My Best Friend's Fiancée

I have a confession to make. I fucked my best friend's fiancée on the night before their wedding. I know what you're thinking. "This guy is an asshole." I agree it was an asshole thing to do without my best friend's knowledge. But I'm not an asshole in general. This is the story of the one time in my life when I couldn't resist the forbidden woman.

Geoff's wedding was on a Saturday. Most of the groomsmen were from out of town so Geoff booked us all into a hotel for the weekend. I was the best man so, naturally, I planned a bachelor party on Friday night. I bought an expensive bottle of whisky and some kinky games. Then me and the other groomsmen dragged Geoff to the hotel's party room for a blast.

About an hour into our party, Geoff got a phone call from Catherine, his fiancée.

"Shit," Geoff said after he hung up. "Our florist went AWOL. I need to help Catherine set up some new decorations."

"Right now?" I asked.

"Yeah."

"Dude! This is your last night as a single man. Catherine can handle some flower arrangements on her own, can't she?"

"She can but I should probably help. Keep the party going while I'm gone. I'll come back when the flowers are fixed."

Two hours later, Geoff gave me a call. "It's taking longer than I thought to set up all the flowers. I don't think I'll be able to make it back to the party. I need to get up early tomorrow, and I don't want to be overtired. I'm really sorry man. Take some videos so you can show me what Jamie looks like at the end of the night."

After that phone call with Geoff, I realized my best friend was really getting married. Me and the other guys were no longer his first priority. Geoff and I were best buds ever since we were kids, but now things were going to be different. This was a blow I hadn't expected to hit me so hard.

I kept the bachelor party going for another few hours but it wasn't the same without the groom. After the party was over, I sat in the hallway by the elevators in the hopes I might catch Geoff before bed. I wanted to at least show him the funny videos we made in his absence.

Around midnight, the elevator opened. It was Catherine.

"Where's Geoff?" I asked.

"He's talking to his parents."

"Do you know when he'll be finished?"

"Mmm. Probably not any time soon. Is everything okay?"

I sighed. "Yeah. There's just some stuff I didn't get to say to him tonight. I'm hoping to catch him one last time before the big day tomorrow."

Catherine bit her lip. "I'm sorry I ruined your bachelor party plans."

I shrugged. "It's not your fault your florist abandoned you at the last minute. I should have planned the party earlier in the evening. Geoff used to love late night parties but... I dunno. Maybe I'm just finding it difficult to adjust to the whole my-best-friend-is-getting-married thing."

Catherine gave me a compassionate look. "Aww." She sat down beside me on the floor. "To be honest, I'm feeling some trepidation about the whole getting-married thing, too. Marriage is a pretty big deal in my family."

"Your father is leading the ceremony, right?"

"Yep. I'm the pastor's daughter. No easy divorce if I screw this up."

I chuckled. "Geoff is a great guy. I'm sure you made the right choice."

Catherine smiled. "I know. That's why we're getting married."

I studied Catherine for a moment. "I'm sensing there's something specific that you're concerned about."

Catherine looked surprised. "Interesting. You should be a detective."

I laughed. "People have told me that before, actually. It's the way you smiled when you said 'I know.' Like you're hiding something."

"I'm not hiding anything but there might be something I'm concerned about. It's probably nothing, though. Also... it's too embarrassing to discuss in the hallway."

I pointed down the hall. "My room is just over there. If you want, you can tell me your embarrassing concerns over some eighteen year old Scotch. I might be able to help. I've known Geoff for twenty years."

"That's Geoff's favorite, isn't it? The old Scotch?"

"Yeah. I bought it for his bachelor party but there's still some left over."

Catherine checked the time on her phone. "Sure. Why not. I'm too wired to sleep right now."

After I poured Catherine and myself some whisky, we sat down on opposite chairs around the coffee table. Catherine took a sip of her Scotch. "Holy crap. This stuff is strong."

"Have you ever had whisky before?"

"Not really."

"You need to sip it slowly. But I might have poured you too much. I won't be offended if you don't finish it."

She put down her glass. "Alright."

I put my feet on the coffee table. "So... What's your embarrassing concern about marriage?"

Catherine shrugged. "It's probably not a real concern. Just... Geoff is the only man I've ever dated so I'm not sure."

"You didn't have a boyfriend in high school?"

