Date: Wed, 17 Jun 2009 18:08:14 -0700 (PDT)
From: Michele Brown <michelebrown@rocketmail.com>
Subject: Charles and I part 2 TG story

"So I will see you at 8 next Saturday?" I asked hoping he doesn't back out.

"You got it!" Charles replied, we both hung up, I was excited.

We spoke on the phone for a couple hours getting to know each other a
little more. He was 28, lived in his mom's basement, was a huge Star Trek
fanatic and worked 2 jobs, one as the shoe department manager and the other
at a book store in downtown. After his father passed away, he has been
taking care of his mom and tried to help pay the house and other bills. He
wouldn't go into great detail, but he did explain he hated labels, but he
was attracted to anything that walks, except animals! He also let me know,
he was nervous when he made the offer of shoes for a blowjob, but he
couldn't help himself he needed some relief and I made it happen. He asked
me what I was wearing, before I could get to myself, and I told him I was
just laying on my bed wearing the shoes I got from him and a pair of
panties, maybe it was me, but I think he was breathing a little too hard if
you know what I mean.

I explained to him my experience with my friend (another story), and let
him know, when I'm in boys clothes, I can't do anything with a guy, but if
I have women's clothes on, I'm good to go (I learned that from my friend,
when he tried to kiss me when I wasn't wearing any femme clothes) – I
know weird but that's me <sigh>.

Next Saturday was a little more than a week away, but I needed to think of
what I was going to wear. I decided to take a shower, and as shaved my
body, I started thinking I was going to need new undergarments, makeup,
always wanted to wear thigh-hi stockings and maybe a new outfit. After work
the next day, I went shopping at my usual store, of course I got the glare
from the old lady at the cash register, but I'm getting dick, she isn't!

As the days went past, I was counting the days and the hours for our
`date'. The Friday before D-Day, I re-shaved my body again lotion my legs,
painted my toenails to the color of the fake fingernails (deep red). Got my
backpack ready for the trip downtown, and went to bed early, wearing my
panties to bed I figure would help me get in the flow of things, but all it
did was make me horny, thinking of Charles rubbing his hands on my ass, and
me rubbing his cock through his pants, as I was thinking of everything, I
needed my own relief I slid my hand down my panties and started to play
with myself, after a few moments, I came like I never came before, with the
cum settling on my stomach, I swiped it off my fingers licking it clean,
thinking of tomorrow night.

When Saturday arrived, I did my chores, my mom wanted to spend sometime
with me, so I went to lunch with her thinking it would make the time go
faster, it didn't. I think I checked and rechecked my bag to make sure I
had everything. I took another shaving shower session, and it was time to
get ready. After putting lotion on, I put my pink bra on (I really need
something to fill these out with one day), matching pink panties, pink
garter belt and the white stockings (I really should have worn them more
than just once in that weeks period, I keep forgetting how tough they can
be to put on). I looked in the mirror, not bad at all, I thought to myself.
I decided to wear a faded blue denim skirt that button up the side and a
black tank top, and a blue buttoned shirt, this way I can hide the bra
straps when I take the bus back and forth, and it was time to cover my feet
and legs. Grabbing the backpack, I left the house to grab the bus; luckily
it was late at night so not too many people were heading to the downtown
area. I sat close to the back where I hid myself, as I rummaged through the
pack finding my fake nails; one by one I put them on sometime reattaching
if it didn't look right or when I accidentally knocked them off rummaging
for something else. I finally was there nervous as all hell, but there.

"Hey cutie!" I heard from behind, it was Charles, we hugged but nothing
more.

"So where do you want to do?" I asked, wanting to kiss him, but definitely
not in public.

"Since the movie theater is right here, let's see a movie!"

Once inside, it wasn't that big maybe 2 or 3 theaters, we get inside our
theater just as the previews started, through the light from the film,
looks like there isn't but maybe 2 or 3 people and they look old! We grab
the seats at the back, I excused myself and went to the men's restroom,
thank goodness, it wasn't too far away from the theater, but it was still
scary. I went into the stall, stopping and listening for anyone to come in,
I undressed, leaving my socks for last, I stuffed my boy clothes into the
backpack, undid my button down shirt and tied it upfront, took the
lip-gloss out and stuck it in my skirt pocket. And pretty much ran out of
there just so that no one saw me. When I open the theater doors, I stayed
in the little hallway, took my socks off and slid the heels on, and walked
up to the back of the theater. He looked entranced into the movie as I sat
next to him. That didn't last, as I leaned over and gave him a kiss on the
lips.

"I was wondering why it took you so long, which restroom did you use?"

