5 comments/  91954 views/  20 favorites

A New Year Pt. 01

By: femmed



Author's note and disclaimer: This is a story containing non-consensual sexual acts (including cross-dressing, bondage, and other fun stuff) performed by a woman on her unwilling slave. In real life, all acts should be consensual - stories like this are only for fantasies and for fueling scenes.

Comments and criticisms are welcome, of course. 

I'm in the process of taking the assorted stories I've written and posted online at various sites, and attempting to consolidate them all at Literotica. Of course, I'm tidying them up - both for spelling errors and to improve the flow of the story a bit. I first posted this one on Usenet ten years ago.

And now, your story.

A New Year    by: Adam Smith

Chapter 1 - The Trap

"Thanks, sweetie." That was Jane, the secretary in our IT department. Although I technically support other departments at the college, all of us end up helping out Jane, as well. Even if it's not in the job description, it's pretty hard to say "no" to your team's secretary if you know you can fix it. After all, if she's able to get her work done, payroll gets filed on time, vacation hours get credited properly, and we're all happy.

Of course, the other reason I am glad to help Jane is that I've always had a little bit of a crush on her. Jane is a pretty blonde Midwesterner, and has that wonderful sweet way about her that some Midwesterners have -- she called everyone "sweetie" and "dear," and always had a smile ready for anyone who was nice to her. I wouldn't call it innocence, per se - she certainly has sex appeal, and since she'd just gotten divorced, only an idiot would think of her as "virginal." But her sex appeal never came across as deliberate. She never wore mini-skirts, or low-cut blouses, but rather just had a way about her that was incredibly attractive. It was obvious that she had great breast and legs, without having to create any false cleavage or resort to any other tricks.

So why didn't I hit on her? Well, there were a few reasons, I guess. First, she was a bit older than me - I was 27, and she'd just turned 35. Second, after the divorce (which was not a pleasant one, from what she said around the office), I wasn't sure if she'd be open to seeing anyone. Third, she was, I thought, way out of my league. And finally, I've never been a fan of intra-office relationships. They can cause too many problems. So I contented myself with enjoying ogling her when she bent over to file things (she may not have worn mini-skirts, but she still showed herself off nicely in jeans and slacks), and the innocent flirting that she engaged in. 

It was Friday afternoon, just before the long New Year's weekend, and we were the last two folks around. We've got a pretty lax office, and between semesters, most folks work from home or take off early. It was about 4, and I'd been thinking about heading home myself, when she'd asked me to fix a problem on her computer. It was pretty simple, but the smile she gave me when I finished was worth it. She was clearly about to head out herself, and was finishing cleaning up while I was working on her machine.

"So," she said, "are you doing anything special for New Year's Eve?" 

"Nope. I've never been a huge New Year's partier. The roommates are out of town, so I figured I'd get a pizza and watch the fireworks on TV. How about you?"

"Oh, not much," she said, as she finished putting away her files, and started towards the coffee machine. "I'll probably get together with someone special and just enjoy the weekend." She didn't put any special emphasis on the words "someone special," but I took it to mean that she was planning on getting laid this weekend. Some guy was going to be real lucky. 

"Sounds great," I said, as I finished up. "This is fixed, now."

"Oh, you're so great! Now we can both get out of here before 5! And - Oh!" That exclamation was made as the heel of her shoe caught on the carpet, and she tripped, sending the contents of the nearly-full coffee pot she was bringing to the office sink right into my crotch. My initial fear was cut short, as it became apparent that this was the leftover coffee from this morning, and was cold, not hot. But as I was wearing very light tan pants, it was going to be hard to hide the huge stain that was now there when I left. Worse, we'd been having a frigid winter, and I knew that even walking the seven blocks home could be a health risk with pants this soaking wet. I could feel the coffee soaking through my boxers, too.

"Oh my god! Alan, I'm so sorry!" Jane made the same connections I did, and said, "there's no way you can walk home like that."

"Oh, it won't be too bad," I lied (it's hard to be mad at someone like Jane). "It's a short walk, and I'll be fine. Besides, it's not like I keep a change of clothes at the office."

"That's an idea! I've got my gym clothes! I didn't make it to the gym today, so they're clean, and sweatpants should be able to stretch enough to fit you just fine."

"Oh, Jane, I couldn't."

"Nonsense. It was my fault, after all. Change in the bathroom, and then I'll drive you back to my place, so no one has to see you walking around in pink sweatpants. I'll wash your clothes and make you dinner - I owe you that much." I haven't really done much kinky stuff in my life, but there's something intensely erotic about a beautiful woman telling you to wear her clothes, and since my pants were sopping, I knew that any reaction I had would be pretty obvious, so I grabbed her gym bag and headed to the bathroom. As I was about to go in, she called out to me. "Oh, there's clean underwear in there, too - in case the coffee's soaked all the way through." I thanked her and entered the bathroom.

As soon as I got my pants off, there was no doubt that I'd need to at least get rid of my boxers, which were sopping wet, even if I didn't bother with her underwear. I couldn't imagine her stuff fitting me, but when I opened her bag, it was obvious that although the panties (pink cotton ones - I should have known that they wouldn't be frilly or silk for a workout, but I was still surprised) were clean, they were a bit well-worn, and although they were tight, they did fit. The sweats were a hot pink, but they also fit (although they were also somewhat tight). Looking at myself in the mirror, I blushed - although sweatpants should be gender-neutral, these were short, tight, and the sort of pink no man would ever wear. To top it off, there were little hearts on the side. I exited the bathroom, to find Jane wearing her coat, ready to go. 

"Looking good, hon," she winked at me, still sounding more sweet than seductive. "You ready?"

I grabbed my coat, hoping she didn't see me blush. "Sure - let's go." The walk to the car was only about a minute - although we didn't run into anyone, I knew there were still folks on campus, and I was incredibly nervous about being seen in pink. 

Jane definitely picked up on it - as soon as we got into her Saturn, she said, "don't worry - I don't think anyone saw you. Although," and she smiled as she turned the ignition, "you do look great in pink." I blushed a bit and brushed it off as a joke. 

The ten-minute ride to her place was filled with the usual inconsequential conversation about co-workers and the like. When we got to her place, she went to toss my clothes into the washer, while I wandered around the living room. I'd never been to her place before, but it was a nice apartment - she'd obviously done well in the divorce. Nice leather sofa, some beautiful bookcases, some hanging plants, and a gorgeous fireplace. The coffee table in front of the couch was solid wood, and looked like an antique. I'd just started to look through the books when Jane came back in.

"Grab a seat on the couch, and I'll make you a drink," she said, heading to the bar in the corner of the room. "You like rum and tonic, right?" The entire office had gone out drinking a few times, and I'd been kidded for not being a typical beer guy.

She brought my drink over and sat next to me on the couch - a bit closer than I'd expected, actually. "You know, Alan, I wasn't kidding about how good you looked in pink. And I don't think I'm mistaken in thinking that you like how I look, am I?"

"Um, Jane, wow. No, of course you're not mistaken, I just didn't think -" I stumbled. I sure hadn't expected a come-on from someone this attractive! 

She took my drink, put it on the side table, and promptly proceeded to straddle me, her jeans-clad legs grabbing my sweat-covered thighs tightly. "I didn't invite you in to think, you know," she said, as she then leaned down and kissed me. It was one hell of a kiss, and I was hard as a rock against her by the end of it. 

"Um, didn't you have plans this weekend?" I asked, my mind mentally cursing my mouth for asking the sort of dumb question that could kill my chances then and there.

"Silly. This was my plan. I've been planning this for a long time. Now," she said, sliding off of me, "let's see how easily those sweatpants come off." She pulled them off of me, along with my shoes and socks, leaving me in only my shirt and her panties. "Wow, those panties show you off nicely," she said, referring to the fact that they were tight enough to outline almost every detail of my bulge. I started to take them off, but she stopped me. "Hold on - we've got plenty of time, and I kind of like how you look this way." She straddled me again, and we spent the next fifteen minutes or so kissing, necking, and dry-humping on that couch. I was so completely aroused by this point, I was sure I'd burst a hole in her panties any second.

"Mmm," she muttered, as she nibbled lightly on my neck. "Listen, I want to take this further, but I need to make something clear - after my ex, I've needed to be the one in control of a relationship. I have trust issues, and this is our first time. I'd feel a lot more secure if I could make sure I knew where your hands were at all time. Would you be okay with that?"

I was near-deliriously horny by this point, and willing to agree to just about anything. "Of course." 

"Great - you take off your shirt, while I grab the cuffs from the bedroom." Cuffs? It took me a second to realize that I'd agreed to that. I'd never been tied up, but for Jane, I was willing to start.

By the time I had my shirt and undershirt off, she was back, with a small plastic bag. She reached in and pulled out a pair of leather wrist cuffs. Each one was strapped on to one of my wrists, and she then clipped them together with the metal studs on them. I was sure that I could probably get them apart, but I was also sure that although my hands were effectively tied together, they could still move around. I pointed this out to her.

"Oh, I've got a solution for that," she said. She wandered around behind me, leaned down, and started nibbling on my ear. "Now, lover, this should keep your hands busy, she whispered," as I felt her place something around my neck. Before I could react, she clipped my wrist cuffs to it, and I realized that I was now wearing a collar, and my hands were locked in place, behind my head. 

"Um, Jane? I'm not too sure about this."

"Oh don't worry," she said, as she came around to the front of the couch again. "I can tell that you're still having fun," she said, looking meaningfully at my still-hard cock bulging against her panties. "And if you ever want me to stop, just say so." She straddled me again, and after another five minutes of kissing, I'd all but forgotten about the collar. My dick, rubbing against her groin (she was still wearing her jeans from work, although the blouse had come off by this point), was as hard as it had ever been, and I was desperate to get inside of her.

She obviously felt the same way, or so I thought. "I think we need to move on to the next stage of things," she said, pulling back from a kiss. I agreed, of course, and she had me stand up and walk around behind the couch. "I'm going to go change into something a bit more appropriate." I smiled, just trying to guess what sort of lingerie she might have. Now, I'm just going to make sure you don't wander off anywhere. Before I could react, she'd kneeled down and strapped my feet to the couch. "Let's give your little friend some breathing room," she said, pulling the panties down to my knees. "I'll be back in a jif," she said, heading into the bedroom behind me.

As I stood there, twiddling my toes through the carpet, I started to get a bit concerned. I had let this gorgeous woman secure my hands to my neck, and put a collar on me, and tie my feet! I could understand her control issues, but it didn't seem very normal for a woman to own a collar, and as I looked at the restraints on my feet, it was obvious that the straps were permanently attached to the couch, not something that a typical divorced secretary is expected to have! My dick started to soften with the waiting and the anxiety.

Chapter 2 - Getting Dressed Up

Although only a couple of minutes passed, they felt like an eternity. Then I heard the bedroom door open behind me, and she came out, stopping about a foot behind me to the right. "Well, how do I look?" I turned my head, as was amazed - Jane was wearing some sort of skin-tight black bodysuit that seemed to be made out of latex. It covered her upper body and crotch, and 

it was obvious that her body was every bit as good as had been hinted at by her work clothes, as her curves were all shown off perfectly.

The bodysuit had a garter attachment, which led to black latex stockings. The only other items of clothing on her were a pair of black high-heeled boots going nearly up to her knees, a pair of black opera gloves, and a studded collar around her neck, one I'd guess matched the one I was wearing (I hadn't had a chance to look at it before she put it on me). She had redone her lipstick, and was now wearing a dark red that made her look even sexier. She was also carrying another plastic bag, although I wasn't really paying attention to it at the time.

My mouth just dropped open - I'd expected a pink teddy, or something. I was speechless. "I guess I'll take that as a sign of approval," she said, nodding over at my penis, which had quickly hardened to its full length again. She hugged me from behind, and started playing with my cock.

"Jane, I'm not sure how much longer I can hold out." It's not like I'm an earlier cummer, but after this much stimulation, it wouldn't take much to get me off. 

"Well, we surely have to do something about that," she said, reaching into the bag. I can't have you cumming on this nice couch, can I?" She reached around me again, and placed a pair of panties on the end of my cock. They were blue panties this time. "These were the panties I wore at the office today," she whispered in my ear, as she started to rub the panties (which were more than a little damp, as she'd also been wearing them we were on the couch), up and down my shaft. "So you've managed to get your dick into two pairs of my panties already."

After only a few more seconds of rubbing, I was ready to cum, and she obviously felt my body start to contract, as she move the panties so that my dick was pointing into the rear of the panties. That orgasm was one of the best of my life, and certainly better than anything I thought I could get from a hand job. I couldn't believe how much I spurted there - the panties were barely able to contain them all, and I knew that after a couple of minutes, my cum would soak through. 

So did Jane, I'm sure. "Wow, Alan," she said, still holding me from behind. "That was impressive." 

As she talked, she took her hands away, and I heard her reach into the bag for something. 

"There's only one problem."

"What's that," I asked, trying to regain my breath. 

"Well, these panties are dirty, and I just used the last of my detergent on your pants."

"Oh," I said, still a bit confused and attempting to think clearly after that incredible orgasm. "Well, I'm sure that afterwards, I can -" Before I could get any further, she shoved something soft in my mouth. "Mmpth," I said, as she reached around me with her other hand and placed something - tape! - across my mouth. By the time I realized what happened, I had her panties, soaked with my cum, in my mouth.

"Oh, that's so sweet of you! Only the nicest guys would offer to do a woman's laundry. And you must be enjoying it, since you're not asking me to stop," she said, clearly realizing that I couldn't ask a damned thing.

She leaned down and pulled my panties back up, covering my now limp penis. "Now, let's finish getting you dressed," she said. I heard her rummaging through the bag again, getting more stuff out. As she emptied it out (behind me, so I couldn't see any of it), she continued talking.

"I told you I'd been planning this for a while. I've seen you ogling me at the office. If you'd asked me out or something, I might not have been as upset, or even if I just thought you were shy, but you just enjoyed staring and using me for your masturbation fantasies." I tried protesting, but my mouth was full, and any attempt to talk only resulted in more of my own cum getting on my tongue.

"So I decided that I was going to have to use you for my sexual pleasure, just like you used me." I hardly felt that some mild fantasies were the same as this, but I wasn't in any position to say. "I wonder if any of your fantasies involved becoming my slave for the weekend. You sure seem to be enjoying it." I wanted to protest, but even as I tried to mumble through the gag, I could feel my dick hardening again, stretching the panties. 

As she talked, she wrapped a skirt around me. It was a plain grey one, loose, and going to just above my knees. I was less surprised, by this point, at the skirt itself, than I was at the fact that it wasn't tight or made of leather. I felt her doing something to my feet, and on looking down, I saw her placing cotton balls between each toe. She looked up at me and smiled. "I'm just going to make your toes nice and pretty. And I'd recommend keeping them still - otherwise I might paint other parts of your body." She gave my ass a swat as she said the last.

"This stuff should dry pretty quickly," she said, while she was painting my toes. "Of course, your toes won't look all dainty, since I don't have the time to give you a full pedicure, but they'll look better." I could see that the color she was using was a bright red. She told me to not to wiggle my toes for five minutes, while the polish tried, and then she moved the bag around to the front of the couch and kneeled on the couch facing me.

"Well, while that's drying, let's work on your face!" What? She reached into the bag, but instead of pulling out a makeup kit, she had two long pieces of wire. She attached each one to the collar, and then attached them to studs on the couch. My neck was now immobilized. She then took out a larger collar, and wrapped it around the smaller one (and my neck and hands), so I couldn't even nod my head without starting to choke. "Now that you can hold still, let's get to work." She pulled out the makeup kit that I'd expected before, and proceeded to put mascara, eye shadow (blue, from what I could see), eyeliner, and foundation on my face. She covered my cheeks with blush. She then frowned as she got to my mouth.

"Well, I hope you're done with your laundry! It's time to work on your lips. It's okay if you gasp a bit when I take the tape off, but I expect you to remain silent!" She then ripped the tape off - it didn't hurt that much, thankfully - and pulled the panties (soaking wet, but only with my saliva) out of my mouth. I gasped for air, and attempted to plead my case.

"Jane, I-". She grabbed my chin with her hand and squeezed my cheeks.

"No no no! What did I tell you, sweetie?" Perhaps the most disturbing thing about this entire evening was that Jane still had that sweet Midwestern voice. "Keep quiet. For the next three days, your only job is to fulfill my fantasies. And whether you believe it or not, you're going to realize that some of the things I'm going to do to you are your fantasies, too." 


A New Year Pt. 01



Still holding my chin in her gloved hand, she reached down and picked up some sort of lip pencil. Although I know there are all sorts of weird types of makeup women use, I had still been expecting a traditional tube of lipstick. After she outlined my lips with the pencil, she got a brush out and painted them. I couldn't see the color as she did it. In fact, I was so distracted by her breasts -- which I now realized were covered in wet-look lycra -- rubbing up against me as she applied the makeup, I almost missed what she was saying.

"You see, I'm good at reading people. And believe me, your body reacts well to the idea of being tied up and controlled. Of course, you might not like everything I do this weekend, but this is about my fantasies. If you get some pleasure, that's incidental." 

"That looks perfect," Jane said, as she put the makeup away. "This isn't my favorite color of lipstick, but this style goes on dry - it won't smear or rub off for hours!" Oh, joy. She took off the large choke collar (but not the wires holding the bondage collar in place), and held up a mirror for me to see. I looked ridiculous, of course. My eyelashes, always long, now looked ludicrous, thanks to the mascara. My face looked darker with the foundation and blush, and my eyes had a light blue shadow above them. But the worst was my lips. The color she used wasn't one of the sophisticated but sexy styles that I'd seen her wearing to the office. It was a bright red, the color of a maraschino cherry.