"No, my parents weren't keen on me dating until after I graduated."

"What about your first two years at college? Didn't you and Geoff meet in third year?"

She nodded. "I had several crushes in college but I was usually too busy to go out. Also, most guys don't like my freckles. I didn't attract very much attention."

"Wow, seriously? All the guys in your classes must have been homosexual. I can't think of any other explanation."

Catherine laughed. "Thanks. Sometimes I wonder if I might lack sex appeal."

I glanced down Catherine's body. She was wearing a stylish blue dress. Modest, but I could still make out the shape of her breasts. Her waist. Her hips. Her legs. "Nope. You're definitely not lacking there. Geoff is a lucky man."

Catherine took another sip of her Scotch, and she shuddered at the taste. "This is related to what I'm concerned about. But don't laugh, okay?"

Now I understood why Geoff liked Catherine so much. Her mannerisms were so cute. "I won't laugh. I promise."

Catherine adjusted her posture uneasily. "I'm worried I might not be capable of having a good orgasm during sex. Geoff seems to orgasm so easily but it rarely happens for me. I'm not sure if it's because he's a man and I'm a woman, or if it's because I'm inexperienced, or... I don't know. What if it's not me? How would I even know? It's obviously not realistic to expect the kind of passion that I read in books, but... argh. This is embarrassing. I probably shouldn't have brought this up. Promise me you won't tell Geoff, okay?"

I wasn't expecting Catherine to pour out her private concerns about her sex life. Especially since she seemed to be suggesting that Geoff wasn't very good in bed. I knew almost everything about Geoff but sex was the one thing I'd never done with him. I had no idea if he was good in bed. Maybe he wasn't. I wasn't sure what to say. "Hey, it's okay. I won't tell Geoff if you don't want me to. But this sounds like the type of thing you need to talk about with him."

Catherine nodded. "I know, I know. But I don't want to give him the wrong impression. I mean... I don't want to give you the wrong impression, either. I'm not saying Geoff and I have a problem. I love him more than anything."

"Of course. I think it's normal to have some concerns when you're getting married," I said.

She nodded again. "Probably. I just... I mean... What if we like fundamentally different things?"

"What makes you think you like different things?"

Catherine nervously twirled her hair. "Well... Geoff is always very careful. Very gentle..."

I waited for Catherine to finish her sentence but she didn't. I was pretty sure I knew what she was trying to say. "But you like it rough?" I asked.

She laughed. "No, I don't want to be hurt."

I could tell that Catherine was inexperienced when it came to sex. "Rough sex is not about hurting the woman," I said. "It's more about the man showing his raw strength and passion."

Catherine leaned forward with interest. "Like what, exactly?"

I was beginning to find it arousing to have this conversation with Catherine. The longer we talked, the more I realized how pretty she was. "Like, if I grabbed your hair and whispered naughty commands into your ear," I said. "I had a girlfriend three years ago who was insatiable when it came to sex. She liked it rough. It was a lot of fun."

"And you didn't hurt her?"

"No, of course not. I loved her."

"So then... how hard would you pull her hair?" Catherine asked.

"It's difficult to describe. I could show you if you want. Is it okay if I touch your hair?"

Catherine sat up straight. She stopped twirling her hair, and she quickly shook her head. "No, that wouldn't be appropriate."

I was surprised by Catherine's reaction. She shut me down pretty hard. "Oh. I think I might understand what's going on," I said.

"What do you mean?"

"The reason why you might not be having the kind of sex you want. You seem to get defensive at the slightest hint of doing something inappropriate. You might need to be more relaxed. And you definitely need to like doing naughty things."

Catherine frowned. Then she picked up her glass of Scotch, and she drank the whole thing in one gulp.

I gaped at Catherine. "Did you just..." I laughed out loud. "Oh my. I've never seen anyone chug a glass of whisky."

Catherine coughed and grimaced from the aftertaste. Then she smiled. "See? I like doing naughty things."

I laughed again. "You're brave. That's for sure. But I'm not sure about naughty. Letting me touch your hair is barely inappropriate at all. But you just rejected me as if I asked you to suck my dick."

Catherine began to laugh and cough at the same time. "Now that would be inappropriate."

I smiled. "Yeah. There's a big difference."

Catherine stood up and coughed a few more times. "I might need to use your bathroom."

I chuckled. "Go ahead. You might want to drink some water, too."

