Halfway There, Part Six

Disclaimer: The content of this particular post includes some pretty harsh treatment. Please keep in mind that I had safe words – “yellow” for slow down or do less, “red” for stop. The things I did were done willingly and enthusiastically, even when I demonstrated reluctant or fearful behavior. I could always stop what was happening to me.

Flint had Lida climb off of my face and applied a pair of wooden clothespins to my nipples. I sucked in a deep breath, trying to keep my composure with them on while he beat me with all manner of things, some familiar and some looking like the antennae that used to be on top of a car in the 90s.

“They really hurt,” I finally admitted.

Flint gave me a look of ‘well, yeah’ before he leaned down and flicked one of the clothespins. I winced hard. “You want them off, then?”

I nodded frantically. “Please, please. It hurts too much. Please.” I continued to beg, my eyes pleading, my body squirming under the pain of the clothespins squeezing my nipples.

“All right, let’s get them off,” Flint conceded, raising a hand to slap the clothespins off of my nipples one by one. The first came off with a painful snap, but the second ended up twisting around the nipple. I wailed in pain. Flint smirked, “bet that really hurts, huh?” He raised his hand to slap it again.

At this point, I was in so much pain that I was barely thinking. While my legs were bound, my arms weren’t. Before Flint could smack the clothespin once more, I reached up and removed the clothespin myself. He stopped, arm still in the air, looking a little shocked.

“You seriously didn’t just do that,” he shook his head. “I’ve never ever had someone do that.” He called the girls over and I covered my face with my hands, feeling embarrassed.

“I’m sorry,” I murmured, “it just hurt a whole lot and I wanted it off.”

I thought he would hit me or give me a spanking, but he just stayed still. “If it’s too much, you use a safe word. Do you know your safe words?” I nodded nervously and he had me repeat them to him. “Otherwise, you take it.”

“But it was all twisted,” I complained.

He frowned. “You don’t think I know what I’m doing, then?”

I shrugged. I felt rather small, ashamed that I hadn’t just used a safe word or allowed him to keep going. I could have taken the pain, but I was having trouble giving off that last resolve of control that prevented me from the kind of discomfort that I didn’t enjoy. Sure, I enjoyed it because I despised it, but I hadn’t even let myself go there.

“I’m better than this,” I insisted.

Flint took out his phone and started scolding me. “I’m going to tell your owner what you did. And I’m not going to tell him that you should get another tally, but I’m certainly going to suggest it."

I groaned. Perhaps seeing that I was kind of beating myself up for it, Flint sat down on the floor and pulled me upright. He held me for a few minutes to make sure I was all right. I think he saw that the scolding hadn’t gone over all too well and I was sort of beating myself up over it. Later on, he’d check in about it and make sure I was all right.

But, at that moment, I kind of beat myself up a little. I’d been messing around like this for quite a while. I wasn’t trying to be a brat and I felt I was better than this kind of thing. I was embarrassed that I’d let Sir down by not demonstrating that he’d trained me well. I’m a perfectionist, even when it comes to stuff like this.

So, I rested my cheek on Flint’s shoulder and reasoned with myself that, at the very worst, I’d just end up with another tally.

Halfway There, Part Five

“So, which breast you want bruised, then?” Flint asked. He likes to punish people for hesitation, I’ve noticed, so I blurted out that I wanted the left one bruised for the sake of avoiding any additional pain than what I was already getting. He cocked a brow. “Left, huh? Wow. Usually people don’t have an answer to that. But you’re just like, fuck this one.” He grabbed my breast in his hand and shook it for emphasis.

He’s got this thing called a rute stick that he uses rather often, and it’s absurdly painful. It looks like a bunch of long matchsticks looped together with a band. On the breasts, it hurts like crazy. I was crying out fairly quickly, making uncomfortable pained eye contact with Lida as I was getting hit.

