An Appropriate Punishment Ch. 03

Firstly, thank you to everyone for your comments and encouraging messages! If you have not read the first two stories in the 'Appropriate Punishment' series, it is recommended that you do, otherwise the full context of this installment may be missed.

*****

Showering that morning, my cock was standing straight up at attention. Despite being super horny and almost perpetually hard for nearly twenty-four hours, I was also strangely so exhausted that I just went straight to sleep that night. Then, when I got up in the morning I had no time to do anything but get ready, as I had been instructed.

I spent a longer time in the shower than usual that morning, for no other reason than following instruction. Ms. Berkowitz had very clearly laid out her expectations. Almost as an echo in my ears, her instructions rang out as I replayed them in my head: "I expect you to shave your penis and balls completely bare. You will also shave a 'landing strip' on your lower belly, and I expect this to be done before your shopping trip tomorrow."

Carefully, gently, and meticulously, I complied with her decree. It felt strange as I was drying off, feeling the full smoothness of my now completely hairless balls and cock. Then looking in the mirror, I was made aware of the almost rectangular strip now effectively pointing down at the base of my hard dick. The sight was both embarrassing and deeply erotic at the same time.

I dried myself off, and then looked down at the clothes I'd brought with to the shower to wear for the day. A simple white T-shirt, jeans, belt, and then simple black socks and white trainers. A simple grey hoodie completed the outfit, except for the last item that had kept me enthralled and awake for virtually the entire night before.

Katie's panties, hidden amongst all of my other clothes, were peeking out from the pile and may as well have been the only thing in the room for all of my fixation. Yesterday morning I had spied on her lifting her skirt for Ms. Berkowitz's underwear inspection, and last night while the rest of the house was sleeping I washed them by hand, imagining the next day when I would be wearing them. I had initially thought that they were silk all round except for a lace trim. Turns out the lace dipped deeper down the font, in a V-shape

I tried to continually delude myself, reminding my own dirty conscience that this was all Ms. Berkowitz's idea. That in itself was true, but the excitement and lust I felt while thinking about the silk and lace cupping my now smooth dick and testicles... it was almost too much to bear, and that was all me.

To make matters more intense, I was set to be shopping with Katie today! She knew full well what I'd be wearing, what we were shopping for, and had already had a good look at me in a pair of tight, pink satin panties. We were shopping for more underwear, well...panties... for me! Then we had to meet Ms. Berkowitz back at the school (on a Saturday?!), and I had no idea what was in store for me after that.

Now was the moment I couldn't take a step back from. Despite having spent the entire day before wearing pink satin panties (with 'I must wear proper panties' printed on the front), I knew that this was really the moment where I could no longer say there was any will in play but my own. Despite knowing that I could not predict the full magnitude of this decision, I picked up the panties and held them open before slipping one foot... then the other...into the openings. I pulled them quite quickly up my legs, having committed to my decision, and immediately felt my groin stir with incredible stimulation.

The silk on my balls, the combination of silk and lace on my dick, as well as the mental realization that I was wearing Katie's panties, all nearly made me shoot my ejaculate everywhere.

Somehow, after a few moments, I managed to regain my composure, and put everything else on over the panties. This seemed to calm me down, and softened my full hard on to a now semi-erection. Having dressed, I grabbed my wallet and keys, and left the house.

...

Standing outside the toy store as Katie and I had agreed, my ears were basically ringing, and I'm sure I was completely out of breath. This was almost worse than school the day before. Here I was, wearing a pair of silky white panties with nothing but my jeans over them. Despite having tried to make sure my belt was on tightly, I was still paranoid that someone might see the lacy waistband peeking out.

"Michael!" I heard a voice shout.

I turned around and saw Katie striding confidently towards me, a huge smile on her face. She looked amazing.

Some tight (very tight) jeans, subtle ugg boots, a loose fitting shirt and tight black jacket, all completed with sunglasses which she took off before giving me a big hug. It was a great sensation for me, and in many ways made me feel comfortable. It felt like this was something we'd organised on our own and were just to good friends catching up.

Gently leaving my embrace, she looked around nervously before asking in an excited but low "Have you got them on?"

All I could do was nod.

