In for a Penny

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."

"Why?"

"I was sent to boarding school..."

He went silent as if I'd known what he meant, but I hadn't a clue.

"Sorry mate...." I started to ask.

He looked at me, then quickly scanned the room for eavesdroppers.

"The idea of spanking and anal sex, and..." He shuddered. "Having a dick forced down your throat is traumatic."

Suddenly I realised he wasn't upset about doing this to Crystal, but that he'd had this done to him. He tried to get up and stumbled, so I grabbed him, and half carried him to my truck. Hoping he'd not puke, I returned to the bar to settle my bill.

Penny took my hand as I handed over the cash and squeezed it.

"You're a good guy, Rowan, looking after him. You know it makes me want you more." I groaned in frustration and wondered what she'd think of me if I dumped Kyle into my truck bed to leave the back seat for us.

"Your mate is a dick!" Billy said, trying to loom over me.

"I agree wholeheartedly. But he's only just a guy I work with." I gestured Penny should give him another beer and dropped another few notes on the bar. "In truth, letting you teach him a thing or two would have been cathartic for me. But expensive for you."

Billy picked up the beer, grinning, and saluted me. I doubted he knew what cathartic meant. Penny gave me a wink and blew me a kiss. However, the kiss was overflowing with promise for more. Fuck! I had to take Kyle home instead of learning how skilled Penny's lips really were.

At the security gate to his house, I remembered a passcode I'd used a few years ago. His dad's security guys pulled Kyle from the truck and carried him into the house. As I put my seat belt on, I noticed Kyle's phone was on the floor of the truck. But I was too exhausted to find someone to hand it to.

I drove back to the bar and found Penny closing. No more booze, but I could watch her wiping down pumps and stuff.

"Your mate, ok?" she asked.

"I'd argue about mate, but yeah. Within a given value of yes."

I held up his phone and realised that if I removed the videos, given both people were out of it, they might not remember. It was a risk, but I sent copies of the videos to myself, and removed the original. Just in case either did.

"So, what's up with 'sad-sack'?" She asked.

I opened my mouth and paused. Penny was a woman of the world, and I wondered if she'd be a better sounding board to my understanding of what Crystal had said. Or if it was more than stoned talk.

"It's weird. But I need a woman's perspective. "

"That sounds like a challenge." She replied with a sultry grin that I felt down to my crotch.

"His fiancée is recovering from an appendix operation, and he videoed her when she was wasted on the drugs from the operation."

I brought out my phone and set up the video to play and handed it over. Penny watched it and handed it back.

"Why would he video her in that state?"

"I think we all agree he's a bit of a dick. If I didn't have to work with him, I'd avoid him like the plague. What do you make of it?"

"That Kyle had a small dick." She held up her hand and let her little finger dangle limply. I had to grin.

"That wasn't the bit I meant."

"Isn't it obvious? She's marrying the guy for his money. And he must have a lot if she's prepared to put up with a micropenis as well as his personality for life. I mean, she's hot as fuck and he's..." She held her hand up, palm down, and rocked it back and forth.

"I think she just said small, but, yeah, his dad's super rich."

"Right, thought so. Anyway, she's just wanting to try some things and scratch that itch before she takes her position as his trophy wife. Better to get it out of the way before she's tied down. But by the sounds of it. She likes the idea of being tied down or up." The look she gave me made me wonder if she liked that.

"So, have you done anything like that?" I asked, trying to sound casual and blowing it at once.

"You want to know If I've been tied up?" She grinned, then brought her wrists together as if handcuffed. "Oh, no, please Rowan. Please don't spank me? I'll let you do whatever you want if you don't." She hammed it up, but damn, the way she said it entered my ears and inflamed my libido.

She laughed as she noticed my expression of lust. Then she jumped up to lean over the bar to check my crotch. But in doing so, she gave me a great cleavage shot. Her bar uniform was a low-cut, tight t-shirt, and her bra made her tits look amazing.

She must have caught my gaze and dropped back to her feet and ensured that her tits bounced for me.

"Actually, I was usually the person doing the tying."

"Oh, right." I replied and tried to sound casual.

