Role Play: French Maid Cross Dressing Husband

Role Play: French Maid Cross Dressing Husband

Role Play: French Maid Cross Dressing Husband Maid IMG 0047

My French Maid Cross Dressing Husband


My hubby writes…. “My fantasy would start as I am greeted by you at the door wearing a sexy silky robe and your breasts are just showing. As you lead me in you tell me how you want your nympho crossdressing husband to be your slutty French maid today and do as you wish. We get comfortable and start off chatting then you say its time to get my in my outfit, you get some sexy black nylons and a garter belt and some silk panties then you fit me with a nice set of full figured breasts and finally the sexiest French maid outfit and a nice blonde wig . As I look at myself in the mirror I’m so excited and horny I feel my cock getting hard. You then tell me its time to do my job and you have me.
“Then its time for me to start doing my chores and you watch me cleaning as you are sitting there stroking your cock getting it hard you tell me that now its time to service your needs and start sucking your cock as a good maid should. As you get harder and tell me that you want me to take it all. I am teasing your cock with my tongue and lightly teasing your beautiful ass . We then lie down as you then tell me you want to suck my cock as well and we are both sucking each other you bring me close to cumming and say it’s not time yet as you want me to fuck your beautiful ass pussy first and stroke your cock.
You are moaning for more and I slide in deeper feeling you squeeze me tightly and you say that its time for you to tease me now so I lay back and you straddle me and rub our beautiful hard cocks together as I’m teasing your nipples. You then say as your slutty maid you want to slide your cock into me and its driving me crazy. You tell me how I’m the best maid you’ve had and would have me again. You then tell me you are ready for me to cum and want to suck my dick and I am more than willing at this point and ask if I can suck your dick so that I can cum with you and taste your sweet juices. We finally cum together and collapse exhausted. We just lay there lightly caressing each other until we have the energy to start again as you tell me you have something in mind that you want to do with me.
“So I’m sitting around here bored out of my mind and horny. I was just thinking about more fantasies to add . You tell me that after you have me all dressed up in the sexy maid outfit and makeup that its time for me to learn how to be a sexy crossdressing maid because you have people interested in getting together with us . You show me what you want me to do during our sessions and what to expect from your friends that you have in mind for me to meet. As expected this gets me even more excited and horny as I want to please you very much.
“Hopefully I’m not going too far with all of this its just my horny mind working while I’m sitting here bored.” 🤪😉
RolePlay: I Can Make Fantasies Real

RolePlay: I Can Make Fantasies Real

RolePlay: I Can Make Fantasies Real

Elviras Sister W IMG 2776

Sexual role-play is all about being someone else. A chance to take a dirty fantasy and make it real, with the help of a passionate partner (or several).

Do you dream of being the stern boss punishing your sexy secretary? Perhaps you want a wicked teacher who’ll correct your bad behavior? A knight rescuing a princess, or an innocent virgin seduced by a dark temptress?

A conversation today reminded me of the power of role-play to help us think outside the box, and live out our dirtiest thoughts. You’d never demand sexual favors from your coworkers or hit on your teachers in real life, but in the privacy of my boudoir you can. I love being able to give that freedom to people; to create an experience that not only leaves them sexually satisfied, but stimulates their imagination as well.

Tell me your dirtiest wishes, and let me bring them to life!

RolePlay Submission: Serious Submission

RolePlay Submission: Serious Submission

RolePlay Submission: Serious Submission Full Body Straight Jacket IMG 1806

Serious Submission

We’ve talked before about bottoming and why I love bending over, but serious submission is something else entirely. Beyond just receiving penetration, it’s a much deeper surrender of control.
To me, it also means something different from pure S&M. Allowing another person to cause you pain is absolutely a deep act of trust, don’t get me wrong, and can be a beautiful show of submission. But it’s not my thing. I’m just not much of a pain slut. My form of submission is a little different.


