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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 ataşehir escort 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.
Number 2. You will always wear ladies’ lingerie and you will only wear men’s clothes over the lingerie when going outside the house. At home, you must wear ultra feminine clothing at all times including with visitors.
Number 3. You will call me Mistress Angela and you will always have my wishes and desires at the forefront of your mind. Everything you do or say should reflect this and if I ask you, you should always be able to explain how you are thinking of me first. As you prove your devotion to me, this may reduce in frequency, but at first, it will be my primary tool for training you to adopt the behaviour I expect.
Now Michael, do you have any questions?”
“Mistress Angela, it is not so much a question as an observation, but ummmm, I wasn’t expecting things to be quite so; how can I say it? Regimented… official sounding. But I see where you are coming from, so ummmm I guess I am happy to proceed. All the rules sound perfect. Thank you for putting so much thought into this tryout week Mistress.
“Would you like me to bring your bags in from your car and show you to our bedroom now?”
“Yes Michael, that is a good idea. And I am glad you suggested it before I asked. Anticipating my needs is something I am looking for in a submissive hubby. Just put a coat on over your lingerie to pop out to the car, it is quite chilly today.”
I get up and go to the hallway. I put on a light raincoat and then go back to the living room to ask Mistress Angela for the keys to her car.
“Is your case in the boot Mistress?”
“Yes, I’ll come with you and then you kadıköy escort bayan can show me what’s upstairs.”
Mistress Angela follows me to the car and I open the boot. I see two large suitcases and a huge hold all. “Shall I take the two cases first Mistress, and then come back for the hold all?”
“If you can manage them, then that’s fine Michael.”
I grab the two cases and put them on the driveway. Then I shut and lock the boot and put the keys in my coat pocket.
Then I pick up the cases. “This way Mistress.” I walk into the house and place the cases by the foot of the stairs. “Actually, I think I’ll take these up one at a time Mistress. They are quite heavy!”
Angela smiles and follows me up the stairs.
“Here we are Mistress. This is our bedroom. Please take some time to settle in. The dressing table is new – just for you and there is one wardrobe completely empty for you, plus all the drawers in the tall boy. I’ll go and get the other two pieces of luggage and bring them up, and if it’s OK with you, I’ll go down to the kitchen and get our lunch ready. Please just call out if you need anything, anything at all.”
I go downstairs to get the second case, then out to the car again to get the hold all, bringing both up and placing them in the bedroom. I am surprised that during all that time, Mistress Angela has not opened any of the cases or done any unpacking at all.
“Is everything OK Mistress?” I ask tentatively.
“No Michael. Not at all. Firstly, what makes you think I am ready to share a bed and bedroom with you? We have never met before today. Would you please move all your clothes and other stuff into another bedroom? Then unpack my two suit cases choosing yourself where you think everything should go. I will sit here and watch you work and when you have finished, we can go downstairs together and have lunch. Then, when you have tidied up after our meal, you can join me in the living room for your first spanking.”
I look at her crestfallen. I got everything wrong and I hadn’t even considered that I should have asked her about the living arrangements. What a fool I am. I can see now so clearly that I was mistaken. My face and my whole chest flushes with embarrassment, but Mistress Angela has more to add.
“You should not make assumptions Michael. Before you can serve, you have to learn. Learn my ways, learn my needs, learn my desires. It’s not all your fault. We have both rather rushed into this you know. I’m not even sure a week will be long enough to discover whether this can work. Anyway no need to look so glum. I hope you can feel positive about all aspects of our relationship – even the discipline and punishment side. The great thing about corporal punishment is that it keeps everything out in the open. It can stop you bottling up any worries about your performance and it can stop me from storing up any anger if you are not serving me properly. I hope it will bring us closer quicker. You’ll see what I mean later…”
My mind is racing nineteen to the dozen. Spanking, discipline, corporal punishment – none of these things were mentioned online. So many thoughts flood my mind as I rearrange all our clothes and prepare lunch and serve it. Meanwhile, Mistress Angela is so light hearted. Her lively conversation over lunch even manages to lift my spirits, so I enter the living room after putting away all the dishes with a big smile on my face and go over to a mistress Angela and give her a warm kiss on the lips.
“I am so glad your spirits have raised Michael. That will make what is about to unfold in here much more bearable for you. Earlier today, you really disappointed me. You had not thought deeply enough about our situation and made several misjudged assumptions about the way our relationship is going to develop, so I think I need to set you straight about a few things. You and I are not going to lead an outwardly normal life with occasional sessions where I dress in black leather wielding a cat-o-nine-tails and whip you to within an inch of your life while you are tied to a set of stocks with a gimp mask on. We are not going to convert the cellar into a dungeon with iron chains and a huge mechanical rack centre stage.
We are embarking on a female led relationship where you are subservient to me and I set the direction of both our lives. The central pillar of this relationship is that you worship me. You show 100% loyalty and devotion. You serve me and obey me. You are my faithful submissive sissy. You trust me to lead us in a direction where we can be happy, satisfied and fulfilled.
