Decent into Debauchery Pt. 01

"Psh...no matter what you wear you will be too sexy for work," I blurted.

Did she just blush?

"I know, but I don't need every girl in the building hating me on my first day!" she gushed, with what seemed like a false sense of bravado.

"Let's go, I know exactly where to take you for your first day outfit." I was attempting to recover and move on.

I locked my arm with hers and started walking, feeling incredibly happy to be this close to her. We walked into the store and I took her to the back to sit her down by the dressing rooms.

"Let me go pick out a few things and you can try them on, how does that sound? We'll do a fashion show!" I said.

"Ok, sounds good—this will be fun!" Chastity sat on one of the lounge chairs.

I went about picking up pencil skirts and matching tops, heels, comfortable dresses for Fridays and a few pairs of thigh high stockings and garters. I wanted her to look incredibly sexy but also fit in her new office without looking like a slut.

"Ok I have a few things here, but first we are going to try this out," I handed her a black skirt, sexy but classy black heels, a silky white blouse, and a set of stockings and garters.

"Uhm, wow! This looks like something I would wear to get laid. Who knew you had it in you? Now we just need to get you in this kind of stuff," she teased as I laughed and led her to the changing room.

I waited outside as she changed, waiting on pins and needles to see how she looked. I could see her putting on the thigh highs from under the door, she lifted one leg and it came down on the ball of her foot draped in smooth nylon. I felt heat start to form between my thighs as I sat there watching the six inches of space the dressing room allowed. I watched as both of her feet, one after the other, slid into the skirt and it disappeared upwards. I enjoyed watching her feet move and turn while she adjusted every part of her outfit. Then watching her slip into her heels was even more arousing than I imagined it would be.

Her feet turned to the mirror and her right heel turned outwards as she inspected herself, not saying a word to me.

"How does it look?" I asked, attempting to remain calm.

"Good actually, should I wear my hair up or down?"

"What do you mean, actually?" I picked at her, "I don't know about the hair—let me see it first."

I watched her feet turn around, the door open and she stepped out with two steps and four sultry clicks on the linoleum floor. She was drop dead gorgeous. I just sat there, taking her in, committing every facet of her beauty to memory.

"Well, say SOMETHING," she said, nervous and slightly irritated.

"You look AMAZING! Look at yourself, you look amazing. You are so ready for work and afterwards, a little fun on the side!" I said, standing up and turning her back to the mirror.

"You don't think this is too much?" she sounded concerned.

"No, It's fine! You look wonderful. Your outfit says, 'I am about business, but there's no reason I can't look good doing it." I said, provoking a smile from her.

"Thank you Brandi! What would I do without you?" she hugged me.

I inhaled her scent deeply while I hugged her back. "I don't know what we would do without each other, girl," I smiled.

"You should put on some of these stockings; I think you would look killer in them. You have those great runners legs," she said, letting me go looking down at my legs.

"Oh stop, I'm wearing jeans."

"So what? Take them off—I want to see what they look like on you. Come on, please? I did dress up for you..." she half whined, half begged.

I put up little resistance and walked into the dressing room. To my surprise, she walked in right behind me. It wasn't like we had never gotten dressed in the same room—hell we were both in the same bathroom while we took showers this morning—it just seemed so erotic in such a close space. She began to disrobe, putting her new outfit carefully back on the bench. I only needed to remove my pants and shoes and put on the stockings. I'm glad I wore decent panties today, I thought, attaching the garters.

"Oh yes. Those look excellent on you," she said from behind me, as I pulled up and attached the last one.

I turned around to face her only to notice she was down to her underwear and stockings and she looked absolutely stunning. I had seen her body over the years in various stages of undress and, as of recently, getting fucked, but it was nothing compared to standing in this small space dressed in what many considered lingerie.

"I would kill for those legs as long as I never had to run a day in my life." She said staring at my legs making me very moist.

"I would kill for your just about everything and still run every day." I laughed, trying to ease my own tension.