A few minutes later, Catherine came out of the bathroom. "I think you're right," she said.

"About what?"

"About the way I rejected you when you asked to touch my hair. I've been taught to react this way towards men ever since I was in grade school. Maybe I'm still giving Geoff the wrong messages."

"Or maybe you just need everything to be lawful. It's not a bad thing."

Catherine shook her head. "Nope. I'm sure I need something much less lawful. I'm just not sure how to get Geoff to play outside the rules when it comes to sex."

I shrugged. "Just tell him what you want. I'm sure he'll try to do it."

"That's the thing. I'm not sure exactly what I want. And I certainly don't want to tell him what to do."

"Ah. In that case you should ask him to experiment. See what works for you and what doesn't."

Catherine scratched her forehead. "Can you show me what you used to do with your ex-girlfriend? Show me how you'd pull my hair or something."

Catherine's request made my erection begin to grow. "Are you sure?" I asked with caution. She drank a fair bit of whisky, and I was wondering if she might be getting tipsy.

Catherine nodded. "Yeah. Do that whispery whispery thing that you described. Just nothing that crosses the line, obviously. Touching my hair is fine."

I thought about what Geoff would say if he was here. It was probably fine. "Alright. Stand up for a sec." I walked over and stood beside Catherine. "If you were my ex-girlfriend, I might do something like this." I pushed Catherine against the wall, and I grabbed a fistful of her hair. I ran my other hand affectionately down her hip, and I leaned into her with a growling voice. "I'm going to kiss you now, and there's nothing you can do to stop me."

I wasn't planning to do anything more than this. But the way Catherine looked at me when I said I was planning to kiss her... it was such a turn on. Her eyes lit up with passion. And fuck. She was even more beautiful up close. The way her long hair fell over her face. Her attractive smile. Her dusting of pretty freckles. I could feel the softness of her skin. I could smell her feminine shampoo. And her beautiful eyes were looking up at me with desire. I couldn't resist her siren's song at such close range. I closed the last few inches, and I kissed her on the lips.

It takes two people to create a good kiss. And let me tell you, Catherine returned a full ten seconds of the most passionate makeout kissing that I'd ever experienced in my life. I felt like she gave me her fucking soul. When I finally released her from the wall, we both stared at each other in awe.

"Holy shit. I feel like I'm floating," Catherine said.

"Fuck. Me too. Are you on birth control?"

"Yeah but..."

A few seconds without kissing Catherine again was agony. I interrupted her mid sentence to kiss her a second time. We stole another ten seconds of passionate sparks and fire. I pulled away to look her in the eyes. I could hardly believe this was happening. I never felt this kind of immediate connection with a woman.

"This is soooooo baaaaad," Catherine groaned.

"I know," I whispered. But I couldn't stop. Catherine's touch felt so fucking good. The bed was only a few feet away. I gestured towards it. "You said you weren't sure how to orgasm?" I gripped her tenderly around the neck, and I brushed the crotch of her dress with an affectionate caress. "I could pin you down and fuck you until you figure out how to do it."

Catherine nearly melted in my arms. "Shiiiiiit..."

I was sure Catherine's expletives didn't mean "no" in this context. I tackled her onto the bed. I took off her shoes, and I flipped up her dress. She was wearing clean white bikini underwear. Nothing fancy by lingerie standards but the shape of her sexy pelvis triggered an intense lust inside me. Catherine was the perfection of feminine beauty trapped in a boring white bikini. I tucked my fingers into her waistband, and I pulled her panties down her legs.

Catherine sat up after I removed her underwear. "I'm supposed to be getting married!" she exclaimed.

I pushed her back down on the bed. "The way we're kissing each other, Catherine? This kind of passion happens only once a lifetime. We can't pass up this opportunity." I slid my hand up the inside of her thigh, and I touched her pussy with my fingertips. "Spread your legs," I whispered.

Catherine groaned. Then she spread her legs out wide. We resumed our fiery makeout kissing while I fucked her with two fingers. She began to thrust her hips with lust. If I wasn't smitten by her erotic kisses already, now I was fucking toast. Her pussy was so wet. And the way she was fucking my hand... she was practically begging for my cock. I was willing to betray my best friend of twenty years. I unzipped my fly and kicked off my pants. Catherine was worth the consequences.

