Date: Tue, 28 Jul 2009 08:56:06 -0700 (PDT)
From: Michele Brown <michelebrown@rocketmail.com>
Subject: Charles and I part 3 TG Story

 	Over the months Charles and I would see each other when we could,
some days it was just me and him talking about things, no sex, no kissing
maybe a hug here and there, but nothing out of whack. The other times, well
we both had smiles when we got home. Even with school and work on my plate,
I made it a point to do something special for Charles' birthday in a couple
of weeks. I bought a pair of clear platform heels, black thigh high nylons
that didn't require a garter belt (yes, I had gotten frustrated with the
other ones), new skirt (black denim) and a pink blouse. I also made another
purchase, a 8 inch dildo and lube, lots of lube. When I got home that night
I wanted to try everything, but I held off, I wanted to be calm walking in
the shoes and using the dildo. The next day was a different story, after
work, I came home went straight to my room, took a shower and tried my new
outfit. I was in heaven with the new stockings, didn't even try to slip
off, the skirt was moderately tight and the pink blouse was sexy, and the
moment of truth, I brought the heels out. Standing up, I slid my foot into
their respective shoe, yeah I was higher up than normal, but the heels push
my ass out filling my skirt to be even tighter, I walked a few steps first
on the carpet then on the tiled floor, tiled was the way to go. I would
walk, trying not to twist my ankle, it would require practice. Tomorrow the
heels and dildo, hope I was ready.

	The next night I came home from school, my mom was out working late
again; freedom of the house was mine! Tonight I was going to be a slut; I
took my shower, re-shaving my body, toweled off everything. I came
downstairs in my bra and panties turning the television on, I started to
paint my toes a nice red color, while they dried I did my school work. Once
they were dried I put the stockings on the look of the red toes coming
through the black was hot, but even sexier once I got the platforms on. So
fucking hot, I couldn't help but to admire my legs, toes...next thing I
know, I'm reaching for the dildo, licking the shaft, and kissing the
head...I know what is missing, I reach in my bag for red lipstick after
applying it, I went back to kissing the dildo leaving traces of my lips all
over it, taking the dildo I try to see how far I can deep throat it,
leaving a lipstick ring after every try. And now the moment of truth, I
grab the lube and pour some in my hand at first I use it on my cock, making
my cock nice and wet, allowing my hand to jerk it off faster than before, I
was about to cum, I needed to stop, I let my lubed hand play with my balls,
with my finger inching ever closer to my asshole. I slowly put one finger
towards the hole, first was more of lubrication the second was my fingers
trying to sneak in, little more lube. Once I felt I was lubed enough, I
used some on the dildo, the redness seemed to smear into the clearness of
the lube, I put the dildo against my asshole, I can feel my own ass
resisting. I went back to using my fingers to loosen me up, once I felt I
could do it, I brought back the dildo to the place where it was not
wanted. Taking a few deep breaths, I slowly move it in; I can feel it going
in, I can feel my hole opening up. Little by little, the dildo moved its
way into my ass, with a bit of push and a series of twists, I felt the
whole head inside me. I let it sit there, my ass trying to get used to it,
I pushed a little more I had the some shaft in me. As I relaxed for a few
moments, I started to move the dildo back and forth; my ass almost had a
mind of its own pushing back and pulling in. In a few moments, without even
touching my cock, I came, and boy did I cum, but I kept the dildo stay
inside me until I heard a car pull into the driveway. I gathered everything
and ran to my bedroom. I tried to do a quick change, but the dildo didn't
budge from my ass, I put my underwear on and my pants. I could hear the
door open, once I knew everything was put away, I could hear my mom's
footsteps coming to my bedroom door, I ran to my desk and without even
thinking sat down hard on the chair forcing the dildo deeper into my
ass. Damn that hurt. My mom knocks on the door, "Hey Chris, can I come in?"

"Sure Mom!" I answered, need to take deep breaths, the dildo luckily was
thick at the bottom so I knew it couldn't go all the way into me, I feared
it would be lost in my ass. But on the flip side, it wasn't a good thing as
my asshole accepted a little more, damn it felt good but it was becoming
difficult to keep my concentration. Oh shit a book! I wanted to look like I
was studying, just as I leaned over to grab my backpack, my mom walked to
the desk. "Studying?"

Acting as if I was putting the book away, "oh yeah, final year lots of
homework" looking up to her. "Are you wearing lipstick?" oh shit I forgot
to wipe my mouth, "no, I had a couple of cherry popsicles while I was doing
my homework? Why is my mouth and tongue all red?" don't be nervous Chris.

"You have red smeared around your lips. Looks like lipstick, sorry didn't
mean to bother you" breath Chris...exhale, inhale. "Your not bothering me,
is everything ok?"

