why do you cross dress how did you start
- Thread starternancyask
- Start date
Lots of questions. I first tried on my mom's bras and panties sometime around 8th or 9th grade, but not much happened for quite some time after that. I was shy, introverted, and studied a lot. I did start lurking around park restrooms at about the same age and enjoyed the stall wall graffiti immensely, but I never hooked up with anyone in spite of several near misses.
I didn't get to live on my own until my early 30's, after having roommates in college and then getting married at an early age. But I started making up for lost time quickly after that, and was soon shaving and wearing full outfits with makeup that I bought both online and in stores. It took me somewhat longer to start going out due to fear of HIV, but within 3-4 years I was sucking off guys (with condoms) while crossdressed at adult theaters and bookstores.
Nobody ever made me do any this, or even provided any encouragement. Looking back, I'm certain that I would have started down this path much earlier if I had lived on my own at a younger age, or someone had been just the slightest bit forward with me in that park restroom. I wouldn't have put up any resistance at all.
I didn't get to live on my own until my early 30's, after having roommates in college and then getting married at an early age. But I started making up for lost time quickly after that, and was soon shaving and wearing full outfits with makeup that I bought both online and in stores. It took me somewhat longer to start going out due to fear of HIV, but within 3-4 years I was sucking off guys (with condoms) while crossdressed at adult theaters and bookstores.
Nobody ever made me do any this, or even provided any encouragement. Looking back, I'm certain that I would have started down this path much earlier if I had lived on my own at a younger age, or someone had been just the slightest bit forward with me in that park restroom. I wouldn't have put up any resistance at all.
after a few years i was 18 and 1 of the guy that hd dressed me up asked if i liked what they did he was kind of feeling me all over i told him i masterbated in the dress after they left he asked me if i wanted to do it againnhe would get me a bra and panties i said ok he was older and i thout it was cool that he was liking me the next day we meet in the woods and i put the things on as he jerked oss then he piy my hand on his cock and strted feeling me he told me to shut my eyes and i did and omg he kissed me befor i knew it i was laying on the ground with him on top of me stell kissing me then i felt him cum on my belly he told me to keep the bra and panties for next time
i called him the next day it was all icould think about he came over to my house and he had a bad it was a bunch more things a pink dress panthhose and a huge bra i started putting it all on and he watched he asked me if i liked being his gf i said yea kind of i sliped the dress om and he also had a wig he said i was beuitfull and kissed me it felt so good the way he was holding me we layed on the bed he asked do you want to be hus gf i said ok he lifted my legs and pulled the panties down he slid his cock in me very slow and omg it felt so good the way he was kissing me at he same time i felt his balls agenst my ass and he started going in and out he said i was going to be the best girl ever it was fast and he pushed in all the way i could feel him squirting inside me it made me cum at the same time
my sister in law had a bf they were over at my house 1 day and he asked if i wanted to see pictures of my sister in law mary i said ok and he showed me a few naket ones he asked if i had any of my wife i said yea and showed him 1 of her in a bra he realy loved her tits he said i needed to get a small spy can then said he would let me have one of his if i could get pictures of nancy he said he had movie of mary and him well i did it and goy some good shots and showed him he puled his cock out and started wacking off looking at the pictures and told me to do the same i did it and after a min he started a movie of mary and handed me his phone then took my other hand and put it on his cock he said jerk me off a bit you dont want you wife to know about this do you i said no plese dont do that he said do a good job and he would not so i rubbed his cock he started rubbing my chest he said he could tell i had girl tits he slid his hand in my shirt as i jacked him off he cam in my hand as he did he said that i eeeded a good bra for next time he said just put one of my wifes bras on i just said oka few days later he called and aked if i had any new pictures i said yea so he was going to stop over he said for me to put that bra on under my shirt befor he got here
well i put it on and put a few pr of socks in the cups then got my shirt on he showed up and right away huged me and started feeling the bra he just kept sayingo yea your going to make a hot slut baby and at that he kissed me but goodhe puled his cock out and had me get on my knees he was taking my shirt off to see the bra he sqid i was so hat that made me feel less shy and he asked me to kiss the head of his cock i just gave it a fast kiss he ,omed i did not know it but he had takin my pic and showed me he said you dont want nancy to see this i said no he said then you know what a good girl should do he slid his cock in my mouth hst the hed he took a few more pictures and started t slide in more and more he held my head as he pushed in agenst my throut he told me to shut my eyes i did and he shuved it in hard it went down i gaged he said thats ok baby take it slow he fucked in and out a bit then in hard again and held my head tight agenst him as i was gaging i relised he was cummng right down my throught
i gaged as he slid out of my mouth i felt so inbrised he got me up kissed me and said i was so good kissed me again he said now next time i had to do the bra but i also had to put on 2 other things and suprisw gum and he lso told me i was not to have sex with my wife i asked why he said he would tell me next time
i gaged as he slid out of my mouth i felt so inbrised he got me up kissed me and said i was so good kissed me again he said now next time i had to do the bra but i also had to put on 2 other things and suprisw gum and he lso told me i was not to have sex with my wife i asked why he said he would tell me next time
3 days went past i did stop doing anything with my wife gary was on his way over so i put the bra on and panties and a slip gary loved it right away kissed me and said he got me somthing it was a wig that looked just like my wifes hair gary puled me to the bedroom and layed on me kissingand feeling me all over he had his cock out and it was betwen my legs he kept saying he was going to treet me just like he would do to nancy he lifted my legs up and i put them around his wast he kissed me i could feel his cock right agenst my hole he said thats it baby we fit perfict then he pushed the head in me omg it hert so bad he kissed me and said its ok baby it will stop he pulled out a brown bottle and held it under my nose and had me sniff it he said it would help he was pushing his cock in now and it stoped herting it started to feel so good i was pushing up agenst him he said thats it baby you like being a slut dont you i just said yes fuck me he kissed me and then had me sniff more of the bottle i was just melting under his controal then he pushed in all the way iy was so good and i could feel him cumming i felt each squirt he had his toung in my mouth as he cam i got every drop after he finished he asked me if i wanted a dress he would get me one i said ok and he said he tryed to hit on nancy when she was at her sisters house i said what did she do he said she let him kiss her and he also felt her tits
Hi nancy my dear,
is this a scientific poll or anything like this? But anyway: just as there are real Men and real Women i am actually a "real" sissy ... and this is why i don't want to hide what i am. And when there are scientists who are interested in the sissy phenomenon i am more then ready to answer...!
