Olivia 1-800-601-6975
I love your comments and questions on My blog!
I also enjoy when you contact Me via IM. This post is a reprint of is a blog comment posted by chrissy who contacted Me first via IM.
((Thank you all for being understanding that I’m not always able to do the free IM Chats in real time.)) I quickly realized that chrissy’s comments needed more individual attention then I’m able to give in the free IM chats and so I directed her to My blog.
About chrissy
chrissy is a crossdresser who, as you can see, has used crossdressing phone sex for years as a way to experience these feelings as a submissive crossdresser. I want to post her entire comment and then in the coming days, I’ll respond specifically to various aspects of her questions and comments.
I think the fundamental issue that chrissy is addressing will ring true for many of us. It’s how to explore erotic needs, desires and sex fetish issues in a way that is safe and sane. Of course, phone sex itself is an ideal outlet AND she, like many of us, struggles to bring the fantasy more into real life. She puts it this way: “Its the struggle for integrity, self honesty and functionality in the real world!!” I can relate chrissy and I suspect our readers (cock control fans you know who you are!) here on My blog can relate as well!
chrissy’s comment (section labels in bold are my only changes)
Dear Empress Olivia,
Thank You so much for Your time on IM, it was really great to have a quick chat. As You instructed, i have posted the gist of our conversation below and i look forward to hearing Your responses at Your convenience.
phone sex and the real world for men in lingerie
i have done sessions on and off with various beautiful LDW Mistresses, and have accrued some real time experience over the years. As a part of my training, i have been required to wear panties at all times; required to buy panties, bras and make up and to tell the sales Girl that the items are for me; required to get my legs waxed, nails done and keep my pubic hair shaved and/or groomed into a girlie triangle above my clitty; i have been made to wear butt plugs; enticed to suck cocks; threatened with chastity and served as a sissy maid at a femdom tea party, plus played with some Dommes in the local scene.
crossdressing crossroad
Recently, i have become aware that i am at a crossroads. i know deep down that i need to integrate my kinks into my life, or to somehow move away from them entirely (which i know is impossible). At present it is a secret i keep, even from partners… and have learnt that through non-disclosure of my kinks i am kind of fucking up the honesty of the relationship. The dynamic of the sex in the relationship is founded on a half-truth…which then sort of leaks out into other areas of the relationship.
i am trying to work out a way of being at peace with it, and living it at an appropriate level in general life. In other words, i want to live my kinks without losing credibility or becoming a walking freak show at the local mall where i buy my panties… If that makes any sense!!
crossdressing conflicts
The conflicts i feel are sophisticated and quite deep… its not just a matter of feeling shame, or suffering guilt, or freaking out about duplicity in relationships. It’s a struggle i wage within myself, a real push and pull between major forces which (to simplify) can be broken down to “light” and “dark”, “feminine” and “masculine”, “defiant” and “submissive” etc. i am trying to figure out an equilibrium that works for me. Sometimes when i get into this stuff i feel a dissolution of self set in that is deeply corrosive… and totally contra-creative … and i can’t go there without abandoning or betraying myself. But when i desist entirely … i feel deeply lonely!!! Even if i am in a vanilla thing and very well loved.
real life issues for men who love to crossdress
i have a very full and successful life with a lot of vanilla friends who i love… but i do not want to lay my kink out in front of them. In other words, i do not want my kinks to encroach on my vanilla life, but nor do i want the vanilla to eclipse my kinks… i say this having recently ended a relationship with a beautiful vanilla woman.
Its the struggle for integrity, self honesty and functionality in the real world!!
And NOW i AM laughing at myself and blushing a rather fetching pink!!
Yours very truly,
chrissy
Dearest chrissy, I’ll be responding to the specifics of your comments and questions in the coming days. Let Me just let you know that you are not alone! We have a variety of essays with practical suggestions for crossdressers and you know you’ll get the personal touch (so to speak) with Me. I’d like the regular readers of this blog to also post comments because even if your kink or fetish is different from chrissy’s I know you have (or are currently) negotiating this path. So, let’s hear from you!
