Cherry Heartbreak

All characters in the story engaging adult activities are represented to be over 18 years of age and all activities are represented to be consensual.

This is more fetish nastiness. Don't read this unless you're into fem-dom toilet slavery. Really. This story is my tribute to the author Callipygia, who I blame/credit for getting me into both the fetish and writing. They made something so twisted into something so very exotic. While they haven't written in close to ten years, you can probably find their stories archived. If you like stories like this, Calli's stories would be worth the effort to find. More than a few of their twists-of-phrase have been stolen from theirs for my own stories, so I may as well give credit where it's due. Thanks.

Clara and I lived practically next door to each other since I was brought home from the hospital three months after her. We knew each other our entire lives and were pretty much joined at the hip. Preschool, play groups, birthday parties; we were there together for each other for just about every moment. She was my blood, even if we weren't related. We were around each other so much that we called each other's parents 'Mom' and 'Dad'. My Dad said Clara was the twin daughter he never knew he wanted.

I remember Timmy Douglas pulling my blonde ponytail during recess once in second grade. My tears and shouts didn't make him let go; what did was Clara, all fists and elbows, jumping on him and pounding his head like it was the playground tetherball. Timmy got a trip to the nurse and Clara got a trip to the principal's office and a few days off from school. But the message was sent; mess with one of us, you've got both of us to answer to.

As we grew, we naturally diverged, but only a bit. We joked that she grew up and I grew out. Clara grew a few inches taller than my 5-foot-5, and a bit more slender. I wasn't fat, just curvy. Thicker hips and legs compared to her longer and a bit leaner frame. Neither of us ended up too much up top. We weren't flat chested, but there wasn't a lot of cleavage when we were in our swimsuits. Like her body, Clara's face was a bit longer than mine, giving her a more patrician look. I had cheeks and dimples.

The rumors that girls have it easier in relationships than boys are grossly overstated. Neither Clara nor I got considerable attention from the boys in our school. Maybe it was us? Maybe it was them? Whoever was or wasn't to blame, towards the end of high school, there may have been a lonely Friday night or two where I would have welcomed Timmy Douglas pulling my hair like he did years before, especially since he had grown into a really handsome jock. Not the king of the school, but royalty nonetheless. But he didn't seem to notice me. That was our problem. I know there were a few guys interested in us, but the guys that we were into just weren't into us.

See, neither of us were 'ladies'. We weren't dainty. Despite her somewhat regal look, Clara had long been kinda tomboyish and loved gross-out humor and there were many times we laughed ourselves hoarse over some unladylike take on classmates, teachers or just people we knew, male or female. Clara's grandad joked that we were "broads". That may have been sexist of him. Kidding! We loved the guy. He could call us broads, jezebels or hussies and we'd still have loved the guy.

We had that bond, but Clara was the practical one, where I was a bit dreamier. She could get to the heart of what was troubling me, since she knew me so well. Crush on someone? She'd get the dirt out of me. Stress about a zit? She'd have me soaking it in witch hazel and treating it before I'd realized it was a problem. And I liked to think I was the same for her but, really, she was better at it.

College came and I stayed in state but lived on campus. Clara wanted to study hotels and left for Las Vegas. She said what sold her on it was the chance to work in her field while still in school. Well, we were apart for the first time in our lives, but we stayed in touch from our dorm rooms over all forms of social media. Through chasing guys, stressing over classes, being chased by guys and all the new life away from home that we could live. It was like we were never apart except for the several hundred miles physically separating us.

Clara returned for Thanksgiving and Christmas breaks, and it was like we hadn't spent months apart. In reality, we hadn't. We compared notes on the few details we hadn't spoken of over Instagram and Tik-Tok. I told her of the liberated sexuality of hundreds of teens living together in the dorms and the drama that ensued. She countered with the unrefined hedonism of Vegas, and the liberated sexuality of thousands of adults in America's largest adult theme park. We were subtly impressed with each other's tales, but noted that neither of us had a guy to show for it.