"Oh my GOD! You have to let me see!" Before I could do anything, she'd grabbed my hand and pulled me away to the nearby bathroom. Quickly deciding that the

Ladies was best she took a quick look in, then back behind us, and yanked me by the arm and took me inside.

Once we were in a cubicle, she locked the door behind us and put a finger to her lips. Then she flicked her eyes down to my belt and back up to me as if to say 'Go on!'

I was obviously a bit too hesitant for her as the next thing I knew she was on her knees undoing my belt buckle, then the button of my jeans, and then slowly...very slowly... pulling down the fly. My jeans dropped to the floor as she tried to hold back a gasp and yet another of those seductive, wonderful giggles that I'd now heard several times before. I couldn't believe that I was here in the Ladies' bathroom; pants down in front of my high school crush...wearing her underwear.

"They look even better on you than they do on me!" she said, having managed to compose herself. My cock was sporting a semi-erection, having not quite got up to full mast in the rush of it all.

That didn't matter for too long, as Katie suddenly started running the tips of her fingers up and down the side of my silk covered shaft! I shuddered from the overwhelming pleasure of it all.

"I'm sorry," she said, "I just had to feel it with the silk and everything. God, you're so hard!"

I somehow managed to say "Of course I am, if you're going to keep doing that!"

She then moved her fingers to rubbing the underside of my balls, resulting in an uncontrollable gasp escaping from me. She laughed almost triumphantly, and then retracted her hand.

"Come on, we can't waste any more time. Lots to get through today!" she said.

I couldn't believe it. My face must have said it all because she looked at me, laughed, and then whispered in my ear: "Don't worry, if you're very good, I'll do a lot more than what I did just now and you might get some release."

That in itself should have made me burst at that point, but once again I held my nerve (and my jizz) and nodded at her. We left the cubicle and on our way out passed a woman, probably in her early forties, coming in.

"You shouldn't be in here!" she said, obviously shocked.

Katie quickly replied "It's ok, he's wearing my panties". Then laughed, grabbed me once again and ran off, leaving the woman looking completely confused and completely shocked.

Once we were clear of the bathrooms, I said "I can't believe you just told her that!"

"I'm sorry," she replied "it was just such a perfect opportunity, and did you see the look on her face?!" We both laughed at that.

"Anyway, you might have to get used to that. Come on, there's someone I'd like you to meet."

Despite getting nervous once again, I couldn't resist following her.

We ended up outside a shop called 'Wendy's'. Very clearly a boutique lingerie store. I had stopped outside, too nervous to go in.

"Don't worry," said Katie, taking me by the arm "you don't have to worry about anything."

Gently guiding me over the threshold, she got me into the store. There was one woman in the shop, buying something at the counter. Having made her purchase, she turned to see us both there arm in arm. She gave us something of a knowing smile, despite not actually having a clue what we were actually there for. In fact, she probably thought we were there to get underwear for Katie, while the opposite was in fact the truth. She walked on past, leaving just Katie, myself, and the shop assistant in the store.

Katie and the shop assistant clearly knew each other, giving one another a quick hug hello. Katie then gestured for me to come over.

"Michael," Katie said, "I'd like you to meet my cousin, Gina."

Gina was another tanned beauty, much like Katie. I guessed she was in her late twenties, with a tight figure, gorgeous curves, and mesmerising dark eyes. Wearing a tight black skirt and white button up shirt, her clothes clung tightly to her almost perfect body. The shirt looked ready to burst its buttons as her large (probably D-cup) breasts tried to escape. She was tall for a woman, and looked me dead in the eye with a smile as she shook my hand.

"Pleasure to meet you, Michael" she said, and I returned the pleasantries.

"Michael," Katie said "I figured it would be pointless going shopping for you unless we knew what size we should be looking for. It can make all the difference, especially for your, um... requirements!" She said the last part with a huge smile and a bit of a laugh. "Gina is an expert and does sizing and bra fittings all the time, so I thought she could help."

"Oh so you're shopping for him today?" Gina said, before bursting into laughter. "Well, let's go into the fitting room and get you measured up."

There was a pause. I looked at them both nervously. "I'm not sure about this," I managed to say.

