Ms Olivia 1-800-601-6975
When did you start crossdressing and/or experiencing a need to be en femme?
There are many different *kinds* of crossdressers. Your experience of being a man in panties is as unique as you are! In fact, you might not even be a *man* no matter what is between your legs. The Experienced Mistress knows the difference between a crossdresser, a sissy and a TV/TG girl.
I listen and learn who you really are
You are unique. Your sexual fantasies are individual and personal. When we do a session I create an erotic fantasy that targets your own experiences and expressions of your desires.
If you simply like to wear sexy panties as Mistress control over a submissive male then there’s nothing worse (for you) then being called a sissy! When you’re a sissy slut who yearns to be told to suck cock for Mistress, chances are you don’t want a lot of conversation about current lingerie fashions! See what I mean?
Your first experiences tell Me a lot
When I ask you about your crossdressing history, it’s not idle conversation. It’s a map of your erotic landscape. I use what you say to push buttons and sexual triggers that you might not even think to articulate to Me. How it all *started* tells Me a lot about you and what you *need* now.
pantyboy tells about the beginning
pantyboy: “I first started wearing panties in college. I had messed around with panties and such before that, but it wasn’t until I had a long term girlfriend in college that I found myself doing it a lot. I loved buying lingerie for her, and she loved wearing it for me, many times I found myself sneaking them and wearing them from time to time.”
I’d like to hear from you. How do you express your feminine and/or submissive side?
Ms Olivia
My Current Schedule — How to talk with Me
The 1st time I experienced crossdressing was when after school when I was ((young)) when my stepmom would sit on my lap and give me lipstick kisses…she was 32 and hot…After awhile I would sneak into her room and spray her perfume on me then try on her lipstick. It would progress from there later in life. It really got me interested when Ginger would put arms around Gilligan and kiss him…I always wanted that to be me with Ginger doing that to me. When crossdressing reached the high for me and point of no turning back was when I was home alone doing laundry and waiting to do my load of clothes was when my roomates gf left load in washing machine/dryer and I saw bra in her basket. She was 34 c/d cup so her bra didnt fit me but I had to touch/feel bra. I took off shirt and put bra on my chest and right then and there I was hooked. Then next day I went to Victorias Secret bought my first bra and then went home wore it and made mess. I started going every 2-3 months adding to my collection thenstarted to buy panties then slips. Also she had lipstick in bathroom and I had to try on and it felt great!!!I didnt want to get cought and I never did in fearing what my roomate would do. I hope it wouldve been just her but it never happened. That was 12 years ago. Thne I found this site and heard audios of mistresses putting makeup on guys as well as bras dresses and I finally found what I was looking for. The audios were hot and I would listen to them with my eyes shut with mistresses doing that to me. As a result I started buying prom/sheath/wedding dresses thanks to MsTia as well as heels and girls sweaters/pants/wigs. Honestly womens clothes are sexier and fit better then my boyclothes. I tried to find women into doing this but none seem interested as I asked ladies at salon but they gave me cold shoulder. They asked why I wanted it done and were worried about my safety and spending $$$ on makeover that would only last for a bit. They dont get the (seduced) feminization. No one in my family know I love to crossdress but I love it its great to dress as women at end of day to relax. Ive called LDW alot and want to start doing it weekly as MsOlivia know how much fun we’ve had in her turning me into her girl while I try to resis but it falls on deaf ears. Ive spent too much money on womens clothes/makeup/ligerie to turn back now. I used to try soo hard to find women into dressing me as girl now Im glad im single which was big reason I never had gf and I can call you and other mistresses . Honestly I think it will be easier now then before to find women into doing this to me if mistresses want to help if not Im ok with being MsOlivias/MsViolets/MsHollys and LDWs sissy lipstick lesbian girl. Great post about crossdressing!!!
