Bottom Boi Ep. 06

"Come on, baby, rise and shine," I got the message and opened my eyes, seeing Mistress Natalie standing by the bed I was lying on.

"How long was I out, mistress?" I asked. "Why do I feel this tired and sore?"

"Don't worry, you had your brains fucked out of you," she replied. "You just need some time to adjust and some food to eat and you'll be good as new. Go make some cereal for us."

Needless to say, I was hungry enough to eat anything at that point. I was still naked and the room still smelled like hot steamy sex. After finishing our breakfast, the mistress gave me an address.

"This is Debbie's address," she said. "From now you'll live there, alright?"

"Yes, mistress," I replied. I wanted to ask if is it permanent but I knew it'll be temporary.

"I'm going out. Don't be late, she's waiting for you," she said then left the apartment.

There wasn't any dress code so I dressed as I do regularly. After the bus ride, I walked for 30 minutes before coming to the right in front of Debbie's address. I rang the bell and in a minute I heard someone was coming. The high-heel sounds were sexy.

"Finally, the package arrived. Come on, get in," Debbie said resting her gloved hand on my shoulder. "Now move your butt, silly boi."

Her height was startling. She had to have been at least 4 or 5 inches taller than me with the high heel. She wrapped an arm around my waist as we entered her house. I leaned against her, feeling her warmth through her robe, all six feet of her pressing against my quivering body. Arms at my sides, I followed her obediently. I could smell her sweet floral perfume.

"Listen boi, Natalie just don't send you here for a vacation," Mistress said. "I bought you from her. Your Mistress Natalie wants you to serve me. Can you do it?"

"Yes, Debbie," I replied.

"Mistress. It is Mistress Debbie, understand?" she said.

"Yes, Mistress," I replied obediently.

"I can take very good care of you only if you let me. I can make you feel things most bois can only dream of. But nothing in life is free. A boi must trust his mistress with all of his heart. Trust. Obedience. Love. Desire. That's what I want from you. You will dress how I want you to. You will behave how I want. You will accept every punishment and reward that I deem fit," Mistress Debbie said.

"Yes, Mistress, I'll do whatever you tell me." I quickly agreed.

"Get on your knees," she chuckled. "I want more than lip service, sweetheart. Your devotion needs to be real." She grabbed my wrist and brought it to the hem of her robe. "Here's your chance to prove it to me."

I slipped my hand under the robe, knowing what I had to do. I grabbed a handful of warm smooth thighs, and it was enough for my balls to clench in anticipation. She was curvy, but I could feel the power. It was almost mesmerizing, to lay hands on her. I caught myself drooling.

"Move your hand higher," she said. "Don't be shy."

I touched the lacy band of her panties. Already I could feel the heat of her pussy and the smell was intense. I carefully reached between her legs, pulling the lacy waistband out of the way, I prodded with my fingers and found something huge and fleshy. It was long, and hard. A realistic dildo.

"You're not getting my pussy so easily, sissyboi" she laughed, grabbing my wrist. "You need to show the devotion and passion for me."

Then, she approached me I was sitting on my knees, put the palms of both her hands on my cheeks, and moved her crotch to my face, so I opened my mouth wide, letting the tip of her cock land on my tongue. She starts using her 12-inch pole grabbing my face in her hands to use my throat as her own personal fleshlight when she planted her right leg on the floor to my left and lifted her left up on my right shoulder.

My throat muscles were still loosened up by mistress Natalie, so as she fucked my face hard and deep, they didn't resist. As her leg leaned against me, I could feel it moving back and forth on my shoulder, her foot sliding up and down my back as she bounced up and down, fucking her massive cock in and out of my mouth slowly but deeply; her glans hilted in my throat in one moment and withdrew to my mouth in the very next. The mere few minutes of this was enough to get my clitty fully hard, my precum flowing.

Then Debbie pushed my face onto her cock as hard as she could and held it there until I started to run out of air before letting me go for a split second and then doing it all over again. It seems like she just loves to suffocate her boytoy with her big strap-on dildo. Well, as she did it for a while, I was getting dizzy once again, and, as she finally pulled her cock out and put her leg down on the floor, stepping away a bit to let me see her spit-covered cock. It was looking delicious.

"Take my cock deep inside your throat pussy, slut," Mistress Debbie grinned.