It is my responsibility to teach you how best to serve me. You will need guidance to reach the stage where you instinctively know how to make good decisions. Part of this process is corporal punishment. This afternoon, for your crass misunderstanding of my intentions vis a vis living arrangements I am going to give you a warm up hand spanking followed by 12 strokes with the rattan cane. Punishment sessions like this will be very controlled and orderly. For the spanking, you will lie over my lap without any panties on and you will always thank me when I have finished – getting escort maltepe straight up afterwards and awaiting my instructions. To prepare for canings, you must place a dining room chair in the middle of the living room and present me with the cane. You will always find the cane hanging on a picture hook in the hallway, by the front door.”
I go out to the hallway and see the cane hanging there on open display for all to see, but I first go into the dining room to get the chair. I place that in the centre of the living room then go to fetch the cane. When I come back, Mistress Angela is sitting on the wooden dining room chair looking beautiful and regal. I offer her the cane. Mistress Angela smiles and takes it from me.
“So eager Michael. Don’t forget it is the hand spanking first. Please remove your panties.”
I slip my panties down while Mistress Angela puts the cane on the floor next to her chair. I step out of the panties and hold them nervously. She looks at me and smiles.
“Good boy! And you have another little erection! We must be doing something right… Now Michael, please lie over my lap and hold onto the legs of the chair. I would like you to try your best not to make noise during your punishment. Try to focus on the reason for the punishment and what you can do in future to make all this unnecessary.”
I take my position, very aware that my little penis is pressing against Mistress Angela’s leg.
I feel Mistress Angela’s hand gently rubbing my naked bottom. I am momentarily in heaven then her hand moves away and… SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!
Three hard smacks rain down on each cheek of my vulnerable bottom. I kick my legs out and let out a long, “Owwwwwwww! … um… sorry Mistress.”
SMACK! SMACK! SMACK! SMACK! SMACK! SMACK!
Six more smacks, but this time I stay still and quiet. Gritting teeth as the stinging spreads over my sensitive bottom. The erotic feeling of being naked over the knees of my dream woman. So beautiful, so sexy and here with me, makes the pain seem more bearable and I am completely engulfed in this fantasy come true. I grind against her as I squirm on her lap. My head swimming with different emotions, but mostly… I LOVE YOU!!
Now, Mistress Angela slows down a bit, aiming another 12 very firm smacks over the whole area of my, now fierily reddening bottom. Each smack eliciting a grunt or a yelp.
Mistress Angela’s hand rests again on my burning bottom, then moves down to my thighs. I relax the tension in my body as I feel her exploring my nether regions and she gently cups my balls in her right hand. My eager erection, still pressing against her skirt covered leg, I moan in confusion. then she gives a more playful slap and says, “Up you get naughty boy, it’s time to give your resilience a real test now.”
I push up off the floor and roll awkwardly off Mistress Angela’s lap, then stand up – my erection standing proud.
“Th-thank you for the spanking Mistress and sorry for getting things so wrong earlier.”
“You seem to be enjoying this Michael. Would you like to have a little lie down on the sofa again, before we proceed with the caning. The cool leather may soothe your sore bottom a little before the main event.”
I lie on the sofa again and Mistress Angela again comes over and kneels by my side. She tenderly holds my little penis and smiles. “It’s so sweet the way you express your feelings through this little thing. You have such a cute little willy I just want to kiss it.”
She lifts it up as she lowers her head and she takes the swollen head between her lips. I swoon
As she licks and sucks feeling myself getting very quickly aroused. I can hardly believe how quick Angela is to initiate sexual contact. She’s only been here an hour and this is already the second time she has got me off. Happy days!
“Oh my God Mistress. That feels incredible. Oh, oh ooooooooh…” I start to shudder and spasm as another orgasm explodes in my loins. I feel myself pumping spurt after spurt into Mistress Angela’s warm inviting mouth as she gently squeezes my balls. She keeps my penis in her mouth as my climax subsides and then pulls up off it keeping her lips right around my shrinking shaft. Then she lies it on my tummy and moves up to kiss me. I open my mouth and she opens hers, allowing all my cum to flow and drip into my mouth. I eagerly swallow my own sperm as she stands up.
Still basking in the afterglow of the most wonderful blow job I have ever experienced, I hear Mistress Angela’s voice… “Up you get, naughty boy. It’s time for the cane now.
I get up from the sofa, feeling a little dizzy. The erotic feelings draining from me as if they left my body with my sperm. I see Mistress Angela bending down to pick up the cane and a real dread fills my heart. My bottom feels much more sore now than it did in the heat of all that passion a moment ago and I hear the cane swishing back and forth as Mistress Angela indulges in some practice swings. She now takes me by the hand and leads me to stand behind the chair. She motions me to bend over and hold the wooden front legs of the chair, my bottom exposed up over the chair back. I feel helpless and so vulnerable. All the erotic excitement gone. Should I call a stop to this? This is not fun any more. This is just going to hurt – like crazy. Something inside me stops me saying anything. Makes me want to remain brave. I can survive 12 strokes, can’t I?
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