I was an awkward sexually frustrated and confused teenage boy growing up in a rural part of the country
who had a secrete fetish for women’s clothing for as long as I can remember so
much so that the Sears catalog was a form of great pleasure and almost to the
point of being pornography for my obsessed young mind. One day strictly by a
matter of circumstance I found myself alone with my beautiful mothers vast
assortment of underwear and lingerie I couldn’t resist the temptation and
decided to become one of the models I so lusted after and dressed in a black
bullet bra and matching panty girdle with a pair of seamed thigh high stockings.
I was in a lustful state of bliss to finally know what it felt like. Do in part
to my lack of caution and my mothers’ astute powers of observance I was caught
after the fact. Much to my pleasant surprise, she was not angry but quite the
contrary overwhelmingly supportive. So much so she was giving me a personal one
on one sexual education impressing on me that my feelings as much as publicly
taboo at the time were perfectly normal and beautiful. To say my mother was
progressively way ahead of her time was a gross understatement. Not a feminist
in way shape or form she was more of a live and let live nonjudgmental person.
As I stated I was sexually awkward, inexperienced, and confused so much, so I
had never successfully masturbated. Hard to believe a teenage boy who didn’t
know the proper way to jerkoff but thankfully my mom showed me how. It may
sound strange but to say it was one of the most beautiful experiences of my
life does not do it justice. After some sexually promiscuous horseplay her
being the constant joker that she was, she was teasing me to the point of tears
by tickling me while unbeknownst to me at the time dry humping me she finally
relented to my begging when she stopped, after a few seconds she said just lay
here while I draw your bath. I asked a bath I always take showers, mom. She said
not today a young lady has to enjoy a bubble bath every now and then especially
when she shaves her legs. I just looked at her with that look of astonishment,
really, she said yes, I told you I had a special day planned a girl’s day
together. What just happened wasn’t planned, completely spontaneous fun but not
planned. She got up from the bed and kissed me on the cheek and said it will be
ready in a few minutes just relax. I did just that rerunning the entire
experience over in my head and could feel myself becoming aroused again when
she called out bath time.
I got up from the bed lust
filled and feeling a new indescribable sort of sexual confidence if you will
from an incredible display of ejaculation that even wowed and impressed my mother.
I walked into the bathroom with my semi flaccid penis unsupported swinging with
every step. My mom was sitting on the edge of the tub looking at my swinging
member saying oh my now that’s no way for a lady to act and of course I looked
down at it and half shamelessly almost said I was sorry but caught myself
because I knew she would have corrected me so I was learning so I just looked
at her and shrugged my shoulders. She smiled and laughed and told me to get in
the tub. I had only faint memories of bathing in the tub way back when so this
was like a new experience and I have to admit the hot water and bubble-filled the tub felt really good and inviting. My mom proceeded to wash my back and places
I couldn’t reach with an oversized sponge lathering me up from head to toe and
it felt great. While bathing we talked and she asked me so how did it feel, I
was a little lost as she could tell by the look on my face, she said your first
time masturbating and cumming. I responded it was great I never knew anything
could feel like that and then my inexperience so looked at her and said
cumming? She laughed and said yes that what it’s called when you finally cum,
release the sperm from your penis. Oh, I’ve heard guys talk about it at school
but never knew what they were talking about. I asked her if women did, she gave
a slight laugh and said yes, we cum do we cum and it feels as great for us as
it does for you. I was all questions now oh really yes really, she replied. I
asked her so do you masturbate mom. She hesitates a bit I guess taken aback by
her son asking if she got off. She smiled and said yes, I do Buddy I
masturbate, and it does feel great. I’ll show you. I responded oh and she said
yes so you know how to please a lady someday. Looking at me smiling saying
guess what I looked at her and she smiled and said you know while you were
stroking your penis, I was pleasuring myself at the same time. I couldn’t
believe the conversation she smiled and said yes because watching you and
helping you with your first time was so exciting, I couldn’t help myself. I had
recalled her hand between her legs but couldn’t see more than that.
She smiled and said I told you I had a special
day planned for us girls so let’s get on with it shall we, we’ll talk more
about masturbation later ok. I said ok mom, she said ok now let’s shave your
legs. I was shocked, to say the least, and had some hesitation all rushing
through my mind at the speed of light, wait I’m a guy we don’t shave our legs,
what if the guys see them, wait, it summertime no one will see them oh crap
what if I wear shorts. My mom with her mom radar in full swing said you don’t
have to if you don’t want to, but me never wanting to disappoint my mom who I
loved so much didn’t give it a second thought and said now it's fine and lifted
one of my legs out of the water. Mom smiled and supported my leg by the ankle
with one hand sprayed shaving cream on my leg with the other lathering up and
down my leg. She then took her razor and gently stroked my leg removing what
little hair I had, not being an overly hairy kid or maybe verging on the edge
of being less hairy than normal it wasn’t long before my leg was smooth as a
baby’s bottom. She smiled and said very nice, as she cupped some bath water and
rinsed it off, ok now your turn as she handed me the razor. The look on my face
was one of horror and what the fuck do I do. She smiled and softly said relax
I’ll guide you. She instructed me to gently pull the razor towards me just
letting it glide over my legs allowing the blade to do its job and reminding me
to keep cleaning it off in the bathwater. I completed my task without cutting
myself and was quite proud. She ran her hand over my leg when she did, I could
feel the stubble. She handed me back the razor and lathered me up again and
said one more time. I completed my task and this time it was as smooth as my
other leg. She smiled and said nice job young lady and held her hand out for
the razor which I placed in her hand. She said ok now arms up I was like what?