I could feel the curves of her dildo even more intensely than before, so as I deepthroated her, getting it in deeper and deeper, I enjoyed it immensely. However, at one point, it turned out to be an awkward position and it wasn't possible to get her cock in deeper without risking an injury. However, an experienced slut like myself is always ready for that kind of situation: I turned away from her and, while still kneeling, I grabbed onto her hips and arched my back backward until my face was right underneath her pussy with my mouth wide open.

"Mmmm, you really are a cock sucker, aren't you?" Mistress Debbie moaned with a naughty tone as she spread her legs around my head, letting her pussy fall down onto my mouth, allowing me to lick them for a while, before replacing them with her cock, which she instantly shoved into my throat and proceeded to fuck my face with. In this position, it didn't take too long for her cock to the hilt inside my throat, which was not only slutty enough but also loosened up by the endless string of anal orgasms that I felt that day. Her sheer size wasn't a problem. In fact, it only made the whole experience far more pleasurable.

In a minute or two, she was fucking my face really fast and hard, filling my nostrils with the strong intoxicating smell of her sweat and pussy juices brewing inside. She tried to step away at that point, but I held on to her tightly, so she just made my knees drag on the floor instead and as she stopped her motions, I started to use my knees and my arms to impale my throat on her cock instead.

"Oh, is that how you wanna play it, you little filthy whore?" she moaned with an angry tone. "Fine, have it your way," she said as she grabbed my face again and proceeded to fuck it as hard as she could, filling my system with organic waves again and again and again. It wouldn't have taken me more than 5 minutes to cum from just having my throat fucked like that.

"Natalie was right. You still need to learn a lot," she said with disappointment. "Maybe a little public humiliation will help your case. Wow, nice timing. I need to buy some new toys anyway. Go clean your face, we're heading out."

"Ok, mistress," I replied.

After 15 minutes of driving, we reached the store. First thing in the door I saw high-platform hooker shoes. Just look at those heels, super hot.

"Take a look around, sissy," Mistress ordered. "And find me a big dildo."

Oh fuck! I browsed through the panties! Then started browsing in the toy section. Nipple clamps! Saw a set with a connecting chain, and weight in the middle. And the butt plugs... shaped like a dick, or not, but big, big enough to...

I needed to find a big cock. Well, a dildo, I'd admit that much. But there were two perv-looking guys over in that section, didn't want to give them the wrong impression. So I went back to the toys and found some cock rings, cock, and balls rings... oh yeah. After a while, the guys wandered elsewhere, so I went over and found a nice big fat one, 9 inches, realistic skin, a three-inch diameter at the base, and a squirter! A reservoir I could fill up with cum, or cum-like lube, and it has a vibrator! I had to have it! Mistress Debbie was in front of the counter with lots of toys and gear.

"Come here, sissy," Debbi ordered. "Don't be shy, only bitches are here."

Look at the goddess behind the register! "You gonna take those to go or will you be eating them here?" the register lady said. Oh my god. I immediately started blushing.

"Oh, one of those shy crossdressers, huh? Yep, definitely the sissy subtype." She licked her lips. Pink lip gloss. "How long have you been training this sissyboi?" the register lady asked.

"Just got him," Debbi giggled.

"Well c'mon already, bring your new favorite toy on up here," the register lady said.

I looked down, humiliated, but I put my stuff up on the counter, and she started ringing it up. My face was so flushed, my blush was probably lighting up the walls all the way across the store. Shit! If I could get any redder. So damn HOT in here.

"You'll need a new harness to hold that in," the register lady said. "Let me bring it for you. So how good is he?"

Oh. My. God. She was relentless! Humiliating the fuck out of me. Shit, I was getting such a hard-on! Oh fuck, if only she would tell me to...

"12-inches deep throat," Debbi smirked.

"Dammn," the register lady said. "Mind if I visit you just for your new meat?"

"Hehe, I'm taking her to the auction very soon," Debbi replied. "So, how much do I have to pay for all of these?"

"I'll give you a special discount if she gives me a special treat..." the register lady offered.

"Time to proud your mistress, boi," Debbi said. "Don't let me down."

"Kneel sissy," the register lady offered. Then I kneeled in front of her. My face was an inch away from her crotch. She put her hands on my face and stroked my face with her finger. As her fingers slide over my lips she said "Lick".

