The Club Pt2 free porn video

## Foreword The reviews online were clear enough. Chez Catherine was a five star, white tablecloth restaurant. The black-tied waiter had sat her down at a small, candlelit table in the corner. A moment later, he brought her a bottle of sauvingnon blanc. "A bottle from Loire Valley, France. Compliments of Ms. Jillian, madam. She wishes me to inform you that she will arrive shortly." With a courteous nod of the head, the waiter turned and left. Kristen stared blankly into the flickering candle as she reflected on why she was here. Last weekend, she had received a mysterious letter from a woman who seemed to know a lot about her private life and personal affairs. Since then, her husband had not returned home and had not answered her texts and voice mails. She'd called into his office Monday morning to speak to him only to find that he'd taken a week of PTO last minute. "You didn't know? Your husband said that the two of you had a last minute family emergency," her husband's supervisor Lisa had said. "Oh, yes. Sorry. He wasn't home and I thought maybe he'd gone to the office out of habit this morning," Kristen had said, lying to cover for her husband. "I guess I'll try his cell again." "You guys are okay, right?" Lisa had asked with genuine concern. "Um, I. Well, yes, I think so," Kristen had replied, some doubt escaping in her voice. "I'll let him tell you about it when returns next week." Ever since then, Kristen had anxiously awaited this meeting. Where was her husband? Was he alright? How did this woman know so much about her home life and her affair with Matthew? Was she about to be blackmailed? These nervous thoughts and more milled through her head as she waited. She sipped her wine. It was considerably better than the grocery store wine she bought for her long baths. She'd always wondered what an expensive wine would taste like. Bordeaux. She'd always wanted to visit France. Did this restaurant really represent an authentic French cuisine, or was it just an Americanized version of French food? It occurred to her that she wasn't sure she could name a traditional French food. A few sips later, the alcohol filled her cheeks and ears with warmth. Her anxiety softened. Foie gras. There. That's one. As she adjusted herself in her seat for a third time, a woman with medium length almond colored hair approached the table. She wore a black overcoat which hugged her body tightly. Her hair, makeup, and heels were perfect. Kristen felt suddenly uncomfortable and small. Was her husband fucking this gorgeous woman? The woman diffused her worries with a real smile and approached her with her arms wide open. Drawn to her, Kristen instinctively stood and hugged her. "Jillian?" she asked hesitantly. "Yes, and you must be Kristen. Thank you for coming. I just knew you would. Please, let's sit." The two women ordered their food and chit-chatted about the inconsequential things that strangers discuss. The traffic, the weather, and how lovely the town's Christmas tree would be this year. Kristen was surprised at how much she just loved Jillian. This woman was calm and in control. Her style was impeccable. Her designer purse, her immaculate nails. She was, in a word, perfect. And yet, Kristen didn't feel threatened by her. More often than not, when Kristen was around other women--especially one as sophisticated as Jillian--she would feel an irrational sense of contempt which was ultimately rooted jealousy. Not so with Jillian. Instead, it was an irrational and pressing need to be noticed by her, even to impress her. After the plates were taken away, Jillian broached the elephant in the room. "Kristen, I'll just come out and say it," she said furrowing her eyebrows. "Your husband has joined a club dedicated to--shall we say-- um, sex." "A sex club?", Kristen asked, not quite believing the words coming out of her mouth. Her husband was in a sex club? "Yes. A sex club. My sex club. A very successful one at that. I'm the proprietor." Thoughts raced through Kristen's head as she imagined what her husband was doing. Who knows, even at this moment he was probably getting a blow job from some college age slut. The thought made her jealous, then angry, then sad. Had she caused this problem? She'd shut down her husband's requests for sex for years. Maybe he'd finally lost it and taken matters into his own hands. Though she felt betrayed, then remembered her own betrayal. Just last weekend, she'd spent Friday night having wild sex with her lover Matthew. She wasn't innocent, she realized. Was this the end of her marriage, her family? She sniffled and wiped a tear from her eye. Jillian reached out and took her hand gently. "Listen, your husband is happy. I can assure you of that. But you should know that you're allowed to be happy too. I want to help," assured Jillian as she gently squeezed Kristen's fingers. "How? What on earth could you do to make this right?" "I want you to join the club, too--as my personal guest." Kristen paused, not sure what to say to that. "Forget about him for now. Just come and have some fun, you might see something--or maybe some things--you like," winked Jillian. "I'll make sure that you two won't see each other when you come so you can get a flavor for the club." Kristen considered the offer. Jillian seemed so sincere. So far, she'd been trustworthy enough. Maybe this was the event that would spice up and ultimately save their marriage? "Well, I guess I will. When should I come?" ## Chapter 1 My refractory period was in hard swing as I sat on the edge of Mistress's bed and gazed at the floor. "I love being Mistress's slutty little girl," I had admitted through hot tears and clenched teeth. But, did I? Truth be told, I felt more than a little gross as I cupped the bra around my chest. It felt alien to me, as did the collar locked on my neck and my own dried semen covering my tummy. The thought of what had happened this morning was not exactly arousing to me. In fact, I couldn't understand how it had ever turned me on in the first place. I was a guy. A straight guy. That's how I saw myself. I was not a girl, or a 'sissy' as Mistress said. I looked down at my penis and wondered if it was actually smaller or if I just thought it had shrunk. The mind plays tricks sometimes. The door opened and Kitten walked in. She was clothed now. Actually, I realized that this was the first time I'd ever seen her fully clothed. She was a beautiful, um, girl. She wore a white ribbed tank top and pyjama shorts. Her blond hair hung gracefully over her breasts whose nipples poked through her shirt. "Looks like someone's feeling squicked," she said eying me. "Squicked?" I asked. She laughed playfully and sat next to me on the bed. "Hmm, how to explain it?" As she paused to consider, she put her hand on my knee. "I guess it's when you suddenly--and usually unexpectedly- -feel repulsed at a sexual act. You're clearly squicked right now. Mistress thought you might be." Repulsed. I would say that's exactly how I felt. She rubbed my thigh supportively. "Don't worry, I used to feel that way, too. You'll get used to it. In fact, you may even come to look forward to what you're feeling right now." Bringing her hand up to my crotch, she leaned in to my ear and whispered, "It's all part of being a sissy." My penis hardened--much to my surprise--and I was entirely too uncomfortable with this situation. She was now kissing the profile of my face and I couldn't bear it anymore. "I, uh, look. I think I'd like to leave. I think you might be right about the whole being squicked thing." Kitten pulled back and brushed her hair over her shoulder. She seemed a little pouty that her advance had been rejected. "Mistress thought you might say that. She says that you're welcome to leave for the day. You've had your session after all. "Oh, in fact, I brought you these." She opened the bag around her shoulder revealing the clothes I wore to the club last night. "Are you sure it's okay?" I asked. "Of course dear," Kitten replied. "Well, I'll give you some privacy." She gave me a loving embrace and left the bedroom, shutting the door behind her. After washing up a little and getting dressed, I was ready to go home. Leaving the club felt a little sad, I reflected. It was like going home at the end of a long-awaited vacation. Or walking out of a movie theater after viewing an anticipated film. I walked through the now empty lobby towards the exit when I caught my reflection in the glass of the front door. I still had the collar on. That wouldn't do. I couldn't leave the club with it on. I reached up to remove it and remembered it was locked around my neck. Damn, I thought. I walked back through the lobby to Jillian's office. She wasn't there. I walked back to her bedroom and to my relief, she was sitting on the bed--apparently waiting for me. "Forgetting something, hon?" she asked knowingly. "Come to Mistress." I hesitated. Despite my mixed thoughts and emotions, I still found Jillian intoxicating. Even so, this was all very sudden. I felt like I had fallen into a hole and that hole was going deeper and deeper. Sexual fulfillment, submission, forced femininity? A few weeks ago, none of these things were even on my radar. Where would this woman take me next? "Now, please," she insisted, tapping her toe on the carpet in front of her. I walked to Jillian and started to sit next to her. "No, kneel in front of me." I didn't really want to, but the truth was, I didn't really have a choice. The leather collar around my neck had to come off if I was to go home. Maybe I could have found a way to cut it off, but I suspected that Jillian would have dismissed me if I'd done that. So, I obliged her and knelt in front of her. "Put your head in my lap." I did so, and felt the warmth of her legs through her nylons. The sense I had cuddling after last night's sex washed over me once again. "I love being Mistress's slutty little girl," the words repeated in my head. "Kitten says she thinks you might need some time," Jillian spoke softly to me as she ran her fingers through my hair. "I want you to know that it's normal to feel what you're feeling. You have my permission to have tomorrow away." Now that I was with Jillian, I didn't exactly want to leave, but a sense of relief washed over me all the same. It would be good to have a break from all this. "This is what I'd like you to do: First, call in to work and take the week off. We have some important business to attend to, and I need your undivided attention. I trust this will not be a problem?" "No, Mistress," I said, my slave brain kicking in. "Good," she intoned enthusiastically. She slid her cold fingers under my shirt to rub my back. "Next, I want you to go to the hotel down the street. Room 302. I'll put the key card in your bag. "I'd like you to stay there tonight. You need to get away from here, but you're not ready to go home yet." "Why not?" Jillian laughed. "Dear, you're missing all your body hair and basically need to be wearing a bra. Do you really think you're ready to see your wife?" My face burned bright red. She was right. I might be able to hide my current condition to passersby, but there was no way my wife would fail to notice this. My butt was more plump, my chest was--well, it was larger. There was not a single follicle below my shoulder-length hair. And then there was my penis. I was actively trying not to think too much about that. Sensing my discomfort, Jillian pressed my face down hard on her lap. "Oh my, hon. It's going to be alright. You just need some time to adjust. That's all. That's why you'll be staying somewhere else for the week. "Also, I'll need your cell phone." "What if someone needs to talk to me?" "Don't worry sweetie. I'll monitor your phone. If something important comes up, I'll handle it." I didn't like the idea of Jillian keeping my phone. My options were limited though, and deep down I trusted Jillian. She raised my head up and kissed my forehead. "Okay, dear, let's get this collar off." With a turn of the key and a click, I was free. ## Chapter 2 The green light flashed and the lock beeped. I turned the handle and entered the hotel room which Jillian had prepared for me. She had chosen a nice enough hotel. It was one of those economical places, but still clean and spacious. The kind you see right off the interstate in suburban towns. There's something so comfortable about these kinds of hotel rooms when you first arrive. The hallway outside seems foreign, even a little scary. It's usually a dimly lit place with the occasional housekeeper