Check Your Taillights
It all started pretty innocently, at least by my standards. For many
years I have been a closet crossdresser and like most, I thought
there must be something wrong with me. The usual bag of emotions and
guilt.
One day I did an online search to see if there was a forum for
crossdressers and sure enough there was. My whole world changed. Not
drastically but change it did. I found there were many others who
felt and dressed as I did and I finally found out I wasn't a sicko
after all, just a little different than the average Joe.
One thing led to another. Because of discussions on the forum I was
able to get up the nerve to tell my wife about my little
peculularity. It didn't go over great with her but she reluctantly
accepted it and I continued discretely dressing when she wasn't
around. I discovered an online boutique that catered to CD's and I
was able to buy all sorts of things. I found that they sponsored a
great website that caters to CD's who like to write stories.
From stories on Fiction Mania I discovered a whole world of
characters I had never realized existed. While reading these stories
I started fantasizing about what it would be like to be those
characters in those situations. Naturally, masturbation was a part of
or inspired by all of this great fuel for fantasy. I also discovered
new porn sites that have pictures and videos of all sorts of these
'characters' and the next thing you know I'm watching training and
hypno videos for sissies and cuckolds. What a whole new world for me!
Turns out, I really liked fantasizing about being a sissy or sissy
cuckold but that's all it ever was. I have fantasized about all sorts
of stuff but would never act on any of it that involves another
person. I am happily married and consider that as cheating on my
wife. Yes, there is the whole school of thought that fantasizing
about sex with anyone but your partner is the same as cheating. I
didn't go to that school.
I have no intention of ever acting out any of the fantasies that
would involve anyone but my spouse. It's all just games in my mind. I
do play out some of the fantasies of other sorts though. Obviously
crossdressing is one of those. I play little games like going outside
in my fenced back yard dressed in womens clothes. I have 'braved it'
(more likely stupidity) out front to the road and back late at night.
I've gone driving around at night with wig and all so most would
think I was a woman if they saw me from a distance. I certainly
couldn't 'pass' any kind of close scrutiny but it was always dark out
when I went driving.
And that folks, was the error of my ways. Sooner or later your luck
runs out. Here's what happened.
I had been driving around 'dressed' late one night while my wife was
out of town. I'd even gone so far as to try my hand at putting on
make-up. I'm not very good at it but it was thrilling going through
the motions just like a real woman. I was wearing a wig as well so it
isn't hard to 'pass' with tinted windows in the dark. Truth is,
nobody pays much attention to other people in cars if you don't do
something to attract their attention.
Well, the one exception to that being the police. Some of them are
scrutinizing every car they see just hoping to find an excuse to stop
it. Yep, and that's what happened to me. All because, just like
everyone else, I never do a vehichle inspection. I not only had a
taillight out but also my tag light was out. Really. To add to my bad
luck, or good luck, it's really a matter of perspective, an
acquaintance of mine was riding with the officer. That sort of thing
happens in small towns. Especially if that person happens to be the
Mayor.
I think the Mayor may have recognized my vehicle so when the officer
said, "Looky here what we got. I think we got us some sort of sissy
fag or something." Tim got out of the police car and came to see for
himself. The cop had his flashlight in my face and I was blinded so I
didn't realize who was with the police officer just then.
The gamut of emotions running through me ran from extreme
embarrassment of being seen as such, fear of being found out by
everyone that knew me, just a hint of question about was I actually a
sissy faggot, all the way to a deep seated thrill at being so
humiliated in front of these men.
Being stopped by the police dressed as I was had the potential to
bring out into public my unusual hobby. It's hard to explain the
excitement of being embarrassed like this, of being found out and
maybe exposed to others as a sissy fag. It's scary but exciting at
the same time. Yeah, weird. I can't explain it but I can't deny it
either.
Now you would think you couldn't get much more embarrassed than being
found driving around dressed as a woman by a cop, especially one that
had just called you a sissy faggot. But...." Oh ho. Umm, Seargent
Brown, may I have just a minute with this, uh, person?"
Holy shit! I recognized that voice. Where from? I knew for certain
that this man knew me and my hopes of people finding out my dark
secret now looked even bleaker. Why had I gone out riding around
dressed like this? What a dumbass!
Once the cop stepped away with his light I could see that it was Tim
Stuart, the Mayor of our little town. We knew each other because I
sat on the city commission with Tim and five others. As a matter of
fact, I was the one that nominated him for the position of Mayor.
See, now is when you become even more embarrassed when you realize
that an esteemed collegue of yours is grinning at you as you sit
clothed in a dress, wearing breast forms, heels, wig and make-up. It
is a whole new level of humiliation when the eye witness knows you.
