Date: Mon, 14 May 2001 19:13:24 -0700 (PDT)
From: Bobbie <Redbagman@excite.com>
Subject: warren and the woodie part 8

Without trying to go into any great detail, suffice it to say that Squire
and I spent many enjoyable Saturdays that spring. We were never bold enough
to enjoy our activities at my apartment but we did enjoy several outdoor
encounters along the river, at the old farmhouse and in other remote
locations.
Squire was always a gentleman about his activity and never caused me a bit
of embarrassment when we were out and about. However, it was becoming
increasingly obvious to me that he needed a better life than he has having
spending his time in my apartment and pickup. He needed a place to run and
be a dog. We took outings in the evening to a park or some other place, but
he just wasn't getting the kind of freedom I thought he deserved. And, my
employment was about to change and I wasn't going to be able to bring him
along and let him follow me around the job site. I was soon to move into the
world of office work and it was going to restrict him even more.

I decided to find him a new home.
I placed an ad in the local paper. For adoption, young mature male collie.
Needs home with space to romp and family to enjoy. Call xxx-3487 for
appointment.

I took the adoption thing pretty seriously and the first couple who came to
see Squire immediately indicated that he was still young enough to "get
fixed" and they were eliminated right up front. Next there was an older
couple and although they would have been great grandparents for Squire, he
needed some younger people to give the attention and exercise he deserved/
The third prospective owner was a young couple. They called and said they
were interested in having a large dog and would I be interested in bringing
Squire around to visit. It sounded hopeful and I drove to their suburban
address. They had a small farmstead with a fenced yard.
Squire and I went to the door and we were invited in. After introductions he
invited me to have a beer and said maybe while we were having a beer his
wife could show Squire around.
Squire and the young woman went out the door to the back yard and Don and I
settled down for a beer and discussion. He told me that they actually had 40
acres of pasture and woodland, but they both worked and Squire would spend
the days in the yard and when they were home he would be free to roam.
That sounded like a pretty good thing to me.
The important thing, he said was that Squire got along with his wife, "he'll
be her companion basically," he said.  We talked weather and sports and
finally his wife and Squire came in and Squire laid down under the table
near my feet. I reached down to scratch his ears and noticed his head was
down there licking his privates trying to coax his penis back into the
sheath. It was pretty obvious to me that someone had been checking out his
equipment.
"So, what do you think about Squire?" I asked.
"I think he will fit right in," she replied and I noticed a bit of
suggestion to her comment.
"Well," I said, "Squire has always been a male and one of the conditions I
have established for his adoption is that he not be neutered."
"We wouldn't think of it," she replied, almost too fast.
"It looks like you have the kind of home that Squire would like, " I said,
"tell you what, how about I let him stay for a week and we'll see if he
^Ñfits in' with you all." "We can decide then,"  I continued, I've brought
along his food and his rug so he will feel at home."
"That would be wonderful," she replied.
"One thing though, I said, If you keep him I would like to visit him now and
then, at least for a while."  I was starting to have a little problem with
letting him go and I was almost to the point of tears.
"Sure, we understand."
"Well, let me take him out to the pickup for one last ride and we will be
back shortly."
"Sure."
Squire and I went out to the truck. He hopped up in the seat besides me and
we had a conversation as we drove down the road. About a mile away I stopped
and checked him out pretty carefully. The wife in the family was into dogs.
At least she had done a pretty good job of jacking him off to check him out.
I felt like he would have a home where his talents would be appreciated. And
he would probably get more action and a country home to boot. It isn't easy
to tell a friend goodby particularly one as close as Squire had been, but
changes were coming in my life and it was for the best. I told him all about
it and I swear he seemed to understand.
We went back and I left Squire behind. It was the first time we had been
apart in the three months or so since we met.
It was really lonely that night without him at the side of my bed.
The next weekend when I went out to see him, he had adopted his new family.
I asked how they were getting along and I was told what a wonderful dog he
was and how he was exactly, with the emphasis on exactly, what they had been
looking for. Everybody was smiling except me when I left.

I never went back.

As I said, changes were ahead for me. The first change was that I moved up
to junior status in my studies and that summer I had an internship with an
architectural firm. They generally offered them after the Junior year, but
with my several years experience in construction, they gave me an early shot
at the internship.  I wound up working there several years.  The main change
it made was I was no longer working in blue jeans and flannel shirt and
boots. This was a "dress up" job that although it was white shirt and
chinos, meant a little more attention to my laundry.

It was a trip to the laundromat that brought a change for me.
My usual routine was to put the shirts and pants with the wrinkle resistant
stuff in one pillowcase, the sheets,  underwear and socks in another.  I
dried the two batches separately and put the shirts and pants on hangers and
just dumped the socks and underwear into the pillowcase that brought them.
The sheets went into the other pillow case.
When I got home I dumped the underwear on the bed and stuffed the second
pillow case in the first and put it on the shelf. Then I folded my underwear
and rolled the socks.

