Credit: https://www.nifty.org/nifty/transgender/she-male/something-different by wood guy
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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This is a strange story for even a pervert like myself, I am an
older guy who lives in a large senior development, a very large one with
active adults. To explain first I am 65 years old, a little over weight,
married, but wife does not know about the fact I love to play with other
guys also. Been having sex with boys since I was a boy and tried many a
thing, but as I have gotten older I seem to prefer to bottom. There are
times I just like being a submissive slut to another guy and let him do
what ever he wants to me or my hole. I tried cross dressing but did not
really become my thing but I can understand why some guys like doing it.
So my wife and myself are part of a committee that helps out in
arranging parties to raise money for other charities. So we were in a
meeting and since I seem to get stuck making the slide presentations, I was
paired with one of the other ladies sort of. Let me explain, her name is
Linda but all the women treat her like one of them since that is the way
she prefers, but the men seem to sense that she may not be a women. She is
very thin and just a little shorter then I am and I am 5'8" so she is maybe
5'6". If I was to guess I say she is in her late 50's or early 60's at
most. I have never seen her wearing anything other then tight fitting
stretch dresses that form to her shape. As she said she sort of looks like
a very thin girl, with small tits, at least it looks that way. One of the
things that I see as a give a way is that she has excessive make up on, and
very perfume, and her face just looks like it belongs to a man, but in
truth none of us men are positive what her sex is. And I should add when
she talks it at least to me sounds like a man trying to sound like a girl.
So here I am at the meeting and the leader asks me to get
together with Linda since she has all the pictures from the last party we
had and she is not very computer savvy. In order to get them over
to me in
the form that I need I made arrangements to go to her house on the
following morning. On the ride home my wife says something and I just kid
back. This is going to be interesting since in most of the meeting I try to
keep my distance from her. Being honest I wondered what would it be like
hooking up with her for sex, I at least imagine she gives great blow
jobs. Then I said "No big deal I just need to go there and arrange the
pictures, then sort them and then copy them off to a USB stick so I can
make a slide show for the next party. Depending on how fast her computer is
should take me a good part of the morning."
The following morning I get up and tell the wife I am heading
over there, she says to me like she always does "be careful", I tell her
sure and think to myself what's to be careful. For one thing I have no
desire to fuck her and I do not suspect we would get in a situation where
she would fuck me, and that is even if she has a cock between her legs. So
I arrive at her house and she lives alone, and when I answer the door she
is in her normal outfit, a tight form fitting stretch dress. She is
friendly like she always is and leads me to her spare room, where she has
her computer located. As I am walking behind her I wind up looking at her
ass, like I always do when I follow women, and to me she has a firm ass
like a tall girl but a young one. Or in truth I have seen the same bubble
ass on some young boys but that a different perversion of mine. Once in
the office she has me sit down and shows me where the collection of
pictures that I need to look at are stored. I thank her and tell her this
will take me a while, she says that's fine she had nothing else planned for
today. As I am looking at the pictures she stays with me and as she is
pointing out some of the better pictures. I agree and select some of them
for the project. She is leaning over me and I feel her hand on my leg and
I do nothing to stop her from doing that. At one point I had my arm down on
the front of the desk and she leaned in real close and seemed to push her
crotch into the back of my hand. Hard to feel with the back of my hand but
with her crotch touching it seemed a little too big to be a pussy. I did
not move my hand and she did not stop pushing her crotch into my hand, and
she sort of had a smile on her face as she was doing it. Being honest I was
not sure what I should do. If there was a chance that she was a transsexual
who liked to fuck then I would go for that idea. I was not sure what to
do, after all, myself and my wife worked in the same group I would not want
it to get back to her. So I played it safe and did not attempt anything,
like say, turn my hand around so when she did it again I would get a real
feel of her privates.
I worked on the pictures for a while and while doing them she said
she be would back in a few minutes, she had to go outside and explain to
the gardener what plants she wanted changed out for more colorful ones. I
said "take your time" and off she went. I was finished with my sorting and
selecting so I closed the window to set up my next step. After I closed the
window I noticed this icon on the screen that just made my eye go to it. I
figured what the hell, she said she would be outside a while so I will take
a peek. I clicked on the icon and it brought up a folder with many pictures
inside, after looking at the first few I realized it was pictures of Linda
with other men, some she was getting fucked or sucking cock, but there were
quite a few of her fucking some of the guys. In the pictures where she was
sucking cock it was not hard to see that she had a good size cock between
her legs. In all of the pictures she was dressed in a sexy girls outfit,
being honest not my thing, but seeing pictures of her fuck some guys was
hot. I guess I was not really being careful and did not realize that she
had come back into the house and back into the room I was working in. I
suspect before I realized it, I had made a few of the pictures of her
fucking guys larger so I could see them better and it was having an effect
on me since my cock was getting hard.
