From Jeannie to Vanessa - Chapter 01

The moderators here at NovelTrove have asked me to add this disclaimer: This first chapter contains content that might be disturbing to some. I knew all along it was a game, but even so it seemed pretty real at the time.


This is a story about a journey, my journey, from girlhood to womanhood. As implausible as it might seem, it’s also a story about the power I gained by submitting to the will of another. It’s a story about how I learned to understand a little more about what makes me tick (and what makes me go boom). It’s a story about a journey into a mirror; such a journey could be of one step, or a thousand, and might very well contain a few missteps along the way. It is, of course, my version of things, with dialogue and events reconstructed from memory and diaries I kept, but I think it hangs together pretty well. I guess, like most amateurs, I’m really writing it for myself. However, I welcome your thoughts and questions.


Part I: Jeannie is pushed over the edge.

The story starts with my love affair with Jack. I was known as Jeannie then. Yep, Jack and Jeannie. We attended small colleges in the South that were located about an hour’s drive apart, but we both came from the same small city. We had attended different high schools but met through a mutual friend who later attended the same college as Jack. The circumstances of our meeting were kind of sweet, but not important to the story I’m trying to tell. The beginning of the story takes place in the mid-1980’s, so no mobile phones, or internet – a very different time from today.

I guess I should say a word about the two of us. Personality-wise, Jack was kind of a nerd. Read a lot of science fiction and fantasy but was a very nice guy, always something interesting to talk about and lots of fun to do things with. I was kind of a nerd myself, a big reader also. I had REALLY been a nerd in high school, heavy glasses, straight hair and dowdy clothes. I was fortunate I had pretty clear skin, blessed or lucky I guess, and didn’t have to deal with the scourge of acne. A few of my friends went to work on me in the summer before my senior year and I guess you would say I blossomed – with my hair combed out and permed, a little makeup, shorter skirts, and contacts (yay for contacts!!!), I was told I looked pretty good. I had some good times with a few guys that last year in high school, kind of making up for lost time, just in time to graduate and head off to a mostly-female college (booo!!!).

At the time this story really begins, Jack and I had been together for almost a year, and had been lovers most of that time. We were somewhat "experimental" as young lovers often are. I say experimental knowing that modern readers may smile faintly when I say that, but these things were new to us (or at least to me). I was nominally a virgin when I met Jack, "nominally" because I had never gone all the way with a boy although I had gone down on a guy before and done some other things that we would have called "heavy petting" at the time. Jack was not a virgin, but I honestly don’t think he had much more experience than I did when we met.

I think I surprised him a little the first time I went down on him (sucked his cock, Jack would prefer me to say) and swallowed. I think he actually held me at arms length for a moment and stuttered something like, "You swallowed my cum!" (a little obvious, I would have said).

I sweetly responded, "Was that OK?"

"Of course it's OK!" he said, and added, "That's what you're supposed to do!"

After that first time, oral sex became a key part of our lovemaking.

Our experimenting was some about location, a little bit about clothing and a lot about fantasies. We made love out of doors often, and sometimes he would have me walk some distance (in the woods) with nothing on but sneakers. We had sex in the student union's "reading room" at my school and once in the choir room of the chapel. He got me to go bra-less in a see-through blouse and walk across campus at his school once, he thought was way sexy. I didn’t have big boobs, just a 34B in the bra department, but Jack really seemed to like them, which pleased me no end.

He was inordinately fascinated by me in short skirts, or any kind of skirt or dress, really. We once sat on the floor at a school function and he managed to insinuate his hand under my skirt and play with my pussy throughout the event. I still can't remember what was going on at that event, I was totally wound up by his "undercover" manipulations, even through the pantyhose and panties I was wearing. Jack enjoyed fondling me, squeezing my boobs through my clothes, rubbing my pussy under my skirt, and so on. Of course I enjoyed it too! I always got really wet when he did that. Although I would often push him away and act embarrassed, I liked it!

Jack discovered garter belts and stockings and wanted me to wear them, but women in our part of the country had long moved on from those complicated underthings to the relative simplicity of pantyhose, and I for one was reluctant to turn back the clock. We had recently become engaged, however, and I put him off by promising that I would wear them for him some after we were married. I’m sure the faint smiles from the more experienced readers will have turned to chuckles or maybe outright laughter at this point, but hey, I thought we were typical church-going southern college kids of the time.

One of the "risque'" things that we did regularly engage in while having sex was domination and submission fantasies. Sometimes I was the maid with the wealthy landowner; other times he was the poor peasant coerced by the queen. Occasionally they were more violently oriented, usually with me acting out the part of the defenseless girl attacked by a home invader. All of these were costume- and device-free; in other words, these were all verbal fantasies, the only physical part being the sex act which was the consummation of the story. Sometimes the fantasy would involve Jack forcibly removing the clothing of the submissive partner (me), turning me over for a spanking or something like that. Although I liked being the “queen,” I got particularly excited when he was the dominant party, and that more and more became the theme of our fantasy love life.

