Date: Thu, 20 Dec 2007 20:58:39 -0800 (PST)
From: gradmma@yahoo.com
Subject: Bobbie

I had like most men wondered if I thought about another man in any way but
as a buddy, I was going to Hell. I was in my late thirties before I
actually wondered what it would be like to see and touch another mans
penis.  Actually that is not quite accurate; I was in my mid twenties
visiting an apartment with my girlfriend and her two gay roommates.  They
were all out for the afternoon and I got bored and started digging around
the bookshelf area and discovered a small stack of Blue Boy magazines. Now
I had never heard of this magazine much less given any thought to a gay
magazine. I opened one up and was honestly shocked to see men posing like
playboy models but with full frontal nudity. I was stunned but I couldn't
put the magazine down. When I got to the letters section and read a few, I
had a massive hard on. I was so terrified of getting caught reading these
magazines that I actually practiced putting them away in a hurry and making
my way to the kitchen unseen so I could look like nothing was going on. I
went back to the pictures and studied the men's dicks; after all I had only
seen other dicks in passing glances. I was definitely intrigued.

I suppose over the years I had masturbated many times to those memories. In
my late twenties I bought a run of the mill porn magazine and in there was
a spread on a transsexual.  I was again shocked. I didn't know there could
be such a thing, a woman with a penis. I was sure I was being tricked by
photography. I asked around sometimes when the situation was right and
found out there were such creatures. I now started having fantasies about
making love to a transvestite and found myself wondering if I could place
my mouth around her dick.  I soon learned that there were entire sections
in the XXX stores devoted to the subject and sometimes under the influence
of alcohol I would buy a magazine. I had to admit to myself that if I was
going to try anything sexually that wasn't white bread, it would be with a
transsexual.

More and more of my sexual thoughts began revolving around sex with a
transsexual. I guess the next phase was to figure out how to meet a
transsexual. It posed a real problem because I was so shy and not sure I
could make myself follow through if I did meet someone.  One night I went
to a Gay club with a good friend. I and everyone else for that matter knew
he was gay but he was harmless in fact he was very likable, even lovable. I
had never dreamed of going into a Gay bar but we were loaded and I decided
to gird my loins and try and be a regular guy.

I was approached a few times to dance or have a drink bought for me but
rebuffed them all, gently but firmly. My buddy just observed and went about
flirting with any one who he knew or wanted to. I remained at the bar,
slowly nursing a beer, then two and three.  Still the guys who approached
me got a cold shoulder. In retrospect I must have seemed stuck up but I was
terrified. Finally I relaxed enough to look around the room and saw a guy
in a dress over by the jukebox, plugging in dollar bills and swaying to the
music trying to decide on songs.

I guess I had had enough beer to let my guard down and I went over and
looked over his shoulder. "James Brown is good." I said.

He turned halfway around and smiled, then punched the numbers for "It's a
man's world."

He flipped the card and at the same time we said,'Oh the Stones." He smiled
and said "you owe me a double coke."

I laughed and said" better yet let me buy you a beer."

"Six more songs and I'll take you up on it."

I have to admit that my suggestions were based more on speed that interest
as I gave him my input.

We turned to go toward the bar, just as James Brown came on. He grabbed my
hand and drug me toward the dance floor, before I could react. "It's your
song he said, placing his arms around my neck and closing his eyes to dance
to the music.

I looked around and my buddy smiled, not dirty or anything but kind of
knowingly. This helped me relax and I put my arms around his waist and
started slow dancing. He had on an off white long dress with horizontal
pleats and I was caught staring at his breast when he opened his eyes.

He laughed," don't expect too much, I'm just starting hormones, it's mostly
filler.

This went over my head; I was too absorbed in my own guilt and
embarrassment.

He pulled in closer and our hips were now touching. I was so afraid I would
get a hard on. Obviously not getting the idea of a Gay Bar.

"I'm Bobbie" he said, looking for my name in return. "Uh, Stan, Stanly, I
croaked.

He smiled and placed his head on my chest and we danced.

At the end, I thanked him and scurried back to the bar.

My buddy came over and asked me what happened?

I said we met at the juke box and I felt obliged to dance since I suggested
the song.

He called my bluff and said," No way, you were interested. Are you
attracted to cross dressers?"

I hemmed and hawed for a couple moments then smiled and said "Yeah."

He threw his arms around me and kissed my cheek. "Sister!"

I don't know why but this one small admission and acknowledgement made me
drop my inhibitions and realize I was ready to try sex with a cross
dresser, she male or whatever the name due Jour was.

I went over to Bobbie who was all alone sipping a drink and said, "I am
sorry, I am new to this could we go out sometime?" "I mean if I haven't
completely pissed you off.

He stood and walked to the bar and asked Ramon the bartender for a pen. He
wrote his name and a couple numbers down and said," Thursday through Sunday
is the best time for me. I would love if you called me Stan."

I blushed, "It's Charlie actually, and I was caught off guard before."

He smiled and kissed my cheek. "I understand."

"You know I am free right now, we could go somewhere quiet and talk, maybe
have a drink."

My buddy was within earshot and tossed me his car keys. "I can get a ride
home!"

I blushed but we headed to the door.

I didn't know how to act in public but I just decided to treat him as a
woman and opened the car door and helped him inside.

