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Licktysplit · 11-02-2020, 01:25 AM

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This is the 100% true story of how I got in touch with my feminine side and life of crossdressing, I owe it to my wonderful mother  <img src="https://janetscloset.com/forums/images/smilies/heart.png" data-sceditor-emoticon=" Heart

" alt="

" title="

"> <img src="https://janetscloset.com/forums/images/smilies/heart.png" data-sceditor-emoticon=" Heart

" alt="

" title="

">    I’ve always been a closet crossdresser for
as long as I can remember, when I first hit puberty like any other young boy my
hormones were on a rampage but not in the typical way sure I enjoyed looking at
women attracted to their breast like a moth to a flame, the shape, the
bounce I loved it all looking for hours at the lingerie pages of the Sears
catalog was a favorite past time of mine and other pubescent teen males but my interest was different I
envied women for being able to wear all those sexy bras and lingerie and I had
an equal obsession with stockings and panty girdles as well. So, one summer day
my mom who I loved dearly a much kinder gentler nurturing soul than my asshole
macho old man tasked me with an important job. I was more than willing to help
her and asked what she wanted me to do. She said she wanted my help painting
her bedroom and I would have to move all the furniture out and put it into the
spare room, I agreed and told her I would take care of it. She suggested for me
to take all the draws out first so everything would be easier to move made
sense. I started on my task and low and behold I came across her underwear
draw. This was like hitting pay dirt for me, I had struck gold she had a
collection of bras that I had no idea she ever wore and how would I. Longline
bras, lace bras see-thru bras my young cock was as hard as a rock but when I
came across her bullet bras I instantly could feel my cock pulsing and I now
had a whole new image of my mom she was one hot sexy lady. Seeing pictures of
her when she was growing up, I instinctively knew she had to be wearing some of
these bras in those photos it was of course the style back then. So, the
overwhelming compulsion to try one on was more than I could handle, and I
succumbed to my lust. I peeled off my white T-shirt and slipped one on and
fought like hell trying to fasten the clasps behind my back, then I got the
bright idea to slip my arms out of the straps and turn it around and fasten it
in front then spin it around and slip my arms through. Something I see my own
wife do as well as many of the women I’ve been with.<o:p></o:p>

<o:p> </o:p>

 I admired myself in
her full-length mirror and the large mirror that was on her dresser, I looked
hot in my book but my breast were somewhat lacking so I looked for something to
stuff the cups with  I rummaged through
her draws and came up with some white cotton socks that I knew she wore when
gardening and working outside. I succeed in filling out the cups of the bullet
bra which by the way I still have to this day locked away. Well, I looked good
but not quite good enough, so I rummaged through some of her other draws until
I came across her panty girdles. My God! she must have had twenty or twenty-five of them. I found a black one that looked like it matched the bra and
removed my jeans and started to slip it on over my tighty whitey underwear and
thought no this isn’t how you look like a woman stupid and slipped them off
kicked them to one side of the room and stepped into the girdle and pulled it
up wiggled my hips as I pulled until it was finally up just over my tummy just
as I had seen in the pages of the lingerie section. I once again admired myself
and I looked even better but still not complete. Stockings! I needed stockings
I continued my search and instantly found them a pair of nude seamed stockings
I slipped them on and the sensation of the nylon against my legs was
indescribably euphoric. I took care not to tear them and sat on the big wing
backed chair my mom obviously used for dressing and slowly rolling them up
until they were fully up my thighs and I clasp them to the garters hanging from
the bottom of the girdle. It took me one attempt and I had them all hooked up,
little did I realize back then but looking through the pages of the Sears
catalog lady’s lingerie section was in a way a crossdressing training manual
for me. I went for the total look and tried on a pair of her heels which fit my
feet way back then but when I tried to stand and walk, I almost killed myself.
Looking back, I could just have imagined tripping hitting my head being knocked
unconscious to be found that way funny now but a horrifying thought back then. <o:p></o:p>

 So, I decided to
admire myself wearing the heels by laying on the bed striking different poses.
I looked much better now I looked hot, being a kid of the 60’s I had long hair
just like everyone else, I grabbed mom’s big silver brush and brushed my long
auburn hair as close to her style as I could get it. My mom and my aunt often
comment I had beautiful hair and that girls wished they had hair like mine, an
added bonus. I took one look at myself in the mirror and could instantly feel
my cock straining at my girdle. I lay back down striking a few more possess and
almost as if on autopilot my hand reached under my girdle and I found my now
leaking precum cock. I was amazingly hard truly something to be admired by both
genders and sexual orientations. I began stroking and squeezing my balls and I
increased my pace until I was feverishly pumping it and lifting my hips off the
bed as if I was trying to meet an imaginary lovers’ thrusts. I orgasmed for
what seems like fifteen minutes continuously pumping cum from my balls until I
collapsed in an unexplainable euphoric erotic state of completion. I knew right
then and there I was destined to be as much of a woman as I could possibly be
but living in that time period in the part of the country where I grew up I
most likely would have been lynched or beaten to death by all the redneck
asshole s who I wanted no part of anyway. I was laying back fantasizing about
being fucked by a man when all of a sudden, the phone rang, and it seemed it
was even louder than ever as it was an alarm that I had committed a crime
against nature and would be dammed all to hell. When I reached for the phone it
was then I realized I had a right hand full of cum and fumbled for the phone
with my left hand. When I answered it was my mom on the other end of the phone
and I instantly felt guilty as hell and wanted to undress as fast as possible. <o:p></o:p>

