The Mammoth Book of Urban Erotic Confessions

by Barbara Cardy

  At last, I told him he didn’t have to worry; I’d keep his perverted little secret to myself. The look of relief on his face was short-lived, though, as I let him know exactly what price he’d have to pay. I told him he had worn male clothing in the house for the very last time. Except for a couple of items I’d keep for those times when he had to go into town, all his suits, shirts and trousers would be donated to charity. I would be getting rid of all his pairs of underpants, too. From now on, he would be wearing frilly lace panties every day. I couldn’t help notice that his cock twitched in my French knickers at those words, and I knew I couldn’t afford to let him think he’d in any way got the upper hand in this situation.

  I reminded him how I’d often said it would be nice to hire a cleaning lady to do chores around the house, but now we only had my salary to rely on, that would be an unnecessary expense, and completely out of the question. Instead, Gerald – or Geraldine, as he would be known from now on – was expected to carry out all the cooking, cleaning, laundry and whatever other domestic work was required. If the tasks were not performed to my exacting specifications, then he could expect punishment. Furthermore, I expected to be referred to as “mistress” at all times. And, as the final humiliation, I told him I would be ordering a chastity device into which I would be locking his pathetic cock, and any relief he received would be on those rare instances when I decreed it. Grovelling on the floor, my husband kissed my feet and accepted every last one of my demands, even though he knew his life would never be the same again. Oh, yes, I was truly in charge now, and I was very much looking forward to the start of our new domestic arrangements.

  To prove that I was as good as my word, I set about removing all Geraldine’s male attire from the wardrobe, apart from one suit, a shirt and a Fair Isle sweater. Everything else was put into plastic bags, ready to be taken to the charity shop. His pyjamas and dressing gown joined them; from now on he would be wearing a frilly baby-doll nightie to bed, and if it made him look ridiculous – well, that was all the fun of dominating my cissy husband, wasn’t it? As for his underwear, the only place for that was the bin.

  The very next day, we went shopping for new lingerie for Geraldine. I took him to the grandest department store in town, and ordered him to go up to one of the female assistants and ask her to show him a selection of items. He had to make it quite clear the underwear was for him; I knew how much this would make him wriggle and blush, but I also knew his cock would be hard in his trousers. After all, it wasn’t rocket science to realize that my husband got ridiculously turned on by having to demean himself in front of women. And I wanted him to have a little bit of excitement before the chastity device I’d ordered over the internet the night before arrived and I took away his power to get an erection unless it was on my say-so. Once the assistant, who didn’t bat an eyelid as he asked her to pick out frilly panties, bras, a sheer baby-doll nightie and a silk robe in his size, had found things that would fit him, he made his choices, all the while aware that I was watching and enjoying his shame. Just to rub in the fact that after today he would literally be no longer wearing the trousers, I whipped out my credit card and made sure the assistant was aware that my money paid for everything.

  That was the start of a whole new regime for poor, feminized Geraldine. Once we got home, I locked his male clothes away in a trunk to which only I would have the key. Then I sent him into the bathroom with a razor and a can of shaving foam and ordered him to remove all his body hair from the neck down. Luckily for him, he’s never had a particularly hairy chest, but I knew defuzzing his balls and arse crack would be something of an ordeal. When he hesitated, I told him to hurry up or I’d take him down to a beauty salon and get them to wax him clean.

  Once he emerged, looking wonderfully smooth, I made him get into a matching set of white silky bra and panties. He did look strangely feminine in his new outfit, and I knew the illusion would be enhanced once the hair on his head had grown longer. The burly businessman I’d married had gone for good, replaced by this willing, submissive cissy.

