It started with my baby sitter, Barbara. I was 9 years old and the terror
of every sitter my parents engaged. Barbara was the latest in a long
string of young girls who would sit for me once and then refuse to come
I gave Barbara the Treatment, too. The issue was usually about what sort
of game we were going to play to keep me occupied and out of trouble.
Keeping me occupied was the price of peace. I tried all the usual things
on Barbara, too: I didn’t want to do this, I didn’t want to do that;
anything she proposed was something I didn’t want to do. I gave her no
peace until, finally, sleepiness overtook me and she put me to bed. I
figured that was the last of Barbara.
But Barbara was made of sterner stuff than the others, or maybe she saw
something the others didn’t. Because the next time my parents went out,
there she was again. And I entered on the same campaign of harassment.
But after I had scornfully rejected all the things she proposed, she said,
“All right; would you like to play dressup?”
For some reason I hesitated over this.
“I mean dressing up. Put on different clothes and see how you look in
them. See how it feels to wear them.”
“What kind of clothes?” I was getting–well, not interested, but curious.
I thought I’d hold off on the harassment for a bit.
“Well, I brought along a couple of costumes. I thought you might like
trying them on.” She dug around in her tote bag and brought out some
articles of clothing.
“See? Here’s a pirate costume. My brother used to wear it when he went
out on Hallowe’en.”
A pirate costume. I was turned off already. But I was also just a little
curious. So I made no objection. I stripped to my briefs and put the
costume on. I made the usual kid noises–“Yaah! I’m a pirate! Everybody
better look out!”–but I quickly lost interest and demanded something else.
So she got out–I forget what it was, but it was some other kid thing. I
put that on and rejected it immediately. The game was beginning to pall,
and I realized that I was in danger of breaking my steady string of
victories over baby sitters. I was ready to refuse the next costume out
of hand. Barbara got a sly look on her face.
“I have one other costume, Brian. But you won’t want to wear it.”
“Yes I will.” Contradict your sitter at every opportunity.
“No, you won’t.”
“Sure, I will. Try me. I’ll wear anything.”
“I’ll bet you won’t wear this. It’s a girl’s costume. A cheerleader
Well, it wasn’t, really. Later, when I got to high school, I found out
what cheerleaders really wore and this was nothing like it. This was a
pinafore, much more modest than a cheerleader’s costume and more feminine.
Barbara must have known this, but she probably thought I wouldn’t know the
difference, which I didn’t, and that cheerleader sounded more attractive.
It did, too; but, more importantly, the thought of wearing a girl’s cos-
tume–I don’t know, but I felt a mysterious attraction for it. The lure
of the forbidden, I suppose it was. Whatever it was, the moment he said
it was a girl’s costume, I wanted to wear it. Wanted it even more than
tormenting my sitter.
So I put on the pinafore. It was a white skirt, a white blouse with
ruffles, and a sort of blue apron affair that went over both. It felt
good. It wasn’t the cheap, sleazy material that the other costumes were
made of; this was the genuine article, and I sensed this. This wasn’t just
a costume; these were real girl’s clothes I was wearing. And they felt
good, very comfortable. More than comfortable: they felt as if they
belonged on me.
“Gee, Brian, you look so cute in that!”
By rights I should have objected to that word “cute.” But I didn’t. I
said, “Yeah, it feels nice.”
“Turn around and let me look at you. Golly, you make a real nice looking
Well, I thought it was a cheerleader’s costume, so I cheer-led, dancing,
kicking, and yelling things like “Fight, team, fight! Rah rah rah!” And
the funny thing was that, while I quickly got bored with yelling, I didn’t
get bored with the clothes, the way I had gotten bored with the other
costumes. That must have been because the other costumes were fake while
this was real. But there was something else, too. The skirt felt nice on
my legs, and the ruffles looked good on me. There was only one thing
“This is okay. In fact, it’s real neat. But I don’t have the right
“You mean panties? You want to wear panties?”
“Well, er, it’s a girl’s dress, isn’t it? Don’t girls wear, uh, panties,
under this?–and stockings? Aren’t you supposed to wear nylons with this?”
