Chapter 5

Right after breakfast, Mother Superior approached me and took me aside. “Toby, you will come to my room promptly at nine o’clock tonight. You will not have any sexual encounter with any other sister between now and then. You will come and be prepared to stay the night. Bring your toothbrush and clean underwear.” Mother Superior turned and walked away. She didn’t even have the courtesy to ask if I had other plans.

At eight o’clock that night, I started getting ready for my night with Mother Superior. I showered then shaved what little growth I had on my chin and upper lip. I even put on a little aftershave. At ten minutes to nine, I put a set of underwear and my toothbrush in a paper bag and went to the supply room to take out the roll-around-bucket, a mop, then headed for the nun’s quarters. Once inside the nun’s quarters, I parked the bucket and mop in the corner, took the paper bag out of the bucket then waited until exactly nine o’clock to knock on Mother Superior’s door.

The door opened. Wearing a light blue floor-length robe, Mother Superior welcomed me with a smile. “Come in, Toby.”

I stepped into her room, and she shut the door. She didn’t have any lights on, but she had candles burning on her dresser and the nightstand. The candlelight gave the room a warm and cozy feel with a suggestion of romance. Mother Superior’s hair is light brown with gray at the temples, a round face, and thin lips. Her eyes are grey. I swear they twinkled when she smiled.

“Very good, Toby, you are right on time. Now put your toothbrush and underwear in the bathroom and strip down to your briefs. I will wait for you out here.

I left my toothbrush and underwear in the bag on the countertop. I stripped down to my underwear and went back out to the bedroom. Mother superior was lying in the middle of the four-poster bed in just her underpants with her hands tied to two of the bedpost. When I looked close, she had only slipped her hands into a loose loop that she could easily slip right back out of again. It seemed Mother Superior was into some light bondage fantasies.

She was watching me with a wary look on her face. Her eyes squinted as she assessed what I would do with my captive. Mother Superior was definitely in her fifties, and like most in that age group, she had put on a little weight. Her breasts flopped to the side, and she had a round tummy.

I thought I had her all figured out when I asked, “So Mother, what’s it going to be? A Countess captured by pirates, a wayward wife? Perhaps a slave to be used by her new master?”

“This is a game, Toby, not role play. You have to tease me until I can’t stand it anymore. If you tease me enough that I take my hands out of the ropes, you have won. You can tease me any way you want. Just about anything goes, except you can’t fuck me.

“What do I win?”

“You can tie me up and fuck me anywhere you want.”

“Anywhere?”

“Yes, Toby, even there. But if thirty minutes go by and I still have not taken my hands out from the ropes, you lose.”

“And if I lose?”

“I tie you to all four bedposts and use your tongue and cock anywhere I want.”

“Anywhere?”

“Yes, Toby, even there.”

“Now, take my bloomers off.”

“Bloomers?”

“Yes, bloomers. Do you think they let us wear lacy pink bikini underwear here? Come on now; you’re supposed to be taking advantage of me in my helpless state.”

I pulled her bloomers down, and much to my surprise, her pussy was shaved clean. She spread her legs as I stared. I had never seen one shaved before.