Ohhhhhhhhh…….thanks for writing that ! I always love to know where the fantasy or fetish starts …. I often recreate the updated Mistress version of that in the phone sex call itself. THANK you for writing all that Peter! I know I’ve said this before….and even done blog posts on it….but, it bears saying again. You’re right…..women who are *civilians* aren’t going to understand the fetish or the fantasy and most won’t want to do it. It’s always best to go to someone who really knows what they’re doing and wants to do it with you! ~grinz~ Hence the Experienced Mistress and your other Mistress favorites 🙂 *lipstick kisses*
Hi MsOlivia! *waves*
So I was thinking about this post, as I am wont to do, and I guess I was wondering as to the definition of cross dressing. Certainly it’s wearing the clothes of the opposite gender, we can agree on that, no problemo. But….. does wearing panties really count if that’s it? Especially if you’re doing so because of the submissive act of say wearing a Mistress’ panties because she enjoys it? That is, is just the wearing of panties enough to be cross dressing if you’re really doing it for someone else? I guess to the letter of the law, but still…. it doesn’t sit well with me unless someone goes beyond that, perhaps wearing more or wearing them for one’s own desire. Sort of like wearing a collar wouldn’t make me a dog. I know that’s not the same thing by definition, but I just feel like something more is needed.
*Goes off to ponder this further*
*waves* great point magnus. No…..I agree that being a submissive man who wears panties for a Mistress is NOT crossdressing. I’ve done lots of post on the difference between a man in panties and a crossdresser or someone who is transgendered. BIG DIFFERENCE. I have heard horror stories about phone sex girls (from other companies) who don’t know the difference and then start calling a submissive man a sissy! ICK….totaly hardon killer! I always go by SELF DEFINITION….so a crossdresser would self identify as a cross dresser. Does that make sense? I’ve never been one to put arbitrary labels on people….and doing this has made Me extra conscious of that 🙂 GREAT comment and thank you for taking your time to post it! 🙂 *wiggles toes at you with a lacy sexy pair of thong panties on My sweet toes* Now…..let’s REALLY talk……… *wink*
Oh my… I’d know I’d be very happy to REALLY talk if I got to do so staring at that thong on those toes. 🙂
*wiggles toes*
Oh magnus….you just wait until I get more blog posts up……you’re going to be VERY happy! *wink*
I started wanting to wear woman’s clothing when I was pretty young … As I got older I ran out of my mom and sisters things to try on, and I realized that although I wasn’t into me, the idea of being dressed head to toe as a woman turned me on just as much if not more than any woman I’d met.
Now I own a few boxes of clothing and toys, in my late 20’s I still get a huge thrill just thinking about being dressed up!
Thank you so much for your comment Staci! Can I ask you some questions? These are the types of questions I ask on a phone sex call …. I’m curious how you identify yourself sexually. And does your sexual identity change when you’re dressed en femme? Can you tell us more? Inquiring minds want to know….and all that ! *hands you lip gloss* 🙂
Sure MsOlivia ask away! 😛
I’m not really sure how I identify myself sexually, but I would say my sexual identity changes a bit… I get more slutty and more subservient for sure 🙂
That’s a GREAT answer staci! I think sexual identity changes over time, circumstances, attention, levels of desire, etc. I’m so glad you’ve shared that! I love a really subservient slut! There’s something just so NAUGHTY about that! *wink*
I have actually discussed this with a couple of the mistresses at EE and no one seems to be able give me a definitive answer on why this would happen but one of my earliest memories in life (and there are not very many of those as I am 42 now) was of being in the living room of the house I lived in with my parents. They were both in graduate school and it was a rental. I was (young) and I think it was the day we first moved in. There was a suitcase full of some woman’s clothes and underclothes on the floor in the living room and the only thing I remember was being drawn to it and then pretty much going to town rifling through all of it. The next thing I remember was getting pulled off of it by some adult, probably one of my parents.
After that of course I don’t remember anything being so young, but the next memory I have regarding crossdressing was when I was (older and still young). That was when I actually started trying my mom’s hose and panties on when no one was around. Got caught once in the laundry room … , was really embarrassed and tried to deny what I had been doing, but mom just told me it was natural to be curious about what women’s clothing felt like and never mentioned it again. I also remember daydreaming all the time when I was growing up about this recurring fantasy. You see my mom used to take me shopping with her to the mall every weekend and drag me around while she tried on dresses and stuff in all the department stores. As expected from any young man, it was pretty boring for me, but having all that time just sitting around the women’s sections I would daydream about being left in the mall after it closed and having unobstructed access to all those clothes and lingerie for the night.
