I don't normally attend works office parties but when they decided to have a school disco themed party i thought this might be fun.The chance to see some of the women in schoolgirl outfits was too good to miss.(I even said to someone afterwards,when asked if i wanted tickets to the next party,that they are not my cup of tea.She said 'You came to the school disco'.To which i replied'I did.But that was only because i wanted to see you in a schoolgirl outfit').I put on some small and stupidly tight shorts,a plain shirt and my old school tie.When i got there i took in the sights.One of the women,w... Continue»
By - Tex Lee
I discovered crossdressing in my early teens when I was once
using the bathroom I noticed my mothers red lipstick on the
bathroom counter. I opened the tube out of curiosity and
twisted out the red phallic looking lipstick and felt
compelled to put it on. I felt a strange and exciting sexual
arousal that I never felt before and soon was wearing
lipstick and masturbating every chance I got. Eventually I
started wearing my mom's and s****r's panties and bra, then
dresses, skirts and high heels. By the time I was 16 I
accumulated a nice little wardrobe of sexy bras, panties,
skirts and blouses make up. I naturally started thinking
what it would be like to suck a cock dressed as a hot slut,
and maybe even take a hard one up my little pussy-ass. This
lead to practicing on broom sticks, sausages and fingering
my ass during masturbation.how embarrassing!
I've been dressing for 20 years now (I am 33) and I've been
with several partners, both men and women while dressed like
a slutty babe but the truly magic event I wish to tell you
about here is completely true and it is an account of my
very first time with a man.
In the summer of 1990 I just turned 17 and my mom and s****r
went away for the weekend to check out colleges for her and
left me alone in the house for the weekend.
I was so very excited on Friday I skipped school and around
noon set out my clothes for the evening and took a nice long
bubble bath. I poured myself a glass of wine and powdered
myself with Chanel No5 powder and slipped into a bra and
panties, filling the bra with several pair of nylon
stockings. I was in heaven sitting there at the dressing
table, taking my time to apply my make-up. Being an art
student I guess I have a flair for it and as you might
suspect love the dramatic, sexy, and slutty look. I applied
foundation to my face, neck and chest then using a brown
pencil drew in perfectly arched eyebrows.
I used a light blue eyeshadow over my eyelid extending to my
brow and a darker blue for the crease on my eyelid. Next I
outlined my upper and lover lid with a soft black pencil
then came several coats of rich black mascara. My penis was
rock hard and I felt those familiar butterflies of arousal
the entire time I was putting on my make-up and I was just
floating on air. Another glass of wine followed then a
little more mascara and I started my lipstick. I love
wearing lipstick and I carefully outlined my already full
lips with a brick red pencil, paying particular attention to
a perfectly shaped and slightly exaggerated Cupid's bow and
full lower lip. I then filled my lips in with a very creamy
red lipstick and topped it off with some clear gloss. My
cock was bobbing with excitement at this point!
I had two wigs I bought and decided on the long and curly
blonde one. I shook it to fluff it out then slipped it on
and lightly brushed it into shape. I decided on a pair of
thigh high black fish net stockings with a say up lace top,
black high heel pumps, 5" tall. Difficult to walk in but oh
so sexy! I wore a tight, stretchy black mini skirt and a
tight white blouse with a wide collar. I spread the collar
and kept it unbuttoned showing off just a peek of my bra and
my miniskirt showed just a peek of my lace top stockings.
I admired myself in the mirror for a long time and a couple
of glasses of wine later I was pretty high and very, very
My told me if I needed anything in their absence to call
Dennis, our next door neighbor.
Dennis was in his late 30's, divorced, and A nice guy. He
helped out my mom a lot with house repairs and he and I went
to a couple of baseball games together. I didn't know it at
the time by mom asked Dennis to look after me while she was
gone and I was sitting at the kitchen table when the door
At first I thought it was my Mom returning early and I felt
the bl**d rush from my face and I jumped up to run but there
was no place to go. The side door out the kitchen was right
next to my escape to the living room and I froze.
Dennis looked as startled as me as we stood there staring at
each other for what seemed like forever but I am sure was
just a few seconds.
He spoke first, apologizing for walking in, then saying he
was Dennis from next door and asking where Jimmy was. I
couldn't speak and didn't know what to say so I just started
to cry. He came closer and asked if it was me and I think I
managed a yes, and please don't tell my mom between sobs.
Much to my surprise he put his arms around me and comforted
me, saying it was OK and I didn't have to worry about
telling my mom.
I calmed down some I suppose and he lifted my chin up and
looked me in the eye. He said I looked really great and sexy
and he understands. He made me feel better and after a few
minutes told me to sit down and we could talk about this. He
saw the wine bottle on the counter and poured us a glass and
we talked a little longer and he somehow seemed very
comfortable with me dressed like this, which in turn made me
feel relaxed and comfortable.
