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With my bottom still throbbing from my recent caning, I returned to my own flat for the night. Lying alone in bed, on my stomach for comfort, I replayed the events of the day. What had been intended as a friendly and romantic gesture, laying a hand on Laura’s shoulder, had backfired. I had misjudged the situation and had paid the price with three strokes of the cane.
The irony is that she had been right about my motives when she had accused me of wanting to “cop a feel”. I would loved to have moved my hand from her shoulder and cupped her breast. That’s what a normal couple would do in private, except we were not a normal couple.
Despite the agony from my caning, I was becoming aroused as I found myself imaging what it would be like if we were just an ordinary boyfriend and girlfriend. At this stage in our relationship, I was sure I would be able to sit alongside her, and slowly slide a hand up her short skirt, then use my fingers to sneak under the elastic of her panties to explore her moist crevasse and love tunnel.
Then I would embrace her, and dexterously, through the thin fabric of her top, use the fingers of one hand to ping open the clasp of her bra, releasing her boobs. Then I would slither a hand up the front of her shirt and fondle a bare breast, feeling its warmth and sensing its nipple engorging itself to my touch. My mouth would then meld with hers, and my tongue would be welcomed inside. Very soon, I would be on top of her and my penis would be penetrating her, driving us both to a frenzy of excitement
Wow! As I feasted on this mental picture, the reality of having a caged penis hit home and I was forced to go into the bathroom and take a cool shower to dampen my spirits. Life with Laura was proving to be a roller coaster of emotions and sensations. She was pushing me to my limits and beyond, yet I could not imagine my life without her.
oooOOooo
One particular weekend, beginning on a Friday evening, sticks in my mind because it marked another milestone in our relationship. Once I was inside her flat, and we had exchanged our customary cheek pecks, she passed me a parcel. “It’s a present for you, poppet,” she explained.
“A present?” I parroted.
“Yes, because I care for you, muffin. You deserve a present.” She smiled sweetly at me.
“Thank you, Miss.”
It was a small box and there was nothing on the outside to indicate its contents. I prised open the taped down cardboard and looked inside. It was a pair of handcuffs, but with no keys!
“What?” I asked incredulously.
“What do you mean, ‘what’? That’s rude! I’m sure your Mum wouldn’t approve of you sounding so ungrateful.”
I was entering dangerous waters. “Sorry, Miss, I didn’t mean to sound rude. I’m just… well, surprised.”
“I bought you them because I do understand how difficult it must be for you not to paw me with your hands when you are making love to me with your mouth.”
Goodness me, she was right. Performing cunnilingus with my hands clasped behind my back was challenging. I so wanted to stroke and fondle her soft, bare flesh with my fingers. But that didn’t mean I wanted to be restrained in cuffs.
“Er… yes, Miss” I replied, unsure what else to say.
“It should save you having to be punished so often, sweetie. It shows I’m not a bitch who sets traps so I can punish you. Eh?”
Most men would agree that was exactly what she was, but I was infatuated with her. “I would never call you that word, Miss,” I explained, in complete honesty.
She paused, with a serious expression on her face. I sensed whether she was weighing up her options. Punishing me for my ungratefulness was one choice but I felt a sense of relief when she broke into a smile. “I’ll let you off this time! Now strip naked so we can try them out.”
The time had passed when I hesitated to undress in front of her. She had trained me well, and soon I was starkers while she was sitting watching me, fully dressed.
“Come here, turn around and put your hands behind your back.”
Seconds later I heard a click followed quickly by another. I was handcuffed.
“They were expensive, sweetie. I didn’t want to buy a toy pair. Only the best for you. Turn back around and get down on your knees.”
I turned to face her and dropped down, while she stood in front of me, my eyes level with her short skirt. Swiftly, she unzipped the skirt and let it fall to the ground, revealing a pair of lacy black panties.
“Pull my knickers down, poppet,” she ordered. “Don’t damage them.”
With my hands secured behind me, there was only one option available, which was to use my mouth and teeth. Heeding her warning to be careful, I gently tugged at various points along the waistband, inching her undies down. The smell of her arousal wafted into my nasal passages as, slowly, her panties descended over her hips. Another couple of inches and they slipped smoothly to the floor.
“Gooood boy,” she remarked, as if addressing a puppy who had picked up a new trick. “You’re a fast learner.”
She stepped backwards, and fell into an armchair, spreading her legs so they were wide apart. There was no need for her to issue a further instruction. Her requirements were plain to see, and I set to work. She was wet… very wet. Her excitement was driving my own arousal, but I knew to ignore my pain. My sole task was to pleasure her to the best of my ability.