Now that I am an adult, my crossdressing has evolved into full on fantasies of feminization and I am actually preparing to start going out in public in a limited fashion someday.
Dear Heather! What a wonderful, detailed sharing of your journey! Thank you SO MUCH! Most of the crossdressers and nearly ALL of the bois who are female inside tell a similar story in terms of age. I do talk with one person who was blessed/lucky to have a loving woman who supported the femme expression and even helped with it in real life! I think that is very important. While ultimately it’s a solo journey to Self (and part of the human experience) when you have people along the way who *get it* the journey is so much more *gentle.*
*lipstick kisses sweet girl!*
Ms. Olivia:
Crossdressing, what a wonderful word. It brings such good times to mind. I have since about 33 dressed in different womens garments. Only during a session with a Dom have I been totaly dress wig and all. But I use to clean a Mistresss home in a pantie and bra. I had use to wear them during the day when I would run out to go shopping. It gave me such a thrill to know what I had on and had always made sure that when I bent over to reach for something my throng always showed. Always waiting for that tap oon the sholder, you little bitch. You are coming home with me and clean my bathrooms. You little bitch.
Thank you for a comment gene! I know as the Experienced Mistress I often use crossdressing as part of the submission….similar to the service work of being a sissy maid that you described. I love that you described that so well, THANK YOU ! 🙂
My first time I dressed up completely was in (young) Grade. My mother was a nurse and she worked day shift. I told her one morning that I wasn’t feeling good. She called me off school and went to work shortly after. I hurried up and left the house and hurried toward my school, which was a Catholic School. I snuck into the school after first bell and worked my way toward the gym. My class had gym first and I waited in a janitor closet while my class dressed for gym. They went outside and I snuck into the girl’s lockerroom. I looked around for a girl named Nicole that I knew was close to my size. I took her clothes but not her shoes, I looked around for some that fit me and took those as well. I snuck out of the school and raced home.
I took a quick shower and used my mom’s razor on my legs. After many cuts I had smooth legs. I took out the bag of clothes. I slipped on the pink cotton panties first. I still remember they had lace around the edges and a cute little bow it front. I felt electric as I slid them on, tucking my member between my legs. I then went for the training bra and put it on, learning how from wearing my mom’s bras. Pink just like the panties. A light pink blouse was next. I remember how fun it was to button them up from the other side. The pink knee-high socks were next. I almost passed out with excitement over how that felt. Then came the best part. The plaid, pleated skirt! It felt so good putting it on and buttoning it in place. I hurridly put on the hush puppy shoes and I was in heaven! Walking around the house, the skirt swishing around my legs. Sitting and having to smooth the skirt under me as I sat. I giggled and laughed with delight all morning.
I got so wrapped up in it I didn’t hear my mom coming home for lunch to check on me. I was in the kitchen getting a drink and I walked out to the living room. My mom was shocked and dropped the grocery bag as she saw me. I freaked out and ran to my room. My mom came in and demanded what I was doing. I broke down and told her how much I wanted to dress like this. I cried and she comforted me. She asked me where I got the clothes and I told her everything. She made me get dressed back in my clothes and scolded me for what I did. She told me to take the clothes back in the morning and hide them in a closet so someone would think that it was just a prank or something. I did and I never got caught dressed by my mother again, but I think she knew I was still dressing.
Dear Melissa, thank you so much for writing about your first experience as a crossdresser! I actually think your Mom sounded very cool about the whole thing. My read of it was that she was more upset that you took the other girl’s clothes than about you wanting to dress as a girl. That might be a mis-read on My part. I think the stealing of the girl’s clothes is risky but I totally understand why you did it. AND, I think this is one of the reasons why any male who cross dresses really needs to have his own en femme wardrobe and ways to keep it safe! I did an earlier blog post about purging and I know the reasons it is done, but it still makes Me sad!