That changed spring semester when I met Kenny. He was in one of my classes and was originally from a town about an hour away from the town where Clara and I were raised. He mustered up the courage to ask me to a film he had to screen for one of his liberal arts elective courses. He was sweet and shy and was just the kind of guy I was looking for.

Naturally, I shared all the details with my bestie. She congratulated me and said she was trying to find her guy, but guys in her school and around Vegas in general were a bit more cynical and jaded, preferring to sample a variety of women and the relative anonymity of one-night stands. They were always on the lookout for something more than the vanilla boy-meets-girl story. Besides, school was going well and her work program and school were really lining up. There wasn't all that much time for a steady guy. She congratulated me on finding one, and in typical Clara form, she made a rude joke about me being knocked up by the end of sophomore year.

In truth, Kenny and I were extra careful about sex. He wasn't my first (thank you, Mr. Nameless Frat Pledge Dude who came two seconds after jamming his little thing into me dry! I'll fondly remember that memory until my dying days!), but Kenny was much slower and more concerned about my enjoyment. Like I said, I wasn't a virgin, but I wasn't the most experienced broad out there, haha!

Still, I had learned enough in my limited experience and from online porn that Kenny had a big ol' dick.

It went unsaid that we were both terrified of an unwanted pregnancy, so Kenny always wrapped up with condoms, while I had gotten my birth control prescription. Kenny was very gentle and took his time easing into me, reading my face for signs of hurting me or going too fast. In time, we learned to pleasure each other, and, while I wasn't a big fan of giving oral sex, Kenny didn't seem to mind going down on me.

That summer, Clara stayed in Vegas, coming back for a few weeks right at the end of July. It was so hot in Vegas during that time that bookings were way down, so she said she didn't need to stay in her work study program.

Seeing her in person after almost seven months, I must admit I noticed a few changes. She looked thinner, like in her face and arms. She wore mostly baggy clothes around, but she said she had found an exercise program she really liked and had made it a real pastime. Another change was a very flash manicure and pedicure. This was different since neither was the kind of thing Clara had been into before. She was always a bit less "girly" than that, so seeing her pad around the pool at my place or in her folks' place with such a refined look was a bit different. Finally, she seemed a bit different. Don't get me wrong; it was still Clara. She'd still lift her leg and fart in the passenger seat of my car and waft it over at me (Hello? Gross!). Same old Clara. But there was a different look in her eye. More mature? Something. I suppose she'd say the same about me. We'd both had life-changing experiences since going away to school, and we simply weren't the same people any more. But she was still my Clara.

Some old high school friends of mine and Clara's were renting a cottage at the lake during that time, and I convinced Kenny to come join us. I didn't have to work too hard, as it had been a few weeks since we had last seen each other, and there were few things more motivated than a young man in need of some sex. And I was certainly hot for him.

The night before we were to drive up to the cabin, Kenny arrived and he finally got to meet Clara. I was so worried they wouldn't get along. I warned Clara to be nice.

"I'm always nice," she giggled, rolling her eyes. Usually, that meant she was going to make some trouble.

"C'mon. He's important to me!" I pleaded.

"I thought I was important to you?" her eyebrows went up and down. Were her brows contoured? Did I not notice before?

"You know what I mean, just come on," I noted an almost whining tone in my voice. The doorbell rang, and as I got up, I added "Please!"

Clara smirked before farting and we both giggled.

I was almost worried when I brought Kenny in, and introduced him.

Instead of shaking his hand, Clara took a slow looping fist and gently tapped Kenny on the shoulder. "'Hey, ya big stud!" I cringed internally, as Clara waggled her eyebrows. She was looking at him, but I knew her performance was all for me. Kenny would have been mortified if he knew how graphically I had described his equipment, as had Clara milked me for every detail about his package over video chat.

But I needn't have worried. He just responded with that goofy guy-ism:

"S'up?"

Guys can be so clueless.

The two hit it off and the night was underway. We stayed at my house but talked on the patio, and out of earshot of my parents. Dad had gotten us some beers (yay Dad!), but none of us were really going hard at it. I had gone inside to use the restroom and get another beer. Looking out the window, Clara and Kenny seemed to be in a pretty serious discussion. I couldn't see her, but Kenny had always worn his emotions on his sleeve and I could tell that look where he was giving serious thought to his next words.