Soon I was eating her out, using my lips and tongue. The familiar groans and moans, and squirms and wriggles, told me I was hitting the right spots. I continued to serve her, focussing on the points that elicited the loudest squeals. All the time, I was rewarded by copious amounts of her precious nectar, as her arousal grew.
I detected the familiar signs that she was close to climaxing, and I burrowed deeper inside her, reaching as far as I could with my tongue. She shuddered and grabbed my head, pushing me still further inside. She reached a thunderous crescendo and, had it not been for her holding me, I would have struggled to maintain contact.
And then it was over. She was struggling to catch her breath as she released her grip on me. My face was covered in her juices but, with my hands pinioned behind, there was nothing I could do except lick my lips and look at her.
“Oh my God, muffin. You were so, so good. Thank you, my little pumpkin.” I felt a sense of pride that I had met—maybe exceeded—her expectations.
But any hope I might be rewarded by being unlocked were soon dashed. “Sadly, after your ungrateful reaction to my present it would not be right to reward you, poppet,” she explained. “I’m sure your mother must have taught you that no one should profit from bad behaviour. I’m sorry about that, my little cabbage.”
The contrived expression on her face suggested she wasn’t at all sorry, but at least I had escaped a spanking or worse. However, I was left extremely frustrated with my penis twitching painfully inside its small cage.
oooOOooo
The next day was Saturday, and I would be spending the whole day with her—I couldn’t wait and was excited at the thought. I arrived at her flat at 10 AM precisely and she enthusiastically invited me in. She was wearing—flaunting is a better word—the most incredibly tight leather leggings. The thin leather clung to her like clingfilm, accentuating the curviness of her bottom and almost revealing a camel toe at the front, although I was careful where I looked. But I so wanted to touch her, to stroke my fingers over the soft leather and explore the topography it revealed.
She saw my bewitched expression. “You like my new leggings, sweetie?” she enquired.
“Oh, my God, they so suit you, Miss,” I replied. “You’re so beautiful, and… and… red…” I stopped myself just in time.
“And what, poppet?” she asked, inquisitively angling her head to one side.
The phrase I had wanted to use was “red hot” but she would not have approved. “And… and ready for the cooler weather, Miss,” I blurted.
Laura couldn’t resist smiling. “Hmmm, you’re thinking fast on your feet today. I hope you weren’t staring at my bum as you followed me in.”
“No, Miss,” I lied.
“Your mother must have told you not to stare at women’s private parts, pumpkin. Eh?”
“Er, yes, she did, Miss. It’s disrespectful to do so.” I tried my best to sound contrite.
I could sense her brain ticking over, deciding whether to pursue this line of conversation. She decided against it. “We’d best get on, muffin. Strip naked for a cage inspection.”
I did so, while she, of course, remained fully clothed, taunting me with her skintight leggings. I stood in front of her, naked and with my hands on my head, while she checked the security of my chastity device.
“Goooood boy,” she concluded, in a patronising manner. “You’re doing well! I’m pleased with you.”
“Thank you, Miss,” I replied, while squirming with embarrassment.
She sat down in her favourite armchair, leaving me standing there, facing her. Then she coyly asked, “You have to sit to pee now, don’t you, poppet?”
“Er…, yes, Miss, I can’t do it standing up with this cage on.”
“No, of course you can’t. What did your mother tell you about using the toilet?”
“Er…, I was always expected to leave the seat down, and I had to be careful with my aim.”
“And did you… were you? Tell me the truth.”
“Hmm… Sometimes I forgot to put the seat down, and occasionally I did miss.”
“Good boy for being honest. So, wearing that cage means you’ll never forget to put the seat down, nor will you miss the target. It’s a winwin, muffin.”
“Yes, I suppose it is, Miss,” I agreed, despite not being convinced.
“Do you feel like a woman, having to sit?”
“Er…, not really, Miss. But I find it inconvenient, especially at university. I have to wait for a cubicle to be free.”
“Welcome to the privileges of womanhood,” she smiled.
She paused, holding me with a hard stare. “I think you would feel more like a woman if you wore knickers. I also think it would help neutralise undesirable male traits, sweetheart. What do you say?”
“What traits, Miss?” I exclaimed, alarm bell ringing at what she was suggesting.
“Oh, just those typical misogynistic characteristics that men have, poppet. You know, showing lack of respect, inappropriate touching, mansplaining, lustfulness, arrogance, bravado, risk taking, agressive driving…, that sort of thing.”
“With respect, I didn’t believe they apply to me, Miss,” I pleaded.