or stranger. Entering the room fills you with a sense of safety. It becomes an island of security in a sea of unfamiliarity. I set down my bag and shed my clothes. I needed a shower. I had tried to clean myself a little at the club, but I didn't want to stick around too long for fear of being pulled into anymore activities. The tangy smell of my cum was still all over me. I felt gross. The warm water was amazing. I'd really needed this. I washed my smooth, hairless body and found myself becoming aroused. Mistress, err, Jillian had not sent me away with panties. I dared not touch myself, though. I felt certain that she'd know. I decided it would be best to leave my penis alone. Still, I found my mind wandering. Before long I was rubbing my thighs and my balls. My penis was right there. All I needed to do was just give it the lightest touch... I caught myself. If I came, then it would all be over. I was sure. Naughty thoughts flitted through my brain. I thought about Jillian's wet pussy lips and the intimate moments we shared last night. About her thighs and her warm hand on my head. I thought about Kitten's perky nipples. There was something about Kitten I found enticing. She was submissive and sweet, everything a man would want in a woman. Except, she wasn't a woman. Still, I couldn't help but think about kissing her neck and fucking her. She would moan in delight and smile knowingly into my eyes as she'd lean forward and whisper in my ear, "You're next." As I rubbed my wet chest and ass cheeks, my thoughts turned to the long, hard shaft of the purple dildo I sucked last night and this morning. I touched my neck, then wrapped my fingers around it and grabbed my ass. I longed for my collar. Sighing in frustration, I turned off the shower. After needing to leave the club so badly earlier, how did I find myself missing it so much now? Clean now, I dried off and exited the bathroom. I looked at my bag and realized that I didn't have any spare clothes--except the stinky ones I just took off. I looked around the room and noticed a pink garment and a note on the bed. Picking up the note, I scanned it carefully. --- Dearest, I've left you some clothes to wear this week. Some are for "in the room", and others are for "when you need to leave". I expect you'll know which are which. There are some other things in the room you might enjoy as well. XOXO J P.S. You've probably guessed already, but no touching! Be a good girl! --- I picked up the garment and found it was a silk nightie. What if I didn't wear it? She wouldn't be able to know that. I looked around the room and considered. If she'd already been here long enough to leave things in the room, then there could be cameras. I decided not to risk it. Besides, what was the harm? No one would see me. I slid the nightie over my shoulders. At first, it felt a little like putting on a shirt that was too long. At least until the spaghetti straps hooked onto my shoulders. I was definitely wearing a nightgown. I glanced in the mirror on the wall adjacent to foot of the bed. A sexy nightgown. Just like this morning in Mistress's bedroom, I found my feminine image sexual and erotic. I loved how my hair draped over the thin strap around my shoulders. The delicate white lace ribbon which wrapped underneath my breasts lent a sense of fullness to them. Turning around, I noticed the ribbon formed a cute little bow at the small of my back. Just above my plump butt. My hands were instinctively wrapped around my cheeks. I could feel their warmth underneath the nightie's silk skirt. I rubbed my breasts. It felt so good. "I love being Mistress's slutty little girl," I moaned aloud, trying the sentence out again. I wanted desperately to touch my penis. I lifted the skirt fold and saw it standing fully erect and was quivering excitedly. All it would take was just a little touch and it would all be over. I looked around the room again. "No touching," the note had read. Mistress was cunning and would certainly find it out if I disobeyed. I brushed aside the sexual thoughts and decided to lay down and watch TV. I turned it to the local news. It was strange to be in a hotel in my own town. The same familiar faces I saw at home were giving reports about weather, local crimes, and high school football. There was a knock at the door. I panicked and mashed the mute button on the remote. Maybe they hadn't heard me. The knock came again. "Ms. Jillian?" called a kindly male voice. "Room service. I'm here to pick up your laundry." That made sense. They thought that Jillian was staying here tonight. She must have ordered me laundry service. I came up with a simple plan. I would open the door just enough to give him my laundry. Then I would close the door. He'd be none-the- wiser. "Just--", I started to answer then stopped. In a higher voice, "Just a minute." I decided I better play the part just in case he saw my appearance. I slid out from under the covers and quickly put my dirty clothes into a plastic hotel laundry bag. Then, I cracked the door enough to pass the bag to the man on the other side. "Thank you, sir," I answered politely in a sing-song feminine voice. "You're welcome, ma'am," the voice answered. "Oh, it looks like I caught you before bed. I'm so sorry." I chanced a glance through the door crack and saw the tall, red-faced hotel clerk trying very hard to look at the floor. On my eyes' way to his face, I caught a glimpse of the bulge in his pants. Apparently, I had not only passed as a woman, but my appearance had turned this man on. I felt a strange mixture of relief, humiliation, and pride at that. "Uh, um. It's okay dear. Thanks for picking up our clothes," I said, implying that there was a man in the room with me so as not to raise any suspicions of my cross-dressing given the men's clothes in laundry bag. I awkwardly shut the door and let out a sigh of relief. This was going to be a long week. ## Chapter 3 I woke the next morning instinctively humping my pillow. My nightie was still securely wrapped around my body so my penis rubbed gently against its silk. With no body hair and the silk, there was virtually no friction. It felt amazing. I caught myself and stopped. It'd be best to get up. I put my feet on the floor and noticed a pair of fuzzy pink slippers. It was cold, so I slid them on. They were soft and wispy on my feet. What would I do today? I needed to call in to work and put in last minute PTO. Mistress was right. I could not show up to work like this. Also, I didn't normally do this sort of thing, so I was sure it wouldn't be a big deal calling in with such short notice. Beyond that, though.. I couldn't hang out with any friends. Maybe I would go see a movie? That'd be a nice Sunday afternoon. That said, I could not go out wearing a pink nightie and fuzzy slippers. The note had mentioned that there would be other things to wear for "when you need to leave". I opened the drawer underneath the ubiquitous room phone. A Gideons bible, pen and a hotel-branded notepad. I opened the drawer below that. My eyes widened in surprise. There was a stack of panties, a few bras of different colors, and an unmarked bottle of my tiny pink pills. Well, not that drawer. I considered taking one of the pills, but decided to stay focused on finding some clothes to wear. After all, I wasn't entirely sure about what those pills were doing to me. Maybe if I stopped taking them, some of these changes would revert. I opened the drawers underneath the TV. A few pairs of heels and collars, complete with locks. The next drawer contained some skirts and tops. Not that one. The one below contained some blouses and pencil skirts. Not that one either. I had three drawers remaining and I hadn't found my "going out" clothes. It started to dawn on me that maybe Jillian meant for me to wear women's clothing out. The fourth drawer underneath the TV contained some more nighties and chemises. My heart was racing as I opened the fifth drawer. Inside were a collection of unopened dildos, lube, assorted toys, and some porn DVDs. I raised an eyebrow at them, but noticed that there was indeed a DVD player in this room. I almost didn't bother with the last drawer, but I couldn't stop myself. Sure enough, no male clothing. It contained garter belts, stockings and leggings. Fuck. What was I going to do? I basically could not leave room. Not just for the movies, but also for food, or anything. I lay on the bed, closed my eyes and tried to think of a plan. I could wait for my clothes to come back from laundry. They should be back at any point. After all, they were picked up yesterday evening. I called the front desk. "Hello, reception." "Hello. This is room 302. Last night my clothes were picked up for laundry service. Do you know when I'll get them back?" "Ma'am, you must be mistaken. Our hotel does not offer laundry services." Did she call me "ma'am"? "Oh, uh. I see. Thank you, ma'am." I hung up the phone and slumped back onto the bed. No laundry services? Then who picked up my laundry yesterday? That was that. I was now stuck in my hotel room. I couldn't leave without being exposed. Then it hit me that maybe I could leave at night, when it was dark. Where would I go, though? All clothing stores were well lit, and anyone would be able to see me. I was out of options. Jillian told me I could have the day off from the club, but I decided it would be best if I went to there tonight. Maybe I could rush her to the next step so that I could get my freedom back. It was now noon. I called into the office and scheduled my time off for an unexplained family emergency. I hoped it would not make too many waves with my boss, Lisa. She was already not happy with my performance as of late. I spent the afternoon making the best of my day. I watched some more TV, and kept rediscovering that I didn't have my cell phone. When that got boring, the dirty thoughts came back. I played with my nipples and ass which is something I started to find so hot. I just loved the idea of being manhandled. Especially in my silk nightie. Moaning aloud, I entertained the thought of someone pinning me against the wall by my arms and groping my ass. Now thoroughly aroused, I put on one of the porn DVDs. It was relatively straightforward porn. It featured a young, seductive woman getting railed by a tall musclebound man. I tried sucking on one of the dildos as I watched him penetrate her and grab her breasts. I was so frustrated. My small dick was straining under the nightie as the porno ended. I teared up, then nodded off to sleep, dildo still in hand. I was awakened from the sensual nap by the room phone ringing, its light flashing red in the now dark room. Apparently the sun had set while I napped. How late was it? I pulled the receiver to my face. "Hello?" I asked. "Well hello darling," Jillian replied chuckling. "I see you're practicing your feminine voice." She was right. I'd answered in the same meek voice I'd used last night with the laundry guy. In fact, I'd used the same voice when talking to the reception desk earlier. And, shit.. Had I spoken that way when I left a voice mail for my boss? "I hope you've had lovely day to yourself," she continued. "Have you taken your pills?" I slapped my thigh in frustration with myself. I had not. "No, Mistress. I'll do that next. I'm so sorry." "It's okay this time. You've had a busy couple of days. Don't forget. Now, did you make any trips out today?" "No Mistress." She chuckled again. "Dear, you must be starving. Anxious about being seen outside in our girly new clothing, aren't we?" She paused for my reply. "Yes, Mistress," I answered meekly. Phone couched between shoulder and ear, I was now rubbing my nipples again. I already knew what was going to happen next. Mistress was going to find some way to make me wear my girl clothes out. "I have a deal for you. Come to the club tonight. The sexier and girlier your outfit, the better your reward will be. How does that sound?" At that moment, I felt a strange, full sensation behind my balls. It started as a warm, tingling feeling and I felt my anus clenching involuntarily. I'd never felt anything like it before. My face flushed and my ribs convulsed. A little whimper involuntarily escaped my mouth. Mistress giggled. "Having fun, girlie?" "I--" I said, trailing off as my body convulsed again and my arms fell away from my breasts. "No cum, right?" "No, Mistress," I said, my voice shaking. "No cum." I let out a contented sigh and fully relaxed. "It's okay honey. Good little sissies have those episodes from time to time. I'm so proud of you. Now, get