I was multi-orgasmic from the beginning of our sex life and frequently would cum so hard that I would actually pass out. Jack worried a little bit about me then, and would usually administer mouth-to-mouth resuscitation (no, really, not just kissing, I mean blowing air into my lungs) until I revived. He told me he did this because he had no desire to fuck a sleeping girl, or a corpse – he wanted me to feel and enjoy the moment as the sex, as he put it, “was not just all about his pleasure.” What a gem! I adored making love with him from the get-go. Thank God for birth control pills!

Another thing that we gradually moved onto was the use of more, well, "pornographic" terms while having sex. We still talked about making love, having sex, "sleeping together" etc., but during the act Jack encouraged words like fuck and cunt and slut. This was a little weird at first; strong language was pretty foreign to me at the time, but I was no prude and I thoroughly enjoyed sex with Jack. I found it easier and easier to say those words. During sex, which is when he most encouraged it, they really became associated with me being horny and turned on and I began to be more and more comfortable using them. I guess I used them more in my mind, sometimes, than out loud, but as time wore on, I definitely found places to use the coarser language I was beginning to learn.

After some of our dominant/submissive games, Jack would hint around with a smile that I'd better be careful when he wasn't with me, I might encounter a dangerous scoundrel that would take advantage of me. I would act mock-scared, fluttering my hands and saying things like "I would just be helpless, they would be able to do whatever they wanted with me" or some such blather. I kind of expected that eventually I would be "helpless" in the hands of a "scoundrel" who would likely look and sound just like Jack…

One night, we had been to dinner together in our hometown and played around under the table and in the car a little in anticipation of more fun later. As usual (and with Jack's encouragement) I had on a short skirt, pantyhose, and white button-up blouse (easy access, you know). One thing was kind of new...Jack had been encouraging me to wear higher heels. Normally I the best I could do was pumps or wedges with about 1 1/2-inch heels or occasionally boots with 2-inch block heels. Jack had saved up some money and took me to a shoe store and bought me a set of shoes with 4-inch-high heels. They were brown suede and had really slender heels...not what you'd later call "stilettos" but still pretty high and skinny and very sexy. So I had these new shoes on that night and was still adjusting in how to walk in them. Jack loved seeing them on me. We had fucked once with me wearing them and he was like a demon! So I expected I would be wearing them a lot more.

When we were home from school, after the "official" date event, we would often drive about 45 minutes to a vacation cabin Jack's parents owned on a nearby lake. There, we could screw with abandon. This time, however, we made a brief stop at his parents’ main house as he said they were out for the evening. Jack said he needed to go to the bathroom. After emerging from the guest bathroom at the front of the house, he encouraged me to go as well. I didn't need to go that badly, but anticipating a medium-long drive (with Jack playing with me, and with me probably sucking his cock as he drove), I figured it was a good idea. While I was in there, I heard some thumps and a door slamming out in the hallway. I was hoping his parents hadn’t come home unexpectedly, although we weren't either of us in a compromising position (remember when you were scared you'd get caught by your parents?) so I carefully turned off the lights in the bathroom, edged the door open and stepped out. The hall (that had been lighted when I went in) was completely dark.

I called out "Jack?" and heard some more thumps and a dragging noise.

Suddenly a hand grabbed my neck from the front and there was a face, hidden by a dark-colored ski mask, inches from mine. Also inches from my face was a very real-looking gun. Now I'm no gun expert; Jack had taken me shooting several times so I knew he had guns and knew about them. I tried to discern from the parts of the face I could see if it was Jack in the mask; the face was definitely the right skin-color so that was a positive clue. I tried to look down to see what the "villain" was wearing, but the hand around my neck was practically lifting me off my feet and kept my head up high. And the hand was tight – it was in the "you're hurting me" range, but I was determined to be tough and play the game, ‘cause game is what I was pretty sure this was. Jack’s “dangerous scoundrel” had finally come to call.

A guttural voice (maybe Jack?) emerged from the mask and ordered, "Turn around, cunt!"

I started to scream then and suddenly, in the midst of opening my mouth, I felt a large rubber ball go in. It was so big it pushed up and down on my wide-open teeth as it went in. I tried to close my mouth against it or say something but the "masked man" was too quick. It was like he was really familiar with how to gag a person. The ball had a wide leather strap through it, a strap that was rapidly pulled around to the back of my head and secured somehow (buckled? tied? I wasn't sure). A bag went over my head and I felt handcuffs (handcuffs?) going around my wrists. It was a little uncomfortable but kind of sexy, in a weird way.

