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One of my earliest sexual memories is having a bath with my mother when
I was about xxxx. We lived in a large, older two-story house in a quiet
neighbourhood of the city. Our main bathroom had an old-fashioned
claw-footed tub that you could fill up to your chin with hot, soapy
water. Mom had me sitting between her legs, facing away from her. She
had a bar of soap and, while she rubbed it gently over my body with one
hand, she gave me a soap-suds massage with the other. I could feel her
hard, erect nipples pressing against my back as both her hands slipped
slowly and gradually down towards my crotch. When she took my little
penis in one hand and started to gently soap it up with the other, it
immediately began to swell into an erection. At the same time, she began
to nuzzle and kiss the back of my neck and I could feel her slowly
brushing her nipples back and forth across my back. I recall that I had
the most delicious feelings go through me while she was doing these
things to me and that I was very disappointed when she stopped, although
she must have played with my little cock for at least five minutes on
that occasion. I recall bathing with her often from then until I was
about xxx or xxxxx and getting the same treatment each time we bathed
together.

Mom was a widow. She had come from a fairly well-off f****y and, after
graduating from university, met and married my father. Mom’s parents
were both dead, but she and her s****r were left enough money so that
neither was required to go out to work if they lived modestly. My father
died a couple of months before I was born. Mom used his life insurance
and part of her inheritance to buy our house and invested the rest to
provide her with an income, while she stayed home to raise me.

Aunt Julie, who is a year younger than my mother, married uncle Tim just
after graduating from university. They were both elementary school
teachers at the time and lived across town from us. Mom and I used to
spend part of the summer with them at their cottage on White Lake. Mom
and aunt Julie, who are now stylishly grey, were both dark brunettes in
those days, but Julie’s eyes are violet and mom’s are dark brown. Aunt
Julie is a little slimmer than mom and an inch taller at five-seven.
Even now, in later life, they are very pretty, sexy ladies with long,
shapely legs and firm breasts. Uncle Tim is a slightly-build six footer,
with medium brown hair that is grey at the temples.

About the same time that mom started fondling me in the bath, she began
to do other things that aroused me. Every afternoon was nap time for
both of us. One day, instead of putting me to bed in my own room on the
second floor, mom took me into her first-floor bedroom. It was a
beautiful feminine room, with curtained french doors opening onto a
private garden at the back of the house. I recall standing by the bed
while she undressed me then, standing there naked, seeing her smiling as
she undressed in front of me while watching my reaction. It was the
first time I remember seeing her completely naked other than during bath
time. I’m sure I was wide-eyed with wonder, and she appeared very
pleased with my response. I had a very sensitive erection that was
twitching up and down as I stared at her beautiful body. My little
dickie had started to get hard as soon as I got a glimpse of her pretty
nylon and lace undies when she slipped out of her skirt and blouse. She
really seemed pleased at that and reached over and tickled it tenderly
as she kissed me softly on the lips and said ‘why, what a little man you
are becoming. We’ll have to show you what to do with your dickie now
that you’re getting bigger, won’t we?’

At that, mom went over to her closet and took out a long, pale blue,
nylon nightgown which she slipped over her head, shivering with
excitement as it slid down over her swollen nipples. Still standing
naked by the bed, I watched as she took a shorter, aqua gown from the
closet and beckoned me with her hand to come to her. I walked over to
her and, as I stood there in front of her, she d****d the silken gown
over my shoulders. It pretty well covered me, and the silky nylon felt
good against my skin and gave me a particularly pleasant sensation in my
erect penis as it brushed the tip of it. I remember mom saying ‘doesn’t
that feel good darling?’ as she then deliberately brushed the gown
against the tip of my penis another three or four times then tickled my
bottom through it for a few seconds. I nodded ‘yes’ as I beamed with the
pleasure of the sensation.

Mom pulled down the bedcovers, wrapped the aqua gown around me, then
picked me up and lay me in the bed before climbing in herself and
pulling the covers over us. She drew me close to her, cuddling me up
against her warm, lovely body. My face was on a level with her breasts
and I could smell her perfume and see her breasts and nipples outlined
through her thin gown. She had me cradled in the crook of her left arm
and had both hands free. I will never forget what happened next.