  He spent the rest of the day cleaning and tidying, supervised by me, of course. I made him dust all the hard-to-reach places like high-up picture frames and curtain rails, and once he’d finished I followed behind him, running a white-gloved finger over everything to see how thorough he’d been. Of course, I found a spot on top of the bookcase in our bedroom where my glove came away streaked with grey dust, and that’s when he knew he was in trouble. Without ceremony, I ordered him to bend over a chair before tugging down his panties and using my wooden hairbrush to spank his arse until it was beet red and hot to the touch. He yelled and squealed as I beat him, promising me he’d do a better job in future, but I told him I doubted that very much. I did take some pity on him, though, wrapping my fingers around his cissy shaft and wanking him to a brisk climax, informing him all the while that this would be the last orgasm he’d have for a long time to come.

  Two days later, the chastity device arrived. Once in place, it stopped Geraldine’s dick getting even half hard. I had thought about buying one of those cock cages which have little spikes on the inside, knowing how painful it would be for him if he ever did find himself getting an unauthorized erection, but that would just be cruel. After all, with the key to the padlock that secured it safely in my possession, I knew he wouldn’t be getting any relief any time soon.

  Our life soon settled into a new and very satisfying rhythm – satisfying for me, that is. However exhausting a day I’d had at work, I never had to worry about doing the chores or cooking dinner when I got home. I knew Geraldine had all that in hand, and if not, then woe betide him. I never ran out of ways to keep him busy, insisting that he wash all my lingerie by hand and bake his own bread. I have to admit that before long he’d become a very good cook, and the instances when I had to paddle his arse for leaving a pan on the stove to boil dry grew sadly fewer and further between.

  The other thing he improved at was giving me oral. When we were first married, it was something he’d done with some reluctance, as a means of getting me to suck his cock, but as I’d taken my first steps at dominating him, I’d encouraged him to go down on me for longer, and his technique grew steadily better. Now, however, he licked me with real enthusiasm, learning how best to tickle my clit and nip gently at my pussy lips, and he didn’t stop till I’d had at least a couple of orgasms on the end of his probing tongue. I think he believed that if he gave me the kind of satisfaction I liked best I would respond by letting him come, though he was foolishly mistaken in that regard. His orgasms were still under my control, and very strictly rationed.

  I must admit that when I told Geraldine none of his old friends would ever know about our new arrangement, I wasn’t entirely honest with him. It wasn’t long before the urge to let other people see how I’d feminized him grew so strong I could no longer resist it. Add to that the fact I’d always found one of Geraldine’s golf cronies, Adam, very attractive, and I was overcome by the temptation to make my husband a cuckold, as well as a cissy slave.

  One evening, I arrived home from the library with Adam in tow. I’d warned him in advance that our home life had become somewhat unorthodox, but even so he could never have been prepared for the sight that greeted him when we walked through the door. My husband, in bra, panties, stockings and suspenders, vacuuming the hall carpet. He squealed, turned off the cleaner, and tried to flee into the kitchen. In my sternest tones, I told him to stay where he was. I’d brought Adam home for dinner, and I’d expected him to be made welcome. Instead, he’d have to witness how I chastised Geraldine for misbehaving, and then I’d be taking him upstairs for sex, which Geraldine was required to watch. At last, the full true misery of my husband’s submissive state sunk in. Adam was not only a good fifteen years younger than him, he was better looking, too – and in his neat work suit he was every inch the gorgeous alpha male, as opposed to the whimpering cissy I now had at my beck and call.

  Geraldine intended to serve freshly gr
illed steaks, which at least meant dinner wouldn’t burn while I dished out his punishment. I ordered him into the living room, and went to fetch my latest toy. I’d found it on the internet: a leather paddle emblazoned with a cut-out reading “SLUT”, designed so that the word would be clearly visible on Geraldine’s arse cheeks when I’d finished beating him, stark white against his red, sore flesh. My husband got into his usual position for such occasions, bent over, gripping the back of a chair, with his legs wide apart so that his sensitive balls were easily available if I chose to subject them to a spot of torment. Adam watched, wide-eyed, as I eased down Geraldine’s panties, baring his smooth, hairless arse. I had no idea whether he’d ever imagined couples enjoyed such bizarre domestic arrangements, but if this was his first sight of the interaction between a mistress and her slave he seemed to be enjoying it, if the obvious bulge in his trousers was anything to go by.

