01-08-21 | Megan Ryder
I have always been a cross dresser and enjoyed it.
Maybe it was too much at times. I some how let the guys
go too far with me. That is a different story. When I
got married I put all my special clothes in the
basement and lived a normal life.
One day I was home from a trip early and found my wife
was doing the laundry. There on the top of the pile
were her pink thongs. I was taken aback and grabbed
them and slipped them on and the warm rush of my past
feelings came back to me. I loved the feel of the silk
on my body. I was running my hand across them and soon
I was feeling my now erect member and soon it was
shooting its results of my rubbing. I took them off and
tossed them into the washer and left the room.
It was a couple weeks later that I needed to go out of
town for the night to repair a customer�s computer. As
I was packing I took a pair of her panties out of her
drawer and took them with me. While on my trip I wore
them the entire time. As other trips came up I took
more and more of my special clothes. I was soon
dressing up and finding new spots to go to and have fun
at.
Well if you call having drinks bought for you and hands
under your skirt and, well later about that. I was
careful to have two bags one normal and one special. I
was packing and again took a pair of my wife panties
with me. On my trip I wore them and as always enjoyed
them.
As usual when I arrived home I would put my special bag
in the garage and leave my normal bag in the kitchen.
She would empty it and do the laundry and that would be
it. It was several days later that when I went to get
fresh pair of under ware it was when I opened my
drawer that there on top of my white boxers was a pair
of her panties. It was the same pair that I was wearing
a couple days ago. I was wondering if maybe it was a
mistake or something. She said nothing.
On my next trip it was normal. I checked my bag and
made sure there were only guy�s clothes in it. Again
several days later, when I opened my drawer there I saw
several pairs of new panties. A thong, briefs and a low
cut boy shorts. I knew something was up now. But what,
I had no clue.
It was a couple weeks later when I fond out I needed to
go out of town that night that I asked her to pack a
bag for me. I arrived home and she was out and there
sat my bag. I grabbed it and off I went. At the hotel
it was when I opened the bag there on top was a pair of
white and pink thongs with a candy kiss taped on them.
I now knew it was known to her what I was doing.
I wore the panties all during my trip and enjoyed them
a lot. I did not think of whom or what or why, just
enjoyed. On my return my wife had made a few comments
that could have been taken several ways. I choose the
way that I understood them. It got to be a regular
thing for her to pack my suit case. Several trips later
it was a camisole then a bra.
The time seemed to fly by at a fast pace. It has been
two years since the first pair showed up and this last
trip the case carried a dress and makeup and heels. The
problem that I was having was that it not only made me
feel good but, I looked good also. Under the wife�s
idea we joined a gym and wanted to keep healthy.
I realize that is a good thing but, truth be told it
was different now. I knew that the diet and gym visits
where doing there job, but I still wondered. My normal
clothes seemed tighter in places and loose in others. I
did not think about it. I did think about the bra that
seemed to be more practical than sexual. How it now
cupped my breasts. I was not wishing I had them I had
them. I knew that in t-shirts it looked like I had
boobs but that was just wishful thinking. My waist had
gotten smaller and my skin was softer and my body hair
was thinner. I just figured that with the diet and
vitamins that it was just a nice side effect.
My wife had convinced me to let my hair grow and in the
sales position I held it did not matter. I was
reluctant when she wanted to have both my ears pierced.
One had always been pierced since I was a teenager. Now
it was both. My wife set up a much deserved vacation
for us. It was going to be a month long. If we needed
and desired more time, she had included a 2 week
extension to the trip. She set up a nice private
vacation resort. It was located on a white sands Mexico
beach area. She packed the clothes and we were off for
much needed rest and relaxation.
We arrived at night and were off to bed. In the morning
she said that she would have breakfast delivered to the
out side deck area. She told me to shower and get
dressed and have coffee on the deck over looking the
ocean views. I showered and dried off. With a robe on I
went to the bed and there laid out was a two piece
bathing suit. There was also my secret make up. I
walked over to the door and saw here sitting drinking a
cup of coffee. She was wearing a similar bathing suit.
I called to her and asked if there was a mistake. She
replied that if I did not do as she requested that it
would be a mistake.
I dressed in the suit and fixed my hair and make up. I
put the robe on and walked to the door way. I
sheepishly walked over to that table and began to sit
down. She looked at me and said that robe had better be
off when I sit down. I took it off and then she looked
at me and said that her work was almost complete. I
asked her what she meant. She explained that just after
we were married that she had known that I crossed
dressed. She also knew that I quit.
It was when I had left her panties in my suit case that
she knew I had restarted wearing women�s clothes again.
She said that if I was doing that then she would assist
in my secret. She explained that several times when I
was out of town she would follow me there and see just
what I was doing. She told me that the gym was just a
way to add a bit to the medical portion of her plan.
I had been taking female hormones for 2 years now and
that is why my body made the changes it did. I was in
shock, but did not react the way I should have. Within
the therapy of female hormones there were additional
drugs to smooth my attitude and emotional feelings.
That is why I now cry on sappy movies. She told me she
created a plan and developed a schedule that was to
change me and still be me. We laughed. A little while
later our maid came up and surprised me.
