Chapter 1
Hi, my name is Michael. I am 44 years old. Twice married, but optimistically starting out on a new adventure. I think I am being more honest with myself than I have been in the past, but I must admit that I have said that before, not least after my second marriage broke down for largely the same reasons as my first one. I have four kids spread between my two marriages and see myself as a family man. I am a professional, having held down several high powered jobs and being a respected member of my local community. However, there is something inside me that drives me to dress in ladies' lingerie and search out women who want to humiliate me. I have to admit that the dominant women have been thin on the ground - most paid by the hour, but the dressing up is something I just can't get away from. I have no desire to pass was a woman, I just love the feel of the clothes and the feeling I get from wearing them, especially the lingerie,
However, here I am, single again, my largest collection of women's clothes ever in my wardrobe, including full outfits, dresses and even jewellery. And I have met Angela!
Angela is incredible. We have only met online, but we have spent a lot of time video calling. She is just 28 years old and a stunning blond beauty. We have talked so much - often into the early hours - about submission, control and being a sissy. We seem to both feel the same about my need to be controlled and feminised. She is the first woman I have ever met who is not immediately put off, or even angered by my need to wear ladies clothes. She seems to understand my natural urge to submit to a woman and also likes the idea of controlling me and leading our relationship. In the past, the only women who have shared my desire for a sub/Dom dynamic have been the dominatrix types with dungeons and latex catsuits and a hefty price tag. Angela is much more natural about the whole thing, wanting to weave it into our whole way of life. The most unbelievable thing is that Angela is coming to visit this weekend and will stay a week. After that time, we will decide what to do in the future. It could lead to me being a full time submissive sissy. It all depends on next week and I am going to chronicle everything that happens here as it happens in full detail.
SUNDAY 20th MARCH
Firstly - Oh my God! What a day. We have had the most intense and shocking start to our adventure together. It is nothing like I had imagined, but it is also immeasurably better than I could ever have dreamed of. Mistress Angela is beautiful and unbelievably superior. I have never met a more impressive person in my life. And it is so effortless. It doesn't feel like playing. I simply worship her. I will try to get Mistress Angela to contribute to this journal, especially if we have any problems, because just one side will never do this story justice. Before she arrives, I actually believe I know what this week is going to be about, but by the time she has been here for three hours, my expectations are completely turned on their heads.
Angela arrives at midday after a two our drive. I am waiting outside my house to welcome her and guide her in. On the outside I am wearing navy blue chinos and a maroon Lacoste polo shirt, underneath I have on my new maroon silk lingerie set trimmed with cream frills and bows. The set includes a suspender belt and I have some sheer tan stockings on as well.
I open Angela's car door and she glided out of her car like royalty. Her long blonde hair is up in a messy bun which shows off her beautiful long neck. She is elegance personified. I lead her into my house, making small talk as we walk. I offer her a seat in the living room and ask if she would like a drink. She sits on one side of the sofa and says she just wants water which I rush off to fetch, giving her a large lowball tumbler with ice and another for myself. I sit opposite her and smile stupidly at her, overwhelmed by her beauty in person even though I have seen her online so many times. She is wearing a lovely ivory coloured silk blouse. Her skirt is above the knees and neatly pleated with a subtle pinstripe design. She has black stockings, or tights and patent leather high heels of about 3 inches. She takes a sip of water, places the glass on the coffee table then stands up stepping to one side of the sofa. I now get to see the totality of her perfection. I can't give you figures for her figure, because I don't know all her measurements, but all I can say to describe her is that from to to toe she is perfection. As beautiful and sexy as any TV personality with a warm winning smile. Ample breasts, firm looking with a little jiggle. Slim waist and hips that flare out below it. Long legs with well defined calves supporting a bottom that seems to have a life of its own. The way it sways when she walks is mesmerizing and it is hard to take your eyes off her when you are in her presence.
"Michael. Take those silly man's clothes off and show me your true self."
I quickly stand up and first take off my shoes. Then the polo shirt and chinos come off and I fold them neatly on the coffee table. My heart is beating fast as I stand nervously in front of Angela, acutely aware of my erection making my silk maroon panties bulge at the front.
"Now that's better isn't it Michael?"
"Yes Mistress, much better, thank you."
"Come closer. I think you may need some help getting comfortable in these tight panties."
I step in front of her and she kneels down, then she gently pulls the front of my panties down and allows my penis to spring free.
"There you are." She takes hold of it in one hand and slowly starts to pull back on the shaft, making my foreskin reveal my swollen head. She moves her hand slowly the other way scrunching up the skin until it covers the swollen head of my penis. "It's a darling little willy. Smaller than it looks online, but very sweet. Now why don't you lie down on the sofa and let me take care of it for you?"
As I lie down on the sofa, Angela turns to look at me, my penis erect in front of her.
She takes hold of it again and strokes up and down a couple of times and I start to tense up almost immediately. Sensing that I am going to cum soon I blush deep red.
"Oh look. It's twitching all by itself." Mistress Angela lets go of my penis and watches it bob up and down in front of her. Then she rubs it quickly until I spurt ropes of cum all up my belly. Angela keeps rubbing to encourage the last few spurts then slows down and let's it lie on my tummy. "There there Michael. It's all over. You can relax again. Angela now proceeds to gather all the sperm I have ejaculated between her palms and brings them over my mouth. She pours the slimy sperm into my mouth whispering, "Eat it all up like a good sissy." I swallow the sperm eagerly and thank her.
Angela now slips my little soft penis neatly into my silk panties and gets up off the floor. She walks over to the big arm chair and sits down.
"Listen very carefully to what I am about to say now Michael. I am going to set out some ground rules for this week we are about to spend together. This is a tryout week, during which both of us can find out whether the kind of life we have discussed and described online can actually work for us in real life. The most important thing is that I am totally in charge. You have chosen to hand over control of every aspect of your life to me. If the experiment is successful, we will marry and I will then have control of all your money, savings and earnings and I will guide our future lives, but for this experimental week it will be only our day to day activities that I control. We must both be mindful of the level of trust you will need to place in me for this to really work. This is not a game. We are not roleplaying. We are test driving a lifestyle. I am in no way forcing you to submit to me. We have agreed as consenting adults that I will lead and you will follow. I will control and you will obey. Do you agree to everything I have just said Michael?"
"Yes Mistress, you have set out our situation to perfection and I am a willing and eager participant in this try out week for what I hope will be our future life together."
"Good boy. I know we have both, separately up to now, been experimenting for years in this lifestyle. We are hopefully going to find out soon whether it can be more than a kink for us both and form a basis for a life together. Now, here is my first set of rules that I need you to agree to and follow without question:
Number 1. I need to be with you for every orgasm you have. You are forbidden to masturbate if I am not there with you.