Bottom Boi Ep. 04

"Mmm, that's it, scream like a bitch. Now take my cock and make me cum," she groaned. "And remember, don't spill a drop of my coffee!"

Relentlessly, she forced her cock deeper and deeper into my tight ass... errr pussy, until I felt her hips pressed against the back of my thighs. The plug had thankfully kept my normally tight hole just loose enough for Her to get deep inside me without too much difficulty. We both noticed how easily She took me balls deep.

"Mmhmm, look how easily you took that big cock. you are such a slut!" I blushed as she said. "Your ass was made for cock. I'm going to keep pounding your pussy until it molds to the shape of my cock."

She started really fucking me, then. The kitchen filled with the sounds of two people fucking with abandon. Well, more like one person fucking and the other person taking it. Slap! Moan! Whimper! Repeat! The front of her thighs slapped against the back of my legs, Her rising moans of pleasure as she plowed into me, and my unmanly whimpers of surrender.

I shook with the effort of holding still each time She rammed her strapon inside me. She was testing me, trying to make me spill her coffee and enjoying every second as her clit buzzed and tingled with excitement. But I managed to focus on pouring her cup without a spill. It took longer to get two spoonfuls of sugar in Her cup and stir it without spilling anything. I had to time each gentle spoon swirl with her pulling out of me between thrusts. I had to stop stirring each time She slammed her strapon back deep in my pussy, my back arching, my body shaking. And right at that moment, I accidentally shake the cup.

"You are in grave danger, sissy," she said.

So she started fuck me even harder, I gave up the rest of my masculinity left and begged, "You own me, Mistress! Please keep me. Pleaseeeee. Please, I will not forget to set the coffee timer again so you never have to wait in the morning. Please, please, I'm begging You!"

I begged and moaned like a slut. I can't even remember all the many ways I begged her for mercy. She just rammed her thick cock over and over inside my battered hole. The more I begged, the harder she thrust and the louder she moaned. It felt like she was trying to fuck me into the counter and I was just a piece of meat she needed to pound. I wasn't a man, I was her fuck toy.

Then I felt her shudder as she came with her strapon buried in my pussy. She slowed down then, having had her first orgasm. Now, each time she bottomed out I felt the pressure of her heavy cock mashing my prostrate again. I was embarrassed at how good it was feeling and how much I wanted her to keep fucking me even after countless sissygasm. I created a big puddle on the kitchen floor. I was surprised by not feeling the chastity around my clitty. I was totally focused on my asspussy that I didn't notice when she unlocked me. But.... when I looked at my clitty I was shocked that I wasn't hard but leaking my sissy white juice in a slow water flow while her cock tip was massaging my p-spot. Without thinking much, I was pushing my ass back at her, desperate to cum even more after knowing I couldn't.

"Mistress, please milk me a little more," I begged.

"No more, my horny little bitch. I came, so I'm done and off to work," she said, smirking and slapping my ass. "Shhh, now be quiet while I enjoy the sight of your well-used pussy gripping my cock."

Her hips finally rested against the back of my thighs with her strapon still buried inside me. I obeyed and stopped begging as she slowly calmed down from her orgasm. Then she started to pull her strapon from my well-fucked hole and stood back, watching me.

I gasped as she finished pulling out, feeling my puckered hole twitch at the sudden emptiness. I sagged a bit in relief, then quickly grabbed her coffee cup. Turning around to face her, I got back down on my knees and lifted the cup up to her.

"Mm, good boi. Now, this is a perfect cup of coffee," she said. "Look up at me and have a taste while you clean my cock."

With that, she tipped her cup a little and poured a few drops on the tip and shaft of her strapon. I groaned, looking at the moisture gleaming on her cock tip. She had a thing about making me taste my own ass on her strapon after fucking me sometimes. She said it turned her on to see how much of a slut I would be for her. I knew my place and was still horny as fuck and not thinking clearly, so I just opened my mouth and obeyed without hesitation.

Sliding my lips down her shaft, I frowned a bit at the slutty act but didn't stop. I relaxed my throat until I swallowed her deep. I bobbed my head sucking her clean, deep in subspace. She casually sipped her coffee, watching me and putting her hand on my head again, guiding my lips and throat up and down her shaft.

Tasting my own ass juices and a faint hint of coffee flavor drove me crazy. I was embarrassed even though I should be used to this by now. She bucked her hips a few times, making sure I gagged and choked beneath her. Then she finished her coffee.