Mom reached down and lifted the hem of her nightie up to her waist, then
I felt her give a little shiver of excitement and moan softly as she
slid her right hand down between her legs. She moved her hips around
rhythmically for a few minutes, purring softly. Then, very slowly and
tenderly, she began to massage my back and shoulders with the fingertips
of her left hand through the soft fabric of the gown I had wrapped
around me. I didn’t know what was happening, but it felt wonderful so I
just lay there enjoying it. Mom had always been very physically
affectionate, so I must have imagined that this was just another way of
her showing her love for me. Gradually her hand crept downwards until
she was fondling and tickling my little bottom. My ecstacy increased by
the moment. My pleasure response went off the scale as I felt the
fingertips of her right hand begin to tease my throbbing little pecker
through the silken gown while she was still tickling my bottom with the
other.

Soon we were both making sounds of sensual pleasure and mom had started
to masturbate my dickie with the same motions she used on it in the tub,
only this time the nylon nightgown took the place of the soap. What a
sensation it gave me! Like all normal boys, I had always enjoyed
touching and rubbing my penis, and loved it when mom masturbated me in
the tub, but I had never experienced a thrill like this.

After a few minutes, mom pushed away from me a little and started to
fondle my cock with her left hand, while masturbating herself with her
right. I watched and listened in awe as she moved and moaned and then
finally came with a cry of passionate release. She had been fondling my
stiff little pecker all the while she was masturbating and clutched it
firmly but gently as she quivered through her orgasm.

Afterwards, she drew me to her, hugging, caressing, and kissing me
tenderly as she crooned ‘oh my darling, that was soooo good, soooo
good.’ Then, because it was nap time, she held me close, her hand
cupping my penis and balls through the silk, while we both drifted off
to sl**p. After that, we often had our daily nap together. Some were
similar to the first time but others were far more exciting, like the
one I will tell you about later.

Every night, after washing me and helping me into my flannel pajamas,
mom would read me a story and tuck me in for the night. The routine
changed the night of the day we had our first nap together though. After
I had washed up and climbed into bed with my bedtime story book, mom
said ‘wait here dear, I have a little gift for you’ and went out of my
room and downstairs to hers. She returned about ten minutes later,
dressed in a lace-trimmed white nylon gown and negligee set, and
carrying the same aqua nightgown she had put on me that afternoon.

Sitting down in the easy chair beside the bed and showing me the gown in
her hand, she said’I know you really like the feel of this dear, so I
want you to have it. Remember this afternoon when I told you it was time
to show you what to do with your dickie now that you are bigger? Well I
know you like to touch and play with it already, and I think thats
wonderful, but there are other nice things you can do to it as well and
mommy is going to teach you one right now. Put away your book and pull
down the covers darling.’ I obeyed her instructions then, as I lay there
with my soft little penis peeking out of the fly of my pajamas, mom
reached over, slipped my pajama pants all the way off and tossed them on
top of the laundry hamper in the corner. She then arranged the nylon
nightie over my naked crotch and legs in several layers.

I lay there uncomprehending, but already beginning to respond sexually
to the touch of the sensuous fabric. When she was satisfied with the
arrangement, she took both of my hands and placed them on the silken
gown between my legs. Then, smiling lovingly and watching my face for my
reactions, she proceeded to move my hands in a circular motion,
demonstrating how I should massage myself with the nightgown. It felt
just as good as before and I very quickly got an erection, which mom
took great pains to encourage with her own gentle fingertip teasing
while showing me how to tease myself through the silky nylon with my own
fingertips. After several minutes of coaching me she said ‘now dear, you
keep doing that while I read you your story’. She then pulled up the
covers as I continued masturbating with my new plaything, saying ‘you
should do that every night darling, its very soothing and will help you
sl**p.’ It was pretty hard to concentrate on the story that first night,
but I certainly enjoyed myself in other ways. I slept with that first of
many nightgowns between my legs for a long time, using it to fondle and
tickle my pecker as it grew year-by-year.

Over the next little while, mom encouraged me to try masturbating with
some of her panties, slips, and nighties that were made of silk and
satin, but I always preferred the nylon ones.