"It started with my roommate in college. I'd dated an older guy, and he did it to me a few times. But when I told my roommate about it, she really wanted to try it. But before you get any funny ideas about us in skimpy underwear lezzing out, it wasn't like that. At least not at first." She laughed.

"At first?"

"Men, typical. Love the idea of women together. I bet you're imagining it now."

"Hey, you brought it up. And to be honest, I'd happily settle for just you."

"Settle!" she said in mock annoyance and pulled the hem of her t-shirt down as if to remove wrinkles. But we both knew she did it to expose a little more cleavage.

"Settle is the wrong word. But you know what I meant."

"I suppose. Could you send me the video? I'll make it worth your while."

"Why? You're not going to post it online and embarrass her, are you?"

"No. I'm not like that." She fluttered her eyelids at me, trying to look innocent.

I thought twice about it, but I wondered what I'd get in return. So, I sent her the videos. Shoot me, I'd been lusting after Penny for ages.

"Thanks Rowan. In return, I'll tell you about what happened between me and my roommate and her boyfriend. But not tonight. I'm beat." She blew me a kiss, and I waited until the files were sent and left her alone.

The following day, Kyle was late to work, and his eyes looked like piss holes in the snow. I handed him his phone and explained how I'd bumped into him and took him home. I forgot about the videos and wondered how soon I could visit Penny to find out her story without sounding too keen. It lasted for 3 days.

"Hey Rowan." Penny greeted me as I walked into the bar. "We're closing shortly. Beer?"

I nodded and sat at the bar. Only a few other people remained this late, and they finished their drinks and left. Penny hurried over and collected the glasses and wiped down the table.

"It's been a quiet night, so I got a head start on clearing up. Fancy joining me for a coffee?"

"Sure." I replied and hoped she meant back at her place. Or mine, I didn't care.

Unfortunately, we headed to a 24-hour coffee shop and ordered decaf. We headed outside and slowly walked back towards the bar and her parked car.

"Anything new?" I asked, sipping my coffee.

"Maybe. I tracked down that Crystal girl from that video."

"Why? And how?"

"I recognised a nurse, and I knew which hospital it was from. Paid her a visit and told her about her fiancé filming her when she was out of it."

"Why?" I repeated.

"Sisterhood, I didn't want her to marry a douche who thought it was funny to film her when she's out of it."

"Fuck!"

"Oh, relax, it didn't work."

"Good, because I deleted the videos from Kyle's phone, and I got the impression he's no recollection of the video or why he got so drunk."

"Oh, sorry. I thought I was doing a good deed. Have I been a bad girl? Will you need to spank me to make up for it?"

She stepped up to a store window and put a hand on it and bent over. Looking back at me in a challenge.

"I'm tempted." I replied, then she wiggled her bum, and I reached out and slapped it moderately hard.

She yelped and jumped and shook her hand where she'd spilt some coffee. Luckily, it wasn't too hot.

"OK, I probably deserved that, but I've got something to make up for it."

"What? The rest of your story about your roommate at college?" I handed her a handkerchief to wipe her hand.

"No, but there are some similarities. And I might get to play the same role twice."

"Meaning?"

"I'm not sure if I should tell you or just spring it on you as a surprise."

"I'm not big on surprises."

"Spoilsport. Ok, I'll tell you about what happened at college. I think you know I'm not the 'live by the rules' kinda girl. I've had many lovers, and in college there was this one older guy who introduced me to bondage. My roommate Izzy often used to bug me to tell her about my experiences. She was repressed about her sex life and tried to live vicariously through mine.

"Her boyfriend was kind of a wimp, but they loved each other. I think Izzy wanted to be wilder but struggled to let go. So, when I told her about being tied up, she found it super exciting and demanded I tell her about it many times. So, I got fed up and suggested I show her instead, just to shut her up. But she blushed and agreed.

"I'd only been joking, but what the heck? I borrowed some rope and stuff from my friend and tied her up. For the record, we were both wearing shorts and t-shirts, not sexy lingerie. It's harder than you think to tie someone up properly. But we laughed as we did it. Until Izzy suddenly asked to be released. Rushing off the moment, she was free.

