Bobbie
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Bobbie
By Alyssa Davis
I wound my way around to the back door and let myself in to Aunt Mary's
house, something I have done routinely for years. Usually I just came over to
visit, since I was very close to my aunt. She was like a second mother to me,
only I was more comfortable talking to her...to confide in her. She never had
children of her own and now, she was a widow. So she considered me like her
own son. And as such I did many chores for her. Now that school was out for
the summer, I had a lot of time to spend with her since it was boring to stay
at home and she always had fun things to do. My mother was very
overprotective of me and wouldn't let me take part in any sports or other
activities so I had few friends my own age. Besides which, I was too frail
and awkward to do much of that anyway. So, instead, I spent a lot of time
with Aunt Mary. She was a lot more fun and interesting and very nurturing. I
was looking forward to getting my driver's license next year at age 16 so we
could go places together and I could be her driver and expand our activities.
This trip, I was delivering a cake mother had baked for Aunt Mary. I placed
it on the kitchen table and called out to her. She was in her living room,
struggling with some sewing...struggling was an understatement, she was
cussing under her breath.
"What's the matter, Auntie...you look like you're having a problem?" I asked
hesitantly, not knowing if this was a good time to say anything.
"Oh, hello Bobbie....I didn't hear you come in. Yes, I'm having an awful time
with this dress. I'm trying to hem it evenly and I cant get it right. This is
my third attempt. It's so difficult to do this properly with the dress spread
out on a table. I wish I had a dressmaker's form to hang it on to get the hem
straight," she replied in total frustration.
"Anything I can do to help you? Maybe I could hold the dress up for you so it
wasn't laying flat," I offered.
"Oh...No, dear...I'm afraid that wouldn't help much, thanks. I tried hanging
it on a door and that doesn't work.it's not the right height," she replied
looking at me, "I doubt if you could hold it straight and steady for the time
it would take me...but, I wonder.would you be willing to put the dress on?
You could be my form...that would help a lot because you could rotate as I
pin it."
"Well...sure, I guess so, if that's what it takes," I responded.
I really wanted to be helpful...she's always been there for me. So what if it
meant putting on a dress, it's only for a short time. I removed my shirt and
pants while she gathered up the dress and placed it over my head and
carefully guided it down my body. I wasn't bashful with her. Heck, she's
known me since birth. Being as tall as her and close to the same size, the
dress fit very well.
"This is very good of you to do this for me Bobbie...I really appreciate it.
And you look very nice in a dress, I might add," she said as she smoothed the
fabric and straightened it to hang properly.
"It sure feels strange...not bad," I noticed as she carefully zipped up the
back.
"To get the length right, I think you'll need to wear my shoes so I can
measure from the floor...OK?"
She went to find appropriate shoes while I stood and twirled back and forth
to make the skirt wrap around my legs. It felt different than anything I'd
ever worn. actually kind of nice. I stepped into the shoes, pumps with 2 3/4
inch heels, also a fit.
"My goodness, you look so nice in that outfit...I cant believe it. I should
look that good."
"Aw Auntie, you're joking. But it does feel odd...but kind'a good," I
admitted.
She proceeded to take measurements and place pins in the new hem as I slowly
rotated. I noticed my image in the mirror across the room. I saw the image of
a young girl in high heels. Could that be me? It had to be. A strange
sensation came over me. I felt comfortable standing there...I actually
enjoyed wearing this dress! I thought I should have been embarrassed, shy,
something other than what I was feeling.
"Auntie...what's it like to be a girl?" I asked, shattering the silence like
a glass hitting the floor. The image of the girl in the mirror was very much
in my mind. Since the work was progressing smoothly, Auntie was now in a good
mood.
"To be a girl? Well Bobbie, I'd say in most aspects, it's fun...you get to
wear pretty clothes and do fun things. People treat you nicely. I certainly
enjoy it, (like I have a choice)," she said smiling. She noticed I was
constantly admiring myself in the mirror from various angles.
"Why do you ask? Would you like to try it for a while? I'd be willing to help
you. I think you'd make a pretty girl. You do have pretty features."
"Oh, I was just wondering...uh.what would I have to do?" The thought of it
began to interest me...more than interest.excite me. What would it really be
like?
"When we're done with this dress, let me help you try something else on. I
think you'll be pleased."
In a short time, with my assistance, Auntie completed marking the hem and
helped me remove the dress carefully so I didn't get scratched by the pins.
She escorted me to her bedroom where she dug in her dresser drawers and
handed me some new underwear with instructions to put them on. I did so
without hesitation. By now the idea seemed very appealing. First, a pair of
panties, then a bra with lace cups which she hooked for me behind my back and
adjusted the straps for the best fit. She stuffed some rolled up stockings
into the cups until they were properly formed to her satisfaction. The
panties were just like my own briefs but of a finer, softer fabric, and a
more snug fit. I didn't think the bra was necessary except to give me shape.
