11 comments/ 24267 views/ 31 favorites Decent into Debauchery Pt. 01 By: LucidlyConfused Edited by Slavegirl70 ***** I woke up early for a run in the crisp air before the sun came up; it was the only way I could clear my head. I got dressed in a pair of tight shorts that were a bit small and a sports bra. Sure, the outfit was a bit revealing, but it was four thirty in the morning—who was up besides me? I began to stretch in the front yard as I thought about the previous night's events...so much vodka. I wanted to puke right there—and I would deserve it. I couldn't believe I drank so much; what had gotten into me? I tried to shrug it off and get on the road, hoping it would make me feel better—or at least make me feel a whole lot worse and cover my penance for getting so out of hand last night. A mile in, I was finding my stride and feeling better, so I began to replay the events from last night in my mind. I remembered going out with my best friend Chastity to celebrate her new job, and her boyfriend Kent was with us. Chastity and I have been friends since high school and somehow remained in close contact despite going to different colleges. We both made it back home after graduation and ended up moving in together while we searched for jobs. It was intended to be a short term thing but her job hunt took a whopping eight months longer than mine, so a celebration was in order. Kent was a good guy, a scruffy type—very outdoorsman and very fit, he was like a cross-country runner who was a lumberjack on the weekends, a comparison that always made me chuckle. They were actually together because of me, and while I was glad for Chastity I was a bit jealous he was taking her time away from me as I had gotten used to spending more and more time with her. I met him after a sign up for a marathon that we ended up helping each other finish only to have him be smitten by my best friend at the finish line. What guy wouldn't? She was gorgeous: a natural blonde with full B-cups, a smile to die for, funny, fantastic legs, a nice bubble for an ass and a heart of gold—in my eyes she was perfect. Mile two, and I thought back to the shots after Kent bought that bottle, and the dancing—oh my god. A wave of embarrassment washed over me as the mocking figure in my jumbled memories attempted to dance with Chastity and she made up for it by guiding my waist and keeping me in rhythm. She was better at everything; I was "the Brains" as she so eloquently put it on a regular basis, even though she was just as smart if not smarter. I was that girl that was somehow lucky enough to get paired with a friend that was a social butterfly when I was a recluse. She could have been one of the most popular girls in school, but her association with me may have prevented that—and I loved her for it. Now as adults I am still a bit shy and closed off but she helps me feel like I have a place. Mile three, time to turn around. The sun was just starting to add color to the horizon. I thought about the ride home, watching Chastity and Kent make out in the cab like they were going to have sex while the poor cabbie drove. I remembered not taking my eyes off them the entire time; I remembered them stumbling into the house still all over each other and pretty much ignoring my existence. I remembered feeling like she forgot I was even with her that night as I walked down the hall following the trail of lust in the form of discarded clothing. I remembered getting to my bedroom door only to hear cries of passion, which at the time seemingly were a siren's song. Mile four, I needed to get home. The memories didn't stop; I walked to her door and listened to her react to every thrust from Kent's well-toned body. I imagined what she must look like under him in the throes of ecstasy; I wondered what her breasts looked like supporting her nipples' quest to reach the ceiling. I wondered if she dug her heels into his lower back and if his cock caused her to paint his back in red hues, with her nails turning his body into a canvas of passion. I wondered if she lay there enjoying the drips of sweat falling on her skin like little hot pins sending pleasure directly to her clit, if her toes made fists and her abdomen gripped him for dear life. Mile five, the sun was peeking over the horizon and I was determined to beat it home. I remembered holding on to the doorknob for what seemed like an eternity, until I got the nerve to turn it and open the door slightly. The glow from the muted TV that had been left on illuminated their silhouettes and the sight before me took my breath away. She lay there with her head buried in the pillow, still able to make noise as if she was screaming into a megaphone. Her back was arched and her ass was thrust up into the air, giving Kent unprecedented access to her pussy, which he used very graciously. He held her wrists behind her back and thrust his cock deep into her over and over at a steady