<o:p> </o:p>

<o:p> </o:p>

Why? I now ask myself but just a guilty teenage boy's
reaction, I guess. She asked how my job was going I said fine mom almost have
the room empty total BS I was barely started. She said that good sweetie I’m
not coming home the regular time I’m working overtime and then I’m going out
with your aunt Martha, so I’ll be home late. She told me to fix myself
something for dinner there was always plenty in the frig. I told her I'd be fine
and then I spotted the big wet stain on the comforter and thought oh fuck! Ah
mom I spilled something on the comforter she asked what not paint I hope I said
no something I was drinking (I only wished I was drinking cum). She said that’s
ok take it off the bed and I’ll wash it when I come home. I protested and said
no I’ll do it, mom, she said your such a good boy, (right now a bad girl maybe)
She gave me instructions and I stripped if off the bed and went about washing
it. The funny thing is I didn’t even think about removing any of my garments
and walked freely through the house and down to the laundry room and did the
wash came back and finished cleaning out the room the entire time dressed in my
sexy outfit. I made myself dinner dressed sat at the dining room table ate and
then and went about finishing up everything I was tasked to do and figured it
was time to get undressed but not before one well-deserved wank. This time I
lay on the couch, closed my eyes and thought about my fantasy lover fucking my
brains out like I had heard my older brother and cousins talk about to local
floozies. I came in one gigantic explosive orgasm but this time I was prepared
with a towel to clean up my mess. I reluctantly removed everything being
careful to place things back where I remembered they came from so as not to be
discovered. I gathered up my boy clothes and went and took a shower got dressed
and sat down watching TV. About an hour later I heard the door open and my mom
called to me when she walked through the door. She kissed me and said well
how’d you do, I just said check it out I had her bedroom totally cleaned out
molding all taped floors covered ready to go. She smiled and said great job I’m
off tomorrow would you mind helping me paint, without hesitation I responded
sure mom no problem even though in the back of my mind I was supposed to go
play ball with my friends but never being one to disappoint my mom I decided to
forgo sandlot baseball for a chance to spend the day with mom. She said ok time
for bed, then she laughed and said well now this might be a problem as her
bedroom was empty and the spare room was full of her furniture. She said oh
well looks like the couch for me tonight. I blurted out why don’t you sleep in
my room mom, Chuck is away at school, she smiled and said sure why not. I went
upstairs to get changed and hopped into bed. When my mom walked upstairs in
stood in the doorway, she was wearing a white linen nightie that was backlit by
the hall light and I could clearly see the entire outline of her perfect body
especially her large pendulous breast being the tit man that I have become she
was at least a 38DD or better and her nipples were poking at the thin material. Her breast were my fixation for as
long as I can remember and probably the reason for my love of large breasted
women. She got in my brother's bed and pulled the covers up and then said it’s
too hot for a blanket and just lay on top of the sheets she rested her head on
her hand and said so pal what's new. I was holy crap mom had that infamous mom
radar shit working how the hell did she know. I stammered a bit and said, nothing mom. She said well we hardly ever get to be alone to talk about stuff
you know like girls, cars, sports. I was relieved oh wait mom what about me
wearing your underwear the voice in my head said. Ah, not much you know I gave
her a quick rundown about so and so’s brother got a new Chevy and this and
that. What about girls I said what about them none are interested in me
sometimes I think it would be easier to be a girl than a guy you know mom. She
laughed and said it’s never easy being a teenager, the entire time my perverted
little mind had me staring at her breast imagining her wearing those pieces of
lingerie I had come across. What I wouldn’t give to see mom dressed like I was.
She said ok bud time for bed we have a long day tomorrow, but we’ll have fun. <o:p></o:p>