I maneuvered on top of Catherine while we frantically made out like star crossed lovers. She gasped when I touched her with the tip of my penis. She knew this was wrong. I knew this was wrong. I just prayed to the devil that she wouldn't tell me to stop. And the devil answered my prayers. Catherine kept her legs spread while I lubed up my cock on her pussy. Then I slid in to full depth. The point of no return. My hormones were on fire.

I grabbed both of Catherine's wrists, and I pinned her to the bed. Then I thrust hard between her legs. I wanted to give her the rough sex experience. But even more than that, I wanted to intoxicate her with so much pleasure that she wouldn't have the willpower to abort. And it worked. Catherine lay spreadeagled on the bed while I kept thrusting. I was fucking her, and she was letting me. Every second we kept this up was a stolen act of sinful pleasure. I wanted this forbidden sex to last forever.

Unfortunately, I couldn't maintain my stamina for more than a few minutes. There was only so much of Catherine's slippery warm heaven I could withstand without a condom. I couldn't hold back my orgasm any longer. This was my last chance to have any hope of saving my friendship with Geoff. I needed to pull out now. I stole one more forbidden thrust. Then I released Catherine's wrists from the bed.

Catherine immediately reached down and grabbed my ass with both hands. "Don't stop," she groaned. She pulled my ass with all her strength. Then she twitched beneath me. And again. Her whole body began to convulse with orgasm while she fucked my cock.

I squirted deep into her vagina. "Uhh... fuck..." It was already too late. I grabbed her shoulders with reckless abandon. Then I pounded my dick into her pussy while I ejaculated with each thrust. It was pure euphoria. Such a sinful bliss. Catherine was Geoff's fiancée, and I was filling her pussy with my seed on the night before their wedding.

After my selfish release, I finally pulled out of Catherine. There was no mess at all. I deposited every last drop of semen deep inside her body. Reality began to sink in. Geoff was my best friend. What kind of asshole was I?

Catherine sat up on the bed. She looked stunned. She reached down to pick up her panties, and she quickly put them back on. Then she curled up into a ball, and she covered her face with her hands.

I wave of emotion washed over me when I noticed Catherine begin to cry. I felt such a strong love and empathy for her. I was the one who seduced her into sex. She didn't deserve to have her wedding ruined by angst and scandal. I quickly put on my pants. "Are you going to be okay?" I whispered.

"Geoff might break up with me for this," she sobbed.

I desperately tried to think. "You shouldn't tell Geoff the truth. You can't tell him the truth. You're on birth control, and I don't have any diseases. There's no harm if he doesn't know."

Catherine wiped off her tears. "I can't tell him the truth."

I nodded. "You should clean yourself up as best you can. Try not to let Geoff notice any residue."

Catherine glared at me. "Sometimes it takes days for all the residue to seep out! What am I supposed to do with Geoff tomorrow night? It's going to be our wedding night!"

I felt so guilty. "If there's anything I can do to help... Anything at all. Just name it, and I will do it."

Catherine shook her head. "There's nothing you can do, now. I just need you to keep this a secret. No boasting to your friends. No sending me secret messages. I don't want to be forced into any situations where I might need to lie to Geoff." She gave me a stern look. "And never try to seduce me again, even if you know I want it."

I nodded quickly. "You have my word."

Catherine walked to the door. "I need to go."

"Wait," I said. "You, um... you liked it, right?"

Catherine stared at me. Then she laughed. "At least now I know what I want. Do me a favor and check if there's anyone in the hallway, will you?"

I poked my head out the door. "All clear."

Catherine squeezed my arm. "I'll see you tomorrow. Hopefully it's not too awkward when I say my vows in front of the entire church." She sneaked out of my room, and she didn't look back.

Despite my asshole move, Geoff and Catherine's wedding wasn't ruined. It's been a year, and Geoff never found out what happened. He's still my friend but we don't spend as much time hanging out anymore. Partially due to my own guilt, but also because he spends most of his time with Catherine. That's what I was originally worried about when he got married. That I'd end up losing my best friend.

Ironically, I think I gained in the friendship department. Because now Catherine and I meet for coffee on a regular basis. It's strictly platonic but our brief fling of soul shattering intimacy bonded us together forever. There's nothing we can't talk about. Our secrets. Our sex lives. Anything. I never expected things to work out like this, but Catherine is my new best friend.