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I was instructed to report back to Laura’s flat the next morning, which was Sunday. After another restless night, I showered and then got dressed, putting on a pair of knickers. Despite my nervousness, my penis started to become excited inside its cage. My mind flitted back to a time when I was sixteen and my sister, Phoebe, had caught me in her room, rifling through her underwear collection.
I had been drawn there by curiosity—and envy—because girls always had more variety in their undies compared with boys. There were more colours, more fabrics, more styles, more textures, and, of course, there were items that had no male equivalent, such as bras, tights, stockings, suspender belts, camisoles and petticoats. I intended to “borrow” one or two items, take them back to my room, and use them to satisfy my ual appetite—not to wear them, you understand, nor to soil them, but just to use them as aids to fuel my imagination. I had done this before, and never been caught. Where was the harm? And what could go wrong?
That day, I had learnt to my cost what could go wrong, and my world came crashing down. Understandably, Phoebe had been furious on discovering what I was doing. Distracted by what I was finding, I had been unaware of her coming up the stairs, accompanied by her best friend, Zoe, who was also nineteen, the same age as Phoebe. They had caught me redhanded.
Ignoring my grovelling, abject apologies, the two girls discussed whether to tell my Mum what I had been doing. It mortified me that she might learn that her son was a pervert, and I begged them not to grass me up.
Smiling slyly, it was Zoe who had suggested my punishment, but Phoebe had enthusiastically endorsed the idea. A quarter of an hour later I found myself parading in front of the two girls wearing a pair of plain, highwaisted, white cotton knickers and a similarly plain white bra stuffed with white socks. Both items were left over from Phoebe’s school days, and both were too small for me, with the elastic of the panties and the band of the bra digging into my flesh.
My ensemble was unmistakeably feminine, but there was nothing remotely attractive about these items—they were nothing like the alluring lingerie that I had been fingering a short while earlier. The bra and knickers were purposefully intended not to titillate, yet here I was, dressed in them in front of my sister and Zoe.
I wanted to die from embarrassment, but, at the same time, I found myself being turned on by the humiliation I was suffering. My ual arousal was obvious for them both to see, so my pleas not to be made to dress like a girl had led to scornful remarks.
“The lady doth protest too much, methinks,” declared Zoe, quoting from Shakespeare.
“Flesh stays no further reason, but rising at thy name,” added Phoebe, cryptically.
I was now speechless with fright and tried to cover myself up, but they would have none of it. “Get your hands away,” hissed my sister.
My fear increased as she took photos on her phone. “You’ve nothing to worry about, unless I catch you doing this again, Stephanie, but, if I do, then…” She left the sentence hanging—she had no need to complete it.
“I bet this is not the first time he’s done this,” commented Zoe, pouring petrol on the flames.
“Is it?” asked Phoebe.
“Er…” I replied, unsure what to say.
“Obviously not the first time then,” concluded Zoe, with a smug look. “What a sicko!” she sneered.
But next, adding to my stress, Phoebe delved into a cupboard and pulled out her old school uniform, last worn when she was eighteen and in her final year at school. Any hope that it would prove too small for me quickly evaporated. It was a tight fit, but soon I was wearing a very short, pleated green skirt, a white shirt, a tie and white ankle socks.
“He needs to shave his legs,” declared Zoe, her eyes sparkling, and her pupils dilated in excitement.
“No!” I pleaded.
“Yes!” replied Phoebe with zeal, and, before I knew what was happening, she had produced an electric shaver. I was told to hitch up my skirt allowing her to run the shaver up and down both legs. I watched terrified as I was denuded of hair, wondering how I would explain that at school, when changing for games. Yet still my arousal persisted, strengthened still further when they forced me to adopt modelling poses in front of a fulllength mirror.
More photos were taken, but even worse was to follow, when the pair made me sit down at Phoebe’s desk and write out, one hundred times, “I must not dress up in my sister’s underwear”. My two tormenters watched the television in the room while I wrote my lines. Upon completion, Phoebe made me add my name to the top of each page and then, to my horror, she locked the lines into her desk drawer. “It’s just for insurance, Stephanie,” she had declared, and she and Zoe burst out laughing.
This had happened six years ago, but it could have been yesterday. Quite possibly, Phoebe still possessed the images and my written lines, to be produced when she feels the time is right. Consequently, I am always careful never to provoke her on the rare occasions we meet up. And the contempt she shows me suggests I have never been forgiven.
My ordeal that day had been a traumatic experience, and had probably marked the start of my obeisance towards women, something that Laura had very quickly picked up on.
oooOOooo
I snapped out of my daydream and looked down at my choice of panties. I had chosen the white pair, for the illogical reason that white seems more masculine than pink or powder blue. I say illogical, because male underwear, whilst it may be white, is not usually made of delicate satin with lace panels.