She said time to shave your armpits I did as requested of me she took a look
and said never mind we can skip that part.
She said ok let’s get you out
of there and get you all prettied up not knowing what was in store for me had
me both terrified and excited, she took me by the hand and led me to her
freshly painted bedroom and sat me down at her dressing table. She places both
hands on my shoulders while standing behind me looking at me in the mirror
saying You know Buddy I really do love this new color don’t you think, I smiled
and said glad you like it mom it's nice, and she smiled and said if you weren’t
such an adventurous inquisitive young man we wouldn’t be having “this” special
moment. I smiled and said I guess not. She reached around from behind me and
give me a big hug and kissed me on the cheek and told me how much she loved me,
and I reciprocated. She said I just want you to know that at any time if this
gets uncomfortable just say the word and we can stop. I thought for a
nanosecond and said no mom I’m good, I’m really having fun. The truth was my fun
was fueled by my raging hormones and lustful hidden obsession with women’s
clothing and especially undergarments. She began brushing my long brown hair
with her big silver hairbrush but not as I did. She held it in her hand and
brushed it and combed it and did a bunch of different things with it. She
sprayed something in it and continued her handy work. I couldn’t believe my eyes,
but I was being transformed into a young lady. She parted my hair to one side
and gave it a little curl and a wave a 100% feminine looks completely departed
from my parted down the middle pseudo young rock n roller. The entire time my
mom was behind me naked except for her radiant smile every once in a while her
large breast would rub against my shoulders and head and I wanted so much to
suck on them and kiss them as I had done earlier I don’t really think at the
time this was done to tease me but rather because of our newfound comfort
level, I could by it she was enjoying herself and this made me feel even better
about what was happening. She smiled and asked what did I think and I smiled
back and said I think I look pretty good. Good, she said your downright
beautiful, ok now for a little makeup you're. She came around front and bent over in
front of my pulling stuff from the draws and I had all I could do from reaching
out and fondling her nice round ass and kissing her ass cheeks, my god it was
so inviting I could feel my cock pulsing. She was standing in front of me and
bent over at the waist so she could work on my makeup and her breast were
hanging there like fruit right for the picking, I reached out and cupped her
large breast in my hand gently she smiled and just raised her eyebrows saying
you really like them don’t you, my almost instantaneous response was oh yes mom
I do I really do well I can't help you grow your breast but we'll figure out something, this had me intrigued. She began with a little eyeliner, some blush, and finally
some lipstick. A very soft pink. Mom wasn’t a big makeup-wearing only on
special occasions when she got all dressed up. I asked about the other stuff I
had seen her wear and she said oh that when I really feel like getting dressed
up, you’ll see one of these days we’ll dress you all up for a night on the
town. I had no idea what she meant by this and just sat silently as she did her
thing. She stood back to admire her work and by doing so gave me a full view of
my new self in the mirror. I was in shock, to say the least. I looked like me
but not me I looked like oh I guess my sister who I didn’t have. I had an
athletic build and still sort of do today. Not overly muscular, just toned no
big masculine shoulders, taller and leaner so the transformation looked natural
and not at all freakish or out of place, being a let developer I guess I had no facial hair, not even a little peach fuzz which normally frustrated me but today this was an extreme advantage making me all the more feminine looking I actually looked like a teenage girl
and a pretty one at that. Mom was beaming she said ok now let’s get you
dressed.
