Home alone Mistress (Wife) & Sir (Her BF of 6 years) are out and about visiting, allowing there sissy her monthly 1 day off, time for sissy to sit looking out at the world on a rainy afternoon with my sissy cock uncaged just thinking of the day 5 years & 2 months ago that my life changed forever. Instead of just thinking I decided to put it down in words.
I had decided to drop into a bar just to relax after a hard day in the office. I had been dealing with some fairly influential people and they always cause stress. The only saving part of the whole process was knowing I was in some sexy lingerie with panties and bra matching. Just before I left my office for the night I slipped into the bathroom and changed into a pair of shorts and golf shirt admired myself in my wonderful lingerie and slipped on a pair of summer sandals and headed for the bar.
I was born in a hospital in Denver Colorado and my mother passed away at the same time as my birth, so I never got to know her. I was raised by my father on a ranch just outside Breckenridge, Colorado as an only child.
It didn’t matter to me that we were both naked as we ascended the staircase, hand in hand, to our bedroom. Why should it bother me? Beach was down in the cellar with Alice, my chauffeur had his own cottage elsewhere on my estate, and so there was nobody else in the house to disturb us. I could see, from her pert nipples, that Rachael was still aroused after our session in the cellar, possibly in anticipation of pleasure yet to come, or possibly from seeing Alice humiliated by Beach in exactly the same way that Alistair had humiliated her in his office.
My biggest mistake …..Continued Chapter 3
The next week.
I woke up with a start and realized I had fallen asleep on the sofa after Brooke had dropped me off. My ass still hurt and burned as I had no idea how many times I had been fucked the night before, definitely more than just a few, for some reason my mind had just shut down and my body took over.
Although I’d been turned on at the sight of Rachael’s pussy lips when she was bent over in my erstwhile husband’s office, I had not enjoyed watching him fucking her. But now that we were both naked, I was determined to kiss those delicious lips and enjoy the taste of her sweet pussy while my soon-to-be-feminised husband, Alice, looked on as she suffered the indignity of being face fucked by Beach, my butler. Her muffled cries and gasps as Beach’s cock slid through her ring gag were really turning me on, so much so that I could feel the moisture running from my pussy down my legs.
This actually just happened and I have no idea where it is going, I will keep you informed as it moves forward.
I work from home and as with many of you I enjoy wearing women’s clothes and being as much of a woman as I can but since I am married I have to be careful.
My wife works late some evenings and she visits family several days a month, which is located out of town and those are the times when I can be who I want to be and enjoy an afternoon or night to myself.
Another uneventful day tidying up after holiday makers and I was just about ready to scream.
When Star showed up and we were going to the restaurant I said to her in a low voice "Why are all of the people who come here such muppets, they can't even pick up a spoon from the floor but they can and do go to get another one. Or the ones who put their tray away but leave everything else on the table, sometimes even their own things, like wallets and phones."
Once I was naked and on my knees in front of Lucretia, the process seemed to take on a life of its own. It almost was like I was watching myself as I begged to be made submissive and obedient. As I explained why I should be forced to look and behave as a female. And although I was frightened and weeping uncontrollably, I was at the same time unbelievably excited. The realization settled over me like a shadow that somehow this was exactly what I wanted.
When I thought nothing could possibly make my predicament worse, Lucretia found a way to make it catastrophic. In order to prevent her from releasing the videos that would destroy me, she demanded that I become her sissy servant. Moreover, she insisted I agree to her terms immediately. Any hint of hesitation would be interpreted as a lack of cooperation and I sensed she would take genuine pleasure in publishing those videos. I was left with no choice. Weeping uncontrollably, I stripped off my clothes, knelt in front of her and pleaded, "Please turn me into your obedient sissy, Lucretia.
I have been waiting for this for a long time. My owner away i felt like it was time to make her happy but failed doing so and upset a Mistress in chat room.
After receiving a few bad reports my owner decided it was time to punish me. I was humiliated on her return by showing my new sissy self of to her friends for the first time.
She was not happy with the way I looked they took me out dressed up to get a mani pedi and then off to the mall for a make over and a new dress. The Female clerk behind the counter enjoyed herself a lot I.m sure.
I was completely immobilized by my predicament. My mother-in-law not only knew the details of what should have been my most closely-guarded secrets, she was also in possession of several hours of video evidence that left no doubt that she wasn't bluffing. I was incapable of any response other than to tremble and weep. And to beg. "Please don't make those videos public, Lucretia. I'll do anything you ask if you promise not to publish them." I could not begin to imagine how devastating it would be for me if those horrible things were made public.