Once mom had introduced me to the sensuous pleasures of nylon lingerie
and taught me to masturbate more creatively, I really looked forward to
our nap times and even to my bedtime. Needless to say, it was
continually drilled into me (gently but firmly) that our ‘playtimes’
were ‘our little secret’ and no one else must ever know about it. I was
a quiet, secure person who enjoyed playing alone anyway, so I wasn’t
often in contact with other people unless I was in the company of my
mother or my aunt and uncle. We always did our errands, banking, grocery
shopping and trips to the library in the morning and, since I wasn’t
attending school, most of our afternoons were free. I say most, because
once or twice a week, mostly on weekends, aunt Julie or uncle Tim, or
sometimes both would come to visit. On those days I had my afternoon nap
alone in my room, while mom entertained her guests downstairs so I would
not be disturbed by any noise they might make. More about that later!

As I said, I always looked forward to nap times with my mother. One
afternoon, when I was about xxx mom said ‘darling, I think its time we
taught you something new. You’re getting to be a big boy now and there
is something you can do for me that would make me very happy. Would you
like to make me happy darling?’ ‘OK’ I answered, ‘what do you want me to
do?’ ‘Just be quiet and let me make you feel good dear. What I’m going
to do won’t hurt and I think you will like it as much as I do.’

We had just come into her bedroom and were both just finishing getting
undressed for our nap time. I stood naked waiting for her as she slipped
into her white nylon negligee. She then took the matching gown out of
the closet and came over to me. After sitting me on the edge of the bed
she knelt down in front of me and began massaging me all over with the
silky white nylon gown, concentrating her efforts on my penis and
thighs. Her gorgeous breasts and erect nipples were in full view through
the diaphanous negligee and my penis soon throbbed into a swollen pink
and purple erection.

When my dickie was as big as she could make it, mom took the gown and
d****d it over my shoulders, covering me almost completely. She slid her
hands behind me, cupping my bottom, then she bent over and began to
gently lick my swollen pecker all over with long, slow strokes using the
tip of her tongue. I stared in amazement while spasms of pure delight
coursed through my body. Then, when I was wet all over from her licking,
she took my cock in her mouth and sucked it tenderly, up and down, up
and down, folding her tongue around it as she did so, and gripping it
gently with her lips. Mom sucked my dickie for about ten minutes that
first time then took me to bed, where she fondled me as usual while she
masturbated to orgasm beside me.

Our life wasn’t all sex mind you! Mom and I did other things together
and I spent a fair amount of time with my aunt Julie and uncle Tim. Mom
had taught me to read and write by the time I was xxxx and was great at
doing arts and crafts type stuff with me. She also took me to the
movies, on educational trips to museums and other places of interest,
and on vacation every summer to the cottage. Aunt Julie would sometimes
take me on a day trip to the park or zoo, and uncle Tim occasionally
took me fishing or for a hike in the woods.

When I reached school age, mom had decided that she was quite qualified
to educate me at home with the help of my aunt and uncle who were both
teachers, and so I started a daily routine of schoolwork in the morning
and recreational time in the afternoon. Evenings were spent reading or
sometimes watching TV, although we were not big fans of TV. There were
much more interesting things to do. Weekends were free for errands,
chores around the house, and more recreational activities.

I was too old for an afternoon nap by this time, but mom still enjoyed a
nap some afternoons and so our sexual activity continued unchanged until
I was about xxxxxxxx, though not as regularly as before. After mom fell
asl**p in the afternoon, I would usually go off and play or read. Often,
I would continue to masturbate on my own until I got bored or fell
asl**p myself. Sometimes I would get up and quietly open mom’s closet or
her dresser and take out a pair of nylon panties, a slip, or a nightgown
and masturbate with it, putting it back as it was when I was finished.

This wasn’t too difficult, as mom’s lingerie was just loose and unfolded
in her drawers, or on hangers in her closet. If mom knew about this, she
never let on at the time. The look and feel of her pretty, lacy silken
undies and other lingerie made my heart pound and my head throb with
excitement and I began to develop a real passion for them. I also began
to experience the desire to try them on.

I kept the nightie mom had given me under my pillow and masturbated
myself to sl**p with it nearly every night, but I had never made myself
come, I didn’t even know what an orgasm was. We didn’t bathe together
anymore either, but mom was very open about her sexuality and liked to
‘show off’ by letting me see her nude or in her lingerie often. For some
reason mom had never mentioned the subject of orgasms to me, although
she certainly had no inhibitions about letting me see and hear hers.