She handed me a white bra,
nothing overly sexy more modest than the bullet bra I had tried on, but it
still looked sexy a white smooth material with lace trim around the edges of
the cups. As her mother intuition was always working, she said yes, I know not
as sexy as the one you picked for your first time but it more every day and
looks very nice on you dear don’t you think she asked I agreed and said yes mom
I like it I really do, she said well now Buddy lets do a little something to help you fill out your bra. She then took bunches of tissue paper and filled the cups so outwardly I had the appearance of having full pair breast after all I was wearing one of her bras, there much better don't you agree. Looking in the mirror I marveled at my full cups and knew this is who I was meant to be I so wanted to be a girl and I truly believe it was the feminine image of me looking back at me is what assured me that being a crossdresser was great and who knows what the future would hold She smiles and told me to stand up and handed me a pair
of white satin panties here honey put these on, and I did as requested they
felt really nice soft n smooth. She had me dress in a pair of white shorts and a
buttoned blue blouse. I dressed and looked at her for approval she smiled and
took the ends of the top and tied them up exposing my navel I had seen her wear
outfits like this my whole life, but this now took on a special sexiness. Mom
put on a pair of white capri pants and a red blouse, she was wearing a black bra
that could just be seen supporting her massive cleavage as she had it button-down just enough, she finished our dressing with a touch of perfume. Just
enough to smell like a lady and not a French whore We left the bedroom and went
down and had lunch we sat around outside on the front porch swing enjoying a
nice summer day having girl talk as she said with her favorite daughter. The
day was one of the nicest memories I have and before long it was time to go in
for dinner but then she said oh it’s so nice out, let's go for a drive. I was
like mom what are you nuts or something. She looked at me and smiled saying
gotcha. The entire dinner time we laughed, and she teased me saying the look on
my face was priceless. She told me you know honey you look so feminine that no
one would know, but they sure would notice a sweet young girl with a big pair of knockers, I glanced down at my chest and actually blushed, saying mom, she laughed gotcha. I said you really think so she smiled and said yes, I really
think so but like I told you we’ll keep this our special secrete and winking at
me for now. This was the beginning of me becoming the daughter my mom never had but swore she was carrying a girl who knows maybe she was right.<br><br>Let’s go have a lite dinner and then get changed into our nightclothes.
Immediately after dinner without even doing the dishes or any of the evening chores she looked at me
and said let go get changed. I didn’t hesitate and said sure let's go so off to
the bedroom we went. When we got to the bedroom she went into her closet and
came out with a box, she smiled and said I bought this and have never worn it
I’d like you to especially seeing how we have the same taste. I opened the box
to find a pair of black satin panties with a leopard print panel, a matching bra, and a garter belt I was speechless she smiled and said try it on honey, it may
not fit great, but we’ll have to get you some of your own soon enough. I rushed
to get my white outfit off so I could try on this new hot looking get up. She
stopped me saying a lady doesn’t throw her clothes on the floor we lay them on
the chair or place them in the hamper for now you can leave everything on the
side table. I did as I was told and picked up after myself and set my clothes
aside. I then began getting dressed first my bra and mom was impressed by my
method of hooking from the front and turning it around etc. she smiled and said
you’re a fast learner, I then slipped on my panties, and then she grabbed my
wrist and said nope panties on last, what if you have to pee, she looked at me
and said don’t think like a man and just pull them aside ladies pee sitting
down garter belt and stockings first. So, I slipped on the garter belt and mom
helped me with my stockings and helped to hook them to the garters and lastly,
she handed me the panties.
She smiled and said my you
look beautiful; she fixed my hair a little and had me freshen up my lipstick
and handed me a black robe she had in her closet and said I’ll see you downstairs
we can watch a little tv if you like. I said sure mom and donned the long robe
and headed downstairs my young cock straining at the material of my black
sating panties. Well, I wasn’t downstairs more than ten or fifteen minutes when
I heard mom walking down the stairs and into the living room, she was wearing a
long white robe that flowed like something you’d see a movie star wear at least
that was my vison of her. She had on a robe, but it was open revealing her
purple nightie the lace trimmed cups
barely covered her large breast supported by two thin spaghetti straps and that
was It unknown to me until later on that my mom hardly ever wore panties even
when she dressed for work. She realized they had a purpose abut she liked the
feeling of freedom she got by not wearing undies but a wearer of stockings and
garters she always looked classy but under her well-dressed ensemble she was
pantiles. She came over and sat next to me on the couch and we made small talk
about the show we were watching which clearly my mind wasn’t on. She poured me
a glass of wine and we sipped as we watched the show, I kept glancing at her
admiring how beautiful she looked and smiled. She looked at me and said what, I
replied mom you're beautiful, no mom you're hot! You’re really hot, she laughed and
said you're just trying to make me feel good, I said no mom I swear you’re so hot
I and hesitated short of saying I want to fuck you. She said what honey I said
no I have to treat you like a lady, she smiled and said oh baby you’re so
beautiful I love you and I replied I love you too mom. With that, she leaned in
and kissed me. That was it, she had knowingly or unknowingly started the launch
sequence. I kissed her back but not on the cheek or soft peck I just had no
control and kissed her right on the mouth. She was taken aback at first but
reciprocated with a tender but full-on mouth kiss. We continued to kiss each
other she began to stroke my hair; I instinctively softly stroked her face. Not
having the faintest idea of what I was doing I just did what came naturally.