Flint must have seen me looking at her, because he gestured for her to come over. “Lida, sit on her face,” he ordered. She did, straddling my head and lowering her pussy onto my face. I leaned up and started licking, but nearly jumped out of my skin when I felt Flint push the hitachi against my bare clit.

I am way too sensitive for it without a barrier, and I was just about to scream feeling it against my unprotected pussy. “Hey!” I exclaimed, “I…I can’t do this when you do that.”

“Then you’d better get back to work,” Flint said, moving the hitachi to a more comfortable area, where it actually felt pretty fantastic, “or I’ll put it back where it hurts."

Lida, already sensitive from Macy’s attentions on her pussy, was squirming on my face. I squeezed my eyes shut and moaned against Lida’s pussy, focusing as best as I could on eating her out despite the vibrations between my legs.

Halfway There, Part Four

“Lida, switch with her,” Flint ordered and gestured towards the armchair. I tentatively moved to rise from the chair, unsure as to who he was referring to, before he continued, “Ivy, come here, take your clothes off.”

I slipped off the armchair and moved over to the couch, sliding out of my clothing along the way. Applying some pressure to my shoulders, Flint had me kneel on the floor and produced a zip-tie. He secured my arms behind my back so my arms were arranged forearm-to-forearm horizontally across my back, my hands resting on the opposite elbows. With a gentle shove, he made me lie back and, in a significantly less gentle move, removed a few coiled lengths of rope and dropped them on my face.

Unravelling one, he shook it out and folded my leg so my knee was bent and my foot was resting against my butt. “Comfortable?” He asked. I nodded as he started to tie my leg into position. Over on the armchair, I could hear Lida moaning.

By the time Flint finished repeating the process on my other leg, I was already a little rope-happy. I settled into position, letting myself relax until I felt the weight of my body and the strictness of the position taking some of the feeling out of my fingers. Flint hauled me up and sliced away the zip-tie, letting me shake my arms out before shoving me right back down.

“So,” he began over the escalating pitch of Lida’s moans. “What are we going to do with you?”

Halfway There, Part Three

Once again, I couldn’t manage to relax until the three had left the room. For all my humiliation in the bathroom, I wound up lying back in an armchair, legs up, with Macy licking my pussy. So, ah, yeah. Guess it was worth it.

Flint had ducked into the shower and Lida was over on the couch. We were attempting to maintain some kind of a conversation. Please don’t ask me why. I guess I thought at the time that it would be a totally polite thing to do. So, I tried my hardest to talk to Lida despite the fact that there was totally a pretty girl on her knees and eating my pussy.

When Flint came out of the shower, I was still relatively coherent, all things considered.

“How’s she doing?” he asked.

I sucked in a breath. “G…good.”

“Really?” He took a seat on the couch. “Let me know. Could she be doing better?”

“N…no,” I stammered out, “she’s doing good."

I guess I was raised not to criticize gifts, I don’t know, but I felt awkward saying anything negative about a person when their mouth was right on my clitoris. She was doing pretty well, but I wasn’t about to point anything out in the position I was in.

"Really?”

I nodded. “R…really.”

Halfway There, Part Two

I half considered using the bathroom on the way out of the restaurant, burrito in tow, but we weren’t all that far from Macy’s place and I figured I would be fine. This, of course, was a mistake.

“I’m going to use the bathroom,” I said when Flint and I arrived at Macy’s. Macy and Lida were over at the store up the block.

Flint shook his head and set his stuff down on the floor. “No, you’re not.”

“Yes, I am,” I huffed. “Come on, I have to pee.”

“Well, you’ll be in big trouble,” he replied, gesturing over to the kitchen. “If you want, you can go on the floor in there, but you’re not using the bathroom.”

“That’s disgusting!” I exclaimed.

