Date: Sun, 8 May 2022 09:57:23 +0000 (UTC)
From: wood guy <woodd_guy@yahoo.com>
Subject: Dressing Adventure Part 1 (Revised)

This story is a work of fiction and contains descriptions of explicit
sexual acts. Some of the parts are real but will leave that up to the
reader to decide. If this type of content offends you or you are under the
age of 18 do not read it.

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Characters My name is Ben, David my close friend, my sister is Susan,

	To start this adventure I should mention, I am a 14 year old boy
and my name is Ben, I guess you say I am on the small side I am only 5 foot
tall and maybe 90 pounds. I have always kept my hair long, shoulder length,
not sure if I liked it that way or just was not crazy about getting it
cut. I have a sister 2 years older then me and as it works out she is a
little bit taller then I am also weighs more. Sports were never my thing,
maybe because I was never very good at it, I was into drawing, painting,
and reading. I started drawing at a young child and showed talent, my
parents realized that, and helped me by making sure I had the supplies
needed to do my art work.

	I spent a lot of time in my studio that was set up in the basement
of my house, My parents realized I needed more room with a few paint
easels, and room for the paint so they fixed up a second room down there
and moved my bed down also. They did this because so many times I would
wake up in the morning and continue the work on a painting that I had been
working on the night before. I mostly did landscapes, and started getting
into paintings with lakes, and for added interest, I add a young girl or
boy my age or maybe a little bit younger just for interest.

	Any artist knows sometimes that you need to do some research into
the subject that you are painting so that it is more realistic. So
sometimes I get on my bike and ride to the few lakes that were near by and
take pictures and also I be searching the internet for yes young girls or
boys to see what they would be wearing.

	I sort of felt like any young boy at 14, I get a certain tingle
when I was looking at the girls and yes I must admit my searches did lead
to some porn, but lets face it hard to find any young girl porn, just
mostly older ones made to look like they were younger. I was sort of
confused since looking at the porn I was getting hard and I discovered the
joy of stroking my cock. Being honest I was not sure it was because I was
looking at the the small girls getting a cock in there holes, or was it in
the back of my mind was it something I would have liked to have done to
me. Sometimes while jerking to the porn I would imagine that I was that
little girl doing all these naughty things with the guys.

	On one of my mornings when I did not have to go to school I woke up
and still being naked, I start working on a painting. I guess I an not the
neatest person so I wound up getting the paint on myself. I liked the
freedom of being naked but did not like the fact that I have to scrub the
paint off of my skin. So I asked my mother for an apron and since we did
not have a lot of money to spare, she said I could have one of her old
aprons that she had for the kitchen. It was not very manly but it sort of
worked and I did like the feeling of the apron on my naked skin.

	While doing my research on the girls, OK let's be honest I was
looking at porn, I started to find boys dressed as girls and was finding it
to be a turn on. Something about these skinny boys like myself dressed in
panties and other girly outfits was sort of hot.  I was starting to feel I
like I wanted to do the try dressing like these boys were.  My chance
happened one day when my mother and my sister went thru my sister's closet
and pulled out all the older clothes that she no longer wanted to
wear. While they were at it, they also went thru my mother draws and pulled
out some of the let's say naughty outfits that my mother had wore when my
mother and father were first married.

	They put them all in a bag and asked me when I could, to drop them
off at the donation center that was close to one of the lakes that I always
ride too. I said sure, I will do it this afternoon since I was planing on
taking a ride there anyway. My father was at work and my mother and sister
decided that they were going to go shopping, so I was left alone. As soon
as I felt that they were gone I decided to open up the bag of clothes. I
started sorted thru the bag from my sister and found a few outfits that I
felt sort of looked hot. Some skirts that after measuring the waist I
realized would fit. They were on the short side but that made them feel
even more exciting. Also there were plenty of panties and I grabbed the
ones that seemed to be made of a shear fabric. I found a few blouses that
were sort of sexy and kept those. There was even her old cheer leading
outfit that she wore one summer when she went to a cheer leading camp.