I pulled her in closer to me and she didn’t
resist so I began softly and gently exploring her perfect body with my hands. I
knew her breasts were ok as she had allowed me to touch them before, I gently
caressed her massive melons gently lifting them and supporting them with my
hand through the sensuous feeling satin material as we continued to kiss. Her
hands were running the full length of my stocking covered legs and she moved up
to my bra covered breast rubbing and massaging them and she began playing with
my nipples. I could not believe I was making out with my mom; her breathing
began to increase, and she pulled away and said softly and gently honey, softly
and gently. I continued to kiss her as directed my hand had never left her
breast and I continued rubbing them through the purple satin material. I began
kissing her more and more I could hear her breathing increase and she pulled
away and leaned her head back with her eyes closed. Again, acting on sheer
instinct I began to kiss her neck. I could feel her begin to melt as her body
became more relaxed, I pulled at her straps exposing her big massive left
breast. She began to moan oh Buddy oh yes, oh yes. I began to squeeze her
breast and continue kissing her neck. She would confess to me later on that I
had found her weak spot, kissing her neck turned her to jelly as she put it.
She took my hand by the wrist and said mommy has two boobs remember and I
didn’t hesitate to message and expose her right tit and rolled her nipple
through my fingers. Without warning, she pulled away from my kissing and grabbed
me and kissed me on the mouth but this time she stuck her tongue deep in my
mouth. At first, I gagged, and she said its ok baby breath through your nose, I
did as she suggested and gave into my animal instinct and stuck my tongue in
her mouth and we French kissed I was to later find out that’s what it was
called. I can only attribute it to the fact that my cock was restrained somewhat
by my outfit that I hadn’t pulled it out and tried to fuck her even though I
had no idea what fucking was all about at that time. She began to fondle my
cock through my panties, she began stroking its outline up and down squeezing
it. She slipped her hand in the top of my panties and said remember I told you
panties last and proceeded to pull them down exposing my hard cock that now
sprung to attention. She pulled them down the rest of the way and I kicked them
off. She began softly stroking my cock and told me to kiss her again. I did as
she asked and began kissing her but not as hard and intense at first, she just
took my hand and I instinctively placed it on her breast and began massaging
it, she told me to come from underneath as if I was lifting it up and run my
hands across her nipples. The more I did this the more excited she got and the
harder her nipples became. We continued this petting for maybe five minutes or,
so she had been increasing her stroking
of my cock occasionally squeezing the shaft. With her free hand, she pushed me
back off her tits and said lay back and relax baby. With one fluid motion, she
slid off the couch and was kneeling in front of me marveling at my cock and its
head that was glistening with precum. Without warning, she engulfed my cock into
her mouth. I was paralyzed with shock and extreme pleasure. Her mouth felt like
warm velvet on my swollen cock. She began to take it deeper and deeper into her
mouth almost swallowing me whole, then she would slide back up the shaft until
just the tip was on her lips. She continued doing this and looked up at me marveling
at what was taking place and I could see the pleasure and joyfulness in her
eyes. She continued to suck my cock and she stroked it with one hand as she
sucked it and squeezed my balls with the other. I winched a little and she
released her grip. I said no mommy please don’t stop.<span style="mso-spacerun:yes"> </span>She was to tell me later just the word please
mommy don’t stop got her totally wet. Her Squeezing my balls was just to let me
know that even though a lady may have your cock in her mouth she is still in
control.
She continued her rhythmic sucking of my cock
up and down and sucking harder and harder, she removed it from her mouth and
licked up and down the entire shaft with her tongue she then put me back in her
mouth but only the head as she sucked on it for all she was worth and began to
stroke my rock hard shaft, she later told me she was fully impressed at how
much control I had and had expected me to blow my load (my words not here’s) in
a few minutes. She then fulling engulfed my rock hard swollen cock fully and
began bobbing up and down on it faster and faster. My entire body began to shake
and tense up and without warning I began
a cum explosion into her mouth. She intently swallowed as much as she could
when she pulled back off of me, I was still shooting cum from the head of my
cock and she went back down on my throbbing pumping member doing her best to
catch every last drop but I couldn’t help spraying her face as my cock was
pulsating like a bass drum with every beat cum spurt from the head. She sucked
me until there was not a single drop of cum left in my balls. I was totally
spent and was drained of every single once of energy, when she removed my still
semi-hard cock from her mouth, she looked down at her bare tits to see I had
shot some cum on them as well. She laughed and said holy fuck Buddy that was
beyond impressive. She knelt between my legs for a minute looking up at me
saying are you ok, I nodded I was fine are you ok I asked she smiled and said
I’m great and as if on que my cock began to pulsate I saw a shocked look on her
face and began to clench my ass cheeks as if to help pump me back up to full
strength. She said Holy crap you’re getting hard again my god you’re an animal,
I never she hesitated saying and got to her feet took me by the hand and said
lets go upstairs and have some more fun now its mommy’s turn. As we walked up
the stairs my pulsating cock bouncing with each step I didn’t resist my
temptation like before and reached out and squeezed her ass, she squealed oh my
Buddy and before she could protest I kissed her ass<span style="mso-spacerun:yes"> </span>and sucked on it, she squealed and laughed saying
you’re an animal now let’s go.
who had a secrete fetish for women’s clothing for as long as I can remember so
much so that the Sears catalog was a form of great pleasure and almost to the
point of being pornography for my obsessed young mind. One day strictly by a
matter of circumstance I found myself alone with my beautiful mothers vast
assortment of underwear and lingerie I couldn’t resist the temptation and
decided to become one of the models I so lusted after and dressed in a black
bullet bra and matching panty girdle with a pair of seamed thigh high stockings.