“No, you don’t wear nylons with this kind of dress.”
“Well, I’d, uh, I mean, I might like to wear nylons, too.” In a lower
voice, I added, “You know…I put on a pair of Mom’s nylons once…and when
she found out I caught holy…er, she, well, she bawled me out and gave me
“Well, maybe next time I’ll bring you something you can wear with nylons.
And I’ll bring you some nylons, too.”
Well, to make a long story short, I sat around in Barbara’s pinafore all
the rest of that evening. The dress was a castoff dress of hers, of
course. Barbara was about five or six years older than I was, a freshman
in high school. Why she had kept her old clothes over all those years I
don’t know. But it felt so nice on me that I forgot all about my plans for
driving Barbara crazy. I couldn’t explain it, but it just felt good.
Then came bedtime and the usual struggle to get me to go to bed. I always
resisted going to bed; that was part of my strategy for tormenting sitters.
But this time it was real, because going to bed meant taking off the dress
and I hated to do that. But Barbara said,
“Okay. You’ve got two choices. Either you go to bed nicely, right now,
and I bring you a nice dress to wear next time, and nylons, too, and the
time after that, and the time after *that,* for as long as you want me to.
OR you make a fuss and stay up, and this is the last time we play dressup.
I won’t bring anything next time. In fact, there may not be a next time.
And you can try another baby sitter, and I’ll bet *she* won’t play dressup,
I was caught. Reluctantly, I took off the dress. I stalled on each
garment–apron, blouse, and skirt–partly as a matter of policy but mostly
because I really didn’t want to take them off.
At breakfast the next morning, my mother said, “Barbara said you were very
good last night! I was amazed. What did she do, anyway? What was the
I wasn’t about to tell her Barbara’s secret, which was actually my secret,
now. So I just said, “We played pirates. It was fun.”
“Well! As simple as that! After all these years and all these sitters,
someone finally stumbled on the secret. Even so, I’m proud of you, Brian.”
I doubt if she would have been so proud if she had known the real secret.
The next time Barbara sat for me, my first question after my parents had
gone was, “What did you bring me?”
“You mean, to wear? Oh, Brian, wait till you see it! I don’t know; maybe
this will be too much for you, too girlish.” And she started drawing
things out of her tote bag. “Here. Panties!”–pulling them out–“And here
are your nylons. And a bra. And a slip. And here’s a nice dress.”
This was heady stuff. I was excited right away, and in fact I felt a kind
of feeling I had never known before. I realize now that it was my first
sexual *frisson*. I didn’t know about sexual feelings when I was nine, but
I knew this was a special kind of feeling, a special kind of excitement.
Barbara and I had started to explore a new and unknown world of forbidden
things, things that boys weren’t supposed to do and that girls weren’t
supposed to help them to do. And Barbara was destined to lead me deeper
and deeper into that wicked but lovely world. It was like some rare,
potent opiate, that set your head awhirl. Hastily, I stripped naked and
pulled on the panties. They were plain white cotton, with just a touch of
lace around the leg openings.
“Now you need a garter belt to hold up the nylons. I hope this fits.”
She handed me the garter belt. And it fit me, well and snugly.
“Now, here are the nylons. You have to be very careful putting these on.
I bought them for you specially, because I don’t have any this size myself.
And if you aren’t gentle with them, you’ll get a run and they won’t look
nice on you. That’s one of the first things a girl learns, to take care
of her nylons.” I was thrilled to hear her say “girl” this way, as if she
were referring to me. “Here…roll them up, this way.” She handed me a
stocking, half rolled up. I finished rolling them up. I had seen Mom do
this, and I knew what I had to do. I put my foot into the stocking. It
was so soft! Then I slowly and carefully unrolled it onto my leg. The
stocking felt funny on my leg. Funny and nice. She showed me how to clip
the stocking top onto the garters, or maybe I should say, clip the garters
onto the stocking.
