My parents going to the city was quite rare while we were growing up. Usually, they would make the trip only a handful of times a year to buy supplies and sign new contracts for dairy deliveries. While automobiles had been invented over a decade ago, they were considered a novelty in our part of the country, so most folks still traveled by wagon. While the distance to the city wasn't more than 30 miles, the amount of time it took to make the round trip mandated that my parents be away for at least two days when they would go.

Ms. Anderson, our new live-in nanny was to be in charge of us while they were gone. I was the eldest, at sixteen years old. The nanny really wasn't for me, but for my younger sister and the twins. She had only been with us for a few months now, having replaced old Mrs. Julian when she went to go live with her daughter in Milwaukee. Ms. Anderson, although much younger than Mrs. Julian, was a very skilled nanny, and most-definitely a no-nonsense woman.

It was unusual but not unheard of in our little community for the nanny's quarters to have its own water closet and bath. Nearly three weeks ago I had discovered that I could gain an unimpeded view into her room through the keyhole lock!

Usually, I would only catch a glimpse of her as she walked from her bureau to the WC for her nightly bath, but that was always enough to help me get up a good head of steam. I would proceed straight to my bedroom and imagine the feel of her bosom as I stroked myself off.

I had also discovered that Ms. Anderson only used one of the two large closets in her room. In the days leading up to my parents' trip, I began to formulate a plan. I decided that when they left, I would try sneaking into the empty closet before she got to her room at night, leaving the door cracked just enough and hopefully get more than a quick glimpse! I planned on escaping after she had gone in for her bath.

At dinner that night, I could barely speak, and I had to work from keeping my hands from visibly shaking. I excused myself from the table, and after helping clear the plates, pretended to go off to bed. Instead, I sneaked into her room, and hid inside her unused closet.

I waited for what seemed like an eternity as I listened to the nanny putting the children down for the night. I could hardly wait for her to step through the door! My penis was already growing inside my drawers. I gave in and rubbed it a bit through the material, but only briefly; I wanted to wait until I could see Ms. Anderson.

A few minutes later she walked into her bedroom and closed the door behind her. Immediately, her fingers began working the buttons of her sweater and blouse. She was humming the same song she used when she lulled the twins to sleep.

I nearly panicked as she came toward my hiding place, thinking that tonight was the night she would decide to use the empty closet! Of course, the closets were side-by-side, and she was just going over to the one that held her clothes. I held my breath as she hung the sweater in her closet. Blood was pounding in my ears, and I was sure she’d hear me! Instead, she just took her blouse down off her shoulders, and tossed it on the bed.

She was now facing away from me, but the sight of the soft skin of her back as it was exposed quickened my pulse. She reached back and unfastened the clasp of her brassiere. This, too, she tossed carelessly on the bed. Letting out a deep breath, she raised her hands and rubbed both of her breasts. Not in an erotic fashion, rather like letting them out after being confined all day in that tight brassiere.

I shifted my weight slightly; this was the moment I had been waiting for! I slid my drawers down my legs, and took my willie in my hands. It was already stiff and pulsing as I began to rub up and down its length.

Still humming, she moved toward the bureau and pulled out the stool. I caught another glimpse of her milky breast as it swayed when she bent to slide the skirt down over her hips. Now sitting in just her bloomers and silk stockings, she turned and began to take down her hair.

I eyed her stockings, remembering the time I had stolen one from her laundry and used it to rub on my penis until I came off. What a mess I made of the stocking! I cleaned it as best I could, and then slipped it back in her laundry the next day, hoping she wouldn't notice. It was a tense week until laundry day came and went with no complaints.

I shifted my weight again, and from my vantage point was able to see her back as well as her breasts in the mirror! I continued stroking myself, quickly, but silently.

Ms. Anderson had finished letting her hair down and rose quickly, walking into her bath room. I waited until I heard the water tap start, and then opened the closet door quickly. I stepped out, drawers in hand, and tip-toed quickly towards the door. My stiff willie was pointing the way. I wanted to get into my own bed so I could finish stroking myself off!

It wasn't to be. "Jared! You stop right there! What are you doing?"

I turned to face Ms. Anderson. She was standing in the entrance to her WC, hands on hips, and from the fire I saw in her face, fit to be tied. She was, however, still dressed in only bloomers and stockings. I tried my best not to stare at the swell of her breasts, or her large, dark nipples.

"I'm just... I..." I was dumbfounded. And I was caught.

"If your father were here he'd whip you until you bled. Or worse!"

"Yes, Ma'am," I admitted.

"You need to be punished, but this is nothing that can wait until your parents get back," she continued. My prospects suddenly brightened; she was right, my father would have skinned me alive. I was willing to take whatever she decided was a fair punishment if he never was to find out.

She sat on the edge of the bed. "Come here," she ordered, and I dutifully approached, ever aware of the sway of her succulent bosom, and my still stiff penis. "You will be spanked. Over the knees, Jared." I must have turned red as a radish; after all, I was sixteen years old! I was nearly a man. However, I knew that I must succumb to her wishes, or I may never live to become a man once my father heard of the deed.

I did as she instructed, laying my hips over her thighs. My smooth, bare buttocks were in the air in front of her, and my still-swollen penis was trapped between her thighs. One of her stockings had slid down her leg, and the underside of my penis pressed against the warm, bare flesh of her thigh, while the top was rubbing against the silk of the other stocking! I knew I was in trouble, but I could not help but be aroused by the situation.

She delivered the first slap on my backside. It stung a little, and brought me to the reality of what was happening. The second stung a little more, and I felt embarrassment wash over me. After a few more, the embarrassment got the best of me, and I began tearfully apologizing to Ms. Anderson. She delivered a few more swats, and then rubbed my crimson backside for a few minutes. Then she ordered me to turn over.

Again, I did as I was ordered, placing my head in her lap. As I did, she began scolding me again, telling me how bad it was that I was spying on her. She called me a Peeping Tom. At that moment, my shame was complete. I could feel heat rising in my face, nearly matching the heat in my rear that was the result of my spanking.

Once again she surprised me by saying, "And I now can guess who made such a mess of my stocking last month!" She had taken the one that had slipped down her leg and was now holding it for me to see. I needn't have said anything. The look on my face gave it away. "I thought so," she said.

To my surprise, however, she reached over, and tied the silk stocking tightly around the base of my penis and balls! I looked up at her in astonishment as she began to stroke my stiff rod. She started slowly at first, then began to increase her speed!

She looked down at me, still with that stern look on her face, and brushed her nipples across my face. I didn't know quite what to do, so I just put out my tongue and began to lick and suckle on them. First one, then the other as it was presented to me. She continued to stroke me, increasing the tempo as I continued to experience her breasts with my mouth.

My first taste of a woman's breast, the silk tied around my privates, and the warm hand stroking my penis was all that I could take. I came off like a rifle, squirting the stuff high into the air in great, pulsing arcs. It landed on my chest, my thighs, all over the silk stocking and Ms. Anderson's hand. Some even made it to her breast!

I lay in her lap whimpering, still under her soft cleavage, with her gently stroking my now slippery penis. She untied the stocking, and said, "We'll not let this happen again, Jared. Now off to bed with you!"

"Yes, Ma'am," was all I could say.