One night, a few weeks after my xx birthday, having just gotten
into bed for the night, I was overcome with the desire to try on my
masturbation nightgown. Mom was downstairs reading, so I knew I wouldn’t
be disturbed. I threw off the covers and quickly doffed my pajamas.
Quivering with excitement and with my heart and head pounding, I reached
under my pillow and drew out the gown. My pecker, which had grown
considerably over the years, twitched in eager anticipation as, with
shaking hands, I unfolded my treasure and arranged it on the bed. I
picked it up and shivered myself into it as it dropped caressingly over
my body.

The sleeveless, calf-length, full-skirted, empire-waisted gown was pale
aqua in colour, with spaghetti shoulder straps. It had two layers of
extremely soft, silky nylon tricot, a thin, see-through outer one and a
thicker, opaque inner one, and it felt wonderful to have it on. I began
stroking and fondling my cock and nipples through the soft nylon. I was
standing in front of the dresser in my room. The sight of my reflection
in the mirror sent a thrill up my spine and propelled me to an even
higher level of excitement! I rubbed and tickled myself harder and
harder, faster and faster until I noticed with shock that my cock was
starting to feel kind of numb and tingly. I had never experienced this
feeling before, but I couldn’t control my excitement and desire at this
point and just kept on masturbating faster and faster. I thought I was
going to pass out from excitement when I came seconds later.

My first orgasm was overwhelming! Spasm after spasm jerked my body as
small spurts of thick, creamy white come shot out of my throbbing cock,
soaking the part of the gown wrapped around it. My knees shook and I
felt so weak that I had to sit down.

As I sat panting in my chair, the last dribbles of come leaking out onto
the gown as I massaged my now-flaccid cock, my first thought was that I
had done something to harm myself and how was I going to explain it to
my mom. Then, as the mind-numbing effect of the orgasm subsided, it
dawned on me that it must be something like the feeling mom got just
before she finished masturbating. But what was that stuff that came out
of my cock? Somehow, I had to find out what it was and if I was OK. I
got up and slipped out of my nightie, tucking it under my pillow before
putting on my pajamas and getting into bed. I immediately fell into a
sound sl**p, one of the best and most restful I can ever remember.

The next morning, as I came into my room after showering, mom was
starting to make my bed. She didn’t do it often, but it seemed to me
that on the days she did she always managed to be there when I had just
come out of the shower. I had a towel wrapped around my waist, but was
damp and naked otherwise. Anyway, there she was, my pillow in one hand
and the nightgown in the other. She noticed the cum stains on the gown
immediately and, turning to me with a combined look of concern and a
smile, said ‘oh my! I think we need to have a little talk dear.’ She
dropped the pillow and gown on the bed and walked over to me, putting
her arm around my shoulder, saying ‘Don’t worry darling, nothing is
wrong. I should have realized sooner that you should know about this
sort of thing. Get dressed while I make up the bed and we’ll talk about
it over breakfast.’

As we sat together in the breakfast nook, mom gave me a thorough
explanation of orgasms, and what happens when men and women ‘come’. ‘I’m
so happy for you darling’, she said as we got up from the table ‘you are
going to enjoy your sexuality so much more from now on now that you know
how to ejaculate, but I think you might want to have me wash your
nightgown more often now, or else try catching your come on a tissue so
its not so messy.’ All the rest of that morning, as I was studying my
lessons, I noticed mom eyeing me from time-to-time. I had never before
seen her look at me with such an open expression of what I now recognize
as lust, nor had her body language and movements seemed quite so
seductive and sensual before.

After lunch, mom came up behind me as I was sitting at the table
reading, placed her hands on my shoulders and her lips next to my ear
and whispered ‘come and keep me company this afternoon darling.’ Without
waiting for a reply, she kissed me gently on the cheek and took me by
the hand, leading me silently to her room. Closing the door, she turned
to face me, kissing me full on the mouth in a long, lingering, soft,
sexy kiss, with her hands gently clasping my head. I felt dizzy and
weak-kneed as she stepped back and began undressing me. Her fingers flew
as shirt buttons, belt and zipper came undone. In no time at all, I
stood naked before her look of unbridled lust. Our eyes met and locked.
I flushed with embarassment but was transfixed by her gaze.