They were the right size and Laura’s insistence that I started visiting the university gym, along with her controlling my calorie intake, had flattened the slight paunch she had commented on. Looking in the mirror, I liked what I saw—and would have liked it better had it not been for my chastity device restricting my enjoyment. However, I dreaded the thought of further visits to the gym now I was confined to wearing knickers, but that was a battle to be fought on another day.
After breakfast, I picked up the matching white bra, and set off to drive to Laura’s flat, being sure to drive carefully rather than risk being hospitalised after an accident. I rang her bell, and she quickly opened the door. After greeting me, and giving me the usual peck on the cheek, she said, “Show me.”
This could only mean one thing, so I undid my jeans and let them slip to the floor. “Hmm… Very nice,” she concluded. “They’re a good fit and they suit you. Give me a twirl…Wow!”
She had seen I was holding my bra. “Why aren’t you wearing it, Stevie?”
“Er, I didn’t think I had to wear it in public, Miss,” I replied, sensing that this explanation would not satisfy her.
“Good grief, Stevie, you’ve driven here in your damn car. Who the hell would have seen your bra? Put it on now, and then we’ll deal with your stupidity.”
I stripped off and pushed my arms through the shoulder straps of the bra. She giggled as I reached behind and tried, unsuccessfully, to do up the clasps. “You’re useless,” she laughed. “I’ll do it this time, but, when you get home, you’re going to practice. I’ll test you next time and if you can’t do it up in fifteen seconds then you’ll have a sore bum. Understood?”
“Yes, Miss.” She quickly fastened my bra and then passed me some rolledup tights to put into each cup. “You need these for shape,” she assured me. “How’s it feel?”
“Strange, Miss,” I responded. “It’s very tight across my chest. I’m very conscious of it being there.”
She smiled, “You’ll get used to it.” I wasn’t convinced she was right, but I did find wearing a bra and panties to be arousing and I was feeling more discomfort down under, inside my cage.
“Now you’ve got the right undies on, we need to deal with your stupidity. Wait here.”
As instructed, I waited, dressed only in my new underwear, while she went to her bedroom, returning a minute later with an eighteeninchlong leather strap. Seeing my quizzical expression she commented, “It’s a tawse, poppet. It’s what naughty boys get when they’ve not been using common sense. Hold out your right arm. Keep it horizontal with your palm facing up.”
Obediently, I did so, and she raised the tawse and then brought it down with a resounding smack on my upturned hand. “Ouch!” I cried.
She smiled, “Now your left hand.”
Again, the leather implement was raised, and a similar blow was delivered to that hand. “Shit! That hurt!” I exclaimed, instantly regretting the expletive.
She gave me a look of mock horror. “What would your mother say if she heard you saying that word?”
“Er, she wouldn’t approve, Miss,” I replied, honestly.
“And neither do I, so we’ll do that stroke again. Ready?”
For the second time, the tawse smashed into my left palm, but I resisted screaming out anything that might be construed as vulgar.
“Lessons learnt?” she enquired, nonchalantly. “You do know I’m doing all this for your own good, don’t you?”
“Yes, Miss, I deserved to be punished. Next time, I will arrive wearing a bra and I won’t use bad language.”
She grinned at me. “Good boy, now put your clothes back on. Then we’re going to give this flat a spring clean because my landlord wants to do an inspection in few days’ time. Well…, actually you’ll be doing the cleaning because I’ve got a biology assignment I need to finish for tomorrow. So, get cleaning, and don’t make a lot of noise. You’d best remove those leather straps from my bed because I don’t want to give my landlord any ideas.” She gave a snigger.
Laura showed me where to find cleaning materials and I set to work. The flat wasn’t dirty, by any stretch of the imagination, but having felt the power of the tawse that morning I wasn’t going to risk Laura finding fault with my cleaning—consequently, I fastidiously cleaned everything, including things that already looked spotless. In the meantime, she was hammering away on her laptop.
oooOOooo
It wasn’t until the early afternoon that she decided we’d both done enough work, so she prepared a light lunch for us both. Not for the first time, as we ate, the conversation took a worrying turn.
“Don’t you think you should be telling your mother that you have a steady girlfriend, muffin? And your sister as well?”
“I don’t think they would be interested, Miss.”
“Oooh! I think they would be. They’ll find out at some point, sweetie. And don’t you think it’s better you tell them you wear lingerie, than they discover it for themselves.”
After the incident with my sister six years earlier, the thought of Phoebe discovering I wore female underwear appalled me. “What! Sorry, I didn’t mean for that to sound rude, Miss, but why do they need to know what underwear I have on?”
“Because they love you and they’re interested in your life, maybe?”