“What?! Twice you’ve tried to take advantage of me by touching me uninvited!”
She was exaggerating, but it would have been stupid of me to disagree. “Sorry, Miss,” I meekly said.
“And I saw the way you were looking at me in these leggings, sweetie. You were practically drooling with lust. You couldn’t take your eyes off me!” She was right, but didn’t wait for an answer. “And there was that time you broke the speed limit driving me to the restaurant.”
“We were late, Miss.”
“Better to arrive late than dead, don’t you think? And as we get more settled into our relationship, you may start becoming more selfconfident and bolder. More of these male traits might start to emerge, so let’s nip the problem in the bud, eh? You need to start wearing panties so you remember your place. Throw out all your male underwear and wear panties every day. It’s hard for man to behave macho when they’re wearing panties, poppet. It’s for your own good. Can’t you see that?”
“No! I would die of embarrassment, Miss. I couldn’t wear knickers, certainly not all the time!” Actually, just the thought of this gorgeous young woman, two years my junior, compelling me to wear panties had caused me to become aroused, yet I was frightened to let her know that.
“You’re misusing the word ‘couldn’t’, my little cabbage. You literally could, because all you have to do is put a foot down each leg hole.”
“By couldn’t, I meant it would be too humiliating, Miss. Someone would see them.” Whilst I could accept Laura knowing I was dressed in knickers, the thought of anyone else discovering this secret scared me to death.
“Hmmm? I really can’t believe that someone like you has never worn panties, sweetie. Eh?”
My mind flashed back to an incident involving my sister, but I decided my safest option was to lie. “No, Miss, never!”
“Hmmm?” she repeated, in a questioning manner. I nervously waited to see whether she would interrogate me further, and cause me to reveal the truth, but she continued, “Anyhow, half of the population wears knickers and feels no shame. Why should it be different for you, unless you’re harbouring misogynistic thoughts, and you think being a woman is something to be ashamed of? Do you think it’s beneath you to wear panties, poppet? Only your inferiors wear them! Do you see people who wear panties as secondclass citizens? Um?”
“No, Miss, no! I don’t see myself as being superior to women. You must know that! I respect women, Miss, all women. But I wouldn’t want anyone but you to know I was wearing knickers.”
“How would they know, unless you were to show them.”
“Heaven forbid! I would never show anyone, not on purpose. But what about if I had to go to see a doctor or a nurse, Miss?”
“What, with a sore throat?”
“No! Perhaps some rash in the groin, or something like that. The doctor or nurse would see my panties.”
“So what? They’re professionals, and they’ll have seen it before, I’m sure. Even if they haven’t, they’re not going to comment. I reckon you’ve been reading too many stories where nurses start poking fun when a man comes in wearing panties.”
I didn’t know what to say, but she continued, “Anyway, it’s not very likely you’ll be going to see a doctor for a problem downstairs, and then they would see your cage anyway.” My God, I’d not thought of that and I gulped at the prospect. She grinned at my reaction and continued, “Just make sure you don’t show people your underwear. OK?”
“Yes, Miss,” I reluctantly agreed. “I’ll make sure not to show anyone.”
“So, that’s settled, then. We’ll get you some knickers and you promise not to show anyone. How’s that for a compromise?”
It was nothing of the sort, and her logic was twisted. However, despite the fears I felt, I did sense myself becoming aroused at the thought of being forced by this beautiful young lady to wear female underwear. “Thank you, Miss” I replied, redfaced.
“There’s no time like the present, so let’s go shopping!”
“Now?!”
“Yes, now! Get dressed.” Feeling jittery, I put my clothes back on, picked up my car keys and followed her out of her flat. A new experience awaited me.
oooOOooo
Being forced to wear female underwear excited me, but that did little to calm my nerves as we drove off to make a purchase. Soon, we were at a large department store, well known over the years for supplying British womanhood with their most intimate apparel. Like most men, I had had past occasion to walk through the lingerie section of shops, and I had always sneaked furtive glances at what was on display. However, on passing through, I had never stopped to examine the merchandise, let alone select something for me to wear. Today, that was going to change.
I felt myself trembling as Laura and I, handinhand, approached an aisle brimming with panties in every imaginable style, fabric, colour and size. The situation was made worse by it being a Saturday, with a large number of women browsing what was on offer. Some of these women had brought their menfolk along, but they were as embarrassed as I was and they tended to be looking down, fastidiously studying invisible marks on the shop’s carpet.
Any hope that I might do the same were dashed when Laura pulled me towards a collection of bikini panties. They were made of thin, satiny material, and bore no resemblance to boy pants. “What’s your favourite colour, Stevie?”
