CHAPTER 28 (2/2)
Claire held it out a few long seconds, grinning at me as she watched the fear come across my face. She began speaking matter-of-factly. "Now... This is just the first one. It's a trainer one, you see? It comes in a set of three. We're going to start you off wearing the smallest one, and by the end of the week we're going to work you up to the biggest." She twirled it around in her fingers, watching my face as I studied the buttplug with trepidation. Claire's grin grew wider as she watched me processing the information.
"You're going to love it. Now, what do you say when someone gets you a gift?" She finally asked.
I knew I had to say the words. "Th-thank you... Mistress Claire..."
"Mmm, good babydick. You're welcome!"
She let out a giggle and then reached into the bag once again. "There's something else!" She said excitedly before pulling out the final insult to my pain: a butter knife, and a sealed stick of butter. "Lube," she said with a sneer. The look on her face said it all: I was about to get to work 'buttering-up' the buttplug - a painful reminder of the event from that morning.
"Now, you butter-up your new toy... Make sure you spread the butter on nice and thick all around, or it's going to hurt going in dry. And while you do that, I'll put on some nice porn for you to jerk-off too." She opened her laptop and began scrolling to a special folder while I opened the butter and began using the knife to spread the butter over the buttplug. I could almost hear my mom gagging and moaning on Brad's dick as I began spreading the butter. It almost felt like I was reliving that morning all over again.
Claire spoke aloud as she scrolled through her files. "Some nice special porn for milksop. His favorite kind. Some nice... She-male porn." I knew she was trying to provoke a reaction from me. Worse still, it didn't matter if I tried to hide my reaction or not because she didn't even look up from her laptop. I continued rubbing the butter all around the buttplug, the threat of having it shoved in dry still ringing loud.
"Ready to have your ass stretched open, butter-bitch?" She said as she looked up over the edge of the laptop. I felt my dicklette shrivel. "Drop your trousers, then." She said as she stood up.
She always giggled when she saw my dicklette caged up with swollen, painful blue-balls after a week in chastity. Of course, before there would be any playtime for me, I would have to withstand her flicking my balls a few times with her fingers. It hurt like hell as she flicked her finger directly into the center of each of my poor testicles (I swear she flicked them much harder than last time), but it was a small price to pay for the chance of an orgasm. The strangest thing of all was that I was beginning to LIKE Claire. Maybe it was because I was beginning to associate her with my weekly orgasm release. Or, maybe it was because of how in a twisted way, she actually had been strengthening my love relationship with Vanessa. Or, perhaps it was just desperate horniness after being denied any sexual playtime for so long. Whatever the reason, I found myself attracted to her when she laughed with pleasure after smacking my balls. I wanted to make her happy. I tried to stand still she whacked them a third time.
Next, she had me shove the butter-covered buttplug up my behind while she watched me with her phone camera. Even though it was warm and slippery, I really had to struggle to get it in - it was quite a bit thicker in the middle than the strap-on and it hurt quite a bit. I could feel my ass stretching until it slipped it, getting itself lodged inside.
"Come here, bitch. I want to make sure it's in all the way." She had me bend over the bed as she gripped the base of the buttplug and began pulling. I felt it straining and stretching to get out as she pulled on it. She kept pulling it out until the thickest part of the bulb was about to pop out - stretching my ass open painfully. She held there with the thick middle stretching me open and began working it in and out on that part, making me clench the side of the bed and groan with pain.
"Oh perfect, your ass is starting to get nice and stretched open," she said as she continued sliding the absolute thickest part of the buttplug in and out of my opening.
"P-please, it's hurting," I begged as the tears returned to my
face. However, unlike the emotionally upsetting tears from earlier, these tears were brought on from real, physical pain.
"Please?" Claire asked sarcastically. "Well, I was going to stop, but since you asked so nicely for me to keep going, I guess I will." She pulled it out once again, making the thickest part of the plug slide past my tight hole which was quickly loosening.
"Uhn, n-no, I mean p-please st-stop," I answered between the sniffling.
"Oh, you want me to stop?" She asked mockingly, sliding the thick part back into my hole.
"Y-yes," I answered, trying my hardest to withstand the pain. Everything in my body was telling me to pull away but I knew I had to bear it and clench the bed if I wanted to be unlocked.
"Oh, well why did you ask me to please keep going, then? You're so silly sometimes!" She shoved the buttplug in one last time, making me collapse forward onto the mattress as the plug lodged back inside my hole.
Next, she had me sit on the bed with my arms at my side. It felt sitting on the mattress with the plug up my behind, but it didn't hurt.
All it took was the sight of the keys to make my dicklette strain in its cage. "Is this what you want, Milksop?" She asked teasingly, dangling the keys in front of me once again. "You want your little dicklette unlocked?"
