36 year old business woman seeking sissy please read.

Hello! I'm a 30 year old single submissive male obsessed with chastity and all aspects of femdom. I'm 5'10, in decent shape, and love anything outdoors. I live in NY. Hopefully, we can get to know each other and see what type of dynamic unfolds. Here is how I would like to surrender submissiveness upfront if you are interested:

I have a chastity cage and padlock that we can use for a clever way to keep me locked completely at your mercy! I bought a realtor's lockbox with a programmable combination feature. Once I put the keys to the padlock in the lockbox, I can take a picture of a randomly set combo without looking, send a pic of the combo to you, mix the numbers up and delete all photos from my Kik folder, all without looking at the combo. This will remove any evidence of it from my phone, and leave you as the only one who knows the code that would allow me access to the keys.

Why am I offering this to you? Well, I LOVE the idea of submitting to a woman who can have some fun with this and flex her newly acquired control.

My goals are to be controlled and find trust where I can be myself. I want to explore sissification more and see where that takes me

Kinks:

Chastity, Femdom, Anal, Foot & heel fetish, Mild CBT, Humiliation, Feminization

Hard limits:

findom, public, bathroom stuff, scarring, blood

Looking forward to chatting if you are interested!

Hell Miss Ashley thank you for taking the time to consider my response. I call myself Samantha as you can see and I'm a 42 year old crossdresser. I started when I was a teenager but I haven't had much time to let my sissy side out in the last few years (been exploring my more dominant side) but I really want to let my inner girl out. That would be my main goal in becoming your (or anyone elses)sub. I'm currently single and I've never been in a D/s relationship before (played with it some but nothing more). For turn ons I love the feel of soft and silky clothes espesically pantyhose and stockings (both on myself and partners) and I adore women's feet either in shoes or out I'm also fascinated if a little terrified at the idea of being fucked in my butt. For hard limits I don't like anything related to feces (in rp or rl), blood or body modificatoin (sorry no tattoos, piercings, etc) and I can't dress in public for privacy reasons. I believe that covers everything and again I thank you for taking the time to consider me. Edit sorry Im in NJ

i do apologize. i had a much busier week than i expected. i will message each of you back next week to see if we can talk more.
i will only take one of you on. i do only have time for 1. and i prefer that 1 to be able to take me on solo as well.

sadly these didnt pan out.

?

Miss Ashley,
Does the lack of a message from You indicate a lack of interest, Ma'am?

MissAshleyToYou said:

First. Do not pm me. JUST DONT

If you do not want it be known that you are responding to this add then you are not who I am looking for in the first place.
I am a very busy woman, but that does not keep me from having urges and needs to want to build an online relationship with a sissy boy.
To Give him rules and tasks and grow with each other. Each relationship is different. But we all have an idea of exactly what we want and need.

I didn't want to write an add. When i parted ways with my last sub i actually planned to take some time off. But i craved more. I need this for me. it is about me. I know how needy you are, but in the end this is all about me. Actually I really thought I had accidentally found exactly what I was looking for. I realize nothing in life is ever that easy.

Let me start off by telling you I am classy. If you are using your cock as a picture of yourself, please know that you are not the sissy for me.
Let me also tell you that this will be a process. A relationship does not happen over a message or 2. If you do not want to build something meaningful, I am not the woman for you.

So. I want you to reply to this thread and in your reply I would like some or all of the following. YOU can add anything you like.

Tell me your age. A rough location. Your personal normal interests in your spare time. Your relationship status. If you have been in a sub/dom relationship before. A turn on and a turn off.
Then I want you to tell me some of your goals for a relationship with a dom and then I want a hard limit from you and something you hope to gain from such a relationship.

Let's see if we can find anyone who can follow directions. Following directions is definitely something I will need from my sub.
Who knows how many there will be who wont read through this.

Good luck in your search if you don't hear from me. I don't expet to have time for those that I do not find I could build a relationship with. I am sure there is someone out there for you.

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Hello Miss Ashley,
I am a submissive man from Southern California. I am currently a straight Male. I have long felt the need to find an online dominant who will take me and turn me into their submissive sissy slut. I have been a closeted crossdresser, but have been absolutely terrified of the thought of being out in public en femme. An optimal dominant would help break me of this.

I have never had the ultimate pleasure of a submissive, that of a dominant to serve, but I feel the need to serve. A strong dominant who knows how to handle a sissy is the best pleasure in life I could hope for. A Turn off for me would include someone who is unsure of themselves.

Hard limits for me are anything that involves bodily harm, ie. Fire, electricity, etc. However body modification is acceptable if discussed and agreed upon before hand.

In my spare time, I enjoy collecting and building legos, reading books and obtaining new knowledge whenever possible.

