Date: Sat, 10 Oct 2020 05:22:19 +0200
From: Lee Mor <my.mail@cheerful.com>
Subject: Skippy and Dash, transgendered teens

   My juvenile ways of thinking changed drastically a few days after I
got a job at a used book store in town. The owner's son, Dash, and I were
of a similar age. Even though he was of a slighter build and had a more
refined affect, he seemed to be much more mature than I. One day, soon
after I started Dash was showing an older man where the adult books and
magazines were. The man was friendly with Dash, putting his hand on his
shoulder and smiling and joking with him. I had to stock some cookbooks
that had been stacked in the aisle and soon forgot what I'd seen.
   But later on when I had a chance I looked at the magazine that dash
had shown the man. It was mostly pictures with short captions. The photos
were of women undressing and posing in quite alluring poses if I do say
so myself. But then something odd occurred  to me. The shape of a quite
attractive woman's face was strange to my gaze. For a second I thought it
could have been a man's face. But that would not have been right. Dash
would never look at pictures of men dressed like women. That was just
queer. I tried to admire the women in the pictures and not think about
the thoughts that crossed my mind unbidden.
   But the next page brought all of the unbidden to the fore. A two page
spread announced itself with a model whose name would become more
familiar as time went on. His, or um, her name was Dixie Taylor. He, no
she was reclined on a day bed splendidly arrayed in a sheer camisole top
that barely reached her belly button Her matching panties were
scandalously short with a wider band along the top and sheer, sheer, did
I say sheer? fabric from the band through the crotch. And there, just in
the middle of it all, the head of an erect penis just poked, ever so
slightly, out of her panties. The covered portion of the erect tenderloin
was disconcertingly prominent, despite being covered and the general
erotic nature of Ms. Dixie's display in toto.
   A flood of questions and judgements and desires all tumbled across my
consciousness. Why did Dash show the old guy this magazine? How did Dash
know his tastes? What goes through someones head when they think about a
man dressed like a woman, a beautiful desirable woman? Why was I getting
aroused when I didn't like the idea of having sex with boys or men? I
physically shuddered. I was vaguely aware of gay men and women. Gay
women, lesbians actually turned me on. i'd finally allowed myself to
believe that two women making love could be beautiful. In the secret
precincts of my mind they did. Thoughts of teachers and classmates and
bookstore customers as lesbians who discover that they have an attraction
to ,,,me comprised my fantasies in those days.
   I went home that night and went to bed and masturbated, somewhat at
arms length from the idea of having sex with another male, but desirous,
nay desperately for the beautiful creature that was Dixie Taylor. She
teased and cavorted in front of me, stealing kisses, placing my hands on
her body and thrilling me with the sensation of her touch. My hands slid
over the globes of her tender young buns and for the first time I
considered the possibility of my erection entering her (or anyone's) anal
opening. I know that I came but don't remember anything about it. The
prelude to the climax was was the context of this fantasy, not it's
conclusion.
 Several days later Dash noticed me looking at magazines in the adult
section. I was embarrassed momentarily until he spoke to the manager.
   "I have to leave for a few minutes. Be back soon."
   My mind moved on to the pleasures life has to offer. There was nearly
no one in the store now. Just the manager, Jane, the barista, Brenda and
a customer she was serving. And then there was me. I had not given the
adult section a full survey of the different content of erotic materials
available. There were magazines for heterosexuals, lesbians, gays, and
trans-gendered people, as I learned they were referred to. The lesbian
topic of inquiry commanded most of my time of late. I had seen tender,
and beautiful women in each others arms and my heart pounded in my chest
as they amorously rolled in the sheets. But my mind was also made aware
of lesbians who were not so gentle and content to play nice. Women would
be naked or nearly so across another woman's lap and being paddled and
their bottoms bright red and tender looking. Sometimes the spankee was
miserable looking, but often she was smiling and shaking her bottom in
the dominate woman's face begging to be spanked some more.
   My hand carelessly drifted to my crotch area and my erection was there
before I knew I was having one. Then I had the greatest shock in my short
life at that moment. I dropped the magazine open to a display of two
young, cute chubby women were glistening with oiled skin and were tightly
embraced.
