A Submissive Sissy

Here you'll find my favorites Sissy & Femdom stories, the best one I've ever read over the net since many years and believe me, that's a lot ! I'm also a wool fetishist, so you may come accross this type of topic around here too... Hope you'll like it !

Unknown Author

The Sweatering of Chris

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I'm generally considered to be quite attractive, and even in high school I was aware of how much guys were attracted to me and how I could use that to control and manipulate them. Most of my "steady" boyfriends were guys my friends were surprised I went out with. They were not the top athletes, but just really nice guys who were thrilled and thankful to have a chance to go out with someone like me. I was even the head cheerleader, and I KNOW that the cheerleader outfit really drove the guys wild. Our outfit consisted of white tennies, red socks, a short white skirt, and a red lambswool turtleneck sweater. Some of the girls liked their sweaters big, but I liked mine tight, and even though there was a rule that we had to wear a bra, a couple of the girls - including me - usually didn't. As I'd jump up and down doing my cheers, my boobs would bounce around underneath the sweater, and I'd see the guys staring at me with their eyes bouncing along with every movement of my breasts. They'd almost look hypnotized!

What I liked about the guys I'd let go out with me was how totally devoted to me they were. They'd spend lots of money on me, take me nice places, and do whatever I wanted basically. And I should explain that when I say "going steady" I mean that the boys had to agree to go out only with me--while I was free to go out with other guys. I don't know why, but I just always liked that kind of setup. If I found out that one of my boyfriends had gone out with someone else, I'd dump him in a second. They'd learn the lesson fast, and when they'd come crawling back begging for forgiveness they'd know to have something nice in hand for me - a nice expensive cashmere pullover perhaps, or something equally pricey - and they'd know never to even hint at dating another girl again as long as I was letting them date me.

I met my husband Chris in college. With him it was just like with the guys in high school. He is really smart and very good looking in kind of a boyish (or even girlish) way, but he's quite small and shy and not very athletic, and never was the kind of guy who was able to date the really popular girls. One day I was walking through the library on campus wearing a pretty (and very short) blue plaid skirt, penny loafers and blue knee socks, and a shetland wool baby blue faire isle sweater set. With my long blond hair and ample figure I was well aware (as usual) of boys' heads turning whenever I walked by. But Chris was different. He actually started to follow behind me from room to room. He tried to pretend he was looking for a book or reading if I looked back, but even when I went into the stacks I could see he was there. So I decided to confront him. When I walked up to him he got all flustered and red in the face, and started to say he hadn't been following me. But I told him I knew he had been, and that I didn't mind. With just a little more encouragement from me, he was soon telling me that I was the prettiest girl he'd ever seen, and that he'd never done anything like that before, and he was so sorry, but he couldn't help it because I was so beautiful, etc. etc. When I told him he could take me out on a date he almost fainted.

Right from our first date I knew Chris was just totally infatuated with me. He was always telling me how beautiful I was, he gave me unbelievable presents (he took a part-time job after we started dating just to have enough money to buy me things), he did most of my school work for me (as I said, he's real smart), and just generally did anything I asked.

Right from the beginning I also knew that he had a special "thing" for how I looked in sweaters. He was always asking me to wear them, and he was always buying me the most gorgeous cashmeres and lambswools and ski sweaters. I bet the first year we dated he bought me two dozen sweaters, and he most liked it when I'd wear one without a blouse underneath. But the real clue that this was more than just liking how I looked in them was that when we had sex he'd like me to keep them on! He would fondle and kiss my breasts through the sweater, but wouldn't want me to take it off. And he was always begging me to put on my old high school cheerleaders outfit - but that's something he's never gotten to see except in pictures.

I went steady with Chris for two years in college the same way I went steady with my high school boyfriends. I told him that if he wanted to go out with me he couldn't date anyone else but that I would want to date other guys and might even have other "steady" boyfriends. So he knew that there would be nights when he was alone while I was out partying, and it turned out that that there were lots of Friday and Saturday nights when I left him working on one of my papers for class while I went out with someone else. And I always enjoyed the sex I had on those dates the most, because of the extra thrill I got knowing that Chris (and often one or two other "steadys") were sitting home alone just because I demanded it of them while I was out having fun and sex with someone else. A few times I let Chris know that I was wearing my cheerleader sweater beneath my coat, but I wouldn't let him see.

The closest Chris really got to my cheerleader sweater was when he did my laundry. That was one task he seemed to really enjoy, because it was the one chance he got to get really close to some of my prettiest intimate items and it was when he could spend some time with the sweaters I'd worn that week. Of course, my sweaters always had to be cared for by hand, and many was the time in college when I'd return from a date with a cum-soaked cardigan or pullover in hand, to give to Chris to wash that night. Knowing Chris would be doing the cleaning made it more fun for me when a date would cum while rubbing between my breasts while I was wearing a sweater. And even washing another guy's cum from the sweater was something Chris enjoyed.