<o:p> </o:p>

Morning came and mom was gone downstairs making breakfast,
she called to me from the bottom of the stairs, breakfast sweetie Ok mom be
right there a few minutes later I headed down to the kitchen and sat down to
eat with mom a treat I didn’t get to do alone hardly at all anymore. After
breakfast she said well you did a great job in the room, we’re ready to go and
you washed the comforter and hung it up to dry a nice job, I said thanks, mom.
Then she looked at me and smiled and held up the black panty girdle and said if
you’re going to wear my stuff you can at least wash it. I was dumbfounded one
freaking time and I got caught. I hung my head and said I’m sorry mom I won’t
but before I could finish, she said it's ok sweetie I understand. I looked up
trying to fight my shame, she said no really it's ok and came over and kissed me
on the forehead. Look you’re at a very confusing age right now and your mind
has no idea what your body is doing so I’m ok with you experimenting as long as
it’s in the privacy of our home and you keep this our secrete. I said ok mom
our secrete I swear. She said ok now let me show you how to wash this. Ok, mom
and we headed for the laundry room I said wait and ran back to where her
dresser draws were piled up and retrieved the bra and stockings. She smiled and
said my, my! you must have looked sexy I just put my head down in embarrassment
she said hey your my kid you had to have looked like a million bucks. We went downstairs
to the laundry room and she held up the bra saying you have good taste like me,
this was one of my favorites. I looked and said was inquisitively she said I’m
an old married lady I don’t dress like that anymore. I said I bet you still
look, great mom. She said well your father doesn’t seem to think so anymore. I
wanted to say that’s because he’s an asshole but held my tongue as I was
taught. She smiled and said thanks bud maybe we’ll see one of these days.<o:p></o:p>

<o:p> </o:p>

She proceeded to teach me the proper way to was lingerie
such as the bra and cum stained girdle I had worn. We then went back to our
painting project, I was busy working when she said I’m going to make us lunch,
it will be ready in a few minutes. After about fifteen minutes she called me
to come for lunch but make sure you go wash up first. I went into the bathroom
there hanging on the towel rack was a blue shiny satiny top and shorts. She
called did you find them, yes, I answered back she laughed and said well, put
them on I want to see how you look. I did as my mom had requested and put on
the outfit. When I came out of my mom had a big smile on her face said my you look
cute, then she tugged at the top and adjusted it so it sat properly and when
she adjusted the shorts, I could feel my member starting to grow. She said oh
these will not do tugging at my white cotton briefs. She said follow me and we
went to her pile of draws in the spare room and she rummaged through her panty
draw and pulled out a pair of nylon bikini full-back panties she said here put
these on, she watched as I sat on the bed and slipped the shorts off and pulled
off my underwear and I thought my now less than flaccid cock was going to
spring to attention, so I quickly pulled up the panties and adjusted my
manhood, she laughed and said that’s something I never have to worry or be
embarrassed about and handed me the shorts and I slipped them on. She smiled
and said much better now let’s go have lunch. <o:p></o:p>

<o:p> </o:p>

While we were eating, she asked me how I felt. I said good
mom actually she said great, so you feel sexy I said yeah, I guess. She smiled
and said it can be fun being a girl you’ll see. I smiled and said yeah, I guess
it can be. Mom said let’s finish putting the room back together and then figure
out what we girls want to do tonight. I worked tirelessly for the rest of the day
dressed as my mom had wanted. She was wearing a similar style pair of black
shorts and a white top tied up, so her belly button was exposed. As we put
stuff back and hung up pictures etc. She said so you think your mom still looks
good. I said heck yeah mom you're gorgeous, all my friends think you're pretty too.
She smiled and said oh do they now I said yes mom they do. Hmm, you make me feel
really good sweetie. I said your welcome mom. Ok let’s finish up so we can find
something fun to do, how about I do your hair later. I said my hair she said
yeah, it’s something girlfriends do to each other. I said ok sure why not.
Thinking to myself wow this is unbelievable. I worked as fast as I could to get
everything finished in anticipation of what lay in store for me. <o:p></o:p>

<o:p> </o:p>

boots66 · 11-03-2020, 07:00 AM

Hello, Lickitysplit. Sounds like a very cool mom. She probably enjoyed sharing your secret with you. That's a very special bond, especially as a teenager, where most times, teens don't want anything to do with mom and dad, the rebellious years. Loved the story. Thanks for sharing. All the best. Maxine

Licktysplit · 11-03-2020, 07:10 AM

(11-03-2020, 07:00 AM)boots66 Wrote: Hello, Lickitysplit.  Sounds like a very cool mom.  She probably enjoyed sharing your secret with you.  That's a very special bond, especially as a teenager, where most times, teens don't want anything to do with mom and dad, the rebellious years.  Loved the story.  Thanks for sharing.  All the best.  Maxine

Maxine thank you very much for the kind words I will be sure to post part 2 oh btw love the boots

boots66 · 11-03-2020, 07:29 AM

I look forward to it. I envy your picture. HOT!!!

Licktysplit · 11-03-2020, 11:40 PM

(11-03-2020, 07:29 AM)boots66 Wrote: I look forward to it.  I envy your picture.  HOT!!!

Thank you for your too kind Who am working so hard to get back to

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