jessicasatin
Posts: 1
Joined: 12/19/2009
Status: offline
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I will start out by saying that I've always loved the feel of lacy
fabric on my skin. I learned this by snooping through my mother's
things she would discard, just as worn panties of pantyhose. In Jr High I would act
sick to stay home and jerk off all day long.
I eventually grew out of it for a while when I started dating. I
always figured that no woman would have me if she knew I liked to
wear a bra and panties. It was funny though - every time a
relationship ended I was in something frilly within a week. I guess
it was just my sexual release when not in a relationship. Seemed
healthy enough to me. No one was getting hurt, and I would have a
great time.
Don't get me wrong; I love sex with women. I just have some of the
most mind-blowing orgasms when I am fantasizing and dressed up. It
was during just one of these orgasms that my life would take a very
strange and fortunate turn.
I had been dating a woman named LeeAnn for about a year. After
several attempts to introduce gender play into our love life, I had
given up a few months before. The sex was getting stale, largely
because I knew I would never have her make me over and play the
dominant role in bed. I just didn't think she had it in her, so I
figured I didn't need to put much effort into our sex life if she
wasn't going to meet my fantasies. After a couple of months without
getting oral satisfaction from me, she'd had it.
"It's the one thing you're good for in bed!" She was pleading for my
tongue.
"You haven't really bothered to find out what I am like in bed, you
selfish bitch!"
Okay, I could have worded that better, but I wanted to get into
something lacy and soon. I figured she'd take the hint, or walk out.
She did the latter, saying she'd be by for the rest of her things on
Tuesday. Good riddance, I figured.
Now, since my last attempt to get all feminine, I had enjoyed some
financial success. I figured this meant I could splurge a little and
buy some neat things I had always denied myself. The internet helped
too, as I could order many of the more embarrassing items on-line. I
got myself a couple of little dresses - halter jobs with zippers in
the back. For some reason, the more effort it takes to get in and out
of the clothes, the better it is for me.
I also got some shoes. I actually decided to indulge a long time
fantasy and out myself as a cross-dresser to a shop girl. I went into
the local lingerie/novelty shop and started looking at shoes. A woman
approached me and asked if she could help. I told her I planned to go
to a Halloween party as a French Maid as a joke on my girlfriend, who
had refused to wear such a degrading costume. LeeAnn and I had that
very conversation the year before, as we were early in our dating. At
my office Halloween party, she dressed very conservatively in a
gangster costume. I pointed out how the VP of finance had dressed as
a maid and had her husband ordering her about. It was a great way for
Francine to let her subordinates know that she can both give and take
orders.
LeeAnn thought otherwise. She thought it was degrading. I was just
using this story as a gateway to get this sales clerk to let me try
on some slutty shoes. The clerk was a cute 20 year old college
student named Leesa. She flirted with me, saying it was cool that I
was willing to take on a feminine role for an evening, if only that.
I eventually picked out a pair of 6 inch platform pumps.
I was looking forward to after work on Tuesday. LeeAnn's stuff would
be gone, and she'd have left the key to my apartment. This meant I
could get dressed up and not worry about being caught. Little did I
know, I was caught before I even got home. LeeAnn had always given me
grief for emptying my pockets into the dish we kept our keys in by
the front door. When I'd bought the shoes Monday night, I had placed
the receipt in my pocket. When LeeAnn was putting her key in the
dish, she saw a receipt from Lover's Package for 6 inch platform
shoes in size 13.
So, nothing looked out of place when I got home, aside from a
picture being missing off the wall. It was something we'd picked out
together, and I was a little pissed about it being gone. When I went
into the bedroom, something else was wrong. I wasn't sure what it
was, but I knew something was missing. I opened the closet to hang my
tie, and then I knew. All my clothes were gone. All I had was what I
was wearing. Hanging from a string in the closet was a pink envelope
addressed to me:
Brett,
I see now why our sex life has been so bad lately. You tried to hint
and suggest what you just should have come out and said. If you need
to get all girly, we could have done that. Of course, the fact you
never were brave enough to tell me straight away pisses me off. If
you want me back, and if you ever want to see a stitch of your male
clothing again, you'll follow my instructions to the letter until at
least midnight tonight. First, you will strip off that clothing and
put it on the patio. I am watching. You will get a phone call with
instructions once you comply.