She had on a baby-blue cotton shirtwaist dress, open at the neck to
reveal the top of a lacy bra of the same colour. She slowly undid the
rest of her buttons and her belt and shrugged the dress off, letting it
fall around her ankles. Stepping back out of it, she held my eyes with
hers as she stood there in her bra and matching lacy half slip. Slowly
wriggling out of the silken nylon slip, she tossed it to me, saying
‘make yourself hard for me darling’. I needed little encouragement at
that point and began to massage my already swelling cock with the slip
as she undid her bra and tossed it in the corner. Her gorgeous breasts
and inviting pussy had my full attention as she slipped her silky blue
panties down her nylon-encased legs. Naked, except for her garter belt
and stockings, she started to fondle her tits with both hands, tickling
and teasing her nipples, while watching my throbbing, swollen cock
grow. Her right hand drifted down to her pussy and she began to
masturbate too, matching my hand move for move while continuing to
fondle her tits with her left hand.

‘Oh my darling, you get me so horny and excited when I watch you playing
with your beautiful, young, hard cock. I’ve waited for this moment so
long darling. Now we can be together the way I’ve always wanted us to
be. Come to me my darling!’ Stretching out her arms, she beckoned me to
her. I went willingly to her, dropping the slip, and we clung to one
another, our lips meeting in hungry passion, our bodies moving together
eagerly in a new-found level of pleasure.

Her hand found my hard cock, and holding it tenderly, she led me over to
the bed, sitting me down on the edge of it before kneeling in front of
me. Looking into my eyes, she began to lick and suck my cock with her
usual sensual technique, but her steady gaze of lust and love brought
the sensations to a new height of ecstacy for me. She licked and sucked
my cock until I began to feel like I might actually come in her mouth.

Sensing my rising excitement, she stopped, stood up and pushed me back
onto the bed, motioning that I should lay with my head on the pillows.
She then climbed on top of me, straddling my thighs, and bent down to
kiss me, her nipples brushing my chest and her hot, wet pussy pressing
against my swollen pecker. Forcing my mouth open with her probing
tongue, she slipped it into my mouth, darting her tongue in and out and
licking my lips in wild passion.

I could feel her wetness as she rubbed her clitoris against my cock and
it seemed like the most natural thing in the world when she reached
down, grasped my pecker, and slid it into her eager, throbbing pussy.
Wow! what a rush it was to finally be in her after all this time. Nature
and my body just took over from then on. She moved so sensuously and
naturally, all I had to do was follow her lead. ‘Fuck me my darling,
fuck me, fuck me, fuck me with your lovely, young, hard cock you
beautiful boy’, she said over and over again, kissing me hungrily and
flicking her tongue into my ears from time-to-time, shocking me to my
very core with her language and wild passion, but also stirring up my
own basic male instincts to respond to her needs.

She continued to move up and down and round and round on my rigid cock
in passionate rhythm, moaning and panting and pleading ‘fuck me my
darling, fuck me, fuck me, fuck me’, until she finally came, crying out
in ecstacy ‘oh yes, yes, oh yes, oooh, oooh, oooh yes darling, thats it,
thats it, fuck me, fuck me, fuck me darling!’

She collapsed on my chest, spent and drained, her face buried in the
pillow beside my head, my still-rigid cock buried in her still-throbbing
pussy, anxious to be satisfied. A minute passed before mom stirred. She
whispered in my ear ‘oh my darling that was wonderful, I love you so
much. Now let me make you come too.’

Sitting up, still straddling me, she began to move on my cock again,
slowly at first, then a little faster as we got together in our rhythm.
Soon my excitement was building to the critical point and I felt sure I
could come this way just as easily as I had when I masturbated the night
before. Mom looked so sexy with her wet, sensual mouth open and eager,
teasing me with her tongue by licking her lips seductively and, when she
took her tits in both hands and started fondling them as I fucked her, I
came almost instantly.

My second orgasm was even more powerful than the first. It felt like I
spurted buckets of come as the spasms went on and on. I couldn’t contain
myself, crying ‘oooh mom, oooh, oooh mom, oooh, oooh, oooh!’ until the
orgasm slowly ebbed. It was my turn to lay back spent and exhausted,
physically and emotionally drained, but totally satisfied in a way that
I had never imagined possible. Silently, smiling and kissing tenderly,
we crawled under the covers and, wrapped in each others arms, fell sound
asl**p until evening. We made love again that night, twice the next day,
and at least once a day for the next week, when finally mom suggested we
needed to get back to a regular routine for a while.