   A young woman, a girl, looked at me and asked, "So you like the plump
ones too?"
   I tried to squawk some inane defensive lie, but didn't have a chance
The girl was on her knees, the next I knew. Her hands were busy doing to
me what I had been doing seconds earlier, caressing my bulge with one
hand and unzipping me with the other.
I was too shocked to even react but my mind did notice that the store was
nearly empty and the girl was leading the charge, keeping my desire high
and my fear of exposure from ruining what I knew would be a highly erotic
experience. She stood and kissed my mouth. French kissed with her tongue
squirming over my tongue. Her hand slid into my pants and it was soon
touching my now throbbing male member The effect took my breath away. I
kissed her back with passion and I searched her body with my hands. She
wriggled so sweetly against my body.
   I had no previous experience to know what to do. Fortunately, she did
and proceeded to do so. She had my belt open and pants unbuttoned. She
got back on her knees and the next sensation nearly made me pass out. Her
warm wet mouth was enveloping the entirety of my being. The entirety of
my being was my cock and its smooth shaft appeared and disappeared again
and again. Involuntarily my hands enclosed her head as she started
turning her head as she went up and down on me. As she continued her leg
got behind mine and soon I was aware that her hand was sliding up between
my buns. I had a sharp intake of breath as her finger found my anal
opening.
   " Oh, GAWD, You are a goddess!" So much for impressing her with my
gift of articulation. She continued to suckle me as she entered me also.
My awareness went from my bottom to my buns and back, from the back of
her throat and its sweet constrictions to to the confounding sensations
of what her fingers were doing in my ass.
   My excitement was beginning to build in the manner made familiar by my
masturbations. She sensed this and made her craven ministrations even
more frantic. I tried to utter that I was going to cum, but she made no
change to her method of delivery. Soom the building sensations squirted
my warm, pearly, gooey cum into her mouth. She was as adept after the
climax as before. her tongue swished back and forth under the head of my
manhood as she milked me for the tiniest last drop. She had been looking
up at me the whole time and now she stood and our mouths closed together.
I was surprised when i realized that the taste in my mouth was my own
cum. Who is she? I had to know this wanton beauty.
   Then just as quick as she had shown up she exited and only said,
"Don't tell anyone you saw me like this." I kind of finished my shift in
a pleasant haze, a little afraid that anyone who looked at me would know
right away, that I'd had sex. In a public place besides that.
   Dash had returned and had brought everyone's' pay check. He was acting
strange. As he delivered each check he he was joking about how little was
in each one. When I looked at mine it seemed like less of a joke. But I
was the new guy and it was my first check. Dash winked at me and quipped,
"I bet you wish it was fat too." I looked right at him. I was confused.
It seemed like I was missing something here.
   As I walked home I could only think of the activities of this
afternoon. Why me, I asked? Don't get me wrong. I could spend half of the
rest of my life with my penis in a friendly mouth. The other half would
be other sexual activities. But I didn't understand why she came on to
me. And who was she anyway?
   I almost forgot to stop at the meat market for a package my mom
ordered. She was having a party with a few of her friends from the
Naturalist Society. There would be a bar and the pool will be open and
yes, everyone will be naked. This was another area of confusion in my
life. Mom had explained it to me several times. Naturalists believe that
being naked was how nature intended us to be, close to nature. But even I
knew that in the winter you need warm clothes. Yet it did seem natural
also and I saw the appeal. And I had not even begun to evaluate the
sexual aspects of it. Well, I had begun, in fact every time I thought
about nudism I got around to thinking of sex. Many spokespeople for
nudism will tell you that its not about sex, its about shedding hang ups
and emotional baggage that wearing clothing causes us to feel. But in my
mind I knew I would be looking at the naked women.., and men, yes it was
unavoidable. Yet I must confess to some modicum of curiosity about
men's bodies. But I knew that I would enjoy looking at naked breasts and
bottoms and vaginas.
   I dropped the package off in the kitchen with Minerva who sometimes
cooks and prepares for Mom's parties. "Skipper, honey. Your mother wants
you to be ready at 7 o'clock. Can you do that?"
   In uncharacteristic snarkiness I cracked back, "All I have to do is
take off all of my clothes and I'll be ready."