I made it a point not to expose my sometimes brown stained underwear to
public view anymore than necessary and it was the presence of that discolor
that comes from cum stains that caused me to just put the underwear in the
pillowcase and fold it at home.

This particular time, someone had left a pair of her underpants in the dryer
and I hadn't noticed them so they came home with me when I finished my
laundry. When I folded my underwear, I discovered them.  They weren't nylon,
but they weren't cotton either, some kind of inbetween fabric and to my
amazement, they appeared to be just about my size.  I considered trying to
figure how to return them to their rightful owner and gave up on that. My
second impulse was to put them in my "rag bag" where worn out clothes went
for cleaning supplies. But, they were to all appearances nearly new and they
did seem just about my size. I wondered just how they might feel and decided
what the heck, at bedtime I slipped into those underpants and they were a
little tight but I got them on.

The smooth slick texture was almost beyond belief. They just really felt
great. Those of you out there who are into that kind of thing know what I
mean.

I tucked my penis down between my legs toward the back and smoothed the
front of the panties. Pretty smooth at that. The next thing I just had to
try was my dry hump masturbation over the corner of the bed and in those
underpants it felt even better than usual. And that was great by the way.

I decided that I would get some of my own and wash them out at home. No trip
to the laundry. Fortunately the town was large enough that I could go to a
department store and purchase these items without raising any eyebrows.

There never was any question about why I was wearing them, they felt sexy. I
even liked to run my hand over my own bottom. It gave me sort of a two way
turn on, the feeling of my hang going over a smooth sexy butt and the
feeling of my butt having a hand lightly caress it.

For a while I wore regular underpants over them when I wore them to work.
I'll admit it gave me sort of a thrill knowing what I had on underneath in
addition to the sipping of the underpants over the panties as I walked.

My next move with the underpants was into the stalls at the student union.
These were supposed to be good pick up points, but my experience was that
they were either a place where guys went to get a quick blow job or to give
one. I decided to be a bit of a tease.

I went into the mens room and took the back stall. There were no handicapped
ones then so the back stall was generally the location for people looking
for action.

I pulled my pants down and set there with my trousers at knees and my penis
covered by the panties.  I tucked it down between my legs and just sat there
rubbing the top of the shaft through the panties.  The stall there had a
hole large enough to slip a penis through but not much more. It was also
enough to see through of course and I was a real tease. I'd run my fingers
alongside my penis until it started to become erect between my legs, then I
would pull it around pointing toward my navel and run a finger alongside it
outlining it in the underwear.

Many times I had fingers motion through the hole, but I put off cooperation.
Often I would after a while of teasing peek through the hole to see someone
furiously pounding at their pud.

Then one day when I went into the back stall the hole had enlarged. It was
big enough for a hand to reach through. Someone had take a keyhole saw to it
and cut a hole about 5 inches square.
I went into my regular routine however and shortly there was someone in the
stall next to me. This time the motion through the hole was a bit less
subtle with the hand reaching through and motioning. I slowly stood up and
turned my backside towards the hole and let the outstretched hand brush up
against my ass. He felt around a bit and then I felt a finger slide inside
the panties.
More caressing and then finally a finger found its way between my cheeks.
Then glory of glories, I felt it go in my butt hole. I pushed back. I loved
it. But I pulled away.
I reached into my trousers and pulled out a condom and offered it to whoever
it was on the other side. I watched as he rolled it onto his erect penis. It
was short and stubby. I backed my ass against the hole and offered it to
him. He fingered it a couple more times and then made an attempt at
penetration, but the angle apparently wasn't good for him and we were
unsuccessful.
I was ready, but as I pulled away to unlock the door to the stall and bid
him enter, he came in the rubber and peeled it off and flushed it away and
left.

Over the next several weeks, I got into the feminine mode big time. First it
was a garterbelt and hose to go with my panties. I wore black so the hair on
my legs wasn't really obvious. Then I picked up a skirt at the local second
hand store. A turtleneck sweater was a good unisex kind of thing and it
covered up my hair on my arms.  I got a nice bra at the second hand store
and I was pretty well fixed.  By the way, those zipper type sandwich bags
filled with water make excellent padding for the bra.  A nice wig wasn't
hard to find and except for the size of my feet and the lack of makeup, I
was it pretty good shape for the shape I was faking.