	In the stuff that was from my mother who is also on the smaller
side she had a collection of naughty underwear that I suspect she wore to
please my dad. There was one set of night wear that had these almost see
thru panties and top cover. The panties had a slit opening from the front
to the back, I have to say you would call the crotch-less . The top sort of
tied closed but because the fabric was so thin it was like wearing
nothing. My mother was I say small but still very sexy, she did not have
big tits but I have seen other men look at here when she walked by and even
some of my friends had said something about the way she looked. After I
went thru the outfits and selected what I wanted to keep and put them in a
different bag.

Being honest at this point I was not sure what I wanted to do with them,but
decided I did want to keep them. I found a good hiding spot for my new
collection of girls clothes. then packed up the rest and put it aside to
drop off later. Once I was finished and since I was alone I decided I
search the web and find a good site that had many pictures of smaller guys
dressed like girls. On one site there were with also big men who were naked
along with these sissy boys. I was finding myself getting hot looking at
the movies of these sissy boys dressed as girls taking cocks into their
mouth. Some of the boys were hiding there cocks and I could not decide what
I liked better the little cocks showing or hidden between there legs.

	I decided to go back into the stash of clothes that I just had
hidden and changed into the outfit of the crotch-less panties, and top
cover. As I watched the movie I stoked my cock as it was out between
opening in the panties. I kept stroking long enough so that when I was
watching this sissy boy take a load from this big guy, I shot my own load
just when the cum from the mans cock was filling the sissy boys mouth.  In
the back of my mind the idea of me being in that situation was exciting.

	I never really thought about sucking a man's cock before but being
dressed in these sexy clothes made me feel like a girl, and a very slutty
one at that. Normally when I jerk off I just do it once and the feeling
sort of goes away and I go back to what ever I was doing before, I had the
desire to jerk off. But wearing the outfit just kept me so horny, I stayed
dressed and found another video of a sissy boy just dressed in a sexy out
fit. He was alone but this one had taken a long skinny cucumber and coated
it with something greasy and slid it into his boy pussy, as he slid the
thin pantie fabric aside that ran up his ass crack.

	My cock was hard again ready for another go at stroking when I
decided I see what it felt like to do just what he was doing. Still dressed
I ran to the kitchen and looked in the refrigerator and found the perfect
thing. My mom had bought a long skinny cucumber which was wrapped in a
plastic sleeve. The only thing I could think of to use as a grease was
mayonnaise. So I took some and put it on a paper towel and brought it back
to my room for what would be next.

	I did not want to get my outfit dirty so I took off the outfit I
had on and decided I put on just my sister tube top. Since I was skinny it
did not look bad and sort of sexy, then I proceeded to do what the sissy
boy in the video was doing.  Before I shoved the cucumber up my ass ,I
opened my mouth and was making believe I was sucking a cock. I had the tip
in my mouth and was imagining that it was a man's cock. The idea seemed
kind of appealing to me. Then after I did that I took the paper towel with
the mayonnaise on it and wiped it on the plastic that covered the
cucumber. I knew this may get messy so I had grabbed a towel from my
bathroom and put it down on the bed. I then moved my laptop on the bed so I
could still watch the video and got on my bed on my knees and bent over and
with my free hand I took the greasy cucumber and slid the thinner end
towards my boy pussy.

	I was getting a tingly feeling as the tip of the cucumber touched
the small opening of my ass hole, or should say my boy pussy. I started
sliding the cucumber in and my hole, my ass was sort of fighting back as
the cucumber was being pushed in. I could see the boy on the video was
doing it easily so I figured I could do the same and kept the pressure
up. With applying more pressure and loosing up my ass muscles , the tip
made it's way inside of my opening. Once the top third slid in I could feel
some pain. so I stopped long enough for my ass to get used to the
feeling. By then boy in the video was moaning and he had more then half the
cucumber slid in his boy pussy. I figured if he liked it so much I would ,
so I kept the pressure up and before long I also had more then half the
length inside my body. I was enjoying the feeling of having something long
and hard in me. In the back of my mind I was thinking would this be like,
to have one of my friends or some man shoving his cock in my boy pussy.