Her argument was weak, and even she didn’t sound convinced, but I had to tread carefully. “Some things are best kept secret, Miss.”
“Uh! I think you’re ashamed at having to wear female clothing, poppet. Am I right?”
I thought carefully before replying. It was ually arousing to be dressed in bra and panties in private, but the thought of the world knowing—my sister knowing—was terrifying. “Er, yes, Miss, I suppose you are.”
“We’ve had this conversation before, my little pumpkin. It suggests you think being female is something to be ashamed of. Yes?”
“No, I’m not saying that, Miss. I’m just embarrassed at wearing female clothing.”
“It wouldn’t embarrass me to wear boxer shorts, poppet, so why should it embarrass you to wear knickers?”
“I don’t know—it just does, Miss.”
“Hmm! I’ll tell you why, and I’m sure a psychologist would agree—dressed as a girl you are no longer able to consider yourself as an alpha male.”
“I’ve never seen myself as an alpha male, Miss! I’ve always treated women with the greatest respect.”
“But, deep down, in your subconscious, you want to be regarded as alpha male, even though you can’t see it for yourself. You’ve been brainwashed, poppet. We live in a misogynistic society.”
I wasn’t going to win this argument, so I meekly agreed, “You’re probably right, Miss, but I’m also sure that you will cure me of any deeprooted misogynistic thoughts.”
She smiled back sweetly at me, “You bet I will, my little cabbage. And do build up the courage to tell your Mum and sister, won’t you?” I nodded, but intended to defer telling anyone, anything, for as long as possible.
oooOOooo
By now, despite us only going out together for less than a month, Laura and I were spending more time together, than apart, yet I still had my own flat, to which I would return each night. That was soon to change.
“I’ve been thinking, sweetie,” she ventured, one evening. My ears pricked up. Usually, when Laura had been “thinking” then some further humiliation awaited me.
“Yes, Miss?” I replied, in a tone that said I was seeking more information.
“It’s stupid you paying rent on your flat when we could both live in mine. What do you think, if we shared this one? We can go halves on the rent, and both save money.”
My immediate thoughts concerned the sleeping arrangements. “You’ve only one bedroom, Miss, and only one bed.”
I needed to step carefully. “You’re mad, poppet! Is that the first thing you think about?”
“Well, er… it seems important.”
She thought for a few moments, leaving me on tenterhooks. “I suppose you’re right, it is important.” She paused for a few more seconds, before saying, “You could sleep on the sofa. Eh? Or, we could get you an airbed, so you sleep on the floor in my bedroom. Hmm? Or… or… you could sleep with me in my bed. What do you think?”
I couldn’t believe what I was hearing. Was she really inviting me to share her bed? Or was she laying a trap to prove her point that I was “ mad”?
“I think it needs to be your decision, Miss,” I replied, after considering my options.
She gave me a sweet smile. “You’re being very diplomatic, poppet. I’m sure you want to share my bed, but we must both use willpower to resist temptation, don’t you agree?”
As she was enjoying oral and I was experiencing next to nothing, she was not being completely honest. But obviously, I didn’t say that. “I do understand we are both making sacrifices, Miss.”
“Quite right, sweetie. Besides, I’m sure that wanking every day was zapping your energy. And denial is making you much more attentive to my needs, don’t you think?”
“Yes, Miss,” I meekly replied. She was right, though. Denying me , and making me forever frustrated, did mean that I served her better. She had made it abundantly clear we were not equals in this relationship and denying me release reinforced the pecking order.
“I’ll buy you an airbed, and then you can sleep on the floor in my bedroom. That way, you’ll be readily available should I need anything during the night.” My penis gave a throb at the thought of what sort of “anything” she might need.
She continued, “You can move in tomorrow. Hands in the keys to your flat, and bring over what you need, bearing in mind there’s not a lot of spare space here.”
“Yes, Miss,” I replied, still trying to take in that I was going to be living with Laura, albeit not as an equal.
oooOOooo
The next day, as agreed, I left my flat for the last time and moved into Laura’s. My flat had come fully furnished, so my personal possessions were few, essentially my clothes, toiletries, books and electronic devices. I squeezed everything into two large suitcases, albeit on the point of bursting open. And I was, of course, wearing a bra as well as knickers because I didn’t wish to experience her tawse again… or worse.
She ushered me inside. “Hmm, you’ve more stuff than I was expecting, but we’ll find a way of fitting it in,” she said, smiling at me. “I need to inspect what you’ve brought, poppet, so open up the cases. I hope, for your sake, I’m not going to find any male underwear hidden in here.”
She stared at me and I felt myself blushing, despite knowing that she would only find a couple of pairs of panties and two bras.
