Quite An Evening Pt. 01

Inside a fancy bathroom, a woman is taking a shower. The woman's name is Annette.

Annette is middle-aged, not particularly tall but not petite either, quite voluptuous; she is a brunette sporting short hair, has olive skin and dark brown eyes. Annette's big breasts have large, brownish areolas surrounding her perky nipples; she has a big butt as well -nice and round, with a bit of cellulite noticeable on her thighs. Her cunt is completely epilated and it looks rather plump too.

Outside, standing in a corner of the bathroom, a crossdressed man wearing a classically-styled french maid outfit and a jet black wig awaits. He is middle-aged as well, fair-skinned, with hazel eyes, slightly plump and not very tall -even wearing heels. A white leather collar featuring white lace on its edges and an O-ring is also worn by the maid around the neck.

This maid happens to be Annette's husband, John. Although it could be said that John hasn't been John anymore for quite some time now; he is now Jeanne, or more accurately, Sissy Jeanne. But how exactly John ended up like this is a story for another occasion.

After some time bathing herself, Annette turns the shower off and steps out; the sissy maid comes along with a towel and quickly begins to dry her off thoroughly. Once finished drying her off, Annette orders the sissy maid to pick up her phone and hand it over to her. Sissy Jeanne does as told immediately.

Annette goes through the text messages that came in while she was taking her shower; she immediately focuses on two.

"We have found a bit of traffic on the way to your place, but we should be arriving in 15 minutes..." read the first message.

"On second thought, better make it 20." read the second message.

Annette grins and then types a brief reply.

Annette now turns to her sissy maid, "OK Jeanne, let's get going, our guests should be arriving within fifteen to twenty minutes..." she says.

"Yes, Mistress," sissy Jeanne replied in a markedly meek voice tone, yet, it is noticeable that sissy still has to make quite an effort in order to sound as feminine as possible.

Now in the master bedroom, sissy Jeanne assists Annette to put on some fancy lingerie; white lace and silk -bra, stockings and a garter belt. Then sissy picks a pair of g-string panties with the intent to put those on Annette as well, but she quickly objects to it; "No, dear. I'm definitely not wearing any panties tonight. Instead go get one of my jewel butt plugs. The chromed one with the heart-shaped, red gem," Annette says.

"Sure, Mistress," the sissy maid replies and quickly goes to get the one butt plug specifically requested by Annette.

"Now help me put it in place," Annette orders to her sissy maid. Sissy Jeanne nods, then grabs lube and adds some to the butt plug. Annette bends over just enough and spreads her buttocks apart exposing her anus; sissy then proceeds to gently slide the butt plug into Annette's rear orifice. Annette let's out a brief whimper as the butt-plug goes in; once it is in place, Annette stands straight again.

The sissy maid continues aiding his Mistress to dress, now helping her in putting on a white cocktail dress and then a pair of white ankle strap heels. Sissy pulls a stool/chair near the vanity in order for Annette to sit on it. Once sitting at the vanity, Annette begins applying makeup on herself while sissy remains standing close by.

After finishing with her makeup, Annette instructs her sissy maid to get a specific pair of earrings and a necklace and then put those on her, which sissy compliantly does. The necklace prominently features a key hanging from it.

Right after aiding her with the earrings and necklace, Annette then tells her sissy maid to sprinkle her with perfume. Sissy Jeanne proceeds to pick up one out of several perfume bottles at the vanity but suddenly Annette objects to the sissy maid's choice. "Not that one, sweetie. This is a special occasion, and you know well which one I do prefer for such occasions, ain't that right?" Annette said in a rather cheeky tone.

"Yes, Mistress. I briefly forgot that this is indeed a special occasion. I'm so very sorry about this and I wish to apologize for my clumsiness," the sissy maid replies to his Mistress as he quickly picks another perfume bottle and starts sprinkling Annette with its content.

Meanwhile, someplace else, a fancy car drives down a street of what seems to be a pretty fancy neighborhood. The car then takes a turn and drives right into a driveway, it stops in front of a gate; after a brief time, the gate opens and the car drives on through.

The car parks on a spot not too far from the house's main entrance; the driver's door opens and from it emerges a lady. The woman exudes arrogance; she is quite tall, slender, middle-aged, with alabaster skin, fiery red hair and blue eyes. Allegedly, her name is Chloe.

The passenger's door opens as well and a man steps out; he is pretty tall, dark-skinned, bald-shaven, with a noticeable athletic build and looking still fairly young -likely in his late 20's or early 30's. He sports a facial scar, but not a particularly ghastly one. His name is Marcus.