"Men's room, I pretty much ran out there." I whispered back, we were
laughing

"Shhh!" someone hissed.

"Guess we better be quiet!" I remarked he held my hand to quiet me down a
little, and we started to make out. Feeling his tongue inside my mouth was
hot, but feeling his hands going up and down my thighs was magnificent! We
stopped for a moment, to see why every one screamed, have to love horror
movies. His hand were firmly planted on my thigh, my hand was slowly
tracing the outline of his cock through his pants. When the scene passed,
he undid his zipper and I grabbed it as quick as I could. Lord almighty his
cock felt good in my hands, the heat he generated, the feel of his smooth
head I wanted that cock in my mouth more than anything else, but there
wasn't much room for us to really have fun, occasionally he would stand up,
acting like he needed to go to the restroom, and put his cock against my
lips, and I would readily accept the invitation, opening my mouth sucking
on the head, then he would sit down again. We stopped what we were doing so
we didn't get thrown out, but it didn't mean the teasing wouldn't
continue. He would play with my stockings and my thigh; I was still rubbing
his bulge. As the movie was preparing to end, I told him I was going to
change again, and he whispered "Don't! I want to walk with you dressed like
that; I have a place we can go to!"

When everyone left I grabbed my bag, and walked out shaking like a leaf, I
never done anything like this before. Luckily with it being dark, nobody
noticed me. We held hands, just joking around about different things, it
felt great to be out feeling the summer breeze on my stocking legs, having
the moon see a different side of me. We made it down to a gay bar and
grill, obviously they didn't care too much about who entered. He sat me
down at a booth and ordered a beer for me and him, and burgers to eat. This
was way too cool, looking around guys were drinking with guys, one corner
is a make out session it was great to see people just be themselves. On the
TV, was a baseball game, funny hearing the guys talk about sports in a
sexual way. There were a couple of other guys in drag, how could I tell,
their legs were hairy...gross! Then something hit me!

"Hey Charles, have a question if I needed to use the restroom where do I
go?"

The poor guy almost spit his beer out laughing, "Around here I don't think
it really matters, besides the 2 guys in drag, have you noticed any women?"

"Guess not, excuse me while I go!" gave him a quick peck and walked to the
room.

Walking to the women's restroom couple of people are looking at me, but I'm
thinking more because I was young than anything else. I get into the stall,
I started to hear something, once I'm done I reapply my makeup, and
curiosity took over, I walk to the other stall and was astonished to see a
guy buttfuck another.  The guy receiving looked like he was ecstasy; I
tried to be quiet leaving as they were enjoying themselves. I made a dash
once I left the restroom to the table.

"Dude! This guy is getting it up the ass in the bathroom!" I was trying to
whisper

"And? Did you enjoy what you saw?" almost mad that I said anything

"It wasn't bad; the guys look like they were having fun. But it's a public
bathroom!!!" pleading for him to understand.

"And what exactly were you and I doing in the theater? Have you ever had
anal sex?"

"Understood, no I never had anal."

"Well, if it is ok with you, I would like to pop your anal cherry, but not
until your ready! Cool?"

"Cool!" the thought of his cock in my ass sounded great, then I thought
about the pain, I always read in those porn magazines, but that guy in the
stall didn't look like he was in pain.  "Ready to go?" Charles was getting
up, finishing his last bit of beer.

"Where are we going now?"

"C'mon! You'll see!"

Again we walked, darker than before same direction.

There on building `XXX' movies...we headed inside the building. He paid for
him and I to see the movie, taking my hand Charles led me to the back with
the cashier reminded him, `No sex in the theater!' loudly.

The room was dark and the air conditioning must have been set to 0, it was
freezing. We stood against the wall. There was a smell to the theater, when
I got my most of my eyesight back, I could see the men in the chairs,
Charles took my hand and led me to a smaller room. There everything came to
focus, there was a guy getting tag teamed by two guys, another `girl' like
me who was the focus of a bunch of guys.

"Stand in front of me!" Charles whispered. "Just watch the fun, way better
than the movies!"

He was right, the guy getting double teamed, just got a face full of
cum. The girl was standing up and getting ready for a near naked guy to
give to her in the ass. She was pretty, slim wearing a black dress and
extremely high heels, her makeup was a mess from the cum of a previous
donor, but that didn't stop her or the next guy from her to giving him
head. The near naked guy pulled her panties down; he gave her asshole a
spit and slowly started to into her, in a few moments she was taking him in
all the way. Watching her was better than the gay guy; she was almost an
artist in her own right. When the guy was thrusting in, she would move with
the flow and deep throat the man. When he pulled out she moved away from
the cock, and her ass would move into the guys cock, it was pure
beauty. The guy giving it to her, would slap her ass a bit and go for
faster shorter thrusts, her heels would click on the floor. The guy getting
head played with her hair, while she tried to keep the rhythm up. I could
feel Charles, behind me, rubbing himself up against me, his hands on my
hips. I couldn't resist I rubbed his cock with my ass, he started to lift
my skirt up, and I felt his cock rubbing on my panties, between the crack
of my ass, and I didn't stop it, it felt great. But in all honesty, I
didn't want to go further when it came to anal, I wanted that to be special
not lost in a porn theater.