"When you finish you may dress and go to work. Wear the shirt I had on earlier so you inhale my scent all day and think of me," she ordered while unbuckling her strapon. "If you are good and dinner is ready when I get home, I might unlock your chastity for a bit again. It looks a lot smaller than before now."

I moaned my thanks as I remained on my knees, sliding her cock in and out of my mouth as she left. My eyes naturally fell on her magnificent ass while she walked out. I finished cleaning her cock and rose to get ready, already carefully planning in my head her dinner.... hoping for relief tonight if she granted it.

"Ohh, I forgot. You'll need to make another plate, honey, we're having my friend Debbie over for dinner," she said.

"Yes, Mistress. I should get dressed before she arrives?"

"Hmm... I don't think so. It might be nice to have a naked servant for the evening... right?" she asked.

"Yes, Mistress. I'll be on my best behavior," I replied knowing she wasn't actually asking.

I froze in place while my Mistress pondered this. Was she really going to ask me to do that? So far all of our fun had been in the house, just the two of us. I couldn't deny that the thought excited me though... I snapped out when I heard her laughing.

"Ah, the look on your face, sissy. It's so easy to mess with you! Of course, you'll need to get dressed, if you were a little more impressive, maybe I'd want to show you off." she giggled, and waggled her pinky finger at me. "Or maybe I want you to be naked."

Debora and my mistress came together at home. She'd been one of Natalie's friends for years, and they knew each other well. She was beautiful and curvy, with fiery black hair. I had always had a crush on her, and tonight she looked especially good - wearing a tight low cut dress showing off all of her best features.

It took a lot for me not to openly stare at Debora's cleavage when she arrived. And just the sight of her got my clitty twitching in its prison, but I knew there would be hell to pay if Natalie caught me ogling her.

I opened a bottle of wine while they sat down to eat, and did my best to look interested in Debora's work stories about a dozen other people I didn't know.

After the food, we all moved to the living room and started into the next bottle of wine. I spent a little while fidgeting, not only had I grown accustomed to being naked all the time, but the chastity cage was sometimes difficult to position comfortably, and Debora seemed to notice my discomfort.

"Everything OK, sissyboi?" Debora asked. "You seem a bit antsy."

"Yeah I'm fine thanks, just getting comfortable," I replied.

"How's the wine?" Natalie asked.

"Oh it's great, I'm running a little low though..." Debora replied.

I started to rise to get a refill, but Natalie put a hand on my shoulder and grabbed the glasses first.

"Don't worry honey, I got these," Natalie said and winked at me as she left the room.

"Wow, you look so pretty now," Debora complimented me. "I wish I had a sissy like you. I met a few but they are not like you, good sissyboi."

"May I know about them?" I asked.

"Sure, why not. A few one-night stands, but no one who I've really liked. I don't know how Natalie managed to lock down a guy like you, this town seems to be full of douchebags." Debora said despondently, leaning back on the sofa. This angle made her breasts look phenomenal as if they might even pop out of her dress, and I had to stop myself from staring again. I couldn't help a quick glance though, and she gave me an admonishing look when I met her eyeliner again.

"Why one-night stand? If " I asked.

"Oh definitely. These men may be douchebags, but they're well-hung, and they know what they're doing in bed!"

"Sorry sissy, does it bother you when I talk about their big cocks?" Debora asked.

"No, it's fine - I just wasn't expecting it!" I replied.

"A bit jealous, maybe?" Debora teased. "Ooo, my bad. Natalie already showed what you two are having fun with. Definitely, you're not jealous, hehe."

"Aaa," I was astonished.

"I'm messing with you, sissy! Don't get all worked up," Debora said. "I just saw you checking me out a minute ago. I just thought I'd tease you a little."

With a quick glance towards the kitchen first, to make sure Natalie hadn't returned, she leaned forward and pushed her arms together, squeezing her boobs so they almost popped out of the dress, giving me another wonderful view.

"But we wouldn't want Natalie to see you staring like that would we?" Debora whispered seductively.

She leaned back again laughing, obviously enjoying my discomfort. I just sat there silently, mouth slightly agape, my clitty aching as it desperately tried to break free. Then Natalie returned with 3 full glasses and another bottle.

"Having fun you two?" Natalie asked.