I don't know if he remembered that I was the one that nominated him
for Mayor and that meant something to him or not. Maybe he was just a
good guy trying to help someone out. I don't know. Tim walked over to
the officer and I overheard him ask if he would just let me go with
the promise to fix the lights. He said he would consider it a special
favor if 'this incident never happened.' Apparently he had some sway
with Sergeant Brown because the cop agreed and after Tim retreived
his phone from the patrol car he walked around and got into the front
seat of my car.
I wasn't expecting him to get in with me and it made things way
worse. I had thought that once the officer agreed to let me off I'd
soon be on my way home. Now, I probably had some explaining to do to
Tim and I wasn't looking forward to that. I mean, how do you get
someone to understand why any sane, grown ass man would want to wear
womens clothes. I have been trying to figure that out myself for
years but I've given up trying. It is what it is.
I did not know Tim real well, mostly as an associate since we both
sat on the same city commission. That being said, you can tell quite
a bit about a person by the stand they take on certain issues, the
manner they conduct themselves in the public eye and how they deal
with the others on the commission and public audience. Are they stern
or are they forgiving? Are they vehemently passionate about their
ideals or are they willing to compromise? Liberal or conservative?
Tim was the stern, passionate, conservative type.
At this point I was freaking out. I didn't really know what to think.
It's one of those things where it seems like time is slowed down so
that you're aware of every excruciating moment yet things seem to
happen so fast your thought process can't keep up. I was mostly
scared, my mind playing scenes of running into people I knew, shamed
because I was a pervert pansy who wore womens panties. All of my
family would find out, my co-workers, my friends, my wifes co-
workers. How could I keep living in this small, close knit community?
My childrens friends would find out, how embarrassing would that be
for them? With social media it would spread like wildfire.
I really wish I could convey all of these emotions, fears and yes,
even excitement that was coursing through me but I cannot find the
words to do it justice. Please stop and take just a moment to imagine
yourself in this predicament and how the recourse of your actions was
about to affect you and all of your loved ones.
No seriously, take that moment and imagine facing family and friends
with that shame. But, if you're reading this then you probably are
the kind to maybe get off on the humiliation part as well. Try to
imagine that part too.
I'm not sure why Tim decided to get in with me but he said, "It's
best if we get moving before he changes his mind." Like a deer in
headlights, I was sitting there in a daze, not knowing what to do. My
brain was overloaded and mostly all I could think was, 'Please,
please, please, don't let anybody else find out about this.' That's
about all I was capable of at that moment. Not, 'Put the car in gear
son and let's get home and get out of these ridiculous clothes.' Not,
'You'd better figure out some way to explain this to Tim or at least
beg him to keep quiet.' No. I was just sitting there frozen.
I finally took Tims suggestion and put it in gear and of course my
first and only instinct was to get home, change clothes and get the
make-up off. That's where I headed. I hadn't even considered that I
would have to take Tim home. I didn't live too far from Tims place
and when I put the signal on to turn towards my house Tim asked if I
was going to make him walk from my house or what? Like I said, all I
could think was to get to the safety of my home but of course I would
need to take him home. I battled with the thought of going home,
changing and then taking him home but that made no sense, especially
since he had just bailed me out of a most awkward situation. But I
was afraid to be out any longer than necessary dressed as I was.
Reluctantly I turned the signal off and continued straight towards
his home. When I pulled into his yard I put it in park, then waited
for him to get out. Tim didn't move so I figured he was waiting for
me to say something. Like, "Thanks for saving my ass." Or beg him to
be silent. Maybe he was deciding what he wanted to say but we sat
there in awkward silence for a moment until I got up the nerve to
speak. "Tim, I don't know how to thank you enough. I mean really. You
can't imagine how embarrassing this is. I just want to forget this
ever happened and I hope you'll forget it too."
"Actually Ron, I've got a pretty good idea how embarrassing this
would be, especially in such a small town where everybody knows
everybody. As for forgetting, I know what you mean but I assure you
there is no way that I could ever forget seeing you dressed like
this," I was still in shock and didn't know what else to say. I just
wanted him to get out so I could go home and strip off this stupid
dress.
"You look pretty shook up Ron. Everything's going to be alright. Why
don't you come inside and I'll fix us both a strong drink?" Tim
suggested.
"Thanks Tim but I think I'll just go home and call it a night," I
replied. I just wanted to get back to the safety of my home.
"I'm really concerned about you Ron. I don't think you realize the
shape you're in. I mean, this is the kind of thing that could make
someone suicidal or something. No, you should come in. I'll makes us
some drinks and we'll talk about this." With that he reached over,
turned my car off and took the keys from the ignition. Then got out
and walked to his door.