What was not weird at all (and was vintage Jack) was the hand that pulled up my skirt and rubbed and squeezed my pussy. It seemed to be gloved, which I thought was carrying things a bit far, but my attention was diverted as the hand continued up my chest and squeezed both boobs and pinched the nipples roughly through my clothes. I was beginning to breathe a little harder through my nose and around the mouth-filling gag, a little from the surprise and fear and a little from something else.

Now the reason that I was so surprised about all the preparation and hardware was that we were college students, for God's sake, we didn't either one of us have a lot of money. So we had a ski mask, ball-gag (yeah, I knew what it was), handcuffs and goodness knows what else invested in this little game (I was pretty sure it was Jack).

But, now that he had me gagged, hooded, and handcuffed, whoever it was frog-marched me out the side door into the garage. It looked like I was still going for a little ride, only more as baggage rather than passenger. I actually thought I was going in the trunk for a minute, but I guess my assailant decided that was carrying things a little too far. I agreed; I did not want to ride in a trunk, no matter how nice the car. Instead, Jack (after not going in the trunk I was a little more confident it WAS Jack) conducted me into the backseat of a fairly large car and laid me down on the seat. This was a little odd, as I knew Jack drove a Toyota compact, but I figured he'd borrowed a car for his "kidnapping."

Another set of cuffs went on my ankles and he then used the seat belts to secure me tightly to the seat before draping a light blanket over me. Just before he covered my head, he put a wire around my neck. In the same growling tone as before, he warned me that if we were to get stopped, I should stay completely silent; if he heard even a squeak from me he would pull the wire. He described how it was run through the seat belt anchors so that as he pulled from the driver's seat it would pull me back into the seat and strangle me. That was fucking scary, and I began to wonder if this was, indeed, Jack. You may think this was crazy, but I was somewhat reassured when my assailant lifted the blanket and roughly fondled me again before heading for the driver’s seat.

Jack obviously wanted to keep me off-balance, and it was working. Although I was still confident it was all a game, I was genuinely terrified that we'd have an accident and the wire would get pulled while I was gagged, strapped, and cuffed in the backseat. And yet, I was also turned on. I was completely helpless, I had been groped in a rough but sexy way twice, and I was looking forward to fucking Jack all tied up or something. I think I kind of passed out at that point. Suddenly we were arriving; I had planned to listen to turns and count the minutes to try to find out if we were going someplace familiar (like the lake house). I think all of that went out the window when the wire went around my neck. At least we hadn't had an accident! The blanket came off of me, the seat belt straps were released and I was turned roughly face down. Another couple of rough squeezes, this time of my ass, and the bag came off and was replaced with a proper blindfold, the kind sleepers use, only it seemed heavier (backed with leather maybe) and was also fastened securely behind my head. ANOTHER piece of special kidnapping gear.

I thought my ankle cuffs would be removed but nooooo...I had to walk, blindfolded, gagged, arms cuffed behind my back, ankles cuffed with a short chain between, AND in 4-inch heels. This seemed a bit much for a fantasy and I was actually getting a little pissed off. I thought about giving Jack a piece of my mind when all of this was done. Fortunately it was a short walk – shorter than I remembered actually (I figured we were at the lake cabin, but things didn't seem quite right) and suddenly I was being pushed down onto my knees (on a small cushion at least, my anger with Jack cooled a bit).

I felt the wire go back around my neck, and the low angry voice once again sounded close to my ear; "Make a sound, or try to bite, and I will yank this wire and it will be the last fucking thing that your mouth does."

The gag-strap began to loosen and the ball was pulled out of my mouth. I tasted rubber, briefly, as I tried to work my stiff jaws a little and I wasn’t surprised when I heard a rustle of clothing very close to my face and then, very distinctly, the sound of a zipper being slowly lowered. Then, without further preamble, a stiff cock replaced the gag.

“Now we are getting down to the sex part!” I thought as I began to work my magic. But I quickly realized my voluntary efforts were not going to be enough to satisfy my assailant. He put his hands behind my head and plainly demonstrated he wanted a deeper penetration. Now, you’ve got to understand that although the movie Deep Throat had been out for over ten years, and even innocent little Jeannie had seen it, the concept of face- or throat-fucking was still somewhat new. Remember that this was before the great Informer, the Internet, had arrived, and deep throat sex was not (or so I believed) a common practice among the more genteel class of society of which (I believed) Jack and I were a part.

However, this character wanted exactly that, and with judicious use of hands in my hair, his fist, and growled orders, got across the point that he wanted mouth open and throat relaxed. Jack was pretty well endowed, and this guy seemed even thicker and longer (no doubt my perspective from being bound, blindfolded and on my knees). I gagged, fought and protested as much as I could but in the end my mouth and throat became just a sleeve for this man’s cock. It seemed like a long struggle, but probably it was really just a few minutes before he pumped a load of hot, sticky cum into me. He slapped my face, hard, and ordered me to swallow all of it. That’s not something Jack would have needed to do, although my “assailant” wouldn’t have known that, I reasoned. I did what I was told and gulped the huge load as best as I could, but inevitably some dripped down my chin.

