Jennifer waited for Scott to finish his wriggling, still tapping his bottom, and delighted in saying firmly, “Now for the last one Scott which you know must be the hardest.” Scott groaned as Jennifer tapped his bottom another six or so times before the tapping stopped, a second passed, then the swish followed by the thwack and the searing pain as this was most certainly the hardest stroke so far. Becky was watching quite awestruck as although she had seen her Mum cane Scott, Jennifer caning him was quite exceptional, and had a markedly different effect on her older brother. He had never shrieked like that before and she supposed the whole tapping method was effective in building up anticipation of pain, and painful it clearly was. Becky was quite breathless when her Mum came over and said quietly, “Can I have a word please Becky?” Becky nodded absentmindedly when at the same time Mum said sternly to Scott, “Face the wall with your hands on your head until I say you can get dressed.”. He tried on lots of tops first until he found one which suited him. I told him how well he looked and jokingly asked if he wanted a bust to go with it! He blushed and told me that he’d wanted to dress up for ages but his ex didn’t want him to. I found an old padded bra and some silicon push ups which gave him some cleavage under the top. I asked if he wanted to go the rest of the way and when he agreed I got out some stockings and skirts I thought would suit him. Luckily I had a pair of boots which were about his size as well, so I took the lot into the spare bedroom and left him to it. I choose some patterned stockings and a saucy black skirt myself and was sitting doing my makeup when he came in and for a second I thought it was somebody else who had come in the house. He’d chosen some sheer black stockings and a fairly short skirt to go with the boots and as he is very slim and feminine looking and has his hair quite long, he looked really good even without a wig. We had some more.
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