I excused myself to go to the bathroom and realized by
aroused state was returning. I fixed my mascara some and re
applied my lipstick, teased my hair a little and returned to
the kitchen. Dennis was now standing and leaning against the
kitchen counter as I returned and I hugged him again to
thank him for understanding. When we hugged I was surprised
by his penis being hard and I felt it press against my
stomach. I felt a shot of electricity run thru my body. I
hesitated for a second or two then dropped my right hand and
felt his penis thru his jeans. He protested but only for a
brief second, then told me I make one sexy bitch. Encouraged
by his reaction I unbuckled his belt, unsnapped his jeans
and reached in for my prize. It was the first cock I ever
felt besides mine and it felt so different. I struggled to
get it out so Dennis slid down his jeans and underpants and
I knelt down in front of him, pulling his pants down to his
Dennis's cock was larger than mine, with veins running the
length and it had a large prominent head, and maybe eight
inches long. I put my right hand around the shaft and kissed
the tip leaving a red lip print on it. It twitched in my
hand and Dennis let out a soft hiss. I kissed the shaft, and
then licked his balls lightly feeling his pubic hair
sticking to my lipstick.
I kissed my way back to the tip of his cock and with my
mouth right in front of him he pushed forward driving his
penis into my open mouth. I placed both of my hands on
either side of his hips and Dennis fucked my virgin mouth. I
remember thinking I liked sucking cock and I knew I was
hooked from this moment on. Dennis's breathing was getting
deeper and I felt his cock grow even more in my mouth. He
put a hand on the back of my head and I suddenly felt the
urge to gag but I didn't. I didn't even realize he was
cumming at first, until I tasted a warm musky taste in my
mouth. Dennis shot several times then he put his hand around
his penis and jacked off into my wide open mouth until he
As he was catching his breath he said this was not good and
we shouldn't be doing this and I replied by sucking the tip
of his softening cock once more.
I stood up and headed off to the bathroom where I once again
reapplied my lipstick, pulled up my stockings a bit, dabbed
on some perfume and removed my panties. I hadn't cum yet and
wanted more and hoped Dennis did too.
When I returned from the bathroom I was happy to see Dennis
sitting on the couch in the living room, with his pants back
on but his shirt off, two fresh glasses of wine on the
coffee table and a joint in his hand! He lit the joint and
passed it to me as I sat down next to him. By the time we
finished smoking the joint and our wine I was cuddled up
next to him, running my hands thru his chest hair and
talking. I guess because of the buzz we had, Dennis
confessed that my mom and he had sex a few times. I
suspected that and k**ded him about having sex with our
whole f****y and my s****r better look out.
Dennis noticed my "clitty" poking out from beneath my skirt,
which I purposely let ride up, and casually stroked it as we
talked. It felt so nice just being with Dennis and I hoped
it would never end and told him so. He responded by kissing
me softly, my first time kissing a man. I reached into
Dennis's jeans and massaged him as we kissed, and he
massaged my penis too. After a few minutes Dennis asked if
we had any baby oil and I told him to take off his jeans and
I would be right back.
Another quick lipstick fix in the bathroom and I squirted
some baby oil on my fingers and massaged it into my ass.
When I returned to the living room Dennis had his pants off
and was kneeling in front of the couch. I sat down in front
of him on the couch and poured baby oil on his cock and
massaged it in. Dennis placed his hands on my ass and I laid
back and lifted my legs onto his shoulders.
I felt his cock at the entrance of my ass and Dennis told me
to just relax as he gently pushed forward. It hurt a little
at first then we both felt it almost pop inside.
Dennis held still for a few moments as my new pussy got used
to a cock in there and it was me that made the first move,
swiveling my hip around his cock.
Dennis squirted a little more baby oil down there then on my
cock and started fucking my ass as he was stroking my limp
dick. Don't know when I have a cock in my ass by "clitty"
goes limp, but it still feels good having it stroked. In
just a few minutes Dennis was fucking me good and I felt
myself start to cum. As I was cumming I really got off on
watching him fuck me with my skirt bunched up around my
waist and stocking clad legs and high heels over his
shoulders. I seemed to cum from deep inside and it lasted
forever! I never came like that before and maybe never
since! Dennis continued to pound me, my ass being numb by
now I never wanted him to stop. Eventually his body
stiffened and he held his breath and he filled my hot little
hole with his cum!
It was now pretty late so after talking a short while and
agreeing we need to do this again, Dennis hugged and kissed
me and went back over to his place. I curled up in a ball on
the couch and slept there all night.