Something I do love is bondage. The surrender of control as ropes bind me tighter and tighter. The feeling of utter helplessness as I struggle futility against a straight jacket. Jerking and tugging against a pair of leather cuffs as someone plays with me. Being bound isn’t just physical, it’s a connection- it is me surrendering myself to my partner and trusting that they will use me properly, and not abuse me. Allowing yourself to be vulnerable to someone is a profound thing

Service and Submission

Service goes beyond letting someone tie you up. When I truly submit to someone I want to please them in every way possible. I want to be made to obey. I enjoy pleasing them sexually, of course! I want them to take charge. It can be anything from serving them tea and giving them foot-rubs, to bending over for erotic fun, but the key is that it is I know i’ve satisfied my dominant partner. Communication is important to me in this
I see the same thing all the time when men submit to me – the need to give themselves to someone, completely. As a switch, I know that same feeling myself. To let them dictate what i do and when I do it- to control me completely, even if only for a short time. Like many of my clients my life is stressful and it’s wonderful to be able to surrender and let someone else make the decisions in an intimate encounter.

Role Play: French Maid Position Available

Role Play: French Maid Position Available

Role Play: French Maid Position Available Maid IMG 0058Edited
Session Inquiry

Hi Dee


I have a fantasy I hope you could help with. I’m coming to see you for an interview for an accountant job at your maid service company. When I arrive, I’m greeted by a large breasted TS French maid employed by you. I let her know I’m here for an interview and she leads me to you. As she leaves, I’m staring at her ass. You get my attention and ask if I like what I see. I reply that I do and you lead me to a room and ask me to wait while you go get a few things. In the room, I notice a slutty French maid outfit hanging up and a pair of black 6″ platform heels.


As I’m inspecting these items, you come in the room. You notice me, but don’t address my interest in the clothing. You ask me to have a seat at the desk and we begin the interview. You first ask casually what position I’m here for. When I say the accountant role, you tell me that position has been filled. You recognize I made all the effort to come in for this, so you say you’ll see what you can do to find a position for me.


As you look through your computer, you pause for a moment, look at me, then the maid outfit, back at me and let me know there is one position that’s open and pays triple what the accountant job was, but you’re not sure I’d want it. Ecstatically, I reply I’d gladly accept this role for that kind of money. You devilishly say that you thought I’d agree to that, so you get up and bring me over to the maid outfit and let me know that I’m going to be your newest maid. Shocked, I try to back out, but you remind me of the money.


I succumb and accept the offer not really knowing what the full extent of the uniform would be. You tell me that your clients expect the best looking gurls and that my male body just won’t do. You go and retrieve the full torso breast forms in the largest cup size available (I’m hoping for F or G at a minimum), hip pads and a waist clincher. After getting me into them, you need to apply makeup. It will be heavy, but seductive in nature with long false lashes. When thinking of what wig to get me, you say that there are no blondes on your team and they are often requested, so you apply a long platinum blonde wig. A perfect manicure is necessary, so you apply long false nails. I get into the uniform and roll up a pair of thigh high fishnet stockings.


Finally, I step into the incredibly high set of heels. Once dressed, you need to make sure I’m trained for everything as calls have already been coming in for the new blonde maid that you “somehow” had already been advertising. This is when you let me know that the maid uniform is simply just a fetish and no cleaning is necessary, only to pleasure the client.


This is when you ask the maid who let me in to join us (if more TS are available, I’m happy to entertain a group). You let me know that she was once like me too, but after earning all the money, went out and bought a real pair of tits and has completely moved on from her previous life as a boy. You let me know that in no time I’ll be doing the same thing.


But first things first. I need to learn to pleasure the clients, so you call the girl(s) over and instruct me to kiss her. We DFK and it gets me aroused. Noticing this, you tell me that I can’t get aroused making out with the clients so now I have to drop to my knees. You tell me to look under her uniform and to pull out her cock. I do and stare at it. You tell me to kiss it, I do. You tell me to hold it and I do. Next, you tell me to open my mouth, stick the cock in and begin sucking. I start doing this and stroking at the same time.


Getting aroused yourself, you approach me and lift your skirt letting your cock out to slap me on my face. I grab it and take it in my mouth. Once both (or all) of you are ready to cum, you stop and let me know there is one more thing. Your clients expect your gurls to take large loads on their faces, so then you both (all) unload and cover my face.