LeeAnn
I didn't know what to do at first. I was dumbstruck. If nothing
else, replacing my wardrobe would be expensive. I knew LeeAnn could
be reasoned with once we were face to face. I had to ride it out
until then, and then maybe we could come to an understanding. I
decided it also might be fun - maybe LeeAnn had more adventure in her
than I had thought. I might as well find out I thought, and I happily
stripped and tossed the clothes through the blinds onto the patio. I
saw some movement, and it was she grabbing my clothes.
The phone rang. "Hey Brett, we're going to have some fun." I was
both horrified and hard as a rock. I heard her car door slam, both on
the phone and outside the door. "What I always loved about you was
your predictability, hon. You always just threw your clothes on the
floor not thinking about what a mess it made, or what you left in
them. Do you know where your wallet is?" Oh shit. "I'll give you a
hint - it's in a pocket, and you won't have any of those to distract
you for the rest of the night. Go look in the top of the two drawers
you gave me. There is an envelope. In that envelope is another sealed
envelope. If you open that sealed envelope, I will burn your
clothing. Follow the instructions. The next time we speak, it will be
face to face. Have a good night, Brandi."
Holy fuck. Here I was, butt-naked in my living room with not a
stitch of clothing, and not a penny to my name without my damned
wallet. I couldn't even mail order clothing overnight without my
credit cards! I decided I better play ball.
Brandi,
You might notice I stopped calling you by that brutish boy's name.
Boys are yucky, and I want you to remember that. I did leave you some
clothes. They are hanging in the den closet. Put them on, and take
the sealed envelope to Leesa at Lover's Package. She helped you pick
the shoes, didn't she? She'll help you some more tonight. Be there by
seven, you wouldn't want them to be closed and be stuck with only one
outfit.
TTFN
Okay, so I'd get dressed and go to Lover's package. I looked at the
clock on the wall, and it was 6:30. I had to hurry. I opened the
closet, and stood both horrified and aroused at what I saw. It was
one of the dresses I'd gotten online, nicely ironed and ready to
wear. Beneath it were the shoes. No underwear of any kind.
Thankfully, the dress was fairly conservative in length and cut. I
felt more and more ridiculous the more I looked at myself. I was a
man in a dress and high heels. And I had to leave, now!
I got lucky in that I made it to my car with no one close enough to
make out the details of my predicament. I got to the store, and there
were three cars in the lot. I figured one had to be Leesa's, one was
probably the other girl working, and the last had to be a customer.
Damn. I had been that late shopper in this place before - I knew the
drill. They'd let him shop for a half hour after closing, but they'd
lock the door at 7. I had to go in.
I walked in and the girl started laughing. She stopped, and said she
was sorry and asked if she could help. I asked for Leesa, and was
told she was in the back with her boyfriend, by the dildos and sex
toys. I walked back that way, trying not to imagine the smirk behind
me. Leesa and her boyfriend - a huge guy who spent entirely too much
time at the gym - were making out hot and heavy. Her eyes opened long
enough between kisses to notice me coming.
"I see your story last night was bullshit." She said as I handed her
the envelope. Her boyfriend was openly laughing at me. After a moment
reading, she asked, "Do you know what this says?"
"No, my girlfriend said not to open it."
"Okay, first things first: she's not your girlfriend any more. She's
your ex - it says here she dumped you last week. It says you are on a
mission to win her back, and asks that I do her a favor." She then
pulled two 100 dollar bills from the envelope. "And she paid me to do
it. You will probably enjoy this all anyway, so try to relax. Mike,
give Brandi a hand."
Mike reached into his pants pocket and produced a pipe. A little pot
might make all this more enjoyable, I thought. I took a hit. I passed
it to Mike. "Take two, you could use the help I think." He chortled.
I took the second hit, and noticed an odd taste to it. I suddenly
felt terribly high. "Did I mention the heroin I put on that bowl?"
My memory of the next hour is vague. I knew they tossed my dress
because my cock had left tracks on it. They then fooled me by
offering to have Leesa model any of the stripper dresses they had at
the store. I picked a sexy Lycra thing with a low bust line, no back
and peek-a-boo holes all over. It had a skirt so short it would be
impossible to not flash panties in the thing. It was hot just
imagining that little minx in the thing.