I sagged between his knees, really kind of broken-spirited for the moment. The assault on my mouth and throat had truly been the most violent thing I had ever personally experienced. It had also turned me on like nothing I had ever known before. It was so hot! I know the feminists out there are clucking their tongues in disapproval – but I could only feel what I felt. I felt a hand – probably the same one that had just slapped me – stroke my hair soothingly. Then, as if the assailant realized he had shown weakness, he yanked my head up by that same hair and quickly re-inserted the gag. It wasn’t really necessary – I was speechless at that moment – but I knew (intellectually) it was part of the continuing domination and control. Then I was lifted to my feet and walked a few steps – staggered, really, dazed and chained and in the still-unfamiliar high heels – and then was laid onto a nearby bed. It was not an uncomfortable mattress, actually. My heart began to beat a little faster – this had all been a LOT of preparation for a little fantasy fuck – and I was still a little disconcerted about how roughly I had just been treated. Jack was always so considerate of me, I guess I was seeing another side of him tonight. Not all bad…

My cuffed ankles were pulled out straight (but still together) and secured to the foot of the bed/mattress; I could hear the rattle of chains against some kind of metal frame. After I was pulled tightly towards the foot of the bed, my arms were pulled pretty far over my head from behind and secured. Then, one at a time, my wrists were released from the handcuffs and secured again by what seemed to be wide leather straps, one each chained to the left and right corners of the metal bed frame. Then the process was repeated with my legs, until I was in the classic damsel-in-distress spread-eagle position on the bed. It occurred to me that throughout the whole process I was fully secured to the bed and released and re-secured one limb at a time. Whoever the hell was doing this knew what they were doing – I would never have been able to get enough leverage to fight back very effectively. And now, to the growing pile of hardware dedicated to this "fantasy" and used on me, I could add a leather-backed blindfold, four leather cuffs, chains and (presumably) locks of some kind. Did Jack rob a bank? Or maybe just an adult toy store? The last thought made me try to giggle, which reminded me just how effectively the ball-gag had me silenced!

I wondered just how Jack would strip me, for it was obvious that I was about to get fucked. Pantyhose and panties make a pretty formidable obstacle for the typical backseat groping session; however, it was quite plain to me that we were well beyond THAT and that my clothes were likely to get ripped and torn tonight. I wasn’t sure how I was supposed to get home in tatters, but I hoped Jack (Jack?) had thought of that since he had obviously thought of most everything else! I didn’t have long to wait. My skirt was lifted up in front and my assailant began to do something that involved pulling on the seam of the pantyhose where the leg joined the crotch. Pretty soon I figured out that he was cutting the hose with a knife or razor and making his own “poor girl’s garter belt and stockings” out of my pantyhose by essentially cutting the reinforced crotch out of the hose.

This took a little maneuvering and lifting of my ass to get at the back. I figured all he needed was access to my pussy, but he seemed determined to cut the material almost to the rear waistband. The next move, of course, was to rid me of the remains of those troublesome (and soaked) panties. That didn’t take much effort – a quick cut from the leg openings up through the waistband and they were pulled away from my now-naked nether regions. I noted – as did my assailant, confirmed with two no-longer-gloved fingers shoved roughly into my exposed pussy – that I was dripping wet. I was being whipsawed back and forth between terror, anger, and excitement so fast that I wasn’t sure what I was feeling from minute to minute. One thing was for sure, however; my pussy wasn’t confused, it was digging the whole experience in spades.

Next up was to get at those boobies, I thought, and I was not wrong. My blouse was unbuttoned instead of being ripped or cut off but the bra underneath was quickly sacrificed to the knife. Rough hands squeezed, twisted and pinched my breasts and nipples, quickly replaced by lips that felt like they were surrounded by a beard (did Jack have a beard? Suddenly I couldn’t remember). My assailant seemed to have dispensed with the ski mask, which made sense since I had been either hooded or blindfolded since the beginning of this experience. So at this point my pussy was soaked and my nipples were stiff and extended – I figured a quick pronging was next on the menu. But I was wrong.

I thought rapists were supposed to be short-order guys, but I had apparently encountered a French chef-style assailant. He continued to suck and play with my nipples until they were beyond hard. Then, he took some kind of thin cord (dental floss maybe?) and wrapped it around the base of each nipple, like little sexy tourniquets. It wasn’t really painful, but certainly unexpected. Then he put a what I thought was a clothespin on each of these engorged nipples. That fucking hurt! At least, it did at first. After a few moments it became more bearable, although with each movement of my upper body I could feel the weight of the pin moving around and exerting different kinds of pressure on the nipple. It would hurt for a few seconds when it moved, then the pain would subside, then hurt again...well, you get the picture.