Ms Olivia
“I also enjoy when you contact Me via IM.”
i have to say, Ms. Olivia, that participation on Your blog is addictive, in and of itself. i quail to think of what could happen on IM, much less on the phone. however, given i currently operate through a w-lan, my IM is so unstable that between that & Your calls, a 5-minute IM conversation could easily take 2 weeks. 😉
as to chrissy’s concerns, i fear i’m of little help, although some of our experiences may be comparable. i’ve done, & probably will do, crossdressing. however, it isn’t who i am. who i am & whatever i do is always within the context of serving &, especially, pleasing the Domme at the center of my attention. perhaps she and i compartmentalize things differently. but, except for wearing panties on a routine basis, my crossdressing is in homage, not out of inner need. even the panties, and today they are sheer hot pink with a little black bow, are in homage to that first Phone Mistress. with each Domme that i encounter, if W/we choose to interact, i try to cleanse my mind & present myself to Her, to the extent possible, as a tabular rasa awaiting Her imprimatur on my psyche. it has helped me bring depth to the interactions, while highlighting for me that one essential constant.
i am a submissive male.
~laughs~ @ coffeeboy’s description of your w-lan! LOL
I’ve got a question …. do you think that there’s a gender difference going on here? I notice with the sissies there’s a more (stereotypical) approach … ie incorporating the ‘sex’ into the whole of ‘real’ life. That is also traditionally more “female” in that men are more able to compartmentalize sexuality. What do you think?
in answer to Your question, Ms. Olivia, i’ve read or heard innumerable times over the years that men think about sex a couple of thousand times per day. if the male of the species weren’t adept at compartmentalization, we’d never get anything done! however, i seriously doubt that the membranes between all these compartments (sex & sexuality, work, relationship, sports, etc., etc.) are all absolutely impermeable, except in the most extreme “alpha male” workaholic cases. for the rest of us, we each land somewhere on a continuum between impermeable & highly porous with sissies landing somewhat (perhaps much) further along the continuum than i consider myself. nor do i think the position is subject to stasis. pressures in one compartment (say workload or the relationship with & demands of a Domme ) can push that position in one direction or another.
i know with my first Phone Domme, because of the chemistry, or for whatever reason, it was essential for me to be “Her keri girl” to the extent possible & my compartmentalization did experience a bit of bleed through. however, once She retired from the phone, a different equilibrium condition set in. some subsequent Dommes have engaged me in feminization, but it hasn’t felt the same. having me dress prior to a call simply accelerated me reaching a submissive state right from the start of the call. since i can never predict what may come next, i never throw anything out. i moved in December & all my femme stuff is safely stashed away in a merlot case, labeled “Hold for Lauren,” a fictitious person who left stuff at my place when she left for Australia on a long term assignment…should anyone ask. lol
@ coffeeboy ….. I love the continuum imagery ….. you’re right that tends to fit with most things and here too as well! Although I confess I got a little naughtily distracted by the impermeable and highly porous writing! LOL And, have to take a (*fans self*) break!
~laughs~
beginnning to wonder, Ms. Olivia, are You inspiring me to suffuse technical descriptions with sensuality, or is it there a filter through which You’re reading what i write, or a blending of the two? lol
LOL coffeeboy…..probably a blending of the two … something I often find that happens with phone sex connections. Personally I LOVE the science because what better way to describe human sexuality than in terms that are very personal to each individual……while I’m not a scientist I have a curious mind and your descriptions capture My imagination and interest 🙂
i seem to be fond of the concept of a continuum in a lot of societal situations. all things are nuanced and thought processes and actions shift almost imperceptibly all of the time. it seems to me that only the faux moral arbiter, who profits from it, sees things in black and white. even the lowly (& much beloved by me) coon hound can perceive a multitude of greys.
WOAH !!! Once again coffeeboy leave a lovely, visual comment! Awwww……coon hounds are great pups! I used to have a dog who was part chesapeake bay retriever/chocolate lab ….. *sniffle* ….. he was the BEST!
I very much relate to chrissy’s comments and have some of the same struggles. While I don’t want to get into the labeling issues, I consider myself transgendered even though I work and live (with an accepting wife) as a male. I was dressing in my sister’s clothes (without her knowledge) long before puberty for reasons other than sexual. My wife knew and was accepting of this aspect of my life before our marriage so I am very fortunate compared to most.
Still, I feel guilty and less than honest in having to hide much of myself from co-workers, family and vanilla friends. I relish my chances to take trips and have vacations where I can be Jamie for a few days. Perhaps, if I were truly transgendered, I would make the decision to live full time as a female but the sacrifices (family and career) would just be too great. So, I compartmentalize my life and feel like a fraud in both roles. Finding this big understanding kinky community hasn’t solved my issues but it has helped. I really appreciate Ms. Olivia’s efforts to help us better understand and deal with our kinks. So, let’s keep talking and supporting each other.
awwww, thank you Jamie Rose …. I feel very strongly about acceptance and compassion (as you can tell). I also think this is an area where we can all begin to really *see* the results of choices. You are well reasoned about the choices you make and why so THANK YOU for posting a comment.