I look forward to hearing from you. Hope to talk to you soon.

Kelly

Building up courage to leave detailed response here...

Sub for you miss

Hi

Myself Sanjay, age 29 from India. I love surfing, cricket and follow current affairs across the globe, MBA graduate and Single. I have never been a Dom/sub but it's my Fantasy.
Cheating is a big turn off for me...
Honesty, being aggressive and posh attitude turns me on.



Looking forward to hear from you!!

It's not easy to find the time. It's not easy to find someone with your schedule. But when it all comes together it's outstanding. All you can do is keep trying and hope for the best. People will come and go, and when they go, don't be bitter. Appreciate whatever time they gave you and learn from all that they taught you- it will prove valuable in the future.

Miss Ashley,

I apologize. I mean to say I am very sorry, Miss Ashley. I found your ad late and then compounded my error by being slow to respond. However, you may still want to read this. Perhaps the length and thoroughness will help explain why I have been slow to put it on paper, as it were, and express myself to you. I go deep, and that's not always easy for me.

Miss Ashley, if you owned me, I wouldn't be at all ashamed for people to know. Or maybe I would be ashamed, but I would just like it because I'm such a needy humiliation slut. I could tell you some stories about situations I've been put in--or have put myself in--like standing in the middle of a women's clothing store dressed in full, sexy lingerie and heels. Mostly I think, if you owned me, I would be proud for people to know.

I do not use my little penis (not really that little) as a profile pic. I use a pic of my backside, leaning into a wall, slightly, showing my red, spanked ass. I have to admit, though, if you look, you can just see my testicals dangling between my thighs. More than one person has commented on how nice a pic it is. As far as naked pics go, I think most people would agree that it's at the classier end of the scale. I like it because it hints at how I'd like to spend my days--naked and well-disciplined.

I'm afraid I'm way too old for you--65, but I'm still in pretty good shape, overall, can still run a little, and appear younger. The other thing you should know up front is that I'm not sure how committed I could be, and I won't be sure unless we try. I had one brief experience with a "Mistress" online. It was kind of fun--that's what led to me exposing myself (not my penis, myself; my penis was in panties) in that clothing store--but I found it unsatisfying because it lacked her actual physical presence and discipline.

Here's what I mean. She ordered me to clean my house while wearing a dress. So yes, I had to go to that clothing store the first time and negotiate finding and buying a dress--needing help with my size (I'm a 12 B) so that I had to talk with the woman who owned the shop--and that was humiliating and fun; but I'm not a great house cleaner and not so interested in doing it. What would make it right in my mind is if my owner makes me clean HER house like that, enforcing her will and supervising with her whip or cane. Even better if she has a friend or two visiting that day. I don't just crave the humiliation; it seems I like and need a little pain and the actual, physical control. I fantasize about bondage all the time, and have greatly enjoyed it when it has occurred. There's just no way to do that online.

So I've been sitting here for an hour or more, trying to think what I should say next. So many thoughts and past experiences come to mind. If you like porn literature and share some of my interests, I could entertain you for hours and hours with tales of my submission--some real-life experiences and some fantasy mixed in. I've been thoroughly whipped and caned--semi-publicly at a party--and marked to a degree that it showed vividly for more than a month. I have some pics to prove that. I've tried on sexy, strappy high heels in the women's department at a public mall store in Phoenix, right in full view of women and the men with them, alike. I heard the snickers and enjoyed them, though I kept my head down. I've been whipped and caned, more than once, in front of 2 men who shared the property with my Goddess at the time--men I really didn't like. I've been clothed in a dress, lipsticked and wigged--even penis-caged--and paraded in front of those same men, and also some women. I've worked in the garden and received packages from UPS while dressed in nothing but a man's thong--and it didn't matter to that woman if my ass was welted and bruised.

I live in Cottonwood, AZ, just down the highway from Sedona, where I used to live until it became unbearable with newcomers and touristas. I'm pretty sure you've heard of Sedona. Who hasn't? I've met people from all over the planet in that town. They named a fucking car after us, for crapping out loud.

I like to garden. I'm currently keeping fish and I have a few tanks that are shaping up nicely with plants, very attractive and interesting, but also a major pain in the ass trying to keep everything balanced. A fish tank is like a biosphere and you (or me) is the god of that environment. It's a responsibility that I take seriously--and painfully when I fail. I was a good ballplayer in my day, softball mainly, and a perennial all-star, usually at 2nd base. I like to watch some sports, football and baseball, but I'm not as enthusiastic as I used to be. Too much money in the games leads to neglect of the fan.

This might trouble you, too. I've never been married, rarely even had a "serious relationship". I'm a troubled and flawed man, but then, if I weren't, would I even be writing? Would I have even seen your ad or been looking for it if my mother hadn't abused me with her hairbrush?