The last thing I wanted was get out of the car dressed as I was even
if it was well after midnight. At home I had the privacy of my garage
but here I was parked out in the open in his front yard. There seemed
little I could do though since he had my keys and I wasn't going
anywhere without them. At no time did it strike me as funny that he
had said he was concerned for my welfare yet seemed willing to give
me something to drink and then presumably allow me to drive home.
I reluctantly got out and headed for his front door. I was in heels
because it hadn't even occurred to me to slip them off. They sunk
into the grass which made walking in heels that much more difficult
and trying to stay on the balls of my feet made my strut look stupid.
It suddenly occurred to me that Tim was married and another bout of
fear coursed through me at the thought of his wife seeing me thus. I
hesitated at the threshhold until I figured it was way past midnight,
she was most likely in bed. For just a brief instant though, I felt a
conflicting sense of disappointment that she probably was in bed and
I wouldn't be exposed to her.
Pointing to the couch, Tim told me to have a seat while he went into
the kitchen to make our drinks. I wondered that he didn't ask what
I'd like but then decided that he probably didn't have that much
selection. He'd probably bring a whiskey and coke. It didn't really
matter, I wasn't that fussy about what I drank. Especially tonight.
The Mayor returned shortly with our drinks and sat across from me in
an overstuffed chair that was obviously his 'throne.' I didn't like
this much as I had to pretty much look straight at him and I was
finding it hard to look him in the face while wearing a dress and
falsies. More silence as Tim looked intently at me. Not knowing what
to say or do I took a long swallow on my drink, nearly draining the
glass.
As I was setting my glass on the coffee table I heard off to my left,
"Hi guys. Or should I say guys and gals?" I nearly wrenched my neck
turning to see who had just made that statement. Naturally it was
Tims wife Gwen. Who else would it be at this time of night? My face
turned beet red for about the tenth time tonight. Could it get any
worse? Well, actually it could have but that was little consolation
right then when I was confronted with the third person, a woman,
seeing the esteemed Commissioner Johnston in all 'her' regallia.
"Hi Gwen," I muttered putting my head in my hands, slowly shaking it
side to side. "Surprised to see me like this, huh?" I give. I just
give. Just thoughts! I didn't actually say that, just felt it from
the core of my being.
"No actually. Tim texted me and told me what to expect. He said you
were quite upset which is understandable."
My head flew up to stare accusingly at Tim for betraying me to his
wife. My face conveyed exactly my thoughts which were anything but
friendly. You'd think in my position I would not want to be the least
bit hostile towards him but I couldn't help feeling that he'd sold me
out.
"WHAT?" he said. "You're the one riding around dressed in womens
clothes, wearing make-up and all, not me!" Staring back with
indignation, he raised his glass in a toast to me and took a drink.
"Fuck you, man," he followed, "I'm the one that saved your ass,
remember. Sergeant Brown does not like fags at all and I assure you
he was going to make it as bad as possible for you. I guarantee he'd
have found an excuse to throw you in jail dressed just like you are."
Once again, even though I should have shown my appreciation he had
pissed me off calling me a fag. "I ain't no fag," I responded
nastily. My mind quickly flashed to a porn pic I had seen and
superimposed over the image of a sexy naked girl was the phrase,
'IT'S OK TO BE A FAG.' I wasn't a fag! I just looked at the pictures,
maybe even masturbated to them. Images of women giving head. It
wasn't the cocks I was concentrating on, it was the women sucking
them. Right?
Gwen came over, sat next to me and glared at Tim. "Cut him some slack
Tim. You know he's upset," Her hand squeezed my knee as she told me
to calm down too. She assured me that everything was alright and I
had nothing to worry about. Handing me my drink she encouraged me to
have another swallow. "Tim, why don't you go make all three of us a
drink, it's not very polite you boys drinking without me." "Oh," she
paused looking at me, "do you want me to call you a girl?" she asked.
"I don't mind, really. It might even make you feel more comfortable
being as you're dressed like one."
"It doesn't really matter what you call me Gwen, I don't think you
could make me feel better about anything right now." Holding my arms
up, thrusting my fake breasts toward her, I said, "Look at me Gwen.
Fake tits. A dress. Wig, make-up, heels. I'm even wearing a garter
belt and hose. No pantyhose for this gurl! How fuckin' pathetic! What
would people think! Hell, I can't even explain to myself why I do
it." I was on the verge of tears now. Tears of frustration. Tears of
shame. Tears for my family who may have to live with my shame
affecting their lives.
"Honey," she said, "It's alright. Nothing bad's going to happen,"
Rubbing my back, Gwen grabbed her drink from Tim and took a sip
before finishing, "Tim stepped in at just the right time. Nobody
knows but the two of us and Officer Brown and he's not going to say
anything since Tim asked him not to. He's bucking for Lieutenant and
he knows Tim will put in a good word for him with the Chief."
