A New Year Pt. 01

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Jane suckers poor Alan into a compromising situation.
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Part 1 of the 4 part series

Updated 09/22/2022
Created 01/04/2010
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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."

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