Of course, she looked hotter than I'd imagined. She came out of the
dressing room doing a little dance. Mike was playing with himself a
bit by now. I was naked and hard as a rock, and wearing high heeled
shoes. It was a bizarre feeling as she approached me. I was feeling
very agreeable and happy as she whispered in my ear, "I want to make
you a deal."
"What's the deal?"
"I will suck your cock right here and now, but you must perform oral
sex at my command one time."
"Deal" I almost shouted it, not thinking of the wording. She bent at
the waist, giving Mike a clean shot of her uncovered snatch as she
took my cock in her mouth. She bobbed her head up and down and hummed
a bit. Her hands stroked my balls as her tongue worked magic on the
head of my cock. I was getting close. She looked up at me and let my
dick out of her mouth for a moment, and asked me, "Should I spit or
swallow?"
"Oh, swallow it!" She responded by taking the hole shaft in -
swallowing my cock. After about four strokes like that, ejaculation
was imminent. Just as I felt it working to the tip of my cock, her
finger shot into my ass. I shook violently, cumming harder than I
could ever remember.
"Just remember, you owe me one." She said as she stood up, wiping a
little stray semen from the corner of her mouth and licking her
finger clean. She then reached behind her, and said, "here, wear
this" as she produced a French maid's outfit. "It's what you like, so
don't be a sissy about it. First, we need to take care of little
willy there." The then had me step into what she called a gaff. Once
on, it pulled my junk totally against my body. Then some lace
panties, and a matching pink bra with some breast forms in it. The
bra straps stood out pink under the black maid's outfit. Just when I
thought this outfit couldn't get more humiliating, Leesa produced a
petticoat. It stood the skirt nearly straight out. I was a mess of
lace and frills, and I was hot as hell even if my cock was safely
limp in its prison.
She then sat on my lap and produced some makeup from a small
handbag. "Just some blush, mascara and lipstick for now" she said as
she layered it on thick. She produced a small mirror, and showed me
the result. I had real cocksucker's lips - bright red and totally
full. I instinctively touched them as I looked. "What do those look
like to you?" she asked me.
"They look like cocksucker's lips" I said, not knowing what else to
say and still being fairly high.
"I'm glad you agree, slut. Mike, come over here." I was horrified,
and my eyes must have said so. "You owe me you little sissy - and I
am ready to cash in. I want you standing bent over, just like I did
for you." By this time, Mike's cock was out and he was standing two
feet from me. "If you don't do this, we're putting you out on the
street like this. No ID, no car keys, no house keys, no money. You'll
be turning tricks or a jailhouse bitch within two hours." Fuck - she
was right.
I did as I was told. I bent over and took the head of Mike's semi
erect cock in my lips. It was wet and had a salty taste. I tried to
just do the things I liked. I teased the head with my tongue, and it
sprang to full erection. I knew from being a man, that the key to the
erect cock is pleasant repetition. I started going down on the shaft
at a steady pace I felt I could keep up. After a couple of minutes of
bobbing up and down, the moaning started. The cock started to twitch
a little. Mike's hands grabbed the sides of my head, guiding gently
the progress of each stroke. Suddenly, he became more urgent, and
rather than gentle guidance, his hands forced my head down on his
cock until it was into my throat and making me gag. The gagging
action only aroused him more. I felt the cum streaming down my
throat, and suddenly I realized something. I was turned on. Just at
this moment, I noticed mike was looking behind me.
I looked over my shoulder, and just beyond my petticoat was a
leather clad LeeAnn wearing a huge strap on dildo. "I think you might
just win me back you little slut." I was overjoyed, until I realized
she was getting closer and closer with that dildo. It then occurred
to me: I wanted her to fuck me like this all the time. If she'd do
that, I'd eat her out whenever she wanted.
"I want you to fuck me," I moaned. "Fuck me like this, and I'll do
your oral whenever you want!" As she entered me from behind, I turned
and noticed that Leesa had been getting pictures of the whole affair.
I guess I was in it now.
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One of my favorite feminization stories - 
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