I was in a lustful state of bliss to finally know what it felt like. Do in part
to my lack of caution and my mothers’ astute powers of observance I was caught
after the fact. Much to my pleasant surprise, she was not angry but quite the
contrary overwhelmingly supportive. So much so she was giving me a personal one
on one sexual education impressing on me that my feelings as much as publicly
taboo at the time were perfectly normal and beautiful. To say my mother was
progressively way ahead of her time was a gross understatement. Not a feminist
in way shape or form she was more of a live and let live nonjudgmental person.
As I stated I was sexually awkward, inexperienced, and confused so much, so I
had never successfully masturbated. Hard to believe a teenage boy who didn’t
know the proper way to jerkoff but thankfully my mom showed me how. It may
sound strange but to say it was one of the most beautiful experiences of my
life does not do it justice. After some sexually promiscuous horseplay her
being the constant joker that she was, she was teasing me to the point of tears
by tickling me while unbeknownst to me at the time dry humping me she finally
relented to my begging when she stopped, after a few seconds she said just lay
here while I draw your bath. I asked a bath I always take showers, mom. She said
not today a young lady has to enjoy a bubble bath every now and then especially
when she shaves her legs. I just looked at her with that look of astonishment,
really, she said yes, I told you I had a special day planned a girl’s day
together. What just happened wasn’t planned, completely spontaneous fun but not
planned. She got up from the bed and kissed me on the cheek and said it will be
ready in a few minutes just relax. I did just that rerunning the entire
experience over in my head and could feel myself becoming aroused again when
she called out bath time.
I got up from the bed lust
filled and feeling a new indescribable sort of sexual confidence if you will
from an incredible display of ejaculation that even wowed and impressed my mother.
I walked into the bathroom with my semi flaccid penis unsupported swinging with
every step. My mom was sitting on the edge of the tub looking at my swinging
member saying oh my now that’s no way for a lady to act and of course I looked
down at it and half shamelessly almost said I was sorry but caught myself
because I knew she would have corrected me so I was learning so I just looked
at her and shrugged my shoulders. She smiled and laughed and told me to get in
the tub. I had only faint memories of bathing in the tub way back when so this
was like a new experience and I have to admit the hot water and bubble-filled the tub felt really good and inviting. My mom proceeded to wash my back and places
I couldn’t reach with an oversized sponge lathering me up from head to toe and
it felt great. While bathing we talked and she asked me so how did it feel, I
was a little lost as she could tell by the look on my face, she said your first
time masturbating and cumming. I responded it was great I never knew anything
could feel like that and then my inexperience so looked at her and said
cumming? She laughed and said yes that what it’s called when you finally cum,
release the sperm from your penis. Oh, I’ve heard guys talk about it at school
but never knew what they were talking about. I asked her if women did, she gave
a slight laugh and said yes, we cum do we cum and it feels as great for us as
it does for you. I was all questions now oh really yes really, she replied. I
asked her so do you masturbate mom. She hesitates a bit I guess taken aback by
her son asking if she got off. She smiled and said yes, I do Buddy I
masturbate, and it does feel great. I’ll show you. I responded oh and she said
yes so you know how to please a lady someday. Looking at me smiling saying
guess what I looked at her and she smiled and said you know while you were
stroking your penis, I was pleasuring myself at the same time. I couldn’t
believe the conversation she smiled and said yes because watching you and
helping you with your first time was so exciting, I couldn’t help myself. I had
recalled her hand between her legs but couldn’t see more than that.
She smiled and said I told you I had a special
day planned for us girls so let’s get on with it shall we, we’ll talk more
about masturbation later ok. I said ok mom, she said ok now let’s shave your
legs. I was shocked, to say the least, and had some hesitation all rushing
through my mind at the speed of light, wait I’m a guy we don’t shave our legs,
what if the guys see them, wait, it summertime no one will see them oh crap
what if I wear shorts. My mom with her mom radar in full swing said you don’t
have to if you don’t want to, but me never wanting to disappoint my mom who I
loved so much didn’t give it a second thought and said now it's fine and lifted
one of my legs out of the water. Mom smiled and supported my leg by the ankle
with one hand sprayed shaving cream on my leg with the other lathering up and
down my leg. She then took her razor and gently stroked my leg removing what
little hair I had, not being an overly hairy kid or maybe verging on the edge
of being less hairy than normal it wasn’t long before my leg was smooth as a
baby’s bottom. She smiled and said very nice, as she cupped some bath water and
rinsed it off, ok now your turn as she handed me the razor. The look on my face
was one of horror and what the fuck do I do. She smiled and softly said relax
I’ll guide you. She instructed me to gently pull the razor towards me just
letting it glide over my legs allowing the blade to do its job and reminding me
to keep cleaning it off in the bathwater. I completed my task without cutting
myself and was quite proud. She ran her hand over my leg when she did, I could
feel the stubble. She handed me back the razor and lathered me up again and
said one more time. I completed my task and this time it was as smooth as my
other leg. She smiled and said nice job young lady and held her hand out for
the razor which I placed in her hand. She said ok now arms up I was like what?