I got in behind the wheel and said, Where to?"

"Do you like music? I have a huge record collection." "Oops pardon the
pun."

As usual this went over my head and I felt so relieved I started the
car. "Which way?"

We ended up several blocks from the bar and found a parking place. I
followed him to the door and then in once he got the apartment unlocked.

I was amazed, the place was done in roaring twenties style, lots of lace
and fringes and woven textures. No sign of a mans prensance.

"Do you live alone?"

"Me and Tina, but don't worry she is not home, she'll be at her sisters
until next Friday.

Bobbie took my hand and led me to the stereo. Next to the cd player there
was a huge rack of cd's, "Put something on and I will make us a drink, is a
martini OK?"

"Sure."

I scoped out the cd's for awhile, actually there were too many good titles
to choose from. I finally settled on Ben Webster. A breathy little disc
that never got faster than sexy.

Bobbie popped her head out and smiled, Ben Webster, very nice!"

She, I had now began thinking of her as feminine, came in carrying two
chilled martini glasses and her hair down around her shoulders. The hair
was wavy from where she had it put up.

She handed me a glass and clinked our together saying,'Ching ching!"

We had a sip and I exhaled hard. Wow is that rocket fuel?" She laughed no
just good gin. Make yourself at home, I am going to change my shoes and get
more comfortable."

I looked some more at the music collection then started snooping around the
apartment a little. She was gone quite awhile because I was just eating the
olives in the empty martini glass as she returned.

"You need a refill. "She grabbed my glass on the way by to the kitchen."

I stood there in shock, she was in a floor length silk nightgown wearing a
simple strand of pearls around d her neck. Beneath the nightgown I could
see her mauve bra and panties as she walked away.

The room filled with the musky scent of her perfume. Not over powering but
intoxicating.

I found myself getting a hard on. Not all the way but blood was definitely
flowing.

The music suddenly stopped so I pulled out an old Stan Getz recording
called the Touch of your lips."

Bobbie returned with a frosty martini for me and looked d me in the eyes,
"Are you trying to seduce me? This is the sexiest jazz record on earth."

I laughed because I felt the same way, and then realized that I had chosen
it.

Bobby took my glass and set it down and laced her fingers around my neck,
we started swaying to the music.

The title track was over before we stopped swaying, Bobby looked me in the
eyes like she could see my soul and turned her head to the side and our
lips met. We lip kissed a little then I started frenching her. She tasted
like heaven.

Her body drew close to mine and I felt an old familiar urge arising.

Bobbie kept dancing but her hands moved to my ass cheeks and she gently
massaged them while we pecked and kissed .

I was smiling from ear to ear; she was making this so sexy.

I let my hands wander, feeling her bottom, running up her back. The night
gown was like an aphrodisiac. I wanted to feel her all over. I swayed her
to the couch and kissed her as I laid her down, my lips following her down.

Bobbie moaned with pleasure as I moved on top of her.

My hands wandered to her breast. As I started to fondle her, she got a
little nervous and said" they'll be bigger soon I promise!"

I was taken aback, I had nearly forgotten she was male, I got my senses and
slipped her right strap off her shoulder and kissed her nipple, licking it
then nibbling the erect nipple. She moaned and whispered something I didn't
catch.

I reached down and slipped her nightgown up. She wriggled out of it with my
help.

I was right; she was in mauve satin panties and half a matching bra, which
I removed.

Bobbie was in a state of ecstasy; every time I licked or nibbled anywhere
she shivered.

Then all of the sudden she mustered her emotions and grabbed me and flipped
me over on the sofa.

With a sly grin, she worked off my pants and bit the buttons off my shirt
one at a time, spitting each one across the room.

I was in full arousal now; I wanted to fuck her and now.

Bobbie took off my shirt, and removed my unaware. My dick bounced in the
air, wanting desperately somewhere to insert itself.

Bobbie smiled and started teasing me with her hand then she started sucking
me. I nearly blew my load right away but she knew her business and backed
off ever time I was ready to cum.

I was teased to the edge of crazy so I grabbed her hips and flipped her
back to the bottom.

Like a magician, I took her panties off before she could react.

She blushed but her cock was now exposed and getting hard.

Here goes nothing I thought briefly as I moved down and licked the tip of
her 7" cock. It got harder and bobbed in the air. I took a close up look
then opened my mouth and took the whole thing into my mouth. I was
surprised, by the feeling, I can't describe it but I was more turned on
than ever, I placed my hand around the shaft and started to give her a blow
job like I had seen in porno films. If this felt good tom her, it felt
twice as good to me. I suddenly wanted her to cum in my mouth. I wanted to
taste her, share our love. "Cum for me baby"

"No, not yet, I want you inside me."

I got the message but I was too far gone, I tightened my grip on her shaft
and started bobbing up and down, desperate to taste her cum. She moaned and
complained." You're going to make me cum!"

"I want it baby, I want to taste you, and you are so sexy, cum in my
mouth!"

Well Bobbie, let out an animal moan and then she shot hot cum all the way
to my tonsils. Before I could swallow, she shot again then again, her cock
slipped out and the fourth shot sprayed all over my face. I was shocked, it
felt fantastic. I swallowed and savored the moment. Bobbie pulled me down
on top of her and hugged me tight, after a few moments she licked the cum
from my face and slyly said "Sorry".