"You ARE rather lucky that Tim happened to be riding with him
tonight, though," she commented, "And not to sound rude or unkind to
you but you really do owe Tim a big debt of gratitude. It really
would have been bad for you if Tim hadn't interceeded. I doubt you
would have been able to keep your secret if the mean old cop had put
you in jail dressed like this."
She was right of course, it's just that Tim seemed to know how to
push my buttons and I wasn't thinking too clearly right now.
Swallowing my pride and some of my drink I looked Tim squarely in the
eyes and thanked him for saving me. There was somethng about the way
his eyes bored into mine. It wasn't quite smugness or cockiness but
it made me feel inferior to him. Made me feel little. Made me feel
like I wasn't even in the same league as him. And there, accompanying
the shame I felt at having to be saved from my idiocy was that deep
seated thrill at being made to feel small and weak and silly and
humiliated.
"Now don't you feel better now that you've thanked Tim?" Gwen asked,
winking at Tim
"Kind of, I guess. I don't think I'll feel much better until I'm out
of these ridiculous clothes and all of this is safely behind me," I
mumbled.
"Come now, deary. It's obvious you enjoy pretending to be a woman and
dressing in our clothes. Why shouldn't you feel ok wearing them if it
makes you feel good. Tim and I don't really care how you dress, do we
babe?" Something passed between Gwen and her husband, a knowing
glance.
"Why should I care how she dresses? That's her business," Tim
reflected "She didn't really sound all that sincere though,
considering the mess she was in," Like I said, he knew just how to
push my buttons.
Did he just refer to me as she? That made me angry. I was about to
respond when Gwen handed my drink to me and raised hers in a toast.
"To special friends," She clinked hers with mine and did a sort of
salute towards Tim with hers before tipping it up and downing the
rest of it. "Well, I'm about caught up with you guys. And gals," Gwen
bounded towards the kitchen grabbing our glasses on the way.
"You really think I don't appreciate what you did for me?" I asked
Tim while Gwen was out of the room.
"No. Not considering how deep of shit you were in."
"How am I supposed to thank you? My apology was as sincere as I can
be, what more could you want?" I queried.
"Well, there are......
"Here you go everybody, a fresh round of drinks," Gwen interrupted,
giving us our drinks. There was still a tension between Tim and I and
Gwen could tell. "So what were you....two.....talking about?
I told her.
"Tim, you don't think Ron is sincere? Why is that?"
"What I mean is, this isn't just your everyday favor. Rons whole life
was about to turn to shit. Not just his but his whole family's. A
simple apology doesn't seem adequate compared to how big of a favor I
just did for him."
"Well, I do see your point. It really would have been bad if things
turned out the way they were headed," his wife said. Looking to me
she continued, "You do see what he's getting at don't you sweetie?"
"Well, yeah. I understand that. Tim did me a really, really big favor
for sure. I don't know how to thank him any more than I have though."
"A woman would know how to show her appreciation. You're pretending
to be a woman. Perhaps you'd like to really experience how it feels
to be a woman and show Tim your appreciating like a real woman
would," Gwens tone had changed from the caring, friendly voice she
had been using thus far to a sterner, almost commanding tone. "It
was, as you say, a really, really big favor."
"What are you getting at?" I asked, "I'm not really a woman. It's
just a game."
"One with far reaching consequences," Tim piped in.
"Honey, you do seem to be a bit ungrateful as Tim has pointed out.
You've already acknowleged just how big a favor it was. I would think
the kind of person you are, or at least the kind of person we all
thought you were, would want to pay your debt."
"Are you suggesting what I think you are?" I stammered, flabergasted
at what they were insinuating.
"Not only is it what a woman would do but a sissy as well. And dear,
you are a sissy if I ever saw one. Look at yourself!"
"Amen," agreed Tim.
Wow!!! Wham, Bam, Slam Dunk ya Ma'am. All in one sentence. God, how
did things tumble so far out of control?
But....for a brief milisecond my psyche thrilled at the thought of
paying homage for my rescue; which was quickly replaced by rightous
indignation. What the hell! These people were sick suggesting that I
suck Tim off to prove my sincerity. That was what they were
suggesting wasn't it? Yes! What else could 'what a woman would do but
a sissy as well' mean other than that?
Gwen said I was a sissy if she ever saw one. Somehow that should have
pissed me off too but coming from her seemed to take the sting out of
it. Was I? I sure didn't look anything like the pictures of the
young, sexy gurls in the videos. They were so hot. But then, wasn't I
trying to emulate them to the best of my abilities. I secretly
desired to look like them. It's not my fault I wasn't as slim and
trim as them. Did I also secretly desire to act like them? THAT was a
good question, one that I had never seriously considered before but
it seemed like maybe now was the appropriate time to do so.