When crossdressing (wearing panties all the way to full feminization) is *held* in phone sex experiences then it IS secret but you also get the benefits of that element of privacy in your real life. I think that expecting the vanilla world to understand or approve of our kinks is not only unrealistic but can lead to frustration six ways from Sunday.
Jamie, can you tell us more about WHY you “feel like a fraud” in both areas? Do you need the two sides/aspects to integrate to feel *whole* …. ie I don’t wear fancy clothes to a baseball game or My high tops to a business meeting. Can you help us understand? I know it’s WAY more than the clothes but I don’t begin to assume that I *get* life as transgendered. I love gender play but don’t consider myself transgendered so I can’t speak from experience about this. I hear the same comment from many people who are transgendered and I’d like to understand more.
HUGS you and hands you a new Mac makeup palette of colors! 🙂 I also believe that life is better with Mac makeup lip glass! LOL
Dear Mistress Olivia,
Firstly, i am honoured that You decided to post my comments in Your blog and i thank You deeply with lots of hugs and kisses on whatever part of Your body You deem appropriate 🙂
i think the question You pose pertaining to gender difference is really interesting. On a certain level i present as a heterosexual guy with kinks, but deeper down (or perhaps in another paradigm entirely) i am more like a woman than a man, and it is possible that my desire to integrate my kinks into my “civilian life” stems from not being able (or willing) to compartmentalize sexuality. my dilema is that i no longer want to separate the various aspects of myself. In other words, i see it as a struggle to integrate the feminine and masculine sides of me on an energetic level… and the way it seems to manifest for me in the material world is through a great, great love of feminine style, fashion, make up and other accoutrements (yes, yes, yes … ESPECIALLY PRETTY PANTIES!!!) and an adoration/worship of beautiful dominant Womem for whom i yearn to surrender. For me it is a process of surrender, of letting go without losing myself, of becoming whole.
But please don’t get me wrong… i also utterly love it and find it sooo sexy, so hot and so divinely fucking delicious 🙂
(and i adore the depth of sex, that space of intimacy that two or more people can create in which the rest of the world peels away and you dare each other to reveal yourselves. i find that sexy. and i believe it to be the shortest route to the expression of the divine in humanity… not the only route, but a valuable one which has been poisoned by those conservatives who presume -through their fear driven lenses- to control. but i digress… so forgive me!!)
Thank you to coffee boy for his interesting comments too!!
Its dawn where i live, sun will be slipping up over that mysterious horizon any second now and i am in a trance after having worked all night.
Your are divine, Empress Olivia… and deeply special for being willing to host discussions such as this.
from my heart to Yours,
chrissy
Hugs to chrissy! A sweet slave sent Me a book….Spiritual Transformation Through BDsm (Sensuous Sadie) and I’ve already read Radical Ecstasy ….. both those books are more BDsm oriented and crossdressing / feminization can be (and is for many) part of the Femdom experience those resources aren’t specifically about fem things.
When you speaking of integrating the two (masculine and feminine) sides of yourself and you use the term energetically I *hear* that this might be a spiritual journey for you. Is it? However YOU define spiritual journey?
I always thought cross dressing was one of the kinks that that was poorly portrayed in the mainstream media,movies,TV etc.
It was always an unpleasant/villainous/hardass male character that was found out to be wearing women’s clothes, usually women’s underwear. The plot discovery was done only for ridicule and to bring the character down a peg, usually to peals of laughter.
Not exactly sex positive for those who found enjoyment in that particular fetish.
It’s hard to put the toothpaste back into the tube when it comes to kinks so it’s very admirable that you are motivated to find a way for this to fit into your life, even if that’s a difficult process.
“This above all: to thine own self be true.”
Great in Hamlet. A hell of a lot harder in real life.
@ John …. you’re so right! It IS important to be true to one’s self AND it’s also important to remember that actions in the real world do have consequences. That’s just reality.
Now…..*some* crossdressers aren’t cruel/weird…..I’m thinking of Madea, Mrs. Doubtfire and Tootsie …. but they’re all men in women’s clothes and they’re careful to keep any erotic aspect out of the whole scene.
MsOlivia, I am not a crossdresser myself (metaldresser perhaps 😉 ) but I do think that probably most kinks could be substituted here. It seems that chrissy’s worries center around whether her kinks are in conflict with the world around her, both close up with her friends and lovers, and a bit more broadly with others.
