“Are you ok Wolfy Boy?” he asks in the here and now. Remembering all of this takes a while, I must have spaced out.

“I’m fine Red,” I reply with a smile and give him a quick peck on the forehead.

“Oh, ok.” He replies, still a little unsure. He begins wringing the hem of his apron back and forth, something he’s taken to doing when he’s thinking, I love it. “If you’ve had a bad day, and wanted to relieve some stress you could…” his voice suddenly becomes really quiet before returning to normal volume “… you always look happier after that.”

I think about what he’s trying to say and it takes a few seconds before it dawns on me. “Oh!” I reply suddenly and he shrinks away, still in my arms. “No sweetie, I didn’t have a bad day and I don’t want to spank you. Thank you for asking though.” I kiss him and force my tongue into his mouth; he lets out a soft moan and places his arms around my shoulders. I wrap my arms around his waist and pull him in tight, placing my thigh in between his legs and rubbing it up and down on his groin, which gets him to let out a little high pitched gasp. The chastity belt stops him from finishing but that doesn’t mean I can’t get him all worked up, in fact I like to get him worked up a few times a day to keep him antsy and attentive.
This is all good for driving him crazy but the best thing I have is his vibrator. I have three rules for it. First; if I find it, I’ll punish him, but I’ll never take it away. Second; if I catch him using it, I’ll punish him even more. Thirdly, and the best by far; if I catch him using it and he isn’t moaning to himself ‘Oh Wolfy Boy’ over and over again, I’ll punish him twice as much. I know he’s going to use it, to try and relieve some tension, which will never work, or if he’s bored. This way, I’m making him secretive about it and afraid of getting caught, like a good little girl, while at the same time I’m making him think about me as his boyfriend while he’s doing it. I’ve hidden a camera around the house once or twice to catch him while I was in class, to make sure he was saying my name. After catching him a few times, and some spankings coupled with a week of hanging laundry outside in his punishment shoes, I’ve passed closed doors in my cottage many a time to hear Little Red chanting ‘Oh Wolfy Boy’ and pleasuring himself. I’ve chosen to catch him sometimes and chosen not to on others because it’s so gratifying to hear him tormenting himself without me having to even lift a finger.

I pull away and ask “Is there anything you should be doing right now?” already knowing the answer. His hands trail off of my shoulders and fidget with his apron.

“Yes,” he answers glumly, shifting his hips and swishing his petticoats like he has to pee.

“Well then get back in there and take care of it. We can have our fun later but if you burn dinner then I’m going to have to punish you.” I reply playfully, pinching his rump while I do so. I let him go and he bounces off towards the kitchen.
I take a seat on the couch in the living room while his Mary Janes clack their way across the wooden floor. I’ve been keeping Little Red like this for almost a year now and still he can surprise me.

When morning finally did come I was ready and raring to go. I woke up before my alarm. I got dressed in a tight blue t-shirt with a cute cartoon wolf on it and some white jeans I picked up at a vintage store. I almost spent a good hour putting on my makeup, spending more time on it than I had ever done for any date. I wanted to look my best, the best part about keeping a boy in chastity is that the more they want you the more frustrated they get, and the more frustrated they get the more punished they are. I fished through my closet to find some appropriate clothes to take my new girlfriend out in; there were some errands I would need to run and what better way to start his punishment than by parading him around in town? I found an old pair of my jeans with hearts stitched into that the back pockets that would fit him pretty nicely, if a bit tight. I found some flip flops and a gauzy white ruffled blouse that would let anyone looking at him see the training bra and wait cincher he’d be wearing right through it. To top it off at the bottom of my closet I found a red hoody of mine with little black furry pompoms on the ends of the drawstrings, when I found it I giggled with how appropriate it was. I fixed myself some breakfast and then brought all the clothes down into the basement where Little Red was still asleep. He probably didn’t sleep very well and I’m sure that his feet and abdomen were aching from the shoes and wait cincher respectively. I decided to start the day off right by feeling him up. I began to rub my hands on his tucked away member through his panties until he groggily started to move his hips in time with the motion, more automatic response than conscious decision. I started to trace the rim of the hole on his backside with my thumb and every time I pressed my thumb onto the rim of his hole he curled in and tried to move away from me. I smiled, already knowing that this was going to make one of the things I had in store for him even more fun. Eventually arousal surpassed his grogginess and he woke up slowly. When he finally opened his eyes and made eye contact with his reflection in the mirror he woke up with a quick start.