She said time to shave your armpits I did as requested of me she took a look
and said never mind we can skip that part.
She said ok let’s get you out
of there and get you all prettied up not knowing what was in store for me had
me both terrified and excited, she took me by the hand and led me to her
freshly painted bedroom and sat me down at her dressing table. She places both
hands on my shoulders while standing behind me looking at me in the mirror
saying You know Buddy I really do love this new color don’t you think, I smiled
and said glad you like it mom it's nice, and she smiled and said if you weren’t
such an adventurous inquisitive young man we wouldn’t be having “this” special
moment. I smiled and said I guess not. She reached around from behind me and
give me a big hug and kissed me on the cheek and told me how much she loved me,
and I reciprocated. She said I just want you to know that at any time if this
gets uncomfortable just say the word and we can stop. I thought for a
nanosecond and said no mom I’m good, I’m really having fun. The truth was my fun
was fueled by my raging hormones and lustful hidden obsession with women’s
clothing and especially undergarments. She began brushing my long brown hair
with her big silver hairbrush but not as I did. She held it in her hand and
brushed it and combed it and did a bunch of different things with it. She
sprayed something in it and continued her handy work. I couldn’t believe my eyes,
but I was being transformed into a young lady. She parted my hair to one side
and gave it a little curl and a wave a 100% feminine looks completely departed
from my parted down the middle pseudo young rock n roller. The entire time my
mom was behind me naked except for her radiant smile every once in a while her
large breast would rub against my shoulders and head and I wanted so much to
suck on them and kiss them as I had done earlier I don’t really think at the
time this was done to tease me but rather because of our newfound comfort
level, I could by it she was enjoying herself and this made me feel even better
about what was happening. She smiled and asked what did I think and I smiled
back and said I think I look pretty good. Good, she said your downright
beautiful, ok now for a little makeup you're. She came around front and bent over in
front of my pulling stuff from the draws and I had all I could do from reaching
out and fondling her nice round ass and kissing her ass cheeks, my god it was
so inviting I could feel my cock pulsing. She was standing in front of me and
bent over at the waist so she could work on my makeup and her breast were
hanging there like fruit right for the picking, I reached out and cupped her
large breast in my hand gently she smiled and just raised her eyebrows saying
you really like them don’t you, my almost instantaneous response was oh yes mom
I do I really do well I can't help you grow your breast but we'll figure out something, this had me intrigued. She began with a little eyeliner, some blush, and finally
some lipstick. A very soft pink. Mom wasn’t a big makeup-wearing only on
special occasions when she got all dressed up. I asked about the other stuff I
had seen her wear and she said oh that when I really feel like getting dressed
up, you’ll see one of these days we’ll dress you all up for a night on the
town. I had no idea what she meant by this and just sat silently as she did her
thing. She stood back to admire her work and by doing so gave me a full view of
my new self in the mirror. I was in shock, to say the least. I looked like me
but not me I looked like oh I guess my sister who I didn’t have. I had an
athletic build and still sort of do today. Not overly muscular, just toned no
big masculine shoulders, taller and leaner so the transformation looked natural
and not at all freakish or out of place, being a let developer I guess I had no facial hair, not even a little peach fuzz which normally frustrated me but today this was an extreme advantage making me all the more feminine looking I actually looked like a teenage girl
and a pretty one at that. Mom was beaming she said ok now let’s get you
dressed.
