Transforming Bobbie
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Dressing For Bob free porn video
Dressing for Bob
by Joyce Domai
My adventures in women's clothing started in the usual way. Mom and Dad
were out, I went exploring, got dressed up and liked it. A lot.
It was my #1 fantasy through high school and college.
After earning a degree and getting a job, I was able to afford an
apartment on my own. I was working as an engineer and doing OK. (Yes, I
was a geek.)
I'd acquired a small wardrobe and would dress up in order to masturbate.
That was the extent of my sex life.
I decided to attend the local community college to study business in
order to fill gaps in my education. At the first class, a guy asked if
anyone wanted to carpool from the town where I was living. I thought "Why
not?" and that's how I ended up meeting Bob.
I was 22, 5' 10" and skinny. Bob was about 35, and overweight. Still, it
was OK to share the half hour ride, twice a week.
It turns out that Bob was fascinated with sex. He'd tell me about his
girlfriends. He'd fantasize about girls in our classes. I was quiet, but
he loved to talk.
Finally, after a few weeks, I had to speak up. I couldn't disclose my
cross-dressing fantasies, but I had to ask about one piece of it. While I
considered myself straight, I had to know what it was like to be a girl.
So, as we neared my apartment one night, I asked, "Bob, I have a strange
question. I really want to know what it's like to give someone a blow
job. Would you just let me blow you?"
"Are you queer?"
"No, not really. I've been pretty sheltered and I just want to know what
it's like."
We discussed it, discussed a little about my sexuality and Bob agreed to
come upstairs. I seated bob in my favorite armchair, got him a beer and
knelt down in front of him. With his help, I got his pants down, played
with his cock and, well, took it in my mouth. I'm not sure I was good
but, after a while, I was effective. As I took his cum in my mouth and
swallowed it, I realized I enjoyed it. I liked the taste and loved the
texture. I licked him clean and he went on his way.
The experience produced several good jerk-off sessions for me over the
weekend. When we got together for next week's ride to class, Bob asked if
I'd enjoyed it. I sheepishly replied that I had. Bob said that he could
use some relief. This developed into our regular pattern for about a
month.
Finally, I had to carry it a little further. I got Bob a beer, turned on
the TV and said I'd be right back.
I already had the panties on. The rest of the clothes were in my bedroom.
I took off my boy clothes. My legs have very little hair, but I'd shaved
them, my chest and underarms that afternoon. For my first time in front
of anyone, I went classic. White bra with rice filled stockings to fill
out the C-cups. I'd been experimenting and I loved this feeling! White
silky blouse and short red plaid skirt. Yes, classic schoolgirl!
I added white pantyhose. (It was my first time and i would expand this to
stockings later.) Patent heels showed off what were, and still are, nice
legs. Foundation, blush and eye shadow were the quick makeup. Glossy pink
lipstick and a mail-order wig, long and brown, completed the outfit.
As I clicked my way back into the living room, Bob turned and his jaw
literally dropped. I cocked my hip and said "Well, Bob. This is how I
want to dress sometimes. Enjoy the look." I got down on my knees and
sucked him like there was no tomorrow. After he came, I got up, got a
glass of wine and sat on the sofa across from him. I lit up a cigarette,
something I was starting to do when I was dressed.
"Do you always dress up like this?"
"No, but I've experimented and I wanted to take 'our thing' a little
further."
"Well, you do look hot and you do give a good blow job. You must be gay."
"I feel like a girl taking care of her man. I don't feel gay. Just call
me Joyce."
"OK, ... Joyce."
Over the next few weeks, I tried several different looks. Business suit,
cocktail dress, even really tight jeans (with the man parts tucked up)
and a tight, sexy top. But my favorites, and I think Bob's also were
short skirts. And as it was now moving into winter, I got to try some
sexy boots, with both the short skirts and a longer denim skirt.
It was good. I'd get to dress up and satisfy "my man". Bob got a great
blow job, as I was getting better at it. I didn't care if he thought of
me as male or female. I loved the feel of my lipstick covered lips on his
cock.
But it was getting a little stale and I knew it was up to me to take it
to the next stage.
The following week, as I was again kneeling in front of Bob, dressed in a
short denim skirt, tight pink cotton sweater, real stockings and my
favorite black heels, I looked up and asked Bob if he'd like to fuck me
in the ass. His eyes got big and he said, "Yeah, Baby. I'd really like
that."
I got up and led him into the bedroom. I took off the sweater and the
skirt. I left on the bra, garter belt, stockings and heels. I got onto my
knees on the bed and leaned forward over some pillows. I directed him to
some lubricant on the bedside table and he applied some to my ready ass.
Bob was an average size guy, but never having had anything other than my
finger in my ass, he felt huge. Nevertheless, he pushed into me and it
hurt! At first. Then I got to appreciating what I was wearing, what I was
feeling and the absolute feeling of fullness. As Bob started to cum, I
realized I was cumming from rubbing against the pillows.
We carried on this way for another few weeks, until the end of the
semester. Even though I could definitely please him, I don't think he was
ready for a transvestite relationship; nothing more than casual sex.
I wanted more. My relationship with Bob emboldened me. I sought out a new
boyfriend. I approached a female friend at work who was a Mary Kay
consultant. She helped me learn about makeup. And she was my first
'lesbian' relationship. I'll write about these experiences later.
Hester
- 07.08.2020
- 15
- 0