“Good morning Little Red!” I chirped happily.

“What the-” he began to ask and already I was dissatisfied with his answer. On one hand I was hoping he’d have made more progress but on the other I was happy to redden that sweet little ass of his again. Five smacks were enough to get some compliance out of him.

“Say ‘Good morning Wolfy Boy!’ my Little Red or it’ll be more spankings for you.” I chirped again, slipping some cheerful menace into my voice.

“Gah-Good morning Wolfy Boy!” he squeaked out in a falsetto of which I was unsure on whether it was intentional or not.

“Good morning Little Red!” I replied happily. “Did you sleep well?”

“Um… yes?” he replied as he tensed up his body, bracing for impact.

“That’s great, because we’re going to have a full day of errands ahead of us. Now I’m going to need to get you all dressed up, so I’m going to have to undo a few of these nasty ropes and locks. Don’t do anything that would make your boyfriend mad now” I said while I waggled my finger in his face. “Otherwise I’ll lock you right up again and spank you for a week, only this time you won’t have your silky panties to protect you. Nod your head and wiggle your pantied little butt if you understand.” I almost clapped when he complied, the chains on his ankles bounced and jingled as he shook his little tush from side to side. “Good!” I proceed to untie him, leaning over him and grinding my pelvis into him while I did so. Once he was sufficiently untied I removed the punishment shoes and knee socks and dressed him in his jeans and flip flops. The jeans had their intended effect of being so tight that not only could you see his panties through them, but you could see the rows of ruffles on them as well. Once that was done I untied him further and stood him up, putting on his blouse and hoody. I wasted no time in leading him upstairs, delighting in how he had trouble walking with all the time he spent bent over the block in heels last night. When we reached the top of the stairs I found my purse and produced some cold cream so I could wipe off his doll like heavy make up. While it probably seemed merciful to him at the time, he didn’t know that he was soon to be heading outside looking obviously like a boy with a tiny girly waist in girls’ clothing. Up until this point he still hadn’t said a word, just silently following me along and not resisting my efforts, I felt a tug on my hand when we reached the door. I’m sure that he had just seen his reflection in the mirror I have hanging up in the atrium. I turned around and saw that he was staring at his feet with the hood up so I couldn’t see his face but I knew what was going on. I turned around and put my hands on my knees, bending down to draw my face level with his, as if I was speaking to a child.

“What’s the problem Little Red?”

“I don’t want to go out,” he said with a trembling pout, there was fear in his voice. Real fear.

“Why not?” I asked; drinking this in hungrily, this was the part I really liked.

“I… I… look like a girl... I can’t do this!” he struggled; he was trying to feel his way through this, trying to find an excuse or explanation that wouldn’t get him punished.

“Well that’s because you are a girl sweety!”

“No but… everyone out there will know I’m not a girl. If they see me they’ll-”

“-laugh at you.” I finished his sentence for him and smiled, showing my canines to him. “So you’re saying that you’re embarrassed because you don’t look like a girl?” I asked with barely suppressed glee. He was playing into this perfectly.

“Yes,” he replied meekly.

“So, if you looked more like a girl would you feel better about going outside?” I asked slowly, letting each word sink in before proceeding to the next. After a long pause, his response was a barely audible affirmative.

“Well don’t worry then, the first place we’re visiting on my errands is going to help you with just that!” I replied instantly, opening the door so quickly and pulling so hard on his hand that I practically took him off of his feet as we proceeded outside. I didn’t have a car, in fact I still don’t, so instead we walked into town. It took us a good twenty minutes for us to get into the town proper. My cottage and the university are up on a hill with the actual town sprawling out into a valley. While there are a few districts and neighborhoods that college students frequent, I intended to go to some of the more remote areas. Not only would the prices be favorable but there was less chance of someone from the school recognizing him. While humiliating Little Red like that was part of the plan, a part that I looked forward to very eagerly, I wasn’t sure of how much he had really submitted to me yet. I couldn’t have him trying to run off to get some help. I would need to break him a lot more before I could try that. I led him by the hand; he trailed behind me slightly, still looking at his feet almost the whole way, hiding behind his hood like a shield, so I took to describing where we were.

“Here we are!” I exclaimed, gesturing with my hand to the corner salon as if it were a palace. “Today I’m going to treat you to a makeover, no need to thank me”

“Thank you,” he replied automatically.

