Online Chat Room to Real sex First Experience with a Housewife
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Online To Real Life free porn video
Online play to sissy life.
How many websites are there dedicated to sissification of males? Plenty.
How many chat rooms are there for submissive men and sissies? Plenty. How
often are these sites kept up to date? Rarely. How often do you get a
decent interaction on one of the chatrooms? Rarely.
It's probably the nature of the beast. After all, the desire for
sissification and humiliation is, I suspect, a sexual thing. The hornier
a male, the wilder his fantasies, so those males with sissy desires will
have increasingly wilder fantasies as they get hornier. But, as soon as
they cum, most men quickly get out of the panties they are wearing, hide
the dildo they were sucking on as they wanked, cut the connection to the
chatroom where they were role-playing as a sissified male sucking on a
dominant males cock.
I believe that the typical male sissy is as described above. There are a
few who are truly submissive and truly desire the lifestyle of a sissy.
And that is why there are those rare websites that keep going and are
regularly updated.
Of course I have described the two ends of a spectrum. There are those
who fall in between these two extremes.
I was, primarily, a 'sexdrive sissy'. The hornier I was, the wilder my
fantasies. However, I leaned towards the lifestyle sissy in that I wore
women's jeans (I had no male jeans), I wore panties (I had no male
underwear) and I kept my underarms waxed. These were my sissy lifestyle
choices. But as I got hornier I would start wearing lip-gloss, bras,
women's boots and would visit as many sissification sites as I could.
It was during one of my hornier moments that I met Ms X on a sissy
chatroom. Of course, as is always the case, I suspected that Ms X was a
male acting as a woman. But hey, I was horny, and so I responded to her
command to privately talk to her. She asked me plenty of questions, and I
answered them honestly (except for my name, age and location which I
changed slightly). She asked what I was wearing, and I described the
female underwear that I was wearing. She told me to take a photo and
email it to her (she provided an email address) telling me that if I did
that she would then email a photo of herself in return.
I figured, what the hell, I'd do it. I spent 10 minutes getting a photo
that showed my body but had my face out of shot and I emailed it to her.
In fact I emailed three to her. I used my sissy email account that I keep
for things like registering with sissy forums and sites. Five minutes
later I received an email from a 'Ms X'. I eagerly opened the attached
jpgs (there were two), and was presented with a photo of the stained
inside of a pair of panties, and a photo of a woman's naked ass. I was
given 30 minutes to come up with an essay describing how I would worship
both the panties and the ass at once.
This was quite exciting, I'd never had this sort of experience before.
And so I did. I wrote an essay explaining how I would wear the panties
over my face as a mask, keeping the stained gusset against my nose and
mouth, and the panties positioned so that my eyes would be visible on
ether side of the gusset as the gusset came down my face. Then with the
mask in place I would kneel behind the owner of the ass and bury my
masked face between those lovely ass cheeks. I sent the essay off.
I got a response telling me to log back on to the chat forum. Ms X was
there when I logged back on. Once we were chatting privately Ms X asked
if I wanted to play in real life. I agreed and we decided that I should
go to an internet cafe in Southampton the following Saturday. I was to
then log on to my email account at 10:00.
Saturday came. I almost didn't go, but then I thought that it was all
anonymous. There was no way anyone would know which cafe I would go to.
So I went and at 10:00 I was logged on and a new message arrived. I was
told to go to the old castle wall that ran along the road at the bottom
of west quay shopping centre. If I were to walk along that wall I would
see a crumpled up bag from the women's clothing store, New Look. I was to
pick it up and go back to the internet cafe to report that I had it.
I went to the wall and there was no one in the road along which the wall
ran. The road is pretty quiet most times, and there is always a lot of
litter there. I walked down the road keeping an eye on the litter against
the wall. Sure enough, about a third of the way down there was a New Look
bag. I walked past it. Was anyone watching? Should I pick it up? What was
in it? My heart was pounding, my mouth was dry. I looked around, I could
see no one. I turned around and walked back. I looked around again, still
no one. As I walked past the bag I quickly bent down and scooped it up as
I went past. The bag was light. Heart pounding madly I looked inside.
There were the panties in the photo!
I rushed to the internet cafe. And logged on, sending an email saying
that I had the bag. I was told to go home and photograph myself with the
panties over my face like they were the mask I described in my essay
earlier the week. Then I was to photo myself tonguing the panties. I was
allowed to cover my face with dark pantyhose, and that was to be the next
part of my assignment. I was to go buy some dark blue pantyhose, that
would fit me. I was to keep the receipt. Once home I was to put them on,
and photograph myself, to show they fitted. If they did not fit I was to
go buy some more until I got a size hat did fit. Once I had a pair that
fit I was to put them over my head, then put the knickers over my head
like a mask and photograph myself. Then I was to cut a hole in the gusset
of the pantyhose, place them over my head so that my tongue could stick
through the hole, and then photograph myself licking the panties.