It was notable since most of the conversation to that point had been get-to-know-you kind of stuff. But by the time I was back outside, they were smiling and any seriousness in the discussion was either gone, or had been a figment of my imagination.

It wasn't long before Clara rose and bid us a good night, saying she had to get ready before our trip tomorrow. I walked her out but on the way in she stuck her head in to the living room. "Good night, Daddy," she sang lightly.

Dad rose from his chair. Mom, apparently, had already gone up to bed. "Going so soon?"

"Yes, Daddy. You know, busy busy?"

"Will I get to see you before you go back?" Daddy could be a charmer when he wanted to be.

She giggled. "I'll check my appointment book. I'll let you know." She winked at him, waving as she left. Daddy stood for a few seconds, looking a bit lost.

The lake itself was great. Catching up with old classmates was awesome and we had lots of good times. Kenny fit in pretty well. He was just cool enough to get along with the guys but not "bro" enough to seem like a dick. I got several compliments from my other girlfriends about landing him. I shared some dirt with them, but nothing near what Clara and I spoke of.

Clara herself laid low. She said she had some client work she needed to catch up with, and locked herself into one of the cabin bedrooms to hold videoconferences for a good part of the day. She even passed when we headed down to the lake to swim and play. She had to put on some make up for the calls, and the transformation was remarkable. The corny, gross broad I knew and loved was replaced with a stunning woman who looked a good ten years older than my friend and every bit the professional woman. Needless to say, I gave her a ton of grief for hiding that "Miss Serious" look during her entire trip home.

She looked a little sad, saying that presenting the image was very important to those clients and that she was determined to be successful. She then excused herself into the bathroom. When she reappeared, she was scrubbed clean and my familiar Clara was back. She mixed and mingled but never stayed too long in any one conversation. After supper, she once again locked herself into a room for more calls, her voice muffled through the closed door.

The trip was great, and Kenny banged me literally morning, noon and night. At one point, we were fooling around in the lake and I had to almost hit him as he grabbed me from behind and moved my swimsuit bottom aside and tried to slip his big thing into me as we bobbed in the water. I warned him that he didn't have a condom on, and there was no way I was gonna chance it for a few seconds of fun.

I could read his face. I knew he was struggling with his desires, but he visibly relaxed when I told him we could slip away into one of the bedrooms after lunch.

"Will you suck it?" he asked.

"Nice try, mister," and I splashed him and then fixed my bikini brief.

After the trip to the cabin, Kenny went home, and Clara left for Vegas a few days later. It was great seeing her, but I sensed us drifting a bit apart. I wanted, no, I needed my friend and we vowed to stay in touch over any mode necessary. And, we did.

Back at university, Kenny and I picked back up and all was good. I had moved off-campus with some friends in a three-bed rental and started to figure our life on my own. Clara and I spoke regularly and my bestie seemed happy and lively when we talked. She still didn't have a guy, or at least a regular guy but that didn't seem to bother her. For both of us, life had a good rhythm and moved along nicely.

Soon, it was the end of the year and once again, Clara stayed behind in Vegas, claiming her work was really taking off. She was now travelling a bit for work, and seemed excited by the new responsibilities.

In a repeat of the following year, she returned for a few weeks at the end of July and Kenny came down as well. There was no cabin trip this year, but Kenny and I slipped away for a few days to hike and camp and have as much sex as we could. We hung out a bit with Clara once we were back, and all was well.

Until it wasn't.

Junior year started and the familiarity of life with school, Kenny and my roommates. It wasn't long until after the Christmas break when Kenny and I started to talk about living together senior year and possibly, maybe marrying after we graduated.

I asked Clara about it, and while she seemed supporting, complimenting Kenny a bit, she also noted that my parents would not be so kind.

"Mom and Dad will flip their shit," was actually how she put it.

"What should I do?"

"Don't whine," she prodded.

I looked at her. "I'm not." I gathered myself up, realizing that I was, in fact, whining.