This was getting ever more confusing. Should I do it? Should I kneel
before Tim and give him a blow job? I wasn't gay. I had never done
anything like this before. Wouldn't this be cheating on my marriage?
I could just say no and get them to understand that that was asking
way too much. I'd find some other way to go above and beyond to show
my real appreciation.
"It's not even reasonable to expect me to do something like that to
show my gratitude," I told them. "I truly am very, very thankful that
you saved my ass but there's got to be something else I can do to
even the score. Money. I could give you some money. How much do you
want?"
"Reasonable!" Tim bellowed. "Parading around in a dress, made up like
a woman IS reasonable?" he scoffed, "You lost touch with reason when
you started wearing panties and the like."
It was then that I heard the click a phone makes when taking a
picture. Gwen had stood while Tim and I argued and now she had the
phone taking pictures of me. I glared at her. I thought she was
alright. I thought she was on my side, kind of. She continued to aim
the phone and asked, "What's the matter Ron? Tim saved you from being
exposed as a sissy crossdresser and from the other commissioners and
people finding out your dirty little secret and you want to be
ungrateful?"
That one sentence pretty much cooked my goose. She had established
exactly whom I was as she videod me sitting there in drag. They could
blackmail me all they wanted and there was little I could do but go
along with their little scheme. Or, do the unthinkable and let the
world find out. Funny comparison when you consider what else might be
considered 'doing the unthinkable.'
"You've got to be kidding me. You two can't seriously think that I
should suck Tim just to pay him back for what he did? But I guess
you're willing to blackmail me to force me to," I countered, "That
ought to be a really good blowjob, huh?" I laughed.
"Ron. Ron. Ron. You're looking at it all wrong!" Gwen tried to
explain. "We're not forcing you really. We're just helping you,
encouraging you to become what you obviously won't admit to yourself.
It's blatantly obvious that deep down you want to be a woman. Can't
you admit that?" she asked. "Look at how you're dressed. Garter belt
and hose you said proudly. No pantyhose for this gurl!"
I felt under attack. I felt the whole world was against me. Why
couldn't I just dress like I wanted? Why couldn't I feel comfortable
in whatever I wanted to wear without others making judgement? It
really was just a matter of what was in fashion at the time. But
people had to make so much more out of it. Romans used to wear robes.
Englishmen, and Americans for that matter used to wear wigs. Scots
wore kilts. Wasn't that just a skirt by another name?
Gwen and Tim were trying to turn me into something that I wasn't. A
sissy.
But.........who had looked at, even masturbated to sissy porn.
Cuckold porn. Who was I fooling? Apparently not them. Myself?
Part of me reasoned that I would have to do this anyway or be exposed
to the public so go with the flow. The more I thought about it, the
more I realized that most likely I wasn't getting out of this one. It
was going to happen sooner or later, maybe it would be better to just
get it over with and finally be able to go home and away from this
nightmare.
As if reading my thoughts Gwen said, "I can see that you're starting
to truly understand the situation, to be honest with yourself. You're
almost there Ron and once you admit your true nature you will find
peace within. Sometimes it's really hard to face the truth about
yourself but that's better than living a lie," she soothed. "It
doesn't mean you have to rearrange your whole life or anything. It
just means you have to look within and admit who the real you is."
The more she talked the more sense it made to me. WAS I REALLY
NOTHING BUT A SISSY CROSSDRESSER DEEP DOWN? Had I been living a lie
all of this time? What is reality? Is it all of what we have done and
acted out in our life or was that just lies?
I'm sorry but I'm too 'reasonable' to just suddenly accept that my
life up to now was just the fake me. I hadn't even known about
sissies and all until just recently so how could I have been faking
whom I was? It just kept getting more and more complicated.
Gwen encouraged me to have some more of my drink and continued trying
to get me to 'understand.' With soothing words she talked about life
and honesty, how most people fool themselves their whole lives and
the ones that faced up to the real you were so much happier. I
listened and drank more of my drink which was starting to have it's
affect on me. Everything she said made perfect sense but it still
came down to the question of, Was I really a sissy at heart?
I told her that what she said made sense but that didn't mean I was a
sissy. Tim was letting Gwen have her lead and sat quietly eyeing me
and nursing his drink. Eventually he got up and made another round of
drinks. I don't know if I should have been drinking so readily as I
was loosening up and letting my guard down.
Gwen started addressing the issue of whether I was a sissy or not. At
this point we were more just in a conversation, the whole blow job
thing on the back burner and temporarily pushed out of my mind. I was
starting to feel almost relaxed, probably just the alcohol. Gwen
asked me, "Which do you feel more comfortable wearing, mens or womens
clothes? If you could wear just what you wanted all the time and
nobody cared what you wore, what would it be?"