There was even a period of about six months when I was also going steady with Chris's room-mate. Partly I think I did that to test Chris and to see if he really was totally devoted to me. Sometimes I'd come over, give Chris some of my school work to do, then while he went off to the library to work I'd stay and have sex with his room-mate. But through it all Chris stayed loyal to me, and on the day of our graduation he asked me to marry him and I agreed--for a lot of reasons, including the fact that he comes from a rich family, is a tremendously devoted guy. But I did make sure that he understood that although I would demand absolute loyalty from him, I would need to have the freedom to goout with other guys even after we were married. He wasn't pleased with the idea, but knew that he had to agree if he wanted to marry me. So in June, 1991, we got married.

Although it was obvious to both me and Chris that I was the "dominant" person in our relationship, we didn't know anything at that time about dominant/submissive relationships, and I'm not sure I even really knew what a "fetish" was--I just thought Chris had a "thing" for women's sweaters. In any case, we quickly settled into a very happily married relationship. Chris became (and still is) a software consultant with an office in the house, while I have worked a variety of jobs, and our sex life was very satisfying (especially to me!). In fact, soon after we got married we drifted into an informal sex schedule in which Chris would satisfy me orally four weeknights per week (but we wouldn't have intercourse those nights), I'd go out with someone else one weeknight and on Saturdays, and then on Sundays I'd have intercourse with Chris.

This schedule, of course, kept Chris really horny most of the time, and I noticed that the hornier he was the more devoted to pleasing me he was and the more obsessed he was with my sweaters. When sweater sets first came back into style, he went crazy buying me every color and material he could find. In fact, shopping for sweaters to buy for me was basically his only "outside the house" activity. But I knew he loved it, although we never talked about his fascination until about two years ago. It was about then that we got a computer and I started discovering the world of adult internet sites and learning about what lots of people do that I didn't know anything about--and I started to realize that I probably had a bit of a "dominant" side to me and that Chris certainly seemed to be "submissive" and certainly had an obsessive interest in any sweater I wore.

One Sunday night I decided to see just how focused on sweaters Chris was. After some mild foreplay, I told him to get undressed and that there was something I wanted to try. In a moment he was standing in front of me naked. I went to my closet, took out a pastel blue angora cardigan, told him not to move, and then started to caress his body with the sweater. I started with his back and chest and face, then moved to his legs and finally his crotch. Boy was he ever excited! He was just dripping, and almost seemed in a trance. I told him to put a condom on so he wouldn't make a mess, then draped the sweater over his cock and around his balls and started rubbing him through the sweater. I told him I wanted to make him cum that way but that it would mean we wouldn't have intercourse that night. Was that what he wanted? Did he want me to stop rubbing him? He hesitated just a moment then gave a low whimpering "no--please don't stop." As I rubbed the sweater against his balls and cock very slowly, I told him that since we weren't going to fuck that he'd have to satisfy me orally first, and then I'd rub him more with the sweater. I then had him kneel before me while I took off my panties, spread my legs and then stood over him. He buried his face between my legs and served me with a degree of enthusiasm that was incredible. After I'd cum twice I had him lie on his back holding his knees up and spread while I took the sweater and rubbed his cock and balls. It took him about 10 seconds to cum.

For the next few weeks that scene repeated itself on Sunday nights. First Chris got to pick one of my sweaters from the closet. He'd look them all over and take about an hour to choose. He'd go through my large collection of sweaters one by one, feeling them, sometimes even kissing them, before choosing. One time it was my thick pink mohair, another time it was my red angora cowl neck, another time my gray lambswool turtleneck. Of course, by the time he had made his choice he was already incredibly aroused. After having him strip and then rubbing him a bit with the sweater, I'd ask him if he wanted me to stop--meaning that we'd have intercourse--or if he wanted me to keep rubbing him with the sweater. He could never bring himself to ask me to stop even though, after a couple of weeks, I started making him finish himself off instead of me doing it for him.

Then, a few weeks later, I added something new again. Before starting to rub him with the sweater, I laid out his selection (he'd picked a pale yellow oversized angora cardigan) smoothly on the floor and told him to kiss it and worship it. He looked at me with a quizzical look and didn't do anything for a moment, but I just told him to go ahead, that I knew he loved and worshiped my sweaters so I wanted to him "make love" to one. He put his face down, and almost immediately became totally focused on the sweater, kissing it, licking the buttons, smelling it, rubbing his cheek against it--it was hysterical! I couldn't stop myself from laughing, but he kept right on going, and it was good he already had a condom on because he actually came without rubbing his cock at all.

