended, but it’s not against the rules.” i said back to her in a sarcastic tone.

Karen’s pussy walls were hugging my cock, as if both were made specifically for one another.

Karen rode me for what seemed like forever. I was in bliss. Looking up at her, watching her feel intense pleasure was wonderful. I was halfway about to cum the entire time, half the time trying my best to not. The urge was strong and almost felt like I had to piss. 

“I’m getting close.” I warned her.

“I want you to tell me when, then pull out and cum on my face.” she said to me. We locked lips once more. Her tongue in mine. Karen continued to ride me, vigorously with passion. I could feel the urge growing, and soon I was in the place of no return.

“I’m gonna cum!’ I exhaled, practically warning her. She did little to help or care, and continued to ride me. “Karen, i’m gonna come soon.” I restated to her. She continued to ride and ride.

“Fuck it” she said aloud. She lowered her mouth to my ear and in a whisper I will remember for my entire life. “You don’t have to pull out.” she whispered to me.

No more than twenty seconds later I felt myself release myself into her as she rode me. Her already wet pussy now mixed with my cum made her sloppy and messy. She used such force as she slid down my cock. I exploded inside her, releasing the biggest load I can remember. As if I had been edging myself for hours.

“You not want it on your face?” I asked out of breath and confused.

“Messier clean up on my face.” She said laughing.

Karen stayed on top of me, our juices mixed and we kissed. This time just our mouths, and more passionately. My cock became limp and fell out of her. As she rose up I saw all of my cum drip from her and landed on my groin, in my pubic region. Without even a warning, Karen slides to her stomach and begins to clean me off with her tongue. She licked, sucked and got every drop of cum off my cock and balls. Not a drop was missed, and she swallowed it all. Before getting off the bed, she crawled up to me and kissed me, using tongue. I could taste myself on her breath, but at that time I didn’t care, this woman had just done everything and more of what I wanted. I like it.

I looked at my phone and had been gone for 45 minutes. I didn’t have time to shower so I threw on my clothing and kissed Karen goodbye. Karen slapped my ass as I exited the room.

As I got back to the bar, Anna shot me a dirty stare as I think she knew why I was gone so long. I just smiled at her and tried to avoid the subject. I picked up where I left off and continued to serve drinks. I figured Karen would appear once more but she never came back to the wedding. I worked until close to midnight. As the party was winding down, my phone vibrated in my pocket. It was a message from Karen.

“Bring me one more drink and Mimosa’s are on me in the morning.”

I just smiled to myself, glad for the invite. I took Karen up on that offer. I stayed the night with her where we fucked another two times. Karen was too hung over in the morning for any more drinks, but we parted ways with a great hug and memories that I will remember forever.

Source: reddit.com/r/gonewildstories/comments/igg3ru/handling_a_karen_at_a_wedding_mf