pace using full, deep strokes. He had full control over her, letting her wrists go only to plant a firm slap on her ass. Home at last I collapsed in the yard, having run faster than intended trying to fight back the emotions that accompanied the previous night's memories. The contents of my stomach revolted as I tried to catch my breath, completing the punishment for irresponsible intoxication. I had watched them both for over a half an hour as he played her body like a grand piano at the opera. He had full, rehearsed control over every second of the affair and that wasn't even what turned me on. It was her, it was how she pushed her ass back to meet his thrusts, how she moaned and screamed, how she begged and coordinated her body in the midst of complete surrender. Hearing and watching her orgasm was enough to bring myself to my own knee-shaking experience, but I couldn't stop watching, touching, wishing. I did a cool-down stretch and some crunches, feeling the remorse for what I had done to my best friend. I broke her trust by watching her with her boyfriend in their most intimate moments. But even worse, the nagging feelings in the back of my mind became very real last night. I didn't just admire Chastity, I didn't just like her—I loved her. I watched as she took his load all over her breasts and licked the tip of his cock, claiming the stubborn semen for herself. She scooped up and ate most of his cum for him, giving him that last image before he passed out next to her, exhausted. His cock was no longer a spear of powerful pleasure but a glistening testament to how amazing Chastity was. I wanted to taste his cock and I wanted to taste Chastity. I made my way into the house and into the shower after peeling off my sweaty clothes and grabbing a bottle of water. A cool shower should calm me down, I thought, as I continued following the trail of memories that brought shame to my conscious self. I watched her chest rise and fall and the slowly drying cum glisten in the low light of the TV. I surveyed the room one last time, attempting to commit the entire scene to memory when I spotted her discarded panties. I had only one thought in that moment and reacted before giving myself time to realize that what I was doing was stupid. I stepped out of my panties, which had wrapped themselves around my ankles, and crept into her room slowly. I grabbed her discarded undies from the foot of the bed and took them to my room, only to inhale her scent while finding my release once more. I stood in the shower stunned at my own actions. I had known for years I had feelings for Chastity but I also knew she would never reciprocate so I never pursued them in any way. What was I to do? I had to tell her...or I had to get this out of my mind and return her panties. Lost in thought, just standing in the shower, I barely noticed when the bathroom door opened. "Ugh! How could you have already run this morning? I feel like I fell off a cliff," Chastity groaned. I pulled back the shower curtain to see her in a pair of sweat pants and a bra, attempting to wash the hangover off of her face. "Yeah I feel pretty bad too, I can't believe we drank so much," I said, still watching her. "Good thing I don't have to work until Monday, this face would make a hell of a first impression," Chastity said, looking over at me and obviously feeling the pain. "There is no way I would let you drink that much if you had to work in the morning. I am not going to let you lose the job you just got, I can't pay rent alone forever." I picked at her, getting the smile I was looking for. "Hurry up, girl! I need to wash this filth off of me and I don't want to do it in a cold shower," Chastity said, sitting on the lid of the toilet, waiting, holding her head in her hands. I closed the shower curtain not wanting to see her face with my next comment. "Filth huh? I'm not sure Kent would appreciate you calling him that" "Shut up you nosy bitch," she teased. "You're just jealous because you haven't had a good fuck in months. If I wasn't such a selfish girl I'd let you take Kent for a spin, but since I am, you will have to settle for me helping you get laid by someone else." "Well, I don't want your hand-me-downs and I don't need your help getting laid. I can get myself laid just fine thank you very much," I said, grabbing a towel and stepping out of the shower wrapped up and dripping. "Whatever you say virgin, if you change your mind I am always here to help," she said, using the nickname she gave me in high school, for obvious reasons. She checked the temp of the water, dropped her sweats, took off her bra and quickly disappeared behind the shower curtain. In that moment I truly regretted not buying a transparent curtain, but reluctantly turned and walked out to get dressed in my room. I got to my door only to hear Kent behind me. "I take it you went without me?" He yawned. "Of course I did, I am not going to wait for