Kat Fucked Up Pt. 01

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Katherine reveals limited sexual past and gangbang fantasy.
5.4k words
4.68
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Part 1 of the 5 part series

Updated 06/11/2023
Created 11/14/2021
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"I've slept with a lot of people," Kat said, scrutinizing me through narrowed eyelids.

"Oh?" I asked her, doing my best to sound bored. "How many?"

"A lot."

"How many people could a 24-year-old possibly have slept with?" I goaded dismissively. "If you started when you were sixteen, had two boyfriends a year, with the random one-night-stand every once two or three years, you'd be up to...what? About twenty partners?"

"Twenty?" she jumped, sounding horrified. "Oh, my God! I'm not a slut!"

"We have different versions of 'a lot.' How many?"

She turned her head slightly and looked at me a bit sideways. "Five," she said, pausing before adding, "...before you."

I stretched and yawned. "That's not a lot. When did you lose your virginity?"

"When I was fifteen," she responded flatly.

"So you've had a new partner every other year since you lost your virginity? You seemed...more experienced."

"Well...I was with the same guy for all of high school and into college. He was horny all the time, so we did it a lot."

"How much is 'a lot?'"

"I don't know," she said, her brow wrinkling in thought. "Two or three times a day. On average."

"Every day?"

"Pretty much," she nodded. She extracted a long, shapely leg from the covers and crossed it over her still-covered leg at her ankles.

"For four years."

"Four-and-a-half," she corrected.

"So that's...," I struggled to do the math in my head. "So he fucked you about...three thousand times?"

"I don't know but it was a lot," she grinned, sensing some measure of triumph in her ability to finally impress me with her sexual experience. "I used to keep track in a diary. I made a little heart-shaped mark each time we had sex on whatever day and totaled them up at the end of each month. I stopped counting at around a thousand. That was less than a year after I lost my virginity to him. To Kent."

"Kent? 'Kat and Kent?'"

She laughed. "Yep. We were your typical high school power couple. Kent was tall, with wavy blonde hair, and blue eyes. We were like Ken and Barbie to the outside world. Anyway, I didn't have much of any reason to refuse after he'd popped my cherry, so I did it whenever he wanted."

"What about...I mean, weren't you worried about--"

"I've been 5'10" since the eighth grade," she interrupted, "and I've pretty much had this body since I turned 15, so my mom put me on birth control early. She didn't want me ending up pregnant in high school like her.

"Shame, really. I've always wondered what it would feel like to take that chance--to know that someone could be...like I said, there was literally no reason in my mind to refuse when I was no longer protecting my virginity."

"Wow. Did you ever get bored?"

"Not for a while. We were young and it was sex and we weren't supposed to be doing it. It was maybe two years before we started to get bored. We were in love, I think. Or at least Kent was and I was too naive to think it might be anything else."

"So what did you do then?"

"When?"

"When you got bored."

"Oh," she said. "Lingerie worked for a few months, but the newness wore off quickly and it became too expensive. Then we tried watching porn. That actually worked pretty well, but not because it turned us on. It was more that it was how we first learned about new positions. We hadn't really thought of much before other than him on top, me on top, and doggy style."

I snickered.

"What?" she asked, smiling. "'Doggy style?' Does that offend your intellect?"

"Of course not. It sounds funny spoken aloud, but I was more amused that after having had sex over a thousand times you could only think of three positions."

"I know. That is kind of funny. Sometimes we improvised out of opportunity. Like in the shower. Or if we were spooning." She paused and was still.

"...so you tried new positions."

"Right," Kat said, grinning broadly. "We went to Half-Price Books and found a few Kama Sutra books. We tried every position. When we found one we really liked, we stuck with it until it got boring then moved on to the next. Some were one-and-done because they were so stupidly uncomfortable. If the drawing has the penis, like, eighteen inches long and curved around someone's leg, then it's either stupidly uncomfortable or that position was intended only for a man with an eighteen-inch-long cock that can curve around someone's leg."

She paused, shaking with silent laughter. "Anyway, that lasted about a year-and-a-half. So we went back to porn for new ideas. Kent came up with a list of a bunch of things he wanted to try, but I refused all of them. It was the first time I'd refused him. That's when our sex life kind of stalled. In the last year we had sex maybe two or three times a week."

"What did he want to try?" I asked a bit eagerly.

She rolled onto her side to face me, grinning like a cat who'd cornered a mouse, then propped her head up with her arm. "You're still leaking out of me. Could you hand me a few tissues?"