But it too felt good. I offered no resistance to any of this.
"You seem so willing to wear these things, my dear...I'm a little surprised
you want to do this. Have you wanted to before now?"
"No, Auntie...I don't know why, but it's seems exciting, and it feels so
good."
Aunt Mary smiled but said nothing.
The next offering was a full slip which I pulled on over my head and down my
body, the cool, form fitting, sheer nylon feeling so luxurious. With each
garment, The sensation within me intensified. I sat down while she showed me
how to put on pantyhose. They felt heavenly on my legs...in fact all the
lingerie was wonderful! While I was admiring myself in the mirror and
savoring the feeling of these new garments on my body, she handed me a flower
printed shirtdress with short sleeves and a button front. I stepped into it
and put my arms through the sleeves. The full skirt fell to just below my
knees.
It was difficult to button since the buttons were reversed for me.
"You'll get used to the buttons...Girl's things button different than boy's."
"I'll get used to it? Oh, will I be wearing them that much?" I inquired
innocently.
"I hope so, young lady," she replied. To my surprise, she called me young
lady. That had an appealing sound.. I was beginning to hope so, too.
Everything fit so perfectly...we were both impressed. Back into the high
heels, I practiced walking in my new outfit.
"Why, you're adorable, Bobbie! You're a natural...you really should've been a
girl. So, how do you feel now?"
"I like it, Auntie. I know I'm not supposed to, but I do," is all I could
say. Why wasn't I embarrassed, I wondered? I actually liked to be dressed
this way.
"Yes, I think you were meant to be a girl, Bobbie. You're not like other
boys...you never were..." She started to say more, but stopped.
"Let me do your face, dear. I think you'll like that too," she added as she
ushered me to the bathroom where she kept her makeup. She applied a pink
lipstick and a touch of blush to my cheeks, telling me that my natural
complexion didn't need anything else, especially for a girl my age. My hair,
which I wore almost shoulder length, was easy to brush up into a feminine
style. She clipped a pair of earrings on me and stood back to admire her
work.
"Instead of a 15 year old boy, you could pass for an 18 year old
girl...you're absolutely beautiful, Bobbie!"
"Thanks Auntie. I feel pretty....I like what I see. Does that me strange or
something?"
"I don't think so...as long as you're happy with yourself, I don't see
anything wrong. Let me teach you some of the finer points of being a girl.
You're welcome to stay this way as long as you wish. My dresses are a bit old
for you, but if you choose to continue, I'll buy you some things more
befitting a girl your age."
She seemed unusually willing to help me.
I thanked her and we began to practice some feminine maneuvers such as
sitting in a skirt, walking in heels with poise, gesturing, general ladylike
things she felt I should know. She even coached me on feminine voice
inflections and vocabulary. I didn't realize there was such a thing, but I
learned that men speak differently than women. I was a willing subject.
I stayed for dinner and eventually and regrettably, I had to revert back to
my boy clothes. I asked Auntie if she could arrange for me to stay with her
over the weekend. A phone call to her sister settled that since it wasn't an
unusual request.
"You're welcome to stay with me but if you do, I want you to stay as a girl.
That means dressing like that every day and behaving as a young lady...and
doing chores. Do you agree to that? In return, I'll teach you to be a lady."
Of course, I accepted. That was my plan. I was excited to try this new
lifestyle, to see what it was like to be a girl.
For the next two days, with constant coaching from Aunt Mary, I started to
develop confidence with my dressing, feminine behavior and applying makeup. I
was getting very acclimated to my new image.
"I see a change in you, Bobbie, and I admit, I like what I see. You've become
very feminine...actually very calm and content.is this what you really want?"
Auntie asked, one evening.
"I don't know, Auntie, but I am happy. This makes me feel good. It feels
right for me. I've never been into boy things, anyway. The stuff you've
taught me and had me do are fun."
"What are you going to do when school starts? You cant go back as a girl, you
know."
"Yes, I know, but I can still dress after school cant I? Will you still help
me?"
"Of course I will, my dear...I'll always be here for you. You may be my
sister's son, but you're also my little girl. But you must not forget how to
act as a boy when the time comes."
"Oh Auntie...I love you," I said as I hugged her tightly. I really felt like
a real girl. At least, now I wanted to be one.
Wearing shorts, pantyhose, and a halter top, and, of course, the high heels
which I'd become quite accustomed to, I helped Auntie with her housecleaning.
It was awkward to work in the heels, but I wanted the practice.
"You look very sexy in that outfit, young lady," Auntie remarked. "Shorts and
high heels, wow! Better watch out for the boys."