I was heavily distracted by this continuing cycle, so much so that I was genuinely surprised when I felt a weight shift the mattress around me and a thick cock part my outer labia. I didn’t have a lot of time to consider what was going on because that dong drove all the way into me with the very first stroke. Believe me, it went fucking DEEP! I certainly didn’t remember Jack’s cock being quite so thick or long. The bastard rode me deep and hard and of course my body whipped up and down on the mattress to the limits of my chains, meaning there was a LOT of movement of the clothespins and very little time for each painful moment to subside before the next one followed it. It was crazy hot and my body was eating it up although my brain was far behind.

In short order (little humor there) I began to feel the orgasm building. Normally this was a slower process, involving lots of foreplay, deep kissing, fondling, and slow, delicious penetration. This was coming on more like a freight train, with me chained spread-eagle on the tracks. Suddenly, I felt the clips come off my nips and the cord rapidly unwound from the bases of same. The blood and feeling returned with a vengeance and the top of my head blew off (metaphorically speaking). I exploded like some sort of literal blonde bombshell and promptly passed out.

Now I mentioned before that I was known for little blackout sessions; Jack usually brought me back to life with a little honest-to-God resuscitation. When no such action was performed, Jack had told me I usually came to my senses within a short time, no more than few minutes at most. Came to I did, and I was in the same position as before, spread-eagled on the bed with arms and legs tightly secured and with chest and crotch exposed. There was something different, though. I could feel my naked butt was on something that felt a little a towel?

And there was DEFINITELY something strange going on around my pussy...a scraping, tingling feel, then some soothing cream rubbed BARE PUSSY! I was being shaved! Holy crap! This was beyond the usual fantasy stuff, this couldn’t be fixed with clean clothes and a bath and fresh makeup! I mean, I didn’t usually take showers with anyone (other than Jack) so there was little risk of exposure but HOLY FUCK! Girls like me didn’t SHAVE THEIR PUSSIES! When I realized what was going on it’s a wonder I didn’t hurt myself, either by yanking at my chains or by getting cut by the shaving razor while I convulsed my whole body. I figured it must be a razor since I didn’t hear anything buzzing and clearly the deed was already done. A little cleanup, some more of the soothing cream and voila! Jeannie in her new career as stripper at your service! I was fucking STEAMED! Now you 21st century girls, stoked by all the nudity on the Internet, can roll your heavily-shadowed eyes all you want. This was a BIG FUCKING DEAL to me. I wondered if Jack was planning to put me to work walking the street!

Unfortunately (or fortunately, depending on your perspective) there wasn’t much I could do, or even say. I mmmphed uselessly and struggled just as uselessly. I guess it didn’t matter much anyway, because as I said, the deed was already done.

Just as I was beginning to spin down a little, I clearly heard Jack’s voice say, in a low tone, from several feet away, “My turn.” A low grunt replied.

At that moment, you could have played me like a fiddle, I was strung that tight. There was really someone else there!!! Holy shit! Someone else had groped me, fucked my mouth AND my pussy, and NOW it was Jack’s turn??? At that moment, to use one of Jack’s more colorful phrases, I didn’t know whether to shit or go blind. As had been made painfully obvious in the last few minutes, I couldn’t effectively do either. I was already blind and know. Another weight shifted the mattress around me, and once again a cock parted the lips of my already-well-fucked but now smoothly-shaved pussy. I was determined not to enjoy it this time, just to pay Jack back for the whole mess he had dragged me into. Jack obviously wasn’t going to take the time to do more tying or pinching of nipples, since he apparently figured I was already “well-primed.” And, as it turned out, he was right.

Jack didn’t slam me like the other assailant had done. He slowly worked his stiff cock into me, gently easing in and out. There was something…something about his movements, against the lips of my freshly denuded pussy...I couldn’t tell if the other cock had actually been bigger or not. My mind was a falling climber desperately grabbing for handholds – was it really just Jack all along? He told me he loved me! We were planning to get married! Surely he wouldn’t have given me me to another man? His pubic hair crushed against the bare skin of my freshly shorn pussy and the feeling was crazy!

I began to slip the bonds of anger and fear and once again melt into the familiar, delicious feeling of making love with Jack. My resolution to fend off the tendrils of lust that were smoking up from my pussy began to melt rapidly away. He continued to work his cock in and out of me. I felt his chest crush my breasts and his arms snaked under my outstretched arms and around my neck. He began to kiss my neck and nibble on my ears. Once again my disloyal body began to respond in the usual way. He was definitely taking it slow, not like he was building up to an orgasm if he had already recently ejaculated. Was it really Jack who had thundered a load into my throat earlier? Had this all been a cleverly designed ruse just to keep me off balance?

My mind began to find a few handholds...and they started feeling a little more secure when he whispered “I love you, Jeannie,” directly into my left ear.