dressed, then come to the club tonight for a reward. Okay?" "Okay, Mistress. I'll do it." What the fuck was I thinking? I swallowed a pink pill and got to work. What was the minimum that I could get away with wearing? I needed something that would show Mistress I was trying, while also not drawing too much attention to myself. I rummaged through the drawers again. There was not a damn thing in there that wasn't blindingly noticeable. Any of these "garments" would draw immediate attention from men and women alike. I came across a white satin blouse and thought it would be understated enough. Especially if I paired it with some blue jeans. An outfit like that was not too dissimilar to what I wore to work each day. Except a blouse instead of a button up shirt. Unfortunately, there were no blue jeans. That's when I noticed the tag hanging from the blouse. It read 2 points. Other pieces had tags a well. Looking at each of the items, I quickly deduced that the more audacious the item, the higher the assigned points. Mistress hadn't mentioned anything about points. Maybe they were how I be graded on my selections? I tallied up all the points I would gain from wearing some flats, some dark capri pants and the blouse. Only 4 points total. Any of the heels alone were worth at least 20 points. There was no way that Mistress would settle for my well below average selection. What if I swapped the capris for the tight black leggings? The leggings were worth 5 points. I tried them on and looked in the mirror. The leggings showed the curve of my ass, and the blouse sleeves flowered around my wrists and over my hands. There. I looked soft and feminine but still had my masculine dignity. After all, the leggings were a lot like slacks that were too tight, and the blouse was like a button down shirt. Still, my point count was only 8. That's when I noticed that my chest and nipples were visible through the blouse. Fuck. There was only one way to hide them and still get away with the blouse. I opened the drawer with the bras. White or black? They were both padded bras, and neither would fit into my blouse unless I unfastened the top four buttons. Ultimately, I landed on the white one since the black one would have been more visible through the blouse. No need to draw more attention. And with the bra and the open blouse went all my imagined masculine dignity. My chest was now hanging out for all the world to see. At least the bra was worth 20 points. The sight of the office slut in the mirror made my penis quite hard wrapped tightly in the leggings. That wouldn't do. The only way through this was to pass as a woman. There was no way I could prevent myself from getting excited while wearing this outfit. What if someone saw it? My cover would be completely blown. I remembered the stack of panties in the bedside drawer. A few minutes later, I was secure in my panties, and my penis was tucked in its downward facing compartment. My outfit was now worth a much more respectable 38 points. Absentmindedly, I found myself rubbing my breasts again. It was almost impossible not to. The blouse made them so obvious and provocative. I wondered if real women displayed the same behavior? The thought of a woman helplessly rubbing her breasts was incredibly arousing to me. I felt the fullness behind my balls again and my anus twitching. Just like earlier on the phone with Mistress. What was that incredible feeling? I tried to shake it off by focusing on my assignment. What would I look like in stockings? After all, it wasn't too much of a transition from leggings to stockings. I slid on a pair of black fishnets. They were worth 30 points alone. There was a problem, though. They kept sliding down. Ah, the garter belts. I slid them on and attached them to the stockings. Fuck it. I was now fully committed. Some combination of frenzied sexual excitement and expectancy of high reward propelled me forward in my task. I selected a tight, black skirt. It smelled of leather and made me feel amazing. As if possessed, I selected a pair of four inch heels and a black leather collar. Without a thought in the world passing through my empty little sissy brain, I locked on both the heels and collar. By the time I selected my accessories (an anklet, a dark red pocketbook, and a matching bow for my hair), my outfit was worth 235 points. I looked up in the mirror to admire my stunning image and ran my hands across my breasts and ass one more time. As the door to my room locked shut behind me, I realized the horrible mistake I'd made. My face flushed red with embarrassment as butterflies filled my stomach. What the hell was I thinking? I just dressed myself in a decidedly feminine outfit--and a slutty one at that. Being elevated an extra four inches, my body was proudly on display. I was practically spilling out of my shirt. If anyone saw me, there would be no way to hide myself. On top of all of that, I'd stupidly locked on the collar and heels. I didn't even have a key to those locks. I tried to calm down. The only way out is forward, I reassured myself, and started walking. A few steps closer to the elevator at the end of the hall revealed another mistake. I did not know how to walk in heels. My resolve was quickly evaporating as I struggled to walk forward naturally. There was no way I could hide my inexperience. The elevator opened up, revealing a young couple making out. He had her fully in his muscular arms and was kissing her neck. She purred as he ran his hands up and down her back. That all changed when they realized that someone else was in the corridor. On seeing me, they immediately stopped and tried not to make eye contact with me as they exited the elevator. The D-ring on my collar jingled as we passed each other. I heard the woman suppress a laugh through her nose. Was she laughing at the fact that they'd been "caught" or was she laughing at me? As if it were complicit in my humiliation, the elevator door shut before I could hobble inside. I pressed the down button. One Mississippi, two Mississippi... I could feel their eyes boring through my feminine facade, seeing me for exactly what I was. Three Mississippi, four Mississippi. The man murmured something inaudible. The door opened. I entered and quickly pressed the ground floor button. Just before the door shut, I made eye contact with them. They were standing outside 304 and she was whispering into his ear through cupped hands. Busted. They certainly knew. Sneaking through the lobby was a little easier since the clerk was away from the desk. On reaching my car I realized I would have to drive in my heels, but fortunately the club wasn't too far away. Before long I was safely inside. ## Chapter 4 Erica was waiting for me by the fire on an Italian leather sofa, reading a beauty magazine in the lap of her slender, shaven legs. Other than her, the club was empty. I learned later that the club was officially closed on Sunday nights so that Jillian could have her playmates and her establishment all to herself. She stood in surprise, her mouth wide open. Apparently, she didn't expect to see me like this. "Well, you look--just like a real sissy." She giggled watching me stumble awkwardly towards her in my heels. "I suppose we ought to go see Mistress," she said as she took my hand. Despite the embarrassment, I was grateful for the support. Tonight we were in the dungeon area of the club. It was a relatively large room with moody lighting and chilly air. There were various bondage tables and benches around the room surrounding an empty raised platform. I gulped as I tried to imagine what it would be like to be up on that platform on a busy night. Perhaps the most interesting feature of the room was a latticework of metal which resembled a spider web. Along the walls were several alcoves. Some were curtained-off aftercare zones. Others were sealed with locking cage doors. I noted one such chamber had curious holes in the adjacent wall. Noticing my puzzled expression, Erica winked at me gave me the blow job gesture with her fist, cheek, and tongue. She was leading me to a soft, leather table in the corner. Several bright white track lights pointed directly down on the table, harshly illuminating the forms of Mistress, Kitten and Katie. As they saw me approach with Erica, Kitten clapped her hands rapidly with glee while Katie held her hands over her mouth in shock. Mistress beamed with satisfaction at the sight of me. "Welcome back, honey," Mistress said with genuine happiness. "I'm so proud of you. You clearly win. I don't know how many points this is, but it's enough to win the biggest prize. Girls, bend her over the table and unzip her skirt. Let's finish her outfit." Suddenly, Erica had me in a tight grip by both elbows behind my back. I struggled to wrench free, but was surprised at how strong she was. I found I couldn't get leverage with these damn heels on. Before I could try again, Katie had me by my collar and Kitten was whispering reassuring words in my ear. "Don't fight it, it'll be okay. Just cooperate." She ran her fingers through my hair as Katie and Erica bent me over the table. "It'll be better that way. Shh, that's it. Breath deep." Someone unzipped my leather skirt and pulled up the flaps. "What's this? Panties too? Very good," Mistress cooed as she gave my right cheek a firm squeeze. "Delicious." I felt ice cold shears slip underneath my panties. With a couple of snips my panties were pulled away. My penis was throbbing underneath me. If someone would just touch it!? "Strap her on the table." Erica turned me around and lay me back on the table. Katie and Kitten attached Velcro restraints around my hips, wrists, and ankles. They were remarkably effective as I struggled against them. I could not pull myself free. The bright lights above us gave my captors darkened faces and bright halos. Mistress particularly looked like a beautiful demon or a sinister angel as she licked her lips in anticipation. "Leave the neck strap off. I want her to see her reward," she said with a cruel smirk. "Yes Mistress," obeyed Katie. Mistress unbuttoned my blouse and commented on my bra. "I see you went with the white one underneath a white blouse. Didn't want to look slutty? We all know you are, though. Right girls?" Then, she folded my skirt onto my tummy, fully exposing my penis. I lifted my head to see what she was doing. She ran her pinky down my chest and bald pubic mound, circling my penis. Then she hooked it gently under my balls--lifting them up and summarily dropping them back down. She bent over and gave the glans of my penis a little peck. I moaned. A combination of being sexually supercharged and having received very little pleasure over the last week caused the little kiss to almost push me over the edge. I thrust my hips up ineffectually against their restraint. "Girls, go get the box we discussed earlier. I need to have a little talk with my new slave." The three others trotted off silently and I heard one of the alcove's curtains open and shut. It was just me and my Mistress. She leaned over me, pressing her warm body against mine. She pulled the hair away from my eyes and stroked my face. "They're all fooled, but I know your little secret." Her voice was low and firm. "This is, in at least some part, a little show you've put on for us. You didn't come dressed like this because it was your idea, or because you really wanted to dress like a girl. Isn't that right?" That wasn't entirely true, was it? I'd selected some boring clothes out of necessity, but at some point I started picking more risqu? selections because dressing up was turning me on. "No, Mistress, I really wanted to dress like a, um, girl." The words fell flat in real time as I realized the truth. I was trying to persuade both of us that I wanted to look like a girl, but I didn't really believe it. Mistress's leather corset creaked as she chuckled. "You're not bullshitting me, honey. Let me tell you what really happened tonight: You left the club yesterday because you had substantial doubts about the transformation you're undergoing. Your worthless little 'penis', your budding breasts, your cute little ass, your lack of body hair, and now your growing desire for cock. You weren't so sure about it all and you had no plans to come here today, but you were scared of being trapped in your room and maybe a little bored. You really wanted to blow your load, but you were afraid that you wouldn't get away with it. "Am I right, so far?" "I--", I started. My anus was twitching again. "Don't deny it." I lowered my head onto