*Gulp* "Y-yes, Mistress Claire. I want that so badly."
"Hmm. Well, I guess you've earned it, shoving that butter covered buttplug in your ass, haha. So, here's the deal." She placed her laptop on my desk so I could see it. "I am going to unlock you, and you are going to keep your eyes on the laptop the ENTIRE time. You are not to look away from the screen for a second. You got it?"
My dicklette strained harder, begging to be released."Yes, Miss Claire," I answered quickly.
She slipped off her shoe. "Good. And since you love feet so much, I'll use my foot to get you off. All you get is the bottom of my foot - you are to keep your hands at your sides the entire time. You move them an inch and I'll send this butter-video to your little girlfriend without a second thought. Understand?" The thought of Claire sending that video to Vanessa made me cringe, but I quickly agreed. My dicklette was straining painfully now, making me wince. I didn't think I could wait another minute to have the cage off.
After I agreed to the disturbing terms - I was to sit on the bed unmoving like a stone and look at the laptop while she rubbed my dicklette with the bottom of her sock - she finally unlocked me. First one key, turning it with a quiet *click,* then after an excruciatingly long time, the other: *click.*
The cage popped off and I gasped with relief as my little dicklette breathed free for the first time in a week. Claire let out a soft giggle at the sight of my dicklette, standing at attention. "I still can't believe that's as big as it gets. It's so tiny, heheh. You know that you're never going to be able to please Vanessa with that, right?"
I could only nod quietly.
Claire sat back in my desk chair. "Have you seen how big Brad is? Can you imagine how disappointed Vanessa will be when she sees it? She's used to Brad now. Can you imagine trying to please her with that tiny carrot after she's spent a week riding on Brad's giant pole?"
Claire was starting to hit a nerve, and she could tell. My face betrayed me. My lips began trembling as I tried not to cry. I think I'd cried more today than ever in my life so far. I wasn't crying because Claire was being mean - I was crying because she was right. I had always been worried that during my first time with a girl I would be unable to please her, and Claire was making me realize how true it was. I'd seen Vanessa riding up and down on Brad's giant dick. I saw her crawling around on the ground worshipping it, just like my mom had. I was starting to realize just how my little dicklette wouldn't even compare after that.
"Little advice, Milksop. Get used to using your mouth. The only way you're going to keep a loose, dick-stretched slut like Vanessa satisfied is with your tongue. You know that Brad's dick isn't the only one that's been inside that vagina, right?"
I nodded, hoping Claire would stop, but she kept going. She knew she was getting to me, and she wanted to keep going until I was a broken down mess.
"At her previous school, she had quite the reputation. Apparently, she went through boyfriends faster than tampons. I heard they nicknamed her the high-school bicycle - all the guys got to have a ride. Her pussy's been so crammed full of dicks and stretched out, she wouldn't even feel your tiny dicklette. Trust me. Give up on trying to use your pecker. Get used to using your tongue. If you eat out her vagina every night, and get very good at it, you might keep. That's the only way you'll ever be able to satisfy her."
I don't know what is more pathetic: the fact that I sat there a blubbery mess while the realization set in that I would never be able to please my girlfriend with my worthless dicklette, or the fact - even through the crying and shame - my dicklette remained hard.
"I'm telling you this for your own good. I'm looking out for you, ya know. I don't want you to try and fuck Vanessa and ruin your relationship."
I nodded. She was right. Sure, she was cruel and mean and degrading, but she was telling the truth. I had to get sex with Vanessa out of my mind. I wouldn't ever be able to compare to Brad in bed - the well-built stud who was experienced and hung, who'd had dozens of babes in the sack already - I couldn't ever hope to please Vanessa as he did. I would have to try to use my tongue to keep her happy and maybe - just maybe - after some months went by, she'd let me feel the blissful pleasure of sex.
"Good. Well, let's get your cummies out of the way now. Remember, don't look away from the screen." She hit play on the video, and of course - a tall, dolled-up shemale appeared up on the screen, with a pair of big tits and an even bigger cock.
Claire stuck her foot up on the bed between my legs and pushed her toes against the underside of my dicklette. Her white sock rubbed against my flesh and for the first time in a week, I felt absolute, sheer bliss.
"Oh MY!" Claire said as she pulled her foot away. From one little touch and my dicklette was already twitching and pulsing. "Your little dicklette is REALLY worked up, it looks like it's about to cum already. Tsk tsk."
It took all my willpower to avoid reaching between my legs and stroking myself off, but I managed to stay still.
"Can't have you squirting your little cummies too quickly. The shemale is able to last longer than you. You're even less of a man than she is, aren't you? I know! Let's make a little game of it. Watch the video, and count out loud how many time she strokes herself. And every, hmm, let's say five strokes, you get one. So, count out her strokes - you'll have to watch her dick closely, hahah - and every time you get to five, I'll stroke you with my foot."