She would have been on my MILF list if I had not known her so well. Way up near the top. For a woman of a generation older than my own, she was exquisite. Intelligent, statuesque, impeccably groomed, she had it all. I confess that she had entered my fantasies more than a few times. Trouble was, she was also my mother-in-law and I knew she could be the perfect bitch.
I woke up feeling as if a hamster had died in my mouth, but I didn't move as I could feel Star's loving arms around me and that helped with the pain from the hammer in my head. eventually I had to move, I had to get rid of what I'd drunk last night.
When I looked in the bathroom mirror I was surprised that I didn't have a furry tongue, but the taste in my mouth was definitely improved by the toothpaste.
The looping video was too much to take, and after two more runthroughs, I’d had enough. Whatever was awaiting me wasn’t going to go away. Half-heartedly, I tried the other doors from the room, finding them locked. Having no real option, I walked across the room, heels tapping out an echoing tattoo on the wooden floor. I tried not to think of what humiliation awaited next, as I knocked on the door.
I awoke the next morning and found that Star was cuddling me from behind. What had woken me was her playing with my nipple rings, my nipples were erect and from the feeling in my groin I'm sure I was wet down there. This was confirmed mere seconds later when Star moved one of her hands and started playing with my shemale clitty.
The next morning after my shower I realized it was going to be a hot day and decided, as I wasn't allowed shorts, I would wear just my tartan mini skirt and a sports bra. A pair of three inch heeled sandals completed my outfit. To cover my modesty I slipped on a black lace thong, a quick flick over the eyes with eyeliner and mascara, a dab of lippy and after a spritz of eau de toilet I was ready for work.
The pretty Asian nurse entered and took only a few moments to take an inventory of her surroundings. Then in a gesture I found utterly charming, she touched her sternum, smiled and said softly , a phrase that to me sounded like, "No eeng greese." It only took me an instantnt for me to understand that she was telling me that there was a language barrier. We wouldn't be able to communicate verbally unless I suddenly received the gift of tongues from the Holy Ghost. I wasn't counting on that.
Did I describe our Friday night lovemaking clearly? On Friday night I make my lover listen to a vivid description of the next humiliations he will be made to endure, as I bring him gently and lovingly to his orgasm. I never want him to be taken by surprise by our BDSM play. If I intend to spank him, he has been told that he is to receive a spanking at least one week prior. Our Friday preliminaries have become one of our favorite activities. Once it became clear that we were establishing ourselves in dominant as is submissive roles, Tommy is put into light bondage for these sessions.
"Something that you don't know, Da.. Jade." Said Becky. "There was a trust fund set up when dad died for his children, he knew you were coming, even if he didn't know what you were going to be. It was set up so that it pays out on your twenty first birthday or when you marry. It's not huge, about twenty thousand, but it will set you two up in a place of your own."
"We can find you an inexpensive wardrobe at the thrift stores, start your makeover as soon as we get home from work on Friday afternoon and spend the whole weekend being girlfriends. Girlfriends with benefits. "Oh, my gosh! Thinking about making love to you when you're a girl is making me so excited I can hardly stand it!"
I was excited and so was Thomas. His response to my description of our upcoming sex play was my signal to continue the game or to back off a little bit.
So I found myself in the middle of town, in a busy shopping mall, dressed in a short skirt, little top, bra, panties and high heeled court shoes, shopping for girl clothes for me, and I found I wasn't nervous anymore, I was excited. I couldn't wait to find out where Star was going to take me first.
"Well, here we are, what do you want to buy first?" Star asked.
"What? Oh! Erm... Well you said an LBD was an essential, so why don't we do the essentials first?" I replied.
I think I had been here for nearly a year when this incident occurred. I was kidnapped. Hood pulled over my head, pushed into a vehicle, driven to a place whose location is a mystery, the whole routine. Except instead of being the cool, calculating hero from the movies, I was the terrified victim, crying, begging and wetting myself. I'm sure my mother-in-law was somehow responsible, but it has been impossible, since my abduction, to know anything for certain. Except that I'm not allowed to leave.
Back at the chalet Star said "Go have a quick shower, keep your hair dry we don't have time to style it tonight."
I came out of the shower and threw on our bathrobe whilst Star finished her make-up. I was still worried about ID, how was I going to get into a club. When she had finished she said "Come here and sit down facing me, I'm going to do your face for you for tonight, then we'll be half way to getting you in the club."