   "I'll bet she'll be real happy if you take shower and comb your pretty
hair, you ruffian. "She messed up my hair with her fingers just to make
fun of me.
   "Are you coming to the party, Minerva?"
   "Its not my kind of party, Skipper." She paused momentarily, "I'm not
saying that its wrong. In fact I agree with the reasons for doing it. But
your Mamma is a braver woman than I."
   I did take a shower and combed my hair and brushed my teeth. Then I
walked to the pool at ten to seven. No one was there yet. I descended a
couple of steps and sat on the edge. The stone pool deck was warm from
the sun light and felt comforting and delightful. A tinkling of giggles
and laughter came through the patio door. Guests were arriving. Normally
guests entered the front door then turned right and went into a guest
bedroom to disrobe. There was a side door that exited to the patio
through which the guests went to join the party. Five of them bubbled out
of the door patting each other on the backs and sipping champagne. Mom
came out the other door all smiles and eagerness to see them. I had to
convince myself that this was a group of nudists even though I was
looking right at them. Most people's reality doesn't consist of this kind
of party. My didn't either, really. This was the first time for me as a
participant. Previous to this I was with an O'Pere along with the other
kids. There were usually one or two, and we watched movies and played
video games. Something else was different this time. There were no men.
   After the fellatio of this afternoon my libido was still at a more
heightened level and the graceful ladies who were moving in my direction
caused my erection to begin to grow.
   "Skippy, please step out and greet everyone." Mom was looking at me
straight on and must have seen my organ's state of arousal. But then I
just told myself, 'Why not?' I just stood up and stepped out of the pool
with my flag flying between half mast and all the way up. As I walked
over everyone was quiet and looking up and down, at me. I walked toward
the closest woman an extended my hand.
   "Hi, I'm Skipper"
   "I'm delighted to meet you Skipper Honey. I'm Char. Your mamma and I
are real close friends."
   "And I am Pepper and this is my wife Tiffany. Tiffany is your friend
Dash's mother. Did you know that?"
   "No ma'am, I didn't know that. But can I ask a question?"
   "Sure, Sweetie. Ask away."
   "If Ms. Pepper is your wife, ah, um, how does Dash's daddy fit in the
picture?"
   "Oh. Well, Pepper started, His daddy and I are friends and we both
wanted a baby, but we didn't want to be married. So we had him and we
both love and support him."
   "Oh, that's cool." I piped up enthusiastically.
   "Hi Skipper. I'm Danae. Your mother and I went to college together.
I'm really happy to meet you too."
   The last one I shook hands with was someone I already knew. Knew and
had lusted for and was having a hard time suppressing that memory at the
moment. Brenda the barista at the bookstore. But her warm smile and
personality were very disarming. "Hi Skippy, fancy meeting you here." She
giggled. For a second or two she seemed like embarrassment might creep
into the conversation, but she deflected it. "So, pretty nice getting
your first paycheck, I bet?"
   The greetings continued for a minute or so when mommy got everyone's
attention.
   "Well thank you for coming everyone. Skippy is at a disadvantage
because he only knew that there was a clothing optional party tonight. He
didn't know that it would just be us women and him. We've never
celebrated Skip's birthday before. "She was caressing my back and half
hugging me. "I wanted to save all of the celebrating for this night. From
time to time he and I have discussed having a 'Mama's day to be naughty'.
And I thought that he'd appreciate it more if it was just us women who
are such good friends already." My eyes were wide open and my jaw was
hanging. I had no idea of what she was speaking of but it sounded so
intriguing and sexy that I did't care that my erection was fully erect
and bouncing on its own. Mom continued, "So honey, you should hug each of
these women and tell them How nice they make you feel." OOOHHHH Gawd! I
had such a wide grin on my face I couldn't stop smiling if I bit my
tongue.
   Char was first again. I pressed into her fulsome figure and wrapped my
arms around her. She put her hand on the back of my head and pulled me in
for a kiss. She had all of the passion of a twenty year old, yet she was
close to fifty. "Char you make me feel happy and I love being naked with
you." She french kissed me and passed me to Pepper. While that was
happening I saw Tiffany kissing Danae and Tiffany's hand was between
Danae's legs. Pepper lived up to her name as I came spinning into her
embrace. She placed my hands on her breasts, then straddled my throbbing
tenderloin and then, none too gently, clapped onto my buns and moved then
independent of each other. I became aware of the sensuality of the anal
opening at that time.