the table and closed my eyes. The pressure was building up again. "Yes, Mistress." She was right again. It seemed that Mistress was always right. "Good girl. So, you decided to play my little crossdressing game and come to the club tonight. But, you tried to dress as masculine as you could get away with." I rolled my eyes behind their closed lids in hidden rebellion to her will. I felt her hands slip into my bra and a give my nipple a cruel twist. "Ouch!" I cried as I involuntarily fought against my restraints. "Look at me when I'm talking to you, sissy!" she demanded, twisting my nipple back the other way. I moaned as the pain of the twist turned into pleasure behind my penis. "Yes Mistress, I--" "When you realized you couldn't score any real points without choosing sluttier clothes, you carefully upgraded as necessary." She paused, scanning my eyes for truth. "So, then you come here and think you'll fool us. But you and I both know the truth. You're still thinking like a boy. Like a greedy, horny little boy. Aren't you?" Her pinch tightened. Tears started down my eyes as I sobbed another acknowledgement. "Well, I have news for you. You're not a boy anymore, and you'd best get used to it. You're a sissy. From now on, you're going to dress like a sissy, talk like a sissy, and act like a sissy. Anything less than that will be punished. Understand?" I was now sobbing uncontrollably. I didn't fully buy into what she was saying, but I couldn't deny that part of myself was truly willing. Part of me wanted to be her submissive little slut and do whatever she wanted. Yes, even to dress, talk, and act like a girl. I couldn't entirely comprehend how I felt about her, or my own identity, but deep down I knew she was speaking truth. "So," she continued, "until you fully accept your reassignment, I've decided to give you a very special reward." Mistress stood up again. "Girls, please come back now, 'Elise' and I are ready for you." Elise? Erica, Katie and Kitten now returned with Kitten ceremoniously carrying a black velvet case. She opened the case to reveal a tiny stainless steel chastity device--not a mere cage either. It was a solid steel piece. My heart started pumping. Erica lifted my head off the table with her hands so I could watch as Mistress rubbed clear liquid on her gloved hands. She gently took my hard penis in her warm hand. "There there, lets get you nice and limp," she cooed as I desperately thrust into her hand. Kitten kissed my forehead reassuringly. I felt my penis grow cold and numb as my erection completely dissipated in Mistress's grasp. It had shrivelled as if shrinking from cold. "That's right Elise, just let it go." Mistress took the device from the case. I couldn't feel any of it. It was horrible. One click signaled that the ring had latched around my balls. She slid the shaft of the much-too-small device onto my tiny glans. Another click signaled that the shaft was attached to the ring. A third click signaled the lock. "There, that's much better." ## Chapter 5 I had a feeling that my journey into complete submission to Mistress had only just begun. She had another special surprise for my "reward" tonight. She'd unstrapped me from the table and allowed me to grab some food from the kitchen and roam free. Free. Hardly. I was locked in collar, heels and chastity device. I couldn't be "free" without being able to leave. And, I couldn't leave without eventually facing complete humiliation. Sure, I could probably cut the collar and heels off, but that chastity device would require surgical precision to remove. The only safe way for it to come off was if Mistress allowed it. I sniffled as again I realized that these thoughts swirling in my head were proof that Mistress was right. I was resisting her. I was resisting complete compliance to her programming. Seeking to preserve my masculinity, scheming ways to avoid my humiliation, considering the risks of cutting off my outward signs of obedience. As long as I thought these things, I was at some concious or unconscious level disobeying her. This key understanding left me feeling completely powerless and emasculated. I was just "one of the girls". Now both physically and in name as well. Locked in the device, my penis and balls hung numb and lifeless below me. It felt so permanent. Like I had been neutered. Now the only way forward was to please my owner in hopes of reward. The thought made me feel impotent and horny and servile. Erica and Katie had gone to the lobby to wait for a guest. Kitten and I were instructed to prepare Mistress for her friend. It was inferred that this "friend" was a man and that Mistress would be enjoying time with him tonight. Ugh. The idea that she preferred the company of another man burned, but I couldn't help but feel useless. Mistress had inasmuch refused to let me fuck her since day one. Not verbally, but tacitly nonetheless. The fact of the matter was that she did not view me as a man, or even as an equal. My new chastity device further cemented that position. Kitten and I disrobed Mistress for her bath. Her body was beautiful in the nude, and I realized that I'd never before seen her completely naked. She had long, shaven legs and pedicured feet. A well-groomed tuft of dark hair framed her hairpin pussy. Her breasts and butt were pleasantly, but not excessively, above average in size. Her almond hair was pinned behind her head and tasteful silver earrings adorned her ears. Even exposed and vulnerable, she exuded confidence and mastery as she unpinned and let down her flowing hair. She was gorgeous. The masculine part of my psyche desperately wanted to grab her, push her onto her oversized bed and fuck her brains out. It would feel so good to slide into wetness and warmth, to grab her tits and to kiss her neck. My penis had started to harden. The blood flowing down there brought a "pins and needles" sensation. I realized that the effects of the numbness were wearing off. It was very uncomfortable, and yet somehow my pleasure was enhanced by it. The erection continued to grow in its trap until the pain from the restriction came. Then the erection left. A whimper involuntarily left my mouth as the feelings of pleasure and frustration struck simultaneously. "Naughty thoughts Miss Elise? Do what Kitten does. She's learned how to be a good girl by focusing on her assigned tasks." Kitten beamed with pride at the praise and started drawing the bath water. She clearly knew what she was doing. Over the next hour, she taught me everything about how Mistress likes to be bathed. "The water must be warm, but not too hot," she'd said. "Scalding water is bad for the skin. The soap must be lathered on slowly. Pay careful attention to her lady parts, but don't excite them. She prefers a sensual, but not sexual bath from her subordinates when preparing for a lover." Before long, it was time to dress her. Mistress had chosen a black, slit maxi dress that showed off her long legs and cleavage. Kitten helped her put on an elegant pair of black heels. She stood admiring her form in the mirror, beautiful and powerful. Katie and Erica had returned now. "Oh my god, you look absolutely amazing, Mistress," said Katie. "And that man out there," she stopped and placed one hand over her heart and flipped an invisible pancake off the back of her other hand. "He's just..." she trailed off. "I know!" said Mistress emphatically. "He's really something. A man among men." She paused and shot me sympathetic glance. "Oh, I'm so sorry Elise. I forgot you're still adjusting to your new role. I suppose you'd better get used to me talking about men. After all, I have some needs that my little sissies will never be able to meet." My face turned bright red and Erica stifled a laugh as I looked down in humiliation. Mistress turned back to the girls. "Why don't you and Erica take off for the night," she suggested. "Well, after you take care of the sissies." Katie eyed Erica with lust. "The work never ends," she said with a smile. "You ladies have a good night. Be sure to lock them in good before you leave. My date and I will be back in a few hours." Mistress left the bedroom, shutting the door behind her. "Okay, sissies. Until Mistress Jillian returns, you'll practice your cock sucking." I glanced over at Kitten who was already taking her blouse off. Katie pulled out two kneeling posts from Mistress's toy cabinet and set them in front of the bed. Katie paused, and looked at me quizzically. "Is something the matter, sweetie?" "Um," I started, confused. I looked over at Kitten. She'd now removed her leggings, bra and panties. Nothing was left, save her collar and chastity device. "Oh, oh. I see. I'm sorry, honey," she interrupted. "Let me explain. You and Kitten are going to spend the evening together sucking dildos. When Mistress returns, she'll decide what you'll do next. I know you have lots of questions, Elise, but for now I want you to be a good sissy and stop thinking. Your betters will look after you now." She turned to Kitten who seemed excited at the agenda. "Kit, will you please disrobe Elise? I think she may need some help taking off her new clothes. I raised my hands in reservation, but Kitten firmly and lovingly continued despite my weak protests. "Just do what Katie wants. Mistress put her and Erica in charge. Don't think, sweetie. Just submit and you'll find it's easier that way," she said as she unfastened and removed clothes. Before long I was wearing nothing except my bra, collar, heels and chastity device. "Leave her bra on," instructed an amused Erica. "It'll help her accept her new identity." She stood behind me and gave my ass a gentle rub and pat. My penis hardened inside its cage again. "On your knees, sissies," Katie ordered. I watched Kitten kneel on her stand's knee pads and then did the same. Kitten obediently placed her arms behind her back as Erica fastened them with a leather strap. With her shoulders back and her tits pushed forward, she looked like a slut ready for action. As I watched Erica fasten Kitten's collar to the post with a short chain, Katie grabbed my arms suddenly and fastened them behind my back. "Like what you see? Just think, honey, when I'm done with you, you'll look just like her." That was a real mind fuck. My cage closed unforgivingly around my penis. Looking down, I could see the curve of my bra-covered breasts poking out. Katie pulled my collar closer to the post and attached it to the post's chain. Then she pulled my hair behind me in a pony tail. Erica had now mounted what looked to be a 5" dildo onto the Kitten's pole and the sissy automatically put her mouth around it. Kit's eyes widened in panic as Erica pulled her chain even closer. I wondered if Kit had expected that and was always taken off guard, or if this was new for her. Erica hooked the chain in its shorter configuration with a carabiner. "Open up, sweetie," Katie said lovingly while holding a penis-shaped dildo in front of my mouth. I opened my lips in submission and Katie slid the tip in gently. Then she attached the dildo to the pole. My chain was left a little looser than Kit's. Even so, I found that the dildo was definitely in my mouth. It was dry at first, but before long my mouth had lubricated it with my saliva. After a few seconds, I found I could move my head up and down the shaft, but I couldn't take the dildo out completely. "That's it. Just empty your dumb little sissy brain and focus on sucking that cock. What a good girl!" Katie cooed as she stroked my lower back reassuringly. I couldn't turn my head to see Kit now, but I could hear her as she gagged and slurped on her dildo. Katie had now attached a wire from the back of the dildo underneath by bra. I couldn't see it, but she'd placed some kind of clamp onto each of my nipples. I'd always thought that nipple clamps would sting, but the pressure of these clamps was only enough to stay attached, and nothing more. Whatever they were, Katie had attached a third one to the spot between my balls and my anus. I could hear Erica whispering following by Kit jingling in her restraints as she grunted and moaned. Erica laughed and said aloud, "You need a few more?" "Oh, yes, please Ms. Erica. Please please," said Kitten, muffled through her dildo. I heard a few squeezes of a manual air pump, followed by a contented, guttural noise from Kitten. "You ready, babe?" Katie asked Erica. "For you, love? Always. Good night sissies. Remember: practice makes perfect!" ## Chapter 6 The lights cut out, the door shut. It was just me, Kitten, and our dildos in the dark. We couldn't talk, or