He smiled, “yeah, it is.” Looping an arm around me, he hiked my dress up and started pushing on my bladder and teasing my clit. I squirmed, trying my hardest not to urinate on Macy’s floor. Thankfully, Macy and Lida arrived before I could. But, Flint just gave a sweep of his arm and said, “all right, everybody in the bathroom. Ivy has to pee.”

This is how I wound up back on the toilet, Flint taking pictures of me to send to Sir while Lida and Macy sat around me on the sink and the lip of the tub. “What is this?” I whined, “a Christmas card picture?"

Halfway There, Part One

My Daddy suggested I wear pigtails.

“Trust me,” she – a reigning queen of rocking the pigtails – said, “they’ll love them.”

I was going to spend the evening hanging out and playing around with Flint, Lida and Macy. While I’m used to people running a little late, I’d started to learn that not only was Flint on time for essentially everything, he was actually usually early. So, pigtails totally made sense when I saw I was starting to cut it a little close.

I was already in Flint’s car when I got another text from Daddy asking for a picture. I blushed a little explaining to him that I had to take a picture for my Daddy, before pulling out my phone to take a picture to send along to her.

Since I hadn’t eaten, I asked Flint if we could stop on the way to Macy’s place so I could get a burrito. (I’d had a rough day, cut me some slack.) To minimize the wait time for said burrito, I took out my phone to call the place ahead of time so I could just swing in and pick it up.

Naturally, this turned into Flint reaching over while he was driving and tickling me as I attempted to keep myself composed enough to place an order.

“You know people who take orders over the phone have to deal with that a lot,” Flint said when I finished the call. “Except he probably thought you were getting fingered or something.”

I huffed, keeping my arms crossed protectively over my torso until we reached the restaurant to pick up my burrito.

“I like your pigtails,” Flint said as we walked towards the door. “I’m looking forward to pulling on them.”

I gave him a thumbs up. “Mission accomplished.”

Piss Shy, Part Eleven

Disclaimer: The content of this story is a little bit harsher and a little more intense than most of the experiences I have written about on here. Please keep in mind that I had safe words – “yellow” for slow down or do less, “red” for stop. The things I did were done willingly and enthusiastically, even when I demonstrated reluctant or fearful behavior. I like to be scared and I like to feel psychologically exhausted, and this experience allowed me to tread some harsher waters. So, I hope you’ll stick along for the ride.

Thankfully, my pussy got sore from the hitachi before I came, so I spared myself the consequences of that. The blindfold came off and went on Lida, who laid down on the towel. Flint put the hitachi on her clit and I ended up holding her hand with one hand while texting Sir with the other to check in and let him know that I had managed to hold off cumming.

It kind of reminded me of that story of how Mozart wrote music with one hand while holding his wife’s during labor with the other. Give me credit here. Texting one-handed is hard.

Lida’s got a hair-trigger as far as cumming goes, so she was launched into this spell of basically rolling orgasms rather quickly. She’s a cute little tiny girl, and she becomes a mess of little pouts and whines when she starts cumming. It’s kind of the cutest thing ever.

“Macy,” Flint said, taking the hitachi off of Lida’s clit, “go take Lida into the corner and have her teach you how to make her cum.” As the two retreated into the corner, Flint pointed between WRM and I, “and you two, over here.” He gestured to the couch.

I looked over my shoulder to see Macy busily burying her face into Lida’s pussy before joining WRM and Flint over at the couch.

Piss Shy, Part Ten

We moved back into the living room and Lida and I mercifully got a little break after the degradation in the bathroom. Flint pulled the blindfold over Macy’s eyes and had her lie down, while I helped Lida and WRM hold her still as Flint spanked her pussy. The slaps were so hard that her skin rippled, but she took the whole ordeal like a trooper. She even handled him hitting her with a toy that looked like the antenna on a car from the 90s.

Afterwards, Flint had me lie back down while the other girls held me. “You ever hear of a hitachi?” he asked as the blindfold went on. I groaned an affirmative and he laughed. “You know what it is, then?”