She handed me a white bra,
nothing overly sexy more modest than the bullet bra I had tried on, but it
still looked sexy a white smooth material with lace trim around the edges of
the cups. As her mother intuition was always working, she said yes, I know not
as sexy as the one you picked for your first time but it more every day and
looks very nice on you dear don’t you think she asked I agreed and said yes mom
I like it I really do, she said well now Buddy lets do a little something to help you fill out your bra. She then took bunches of tissue paper and filled the cups so outwardly I had the appearance of having full pair breast after all I was wearing one of her bras, there much better don't you agree. Looking in the mirror I marveled at my full cups and knew this is who I was meant to be I so wanted to be a girl and I truly believe it was the feminine image of me looking back at me is what assured me that being a crossdresser was great and who knows what the future would hold She smiles and told me to stand up and handed me a pair
of white satin panties here honey put these on, and I did as requested they
felt really nice soft n smooth. She had me dress in a pair of white shorts and a
buttoned blue blouse. I dressed and looked at her for approval she smiled and
took the ends of the top and tied them up exposing my navel I had seen her wear
outfits like this my whole life, but this now took on a special sexiness. Mom
put on a pair of white capri pants and a red blouse, she was wearing a black bra
that could just be seen supporting her massive cleavage as she had it button-down just enough, she finished our dressing with a touch of perfume. Just
enough to smell like a lady and not a French whore We left the bedroom and went
down and had lunch we sat around outside on the front porch swing enjoying a
nice summer day having girl talk as she said with her favorite daughter. The
day was one of the nicest memories I have and before long it was time to go in
for dinner but then she said oh it’s so nice out, let's go for a drive. I was
like mom what are you nuts or something. She looked at me and smiled saying
gotcha. The entire dinner time we laughed, and she teased me saying the look on
my face was priceless. She told me you know honey you look so feminine that no
one would know, but they sure would notice a sweet young girl with a big pair of knockers, I glanced down at my chest and actually blushed, saying mom, she laughed gotcha. I said you really think so she smiled and said yes, I really
think so but like I told you we’ll keep this our special secrete and winking at
me for now. This was the beginning of me becoming the daughter my mom never had but swore she was carrying a girl who knows maybe she was right.<br><br>Let’s go have a lite dinner and then get changed into our nightclothes.
Immediately after dinner without even doing the dishes or any of the evening chores she looked at me
and said let go get changed. I didn’t hesitate and said sure let's go so off to
the bedroom we went. When we got to the bedroom she went into her closet and
came out with a box, she smiled and said I bought this and have never worn it
I’d like you to especially seeing how we have the same taste. I opened the box
to find a pair of black satin panties with a leopard print panel, a matching bra, and a garter belt I was speechless she smiled and said try it on honey, it may
not fit great, but we’ll have to get you some of your own soon enough. I rushed
to get my white outfit off so I could try on this new hot looking get up. She
stopped me saying a lady doesn’t throw her clothes on the floor we lay them on
the chair or place them in the hamper for now you can leave everything on the
side table. I did as I was told and picked up after myself and set my clothes
aside. I then began getting dressed first my bra and mom was impressed by my
method of hooking from the front and turning it around etc. she smiled and said
you’re a fast learner, I then slipped on my panties, and then she grabbed my
wrist and said nope panties on last, what if you have to pee, she looked at me
and said don’t think like a man and just pull them aside ladies pee sitting
down garter belt and stockings first. So, I slipped on the garter belt and mom
helped me with my stockings and helped to hook them to the garters and lastly,
she handed me the panties.
She smiled and said my you
look beautiful; she fixed my hair a little and had me freshen up my lipstick
and handed me a black robe she had in her closet and said I’ll see you downstairs
we can watch a little tv if you like. I said sure mom and donned the long robe
and headed downstairs my young cock straining at the material of my black
sating panties. Well, I wasn’t downstairs more than ten or fifteen minutes when
I heard mom walking down the stairs and into the living room, she was wearing a
long white robe that flowed like something you’d see a movie star wear at least
that was my vison of her. She had on a robe, but it was open revealing her
purple nightie the lace trimmed cups
barely covered her large breast supported by two thin spaghetti straps and that
was It unknown to me until later on that my mom hardly ever wore panties even
when she dressed for work. She realized they had a purpose abut she liked the
feeling of freedom she got by not wearing undies but a wearer of stockings and
garters she always looked classy but under her well-dressed ensemble she was
pantiles. She came over and sat next to me on the couch and we made small talk
about the show we were watching which clearly my mind wasn’t on. She poured me
a glass of wine and we sipped as we watched the show, I kept glancing at her
admiring how beautiful she looked and smiled. She looked at me and said what, I
replied mom you're beautiful, no mom you're hot! You’re really hot, she laughed and
said you're just trying to make me feel good, I said no mom I swear you’re so hot
I and hesitated short of saying I want to fuck you. She said what honey I said
no I have to treat you like a lady, she smiled and said oh baby you’re so
beautiful I love you and I replied I love you too mom. With that, she leaned in
and kissed me. That was it, she had knowingly or unknowingly started the launch
sequence. I kissed her back but not on the cheek or soft peck I just had no
control and kissed her right on the mouth. She was taken aback at first but
reciprocated with a tender but full-on mouth kiss. We continued to kiss each
other she began to stroke my hair; I instinctively softly stroked her face. Not
having the faintest idea of what I was doing I just did what came naturally.