even see each other. The bedroom was completely unilluminated. No lamps, no bulbs, not even an alarm clock. I considered that Mistress may have had a "no electronics" policy in her bedroom. That seemed plausible given the sundry activities which took place there. There was, however, the sound of Kitten blowing her dildo. For the last fifteen minutes, that's the only sensory stimulation I experienced. Slurping, gagging, and an occasional moan or whimper. I couldn't understand the attraction. Even if Kit were 100% into men and dreamed all day of sucking cocks it would be strange for her to continue with such persistence with an inanimate object for so long. Despite my apathy towards my dildo, her sucking and slurping and gagging were turning me on. The strange sensation of my mouth being penetrated against my will by this sex toy suddenly rushed over me. It was there, in my mouth. I couldn't escape it, and yet I felt secure and contained with it there. I ran my tongue along the bottom and felt the hard, silicone ridge of its frenulum. Then I pulled my head even further away from its base to its glans. The clamps attached to my body vibrated just a little. I whimpered in pleasure as I understood what was happening. The attachments on my body were rewarding me for servicing the dildo. Stuck in the dark with nothing to do, and being unable to leave or even sleep due to general discomfort, I found it difficult to not participate. Hell, the damn thing was in my mouth and I couldn't take it out. What was the harm in enjoying the pleasant feelings? The vibrations started again as I slid my head forward to its balls. I moaned onto the dildo as my saliva ran down my chin and onto my breasts and bra. Up until this point, the saliva had been kept at bay. With the movement, though, I was now making a mess of myself. I pulled my head back again and found the weak vibrations resumed. As long as I continued to pleasure the toy, the clamps would continue to pleasure me. Maybe that's what kept Kitten so fully committed to her dildo. After a few iterations of this, I realized that the vibrations were actually mild electrical currents. They felt like someone was gently and rapidly thumping my nipples and perineum with a mechanical precision. It wasn't long before I was greedily fucking my face onto the dildo. Every stroke of my mouth gave prolonged the pleasure just a little longer. I found I could increase the current by rubbing my tongue along the shaft as I went. Saliva was now running down my tummy and into my shaved pubic mound. I was wet all over as Kitten and I moaned and gagged together in the dark for a couple of hours. Even locked in my chastity device, my desperation to cum had reached its peak when the door opened and the warm light from the lamps turned on. It was blinding after being in the dark for so long, but I was glad to be able to see again. "What's going on in here?" asked a deep male voice. "Oh, these are my two little sissies," Mistress said with a smile in her voice. "They're practicing cocksucking tonight. You don't mind if they watch us, do you?" "Well, it's kind of strange, don't you think babe? Sissies are guys, right?" "Oh, hardly. I mean, just look at them," Mistress said, tugging my ponytail back. I found myself looking wide-eyed into the face of my Mistress's lover. He was a tall, fit man who was wearing a jacket and tie. That, with his salt and pepper hair and beard made him what most women would say was classically handsome. He squatted down next to me and cupped my breast in one hand and wrapped the fingers of his other hand around my neck. That caused the dildo to shift in my mouth which in turn sent a pulse to my clamps. To my embarrassment, I moaned involuntarily. I blushed as I realized that I just moaned because a man touched me. The thought sent a shiver down my back. "I see what you mean, I think this one wants me. Either that, or she's enjoying her activities a little too much." He took his hands off me and I found myself missing them right away. He stood and took his jacket off, throwing it on the bed. Mistress cupped her hands around his lower back and they kissed passionately. He moved his kiss down to her neck as she loosened his tie and unbuttoned his shirt. Underneath was a tight wifebeater undershirt. She pressed her body into his chest as he held her in his big, strong arms. She hooked her long legs around his, rubbing her thigh against his groin, as his hands went south to her ass. He slid them through the slit in her dress and grabbed her cheeks firmly. Mistress purred with excitement. I found myself incredibly jealous and intimidated. This lucky guy was getting to do what I wanted to do with Mistress from the beginning. And, for whatever reason, Mistress seemed to be really into him. Why not me? What made it worse is that she wasn't interacting with me at all. This was all about her pleasure, not mine. The feelings of inadequacy and rejection lit a spark behind my balls again. I sucked at my dildo with renewed enthusiasm. She looked into his eyes with intensity and sunk her nails into his chest as she squatted down in front of him. Then, she unfastened his pants and pulled them down to reveal a rather large bulge in his boxers. Her eyes widened in joy. "Mm," she intoned as she planted a kiss. She pulled his boxers down and out came his large cock. It was at least seven inches, but what was most impressive about it was its girth. She enthusiastically wrapped her lips around the monster and a fluffed it to peak hardness. He placed a hand into her almond hair and firmly guided her head. Content with its hardness, she looked up at him longingly, then stood again. He pulled the straps off her shoulders and peeled off her dress. Then he picked her up and lay her down on the bed. As he slid in, Mistress howled in ecstasy. I realized that I could never do what he was doing. Even when I was full "man", I never made my wife feel like that. The thought ate away at me, simultaneously tearing me down and turning me on. I pushed my dildo deep into the back of my throat. The subtle thumping sensation at my nipples and taint continued as I gagged, but nothing I did was quite enough to push me over the edge. I watched as the man thrust his hips back and forward, his well-toned butt flexing as he went. Mistress was gasping and wailing now as he shoved his cock deep in her pussy. She squealed in delight with each undulating motion, her fingers wrapped around his abdomen. This moment of protracted paradise stretched out for at least half an hour. Everyone in the room on the edge of orgasm, but nobody able to reach it. Simultaneously heaven and hell without end. Then suddenly, it was over. The man and Mistress convulsed together as she cried from joy. They lay quietly with each other for a few minutes and cuddled. Kitten and I continued sucking. After a few moments of silence, Mistress whispered to her lover. "I don't see why not," he agreed. He helped Mistress out of bed as she limped over to Kitten. I stopped sucking a moment so I could hear what was going on. First a click, then some jangling metal. "Kitten, be a dear and clean us, will you?" said Mistress hoarsely. "Yes, Mistress," said Kitten. I heard some more slobbering and sucking as presumably Kitten sucked the cum off the man's cock and out of Mistress. "Good girl. Thank you Kitten. Why don't you and Elise have a sissy sleepover at the hotel tonight?" Mistress stood in front of me now. "You don't mind having some company tonight to keep you warm?" suggested Mistress with a smile. I shook my head no and whimpered as and more current pulsed through my body. "Excellent. I have one more task before you leave, sweetie. So that you don't feel completely left out, that is." She unfastened my carabiner and chain. As she removed the dildo from my mouth, a flume of spit came out and covered me. My jaw ached and I realized that my knees were hurting, too. "Can you give his balls a kiss and thank him for fucking your Mistress?" she asked lovingly as she unbound my elbows and let my hair down. My cheeks burned with humiliation. The man's softening, but still-hard cock was now in front of me. It was glistening from cum, saliva and Mistress's juices. "Go on," he said. "Do as your Mistress says." He put his hand behind my head and guided my lips to his scrotum. His balls were big and heavy. They smelled of sweat and sex. If I weren't so turned on, this would have been gross, but I couldn't help myself. I was now giving his balls a passionate, drawn out kiss. They felt warm and soft and firm on my lips. He released my head, the side of his cock rubbed against my ear and cheek as I pulled away, leaving a trail of juices. "Thank you, sir, for fucking my Mistress." ## Chapter 7 It was two o'clock in the morning by the time we had left. I put my clothes back on, thankful to have some measure of modesty again. It's hard to explain how weak and vulnerable I felt in front of a man-- well, in front of a man like THAT. He was everything I was not. Tall, strong, hairy. Nice, but not a pushover. Gruff, but not aloof. He seemed to be completely on top of the situation around him. Able to inspect and adapt to curve balls. Mistress was clearly taken with him. Her chiseled authoritarian exterior melted away when he was around-- turning her into a sweet lovestruck girl. When I shut the door to the bedroom, Mistress was flirting and laughing with him under the covers as he tickled her. If I was honest with myself, I had to admit that I was a little taken with him, too. The way he'd fondled my breasts as he looked into my eyes. When he forced me to kiss his balls, I felt like a little whore for him. Kitten drove us back to the hotel in my car. The reception clerk gave us a strange look as we clomped past her desk in our heels. I was too tired to care what sordid thing she thought we'd done or might do. Besides, she was right. Now we stood in front of my room. With a beep, the door opened and in we went. Home. Or at least, "home away from home". And I felt safe with Kitten. I felt certain she wouldn't violate me the way the Mistress or the other girls would. Kitten pulled a key out of her wristlet and unlocked my heels. She explained that the collar had to stay on tonight because Mistress expected it. We were too tired to clean ourselves up and opted to go straight to bed. I curled up next to her warm body and spooned her. My chastity device nestled in between her cheeks. Her hand reached back and stroked my hairless legs and I kissed her shoulder and she contentedly snuggled her back to my breasts. I don't know what I expected to do with her. We couldn't fuck because of our chastity devices. Even if we didn't have them, would I be comfortable fucking another guy? Was I gay? My thoughts turned to earlier when I'd submissively kissed another man's balls. No, I'd been forced to do that. And, the only reason I was into Kitten was because I found her exquisite feminine features incredibly attractive. I cupped her breast and ran my hand down to her locked up penis. Like mine, the device was solid steel. There was no way she felt any pleasure from my touch. There was a ring at the tip of the device. I realized that it must pierce through her penis in order to hold the device in place. My device was held in place by a ring around my balls. I decided I'd best not play around with the piercing. My hands went further down where her balls used to be. "You must be hornier than you are sleepy. You like my little clitty Elise?" I took my hand away, but she grabbed it and put it back. "No, go on, please. You can play with it. It doesn't hurt. Just be gentle." 