There I was in a female�s bathing suit and there was
not so much of a blink your eye. She left and we
finished the coffee and headed down to the beach. We
walked and did some small talk. She did tell me to have
fun and she has set up everything. She made it clear
that I was to do as she requested. We found several
chairs and towels near the ocean. We sat down and
relaxed. Close to lunch we placed our order and decided
to go in to the ocean.
I was in heaven walking dressed as a lady and it was in
the day light. We returned to the chairs and enjoyed
our lunch. We decided to walk down the beach a while.
There were several cabins and tents in a gathering. We
walked up to one of the tents, and were told to walk in
and have a seat. Again, no looks towards me. In a
minute or two a lovely lade told me to follow her.
I walked behind her and we entered a small shower area
and she requested that I get undressed. I slid off my
top and stepped out of my bottoms. She turned on the
water and from above a warm shower began. She took a
wash cloth and soap and began to wash me. She washed
every where. While I was lathered up she began to shave
my legs and underarms and face and chest. There was not
a lot there. She shaved down below into a landing strip
design. She then sat me down and someone worked on my
hair while they also painted my toes and finger nails.
When I was done she handed my suit back and told me to
dress and I was to meet my wife out side by the bar.
When I went out side she was sitting down at a table
with a couple men in bathing suits. They were talking
and laughing. I sat down and a waiter came over with a
drink for me. I took a taste and she had ordered my
favorite drink.
I was relaxed in heaven and dressed and shaved and in
the sun. I listened to there small talk and had we had
several more drinks. I was feeling great. I was
becoming very relaxed and the guy next to me seemed
cute. I have no idea where that came from but he seemed
cute. We talked and drank some more. I was feeling
dizzy and buzzed and it was nice to feel that way.
The one guy said he needed to excuse himself for a
minute. My wife stood up and said that we also needed a
minute also. We walked over to the ladies room and
entered and used the booths and relived our self�s. As
we looked into the mirror she smiled and asked if I was
having fun. I said yes.
We walked out and as we sat down she said that the guy
was hot and I should go for it. Before I could answer
the guys came back and sat down. We ordered some finger
food and more drinks. We all talked and laughed. It was
then that I realized that he had put hid hand on my leg
and was rubbing it and while doing that he was moving
his hand up to my thigh.
I was now feeling rather warm and relaxed. I glanced
over to my wife and she was watching what was going on
and just smiled at me. I felt his hand slide up and
then touch my manhood and then slip between my legs. I
relaxed my legs and let him slide his hand down
further. I had no idea what was going on but I did not
care.
The next thing I knew we were standing up with fresh
drinks in our hands and walking over to the beach area
was they had large umbrellas set up on the beach. We
sat on some towels and enjoyed the sun and was soon
leaning back and relaxing. I soon felt that hand again
and then it was on my belly and then it was on my
chest. I turned over thinking I could get some rest and
the hand just kept on rubbing me.
He started again on my back and in no time had undid
the top and let the straps fall to the side, I felt his
fingers slide under the bottoms and begin to ease them
down I it did not bother me at all. I could tell they
were lover as I felt the breeze over the crack of my
ass. I could then feel both hands slide down my bottoms
until they were off. He began to spread my legs and
started to rub my inter thigh and down my crack.
I was getting turned on something fierce. He then
rolled me over and there I was naked to the world. At
that moment I wished my member was bigger. It was in
the open. I had felt it had been bigger in the past and
now my ball sac was very small as well as shaft. I
always figured it just grew more when excited and just
smaller when not. I felt him grab my now erect member.
I am embarrassed as I know it on al its glory is the
size of my little finger. I soon feel him spread my
legs real wide and kneel between them. I feel his now
wet lips on me and soon he is putting me inside is
mouth. I am starting to buck my hips and match is
stride. I feel that I am about to cum when he digs is
fingers into my flesh and I shoot down his throat.
With in a flash he moves his body up and then I realize
that he is naked and is stroking himself. I look down
and he grabs my hand and places it on his manhood and I
start to stroke it slowly at first then he moves up and
he moves so close that I release him and he now has his
manhood next to my lips and starts to push it into my
mouth. I open my lips and allow him to enter. He starts
to slide it in deeper and the withdraw it then enter
and withdraw.
I am now hungry for his load and fast. He cum�s rather
quick and a lot. While I am in the after glow, he rolls
me over and his friend now is moving over and I feel
him move in between my legs. I soon feel his finger
near my ass and then poking around and then I feel this
cool lotion on me and his finger slides in and out and
then he moves and straddles me and begins to push his
dick in me. I can tell he is rather large as the pain
and pressure is intense.
I feel him enter slowly and with long thrusts picking
up speed as he starts his run for the gold. What seems
forever or just a minute or two? He rams it all the way
and stays there. I feel the cum creating a swelling in
me and when he retracts I can feel it leaking down my
leg. I am relaxed and content.
I hear movement and my wife leans down to my ear and
says that I look like I have enjoyed myself. She then
says that this is just a taste of what will be happing
for the next month to me. She says that if that is a
problem she will just increase the pills and make me
beg for it. She laughs and says that is just what she
will do...
doingbothways@yahoo.com
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