"Jane, please! This is ridiculous!"

"Dammit, Alan!" This was the first time she'd really raised her voice all night, and it startled me. She sighed, again grasping my chin and squeezing my cheeks. "If there's one thing that really frustrates me about guys, it's that they only think about themselves. You've gone and had your orgasm, and now you aren't even worrying about making me happy." While she was saying this, she had reached behind me with her other hand, and I felt a strap on the back of my head. "Much as I'd love to put your mouth to good use on me, I'm afraid I'll have to do this instead."

As I started to ask her what she was talking about, I felt her shove something in my mouth. Unlike the panties, this was solid. I felt her adjust the strap, and I realized that she had placed a ball gag on me. I'd seen them on the internet, but never even seen one in real life before. 

"There. That should keep you from talking, although I'm afraid I'll still have to punish you." This wasn't punishment enough? "That gag shouldn't be too big for your mouth, and it's one that has airholes in it, so you should be fine." In fact, it felt more like plastic than like the hard rubber things I'd seen on websites. Airholes or not, I still couldn't make any sound more articulate than a grunt. Jane unclipped the wires from my collar, so I could now move my neck, at least.

"Now," said Jane, as she hopped of the couch, with the much emptier bag in hand, "we need to come up with your punishment." I had a feeling that I'd have "earned" the punishment no matter what I did, just as I was now certain that everything from the spilled coffee to the pink sweatpants to making me come before she did was planned. 

"But before we worry about your punishment, let's check out your nails. She crouched down and lightly touched my toes. "Yup, all dry!" Jane then slid one of the bolts that my leg was attached to up about two inches, forcing my foot off the ground. She then slid a high-heeled sandal onto my foot. It was slit so my bright red toes were still visible. She did the same with the other foot. I watched as she slid the bolt, to see if there was any chance of my lifting my feet out of the restraints, but I saw that she had to press something on the bolt to slide it up. When she had the other shoe on me, she strapped both to my ankles (no chance of slipping them off) and stepped back to admire her work.

"Well, aren't you just perfectly feminine?" She paused, looking over me. "Actually, we need to do something about that hair." She started rummaging through the bag again, and I figured that she was looking for a wig. 

Then I heard a buzzing, and realized what she was talking about - she was shaving my legs with an electric razor! She was thorough, shaving my calves and lower legs until they were nearly perfectly smooth. "We'll take care of the last of the stubble later," she said. She didn't shave above my knees, probably because the skirt covered everything else. But she did get back in front of me, using the razor to shave off all of my chest hair! I'm not the hairiest guy in the world, but I felt strange not having any hair at all on my chest.

"Well, I think that looks just about perfect." I was tied up, with my arms bound to a collar, wearing a skirt, panties, and high-heeled shoes (which combined with being unable to move my arms, made it hard to catch my balance), with red-painted toenails, garish makeup, and a ballgag, and Jane called it "perfect!" 

I heard a click and there was a flash of bright light. I was disoriented for a second, but then I realized what she was doing - she was taking pictures! She stepped to the side to get a profile shot, than took one focusing on my feet. She finally stepped around in front of the couch and took some more pictures of me. The camera was a digital camera - in fact, I remember Jane asking me for advice on which model to buy! She leaned in, kissed me on the cheek, and said (as she headed back into the bedroom), "I'll be back in a minute! I just need to load these up to my website."

She didn't have to say anything else - I could read the implicit threat there - if I tried to do anything (not that I could, tied up as I was), she had blackmail material on me. I'd seen the makeup job, and I knew that anyone who knew me would be able to recognize me in the photographs. I could only stand there and wait, trying not to fall over, as she uploaded the pictures. I had no idea what Jane had planned for me, but I knew that this was already going to be the most unforgettable weekend of my life.

Chapter 3 - The Long Night 

"Well, that's done, anyway." I jumped when I heard Jane's voice. She hadn't shut the bedroom door, and the carpet was soft enough to absorb the sound of her footsteps. "Now, we need to start thinking about your punishment for that little burst of backtalk."

She reached around me from behind and started rubbing me all over with her hands, while rubbing her breasts against me. I noticed that she'd taken the glove off her right hand, although her left was still in rubber. She gently squeezed my cock through the skirt, and when she felt it hardening again, said, "well, I'm glad to see you're still enjoying yourself. Let's see if you'll be as happy when I put on your next piece of clothing." 

Before I could begin to wonder what that might be, she came around to the front of the couch and crouched in front of me, so that our faces were at the same level. She bent her head down and sucked on my left nipple, gently biting it. Although I'd occasionally had lovers who would play with my nipples, I'd never had this sort of sensation, and the newly shaved skin was extra sensitive. While I moaned in ecstasy, however, I felt a sharp pain - she had placed a nipple clamp on me! It looked like a small tweezer attached to a chain, and even as she lowered her head to the other nipple, and I did my best not to let her get it hard, I knew exactly what would happen. Sure enough, in no time at all, I had a pair of nipple clamps on me, with a chain connecting them. The pain wasn't excruciating, but I could see that there were slider rings attached to the clamps, and I knew that she could tighten them anytime she wanted to.

"There! Didn't you start to get curious when I didn't put a bra or something on you? I think these are so much sexier!" Jane snapped another photo. "Now, I don't think I'll tighten these now, but if you're not a good boy, I may have to play with them later." She gently kissed my now extra-sensitive nipples, and then stood back up, in front of the couch. "Of course, you talked out of turn twice, so I need to come up with some other punishment for you, too."

She reached out and grabbed the chain connecting the two clamps. The pain intensified, and she pulled on them, causing me to completely lose my balance (thanks to those high-heeled shoes), and fall over the top of the sofa. While I was still disoriented, Jane attached the chain to a hook on the edge of the couch, and I was immobilized. She then unattached my left hand from the collar on my neck, and stretched it out to my left, where she reattached the cuff to yet another hook. After repeating this action with my right hand, I was completely tied down. On the plus side, since I was now resting my weight on the top of the couch, the shoes were no longer hurting my calves.

Jane walked around behind me. I had a pretty good idea of what was coming next. The heels and the angle at which I was strapped down meant that my butt was sticking high into the air, and given all her talk of punishment, I figured she was planning on spanking me.

Her words soon proved me right. "Aw, isn't that cute - your cute little butt is just sticking up into the air, practically begging for a little swat." She lightly smacked me as she said this. She flipped up the skirt, and pulled down the panties. "How many spankings do you think you deserve? Five? Ten? Oh, let's just go for an even twenty."

I hadn't been spanked since I was a kid. I figured it couldn't be that bad, and the first few weren't. The first five or so were with her bare hand, and although the stung, they weren't too bad. The next five were with the hand in the rubber glove, and I swear she was also swinging harder, because those five hurt like hell. My ass felt like it was on fire by the tenth swat. 

"Well, that's a good start, but those swats are hurting my hands. And your ass just isn't getting red enough. Let's see if I can't improve things for the final ten." The next swing hurt more than the first ten combined. I had no idea what she was using, but it felt like a paddle. Each swing was progressively harder than the last, and by the twentieth, I was on the verge of tears, and I was wondering what the hell she was using. When she walked around to the front of the couch and sat on the coffee table, I saw - it was a hairbrush, with a solid wooden handle. "It's one of the few toys I can leave out when my parents come to visit," she giggled, as she ran it through her hair.

Jane spread her legs, so I could see the outline of her lips, and the small damp spot that had leaked through the lycra. "Now, we've got a problem. I brought you back to amuse me, but I was expecting a few orgasms out of you. But you had to talk out of turn, which means your mouth is out of commission. And you went and wasted your penis before I even got started! So we need to find a way to make me happy." 

She pulled yet another item out of the bag. It was a contraption of straps and buckles. I couldn't figure out what it was for, but she expertly strapped it on herself, and although there were some extra straps hanging by the side, there was now a large buckle right over her clitoris.

"This is a slightly modified belt for strap-ons. The first modification is this buckle, which allows me to swap different dildos onto the end. I'll show you the other modification later." A dildo? This was too much - I'd never had as much as a finger stuck up my ass. Now I was having visions of something as large as my forearm shoved up it. I'm sure Jane saw the fear in my eyes, because she took her time rummaging through her bag of toys, before finally pulling out what turned out to be a surprisingly small black dildo - no more than four or five inches, I'd guess. The term "anti-climatic" came to mind, but I wasn't planning on letting Jane hear that, even when I could speak again.

"Don't worry. I've got bigger ones, but I wanted to warm you up with this one, first." Jane stood up, and showed me the back of the dildo, which had a pair of bumps on it that she explained would rub against her clit through the bodysuit. She then clicked it into place. It looked a hell of a lot more ominous sticking out from her like that. Then she walked behind me, and I the next thing I felt was something cool being rubbed on my ass. It felt great at first, since my ass was still stinging from the spankings, but she then started slipping the lube into my asshole, inserting first one, then two of her gloved fingers. It didn't really hurt, but it definitely felt uncomfortable.

Then she slammed into me. I didn't think that such a short dildo could hurt so much, but I just hadn't been prepared for having something inserted in my asshole like that. Jane thrust in and out of me for a while, actually pulling all the way out and reinserting herself each time. Then, as she started to get more excited, she simply leaned into me, keeping the dildo inside of me and just wiggling her hips to get herself more stimulated. While she was doing this, she also started nibbling on my ears and neck, and lightly flicking both my nipples and the clamps. Between the various pleasurable and painful sensations, I was completely disoriented.

Eventually, I heard and felt Jane start to shudder, and she clearer reached an orgasm. She slumped on me for a few minutes, idly toying with my nipples. Then she murmured, "thanks, lover. I guess you were able to get me off without using your dick or mouth. Now it's time I show you the other modification I made to the strap-on belt." I felt her reach back and do something, and then she slowly backed away. As she backed away, I felt the dildo stay inside of me!

"You see, there are extra straps on this belt, so I can use it to strap the dildo inside someone, too." As she said this, Jane reached around my waist and attached two of the straps together. She then flicked the base of the dildo a few times, making me quiver. As she tightened the straps, she grabbed my cock, which was now rock hard, thanks to the prostate stimulation she had been giving me. "Well, looks like your penis is finally ready for some action again. A little too late, though. You won't be using it again tonight." 

Jane then walked around to the front of the couch. She thrust her crotch, now fully soaked through with her juices, right at my nose. "See how worked up you got me, lover?" As she said this, she grabbed my hair and all but ground my nose into her wet spot. Her smell was intoxicating, which only made my immobilization more frustrating.

Jane walked around the couch again, taking more pictures with that camera. She pulled the panties up and flipped the skirt down between shots, so she had pictures of me in plenty of different poses now. After uploading them, she came back into the room, and without warning, pulled off the nipple clamps. My initial relief vanished quickly, as the blood rushing in made my nipples feel like they were on fire. Jane either didn't notice, or didn't care, as she removed my arm buckles from the sofa and reattached them to each other. She then did the same with my ankle cuffs, attaching them to each other. With the shoes I was wearing, standing up was almost impossible. 

It turns out it wasn't necessary, either. "Now," Jane said, as I tried not to trip, "It's been a long evening, and since we've got a full day tomorrow, we need to put you to bed now." 

She reached over and attached something to my collar. "Since you're dressed like my bitch, and since you just got fucked like a bitch, you need to be walking like one." Hearing her use such harsh words in that sweet Midwestern voice of hers was almost surreal. Although crawling was harder than I'd expected, with my hands and feet so close together, I was able to crawl into the bedroom that she led me to with the leash. She led me into the bathroom, and finally let me stand up so I could piss before bed.

Jane then tied me down to the bed. Instead of attaching my cuffs directly to the bolts in the bed, she was nice enough to attach the cuffs to nearly-taut pieces of rope, which gave me a few inches of movement. After securing my legs to the bed and removing the shoes, Jane crawled up and straddled me, resting right on my rock-hard cock. Her weight also placed more pressure on the plug that was still in my butt. She smiled sweetly down at me. 

"Now, sweetie, let's go over a few ground rules for the night. First, I will remove your gag in a second, because it won't be easy to get to sleep with it in your mouth. I don't expect you say a word, however, unless you want to spend the night wearing those nipple clamps again!" 

I shook my head vehemently. 

"Good. Second, yes, you will be wearing the dildo all night. Don't worry - it'll soon feel like a part of you. And finally, sleep well. Tomorrow's going to be a busy day. I intend to put your mouth to work doing all the things it couldn't do tonight." With that, she leaned forward (deliberately grinding her groin into mine even more), removed the gag, and left the room, leaving me alone in the dark, wondering what else she could possibly have planned for me.



A New Year Pt. 02



Chapter 4 – Dressing for Success

"Good Morning, sweetie." Jane's cheery voice woke me from a dreamless sleep.

It took me a second or two to get my bearings. I normally feel pretty lousy when I wake up. And that's when I'm not in bondage. Today, I really felt like crap. My arms were still tied to the bed, and although Jane had tied the ropes loosely enough to let me wiggle around a bit, my arms were still cramped from having been in the same position all night. My face felt funny, and I realized that it was the dried makeup from the night before. The gunk on my eyes felt especially heavy. And worst of all, the plug in my ass made me feel bloated.

Jane, wearing just a bra and panties, sat down on the bed next to me and started rubbing my chest. "I hope you slept well. I've got so much planned for today, and I don't want you running out of energy on me!" A glance at the clock on the bed showed that it was 10:30 – I couldn't believe how well I'd managed to sleep, all things considered. 

She then straddled me, grinding her groin into mine. I always wake rock hard (although more with the need to pee than anything else), and the plug and her grinding had me even harder than usual. "I'm so proud of you – you remembered that I don't want you talking!" As if I could forget the pain of the nipple clamps I'd had to wear as punishment!

Jane reached over to the bedside table and picked up a jar that she must have brought with her that morning. "Before we do anything else, we need to get you cleaned up." And with that, she used a washcloth and the cold cream in the jar to wipe off my makeup. While she was getting my face clean, she was still rubbing her crotch into mine, and I was just about on the verge of cumming by the time she finished. Whether she sensed it or not, she got off of me before I could go over the edge.

"Time for us to shower." Us? That could be interesting, at least. She undid my arms, attaching each to the collar, then undid my legs and led me to the large bathroom. She had me lean over the tub, and attached my collar to the edge (I was no longer surprised that Jane seem to have ways to secure me everywhere in her house). She then wiggled the plug out of my butt. It hurt a bit at first, but the feeling of relief at having it out was much great than any discomfort. I heard her drop it in a bag, and then she let me up, and sat me down on the toilet.

She attached one of my wrists to the wall, securing it with a lock, and said, "You've got five minutes to take care of your business, while I take care of a few things." She walked out with the bag, and I found that I did, indeed, urgently need to use the toilet. While I used it, I looked around the bathroom. It was absolutely huge, with two sinks and a large mirror, lots of open space (it was obviously meant as a dressing room as well as a bathroom), and a huge tub, one that was big enough to be used as a hot tub, and which had a shower curtain attached, as well. There was a toothbrush sitting on the sink, and I was hoping Jane was planning on letting me use it next, as my mouth always feels disgusting when I wake up.

I also pondered my situation. Jane had not, since first tying me up, left me in a position to ever get away. And she'd also taken lots of pictures of me in rather embarrassing situations, and uploaded them somewhere. I was sure that with one hand free, I could probably overpower her when she came back. Of course, I wasn't sure I could get away after that. Jane had me trapped. I just wish I knew what she was planning.

When she came back and clipped my arm cuffs back to my collar, I started to head to the sink, but she said, "no, hon, we'll get you in the shower first, and then we'll take care of your teeth." She had me climb in the tub, and clipped my ankle cuffs to two wires attached to eyelets at the bottom of the tub. She then removed my arms from the collar and attached each to a hook in the wall, so my arms were now secured in front of me, but each at a 45 degree angle. She finally attached yet another wire to the back of my collar, holding my head in place. I was, once again, completely immobilized. 

Jane then turned on the shower. It was one of those shower heads that could be detached, and she used it to wash me. She stood behind me while she was doing it, reaching around me to soap up my chest, and later, my groin. Needless to say, as she soaped me up, I got hard, although Jane didn't make any comment. She also took her time washing my ass, sticking a soap-coated finger up my asshole, and then spreading my cheeks and spraying me with the shower head. 

When she was done washing me, she reached around and showed me something else – a bright pink razor, obviously the kind women use on their legs. "Now, don't worry, lover. This won't hurt as long as you stay real still. But I need to shave you close, since I want to make sure you look like a perfect lady!" Jane was true to her word, not cutting me at all in the process. She shaved my legs first, then moved up, shaving away my pubic hair, the hair around my asshole, and on up to my chest hair. I couldn't tell if she was using just shaving cream, or one of those things like Nair that keeps the hair out for weeks. Either way, trips to the gym were going to be interesting. I'd have to tell folks that I was a swimmer or something.

When Jane was through, she removed the chain from my neck, and I heard her press a switch. The hooks that my arms were linked to started to lower, and as they did, I had no choice but to kneel, as the hooks lowered to about two feet above the ground. When they had stopped, Jane reattached the chain to my neck. She then proceeded to wash my hair. When she was done, I heard some rustling, and Jane threw her bra and panties in front of me. "My turn to clean up," she said. For the next few minutes, I could only hear her as she took care of cleaning herself, and I was tortured by having to imagine her body, which I still hadn't seen without clothes.

As she was cleaning, I tried to figure out just where things were headed. Jane had said that she'd planned this for a while, and she's clearly spent a lot of time and money setting up her apartment for bondage. Had she done all of this just for me, or was this her lifestyle anyway, and had she simply decided to have some fun with me? And where did she even get that much money as a secretary?