	I suspect the feeling and the thought of a real cock fucking me was
more then my imagination could handle and I felt my cock shooting a large
load of cum with out me ever stroking my cock. Not sure what was happening
to me but all I knew was I was so turned on by the clothes and the feeling
of something long and hard inside me. Even after cumin the second time I
was still turned on, so not sure why but I turned on the camera on my
laptop and started to record myself dressed up with the tube top and still
sliding the cucumber into my pussy. At one point I laid on my back raised
my legs up high and let the camera get a good view of my hole being
stretched by the cucumber.

	While doing this I closed my eyes and was moaning and not sure why
but I was talking to the camera as if it was a guy and saying how good it
felt. I was telling it how I would love to have this done to me by a real
cock. And for an little extra, I though back to the video where the sissy
boy was sucking the mans cock.  I said I be more then also happy to take
who ever I was pretending to be talking too into my mouth. While this was
going on my cock was hard again and yet again my cock started pumping out
another load of cum. I suspect cumin brought me back to reality and I
stopped. I guess I should have deleted the video I had just taken but then
let's face it we do not always do the smart thing when we are horny. So I
saved it on my laptop figured maybe I want to watch it again.

	After that I cleaned up had to take a shower to get all the dry cum
off of me and the mayonnaise from my well used and stretched ass hole. I
then put all my girls clothes away and put them in a hiding spot. I then
felt it was late enough and my mother and sister be back soon so I went
back to my normal life, I did think back to what I did in my new adventure
an it still turned me on some.

	The rest of the week was pretty normal. I went to school and the
only difference was when I went into gum class I found myself looking a
little bit longer as the guys around me took a shower. For the first time
realize that some of the guys seemed to grow a little when they spent time
washing there cocks. I tried to make it not so noticeable as I was checking
the boys out. I realized that one of the boys that happen to be one of my
close friends was one of the boys who did firm up and have to admit was
rather bigger cock then the other boys. David was about a year older then
me and at least 6 inches taller and had at least 25 pounds on me. We been
friends since we were very little but we sort of grown apart some, since he
was more of a jock and being honest I was poor at any of the sports I
tried. I guess I did look a little too long and on the second time as I
checked out his package I noticed a sly smile coming from David.

	The next class was science and both myself and David were in this
class. I have to admit David was better in sports, but I guess you consider
me a nerd and I was much better at science and looking at our grades it was
easy to see that. While in class David asked me if I would help him get a
better grade in class since if he did not get at least a C or above, he be
sidelined on his sports team. We had a science project that had to be
completed by a two student team, he figured if we teamed up I pull his
grade up. I said OK to that but I wanted to be sure he was going to pull
his weight, I did not feel I should be doing all the work and him getting
half the credit, after all what was in in it for me.

	It has been a while since David had dropped by, but not a great
shock to my parents when I told them we had this project together. After
all when we were younger David and myself hung out together all the
time. We had set it up that we start the project on Saturday when we were
both off and I had free time, and David did not have practice. The project
was not hard it had to be something to help the environment so after a
little research we decided to do something that used water ponds to store
the energy from a solar field so that it could then be used at night when
the solar cells were no longer useful.

	David was good with the computer and also was good at the software
used for presentations, so I worked on the calculations needed to determine
how much water we need to transfer to the ponds using the excess power that
was created during the day. Being honest it was mostly guess work but the
the idea had to be some what believable with stated facts. David did all
the web preposition that we used to explain what our project was about. We
had 4 weeks to work on this so there was plenty of time.

	During the time we were working on it my father called up and said
he was taking my mother and sister shopping so he be out for rest of the
day. Since by then it would be dinner time he said he was going to stop for
dinner and be home by say 8pm. He said if I was hungry the two of us could
hit the left overs in the fridge. After working on the project for a few
hours we had a lot done and was way ahead of the time line for the project.

	Since David was on my computer he said he had a good idea to spend
some of our time and he opened up my browser and was now looking at some
porn sites. I know it was silly of me but since my family did not know
anything about computers I did not make sure my history and sign on
information was not stored.  David went to one of the sites that I had a
sign on and of coarse when he brought up the page, the PC automatically
signed me in. Since this site kept track of my history all the things I had
looked at, were in a list of favorite videos that it felt I would like to
see again.