"Thank you, Auntie...I will," I replied with a wink and a smile. "I need the
practice with the heels." It never occurred to me about boys from a girl's
point of view. I was just getting interested in girls, but now as a girl,
what do I do about boys? Oh well, I thought, I'll worry about that when the
time comes.
The first night I stayed over in my new persona, Auntie gave me a long blue
nylon gown to sleep in. She suggested I keep my panties on. Usually, when I
stayed over, I'd sleep on her sofa, but this time, she invited me to sleep in
her large bed with her, since we were both women. She really accepted me as a
girl! As we lay there, we talked about my feelings, what I wanted to do, what
girls do, boys, how I should act...etc. until I fell asleep. That was the
first of many such nights. Two ladies sharing a bed having girl- talk.
For that entire first weekend, I was a girl...three days non-stop total
femininity. Auntie didn't let me forget for one moment that I was a lady. I
was in total ecstasy. On Sunday, we went out in public, shopping at a large
mall. Again, I should have been nervous going out in a dress, but I wasn't. I
was actually eager to be seen that way. She bought me my own underwear,
including panties, a padded bra sized for a teenager, some hose to be worn
with garters plus pantyhose, and a garter belt. All the clerks naturally
assumed I was female....but why not, I looked, felt, and acted like one. We
went to buy shoes for me, suitable for my age. I was able to try them on and
practice walking in heels which, by now, I did with ease. I was completely
confident sitting in a skirt with the shoe salesman at my feet and keeping my
legs together. I had learned my lessons well. Auntie was proud of me.
As we continued to discuss my wanting to be a girl, Auntie explained that it
might not be possible for me to continue this forever. I told her I was very
happy as a girl...that I didn't want to be a boy, at least not live as one.
She agreed to help me on a part-time basis to fulfill my desire to be a girl
until I come of an age when I could decide for myself which direction I
wanted to go. But for the time being, I'd have to live two lives. She made me
understand the problems. We talked about the downside of being a woman...how
women are talked down to and patronized. How a woman must always keep her
guard up with men. The glass ceiling in the business world. I was willing to
accept all that. I told her it wasn't easy being a man either, especially
when you don't conform to the stereotype of a "jock". I had developed more
confidence in myself as a girl than I ever had as a boy, probably because I
was now better looking and felt better about myself.
We went in public a lot more as mother and daughter. Although her clothes fit
me, she bought me many things more for a teenager. Dressed as a girl, I was
paying notice to boys and they were noticing me. I was comfortable talking to
them when they would approach. It finally happened when one boy started
talking to me, we got acquainted, and he asked my out on a date. I though he
was handsome and nice, and before I realized it, I accepted. Auntie thought
it would be OK as long as I was careful and remembered to be a lady. She was
as confident of my femininity as I was.
Dressed in a skirt, sweater, stockings and heels, I wore a panty girdle just
in case, both to conceal my genitals and in the event he got frisky and tried
to "feel" me. My date picked me up at the assigned time, and we went to a
movie. During the show, he put his arm around me and it felt good. Afterward,
we went for a bite to eat, followed by a long walk. We talked about
everything and nothing...boy/girl conversation. He was trying to impress me
and I was trying to please him. I made a conscious effort to watch my
vocabulary and tone of voice to keep it feminine. Otherwise, I was completely
relaxed as a young lady on her first date. Taking me home, he thanked me for
a nice evening and kissed me goodnight. I had never kissed anyone before, boy
or girl. My first kiss and it was with another boy! But now, feeling like a
girl, I returned his kiss warmly, as a girl would, feeling secure in his
arms. This was further assurance to me that I wanted to be female. I wanted
more kissing but I withdrew before it went too far. When I related all this
to Auntie, she was proud of me for handling it so well. She had been
confident I would. She was also not surprised that I enjoyed it.
When school started again, I was back to being a boy, in practice but not in
spirit. I could only be a girl on the weekends. Well, better than nothing. I
became aware that I didn't look at boys other than as competitors in the
scheme of things, but I now looked at girls differently. I looked at them
with envy...I studied them, their actions, movements, dress. I felt I could
relate to them, after all, I had experienced how they felt, their thoughts,
how their clothes felt. I now, more than ever, wished I could be one of
them...a sister. Yet, I still felt a sexual attraction to them. Maybe I had
changed too because the girls were friendlier to me than ever before. Maybe
they sensed the sisterhood I was feeling. I didn't exude the usual bravado
that boys my age exhibit. I established relationships with girls that had
never happened before. One girl in particular, Evie, I found especially
attractive. We went out on a date, ending in the inevitable kiss. This time.
I was the aggressor as boys are supposed to be and as much as I could be. I
didn't enjoy having to do it, but it was expected. The kiss was just okay,
but it made me realize I really enjoyed being kissed by a boy more. Maybe
because I liked being held securely in his arms and being submissive in the
act.
