Chapter 3 Penny's Makeover
This chapter doesn't have much sex in it. It's important background for what's to come. Some of you may choose to skip it. But for those who read on, you will have a better understanding of Penny's transformation.
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I made some mental notes from our Library session. Penny was insecure around Maya. I will need to explore this with her. But I also found it curious she allowed herself to be submissive to another woman.
It was a surprise for Penny to walk into my session. A good one but just unexpected. I know she will have a few days to heal. We will have to step up her training when she arrives on Friday. Two days with her. This will be fun.
When Penny arrived, she stepped in, removed her clothing, and sat on her knees on the floor in the middle of my main room. I walked out of the kitchen looking at her beautiful hair and pert little body noticing her nipples harden when she saw me walk in. A good reaction I thought.
I sat on the sofa and patted the seat next to me, "Come here, Penny."
She rose and sat next to me pressing close to my body.
"Tell me what you thought about the visit to your library this past Monday."
"That's a big question," Taking a deep breath, "What I experienced physically is on the surface but the real question is what was the mental impact."
"Tell me. What are your thoughts?" I asked.
"I had to wonder if you actually planned the entire thing Gio."
"Talk to me about that."
"I'm curious about my own id. I love being your submissive Gio, but I can't help but ask myself why. I like the play. I wonder why I enjoy humiliation. I haven't arrived at actually enjoying pain yet but I can tell you the punishment I received ultimately made me incredibly horny. Is that the same thing? My genitals were screaming Monday night. By Tuesday morning, they were so swollen that a mere touch sent shock waves through my body which were intensely pleasurable- feelings I had never experienced before. It made me want to touch my abused self to feel those spikes of pleasure."
I guess it's just the way I tick. I like to analyze. Don't get me wrong, this experience is extraordinary. And I am grateful to be your student. It's a little scary but I feel like I'm unlocking aspects of myself that have been repressed by social norms. It's a lot to absorb Gio."
"And what about Maya? What about your encounter with her and what happened?"
"First of all, she is shockingly beautiful. Are all of your subs that beautiful?"
"She's a client."
"What? Wait. Have you done this before? Is that what you were doing the day we met?"
I smirked at her.
"Oh, you are slick. Why in the world a college library?"
"No one goes to that second floor but the women I bring there don't know that."
Penny smiled, "You're right. That's the research floor. No one really uses a library for research anymore."
I continued, "Maya is in a dead marriage and needs mental and physical stimulation just like the rest of us. She has too much to lose by leaving her spouse so there is an arrangement. Let's move beyond who she is and talk to me about what you felt with her presence between us."
"I have to admit I was intimidated."
"Why?"
"She was tall, had beautiful big breasts, and a nice round tight ass. I am short..."
"Petite. Go on." Interrupting me, making eye contact.
"I'm petite, with small breasts, and look like a girl, not a woman. I felt inferior, weak, nonpareil."
"Do you want to know what I think?"
"Please?"
"First of all, your mind and soul shine." I could see Penny relax and appreciate what I was saying.
"Secondarily, you are different. I find your qualities incredibly attractive and desirable. Your petite frame, beautiful puffy nipples," I reached out and stroked her slit, "Your magnificent mound and your tight little ass. You are as perfect as any so-called 'beautiful' woman', whatever that is. If you felt inferior, the question I would ask is did you enjoy that?"
I could see Penny thinking about that. Looking at me she cocked her head to the side and said, "I hadn't thought about that. Maybe? Probably?"
"I believe a part of your submissive nature is to enjoy being diminutive. Accepting your 'role' in play is your baseline. You are correct. This is innate. But our cumulative experiences in life too often hinder our ability to open ourselves to truly be free of what our society has programmed us to believe is right and wrong. Good and bad and even what should be pleasurable and painful. Am I boring you?"
"No please, this is fascinating," she said.
"So, Pleasure in pain is such a misunderstood concept, sociologically, most people are denied the personal growth we can achieve through our experimentation and true self-awareness.
And I would go so far as to say being treated as a lesser excites you. Do you think that's true? Why did you spread your labia to be stricken? You knew what was coming."
Penny put her head down and turned a little red. "Because I wanted to surrender to her...and you."
"Oh, so you were willing to be submissive to us both."
"Yes." Very quietly.
"We're going to have fun today Penny." She perked up. "Get dressed. You are going to the beauty parlor."
"What? Wait! I've never been. Why?"
"We are going out tonight and I want to show you off. You will have your hair and makeup done and then you will be fitted with a new outfit for this evening."
"Wow. Really? OK" now very excited.
As I called the car, Penny climbed between my legs, pulled my cock out and swallowed me whole. She worked my member with much-improved skill.
As she was sucking me, "I hired a car for the day. You will be driven to your beauty appointment and Maya will meet you to go shopping." Penny wiggled her body and looked up at me smiling and took me deep down her throat.
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I was a little nervous but I shouldn't have been. "Hi I'm Penny Addams, I have an appointment."
"Yes Penny, right this way."
I was taken to a chair and as I sat, a man approached me. He was not what I expected for a hairdresser. "Hi, I'm Marcus. I love your hair! I know exactly what we will do."