I wore the clothes in my room at home and studied my overall image. After a
careful assessment, I decided that I would remove the hair on my legs. The
first attempt was with that hair remover and I really didn't care for either
the odor or how it left my skin feeling although it did make it very smooth.
Then I discovered bikini wax kits.  Suddenly I has hairless legs and a
couple weeks later I removed the hair from my arms as well.
That left only the growth around my asshole and I found that with a little
care and a good mirror I could use the wax strips and remove that.  I left
my pubic hair and found that if I pulled my penis back between my legs, I
had a pretty good fake slit in front although as you will see later I worked
to displace it forward.

Once I got really comfortable with the whole thing, I bought some sandals
that weren't dressy but didn't look all that tacky.

There was an adult arcade about 40 miles away that had the reputation for
its glory holes and so I decided that since it was out of town, it would be
a good place to start my career as a crossdresser.

I worked on my plan for quite some time.  That involved making another
purchase, a purse.
Anyway, I packed my clothing in a small bag. In my purse were two dozen
condoms, tampax, a tube of generic preparation h, a bunch of beeswax
suppositories, some clean ups and a bunch of notes.  I hadn't figured out
how I was going to handle the voice thing so I wrote notes.

In addition to my clothes, I packed a fleet enema. About half way to the
next town and the arcade there was a roadside area with a handicapped
bathroom that was unisex and had a lock on the door.  It would serve as my
changing station.
 I drove to the rest area and went in with my bag in hand. While there I
took a quick enema to clean the lower bowel area and then gave myself an
ample application of the preparation h look alike.  It lubricated my lower
bowel nicely.  I dressed with my hose and garter, panties and a panty
girdle, a slip and of course my bra with the water bags that gave me a c
cup, the turtle neck and the wig.  I dusted just a little powder on my
cheeks and barely touched my lips with a very light pink lipstick.

Once I was in the car, I was so excited I could barely drive.  I made it to
the arcade and slipped some white gloves over my obviously male hands.

Into the arcade I went and I admit I turned a few heads.  I went to the next
to back stall in the arcade and checked to make sure it had a glory hole and
it did ^Ö one on either side.

Once in the stall, I slipped the latch and put a $20 in the video machine, I
planned on it running for a while.

I took two pieces of paper from my purse and taped a flap over the glory
hole, not that I didn't want anyone watching, I just wanted to know when
someone showed up. It didn't take long. I saw the paper wiggle and I took it
down.
For a few moments I caressed a breast and my inner thigh with a hand and
then I moved the skirt up a little bit. I rubbed my way through a couple
minutes more and then I brought the skirt up to the point I had thigh
showing above the hose. I did a quick peek through the holes and It was
obvious that I had watchers. I pulled the dress up over my waist and started
rubbing my crotch. The girdle hid my masculine bulge. Then I stood up and
released the waist band of the skirt and stepped out of it. I was putting on
a pretty good show.
I turned and put it back over the chair and returned to my rubbing and
squeezing of that water filled breast substitute.

When I thought I had it fine tuned enough I pulled the girdle down to mid
thigh. I started working my hand like I was really rubbing a slit.

Soon I slid out of the girdle. I stood, turned my butt toward the screen to
get the best light on it and reached into my purse. I got out my notes, a
tampax and a couple of suppositories.  I turned my butt toward one side and
pulled my panties down just enough to give a shot of my smooth asshole. I
slowly inserted a suppository.  I then turned to the other side and repeated
the action for the benefit of my second watcher.
Then Giving each a side view I got out a tampax and inserted it in my ass.
It was wild and I thought I was going to cum just doing it. I could hear the
sighs. I turned back to my sitting position and handed a note through the
one side. On it was written, would you like to remove my tampax? Knock once
and return the note.
Talk about a quick reply. I moved my ass toward the hole and pushed the
string up into the hole.
A gentle pull and it popped out. I immediately put a second one in and
repeated the offer to the otherside.
Offer accepted.
Then I passed a condom through the hole to the first side. I watched as he
rolled it on. I handed one through the other way. Again I watched as he
rolled it down the length of his cock.

I backed my ass up to the first hole and motioned with my fingers in the
second hole for him to put his cock through.  The guy on the first side was
tremendously excited and although he got his cock head into my ass, that was
all and he was filling the end of the rubber.  The second fellow got a
couple of strokes in my mouth before the first one shot his wad and he did
just a little bit better with his ass work but he only managed about half an
insertion, maybe a couple of inches in me before he shot off.

As is the case in the arcades it is "Cum and go." and it was start over
time. I taped over the holes and re-dressed. The second time around I left
off the girdle and left the skirt on. I only worked one side at a time and
unfortunately, the results were the same as the first time. I just wasn't
getting much penetration from it.

During the afternoon, no less than 8 guys got their jollies without really
giving me a good penetration. By that time and having spent a little over
$30 in the video machine, I redressed and with as much dignity as a arcade
whore can muster, I left. But not before taking down a phone number that was
written in the booth.

Comments appreciated