I rolled to my right and reached for the box of facial tissues, but was shocked when she poked a finger at my anus. "What the fuck?" I started.

"That was one of the things he wanted to try that I said 'no' to," she laughed. "I can see you're not a big fan of it either."

"My 'fandom' isn't an issue. It's the lack of warning."

"So I could put something in your ass if I wanted?"

"I didn't say that."

"Then we're on the same page after all," she snickered.

"I didn't say that either," I responded, watching her for a reaction that didn't come. "Was that all he wanted?"

"No. He wanted to have sex in public and in front of other people. I said 'no' to both of those, too. Then he wanted to tie me up, blindfold me, spank me, you name it. I would have said 'yes' to everything, but he was also talking at the same time about having a threesome and I didn't want him to try something while I was tied up that I wasn't ready to agree to, so..."

"You weren't into being pleasured by a man and a woman at the same time?"

"It was more about him having sex with the other woman," Kat said, a frown on her face. "He insisted on it, almost desperately. When I balked, he tried to tempt me with a tit-for-tat and said we could also have a threesome with one of his male friends to make things fair, but that felt too much like we were giving up on each other. It may not have been the proverbial 'final nail in the coffin,' but it meant we were talking about collecting the funeral insurance."

"Wow. So after that you called it quits?"

"No. I did the threesome with another man to see if he really meant it or was just offering it up in the hopes that he could have permission to have sex with one of my friends. It didn't work out."

"He didn't like it?"

"Pretty much."

"What was it that he didn't like? Seeing you have sex with someone else?"

"I don't think he cared about that. I think seeing a live sex act turned him on. But seeing me have my first orgasm during sex and it not be with him? Seeing me have anal sex for the first time and it not be with him? Seeing me have sex in public for the first time and it not be with him?"

"Holy shit," I snorted, trying to process what she was saying. "You had sex with a man over three thousand times and never had an orgasm?"

"I had plenty of orgasms when I masturbated," Kat admitted. "But never with him."

"Why keep on? That should have been your first clue."

"It felt good," she said simply. "I like sex. I liked Kent. And I didn't really know any better."

"First orgasm, first anal sex, first public sex...that must have been some night."

"It was," Kat said. "It was like an awakening. That guy wasn't very big, but he knew how to use what he was born with. I don't know what he was doing behind me, but he hit me in all the right ways. Kent was in my mouth when I orgasmed. He was more shocked than I was."

My eyes were wide. This wasn't the Kathleen I knew. She was lost in her thoughts and didn't notice my surprise.

"I don't know what happened but something clicked," she reminisced, her eyes on the ceiling. "I pushed Kent away and went wild on this guy. After my second or third orgasm, I demanded that he fuck my ass. Demanded. I mean, my fingers always wandered when I masturbated and I knew it felt kind of good when I was doing the touching.

When I couldn't take anymore, I dragged him out onto the balcony of our apartment and he fucked me from behind against the rail. I could see people standing on their balconies watching. I think I came two or three more times out on the balcony. That night I made Kent sleep on the couch while I fucked this guy in our bed until I passed out from exhaustion."

"Jesus, Kat."

"I know. It was a rotten thing to do to Kent after we'd been together for so many years, but part of it was that I knew we were done and part of it was that Kent did, too, and was trying to use me as a launch pad to fucking other women.

I think I was angry somewhere inside and it boiled to the surface that night. Stupid thing was that Kent wanted him and the guy to use some sort of numbing lube, so they would last a lot longer. That totally back-fired. Kent couldn't keep an erection and the other guy took forever to orgasm."

"How did Kent face his buddy after that?"

"He wasn't Kent's buddy. He was a random guy from my biology lecture hall. He was nice looking, dressed neatly, and was always clean. He smelled like soap and cedar. And he always had a big bulge in his jeans.

I'd only ever had sex with Kent and he was a little lacking. Poor Kent. He wasn't exactly small, but I didn't want to take the sort of sexual leap Kent was suggesting only to have someone who was the same as Kent or smaller."

"I thought you said the guy wasn't very big."

"He wasn't. He was about the same size as Kent," she smiled. "Stupid Ralph Lauren jeans must be made to make guys look like they're big regardless of how big they are. But it worked out in the end." She was quiet again and stared at something on the wall past me. "No pun intended," she said softly, and grinned.

"So," I urged again, "a random guy, huh?"