your sleepy butt to get out of bed," I retorted, playfully turning around to see him only in boxers but sporting a prominent morning erection. "Your dick is none of my business Kent, wear pants," I said, halfway joking as I turned and walked into my room, closing the door behind me. I resumed getting ready for the day, pausing momentarily to hide Chastity's panties amidst my own until I could find an opportunity to return them without being noticed. I got dressed and grabbed my keys to get breakfast, since there was no way Chastity would be cooking and I needed to get away from her for a little while. I could hear the shower still running as I walked up to the bathroom door, so I opened it. "Hey, I'm going to Platt's for breakfast. You're on your own, be back later." "Oh ugh, yeah, yes ok, bye girl, later, ugh," she replied in a deep throaty moan. I froze. He was in there with her—they were at it again! I stood silent, waiting for my brain to tell me to leave, waiting for the feeling of shame to return. Instead I felt a familiar heat in my cheeks and dampness between my thighs. "Don't stop, she's gone," Chastity moaned, completely unaware of my presence. The bathroom was filled almost immediately with her moans of pleasure. I realized that he had to be eating his own breakfast and enjoying it a lot to elicit such moans from my friend. I slipped out of the bathroom and sat in the hallway next to the door, leaving it open slightly so I could hear every bit of what was going to happen. Her moans were intoxicating to me, guiding me to drop my shorts and fight back my own moans right there in the hallway—not ten feet from where I had done the same thing the night before. I was sitting in the hallway, shorts and panties at my ankles, spreading my legs as much as I could, while slowly sliding my hand up and down my needy slit. I imagined it was me on my knees in the shower with her, drinking in every bit of her essence while the water cascaded over me. "Uh god, just fuck me Kent!" she moaned. The next sounds were of his pelvis slapping against her ample backside and her acoustic soundtrack of pleasure. I was completely engrossed in the sounds of their lovemaking, pushing my fingers deeper into my pussy in rhythm with his thrusts and her moans. I lifted the front of my shirt and exposed my breasts pinching my nipples hard while I pictured the scene playing out on the other side of the door. "OOooooohhh...yeesssssssss...ugh yessss...mmmm, damn you make me come so good Kent!" she barely managed to articulate. "That's right, and don't forget it! Now bend over the sink, the water is getting cold," he replied, ready to burst himself. I heard her giggle and turn off the water and I slowed my own thrusts to prolong my own orgasm. "I want you deep, take me like this!" she moaned and giggled to her lover. 'SMACK' "God you have a fantastic ass, one of these days I'm going to fuck it," Kent said right before he began to enjoy her pussy once more. I had to assume she was on her knees with her ass up for him right on the floor. I looked at the door in front of me and saw the bathroom rug slowly sliding back and forth under the door with every thrust; she was right behind the door! With my clothes in disarray making it hard to move silently, I inched my way to the door and placed my back on it. I loved feeling this close to her while I touched myself; she had to be only inches away. She moaned and I bit my lip, she cried yes and my back arched, he thrust harder and I pinched harder. I was as much a part of this as they were and they were oblivious to me! That thought alone drove me over the edge. I came and came hard, biting my lip to keep from moaning, gripping the carpet and struggling to hold my breath. My legs shook while he continued his assault on her pussy; lightning bolts struck my sensitive clit while she moaned for him, all adding to the wave after wave of pleasure washing over my body. I quickly recovered and got up, knowing I had to leave before they finished. I stood at the door a bit longer on my wobbly legs just listening to him take her before I could bring myself to leave. Once in the car driving to the diner, the gravity of what I had done hit me once more. I did not want to be ashamed of myself any longer. I liked my friend. There, I said it. And just because she's the one I want to engage in a sexual relationship with, that doesn't make me a lesbian. I enjoyed listening to her and her boyfriend have sex, and as a matter of fact I would love to watch them again! That desire has to have a name... I sat down at one of the tables near the window and ordered my breakfast, then whipped out my phone to do some research. I had to figure out what my newly discovered obsession was called. I wasn't overly well versed in the language of sexual fetishes, but it didn't take me long to discover what I had been doing was called voyeurism. I read as much as I could about it and