Bottom Boi Ep. 05

Bottom boi perspective

I ain't quite ready for what greets me in the bedroom. Natalie is lying on her back on our bed, still mostly wearing her low-cut dress, but her breasts are spilling out, with Debbie's hands massaging them... as she sits, completely naked, on Natalie's face. Natalie's eyes are half closed in the heat of the moment, but she notices me entering the room.

"Oh... sissy... I think that's you..." Natalie clearly wanted to give me some detailed instructions, but can't focus now, with Debbie's tongue deep inside her.

"Kneel!" Natalie ordered.

I dutifully take a place at the end of the bed, looking up at the face of my beautiful mistress, as if someone else is giving her what she needs. The butt plug moves uncomfortably inside me again, and I could swear my dick is so hard it's going to shatter this cage. But I tried to keep my cool and clenches my fists to try and relieve the tension.

As I watch, Natalie changes position, glancing up at me with a wink, before bending down so she can return the favor, and begins gently teasing Debbie's wet mound with her tongue.

After a few minutes, Debbie climaxes loudly, and they move again, swapping 69 positions, Debbie idly kissing up Natalie's thighs, and rubbing her clit with her fingers slowly. The initial intensity has faded a little, but they're not showing any signs of stopping. They seem ready to enjoy each other all night long. I have been shifting in place uncomfortably for a while, I would give anything to be involved, but can't ignore that Mistress Natalie told me to kneel. But even if I could get on the bed, my chastity would stop me from enjoying it the way I wanted to.

"May I join, Mistress?" I asked.

"I wondered when you'd chime in... you know it wasn't that long ago that you didn't like performing oral. All you cared about was pumping your little willy in me a few times and then falling asleep. It's such a good improvement, really. But this is a punishment. Don't ask again, if we need your help we'll tell you." Natalie said dismissively.

Debbie paused for a second and whispered something to Natalie, and she nodded and then gently maneuvered her back to keep attending to her next orgasm. They'd both lost count at this point, but I was extremely aware I'd had precisely zero.

A little later on, I started to think they were winding down. They were cuddling in the covers, making out and occasionally getting handsy, and he was hopeful they could all go to sleep soon. He wasn't sure he'd find it too easily, but it was better than the torture of watching more.

"I wonder if you should get out your toy now Natalie," Debbie said suddenly, looking straight into my eyes, then she sat up straighter and tried to glance around subtly.

Natalie gets out of bed, opens one of the drawers, and pulls out... a strap-on. The dildo itself is around 8 inches long and attached to a leather harness. She walks over and stands next to me.

"Now give it a nice sloppy kiss," Natalie said. "Good boi. That's enough. Don't be greedy."

"You see, this should go around you nicely, giving you the perfect cock. I don't have to worry about your little dicklet getting overexcited too soon," Natalie explained as she adjusted it to stay tight to my body.

Debbie laughs and comes to sit on the end of the bed.

"Oh my god, it's just so much bigger than the cage! It hides it completely from above, you can pretend that little thing never existed!" Debbie mocked me.

"Debbie actually wanted me to get a bigger one you know, but I think I need to ease into it," Natalie said, giggling at the look on my face.

"Now fuck me darling" Natalie commanded.

They pull me down onto the bed, Natalie lying on her back, as Debbie guides the head of the strap-on towards her pussy. Once it's in, Debbie sits back to watch, and I see Natalie's eyes roll back and she lets out a silent gasp as I slowly insert the full length. I can almost pretend I feel it, but the frustration is sending me crazy as my cage bobs up and down, straining to feel her warmth.

I begin to thrust, my Mistress starts making noises I've never heard before. Debbie has spent a long time warming her up, and now she's going to get her true climax from my pretend penis. As I lose myself in the moment, Debbie draws nearer and begins to massage my balls while her other hand prods gently at the plug in my ass. She leans close and whispers goading and teasing words in my ear, which I can barely make out over my moans. With her encouragement, I ravished my mistress like never before.

We spend a while like this, changing positions as Natalie enters new worlds of pleasure, but always with me as a toy, never truly participating until we all 3 eventually collapse on the bed. Natalie is still moaning as she slowly comes back to earth, and I almost whimper with relief that it is over.

