Date: Fri, 8 Dec 2000 12:59:50 -0800 (PST)
From: Bobbie <Redbagman@excite.com>
Subject: Trying to be a girl

An experiment with Trans
Attempt 1 and 2

Sometimes relating an experience is easier than fitting it into a
particular category of experience.  Such is the one I am about to relate.
A few years back, I once again began longing for a little male to male anal
experience, having had some during my teen years and not really any
since. I really wasn't psychologically suited to just straight gay
sex. Somehow there were some problems in my psyche as it related to that
and I began to find some interest in some kind of cross dressing or drag
experience.  I'm not going to try to further explain the situation other
than to give the basics, I decided to at least mimic a woman and attempt to
engage in an anal experience.  Got that?

Having made my decision, I tackled the project with considerable
preparation. The first part of the project was to prepare a
wardrobe. Having made a number of trips to the second hand stores and
others, I wound up with a pleated skirt (red plaid), white combination
garter hose(The kind that have straps and a waistband like a fake garter
belt), a panty girdle, a white half slip, a turtleneck pullover with long
sleeves (to disguise my male arms, and white gloves) I practiced and after
a period of time was able to conceal these underclothes under my regular
denims and shirt so that I could enter an adult book store looking pretty
much like a normal horny male.

The second step was the practicing of bending over. Using some mirrors to
check myself out, I found that with practice I could pull the underpants
downward and forward in such a way that they would cover my penis and
scrotum. I also worked on a bend over that would open me up for maximum
advantage, if you know what I mean.

Having refined my technique for that and a seductive wiggle to lower the
girdle and panties, I felt reasonably close to ready.  Next a couple of
days before my event, I spent a considerable amount of time squatting over
a mirror in the bathroom removing the hair in my anal region.

I then sat down at the computer and printed out a series of questions and
requests to be handed through the glory hole.  A also prepared a couple of
flaps complete with tape to tape over the glory hole while I changed out of
my denims into the costume.

I also considered my seductive technique to be used. Prior to going on my
adventure, I did an enema cleaning my lower bowel. I also thoroughly
lubricated it with hemorrhoid preparation from a tube. Not preparation h
but a similar lubricant. In my shirt pocket, I had several condoms (the non
latex poly something or other kind), Several bullet type suppositories and
even a couple of tampax.

I was ready for my adventure.  With a pocket full of quarters, I headed for
an arcade.  I taped my shield over the hole and settled in and slipped out
of my denims into my womanly costume.  I was ready. I removed my flap over
the glory hole and waited. The first fellow who showed up was quite
obviously short on equipment to do the job through the hole. I closed the
flap on the hole and after a bit he left.

The second fellow looked just about right.

I passed a note through to him asking if he wanted to watch me strip. He
was interested. I did my short strip pulling the panty girdle down and the
panties forward.  I teased up and down my thighs and pulled me cheeks
apart. I flipped the skirt over my back and there was no way for him to see
any male features.  I then slowly inserted a suppository and started
wiggling my rear toward the hole. I pulled away briefly and slipped him a
note asking if he wanted to see me insert a tampax. He responded very
affirmatively and I carefully worked the tampax into my butthole and pushed
the plunger.

I let out a low moan and then asked if he wanted to remove it for me. I
backed up against the hole and he slowly pulled it out and I assume watched
while I inserted another suppository. I then slipped the note through
asking if he wanted his cock in there.

It was immediately through the hole. I rolled a condom on and backed onto
his cock.  The head moved slowly towards opening me but I must have been
too hot for him or something because he barely got his head started good
and he withdrew and I watched through the hole as he removed the condum
full of cum and then left.

A second fellow showed up shortly and we went through the procedure
again. He tried hard, but unfortunately he had a rather large girth and had
difficulty lining up and getting it inserted. The rubbing however was
enough and he also removed a rubber full of cum, although I was still
essentially untouched.

Having spend a considerable amount of time and after waiting for quite a
while with no one showing up, I called it a day.

I was determined however, more so than before to have this "slut"
experience and began doing some advertising on the internet. After a couple
of weeks I contacted a hot one. Initially I advertised that I was looking
for anal sex and then in the case of every contact carried on a little
correspondence and let them know what I was after.

Most lost interest when I mentioned the dressing part.

Finally, one fellow started out with meet me at this rest area. When I
knock on the stall hand me a rubber and turn around and bend over and I'll
do the rest.  We worked over the details and finally arrived on what I
considered would be a major event.  I was to meet him in a parking lot and
we would go to a friends house where the three of us would carry off this
event. I was going to be dressing as a woman, the plans included an enema
from one of the fellows and then some three way, nots of insert and finally
some anal sex.

I increased my wardrobe to include a full black slip, black hose, and even
a black bra.  After some experimentation I managed to find a way to use
double baggies with warm water to pad the bra.

I purchased some additional enema equipment (a couple of fleet enemas and a
bulb douche), more supplies, tampax, condoms and just in case we wanted it
a butt plug.

The encounter would involve a drive of some sixty mile and enroute I
stopped at a rest area along the highway to change. Once again I put my
feminine things on under my denims and prepared to resume my trip. I
entered a handicapped bathroom (they had locks on the door and more room)
and took a quick enema and emptied my bowel wanting to be clear and clean
for any activity that took place when we got together.  I noticed several
condoms and lubricant on the floor indicating that the room was used by
others with the door locked for privacy.

Once I completed my trip I waited for a while in the parking lot as
appointed until a fellow I'll can Ron drove up to meet me.  He started a
casual conversation and then asked "Are you redbag?"  Bingo, we had made
contact.

He directed me to follow him and we drove to a residential area. He
instructed me to wait for a minute or two while he took care of things
inside.

The plans were running a mile a minute through my head, The enemas, the
slinking around in the slip and then the final undressing and the eventual
sex.  Ron came back to my car and told me that his friend had decided
against it. He really liked teenage boys and wasn't "in" to the
crossdressing thing or enemas.

I offered to get a motel room, but Ron was afraid of being seen but did
offer to go to a roadside park and let me bend over.  That wasn't what I
was wanting at that point so my second attempt failed.

More later