She smirked. "I mean, I knew him. We'd talked before. So he wasn't exactly a stranger. He wasn't truly random, like a pick-up at a club."

"Still..."

"Yeah," Kat acknowledged. "Still. It was the closest I'd come to a one-night stand. I hadn't intended to...fuck him all the time. Or even another time. I...I just couldn't stop."

"Wow. So you transitioned from one long-term relationship directly into another?"

"No. I still thought of Kent as my boyfriend. Patrick was a friend with benefits."

"Did Kent--wait, 'Kat and Pat?' Are you fucking with me?"

"No."

I waited for her to smile at her obvious joke, but she didn't. "Did Kent know?"

Kat looked my face over like she was trying to figure something out. "Yes," she said quietly.

"Yes? Like 'yes, he knew' or 'yes, he suspected?'"

"He knew. The only way I would sleep with him after that night was in a threesome with Patrick."

My eyebrows climbed my forehead. "Seriously?"

"Seriously."

We were quiet for a few moments.

"Maybe I am a slut," she said under her breath, to no one in particular.

"How does that revelation make you feel?"

She smirked again and her eyes came to rest on me. "I don't know, Dr. Freud. Should we move to the couch and assume a more professional position?" For whatever reason, I wasn't amused. My brain was contemplating the possibilities. The smirk fell from her face. "What are you thinking?" she asked.

"Nothing, really. Just processing," I lied. "This is heavy stuff."

"Do you think differently of me?"

"Yes and no. You're still the same person, but now there's more to you. Does that make sense?"

"Sure," Kat responded, sounding a bit undecided.

"So how long did that go on?"

"Kent and Patrick? About a year. But I fucked Patrick every chance I got. I even started my diary again to keep track of how many times and ways. It was a fun game that got me through rainy days when Patrick wasn't around."

"How many times did you fuck Patrick?"

"I don't remember exactly. About 400 times before he transferred to Georgetown to be closer to home. It was more difficult to keep track with him. Kent was a pump-and-dump kind of guy, who came back for seconds and sometimes thirds and fourths.

Patrick was all over the place for half an hour to an hour. Except the times when we ducked into a janitor's closet or the men's room or wherever between classes. Then he was pump-and-dump like Kent." She paused before adding, "But it was so much hotter."

"You were having two-to-three threesomes every week for a year, then suddenly stopped?"

She smiled and looked directly into my eyes. "Yes."

"No--what should I call it?--withdrawal symptoms?"

"Of course not."

"All that sex for years, stopped cold, and you were...your body was fine with it?"

She looked at me like I'd farted. "Yes."

I didn't believe her and her face reflected my disbelief. "Did you stay with Kent?"

"No."

"New boyfriend?"

"Not until you," she smiled.

"So you had three one-night stands before we met?"

"No."

"Three fuck buddies."

"No."

"You're intentionally making this difficult."

Kat laughed and snorted, then threw her hand to her mouth, blushing. "That was attractive," she grinned, her eyes wide. "They weren't boyfriends and they weren't fuck buddies. They were more like brief flings."

"Brief flings that you fucked a thousand times before moving on?"

"No," she frowned. "More like a few times each before realizing I wasn't going to get what I wanted out of them physically or emotionally. I couldn't orgasm with them and I wasn't feeling anything special or exciting about them in the end. If it were love, I might have stayed with them, but it wasn't, so I didn't."

"Sometimes it takes time," I offered.

"It didn't with Patrick," she stated firmly. "Or with you."

"To orgasm or to fall in love?" I teased.

"Either. Both."

"Are you in love with me, Kathleen Turner?"

She frowned. "Don't call me that. I can't wait until I'm married and I have a good reason to change my name."

It didn't get past me. She was intentionally avoiding the question, so I humored her. It was rare that she spoke so candidly about her past and I wanted her to continue. "You could go by your middle name."

"I tried that in college, but too many people still called me 'Kathleen' or 'Kathy' or whatever. And 'Ashley' sounds so sorority, anyway. Kent always used my initials, which just happened to be the first three letters of my name, when he left me notes and some of my girlfriends saw and started calling me 'Kat.' It eventually stuck with our college friends. My high school friends still call me Kathy."

"It's difficult for me to see you as a 'Kathy.' Were you in love with Patrick?"

"I don't know," she responded softly, the distant look returning to her face. She brushed back a lock of golden brown hair. "Maybe." Then, more quietly: "Probably. Why can't you see me as 'Kathy?'"