"Oh don't be silly!" said Gina. "Come, I'll take you to one of our private fitting rooms." She then came up behind me and gave me a slap on the butt before giving me a gentle nudge in my lower back to get me moving.

In a complete trance, barely able to tell whether or not I was in some weird dream, I moved forward, and found myself standing in the middle of a rather large cubicle with nothing but a curtain keeping it open. Katie took a seat on the small bench, next to the mirror.

After dashing back out of the room for only a moment, Gina came back in, a tape measure round her neck.

"So what are we measuring for today, exactly?" she asked, with her hands on her hips and a huge smile on her face as she grinned first at Katie, then at me.

"Are we getting him fit for a bra? Corset? Panties? What's the story?" she continued asking.

Katie simply left the question to me. "Well, Michael?" she said invitingly.

After taking a deep breath to steady myself, I said "Just panties, nothing else."

"Ok." said Gina, slightly disappointed but thoughtful at the same time "Well then, take off your shirt, drop those pants, and let's get measuring!" She had basically taken charge but saw that I was still very nervous and hesitant.

"Come on Michael," she coaxed "if I'm going to do this properly, I'm going to need to take accurate measurements around your waist and legs. Here, maybe this will make you feel more comfortable..."

With that she unbuttoned and unzipped her skirt letting it drop to the floor. My jaw dropped directly onto my chest as she stepped out of the pool of fabric that had gathered around her ankles. Her long shapely legs were enveloped in very fine stockings, held up in by a lacy black garter belt, the straps of which laced underneath her matching black and white lace panties. Her shiny black heels completed one of the sexiest images from my mind, real or imagined.

"Now it's your turn" she said, hands once again on hips and indicating my (now bulging) crotch.

"Come on Michael, fair's fair." piped in Katie.

Nervously and slowly, I unbuckled my pants, ready to reveal my naughty secret for the second time that day. I let the jeans fall straight down, and then stepped out of them.

Gina barely missed a step, apart from raising her eyebrows extremely high for just a second. Then, looking directly at the growing presence in my crotch, she cooed her seal of approval without even acknowledging my package, saying "Ooooo, very nice. Alright, off with your jacket and shirt, your turn to go first."

I complied, knowing that the big reveal had already been done. Now standing wearing nothing but Katie's white, silky panties Gina came towards me saying "Right, let's get to work."

She knelt down in front of me, pulling the tape measure from around her neck. First, she measured my upper leg, right up at the lacy waistband of the panties. Pulling a notepad from the breast pocket of her shirt, she took down the measurement and then moved to the other leg as a comparison. While moving her hands, the back of one of them brushed the silk that was tightly holding up my super sensitive balls. I shuddered uncontrollably.

"Oops, sorry about that" she said. She took the measurement of the other leg and then gave just a light tug on the lace of the leg opening, putting it into place.

"Those panties are gorgeous!" she said. "Where did you get them from?"

Katie stayed quiet about that one, as I looked to her for support.

"Uh, it's a long story" I said, which was partly true.

"Well, I hope you didn't steal them!" said Gina, letting that one go.

Then she moved up to my waist, taking the tape directly around the waistband. She skillfully lifted the tape over the tip of my erect cock as it poked up towards her chin. She then stepped back to make a note on her note pad.

"Alright, Michael," she said, "I'm afraid I can't make a complete assessment about your sizing without knowing what we're working with in those panties of yours. Take them down, and we'll get you measured up."

She said this quite matter-of-factly, despite the fact that what she was actually suggesting was measuring the dimensions of my penis.

"Excuse me, what?" was all I could say.

"Michael, if we're going to find the right size and fit for you to wear girls' panties, we're going to have to know what you're packing behind them!" she said, clearly frustrated at how much time I was wasting. "We wouldn't want to be squashing your bits too tightly now would we?" she laughed.

She noticed by my body language that I had started to see it from her point of view.

"Come on," she encouraged "pull those panties down, just enough so I can get some measurements for your little friend down there."

Before I knew it I'd hooked my thumbs into the sides of the panties, and pull them down to my upper thighs, my dick now pointing hard and straight up into the air in front of me.