Well, by then I decided that it was time Chris and I had a real talk. From my explorations on the computer I'd learned a lot more about female domination and that not all submissive men are the same. From what I could tell, Chris was not interested in leather and rubber, and didn't seem to want to be really hurt, but he did love to serve me and the more humiliating I made the situation for him, the more his cock seemed to respond. Also, I went through Chris's files on the computer one day, and saw he had downloaded a number of stories. Some of these were "sissy maid" stories, and all of them involved female domination with a lot of humiliation. One story, I realized, was something he had written himself as a fantasy, and it was all about me making him dress as a woman (in sweaters of course) and about me making him serve as a "maid" to me and one of my boyfriends.

So I decided we would have a talk. I starting by telling him I'd discovered the fantasy story. I think he really wanted me to discover it, but when I told him he looked shocked and actually started to cry, telling me how sorry he was and that it was only a fantasy. At that point I had him take off his clothes and kneel in front of me, and then I told him I thought the story was true about what he really wanted, and that there was nothing the matter with his feelings and that in fact I thought what he wanted was very sweet. I then went to my closet and got out a mauve lambswool sweater set, showed it to him, and told him I thought that what he really wanted was to be feminized and to wear soft pretty wool things and to serve me. He just looked down and cried some more but he didn't disagree. I also told him I thought he really liked it that I slept with other men and that he'd rather be my sissy servant dressed in a pretty sweater set than my lover. Again, he just looked at the floor crying without saying a word. At that point I went to my dresser and got out a pair of panties and a bra, then went back to Chris and told him to put them on. He kept whimpering how sorry he was, but he did as I told him. He fumbled quite a bit with the bra, which had me in stitches. Finally I showed him how to start with the clasp in front, then turn it around and slip his arms through the straps. I put a balled-up stocking in each cup to give him some shape, then I told him to put on the sweater set, and got him some pantyhose and a skirt. When he was done I made him look at himself in the mirror, and told him that what he saw was my new sissy maid Chrissy and that he was going to spend almost all of his time that way from now on and that his days as my lover were over--that I had other men to have sex with and he would probably never be having sexual intercourse ever again. He cried even more when I said that, but when I demanded to know if he understood and agreed, he did manage to whimper a soft "yes."

Of course, if I was going to feminize Chris he needed a wardrobe--I didn't want him wearing all my clothes (even though we are basically the same size except that I'm a bit taller). I told Chris what the plan was, then told him he could take off the skirt and put on some pants, but he had to keep on everything else! He stared at me with this terribly pained expression and said he couldn't possibly go to the mall like that. Before saying anything in reply, I got two kleenex from my purse, and added one to each of his bra cups. Then I told him that of course he could go out like that--he just had wear a coat and no one would know what he had on, but if he kept complaining, I'd keep adding padding to his bra until even with the coat on there'd be no hiding what he had on. He got quiet at that point, put on a coat, checked himself in the mirror, saw it was pretty much OK (you could see a bit of the sweater--I'd made him button the cardigan right to the very top--at the top in front right at his neck, and the ends of the sleeves poked out a tiny bit from the arms of the coat, but that was about it, and the padding I'd put in the bra only showed through the coat if you really looked) and off we went.

What Chris didn't know what that I had planned to make sure that some people at the mall did know what he was wearing! Our first stop was Victoria's Secret to buy some panties, bras, garters, stockings, and nighties. Chris was obviously embarrassed going into the store, but as soon as we started looking at panties he got totally engrossed in what we were doing, and I could tell he was really excited picking out panties for himself. After a minute or two a young woman came over to help us, which brought Chris out of his trance a bit. She started to comment to Chris on how pretty the panties we were looking at would look on me, but I immediately interrupted her with the correction that in fact the panties were for Chris! Chris's jaw just dropped when I said that, and the salesgirl stared at him and almost started to laugh, but she kept control (I assume it was part of her training at the store to not react to anything odd that a customer might want) and in a rather matter of fact way asked him his size. Chris, however, was unable to speak, and just docilely let me and the salesgirl lead him around the store as we picked out about a dozen pairs of panties for him.

We then moved on to pick out a couple of garter belts and some stockings. The salesgirl did a good job of maintaining her composure and acting as if she helped pick out lingerie for men to wear every day. So instead of whispering and acting like there was something odd, she would simply point to items we might like, ask me if I liked them and also ask Chris and say things like "that would be really pretty on you". But I also realized that she had noticed the bits of mauve lambswool peeking from his neck and cuffs (I think the pearly button at his neck was the giveaway), and though she was trying not to stare, her eyes kept coming back to those areas. Obviously she was trying to figure out what he had on under his coat. I decided that she had been so nice that it was unfair to keep her wondering, so after looking around and noticing there was only one other salesgirl in our part of the store and no other customers, I told Chris I thought he should take off his coat. He started to say that he was fine with it on, but I gave him a stern look and he submissively followed my "suggestion.

