Date: Mon, 29 Sep 2008 14:51:55 EDT
From: TexLee29@aol.com
Subject: My Private History Lesson

Gawd, I will never forget that first time I got laid...I was on my back on
the edge of the bed and he held my legs back and spread apart as he licked
my anus and darted his tongue in and out of my awaiting hole. I opened my
eyes and saw his hands gripping both my ankles and I glanced at my black
lace stockings and my high heels pointing almost to the wall behind me. He
rose up and coated his cock with his saliva and put his dick at the
entrance to my asshole and looked at me with a wicked smile.

"Fuck me Mr. Williams," I cooed.

Our eyes were locked as he slowly and gently pushed his cock in my
ass. Numb from the excitement and no doubt the alcohol, I felt the head of
his big hard cock push against my ass then effortlessly seemed to glide in
as it passed my sphincter.

"Oh baby your so tight" he said, our eyes still locked together.

I pushed out my ass hole like I was making a bowel movement and
Mr. Williams cock slid right in the rest of the way, completely buried deep
in my ass, his balls against my fanny and his cock touching my prostate
sending an electric-like rush through me.  Mr. Williams was fucking my ass
and I thought about what was happening... Here I am, a 17 year old gay
tranny boy, dressed as a slutty whore, and getting fucked in my ass for the
very first time...by my high school history teacher...

I knew I was gay or at least bisexual by the time I was 11 or 12 but really
didn't fully understand it then. At 14 I was attracted to girls and
fantasized having sex with a girl, but I was especially excited about being
a girl and having sex with a boy.  I was raised by my Aunt Margo and bless
her heart she supported me and allowed me to dress up as a girl around the
house but preferred I dress in a more modest and androgynous way for school
and in public.

When I was 16 I had sex for the first time with my cousin Cindy. She
thought me how to lick her pussy and she blew me and I loved it but my
fantasy was still to blow a boy. At high school I was know as a twink or
fag and being labeled didn't bother me, in fact made me even more
determined to be true to who I am. That's when I met Billy and he invited
me over his house after school one day. Once at his place we he pulled out
some gay magazines he had hidden under his bed and we smoked a joint and
got naked. Next thing I knew he had his cock in my mouth and I tasted his
cum for the first time, and loved it!  The very next day after school I
invited him over to my house and I put on a bra and panties and blew him
and from that point on knew my fate was sealed. I started dressing like a
girl every chance I had, and blowing Billy almost daily until he moved away
several months later. I continued dressing up and experimenting with
makeup, walking in high heels and developing girlie mannerisms and thought
I was pretty good it by the time I was 17.  I usually dressed at home and
teased guys on line with my cam, anxious and excited to return to regular
sex with a guy.

Now to Mr. Williams...  I had a crush on Mr. Williams from that very first
day of school. He was in his early 30's, single, and a gorgeous hunk in my
mind. He was about 6'2" tall, and built like an athlete with a hairy chest
and longish sandy hair. As he stood in front of the class teaching us
American history I was lost in the fantasy of being dressed as his slutty
whore and sucking what I imagined was his huge hard cock. I think he may
have sensed something because he was always real nice and friendly to
me. One time after class I made an excuse to ask him some questions about
our lesson that day and he told me I was cute, sending my head spinning. I
became almost obsessed with Mr. Williams but try as I might, couldn't
figure out a way to be with him and dress up like a girl and wrap my red
lipsticked lips around his big luscious cock.

I had almost given up my dreams when opportunity dropped right in my
lap...or his lap, lol. (pun intended) It was raining hard after school and
I was standing just inside the doors waiting for the rain to let up for my
walk home. As the teachers were filing out and running for their cars,
Mr. Williams passed by to do the same. He said hello then stopped and asked
if I wanted a ride home! I couldn't believe my luck, and stammered a weak
"yes, that would be great". We ran to his pick-up truck and we both got
soaked in the process. As he pulled out of the parking lot Mr. Williams
asked if my parents were home and I told him I live with my Aunt Margo and
she would be home around 6 or 6:30.  I wasn't real sure why he asked that
question but I was delighted to finally be alone with the man of my
fantasies!  We pulled into my driveway and it was still raining hard.
Mr. Williams suggested I wait a minute until the rain settles down a
bit. We made some small talk, mostly about school stuff then he said if I
wanted to smoke a joint there was one in the glove compartment. Wow, I
thought, this is so cool!

I reached in and pulled out the joint and I scooted over so he could light
it for me. I took a big hit and passed it to him and our eyes locked for
just a second or two. In no time we were both pretty buzzed and I didn't
move back over on the seat as I put it out in the ashtray.  We were both
silent for a long minute then Mr. Williams commented on how the windows
were all steamed up, as he put his arm over the seat behind me.  All kinds
of thoughts were racing through my head but all I could manage to say was
"yes, they sure are". Another long silence followed.  I decided it's now or
never and I moved closer to him and rested my head in his shoulder and much
to my delight he put his arm around me. I glanced down and saw the outline
of his cock through his trousers and it was hard! I put my hand on
it. "Mmm" he whispered. Encouraged I rubbed it gently and looked up at him
and to my surprise he kissed me!

We kissed for several minutes, his tongue darting in and out between my
lips. I fumbled one handed with his zipper until he brushed my hand away
and did it himself, pulling out his hard cock. It was bigger than Billy's
was with a large purple head. I stroked it as we kissed some more and
Mr. Williams breathing got heavier. I broke off our kissing and finally
after all this time of fantasizing about sucking Mr. Williams, put my lips
around his cock. It filled my whole mouth as I took him all in until I felt
his pubic hair tickle my nose. I was in a trance or something and have no
idea how long I sucked his cock. Mr. Williams gently rubbed my back as I
sucked him until moaned and stiffened and I tasted his first spurt of cum,
then another and another and I milked him with my lips until he stopped,
literally filling my mouth with his musky juices.

"Gawd you're good at sucking cock Randy" he said.  "I've been fantasizing
about doing that for a long time." I cooed.  "Guess I have too." He said.
"Really, have you?"  "Yes".  "Well then next time I want to do it right" I
said.  "Right?"  "Uh-huh, I like to dress up in sexy girly clothes, so I
want to suck you as a girl" "Really? That would be fucking awesome!" he
said.  "And maybe you can fuck me too, that is if you want to"

With that he kissed me again, no doubt tasting the remnants of his cum in
my mouth.

"You know I can get in a lot of trouble doing this" he said.  "It's our
little secret, Mr. Williams."  "I hope so, sweetie" (He called me sweetie!)

"How about I come to your place on Saturday and I will show off my sexy
outfits for you?  "Yes, I would love that" he quickly replied.

We kissed again and I reluctantly got out of his truck and made a dash for
the door in the still pouring rain. I turned to wave goodbye and
Mr. Williams waved back with a nice big smile on his face.

That night he called my cell phone late at night and we talked dirty to
each other as he masturbated for me and I fell asleep dreaming of our
Saturday rendezvous.

Wanna hear more?  It gets even better...