After she introduced me to sexual intercourse, and a short time later to
mutual oral sex, mom and I only masturbated together during foreplay,
although we each still did it regularly on our own. Now that I was
older, mom started going out alone to shop or to visit my aunt and uncle
more often, which was fine with me. My lessons and hobbies kept me busy
and I enjoyed having time to myself to pursue my ‘other interests’.

I had really started to enjoy wearing my nightgown whenever I got the
chance, and was even so bold as to sl**p in it some nights, but was very
careful to change before mom got up in the morning. Many times when mom
was out of the house for all or part of the day, I would go into her
room and dress up in her lingerie and sometimes her other clothes too. I
loved the thrill of wearing silky, sexy, feminine things, especially
when I had them on and masturbated while standing in front of a mirror,
and began to enjoy the sensations of my own budding feminine feelings. I
was always attracted to pretty girls and women, especially my mom and
aunt, but I was also turned on by women movie stars and pictures of
pretty women in magazines, so it felt kind of funny when I began to
realize how much I enjoyed acting and looking like a girl myself.

The only man I really knew well was Uncle Tim. He wasn’t ugly by any
means but he didn’t strike me as attractive, although I’d heard mom say
he was handsome and aunt Julie once said he looked distinguished. He was
always nice to me and very affectionate and I really enjoyed the ‘guy
things’ we did together, like fishing, canoeing, hiking, and going to
baseball games. Once I started advanced courses, I would go over to
uncle Tim and aunt Julie’s a couple of evenings a week for help with my
lessons. Aunt Julie was usually out somewhere and uncle Tim would be
there to help me, then drive or walk me home afterwards. Sometimes, I
would stay over at their place and go home the next day.

Uncle Tim and I were alone Friday evening, sitting on the couch in their
living room after finishing my lessons. Aunt Julie and my mom had gone
up to the cottage together and I had been invited to stay the weekend
with uncle Tim.

Lately I had noticed some unfamiliar magazines laying around the room
when I was there for my lessons, so being a reader and naturally
curious, I picked one up to have a look when uncle Tim went to the
kitchen to get us some cold drinks. I recall the title having the word
‘swing’ in it, and there were pictures of nude men and women on the
cover. I felt a sudden flush of embarassment, mixed with a thrill of
excitement and an immediate response in my crotch as I quickly thumbed
through a few pages of very explicit sexual photos and ads. I hurredly
put the magazine back in its place as I heard uncle Tim come into the
room.

I soon realized that he must have seen me looking at the magazine from
what happened next. As we sat sipping our drinks, he suddenly said
‘Teddy, now that you’re getting to be a man, do you ever have wet
dreams?’ Now mom had told me all about wet dreams when I first started
to ejaculate, but I rarely had them, probably because I masturbated so
often. Uncle Tim and I had never talked about sex before, but I wasn’t
too embarassed because we were good buddies and I trusted him enough to
talk to him about nearly everthing else. He had always given me good
advice and been non-judgemental with me.

I said ‘sometimes I do’. He continued ‘have you started to masturbate
too Ted’. With quickly reddening face, I gulped and nodded ‘yes’ in
answer. ‘No need to be ashamed of it Ted, its perfectly normal and very
enjoyable. As a matter of fact, I still do it myself whenever I get a
chance.’ I didn’t know what to say, if anything, but uncle Tim went on
‘you know Ted, when I was about your age, I had a couple of buddies and
we used to get together sometimes and have whats called a circle jerk.
Thats when guys get together and sit in a circle watching each other
masturbate or jerk off. We would go to one of the guys houses when his
parents were out or do it out in a secluded spot in the woods we knew.
Masturbating can be a lot more fun when you do it with someone else.
Would you like me to show you what I mean?’ Mortified, but still partly
hard from seeing the sexy photos and becoming more sexually aroused by
the moment, I gulped out a barely audible ‘I guess so’.

‘Don’t be nervous, hon.’ said uncle Tim, as he moved over to the
opposite end of the couch from me and slid his right hand down and began
to massage the growing bulge showing at his crotch. Putting down his
drink, he unzipped his pants with his left hand and slipped his right
hand into his open fly. I could see by the movement in his pants that he
was stroking his dick with his fingertips. He smiled over to me and
motioned for me to start playing with myself too. With shaky hands I
managed to get my fly open just as he pulled his pecker out of his
pants. It was only a little longer than mine, but quite a bit thicker.
Like mine, it was circumcised. We had seen each other’s cocks lots of
times over the years when we were changing before and after swimming at
the cottage, but this time was in an entirely new circumstance-I had
never seen anyone else with a hard-on before.