Both are dressed sharp. Chloe wears a black, tight halter top dress and black stiletto heels; the outfit allows to see some skin and she has umpteen freckles. Marcus wears a gray suit with a white shirt, no tie. They both walk away from the car and head straight to the house's main entrance.

At the door, Chloe rings the doorbell. They wait there for a brief moment before the door opens and there it is sissy Jeanne to greet them.

"Good evening, Mistress Chloe... and the gentleman here," sissy Jeanne says with a bit of a stutter. Sissy looks slightly surprised for a bit, but soon enough tells the guests to please come inside and curtsies accordingly. Chloe politely thanks sissy Jeanne, albeit in a haughty kind of way; she has a thick accent, which sounds European. Once inside, the guests are both greeted by Annette as well.

"Hey, Chloe!" says Annette while kissing Chloe on one cheek and Chloe kisses her on one cheek as well. "Hello, darling. It took us just a bit longer than expected but here we are at last," Chloe says.

Annette now turns her attention towards Marcus, "And let me guess, this hunk right here must be Marcus," she says while smiling flirtatiously. Marcus reaches out for Annette's hand like for a hand shake, but then twists her hand upwards as he bows down to actually kiss Annette's hand instead; "Indeed, Ma'am. Most pleased to finally meet you in the flesh, and I really have to say that you look even better in person," Marcus says while smiling.

Annette flushes all flattered by the compliment; "Oh! Nice to meet you too," she replies and then giggles. "I told you that he can be pretty charming, didn't I?" Chloe says as she grins at Annette.

Chloe now turns to sissy Jeanne and asks rather mischievously, "I couldn't help but notice that sissy here seemed quite surprised; she wasn't expecting a male guest coming with me, was she?"

"Jeanne was well aware that you were coming accompanied by a male guest, but it's just that she wasn't expecting someone like Marcus. See, I kept any sort of physical description from her. I wanted to incorporate a bit of an element of surprise into this... I mean, I thought it would make things extra interesting and even more exciting," Annette claims while grinning.

"Good thinking there, hun," Chloe remarks.

"Still, we must make the proper introductions. Marcus, Jeanne here is my sissy hubby and she will be mostly serving as our maid for tonight's dinner, but that being said, Jeanne might very well be joining us for other activities later on as well... Jeanne, Marcus here is a very good friend of Mistress Chloe and, as you have already found out, he will be her companion for this evening -at least during dinner," Annette says with a wicked grin.

Marcus turns to sissy Jeanne with some hesitancy, "Nice to meet you... Jeanne." Sissy curtsies and then replies he is pleased to meet him as well.

"Good Girl! Now be an even better maid and show our guests the way to the dining room," Annette tells her sissy maid. Sissy complies and leads the guests to the dining room.

Annette, Chloe and Marcus now sit at the table while Sissy Jeanne serves appetizers for them to eat. Sissy Jeanne pours sweet Vermouth on the ladies' glasses, then stands right next to Marcus and asks him if he would like to drink some aperitif as well; he says no.

"Can I offer you something else? Like a cold beer, for instance?" sissy says.

"That would be nice," Marcus replies.

"Would you like an Ale, Stout or perhaps a good old Lager?" sissy asks.

"Lager will be just fine," Marcus says.

"Right away, Sir," sissy exclaims in compliance, then excuses himself as he retires to go get Marcus his beer.

All the while, Annette strikes a conversation with Marcus. "So Marcus, what is exactly what you do for a living? Chloe told me that you work in something security-related. Are you like a bodyguard?" Annette asks.

"Kind of. I work for a private military contractor; most of the time as a consultant, but sometimes also as an operative," Marcus responds.

"Whoa! That sounds like a rather -for lack of a better way to put it- dangerous job, Marcus. So I reckon that you must have quite a military background," Annette remarks.

"Well, as a matter of fact, yes. I did serve with the Marines, doing tours in both Afghanistan and Iraq," Marcus states.

Annette turns to Chloe and exclaims, "No wonder why he happens to be in such a great shape."

Annette now turns back to and smiles flirtatiously at Marcus, "I think that you must be even more irresistibly handsome wearing those Dress Blues... Just picturing you like that and... Oh my!" she says.

Marcus flushes a bit. "You flatter me so much, Ma'am. Thank you for your compliments, those really mean a lot coming from a lady such as yourself; I've been a longtime fan of yours," he replies while smiling back at Annette.

