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John and Maria having some fun (F/M CD)

Posted: Thu Jul 11, 2024 9:55 pm
by GagFan96
This is my first time writing a story about a cross dresser so I hope it doesn't suck. Thank you captured_prize for your advice I hope you enjoy it. Any and all feedback is welcome in the comments.


In the twentieth floor high rise apartment lives a young but skilled and confident stock broker making his way in the unique world of wall street. He is John Grayson a tall man of just over six feet, athletic but not bulky build from several years of wrestling experience, green eyes, tan caucasin skin, and buzz cut style hair. He spends most of his time in the office trying to maximize his profits any way he can. Although now that he is alone in his apartment he slips into his bedroom and removes some his clothes and as he does this a women enters his apartment locking the door behind her. The young woman was Jhons girlfriend Maria who works at a hotel as a concierge.

This women is young much like John but she is much shorter at five foot six, she is thin but obviously not as athletic as John, has blue eyes, and long blonde hair that she currently has in a ponytail. The young woman takes off her shoes and goes to sit down on the black leather sofa in their living room. She is wearing a tight dark red blouse, black skirt, and dark red leggings. "Hey baby I saw your car in the garage your home early, how was your day?" She calls out after getting seated.

Jhon enters the room still removing some of his work clothes. "Hey baby, my day was great, had a few meetings and even got off early, what about yours?" He asks before walking up to the couch leaning down and giving her a kiss.

After they kiss for a moment she smiles at him and replies. "It was awful so many rude guests and my boss is such an asshole, but it's a lot better now. Do you want to switch today?" She asks smiling at him and responds in kind by lightning up in jubilance.

"Yes, yes I do, mistress." He replies as she stands up, takes his hand and leads him to the bedroom, then gently pushes him onto the bed.

"Okay then I'll choose your outfit, you shut your mouth and get yourself ready mentally." She says authoritatively to which he responds with only a nod of agreement.

John and Maria most of the time had a rather traditional relationship despite not yet being married. John took charge and was the breadwinner and did all the traditional things men do l, and Maria took the traditional feminine role of cooking and cleaning and being the more submissive partner. Most of the time anyway every now and then they enjoyed switching it up and having Maria take control. But when Maria took control John got to engage in an activity that he really enjoyed doing in private with Maria, that activity being cross dressing which not only John loved but Maria loved picking his outfits for him and getting to control him, it was a feeling she craved every now and then.

John sat quietly on the bed breathing deeply and focused on his alternate persona that he has when he cross dresses. When he dresses like this he stops thinking of himself as John the confident, dominant, competitive stock broker and he becomes Lila, a quiet, submissive, cooperative woman who loves being tied up and dominated especially by Maria.

Maria returns from the walk in closet with a white summer dress with yellow flowers on it, a black long haired wig, pink two inch heels, and light blue panty hose. "Are you ready?" Maria asks placing the close next to John. He nods looks over at her and smiles. "Good now Lila, get dressed and then come to the living room, understood?"

"Yes Mistress Lila replies in a higher pitched voice then Johns natural voice. Once Maria leaves the room he quickly gets dressed in the panty hose, heels, dress, and the wig. Then she applies some light blue eye shadow and red lipstick then proceeds out to the living room where she she's Maria siting in John's favorite leather chair he uses for gaming. Lila calmly approaches with her head bowed and she can see the rope, tape and clothes on the nice glass living room table. "Is all that for me mistress?" Lila asks excitedly.

"Of course who else would it be for dear, now lay on the ground and put your hands behind your back." Maria ordered, and order that Lila happily complied with. "Good girl, you now your place." Maria taunts her a little as she stands up and grabs the rope.

She begins by tightly wrapping the rope around Lila's wrists five times, then between her wrists a few times before tying it off with the knot out of Lila's reach. Then she used more rope to tie her arms to her body just below her chest. Afterwards Maria moved to the legs and similarly bound Lila's thighs, and ankles with rope. Then grabbed one of the clothes and tied it around Lila's eyes plunging her into darkness putting her into an even more submissive position. "Open up dear." Maria says and immediately stuffs another cloth in Lila's mouth as soon as she complies. Then to finish it off she grabs the duct tape and peels of five strips and plasters each one over Lila's mouth one after the other. Satisfied with her work so far she stands up and admires her bound crossdressed submissive, who starts wriggling on the ground and Mmmpphhing into her gag. "I'm sorry what was that I can't hear you, I think you have something in your mouth." Maria taunts Lila as she bends down and gives her butt a few good spanks eliciting some good groans out of her bound submissive.

Lual spends the next several minutes trying to get free from her bounds but Maria is really quite good at tying knots and can't pass up a chance to playfully torment her boyfriend when she gets the chance. Maria has a blast watching her cross dressed boyfriend struggle to get free from the bounds she put him in but eventually after about twenty minutes or so Lila gives the signal. Which for them was Lila snapping her fingers three times. Maria begrudgingly but slowly unties her giving her but a few good spanks before she does. Then she allows her to remove the gag herself. "So did you have fun?" Maria asks playfully which Lila responds with a smile and a "Yes mistress."