I started cross-dressing in college. It began with growing my hair very long (waist-length by the time I was finished) and having a girlfriend that liked brushing and styling it – usually in very girlish ways (pigtials, braids, buns, barrettes), I basically lived with her and her two female friends in the first floor of a duplex off campus – I had the longest hair in the house. So eventually after styling it, it led to make-up, nail polish and waering clothing. I balked a little at wearing dresses, but was convinced that with my hair in curlers and wearing make-up, why not? I was now a girl anyway, I was told. Eventually, female clothing is all that I wore, except when I went to class. Christmas came and I got nothing but female items – bra/panty sets, nighties, skirts, a purse. They even had me going out with them to movies, clubs – fortunately I could pretty much pull it off. Then, over the following summer, I went home and lived with my mother and sister. My mother was asking if I was ever planning to cut my hair (it was past my bra-strap by then), and started referring to my sister and I as her daughters. She was surprised when I showed up for dinner one night with my hair in high pigtails – my sister was in hysterics and went and got some pink ribbons to put in them. My mother said that I looked like a sissy, my sister picked up on that and that became my new girl name around the house, as I gradually wore my hair in girlish ways more often. Then one night, my sister lent me a dress, and made me up for dinner. My mother just shook her head, and asked me (1) if I now liked boys and (2) if I was considering a sex-change. I said no to the sex-change, but my sister immediately offered to start setting me up – she had a gay friend and said we’d be cute together. And I knew they had finally accepted me when they also got me female gifts for my birthday, and the card on the presents read “Sissy”. I was in heaven. My girlfriend eventually left me for a “real man”, but we continued to be girlfriends. Both she and my sister continue to be supportive to this day.
That’s a wonderful story sissy lynn! I love that people in your life are supportive! I do think that is very important for everyone…whether a sissy cross dresser or a Femdom Mistress. When we have people in our lives that know *who* we are it sort of *frees up* all sorts of other emotions!
So, it’s a holiday again and I’m curious, what’s on your Santa-baby list? Hmmmmmmm Cute clothes, shoes, accessories? Maybe some more makeup? I just got a bunch of sexy lingerie (I know, before the holiday but hey, it’s always wonderful to have new lingerie!) What are you wishing for? Hmmmmmmmm?
Thank you Ma’am – I’m glad you enjoyed the story [curtsey]. However, not all of the women in my life have been that supportive. Some were quite mean and I’ve been called a lot of humiliating names – and made to do some humiliating things. And to their dismay, I loved every minute of it!!! For Christmas, I only exchange gifts with my sister. My “hints” to her are a new doll (I have a collection), new hot pink fuzzy slippers (to go with my robe) and some “Hello Kitty” hair accessories. She giggled and shook her head when I mentioned that last one. I agree with you on sexy lingerie – a girl can never have enough. My list for me would include new boots, new panties and a new “toy” – as lifelike as possible. Oh and of course, my fantasy gift is being allowed to be your sissy maid and serving you and your friends!! Happy Holidays Ma’am [curtsey]
I hope you had a wonderful holiday sissy lynn! Tell us….did you get the doll you wanted?
(answer with bows in your hair!)
My first time crossdressing was as a young boy, playing at the neighbours house with a young girl. She asked me to put on one of her dresses. We were too young for this to be a sexual thing, but still it felt to exciting for me.
The second time was at age (older). I had a job at a shoe store and one of my tasks was to empty the trash each day. One day while emptying the trash from the restroom, I found a pair of purple pantyhose with a run that had been discarded. I locked myself into that restroom, undressed, and then put on those used pantyhose. It felt so good on my legs! It was so exciting that I couldn’t help touching myself, and I found myself masterbating in those worn pantyhose. I wondered which of my co-workers discarded them as I soiled those pantyhose with my cum. Afterwards I knew I was different from most guys and I felt ashamed. But I have since come to accept, embrace and enjoy my inner sissy.