"Oh yes, I'm just making fun of your sissyboi a little, and telling him about my latest romantic exploits," Debora replied. "How big and great they were in bed."

"My sissy is not just great in bed. Didn't you see today's kitchen event?" Natalie laughed with Debora.

As Natalie sat down, Debora leaned in and stage-whispered to her, "So, Natalie tell me about your sissy. What's new other than that big, thick cock."

I immediately went red and looked at my Mistress. She raised an eyebrow and met my gaze, still deciding how she would answer.

"His one's getting smaller every day" Natalie giggled.

"Nice, I love micropenis," Debora said.

I relaxed a little after that, and the conversation calmed down a little bit for a while, as they made a start on the next bottle.

As the evening wore on, I was just enjoying the night, until Natalie left the room again, to go to the bathroom.

"So tell me how small it is now, sissy," she said. "The cage is little but I want to know your erect clitty size."

I was so confused, about what to reply.

"Well, how about a little trade? I'll flash you... if you show me how hard your clitty can get inside it," Debora offered.

"No way," I replied. "I can't do that."

"Oh come on, just for a second," Debora thought for a second before continuing, with me too stunned to reply. "How about this; I'll show you my tits first and you can stand up afterward, and show me you didn't just get a boner from them."

"You won't tell Mistress Natalie, right?" I asked.

"Yess!" Debora whispered.

Debora sat up straight suddenly and began slowly pulling back the fabric of her dress to reveal more and more of her breasts. Knowing she had to give me a boner, she took her time, both of them keenly listening for the sound of plumbing or footsteps from above.

"Make sure you pay close attention sissy, I want to see your cute soldier at full salute," Debora said.

I would have been fully erect about 5 minutes prior if it wasn't for the cold embrace of my chastity cage.

Debora finished her slow teasing reveal and bared her breasts in their full glory for me to see and I was almost salivating at the sight of them. She licked her finger and started slowly rubbing it around one of her nipples, biting her bottom lip seductively.

"Wait WHAT?! But you were loving it!" Debora exclaimed. Just as I began to make an excuse, we heard the voice of Natalie from across the room, behind me.

"I wonder why that is sissy? Aren't you aroused by Debora's perfect tits? Even I get excited at the sight of them," Natalie mocked.

My stomach dropped, as I slowly turned around to see Natalie staring at me from the doorway.

"I leave you alone for 5 minutes, and this is what you get up to?" Natalie asked.

Debora started to stand up to protest, but Natalie stopped her.

"Don't worry Debora, I don't blame you. My sissyboitoy should know better," Natalie said. "We need to see what's going on inside your cute clitty cage?"

She turned to stare straight into my eyes, as the reality of the situation started to sink in for me.

"Sissy, It's time for an inspection," Natalie ordered.

Her tone of voice said even more. She had a fire in her eyes and was clearly not in the mood for refusal, objection, or any hesitation. I'd fucked up. Big time. The only way forward was to comply immediately.

I took a wide stance in front of the two of them, hands clasped behind my back.

Debora crouched down in front of me to get a better look.

"May I..?" Debora asked Natalie, pointing towards my caged clitty, and Natalie nodded her assent.

Debora gently lifted it up, taking the weight, and taking a look from multiple angles.

"Aww," Debora muttered something to herself, before speaking more loudly to Natalie, "It's so small!"

Debora glanced up at me and continued inspecting.

"If I lined you up next to my last one, I don't think I'd even be able to see this thing!" Debora laughed loud.

Debora let my whole package sit in the palm of her hand, as she continued, "I think just the head of his cock would be bigger than your entire dick and balls, sissy!"

Natalie laughed with glee and looked up at me as my cheeks turned almost crimson with embarrassment. "Go and get us another bottle of wine. Some snacks too, and some water. I'm going to fill Debora in."

Without waiting to hear a response, she led Debora to the sofa and they started talking in hushed tones. I jumped into action, still desperate to avoid upsetting Natalie any further with disobedience.

I returned a few minutes later, laden with drinks and some quick snacks I'd assembled, to find Debora leaning over Natalie's phone as she swiped through some pictures, both giggling intermittently, but they quickly stop as I entered the room.

"There you are. I've told Debora all about our situation and having seen some of the evidence, she agrees a little dicklet like that needs to be locked away," Natalie said.