A while ago I met a woman--I went looking on fetlife (do you know fetlife?), really for a friend into the life that I wouldn't have to hide from--and I served her twice. She had to have some surgery a few months ago, and she told me to stay away. She hasn't come back to me, and I haven't pushed, but I suspect she tired of me that quickly. We weren't really compatible. She is looking for men who will willingly submit; I'm looking for an aggresive, verbal Goddess who will dominate and MAKE me submit.

The first time I served her, I licked her pussy and her asshole for 3 hours and she never made a sound except for sighs and moans; never even said hello. I slurped up an unbelievable amount of girl cum during that time. She is, without doubt and far and away, the juiciest woman I have ever known. We never even spoke until, finally, I told her I just HAD to pee. That broke the mood--after 3 hours, so that was probably enough. Even then, we barely spoke. Just enough to trade some basic info and then she threw me out.

For the record, after I served that Goddess the first time and she found out how much I like licking ass, she told me that's what I'd get a lot of, and she did deliver on that promise the 2nd time.

A lot of the stuff I've mentioned--the pubic beatings, the garden--I had an on and off relationship with that woman for about 2 years. She claimed to be dominant, but she wasn't really. She had a full pantry of B&D equipment including whips, canes, restraints, gags, and even a cross always set up in her living area, and she liked humiliating me, but she wasn't really forceful or demanding, and her attention to anything is wavering. So in the end, that wasn't a satisfying relationship for me, either.

I don't want you to think that I'm an unpleasable bitch, I just desire what I desire, and that's a woman who will demand and take, not a woman who will request and accept. It doesn't seem like that should be as hard to find as it has been.

Most of the women I have known really want the power; they just don't seem to be honest with themselves. I mean, if I walk up to a woman who I might even know finds me attractive, and I get on my knees and beg her to use me as her slave, she's going to think I'm weird and walk--or run--away. I don't get that because most every woman I have known, when she lands her man, never stops trying to dominate and change him. It just doesn't take the form of B&D or D/s. It's like fully clothed D/s in a very slow, sub-surface, manner. And yes, that too, is unsatisfying for me. But you know what I'm talking about. Most women won't stop until their man is dressed the way she wants, for example; and then there's adjustments to his saloon schedule after his work and what time he is required to be home, and she even dictates who his friends can be in many cases.

I want a woman who will operate out in the open, with both of us--and almost anybody else SHE wants to include--fully cognizant of the situation and what we are doing. I'm not looking for subtlety; I'm looking for a woman who will boss me and make no secret of that fact. I'm looking for a woman who will flaunt her power over me and make me pay, even publicly, with my submission. I don't want to submit willingly; I want to be dominated in VERY certain terms. I'm looking for the woman who will collar me, leash me, cage my little penis, and walk me, naked and exposed like that, down along the creek where people like to gather. Maybe that's an exaggeration; maybe not.

I've been to that creek on my own, sort of. A couple times after a beating that left very visible, almost electric, marks and welts, that woman liked me to go there wearing nothing but a thong and sort of hang around. I was into it, and one time, the best time, 2 women surprised me standing on the bridge like that, looking into the creek, and one of them greatly enjoyed engaging me in conversation.

Alright. So, I like to be thorough, and maybe you can tell I'm a writer and a fairly intelligent and thoughtful man. You gave me some specific tasks to fulfill in your ad. I think I still have these to tell. If it isn't yet clear, I would hope this relationship might develop into an actual, physical, face to face--or face to pussy and ass, or cane to ass--relationship. Of course, the thing I hope to gain from this relationship (eventually) is a woman, or Goddess, who will rule me absolutely, and keep me well beaten, well disciplined and obedient, and always devoted to her and her pleasure and satisfaction, while not forgetting that boys need to experience a little pleasure, too, even if it's just through his service.

I think I've covered some turn-ons. A turn-off is more problematic. With all the things that turn me on, you know, what can possibly be left to turn me off? Well, half-assed domination, control, and humiliation would be one thing, a woman too chicken to take that walk with me on her leash, for example.

I'm also not into loving intimacy with a man. I will service a man if that pleases you, but strictly with my mouth in the neighborhood of his middle. I don't want to go to either end of another man. Don't want to kiss him. Don't want to suck his toes--will absolutely refuse, in fact (there's your hard limit, or one of them). I'm not at all attracted to men. I will suck a cock, can even be made to lick his clean ass I found out one time, but it's not because I'm attracted; it's because my fantasies run to, "what's the most humiliating thing my Goddess can possibly make me do?"