"Okay, now it's time for you to put your mouth to work, just like I said you would yesterday." Now this was something I'd been looking forward to! But before I realized it, Jane had slipped a pair of swim goggles over my eyes. They completely obscured my vision, only allowing me to see a little bit of light.

" Not to be immodest or anything, sweetie, but my body is, as you know, damned hot. You'll have to earn the chance, to see me naked! Now stick your tongue out and don't be squeamish – I just cleaned myself thoroughly, and it's as clean as it'll be all day." 

I had not idea why she thought I'd have a problem with eating her out, but before I could work out what she'd meant, Jane grabbed my head and pulled me forward. As my tongue touched her, I realized that she was having me lick her asshole! By the time I'd even thought to pull back, Jane had already yanked me tight against her, and I clearly had no choice, and just started licking. 

At first, it felt not much different than eating someone out, as I was mainly just licking around her hole, but Jane pulled harder and made it clear that my tongue was supposed to go all the way inside her, so I did. This was a truly unique feeling. The closest I could think of is an ex-lover who would suck my tongue when we kissed, but this was much more intense, and much tighter. Whatever I was doing was obviously working, as Jane hit at least two orgasms during the ten minutes she had me working on her. When she was done, she stepped behind me and pulled off the goggles. I still hadn't seen this most beautiful woman naked.

Jane again removed the chain from my collar and flipped the switch, allowing me to stand up. When this was happening, I heard her getting dressed out in the bedroom. After about a minute, she came back in, wearing a terrycloth bathrobe and carrying a towel. She dried me off, then reattached my arms to my collar and helped me out of the tub. She attached one of my ankle cuffs to clip next to the sink, handed me a toothbrush with toothpaste, and left me to brush my teeth while she fetched some more stuff.

Brushing your teeth with your arms tied to your neck is, believe it or not, probably harder than it sounds. But it can be done. Since my hands were close to each other, I could switch the brush between hands, allowing me to get most of my mouth clean. I'm sure the job I did wouldn't be approved of by the ADA, but at least my mouth felt a lot fresher. Still, it took about five minutes, and only when Jane came back (carrying yet another bag full of things I probably didn't want to know about) and filled a glass with water could I finally rinse and finish.

When I was done, Jane reached into the bag and pulled out a pair of white stockings. "I know you'd probably prefer the slut look, after your performance last night, but since I intend to have you doing work around the house today, I thought the maid look was the way to go." Before she started, she tied a belt around my waist and tied it to a hook in the counter. She then removed the ankle straps, lifted my left foot, and rolled it up my leg. She repeated this for the other leg. When she was done, she rubbed my lower thighs (where the stockings ended) and said, "now, don't these feel nice against your smooth legs?" I wasn't sure about the stockings themselves, but her rubbing my thighs certainly was enjoyable.

"Now it's time for your shoes." Jane lifted each of my feet and placed a black shoe on them. I didn't have the greatest view, but they were clearly bigger than the shoes of the night before, and they covered my entire feet (definitely not sandals this time), as well as part of my ankles. They also clearly were heeled, as I could feel immediately after she'd placed both of them on me. 

There must also have been buckles of some sort on them, as I felt her secure them to each other. She then removed the belt and attached a garter belt in its place, which she promptly attached to the stockings. Jane then led me out into the bedroom again, which was a long journey, as there was only about a foot of chain between my ankles. I was able to see my legs more clearly. The stockings were a white mesh, not solid white as I'd thought, and the white garter belt matched them perfectly. The shoes were solid black, with a wide toe, and the buckles on the ankles made them look almost like mini-boots. They weren't the sexy sort of shoes one might expect on a woman, but they had the functional look a maid's shoes might have. Except most maids didn't have two-inch heels to walk around in, I'd bet.

Jane strapped me into an armchair, securing my neck, hands, and feet. She then strapped each of my fingers into a restraint as well. I was as immobilized as I was last night, and, I suspected, for much the same reason.

Indeed, Jane plopped down in my lap with a makeup kit, and once again got to work painting my face. While she worked on me, she squirmed around in my lap, so I have to admit, I wasn't completely paying attention to what she was doing, although the routine seemed somewhat more elaborate than last night – she started by shaving me, and uses assorted powders and brushes and other stuff I'd never even seen before on me. When she was finished, instead of untying me, or holding up a mirror, she blindfolded me instead.

"Don't worry. I just don't want you seeing how pretty your nails look until I'm done." I really wasn't surprised to hear this. After all, why else would Jane have tied my finders down? She spent about ten minutes on my nails, and from the pressure she put on them and the filing noises, I figured out that she must be putting some of those nail extensions on me. I had no idea how one removed those, but I was sure that there had to be some way to remove the nail glue that was used. When Jane was finished, I heard her footsteps leave the room, and she yelled back at me that she was going to finish getting dressed while the nail polish dried.

A few minutes later, I heard her come back in, and she freed my arms and neck (but not my feet), letting me stand up, finally. Still blindfolded, I felt her raise my arms and attach them to what I guessed were hooks hanging from the ceiling. Jane then set about getting me dressed.

The first thing I felt her put on me was around my waist. At first, I was confused, since I already had a garter belt on, but as I felt the silky material on my buttocks, I realized that she was again placing me in panties, and that these must be the kind that fasten on the side (saving Jane the trouble of having to slide them over my legs). As she guided my penis through a hole in them, I realized that these weren't typical panties at all. As she fastened the clasp on the panties and my dick started to get hard, I realized that the panties had, for intents and purposes, a built-in cock ring!

I then felt her wrapping something around my torso. At first, I assumed it was the maid's uniform, but then I felt my waist start to constrict as she tied something in the back, and I realized that Jane was placing me in a corset. I now understood why she'd raised my arms, as it stretched my torso, and made the corset easier to put on. As she tightened it, I couldn't avoid groaning. I felt the skin under my chest pushed up, and by the time Jane was done, it was a lot harder for me to draw a deep breath.

Jane stood up, walked back in front of me, and leaned in, lightly brushing my lips with hers. "I'm sorry, sweetie," she said, still with the so-innocent sounding Midwestern voice. "I didn't mean to hurt you. And I really didn't mean to make you cry out. After all, I don't want to cause you to break my rules. We'll work on that later." She then wrapped yet another piece of clothing around me, one that went up to my neck and down to my thighs, and I guessed that this was the maid's uniform. 

Jane removed my arms from the hooks in the ceiling, and reattached the cuffs to clips on the side of the uniform. She then removed the blindfold. I could finally see how Jane had dressed herself, and it was worth the wait. She was wearing the same (I assumed) boots she wore the night before, but everything else was new. Instead of a bodysuit, she was wearing black stockings, a black leather skirt (ending just above her knees) with a huge slit on one side, exposing most of her upper leg (and confirming that she was wearing stockings and not hose), and a light white sleeveless vest, with only one button fastened. Under the vest, I could see a leather bra that barely covered her breasts. I could feel my hard-on straining against the cock-ring. 

Jane had also put on some makeup – dark red lipstick, and a little bit of eye-shadow. I had a hunch that she spent a lot more time on mine than on hers. Looking down at my hands, I saw that the nails that Jane had glued on added about an inch to each of my fingers. They were also bright red. Jane's nails were a darker, more professional, red, and they were actually slightly shorter than mine had been before she extended them! I couldn't imagine how she expected me to do anything with my nails like this. 

"Don't you look all pretty?" Jane snapped me out of my momentary reverie. "Just one or two finishing touches here." She placed a white maid's cap on my head. It had strings on it, almost like a bonnet, and she tied it loosely below my chin. She then fiddled with the uniform around my shoulders, and unrolled two sleeves. 

"Let's take a few pictures, shall we?" As if I had any choice in the matter. She picked up the digital camera and snapped shots of me from the front and from behind, then picked up a Polaroid and walked out of the room to go upload them. I once again took stock of my situation. 

Although I was, if anything, in a worse bind, thanks to the second series of photos and my fingernails, nothing Jane had done to me today had been as uncomfortable as what she'd done yesterday. And although the I hadn't had the opportunity to come yet today, I couldn't deny that I was turned on. Maybe this wouldn't be so bad after all. 

Chapter 5 – Maid Service

Jane came back into the room carrying a small bag and a mirror. "I know you want to see how pretty you look in your maid's outfit. But first, we need to do something to make sure you don't break the 'no talking' rule again." She grabbed my face and squeezed my face, forcing my mouth open. Before I really knew what was happening, she had shoved something in my mouth and pulled the strings on the bonnet tight, forcing my mouth closed over it. I felt something going back a couple of inches into my mouth, and I realized that she'd shoved a dildo into my mouth! While still holding it in my mouth, she looped a string that was attached to the dildo through the bonnet, and behind my head. I tried pushing it out with my tongue, but it was securely in place. It went about two inches into my mouth, and tasted of plastic.

"There. That should help you keep quiet. Now, lemme show you how good you look." Jane held up the mirror, moving from my feet up so I could get a look at everything she did.

Above the maid's shoes (attached to each other with a short chain) and white stockings, I now had on a classic French maid's costume. It was black with white ruffles, and went down to my lower thighs, making it look more like the costume a maid in a porn movie would wear that what a "real" maid might have on. My waist, thanks to the corset, was much thinner than normal, and the contrast made it appear as if I actually had some breasts, although the uniform was cut high enough to hide any sort of cleavage. It was not cut high enough to hide the studded collar, of course. The sleeves of the costume covered my arms down to my wrists, and my red fingernails seemed much more appropriate now that I had clothing on, although I'd never seen a maid who wore nails like these.

But it was my face that really astonished me. At first, it seemed like a variation of what she had done last night. But she had spent a lot more time on me this time, and the detail showed. My eyes had blue shadow again, but this time, there was some sort of layering of colors, so that it moved from light aqua near the top to a deep, dark navy at the bottom. My nose looked smaller, which I realized was due to the amount of foundation and powder she had used. Although I could feel what felt like a layer of gunk on my face, I couldn't recognize where the foundation ended and my skin began in the mirror. 

As for my lips, Jane had used the same dark shade on my that she'd used for herself. But, again, she'd put a lot more detail into it. The color was a dark red, but there was an outline of a brighter red. I guessed that she's used some sort of liner that was a tad brighter than the rest. She'd applied both more heavily than last night, making my lips appear thicker than they really were. The effect was the sort that could be neutral in some cases, but in this case, since my lips were wrapped around a thick (but not too long, thankfully) dildo, it was unquestionably erotic. 

The dildo was apparently modified a bit (not that I was an expert). Only about an inch stuck out from my mouth, and from what I could see, it was black, and had a metal ring attached to the end of it. The strong from the bonnet had been tied through the ring and then around my head, but I assumed that the ring was somehow also used to attach the dildo to a strap-on setup, like the one Jane had used on me last night.

"Now, let's have breakfast." Since I hadn't eaten anything since lunch the day before, I was starving. Jane grabbed me by the arm and led me into the dining room. Between the heels, the corset, and the chains connecting the shoes, it was slow going, but Jane finally sat be down at a chair in the dining room. She strapped my arms, leg, and neck to the chair and then went into the kitchen. She came out with a tray loaded with two plates of eggs and bacon, orange juice, and coffee. She placed one serving in front of me, and proceeded to set the other one at her end of the table. She started contentedly eating, while reading the newspaper.




A New Year Pt. 02



After about five minutes, the smell of bacon and coffee had made me ravenous. When Jane finished up, she looked up at me and feigned surprise, in her ever-so-innocent sounding voice. "You haven't touched your food! What's wrong?" She walked over to me and pretended to just notice the problem. "Silly me – all tied up like that, how could you eat. I suppose I could remove the dildo and feed you, but then you might talk or something. I've got a better idea!"

She did something to the headrest of the chair, and I felt my head tilt all the way backwards, as the headrest pulled the collar. She then fiddled with the dildo, and started pouring the orange juice into it – I realized that the ring was there to open up the dildo. She closed it, and I attempted to slurp down the juice, but nothing came. 

"This is a very special little cock, honey," Jane said. "You can suck on it all you want, but it won't spurt until I say so. Fortunately, I'm very good at making cocks spurt." She pressed a button on the bottom of the dildo, and a little bit of orange juice entered my mouth. I almost choked – it's really hard to swallow with a dildo in your mouth – but I was able to drink it down. Jane kept squirting orange juice into my mouth until I'd had the entire glass. She then got a glass of water and repeated the process, probably to clean out the dildo.

"There's no way to fit eggs and bacon through that, I'm afraid. Guess you'll just have to make due with the OJ." I was still starving, but the OJ had taken a little bit of the edge off, at least. And it wasn't like I could complain. 

Jane cleared off the table, untied me, and walked me back to the bathroom. "Now, it's time to earn your keep as my maid. After all, I'm feeding you and clothing you, so you should do something for me." As if I'd asked to be dressed like this. Jane attached a chain to my left shoe, and clipped it to the same clip at the bottom of the sink. This chain had enough slack to allow me access to most of the bathroom.

"Now, I expect you to clean this bathroom. There's a brush and all the cleaning supplies you'll need under the sink. I've got to run some errands, but I'll be back in a couple of hours. I expect this room to be perfectly clean when I return." Before I could breathe a sigh of relief at the prospect of a few hours to relax, Jane's usually sweet voice took on a more menacing tone. "If it's not perfectly clean, you're going to really regret it."

With that, Jane was off. I still wasn't too worried – the bathroom was pretty clean to begin with, and two hours should be plenty of time to make it sparkling. I reached down to open the cabinet below the sink, and that's when I realized the trap I was in. The corset made bending over almost impossible. And since almost everything I had to do to clean the bathroom involved bending over (and frequently getting on my knees). It was going to be a long morning! Even worse, the more I moved, the harder my penis became, as the combination of the cock ring and the bondage constantly aroused me.

Some time later, after tripping multiple times and feeling like I'd wrenched my gut a hundred times, I heard the door open. "Sweetie, I'm home!" Jane stamped into the bathroom, dropping some bags in the bedroom outside. "Wow! You've really made some progress! Before I look things over, take care of something out here. She walked out to the bedroom and grabbed something from the bed. It was a video camera! "Since I didn't want to miss your maid performance, I figured I'd tape it. As soon as I start uploading it, I'll take a look at the job you did here."

She taped me? The pictures were bad enough, but this was starting to get out of hand. And what could she accomplish by uploading it? The pictures should have been enough, if she just wanted to threaten me. 

Jane came back in, and started the inspection. The sink and bathtub passed with flying colors. The floor passed her white glove test, and I'd even remembered to wipe all of the smudges from the mirror. Then came the toilet. She gave the toilet a thorough inspection, even running a white glove under the rim! I knew I'd cleaned the bowl well, and I tried to get under the rim, but there's only so much you can do – it's not easy to see anything under there. Needless to say, Jane found some dirt under the rim, and held up her dirty white glove.

"Oh, that's too bad, sweetie! You came so close!" As usual, she sounded so sweet in that middle-America sort of way. Of course, I didn't doubt that this was as rigged as anything else – even if I'd managed to clean the toilet, she'd have found another way to "punish" me. If only I'd been able to realize how deceptive that voice of hers was a day ago.

Wow! Had it really been less than 24 hours since Jane had enslaved me? It's amazing how much things can change in such a short period of time.

"Now," Jane was saying, "all that shopping made me hungry, and although I can't imagine you really exerted yourself too much, given the state of things in here, I'm sure you wouldn't mind some food, either." Talk about an understatement! I was starving, and she had to know it!

I wasn't surprised to discover that lunch was essentially a repeat of breakfast. Once again, I was strapped into a chair, and once again, I was forced to watch Jane eat her lunch (a wonderful-looking fresh sandwich from a local deli that she'd obviously bought while she was shopping), while my equally-appetizing sandwich sat in front of me. 

After finishing her meal, Jane walked around to my chair, and I expected her to once again lean my head back and let me have something to drink. Instead she undid all but my feet straps, and had me stand up. I was thirsty and hungry, but standing in the corset was much easier than sitting, so I didn't mind. 

Chapter 6 – Going for a Ride

"I think you've done enough as a maid. At least, for today. Let's get you out of these clothes!" I was so relieved to hear this, and within a couple of minutes, she had removed the maid's uniform, the shoes, and the corset. When the last came off, I breathed a huge sigh of relief, as I felt my tortured ribcage start to expand back into its natural position. I was now wearing just the stockings, the garter, and the bonnet.

As Jane attached a leash to me, and started to lead me to the bedroom, I realized that I'd somehow stopped considering the collar (to which the leash was attached) or the straps on my wrists and ankles to be clothing. Jane didn't seem to have any intention of taking them off this weekend. But I felt more free than I had all day – the lack of the painful corset crushing my ribs and the shoes hurting my arches meant that this was, comparatively, paradise. 

When we got to the bedroom, Jane tied me down to the bed, spread-eagled, just like the night before. Of course, since it was only a bit before three in the afternoon, I assumed she wasn't about to put me to bed. After securing me, she blindfolded me. This was my second time today being blindfolded, and I really didn't like it – being bound is bad enough, but not being aware of what's going on around you is pretty frightening. However, since I was still wearing the bizarre penis gag, I couldn't exactly say anything about it. I heard Jane moving around for a few minutes, then I felt her weight on the bed.

"Now, after all that hard work in the bathroom, you surely deserve a reward," Jane said. "Not only will you be allowed to cum, but I'll even use my mouth! And if you're wondering why I blindfolded you, it's because you haven't earned the privilege of seeing my mouth around your cock yet!"