I was caught, what could I say? She came over and asked if I liked
the pictures and I had to say yes, then she said "I notice the pictures you
enlarged looks like you like to be on the receiving side" I had to answer
"yes I do". Without saying another word she bent over me and had her hand
in my crotch and was fondling my hard cock. She then had me stand up and
she pulled down my shorts and underwear and my cock exposed. I am not a big
guy maybe that is why I like being on the receiving end, but I say I am
maybe six inches and average width. This may sound crazy but in my mind I
preferred a cock like mine for sucking since it fits in my mouth so much
better then a long cock. But if I was being the one getting fucked then I
like guys that are really hung, just something about a long fat cock as it
stretches my man pussy.
I was in heaven when she slid down to the floor and started sucking my
cock. I am a good cock sucker and have to admit she knew what she was
doing. She sucked me a while then got up and pulled off my shirt so I was
now naked. I told her "I do not have a lot of time, so let me set up the
transfer process so it can run while we are doing something else." She
then had a smile on her face and she asked me "Since we're short of time
what would you like to do?" I just pointed at the picture of her having
some guy bent over and she was fucking his ass.
She said "Fine with me, you set up what you need to and I will be
right back, I need to change into something more comfortable" I worked as
fast as I could and the photos that I came for were starting to be
transferred to the USB drive. This would take a good while, when the
process started Linda called out to me and said "if you can, break away for
a while." I said "yes the copy started and will be finished in about 45
minutes." She then said "good, that will work, come into my bedroom," so I
did. I was still naked but my cock had went down, when I walked in her
bedroom Linda was wearing the same outfit that I had seen on the girl in
the photo. It was a sheer pink baby-doll sleep wear, she had pink ankle
socks and no panties which looked hot because when I entered the room she
was just slipping on the socks so her ass was in full view. I looked up at
her top and she did have tits, small but on a thin frame I say just like
say a twelve year old girl. I forgot to mention young girls are a turn on
for me also. She knew I was looking, so she shook her ass a little and said
"sure you do not want my pussy, it is nice and tight? But when she turned
around her good size cock was visible through the shear fabric that made up
the outfit. I had decided that I wanted that cock in me, so I said "if it
is ok with you I like to be the one on the receiving end." She then said
"since we do not have a lot of time lets not waste any", she had me come
over to her makeup table and told me to lean forward and she grabbed a anal
plug off the counter and looking at it, I could see it was slick from oil
that she must have just applied.
The plug felt so good as she slid it into my ass. I was tight
since it been a while since I been fucked. She hit a button on the anal
plug and it came to life. The thing was vibrating and also seemed like the
very tip was getting bigger, felt like it was growing in my ass. Then she
said "while that's working on your hole, I need you to work on this." She
then put her hands on my shoulders and pushed them down and I was on my
knees, with the anal plug doing a job on my hole and really making me
horny. She then positioned her cock in front of my mouth and I opened up my
mouth and I leaned in and here I was sucking Linda's cock. Her cock was
growing as I did and when she was as hard as she was going to get she was a
good 8" and some what thick. I suspected she knew her cock would be hard to
take in with out the step to loosen up my ass with the anal plug.
She then had me get up and lean against the makeup table sort
of bent over, she then removed the anal plug from my hole. As she took it
out and put it on the counter I realized I was right, the plug was a lot
larger than it was when she inserted in me. As soon as it was out she had
me lean over the counter and she slid her big cock in and started slowly
going deeply into my man pussy as she could. It was strange having Linda
fucking me but it felt fantastic so I did not care. She fucked me a while
and every once in a while she seemed to move my position to the side a
little. She had to be fucking me for almost thirty minutes, she would go
for a while then slow down or stop and then go again, just teasing my man
pussy but at the same time lasting really long. I knew what she was doing
when she get close to cumming she would slow down or stop so she would cool
down some. I did this myself when fucking knowing that when I did cum my
load would be more intense and more cum would come out.
The crazy thing is my wife never liked that, when we were younger she said
I fucked her too long and she was not crazy about me cumming a lot. I guess
that is why I also liked men I hardly ever met a man or boy cock sucker who
did not like a big load.
But then I felt her cock tense and she pulled my hips in and her cock was
buried all the way in my body, when she started filling my cavity with her
cum I could feel the wetness and I have to say I loved it. The whole
experience was sort of strange to me but still very hot, I figured I would
have to make some excuse to come back here again. Also at the last moment
she let me know she had taken some pictures of her fucking me so she could
remember it, but she added "I made sure I blocked your face" just like the
other pictures I had seen on her computer.
Before I collected all of my stuff and the photos I needed I sort of let
her know that if she had a few guys over and she needed a bottom guy just
let me know, I would make some excuse to stop over. She smiled at me and
said "did you like you man pussy filled?" and I smiled and said I loved
it. She said she knew what it felt like and she loved it also but sometimes
she likes to be the top. I said I was glad that was the case this time..
Hope you enjoyed this story email me at woodd_guy@yahoo.com