finally ended up on a forum for those with similar interests sharing their own personal stories. Some were a bit on the creepy side, however others were incredibly erotic tales of watching neighbors, patrons in nightclubs, and even couples in parks. I read story after story, not realizing that I had been sitting at the table for over an hour and my phone was beginning to die. I quickly paid for my meal and headed back home, only to discover Chastity and Kent were out. Fine by me I could use the privacy. I went straight to my room and opened my computer so I could continue reading stories of other peoples' exploits. While grasping Chastity's panties firmly in hand, I read intently for another hour before I decided I wanted to share my own story. I wrote about watching Chastity and Kent the night before, sparing no detail. I wanted readers to feel how I did while reading their stories. I felt myself getting damp revisiting my memory of last night in such detail, but I promised not to touch myself again until it was done. So I inhaled Chastity's scent off of her pilfered panties and went back to typing. Just as I finished and posted the story of my first voyeuristic experience my phone rang—it was Chastity. "Hey, what's up?" I answered the phone, while putting her panties to my face. "I need help, please tell me you are not busy," she said, sounding pretty down. "No, you know I always have time for my bestie." I attempted to lighten the mood. "I have no Idea what to wear for work, will you help me go shopping?" she asked. "Of course I will! Where do you want me to meet you? I am on my way." I responded, getting up from bed and closing my computer. "Meet me in the food court at the mall—and thank you! I have no idea what business casual means," she sounded relived. I laughed, "No problem. See you in about 15 minutes." I quickly hid her panties and changed my pants to go to the mall. I drove quickly, excited to spend time with my friend and secret lover, when my phone vibrated. I assumed it was her texting me to hurry, so I was all smiles when I looked at my phone, until I noticed it was actually an email from someone I didn't know. I waited to check it until I got to the mall parking lot where I could read without getting into an accident. The subject line simply read, "Well done." I did not recognize the name, all I could tell is that it seemed to be sent by a female. Hello C_Lover_43, Your story was absolutely intoxicating. I enjoyed it very much and your wording was impeccable. I truly felt as if I was there with you. I can tell you are new to this, but not just from the recent date on your profile. You are clearly enthralled with, yet so unsure of how to enjoy your newly discovered pleasure. I want you to know it is perfectly acceptable to enjoy watching others take pleasure in their bodies and it is even more acceptable to be attracted to your friend. It is also apparent that you are trying to come to terms with those feelings, and as a fellow watcher I wanted to offer some advice. If you want to watch even more, consider installing a small camera in your friend's room. They are inexpensive at most electronics stores and you can watch whenever you please. But be warned—you will ruin everything if you are caught doing this. Next, If you want your friend to become more than a friend, maybe stop treating her like a friend and start treating her like your girlfriend. Ease into it, but do the things for her you would want her to do for you if you were in a relationship. Get her things, give her massages, and take care of her with sincerity. I look forward to hearing more tales of your exploits and please feel free to contact me any time you like. XX Mistress T I was stunned; it was so much to take in. I was elated someone enjoyed my story, I was confused about my feelings on a camera and I was aroused at the thought of treating Chastity like a girlfriend. Who was this woman, this Mistress T? The name that came up on her email was Josephine Taylor, I started to respond to her but my phone rang just as I was about to hit "reply." "Hey, are you coming or what?" Chastity asked. "Yeah, I'm right outside. I'm on my way in." "You ok? You sound a bit off." I composed myself quickly and began to get out of the car. "I'm fine. It is just so sweet that you would invite me to come help you shop. You haven't asked me to do this in years; I am honored." I said with a playful tone, but meaning every word. "Oh hush girl, get in here," she giggled. I quickly made my way to meet her, my mind focused the entire time on Mistress T's words, wondering how I could treat Chastity like a girlfriend. I stared into her eyes while she rattled off the stores she wanted to hit up, and how she was stuck between buying work appropriate and sexy attire, when a compliment ran across my mind and out of my mouth before I had time to tailor it. 