Chrissy
Ahhhhhh, Chrissy…..I don’t think ANYONE is in the category of “like most guys” or even “like most girls” …. I think most people are more in the middle or the gradations of gray between black and white. I think the whole concept of normal is a myth, sort of like an Urban Legend. I know from being in the Femdom fetish world that people do have sex secrets. I suspect that the sex secrets is more normal than so-called normal (whatever that is! LOL) Thank you so much for leaving a blog comment! *kiss*
I am glad that you made that distinction between a man who just wears panties and one who is a cross dresser, I never understood the difference until now. I would wear a pair of Mistress Mandy’s panties if she wanted 🙂
Oh MY Matty! There’s a HUGE difference between a man who wears panties for his Mistress as a sign of submission or simply to please his Mistress and someone who is a crossdresser! As you know, I’m all about the nuances in the various erotic pleasures and fetish fantasies! Even with a sex fantasy that *looks* totally identical to another, there are ALWAYS nuances …. I think that is one reason why I love this career, I enjoy finding and then creating totally individual fantasies that are personal to each person! 🙂
You are right about my mother. She was and is very supportive of my desire to become a woman. She was the one who told me about my therapist I am seeing now. I have come to realize that I am a woman trapped in a man’s body, and I am going to correct the mistake. I have my own complete wardrobe now. It is sad when I hear of purging in my support group. I went through that. I am done pretending to be someone I am not.
*nods* Excellent Melissa! In My experience, cross dressing doesn’t just *go away* …. in fact, it gets even more intense after the purge. I know that people, being people, will do what they do….but I also know that it’s smart to be realistic! And this sure is one of those things. I think I’d like your Mother, she sounds like a wonderful woman! 🙂
Thank you for the nice compliment. Yes, my mother is so wonderful and supportive. I love her to death. Anyway, purging does make the desire more intense over time. The last time I purged, I actually cried for days. I felt like I was throwing my real life away. It didn’t take long for me to finally come to the realization of who I am. I will never purge again, except for my male clothes! Which will be soon!!!
You said it very well Melissa….. I often get the sense that *purging* is such a deep loss. I had a fire many years ago and lost everything so I do have some sense of the loss of possessions that have an emotional history. I can’t imagine the pain of purging …. but you know I’ll sure urge you to get rid of the male clothes when that time comes! *lipstick kisses*
My first experience crossdressing was when I was (young) and home alone. I went into my sisters room and saw a pair of pretty pink panties on her bed. I had matured early so I got hard on. I put them on and after searching her closet I had a black mini skirt, lacey pink bra, and a black top with poofy sleeves. I loved how it felt on me especially the panties. My sister never found out, but I did it a few other times that year. I told some of my girlfriends in high school and although they broke up with me they were better friends. They said that I always had seemed like a pantie sniffer to them with my feminine face on my masculine body and my 4in. small penis. They taught me to be a girl and called me Christina and with them I discovered that I was gay. I now live with my parents who don’t know anything, but I’m soon moving to seattle to be with my master.
Wow, Christina! Thank you so much for telling us your story! Please keep us posted. I love Seattle and I do know that moving can be stressful and joyful all at the same time! Have FUN!
My first time dressed as a girl i was about (young) and my mom and sisters helped me and they thought it was going to be the last time but i was hooked . So from that day on all i wanted to do was dress like a girl the way i was ment to be. When i got in (school) i met a boy that thought i was a girl we became friend and one day he told me that he wanted to kiss me and i told him that would be ok with me from the first kiss i knew i was really a girl. He spent the night with me on a weekend and thats when i went down on him and i loved it . My mom told me later that she saw me sucking that boy. but mom knew that i really was a girl so we never went back to being mom and son it has always been mom and daughter.
Thank you
BobbiFaye
WOW, I love that BobbiFaye…..like with most things there is an *intuitive* feeling of rightness. I’ve noticed that crossdressers, sissies and girls trapped in a supposed boy body all have that in common — it’s a feeling of *rightness* when you get to where you’re supposed to be!
It’s great that you’ve got family acceptance and support for your true gender!
*hugs*
Ms Olivia
I first started Crossdressing back in 2008.While this time i was downloading audios on Getgirlie and Teasemania alot. I also got my sissy name to. I also was wearing my moms panties and stockings. I now have many pairs of panties. I also now have a pink baby doll sheer nightie. I tend to wear my panties each day to. I an 26 years old. I love Feminization and Fantasy of being a sissy with you mistress Olivia.
You are delightful angelica! You’re very *trainable* as a sweet (and sometimes naughty) sissy. *wink*
I submitted something yesterday 3/7/12 & it never showed up?
I started wearing dresses when i was ((younger than I am now)). If this works I will send rest of my life in dresses *G*.
You are by far the most beautiful woman at LDW. We “girls” are very fortuante to have you to chat with.
Huggs,
Sissy malissa