Go ahead sweetie, take a look at yourself while I get a few other small things.” Rebecca said as she walked over to her closet. Hi, Daddy.” The look on the employee’s face, whose name tag her hair had finally uncovered, and read Jessica, turned a bright red. I looked from Jessica to Katie’s dad to Katie. Katie just smiled.

is getting into skirts, corsets and heels - DeviantArt Jeff is getting into skirts, corsets and heels - DeviantArt

I find them so interesting. They make the wearer look so sexy, and I cant help but to wonder just what it would feel like to wear one” Jeff said without much thought. Why thank you” she replied. “However, it probably has more to do with the stricter corset I’m wearing tonight.” She said smiling.I think that you have found your shoes. One thing you will learn is that a woman never has enough shoes or purses.” Oh come on silly. It’s just a little bit of fun. Just go with it and enjoy yourself!” Rebecca said, completely blowing off Jeff’s complaints. “Alright sweetie, give your new shoes a twirl. Lets see how you handle those new heels!” And with a sharp slap to Jeff’s bottom she sent him off around the room. As the corset continued to tighten Jeff couldn’t help but notice how sensual and erotic the whole experience was. From the firm way it held him, to the way it started to mold and shape him to its shape. Just when he thought she had finished lacing Jeff felt her give the laces sharp tugs before she started to tighten the laces even further. When she was finished Jeff became aware of how the firmness and pressure the corset restricted his breathing. He immediately learned that he would have to take short shallow breaths. giggle* Silly it’s a butt plug. I know it feels strange and weird right now but once you get used to it you wont feel right without one. And once you start walking around again on your heels you will see exactly why I thought a butt plug would be a good idea for you.”

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And, Morgan, you need to come over and meet Katie’s mom, and I’m trusting that you will take care of Katie, and if you guys do decide to do any thing foolish, for God’s sake, use protection.” He said to me. Katie turned as red as a Coke can. Really? Wow, I can’t say I have ever met anyone who has ever worn a corset. I have seen them in some movies and all, and I must say they have always intrigued me, but it seems like most woman don’t wear them anymore.” Then with a pause Jeff continued, “I’m sorry you must find this a little uncomfortable.”

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Daddy, this is actually my boyfriend” she said giving this really cute smile after she said it and the surprise must have registered on my face. Her dad was smiling at me from across the desk. Ok,” she replied “Were you wanting loafers, boots, sandals and what is your shoe size?” She looked at my feet. You should wear panty hose to church instead of tights,” she said. “They will look more adult; tights make you look more like a young girl.” Jeff stretched his hands out to either side of himself to feel if Rebecca was still here. She wasn’t in bed so he assumed that she had gotten up already. It was at that point that Jeff’s senses really started to alert him that something was different. For starters Jeff felt like he was engulfed in soft satin. He just shrugged that off as not being accustomed to the sheets Rebecca had on her bed. But not so easily explained was the weird weight he felt on his chest, the odd feeling of being full in his butt, why his waist felt stiff and constricted, and the fact that his morning hard on seemed to be obstructed and unable to get fully erect. Daddy, Her name is Morgan, His name is Josh. The reason that he looks an awful lot like Jen is because he is Jen’s younger brother, and is currently being punished for wearing his sisters clothing. He has to dress like this for the next 5 months.” She giggled. “I like him regardless of what he is wearing.”

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Well how could I say no to such a beautiful woman who made my trip over so enjoyable” Jeff sheepishly replied.It took Jeff awhile, but after getting accustomed to the feeling of heels, and a few shaky laps around Rebecca’s bedroom, Jeff began to feel like he was walking like a pro. However, Jeff’s pleasure was short lived as Rebecca stopped him and told him “You have your balance down, but your still not walking like a woman. Swing your hips and give yourself a sway. That’s the only way you will look like a woman in heels instead of a man.” I spend a lot of money on new clothes for you and you wear Katie’s stuff.” She said with a smile on her face. I grinned. Well, seeing you in my corset and panties really turns me on, and you look so feminine and adorable. I was thinking that perhaps you would let me finish off the transformation and see how you looked as a woman.” She said as she sauntered over to Jeff and once again began to gently stroke his groin through the satin panties. “Please sweetie?” Ummm…Everything?” Jeff asked, a little nervous about getting naked in front of someone he didn’t really know all that well.

My Mistake, Chapter 5 | BigCloset TopShelf

Daddy,” Katie responded turning a crimson color because of her dad’s pet name for her, “I’d prefer to tell you in your office.” Mr. Richardson, I would never think of harming Katie. I love her too much, and as for our relationship, we just started going out. Although, I do worry about Tuesday, I’m not sure how I’ll be handled at school and I’m kind of nervous about it.” So, Katie, Who is this young lady that looks an awful lot like Jen?” He asked. Katie squeezed my hand to confirm my worst fears that she was going to expose me to her father. Little did I know that he would be perfectly accepting, almost adopting me as another daughter. It wasn’t until halfway through the trip before Jeff finally got up the nerve to talk to her. He had noticed that she was reading an article about models in her magazine and promptly asked “Sorry for being nosey but I noticed what you are reading, are you a model?” Jeff took her suggestions and tried to sway his hips but it wasn’t to long before Rebecca stopped him and said “Your just not getting it. Your movements are either way over the top or just look forced or unnatural. Now I could have you prance around this room all night before you got it down, but I think I know something that will give you that natural sway. Now I don’t think its necessary…” she said as she reached into her nightstand drawer “but it will most definitely get the job done. Now come and lay across my lap.”

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Jeff practically melted as Rebecca ran her hands over him. He couldn’t help but think that she had a point. With that he took the panties and slipped into them. He was amazed at how wonderful the silky material felt as they slid up is legs. Enjoying the experience, Jeff couldn’t help but think that perhaps Rebecca was right; they were not that different from his boxers. Sure they were much more smoother, felt really nice, and were cut differently, but they were actually quite pleasant to wear. Yeah, what about her?” he asked with a curious look on his face, almost as if he knew something about her that we didn’t. Business went well and before Jeff knew it all his meetings were done and he had a week of vacation to spend however he wanted. Initially he had planned on spending it catching up with family and friends. However, the conversation and company of the plane trip kept playing in his mind and it was only a few hours after his last meeting before Jeff found himself standing in front of the door to Rebecca’s apartment. Jeff stood frozen watching Rebecca’s perfect figure walk down the hall, teasing him to follow. Without much thought to it Jeff began dreamlessly walking towards her room despite knowing what laid in store.