I quickly began counting off the strokes as the shemale jacked herself off. "One, two, three..." It was so humiliating having to fixate on the big dick on the screen. When I got to five, I was rewarded with another rush of pure bliss as Claire pushed her toes up the shaft of my tiny dicklette, up to the head. I began counting again, getting rewarded with another wonderful foot stroke after another five. Just from two little strokes, my dicklette was already leaking precum. I knew I was going to cum soon.
Claire knew it too, apparently, because she stopped. "My oh my, your little baby-dicklette still looks like it's about to cum. I think we'll have to up it, to ten. You still probably won't be able to last. That means you're like one-tenth as much man as a shemale! Hahah!"
True to her word, she gave me another stroke with the bottom of her foot once the count got to ten. I no longer cared that I was staring at a dick. I no longer cared that I had a buttplug shoved up my ass. All I wanted - I needed - was to feel another stroke on my dicklette. I counted diligently, fixating on the dick as if my life depended on it. Claire had won. She had me so well trained now. I really was her bitch, through and through.
Just when I could tell my orgasm was about to hit, she took her foot off and sat back in the office chair. "You know..." She said thoughtfully as she slowly spun around in the chair. "I was thinking about what you said earlier, about how I'm too generous for letting you have your little cummies every week."
Oh god. Why did she have to torture me right now. I was so close! The only thought that went through my head was: 'Please put your foot back, please put your foot back, please put your foot back!'
"I think you might have been right. Once a week does seem a little too good for you."
"What?" I asked impatiently, frustrated beyond belief that my orgasm was so close. The shemale continued jerking off on the screen, getting as much pleasure as she desired.
"Yea, you know. You haven't really done anything to earn a release. You've been out of school most of the week, and barely done any of our homework."
The frustration was unbearable. I have to give myself credit, however: even though I wanted so badly to jerk myself off, my arms remained glued to my sides.
"Claire... Please," I begged softly.
She spun back around to face me, glancing down at my dicklette. "Yea. I don't want you thinking you're allowed to cum every week, no matter what."
"N-n-no, please," I began begging louder. "I-I won't think that!"
She put her fist under her chin and rolled her eyes up to the ceiling thoughtfully. "Hmm... No, I think we better play it safe and have you wait another week. Don't you agree?"
"B-but, Claire... Oh my God... Please..."
She uncrossed her legs and stomped her foot on the ground violently. "I SAID: DON'T YOU AGREE?"
Her loud, angry voice scared
me back into submission. "Y-yes, I agree," I answered cowardly.
A smile crawled across her face. The sound of the shemale's loud moans filled the air as her big cock gushed out cum, while I sat there helplessly.
"Good." She pulled out the little dick-cage, and my heart dropped. My thoughts were racing. 'Is she really this cruel? I don't think I can survive another week. Surely she isn't really going to lock me up. She must be testing me.'
I stood still, my heart racing as she moved closer towards my dicklette with the cage. "Now, of course, the cage isn't going to go on with your little dicklette all erect like that. You know what that means?"
I nodded, but couldn't find any words to speak as she held up her fingers in a 'flicking' position.
A cruel smile crossed her face as she moved her finger under my swollen, throbbing testicle and gave it a good, hard flick. I closed my eyes and yelped as my emotions overtook me. WHY was this happening? Why... *Flick!* More pain. More giggling. My dicklette shriveled smaller.
I felt the all-too-familiar touch of the plastic cage covering my dicklette. I couldn't move a muscle. I heard the key click locking it shut.
"There! See, it's just one more week. That's not so bad, is it?" She asked with a huge, sneering grin.
"N-no, Miss Claire."
"Good. Hehe. This was fun! I'll see ya at school tomorrow." She stood up to walk out. I was still doubting if I was really being left locked up or not. I kept expecting her to say she was kidding and let me out, but she didn't.
"Oh and by the way, milksop." She stopped at the door. "You'll be wearing that buttplug to school tomorrow. We'll be checking to make sure. You need to wear one every day, so we can train your ass up to the biggest one, remember? I left the butter on the desk for you." I couldn't even muster a response.
"And if we check and see that you aren't wearing it at school tomorrow... No cummies for another week. Don't test me on this. Okay, bye!" She put her hand over her lips and blew me two loud kisses: "Mwah! Mwah!" before disappearing out the door.
I broke down. It was more than I could handle: the thought of being unable to please Vanessa, being Brad's 'buttering-boy' while he fucked my beautiful mom, the fact that I had to wear this dickcage for another week with my swollen, painful balls... I lost control and began sobbing, burying my face into the pillow. The buttplug ached as I moved, and I realized that was just one more thing I had to deal with: pulling it out before sleep.
Claire had successfully transformed me into the biggest loser on earth.