The salesgirl actually gasped at how he looked without the coat (of course, with just the sweater on the shape of the padded bra showed clearly too), but although I thought she'd start laughing she didn't. Instead she just looked and said very sincerely what an absolutely gorgeously pretty and feminine sweater it was and she told me that she thought Chris looked rather adorable in it--soft and sweet and cuddly. Chris just stared at the ground, but he did smile a bit when she said that--the first time he smiled since we'd entered the store

Chris lost his smile, however, when he saw that the other salesgirl in that section of the store had also noticed him, and she was laughing--and she called the cashier over to take a look too. And to make matters worse, just at that moment two girls who looked to be in their early teens happened by, and they just stared at Chris while they giggled uncontrollably. Chris turned his back to them, but they moved across the room for another look. As we turned our attention back to picking out garter belts, I could see the girls continue to follow us while whispering constantly to each other. Then, much to my amazement (I couldn't believe their nerve) one of the girls actually came over and, after a quick glance back at her friend for encouragement (and while giggling so much she almost couldn't get the words out) she said to Chris that she had a sweater almost just like his, and it was one her her favorites. Then she started laughing again. Well, at that point the salesgirl told the girls not to be rude and motioned to the other salesgirl to move the two teenagers out of that section of the store.

I did let Chris put his coat back on at that point, but told him not to zip it up. That way, other customers would not easily notice what he was wearing, but there was some chance they would, and certainly there was no chance Chris could forget for even a moment that from waist to neck he looked more female than male. In any case, we next we moved to the nightgown section. We ended up getting him two sheer baby dolls (pink and red), a blue full length sheer, and two floral-patterned flannels. All this of course was a large sale for that salesgirl, and as she was ringing it all up she made of point of telling us that she'd be happy to help us any time we needed anything more, and that she'd also be happy to help set things up for us with salesgirls she knew at the department stores in the mall that she knew would be very helpful and understanding. She even took Chris by the hand and told him again that she thought his sweater set was really pretty and that he looked just adorable and very feminine in it, and that she hoped we would return. I thanked her for all her help, had Chris thank her, and told her we would undoubtedly be back but that next time it would be with Chris fully dressed and living as woman. Well, by then Chris was starting to fully comprehend his predicament. He looked at me, barely holding back tears, and in a quivering voice asked if I really meant to make him live as a woman full time and forever. I told him yes--that was what I wanted and I intended to make it what he wanted to. One of my goals for the shopping trip was to impress upon Chris that since he was going to be feminized it would be better for it to be done right--so that he could pass as female rather than looking like a crossdressed man. The idea was to show Chris that continuing to live as a male was no longer an option. It seemed to me that the best way to get Chris to really understand the situation he was now in, and to get him to accept the need for the kind of permanent transformation that I had planned for him, was for him to experience what things would be like if he at all resisted my feminization program for him--no matter what it might entail. In order to help make that point clear to him, before leaving the store I made Chris remove his coat again, then told him to go by himself and have his ears pierced in the mall and then to meet me at the car! He looked at me pleadingly, but my stare made clear that I was not going to change my mind, so he submissively handed me his coat, and started walking out of the store and down the mall. I saw him trying to keep his arms folded across his chest to hide the obvious effects of the padded bra, but given that he was wearing the mauve sweater set, I don't think he was accomplishing very much. I almost felt sorry for him, but reminded myself it was for his own good. Well, when he got to the car about twenty minutes later he had silver studs in his ears and he was totally in tears (and out of breath from running), and between sobs he begged me never to do that to him again. I told him to tell me everything that had happened. He said it took him a while to find the ear piercing place--he was afraid to ask directions from anyone, and everyone was staring at him so he tried to just keep on walking until finally he saw the place in front of one of the large department stores. However, he then had to wait in line under the constant stares and giggles of passing shoppers. He said the woman doing the piercings was very nice and told him she did lots of men, and she thought it was kind of cute. I asked him if he understood that the only way to avoid this kind of humiliation in the future would be for him to help me feminize him to the point that he could pass easily as a female in public. I told him I planned to make it so his figure would do proper justice to a nice soft angora pullover. He said he understood and that he would go along with anything I asked. Even, I repeated, if it meant transforming him so that he could pass as female while wearing a tight sweater and no bra? It took a moment for the meaning of my words to sink in, and then he gave me a pleading look, but I just said that the alternative was more experiences for him going out in public looking like a man in a dress. Sobbing, he said he'd go along with whatever I thought was best.