The slow fucking, the incredibly sensual feel of his pubic hair grinding against my newly bared flesh, the hugs, the kissing, and oh the sweet, sweet words allowed me to let go of my uncertainty and to simply enjoy the sensations. My arms and legs were stretched out and secured but not uncomfortably so; the blindfold merely denied my eyes a chance to see a face that I knew well and would soon see anyway; even the gag that kept me silent only added to my submissive posture beneath him, a fantasy we had often enacted before, albeit not quite so realistically.

Soon my hips got into the rhythm. As restricted as my movement was, I could still love him back. And love him back I did. I could feel the orgasm building from miles away. It traveled more slowly, this time, not like the freight train that had hit me when the other man (it had to have been Jack! my brain insisted) had so cruelly toyed with my nipples and then hammered my pussy like he was driving a railroad spike. Jack began to thrust in me harder and faster; he was still not tensed up like he would be when he was about to cum (that’s because he already did! my brain desperately said) and so I relaxed into my own pace. When my orgasm did arrive, it was still suitably volcanic. I tried my best to call out the things I would usually have said at that moment but the ball-gag once more defeated me. And true to recent form, I passed out again.

I came to in a different position this time. I was still secured, spreadeagled on the bed, but face down. My head was turned to the right, but the blindfold was still on so little had changed in that regard. One thing I noticed quickly is that my hips were raised on something soft, a pillow perhaps. What the fuck? Again, remember when and where we were. I had no fucking clue what was about to take place. But I didn’t have long to wait to find out. The first thing that happened was “ten of the best” you might say. I would have screamed but, you know, I was gagged. It didn’t stop me from trying, though. Each time the (whip? belt? paddle?) bit into my tender and heretofore unmarked ass-flesh I flinched as far away as I could, which of course was no-fucking-where at all. And it wasn’t done in a hurry; there was a noticeable pause between each blow. Now Jack had spanked me a few times as part of one of our fantasy games, but this, as the Monty Python characters would say, was something completely different. By the end, I was sobbing. I could feel my tears soaking the material of the blindfold.

Suddenly a book title came unbidden into my head, something Jack had read and gave me a copy to read also...Story of O, by Pauline something. Oh my God, I thought, here we go. There was more coming. And I didn’t have very long to wait. A hand began to gently smooth cream over the fresh welts, soothing the pain a little (sweet, I thought) but then the hand moved to push something that felt very similar to that cream into and around my anus, making sure it was well-lubricated. Oh holy shit. When I read about that in the book I didn’t think people did it for real. I mean, homosexual guys apparently did it, and some very experimental lovers, but southern college students? Oh holy shit. I guess I was about to find out. First a finger, then another, spread my tight virginal asshole. It didn’t hurt, exactly, it felt, well, different, in a way that was hard to describe. Then I felt the weight coming back onto the bed. I couldn’t help it, I began to tense up.

A face came close to my right ear and Jack’s voice whispered, “Try to relax! It will be easier!”

How the fuck would he know? My mind spun off into the possible answers to that question for a moment and then was rapidly drawn back to the present when I felt a blunt, fleshy object pushing against my little well-lubed rosebud. I quickly remembered his admonition to “relax” and did my best to do exactly that. And it did help. There was definitely some “discomfort” (as a doctor would say) but it wasn’t so bad. I could clearly feel the instant that the head of his cock popped through the tight ring of resistant muscle. Then, inexorably, the rest of Jack’s not-inconsiderable shaft was pushing into my ASS. It really didn’t hurt that much, it just felt really weird. I was consoled somewhat by the fact that it WAS Jack. Jack hadn’t been the first man I gobbled cock for, but he had been my first full-blown screw and now was taking my anal virginity as well. I figured my ass must be pretty tight on him, because he was taking it REALLY slow and easy. That made it easier for me as well.

I started, actually, kind of enjoying it. It certainly wasn’t the same feeling as regular pussy-fucking (the ass has no clit) but, as I had discovered earlier I was getting into the helpless feeling of being bound. Make no mistake; whether I enjoyed it or not, it was happening. There was no “pretend” about the leather and chains holding me down, and there had been no “pretend” about the knife that cut away my pantyhose and underthings. There had definitely been no “pretend” about the razor that shaved my pussy (I could feel the inside of said organ getting wet again) or the strap or whip that had struck my sweet cheeks. As I felt Jack reach the full depth of his cock and felt his heavy balls slap against my bare labia, I was reminded of the violence of his assault on my mouth and throat. My pussy began getting even wetter! Holy crap, what was I turning into? Jack withdrew his cock almost out of my ass and then plunged back to the hilt, a little faster this time. Then again. And again. As he sped up his assault, almost like he really was building up for an orgasm himself, my motor began to run a little faster also.