"She's been telling me about your improvement in other areas though... I'd like to find more out for myself." Debora added. She shifts closer to the edge of her seat and slowly spreads her legs. I'd already seen the lack of a bra, but now I can see she was not wearing anything under her dress, presenting a beautiful shaven pussy, and begins rubbing her clit slowly.

"Get to work" Natalie commanded, as Debora stops rubbing and leaned back with her eyes closed, waiting for me to take over.

"Let's see how good your puppy's tongue is," Debora said.

I was expecting to get punished and if this is all I have to do then I'm happy to oblige. Natalie was watching passively, sipping on her wine as I dropped to my knees in front of her, and slowly started to use my tongue to explore her body, working my way up her thighs to start gently licking her clit.

Debora reached down as I started working, running her fingers through my hair, pulling my face tighter against her, and moving my head to ensure I was hitting the right spots. She lifts one leg to rest on my shoulder, her knee wrapping around my back, anchoring me in place further. My clitty was desperately trying to get out of the cage, pushing the cage away from my balls as it tries to reach its full size.

Debora moaned quietly as I continued, and after a few minutes, Natalie began to talk.

"I'm extremely disappointed with your behavior today. You've been so good that I was considering unlocking you while we had sex. But that's not happening anymore."

I felt a sudden coldness against my asspussy, jumped slightly, and stopped licking for a moment but before that Debora pulled my face even further into her crotch and pulled my hair to remind me of my job.

"Don't worry, it's just a little bit of lube..." Natalie said soothingly.

She rubbed her finger against my hole to spread the lubricant, and then slowly started pushing a finger inside making my whole body tense up, as I tried not to pause in servicing Debora.

My mind began to race as she spent a minute or so slowly pushing her finger in and out of my ass and then a big dildo began to push against my pussy.

"It's just a little bigger than the last butt plug," Natalie said. "You get used to the last one. Something to keep you on your toes a little, and maybe remind you of who's in control here the next time you think about misbehaving."

Debora moaned even louder, she was clearly enjoying my punishment and began to rub herself harder against my face, getting even wetter as her juices rub all over my face. She released my hair and grabbed my forearms, pulling me closer with both her thighs pressed to the sides of my head.

The stretching in my ass eases suddenly, but with a jerk, I can feel the full length of the plug push into me. Natalie has pushed it past the widest point, and my hole is fully plugged. I let out a muffled cry, half pain, and half relief, as she laughed contentedly.

"I've been thinking about some other steps we could take. Debora and I both know that staying in the cage for a while actually makes your tiny thing even smaller," Natalie said. "I was thinking about ordering an even smaller one, to make sure it stays snug. Any objections my sissy pet? I wonder how small we could go."

I let out another stifled moan, wanting to protest, but not wanting to annoy my Mistress anymore.

Debora laughed and chimed in between moans of her own.

"It's basically useless already sissy.... if it can't give Natalie any fun in the usual way, at least let her enjoy shrinking it!" Debora giggled.

I was reeling from the thought of it. It honestly excited me a little and I agreed to give my mistress complete control of my clitty. It's been fun so far.

"Your puppy is really good. I need to think about this payment," Debora said, as she suddenly released me from her grip, and relaxed back onto the sofa, still moaning from the residual pleasure I'd been able to give her. She exchanged a quick look with Natalie after recovering and then started to head upstairs. Once she was gone, Natalie turned her attention back to me.

"Today though, I was thinking about a threesome," Natalie said slowly, staring at me with a cool smile. My emotions are all over the place, is this a reward for my work just now? To make the butt plug feel more palatable, I didn't sit down properly, and not any time soon.

Natalie could clearly see my thought process, and her grin widened as I started to feel optimistic.

"Can we do this, Misstress?" I asked obediently.

"Well, in a way. I think it's time for bed, and I think ours has room for 3," Natalie said. "Keep your hands to yourself though sissy, or you'll really get a punishment. I need you to tidy up down here, and then come up to the bedroom."

I didn't dare reply, and she didn't wait for one. She quickly followed Debora, and I set about cleaning up - once again just trying to process how this had happened so quickly. Had Natalie set me up to fail? Or was really so stupid as to try and get a glimpse of Debora's breasts with Natalie just in the other room? I decided to blame the alcohol and focus on getting up to bed as soon as possible. The new buttplug addition to my rear wasn't exactly helping, every movement I made seemed to press into me somehow.