She sat on my bed and looks down, "Chris, I know I haven't been around much
and you pretty much have been running the house lately making sure
everything is done. On top of that, with your school and work, but I need
to know something. Have you been going to gay clubs in drag with a guy?"

I couldn't answer; I couldn't move I felt my face flush red.

"That wasn't red popsicle either was it?"

"No, it was lipstick and yes, I have been going to the gay club." Looking
down not even wanting to look her in the eyes, I hated myself, I hated what
I had done...all of it! There was no punishment worse than disappointing
her. Tears rolled off my face, as I looked down. "I'm sorry mom!" was all I
could murmur.

"Don't be sorry it should be me, maybe I should..." I cut her off

"It has nothing to do with you mom, this is who I am. Has nothing to do
with you raising me, it has nothing to do with you being a strong woman, it
has nothing to do with pissing dad off, it's about me. I know I am an
embarrassment right now, but what I do doesn't change the fact, I love you
mom. It doesn't change the fact I do what I can around the house, and try
to help with bills." I spat out. Even I was surprised by what I said. Even
surprised my mom, she sat there no tears, no anger just nodding her head in
agreement.

"So Chris, do you want to be a woman? Are you gay?"  I really could have
used a drink at this point, how much do I tell her and how much do forget
to mention? "No, I don't want to be a woman! I enjoy the clothes and the
feeling it gives me, but I would not do it full time. The gay question is
tough, I really like girls, but when I am in drag, I feel feminine want to
have fun with guys!" I could see this was tough, maybe I shouldn't have
said anything about guys...

"How far have you gone with a guy?" She looked scared of the answer

"Want me to be honest?"

With a deep breath and a heavy sigh, "Yes!"

"Oral sex" I was shaking

"How many guys have you been with?"

I lied, "Just 2 guys!"

"Who?" damned questions were getting tough to answer

"Remember Bill? Him and I fooled around and Charles"

"Is Charles the one who takes you to the gay club? Who is he and how did
you meet him? I'll be right back, you want something to drink? I'm sure you
need one as much as I do."

"A beer?" might as well ask for something, drinking beer is not as bad as
sucking a guy's cock at this point. She came back handed me a can of beer,
she had a wine.

"I met Charles when I was looking for women's shoes at the department
store. He is the manager there. And yes he is the one that takes me to the
clubs.

"Ok, we are going to continue with me asking questions, but I want to see
the outfits you bought!" I was hoping this would end soon. I went into my
closet, opened my chest of treasures, and presented her with my blouses and
skirts. "What about makeup, bras, panties, shoes? I want to see them all!"
I went back grabbed the rest and went under my bed and grabbed the new
items, hearing my mom gasp when she saw the platforms. "Nice selection,
don't know about the stripper heels, but the rest is nice." Get dressed and
come down stairs so we can finish talking.

"I am dressed" I was a little confused.

"Uhm no, get dressed in your female clothes" she snapped back "and bring
the stripper heels I want to see if you can really walk in them."

She left the room, and I gathered my clothes. I stripped off my boy
clothes, and started to get dressed. I also did something I wanted to do,
take the dildo out! In one of my uncoordinated moments, I reached between
my legs to take the dildo out, it was even more stuck, I started to
panic. Perfect the first night I talk to my mom about this stuff, and she
will have to take me to the hospital to take a dildo from her son's
asshole. I laid on my side on the bed, reaching back, I slowly moved the
dildo out of my ass. Then with a little tug, I was able to get it out of my
ass. Thank God! I reached back feeling my hole, the fucking hole felt like
the Grand Canyon. I hope it goes back into shape..."Chris, get dressed I
want to see you now!"

"Can I take a shower first? Just feel sweaty"

"Fine, I'll be back. Just be ready when I come down!"

 I wasn't kidding; I was sweating the cool water hitting my hairless body
felt good, after the shower I put lotion on my legs it was time to get
ready.  I got dressed in my pink blouse, black denim skirt. No nylons but I
brought them with me. I slid my foot into the white slides they helped me
with Charles; I hope they work for me with my mom. When I left my room I
could smell cigarette smoke, my mom quit smoking a few years back, why did
she restart?

I followed the smell of smoke into the kitchen, where she sat. Her back
towards me, she must have heard the sound of my shoes, as she turned
around. "Oh my God!" was all she could say with a cigarette in her mouth
and a glass of wine in her hand. "Well, definitely not what I expected. At
least you shaved, and actually that is not a bad outfit." I sat across from
her, trying to sit as girlish as I could, she stood behind me and started
to work on my hair. "You always had pretty hair! So tell me about Charles
and I want details, treat this as a girl talk."

As I spoke about how we met, the first time I sucked him and how we would
just meet when we could. I could feel her tensing up occasionally and
relax. "How did you find out mom?"