'Clitty' was a good word. It was very small. Her chastity enclosure couldn't have been taller than half an inch, making the ring coming out of the tip bigger than her 'penis'. "It's called a Prince Albert piercing. Mistress had it installed early on for not taking my feminization seriously enough." she said, pausing to giggle. "As you can see, that's not really a problem anymore. Now the piercing is used to hold the device in place since I had my balls taken. The device itself blocks all stimulation, just like yours." "Can you even cum?" I asked, not having ever considered the question before. "Of course," she said. "It's been a while, but the last time I came, I made a big mess." She paused, as if holding something on the tip of her tongue. "What is it?" "Well, it's just that I can't have children now," she said quietly. "That's the only drawback." "Oh," I said feeling bad now for pressing the point. "Hey! You asked, dummy. Besides, I knew what I was getting into. Mistress was right. I was just a little girl. I didn't need my balls anymore anyway," she said turning around. She smiled at me and kissed my lips. It was a long and passionate kiss. I felt my penis harden in it's prison. I involuntarily started thrusting at her and our steel enclosures clanked ineffectually against each other. Being with her was a strange, yet not entirely unfamiliar feeling which I couldn't place. The smell of her hair, the taste of her lips. Her smooth, firm ass in my hands. She ran her hands up and down my naked breasts, and she kissed each one. The sexual frustration was real. I understood why Mistress had us locked up now. As if reading my thoughts she kissed me again, then she turned away and fell asleep in my arms. The next morning I awoke in spite of the room's light-blocking curtains. Kitten was drawing a bath for us. Being a sucker for the comfort of daily routine, I've found that I'm rarely excited about the prospect of taking time off. It disrupts my schedule and causes me to miss my planned goals. That said, I can honestly say that vacation is critical for self-development. It is precisely the act of breaking out of that comfortable routine that causes us to re-evaluate the current state of our lives. Vacation is a chance to make room for the unexpected. To entertain the possibility that life could maybe be different, or better. In looking at these last few days, I would say that leaving room for the unexpected is just as important as any planned objective we might commit to. These thoughts ran through my head as Kitten lowered her naked, lithe body onto mine. Displaced, the warm bathwater rushed upwards to cover us. Never in my wildest fantasies would I have ever imagined spending my vacation like this. She lay against me in the tub and I kissed her head affectionately. Lovemaking in mutual chastity is a difficult endeavor. It's an exchange in sadism and masochism where each lover is simultaneous the victim and the victimizer. She stroked my neck. I kissed her lips. Each reciprocation was a sign of affection, a plea for help, and a subtle act of revenge. She sucked my nipple. I humped her thigh. At the end of it all is a mutual recognition of the shared burden. Both slaves, neither of us were in control of our own fulfillment. Mistress, a goddess both loving and ruthless, held the keys to paradise. Even so, I could tell that Kit was holding something back. It was clear that there was a line she that she could cross, but was unwilling to do so. At least not yet. That whole week was a blur of pleasure and frustration. I spent my days dressing up having short sessions at the club. I spent my nights curled up next to Kitten in our hotel room. ## Chapter 8 On Thursday at what would typically be my lunch hour, Kitten and I drove to the club for my mandatory daily session. She led me through the lobby and down the guestroom-lined hallway. My heart sunk when I realized that this time we were not going to Mistress's bedroom, but rather to the exam room. I'd not been in there in over a week. Since that point, my relationship with Mistress had become more familiar and personal. The exam room felt like a step backwards and I now felt irrationally nervous about what might be coming next. Kitten held the door open for me as I entered. Mistress was inside adjusting her hair and makeup in her compact. She did not stop to acknowledge me. Before Kitten could shut the door, she called, "Stop." Kitten paused and looked inside expectantly. "You'll be joining us today Kitten," said Mistress ominously. "Yes, Mistress." Kitten entered and closed the door. "You sissies seem to be getting along very well. Come here. Both of you." Kitten and I approached Mistress cautiously. Something about the tone of her voice filled me with dread. I looked at Kitten, who also appeared suddenly concerned. "She can't help you, honey," Mistress said to me curtly. "I'm surprised you haven't figured that out yet. Remember what we talked about the other day? Stop thinking like a boy." I wasn't really sure how to respond. How was I thinking like a boy? I'd dressed en femme for the last few days, complete with bra, panties, and stockings. When I wasn't in feminine clothes, I had to contend with my breasts which I couldn't help but touch and fondle. And this stupid chastity device blocked me from even playing with my penis. How could I be any less masculine? "Mistress, I don't understand. What am I doing wrong?" I asked with an unexpected note of desperation escaping. I was confused, but I had a sense that Mistress was serious. I hadn't intended to disobey her, and I didn't want to even have the appearance of doing so. Surely there had been a misunderstanding. "It's simple. You're falling for her and you're starting to think of yourself as her 'boyfriend'." Kitten and I unwittingly unclasped our hands. We'd apparently been holding them since Mistress called us to her. I turned again to look at Kitten who was now trying not to make eye contact with me. Fuck. She was right. I was in love. Well so what? Can't I be in love with her? Mistress chuckled, and repeated "You're thinking of yourself as her 'boyfriend'. Isn't that right?" And she was right. That's exactly how I felt. The last time I felt this way was with my wife years ago. I used to feel so big with her curled up in my arms. I'd stroke her hair as she would nestle her head under my chin and rub my chest with her hand. That was a really good feeling and there was a part of me that longed for that kind of connection again. Kitten had rekindled in me that feeling. I suddenly felt uncertain of the person I was becoming and ashamed of what I'd allowed to be done to myself. In my shame, I found myself crying again which further compounded these feelings. These fucking pills. "There, there," Mistress consoled. "You two little sissies can have all the fun you like together after you've been fully broken." She slipped her pinky into the D-ring of my collar and pulled me close to her face. "And, I'm the one who decides when that's happened. Your 'girlfriend' is, but I'm afraid that you're not little Miss Elise. "And, your 'girlfriend' knew that, too," she said turning to Kitten. She wrapped her other hand sternly around the poor girl's jaw. "We talked explicitly about your role as Elise's friend. You were not to entice her. Do you remember?" "Yes, Mistress," said Kitten apologetically. "I'm so sorry Mistress. I just--", she stopped as Mistress shushed her. "Shh shh shh. It's okay dear, I know it's hard for little sluts like you to hold back when you're around cock--not that little Miss Elise has much of one anymore," Mistress said looking at me sympathetically. "This is how we'll fix it, ladies. You're both to be punished in front of the guests tonight. I've put Katie in charge of executing the punishment as I have a prior engagement this evening. If I hear a positive behavior report on your performances as good little sissies, then I'll let you be girlfriends. If you perform badly, though, one or both of you will spend a few days reflecting on sissyhood downstairs." Kitten visibly gulped underneath Mistress's clasp. "Now, Miss Elise, be a good girl: strip and get on the table." As I peeled off my tight gray leggings, I noticed that Kitten, too, had quickly snapped back into her submissive role. Without having to be asked, she opened a little black case previously located on the nearby counter-top. Inside was a bottle of the clear solution I'd been receiving by needle the last few weeks. By the time I had assumed my hands and knees position on the exam bench, she had filled a syringe with the cocktail. Kitten, still avoiding my eyes, was firmly intent on fully obeying Mistress. It was as if Mistress's observations had flipped a switch in her mind and she was now awake and aware of herself. I tried again to make eye contact, but she carefully looked away in a display of dispassion. She was tearing up. Mistress wiped my left butt cheek with a swab. "You see Miss Elise? Kitten understands her role. You'll soon learn yours." As we waited awkwardly some long seconds for the chlorhexidine to finish disinfecting, Kitten began to sob. I felt the little pinch of the needle followed by the familiar slow burn of the syringe plunging the mystery drug into my body. "Did you take your pink pills today?" Mistress asked me, now ignoring Kitten. "Yes, Mistress." She unlocked my chastity device and pulled it off. God, it felt so good to be free. Even though it was the first time I'd been unlocked in 5 days, my penis had not hardened. It hung below me puny and soft. "Kitten, clean her clit and replace her belt." "Yes, Mistress," Kitten said, sniffling, as she grabbed some wipes. "Be gentle but quick, she's very horny. I don't want her cumming." Kitten's little fingers pulled my heavy balls aside and wiped underneath and around them. I never knew just how good having my balls caressed could feel. She worked the wipe up and around my penis. Then it was over. With two clicks my chastity belt locked in place again. "That's very good," said Mistress patting Kitten's butt affectionately. Then, she cupped my balls and chastity device in her hand and gave them a gentle squeeze. "Despite your acting out Miss Elise, and YOUR disobedience Miss Kitten, I'm still very proud of both of you. "Now, clean up a get ready for tonight. Why don't you help each other pick outfits?" A half hour later, Kit and I stood in the boudoir. "Mistress knows best," she said as she thumbed through the outfits hanging in the closet. I tried to give her a reassuring hug, but she pushed me away. "Look Elise, I think it would be best--right now--if we weren't physical. She was right about me, and she's right about you." She paused and sighed. "She's really good at reading people." I stepped back a little to give her space. Even though her spirit was broken, I felt mildly encouraged. If Mistress was right, then that meant that Kitten had a thing for me. As a man that felt really good. She seemed determined to find a sufficiently embarrassing costume for me to wear. Little black dress? No, too assertive. Sailor girl? No, too nerdy. School girl, cheerleader? No. Too juvenile. She huffed as she continued through the racks of clothes. I couldn't tell if her zeal was motivated from sadness, guilt, or fear. She rolled her eyes as she pulled out a French maid costume. "It may be a stereotype, but it's also a classic," she mused. It was a two piece uniform. The top was black and lined with white tulle. It was held up by thin straps which connected just above my breasts with cute little bows. Its shoulder-less sleeves wrapped around my skinny upper arms. The skirt hung just a little too short below my exposed midriff. It, too, was lined with tulle and sported a decorative white lace apron. "It's not quite right," she thought out loud. "I know!" She placed frilly white lace cuffs on my wrists. Then she slid a pair of white stockings up my legs. "Perfect!" she said, putting on her brave face. She seemed to be feeling a little more encouraged now. She selected a pair of heels and locked them on my ankles. Then she applied makeup. Though this was my first makeup experience, I could tell she was making it look as slutty as she could. Bright red lipstick, too much blush, and excessive eyeshadow. Finally, she put pigtails with bright red bows into my hair and attached a black leash to my collar's D-ring. "There, all done," she said taking my hands in hers. Her touch was electric. She looked into my eyes with a mixture of longing and compassion. "Look, don't worry about the punishment tonight. I've learned to just pretend like everything is alright and carry on like normal. When it's time, it's time. Just try to relax, go with the flow, and enjoy yourself." At that moment, Katie clomped into the boudoir accompanied by a tall man wearing nothing but a black leather collar, a hood, and some arm/leg cuffs. Katie herself wore a similarly styled corset and skirt. Her breasts were hardly contained behind the laces, but I found myself staring at the man's cock. He was a show-er, I reasoned, given his cock appearing thick and meaty even in its flaccid state. His thin foreskin wrapped tightly around his glans which served to highlight its helmet shape underneath. I caught myself wondering what it would feel like in my mouth which caused me blush involuntarily. I turned my head to hide the embarrassment, but remembered that my makeup was already hiding it, and that caused me to blush