I didn't have to think about that at all! I knew the answer because I
had decided that long ago. I always wore panties. If I could get away
with wearing a bra or hose under my mens clothes like in the winter
time, I did. Any chance I got to wear womens clothes, even if for
just a few hours while my wife was out, I did so. I loved the feel of
the different textures. I explained that it wasn't fair that women
got to wear all sorts of jewelry like earrings, and bracelets, and
belly rings and anklets, and toe rings. And accessories like hair
bows and different purses to match their outfits. All different
styles of shoes. How many different kinds of outfits did women have
to choose from? Dresses. Skirts. Pants. Capri's. Short shorts. Tunics
with leggings. All kinds of styles of tops. What did men have to
choose from? The more I explained my point of view, the more excited
I got. And Gwen could tell.
Tim could tell too and I gave him a look that said, 'You should be on
my side, you're stuck wearing the same crap that most men have to
wear.' He just kept leering at me. "WHAT," I said. "You know exactly
what I'm talking about."
"No, Ron. I'm a man and I'm perfectly content wearing what I have.
That is exactly the point that Gwen is making. MEN don't wear dresses
and capri's and anklets and belly rings. But SISSIES do! You're
wearing a dress and falsies and wig and heels and jewelry right now,"
Tim implored. "That...makes...you...a...sissy."
"No, that makes me a crossdresser, it doesn't make me a sissy. It's
not the same."
"Same difference to me," sneered Tim.
They were confusing crossdressing with being a sissy.
And speaking of confusing, while I was trying to convince them I
wasn't a sissy I was feeling a giddy excitement at being humiliated
in front of them. Of being looked at as a sexual object. I guess the
alcohol was starting to have it's way with me because Tim was no
longer pissing me off even though his attitude and demeaner hadn't
changed a bit. Was it my attitude that was changing?
"I can't really say that a crossdresser and a sissy are the same.
Certainly all sissies love to wear womens clothes though but that
doesn't mean you're a sissy just cuz you crossdress. It really
doesn't matter in this case though dear," Gwen stated while lightly
running her hand up my inner thigh. "You ARE a sissy, you just won't
admit it." Another flash of an image, a beautiful woman kneeling in
front of a well hung man, the words, 'ADMIT IT. YOU LOVE BEING A SEXY
ASS SISSY'
Damn it! The rush I got from her rubbing my thigh brought goose bumps
to my skin. It was impossible for me not to imagine that I was a
woman, the object of sexual attention and I was so getting off on the
attention and sensation of the hand rubbing my nylon clad leg. I
couldn't deny to myself that I loved the feel of my shaved legs,
encased in nylon hose being carressed by her soft hands.
"You like how it feels being carressed while wearing nylons, don't
you sweetie?" Gwen whispered. "That's something sissies get to
experience all the time, girl."
"Umm, hmm," I muttered a little too enthusiastically.
"Think how it would feel if you could be treated like a woman. Like
the woman that you pretend to be all of the time. Doesn't it make
sense that if you feel so good, so comfortable wearing womens clothes
that you would also feel good and comfortable being treated just like
a woman?"
How could I argue with that? Hadn't I fantasized about that very
thing. I have actually felt jealous of all those sissies in the pics
being able to look so incredibly identical to a real woman; except
for one 'small difference.' So hot, so damn sexy. Every bit as sexy
as a real woman. The training videos made you think that sissies were
even hotter, sexier and better than a real woman. Men would prefer a
sissy over a real woman if given the choice.
Was that true? Would men prefer a sissy over a woman? All of the guys
in the videos sure seemed to enjoy the sissies. But then, wouldn't a
sissy know how to please a man even better than a woman. How about
Tim, would he prefer a sissy? I guess he'd already shown his hand.
Would I really like being a sissy? Would I be able to live with
myself if I took that plunge? Was I actually even seriously
considering it at this very moment? It appeared so. What did that say
in and of itself? So many questions!
"Alright, I've had enough of this crap," complained Tim. "Either get
your ass over here and show that you really do appreciate me bailing
you out or get the fuck out of here and let the dice land as they
will."
I pretty much knew what that comment meant. My life would be ruined
if they told anyone. There really wasn't any chance of me getting out
of sucking him off, all of this had just been diversion, a putting
off on my part. There was no question of would I end up doing it. I
really didn't have much of a choice, did I? The real question was
would I embrace the supposed sissy within and enjoy doing it?
Draining my recently refilled drink for courage I stood and almost
fell. I hadn't realized how drunk I'd become. That was probably for
the best. Tim seemed surprised when I continued his way instead of
towards the exit. He had to be fairly drunk as well and I guess he
had forgotten that he still had my keys because either of my
decisions would still have required me to approach him but it was
obvious by the look on his face that he was shocked that I'd give in
to their demands.