  Assured that I had a willing and eager audience, I set about beating Geraldine’s backside with vigour. Again and again my arm came down with force, the paddle whacking against his cheeks. With no gentle warm-up before the main action, he really felt every one, shrieking like the cissy he was in response. By the time I’d finished, he was visibly branded a slut, and Adam’s cock looked like it was trying to bore through the front of his trousers.

  I couldn’t wait any longer to get the fucking I needed. The combination of Geraldine’s tongue work and my biggest dildo might usually be enough to satisfy me, but nothing compared with the feel of a real cock, thick and hard, sliding into me. Slipping my hand into Adam’s, I took him upstairs.

  He seemed to know that I needed to be seduced, or maybe he just wanted to rub in the fact he was about to get what Geraldine had so obviously been denied. Whatever the reason, he undressed me slowly and sensuously, taking time to kiss my skin as he bared it. When he had me down to my bra and panties, he stripped off himself. My mouth watered at the sight of his gym-toned body and straining shorts, and when he slipped down his underwear to reveal the biggest cock I’d ever seen, I almost squealed with anticipation. My husband had nothing to complain about in the dick department – apart from the fact his had been locked away and denied relief for the longest time – but Adam really dwarfed him. I knew I needed to be very wet to take him, so I told Geraldine to get on the bed and lick my pussy. He did as he was told, his tongue flickering over my secret folds and causing my juices to flow. He would have brought me to orgasm without a murmur, but I stopped him short: the only one who’d be making me come tonight was Adam.

  That didn’t mean I couldn’t have some fun with the poor cissy; I never tire of finding new ways to humiliate him, and now I saw some delicious possibilities opening up. My sex might have been good and slick, but Adam’s cock needed lubricating if I was going to take it without problems. The cruellest of smiles on my lips, I told Geraldine to get down and suck that beautiful thing. He hesitated for only a moment, looking at me as if to test whether or not I was serious. My expression must have given him all the answer he needed, for he then bent to take Adam’s plump cockhead between his lips.

  I watched with an unbelievable sense of triumph and excitement as Geraldine sucked Adam off. Indeed, if I’d known how much the sight would make my juices flow I wouldn’t have needed my husband to lick my pussy. Soon, Geraldine had as much of Adam’s meat in his mouth as he could manage, his head bobbing onto the upright length. Adam’s eyes were closed in bliss, and though I was sure he’d never had another man give him a blowjob before, he seemed to be revelling in what Geraldine was doing to him.

  At last, I couldn’t wait any longer. Lying back, I spread my legs and invited Adam to fill me up. As his cock slid into me, I was vocal in my enjoyment, wanting Geraldine to know just how good this was. Adam fucked me hard and fast, while I clung onto him and urged him on to give me the kind of shafting my feminized cissy husband never had. Geraldine knelt beside us, seemingly unable to tear his gaze from the sight of Adam’s long, thick shaft emerging from and disappearing back into my juicy hole. I could only imagine the tormented emotions that might be going through his mind. Then Adam’s dick jerked and shot its load deep inside me, and I raked his back with my manicured nails as my own body melted in orgasm.

  When Adam pulled out of me, his cock covered in a mixture of both our juices, I ordered Geraldine to lick him clean. This time there was no hesitation as he knelt over Adam’s sweating, satisfied body, and that’s when I knew I had truly gained the upper hand in our marriage, now and for all time.

  That was three months ago, and Adam has been my lover ever since. Geraldine continues to keep the house clean by day and worship Adam and me with his talented tongue by night. For all that I keep him frustrated and humiliated, I know that my husband is now the happiest he has ever been – and so am I.

  Second Shift

  Stephen, Dallas

  My wife and I had been married almost five years but had rarely spent an entire night together in the same bed because she worked a day job and I worked the night shift. Our sex life was pretty good, even though it was mostly limited to weekends, but Carol and I certainly weren’t having sex as often as I would have liked to and she knew it.