[BDSM]

We don't talk anymore after that - all three are exhausted. I take off the strap-on and turn off the light, lying down as we arrange ourselves on either side of me. Debbie falls asleep first, on my left, one arm draped across my abdomen, hand lingering agonizingly close to my pathetic caged clitty. Natalie falls asleep next, one leg wrapped around me, and her hand cupping my breast. I spend a while staring into the darkness, as my clitty slowly softens and allows me to find comfort, before slowly drifting off.

I drift in and out of sleep for a few hours in the morning, unable to move without disturbing the women. I consider what happened last night - does this mean Debbie will be involved again? If I can be good next time, and get a night out of the cage, maybe this will all work out. Some of the things they talk about are... extreme.

Debbie finally begins to stir, quickly extracts herself from the bed, and starts getting dressed, which wakes Natalie in turn. Natalie and Debbie start chatting as if they've had a perfectly normal night in, and I just listen as normal about the plans they both have for the day.

"Sissy, show Debbie out, will you? I'm going to hop in the shower!" Natalie said before disappearing into the bathroom.

I follow Debbie down the stairs, quietly.

"Well, it was uhhh, good to see you, sissy! I knew things might get a little spicy after I flashed you, but..." she said, slightly sheepishly, "Natalie and I fooled around when we were together. Now kneel."

"Yes, ma'am," I replied but I didn't know why I said, ma'am.

"It is Mistress. Looks like Natalie didn't lie about it. You do need some special care," Debbie said pushing my head toward her naked pussy. "I am going to break you..."

Kneeling down at her feet, my tongue buried in her pussy, she stares down at me. Innocent, inexperienced, yet with an insatiable willingness to submit. To serve. I think I'll never forget the look on her face as she says it, the confident smile, as if it's not a mere statement. It's a promise.

I stay silent as she talks, not really knowing how to respond. She let my head go and then I stand to open the door for her. She looks pleased to see me so submissive. She takes this as encouragement. Then out of nowhere, she quickly grabs my caged manhood and gives it a light tug at the doorway which makes me let out a little yelp.

"Maybe next time I'll bring one of my boy toys... I know she liked the strap-on, but I wonder how she'd deal with a big cock like that dildo next time. You could watch, of course, keep us both warmed up in between maybe... and clean our pussies. Ohh, and I let you kiss me too before I swallow those big loads," she trailed off starting to daydream a little, before catching herself. "Anyway, I'll definitely see you soon. That is too much fun not to do again. Too many bois these days just want to fly too close to the Sun, only to step away moments before they actually feel the fire on their skin. But I want to burn you down, baby, I want to shake you to your core and make you mine."

My caged clitty twitched at the mere thought before she finishes her sentence.

Once Debbie leaves, I slowly start to climb the stairs and mistress Natalie is wearing some lacy black lingerie and doing her makeup in a mirror.

"You can lie down for a minute honey, I'll be ready in a second."

I don't object to getting comfortable on the bed and letting my eyes close.

"That was a long night... I hope it wasn't too torturous. I could see your little willy trying to break out of the cage, you really shouldn't have been such a pervert with Debbie you know. I really was thinking about letting you out for a night," Natalie said. "Now you have to be taught a lesson."

She pauses for a moment, and I consider trying to defend myself but doing nothing will be better.

"You did very well though. Debbie seemed very satisfied," she said.

I open my eyes and sit up to reply, "Thank you, Mistress, I r...", before catching sight of her.

She turns around, the strap-on attached at her waist, s new dildo pointing right towards me. Was she wearing that when I came back in? Or did she sneak it on?

"I think we're out of lube, you'd better get this nice and wet if this is going to work," she ordered.

Mistress doesn't let me look at it from a distance for too long, though. She pulls me out of bed and down onto my knees, her hands on the back of my head as she pushes her cock into my mouth. She pushes my shoulders down, forcing me on my knees, where I get a real good look at it, and it is nothing short of amazing. Her cock stands at a little under 12 inches maybe, and it is definitely thicker than any cock she has used before.

"Do you know what makes it truly amazing, sissySlut?" Mistress asks. "It's not only its size, but its unusual shape. An unevenly shaped cock is the best toy to play with, as it stimulates parts inside you that usually don't get that much attention."

