Date: Sat, 25 Jul 1998 06:01:42 PDT
From: Lonny Nylon <>
Subject: Life with Mom and Uncle Tim

Life with Mom and Uncle Tim

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 

Mom was a widow. She had come from a fairly well-off family and, after 
graduating from university, met and married my father. Mom's parents 
were both dead, but she and her sister 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 draped 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 

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 sleep. 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 
sleep." 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 
draped 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 
asleep 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 
asleep 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 sleep 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 xxxxxxxxxx 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 sleep, 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 come 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 pecker 
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 
asleep 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 sleep 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 

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 Teddy" 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 Ted". 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 Ted" 
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 Ted, 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 Ted, are you shocked?" he said, moving to stand 
right in front of me. "I don't know, I replied, still unconsciously 
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 Teddy?" he asked huskily. I 
nodded a silent yes in answer. "Have you ever tried dressing up too 
Teddy?" 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 Ted, 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 forced 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.

"Look Ted", 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 Ted. 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 

"Well, I have a feeling she would be very understanding about it Ted. 
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 Ted-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 Ted?, 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 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 pecker 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 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 pecker had sprung into an erection as soon as I began exploring the 
contents of the dresser. I quickly grabbed a lacy, baby-blue, nylon full 
slip and put it on. As I stood in front of the mirror smoothing the 
folds of the slip, I sensed a movement behind me. "Go ahead Ted, 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 Teddy?" Yes, I nodded in reply. Slowly, he turned me to face him, 
staying so close to me that our peckers, rigid under the 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 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 silken fabric of the slip. I just massaged his 
back and shoulders, not knowing what he wanted me to do. I ached for him 
to masturbate me. He must have sensed my need, for soon he reached up 
under my slip 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 pecker 
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 Teddy, yes, thats it, thats sooo good! I 
love it, I love it!"