tagTranssexuals & CrossdressersPunished for Cheating

Punished for Cheating

byundiecontrol©

How my life had changed in the two months since I had taken in Caroline as my lodger. The arrangement seemed ideal at first – I was a newly divorced male and she was a single girl. Of course, I should have foreseen that the 30 year age gap might present a problem but that is the wonder of hindsight.

My few clumsy passes appeared to annoy her but not to the extent that I had expected. When, through being nosey, she stumbled across my collection of panties, together with photos of me wearing the panties, she chose to exact revenge by blackmailing me. Of course, I should have resisted these initial attempts, but, instead, I complied with her demands and soon I was sliding down a slippery slope, as she accumulated further damming evidence and increased her demands.

And so it was that, at 7.15 am on a Wednesday morning, having freshly showered, I found myself selecting the white panties and bra that I had been instructed to wear for work that day. Up to now, she had only made me wear bras at weekends – and only indoors. In fact, this would be the first time I had worn a bra to work – ever! I was dreading it, but her hold over me was now too strong for me to refuse.

But I had no time to waste. Miss Caroline (no longer just plain "Caroline" to me) required that her light breakfast was served in bed at exactly 7.30 am each morning, with me wearing the underwear selected by her for that day.

So I slipped on the panties and then put my arms through the straps of the bra and reached behind to do it up. Miss Caroline insisted that I put on bras in this way, rather than doing them up at the front around my waist and then hoisting them up. I had been made to practice in front of her until I could do it within a few seconds.

Dressed in my lingerie, at precisely 7.30 am I knocked on her bedroom door. Only four weeks ago, this had been my bedroom – the master bedroom with en suite bathroom – but now it was Miss Caroline's.

"Please enter," replied Miss Caroline, as polite as ever. She was lying in bed, with the covers pulled up so that nothing intimate was revealed. While disappointed, I was also rather relieved because any sign of sexual arousal on my part would have been dealt with by severe punishment.

It was humiliating for me to stand there in just panties and bra, but I knew I had no choice in the matter. "Good morning, Miss," I announced, trying to sound as chirpy as possible, "I hope you slept well?"

"Yes, thank you, Sharpe. Please put my breakfast down here and then present yourself for inspection."

Following a familiar procedure, I put down the tray as instructed and then stepped back several feet and stood smartly to attention with my hands resting flat on the top of my head.

"Good boy, Sharpe. I must say you are quite well turned out today but I would rather you displayed a smoother image under your panties. Trying using some tape tomorrow." She aimed her digital camera at me and took a few shots to add to her dossier.

"Turn around so that I may see the side and then the back." I saw the repeated flashes of the camera as I complied with her commands.

"Not so good from the back, Sharpe. Your panties are slightly skewed and the label of your bra is on display. I'm afraid I expect to see greater attention to detail. I will not tolerate a sloppy appearance. Is that understood, Sharpe? Otherwise, you can expect to be punished."

"Yes, Miss, I understand, Miss."

"Good! I assume your underwear is clean, Sharpe?" she enquired.

"Yes, Miss, fresh on today."

"And have you sewn a white sock into each cup of your bra, Sharpe?"

"Yes, Miss, I did that last night before bed."

"Well done, Sharpe. But I want you to remind me why you are having to wear a bra to work today for the first time."

"It's because I cheated yesterday, Miss. I changed from panties to boxers just before leaving for work."

"Yes, Sharpe, that was really very silly. Even more stupid was leaving your discarded panties where I would find them. Not very clever, Sharpe, and now you are paying the price. Wear a bra to work for the rest of this week, and receive 12 strokes of the cane at 6.00 pm on Saturday! I see that the marks from your last caning have disappeared from your thighs so you are probably overdue for your next caning anyway."

"Please, Miss – please reconsider the caning. I don't think I can take 12 strokes."

"You should have thought about that before cheating. Now you may put your arms down and sort out the label on your bra and adjust the position of your panties." Resignedly, I did as I was told.