Well, since I'm a slut with some mileage, the shape of the mistress' cock pretty much screams pleasure to me. It's the sexiest one that I have ever seen. Its helmet is one of its thickest parts, and right at its crown, the shaft is the narrowest, but its underside gets thicker progressively, getting thickest an inch before the middle, at which point it gets narrow until three inches before its base, where it gets visibly less narrow than at the glans, and the final three inches are just flat; at least when viewed from the side. From below, you can see that her cock has a totally different shape, and the curves on its sides don't match those on the top and bottom parts of its shaft.

The view from the top and the bottom of the Mistress' shaft matches the one from the sides only right next to the glans, but the upside is almost flat, with the exception of its veins, and the underside gets thickest about 5 inches down its length. The sides of her cock are symmetrical, and they slowly get thicker until about 3 inches from the tip, at which point they abruptly get narrower, being flat for about 3 more inches before getting progressively thicker again, getting thickest right at the base. All in all, it's the fattest part of the dildo, with a circumference of almost 7 inches, and the narrowest is just under 6.

I want to say something, to praise it, to tell her how I feel about it, but that cock simply takes my breath away. My clitty starts to throb and leak precum as I observe hers, but I can't even bring myself to moan, let alone speak.

"Yesterday was fun... today is just getting started," she said.

Then, she takes her cock out and I kneel there with my mouth wide agape, examining it from all sides and admiring its size and shape. My clitty is already drooling ridiculous amounts of precum, soaking our carpet with it. In about a minute, Mistress grabs my hair and pulls my head back before aiming her cock at my mouth and shoving it as hard as she can with her powerful hips. This doesn't happen to me normally; her cock makes me gag, choke, and cough, but that doesn't stop her. She doesn't let me take my time to catch my breath; instead, she keeps fucking my face and even plugs my nose with her left hand while using her right to keep my head in place for her to fuck.

It isn't until I start to actually run out of breath that I realize how strong she is. For the life of me, I can't break away from her grasp, and I'm almost fearing for my life at that point. I'm getting dizzy, my jaw is beginning to hurt, and my throat is already sore, but she doesn't seem to be slowing down until suddenly, she takes her left-hand fingers off my nose and uses both her hands to push my head down, impaling my throat onto her massive cock as hard as she can, holding it there for a few seconds before finally letting it go and pulling her cock out of my mouth.

I cough and gasp loudly, my head still spinning like crazy, but I can't help staring at that huge invader that's still connected to my throat via numerous strings of saliva, much of which covers my chin as I cough it out and the strings break. At that point, my survival instinct is completely replaced by blind dumb lust, and I'm not even trying to fight back. At that point, I think that if she gave me a choice to choke me to death with her cock or never see it again, I would pick the former. Mistress Natalie actually uses her monster cock to hack into my instincts and senses and mold them to her own liking, without even making me cum.

She stands there with her cock staring me in the face from a safe distance, but I can't help myself. I crawl over to it, impaling my slutty throat on it again. I can hardly get over half of it in there, but with the size and shape of her cock, it's just enough to make the orgasmic waves start to form deep inside me, washing over my body. At first, her crown stimulates my throat as it pushes its way in and out, then the thick sides of her cock as I turn my head to the side, attempting to get more of it inside. In the end, it's the feeling of the thick middle of her cock making its way in and out of me.

My throat is stimulated in subtle ways the likes of which I've never felt before. Emma's cock reaches places in my throat that were never reached before, and I love every single second of it. If she just went on doing this to me, I could have a double orgasm right there. The one thing about my mistress that always turns me on is the fact that she doesn't care how I feel. This is all about her, what she likes, and all the pleasure I'm feeling is just collateral damage her cock is causing as it attempts to please itself. Sure, she will look to please me as long as it's not an inconvenience to her, but that's not her primary goal.

I'm already messed up with spit and precum, but I don't care about it anymore. Her cock has complete control over my mind. Instead, she steps away from me and pushes me towards the bed, making me fall down on my back, breathing erratically, scared about what's about to come next. But as I said, my lust is greater than my fear. She walks over to the bed while stroking her spit-covered cock with her right hand. I lift my legs up, making my naked and cleaned-out ass stare at her automatically, inviting her. A little smirk on her face tells me that she likes what she sees.