"I saw you and him leaving one of the clubs, then waiting for the bus, your
backpack gave you away. I tried to think it was someone else, but one day I
went into your room and found your stash of clothes." As she pulled my hair
making a tighter braid. "I cannot give you my blessing to see him, he is
much older, but you're also mature enough to handle things on your
own. Just be careful with him. As far as you dressing up, I can handle it
ONCE in awhile, NOT all the time, understand?"

"Yes!"

"Let me see you in those heels" she stopped her hair work, allowing me take
the shoes off and put the other heels on, when I stood up she was looking
up at me. "So are they for going out? Or are they for seducing?"

"I would rather not say right now" I tried to avoid the question, as I sat
back down for her to braid the other side of my head. She was just staring
at me; I could feel her eyes burning into my brain, looking for the correct
answer. "Seducing, I wanted for Charles and I to do anal." I said it, oh
hell I said it. She went back to working my braid, not saying
anything. "Just make sure when you do it, be relaxed and make sure he
doesn't ram it in, that's only in porn. Take it slow, you and he will enjoy
it much more."

"I'm sorry?" I couldn't believe what she just told me, but I couldn't pass
up an opportunity to ask her questions. "How do you know?"

"Chris I'm your mom, you really shouldn't be asking me...it is a girl's
night right? I love to do anal and no your dad wasn't the first." Now I
didn't know if *I* wanted to hear this, but she had to listen to me. She
finished my last braid, left the room bringing back her makeup kit. Doing
my makeup she continues with her story. "I was about your age, I wasn't new
to sex, so the guy I was seeing he was a college senior, he picked me up
for a party. It was him, his frat friends and one other girl besides me."
Well the drinking was heavy, and someone dared me and the girl to kiss, we
started kissing. Well the kissing turned into fondling; we were in our own
little world. Until the guys started taking their clothes off. We were the
center of attention, both of us girls were sucking cock and getting fucked,
I was on top of some guy with his cock buried in my pussy. When I felt
someone behind me, it was my boyfriend with his cock aimed at my asshole, I
begged him not too, until he did the whole `if you love me" bit, I made
sure he used lube. At first it hurt, then I noticed the girl was getting
double teamed as well, and watching her take it turned me on. My boyfriend
cumming in my ass, then another guy entering I didn't want it to stop. But
that wasn't the first party nor the last, unfortunately your dad didn't
like anal sex when he left the first thing I did was go to a bar (I know I
told you I was out working) found a stud and had him fuck me until my
asshole was hurting."

"And how many times did you say you were working late and you were actually
getting laid?" not that I was mad; she needed sex just like me.

"Once a week, that is how I saw you and Charles, I was looking to go to a
bar for some action. There you are all done, take a look in the mirror. You
obviously won't pass but at least you look better." I checked the mirror, I
looked way better I even loved the pigtails she gave me. Damn if I could go
out. Then I hear her taking the car keys.

"Where you going mom?"

"All this talk about sex, I getting wet and I need to get fucked. Did you
want me to drop you off at the club and you can take a cab back home. No
men in the house, if I can't bring anyone, neither can you!"

I thought about it, if I go to the bar I could call Charles to meet me
there. "Sure, let me get my bag." She stopped me and gave me one of her
oversize purses "You may want to use this instead, this way you can change
shoes when the stripper heels become a pain. I also have some makeup and
condoms in there, just in case."

We walked out of the front door, I was nervous, wanting to take the
stripper heels off but she wouldn't let me. We got to the car; as soon as
it was unlocked I jumped in as soon as I could. "Where's your stockings?"
she asked. "Inside, I don't need them!"

"Go and get them! It completes your outfit, leave the heels here and run
back in and get them!" I did as she said, I ran damn did I run. As we
drove, I put the stockings on with her giving me pointers on how not to put
runs in them. Once we got there, I slid my shoes back on, she told me to
have fun and I wished her the same. I walked into the bar, went straight
for the payphone to call Charles.

"Hey Charles, did you want to come down to the bar I have a surprise for
you."

Charles walked into the bar with one of his friends, he came over to me
gave me a hug and kiss. "You look good! I love the look, who did it for
you?"

"I'll explain later. Who is your friend?" I was a little mad; it wasn't
just me and him

After a quick introduction, friend's name was Tim; Charles ordered drinks
for all of us. He asked about the shoes and outfit, I told him they were
part of his birthday present. "What's the other part?"

"Once you and I are alone I'll show you." Teasing him as I rub the platform
against his leg, I could see

"I guess it won't be today, Tim is my ride here and back. Just tell me,
seriously I'm too old for games."

"Step outside with me, please!" I pleaded.

"We will be right back Tim." I took him outside to the side of the
bar. Before I even said anything, I kissed Charles on the lips, I missed
his tongue. He broke it away, "Is this the birthday surprise? I hope there
is more."

"Nope I wanted you and I to be alone, tonight I want you inside me. I want
you take my virgin ass."