“Hell,” I replied with a huff. “This isn’t fair, I’m not allowed to cum.”

I heard Flint plug the hitachi in and felt its end push up against my pussy. “Well, then don’t.” He switched it on and I gritted my teeth, breathing hard and trying to keep myself under control.

I’ve never had a hitachi pushed up against my pussy before without panties or stockings to act as a buffer, and I soon discovered that I am entirely too sensitive for it. I kept arching up and away from it, exclaiming that it was just entirely too much. To add to the discomfort, WRM shoved some of her fingers into my pussy. She’s got long nails, which just do not work with fingering at all (I don’t know how the girls in lesbian porn do it). Overall, the whole ordeal was profoundly awful, so I guess I didn’t have to worry about cumming.

That is, until Flint took charge of the situation once WRM withdrew her fingers and, thankfully, the hitachi was removed from my pussy. “Macy, come here,” I heard him say, “Learning experience.” I felt his fingers – they were large enough that I figured they weren’t Macy’s – slip into my pussy, which was still sore from WRM’s nails. “Here’s how to make a girl cum.”

My eyes widened under the blindfold and I tried to squirm away, “no! I can’t!”

“Now, take two fingers and try to find the spongy part right up in the back,” he explained calmly, didactically, totally ignoring my protests. I whined as I felt his fingers brush my g-spot. He patted my pubis almost clinically, “it should be right here but on the inside."

His fingers slipped out of me and I felt Macy’s slip in in their place. Lida and WRM held me down while Flint took a cold water bottle and rolled it over my body. The low temperature almost burned, and the condensation left in its wake made my skin incredibly sensitive as he started slapping it.

"You’re a whore, you know that?” Flint said as he grabbed my throat, choking me while Macy ground her fingers into my g-spot. “You met these people, what, a week ago? Do you know anybody’s last name here?”

“N…no,” I stammered out as he let go of my throat. Something in me snapped out of the seriousness of the situation, and I started laughing. I didn’t know anybody’s last name, and I absolutely loved that. The whole situation was absurd, preposterous. I’d thrown myself into the belly of the beast, finally attended a play party in my new city, and suddenly I was involved in a fivesome (orgy?) with four people I’d just met. “I’m a whore,” I said between laughs, “I’m a whore.”

Flint grabbed hold of my throat once more, which pulled me back into the situation. Macy ground my g-spot harder, and I lurched forward as I felt a splash from the bottle of cold water being dumped onto my chest. I gasped loudly and Flint slapped my breast, the cold water intensifying the pain of the hit.

I forget what I said now, but it was something super sassy towards Flint. Suddenly, I felt pain tearing through my chest and upper rib, and I though that Flint had hit me with the bottle. Turns out, he just slapped me a little harder. Regardless, I curled up, groaning in pain. “You asshole. You’re a jerk.”

“Glad you figured it out,” Flint rolled me back into position on the towel and I felt the hitachi being applied to my pussy again. “Now, I don’t care that you’re not allowed to cum. You’re here to entertain us and we’re going to make you cum.”

“I’ll get in trouble!” I argued, arching off of the hitachi.

Flint applied pressure to my hips, holding me down. “Good.”

Piss Shy, Part Nine

I went to rush out of the bathroom when Flint ushered the group back in, grabbing my shoulder and turning me around. Lida slipped out of her pants and underwear, stepping into the bathtub and squatting down.

Now, tumblr. I’ve seen some shit. I’ve watched a dick the size of my forearm get stepped on like a bug, that guy from my frat has tricked me into watching a prolapse porn (EUGH), an anon on here once sent me a 10 second video of himself jerking off that ended with him whispering, “I love you” (OH MY GOD IT WAS AWFUL AND IF ANYONE EVER DOES IT AGAIN I WILL RIP YOU TO SHREDS.) But, nothing was more “oh my gosh I can’t look but I can’t look away and I don’t know how I feel about this but I think I might like it” than watching Lida pee into the bathtub, wipe herself with her hand, and then lick her hand clean.