I used to think that would be just, simply, being dominated by a woman, but fantasies grow over time. So yeah, while this next thing has never even come close to actually happening, I could even be restrained and force-fucked by a man for your amusement--assuming you might find that amusing. I know of a woman who likes to do that to her sub every once in a while, just because it's so fucking humiliating for a man to be dominated like that by another man--ha! That's the deal, isn't it? You're not looking for a man. You're looking for a sissy, right? Being restrained, wearing panties, stockings, and heels; maybe even the penis cage, in front of a real man, making me suck him to full erection before he fucks me up the ass while you sit smiling, maybe giggling, or laughing and taunting out loud . . ..

I could be reading you wrong, but seems like that's a place our interests might converge. But only if you're truly dominant.

Of course, before you ever let any man get anywhere close to my ass, I fully expect that you will make me your bitch first. I won't say there's never been anything up there, but it was slight and it's been a very long time, save one very narrow probe while a woman spanked me across her lap. I found out I enjoyed it, squirming and bucking against it to get the most from it. So, if you want to strap on a big one, shove me down over some piece of furniture, and assert youself, well, it's not a foreign thought in my mind and, as I understand it, it's very humiliating for the boy, and really establishes who's the boss. I've heard the boy is never the same, after.

A hard limit. I already gave you one. Scat would be another. While I am, or could be, into all kinds of ass play, scat is out. Unbelievably after everything I've confessed, I still retain some germaphobic tendencies, not to mention how absolutely distasteful; but more than anything that's a health, and just sensibility, risk I won't take.

Respectfully, Miss Ashley, I gave a way lot of thought to the limit thing before I ever started writing. That's another reason for my tardiness. I'm a smart boy. I suspect you want a hard limit because, then, when you can finally make me cross that line, you will know you have conquered me. I'm pretty sure you can find another way to achieve that affirmation. Breaking the limits like that might be valid with most guys, but considering where I've already been, I've already crossed most of the lines that I ever will. I'm sorry you weren't the one to make it happen, sorry to deprive you that one thing if that's where you wanted to go.

On the other hand, there is still much to explore. I actually contemplated telling you a lie, giving you a hard limit that I've already conceded, just so you could have the enjoyment of taking me past my point, but I don't want to build a relationship on a lie. Even though it's not a hard limit anymore, being buttfucked by a real man, something I've actually fantasized about when I'm feeling especially needy, maybe you could look at that as a hard limit. It really is still just a fantasy, and one I'm not totally sure I would go along with when it actually comes up. Or even you doing me first with a strapon. Like I said, something has been up there, but I've never been close to being well and truly fucked up the ass by anybody. I've never had anyone "own" me like that. I can imagine it, though. Maybe even after a rough day for you, when you come home and just need to take it out, harshly, on your obedient little sissy as you pound into me hard and fast.

Have I covered what I hope to gain from the relationship? Real, sincere fulfillment for both of us, especially you, is where I would hope it would go. Regardless of what I've confessed, here, I would hope we are compatible enough that your desires would feed, and become, my purpose.

Thank you for reading, Miss Ashley. Like I said, I'm pretty sure I'm too old for you, especially with an eye for your future. You really need a younger guy, younger than yourself. That shouldn't be hard. Most women don't realize how many eager, closet subs are out there. I think most men, though it's not something we typically talk about, have submissive fantasies.

Maybe you could introduce me to your mother or aunt. I mean, only if the woman is single, or at least, free to play.

Most sincerely, and I think you can tell,

dave

PS, Miss Ashley, I've danced around it in this message, but never stated it clearly, and maybe this can keep me in the running, even at my age. My jerkoff fantasies--yes, I'm a little jerky boy, and a panty sniffer, too, when I get the chance--often stray to cuckold thoughts. Can you, would you, imagine an older, obedient sissy like me who is not only ok with it, but who will actually find you the young, real men who can satisfy that part of you that maybe I can't, even if they're just mostly eye candy and a big hard cock? Can you imagine me serving the both of you, actively working to increase the pleasure he gives you?

Thank you, Miss Ashley.

i guess i need to check in more often.

i am unsure as to the status of your search.
i will provide information to see if we have any compatibility and whether i can capture your interest.
i have some characteristics that may put you off.
I am 66 years old and married. i am not seeking a real life relationship, only an outlet for my sub desires and fantasies. i have had experience with professionals, but no real life sub relationship.

i am located in Western Massachusetts.

i enjoy travel, reading and the blues, among other interests. watching professional sports. Big Bang Theory.

i think not wanting a real life relationship is probably a pretty hard limit. My interests lie in the areas of spanking, goddess worship, bondage, pegging. Following orders. Pleasing.

i hope you find something that interests you in here, although i am not optimistic

check in

MissAshleyToYou said:

i guess i need to check in more often.

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hello Mistress.

How are You? I do hope that You are still alive!

I cant brlieve