If I'd had to bet, I'd have said that Jane would not give the world's greatest blowjob. She certainly had gorgeous lips, but I still had that lingering image of that sweet, innocent person, and it was hard to reconcile that with those lips being wrapped around my cock. But as soon as I felt her mouth on me, I knew that I'd once again underestimated her. Jane started slowly, nibbling very lightly on the head of my penis, then kissing it. She then slowly worked her mouth around my entire cock (which was painfully hard, thanks to the panties). Soon, she was sliding her mouth up and down, and I was in ecstasy. As she worked on me with her mouth, she released the cock-ring, and I could feel myself get ready to cum. Just as I started to, she pulled her mouth off of me, but continued to stroke me with her hand. I felt like I orgasmed a pint of semen.

I felt Jane shift on the bed, and she did something with my gag. It felt heavier all of a sudden. She then removed my blindfold, and I could see that she'd attached something that seemed to extend the gag into the air. It took me a second to get it from my perspective, but I realized that she had attached a dildo-extension to the gag!

"Now, you know the rules – if you get to orgasm, I get to orgasm too. And since your dick is all tired out, we'll have to use this substitute." I found this really appealing – at last I'd finally get to see Jane naked! But she then put the blindfold back on. "Sorry, sweetie. I just wanted to give you an idea of what was about to happen. Just as you haven't earned the right to cum in me, you still haven't earned the right to see my cunt." As I adjusted to my renewed blindness, not to mention the shock of hearing Jane use the word "cunt," I felt her shift.

Jane first put her knees beside my head, bracing my head in place. Her feet (with boots still on) were draped over my shoulders. I felt her grasp the dildo, and lower herself onto me. She slowly slid up and down the dildo a few times and I found myself starting to get hard again as I felt her obviously-shaved pussy rub against me, and as I smelled her arousal. Then, things got rough. Jane started really riding me, moving up and down hard enough to make my jaw, already aching from being wrapped around the dildo for hours, extremely sore. When she would stop moving up and down, she'd squeeze my head even tighter with her knees and gyrate on the dildo. 

Throughout this, she was moaning and even screaming a bit as she guided herself to multiple orgasms. I couldn't tell you how long she rode me – between the bondage, the blindfold, and my aching jaw, I couldn't focus that well – but she had at least four orgasms before she finally slid off.

After Jane spent a few minutes recovering (as did I) I felt her slip something – a pillow? – under my head, raising my neck up so that my head was pretty much vertical. "That attended to one of my holes," she said, "but my ass needs satisfying, too." I felt her straddle me in reverse, her ankles grabbing the back of my head, and she slowly slid onto the dildo. I assume she lubed it at some point, as she slid right on. For the most part, this wasn't as bad as the first ride, as Jane went much more slowly, but my neck was seriously cramping from the angle she had me at. She took herself to two quieter orgasms, and the mental image of her ass coming within inches of (and occasionally bumping) got me hard again.

When Jane finally stopped, she removed the blindfold. She had put her clothes back on, much to my disappointment. She cuddled up to me on the bed and started rubbing my chest. "That was real nice, sweetie," she said in that sweet voice, as if I'd just helped her collate some papers, "and I think it deserves a reward. Looks like your dick is all hard again." 

She started stroking my dick ever so lightly with her left hand, while stroking my face with her right "It would only be right if I made your dick spurt again, wouldn't it?" I nodded as best I could, and she grinned and sat up. She rested her hand briefly on my penis, looked me right in the eye, and said, "I hope you didn't misunderstand me and think that I was going to make this dick spurt, did you?" I was confused. Wasn't that what she'd just promised?

Then she reached for the dildo, and pressed a button, and I felt something sticky and salty spurt into my mouth, and as I swallowed it to prevent myself from choking, I recognized it from the night before as my own cum! As she sat there and squirted my own cum into my mouth, Jane leaned in and whispered in my ear, "sweetie, it's only fair. This was the dick I rode, so it's the one that should come. And besides," she added, with a smile in her voice, "you needed to eat something, and this is the only protein I can fit through the gag!" As she finished – she must have filled the dildo with the entire load I'd spurted earlier – she started to untie my legs, and I wondered if I'd ever get the taste of my own cum out of my mouth.

Chapter 7 – Latex

The next half hour was largely a repeat of our morning experience, as Jane removed the makeup and the dildo attachment on the gag, then walked me into the bathroom for another shower. The entire routine was the same, except she didn't shave me (of course), and she didn't have me perform analingus on her. Instead, after she'd completed washing herself (again standing behind me so I couldn't' see her), she turned off the water. I was still on my knees. She removed the now-sopping bonnet, pulling out the penis gag that had been in my mouth for the last six hours or so. I flexed my jaw muscles a bit to loosen them up, but before I could say anything (by this point, I wasn't too worried about the "rules"), Jane reached around me, grabbed my jaw, and shoved something in my mouth. 

"This should be a lot less painful, sweetie." As she fastened it, I could feel that what she'd shoved in my mouth was some sort of sponge. It was a tad moist (and I greedily sucked down the water that was on it, since I was only thirstier than before), and although it was big enough to fill my mouth, it wasn't that painful, as I could move my jaw a bit more. There was a piece of plastic or something attached which prevented the sponge from going to far into my mouth, and once Jane finished tying the plastic strap to the back of my head, I couldn't push it out, either.

Jane finished drying both of us off, and then let me up and walked me into the bedroom. She had changed into a black bra (it might have been the same one as before) and a gray pair of panties. Since neither seemed particularly special, I guessed that she was planning on putting something else on. If there was one thing I was certain about, it was that Jane put a lot of thought into how she dressed herself

Jane walked me over to the foot of the bed, and strapped my feet to the chain at the bottom of the bed frame. She then walked around the side of the bed, grabbing me by the collar as she did so, and forced my head all the way down to the mattress, bending me over the footboard of the bed, and pulling my feet off the ground. She attached a chain to the collar and attached the chain to the wall, so my face was basically shoved into the mattress. She then secured my arms to the bed frame, completely immobilizing me. "I'll be back in a second, honey. I just need to get dressed. And upload the tape of our little workout, of course." I hadn't seen the camera, but I shouldn't have been surprised any more.

Jane took her time getting dressed, no doubt deliberately, leaving me alone, naked, and tied up, with my ass sticking up into the air, and a view of nothing but a few inches of mattress. Once again, I tried to figure out what Jane's plans were. Even if she released me tomorrow or Monday, I would have to find a way to remove the nails before then, and I certainly wasn't going to be going to the gym (or out on many dates) until my hair grew back. And why was she recording everything? The photos were blackmail enough, if that's all she wanted, and if just wanted to tape the sessions for her own viewing pleasure, she didn't need to upload them to a website, right?

After about ten minutes, I heard Jane walk back into the room, and she was clearly wearing shoes with heels on the now. I couldn't see how she was dressed yet, alas. She gave me a playful swat on the butt and said, "now it's time for your punishment, sweetie. You didn't clean the bathroom like you were supposed to, remember?" As if I could forget. I heard her rummaging through some bags behind me, and dumping some clothing on the floor.

"Before we start with the punishment, we need to get you dressed." I felt her attach yet another strap to each of my thighs, and attach those to the footboard. I figured that this meant she had to take the straps off, and indeed, she then removed the strap from my ankles. I felt her start to rub some sort of powder all over my legs, and then she grabbed my right ankle and started rolling something up it. At first I thought it was just a stocking, but from the weight of it, it was obviously latex or something similar, and my leg, even with the powder, started getting hot. She rolled it up to my knee, then repeated the process on the other leg. She then continued rolling the stockings up until they were at my thigh, just below the straps. I then heard her rummaging again in the bag.

"Now," she said, putting on a very business-like voice, "as I'm sure you know, I believe in fair play." I couldn't voice the sarcastic responses that came to mind. "I only allow myself orgasms after you've had one, and after all those orgasms you gave me this afternoon, I even let you come again. And we both had to walk around all day wearing panties, of course."

Her "logic" was ludicrous, of course, but I knew that even without the gag, anything I said would have been pointless. She was technically correct, of course, but only in a way that allowed her to pretend to rationalize her games.

"So, since you had the opportunity to stick a dildo in my ass, it's only fair that I get the same chance for you." Opportunity? As if she'd given me a choice. Of course, I'd suspected that this was coming ever since she put me in this position – I had learned something from last night, at least.

"Since you can't see behind you, let me show you the toy I bought today." She reached over me and placed a dildo in front of me. My eyes widened in shock – this was huge! It was easily twice the length of, and much thicker than, the dildo she had me wear last night!. It had a large piece of plastic on it that was obviously designed to make sure it stayed in – this was obviously a traditional buttplug, not a dildo. Seeing my reaction, Jane explained, "oh honey, don't be so silly. Naturally, you couldn't expect me to use a plug on you that's smaller than the one you fucked me with, right?" 

Jane then walked around behind me, and I felt her start to lubricate my ass. She then started to insert the plug into my ass. She worked it in slowly, pushing against my sphincter until it opened up and practically sucked the plug in. I couldn't even begin to describe how this felt. I thought I was as full as I could be the night before, but this plug was so much bigger. I felt like it was touching my stomach, and I couldn't believe I could hold it. It hurt a bit, but since she wasn't fucking me with it, it wasn't too painful.

Jane let me adjust for a minute or two, then reached around to grab my penis. "Well, I think you must like having a huge dick inside you." I didn't agree, but the pressure from the plug against my prostate had, indeed, made me as hard as a rock. I felt her start to roll something down my penis, and I realized that it was a cock-ring. I would be hard for a while. She then rolled something else down my penis, and I could feel that it was a condom, and it was very tight.

"This is a special condom, aimed at smaller guys," Jane said into my ear. "Oh, don't feel insulted – it's not that you're small, it's just that I wanted one that would be nice and tight, and since you won't need any slack in it – it's not like you'll be coming again any time this evening – this one was perfect." I was much less concerned with her opinion of my size than about the idea of not coming again that night. 




A New Year Pt. 02



Jane continued to roll the latex up my legs, and as it started to cover my ass, I realized that these weren't stockings – they were latex panty hose! They were also crotchless, apparently, as I felt nothing covering my scrotum. She flicked her finger against the latex covering the buttplug, and I felt the vibration going all the way up my anus. I couldn't decide if I liked it or not. 

Jane grabbed one of my hands, and made a "tsk"ing sound. "Sweetie, we can't possibly put you in gloves – these nails will ruin them. Let's see what we can do about this." She got something out of her bag – this was still clearly part of her plan – and laid washcloths beneath each of my hands. She then proceeded to trim my nails down to the top of my fingers, after which she started to apply nail-polish remover.

On the one hand, I was greatly relieved – obviously the fingernails were not a permanent thing, and wouldn't affect things next week at work. On the other hand, Jane was obviously preparing something nasty for me, and I wasn't looking forward to it. Worse, while she was working on my nails, Jane was lying next to me on the bed, and was alternately nibbling on my ear, kissing my neck, and rubbing the heel of her shoe against the latex-covered base of the buttplug. Obviously, my penis couldn't get any harder, but this constant state of arousal was starting to make me dizzy. The lack of food or water, as well as the way my legs were starting to sweat thanks to the latex, weren't helping. 

I couldn't even begin to guess how long Jane spent getting most of the polish off my nails, but when she was done and had wiped the nails clean, she grabbed my left wrist, rubbed lots of powder on it, removed the bondage strap, and rolled a latex glove up my arm. It went all the way up to my armpit – I didn't realize they made gloves that long! She then repeated the performance on my right arm, and ran some sort of strap that was attached to the glove across my back, between the top of the two gloves. She ran another strap across my chest, and repeated the same steps at my elbows, and tied my wrists to the latex hose. My arms were now not only encased in latex, but they were tied to my side!

Jane placed what felt like a shower cap on my head, and started to roll something over my face. It was powdered on the inside, and it smelled like talc. I realized, as she pulled the mask completely over me, that it, too, was latex. It had holes for my nose, ears, eyes, and mouth (not that the last did me any good), but otherwise completely covered my head. She then removed the collar, although I didn't try to stand up. She knelt behind me, and I felt her lift my right leg off the ground, and she slipped a boot onto me. As she zipped it up, I realized that the boot went nearly up to my thigh! I couldn't imagine wearing this! She pulled another boot onto my other leg, which was just as long. Jane had only been wearing boots that went up to her knees, but she expected me to wear these? 

Jane had me stand up, and as I lowered my feet to the floor, it was obvious that the heels were even longer than previously. She draped something else made of latex over my head, and I realized that it was a vest of some sort. She attached it to the arm straps, thus removing what little freedom my arms had. Her final piece was another collar, this one rubber as well. I was dripping with sweat now – my entire body, with the exception of a few patches here and there, was covered in rubber. Worse, the water from the sponge gag was gone, and sucking on the sponge was drying up my mouth, making me even thirstier than before! On top of that, the pressure from the dildo, combined with the heels, was putting a lot of strain on my back and ass.

Jane finally let me see how she was dressed, as she walked in front of me and posed. I'd expected a repeat of last night's costume, considering her theme with my attire. Instead, she went for the leather look, wearing a leather halter top, a collar, a miniskirt, and knee-high boots over black fishnets. This skirt, unlike the one from this afternoon, couldn't be worn in public – it was short enough for me to see the leather underwear she was wearing. She'd also changed lipstick, wearing a brighter shade of red that made her lips look absolutely cruel. For once, I could look at her and not see the woman who appeared so innocent. That didn't make her any less attractive, however.

Jane didn't pose – after stepping in front of me, she pulled out a mirror from under the bed, and I finally got to see myself. I couldn't even recognize myself! I was like some sort of weird latex doll. My entire body looked like a black latex dummy. Even the condom she'd used was black, which made my ever-hard member appear to be some sort of joke that someone had glued on. Since I also had on five-inch heels and the vest had breast forms sown in, I looked like a she-male. If it weren't for my eyes and my exposed scrotum, someone would have had to look long and hard at me to realize that I wasn't some sort of weird toy. After snapping a few pictures, she was set.

"Like what you see, sweetie? Good. Now it's time for the punishment!"

Chapter 8 – Punishment

What? Dressing me in latex so I was sweating like crazy, placing me in a gag that made me thirsty, sticking a giant dildo in me, and making me walk in these heels wasn't punishment enough?

Jane didn't give me any opportunity to answer, alas. She grabbed me and pushed me into the living room. Between the heels and my arm bondage, it was a slow, painful walk. I was guessing that she didn't consider this punishment, either.

I was right. When we made it into the living room, Jane kicked out my legs, and without my arms to balance me, I fell forward right onto the ottoman. She tied my knees to the legs of the ottoman, attached the collar to the front, and stepped out of the room for a moment. I heard her come in and stand behind me before she spoke.

"Now, last night I tried punishing you with a light spanking, and it didn't seem to have much of an effect. So we'll start your punishment with something a little more serious tonight."

Before I could wonder what she had in mind, I felt an incredibly powerful slap against my ass. The latex seemed to magnify the power of her slap, but I knew she wasn't using her hand, or even a hair brush. She spanked me ten times on each cheek, and five times right in the middle of my ass. All of the spankings made the dildo twitch inside of me, on top of the pain from the smacks themselves. Jane then casually tossed the leather paddle she'd been using in front of me – so I could see, after the fact, how I'd been tortured.

"Now, let's move on to the really serous punishment."

For the next half hour, Jane abused me, moving on to spankings with a ping-pong paddle, a hardcover book, and a ruler. She then moved on to whipping me, first with a cat o' nine tails, and then with a riding crop. With each item, she used the same pattern – ten swats on the left buttock, ten on the right, and five in the middle. With the two whips, she also hit my back. The latex probably prevented my skin from being shredded, but it still hurt like hell. 

By the time Jane finished, my ass was so sore, I could barely even feel it anymore. And my asshole felt like it had been fucked all night. On top of that, my back was sore from the whipping, and I was now drenched in my own sweat, with the latex holding it all in. My mouth was now completely dry. I'd do anything to get this to stop. And to think, just a few hours ago, I was thinking that Jane wasn't treating me so badly, and that the weekend might be fun.


Jane left me tied up as she heated up dinner in the kitchen. She walked back in and spun me around so that I faced the coffee table. She then placed her dinner on the table – it was spaghetti with a marina sauce, and it smelled wonderful. She sat on the floor and ate slowly, leaning on my head as if it were an armrest. With each bite, she'd hold the fork under my nose.

"Doesn't this smell delicious, honey? I'm a great cook. Too bad you've got that gag on, or else I'd let you try some. I was salivating even more now, and the sponge was sucking it up, of course. She also made sure that I got to smell the wine she was drinking. I was so thirsty, I couldn't even think about anything else. When she finished, Jane knelt in front of me to pick up her plate, and brushed her ass against my face as she slowly stood up. Between hunger, thirst, and horniness, I was being driven mad by my desires.

When Jane got back from the kitchen, she was carrying a large shopping bag. She untied me and walked me back into the bedroom. Thanks to the pounding my ass had taken, this walk was even more painful than the previous one. To "encourage" me, Jane would swat my ass if she felt I dallied. When we got to the bed, she had me lie down on it face-up. She tied my legs down, leaving my upper body a tad mobile, but because of the way my arms were tied to my sides, I really couldn't do much, especially when Jane crawled on top of me and sat right below my crotch.

"Well, what do you know? You're still hard!" As if I had any control over it, at this point. "It would be a shame if I wasted this."

She then moved up and slid right onto my cock. I realized that she must have removed her panties at some point. I attempted to sit up, but she kept a hand placed on my chest, keeping me down, so I still didn't get to see her naked. 

Jane rode me to two orgasms, and although it felt wonderful, the cock-ring prevented me from orgasming. Worse, the whole time she was fucking me, she was making me sweat, and putting pressure on the huge plug inside of me. I was so frustrated at this point, I was on the verge of tears again. When Jane slid off, I was almost relieved.