I’ve stated before in my comments to Your posts both that I generally like the way I turned out and that my kinks and fetishes do not exclusively define me. My fetishes are part of me, but so are many other things. I revel in being a geek. I like to ski. I am a good neighbor and a good citizen. I work hard and am good at my job. I vote. You get the picture. Just because I love to see sexy women’s feet and would love to be tied up and dominated does not take away whatsoever from any other part of me. All of those things make up magnus.
I am also aware that we all wear a mask of sorts. That is, we share with others what we want them to see. I don’t mean to say that we lie to them about who we are, but we don’t share everything with them either. And I think that applies to everyone no matter how close they are. I mean we do share far more with those close to us, but I don’t think we ever share every last thing. I feel fortunate to know people that I can share my kinks with, both here at EE and with some select friends, but the world at large won’t know since I don’t think they would understand.
So with that in mind, in chrissy’s case, her kink can be something that for herself or for some people she may know who can understand it. She’s not being untruthful at all to those she keeps that part of herself from.
@ magnus ….. yes, the whole thing of crissy’s post (and for others) it is all about the *stages of life* …. and it’s experienced differently with each person. We are each unique and so our issues and life journey will be unique …. BUT, there are common themes between people.
Re: the issues of masks. I totally agree with you and I, personally, don’t find the mask wearing to be BAD. I don’t share everything with y’all, with My guy, with the people I know around Me …. and all that. I don’t think that just the mask is a bad thing. But, rather the MOTIVATION behind the mask. For example, there’s something called the *withhold* where I don’t share as *punishment* … now, that is totally poison to intimacy and connection.
That actually makes Me think of something to say to chrissy. I really should ask her about her motivation about WHY she wants everyone to know. When making any life changing decision, it’s best to check and see personal motivation and expectations. Because if you can identify the motivations/expectations from any activity then you’ll be able to see if you’ll be able to actually GET what you want. My experience is that when approval is sought from outside …. well, it’s tricky. Always best to have internal standards and rewards. You totally get this, don’t you magnus? !
PS you ski? LOL I’ve been snow skiing once……I looked totally cute in My snow bunny outfit sliding on My ass! Then I seduced the ski instructor and stayed inside! LOL
Well, I can hardly take the role of a spokeperson for the transgendered but I will try to explain why I feel like a fraud in both of my roles. At work and with most family and friends, I feel I am hiding my other self for fear of being outed as a crossdresser or as being transgendered. I think I am a kind and understanding leader at work but know that exposure would ruin my career and damage my family. So, I feel I am playing a role to keep everyone comfortable. This doesn’t mean that I want to show up at work as Jamie or transition on the job but I have to be careful in hiding a big part of myself. I have to be careful that family and vanilla friends don’t drop by when I am entertaining my transgendered friends. I think my feelings of guilt and being a fraud as a male come from all this necessary secretiveness and fear of exposure.
I have transgendered friends that live as women. I admire their resolve, confidence and conviction to live their life openly as they see it should be. Jamie feels a fraud because I say I am transgendered but I stay mostly hidden for fear of losing my career, vanilla friends and some family. It seems reaonable, logical and safe but not very brave or committed to being true to one’s self. So, if you can stand to listen to this a little longer, I seem to be playing roles and not really know what or who I am. I am a bisexual, transgendered, switch or, as they say, “Give me ambiquity or give me something else”.
@ Jamie ….. I think that fear of various repercussions is totally legitimate. You mentioned feeling like you’re playing a role to keep everyone around you comfortable. That is also a ‘human being’ kind of statement. Magnus talked about the masks we all wear…..it ‘smooths’ human interactions. I guess the key is to find a sense of whole self in a community that fits … might not be perfect …. but much of life is that way (not perfect, but damn good anyway!).
Now, aren’t you BOTH though? Jamie AND your male self. Native Americans traditionally have had 3rd and 4th genders. Eastern spiritual teachings have transgendered humans as MORE rather than less. I have to shake My head and wonder, why we (western American culture) put others in a ‘box.’ YOU obviously don’t fit in a box and I know MY LIFE is much richer for knowing (the little I do know) ALL of your unique YOU-ness! *sigh*
I do indeed get this, MsOlivia. Only chrissy can say what chrissy’s motivations are. I do know though that sometimes people get wrapped in what they want that they don’t see the bigger picture. I am NOT saying this is one of those times, but it is something to keep in consideration and to be sure it’s really for the best. Sadly, we do not live in a time where all kinks are accepted universally by all people and in all places. I would hate for a life changing event to have more downs than ups.