“Didn’t I tell you not to thank me?” I asked, already raising my hand to slap his ass. He squeaked and ducked out of the way, my hand met air. I stood frowning for a few moments before I giggled and grabbed him by the waist. I stepped in and began to kiss him and forced my toungue into his mouth, not giving him a chance to respond. He put his hands around my waist and I pinched his bum fiercely; always continue punishment on a single part of the body if you can, that way it’s sore and has more impact with less work.

“Red, put your arms around my shoulders when I kiss you, remember to bring in your stomach, stick out your chest and your tush.” He did so and I kissed harder. “Now moan sissy.” I commanded while I rubbed my thigh up and down on his crotch. He did as he was told.

“Can I help you?” barked a heavily accented voice. I turned to the side and realized that the salon’s door was open and a very grumpy looking middle-aged Asian woman was standing in the middle of it. I stepped back from Red instantly to face her.

“Oh hello! I’m the 9 o’clock.” I said while eyeing Red standing in the middle of the sidewalk, blushing so hard that he looked like he was wearing the doll make up again.

“You’re late, don’t be late next time.” The proprietor snapped before stamping her way inside. I followed her inside and Little Red trailed behind me. The inside was a typical Asian-run hair and beauty salon, including tacky Asian-esque pictures plastering the walls that nobody likes, not even the staff. The only other person in there was a tiny older woman who I could surmise was the mother of the owner. Her myriad wrinkles framed her face into a near permanent smile, a stern contrast to the scowl of her daughter.

“You said you wanted a body wax yes?” the owner asked, eyeing me up and down the way a butcher looks at meat. I stepped to the side to reveal Little Red behind me, who was busy occupying himself by looking at the tacky pictures and trying as hard as possible not to exist.

“He’s the one who needs the full body wax,” I indicated.

“He?” she asked while leaning forward like a snake eyeing a mouse. Red looked at the floor. The owner reached into her apron and pulled out a comb; with a quick flick she used her comb to flick his hood back. Her scowl dissolved into a smirk. “Ah, I see. He!” she chattered something over her shoulder to her mother in Korean and her mother broke out into a bout of laughter larger than the woman herself.
“Do’hohohoho!”

“Ok then. Boy, go take off your clothes and then lie down on the table here” the owner demanded while gesticulating with her comb like a conductor’s baton. I looked around at the salon that was empty save for the two women in charge. I had made this appointment hoping that the salon would be packed, but you can’t get everything you want. Red froze like a deer in headlights.

“Is there some kind of back room?” He asked sweetly while glancing around for some route of escape.

“No, bathroom broken, toilet clogged, take off your clothes” the owner snapped, I wasn’t sure if she was displeased with his response or the state of her bathroom.
“You heard her Red, take it off” I chimed in. He flushed and began to slip off the hoody slowly. I watched the two women and watched their eyes widen as they took in his attire. The stark lighting in the salon made it easy to see through his gauzy blouse at his training bra and waist cincher. When he took off his jeans to show his frilly panties the wide eyes turned into a bout of laughter. They cackled like hyenas.

“B’ahahahahaaa!” the women laughed, clutching their sides while looking at Little Red in his attire. I could see him begin to tear up as he undid his blouse, unlaced the cincher and struggled with his training bra.

“You having trouble taking off your bra?” The owner asked between hysterics. “A boy like you must have a lot of experience putting them on but not a lot taking them off!” She laughed at her own joke until Red finished taking off his training bra. When he finally did she settled down and waved him onto the padded table. “Lie down here girly boy, we’ll start by waxing your legs. Don’t worry I’m not going to get any onto your nice underwear.” She surpressed another laugh as she went to fetch wax and Red buried his face into the padded table as deep as it would go to avoid looking at anyone. When the owner prepped and applied the first strip I leaned in to watch his reaction. Red yelped in pain when she tore off the first strip and all the hair in that patch went with it. He kept squeaking as she went up and down his legs, tearing all of the hair out by the roots.

“Quit being a princess-baby! Beauty is painful.” The owner admonished him while she worked, the owner’s mother cheerfully chimed in with words of advice we couldn’t understand before she began laughing again.