I put on the other stocking and clipped it. I looked down on my stocking-
clad legs. They looked so neat!…all smooth and nice, and with that
darkish color that nylons give your legs. And I liked the way they felt
on my legs, sort of squeezing them, but not too tightly. By this time, my
plans for driving Barbara crazy had all been forgotten. Barbara wasn’t a
sitter any more; she was a collaborator in a forbidden, dangerous, highly
“Now you need a bra. All I had in anything like your size was an old
training bra, and I don’t know whether it will fit you. Here, try this.”
I didn’t really know what a training bra was. The thought passed through
my mind that maybe it was a bra for training boys to wear dresses. But it
had been hers, so that couldn’t be what it was. But I liked that idea; it
appealed to me powerfully. The idea–oh, gosh!–of being *trained* to wear
girls’ clothes was exciting. She slipped the loops over my shoulders and
fastened it in back. It was a little loose, but I didn’t mind.
“Well, I guess it’s okay,” Barbara said. “But you’re kind of flat chested.
You need to pad it out with something. Do you have hankys–I mean, hand-
I didn’t have as many as I would need for this, but I had socks. I raced
up to my room, feeling the air on my body and the funny, cool feeling of
the air on my nyloned legs. How nice that felt! I came back, stuffing a
sock into each cup of the bra as I went. By the time I was back in the
den with Barbara I had a fairly respectable pair of little boobies.
“Oh, Brian! You look darling…. Oops, I guess I shouldn’t have said
that. You look very nice, Brian.”
“No, that’s okay, I look darling.” I put my hands over my head, stretched,
and turned slowly around. “I like looking darling.”
“Stop it, Brian, you’re acting too much like a girl.”
“Well, I am a girl. I mean, you’re making me into one. How do you think
I’m going to act?”
“Well, okay, we’re making you into a girl. But you’re acting silly, just
the same. Now here’s the dress.” After the excitement of the panties,
stockings, and brassiere, the dress looked like an anticlimax. It was a
plain blue affair, sleeveless. The top buttoned up the front, and a zipper
at the side drew in the waist. I put it over my head and wriggled into it.
Suddenly it dropped into place about me, almost as if it knew that I was
supposed to wear it, that it was supposed to be on my boy’s body. I
fumbled with the buttons and realized that they buttoned the other way.
I got it buttoned and pulled the zipper tight. I started to walk over
to a mirror too see how I looked, but Barbara stopped me.
“Shoes, Brian. You can’t go running around in your nylons that way…”
(“In my nylons!”…In *my* nylons! I liked the sound of that.) “…or
you’ll ruin them. Here, put these on.” They were a pair of high heeled
shoes. “Now these are good shoes. The other things are old clothes,
except for the nylons, which I had to buy. But your feet look too big for
my old shoes. These are shoes I wear now. Be very careful with them.”
High-heeled shoes! Somehow I hadn’t anticipated that. With trembling
hands I put them on and buckled them. Then I stood up, and almost fell
down again. I was going to have to learn how to walk in them. I tottered
carefully over to the mirror. I was a strange sight. From the neck down,
I was a pretty girl in a blue dress and nylons. From the neck up I was a
boy with a funny look on his face. So I was careful to look only at the
part of me below the neck.
But everything felt so *nice!* I had that same feeling I had had with her
pinafore last time, the feeling that somehow these clothes belonged on me,
that they were right for me.
“Oh, Brian, you do look lovely! You’re enjoying this, aren’t you? Come
here and let’s put some makeup on you.”
I came back and Barbara got out her compact and a lipstick. She dusted
some powder on my cheeks, then started carefully applying the lipstick.
I stopped her.
“No, let me put it on. I want to learn how.” Naturally, I put on too
much. Barbara got a tissue and carefully wiped off the excess.
I wish I could put into words how I felt. The dress suited me, the hose
suited me, the bra and panties felt nice next to my skin. I looked in the
mirror again. My face looked better, but my hair…it wasn’t really long
enough. I wore it long, longer than most guys, but not really long enough
for a girl. I thought, “I’m going to have to let it grow out…” and then
I realized what I was thinking. Unconsciously, I was planning to do this
again, to dress as a girl again, and to keep doing it whenever I could, and
to try to change my appearance–well, to change my hair, anyway–to be more
convincing as a girl.
“All I need is perfume,” I said.