"At the time I thought she felt awkward about what we'd done. But she admitted the next day she was so worked up; she ran all the way to her boyfriend's place. And insisted on fucking him that second, even with his boyfriend's roommate in the room. The roommate promised not to watch, but he was just a guy."

"Ow!" I replied.

"Would you have kept your word at that age?"

"Probably not."

"Anyway, a few days later, she asked if we could do it again. Only this time, she wanted to be in her underwear. She'd read that exposure made it better. No idea where she'd read that. So, we did it again and I have to admit even I found it exciting. My little friend was helpless, and I was sorely tempted to do more." She looked at me and I just nodded. Trying to keep my face neutral.

"I caressed her skin and bottom, and Izzy was panting when I released her. It was funny that she demanded I drive her over to her boyfriends. But luckily, she'd warned him in advance, and they had the room to themselves. When she came home the next day, she had that freshly fucked look on her face.

"For once, she had a tale to tell me. She'd woken her boyfriend up in the middle of the night and dragged him outside and got him to tie her wrists together with his dressing-gown cord. Then, in the shadows of the building, she'd begged him to force her to give him a blow job. I had to laugh when I next saw Justin. He must have known Izzy told me, as he blushed mightily.

"Nothing happened for a few weeks, then she asked me to do it again. While it was fun, I asked her what was in it for me. I mean, she got turned on and ran off to get fucked, while I stayed home alone and frustrated. Her reply surprised even me."

"Why?"

"Are you sure you want to know? It might shock you and I'd hate for you to think less of me." She was feigning being coy.

"I think I can cope."

"If you're sure? Izzy knew that not all my lovers were men. So, she offered that if I tied her up again, I could touch any part of her, and she'd be in no position to stop me. Also, if I wanted her to use her mouth on me, she would."

"Wow."

"Because I'm Bi or..."

"Bi doesn't bother me. Just you gave the impression she was more conservative." I think my honesty earned me points.

"I did too. We talked about it for a while before we did it. And it was something. We'd seen each other naked many times, but both being naked as I tied her up was a turn on. Way more than when my friend had tied me up. I explored all her body most thoroughly and even used her toy on her. Then she sucked on my tits and pussy."

The last she added, like she was adding milk to a shopping list. But when she looked over, her eyes were burning with remembered lust.

"And did she enjoy it? Did you?" She chuckled at my force casualness.

"Yes, to both. It wasn't my first time, but I worried about Izzy's reaction in the cold light of day. She was a little awkward, but she admitted the reason was because she'd cheated on Justin. She and I were fine, and she was spending more time with her boyfriend. By the sounds of it, they were now more experimental in the bedroom and outside. Izzy seemed to have developed a kink of slightly risky outside sex. Have you done that?"

"I may have had sex in nontraditional places." I replied with a grin.

"What's the wildest place?"

"Oh, that's a hard one."

"A hard one or a hard-on?" She said and her hand rubbed over my crotch.

I know she was teasing me, but her hand froze as she realised that I'm nothing like Kyle down there. Definitely above average.

"In an insect house at a zoo." I replied.

"How?"

"It was a nocturnal room and almost dark. We stood in the corner and kept quiet as people walked past within a few feet of us."

"OK, anywhere else?"

I laughed. "How about uncomfortable and risky? I was seeing a girl who had a chip on her shoulder about her older sister and her kids. She didn't like that her parents would do nothing but talk about grandkids and continually pester her when she'd finally give them some.

"We were at her sister's house for a BBQ, and she dragged me off and we had sex in a kids' playhouse. It was about 3 feet off the ground on a tree stump and tiny. I've no idea how we managed or didn't get caught by the kids. What about you?"

"If you're lucky, I might tell you 1 or 7. But back to Izzy. About 2 weeks before summer break, she told me Justin's birthday was coming up and hoped I'd help her out with something special."

"Jelly and ice cream?" I teased.

"Whipped cream potentially, and I suppose KY is a jelly of sorts. Her original plan was for Justin to come over and I'd show him how to tie her up properly. We'd both be fully clothed and do nothing to hint that we'd done more than that. She'd explain to him why she'd been doing more with him, was because I'd told her about being tied up and her wanting to try it."