even deeper. Katie laughed at me as she noticed my unease. She was clearly empowered by Mistress's absence. "You look adorable when you're cock hungry, Elise. And, I'm sure Mistress will find your outfit delightful. How does it make you feel, honey?" "Like a slutty maid, Ms. Katie," I said not able to make eye contact with her. "Can you please say that in a higher pitch, and more enthusiastically? Mistress wants you to start sounding like a girl, too, from now on. "Yes, Ms. Katie, my outfit makes feel like a slutty maid," I repeated in my feminine voice. It felt only a little unnatural. "Tell me how you love your outfit, sissy. Say it like you mean it." "Oh, yes, Ms. Katie, I love my girly little outfit," I said, acclimating to the voice. "Ladies, guests are starting to arrive. Here's what's going to happen tonight. Because Kitten was willfully disobedient, her punishment will be more severe, and so she'll go on stage first. Until then, Elise will be on barmaid duties." She turned to the man next to her and gave the head of his cock a little tickle. "Adam, why don't you take Ms. Kitten downstairs and cuddle with her until the dungeon is ready for her figging. At this Kitten's eyes widened in horror, and the man grunted as he grabbed her by her pencil-thin biceps. The sight of her struggling in his big, strong hands was extremely arousing. It wasn't because of Kitten, though. Don't get me wrong, Kitten is sexy creature and I love her. It's just that I couldn't help but think of myself struggling in his arms trying to get away. He grabbed her collar with one hand and wrapped his alternate arm around her waist. Then he pulled her ass first toward his body, his large cock pressing against her. Kitten was now gasping. I was sure that it was from excitement and not because her collar was choking her. Katie approached her and gave her face a sadistic caress. "This is not going to be pleasant for you, dear. But, maybe you'll learn a lesson tonight." She gave Kitten a little kiss on the cheek and Adam carried her out of the boudoir. Katie turned to me. "Ms. Elise, why don't you run along and entertain the guests. I'll come get you when its your turn to join Kitten." ## Chapter 9 To my chagrin, the dungeon was full of guests. Various cliques of men and women--both tops and bottoms--stood (or in some cases crawled) about the room. Despite being just one more piece of meat among such a crowd, I felt exposed and on display in my French maid uniform. I could feel eyes leering at my tits and searching for evidence of my locked up clit. I hobbled toward the kitchen--ostensibly to get a tray--but really it was to hide. "Why are you in here? Get your ears on and get out there, sissy," said a voice over my shoulder. I turned to find Erica, who was standing next to a server station. She was holding out a pair of cat ears and a tray. I grabbed one of each, putting the ears on my head. My cheeks burned with embarrassment. She put a finger under my chin. "You look adorable. Everyone out there will think the same thing. Don't be nervous, just go have fun. If you're a good sissy, Mistress may reward you later." "Yes Ms. Erica. Thank you," I said, trying my best to smile. Back in the dungeon, I minced (mostly because I hadn't yet discovered how to walk in my heels) over to a group of guests, two men and three women. I chose this group because they seemed normal enough in their non-fetish wear. "Can I offer you a drink, sirs and madams?" I asked timidly. One of the women saw me and covered her mouth giggling while the adjacent woman elbowed her sharply. "I'll have a Jack and Coke. My girl wants an amaretto sour," replied one the men. "Yes, sir," I said starting to walk off. I jerked to a sudden stop, and realized that someone had grabbed my leash. "And, I'd like to have one of you," said a different man. He reeled me in closer and wrapped an arm around my waist. My tits were now pressed against his chest and he was looking directly into my eyes. "Maybe when you return you can take a short break with me," he suggested. Fuck. I needed to get away. This was really squicking me out. My heart raced as I squirmed without effect in his hold. "Honey, give her a break. Can't you see she's a new sissy?" said a nearby woman in a black skirt. The man let me go. "You okay, dear?" the woman asked, putting a supportive hand on my bare shoulder. I looked blankly at the floor in humiliation and nodded yes. "Aw, you are new, aren't you? Well, my husband has a thing for sissies, and he can be a little aggressive sometimes. Why don't you go do your job, and I'll keep on eye on him." "Thank you miss," I stammered and quickly pranced back to the kitchen. This was going to be a long night. Fortunately, when I returned the man and his wife were nowhere to be seen. As I gave the guests their drinks I heard the sound of a glass being struck. My eyes found the source. Kitten had entered the dungeon. Now nude, aside from her collar and chastity device, she was held firmly in Adam's hands. Katie stood next to them holding a wine glass and a fork. "Good evening everyone. Ms. Jillian apologizes for not being here tonight, but she welcomes you all. This evening we have a special event for the enjoyment of all. It seems that Kitten here has disobeyed an explicit instruction from Ms. Jillian, her mistress. "Do you have anything you'd like to say, dear?" "I'm so sorry," Kitten sobbed. "I promise to obey next time, just please don't punish me." Most of the room laughed at this, prompting even more tears from Kitten. "I can tell you're genuinely sorry about your infraction, dear," Katie said contemplatively. "I also know that you've been a good girl for months now..." She paused. "However, I'm afraid that bad behavior is simply not tolerated. Your mistress, has permitted me to punish you tonight by figging." Kitten's eyes widened in horror again as the room cheered expectantly. Figging? Katie had mentioned that word earlier. I didn't know what figging was, but apparently it was something that absolutely terrified Kitten. She panicked desperately, flailing in Adam's strong arms. "What a slut," a woman murmured to her friend. "The ones that fight it the hardest are the ones who want it the most." "Right?! It's hard to believe she ever thought she was a man." her friend whispered back. "Shh, shh, dear. Next time, I know you'll be a good girlie," Katie said in cruel sympathy. "Adam, dear, please strap her on the exhibition table." The crowd applauded, drawing more spectators from the private rooms. For reasons I didn't understand, I felt guilty. Sure, I was also contending with my own punishment, but I it looked like hers was much worse. I started to walk over to her to comfort her, but found myself detained again by my leash. Fuck, it was the man again. He pulled me backwards and sat me on his lap. "Why don't we enjoy the show together?" he suggested. His wife appeared again. Thank goodness. A wave of relief washed over me. "Hello, dear. It seems my husband will simply not be satisfied until you spend some time with him." She raised a ball gag to my mouth. "Open up sweetie." "No, I won't--" I started as she put the gag in between my teeth. "Let me go!" I shouted into it, but all that came out was "Mmmph, mmmph!" "I'm sure you'll have lots of fun. I'll be right here with you." I squirmed as her husband's bulge hardened against my ass. He held me tight in his arm as he reached under my top and played with my nipples. I looked down at his hands helplessly as he groped and fondled me. His wife had meanwhile raised her skirt and was now playing with her clit as she watched us. She was getting off on this! The two friends had turned now and were watching me with obvious amusement. "There's another one. She definitely wants it, that one," I heard them say. Her husband was now rubbing his hard cock against my butt through his jeans. Overwhelmed by humiliation, the sense of tightness behind my balls returned. It felt incredible, and my eyes rolled back as my lids shut. "That's it sweetie, just let him enjoy you," the woman said between heavy breaths. Her fingers were now vigorously swirling underneath her dress. She spread her legs and leaned into her husband's shoulder. His fingers were now pinching my nipples. With his other hand, he cupped my balls and chastity device. I was now thoroughly engaged and no longer needed to escape. "Looks like the show is about to start," he said, kissing my neck. "Mmmph," I groaned into my gag. I opened my eyes to see Kitten displayed on the dungeon's platform stage. She was bent over a black leather upholstered bench, her feet spread apart by a shoulder-length ankle bar. Her elbows were tied behind her back with some purple jute rope. Katie stood behind her holding a tray of small, indiscernible white objects. I couldn't tell what they were. She held one in the air so everyone could see it. Then she slid it up Kitten's ass. Kitten let out a blood-curdling yelp as she struggled helplessly in her bondage. "Looks like she was a bad little girl," the man said. He slid his hand up to my neck and grabbed it. "Not like you. You're a very good girl." His wife knelt in front of us. She reached underneath me and unzipped his jeans. Before long, his cock popped out from underneath my skirt's white lace trim. "Mm, she sure is," she said greedily eying his cock. She spit in her hand and lubricated his shaft. Then she began to suck, all while fingering herself. The tightness in my ass welled up and I found myself shaking from an orgasm. The rush felt amazing, but it wasn't at all like an ejaculation. There was no cum, and I was still achingly horny. His wife looked up at me, popping his cock out of her mouth. She grinned. "It looks like she's starting to adjust, sweetie." Adjust? I wasn't at all squicked anymore. I felt so girly and content as my hands massaged backwards along her husband's thighs towards his ass. He now had me by my left breast and my neck. I leaned back into him, smelling his musky scent. I shook from a chill, or maybe an aftershock from my orgasm. "She sure is, babe," the man agreed, tightening his grip on my neck. I moaned loudly, pinned in his grasp. I was sure that at least some guests nearby were watching me, but I didn't care. All I wanted was to just be there in his arms as he put me in my place. "It looks like we're having fun aren't we?" I opened my eyes to find Katie towering over me in her heels. "Such a naughty girl," she continued. "I'll need your help with Kitten. I'm sure Randy and Liv will be back next week to finish up with you, right?" "Oh of course, Katie," Liv said now stroking her husband. Randy, who seemed a bit disappointed, gave my nipple a sharp squeeze. "Mmmph!" I exclaimed. "I expect you to be here again next Friday, young lady." "Mmmph, hmm," I said, blushing. The couple stood, and Randy wrapped his arm around his wife's waist and down her skirt. She giggled from surprise and leaned her body against him as the two ambled down the hall presumably in search of a private space. ## Chapter 10 "Come on girlie, it's your turn now," Katie said tugging playfully at my leash. She gestured to the wooden platform in the center of the crowd where Kitten was trussed up. The stage was only raised half a foot or so, but it was going to be enough to put me on display in front of the whole room. I stepped onto the platform, my heels scuffing against its unfinished planks. Kitten lay face down across a table with cut outs for her face, breasts, and clit. Now gagged like me, tears streamed down her cheeks as she was twitched uncomfortably in her bonds. "On your knees, Elise," intoned Katie forcefully. Adam's strong arms compelled me onto my knees in front of a kneeling post in Kitten's field of view. The sight of her naked form writhing in obvious pain filled me simultaneously with guilt and also arousal. We looked at each other helplessly. Adam tied my arms behind my back to the post and Katie pulled my maid uniform top down below my tits. Then she unfastened my gag. A trail of saliva gushed from my mouth and all over my breasts as the gag was removed. Then, Katie removed Kitten's gag as well. "Do you want to say anything to each other before I administer your punishments?" Katie asked us. The dungeon crowd had quieted to a low murmur. I wasn't exactly sure how to reply. What would Mistress want me to say? Actually, I wasn't entirely clear on why I was being punished. Kitten, on the other hand, had a look of raw defiance on her face. I'd not seen her like that before. "I can see you need an attitude adjustment," said