“No, Brian. Cologne is out. Because you won’t be able to wash the scent
away, and there’ll still be some on you in the morning, and your mother
will know. Girls notice things like that.”
I suppose you could date the beginning of my life as a crossdresser from
that disastrous time I put on Mom’s stockings and got caught, but I’ve
always dated it from that second evening with Barbara, when she dressed me
up completely, even to putting on makeup.
That evening was the first of a long series of evenings. Barbara became
my regular sitter. And with each visit she feminized me more thoroughly,
more convincingly, more deeply. I don’t think Barbara was into the femin-
ization business generally–that is, I doubt if she had ever feminized
any boy before, or any man later on. But there was a certain mysterious
chemistry between us that had been there ever since that very first time;
she sensed a need I hadn’t even been aware of, and responded to it.
My parents were delighted, because their problem child had suddenly become
so docile and cooperative with sitters, or with Barbara, at any rate. And
in fact on the few occasions when Barbara couldn’t make it and my folks
had to use another sitter, I gave no trouble. Barbara’s dressup games had
broken my habit of tormenting sitters, and when she didn’t come I was too
bored to make trouble. I just sat at the computer and played games.
This went on for a few years, with Barbara saving everything she herself
had outgrown so we could use it in our games. She told me once that every
time she got something new, she would think, “I wonder how Brian will look
in this.” When I was eleven, Barbara bought me a couple of pairs of
panties of my very own, which I hid inside the case of my computer. I
couldn’t wear them very often, but sometimes after school, if Mom wasn’t
home, I would open up the computer, fish out the panties, and wear them for
a couple of hours until Mom got back. I could usually predict when she
would arrive, but when I missed it and she came home before I had changed,
I would just slip on my pants, go into the bathroom, change into regular
boy’s briefs, and flush the toilet.
I remember one evening in particular. I must have been twelve by then.
Barbara was old enough to drive now, and this evening she had driven over
to my place. After my folks were gone, she went out to the car and got a
big suitcase out of the trunk. Inside, she opened it up; she had brought
a complete outfit! The dress was a strapless evening gown, with all the
We set to work. I stripped and Barbara handed me the panties. These were
black and covered with lace. I began to get hard. I hadn’t worn black
panties before, and they were sexy. Barb didn’t know about “gaffs”–those
things you wear to tuck your penis out of sight–and of course I had never
heard of such a thing. In any case, the gown would be full enough to cover
it up. I just put the panties on with my penis pointing up underneath
them. Then I put on the garter belt she had brought, also black and full
of lace, and a pair of black nylons. Wow!
She gave me the strapless bra, also black, and what a contraption that was!
It was like the top half of a corset, with bra cups, or actually half-cups,
at the top. Barb warned me that it would be uncomfortable, and it was,
terribly, but I was excited to be wearing it. She had also brought a pair
of breast forms. Not real ones, which were expensive; she had sewn little
pink silk bags and stuffed them with something–I think it was chunks of
foam. They didn’t look terribly real, but they were good enough to fill
the bra cups.
The gown itself was blue taffeta, and I fell in love with it. It went on
marvellously, and was just the right length. “This was my first strapless
gown,” Barbara said. “I’ve been waiting for you to grow into this, because
I knew you would look just scrumptious in it. And you do!”
I spun around in the dress, making the skirt billow out and swirl around
me. Then we set to making me up. Barb had brought everything this time:
foundation, blush, mascara, the works. Slowly and patiently she made me
up, stopping now and then to examine her work. She let me apply my own
lipstick, which by now I was an expert at doing. Finally she got out a
pair of earrings and clipped them on me.
“Oh, you’re just such a *darling!* Come, look at yourself in the mirror!”
We went over to the mirror, and I didn’t recognize myself. Her makeup had
transformed my face to the point that it no longer looked like me. Many
years later I read a lot of transvestite fiction, and in those stories
there is always a moment when the young man, transformed, looks in the
mirror and sees a lovely girl there. I always believed that, because I
remembered this evening with Barbara, when that had happened to me: I
really had looked in the mirror and seen a girl. I couldn’t get over it:
that girl was *me*, Brian!
