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.