  Last summer when my wife’s younger sister – younger by only fourteen months – was between teaching jobs and was moving cross-country for her new job, my wife invited her to spend the summer in our guest room. They had always been close when they were children, sharing just about everything, and my wife thought it would be a great opportunity for the two of them to reconnect. I had always liked my wife’s younger sister so I had no concern about her spending the summer with us. Little did I know that I would get to know Amanda better than ever before.

  At first it meant having to adjust to little things like having to share the only bathroom with a third person and altering meal preparation to accommodate a third set of taste buds. Some of our evening activities changed as well, when the time between my wife’s arrival home in the evening and my leaving for work at night was filled with the two of them reminiscing about their childhood and discussing everything that had happened in their lives since reaching adulthood. I didn’t mind too much because I could always find something to watch on television.

  I quickly learned to tune them out, but occasionally I overheard snippets of conversation between the two women when they discussed Amanda’s love life. I knew my sister-in-law had not been seeing anyone for quite some time, and I once heard her ask my wife if Carol could set her up with someone for the summer. I don’t remember what caught my attention right then, but I never heard my wife’s answer.

  Amanda soon became comfortable enough around me that she stopped getting flustered when her robe gaped open or I accidentally caught a glimpse of her rear end as she stepped from the bathroom and ran down the hall to her bedroom following a shower.

  She shared a similar build with my wife – busty but slender – and both wore their blonde hair roughly shoulder length. I didn’t have any problem telling them apart when they were facing me, but one naked butt hurrying down the hallway looked much the same as the other and my cock always twitched at the sight.

  By the time Amanda had lived with us for almost a month, pretty much all barriers had come down. She had no qualms about brushing against me in the hall or leaning over me if she wanted something, and she didn’t pull away if our feet accidentally touched under the dinner table. She had even stepped into the bathroom while I was showering so that she could retrieve whatever beauty products she was after. I’m not sure how much she could see through the steam-covered glass doors of the shower but I suspected she had looked more than once. I know I snuck a peek at her the one time I caught her in the shower when I really needed something from the bathroom, and I knew from that glimpse that Amanda’s areolae were larger than my wife’s and that she apparently did nothing to tame the wild tangle of blonde hair at the juncture of her thighs.

  I found it difficult to shake the image from my mind and once even jerked off in the s
hower while thinking of my wife’s sister – after first ensuring that I was home alone, of course!

  One morning mid-summer, only a few hours after I crawled into bed, I felt someone snuggle against me. Thinking my wife had taken the day off without telling me, I wrapped my arm around the woman in my bed and pulled her close. It didn’t register at first that the woman in my arms had slightly larger breasts and slightly narrower hips than my wife. I was too sleepy to notice things like that.

  A hand wrapped around my nocturnal erection – nocturnal only because I was sleeping, not because it was actually nighttime – and pulled back the foreskin. A moment later the woman in bed with me shifted position and took the head of my cock in her mouth. She painted it with her tongue, quickly licking away the drops of pre-cum that oozed out.

  Her knees were beside my chest so I encouraged her to swing one leg over me. She did and her pussy was a mere inches from my face. I fluffed the pillow beneath my head, providing more support to my neck as I snaked my tongue out and licked along her pussy slit. I opened my eyes when I felt hair. My wife kept herself shaved and I knew at that moment I wasn’t tonguing my wife’s pussy. I also knew at that moment that I didn’t care.

  Amanda quickly took my entire length into her oral cavity and then drew back until her teeth caught on the ridge of my spongy soft glans. She cupped my balls in her hand and stroked the sensitive skin behind them with the tip of one sharp fingernail. A moment later she drew the entire length of my cock into her mouth a second time and then a third. Then she held just the head between her lips as she pistoned her fist up and down the length of my saliva-covered shaft.

  While she did that I sucked the loose flaps of her inner lips into my mouth and lightly chewed on them like pussy pink bubblegum. Then I teased her swollen clit with the tip of my tongue. While I tongued her clit, I slipped a finger into her rapidly lubricating pussy. A moment later I slipped in a second finger and I stroked the inside of her pussy with my two fingers as I continued tonguing her clit.