Katie curtly. Then, she walked behind Kitten and produced a thin cane. Kitten, who had not seen the cane, was taken unaware when Katie smacked her ass with it. Whatever was inside her ass had clearly compounded the pain as she wailed and violently convulsed on the bench. Katie struck her again. "Fuck, oh, please, no!" Kitten screamed in agony. "I'm sorry, I'll be a good girl, I promise. Please!!" Katie hit her several more times until Kitten was a puddle of exhaustion and tears. Despite the sadistic thrill in Katie's eyes, I knew deep down that Katie was only a stand-in for Mistress. It was really her desire--not Katie's--that Kitten be punished so horrifically. Surely this was the worst punishment that Mistress gave to misbehaving slaves. Right? I felt a hand on my naked shoulder, and craned my head backwards. It was my Mistress, looking down at me as if she'd been reading my thoughts. She ran her fingers through my hair, petting me ingratiatingly. "You certainly look the part tonight, dear," she said to me, smiling in her usual fashion. Despite my deep seated fear of her, knowing she was nearby was oddly comforting. I rubbed my head against her hand in an act of gratefulness and submission. She wrapped her leg across my chest and I kissed the soft skin of her thigh obediently. Katie had now finished caning Kitten and was gently rubbing her butt cheeks. She leaned down to Kitten's ear and whispered something to her as she fingered her ass. Kitten's eyes widened with unexpected glee. "Do you want to watch your bestie fluff her first cock for you, little Kitten?", she asked aloud for me to hear. "Oh yes, Ms. Katie," she sniffled in reply, wiggling her butt expectantly towards Katie's finger. "I think it would be good for-- her--to taste. To enjoy her, I mean, so I can--" her words stopped as she moaned in pleasure from Katie fingering her hole. My heart was racing. I tried to get up, but I was firmly attached to the post behind me. Mistress flexed her thigh under my neck, restricting my movement further. I had no choice but to kneel and wait for the inevitable. Hearing what she needed to hear, Katie abruptly stopped fingering Kitten and stood. "Good girl," she said, kissing the back of Kittens head. She glanced over my shoulder to Mistress and nodded. "I'm sure you'll do the same for her in the future, won't you dear?" "Oh yes, Ms. Katie. Yes!" Fuck. They planned for me to be fucked by man at some point. I wasn't ready for it, and that wasn't who I was. I was in way over my head now. I struggled against Mistress's thigh as she gave gave my nipple a sharp pinch. I whimpered in pain. "Adam, do you want to fuck the sissy?", Mistress asked. The large submissive man had been standing obediently out of the way while the ladies had their fun with us. He now grunted agreeably behind his mask as Katie led him to me. Next to my face, his cock seemed larger than I'd originally thought. "Kiss the real man's cock, sweetie," Mistress said, kneeling next to me. She placed her hand in the small of my back and gently encouraged me forward. "We all know that you're a little submissive sissy. There's no shame in wanting a big cock in your mouth." As I moved closer to his flaccid dick, I couldn't believe what was about to happen. Adam's thick and veiny manhood hung proudly below his trimmed bush. I planted a soft kiss on the tip of his rim. He gave a satisfied grunt as his glans emerged from the fold. "That's it, sweetie. Go on," urged Mistress. She pulled the hair away from my eyes as I wrapped my lips around his penis. It was very different from the dildos I'd sucked up until now. Contrary to the cold, hard and smelly rubber of those kinds of toys, his skin felt warm and supple against the roof of my mouth. Like a very fine, very soft velvet. It had now started to subtly harden as my tongue naturally teased his frenulum. His foreskin slid back and I lubricated his shaft by sliding my face forward. Mistress's loving hands stroked my hair as I pumped my head up and down Adam's cock. Another difference between the dildo and the real thing was the man behind the cock. Adam involuntarily thrust himself deeper into my mouth, causing me to gag and pull back. Anticipating this, he grabbed the back of my head and thrust me forward again. "What do you think Kitten, do you still want her 'dick' in you?" asked Katie. Kitten laughed nervously. "Oh, no, Ms. Katie, definitely not," she said a little too emphatically. "She has a little clitty, just like mine. It could never satisfy me. Besides, seeing how much she's enjoying Adam, I think she'd rather take a dick in her." "I think so, too, Kitten," Mistress said warmly. She pat my ass and chided, "Looks like you'll have to settle for being friends, after all." She gave my hair a gentle, but firm tug backwards. "Look up at him," she ordered. I hesitated with my eyes, worried that I'd be squicked out if I looked up at the man I was sucking off. This provoked a sharp swat on my left butt check, and I quickly looked up at the masked man. "Now, you'll look directly up at his face while he fucks your mouth." Adam was now breathing heavily as he thrust in and out. His size, in combination with how deep he was going had caused my eyes to water, and my eyeshadow to run. Mistress placed her index finger against my anus and tapped it. The sensation surprised me as another dry orgasm racked my body. His pace increased, his breathing forced through his mask even louder. In a sudden moment of climax, his cock hardened completely and he shot his hot sperm to the back of my throat. He came so much it coated the roof of my mouth and underneath my tongue. Instinctively, I pulled my head back to spit out the salty, bitter liquid. Mistress quickly stopped me holding my head in place with the cock still in my mouth. "I think you know what's expected of you." I did. It's difficult to swallow on command, and even harder with the large cock in my mouth, but still I managed. As I swallowed his cum, my Adam's apple rubbed against my collar in one last reminder of what I was. A feminized male sex slave. "Adam, I think you enjoyed yourself a little too much, honey. Do you have anything left for Kitty?" she asked playing with a hair on his chest with her index finger. Accepting her challenge, Adam walked over to Kitten. As he stepped away, Mistress untied my arms from behind my back. I fell forward on my hands and trembled from an aftershock of my earlier orgasm. Mistress laughed at my obvious outwards signs of enjoyment. "See Kitten, she's just a little sissy, just like you." I chanced to looked up at Kitten. She was now having her own sissy moment. Adam was rubbing his still-hard cock on her lubed up sissy hole. He smacked her ass hard as he shoved his cock all the way in. Kitten's eyes widened in shock and pleasure as he fucked her brains out. One club member in a tie took the opportunity to get a free blow job. Kitten graciously took his cock in her mouth. "Soon, sweetie. Soon," Mistress said tickling my hole with her nails. We both knew what she meant. "Next time you fluff, maybe go a little easier. If you ever make my lover cum before he gets to me, it'll be you getting figged next time." Kitten moaned in ecstasy a final time as she came all over the floor beneath her bondage table. Mistress slapped my ass, and I knew what was expected. I crawled beneath her and lapped up all her sissy juices. She tasted much sweeter than Adam. After pointing out a few spots I missed, she invited me to give my sissy girlfriend a kiss. It was an awkward angle, but Kitten and I shared a passionate, cum-filled kiss. After Kitten had received a few more fuckings from the guests, the evening had come to a head. Mistress thanked everyone for helping break in the sissies, then made rounds to say farewell to the guests. Meanwhile, Adam carried Kitten and I to Mistress's bedroom. The two of us were in shock and too exhausted to talk. We took turns in the shower, and then spooned together in Mistress's bed. As usual, I was so horny but there was nothing I could do. I'd not cum in days despite being held in near constant arousal the whole time. She giggled at me as I involuntarily rubbed my caged penis against her butt. A couple of hours later, Mistress entered and crawled into bed between us. "There are my sissies. You two did great tonight. Now, come love me." I kissed her and rubbed her breasts with my hands, but she pushed my head down to her pussy. I ate her out while Kitten made love to her above. Despite my unfulfillment, I was too tired to be overly frustrated. I gave her my very best and she came several times. The three of us fell asleep. Two sissy slaves and a real woman. ## Afterword As the black-tied waiter arrived to carry away their plates, Jillian cupped her hands and considered the situation carefully. Going into this meeting, it had been her plan to reveal to Kristen the truth about her sissy husband--who at this moment was serving drinks at the club for the first time--while also revealing the truth about herself: A talented and beautiful woman like Kristen should have a strong, bold man. A successful man to complement her: a successful woman. A man like Matthew, or any man she wanted. After all, there was reason why she and her husband didn't get along. Sure, he had a well-paying job with benefits. They had a nice enough home and nice enough cars. They spent a reasonably acceptable amount of time with each other, and he was agreeable and helpful to her often enough. The truth was that for her husband, these things had been requirements. Mere check marks that had been made over the years to satisfy his wife. To prove that he was good enough for her. Deep down Kristen surely knew his ulterior motives and that good enough wasn't. What he'd failed to realize was his own needs. Needs that his wife could not meet, nor would she if he'd even known to ask her. Kristen could only ever be puzzled and isolated. Unable to find true intimacy with her husband. Jillian was not entirely altruistic, but reveled in the joy of leading others to find their way. It was a quality that made her the best kind of domme. Jillian wanted to help Kristen just as she'd helped her husband. Unfortunately, Jillian's plan had grown more complicated. For reasons that she hadn't yet fully accepted, she'd compromised her own values, and now she had to live with the consequences. She had a secret that she wasn't ready yet to reveal to Kristen. What was worse, was that she wasn't sure that she'd ever be able to. Now, she held her hands both her fragile new sissy and her new sissy's fragile wife. She'd put herself into their lives in order to gain Elise, but it was never her intention to hurt Kristen, and she feared that hurt was inevitable. "Well, I guess I will. When should I come?" Kristen asked. To the club, she meant, but Jillian couldn't help but smile at the oddly phrased, yet innocent question. With a submissive personality like Kristen's, Jillian's response would normally be, "When I say so." In fact, Kristen was quite submissive. Throughout the meal, Jillian had noticed that Kristen was nervous, even lacking self-confidence. Almost as if she were at a job interview and she'd all but psyched herself into flubbing it. Jillian thought it cute and realized for the second time that the girl needed someone to guide her. To look after her needs. Of course, that was Jillian's specialty. So, she'd taken charge by ordering Kristen's entr?e for her. Kristen had seemed surprised at Jillian's boldness, but made no complaints. Later in the meal, she'd even thanked Jillian for suggesting something for her, and admitted that she'd not been sure what to order at a French restaurant. Kristen's agreeable and accommodating nature played right towards Jillian's strengths. Realizing this, Jillian had now found a solution for her crisis of conscience. With Kristen's question hanging in the air, Jillian gave a conspiratorial smile and asked, "Dessert?" "Oh no, I can't. I'm on a diet, and--", Kristen started. "No, no, no. I insist," Jillian interrupted. Kristen, enamored again with Jillian's confidence, was now smiling to herself, apparently happy that dessert was coming despite her previous protest. Jillian expected this typical submissive behavior and pretended not to notice Kristen's satisfaction. She turned to the waiter and ordered them each cr?me br?l?e and an espresso. The two sat in silence a moment as the waiter disappeared with their plates. "Listen," Jillian said, grinning. "I want you to come this weekend. Tomorrow night, in fact. Trust me."