Barb had taught me to dance by this time. We put on some records and began
to dance. Barb herself was just wearing jeans and a T-shirt that evening,
and when I caught sight of us in the mirror, it looked as if she was the
man and I the woman. (Barb led, too.) My gown swirled about me as we
danced, and my earrings danced, too. I’m sorry to say that Barbara never
took me out of the house dressed up; what a wonderful thing it would have
been if we could have gone to a ball that night! How I would have loved
to be the belle of the ball, with all the guys looking at me with admiring
The big change came the next year, when I was thirteen. Barbara was a
senior in high school then. One evening when I was dressed up, the door-
bell rang. I was petrified. I had on a frilly pink dress and was in full
makeup and heels. Barbara went to the door, and I could hear her arguing.
“George, I’ve *told* you not to come see me when I’m sitting with Brian!”
George was her current boyfriend. He was good looking, but a little crude
in his manners, and I didn’t like him much. But while Barbara was shouting
at her, he must have pushed his way past her, because I heard him coming
down to the rec room, pursued by Barbara. I would have run to my room and
hidden, but he was already half way down the stairs before I thought of
this. I was caught.
George stopped dead in his tracks when he saw me. “Who’s the girl?” he
asked Barbara, who by this time was right behind him.
“Where’s Brian? Where did…?” He stopped suddenly and a look of recog-
nition dawned in his eyes.
“Well, well, well! *You’re* Brian, aren’t you, little girl? Little girl
Brian. Brianessa. Brianella!” He started to snicker.
“George, you’ve got to keep quiet about this,” Barbara warned him. “You
breathe a word about this to anybody and it’s all over between you and me.
George gave a gulp. “But it’s too much.” He gave a short laugh, a sort of
a snort. “Brian as a little girl. He is, too. He looks just like a girl.
It’s perfect.” He turned to me. “Hey, little Brianella, can you give us a
I shuddered. I didn’t like the way this was going at all. George advanced
on me and reached out. Then suddenly I knew what to do. Before he could
grab me, I forced myself to grab *him*. I made myself throw my arms around
him, give him a big hug, and plant a kiss right square on his lips.
My tactics worked. He had planned to embarrass me, but when I took the
initiative away from him and, instead of ducking and running, forced myself
to grab him and kiss him, he was the one who was embarrassed–but not too
embarrassed to hold me a little longer than I held him and to prolong the
kiss. I felt his lips starting to open and broke away.
After a few minutes, Barbara succeeded in getting rid of George, but that
wasn’t the end of it. George lived a block away from us, and one afternoon
the next week, as I was coming home from school, he waylaid me.
“Well, if it isn’t Brianella!” he said. “Are you wearing your panties,
I said No.
“Why aren’t you? You’re such a nice little girl! And you give such nice
kisses to your boyfriends.” He had remembered that. My little triumph
over him that evening last week was about to turn around. I had won the
battle; I was about to lose the war.
“I think I’d like a little girl of my own,” he went on, “and I think you’re
just the one. Come on.”
He grabbed my arm, not painfully, but hard enough to keep me from pulling
free. We went to his place and in the back of his house. There was a
garage there, taller than most, and in the top of the garage, there was a
sort of loft. We stopped before a ladder.
“Go up,” George said.
I stood there.
“Get up there, you little faggot, or I’ll beat the living shit out of you!”
I slowly climbed the ladder.
The loft was full of junk–old tools and boxes mostly. George sat me down
on a box and stood before me.
“Now we’re going to see just how good a girl you are.” He opened his fly.
“Pull it out.”
There was no doubt what “it” was. I was thirteen, now, not an ignorant
little nine-year old kid, and there wasn’t any doubt in my mind about what
George wanted. I just sat there, petrified. But there was something else,
too. I had been bullied as a boy, as I guess most boys are, except maybe
for the bullies themselves, and the adrenaline was running. But there was
something else. It was like the excitement that I felt when dressing up
with Barbara. I realized that this was a turning point. If I did what he
wanted me to, he was going to make me do it again. And again, and again,
just as I had gotten into dressing with Barbara again and again. He would
turn me into his personal sexual servant. And there was something about
I reached into his fly. I felt his shorts inside. I could feel the fabric
stretched by George’s growing erection. I started fumbling for the opening
in his shorts. George loosened his belt a notch and undid the top button
on his trousers. I found the opening and reached inside. Hair. I felt
his thick, curly pubic hair. Working downward, I felt the base of his
penis. My heart skipped a beat. George opened the fly wider with his
hands. With some difficulty, I worked his penis, which was hardening
rapidly, out through the opening in his briefs and out of the fly.