"Wow, you're a true slut, aren't you?" Mistress says. "Prepare to have your ass torn apart."

Mistress moans as she takes a bottle of lube from under the bed, applies a generous amount of it to her cock, and throws it back down as she spreads it over its length.

"You just needed some extra encouragement to push my monster inside your throat," she giggles.

"Y- Yes... P- Please, fuck me," I answer in complete ecstasy. I can't believe that I'm already that horny, that I already want it that much. She's a true expert, able to drive me this crazy by fucking my face. She doesn't say a thing; when her cock is nice and greasy, she silently approaches me and points it at my ass, resting its tip against my boipussy.

I think at this point she will start teasing me or fingering me or using dildos on me to prepare my ass, but Mistress doesn't give a shit about things like that. Instead, she just proceeds to push her lubed-up cock into my ass, which is so sudden and unexpectedly stretched to its limit.

"AAAAAAAAAAH!" I scream in pain as her cock spreads my asshole apart as she pushes her thick tip right through it. As she mounts me, she puts her hands on my thighs and spreads them apart while climbing the bed and kneeling on the edge of it.

"Oh god, please stop! aaaaa," I beg her to give me a break, but she puts a hand over my mouth, shushing me as she keeps pushing.

I try to fight it, to push back, to escape her grip, but in the position I'm in, it's literally impossible. My lower body is pinned down by her, and every attempt to make my escape by pulling my upper body away would only make my asshole hurt even more, feeling the full pressure of her massive cock inside it.

"Let it go, baby. Your ass can take it. Let it go," Mistress orders, and I oblige. Drenched in sweat, shaking with pain, and feeling like I'm being obliterated, I just let her have her way with me and try to relax.

It was difficult, however, since her tip was not even all the way in yet, but it already hurt that much; Still, since the moment I relaxed my muscles, it took a mere few seconds of little back-and-forth movements for her glans to finally pierce my sphincter and make this feel a lot better. Due to all the pain, my caged clitty had gone slightly limp, but it was getting hard again as she kept fucking me using the same little movements she had used before without taking her glans out, just pushing her cock deeper and deeper inside me with each thrust.

There was still quite a bit of pain, but nowhere near as much as there was before her tip were all the way in. I was thankful for the fact that she applied lube so generously since I was pretty sure that her cock would kill me if she didn't.

"MMMMM! MMMMMPH! MMMPH!" Mistress Natalie's hand was muffling my moans as she slowly fucked my ass, getting her giant cock deeper and deeper inside it, conquering new depths with every thrust. After a while, she finally removed her hand from my mouth, so I was about to moan loudly, "MMMMPH! MMM- AAAAAH! AAAAAH! OH, FUUUCK!"

"Yeah, you're beginning to like it, aren't you?" she asked me and she was right. I was truly beginning to like it, as the familiar pleasurable sensation started to emerge behind that pain, but the pain was still a dominant feeling. Still, it gave me something to hold on to and make this part a lot more bearable. She was just hovering over me as she slowly got her cock in deeper and deeper without even breaking a sweat, while my whole body was drenched and shaking.

"OH, YES! AAAAAH! OOOOH! AAAAAAH! OH FUUUCK! AAAAAAH!" I moaned as her cock wasn't even two inches in at the point when I could clearly feel its sides push my sphincter wider and wider apart and the pain, which I was just beginning to get used to, came right back in full force, so my moans turned into screams again. This time, however, it wasn't agony, but a delicious mixture of pain and pleasure that I came to love so much over the years, except far more intense than ever in both regards.

I don't know for how long she fucked me like this, but it wasn't long enough considering her cock size and how suddenly she entered my ass, so the pain just wasn't subsiding. I think she was going in as fast as she could without permanently injuring my ass since I could see by her expression that she was getting bored and hardly controlling herself, wanting this part to be over as soon as possible. I, on the other hand, was enjoying it immensely. To me, this was it, the pleasure I had never felt that intensely before.

"You're close, aren't you?" she asked. "But don't even think about it. I promise if you break one more rule I'll bring Debbie to fix you properly. I never spend this much time with a sissy slut before."