	So here David was presented with many videos of boys dressed in
sexy girls clothes and some were more then just being dressed, some were
taking the part of the girls with other boys and some men . I tried to take
the PC away from David but he stopped me and said he had noticed me looking
at the other boy's cocks in the shower and wanted to see what I was really
into. David is a lot bigger then me so I figured it was not in my best
interest to try to take away the computer, if anything the only thing that
would happen is that I break it. I figured what the hell I guess part of my
secret was out, so how could it get any worse.

	I was soon to find out while David was looking at the porn I
noticed that is cock had tented his pants. He did not even try to hide
this, but instead he even went as far as taking off his pants and
underwear. So here was David sitting at my desk with his hard cock on
display and I was unsure what to do, should I tell him I wanted to suck him
or not. This was fixed in a few more minutes more when for some unknown
reason David went into my file explorer and looked at the files I had down
loaded or stored.

	There it was the movie of me dressing up and playing with the
cucumber, he hit play and here I was doing my thing. I had started the
movie while still dressed in the crotch-less panties and shear top. I then
changed into the tube top and used the cucumber like a dildo and taking it
in my mouth and them my ass. There was no way of hiding what I was doing
and since the video showed me cumin while I was being fucked by that
cucumber, all my secrets were out.

	David watched the whole video till the end and then started it
again but this time he looked at me and said no need to jerk myself off
when it seems I have a cock sucker who is willing to do it for me. So he
grabbed my hand and placed it on his cock and had me stroking his
cock. Then he looked up and said it would feel better if my cock was wet,
and while saying that he moved his chair around spread his legs and took my
head in his hands and guided me down between his legs. I realized I was a
natural for doing this, I took his cock into my mouth and was soon sliding
his shaft inside my mouth and at the same time using my tongue to run over
the ridge of the helmet on his cock. I was still dressed and felt like I
wanted to strip, David held my head and did not let my mouth let loose of
his cock. I could feel him getting harder and felt it pulsing and next as
he held my head he started shooting his load of boy cum into my waiting
mouth. I did not have a choice I had to swallow every drop. The next part
was something I wanted to do, I used my mouths suction action to pull every
extra drop of cum that was still inside of him as I milked his cock of all
of his load.

	Once done I guess I could not help from hiding my smile as he
pulled his now drained cock from me. David looked at me and said that was
the best blow job he ever had , but did add that in truth he did not have
many since only one of the girls he went out would do it, and no where as
good. He did add in that she never would have let him cum in her mouth and
doing so was so much better.

	I was hoping that David was going to let me get undressed and
return the favor of giving me a blow job but that did not happen. He went
off to my bathroom washed up his cum cover cock and got dressed. Soon after
that he left and said we have to get together again to continue to work on
the project. He did ask that we set up a time when we had time to work on
it with no one home since he like to repeat what happened today.

	We went a few days and I had met David in school but we could not
talk, and he acted like everything was normal between us. It was set up
that on the next Wednesday my sister had something at school and my parents
were going with her, so the house would be empty. I made the excuse that I
had set it with David to work on the project since it was one of the free
nights that we could get together. I told David of the situation and he
said he could make it. The day that we were suppose to meet, when still at
school David pulled me on the side and said that he wanted me in the outfit
that he saw me on in the video. We were trying to keep this as quite as
possible so I shook my head as to say yes.

	Once my parents left the house I went into my stash of outfits and
picked the one with the sexy top and the crotch-less panties. I was not
sure how how David was going to react when he saw me and my cock sticking
out. I was a little bit nervous but after a few minutes dressed up I sort
of relaxed.  My cock had gone down and that gave me a good idea. In the
porn I had watched I had seen where a few of the sissy boys had tied a
string on there cock and pulled it back thru there legs so from the front
they looked like a girl. So I did just that, I took some thicker yarn so it
would not cut into me and tied a loop on one end. Then I slid my head of my
cock in the loop and from the back pulled it so that it went in between my
legs and then I tied the end too my waist so that my cock was pulled back
out of site. I did realize that with my cock in the loop and pulled I was
less prone to get hard since it hurt when I started to firm up.