I still was having trouble truly convincing myself that I really was
a sissy at heart and that this is something I wanted to do. Maybe if
it had been with a stranger it would have been easier to wrap my mind
around the idea. But the embarrassment of it being someone I knew,
someone I socially knew as a peer of mine in the public eye made the
'true sissy' in me relish this exactly as it had unfolded. This
mixture of thrill and humiliation was slowly taking over my sense of
reason and as I started to kneel between his legs, my cock stirred
and started to harden.
Was I really going to go through with this? With my inhibitions
lessened by my drunken state it seemed that I was. I couldn't look
Tim in the eye so I stared at the floor.
"Open my pants and get it out sissy. I want to see your painted lips
around my cock," he ordered.
I had to look up to get at his zipper but still would not let my gaze
take in his face. When my eyes got to his zipper, there was already a
huge bulge. With shaking hands I fumbled with his belt, then even
moreso with the button on his pants and finally slid his zipper down.
His cock was big enough that the head of it was poking above the
waistband of his underwear.
Raising up slightly he ordered, "Pull my pants down my legs and then
my underwear."
I worked his pants down around his ankles, my eyes the whole time
never looking away from that big purple head sticking above his
underwear. Then I pulled his underwear down, at this point anxious to
see the rest of his big cock. Even if you're not gay, it's hard not
to stare in fascination at a large cock, I don't care who you are.
Well, maybe if you happen to have one of your own you wouldn't but I
wouldn't know about that.
"See. Large cock. No panties, girl. I'm a man. You on the other hand
are wearing panties and all sorts of womens undergarments which means
you are not a man. You're a sissy," Tim slurred, "Look at you,
staring at my cock! You like it don't you?"
"Maybe," I stuttered.
"Maybe hell. You like my big cock don't you sissy?"
He was right. I didn't want to admit it. Not to myself. Not to him.
But he had me dead to rights. I did like it. I was fascinated by its
size. I imagined how it would look splitting a womans pussy apart.
"Kiss it sissy. Kiss the head then lick your way down to my balls.
And then, since you're down there suck on them," Tim demanded.
I didn't. I just sat there on my haunches staring at his penis. I
couldn't make myself do it even though I knew I would have to. Even
though I knew deep down I wanted to. This was Tim, a fellow
Commissioner, someone I'd sat in countless meetings with. Someone I'd
sit in many more with. Someone I'd help decide important matters
with. A fellow respected member of local politics. How could I?
Grabbing my hair, actually my wig which he almost pulled off, Tim
screamed, "Now faggot," as he pulled my face into his crotch.
My nose and face were crammed against his stiff cock. I could smell
the muskiness of his cock and balls and feel heat radiating from his
hard member. It was humiliating having a man cramming your face into
his naked crotch but it sent tingles of excitement through my whole
body.
The realization that I was helpless, not just because he was a strong
man and I was kneeling between his legs but also because my fetish
would be exposed to the world was humiliating and yet a relief also.
It released me from having to make the choice. There was only one
thing I could possibly do. Without further thought it was like a
switch flipped and turned me into the sissy I guess I was destined to
be.
The hypno videos had had their affect on me and without further
hesitation I slid my lips up to it's big purple knob and gently
kissed it. I'd done it! Now I am officially a fag. I purposely kissed
a mans cock and was about to do more. And not because I had to
anymore but because I wanted to. That's right! The barriers within
had finally broken down and I no longer fought with myself about my
new true nature. Tim released his grip once I'd finally given in.
The feeling was so delicious knowing that I was a faggot cocksucker,
the naughtiness and perversion of wantonly worshipping another mans
cock felt so dirty but oh so good. I kissed that glorious head again
and greedily licked my way down to his swollen balls. I sucked one of
them into my mouth and felt a charge of electricity run through me as
my mind registered that I had a mans nut sack in my mouth.
Smack went Tims hand against the side of my head. "GENTLE BITCH! You
know a mans balls are sensitive."
Yes, I did know that but in my newfound eagerness all I thought about
was sucking on his cods and I wasn't thinking about him. The shock of
him hitting me made me spit out his nut and I much more gently sucked
his other nut into my mouth.
"That's better slut," he commented.
I was, wasn't I? A slut. I liked that thought.
With a deep sense of pride for getting it right this time I demurely
looked up at his face as his codsack draped from my hungry mouth. My
vision was partially blocked as I peeked through the brown locks of
my wig which was still askew. Somehow it now seem right and normal
for me to be looking up at a man from my painted face with hair in my
eyes while kneeling between his legs.
Tim smiled. He knew there was no more conflict. He now had his little
sissy bitch right where he wanted her to be which ironically was
right where she wanted to be too. "Would you like to suck my cock
bitch?"