I was really happy that whoever was doing this was keen to endure my
anonymity and so I did as instructed. Because I wear women's jeans I knew
what size pantyhose to buy and I duly bought them, got home, took the
photos and sent them off once I was happy that I could not be identified
from them.
The next task I was given was to write an essay describing the whole
experience until now ensuring that I described my feelings as well. I was
to describe how the panties smelt and tasted and how smelling and licking
a strangers panties made me feel. I did as instructed (the panties smelt
like women's perfumed deodorant and didn't really taste of much).
In response to that essay I got some photos of the woman wearing the
panties I had picked up. There were 5 of them. They showed her pulling
them up into her ass crack, pulling them against her pussy, rubbing
herself through the panty material, her leaning forward the panties
pulled down to show her ass cheeks and one of them hooked on her neatly
painted toenails. None of the photos showed her face. But she did have a
sexy body.
Together with the photos were instructions to log on to the chat site at
16:00. I did. Enthusiastically! Our conversation determined that I did
live close enough to Southampton to get their easily and that I ran and
cycled as exercise. Between us we agreed that I would go run on the
Southampton common the following morning. I agreed that I would start at
the paddling pool at 07:00 in the morning and I would then run a circuit
of the park. I would wear a pair of long legged leggings and a t-shirt
long enough to cover my ass. I would bring the panties with me and would
in fact wear them over my leggings. The panties were a royal blue nylon,
and I figured that although they would stand out against the black of my
leggings, they would not be glaringly obvious, and with a long enough t-
shirt they could be hidden. And so I agreed. She told me that she would
be watching me. She then explained that she got sexual excitement out
watching a sub male follow her instructions, the wilder the instructions,
the more turned on she got. She explained that she would make it exciting
for both of us. So, what she wanted was for me to run three circuits of
the common, each time stopping at the paddling pool gate. If I wanted to
take the game up a notch then I was to ensure that the panties over my
leggings were visible so any t-shirt I wore must not go further than
halfway down my ass cheeks. If she were happy I would find another item
of clothing at the gate (in a discarded new look bag) after my first
circuit. If I wore that item for my next circuit I would find a third
item to wear (this time in a discarded boots bag) on my final circuit,
and if I wore that I would find a final item to take home with me.
At 07:00 the next morning I was doing some stretches at the paddling pool
on the Southampton common. I was wearing two t-shirts, a long one on the
outside and under that a shorter one that clearly allowed the blue
panties to be seen. As I stretched I looked around. Sunday morning. It
was quiet. I could see one person walking their dog in the distance. I
took the long t-shirt off, and feeling really turned on and excited I did
some stretches to show my panties. Of course I checked there was no one
nearby before I did so :-). And then I started my run I passed two male
and a female runner on that first lap.
My heart started racing as I approached the paddle pool gate. There was a
bag there. I stopped and picked it up. Inside was a tube of lipstick and
a can of women's perfumed deodorant. What the hell I thought, I put some
lipstick on and sprayed myself with the aerosol. It was very definitely a
feminine smell. But by then I was so turned on and into this game that I
threw caution to the wind and sprayed myself liberally with the stuff. I
started my second circuit. I passed the same woman who was obviously also
doing circuits. Of course I wondered if she was Ms X, but she treated me
as if I, as a male, were a potential threat to her and she clearly
avoided eye contact. I passed three dog walkers and being aware of my
very feminine fragrance I tried to steer clear of them as much as the
path would allow.
Back at the gate I found another bag. I looked around, no one around, and
picked it up. Inside was a t-shirt. It was pale pink, very pale pink
admittedly, but it was pink all the same and it did have feminine cut
sleeves. Looking round I went to some nearby trees and quickly took my t-
shirt off and put the new one on. Then before I could back out I launched
into my last circuit. I now had two of my t-shirts rolled up in my hands,
and a tube of lipstick and aerosol. As I ran I looked down at myself. The
t-shirt was a bit short, in fact it was shorter than the one I had been
wearing for laps one and two. I ran my fingers around the hem as I ran
and was nervous to fins that quiet a large amount of my bum, and
consequently the panties, was not covered by the t-shirt. I picked up my
pace. I passed a number of dog walkers on my final lap but I avoided eye
contact and just ran past, too nervous and embarrassed to look for their
reactions to how I looked.
At the gate was another bag. Inside was a pair of shorts and a note.