"You're not going to cut it off are you?" I was looking at him and he was definitely not gay. This was a manly man.
"No I'm just going to trim the ends and we will make you look elegant for Gio."
"Oh, you know Gio?"
"Personally and from our business relationship here. Sure." As he wrapped a cape around my neck.
As he washed my hair I couldn't help but feel his body close to mine and his warmth. And his smell. He smelled really good. It made me a little horny.
He would lightly touch my body with his as he was blow-drying my hair. Was this normal? I didn't mind but I didn't know what to think. He made a lot of eye contact and asked me a lot of questions about where I was from, school, my major, what year, and all that stuff. The entire time, my back was to the mirror.
When he spun me around, I didn't recognize the woman in the mirror. My hair was up, but there were loose strands all around. I looked...elegant. It made me feel so good.
"How do you like it?"
"Oh, Marcus! It's amazing. I love it!"
"OK, let's get your makeup done."
"God, I hate makeup."
"I know, but you will like what we do."
"OK"
I sat in a chair and this pretty young girl started working on me. Same kind of small talk. I found she was an aspiring Movie Makeup artist and had actually competed on Face Off which was exciting. Her name was Cindy.
"I don't normally wear makeup and really don't like it."
"I understand completely. Let me show you an invisible makeup technique and we'll use a muted rose lipstick. I think you will like the look."
We talked and before I knew it, I was looking in the mirror at a transformation I didn't know was possible. For lack of a better word, Beautiful.
That word had never in my mind, ever had an association with me. I knew I had makeup on but it didn't look like it. My lipstick looked like I had rosy lips from having just given a blow job. I couldn't even tell it was lipstick.
"Here, take these. You might want to do a touchup by tonight. If you want a lesson in the future, let me know, I'm here."
"Thank you so much, Cindy." I felt so good.
I walked out the door and into the car and I was surprised to see Maya. As always she was intimidatingly perfect. But this time, with no bra, a see-through blouse, and leather pants, I thought I could be a lesbian she was so hot.
"Hi, Penny." She said with a smile. "Do you like shopping?"
"Doesn't every girl?"
"I suppose so," with a chuckle.
We didn't talk much. I felt a little uncomfortable and awkward. Still intimidated.
"We're going to dress you for a wonderful evening with Gio." She said as we approached the store.
I knew it well having walked by many times admiring the sexy clothing in the window.
Maya got out and walked in and I followed like a puppy dog.
She said, "What size? 0?
"Yes, a zero or a one depending."
She pulled dresses off the rack like she had a personal relationship with each of them.
Into the dressing room, we went and she stood there looking at me. I realized it was my cue to strip.
I took off my top and jeans and stood in front of her my nipples hardening.
Maya looked at me and simply waved her hand toward me, "Common, it's not like I haven't seen you before."
I got out of my bra and panties and stood naked in front of her.
Try this on. It was a beautiful chiffon dress that fell maybe 3 inches above the knee. I saw myself in the mirror and it was lovely.
Maya wrinkled her nose and waved for me to take it off.
The next dress was a glitter Mesh mini. It had a slit up the leg past the groin. It was super hot. When I looked at myself I saw pretty much all of myself. I know it was supposed to be worn with nude undergarments but it was very daring with nothing on underneath. Very peek a boo. As I turned and looked in the mirror, at certain angles you were given the appearance of my nudity underneath. Very daring.
Maya smiled. "You look hot. And it's a perfect fit too."
I looked up to her, "Really?"
"Oh girl, I'd fuck you." And we both giggled.
"I'd like that," I said. She put her hand on my shoulder and it gave me tingles as our eyes met.
"Shoes," she said as she walked away and I got changed.
"Size? Are you a five?"
"Yes." As I sat.
She produced and slipped on a pair of five-inch stilettos. I'd worn heels before but these things were ridiculous. They made me feel like a balerina on her toes. And they were Jimmy Choo. That blew me away. Gio was buying me Jimmy Choo's!
"Paul, stop at Jason's on the way back," Maya said after we got in the car.
"One last thing I want for you Penny." She said.
We stopped and my heart sank a little as I saw it was a sex shop.
Maya was no more than 5 minutes and she showed me the package.
"What do you think about wearing these over your high heels?"
I looked at the ankle bondage restraints and simply said, "Oh yeah. I love it."
As we drove, she put her hand on my leg looking straight forward.
I just sat there and when we arrived she leaned over and kissed me on the cheek and said,
"Have fun."
"Thanks, Maya."
In the beauty parlor, Penny was surprised to find intuitive stylists who understood her needs, as Marcus, a manly man, trimmed her hair and made her feel elegant, and Cindy, an aspiring Movie Makeup artist, applied a flawless makeup that enhanced her natural beauty, making her look as if she had given a blow job without any apparent lipstick.
Later, Penny met Maya at the shopping center, who guided her through a selection of revealing outfits, eventually choosing a glitter mesh mini-dress that daringly revealed her silhouette, pairing it with five-inch stilettos and ankle bondage restraints, turning her into an alluring figure ready for an evening with Gio.