   "Oh god Pepper, Oh my god"
   "We'll have time for more later, handsome." Tiffany was on her knees
as I turned around and my male person-hood entered into someone's mouth
for the second time today. But only briefly. She stood, kissed and sucked
on both of my nipples and milked me several strokes. I forgot who was
next. I'm sure I enjoyed it but sensations and conversations, such as
they were and sex play was running together now. Soon Mom said that we
were going to take a break and have some hors d'oeuvres and pool play.
   If the day was full of shocks there was no reason to stop now. Mom had
a tropical plant of some sort on the patio. The pot it occupied had
wheels on the bottom. She pushed the whole thing aside revealing the hor
d'oeuvres tray. It was a woman. But not just any woman. It was the woman
who was in the bookstore today. It was the woman who showed up out of
nowhere and sucked my penis, which was now dripping what I was to learn
was Cowper's fluid, aka precum.
   At that moment Danae's body impressed itself on my back. Her nipples
and breasts I felt first. Her genital area them touched my buns so
sweetly. One arm came around my chest and found my nipple. To my surprise
it was erect, too. Her other hand went low and lower and grasped my
wee-wee. She knew about precum and massaged the head of my organ with the
warm slippery stuff coming out of its tip. As we stood there, the others
were having canapes lifted from the woman, the girl really, from her
tummy and her pubic area. While I stood in rapt pleasure I was only
vaguely aware of the women snacking until one of them lifted a cracker
and avocado assemblage and revealed to me by its removal, a penis.
   I weaved back and forth for a second and looked at the human appetizer
tray again. It was Dash! The intellectual, quiet but cool kid that I
worked with. But why was he dressed like a woman? And why had he sucked
me off? And why was he here lying naked with snack food on his body?
   "Are you okay, Skip?" Danae asked while nodding at mom to get her to
come over.
   "I know him...her!" I pointed at Dash. I felt weird thinking of the
desire and arousal I'd felt earlier. And now too to be honest. She looked
so sexy with her hair and make up, those charming strappy sandals and her
poise and self possession. I actually thought about telling everyone
there that Dash and I had had such a fun afternoon break. Brenda was
lingering by Dash and then she reached over and masturbated her. She was
sliding her hand up and down her shaft. Then in view of everyone she
drooled a copious amount of saliva directly onto her..,I'll call it her
clitty and jacked him slowly while pushing her breast into Dash's mouth.
   Mom and Tiffany were standing by me now. Tiffany had her arms around
mom. Seeing this nearly made me cum right there. Tiffany then asked,
"Skippy have you tried the champagne yet? I bet you'd like the bubbles."
   Then mom interjected,"Oh, oh, Tiffany's serving Champagne everyone!"
Tiffany looked at Dash and said, Watch who gets my kisses sweetie."
   She drank champagne from the bottle, while mom said I should take a
deep breath. I got about half of a deep breath and then I felt Tiffany's
lips on mine and was beginning to think of how nice they felt. But then
her tongue forced open my mouth and champagne poured forth from her mouth
to mine, while mom was telling me to swallow fast and often. I did what
mom said and swallowed and swallowed and swallowed. Finally I couldn't
keep up and champagne gushed out of my mouth and dribbled off of my chin
onto my chest. This was apparently a signal and several tongues were
licking me, everywhere, chest, nipples, legs, scrotum and yes, my tender,
young erection. After a moment of being overwhelmed I started joining in
and grabbing breasts and kissing necks and ears. At one point I was
licking someone's shaved pubic area. Later I checked and it was mom's.
She was the only one shaved completely. The others were trimmed, quite
nicely too.
   About this time Dash was removing the remaining appetizers from her
supple delicious body. Tiffany was sitting on a chaise lounge and
summoned Dash. "Across my knee." she said firmly. "What did we say about
that little sissy clitty before the party. "Say it so everyone can hear
it you swishing little sissy."