'Oooooh, naughty boy. Such pretty panties and t-shirt. Cover them up with
these shorts. When you get home write an essay describing your experience
today, remember, include as much detail as possible. It must be no less
than 1500 words and I want to receive it by 1 PM or I will assume you no
longer want to play.'
I put the shorts on, they were black with shock pink trim. Turned on by
the tone of the note, and the faint smell of perfume on the shorts, I
slowly walked back to my car, taking my time *(after making sure that
there was no one nearby of course). Sitting in the car I looked in the
mirror to see what the lipstick looked like, it was very dark. I drove
home with a huge erection.
Once home I looked at myself in the mirror. Wow, the shorts looked a lot
more feminine than I had realised. The pink trim was very obvious, and
the cut was unlike anything I had seen on male shorts. I took them off to
try see what I had looked like as I ran around with only the t-shirt on.
I turned my back to the mirror and looked over my shoulder to see what I
looked like from behind and was really shocked to see that the t-shirt
was a lot higher at the back than my 'short' t-shirt had been.
Excited, and still wearing the panties, shorts and t-shirt I started up
my computer and started on the essay. Reliving the embarrassment and
excitement of the morning was almost as exciting as the events of the
morning, and I wanted to get as much of it down on paper as I could
remember, so I described everything in detail, the clothes I wore, how I
felt at every stage, what I did. When I'd finished the essay was 2372
words long. I ran it through a spell checker and emailed it off. I
checked my email every thirty minutes. Hours passed with no email from Ms
X. Finally when I checked just after 8 that night there was an email from
her.
The email itself congratulated me on doing so well and being such a good
sissy. It also congratulated me on submitting such a well written essay.
Ms X said that she had got really turned on reading it. She had made some
changes to it and attached it to the email for me to see. I opened the
attached word document and was presented with the essay that I had sent
earlier but unlike what I had sent, this one was illustrated. Illustrated
with photos of me! Doing the things I had described in the essay! The
paragraph describing my first stretches was next to a photo of me
stretching. Where I described taking off the longer t-shirt, there was a
photo of me taking it off. There were photos of me looking through all
bags, or taking things out the bags, photos of me running with panties
visible, with girlie shorts visible, walking into the trees in my t-shirt
and emerging with the pink t0-sirt. The disturbing thing for me was that
most of them included my face in the photos.
I logged on to my email account. There was an email from Ms X, with 14
attachments, all jpgs. My heart was pounding as I went through the
pictures. They provided an overview of what I had done that morning. The
first showed me arriving, the next I had taken the long t-shirt off, the
next showed me from behind as I started to run (and yes, the panties were
visible) and so on.
As I was coming to terms with what I was reading, another email arrived,
also from Ms X, also with a large attachment. The email read simply 'What
do you think of the draft of my new book?'. I opened the attachment and
was presented with a pdf. The cover page had a photo of me walking back
to my car, pink t-shirt and girly shorts easily visible. The book was
entitled 'The life of a sissy (through the eyes of his mistress)'. The
pdf was a narrative of everything that Ms X and I had done from our first
meeting on that forum and ending with my report of that morning. Ms X
explained everything that had happened from her point of view and used
many excerpts from our forum chats and my emails to show that I was a
sissy and that I had done all these things voluntarily. In this document
even the photos of me with the panty mask, even though my face could not
be made out, were really incriminating as the photos of me running
clearly showed me wearing those panties, and those photos had my face
clearly visible. In fact one of the chapters even covered how I wore
panties both as a mask and as outerwear, and Ms X had put many photos
next to each other to show that the panty on my face was the panty over
my leggings.
Another email arrived. 'Log on to the forum sissy.'
I did. Ms X went private with me as soon as I logged on. She explained
that she did not want to ruin my life, and that if I did everything she
said then no one but the two of us would see that book. However, if I
didn't agree then she would email it to people I knew, and as she had
followed me home from the park, she knew where I lived and would easily
be able to find out where I worked. She did point out that nothing we did
would ruin me, and it would probably appeal to my desire for humiliation,
she was just putting the book together to give me extra incentive to play
as she wanted me to.
Naturally I agreed to play. Later I received an email for my mobile
number, which I sent to her. Nothing happened for three days, then one
afternoon my mobile rang. It was Ms X.
'Hello?'
'Hi sissy, it's Ms X.'
'Hi.'
'What did you have planned for this evening?'
'Nothing.'
'Good, because we're going shopping. What is the earliest time you can
leave work?'
'Three thirty.'
'Very well then, leave work and go to Festival place in Basingstoke. I'll
phone you at four thirty, make sure you're there.'
I plan to continue this story. Feel free to let me know what you think,
and any ideas you'd like incorporated. My email is
[email protected]
Kierra
- 06.08.2020
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