It was great to think that not long ago that my Little Red was on campus holding down two girlfriends at the same time. Now he was in a salon getting his whole body waxed while wearing frilly panties and being called ‘a princess-baby’. It made me hot enough that I had to step outside while they worked just to get some fresh air. At this rate if I was going to make it through day, I was going to need some relief. Just because Little Red was in chastity didn’t mean I couldn’t have some fun. I was going to have to wait on that though. When I finally came back inside, they had finished waxing Red’s legs, arms, underarms, chest and face.

“What’s next?” the owner asked, already satisfied at a job well done.

“Can we shape his eyebrows to make them more delicate?” I asked.

“You sure? Gonna look pretty strange for a boy to have thin delicate eyebrows. Even on this one.”

“Red? Don’t you want thin girly eyebrows?” I asked with a wicked smile. He nodded glumly and with a few expert applications and rips, Red had delicate alluring eyebrows. I had to give it to her, the owner was very good at her job, and still is.

“Anything else?”

“Can you wax away everything down there?” I asked in a stage whisper, making a vague gesture with my hand, enough to indicate what I wanted without being impolite.

“Really? On him? It’s gonna hurt, you know that right?” the owner asked with disbelief.

“Yes, I don’t think he wants it.” I assured her and patted her on the arm.
“Really? Down there? What about in-between his-“

“There too, Red wants to be smooth all over, and in every nook and cranny.” I replied confidently. It gets pretty easy to make decisions for someone else after a bit.

“Alright then… if you insist…” the owner replied, already divorcing herself from the consequences. “Girly boy, lose the sexy underwear and lie down face up.” Red, hands shaking, removed his lacy panties, revealing his chastity belt. There was a powerful, confused silence. “I said lose the underwear, what the hell’s that?” she continued, indignant. I sidled up to the owner and her mother and spoke to them in a low whisper I knew Little Red could hear.

“That’s to keep his little boy parts out of the way, believe me when I say ‘little’. He used to be my boyfriend but I thought he was too wimpy so we’ve agreed that now he’s going to be the girl, and I get to be the man of the relationship.” This inspired fresh snickering from the ladies. The owner’s mother advised me in Korean while waggling her finger at me.

“My mother says you should ditch girly boy, find yourself real man. He should find real man of his own. Make you both happy.” The proprietor told me.
“I’ll give it some thought, but right now I think I’m going to have myself some fun.” I replied and winked. The ladies smiled and snickered again.
“True, before you buy a horse you have to spur it around the yard a bit.” The owner went over to the table to continue waxing Little Red. Before she could ask me to I went over and undid the heart shaped padlock holding the chastity belt on. I slipped it off him, rubbing down his silky smooth legs as I took it off. I liked them this way, boys always have good legs.

“The only time you’re ever going to see this little thing of yours is when you’re getting your panty area waxed.” I whispered to him. “And when you take your little baths, of course. I’ll take your little thing and soap it up, getting it nice and clean. But don’t get any ideas, because the second it’s clean, away it goes and back you go to being my cute little virgin girlfriend.” I could see he was starting to develop an erection, perfect. That was all dispelled when the first strip of wax ripped off the majority of his pubic hair. Little Red bucked on the table and tears started to form in the corners of his eyes.

“I know it hurts girly-boy, but after this we apply lotion, hair won’t grow back as quickly next time. Visit enough times and there’s no hair at all.” The owner said, getting a new strip ready on his bikini line.

“Did you hear that Red? We come here enough times and you’ll never have any hair on your body or little private parts ever again. Won’t that be great?” I practically sang with enthusiasm. All Little Red could do was nod, the little tears rolling off the side of his face. In a few minutes his bikini area and back door parts were all smooth and hairless, every nook and cranny just like I asked. When that was done we rubbed the lotion on the freshly waxed areas, I volunteered to do those lower areas that the owner didn’t want to touch. With an oiled up finger I clandestinely explored Little Red’s rear, I looked at him while I did this and I could tell that his will to resist was spent after the waxing he had to endure. All he did was squirm, flutter his eyes and take in little gasps. I found it very exciting but I stopped before anyone could notice. When that was done I locked Little Red back into his chastity belt and put on his frilly white panties. Dressing and undressing him so often made it feel like I had my own life size Barbie-doll, which I guess is part of the fun. They still had to do his hair and nails, so I didn’t bother with lacing him back up into the waist cincher just yet, but at the last second I put him back into his training bra, pinching his nipple through the light padding, before they started again. I had already told them over the phone what hair style I had wanted for Little Red and I wanted to be surprised by the results, so I left to get some coffee while they worked. I would need the energy after all.