Family Friend, Jane

One summer, when I was 18 years old, my parents went on a vacation. My parents were going to be gone for three months and they didn't trust me to be alone for that length of time. I didn't know how to cook for myself, and I didn't know how to keep the house clean. I had lived a sheltered life where my mom had done all of the housework and I just studied and did my homework. So they had a family friend, Jane, who had just graduated from college, come to baby-sit the house and me. Jane's family used to live down the block from us, and Jane used to baby-sit for our family. As a baby-sitter, I recall her spanking me, since she had permission from my parents to punish me. It worked out well for her to watch over me since she was able to cook good meals for me, and she kept the house clean. Before my parents left they told me, "Jane will be in charge of everything while we are gone. If you get into trouble, we have given her our full permission to discipline you. So don't get into trouble." I was basically a good kid back then, so I thought I had nothing to worry about.

But at age 18, my hormones were raging, and I was alone with a woman, who was only five years older than myself. I didn't know a lot about the opposite sex, hadn't gone out on that many dates, and I wanted to find out more. Our house had a guest bedroom, and that is where Jane was sleeping.

One day, when Jane had gone grocery shopping, I went into the guest bedroom. I wanted to see and touch her bra and panties. I had seen catalogs were they showed women wearing them, but I wanted to see what Jane wore, and what they looked like up close. I guess I got carried away, because I spent more time than I thought, looking and feeling all of her bras and panties. I also wanted to see how it felt to wear her thin smooth panties, so took off my slacks and underpants, and tried on a pair of her panties. To my surprise, that was when Jane entered the guest bedroom. She caught me, wearing her panties, with the dresser drawers open, and me fondling her other panties.

"You naughty boy!!" Jane exclaimed. "You should never go through the clothing of someone else, and you should never wear another person's underwear, especially of the opposite sex."

"I'm sorry," I said.

"You will really be sorry, once I punish you for going through my clothing." Jane next sat down on the edge of the bed and said, "But before I punish you, let me have a closer look at what you look like in my panties. Come over here." I had an erection already from the silk panties, and they were so sheer that you could see everything. So I was quite embarrassed, but I walked over to her anyway.

"Put your hands on top of your head and keep them there while I examine you," Jane said.

Then her fingers touch my penis and my bottom. "You act like you enjoy wearing my panties. Did you know that girls shave themselves so that they look better when they wear panties? Let me pull down the panties and see how much hair you have." She pulled down the panties, and now I was standing before her, naked from the waist down. "If you are going to wear my panties, you should have no hair down there. So let me get my razor, but you stay there with your hands on top of your head."

So she went into the bathroom and came out with a razor and some shaving cream. She put the shaving cream all around my penis and balls and shaved me. While she was shaving me she said, “This will make you look like a girl when you wear my panties.” After she was through shaving me, she got up from the bed again and came back with a wooden hairbrush and a paddle. “Now I am going to spank you for going through my underwear,” Jane said. “You can take you hands off the top of your head, now, and lie on the bed over my lap for your spanking.” Jane was wearing jeans and soon my penis was between her legs, as I awaited my spanking. “First, I’m going to start you off with a handspanking, then I will use the hairbrush, and then the paddle.”

The handspanking wasn’t too bad, but by the time she had used the hairbrush and the paddle on me, my bottom was really hurting. While she was spanking me with the paddle she said, “After your spanking, I’m going to take you shopping with me so that you will have your own panties to wear while I am here.” Soon, my spanking was over, and then she had me pull up the panties that I had on of hers, and put my slacks back on. “You should grab a pillow to sit on in the car, you are going shopping with me.”

So we went to several women’s lingerie shops, and she got me some panties. It was so embarrassing, she told the sales clerks that the panties were for me to wear, and at one store she even had me pull down my slacks so the clerk could see the panties that I had on. What made matters worst, the clerk also noticed my red bottom, and Jane told her that she had just spanked me.

So during the remainder of Jane’s stay, each morning I had to drop my pants for her and show her the panties that I was wearing. She also shaved me every three days, so that I would like a little girl down there. Jane also found a few more things to spank me for, so I got used to going over her lap for a spanking.

After my parents got back, I wore my regular underwear, again. But I do miss my old family friend, Jane. Now that I am older, I hope to visit her someday, and bring the panties that she bought me. Who knows, she may even spank me again!