I am not a great skier. I’d call myself an intermediate, but I find it a lot of fun and I got some new skis last year that I had to wait a whole 9 months to try out. And I am sure that You looked uber cute in Your skibunny outfit, on Your ass or otherwise. And *grumble grumble* lucky ski instructor. 😉
I agree magnus. It’s great to have the freedom to talk about kinks and stuff on a phone sex call …. but when someone starts talking about altering the whole of their life I really do try to help kind of reign them in and ask the question, “Are you SURE you want to do this?”
Dearest Miss Olivia,
The question of how one defines “spiritual” is a huge one. Personally, i resist using that term because like so many other things it has become commodified, or branded over the last couple of decades. But yes… in a sense the process is “spiritual” if You can accept a definition of spiritual that equates roughly to “connection”. Connection to the feminine, connection rather than obsession when serving a Mistress, connection to my friends and lovers… i guess that when i am being covert i am to some extent severing the connection.
To answer Your second question (“her motivation WHY she wants everyone to know”)… to be honest, i don’t really want EVERYONE to know, rather i want my partners to know about and enjoy my kinks. i guess my motivation for this is to live “above the surface” as much as possible, i don’t like keeping secrets from people i love romantically.
There are other people i definitely DO NOT WANT TO KNOW … my teenage son, for example, family members, vanilla friends and clients at work etc. When i say that i am looking for integration i don’t mean unfiltered disclosure which i think would run the risk of breaching the safe, safe and consensual protocols that i hold so dear. Having said that… i must admit to experiencing the thrill of (erotic) shame when i am buying panties and the sales girls know they are for me… but its a fine line and i certainly don’t want to enrol them (manipulate them)in my fantasy unless they are totally up for it (which happens about half of the time). In truth, i think i will be happy when i meet a Dominant Woman whom i love, and whom loves me to be Her sissy at least part of the time.
So, its an very interesting question that has no particular answer… it is more a process actually.
Interestingly, i feel a little thrill when You refer to me as “she”, and also when a woman that i work for addresses and introduces me as “chrissy” … Another new development is that it looks like a local Mistress is going to take me on as Her maid (so, i guess i will be exploring this all in a very hands on way in the coming months!)
Thank You Miss Olivia for this wonderful blog… and to all of you who are contributing to the discussion, i find your comments very elucidating!! So, thanks!!
Yours very deeply, Miss Olivia
chrissy
Ahhhhhh chrissy, Of COURSE I interact with you as she and her…..because you ARE feminine to Me!
That’s all good to know about the unfiltered disclosure…..I THOUGHT that’s what it was, but wanted to hear you say it. I’m not a fan of unfiltered! ~laughs~ Except, of course, in situations where safe, sane and consensual applies and then the unfiltered is part of the JOY of that relationship! Of course, the very nature of phone sex allows for unfiltered…..which is part of what draws Me (and many of us) to this forum!
You mention wanting to live ‘above the surface’ as much as possible…..ahhhhhhh, honey I get it. Me too! One of the most powerful human needs is to be SEEN and HEARD as you really ARE! And, with any intimate situation that need grows. Whew! Have you tried to talk with the women that you date? You mentioned the vanilla woman that was great …. I know there are women who are accepting and even encouraging to varying degrees. Jamie Rose talks about her wife and how she ‘negotiated’ these shoals before marriage. I don’t pretend to understand what you are going through, but I do *get it* in terms of empathy, understanding and compassion.
Let us know what happens with the sissy maid gig! I love doing sissy maid phone sex calls …. ~laughs~ …. oh yes, visualizes chrissy on her hands and knees doing clean up duty! LOL *wink* We WILL want to know!
Ms. Olivia, i was preceded into my parents household by a black-and-tan hound, on advice from the good folks at Planned Parenthood to divert pressure from “trying” to have a child. he was the first of three dogs my folks had. once married, we adopted a German Shepherd/Golden Retriever/Wolf(?) mix and a Blue Tic/Walker mix (pure WV coon hound). being sans dogness feels unnatural, but at this point in time, it would be unfair to the dog to have one. & i’ve a definition of a real dog for you. if it leans against your leg to be petted, it better at least bang against your knee. 😉
@ coffeeboy……I love your definition of a real dog! LOL My dog lives a nice long time and died of old age with white hair all over his face! Awwwwwww. I, too, would love to get a dog but each time I think about it I get to missing him and I don’t. So, I have kitteh’s right now!