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. Decent into Debauchery Pt. 01 I think I did a good job tonight treating her like my girlfriend. I wore stockings for her and cooked her dinner and we had an amazing time together. You have been right about everything else, I hope you are right about me getting on my knees for her; just the thought of it has my hands gravitating away from the keyboard. I am wearing the stockings as I writ this, although it was not at your request. I already had them on for our dinner tonight. But I am wondering what you meant when you said, 'if you were right about me?' What else do you know about me that I don't? B I hit send and re-focused my attention on Chastity. She seemed to be having a hard time falling asleep, turning over and over. I enjoyed watching her, even her restlessness was a dance of beauty for me to admire. She was teasing me without even realizing it. I pinched one nipple and slipped two fingers inside my pussy and started a slow deep rhythm, just watching her fight for sleep and listening to my own breath. I felt my orgasm growing in my abdomen but I needed it to come slowly and hit hard so I removed my fingers and ran circles around my clit with my wet digits. My hips gyrated as I imagined lying in that bed next to her, touching her, pleasing her, being used by her; I wanted to be her object of pleasure. My breathing was getting deep and ragged when I noticed her hand moving under the blanket. I froze. Was she doing what I thought she was doing? Her hand was on her breasts, pulling at her nipples slowly while she seemed to look straight up at me. It seemed as if she was rounding the first turn on her pleasure coaster. I began to mimic her movements, joining in her quest for relief. My eyes did not avert from her as I learned how she enjoyed playing with herself, she started with heavy breast play before she even attempted to touch her pussy. She tweaked her nipples, twisted them, even licked them and bit them. She began to slowly tease her hand down her body while still pulling on her nipple and I leaned in closer to ensure I did not miss a single detail. DING! I almost jumped out of my skin; I was so focused on Chastity and her exploring hand. I clicked the message and let it open while I continued to stare at my secret lover giving me instructions on how to please her. I glanced over for a second to see the message when big, bold letters caught my eye. B, REMOVE YOUR HAND FROM YOUR PUSSY! Tonight is about enjoying the act of watching, you will not touch yourself you will only watch. You have an opportunity to truly dive deep into the world of voyeurism; do not dilute it with nonstop orgasms. I have no issues with you being crass; it is honest and therefore follows the rules. I am glad the two of you had such an enjoyable time. You must continue to do things like this at least once a week. It can be your sexy date night. As long as you have the stockings on when you reply to me I do not care what encouraged you to put them on. I care about rules being followed and getting to know my curious B. What do I know about you, I know that you immediately stopped touching yourself even though you hate it. I know you get wetter every time you get a message from me; I know your clit swells with the thought of doing as I tell you. What I know about you is what you are soon going to realize, you are submissive. Take some time and look it up and tell me if I am wrong. If I am right the next message you send needs to include a picture of your stocking clad legs. Good night B. XX Mistress T My hands were on the keyboard, my pussy was soaked, my dream girl was touching her pussy for me to see and I couldn't get myself off. I was conflicted. Was I a submissive? What does that even mean? I mean damn, I just got used to this voyeur thing and now I'm something else as well? I watched while her hand moved under the blanket and her mouth hung open while she worked on maintaining a rhythm of moaning and breathing. I felt my clit burn with the need for attention, only to be mocked by the first line of Mistress T's last email. I watched her intently, wishing I could join in her pleasure physically. Mentally I was with her, but of course it was a tortured pleasure not being able to touch her, or myself. Her orgasm was one of the most beautiful things I had ever seen. The way she writhed, the sound of her moans, the way her back arched and she pushed her nipples into the air...it was art in motion. She fell asleep soon after and with no other choice, I got ready to follow suit—completely frustrated and soaked. I lay in bed in the dark and I knew that from this point forward, my life would not be anything close to what it was a week ago. I had a secret girlfriend and a Mistress; my life was getting better by the day. As I smiled and began to drift off to sleep, I decided that tomorrow I would take some pictures for my Mistress and try once again to get into my best friends panties. DING!