"Yes, you are," she paused before beginning again. "Look, what's the hurry? You can't go whining like that to your parents. They'll totally shut you down. You know that." I know she knew it as well as I did. "Kenny's a good guy, but are you really sure you want to go down this road? Now? With him?"

"Well, it's not right now, it's next school year," I reasoned

"Just a few months," she responded. "Sooner than you think."

"And why not him?" I continued on. "I love him and he's a good guy. His dad is taking him on in the family firm, and he can be a good provider. His dad makes good money."

"I'm just saying you should really live a little. You never know what's out there if you just play it safe."

"Play it safe?" I asked with a bravado I didn't really feel. In fact, as usual, Clara knew me better than I probably knew myself. "Moving in with Kenny is about as far from 'safe' as I could be. There a lot of risk there, y'know?"

"Well, I'm just saying," Clara rolled her eyes in that way she had, knowing she was right and that I was just too dim to see what she saw. "You could always come out here and stay with me..."

"What would I do out there?" I asked, my voice quavering.

"Don't whine." I straightened up as if shocked. "What would you do there?" She had a point.

Well, that call didn't go like I thought it would. But, being honest, I didn't know how it would go. What should I have expected? Telling my best friend that I was ready to cut her out of my life and become part of a married couple so early in my life? And, to her, she was just looking out for me, having my best interests at heart, even if I couldn't see it by making me think things over.

"You're right," she smiled. "I guess I need to think this over."

It was about three weeks later, around the time I was going to have to make a decision about my future plans, when I got an anonymous email with an encrypted link in it. I didn't click the link, being wary of getting phished. I thought about it for a day, but came back to it, early in the morning when my self-control is at its lowest and I impulsively I clicked it.

And my world turned upside down.

The page was a series of video stills of Kenny, nude and tied up in various positions and, in all of them, his manhood was very, very hard. Beneath the images was a directory of several large video files. One file was titled "Play me", and of the dozen or so files listed, it was the smallest. The other files were named "Kenny" with dates, going back a year and a half, if I was reading them correctly.

I looked around the room, both terrified that this was a prank, and terrified that it wasn't. It was just me; hell, there was no one home as far as I could tell, and my room door was closed.

I was frozen. It seemed like my mouth was instantly dry and the sound of my heart pounding in my ears was deafening. What could possibly be behind all this? My hand seemed to move on its own. I clicked the link.

"Why are you here?" The screen was black and the voice speaking was electronically distorted.

Kenny's face appeared onscreen, red and sweating like he did when exercising heavily. "You know why," he sounded miserable.

There was a hissing and a loud crack. Kenny jumped wincing in pain and sucking in air. It took a moment before he answered again, unbidden as tears ran down his cheeks.

"I'm sorry Mistress. I'm here because my girlfriend can't fuck me as good as you do."

Kenny's face disappeared in an edit and the scene cut to an angle, presumably on a bed or floor, with the camera between Kenny's legs aimed towards his huge, bare penis as it disappeared into a hairless vagina. Unlike when he was with me, his big cock slid in easily and down to the balls. The owner of the pussy was obviously very fit, judging by the visible abdominal muscles. That and the tattoo of a cherry and a valentine heart, broken in two, next to it, inches above the hole my boyfriend was buried in served as the only identifying marks of my love's partner. Her stomach actually bulged from the inside near her navel from his fat mushroom head rearranging her guts.

Once Kenny was fully sheathed in the velvet grip of the mystery woman's lower lips, he groaned with the deepest, most honest pleasure I'd ever heard from him. The camera pulled back, as Kenny's lover's hips ground in circles centered around his thick root. She straddled his hips in a deep squat. Fire engine red patent leather boots went up to her knees, with savage looking stiletto heels at least six inches high. Matching gloves and a hood covered up her hands and face, but the rest of her was on display, lean and muscular. Large breasts, implants by the way they stood out, but implants of the finest most natural look, stood out lewdly and swayed as she began to rise and Kenny's thick cock reappeared inch-by-inch, now slick with her juices. Muscled thighs flexed as she rose back up, just to the point where only the large fleshy head was still in her. She reversed course, swallowing him once again, earning another appreciative groan from him.