Since the ass has no clit, I figured I was in for a “duty fuck” without much resultant pleasure for myself. But, apparently the female body can hold some surprises even for the female whose body it is. The harder he fucked my ass, the hotter and more excited I got. Jack thrust harder, and faster. I could feel his hands in the mattress alongside my raised hips – he was up on his knees, hammering me as hard as he could. It definitely felt like he was working up towards cumming IN MY ASS. The more that thought pinged around in my tiny compressed bean-brain at that moment the hotter got. I would never have believed a woman could get that excited with someone fucking her ass, but with Exhibit A plainly about to happen, I rest my case Your Honor. Just as I began to wonder exactly what it would feel like to have Jack cum in my ass, I didn’t have to wonder anymore. I could feel the hot jets of cum spurting against my….I would have to look it up, I had no clue, I was a frigging English major…oh my God, oh my God, oh my fucking God!!!!...and I passed out again.

Holy crap, this was getting to be more of a habit than normal. The good news was, Jack brought me back to life in his usual fashion – life-giving mouth-to-mouth. Or was it just passionate kissing this time? Whatever it was, I was in his arms, the blindfold and gag were gone, as were the...wait just a damn minute! My arms were behind me still, the handcuffs were back on, and this time something was holding the elbows together as well. My ankles were also still cuffed together. We were sitting on the couch in his parents’ main house and he was holding me in his lap. He had a washcloth and was doing his best to clean the remains of smeared lipstick, tear-stained eye shadow – and probably dried cum – off my face. The immediate question forming in my head was, “Why am I still chained up?”

Evidently Jack could see that question bubbling up because he laid a finger on my lips and said, “Just a moment – do we still need the gag?” THAT caught me up short. I quickly shook my head and he smiled. “All will be explained. Just be patient, Jeannie.

“Let me ask you do you feel? And before you answer,” he added, as my mouth began to open, “think for a minute. How do you really feel right now?”

That was an odd thing to say – I felt exhausted, violated, angry, sore, betrayed, still a little fearful, and….something else. The more I considered, the more I realized, and with a slow smile I finally answered, “I feel horny. And tired. And a little sore. But,” I added, looking around, “I do have a lot of questions.”

I saw a wave of relief – and pleasure – pass quickly over Jack’s face. “Let me answer two of what I think must be the top questions in your mind. Number one, it was me. All the time.”

At that, I sagged in his arms, relief flooding through me. Then I remembered the way he grabbed my neck at first, the brutal mouth-fucking, the whipping, and I started to speak. But Jack was already talking again.

“Number two, we never went anywhere. I took you out to the car, my parents’ extra car, actually, and we drove around a little, but once I realized you were out, I drove back here and waited for you to come to. My parents are actually out of town, not just away for the evening. If you hadn’t passed out like you did, I would have driven around a little more to confuse you. Also,” he held up some red strings, “this is licorice candy. It feels like wire when it’s around your neck, but it breaks pretty easily.” He demonstrated by pulling a piece apart. “You can actually eat it, but I hate licorice, so not for me,” he said, dropping the candy back into a paper bag. “And now for the question that’s probably at the tip-top of your list?” he inquired.

“Why am I still chained up!!!” I blurted out.

Jack didn’t answer immediately, but just looked at me. The longer he did that, the more uncomfortable I felt. Not physically uncomfortable, more like something in my head was sitting sideways. And hornier. That part I kind of understood. Although I was more-or-less clothed, there was no mistaking the feel of my unfettered boobs under my blouse, or the strange feel of my freshly shaved pussy under my skirt, or my bruised lips from the oral assault, the aching jaws from being gagged long? or the not-quite-raw feeling of my asshole, or the no-shit throbbing of my ass cheeks. But there was no denying that, with all of those mixed feelings, also still being restrained and helpless, I felt...horny! It was almost funny. I had been gagged, bagged, cuffed, kidnapped, shaved, whipped, fucked in all three holes, and my body was telling me I was ready to do it all again! What the hell? And then I knew the answer. I was still chained up because it turned me on. And Jack had seen it, had been able to figure it out from our “costume-free, device-free” fantasy life.

“Because you love how it makes you feel,” he leaned close and whispered, “and I love it too.”

And he definitely did. Another thing I could feel, sitting on his lap as I was, was the distinct stiffness in his pants, this after two orgasms (at least two, I didn’t know if either of the “normal” fucks had resulted in an orgasm for Jack, although they certainly had for me).

“There are going to be some new rules in our relationship,” he added, “and you might find them a little inconvenient or uncomfortable at first, but we’ll get through this...together.”

I could only guess. Going to the movies in my current state was going to arouse comment, for starters, and would likely require a wheelchair or a laundry cart.

“No, I’m not going to keep you chained up all the time,” he said, answering my unspoken question, “but I am going to find ways to remind you of exactly what went on here, and what it has revealed about you.”