"Please girl, whatever! Here is the deal: I will get everything you picked out, but only if you get a few pairs of those stockings for yourself. Deal?" she asked, turning me around and looking at my backside, making me blush while watching her in the mirror.

"It's a deal. However everything is my treat. You deserve to get spoiled from time to time." I was remembering Mistress T's words.

"Oh my god, that is so sweet!" she said, hugging me once more. "You are the greatest friend! Can I at least pay for lunch? All this 'sexy' is making me hungry," she giggled.

"All this 'sexy' is making me another H-word," I responded too quickly to stop myself.

She immediately burst into laughter. "You are so right—Kent is going to get a workout tonight!"

Mentioning his name for some reason was like a punch to the gut, so I faked a laugh and began to get dressed, while she followed suit engaging in more talk about Kent and his sexual poweress. I wanted to say, 'I know girl, he does fuck you really good, but I could do so much better.' I wanted to say, 'Why don't you let me watch the two of you, since he is so good?' I wanted to beg. 'Please let me lick your cum off of his cock just once.' I wanted to say a lot of things, but instead I just laughed and made a few remarks about hearing them sometimes.

I paid for all of the clothes and then we had good conversation over a pizza, which I was going to regret when I ran in the morning. I made sure to subtly flirt with her and speak to her as if she was my girlfriend. I could tell she noticed at some points but just brushed it off, so I dialed it back a bit. After we ate we packed all of her new clothes into her car and she headed off to run more errands. I sat in my car and looked up the nearest electronics store. If she was going to brag about Kent, I was going to watch.

It didn't take long before I was browsing through security system cameras and a young man walked up to me, "How are you doing ma'am do you need any help, looking to beef up your home security?"

"Uhm, sort of. I have this neighbor and I think he is swimming in my pool when I am not home. So I only need one camera and I need to be able to hide it so I can catch him in the act." I blurted, surprised at my ability to come up with a lie like that off the top of my head.

"Oh, ok ,that is no good...well, in that case ma'am may I recommend this model here? It is discreet and wireless so there is no drilling required," he said.

"Yes, that is nice...does it have a night vision mode?" I asked.

"Oh no, If you want to go night vision and even motion detection you want this one here. It is a bit more expensive but it is smaller and comes with everything you could need to catch a trespassing neighbor and it comes with a two-year warranty," he said, confident he had made the right recommendation.

"Ok then, this is the one I want." I said, and with that I dove deeper into the dissolution of trust in the one relationship I cared about the most. But I had to see, I had to watch.

I called Chastity on the way home under the guise of me cooking dinner and needing to know what time she would be home. She gave me a couple of hours, so I put my plan into action as soon as I walked into the house. I unpacked the box and read the instructions, to ensure I got it right the first time. I installed the software on my computer and made sure it worked before I walked into her room and ran into the first kink in my plan, where do I hide it?

I sat on her bed trying to figure out where in the world I could hide this thing so I could see the bed clearly and nothing was coming up as a viable place to not be seen eventually. I flopped back on the bed, defeated; I should have thought this through before jumping to buy this stupid thing. This had to be a sign that I shouldn't be doing this. I thought to myself, when I noticed the vent above her bed. She kept it open because she loved to feel the air when she slept. I hopped off the bed and went to grab a screwdriver to take the vent cover off. I stood on her bed, took the cover off, stuck the adhesive side of the camera on the inside of the vent and screwed the cover back on. I laid down in her bed to see if I could see the camera and with a bit of determination I could make it out, but otherwise it was invisible. I rushed back to my room to check the feed. Minus the lines from the vent crossing in front of the camera, the feed was perfect; I had a complete and full view of her bed.

Satisfied with the camera placement, I opened my email and decided now would be a good time to respond to Mistress T, before I began to make dinner for my unsuspecting lover and her boyfriend.