I pulled her in closer to me and she didn’t
resist so I began softly and gently exploring her perfect body with my hands. I
knew her breasts were ok as she had allowed me to touch them before, I gently
caressed her massive melons gently lifting them and supporting them with my
hand through the sensuous feeling satin material as we continued to kiss. Her
hands were running the full length of my stocking covered legs and she moved up
to my bra covered breast rubbing and massaging them and she began playing with
my nipples. I could not believe I was making out with my mom; her breathing
began to increase, and she pulled away and said softly and gently honey, softly
and gently. I continued to kiss her as directed my hand had never left her
breast and I continued rubbing them through the purple satin material. I began
kissing her more and more I could hear her breathing increase and she pulled
away and leaned her head back with her eyes closed. Again, acting on sheer
instinct I began to kiss her neck. I could feel her begin to melt as her body
became more relaxed, I pulled at her straps exposing her big massive left
breast. She began to moan oh Buddy oh yes, oh yes. I began to squeeze her
breast and continue kissing her neck. She would confess to me later on that I
had found her weak spot, kissing her neck turned her to jelly as she put it.
She took my hand by the wrist and said mommy has two boobs remember and I
didn’t hesitate to message and expose her right tit and rolled her nipple
through my fingers. Without warning, she pulled away from my kissing and grabbed
me and kissed me on the mouth but this time she stuck her tongue deep in my
mouth. At first, I gagged, and she said its ok baby breath through your nose, I
did as she suggested and gave into my animal instinct and stuck my tongue in
her mouth and we French kissed I was to later find out that’s what it was
called. I can only attribute it to the fact that my cock was restrained somewhat
by my outfit that I hadn’t pulled it out and tried to fuck her even though I
had no idea what fucking was all about at that time. She began to fondle my
cock through my panties, she began stroking its outline up and down squeezing
it. She slipped her hand in the top of my panties and said remember I told you
panties last and proceeded to pull them down exposing my hard cock that now
sprung to attention. She pulled them down the rest of the way and I kicked them
off. She began softly stroking my cock and told me to kiss her again. I did as
she asked and began kissing her but not as hard and intense at first, she just
took my hand and I instinctively placed it on her breast and began massaging
it, she told me to come from underneath as if I was lifting it up and run my
hands across her nipples. The more I did this the more excited she got and the
harder her nipples became. We continued this petting for maybe five minutes or,
so she had been increasing her stroking
of my cock occasionally squeezing the shaft. With her free hand, she pushed me
back off her tits and said lay back and relax baby. With one fluid motion, she
slid off the couch and was kneeling in front of me marveling at my cock and its
head that was glistening with precum. Without warning, she engulfed my cock into
her mouth. I was paralyzed with shock and extreme pleasure. Her mouth felt like
warm velvet on my swollen cock. She began to take it deeper and deeper into her
mouth almost swallowing me whole, then she would slide back up the shaft until
just the tip was on her lips. She continued doing this and looked up at me marveling
at what was taking place and I could see the pleasure and joyfulness in her
eyes. She continued to suck my cock and she stroked it with one hand as she
sucked it and squeezed my balls with the other. I winched a little and she
released her grip. I said no mommy please don’t stop.<span style="mso-spacerun:yes"> </span>She was to tell me later just the word please
mommy don’t stop got her totally wet. Her Squeezing my balls was just to let me
know that even though a lady may have your cock in her mouth she is still in
control.
She continued her rhythmic sucking of my cock
up and down and sucking harder and harder, she removed it from her mouth and
licked up and down the entire shaft with her tongue she then put me back in her
mouth but only the head as she sucked on it for all she was worth and began to
stroke my rock hard shaft, she later told me she was fully impressed at how
much control I had and had expected me to blow my load (my words not here’s) in
a few minutes. She then fulling engulfed my rock hard swollen cock fully and
began bobbing up and down on it faster and faster. My entire body began to shake
and tense up and without warning I began
a cum explosion into her mouth. She intently swallowed as much as she could
when she pulled back off of me, I was still shooting cum from the head of my
cock and she went back down on my throbbing pumping member doing her best to
catch every last drop but I couldn’t help spraying her face as my cock was
pulsating like a bass drum with every beat cum spurt from the head. She sucked
me until there was not a single drop of cum left in my balls. I was totally
spent and was drained of every single once of energy, when she removed my still
semi-hard cock from her mouth, she looked down at her bare tits to see I had
shot some cum on them as well. She laughed and said holy fuck Buddy that was
beyond impressive. She knelt between my legs for a minute looking up at me
saying are you ok, I nodded I was fine are you ok I asked she smiled and said
I’m great and as if on que my cock began to pulsate I saw a shocked look on her
face and began to clench my ass cheeks as if to help pump me back up to full
strength. She said Holy crap you’re getting hard again my god you’re an animal,
I never she hesitated saying and got to her feet took me by the hand and said
lets go upstairs and have some more fun now its mommy’s turn. As we walked up
the stairs my pulsating cock bouncing with each step I didn’t resist my
temptation like before and reached out and squeezed her ass, she squealed oh my
Buddy and before she could protest I kissed her ass<span style="mso-spacerun:yes"> </span>and sucked on it, she squealed and laughed saying
you’re an animal now let’s go.