I licked the proffered finger with my tongue. She slid it into my mouth, letting me get it good and wet. Then she took out and slid her hand down to her sex where she worked it around for a moment. It came back up to my mouth a little later and I licked at it, making it wet, and cleaning it of her fluids. She returned to fingering herself.

The next time it came up from her crotch it hovered in front of my face and she said "Do you want to lick it?"

"Oh god yes, I so want to lick it."

"Stick out your tongue," she said in a lilting tease.

I stick out my tongue and make slow licking motions the way I know she likes me to lick her crotch. She teases the tip of my tongue before plunging her finger into my mouth briefly. Then she slides it back to her crotch.

"Tell me how much you want to eat me," she asked. "Would you like to be my pussy licker?"

"Yes please," I said in a half whisper half whimper. "I would very much like to lick you. I would love to caress your lips and your clit with my tongue."

"Tell me how you would do it," she ordered.

"I would lick them so lovingly and gently. Just the tip of my tongue up the sides of your labia. Over and over again. Like licking honey off a bee's wings. Up one side and down the other. I would reverse the direction every now and then, but not too often. I know how my mistress like me to build it. And when you are wet enough that my chin is covered in your love I would start to lick more firmly."

"Yeeess." She hissed. "But I'm not sure you deserve to lick it."

"Of course not" I replied. "I am not entitled to taste you. But if my tongue would be pleasing to you, then I would be honored."

"Now eat it like a good boy."

"Yes ma'am. Thank you. You won't regret this."

"Shut up and lick me," she said lightly.

And I did just as I had described. At first, I could tell her arousal is minor at best. But as I traced the tips of her labia over and over with the tip of my tongue this changed. Soon her hips were no longer still.

"Is your clitty hard in your panties?" she panted.

"Oh god yes."

"That's a good boi. That is so hot. Make me cum now. Suck my clit. Suck it hard," she moaned loudly.

Her world exploded as I suck for all I'm worth. Her legs were like a vise on my head and she grabbed my hair and groaned out her orgasm.

When she was settled down she stroked my head. "That's how a good boi should behave. He's super good at it. I have changed my mind. I'm giving these toys away for free to you. Consider them on the house. I'll definitely meet him in the auction."

"Thank you very much," Debbie replied.

Then we came back to her house. She was quiet all the driveway. She sat on the couch.

"You did well but practice makes perfect. Time to teach you more pussy stuff," Debbi said. "Now undressed."

I put off my dress as she told me and I was so afraid because I came in my pants while they were humiliating me. I tried my best to not come but it was impossible. Two goddesses were talking about me. How could I resist?

"You came while you were eating her pussy? Hmm, you are into exhibitionism," Debbie said. "Less work for me to prepare you for the auction. You ready?"

"Ahh, yes, mistress. I'm humbled to receive your blessing. Please use me."

I reached around her waist and slowly slid down her High-Waist Wide-Leg Pants. I took time to stare at her panties as my Mistress Natalie taught me. Cupped my hand over the pelvic bone and pressed against the heat of her warm pussy. Slid my hand down to feel her lips under the material; felt the slight dampness. Moved my face closer and run my tongue over the same area. Pushed my face into her vulva, all the while sliding my fingers under the sides of her panties and slowly inching them down until they were around her knees. Moved back, looked at her, and slid her panties off the rest of the way.

"Now that my beautiful pussy is exposed just take a good long look at it; savor it because, in a matter of seconds, you will be up close and personal with God's greatest creation," Debbie said. "Remember that every pussies aren't alike. They all have their own beauty about them. It's your job to find what's beautiful about the pussy staring you in the face. Maybe it has long lips or tight lips or a hooded clit or an exposed clit. Whatever it is...let her know. But only when she asks, understood?"

"Yes, mistress."

"The inside of a woman's thighs are two things: soft and very sensitive. They are a great starting and ending point. There is plenty of areas to start getting her in the mood. Lick all around the thighs and every once in a while skim or breath heavily over the vulva. There is absolutely no rush to get to the clit," Debbie said. "Remember if your woman is one who doesn't mind her anal area attended to, and you're up for it, give that some well-deserved attention - and you're finally ready to lick that pussy just remember variety is the spice of cunnilingus. Rub your face over her."

I nodded.

"Sissy, are you ready to give my pussy a French kiss?" Mistress Debbie asked.

"Yes, Mistress," I said and moved forward to give it while she moved backward one step and I fell on my fours.