“Kiss it, little girl!”
I moved toward it. It was sweaty and smelt of masculinity. I put my lips
to the end of it. I could feel how smooth the skin was. Soft and tender,
and yet hard. I kissed it.
“That’s my girl. Open your lips and suck on it.”
I opened my lips, but kept my teeth clenched. He pushed the tip in past my
lips. I realized that my own penis was hard, too. And in a sudden rush of
excitement I *wanted* his cock in my mouth. I craved it. I wanted to be a
girl for him. I opened my mouth wide and pushed my head onto his penis.
It was too long for me; I got only about three quarters of him into my
mouth. I ran my tongue over the bottom of it.
“Yeah, that’s the way. Suck on that cock, girl. You’re my girl, now.
*My* girl. My own private girl who’s going to…ahhh!…who’s going to
suck me off any time I want it. Come on, keep sucking that cock, girl!”
I continued running my tongue around it. I drew my head back, so my tongue
was right under the base of the crown and licked it.
“Yeah, that’s the way,” he said again. “You like that, don’t you! You’re
a real natural, a natural-born cocksucker. You’re my own little slutty
girl now. I bet you wish you had your panties on, don’t you? Then you’d
be a real girl. A real cock-sucking girl.”
I guess there’s a sort of instinct that certain men have, that tells them
how to suck a cock. I had never done this before, but somehow I knew just
what to do.
“Take that cock into your hot little cunt, Brianella. Suck on it with your
cunty mouth. Don’t you wish you had lipstick on? You could leave red
lipstick marks all over my cock!”
I tightened my lips about his penis and started working up and down the
shaft. I kept moving my tongue as I did so, so I was licking him and suck-
ing him, both at the same time. George kept calling me his slutty girl and
his little cocksucking cunt.
Then suddenly he stopped talking. I felt his penis grow harder in my
mouth, and hot. Then he gave a gasp. I felt the pulsations along the
bottom of his cock, and he began to come in my mouth. I didn’t dare
swallow. I didn’t want to; I was afraid it might make me sick. His cum
was jetting into my mouth, filling it up. Just when I thought I wouldn’t
be able to hold any more, his spasms tapered off.
George held his cock in my mouth as it softened. Then he pulled my face
right up to his body, sealing my lips.
“Swallow it! Swallow.”
I thought I was going to be sick. But there was nothing I could do. I
tried opening my lips, but he just pressed my face harder into his crotch.
“Come on, tramp. Swallow it!”
I swallowed. And again.
“Okay, little Brianella. You’re a real girl now. A girl that sucks guys’
cocks. A little cocksucking girl.” He released me. “Here. Lick it
I put my lips back on it and sucked the last drops of cum off the head.
“You’re my own slutty little cocksucking girl now. Brianella. Nellie!
That’s what your name is going to be up here. Nellie.” He started tucking
his penis back into his pants. “From now on, you’re going to do this for
me any time I want you to, Nellie. And I’m going to want it a lot.”
As he zipped his fly, he said, “Next time I want you to wear your panties.
Next time you’re going to strip down and suck me off wearing nothing but
your panties. Got that? You’re a little girl and little girls wear
“Not on gym days,” I objected.
“Every day,” he said. “You can change in the john before gym if you don’t
want the guys in gym to know what a little girl you are. And you can
change back after.”