After resting for a minute, Jane looked at me with a perky little "surprised" expression and said, "I can't believe it – I forgot that I had something for you! You need something to drink!."

I was so relieved. I'd finally get the gag off and get to relieve my parched throat. I should have known better.

Jane reached into the bag and pulled out what looked like a baby bottle, except it was open at both ends. She took one end and screwed it to my gag. She then slid up the bed and braced her knees against my head, so the bottle stayed upright. If it hadn't been for the bottle, I might have had a chance of seeing up her skirt.

She reached into the bag again and pulled out a tiny bottle of Evian water – this was the really small bottle that you get served on airplanes, barely enough to fill a plastic cup, but it looked like ambrosia. She poured it into the bottle and I felt the wonderful water start to seep through. I sucked it down greedily, and within a few minutes, I was done. The water tasted wonderful, but it didn't even come close to quenching my thirst.

Jane looked down at me. "Are you still thirsty?" I nodded as best I could. "Well, let's see if I have anything else for you. She unscrewed the bottle, and removed part of the plastic clip at the front. She then crawled up over my face – carefully using the skirt to hide any glimpse of her pussy – and sat down on the sponge in my mouth.

I knew what was coming, even as I hoped I was mistaken. Sure enough, as her knees closed against my ears, I tasted a warm, salty, and slightly bitter liquid seeping through the sponge. I attempted to stop sucking, but between the gravity forcing more urine into the sponge, saturating it, and the thirst that made my mouth instinctively pull on the sponge, I ended up drinking every drop, god help me.

"Once I saw that you'd failed to clean the toilet, I thought this might teach you a little lesson," Jane said, as she squeezed my head with her knees and watched me drink. "Besides, my plumbing needs some work, and by having you dispose of my urine, I can avoid putting any more stress on the pipes than I have to."

Jane continued peeing for what felt like five minutes. She must have saved an entire day's worth of piss for me! She waited until I'd sucked it all down then slid off the bed. After putting everything away in the kitchen, she came back and replaced my latex collar with the leather one, and attached it to the bed again. She then proceeded to remove all of my latex restraints (and replacing my leather cuffs), from the mask to the hose, finishing with the cockring. But she left the condom on, although she pulled it up slightly, creating about an inch between the end of my dick and the end of the condom.

I was now naked other than the collar, the cuffs, the condom, and the gag. Jane looked at me and smiled.

"It's funny. After all the paddling and the humiliation, you're still hard, even after I've taken off the cock ring. You know that that tells me, sweetie? That you really do enjoy being a plaything. That, or the thought of seeing me naked really drives you nuts." Much as I wanted to deny it, I was, indeed, still hard.

"Even though I said you weren't coming again today, I think you've earned the right to orgasm inside me. Of course, I'm not ready to let you go bareback, so I'll use this condom." She then hopped on me and started riding me again. Between the huge state of arousal I was in and the dildo that was still inside of me, I came in an explosive orgasm in less than a minute. Jane did not look pleased.

"Sweetie, just because you earned the right to orgasm doesn't mean that you could squirt so quickly. I expect my men to last." Jane then got off of me, pulled the condom off, and attached to more lines to my collar – my head was now trapped, so I couldn't turn it at all. She then grabbed the condom and emptied the cum I'd shot into her hand. She took it and rubbed it all over my face, managing to cover just about every inch with my sticky semen. Every inch of my face, including my eyebrows, was covered with the gunk.

Jane walked away, once again making a comment about uploading some pictures, and in the ten minutes she was gone, I felt the cum on my face dry. It felt like I had a layer of clay on my face now. Of course, I knew that this had been a part of her plan; there was no way Jane could have expected me to not be on the edge after a full day of teasing, after all.

"Sweetie," Jane said, as she removed the two cords that immobilized my head, "this should teach you to only come when a woman is ready. Now, I think it's time to go to bed. Tomorrow, you're going to experience an entirely different kind of facial." I had no idea what she meant, but it sounded ominous.

Jane was about to leave, when she turned around, Columbo-style, and faked a surprised look. "Oh, I forgot about that plug. You can't sleep with one that large inside of you!"

She reached between my legs and slowly pulled the plug out. It seemed to take forever, and when it was finally out, it felt as if my anus remained wider than before.

She then pulled out a smaller plug – smaller than the one from last night, even, although it was a bit thicker – and lubed it up. It slid right in, although it was still somewhat uncomfortable.

"This should be better. Much smaller than the other one." I was relieved – I wouldn't be comfortable tonight, but other than the gag, and the cum, it wasn't that much worse than last night. Then I felt Jane reach between my legs and flip a switch, and the plug started to vibrate.

"That should give you some pleasant dreams, sweetie." Jane snapped one final picture of me, then turned of the lights and closed the door. As the door shut, I felt the vibrating plug start to nudge my prostate, and I knew this would be a longer night than the last.



A New Year Pt. 03



Chapter 9 -- Dressing For Success, Again

In spite of the vibrating plug, I somehow fell asleep. When I woke up, it had stopped vibrating. I didn't know if the plug had run out or if Jane had taken pity on me. It took me a second to realize that the gag had been removed during the night as well; I guess Jane really had decided to take it easy on me. I'm normally a light sleeper, but the last two days had worn me out, and I had no memory of her removing the gag.

I rested, dozing on and off, and evaluated how I was feeling. My face was still sticky with my own cum, my asshole was filled with a plug, and I had sore muscles from being tied up. But I was also rock hard, and had experienced two intense orgasms over the last two nights. I wasn't sure if that meant that I really liked everything Jane was doing to me, or if my body was just capable of overlooking some of the things she'd done. 

I dozed until Jane came in to wake me with a kiss. 

"Good morning," she said, once again straddling me and sliding her panty-glad crotch slowly against my cock. "Oh, that feels so nice! But we've got a lot of stuff to do today, so I can't play with it now." As she said this, she slid up my cock, and I could feel the warmth of her pussy through the thin panties. If she hadn't slid off when she did, I might have come right there. 

"I'll tell you what," she said, as she started to untie me. "If you're a good boy today, not only will you get an orgasm, but you might get to see me naked. Does that sound fun?"

"Yes, Jane."

She smiled. "That reminds me. Calling me 'Jane" is a little too familiar, isn't it? I think you should call me something else. How about you call me 'my queen?'"

I knew that, even though she'd phrased it as a question, I didn't have a choice. "Sure, my Queen."

She grinned, leaned down, and kissed me. As she pulled back, she giggled. "I like the sound of that. 'Queen' means so many wonderful things." I wasn't sure what she meant, but assumed that she was happy enough with the title and the implied ownership she had over me.

The morning routine wasn't much different from the one the day before. I was allowed to use the bathroom, then given a shower, forced to perform analingus, and dressed once again. This time, however, I was placed in boxers, sweatpants, a hooded sweatshirt, and a pair of sneakers. Everything seemed mundane, but I knew there had to be a twist.

Sure enough, after Jane finished dressing me, she sat me down on the couch, where she placed the pair of frosted goggles over my eyes again. She followed that by guiding my hands into the pocket on the front of the sweatshirt, where she quickly bound them together.

Jane left me waiting for a few minutes, presumably to change out of her bathrobe. When she came back in, she straddled me and gave me a long, deep kiss. It was, goggles and cuffs aside, not dissimilar from the way things had gotten started two nights ago, and I was hard almost instantly. She suddenly pulled away mid-kiss, and before I realized what was happening, I felt her shove the ball gag in my mouth.

"If you hadn't already noticed," she cooed in my ear, "I really like gags. If I didn't like using your mouth for other things, I might keep you gagged even more. You have no idea how much seeing you like this turns me on." 

As she talked, Jane rubbed against me, and between the way her groin felt on mine, and her breath in my ear, I was nearly ready to burst. Suddenly, she stood up.

"I've got a lot of other gags I plan to use on you, but for now, we've got places to go." She led me away, and I realized we were heading outside. I knew that I could try to run away when we were outside, but I couldn't remember how many steps there were before the car, or where the street was in relation to the front door. Getting run over or breaking my neck weren't appealing alternatives.

Jane led me down a bunch of steps to the car. I knew it was early Sunday morning, so I guessed there was no one around to see me as she buckled me into the passenger seat. With my hands tied, the seat belt effectively became yet another bondage device.

After she sat in the driver's seat and turned the car on, I felt the seat begin to move, and realized that Jane was lowering the seat back, so I was lying down.

"I figure you don't want anyone seeing you with that gag on through the window, right?" I'd have thanked her, but my mouth was full.

Before we got started, I felt a cloth on my face, and soon detected a smell that I recognized by now as Jane's scent. "These were the panties I slept in last night. I figured you might enjoy them." Sure enough, I felt my cock hardening.

With my eyes covered, and distracted as I was by Jane's odor, I had no idea how long we were driving, or where we were. At every traffic light, Jane would reach into my sweatpants and lightly squeeze my cock, constantly keeping me at full attention.

Eventually, we stopped, and Jane removed the panties and let me out of the car, leading me a few feet into a door that jingled as it was opened. She walked me a few feet in, then sat me down and removed my pants and sneakers. She then untied my hands, removed my sweatshirt, and reattached the cuffs to my collar. Other than the collar and the cuffs on my wrists and ankles, the only thing I was wearing was the pair of boxers.

Jane then removed the goggles, and I looked around I was clearly in a beauty salon. There were the usual reclining chairs, hair products, makeup, and other stuff I'd have expected. A curtain had been drawn across the front of the salon, so I couldn't see the name of the salon or the door.

"This place is normally closed on Sundays, but I made some special arrangements for you." Jane giggled a bit as she said this. "You can come out, girls."

Two women walked out of the back room. The first one was short, with straight black hair that went down just to her neck. She was probably about thirty pounds overweight, but carried it well, with the weight all in her breasts and ass. She was wearing a long white skirt, a form-fitting sweater, and plain sneakers. She appeared to be in her teens or twenties.

The other woman was taller, around my height, with long, wavy brown hair, and a slim, but still lovely, body. She looked to be around 40, but was put together extremely well. She was wearing a tight black dress that flared out over black stockings, and very sexy red stilettos.

Jane informed me that the shorter girl was named Randi, and that the taller one was Donna.

"These ladies are going to give you a professional makeover. And as a treat, they're also going to get to play with you. I've given them only two rules: They can't let you have an orgasm, and they have to record everything. I expect a good show to watch tonight!"

With that, Jane kissed me on the cheek and left.

The two new ladies grinned at me. Donna wore bright red lipstick, while Randi wore a darker shade, closer to a brown. Both had full, lovely lips. Donna was the first to speak.

"Oh, this should be fun," she said, walking up to me. "We've got you for four hours, and we certainly won't need that much time to handle your makeup."

Randi joined her, standing behind me on the other side. Each started tweaking a nipple as they talked. "We're so happy Jane gave you to us. There are things none of my boyfriends have ever let me try," Randi whispered in my ear.

Donna giggled. "She's only eighteen, and you wouldn't believe the things she's done. As for me, I've had a fantasy I've been dreaming about for years."

With that, Donna moved down to my feet, and before I knew it, had attached a small length of rope between my two ankle cuffs. She then unclipped my hands from my collar -- Jane clearly must have given them the keys at some point.

"Kneel," she ordered. 

I did so, and she tied my wrist cuffs together with the rope as well. There was about a foot of rope between each hand and each foot; not much room for me to maneuver. 

"Randi, take care of him while I go change, okay?" She went into the back, and Randi straddled me, sitting down on my back. Although she was very pleasantly plump, she was short enough that her weight wasn't a huge bother, at least for now.

"I'm not normally into ponyplay, but there's something nice about sitting her with a man under me like this." As she talked, Randi lightly ran her fingernails down my back. As I recalled, her nails were pained a metallic blue, a color that worked for her, even though it would have seemed out of place on an older woman. 

"I know what you're thinking: How can someone so young be this experienced? I've been having sex since I was fifteen, and I knew that I wanted to dominate boys long before then. Trust me, I know what I'm doing." She leaned forward so that her breasts brushed the back of my neck through the sweater. "And I bet the idea of a woman as young as me controlling you is exciting, isn't it?" 

I couldn't deny it; I was still hard.

Just then, I heard footsteps, and Donna returned in an outfit that floored me. She was wearing a latex halter top that clipped closed in the front; it showed a huge amount of cleavage, and hugged her breasts perfectly. She was wearing a latex cheerleader-style skirt, which flared out but still show the curve of her body. If I was disappoint that it wasn't skintight, that changed quickly, as Donna had put on a pair of latex boots that went to her thighs, vanishing beneath the skirt. With the platform and heels of the boots, she was easily over six feet tall now.

Randi got off me, and Donna asked, "so, do you like it."

"It's incredible," I responded, truthfully.

Donna looked at me for a second. "That was a rhetorical question; I could see your reaction. Fortunately, I've got uses for your tongue, but maybe we'll gag you later." 

She grabbed something off one of the chairs and walked over to me. It was a pink leash. I wasn't surprised in the least to see her reach down to attach it to my collar. As she did, I noticed that her nails were painted the same shade of pink.

"Now, I want my pet to follow me so I can feed him." I hadn't realized just how hungry I was, but I hadn't had breakfast that day, and I'd eaten too little the day before, as well. I did my best to follow her, but the short ropes made it hard to move quickly. Even with the high-heeled boots, Donna had a huge stride, and "accidentally" ended up tugging the leash more than once as she led me across the store.

She stopped at another salon chair, no different than the first one, as far as I could tell. I didn't doubt that the whole point was simply to make me walk. I also didn't doubt that Randi was catching it on camera.

Donna sat in the chair, dragging the leash so I was forced to kneel at her feet as she lay the chair back, reclining fully.

"I've always wanted to have a guy lick my boots. Start by kissing the heels, then lick your way up."

I did what she asked. The latex seemed new; other than rubber itself, I wasn't tasting anything, which was a relief. As I worked my way up her leg, I had to lift my hands up to lean on the chair. As soon as I did so, Donna yanked the leash.

"Stop. I can't have your filthy hands touching me. Randi, can you help?" As she called out, she hooked her boot behind my head and pushed me down against her other boot. THe smell of latex was nearly overpowering.

I hadn't realized how close behind me Randi was, but I once again felt myself with her weight on my back, as she leaned down and undid the rope from one of my hands. Before I had a chance to think, she'd pulled my arms behind my back and clipped them together.

"Hmm, that's not bad for a start, Randi. But don't you have something better?"

"Oh, of course I do! I just needed something to hold him temporarily!" Randi stood up and I heard the too-familiar sound of buckles and gear being pulled out of a bag. 

I soon felt her strapping leather around my arms, right above my elbows, and also placing some items near my wrist. I tried to figure out exactly what she was doing, but before I could, she'd unclipped my cuffs and forced my arms up at ninety-degree angles. My arms were immobilized.

"Oh, that's lovely," Donna said. "You should show our pet what you did. I heard the click of a camera, and Randi held the digital display in front of me. A big leather cuff covered my forearms, holding them together, while straps at my elbows attached to the cuffs, holding them in place. For good measure, the arm cuffs had also been attached to the elbow straps.

"Randi specializes at immobilizing boys. Now, let's have you get back to your licking."

With my arms immobilized behind, me, I had to rely on Donna's leash for balance, and let myself simply get dragged wherever she wanted me. She eventually stopped and pulled out a jar of peanut butter.

"Now let's see you actually clean a dirty shoe." She spread a long run of peanut butter up her leg and pulled my tongue to it. I was starving, and the protein tasted wonderful. When I'd finished all of the peanut butter, my mouth was right at the point where her skirt dangled over her boot.

"You have no idea how hot it makes me to see a man use his tongue like that. Would you like to use your tongue on my pussy?" When I hesitated, she yanked the leash hard. "That was not a rhetorical question!"

"Yes, Ma'am, I would!" 

She smiled. "Good. But I know that Jane's been depriving you of the sight of her naked. If you haven't earned the right to see her pussy this weekend, I don't think you've earned the right to see mine, either."

Randi stood over me again, and this time wrapped something black and gauzy around my eyes. She wrapped it two or three times around my head, and it got gradually less translucent. I felt Randi lean down and whisper in my ear. "That was one of Donna's stockings. And here's the other." She slid the stocking over my head just enough to cover my eyes, then tied the rest of the stocking around my head to further blind me.

"Now," Donna said, "before you worship, let me tell you what's underneath my skirt. I'm not wearing any panties, of course, but I do have two thigh straps on. Once I lift my skirt, I'm going to clip your collar to the straps, and your mouth will be inches from my pussy. I'll then use your leash to guide you. You'll be released only once I'm satisfied."

She paused, and I thought she was about to ask me if I understood. Instead, I felt myself yanked up, and I heard the collar click even as I felt her thighs against my ears. She pulled the leash a little bit more, shifting her thighs, and my mouth was now in contact with her pussy.

I licked and sucked away. She did, indeed, have a wonderful-tasting pussy, and she was dripping wet already, clearly turned on by my bootlicking. In fact, she had her first orgasm almost immediately, and hit a second one just minutes later. Between her thighs and the skirt, I couldn't hear much, but I definitely heard her moaning. By the time she'd hit her fourth, my tongue was getting seriously tired.

The second I let up, however, she yanked the leash hard, pulling my mouth right against her pussy. Further, she crossed her thighs, pushing the back of my head with the top of her boots. My nose was pressed against the hairless top of her crotch, and I had no choice but to keep licking to give myself a chance to breathe.

At the same time, the area between my crotch and anus was resting on the metal footrest of the reclining salon chair. It was uncomfortable, but far from my focus. What I hadn't realized was that the pressure had softened my erection. As I licked, I felt Randi pull down my boxers, grab my penis and balls, and wrap something around them. It didn't hurt, so it was the least of my worries at the time.