The question sounded innocent enough. “Black, I think,” I quietly answered.
“Hmm… I think white would suit you better, or pink.” She was using a louder voice than me and I felt myself redden. “We’ll get a pair of each. And these powder blue ones are delightful, so we’ll get those as well. What size are you, Stevie?”
“I don’t know,” I whispered. That was a mistake, because the next thing I knew she was holding a pair up against me. All I could do was hope that a sinkhole would appear at that moment to take me away.
“We’ll go for a size bigger, poppet,” she decided. She pulled three pairs of knickers off the shelf—white, pink and blue. “Hold on to these, sweetie,” she told me. I did so.
“Don’t screw them up,” she hissed, when she saw me trying to hide them from sight. “What would your mother say if she saw if you behaving like that?”
I mumbled an incoherent reply. “I didn’t catch that. Speak more clearly,” she remarked, well aware of my embarrassment.
“She would be disappointed, er… Miss.” I dropped my voice on saying that last word.
“Because of your silly behaviour, Stevie, we’re going to buy the matching bras as well. That will teach you a lesson, won’t it? Follow me.”
I did, and we moved to the bra section, which had an even more bewildering choice than the panty section. It turned out that colour matching was Laura primary consideration, as she personally felt it was important to wear bra and knickers of the same colour. “Do your mother and sister coordinate their bras and knickers, poppet?” she asked.
I blushed and sought to answer her question. “I… I… don’t know… I think so, yes. But maybe not… Sometimes, possibly.” In truth, I was clueless.
I looked at her, and saw she was grinning at my mangled reply. “I’m pulling your leg, silly!” she said. “What size bra do you take, pumpkin?” she asked, putting on an innocent expression. In her hands, she held three lacey bras—white, pink and blue—that complemented the three pairs of panties.
Feeling flustered, I replied, “I… I don’t know.” It was a truthful answer but not an answer I wished to expand on. Anxiously, I looked around, praying there was no one within earshot.
Laura didn’t question me further, instead saying, “Slip your fleece, off.”
Fearing what was to come, I removed my fleece, and she quickly wrapped the bra around my chest. “This is not the proper way of measuring size, but I don’t want to cause you unnecessary embarrassment, muffin,” she remarked, in a matteroffact way. By now I had turned scarlet, but I sensed that raising any objections would only lead to further public humiliation.
“I think I guessed right,” she assured me. “This one should fit, and it’s a 38C, so I’m not giving you enormous boobs—sorry!” She smirked, but I found it impossible to smile back.
She passed the three bras to me. “We’ll get you these, Stevie. Get your credit card ready!”
Together, we walked to the cash desk, and I prepared to pay for my purchases. The young woman behind the counter checked the labels on the undies and then looked at Laura, doing a double take. “Are you sure you’ve picked the right sizes, Madam,” she queried.
“Yeah, the sizes are fine, thanks. These are not for me.” For the second time, I needed to be swallowed up by a hole in the ground, even more so when Laura gave a sly smile in my direction. Luckily, the assistant made the reasonable assumption that Laura was buying for a female friend or relative, although she did look puzzled when it was me who proffered a credit card for payment. However, nothing was said and soon we were making our way out of the shop.
Only when we were in the car could I bring myself to ask Laura the question that was foremost in my mind. To have raised it in the shop could have provoked a loud telling off that anyone close by could have heard. “Surely you’re not expecting me to wear panties and a bra all the time, Miss?”
“We’ve had this discussion already. So, yes, you wear panties instead of your men’s underpants—every day.”
“But I don’t have to wear a bra all the time, do I, Miss?”
She chose to misinterpret my question. “Not all the time, silly. I take mine off in bed and in the shower.”
“No, Miss, that’s not what I meant. Are you expecting me to wear a bra in public?”
She hesitated before replying, which I took as being a way of winding me up. If so, it was working. “Hmm… well, let me think… No, stupid, of course not—unless you want to?!”
“Oh, God, no, I don’t. People would notice. I would be a laughingstock.”
She laughed, “I’m not completely stupid, you know. But you can wear the bra when we’re in my flat… and maybe… possibly maybe, occasionally outside… at least to start with…” She left her final sentence hanging, leaving me wondering what she had in mind.
“But remember, poppet, you wear the knickers all the time. No excuses, and if I ever discover you’ve been wearing male underwear, your backside will be sore for days. OK? And a clean pair every day, handwashing the worn ones. Understood?”
“Yes, Miss,” I replied, feeling both frightened yet exhilarated at what my future held.