"Arm binders, dear. You're in level 2 bondage today and you know why. " I turned my back to Miss Marilyn and allowed her to begin immobilizing my arms in those horrible restraints. I also expected to be hobbled at the ankles and gagged. The leash was a given. My punishment for pretending I thought I should be working in the laundry room when a uniquely loathsome client was scheduled in my appointment book. So this morning, I had finished my hair and makeup, put on the seductive lingerie that had been set out for me and presented myself to Miss Marilyn, as ordered.
Every imaginable variety of sissy can be viewed at this convention, of course. This makes people watching the number one spectator sport, and it doesn't cost a dime, once you're inside. (Actually, hanging around one of the entrances watching the crowd arrive makes for a pretty good show in itself.) In past years, the new sissies fascinated me the most. The ones who were being put on display for the very first time. The ones who hadn't completed their first year as sissies. Many of them hardly feminized beyond what they were wearing.
I awoke the next morning feeling great. I may have lost all of my possessions but I had a girlfriend who loved me and I was having the best sex I could imagine. If she was little kinky I didn't mind, I was having fun.
I slipped out of bed and put the kettle on for morning tea. Star stirred at the noise the kettle was making and getting up went to the bathroom. I took the tea back to the bed whilst Star was showering. She came our looking far more alert than when she went in.
Yes, the concourse is crowded with the vendors' displays and presentations. All those articles, all those services supporting the culture of women who turn men into submissive slaves who look and act like girls. But there is a whole other category of offerings, not visible to the casual visitor. Access to these offerings requires proof of membership in one of three organizations or the accompaniment by a member.
I followed the two of them from the room, noticing how their lovely gowns accentuated their figures, as they rattled off instructions. I was beginning to feel sick with fear, moving slowly and hampered by the skirt and heels. I was going to get found out, I just knew it.
We entered a sitting room, where Rebecca unlocked a heavy case. The diamonds!! I’d almost forgotten about them in turning my thoughts to escape. I was pulled out of my thoughts by Elizabeth’s sharp snap.
The Sissy Rodeo is always held in Las Vegas, as you might have guessed. Lots of convention space, but more importantly, our gathering is well-suited to this odd town where ignoring reality is a practiced undertaking. In most places, this convention would be ranked well south of outrageous, but here, no one gives us a second thought. In Las Vegas, weirdness is as common as gravity anywhere else. Still, not everyone is drawn to the event. And yes, attempts will be made to draw males unaccompanied by a supervising female into femininity. But not aggressive attempts.
The competition in which Loretta defeated me is known as Satisfied Sissy. For those unfamiliar with the culture of training young males to strive to their utmost to imitate submissive girls, a few words about how the game is played: Two sissies are dressed in similar female outfits. Their clothing is always selected with an emphasis on feminine detail and absurdly intricate undergarments. The audience insists that every detail of their grooming be as perfect as possible.
It wasn’t going to plan. It always went to plan. Always. Except now, when it wasn’t.
The plan was to steal the Duchess’ diamonds on the day of the charity reception. It hadn’t been difficult to buy delivery details, and it hadn’t taken long to find a staff member to make the acquaintance of over a few romantic evenings and who would spill some details of her place of work.
The only downside was that the only plan I’d come up with was to impersonate a maid. Still the fee I was offered to do it would be enough to put up with that, and no-one would ever find out.
It was just impossibly bad luck drawing Loretta in the very first round of this year's competition. I know I can't beat him and even worse, this is the last time I'll be eligible to compete. I won't be classified a sissy next year. I'll probably be the newest bride in a sultan's harem. But for now, Loretta has already taken me into his amazing mouth and I haven't even begun to free his cock from his panties. I utter a soft moan of frustration as I helplessly ejaculate in response to the attentions of his lips and tongue.
It was my first job since leaving school, it wasn't much just cleaning tables and sweeping the floor in the snack bar of a holiday centre. But it was a job, and I was lucky to get it in the present economic climate. The hours were good, twelve noon to seven in the evening with an hour for lunch, to be taken between twelve and two and an hour for an evening meal, to be taken between five and seven. so in reality I was only working for five hours a day six days a week. It was minimum wage but two meals a day and accomodation bumped it up a bit.
"You look like you want me to stop. I really thought you'd last longer. Very well. We'll start wrapping this up. But we're not quite finished. I'm going to keep giving you more spanks until you tell me to stop. And how will you tell me when you've had enough? Darling, I'll stop spanking you when you beg sincerely to be my sissy. When you convince me that you want me to make you as girly as I possibly can. 'Kay? Understand the rules? Beg me to be my little girl and the punishment stops. Insist that you're still a boy and I'll just have to keep putting red marks on your bottom."