	I did find in my clothing stash a see thru robe that I put on and
decided that I use that to answer the door when David showed up. It was
almost time so I was all ready, I heard the door bell ring and peeked thru
the door hole and saw it was him. I opened the door and greeted him like I
was his slutty girl friend having my stud over to fuck the hell out of
me. I guess in the back of my mind that what I was hopping for.


	David looked at me all dressed and and said Ben in a very perverted
way you look so sexy, and if it would have been dark in here you could have
almost passed as a girl with your thin body and the out fit you are making
me very horny. David said "Ben I want you to turn around for me I want to
check you out". I did as he asked and when I had my ass facing towards him
I sort of bent over a little. When I did he reached out and slapped my ass
in a friendly way. Then he said open the robe so I can see you
better. Being honest the robe was so shear not sure it blocked anything but
after all I was his little slut.  I had decided that what ever David wanted
he was going to get, after the last fun we had together I was willing to do
anything he wanted no matter what it was.

	When I swung around with my front facing him he looked down where
my cock should be sticking out and he looked and said I like what you did
with your cock, it almost like you have a real pussy there. I smiled at
David and in a sort of girls voice said I will do anything to please you
David. With that he just smiled and said the only thing that would be
better is if I had some small tits, I thought about it for a minute and
said I have an idea and will be right back. I ran back to my room and since
I still had the stash out of the clothes I found the training bra and the
padding that my sister was getting rid of and real fast put them on. The
bra and the pads were skin color so it was like they were part of me.

	I came back to where David was and by now he was sitting on one of
the chairs in the family room with one exception, he was now naked and
sporting a nice hard on. I walked in and he looked up and noticed my new
little tits and said I like it, just the little extra touch that adds to
outfit. With that he said my cock needs attention get down on your knees
and take care of it. As I was getting between his legs David said maybe I
will call you Susan since you look a little like your sister, and I for one
would have loved to have her sucking me. I went along with this and in as
sexy way I could I lowered my mouth to his hard organ and took him into my
mouth. Other then the other day was the first I ever had a cock, but I sort
of figured it out. I did what I thought I would like and I was for sure
getting a good reaction from David. I realized he really liked when I was
using my tongue to circle the ridge of his helmet of his cock. I could tell
he really liked that. by now he was holding my head and telling me how good
it felt and saying Susan you really do know how to suck a cock. I pulled
back and asked David if he wanted me to get naked and he said no it is
really hot with you dressed like a girl.

	Then he looked at me with a sly smile and said get back to what you
were doing I have a gift for you. It did not take a genius to figure out
his gift was going to be a big load of cum straight into my mouth, and
surprising to me I really wanted it. I had this utmost desire to taste his
cum as it went into my mouth. I had been thinking about this before we
started and thought that if he was to cum in my mouth again I would hold
the cum in and use my tongue to give his cock a cum bath and at the same
time I hold the cum in my mouth till I was ready to swallow every ounce of
it.  I knew when he was ready since his cock started getting even harder
and then I felt the pulsing and could taste his fluid, pulse into my
waiting mouth. I did what I said I would and took the cum with my tongue
and made circles around his cock. I could tell he liked it from the grunts
that he was making and also since he was still pumping more cum into my
mouth.

	After a few minutes of me still sucking his cock he had me stop
said his cock was too sensitive, so I stopped and asked in a very feminine
voice if he liked it and David said " Susan you are so much sexier and
hotter then any girl I been with", I have to admit I took that with a smile
and realized that he did have a few girl friends but from our talks before
he was lucky if he got a girl to suck him, Very few of the girls in our
school did let boys fuck them. So we stopped a while and went to my room
and worked on the science project a while. David asked me to stay dressed
as I was and he preferred to still stay naked.  Once in a while while we
were working close I run my hand over his cock to get him hard again and
once I bent down and took his cock back into my mouth and sucked him but
not long enough for him to cum.

	Being the slutty girl I was I had plans for the next load of cum
and it was not to go in my mouth. So as we were working on the project I
went over to the bed and bent over like I was looking for something and
with the panties I had been wearing my hole was in plain view. I had
loosened the string that hold my cock so it was not in the way of my boy
pussy. As I notice David looking over I teased him by shaking my ass a
little, this did the trick because I could see his cock growing again. I
put my hand down and bent over more making my boy pussy a perfect target
for his hard cock.