The guy getting double teamed got up and left, the girl was getting more,
until a new person stood next to us. He tried to feel my legs as Charles
was dry humping me, I was scared, didn't know if Charles would be upset
this guy was trying something or upset with me for allowing it. As the guy
got bolder he pulled his cock out and started to rub against me. "It's ok,
I'm here" was what Charles whispered in my ear, he continued to dry hump
me, soon my heels were clicking to Charles thrusts, then he did something I
didn't know he would do, he whispered something in the guy's ear, I
couldn't hear but Charles was now standing in front of me, and the guy was
behind me continuing what Charles was doing. Charles and I were kissing,
his cock was up against me, forcing my ass closer to the guy, and then I
felt the warmth of cum on my ass. Charles sat me down in one of the chairs,
and put his cock in my mouth, I was so into sucking his cock, I didn't
realize another guy was sitting next to me I slid my feet from the shoes,
and knelt in front of Charles just losing myself in his cock, the guy
sitting next to me, was standing waiting for his bj, but I wasn't going to
do it, I had a focus, I wasn't going to lose it.

"Grab his cock!" was all I heard, looking up he winked at me, I stopped for
a second to grab hold of his cock, I went back to work, blowing Charles and
jerking this guy off. I could hear this guy asking me to suck him, but I
wouldn't until Charles took himself out of my mouth and had me face the
other guy, I took his cock and put it in my mouth, just sucking on the
head, then going further down his cock, I sucked a little more, I went back
to Charles' head, licking and sucking, looking up the were playing with
each other nipples, then I felt the tension in Charles' cock, he pushed my
head off his cock, and shot a load over my face, that set off the other guy
as he unloaded in the side of my face and my hair. I got up, to see the
girl still having fun with 2 more guys, as I stood up to get my shoes back
on, she waved and gave me a wink, and she went back to work giving a sloppy
blowjob.

Grabbing the back pack, Charles led me to the bathroom, after 5 minutes of
washing cum off my face and trying to get it out of my hair, and trying to
wipe off any dried cum off my ass, we left walking back to the bus station
for me to head back home.

"Are you upset with me?" he asked, he took my hand into his.

"What do you mean?"

"For having you give that guy a blowjob and the other guy rubbing up
against you."

"Little confused."

"Confused? About what" I could feel a tinge of anger

"Well I thought you and I were on a date, and well it turned out this
way. Maybe I read things the wrong way, but I thought you and I were gonna
have the fun." As we got to the bus station we sat down.

"Listen, you are awesome to hang with, I really would love to pop your anal
cherry and I enjoy being with you. But, we can't date, I'm way older than
you, your still in school, we don't have much in common other than
sex. Don't be hurt, just being honest!"

I really did want to cry, but I understood what he was saying, but it still
hurt.

"You ok? It's ok, to let me know."

"Yeah, I'll get over it! So do I still get shoes for free?" really trying
hard not to cry Laughing, "Not all the time, but I think that's doable."
With that he kissed me on the lips and held me. It felt good, just being
held like that and I looked down!

"Oh shit, I need to change!"

"You better hurry you only have a couple of minutes!"

I hid behind the station, putting my jeans on quick, grabbed my tennis
shoes and put them on, `damn the socks' I thought to myself. I stuffed the
heels back into the bag, "hurry I can see the bus coming!" I rushed to fix
my shirt, wiped the gloss off my lips, fixed myself up, and got my money
out for the fare. Went back upfront, looking down the street, I don't see
anything "Where's the bus?"

"I was fucking with you!"

I playfully hit, and we sat and talked until we saw the bus coming, he told
me to call him if I wanted to, gave me a quick kiss, and he went to wait
for his bus, as he saw me off on mine. On the way back home, I had a lot to
think about, reaching into my bag, I saw my nails, explains why the bus
driver looked at me, I grabbed my walkman and listen to some music, peeling
off the nails. Thinking about things, I had fun, would I do it again?

Guess you will have to wait for the next story...



Hugs and Kisses to those who wrote me.

If you like what I wrote please email me at michelebrown@rocketmail.com