In fact i don't see it as cross dressing since i don't dress as a real Woman would do. i actually prefer pink sissy clothes and frillies and so on that a real Woman wouldn't wear ... well, i think a slut would do but that is just because she loves to serve the expectations of Men. But i think that at least my chastity cage isn't anything that could be misunderstood.
i don't know whether this counts but maybe i started being sex years old when i realized that i wasn't a real girl! Before i was actually raised like a girl ... and of course i always used to see my Mommy as my role model...
my first "love" was one of my Mommy's nighties and some of Her silky panties ... and when i was nine they became my first "wet love" as well...! So to use a term of my sissy friend dollyanne i became some kind of pantysexual instead of hetero or homosexual ... or bi or whatever...!
Uhm ... make me do what exactly...? Dress me as a girl first? Mommy! Taught me to be a real sissy? Mommy and Daddy! Trained me to please real Men? Mommy and Daddy and Their BDSM friends!
Well, everything my Superiors like to tell me...! But of course They know my soft and hard limits and wouldn't force me to go beyond the hard ones...!
Yes, for sure i do! As every true sissy should!
Tehe ... wherever i find nice things! i buy them at amazon or specalized shops like birchplaceshop but also in department stores or local shops. And especially it feels wonderful when the sales ladies or sometimes even the shops software system adresses me as a "Miss" ... it gives me the feeling to be true and to be seen as what i really am...
yours,
sissy moan
is this a scientific poll or anything like this? But anyway: just as there are real Men and real Women i am actually a "real" sissy ... and this is why i don't want to hide what i am. And when there are scientists who are interested in the sissy phenomenon i am more then ready to answer...!
nancyask said:
In fact i don't see it as cross dressing since i don't dress as a real Woman would do. i actually prefer pink sissy clothes and frillies and so on that a real Woman wouldn't wear ... well, i think a slut would do but that is just because she loves to serve the expectations of Men. But i think that at least my chastity cage isn't anything that could be misunderstood.
nancyask said:
i don't know whether this counts but maybe i started being sex years old when i realized that i wasn't a real girl! Before i was actually raised like a girl ... and of course i always used to see my Mommy as my role model...
nancyask said:
my first "love" was one of my Mommy's nighties and some of Her silky panties ... and when i was nine they became my first "wet love" as well...! So to use a term of my sissy friend dollyanne i became some kind of pantysexual instead of hetero or homosexual ... or bi or whatever...!
nancyask said:
Uhm ... make me do what exactly...? Dress me as a girl first? Mommy! Taught me to be a real sissy? Mommy and Daddy! Trained me to please real Men? Mommy and Daddy and Their BDSM friends!
nancyask said:
Well, everything my Superiors like to tell me...! But of course They know my soft and hard limits and wouldn't force me to go beyond the hard ones...!
nancyask said:
Yes, for sure i do! As every true sissy should!
nancyask said:
Tehe ... wherever i find nice things! i buy them at amazon or specalized shops like birchplaceshop but also in department stores or local shops. And especially it feels wonderful when the sales ladies or sometimes even the shops software system adresses me as a "Miss" ... it gives me the feeling to be true and to be seen as what i really am...
yours,
sissy moan
I was 12 the first time I dressed. My older cousin lived with us and loved her slutty lingerie. From the moment I put her stockings panties and bra on I felt amazing. It felt so right. I dressed in hers and my mothers lingerie, heels, and outfits whenever I was home alone for the next 4 years. I had been attracted to women's legs in stockings for as long as I could remember, I realised the moment I put them on for the first time that I was attracted to them because I wanted to be them. I was however confused and thought something was wrong with me and confided in someone much older than me that I dressed in lingerie and it made me feel hotter and sexier than anything else ever could, I was 16 at the time. He said it was okay to feel that way and if I was comfortable to do so I should wear the lingerie that made me feel the sexiest under my clothes the next time I went to see him. I did and showed him what I looked like in it. He told me to leave my clothes off as we spoke. With a month and 2 more visits to him I was sucking his big cock while dressed and things progressed from there.