“Gooood boy,” she said, after searching through both cases. “You’re quickly learning that I expect total obedience. I’m sure that your Mum would be proud of how you’re turning out.”
“Thank you, Miss,” I replied, as always hoping that my mother stayed in the dark.
“Besides the obvious, there is another reason why you weren’t to bring male undies. It’s because I’m not supposed to have a boy sharing this flat. Having boxer shorts or Yfronts lying around would be a giveaway when my landlord inspects.”
She saw my puzzled expression and took some delight in expanding on what her landlord allowed and didn’t allow. “He doesn’t mind me having another girl living here, sweetie, but not a boy. He says girls are far less trouble, and he’s right. So, if he visits he won’t mind seeing more bras and knickers hanging up to dry, but he would be upset to see men’s underpants.”
I felt a sense of panic as I sensed the direction the conversation was going. “Hmm, some of your clothes are too masculine, sweetie. We’ll have to buy you some things that are more… well, androgynous.”
I felt butterflies in my stomach. “Sorry! You don’t mean feminine, Miss, surely?”
“I didn’t use that word, did I?! I mean we buy you something that is more uni.” I gulped. It seemed she had set a trap suggesting we shared her flat, and I had walked into it.
“Uni?”
“Yes, uni!! Have you lost the ability to understand plain English?! I’m not suggesting we buy you dresses, poppet, although you might enjoy one, now I know you like wearing panties so much. I’m sure you would love the way a flowing dress would swirl when you walk and turn.” She paused to gauge my reaction and the cunning smile she gave told me that it was just what she was expecting.
She failed to stop a little giggle and continued, “We’ll chuck out anything you own that would only be worn by a man—or a butch ! And we buy you stuff that my landlord will think belongs to a girl.”
“I don’t follow,” I replied, in desperate need of some better explanation. “Can’t I just hide my stuff, Miss?” I asked.
“No! He’s likely to mooch around, opening drawers and cupboards. He’ll see there’s a bloke living here.”
“Surely, he wouldn’t do that, Miss? That’s creepy.” Even as I said it, I could not help but think of the occasion involving my sister, when I had invaded her privacy in just that way.
I didn’t have a chance to reflect further as I saw that Laura was shaking her head. I was testing her patience. “Stop arguing with me, because I know best. This needs to go for a start,” she said, holding up my suit.
“But I would need that if I had an interview, Miss.”
“Then it can live in the boot of your car, poppet. Not in this flat. And there are these shirts. The buttons are on the wrong side.”
“But that’s how they always are…” I trailed off. “Oh, I see what you mean, Miss.”
“And no girl would wear these boring trousers, muffin. There’s nothing attractive about them.” She shook her head in apparent disdain. “And look at these ugly black socks?! This lot is going to go, and instead, I’m going to buy you some new stuff.”
“I can’t let you do that, Miss,” I protested, adding, in desperation, “It would be too expensive.”
“No, I’ll treat you, now we’re sharing the rent? I can afford it. Just leave it all to me, poppet.”
That thought scared me. “I can’t go around looking like a girl, Miss,” I pleaded.
The look she gave me told me I was testing her patience to the limit. “For God’s sake, Stevie! We’re talking uni, not girly! I’m getting fed up with this negative talk. Do you want to go over my knees again? Yes?”
Actually, yes I did and the thought of being spanked by her, despite the pain it would cause, was making my penis twitch. But I knew what reply she wanted, and it wasn’t a yes.
“No, Miss, I don’t need to be spanked. I understand what you are saying.”
“Hmm? I wonder if you do,” she pondered. “I think you need some quiet time to reflect on what I’ve been telling you. What do you think, muffin?”
I knew exactly what she wanted. “I’ll go and face the wall to think, Miss, with my hands on my head.”
She smiled at me, “Good boy! But let’s do your quiet time a little differently today. Strip down to your bra and knickers, then I’ll cuff your hands behind your back, and then you can stand in a corner for half an hour. That way, you can spend time meditating while I admire your cute bum. How does that sound, poppet?”
Dreadful! “It sounds very sensible, Miss,” I replied, knowing disagreeing was pointless. “I will use the time to think of the positives.”
“Goooood boy!” she exclaimed, “And when you’ve finished you can tell me why my ideas are so sensible. Come on… get a move on!”
And so, for the next thirty minutes, I stood in the corner, my nose almost pressed into the wall, wearing just a pink bra and panties, and with my wrists secured behind me. The thoughts I had was that she had tricked me into giving up my flat, only later explaining the “uni” dress requirements. Nonetheless, as I was standing there, feeling utterly humiliated, my penis was throbbing inside its tiny cage. She was forever testing the boundaries of my submissive tendencies, and she knew how to press all the right buttons. I just had to hope that she knew what she was doing, and that we both wouldn’t come to regret her actions.