"There we are!" said Gina, "Nice landing strip by the way, and shaved balls too! You're full of surprises. Now... let's see what we're working with."

She put the end of the measuring tape right at the tip of my hard cock, and pressed down all the way until she had it taught at the base, right above my incredibly sensitive scrotum.

"Six inches, almost exactly!" she proclaimed loudly. I was quite embarrassed to know that Katie now knew my exact size, while Gina proceeded not only to then measure and record my girth, but also the width of my balls! For a second I thought I saw some kind of lust or craving in her eye, like she wanted to feel my balls in her hand, but she maintained her professional approach.

"Right," she said "almost there. We've got you measured with a boner, but we need to know what you're like flaccid, so um...I'm going to step out now, and hopefully you'll have a chance to calm down."

With that, she stepped out of the fitting room, leaving me standing there with silky white panties round my thighs and my rock hard cock pointing up in the air.

I grabbed the sides of the underwear with both hands, but next thing I knew Katie had her hands over mine, stopping me from pulling them up. She took my hands in hers, and moved them to the back of my head.

She then ran her hands down the side of my body, to the top of the panties at my thighs, and slid them down to my ankles. Stepping around me to stand in front, she quickly took my cock in hand, and stroked me firmly but not too quickly.

"I bet you're pretty close to shooting your load!" she said. "Seeing my cousin in her panties, while wearing mine, I bet a cheeky perve like you was ready to spurt on the spot. Well...it's your lucky day. I'm going to give you a chance to cum in my mouth, and if you don't do just that in the next 60 seconds, then I'm going to make today far more embarrassing than you can possibly imagine, ok?".

I nodded my assent, knowing she meant every word and barely able to remember where I was given the way she was stroking my dick. I was surprised at how quickly her tone had changed from earlier that day, even from the day before.

She knelt down in front of me, gave me a very quick lick on the balls, and then engulfed me in her mouth. I could never have predicted that my first blowjob would be this good! Her tongue was at work all over and around my cock, while her hand firmly stroked me at the base.

I didn't need the full sixty seconds. I reckon I came in about thirty-to-forty, and it was the best cum I had had up to that point in my life. She must have swallowed, and swallowed, and swallowed, to take all of my pent up sperm from the last couple of days. I could barely stand from the ecstasy of it.

With a final gulp, she wiped a little excess off her chin and smiled at me before whispering "Good boy!" in my ear.

Her sister suddenly came right back in, with almost perfect timing, asking "Have we finally calmed down now?" She looked at my now softening dick and said "Ah good, that looks considerably smaller now."

She proceeded with my flaccid measurement (three-and-a-half inches), and even commented that my balls seemed to have decreased very slightly in size, but said nothing further. I got the impression that she knew exactly what was going on, but was declining to say anything.

She then proceeded with some recommendations.

"For a guy of your size and, well...size... you'll want to go for briefs and bikini panties more than anything else, and I'd say you'll be alright with Medium for the most part. However, if you really want to wear thongs or g-strings, I'd recommend going up to a larger size, though you may find that they don't hold everything particularly well. Would you like me to help you find some nice sexy panties?"

Before I could answer, Katie chimed in. "Actually, Gina, we might come back shortly. Now that we know what size to look for, we need to check off a few items on the list."

"That's fine!" said Gina "See you in a bit!"

With no further ado we left Wendy's, but before we got too far, I actually stopped and held Katie back. Looking at me with a surprised, if slightly confused expression, she said "What is it Michael?"

"I just wanted to say thank you" I said quietly, "that was..kinda my first blow job ever."

"Really???" she asked, obviously amazed. "Well, it's a pleasure. I certainly enjoyed it. You've got a nice hard, thick cock!" she said playfully. "It's a nice length too, not small but not scary either. Between you and me, I'm dripping wet, super horny and I'm hoping you can help me sort that out later. But right now, we need to get a move on, we've got to get you some panties before Ms. Berkowitz has us both in serious trouble." Having dropped that incredibly sexy bombshell, we headed off to get our shopping done.

Unsurprisingly, we did head towards the women's underwear section of the department store, but ended up browsing the aisles of the pre-packaged section. Browsing through the three-pack options, Katie seemed to have found one that she liked.