Back in the living room, Lida, WRM and I held down a blindfolded Macy while Flint repeatedly slapped her pussy. All things considered, she took it like a champ.

“So, what’d you think of that?” Flint asked, “in the bathroom with Lida. She hasn’t used a toilet since, what, Christmas?” Lida blushed and looked down at her hands.

I shook my head and chuckled, “I’ve gotta walk that off.”

Piss Shy, Part Eight

Flint reached under my armpits and hauled me up to my feet, leading me into the bathroom. He sat me down on the toilet and guided my hand over to the toilet paper. I sat, waiting for him to leave, until I realized he was still standing there.

“I can’t do that with you here,” I said, tugging the blindfold off of my eyes. WRM walked into the doorway and I threw my hands over my eyes, “oh my gosh, everyone get out and close the door. I don’t need an audience.”

“Actually, I think you do,” Flint replied, leaning out the door and calling Lida and Macy inside.

It took me forever to be able to urinate in front of Sir. At first, he had to stand by the sink and look away. Then, he had to stand in front of me while I looked away from him. Then, he had to hold my chin and look in my eyes until eventually I was finally comfortable enough to do it. But it was a whole process. A process that wasn’t about to be circumvented in front of a whole audience.

“I can’t,” I insisted.

Flint shrugged, “well, you’re going to have to.” He stepped out for a moment and I stared anxiously at the group in the doorway, but my fear peaked when he returned with a box of black latex gloves.

Yeah, apparently they make black ones, go figure.

He snapped the glove onto his hand and knelt down in front of me. “You’ve got to the count of ten or I am going to go down there and make you.”

I gazed back over to the girls in hope of some sort of clemency, but found none. “Can…can we turn on the water and talk about oceans?"

WRM reached for the faucet. Flint raised his hand. "Don’t turn it on.”

I bit my lower lip and looked at my feet. “Can everybody just leave the room for a minute?”

“Nope,” Flint replied and placed his bare hand on my stomach, applying pressure to my bladder. He brought the gloved hand just below my clitoris. “So, what I’m going to do here is massage the clitoral -”

“I know what you’re doing!” I shrieked over his explanation.

“ – to essentially force the urine out of you. And you’ve got ten seconds to do it yourself or I’m doing it for you." Flint smirked, "remember your safe words?"

I nodded, "yeah, yellow and red.”

“And?” He asked, ensuring I was actually still game and consenting to what was about to go down.

Part of me wanted to call it off right then, but part of me liked the tension of it, how absolutely nervous I was. I enjoyed the catch 22: I needed to relax to get myself out of the situation, but there was no possible way that this sort of situation would enable me to relax. The closer I got to the bottom of the countdown, the more tense I became. And as much as I despised the total violation of him forcing me to urinate, I would be lying if I didn’t say I couldn’t close my eyes right now and still picture myself in that bathroom, seeing the smirk on his face, and revisiting that swelling nervousness with at least a remote feeling of arousal.

“I have to pee,” Lida said.

“Good!” I exclaimed, “good! Let her go first.”

“Lida doesn’t pee in the toilet, silly,” Flint replied, not leaving me any time to contemplate what that meant before adding, “now, come on.” He resumed counting and I squeezed my eyes shut, begging every last inch of my urinary system to just cooperate. When he reached the end of the countdown, Flint rose to his feet and removed the glove, patting my cheek. “Next time, you’re going to be expected to do it. Or I will go down there and I will absolutely do it for you. Are we clear?” I nodded and he ushered the girls out.

The second the last set of feet left the bathroom, I was finally able to urinate.

“It happened!” I exclaimed, “floodgates are open."

"Oh, you’ve got to be kidding me,” Flint called from the living room.

Ivy

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Piss Shy, Part Nine

Piss Shy, Part Eight