"If you want I can have Tim drop me and you off at my house. But I don't
want to do that to Tim, he did take me down here to see you."

I hate it, but he is right. I guess I would have to wait. I'm sure mom
didn't have to wait long. We walked back into the bar, we stayed there just
bullshitting. Tim was a pretty nice guy, as we kept drinking Charles was a
little mean towards him at times. When Tim went to the restroom I asked
Charles why he treated Tim like that. "He can be stupid, the only reason
why we are friends I get him movies cheap and he gives me car rides. Just
like the only reason why you and I hang out, I have a dick you like to suck
and you have the lips to suck my dick!" Damn talking about feeling like a
whore. Tim came back to the table and asked if we could leave, I agreed ,
Charles was about to pass out, so Tim and I tried to walk him out to the
car, once we got there, we dumped him in the backseat. I started to walk
back towards the club when Tim asked if I wanted a ride, plus he need ed
help taking Charles to his room. I agreed, once we got inside the car. We
could hear Charles snoring in the back, we tried to talk about different
things mainly how him and Charles have been friends since high school, and
he told me about how he went to jail for Charles, I guess ole Charles was
drunk and tried to pick up a straight guy. The straight guy kicked his ass
until Tim stepped in and beat the snot out of the guy. When the police
arrived they grabbed Tim and arrested him for assault. Once we got to
Charles' house I kicked off the stripper heels and put on the wooden heels
a lot lower and hopefully easier to walk in to carry the big doofus. Once
we got him in the doorway I kicked my shoes off to walk down the stairs,
there was a couple of scary moments where we all almost fell, but we made
it. "Charles?" his mom called out. I looked at Tim, "she can't see me like
this!" Tim stepped out into the light, "It's me Mrs. Silverman, I brought
Charles home." "Is he drunk again?" she hissed. "Yeah, he had a little too
much." I can hear her groan in a displeased manner. "Why is it every time
he goes with you Tim he gets drunk? Don't you know he has a job and me to
take of?" I could see Tim being upset, "I'm sorry, I won't let it happen
again!" Again another groan, "Whose heels are these? What are they doing
here, did you decide to pick up a whore and use Charles' room for your
enjoyment?" Tim looked at me panicking "I partially stepped up, "No
Mrs. Silverman, this is Chris, I spoke to you on the phone, those are from
me. We went to a costume party, and I went as a prostitute. Couldn't find
any shoes except those in my size." Shrugged my shoulders looking at Tim, I
hope she buys it. "Good Night!" as she slammed the door. Tim and I gave a
look of relief.

We went up the stairs, I grabbed my heels and we got into his car. He asked
where I lived, which was 30 minutes away from the area. He asked how
Charles and I met, I told him everything, including the first night we went
out. "Sounds like Charles! He is always trying to get people involved into
his fantasies." Tim sounded pissed, I figured I might as well leave it
alone. After a bit of nervous silence, he asked me if I enjoyed that
night. I told him it wasn't bad, just didn't care for not knowing how he
felt. "Do you love him?"

"No! I like him as a friend with benefits, but nothing more." My stomach
grumbled I guess he heard it.

"Did you want to stop somewhere to eat? I'm getting a little hungry myself"

"As long as it is not a sit down restaurant, anything open for drive thru?"

It took a few minutes but we finally found a burger place open 24
hours. Unfortunately you had to walk up to the window, but Tim was cool he
walked up and ordered for us, I tried to pay him, but he wouldn't allow
it. There was a little park across the way, we parked over there, I put my
stripper heels back on (what?!? They really are comfortable once you break
them in) and we walked on the cement to a bench in the area. It was just
nice Tim and I just spoke about things, different things including
sports. He asked why I dressed up, he was hesitating to ask, I explained
every thing since I was a kid. Once we were done, we decided to just to
take a little walk to help get the food down. As we were walking I asked if
he was gay, straight or bi? He told me he was straight, I left it at
that. Before we got to the car, I asked for one favor if he didn't mind, I
just wanted to give him a hug for being so awesome, he said no problem. And
we stopped and we hugged, I took a chance and gave him a kiss on the
cheek. He just smiled, walked me to the car and opened the door for
me. When he dropped me off at home the sun was rising, I took my heels off
and ran into the house. I looked in the garage and my mom's car wasn't even
there. The bed wasn't slept in, the little hussy never made it home. I
brewed some coffee, and sat on the couch waiting for her. I must have dozed
off when she made it through the door, I woke up with a blanket on me.

I had a lot of doubts in my head about Charles, could he really be this
much of an asshole? Speaking of assholes, do I let him pop mine? So many
new questions, but I'm tired and need to get some sleep. I slipped out of
my outfit, took a long shower, pulled the curtains shut and went off to
bed.


Thank-you to everyone who has replied to me...hugs and kisses.
Michelebrown@rocketmail.com