	I had been thinking about having David fuck me so I was prepared I
had gone into the kitchen before he came and brought to my room a fat
carrot and grabbed some hand cream to make it slippery. I had put this on
my night table and as David watched I reached over and took the greased up
carrot and slid it into my boy pussy. I looked back and smiled and said
just making it easy for you to fuck me. With that David got up and being
led my his hard cock he made a straight run and as I pulled out the carrot,
he slid his cock into the empty void. I could tell from the smile on his
face he was enjoying it and from the smile on my face he knew I was
also. He was taking long strokes and almost pulling all the way out before
he slide his cock back into me, I was loving the feeling and so was he.

	We did it this way for a while then David said he wanted to try
something different, he asked me to lay back on the bed face up. I pulled
back the blanket and laid as he requested with my back on the sheets. David
got on top of me and we were face to face and he started kissing me. I
never kissed a boy before but dressed as I was and in the frame of mind I
was it all seemed natural. David was kissing me and rubbing his hands over
my fake tits, he was treating me just like a girl, and I loved it. I was
getting so hot and I asked or I should say begged that David finish fucking
me I needed his cum deep in my boy pussy. With that he had me raise my legs
bent me over and with now access to my boy pussy he slid his cock back into
me. Since I was bent over my now free cock was sticking straight out and
pointing at my belly.

	David was fucking me and also kissing me and once in a while he
take his mouth off of me to tell me how good my boy pussy felt covering his
cock. I was so excited my cock started pulsing and I was shooting my own
load on my belly as he kept his pounding up. It took him a while to empty
his load into me and long enough for me to cum twice with out ever touching
my cock.  When David did cum he pushed hard into me and made sure he
deposited his cum deep into my body.  When he was satisfied that he had
given me all of his cum he pulled back and stood up.

	 I was looking at his dirty cock as it was still semi hard, David
looked at me and said you are such a cum slut and I had to agree with that,
he said it is only fair you clean me up since I did take care of your
perverted needs, and again I had to agree with that. He moved over so he
was close enough for me to take in his cock in my mouth and I used my
tongue to clean him up. As I was doing that he noticed the cum I had
deposited on my belly and he used his fingers to scoop up the wet cum and
stuck his finger into my mouth so that I was now eating my own cum. He had
me do that till he had wiped up all the cum that was on my belly. Felt
strange doing this but have to admit was fun, we were both a mess so David
said lets jump into the shower.  For this I stripped and it was now just
two boys in the shower not any sign of the sissy boy I was a few minutes
ago. In the shower David helped me clean up so it was nice to have his
hands run over my body including my cock and he did run his fingers in my
ass to clean up all the cum and hand cream.

	I guess doing this turned on David again and I was rearing to go so
here I was down on my knees again sucking his cock. David did stop me for a
second and turned around and bent over a little and told me to lick his ass
hole. I never done this before but was willing too, so I used my tongue to
first circle his hole then on his request I pushed my tongue deep into his
hole, I could tell he liked that. After I ate his ass a while he stopped me
and to my surprise he got down on his knees and took my cock into his
mouth.  Sorry to say way too soon I was ready to shot my load, he could
tell that I was going to cum so he pulled back and let my cum shoot on his
chest. He looked at me and said what are you waiting for lick up your
cum. With that I went over and licked up every ounce of cum off of his
chest.

	Once I was done he got up and indicated to me he was requiring
another blow job, so I was back on my knees sucking the last ounces of cum
from his well used cock.  One he came we dried off and both got dressed
into our normal clothes. There was still a few hours left before my parents
would get home so I took all my sheets that were now dirty from cum and
also my sexy outfit and thru them in the wash, I have enough time to wash
and dry them and stash them away before they be home.

	I was a little confused I was not sure what I liked better being
dressed up as a sissy boy or just naked and having David and myself enjoy
each other. I suspect in the days to come I have more adventures and no
reason to select one or the other since they were both fun.