"Kathy is a plain, brown-haired girl hiding behind a stack of books hugged tightly to her chest," I teased. "She avoids eye contact, mends her own glasses, and wears sensible shoes."

"I'm a plain, brown-haired girl who avoids eye contact and wears sensible shoes."

"Uh-huh." My eyes traveled across her breasts and down the length of the long leg that was flopped lazily over mine. Aside from a ridiculous tribal tattoo near her ankle, her body was flawless. I knew she knew what I was thinking. Usually after noticing the open book that was my face, she subtly hinted that she wanted to know I saw more than just her physical appearance.

"Well...don't discount Kathy," she said. "You never know what she's hiding under her skirts."

"Sensible, white, cotton granny panties." I imagined Kat in plaid pleated skirts complete with white, knee-high stockings and sensible, white, cotton granny panties...standing at half-mast around mid-thigh.

"They're comfy," she persisted.

"Comfy Kathy."

Kat relaxed and let her head hit the pillow. I was content to be quiet and dwell in my thoughts of Nympho Kat willing to fuck whenever and however I wanted, of public sex with Exhibitionist Kat, of Cumslut Kat wanting to know what it was like to be worried that she might get pregnant, of Spitroasted Kat having a hundred threesomes.

"What are you thinking now?" she asked, sounding like the first girl I went to a movie with in junior high school. "You have an odd look on your face."

"Where...what did you do in all those threesomes?"

"You mean 'where did they...?'"

"How did they fuck you?" I said 'fuck' with a nasty little emphasis that wasn't lost on her. Her eyes narrowed but her fake scrutiny was betrayed by traces of a smile.

"Mostly it was one of them fucking me while I blew the other, but there were times..."

I waited, but she was quiet. "There were times?" I urged.

"There were times when I would be on top of one and the other would take me from behind."

"Both in your...?"

"Sometimes." Her eyes scanned my face. "And sometimes not."

I couldn't hide whatever I was feeling and knew my eyes were the size of dinner plates. "How...did it hurt? Was it...I don't know...difficult? How did you even...how did...how did it come up? Did it just happen? Did--"

"Whoa, whoa, whoa," Kat interrupted, now looking inexplicably perturbed. "One at a time."

I let a few moments pass to gauge how much her attitude had changed before continuing. "Okay. Did it just happen or was it planned?"

"Neither. They'd been trying...I don't even know if it was 'they.' I guess it was really Kent. Sometimes I would fuck Patrick and Kent would watch. After a few weeks I remember being on top of Patrick and Kent coming up behind me. I blocked him. I reached back and jerked him off, but his attempts became a constant thing.

One night I just relented, partly out of pity and partly out of lust and partly out of sadness, I guess, because our relationship was hanging on by a thread and our days as a couple were numbered. What we were doing was a farce. I don't know...I guess it had been a farce for years at that point. Maybe it was always a farce." Her eyes again found some distant spot and she went quiet.

I waited for some time while she traveled through her memories, then shifted to alleviate the pressure her leg was putting on mine.

"Anyway," Kat continued, roused from her reminiscing, "it took weeks of him trying before I just let it happen. It was only the second time I'd outright refused him anything."

"Was it difficult?"

"No," she responded nonchalantly. "I just relaxed and pushed back against him. Anal sex isn't that difficult if you're relaxed, and lubed, and know what to expect. It also helps if your partner is a little on the thin side."

"How did it feel?"

"Full."

"Whether there was one in your...one from the front and...or both from the front?"

She laughed. "Full. Whether I had two dicks in my pussy or one in my ass and one in my pussy. Full."

"That's it?"

"No. It's hard to describe. It's mentally intense. That knowledge--'I have two dicks inside me.' It's different than fucking one and blowing the other. Those are separate enough that the intensity just isn't there.

The mental intensity made it enjoyable enough the first few times. It was something completely alien and new, you know? But mostly I felt full. When they worked out a rhythm...it was as physically intense as it was mentally intense. It was mind-blowing."

"So you were finally able to orgasm with Kent?"

"Orgasm? No. But it was still intense. I usually came after he pulled out."

"Ouch."

Kat pursed her lips. "I know. There was something about Kent. And," she continued, "there was something about Patrick. Whatever that 'something' was, it couldn't have been more polarized. I came if Patrick breathed on my neck. Kent could go down on me for two hours and...nothing. It was some sort of mental block."

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