"Oh come on, Marcus! You can drop the whole Ma'am thing right now; you won't be calling me Ma'am anymore, do you understand? From now on, you just call me Annette -And that's an order, soldier," Annette ripostes in a stern yet playful tone.

Marcus smirks evidently amused by Annette's words. "Alright... Annette," he responds.

"Chloe also mentioned to me that you two met at a swinger party," Annette says.

"Yes," Marcus replies and then continues, "That was about two years ago at a common friend's place; she owns this somewhat secluded house right off a slope -not a very steep one though; nothing too fancy but a lovely place regardless. It has this nice view of a lake and the surrounding woods... Anyway, seems like I digress, ain't I?"

All three cackle for a moment and then Marcus resumes his account, "Now back to subject, the party. Well, that was one heck of a party and probably one of the best I have ever been to, hands down.

"When I arrived there it was already nighttime. Some pretty intense stuff was already going on in all bedrooms, the Jacuzzi, every corner of the house... So instead of jumping right into the action, I decided to go around the house for a bit first.

"That was when I caught a glimpse of this statuesque lady sipping some wine and wandering around as well; I got smitten almost immediately... I mean, what can I say? Chloe and I really hit it off from the get-go, so we have remained pretty close ever since."

"You will soon find out exactly why, dear," Chloe remarks as she winks and grins at Annette.

Sissy Jeanne arrives with the beer and proceeds to pour it into a glass which then hands over to Marcus; "Your beer, Sir," sissy says with deference and Marcus thanks him.

"Annette, I really have to commend you for how subservient sissy here has become; the progress definitely shows," Chloe remarks.

"Oh! Thanks, Chloe! I feel so damn proud for what I've been able to accomplish so far; but as flattered as I am by your praise, I must state that none of this would have really been possible without your help and guidance in the first place... Look, let me show you something," Annette says and then orders her sissy maid to lift his skirt. An utterly embarrassed sissy Jeanne complies with utmost deference.

Sissy is wearing a garter belt and stockings but no panties whatsoever and his genitals are stuffed inside a cute-looking, satin and lace pouch. Annette removes the pouch and exposes sissy's genitalia, which is locked inside a metal chastity device, to the guests. It is fairly evident that sissy is pretty far from being well endowed. The chastity device has a silver chrome finish and it is locked with a heart-shaped padlock.

"GOOD!!! You did get her the chastity device," Chloe exclaims.

Annette grins and winks while grabbing and showing the key hanging from her necklace. "This sissy is very much locked in. In fact, she has been for nearly two weeks now! I got her a metal one and a plastic one. But wait, there's more... Jeanne, turn around and bend over," Annette utters.

Sissy does as told, showing his bum-hole stuffed with a hot pink butt plug.

"Oh, that is just lovely!" says pretty excited a wide-eyed Chloe, "So you have been keeping on with her anal training, I see."

"Sure I have. I butt-fuck the hell out of my sissy bitch at least thrice a week. Also working on that pretty ass of hers taking longer-sized dildos; currently she's able to manage a 6 inch dildo up her sissy-cunt, albeit just barely," says Annette with yet another mischievous grin across her face.

Chloe swats one of Sissy Jeanne's butt-cheeks while grinning. "Good! Look what a cock-hungry slut you have turned out to be after all, sissy!" Chloe exclaims.

Sissy Jeanne flushes while bowing his head down, both Annette and Chloe burst into hysterical laughter.

"OK Jeanne, I think it's time for the main course, our guests must be starving. Go take care of that, NOW!" Annette says.

Sissy Jeanne stands straight once again, turns around, curtsies and leaves for the kitchen in compliance to Annette's order.

Time has passed, dinner is well over by now; sissy Jeanne is busy doing the dishes when Chloe walks into the kitchen.

"Are you done there yet, sissy?" Chloe says.

"Almost, Mistress Chloe," the sissy maid mutters.

"Well, you better hurry up. Annette and Marcus are pretty much ready by now and must be heading to your bedroom soon enough. So listen, once you are done with the dishes, you will be coming with me to get you ready for what is to come-- UH!!! WHAT A THRILL!!! I will be waiting for you outside," Chloe replies and then leaves.

Once sissy finally finished with his chore, did as told and he is now seen walking right behind Chloe, heading to some room in the house. Sissy looks pretty thoughtful along the way.