Mistress T,

Thank you for showing interest in my story, the kind words were inspiring and motivated me to be prepared to write more. Surprisingly your assessment of me was correct, and to be honest it is a bit strange to have someone I don't know figure out so much about me from one story. I, however, don't know anything about you. I checked your profile it had very generic information and you have not submitted a story so that leads me to feel a little bit at a disadvantage. With all that in mind, would you like to tell me about yourself? I would like you to know I took your advice on both issues. I purchased a camera and it is now securely located in her room and I have been treating her like my girlfriend to the point that I believe she notices it. We went shopping today and shared a moment of intimacy trying on stockings, but it only led to her mentioning her boyfriend so I still have work to do, Wish me luck.

C_Lover_43 A.K.A. "B"

I read it a few times and changed some things around before I sent it. I wondered why I got nervous sending her a reply; she was a stranger, although she now knows one of my deepest secrets. I guess the real question was why did I feel so comfortable telling her? She could be a lunatic. I looked at the clock; I didn't have time to fret, so I went to cook dinner.

I had dinner made and the table set for three faster than I thought I would, so It left me time to put on a pair of the stockings Chastity liked so much under a pair of short shorts so the tops were still visible. I felt incredibly sexy in them, which it was amplified by the fact that Chastity asked me—no made a deal with me—to get them. She wanted to see me in them and I loved it. I was still admiring myself in the mirror when I heard the front door open.

"Brandi I'm home—dinner smells great!" She yelled from the front of the house.

I didn't say a word; instead I just walked out to greet her and waited for her reaction to my outfit of stockings, shorts and plain, black v-neck t shirt. I walked in on her in the kitchen, standing next to the stove, opening a pot and inhaling the scent of its contents, when she saw me.

She stopped in her tracks and put the lid down slowly as a smile creeped across her face.

"I love the way those look on your legs, but seriously, short shorts? No, that just ruins it. You have two options when wearing stockings, Virgin: a skirt or just panties," she said, still appreciating the way I pulled the look off.

"Well then, get ready for dinner; I assume it will be just the two of us tonight?" I asked, maintaining eye contact while pulling my shorts down and stepping out of them to reveal the thong I was wearing.

I tried to remain as relaxed and calm as possible like I hadn't just taken off my shorts at her request, like it wasn't a big deal.

"C'mon put those bags in your room and tell me about the rest of your day the table is set." I walked past her after kicking my shorts to the side.

She was speechless it seemed. She did not say a word, just went to her room with the bags and I began to wonder if I had gone too far too quickly. She took longer than I expected in her room so by the time I heard her coming back I had already fixed her plate and was full of nervous butterflies.

Should I put the shorts back on?

Did I upset her?

Why did I listen to that damn Mistress T?

God she is going to hate me forever!

My nerves were quieted the instant I saw her come around the corner to the dining room. She stood there wearing nothing but her bra, panties, stockings, garter, and a tall pair of red heels that completely contrasted all of the black lace she was draped in.

I love you Mistress T.

"Oh don't look at me like that; you started it. Tonight seems to be 'sexy dinner with the girls' so I made sure to dress the part." She said in a very comical tone keeping me on edge.

"Well, 'look the part' you do! And of course you had to one up me with the heels—always a competition with you, Chastity." I giggled, trying to hide my arousal. "Sit down, tell me about the rest of your day and eat with me."

The rest of the night went flawlessly with us talking back and forth about her exploits for the rest of the day, and with every glass of wine another compliment or admiration was admitted. I cleaned up the table and felt her eyes on my ass when I walked to the kitchen, she helped me with the dishes and I stole several glances at her breasts. We continued to talk and continued to drink after everything was cleaned up, continuing our conversation on the couch in the living room.

"So are you ready? You have been out of the workforce for some time now. I don't mean are you ready to work, I mean are you mentally prepared for what the workplace brings?" I asked, feeling like I was over-explaining my question due to the effects of my fourth glass of wine.

"I don't know any more really, I feel like I can do the work and that as a people person I will do well with my coworkers, but to be honest, I've gotten very comfortable with you taking care of me. I know I don't say it enough, but thank you for always being here for me and looking out for me. I mean what you did today was wonderful. You are going to be the reason I feel sexy and confident tomorrow, you are a true friend," she said with the utmost sincerity.