"Not so fast, princess," Debbie taunted. "I need to punish you first for your cum crime. Follow me."

I followed her to the bedroom where she was patting the bed to lay me down. I laid on my back. She grabbed a pillow and put it underneath my ass, Debbie turned me to my left side so that my left hip was resting on that pillow, while my knee was resting on the surface of the bed. She then grabbed my right leg and lifted it up on her right shoulder before pushing the full length of her lubed new cock into my ass in one thrust, making me moan loudly: "AAAAAAAAAAH!"

"Yea, take that sissy. Do you want some attention on your caged clitty," Debbie said slapping my clitty continuously. "How's that feel."

Her hard fucking has no mercy until I sissygasm twice in a row.

Despite the fact that she just made my cock cum twice already, my caged dicklet was already leaking precum again, and as she continued to fuck hers all the way in and out of my ass, it was pushed over the edge for the third time. "AAAAAAAH! AAAAAH! OH, GOOOOD! OH, MMMMM!" - I moaned like the filthy slut that I am, my mind hijacked by the sensations of the curves on Debbie's cock stimulating the points of my ass that had never been touched before, of its huge helmet digging in and out of me at the faster pace than ever, of my own clitty spraying its fluids all over myself and the left side of the bed.

"I'll fuck all the sissygasm out of you," Debbie grunted.

I was feeling like this was enough to make me experience another sissygasm immediately, and I'm sure that it would have had Debbie just let it happen. She kept fucking me faster and harder with every thrust, making me feel helpless, almost blowing me away with the whirlwind of sensations that her cock was filling my every nerve with, and just as my dam was about to burst into tiny little pieces again, she pulled her cock out of me entirely and sat down on the corner of the bed with her back turned to me, looking back at me over her shoulder.

She was so hot from behind there, despite the fact that I couldn't see the most important part of her body from that angle. I understood the meaning of her look immediately, so I did my best to get myself up, but my knees were so weak and my limbs so out of control that all I could do was clumsily crawl over to the corner of the bed where she was sitting with her sexy face looking at me over her strong shoulder. Fortunately, Debbie was as impatient as I was - she used her left arm to pull me up and when I was close enough, she used her right to throw my right leg around her, until she was sitting in that corner with her huge cock leaning against my ass and back while my legs were spread around her, unable to reach the floor.

From that position, Debbie just grabbed my ass with both hands and lifted it up on her cock, impaling it, and forcing me all the way down to her rubber balls within a second. I wanted to moan and scream again, but her lips shut my mouth, so I was unable to. But I didn't care. As soon as her cock pierced my asspussy again, horny and electrified, I put my hands on her shoulders and began to ride it myself. As I pushed myself off her shoulders and let myself land back down on her lap, our kiss finally broke and I started to scream into the air.

"AAAAAAH! OH GAAAAHD! AAAAAH! OOOH! MMMMM-AAAAAH! FUCK MEEEE- AAAAAH!" - I made these loud high-pitched moans like a sex-crazed slut while bouncing on her cock, and she helped me out a little, using her hands on my ass to make sure that I'm all the way up before I let myself go, and that her cock hilts as fast as possible when I start falling down again. Other than my moans, the room was finally filled with the incessant loud rhythmic sound of our bodies slamming against each other: "THWAP! THWAP! THWAP! THWAP! THWAP!"

My arms were starting to get tired, but it didn't matter; the less I was able to push myself up and down Debbie's cock, the more she did it for me, until eventually, it was her doing all the work, gripping my buttocks tightly and bouncing me on her monster faster and faster. At that point, I was only using my arms for balance, holding on to her for dear life while she fucked me hard and fast. She completely dominated me, making me feel helpless, which turned me on so much I could feel the new orgasm coming, so I started to roll my eyes back willingly, even before it took over, anxiously waiting for it, submitting myself completely.

It didn't take too long for me to feel the surge of orgasmic bliss electrifying my insides and spreading all over my body. As it spread to my arms, they just dropped, so I couldn't hold on to Debbie anymore, and my back started to arch backward before she moved her left hand up, grabbing it, preventing me from falling to the other side, but somehow not slowing down the rhythm of her ruination of my poor little ass. As it finally spread to my head, I unleashed a loud moan, which turned into a weird slutty scream all by itself, before finally being distorted and going silent: "MMMMM-YEEEEAAA-EEEEEEeEeEeE-"