Transcripts Ch. 07

I sat up, propped up on my elbows, "What's unhealthy about that?" I asked.

"It's not something that you should be thinking about, it's not for you and I think you need to understand this. I want you to take this lesson on board and learn from it."

"Okay, I will try not to stare at women's bottoms again. I will look away and think about something else." I said apologetically.

Jenny rose up from her stool, with the wooden spoon gripped in her hand. I remembered the last time she had slapped me, and flinched. "I'll need you to lay back, put your hands behind your head and spread your legs," she said. I obeyed and shifted my position on the couch. "Don't talk! I need you to be silent."

Jenny turned around, facing away from me. She hitched up the hem of her dress above her waist, revealing her peach shaped bottom. I saw the thong panties, a slender piece of silky, white that bisected the dark skin of her cheeks. My penis rose, engorged with excitement, I thought about wrapping my fingers around my erection and masturbating. Jenny bent forward, pushed her bum out and twerked. As she shook her booty close to my face, I had a view of the outline of her pussy lips through her gusset.

Abruptly and without warning, she straightened, swivelled around fast on her heels, and brought the wooden spoon down hard between my legs, smacking me squarely on my exposed genitals.

"Oww!" I bit my lip, trying to curl myself up in a ball. She slapped down quickly again, catching my testicle. Tears welled up in my eyes. "Please stop, I'm sorry." I tried to bring my knees up and my hands down to protect myself. Jenny grabbed my knee, forcing my legs further apart and hit me once more.

"I said no talking! Keep your legs open and your hands out of the way," She hissed. "Otherwise you'll get extra smacks." I did as I was told, crying as she slapped me three more times in quick succession. Jenny stopped, stood back and adjusted her dress. She looked down at my now flaccid penis, accessing her work. "Now everytime you take a look at a woman's pretty behind you'll think about this pain. If I hear any more reports from my sister or any other girl that you've been staring at them, you will feel the back of the spoon again."

I gasped through the tears, felt the intense pain in my lower abdomen and groin. I looked down towards my penis, that had now shrivelled up, leaving a pool of dribbled semen. My scrotum felt as if it was on fire. I trembled, thought about the damage that she might have been caused.

"Clean up that mess with your fingers, then lick them," Jenny said sternly. "I want to see you eat your cum, just like you did for Amy."

I did as I she asked and licked my mess from my fingers. Jenny opened the curtains, and went over to the armchair. She picked up the carrier bag, that she had earlier placed by the side of the chair. Then returned, put the bag down on the top of the trolley and stood over me.

"Sit up now, swing your legs off the couch and stand up please," she ordered. I winced as my feet touched the floor, straightened myself up, holding on to the couch. "Now tuck your little willy between your legs and pull your panties up."

I felt sore and tender as I pushed my limp penis back and eased the soft panties up over my hips, then closed thighs tightly. I stared down at the front of my knickers, my tucked genitals left a slight bulge.

"Good, if only you had wider hips and a rounder arse, you might almost pass as female. Perhaps one day when we've had your clitty pinned back with piercings and you've been taking hormones." Jenny said, regarding me with narrowed almond shaped eyes. "I have something for you," She reached for the bag from the trolley, opened it up and pulled out items of clothing. She held up pairs of women's leggings and brightly coloured loose t-shirts. "From now on you'll wear these while you're working here. I've chosen a variety of colours, but I'll let you decide what you want to wear first."

Jenny placed the clothes next to me. Three of each in shades of white, bright yellow, hot pink leggings and matching tops. The t-shirts all had a rainbow motif across the chest. I looked into Jenny's eyes, her expression was serious. "Do I have to wear these? People will laugh at me," I pleaded.

"Don't be so silly they're just work clothes. Wear them while you're here, not all the time." She then produced a pair of women's light blue slip on shoes from out of the bag, and placed them next to the pile of clothes. "They are in your size, try them on and stop being such a cry baby. You do get to choose which colours to wear first."

I gave a sigh with resignation, before looking through the colourful collection of garments, I opted for the white pair of leggings and t-shirt. I held them up, before I stepped into them and pulled the tight, stretchy nylon up my legs. They fitted snuggly, but were short, three quarter length, my lower legs were on view and exposed. After I pulled on the matching white top, I looked down at the rainbow across the front and felt ridiculous.

"Lovely, don't forget the shoes." Jenny said, urging me to slip them on my bare feet. They fitted perfectly, I wondered how she knew my size?

"You look great, they are so skin tight. Give us a quick twirl?" Jenny said, looking pleased with herself. I turned around slowly, sore and aching. "Oh, visible panty line, your red knickers show right through. No one will notice once you're wearing your tabard. Unless you bend over," Jenny laughed.

"I'm bent over most of the time while I'm mopping the floor," I said. The shoes and clothes felt weird against my skin. I would have to get used to the lifestyle changes, and wondered where would it all end?

"Now I have one more item that I want you to have." Jenny reached into the bag once more, pulled out a large black dildo. She wrapped her painted fingernails around it and pointed the sex toy towards me. "You need to start using this rubber cock, instead of wanking yourself off. When your in your bed. Go ahead and feel it."

I studied it in her hand momentarily, then reached out and took it from her. The black silicon felt cold and textured. It was around seven inches long, girthy, realistic and lifelike. There was a suction cup on the base. I had bought Amy something similar once, that took batteries and vibrated.

"You can stick the base to the wall or to a chair, Jenny said. What do you think, you love it, don't you?"

"Thanks, I don't know what to say," I replied, feeling awkward and ashamed. "What about the butt plug?"

"Remove it before you have fun fucking yourself at night. You might even squirt a little if you try hard enough," Jenny laughed, looked at her watch. "That about wraps up today's session. Can you be here at the same time next week?"

"Yes of course. Tuesday afternoon at four as usual?"

"That's it. You can leave your clothes here, and the dildo and change when you finish," Jenny picked up her notes, strode confidently over to the armchair. I was not sure what to do next, dressed in women's casual clothes with a black dildo in my hand. I stared over at Jenny as she settled down in her seat. "Well what are you waiting for? You have work to do."

"Yes, I'll see you next Tuesday," I said, gathering my thoughts before I made my way gingerly towards the door, humiliated and sore.