Randi then flipped away the footrest, and I felt something wet against my asshole. She was lubing me up, but I was in no position to say anything (in fact, my protests only caused Donna to pull my mouth harder against her. I felt a dildo slide into me, and even as my prostate began to react, my cock was unable to expand. I had no idea what Randi had done, but I clearly wasn't going to come.

As the plug slid into place, Donna shuddered one last time and finally let me go.

"Oh, I think you might have tired her out," Randi said. "Why don't we get started while Donna takes a break?"

With that, she grabbed the leash and stood me up. As she removed the blindfold, I glanced down at my crotch, and saw that my cock and balls were encased in a tight rubber pouch. They simply had no room to grow.

Randi saw my look. "It's for you own good. Jane would get mad if you came without her permission!" She lifted my boxers back up, but slid the cock pouch out through the hole in the front.

She marched me over to the chair I'd been in earlier, and had me sit on the end of the chair. After buckling my feet to the footrests, Randi attached thigh straps to me, undid my armbinder, and attached my arms to the straps. She pushed me down, and quickly wrapped a tight strap around my chest.

"These portable bondage kits are wonderful. I can immobilize someone anywhere." Indeed, I was pretty immobilized already, but Randi had more in mind. She tied two more cuffs around my knees, securing them to the chair as well, and attached another loop to my collar. She also pulled the leash behind the chair and hooked it on the wall, locking my head into place. I was completely attached to the chair. 

"Ooh, I love it when a man is immobilized! Now I can start really having fun!" I wasn't sure I liked the sound of that, but all Randi did was remove her skirt, revealing a pair of lacy booty shorts. They hugged her incredible ass perfectly, and although the black lace hinted at the wonders underneath, they still fully covered her. The back of the underwear disappeared into her ass, making for an alluring sight.

"So, what do you think of my ass? Wait, don't answer that." She reached down to my crotch and felt the rubber packet. "Mmm, feels like you're straining in there. I like that."

She climbed onto the chair, straddling my chest. "Donna went for the blindfold to avoid having you see her naked, but I'm happy enough to have you lick me through my underwear."

With that, she turned around and sat her lace-covered pussy on my mouth. I was still tired from my workout with Donna earlier, but I did my best to please her through the thin layer of fabric in my mouth. But it soon became clear that this wasn't Randi's concern.

As I watched, almost in disbelief, she shifted her weight backwards, and before I knew it, had planted her ass right on my nose! With my mouth still covered, I couldn't breathe! I tried calling out, but as I mumbled, I felt Randi shudder a bit; it was clear that my struggles were turning her on.

It felt like forever without a breath, but I know I never lost consciousness, and it was likely only twenty seconds or so. Eventually, Randi lifted herself just enough for me to gasp before sitting down again. She repeated this a handful of times, before turning around and sitting on my chest.

"Having fun?" She had a twinkle in her eyes as she asked, and I knew she wasn't expecting an answer, even if I wasn't too out of breath anyway. "I love sitting on your face. Your mouth does such interesting things when you're trying to breathe. But here's a little secret: Much as I love this, the stimulation isn't quite enough to get me off. So I end up a little bit frustrated, and need an outlet. "

With that, she shifted back around and sat over my mouth, although she wasn't covering my nose yet. 

"Hey, Donna, can you see if he's enjoying this?"

"His mouth is filled with your panties and he's got a perfect view of your ass. I'm sure he's loving it. But let me check, anyway." I felt Donna's hands at my crotch, and in a few seconds, she'd removed the rubber pouch that had constrained my cock. Sure enough, I was hard in a few seconds.




A New Year Pt. 03



"Hmm, that looks good, but it could be the plug against his prostate," Donna said. I felt her slide it out. "Nope, he's still hard. He must love what you're doing!"

Before I could protest, Randi leaned back again. Even as I struggled for breath, I couldn't deny that my cock was staying rock hard, and there was something amazing about having a perfect ass over my face.

When Randi leaned forward the third time, allowing me to breathe again, she didn't lean back. Instead, I heard her say, "remember what I said about needing an outlet?"

I felt something sticky placed on my chest. I wasn't able to figure out exactly what I was feeling until Donna leaned down and whispered, "that's plastic wrap, baby. To help preserve you." 

I felt another sheet layered over my crotch, flattening my hard cock against my stomach. A third sheet was stretched out over the area between the first two (overlapping a bit on both ends), and then I heard Donna walk away and come back. Through this entire time, Randi remained sitting over my mouth, although I felt her idly rubbing herself through her panties.

"Now I can finally get my release. Donna mentioned how great I am immobilizing my playthings, but that's because I need you still for the stuff I really like. Facesitting is nice, but I can't get off without a little bit of pain."

That did not sound good, but my protests were, as always, muffled.

Randi leaned forward a bit, although she was still resting on my mouth, and I felt a sharp, burning sting on my chest. I felt another one next to it, but still couldn't figure out what she was doing. Then it hit me: She was dripping wax on me!

The pain wasn't unbearable, but it did startle me, and my muffled yelps clearly excited Randi, something I felt both in her shuddering and in the way she poured the wax. After splattering my chest and stomach, she paused and leaned forward a little bit more.

Before anything could happen, Donna leaned over again and whispered, "the best part of this is that Jane says that you asked for it."

What? I'd never talked to Jane at all about sex in any way, shape, or form! But then I remembered; I certainly had talked to her about wax. It was a few months ago, and it was a casual conversation about stupid things we'd done as kids. When I was at summer camp when I was young, my friends and I would did our fingers in the low-temperature wax used to make candles for arts and crafts, giggling at the sudden burst of almost-pain before it began to cool.

The wax here was hotter, although not unbearable. But then I felt the wax hit my cock, and the heat was much more intense on the more-sensitive skin down there! Fortunately, it cooled quickly, but there was a residual burning pain that lasted until the next drop hit.

Randi kept at it until my cock was covered, and I felt her shudder her way to at least two orgasms. The small blessing was that as she shuddered, I was able to breathe through my mouth as well as nose. Another nice bonus was that as she continued to come, Randi's juices soaked through her panties, which tasted wonderful.

I felt the plastic wrap lifted off of me, and then Randi twisted around, once again sitting on my chest. Her face was flushed, and she was holding the candle -- a bright red pillar-style one -- in her hands. With a wicked grin she pursed her lovely lips and blew the candle out, and handed it to Donna. 

Donna, in turn, gave the plastic wrap to Randi. It was splattered with red wax, but the section that had been above my cock was molded. They'd managed to cover my entire cock, and made a impression of it. 

"See, Donna, I told you he'd like it. He stayed hard the entire time!" Much as I wanted to protest that it was the tight plastic wrap or the presence of Randi's wonderful ass that entranced me, I knew that wouldn't be believed.

"Is your cock sore?" I was surprised to get a question approaching concern from Randi. As I opened my mouth to answer, Donna reached from behind me and shoved a ballgag in my mouth, strapping it behind my head. "It's okay, sweetie. We pretty much knew the answer already."

Donna pulled a rolling table over to the side of the chair, and Randi reached down and grabbed something off it. "I think it's time we did some of that makeover work that you're here for. But while I'm working, I bet that Donna can do something to soothe your cock.

With that, Randi started a very slow and thorough process of applying lipstick to me. With the gag shoved between my teeth, my lips were forced open, allowing Randi full access. I tried to pay attention to everything she was doing, but I was soon distracted when Donna poured something cold on my cock. 

"Does this feel nice, sweetie?" Not that I could answer, but I had to admit that it did. She very thoroughly spread the liquid, and then I felt her spreading it on the side of my cock that hadn't been touched by wax. She also spread it on the head of my cock, and it felt almost as if she was using a paintbrush. Whatever she was doing, it clearly wasn't just about soothing me!

All this time, of course, Randi had been working on my face, and they both finished at about the same time. Randi finally got off the table, and I felt relief I hadn't known I'd needed; no matter how attractive the girl, having her sit on your chest for a while can be exhausting.

"Want to see how pretty you look?" Randi held a mirror up to me. The ballgag they'd used was a solid black one, and the lipstick Randi had applied was a classic candy apple red. It glistened and looked like it was wet.

"I love the contrast," Donna said.

"Yeah, that's what I was going for. But we need to test it before we get on with the rest of the makeup."

"What do you have in mind," Donna asked, faking innocence.

"Oh, I've got an idea. You got to wear kinky clothes earlier. So it's my turn." With that, I heard her drop her panties to the floor. With my head locked into place, I couldn't even turn it to look at her, and they both knew it.

While Randi got ready, Donna looked me in the eyes and grinned. "You know she's naked just a few inches from you, and you can't see her. Doesn't that drive you a little bit nuts?" As she said it, Donna slowly dragged her pink fingernails down my chest and stomach. When she got to my cock she leaned over and blew gently on it. I nearly came right there.

"Careful, Donna. You don't want to send him over the edge." With that, Randi walked back into view. I could only see her top, but it was incredible. She was wearing a black push-up bra made of wet-look lycra, and her cleavage was simply incredible. She wasn't wearing anything else that I could see, but when she hauled herself up to sit on my chest once again, I could see that she was wearing shiny black vinyl panties. 

But the part that amazed me was that there was a small plastic phallus sticking out of the front of the panties. It was about as thick as the second dildo Jane had used on me, but only stuck out about three inches.

Randi grinned wickedly. "Jane told us she hadn't really explored your skills at sucking dildos much yet. And we need to see if that lipstick will stay on." This didn't have me too worried; the phallus looked smaller than the one Jane had gagged me with the day before, at least.

Randi took out the ball gag and slipped the fake cock into my mouth. It tasted of rubber, but wasn't uncomfortable.

"Suck it, baby," Randi said. She was leaning over me, her knees on the table above my shoulders, angling the dildo downwards into my mouth. I gave it a few experimental sucks, and Randi moved in and out of my mouth, moaning slightly as she did so.

"I don't know if you noticed, but the dildo isn't just attached to the panties. It actually goes through a hole and into me. So when I shift forward like this," she gasped in pleasure, "I get something out of it, too. 

"And there's another secret." she paused, looking me straight in the eye with an evil grin. "It's not two separate dildos; it's one long double-headed one." With that, I felt her push forward, and even as her pelvis pushed against my chin, I felt at least three more inches of the dildo enter my mouth, covered in her pussy juices. I heard a click, and knew that she'd locked the new length into place.

Randi thrust downwards into my mouth more times than I could could, only pausing to make sure I was actually sucking, and grabbing my hair to keep her balance. I could tell that the other head of the dildo was working its magic on her. However frustrated she'd claimed to be after "just" sitting on my face, I didn't doubt that she'd gotten over that my now.

Two orgasms later, my mouth sore, Randi collapsed driving the dildo down one last time. She slid off, pulling the dildo out with her. I was almost shocked that she hadn't left the dildo in my mouth.

While Randi caught her breath, Donna came up and looked at me. "Hey, great job! The lipstick didn't smear at all!" She leaned down and gave me a long, intense kiss, her tongue exploring my mouth as she held my chin in her hand. "Of course, " she said, coming up for air, " we could have just done the kiss test, but then Randi wouldn't have had as much fun, would she?"

Randi had recovered her breath, and quickly changed back into her earlier outfit, skirt and all. She walked up to me and said, "okay, now it's time to get to work on the rest of the makeup. Instead of sitting on my chest, she sat in a high-seated chair next to me, once again fitted me with the ball gag, and began to work on my face. The process wasn't dissimilar to what Jane had put me through yesterday, but it was even more thorough. 

Donna touched my hand lightly. "Jane seems to have already done a great job on your fingers and toes. I don't think there's any point in trying to top her. I guess I'll have to find another way to occupy myself."

I then felt, much to my surprise Donna start to rub something onto my body. I mumbled in confusion, and Randi leaned down and whispered, "oh, we've just got some extra makeup lying around, so Donna figured she's get creative. Nothing to worry about!"

Of course, I knew that everything was something to worry about. But I also couldn't exactly do anything about it. While Randi worked on my face, I felt stuff being applied to my chest and stomach. Some of it was liquid, and some felt like lipstick, but it was hard to really keep up with what Donna was doing. 

Both women soon finished, and stepped back to admire each other's handiwork. They each seemed impressed by what the other had done, and Randi giggled when she looked over Donna's work. That did not make me feel good. 

"Should we show him, Donna?" 

"Let's finish up first." 

With that, the two ladies started messing with my hair, pulling and pinching. It felt like they were putting a swim cap on me. As soon as I felt something brush the side of my face, I realized that instead of styling my hair, they were putting me in a wig. The pinching, I guessed, was from the wig clipping to my hair through the cap. The few strands that I could see were clearly dark black.

When they were finished, Donna went and grabbed her camera. She took a few pictures of me, moving from head to toe, and then brought the camera up for me to see their work. The first picture was of my face. I was wearing a black wig, with straight hair down past my shoulder. My lipstick was bright, shiny red. My eyes were highlighted with green shadow that was striking. Both would have looked silly with hair any less dark.

What really amazed me, though, was my face. Randi had applied enough powders and stuff to it that it had actually taken on something of a feminine shape; someone at first glance might not realize it was a man's face underneath, and even if they did, I wasn't sure they'd know it was me. Then again, I didn't doubt that they'd filmed most of the process.

"Do you want to see what I wrote on you?" 

With my head secured, I couldn't even nod, but Donna figured out my answer.

"Tough. Jane gets to see them first. She can decide if and when you're allowed to see them."

"Speaking of which," Randi said, "we need to get him dressed."

Donna got to work on my feet, putting a pair of stockings on me very carefully, removing and reattaching the cuffs at each stage. At the same time, Randi released my hands, sat on my chest, and pulled a dark gauzy garment over my head, pulling it over my entire chest. I felt something cold on my thigh, but before I could register what was happening, Donna had cut away my boxers.

Once they were both done, they adjusted the chair to the sitting position, leaving only my wrists once again locked to the collar, which in turn was still secured by the leash. I looked down, and saw that they'd put me a black two-piece body stocking. The only part of me that wasn't covered by the stocking ensemble was my groin. All of the words Donna had written were covered up, but I could see what she'd done to my cock: She'd painted it completely with red nail polish, using a color that mirrored my lipstick!

Donna reached down and stroked my cock. "I see you like my little art project." I wanted to say just the opposite, but her stroking made kept my cock rock hard regardless of what I thought.

Although it had taken me a second to notice, the body stocking also had sewn-in breast inserts. They were obviously fake, but I suspected that they'd look real under a sweater.

She next slid a pair of black platform heels onto me. The heel looked to be about six inches long, although it was at least wide, instead of the stiletto I'd been afraid of. The platform was two or three inches, which meant the heel wouldn't be so bad, but I knew that I'd still have balance issues.

Sure enough, I nearly fell as soon as they had me stand up.

"Oops," Randi giggled insincerely.

They slowly walked me around the side of the chair, and then Randi grabbed the leash and pulled my neck so that I was bending over the chair, my ass in the air. I didn't doubt what was coming next.

Sure enough, I felt a large, lubed plug slide into me.

I thought that Randi would let me up, but I felt something cold on my ass. It turned out that Donna had yet one more "message" to write on me. 

Once the nail polish on my ass had dried, Donna had me step into a pair of panties (while Randi still pulled on my leash). As she slid them over my crotch, she held my cock flush against my stomach. I felt the cloth pull tight over my cock; whatever panties she'd used felt very small on me. Donna had me lift my legs again, and much to my surprise, I felt a second pair of tight panties settle over me. She repeated the process again.

Randi giggled. "Ever heard of body shaping panties? That's what you've got on. They're thin and tough and meant to layer. With three on, you can barely see your bulge!" I didn't doubt it, but it was also a lot of pressure on my cock.

They stood me up, and I saw that the panties, which came partially my stomach, were the same black as everything else.

Next came a waist cincher, not as tight as the one from yesterday, but enough to still reduce my stomach and bulge out my chest. This was followed by a tight black turtleneck that they put on me one wrist at a time.

"Now, I get to have a little bit more fun with immobilization," Randi said cheerfully.

She had me stand with my feet together, and wrapped a short leather skirt around my legs. She laced it tightly. She then took each hand from the collar and placed it in a pocket on the skirt. The pockets had a hole in them, through which she attached my wrist cuffs to my thigh cuffs.

"That's one of Randi's best inventions," Donna said. It's a hobble skirt, but she customized it so it would work with cuffs. I'd never heard of a hobble skirt before, but given the way everything above my knees was held tight, I could figure out what it was.

Randi kneeled down and clipped my shoes together. I could see a short, maybe three-inch chain between them.

"Now, let's get you back to Jane." 

With that, Donna yanked on the leash, and the only reason I didn't fall over was that I don't think Ib could have. They marched me towards the door, and I did my best to move, although it felt like it was taking hours. Whenever one of them decided that I was "slacking," Randi would swat me on the ass, stinging even through the leather.

I was surprised to find that the door didn't open to the outside, but to a garage. The salon was clearly in an old converted house. Inside the garage was a van with tinted windows in the back; no one on the outside could see anything past the cab.

Donna led me to the back of the van, opened the doors, and gave me a push. I fell onto a cushioned floor, and Donna got inside and pulled me the rest of the way in. She attached the leash to a hook in the floor and did the same with my heels.

I felt more trapped than ever. I'd been used sexually for hours, feminized, had yet another plug inside me, and was completely immobilized. And worried as I was, all I could really think about was how rigid my cock was, encased inside multiple layers of spandex and leather, and how much I wanted to see Jane -- as well as these two newer women -- naked.

As Randi started up the van, Donna grinned and said, "here's a little something to keep you eager for the rest of the day."