"Good! That's much better, Sharpe. I'm now turning on the tape recorder and I want you to introduce yourself and describe what you are wearing."

"My name is Dave Sharpe of London and today I am dressed in white cotton …"

"STOP! You have been told before to use the possessive adjective. Your underwear is your personal possession. Now start again, Sharpe."

"Sorry, Miss. My name is Dave Sharpe of London and today I am dressed in my white cotton panties, size 14, that are in a full brief style. I am also wearing my white seamless bra, size 38C, which is underwired and moulded to provide shape. It is of a conventional design with shoulder straps and a back fastening. A white sock is sewn into each of my cups to provide firmness."

"Good boy, Sharpe – nicely described. And what do you plan to wear over the top of your lingerie?"

"I was hoping to wear my black suit and a dark blue shirt, Miss."

"Umh… I agree with the black suit but don't you think that a white shirt would be so much nicer?" I didn't get chance to answer before she continued, "So a white shirt it is. Go and fetch your clothes, including a white shirt, and report back." I felt me stomach sink at the mention of a white shirt.

I hurried to get my clothes and, when I came back, Miss Caroline instructed me to put on my shirt and button it up. I did so as quickly as possible, my fingers trembling. I then put on my tie and, next, my trousers, socks and shoes. She told me to leave my jacket off and I was very conscious that my bra would be visible through the shirt, particularly from the back.

"Good! - you pass inspection, Sharpe. Now it's my turn to get dressed. You know the routine - go and face the wall with your nose up against it and your hands flat on the top of your head. Do not, under any circumstances, turn around until you are told to do so."

I quickly assumed the position. It was what I had to do every morning – Miss Caroline was insistent that I should never see her except when she was fully dressed. As far as she was concerned, our relationship was entirely asexual.

I knew from experience that Miss Caroline took about 45 minutes to shower, get dressed and apply her make-up. She was never in any hurry and seemed to care little about my discomfort. It wasn't long before my arms began to tire. My bra was also slightly too small and the underwiring dug into my chest, causing me further discomfort.

But how I longed to see her naked, or in her lingerie, but I knew that the punishment for turning around, even for a second, would be extremely severe if I were caught, so I kept my nose to the wall and my hands on my head, trying to imagine what she was doing from the odd noises that drifted my way.

Slowly my discomfort turned to pain - and then to almost agony. "How long can she possibly take?" I wondered to myself out of exasperation. "Hurry up, for God's sake!"

Eventually, she summoned me to turn around and put my arms now. They were numb from the position I had maintained and I rubbed them to get the circulation back. I looked in her direction - as I expected, she was attractively and expensively dressed, and entirely at my expense.

"Please come here, Sharpe," she requested. "Hold up your tie. I am going to put two stitch knots into your shirt to hold it together. With these in place, you won't be able to take off your shirt - and if you can't take off your shirt, you can't take off your bra. It's a pity I can't trust you to behave but after yesterday's little performance I can't take the risk. I'm sure you understand."

I held up my tie and she produced a needle threaded with pink cotton. Very deftly, she threaded the needle backwards and forwards and sealed my shirt shut at two places - one three inches below the collar and the other six inches further down.

"That's done," she announced. "Cover the stitches with your tie. Good! If those stitches are not in place when you get home for inspection this evening you can expect to be very severely punished. It will be a double caning for you on Saturday! Do you understand, Sharpe?"

"Yes, Miss, I completely understand", I replied meekly, swallowing hard.

"Oh! And by the way, I will be phoning your manager to check that you attended work today. Don't think you can bunk off! Now put on your jacket and get off to work to earn some money for me to spend."

So I went and put my jacket on and left for work, knowing that this would be a day when I would have to keep my jacket on at all times. I had to hope that the forecasters had got the prediction of a hot day completely wrong. It was with much trepidation that I caught the tube that morning …

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by Anonymous12/20/13

Not worth reading

Not a single, redeemable thing about this mess.

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