After seeing me, you let me know I’m ready and my first client is on his way to pick me up…


RolePlay: Moms Friend Seduces Son

RolePlay: Moms Friend Seduces Son

RolePlay: Moms Friend Seduces Son Pink/Salmon Baby Doll Nighty IMG 1230 Edited

A customer emails….

“Hi Miss Dee

I’m looking for someone to fulfill a long-held fantasy of mine: a roleplay scenario between a young man and his next door MILF neighbor. I think you would be perfect for the part.

Here’s the scenario: I’m an young, sexually inexperienced college student that has terrible luck with women. You’re my gorgeous, mature next door neighbor who happens to be friends with my mom. You hear from her about my women problems, and decide to invite me over to talk and give some advice.

Our encounter slowly heats up, and things become more intimate. Out of concern, sympathy, and lust, you decide to teach me how to please a woman. I obviously eagerly agree and submit myself as your student. One by one, you tell me how to kiss your lips, neck, and every other part of your body exactly how you like it. You are kind and motherly, yet stern and dominant. I want to nuzzle your breasts like a child, and later worship your cock like a slave.

When you’re on top of me, teaching me how to eat out your asshole, I want you to tell me how much of a good boy I am. I think you get the idea 😉 I could send you more details over email, if you like. Although I’d like to finish with fucking you! I will enjoy it even if it doesn’t happen.

Other turn-ons: cum, oral, dirty talk, kissing, using my tongue
Turn offs: spitting, dirty feet or other parts, urine, pain

Will G
Please let me know if you’re interested. I think 40 minutes should be enough time, but I could go up to an hour if you prefer. I’d like to hear your thoughts.”

RolePlay: Fantasy StepMom

RolePlay: Fantasy StepMom

RolePlay: Fantasy StepMom

Hello again my beautiful Step mommy Dee 🙂

I just went scrolling through your site again ( I cant stop myself :p ) and those beautiful daily pics, the ones you are near a pool on a gorgeous backyard hehe… that look momma… that hot, sexy and super arousing flashy green see through… its just confirmed my choice, when we will finally meet.

I want you to be my hot step mommy, always super sexy like those pictures( you are totally sexy in all of your pictures, but these specific ones just stirs up something deep in me.. 😉 ), the step mommy who always lets me see under her skirt from afar, while the Christmas party is going on, subtly but keeping me wondering if its intentional 😉 the sensual step mommy who comes and tell me goodnight while I’m gaming, and while she is hugging me goodnight, she gently rubs her magnificent tits in my face and subtly brush her hand on my already hard dick, and leaves… leaving me to wonder again if its intentional.

The step mommy who would come out of the bathroom after her shower with nothing on but a small towel that barely covers her beautiful breast or her ass that is to die for… while looking at me with eyes and a smile that sends waves of arousal through my body, then again leaves me wondering.. I want you to be the step mommy that I’ve always fantasized about, that I always had the impression that you wanted me too, but I was too shy and unsure to try and confirm with my beautiful mommy 🙂 then when we meet you could be my step mommy who has enough of waiting for me to catch on your hints, and you just take me and teach me how to please you, (and by that, “surprise” me with your gorgeous cock 😉 ), you teach me how to use my mouth to worship my step mommy( I fantasize about my step mommy Dee being kinda dominant, like in your post about t he assertive woman 😉 ).

I might be a little reluctant, but you are my step mommy, the most beautiful woman ive ever known, the woman I’ve always fantasized about all my life, so I’ll do anything to please you( even if I’m surprised by your gorgeous cock 🙂 ) I’ve been reading a lot of erotica with trans step mom or aunties and I love it!! Its such a hot fantasy 🙂 I/m so glad i discovered this through you, and…

also I have never actually been into the foot fetish but I gotta say that the way you talk about it, and again that picture of you in that green see through where you are sitting right next to the pool and you kinda show of your beautiful legs and feet, it made me realize how sexy it can be hehe, id be open to a little bit of foot play?( don’t know how you’d call it) you could surely teach me about all those things, once you show your stepson what you really want 😉

You are so beautiful 🙂