Colleague's fiancée & her fuck-et pre-wedding list
What would you do if your potential love interest invites you to satisfy your boss's future daughter-in-law's unusual needs before her wedding?
This is a story about fulfilling a woman's sexual bucket list before she becomes a trophy wife. It has role play, reluctance, BDSM and anal sex.
A special thanks to RF-Fast for helping to proofread and ensuring the story is in good shape.
In for a Penny
"Man, my girlfriend's a freak." Kyle slurred and waved his nearly empty bottle of beer about.
I nodded and glanced wistfully at my beer. I'd drunk less than 1/2 an inch in the last 40 minutes and it was getting warm and flat. From the other end of the bar, Penny, the true reason for me visiting this bar, gave me a sympathetic look.
I'd been coming to the bar on the nights she worked late, and we'd chatted, flirted, and even made out just a little. Goth chicks aren't my thing, but she was funny and sexy as hell. I was fairly sure it was only a matter of time before we went from chatting vertically to something more horizontal, where our mouths would be otherwise engaged.
Rewind the clock by an hour, to see how I reached this point.
"Rowan?" a familiar female voice spoke through my phone. Ah, Penny. Not the love of my life, but the subject of my current hopeful romantic attention.
"Hey sexy, what's up?"
"Your mate Kenny is here and messed up."
I was confused. I had no friends called Kenny.
"Do you mean Kyle?"
"Blonde, uptight, and looks like he was born with a trust fund up his ass?"
"That's him. What's the matter?"
"A few guys frog marched him in here and dumped him at the bar and fucked off. He's pretty wasted and 'training wheels' is looking like he's gonna get upset."
"Fuck! I'll be there in 10. See if you can keep Billy calm. Give him a beer on my tab."
"You don't have a tab."
"I think it's worth giving me one to keep the peace."
I hung up and swore. 'Training wheels' was a private nickname for Billy, who thought he was a hard assed biker, but kept crashing his bikes. Not a name I'd say to his face, but we had a certain amount of earned respect for each other.
He thought I was some sort of softy in a suit when I first started going to the bar. Gave me some lip, and we ended up settling our difference in a local gym's boxing ring, bare knuckles. He didn't know my dad and granddad worked in steelworks and I'd been taught boxing almost as soon as I could walk. He broke my nose, and I cracked three of his ribs. I paid his medical bills because I was ashamed. I'd lost control, and we became frenemies.
I'd been hoping to see Penny for the chance it would lead to us spending the night together, but no doubt that was scuppered. I walked in and sighed as I saw Kyle sitting at the bar. I glanced at the pool table and saw Billy waiting for his shot. He saluted me with a beer, and I gave him a nod.
"Kyle. What's up Buddy?"
Penny gave me a relieved look and put a bottle in front of me. Kyle twisted around, shocked to see me.
"Rowan, what the hell are you doing here?"
"This is sort of my local?"
He frowned, as there were plenty of bars closer to my place. But he wasn't the sort to think about others even when sober.
"I needed a drink," he said.
"Looks like you've managed that, and then some. So?"
"What?"
"What I meant is you're not really a solitary drinker. Something must have happened, considering the excessive amount you put away. Is Crystal ok?"
Crystal was his girlfriend. Sexy, tiny with big tits, and while I don't like to pigeonhole people, she was a bimbo. Ideal for Kyle, really. I was only friends with him through work and his dad was the company owner.
"She's in hospital."
"Damn, is she ok?"
"Appendix ruptured." He replied. Well actually, it took him three goes to get it right, but who's counting?
"Is she going to be, ok?"
"Sure, but..." He went quiet, and I sat and waited.
And waited and waited. Eventually I had to poke him and ask again.
"What?"
"Crystal? I asked if she'd be, ok?"
"She'll be fine, but fuck..." he pulled out his phone and handed it to me and drained his beer and gestured to Penny for another.
She looked at me and I decided it was worth it and nodded.
I knew his pin code because I'd had to help him set it up. The video app was open, so I clicked on the recent gallery and found a video with a still of Crystal in a hospital bed. I hit play.
First off, it was obvious she was high as a kite from the drugs. She garbled and giggled, and I wondered why Kyle would video his girlfriend in such a state. It could only be to tease her later. The video stopped, and I selected the next. Crystal was slightly more lucid, but not significantly.
"Kyle, I love you so much. I'm so looking forward to us getting married. But I need to get some things out of the way before I settle for your small penis."
Ok, I might have paraphrased that and cleaned up what she said, but I kinda felt bad for him. I'd want the woman I married to marry me and not my daddy's money, even if she was hot. However, the next things she said were freaky and I can't say it didn't turn me on.
"Honey, I need to be tied up and whipped. Have a guy with a big dick fuck my throat until I nearly pass out, then pound my ass. Treat me like a $2 whore."
Kyle was conscious enough to follow the video.
I shook my head. "Mate, you don't have to take that seriously. She's completely out of it."
"Yeah, but it's not the first time. My dad basically told me I had to marry her, but..."
"You love her?"
"Yeah, but?"
"But I can't do what she wants."