Evie and I got better acquainted and eventually become close friends. We
discovered we had a lot in common. (More than she expected.) Eventually, I
confided in her that I liked to wear girls clothes. She accepted that with
little surprise admitting that she thought I was different than the other
boys. And she wasn't offended. She wanted to see me dressed. Feeling I could
trust her....wanting to trust her...I arranged for her to visit me one
Saturday at Auntie's house. When she arrived, I answered the door.
"Hi, I'm Evie...is Bobbie here? I'm supposed to meet him at this address."
"Hi Evie...I'm Bobbie."
Her jaw dropped in astonishment when she saw me. I was wearing a miniskirt,
hose, a sweater over my padded bra, and high heels. I had red lipstick and
matching red fingernails. My hair was styled.
"My gosh, Bobbie, you're beautiful! You had me fooled completely," she
exclaimed.
We sat down to talk, as I crossed my ankles, keeping my legs together in the
short skirt. Evie was still speechless. I finally broke the silence.
"Well, are you offended, pleased, what? Say something. What do you think of
me now?"
" No, of course not! Why should I be offended? I think you're wonderful. You
obviously enjoy doing this. You're a beautiful girl, AND a wonderful guy. I
get two for one. Offended? No way!"
I was totally relaxed after that confrontation. We spent the afternoon
chatting as two girls. I explained how I started and how I felt. Evie was
very understanding. We went out that night as girlfriends. That was the
beginning of a beautiful friendship although she was sworn to secrecy. Evie
taught me things about being a young girl that Auntie had either overlooked
or forgotten. She further enhanced my desire to be a female.
We were the closest of friends, both as girls and as boy/girl through High
School. We ultimately grew intimate, since we were dressing together, and as
a girl, I could spend weekends with her at her house sharing her bed, as
girls do. Sex with her was wonderful especially when her parents were around
and completely unaware of my true gender. She grew to love lesbian sex, which
we both agreed was safer. Imagine, I was welcome to sleep with her in her
parents home. I was treated like royalty...female royalty. I could prance
around in my lace nightgown and a robe and they never suspected I was
anything other than a young lady.
After High School, Evie and I enrolled in college together and shared a small
apartment. I wanted to register as a female but it was too much trouble and
confusion changing identities. Auntie and I discussed my changing genders
permanently. In other times I would have done it, but now, with Evie, I
wasn't sure...I loved her and wanted to marry her, but I still wanted to live
as a woman. So, I continued the dual life. I attended classes as a man, but
we'd go out and socialize as two women. Over summer vacation, we took jobs as
library aides at the college as two women. I was still more comfortable
living in a feminine persona. My hair was very long so I kept it in a
ponytail, my ears were pierced for earrings, I kept my skin and complexion
feminine with cosmetics and skin care treatments. I kept my weight down with
diet to maintain a feminine physique although I was naturally thin anyway. My
body was completely shaved, and from all the years of wearing a bra and some
breast exercises along with the use of herbal hormones, I had developed a
small bust, enough to show a little cleavage with the right bra and making
wearing a bra a necessity. I had mastered how to apply makeup and do my hair
so that I looked like a natural woman, and I felt like one. The summers were
too short...working as a woman in the company of other women was heaven.
Soon after graduation, Evie and I married, a small but traditional ceremony,
after which, we honeymooned as two women. Evie was content to let me live as
I please as long as I agreed not to have sex change surgery. I did indulge in
electrolysis to further effeminize my body. Evie got a job as a teacher,
having gotten a degree in engineering, I found a job in technical sales
requiring a lot of travel which afforded me the opportunity to crossdress
when out of town. I tried making some sales calls as a woman, posing as a
substitute for my male self who, I said, was detained, or some other excuse.
I found it to be very advantageous, getting me access when and where male
salespeople couldn't, or just the novelty of being a woman in a male
dominated field. One of my largest accounts was a female owned business where
the owner was a feminist. As a woman, I was received graciously. As a man,
she didn't want to talk to me. I also discovered how men were so easily
influenced by a short skirt and nice legs. A few drinks and a few kisses when
necessary and many deals were closed. I could see how women can sleep their
way to the top of an organization. And I still enjoyed being held, romanced,
and kissed by a man. I often wanted to go farther but couldn't risk it..
In time it got too complicated trying to balance two personas, one being
fictitious, so I went off and became my own salesrep, as a woman. This
allowed me to live en femme full time....my dream. I've been happy ever
since. I'm convinced I was born to be a woman as I'm sure Auntie knew from
the beginning.
If I knew who the doctor was who identified me at birth as a male, I'd sue
him for mal-practice.
The End
Angelica
- 14.09.2021
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