So that’s what I did. A couple of times each week George would lie in wait
for me on my way home from school, and I would climb up in the loft with
him and suck him off, wearing nothing but my panties. George always talked
to me while I was sucking him, calling me Nellie, calling me a fairy and a
slut, calling me his little sex-girl and calling my mouth a cunt. It took
me a couple of months before I began to admit to myself how much I loved
these sessions. The first inkling was one afternoon when I expected to run
into George–it had been three days since our last encounter–and he didn’t
show up. I was disappointed, and I realized with a shock that I had been
*looking forward* to sucking him off. Why it took me so long to realise
this, I don’t know, because evenings after I had been with George I would
masturbate, remembering what it had been like with him.
And George was right. I was his little cocksucking girl. And once I knew
that and realized that I *liked* being his little cocksucking girl, I set
myself to become the best cocksucker I could. I don’t know whether he ever
got blow jobs from Barbara. I kind of doubt it, because she somehow didn’t
strike me as the kind of girl who would do that, although you never know.
But I was going to make sure he got better blow jobs from me than he ever
could from Barbara, or from any other female girl. I was going to be the
best, the hottest girl he ever had.
George devised a further refinement. He had me bring a selection of my
girl’s undies and leave them in the loft, hidden in one of the boxes. Then
he would have me strip and put on various garments. He also got some kind
of padded blanket or quilt from somewhere, so we could lie down for sex.
Barbara, of course, knew nothing of all this. She was still supplying me
with things to wear, stockings and pantyhose as well as panties, and I told
her that I had a hiding place for them. I didn’t tell her that the hiding
place was a box in George’s loft.
Barb would ask me sometimes what I wanted and buy it for me. This was the
way I got my black bra and panties, almost like the ones I had worn with
the evening gown. The evening when I put them on for her was memorable,
because the panties were silk, or satin, or something like that, and the
combination of the color and the smooth texture drove me wild.
Once, when she asked me what I wanted, I fished out a catalog for her.
Victoria’s Secret, I think it was. I pointed to a teddy I had seen there–
black and lacy, with long ruffled garter straps on it.
“Oh, Brian, that’s *terrific*,” Barbara exclaimed. Her voice dropped; it
got a low and sexy sound that it often had when she and I were playing
dressup. “You’d look adorable in that. But it’s so expensive. I can’t
get you that. Look at the price!”
I handed her the money. “I know it is,” I said. “I’ll pay for it. I’ve
saved up. Just get it for me. Or one like it. Please.”
What I didn’t tell her was that I wanted it for George. The moment I had
seen that teddy in the catalog, I knew I wanted to suck George off wearing
And I did. I brought it over to George’s place in an old paper bag. I
showed it to him, holding it up in front of my body, and his jaw dropped.
This must have been the first time that he realized that I was as much into
these sex sessions as he was.
“Oh, man! Oh, man!” he kept exclaiming. “C’mon, Nellie girl, get into it
and do me!”
I put it on and lay back on the improvised mattress-quilt, striking a girl-
ish pose I had seen on a model in the Victoria’s Secret catalog. George
was upon me in an instant, stripped to his briefs, straddling my chest, and
pushing his cock into my mouth.
Two days later George was waiting for me again. When we went up into
the loft, I had a surprise. There were two other guys up there already.
George turned to me.
“Welcome to the club, Nellie. This is the Nellie Club, and you’re the
guest of honor. This is Andy and this is Fred. Go get that thing,
whaddaya call it, that teddy, and put it on…. Guys, wait till you see
I knew what was coming and was excited. This was *really* being a girl!
I was going to be a girl for these three guys! I went and got the teddy
and put it on; then I put on a pair of black nylons and clipped them onto
the garter straps. Then I put just a touch of lipstick on my lips. The
guys were naked by the time I was ready; they gave me a chorus of whistles
when they saw how I looked.
Well…this is the story of my crossdressing, not of my sexual adventures,
so I’ll just draw the curtain over the scene that followed. Let’s just say
that they were *very* satisfied with their girl, and that their girl was
*wonderfully* satisfied with them. I ended up with cum all over my face.
My teddy was quite thoroughly mussed up by the time we were through, and my
stockings were in tatters, but it had been worth it! This was the first of
many meetings of the Nellie Club, whose membership grew over time, and they
were always thrilling.
My initiation into girlhood was complete. I was never going to need
surgery, I was never going to need hormones. All I would ever need was
a pretty dress and a nice man to use me.