I remained silent at first. He looked at me for a few moments without speaking, and I decided to interject. “Do I get a vote?” I asked.

“Yes,” he replied, “always. But I’ll make the final decision. You have a submissive nature. We both know that now,” he continued on, when I made as if to say something, “and I’m going to help you fully realize it.”

“Can you give me some examples of the new rules?” I asked.

Jack replied, “Certainly. Your pussy is going to stay permanently bare. Shaving it will be a pain, and chemicals can be messy and smelly, but I understand they’ve recently developed a laser system that’s permanent. I’m sure it’s expensive but we’ll work through that. And I want it bare in another sense, or at least readily accessible to me, all the time. I’m going to insist that you wear a garter belt and stockings, without panties, except when you are having your period. I know you can’t wear a dress all the time, so we’ll look for other options that meet my requirements. I understand there is a style of women’s pants that have zippers from back to front, I think they are called “drive-in movie pants,” that may serve our needs. Also, I’m going to have you wear a collar. We’ll come up with something stylish that won’t arouse too much attention, but it will be something meaningful to both you and I. Oh, and I want you to continue to practice wearing the new heels, because you’ll be getting some higher ones soon.”

If I both of my hands had been free they would have been helpful in picking my jaw up off the floor, so without that assistance I had to use my own sore facial muscles. He was obviously completely serious. It took me several minutes to digest both the concept and the specifics of these new “rules in our relationship.” While doing so, I thought I would buy a little time by asking a question that had bugged me from the beginning of this fantasy experience.

“Jack,” I asked, “where is all the money coming from? Even the things you used tonight, the gag, the two sets of handcuffs, the leather cuffs, the blindfold, that stuff costs money. Now you’re talking about lingerie, new clothes, new shoes, special jewelry, and laser hair removal for goodness sake. You said yourself that had to be expensive.”

“I got a job, of course,” he responded. “Now that I’m in my third year in the engineering curriculum I found a position as an assistant to a local civil engineer. It actually pays pretty well, and it could potentially lead to a permanent position when I graduate. I have to start thinking ahead if I’m going to support us after we’re married. And clearly, I have responsibilities for you now.” He looked me straight in the eye. “If you are going to be my submissive, I have to be able to take care of you in the manner to which I want you to become accustomed.”

I giggled a little at his twisting of the common phrase, and the loaded word “submissive” titillated me more than I wanted him to know just yet.

“What if I don’t want to cooperate? What if I don’t want to wear stockings, or higher heels or a collar? What if I don’t want to keep my pussy bare?” I teased. Actually, I had been oozing out of said bare orifice for some time now, but I wanted to know more.

His right hand moved swiftly up under my skirt and probed the wetness he found there. “You, of course, are free to refuse,” he replied, “but I don’t think you will.”

“I’m free to refuse? I can say no? If I don’t want any of that, can we go back to the way things were before….before everything that happened tonight?” I asked.

He didn’t say anything. He just looked at me. I already knew the answer. Nothing could ever change what had happened between us that night. And my dripping pussy wasn’t alone; my tight little bum was already twitching for a second go-around with his cock.

He reached around behind me and undid the strap that held my elbows together. He pulled out a set of keys and opened my handcuffs and then my ankle cuffs.

Without another word, I crawled off the couch and got on my knees at his feet. Then I looked up into his eyes and whispered, “Please Jack, take me. Take me however you want me. I’m yours.”


The ride home that night was quiet. We both knew an important line had been crossed. What it would ultimately mean was unclear as yet.

The immediate challenge was to get rid of the remnants of my poor bra and panties. I pulled myself together as well as I could, and we consigned the mutilated underwear to a dumpster at one of the local parks. I told Jack I would get rid of the remains of my pantyhose after I got home and was able to undress properly.

Jack kissed me deeply at the door to my house, telling me he would pick me up in the morning to go shopping. I often invited him in, but tonight I wanted to take no chance that a parent would wake up and come to visit!

Next stop was my room, where I got out of my outer clothes and removed what was left of my pantyhose, stuffing it into a plastic bag that went to the bottom of my suitcase for transport back to school on Sunday. Then onto the bathroom, where I wanted to get some makeup remover to finish up the job Jack had started with the washcloth.

The face looking back at me in the mirror stopped me for a moment...what I saw with the makeup scrubbed off was the bookish "plain Jeannie" I had known in high school. It was almost as if the crazy evening with Jack had taken me back. Who was I becoming?

I reflected for a moment. I had been beaten, robbed of my dignity, taken against my will. There were a number of things that I could point to tonight that I would never have willingly agreed to. And that they had happened...I couldn't imagine living my life without the experience. And I couldn't imagine not doing them again. I wasn't looking forward to being hurt again, but the taste of powerlessness was so delicious that I wanted more.

Another look in the mirror before I stepped into the shower. What did she see?

-to be continued-