Chloe and sissy Jeanne get inside one of the house's bedrooms. Chloe speaks up as sissy listens, "OK sissy, surely I do not need to remind you that at this point, we have come so far that it would be pretty much pointless wanting to turn back to what was once, so instead we keep going forward. I think that you will definitely agree on that, right?"

Sissy Jeanne remains silent for a moment, then replies with a bit of stuttering, "I guess so, Mistress Chloe."

"You guess so?.. Come on, sissy! Are you serious???!!!" Chloe says in a stern tone, then continues; "Let me remind you that you were the one who brought this up to your wife to begin with. She agreed and said she was all willing to try this out -and I do believe she is down with it, absolutely- and you were undoubtedly the one most eager to see this whole thing through in the first place... Well, this is it, sissy! I know that you have been wanting all this to happen, so badly and for so long... And look! Now it is very much happening! It is just like that old saying: be careful what you wish for because it may come true."

Sissy Jeanne bows her head pretty low and he is heard sniffling. "It's just that..." at this point, sissy's voice cracks and then his natural, masculine voice tone comes out as he continues while sniffling; "I'm not very sure if I will be able to carry through with what is about to happen. I'm so scared. What if this turns out to be not such a great idea in the long run and it actually ends up ruining our lives?"

Chloe approaches to sissy. She gets pretty close to him, places one hand on sissy's chin and then slowly lifts his head up until they meet eye to eye, then grabs sissy's hands; "Calm down, sissy," she mutters.

"Last time I think I was fairly able to handle it because they went away to a motel room and, chiefly, I wasn't actually present during the act. I mean---" sissy says but then gets interrupted mid-sentence by Chloe.

"Look sweetie, I know this is uncharted territory you are about to enter. It is only natural that you feel scared by the thought of it. That is understandable, but to quote another old saying: you cannot make an omelette without breaking some eggs.

"Consequences, they are inescapable. Whatever we choose to do or not to do in life will always carry consequences with it; be those consequences good, bad or a bit of both. We can only be in control of so much in life; this world we live in, contrary to what many people like to think, is plenty more chaos than it is order. A lot of times our only option is simply going with the flow -like a driftwood- and that is it.

"It is one thing to show you a path, and another one is you walking down that path. If all this would turn out to be a terrible idea in the long run or not... Truth is, you will not be able to find out if you do not carry through with it. So, either you decide to take the risk -consequences and all- and find out if this is indeed what you always really wanted... Or just throw away all that we have been working on so far and pretend none of this happened; but you would be fooling yourself because it did happen, and things likely will never be the same again anyways.

"It is your call, sissy. What is it going to be?" Chloe ends her speech.

Sissy Jeanne stares for a moment into Chloe's eyes and then simply nods.

Meanwhile, in the master bedroom, Annette and Marcus chatter some while waiting for Chloe and sissy Jeanne.

"They are taking a bit long, aren't they? Let me text Chloe to ask her what's going on," Annette says, but as soon as she finishes that sentence, the door opens and Chloe comes through with sissy not far behind following her.

Sissy Jeanne is led by Chloe with a leash attached to the collar on his neck; he is now wearing a golden blonde wig and sexy lingerie. Sissy's lingerie (bra, garter belt, stockings -no panties) is hot pink, mostly made up of fishnet fabric. He also wears a pair of ankle-strap heels, hot pink as well. His still locked-in-chastity genitalia is very much in plain view now.

A wide-eyed Annette cannot hide how impressed she is by what she's seeing. She quickly approaches to her sissy and gets real close to his ear, then whispering in these words, "You look so gorgeous, darling."

Annette and Sissy Jeanne are now face to face, smiling at each other. Chloe handles the leash to Annette and steps aside. Sissy Jeanne throws himself down on the floor and kisses Annette's shoes. After this, sissy stands up and Annette then leads him to their marital bed; standing not too far from them is Marcus. Chloe now sits on a chair at one corner of the room, quietly watching.

Annette detaches the leash from sissy's collar. "OK... Take off my clothes, sissy," Annette utters; sissy does as told, stripping Annette right down to her lingerie. Subsequently, Annette orders sissy Jeanne to finish baring her off by also removing her bra and shoes, which sissy compliantly does as well. "Good gurl, now go undress Marcus," Annette orders now.

Sissy seems to hesitate for a bit, but soon walks towards Marcus and begins undressing him. Sissy strips him right down to his boxers. Marcus is indeed very much ripped; he sports some scars and tattoos over his body -some of the tattoos with prominently military motifs.