She leaned down and placed a pair of headphones over my ears. They were the high-end noise-canceling kind, and even before she turned on the MP3 player attached to them, I was unable to hear anything beyond them.

When Donna hit "play" on the MP3 player, I immediate heard the sound of a woman orgasming, loudly. It sounded like something recorded from a porn movie. It went on for about a minute, then faded into the sound of a different woman. This was clearly a loop tape of nothing but sounds designed to make me horny.

As Donna stepped out of the door and the van started up, I wondered what else Jane and her friends had in store for me.



A New Year Pt. 04



Chapter 10: Orgy.

I have no idea how long it was until the van stopped. The assorted tracks of females moaning blurred into each other, and I wasn't able to fully pay attention to what was happening. 

Eventually, the van came to a stop, and Donna once again got into the back. Instead of releasing me, however, she merely sat on my chest and grabbed the MP3 player. She wore a wicked grin as she stopped the "music" I'd been listening to.

Much to my surprise, Donna reached down and removed my gag, although with the headphones on, talking seemed pointless. She then flipped her latex skirt up over my face. I felt her hand push down over my nose, and as I opened my mouth wide to breathe, she positioned her pussy on it and sat down.

She released my nose then and slid the skirt back, so that she was looking in my eyes.

All of a sudden, I heard Donna's voice coming through the headphones. She'd recorded a track just for this?

"Sweetie, remember when I said that I had a fantasy I'd been dreaming about for years? Well, I've had guys lick my boots before, and I've certainly had guys eat me out. So those weren't exactly fantasies, where they?"

Even though there was a pause, I couldn't answer. I suspected that her previous experiences hadn't been quite as bondage-heavy -- even at twice Randi's age, Donna seemed more innocent -- but I was more concerned with what she had in mind now.

"Jane said that you'd also drank her pee. That's one of my longest-held fantasies."

I wanted to protest, since yesterday, I'd at least had a sponge gag to control the flow. Here, I had Donna already sitting on my mouth. There was nothing I could do.

I felt Donna's thighs contract, and a steady steam of piss hit me. After a few seconds, my mouth was nearly full, and Donna lifted herself slightly and again pinched the latex skirt over my nose, allowing -- forcing -- me to swallow and then to open my mouth again. 

She repeated the process six times. Throughout, I wondered at the irony that even though I had this gorgeous woman sitting with her vagina on my mouth and peeing into me, I still couldn't see her naked, thanks to the leash holding my head and the latex skirt.

Donna never took her eyes away from mine. It was clear that she was as turned on by the look in my eyes as anything else.

When Donna finally let up, she placed her vagina over my mouth one last time and played another track on the MP3 player. "Now lick me clean!"

I suspected I had her shaved pussy clean in only a few seconds, but not surprisingly, she had me lick until she'd had another orgasm.

She then slid off, removed the headphones, and unattached the hooks at my leash and heels. Of course, with the full bondage ensemble, I was still basically stuck.

I heard the door open, and three pairs of hands helped pull me out of the van. We were in yet another house garage. It took me a second to get my bearings, but I remembered that Jane had been street parking before. Where were we?

"I know what you're wondering," Jane said. "I do have a garage, but if I'd pulled in here on the first night, you might have gotten a bit suspicious."

I looked around, and aside from the washer and drier and the usual utility shelves one would expect in a garage, there was also what appeared to be some sort of modified stockade device, as well as a cage and a few other items. Even before the knowledge I'd gained over the last few days, I'd have realized that something was up if I'd seen those.

"Don't worry, sweetie. I'm not planning on using anything here. Yet." All three of them were grinning.

"Now, let's see what you look like." Jane walked around me, examining everything Donna and Randi had done. She squeezed the hobble skirt over my cock, oohing when the girls explained the layers of Spanx they'd put over my cock to restrain it. She swatted my ass when they mentioned the dildo, sending a jolt through my body.

She finished looking over me and said, "I love the heels you chose." She looked me in the eye when she said so, and seemed to be waiting for a response.

"I didn't exactly choose them, Jane."

"Don't be silly! I've been watching you for months, remember? You always would steal glances at my feet. I thought it was a foot fetish at first, but you didn't seem to care if I wore sneakers or mary janes. So I played around a bit. You seemed to get more distracted when I was wearing higher heels. And you nearly walked into a wall on the day I wore platforms! "So tell me again that this is what you wanted!"

She had me. Of course, it wasn't what I'd wanted at all, but I did find her attractive when she wore these heels.

"I wanted these shoes."

"Good boy. Now open your mouth."

I knew that there was no point in resisting. She put a bit in my mouth and wrapped the gag around my head. I thought the gag was small at first, but then she started pumping it, and I realized that it was inflatable. After three or four pumps, my mouth was pretty full.

"This is your punishment. Not just for disagreeing with me, but for forgetting to call me by my proper title."

Crap! I'd forgotten to call her "my queen."

"Now apologize."

I tried to say, "I'm sorry, my queen." It came out more like, "I auugy y een."

"I could almost understand that." She gave one more pump, filling my mouth entirely.

The girls giggled, and Donna grabbed the leash and led me -- slowly -- inside. 

They took me into the bedroom and pushed me onto the bed, attaching my leash to the headboard. Jane had changed the sheets, and I was on top of a leather-topped mattress.

"Did you two take lots of pictures?"

"Oh, we got plenty," Randi said. "And lots of video, too. His entire transformation has been recorded."

"Great! And you hopefully had some fun with him, right? The girls laughed, while I could do nothing but lie face down on the bed, immobile.

"Now let's get changed for the next part, okay?" Instead of hearing them leave, I heard the sound of clothing being removed. Of course, I couldn't turn around or move to see any of the changes.

If I'd had any doubts that they were doing this to tease me, they were shattered when I saw Donna's latex cheerleader skirt thrown onto the bed past my head. This was followed by the rest of her clothing, as well as the clothing that Randi and Jane had been wearing.

After a few minutes, I felt a weight on the bed, and Jane crawled onto my back. She reached around my head and placed the familiar pair of goggles over my eyes.

"Much as I love how Randi bound you, we do have to make a few changes. Don't worry about the shoes, though; they're staying." Oh joy.

The girls stood me up and moved my cuffed hands from my thighs to my collar. They then removed the hobble skirt, although the chain on the shoes kept my legs mostly together. They next rolled down the slimming panties. Horny as I was, the constant pressure of the panties and the skirt meant that I was only at about half mast, and before I had a chance to grow again, I felt my cock and balls again sealed in a pouch.

I was leaned over something -- a chair back, I'd guess -- and felt the dildo slowly removed from my ass. The ladies followed this by sliding a new pair of panties onto me. The final steps involved removing my sweater (unlocking my wrist cuffs first, of course), and then wrapping what felt like a tube top around me.

They had me stand up, and then removed both the goggles and the horrible inflatable gag. 

The sight that greeted me was the mirror, and not a whole lot had changed. The top was a tight leather tube top, which hugged the fake breasts well and made them seem real. The panties were black, of course, and were crotchless, allowing my cock-pouch to show through. 

But when Jane turned me around, I was blown away. All three ladies were wearing matching leather dresses, which hugged their hips, showed a nice amount of cleavage, and ended inches shy of their knees. They also had black stockings, and amazing black buckled knee-high platform boots, all with sharp heels. Other than lipstick in varying shapes of red, that was it. Simple, and gorgeous.

Jane grinned. "You like what you see?" 

How could I not? "Yes, my queen."

Jane smiled. I'd passed that test, at least.

"Wouldn't you like to have sex with all three of us at the same time?"

I knew the question was a trap. But even if I'd had a choice, I'm not sure I could have given a different answer. Randi, short, plump, and more experienced at a barely legal age than I was a decade later, had a propensity for cruelty that worried me. Jane, my crush of so long, was utterly devious. And Donna, at least ten years older than me, seemed to view playing with me as a new, liberating experience. But the thought of being with all of them still got me excited.

"Yes, my queen."

They all smiled. "Of course you do. Get on the bed and kneel!"

It was tough with my heels and my hands bound, but I managed it.

"No, move over a few inches." I figured that Jane was messing with me, but I did so. It's tough to shift without putting your hands on the mattress!

When they felt I was in the right place, Randi and Donna got on each side of me and wrapped a pair of straps around my shins, right below my knees. I felt a click, and realized that they'd somehow attached my knees to the bed.

Jane grinned. "One of the great things about leather, sweetie, is that it's easy to put hooks and eyeholes into it."

They followed this up by attaching a chain to the back of my panties -- where I guess another hook had been added -- and to the headboard. Randi then hopped off the bed, grabbed the leash, and threaded it through a hole in the mattress. With a grin, she started pulling on the leash, and thus pulled my head and upper body down. Since my waist was stuck facing straight up, I didn't have much room to move, and soon found myself in the classic doggie-style position as Randi secured my collar to the mattress at the edge of the bed. Once my head was locked into place, they removed the chain from my waist, but in the position I was in, I couldn't move.

Things got even stranger next. Jane pulled a small leather ottoman about a foot in front of me, took my left hand, and secured the cuff to a stud on the ottoman. She repeated this with my right hand, but added an extra twist. She took a condom and slipped it over both my index and middle fingers. She then slipped three more over them, wrapping a rubber band at the base to keep them tight. A little flesh-colored adhesive tape held my other fingers shut.

The ladies stepped back to admire their handiwork while Jane took a few more pictures.

"You know what the best thing about this is, sweetie? Every single one of those clips and buckles is hidden out of sight. Of course, we still have one thing to hide."

With that, Donna kneeled on the ottoman, the skirt falling over my hands. She reached under and guided my double finger into her. She was wet enough that I glided right in, as she gasped.

Randi stepped between my arms. I wasn't surprised in the least that when she lifted her skirt, she was wearing what appeared to be the same panty/strap-on combo she'd used earlier. "I bet you missed this," she said as she slid into my mouth. I didn't in the least, but couldn't so anything about it.

Finally, I heard Jane get up behind me. I wasn't surprised to discover that my panties had a hole in the ass for easy access. I felt the lubed tip of whatever strap-on Jane was wearing brush against my hole.

"Oh, honey, I forgot to tell you what Donna wrote on your ass. It says, "fuck me here, and has arrows pointing right to your asshole. Isn't that cute?" With that, she slid into me, using a phallus that was certainly bigger than the one they'd taken out not that long ago.

For the next hour, I was their fucktoy, as they pumped my mouth and ass, and rode my fingers. They would occasionally switch positions, with all of them getting a turn at each "station," Fortunately, Jane switched to a different dildo when she pumped my mouth ("because you've been so good," she told me), but it was still humiliating and extended. I'd swear that the dildos got bigger with each woman.

The two older ladies eventually tired out (well after I did), but Randi, who'd been taking a turn reaming my ass, wanted to try one more thing, and Jane agreed to help.

Randi stood out of her panties, leaving the dildo stuck in my ass. She then wanted around to her initial position in front of me, turned around, and knelt over the ottoman. This placed her gorgeous leather-covered ass just inches from my face.

Jane sat next to me, her leather-clad body brushing against mine.

"Randi wanted to give you a special treat, so since you've been so good, we figure you've earned the right to see her ass." Randi lifted her skirt, and there was, indeed, a nearly-perfect ass!

"Tell her what you think of it," Jane whispered in my ear.

"It's an amazing ass." I wasn't lying.

Randi giggled. It was exactly the sort of giggle I might have expected from a girl her age flirting at a party, but in her case, I knew she had something planned.

Sure enough, she slid the ottoman backwards, pushing her ass towards my face. At the same time, Jane held my head straight and guided my lips right to Randi's asshole. "You know what to do," Jane said. Given no choice, I went to work.

I soon felt hands at my collar, and realized that Jane had clipped my collar to Randi's thighs and removed the clips from the bed. I was trapped licking her asshole until they freed me, with my nose pressed against the top of cheeks my only source of air. 

Periodically, Jane or Donna would push against my head, making sure that my tongue was deep inside of Randi. After three loud orgasms, Randi finally decided she'd had enough, and I was released.

Jane undid most of my restraints, leaving only my head in place. The others got their clothes, and also picked up a bunch of mini-video cams. "We should have lots of fun editing these, " Randi said. Jane hugged each of them goodbye, and each leaned down to give me a kiss on the cheek.

"I'd kiss you on the lips, but I know where your mouth has been," Randi giggled.

"Thanks, sweetie," Donna said. "Come into the salon anytime you need a touch-up."

Once Jane walked them out, she came back in and sat on the bed. 

"Now, let's get you cleaned up."

Chapter 11 -- Take a breath.

The routine this time wasn't too different from the last few times. I was once again led into the bathroom, chained and showered. Jane spared me the analingus this time, though, and when I was clean (and still naked), she led me back into the bedroom, where she tied me down again. 

"I need to run a few more errands, and I'm pretty sure you're worn out. Why don't you take a nap? This should give you some sweet dreams." With that, she slid a pair of panties over my head, with the crotch landing right over my nose. As she walked out, I tried to think about where my situation was headed, but Jane had been right; I was just exhausted, and even with her intoxicating smell in my nostrils, I fell asleep in minutes. 

I woke up to the sound of the door slamming later. I had no idea how long had passed, but I certainly felt refreshed. I heard Jane's heels click across the floor as she approached the room.

"I hope you had a good nap. I bought some really nifty stuff." With the panties over my head, I couldn't quite see her even as she sat down on the bed. She leaned forward and wiggled her fingers in front of my face. She's clearly had a salon treatment, and now had very sexy black fingernails. 

"You like? Of course you do, silly! I do pay attention to how you react to me at the office, after all. Whenever I wear black polish, you can barely take you eyes off of me. More than usual, that is." She giggled and ran the tip of her index finger across my bottom lip.

She sat down on the bed, and I heard the sound of her heels dropping. "I also got a pedicure, of course." She stretched one shapely calf out over me and wiggled her now-black toenails in front of my face. 

"Don't think I didn't notice how much you liked looking at my toes, either. Every time I'd wear open-toe shoes, you'd keep staring at my toes. And you've got some sort of attraction to weird polish colors, too. When I wore the blue polish last week, you practically walked into a wall staring at me!" It was true. And her current black pedicure was just as enticing.

"Why don't you show me how much you like it?" Jane moved her foot down to my mouth, rubbing her big toe against my lip. "Kiss my toe." 

I did so, giving it a light kiss.

"Now kiss the rest of my toes!" She slid her foot along my lips until I'd kissed each digit. She the slid the big toe back to the center.

"Now, suck my toe!" She bent her foot slightly and slid the toe over my lip and into my mouth. I licked it tentatively. 

"No, suck it like it's a tiny little cock!"

I did as Jane demanded, sucking and licking the toe for a few minutes. After a bit, I felt her shift the rest of her foot against my mouth, and she shoved the second and third toes into my mouth as well. I sucked and licked, but before I knew it, she'd shoved her entire front of her foot in my mouth, and was bracing her other foot against the back of my head. Jane's feet were not large, thankfully, but the entire foot was every bit as wide as some of the dildos she'd had me suck. Her toes had a slightly musty taste to them, but for the most part tasted clean.

"I told you I had plans for other gags. Using my foot's one of my favorite ones. It keeps you quiet and it keeps me entertained." Her breath was becoming ragged at this point, and I suspected she was actually going to come from my attentions. I couldn't tell if she was also masturbating while I sucked, or if it was just the toe action itself that excited her, but either way, she soon came.

She then got up and walked away for a bit. With her heels off and my eyes still somewhat obscured by the panties, I wasn't sure where she'd gone, but in a few minutes, she came back to the bed and slid the panties off my head. She also placed a curved pillow below my head. I did finally get a glimpse of what she was wearing, but was surprised to see that it was a rather conservative full-body dress. 

"Disappointed, sweetie?" Jane had obviously caught my reaction.

"Of course not, My Queen." I figured that even if she saw through the lie, remembering her "title" would help.

She smiled. "Mmm. 'Queen,' indeed." She reached down and grabbed something, and fiddled with the pillow. I couldn't quite tell what she did, but I felt a soft cushion against my neck, and my collar was locked into place.

"Do you know what 'queening is, hon?"

"No, My Queen."

"Well, I'll explain it to you in a bit. But first, let me go change into something more appropriate."

She walked away, and a few minutes later, I heard heels clicking on the floor as she approached. She stopped just out of range, and with my head effectively locked into place, I couldn't see her.

"You saw me in lots of leather yesterday, but I decided to go a little more extreme today." Jane lifted her foot and showed me the sexy black leather high-heeled ankle boot she was wearing. "I'd know you liked this even without watching you at work. There's not a guy on the planet who wouldn't be turned on by these." 

I could also see the bottom of what looked like leather pants, but it wasn't until Jane climbed on the bed and straddled my chest with her knees that I got to see what she was really wearing. It was a full leather bodysuit! It hugged every one of her curves, swelling at the breasts and showing off her hips perfectly. 

Jane grinned through her bright red lipstick. "You like it, I'm guessing?"

"Yes, my queen." I said. She'd already glanced behind her and seen how hard I was.




A New Year Pt. 04



Jane stood up and walked around to the head of the bed, leaning over me. "You know, you always told me how much you'd enjoyed that summer in England. Do you remember when we talked about all those words that mean different things? like 'Bobby' and 'boot' and 'lift?'"

As I nodded, she got up on her knees on either side of my head. With the strange pillow device restraining me, her knees weren't touching me, but I still had a great view of how tightly the catsuit hugged her ass and crotch.

Jane looked straight down into my eyes. "Care to take a guess what 'queening' means over there?"

As I opened my mouth to answer, Jane quickly lowered her crotch right onto it, silencing me.