The sight of uncle Tim’s erection really aroused me, especially when he
was masturbating with long, slow strokes and making sure I had a good
view of his self-pleasuring. I was pretty nervous at first, so it took
me a few minutes before I calmed down and was able to concentrate on
making my own cock hard and excited too. It was easier to keep my eyes
on his swollen pecker than to watch his face, and it really began to
excite me when he took his pre-cum off the tip of his cock and licked it
off his fingertip. When he saw how it affected me, he said ‘go ahead and
try it, it tastes nice hon’. The head of my pecker was covered in
pre-cum already, so I followed his lead and tried it myself. It really
did taste good, so I did it again every time he did.

After about five minutes, uncle Tim said ‘I’m getting pretty hot baby’
and he stood up and began undressing. Imagine my surprise when he
unbuttoned his shirt to expose a pink nylon camisole with lace-trimmed
neck. He maintained his composure as he proceeded to take his pants off,
revealing a pair of nylon panties that matched the camisole, then turned
to me saying ‘well babydoll (I was really begining to love the little terms
of endearment he used with me, and I hoped he would continue with them!),
now you know another of my little secrets.’

Well, he didn’t know the half of it! When I saw him dressed in that sexy
lingerie, it was like a giant weight had been lifted off me. I wasn’t
the only male who liked to dress up in women’s underwear. My own uncle
was the same as me. ‘So baby, are you shocked?’ he said, moving to stand
right in front of me. ‘I don’t know, I replied, still u*********sly
rubbing my swollen dick and unable to pry my eyes off the throbbing
pecker sticking out the leg-hole of his silky pink panties.

‘Does the sight of my big cock excite you darling?’ he asked huskily. I
nodded a silent yes in answer. ‘Have you ever tried dressing up too
baby?’ Wow, I thought, what do I say now? Its almost like he can read
my mind. I answered with another nod and mumbled out ‘yeah, sometimes.’
‘Oh honey, thats great’ he replied. ‘I’ve often thought you might be that
way too. Now that I know, there’s all sorts of things I can teach you
about. That is if you’re interested and not too shy. Would you like to
know what I have in mind?’ ‘Alright, I guess’ I f***ed out quietly,
while inwardly my heart and head were pounding because I was so sexually
aroused at the sight of his cock and his gorgeous, silken lingerie.

‘Honey’, he said ‘aunt Julie knows that I like to dress up like this
and she enjoys it when I do-it really turns her on sexually. As a matter
of fact, she even buys me lingerie that she thinks I’ll like to wear and
helps me dress up sometimes. She’s a great lady, baby. I’m sure she would
be thrilled if she knew that you liked to play dress-up too. The proper
term for it is transvestitism or cross-dressing and there are a lot of
men who do it secretly. I belong to a private club where all the members
are transvestites like me. We meet regularly to dress up, and often a
couple of us will meet privately at other times for mutual masturbation
and other sexual fun. I’m very lucky to have a wife like aunt Julie who
is so supportive of me. Does your mom know that you cross-dress Ted?’ ‘I
don’t think so uncle Tim, I replied. At least I haven’t told her and she
hasn’t said anything about it to me. I only do it when she’s not
around.’

‘Well, I have a feeling she would be very understanding about it honey.
I’ve known your mom a long time and I know the kind of person she is. As
a matter of fact, I know that she knows I enjoy cross-dressing-aunt
Julie told her about years ago, with my permission of course. Come with
me baby-I have something to show you.’ At that he turned away from me,
his still-rigid cock wagging from side to side as he walked out into the
hall leading to the bedrooms. I got up and stuffed my now-flaccid penis
back into my pants and hurredly zipped up my fly as I followed him down
the hall to the master bedroom.