I scooted in close to her and wrapped my arms around her, pulling her to my chest and enjoying feeling the warmth of her body on mine.

"You know I will do anything for you; you are my favorite person in the whole wide world, Chastity, and I love you," I confessed to her—shocked at my own admission.

"That is so sweet Brandi I love you too." She hugged me back while leaving me with the feeling she hadn't really understood the true meaning of my statement.

"Go to bed girl, you don't want to be late on your first day," I said, looking into her eyes and brushing hair out of her face. "You are going to do great tomorrow, get some sleep." I kissed her on the forehead and immediately got up.

"Ugh, work! I don't want to go. Just be my sugar mama forever," she groaned, obviously playing while walking down the hallway in front of me.

"Only if you ask me nicely and start putting out," I matched her playful tone and placed a firm slap on her backside, followed by a barrage of laughter.

"Quit it," she laughed, "you're the one that needs to learn to put out, Virgin."

"I think I got it under control there, now go to bed."

"Masturbation doesn't count as getting laid..." she sang, disappearing into her room.

"Well, we're about to find out!" I said loud enough for her to hear me and walked into my own room.

I heard her laugh at my response and I immediately grabbed my computer and opened the camera program to watch her get in bed. I removed my shirt and bra and waiting for the feed to load, I noticed it had one saved video. It must have been from when she changed before coming to dinner! I resisted the urge to watch it now. The feed came on, a tinge of blue from her TV and only her shadow cast on the bed while she presumably removed her clothes and got dressed for bed just out of view.

I began rubbing my clit slowly through the thong just watching her elongated shadow move so eloquently. I was completely immersed in her every move when my computer let out a resounding DING! It was an email alert and it was from Mistress T. I moved the video of Chastity to one half of the screen and my email to the other half to read what she wrote.

B,

I was looking forward to your response. I knew it would not take long; you tend to be very easy to read even through messages. As you can tell, I am very good at gauging people. It is what I do personally and professionally, and just to add a bit of who I am for free, I am a lawyer. I will give you bits and pieces about me as we continue to talk but you must earn them with your honesty. You took my advice and for that I will offer you two more bits of information about me, first I am older than you. I can tell purely by the way you speak that you must be in your mid-twenties, which gives me at least a decade on you. Second I am very much a fan of women who enjoy the feeling of nylon against their skin.

I hope you have chosen carefully B. A camera in her room is very dangerous, but also invigorating. I can only imagine that you are watching it, touching yourself to her doing something completely non-sexual, just because you love the way it feels to secretly see her. Make sure you continue to take care of her. Be her girlfriend before she knows you are her girlfriend. Cook her dinner, offer her massages, give her compliments, do everything you see her boyfriend not doing. You will be on your knees for her in no time.

I have two rules for you and they are simple and will be easy to comply with, but I do expect compliance. One—I expect complete honesty from you at all times. Two—you will wear stockings whenever you reply to me. If I am right about you, and I believe that I am, neither of these will be a problem for you. Speak with you soon.

XX Mistress T

Everything about that message had me aroused and on edge. How was she doing this to me? She was absolutely right about me. I was doing what she said I was doing this very moment. I looked over at Chastity just now slipping into her bed, completely naked with the low light from the TV highlighting her curves. I slipped one finger under my thong and dipped it into my wet pussy. I re-read the message from Mistress T and knew I had to reply back to her soon, plus it would help prolong my own orgasm if I was typing in between rubbing myself. So I hit reply and began to type:

Mistress T,

You sound like a fascinating woman; I look forward to earning chances to learn more about you. I hope I can be honest with you. For some reason I have been feeling very drawn to you and I feel as if I can tell you anything. You were right about what I am doing right now; I am watching her get comfortable in her bed and she is completely naked. She looks amazing and the two of you are making my pussy leak. I apologize if that is a bit crass, as I have had a few glasses of wine this evening.