"It means 'face-sitting,'" I heard her say, as she filled my mouth with her leather-covered crotch. "And I think you'll find that leather is a little less forgiving than the lacy cotton Randi wore!"

With that, she shifted so that her ass settled right on my nose, and for the second time that day, I found myself unable to breathe. My senses were dominated my leather. I could feel it, taste it and smell it, and all I could see was Jane's leather-clad back.

I felt myself starting to go a bit dizzy, either from the lack of air or the smell of the leather, but before I could lose consciousness, Jane shifted forward enough to allow me to breathe through my nose.

"Wow, Randi was right," I heard Jane say. "You really are into this." She leaned forward and gave my cock a squeeze. I'd remained rock-hard throughout. I tried to protest that I was not a fan of "queening," but with Jane's crotch still on my mouth, no words could come out.

"Oh, that felt nice, even through the leather! But I think we could have even more fun!" With that, she spun herself around again so she was once again seated on my chest. It felt good to finally work my jaw muscles a bit.

"That contraption over your head is a custom-made smotherbox. I think you can guess the point of it!" Jane ran her black-painted fingernail along my lip as she talked. "It allows me to keep your head still so that I can cover you whenever I want. But let's add something to it, shall we?"

With that, she slipped a leather blindfold over my eyes. I felt her shift around, and even though I couldn't see it, I knew that I'd be smothered again soon. Sure enough, I felt her settle down and cover my mouth and nose again.

Jane repeated the process a few times, spacing things out at different intervals, so I was never truly sure when she'd cover me again. The fourth time, she pulled a particularly mean trick, and just as she pulled away and I was about to inhale, she sat right back down, and I found myself inhaling nothing but leather. I was afraid that I'd actually lose consciousness that time, but she pulled off in the nick of time. Even with the blindfold on, I didn't doubt she was grinning.

Even as I got used to grabbing a breath whenever I could, Jane added another item into the mix. As she settled on my face again, I felt her playing with my nipples, pinching and flicking them. And all of a sudden, I felt a burst of pain. She'd put nipple clamps on me again! These were definitely tighter than the ones she'd used earlier, and the pain made me shout into the leather mound over my mouth.

From Jane's squirming, that was exactly what she'd wanted, and she spent the next few minutes both smothering me and flicking my nipples and adjusting the clamps, indirectly using my mouth to give her pleasure. There were moments when I was afraid that she'd forget how long she'd been sitting on me, but it was only when she finally orgasmed that things really got tense. As she shuddered, she pressed her ass firmly into my nose, nearly breaking my nose.

Jane finally slid off and turned around. After removing the clamps (which, after a fresh burst of pain as the blood rushed back in, was a relief), she asked me, "how are you doing, sweetie?" I couldn't see her eyes, but she did sound concerned.

"Honestly, near the end there, I was afraid you were going to break my nose."

"Oh, I'm sorry, hon! I hadn't even though about that, but sexy as the leather is, it doesn't really offer a lot of give. Hold on -- I think I've got a way to fix that."

With that, she slipped off the bed, and I heard her heels click away. When she returned a few minutes later, I didn't realize it until she'd climbed on the bed. She'd obviously removed her shoes. I felt her kneeling above me again, 

"Open up," she said. I knew better than to resist, but was shocked when I felt the contact of flesh against my lips. It took me a second to even process that she'd lowered her very naked and wet pussy over my mouth. And by the time I realized the implications of that, she leaned back, embedded my nose in her crack. It wasn't thankfully, buried in her asshole, but closer to the top of her crack. The skin did have a little more give than the leather, although breathing was still a challenge. 

After yet another orgasm, she shifted around, sitting next to me on the bed.

"You know," she said, "the pants weren't the only thing I took off." I felt her lean down and rub against my cheek. It took me a second to realize what I was feeling, but it was her nipple!

She rubbed it against my lip, and I strained to take it into my mouth. Alas, I was secured down tightly, and couldn't.

"Oh, poor boy. So hungry for it!" Even with the blindfold, I knew she was grinning as she said it. 

She slowly teased me, rubbing her nipples around my mouth and against my cheeks, never letter me taste them. After a few minutes, she relented and lowered one breast to my mouth. I sucked in her nipple and heard her gasp in pleasure. After a few minutes of my attention, she switched to the other breast. Then, just as I'd gotten completely caught up in the joy of the moment, Jane shifted forward, covering my nose with her breast!

Even as I struggled for breath, I knew that biting down on her nipple would make things worse, not better.

After a few seconds of my pointlessly struggling, Jane lifted herself up. "I'm sorry, sweetie! I guess I just got caught up in the fun!" I heard the teasing in her voice, of course. Not that I'd ever doubted she'd done that on purpose.

She leaned down and gave me a quick peck on the lips.

"But that's enough of that. Let me just get changed, and then you'll have to make a choice. 

With that, she walked away, leaving me blindfolded and confused.

Chapter 12: Decision

I heard Jane walk back in a few minutes later, and braced for whatever new torture she had planned. Much to my surprise, she untied me, removed the smotherbox, and even took off my collar. She slipped the blindfold off and sat next to me as I sat up.

She was wearing a pink sweatshirt and jeans, and had switched to a pink lipstick. I wouldn't go so far to say that she looked wholesome -- not after the last few days, and she still was wearing tall heels -- but the look was certainly closer to what I'd grown used to from her at work.

"You don't have to use my title for the next few minutes. I need to ask you something."

I wasn't sure how to react. Was this some sort of trap?

"Okay," I said.

She smiled at my cautious tone. "Remember how I said that if you were good, you might get an orgasm? And get to see me naked? This is where you get to make that decision. I like you. And I've known that you've had a crush on me for a while. But I've got special needs, as I think you've figured out."

She lightly brushed her fingers against my cock, which had been at half-mast, but instantly sprang to full attention.

"And I think it's clear that, no matter what you might think, at least a part of you is enjoying this. So I want to make you an offer. You've got two choices: First, you can leave here tonight. I won't stop you. If you do that, I'll pretend this weekend never happened. I'll smile professionally at work, but you'll never have another chance to be anything more than a co-worker. And if you're thinking of telling anyone what happened, I doubt they'll believe you, but I'm pretty sure you wouldn't do that." She smiled again, and I realized it was true.

"The second choice is that you agree to be my slave."

"What does that entail?"

"First, you move in with me. To the outside world, we'll be just like any other couple. And we will be a couple; I can't keep up this level of activity every day!" She grinned. "I like you because of our conversations at work about movies and books, so you'll still have free time to read and see friends. And I wouldn't dream of doing anything to interfere with your job."

"As for what I will do to you, I don't want to spoil all the surprises, but I think you've figured out that I like bondage a lot, and dressing you up, and a lot of other nasty stuff. I'll do everything I've already done to you, and some stuff you haven't even thought about. But I can make a few promises: First, you'll have at least one orgasm a week. Second, the only people I'll ever share you with are Randi and Donna. Third, nothing that'll damage you. I'm not saying you'll never get spanked, because you know that'd be a lie. But I get off on control, not pain. Make sense?"

I nodded

"And finally, you'll never be bored."

She grinned, and I smiled back. Whatever else I could say about the last few days, I was certainly never bored.

"So, how long do I have to think about it?"

"Oh, I know it's a big decision. How about ten seconds?" She grinned.

I wanted to protest. I still wasn't sure how I felt about being Jane's pet. On the one hand, she'd had me do some stuff that appalled me. On the other, she was still one of the most attractive women I'd ever known, and I couldn't deny that even as I thought about the last few days, my cock was still hard.

"Okay, I'm yours."

Jane smiled and hugged me. "Oh, I'd knew you'd agree!"

Her thighs brushed against my hard cock, and I slid my arms down Jane's back, planning to finally reveal her wonderful breasts, but she pulled back

"Hold on there! What did you think you were doing?"

I was confused. "I'm sorry, Jane. I thought that you'd said that if I agreed, well, you know. . . "

"Oh, that's you'd get to see my tits and fuck me?

"Um, yeah."

Jane smiled. "Oh, I love that you're still that innocent. I wasn't lying, of course, but those will happen on my terms. Kneel in the middle of the bed!"

I did so.

Jane stood up in front of me. With her heels, my face was level with her breasts, but I barely had time to notice how tightly the sweatshirt hugged her before she commanded me to look up into her eyes.

"Now, pet," she said, taking something leather out of a bag, "this is my ownership collar. If you earn the right to wear this, you'll wear it whenever you're not at work, and it'll let anyone know you're mine. If you want it, beg me for it!" 

"Please, My Queen," I said, looking earnestly into her eyes, "may I wear your collar? I'm begging you to let me be yours, and for you to use me."

"That's a start. Do you understand that if I take you, I'm going to use you only for my pleasure, however I see fit?"

"Yes, My Queen."

"And that if you wear my collar, you give up your right to question me, to fight me, to do anything I don't feel like?"

"Yes, My Queen." I was excited, but also scared.

She smiled, leaned down, and softly kissed me on the lips. Even as I got lost in the kiss, I felt her wrap the leather around my neck. It didn't feel much different from the old one. She also attached a leash to it.

"This is the same type of collar as the other one." As she said this, Jane kneeled on the bed and slid around behind me, whispering the words in my ear. "But it's got the words 'Jane's Pet' on it. If you're good, I might let you see it."

As she talked, she attached my wrist cuffs to each other, then had me shift so that I was sitting instead of kneeling, with my feel facing the end of the bed. It was tricky, but I managed it. Jane promptly attached my ankle cuffs to the bed, then stood on the floor in front of me.

Before I realized what was happening, she had kicked off her shoes and started wriggling out of my clothes. Alas, she wasn't naked, but was down to a black bra and a pair of peach panties that tied on the side.

She kneeled on the bed and slid a bit forward, sitting right in front of my hard cock.

"Your begging earned you the collar, but you've got to work a little more to see my tits and especially my amazing pussy."

"Just tell me whatever I need to to, My Queen." 

Jane smiled. I'd clearly said the right thing.

"Well," she said, pretending to think. "I do think I can give you a consolation prize."

She turned around and leaned forward until she was on her knees, her gorgeous ass sticking up in the air.

"You've never been very into politics at work, but you could make me very happy with some ass-kissing right now!"

As she said it, Jane tugged lightly on my leash, and I took the hint and leaned forward. It was tough, with my hands and feet immobilized, but I was able to kiss her left ass cheek, and then her right.

"Sweetie, only friends kiss each other on the cheek. Kiss me in the middle." I did so, smooching the center of her panties.

"Okay, you've earned your first prize." With that, she untied one side of her panties, letting them fall to the side and revealing her asshole. I was barely two inches away from her ass, and not far enough back to see her pussy, alas.

"See! You're finally starting to see me naked! Now, give it a real kiss, honey. With tongue." 

I leaned in and repeated the actions she'd taught me in the shower. As I stuck my tongue in, Jane pulled the leash forward, and my tongue was driven all the way in. I was able to roll my eyes upward enough to see that Jane had tied the leash around her waist, effectively sealing me to her.

As I licked, Jane pushed against me, slowly bringing me back to an upright position, then pushing me down so I was flat on the bed, my tongue still stuck in her asshole. She sat firmly on my face, and even though my bound hands under my back made me uncomfortable, I knew that I had to focus on satisfying her. I thrust and licked with my tongue for what felt like hours, but were likely only a few minutes, and then felt her shudder. She untied the leash and slid off my mouth, but slid her panties on before I could glimpse her pussy.

"You've earned two more rewards," she said. She then took off her bra, and I lost track of that what she was saying.

"Like what you see, sweetie?" She grinned. Her breasts were as perfect as I'd expected, and my erection was now painfully hard.

"Now, you get to make a choice again. Do you want one orgasm tonight, or two?"

I blinked. Had I misheard the question? 

"Two, please, My Queen."

"I thought so. Let's work on one of them right now." She reached under her skirt and untied her panties again, letting them drop to the ground. With a grin, she straddled my crotch and guided my cock into her pussy. She was wet and clearly excited.

"Needless to say, lover, you get to come when I say you do," Jane said, as she started to ride me. My hands beneath my back made me uncomfortable, but not enough to slow me down, alas. I could feel my orgasm coming, and watching Jane's beautiful breasts bouncing only hastened things.

"My Queen," I panted, "I'm not able to hold it in much longer."

"It's okay, my pet," Jane said, even as she continued to ride me, "I give you permission."

The words had barely left her mouth when I came, shooting inside her again and again. I'd been teased and aroused more times that day than I could count, and I must have spurted more than ten times.

Jane collapsed and nuzzled my neck. "It's okay, lover. I knew you wouldn't last long that time. But you pleased me, and you earned your next prize."

She slid off me, and quickly removed her skirt. Beneath it was her gorgeous pussy, with the hair neatly trimmed and demonstrating that she was, indeed, a natural blonde. 

"See, you got your prize, and are finally allowed to see me naked. Was it worth the wait?"

"Yes, My Queen."

"Now, let's have you earn your next one." Jane slid up the bed towards my head. "Open wide."

As she dropped her pussy onto my mouth, I tasted my come as it dripped out of her. She rode my face long after I'd eaten all of my come, having me tongue her to two more orgasms.

She finally lifted herself from my head. "Yeah, I'd say you earned that second orgasm tonight, sweetie. I can't even count how many times I've come today!"

With that, she slid down and took my cock in her mouth. I'd thought I'd be too sensitive after the previous orgasm, but my body responded to her tongue, and soon I was hard again. It took longer this time for me to come, but I still doubt I lasted more than a few minutes. Much to my (pleasant) surprise, Jane actually swallowed all my come this time.

As I lay there gasping, I felt her doing something around my cock, but before I really had a chance to wonder what was going on, I heard a click and felt something tighten around my now-flaccid member,

"Just a basic chastity belt, sweetie. I told you you'd get at least one orgasm a week, but this makes sure I get to determine when!"

"Now, let's get your ready for bed!" She took me to the bathroom and allowed me to quickly use the facilities and shower before guiding me back to the bedroom. The belt meant that I'd had to pee sitting down, but wasn't too uncomfortable. So far.

Jane stood me in front of the bed and stood behind me. She had me hold onto the footboard of the bed and lift my legs one at a time, and I felt her slide heels over my feet. These were much more severe than anything she'd used before -- my feet were practically vertical! There was also clearly a platform, as I was now much higher than before.

I felt Jane sliding something up and over my head, and soon found myself looking through a pair of eyeholes. Even before I could question her, she forced something leather into my mouth and locked it into place. She turned me around, and looking in the mirror, I saw that I'd had a tight-fitting leather hood placed over my head. Only my eyes remained uncovered. My feet were stuck in black patent leather ankle boots with a ridiculous platform that had to be at least four inches, and another four inches of heel. I saw little locks ensuring I couldn't get out of them, not that I suspected I'd get the chance.

Jane spun me back around, and with the heels, I nearly stumbled. I felt her attaching my boots to the bed, and with a gentle push, I tumbled onto the bed. The heels and the restraints kept my legs on the ground, and made my ass jut up into the air.

I felt Jane hop on the bed, and wasn't surprised at all to feel her lube my ass. That was followed, of course, by a dildo, easily as big as the ones the girls had used on me earlier today. Once that was in, she stood me up, turned me around, and rechained my ankles. 

"Enjoying this, sweetie? I figured you might actually want to watch me restrain you this time." Jane hadn't bothered getting dressed after the shower, and I could gladly have just watched her.

She grabbed a large leather item whose purpose I couldn't quite figure out and wrapped part of it around my neck. It had a collar that covered my other one, and which attached to a piece of leather that ran down the center of my chest and spread out to cover my abdomen. Once she'd finished wrapping it around me, it covered my stomach and throat, but left large openings around my nipples. I'd guess that it was designed for a woman, given the size of the openings, which clearly were meant to expose the entire breast.

Even though I could see what was happening, I hadn't figured out exactly what was going on until Jane had me slide my right arm into a leather sheath. As she got behind me on the bed and pulled the sheath around to my back, I realized that she'd placed me in a straitjacket! Although this certainly wasn't like anything I'd seen in the movies. She repeated the process with my left arm, locking both arms into place.




A New Year Pt. 04



Jane then got a long leather skirt out of the closet and wrapped it around my legs. She pulled it tight, and I realized that it was a hobble skirt, just like I'd worn earlier in the day. This one, however, ran down to the top of my boots, and when Jane zipped it, my legs were immobilized.

She grinned. "Where do you think Randi gets her best immobilization tricks?" With that, she freed my ankles from the bed, pushed me onto it, and helped slide me up until I was all the way on the bed. She attached my collar to the headboard and my feet to the top of the footboard, then promptly crawled onto the bed, straddling me and grinning down at me.

"Isn't this just perfect?" Jane asked. "You're tied up and completely at my whim! I could do anything with you." She paused as if thinking of something. "Well, not anything, since your mouth and cock are both hidden away. But I could place some lovely pressure on your prostate, for instance." She sat down on my crotch and ground into me a few times, and sure enough, the pressure on the dildo was both wonderful, and frustrating, as my cock was unable to get hard in its cage.

"Or, I could do this," she said, lowering her head and taking my left nipple in her teeth, sucking and biting until I moaned into my gag.

"But," Jane said brightly, "I think it's been a long day. Tomorrow's the last day of the long weekend, and I've got so many nasty things I want to do to you before we have to go back to work on Tuesday. So sleep well!"

With that, she got up and turned off the lights, only turning back to say, "by the way, sweetie, Happy New Year!"

As I lay there in the dark, tied, gagged, and stuffed, I had to wonder what I'd agreed to. I knew I could have walked away, and I wasn't sure I wouldn't regret choosing not to, but I also desperately wanted to know what else Jane had planned for me. Indeed, it was definitely going to be a new year for me on many levels.