When I stepped into the room, uncle Tim was standing in front of the
open closet taking nightgowns and negligees off their hangers and
tossing them on the bed. He already had a pile of a dozen or more and
was still adding to it. ‘Aren’t they gorgeous baby doll?, he said. And wait
till you see whats in the four-drawer dresser over there. I’ve been
collecting lingerie for years and can’t bear to part with any of it.
Aunt Julie and I share our stuff, so don’t be shy. You’re welcome to
wear anything you like, but for now you might want to just strip down
and try masturbating with some of these pretty playthings. I don’t know how you feel about it, but I can never get enough of the feel of soft, silky
nylon on my pretty penis and the rest of my body too!’

Without waiting for further encouragement, I quickly stripped naked and
walked over to the dresser he had indicated, my heart and head pounding
with excitement. The dresser, one of two in the room, had a large
mirror. I opened the top drawer first. It was full of panties, bras,
stockings, and garter belts of all colours and styles. The second drawer
held a huge collection of half-slips, nighties, and camisoles, all nylon, some
matching sets, some plain and some lace-trimmed, and loads of half-slips
of different lengths, colours, and styles. The third drawer was full of
full-length slips. There must have been three or four dozen altogether!
The bottom drawer contained silk, satin, and nylon pajamas, teddys,
merry widows, and a collection of dildos, vibrators, and other sex toys.

My little boy penis had sprung into an erection as soon as I began exploring the contents of the dresser. I quickly grabbed a lacy, baby-blue, nylon tricot
baby doll gown and slipped it on. As I stood in front of the mirror smoothing the folds of the nightie, I sensed a movement behind me. ‘Go ahead sweetums, enjoy yourself’, uncle Tim said as he put his hands on my shoulders and began
gently massaging them, while looking at me in the mirror. I hadn’t
noticed him come up behind me as I was going through the dresser full of
lingerie. He had taken off his pink camisole and panties and was now
wearing a full-length, pale green nylon nightgown and negligee set. It
was beautiful, with lovely lace trim, and the sight of him and the feel
of his touch sent a frisson of sexual excitement up my spine. ‘Mmmm!’
he murmured as he felt me shudder in response to the thrill of his
caresses. Then he began to stroke my arms, saying ‘you like this, don’t
you my darling little girl/boy?’ Yes, I nodded in reply. Slowly, he turned me to face him, staying so close to me that our cocks, rigid under the filmy, silken fabric of our lingerie, brushed together as he did so. My ass was up against the front of the dresser as his hands slipped down to my wrists,
gripping them firmly as he pushed gently closer, forcing his throbbing
cock against mine, moving his hips sensually round and round as he
moaned in pleasure.

After a few seconds, he pulled back and, without a word, led me by one
hand over to the bed and motioned to me to get on it. I was in a trance
of sensual delight. There was a pile of nylon tricot gowns and negligees on the bed a foot thick. I crawled onto the middle of the pile and turned to
face uncle Tim as he joined me. We were both shaking with excitement as
he drew me to him, kissing me on the lips as he put his arms around me.
It seemed the most natural thing to respond to his kiss and I just
melted in his embrace, putting my arms around him too. His hands began
exploring my hips and ass as we continued to kiss, tickling and
caressing me through the filmy, frilly folds of my precious baby doll nightie.
I just massaged his back and shoulders, not knowing what he wanted me to do. I
ached for him to play with my little boy/girl penis. He must have sensed my
need, for soon he reached up under the filmy hem of my nightie and started to
stroke my inner thighs. When he finally touched my cock, I was in absolute ecstacy.

Teasing it gently with his fingertips, he soon had my swollen little penis
throbbing and aching for more. After wrapping a nylon gown from the pile
around my cock, he grasped it in a loose full-hand grip and began to
masturbate me with long, slow strokes, I could feel my pre-cum start to
ooze out the tip, and moaned with delight. As I responded willingly to
his lovemaking, his kisses became more passionate and he began slipping
his tongue into my now-eager mouth with increasing frequency. I fucked
his tongue with my mouth in return. My passion and arousal overcame any
shyness I had left and I groped for his pecker with my right hand.
Taking my cue from him, I stroked and rubbed his rigid cock through his
silken gown the same way he had been masturbating me, and was spurred to
new heights of ecstacy by the reaction I got from him. He writhed and
moaned in pleasure, saying ‘yes Darling, yes, yes, thats it, thats sooo good! I love it, I love it!’ OOooooo, I’m cumming sweet darling….cumming just for you!’ And his pretty cock began to spurt his silky, sweet white cum all over my gown soaking it warmly and making it feel so oily slick against my skin!