   "I was supposed to keep it tucked between my legs so that Skippy
wouldn't think I was trying to act like a man in his presence. And I was
to maintain a womanly bearing just in case he deigned to fuck my pussy."
   The combination of the champagne and my confused feelings about Dash
kept me from internalizing what Dash had just said, for a moment anyway.
I looked at mom. She was pouring oil over Char and herself and they began
slow dancing. The other women had grouped up in ad hoc groups. Dash was
laying across his mother's lap, his proportionally small clitty organ was
so erect it must have been painful. Something else was painful with a
certainty. Tiffany had just given him a smart crack on this bottom. Why
had she done that? I felt anger, real anger for the first time in recent
memory. Poor little Dash. CRACK, another had landed and he had red spots
on those poor tender buns. I was walking over there. Tiffany saw me and
got up from the chaise.
   "She needs you now Skippy." I was going to say something angry, but
when I saw Dash she looked so sweet and innocent. I sat down and pulled
her into my lap. Her buns felt warm and my erection stirred. We kissed
and caressed.
   "I didn't know it was you this afternoon. You silly girl. I was
fantasizing about you ever since."
   "Mommy's right, I am just a sissy. And I'm waiting for a strong
handsome man." Her hands explored my chest and shoulders. "If its your
mom's day to be naughty, well maybe you can be naughty too and fuck me
Skippy. I could milk your man muscle with my pussy muscles." I didn't say
anything, but just maneuvered us so that Dash was laying on her tummy. I
parted his buns and massaged them independently from each other. I
delivered a mouthful of spit into dash's pussy. While I hovered over her
my pole poked and prodded and finally penetrated. I entered slowly and
with extremely heightened sensetivity and excitement. I moved in and out
while it was easy and kept going deeper with each thrust. Dash was good
as her word and her pussy muscles constricted and manipulated my prong.
My god it was wonderful!
   A moment later someone was pouring warm, scented oil on us and then
began massaging it around our writhing bodies. It was mom I think who
worked the oil between my buns and lovingly into my anal opening. Waves
of pleasure washed over me. My muscles hugged and crushed Dash to me. Our
oil slick bodies locked in rhythmic pumping sex. She was so sweet and
desirable. Her wonderful buns pushed back at my pubic area so tenderly.
Then I screamed.
   "I'm cummming! Oh gawd, oh god, oh god Dash sweety. Oh, baby. My
beautiful baby I love fucking you. And I'll love having you for my
sissy." Her buns constricted around my wee-wee and she cooed as I spoke
sweet things to her.
   Right then, her mom Tiffany came over and asked me something.
"Skipper, would it be okay if I gave Dash fellatio now. Because if you're
going to be her daddy and use her for your pleasure, well it wouldn't be
right for you to have to give her sexual satisfaction." I could see that
the champagne was having an effect on Tiffany, but she continued. "And
you need to know that now as Dash's daddy, you can have me service your
needs if you like. Tiffany was accommodating and tender fellating Dash.
   Mom had told me once that Tiffany got angry with a man who she was
seeing and told him that the term 'blow job' was such an ugly name for
something so beautiful and generous. I agree. Not only that, the so
called "dirty words" are a distraction from what is happening that the
full enjoyment of the acts of love would be hindered.
  That night I went to sleep with mamma. Dash slept on a air mattress on
the floor at the foot of the bed. She looked so cute with her choker and
peach colored chemise.  Momma suckled me to a delightful erection. She
guided said erection to where it would do the most good and I was blessed
with an hour of gentle, gracious, erotic love making with a gracious
lady.
   Soon Brenda moved in with us also. She had a desire, which mom and i
were eager to satisfy. Brenda liked to rim our anuses. I bet if it could
be studied, all mammals would enjoy that particular activity. Of course
Brenda an mom fucked each other in every room in the house and out doors
too. I and to a limited extent, Dash joined them from time to time.
Despite the fact that I'd never known about sissies and "daddies" before,
we both grew into those roles quite well. The bookstore was witness to
sex parties and desperate quickies.
   We improved the adult section and made it appropriate to to document
the founding activity of the human race. Congratulations if you're
reading this. It means you're one of them.