With a mouthful of nut I mumbled, "UMM HMMM," nodding my head slowly
so as not to hurt his sensitive nuts. I was thrilling in the pure
degradation of sucking on a mans nuts but I was anxious to suck his
cock into my mouth and see if I could get the whole thing in. Why?
For his pleasure? NO. For mine? Yes! Just for the pure sluttiness of
swallowing all of a mans cock down my throat.
"Lick my nuts while you beg to suck my cock you little whore," Tim
commanded.
With the devil in my mind I pleaded, "Please let me suck your cock
Tim. Please, please, please let me suck your marvelous cock down my
throat. Please, please, please, I really, really want to suck on it
so badly!" The taste of his nutsack was salty and delicious and I
reveled in the perversion of doing it. It is difficult to talk and
lick at the same time but I gave it my best shot. It came out slurred
and in broken sentences but he knew what I was asking. It made it
seem that I was all the more desperate to get his cock into my mouth
and the truth is, I really was.
"What do you think, Gwen? Does she seem sincere yet?"
Wow. I had forgotten all about Gwen at that point. My face turned
crimson one more time when I realized that she had just witnessed me
begging like a child for candy. Sissy candy. My own cock was so hard
it hurt and the more embarrassed I felt the more it throbbed. 'What a
pathetic little slut you've become almost getting a nut just from
knowing that Gwen heard you beg for cock' I thought to myself.
"Well, she sure is eagerly licking your balls but I don't think
that's because she appreciates that you saved her ass. No, I think
she just likes your big hairy balls and I don't think she has even
thought about how big a favor you did for her."
At this point, that was true. I'd come a roundabout way of arriving
here between Tims legs licking his nuts but in truth all I was
thinking about was getting his big cock into my mouth.
"Typical sissy slut for ya," Tim answered. "All they think about is
themselves when they know all they're any good for is pleasing a REAL
man."
Clearing her throat, Gwen cocked her head and looked at Tim,
"Sorry Babe," Tim added. "And maybe being a little play toy for a
REAL woman."
I'd completely forgotten how this all had started out. Sissies were
like that, getting so caught up in thinking about cock or daydreaming
about cock or better yet worshipping cock that everything else just
slipped their little minds.
And now acting the part of the true sissy I now was, which wasn't
really acting at all, I began begging, because sissies love nothing
more than humiliation, "Oh please forgive me Tim for getting so
distracted by your big beautiful cock. You're right, I was only
thinking of myself and not appreciating how much you did for me." I
had stopped licking his balls and looked up into his face.
"From now on, call me 'Sir' in private. And never call me Tim again.
Only my friends call me Tim and you're not a friend. Friends don't
suck your dick, only little bitches do! And your my little bitch
now."
"Yes Sir," I replied. Oh that felt delicious to call him 'Sir' like
that. To aknowlege his superiority over me. And speaking of
delicious, let me get back to licking his balls and begging to suck
his cock, I thought.
"Sir," I began, "thank you so much for saving me from that mean old
cop. It would have been just terrible if anybody had found out about
me wearing womens clothes. Please let me suck your cock to show you
my appreciation for saving me. I'll give you the best blowjob you've
ever had, no offense ma'am," I mentioned looking briefly towards
Gwen, "to show you just how much I really do appreciate your
kindness. And, please, please, please don't tell anybody on me, Sir.
Please."
"You stupid little cunt. I'm not going to tell anybody. Why would I
do that?" he answered. "If I told, you'd have to move far, far away
and then I'd lose my favorite little cock sucker. As long as you're a
good little bitch there won't be any need to tell. Now give me the
best blowjob I ever had whore!"
I licked my way up his shaft to his swollen purple head. My tongue
traced circles around the shape of his 'helmet' and then caught the
precum that was oozing out of its slit. Ummmmm, ummmm, ummmm, salted
just right! I pulled my tongue away just slightly making it trail
between the tip of my tongue and the tip of his cockhead. Then my
lips eased down to gently kiss the 'little mouth' before sucking in
that delicious precum. My eyes looked straight up into his
acknowlging that I was his eager little cock sucker. I was his little
bitch and if my eyes didn't convey that very well, then my mouth
certainly made up for any doubt.
'Sir' leaned back into his throne and closed his eyes concentrating
on my ministrations to his sweet cock. I desperately wanted to
swallow the whole thing down my throat but I refrained, remembering
that this was supposed to be about his pleasure, not mine. Even
though it might not have been what I most wanted to do, it was still
a great pleasure for me taking my time making love to his cock with
my mouth. It was a very sweet torture holding back on my desires and
concerning myself with his first. That alone was reward enough in and
of itself. For a sissy nothing is better than pleasing ones Master.
There, I said it.
I'd like to try to make you understand this little conflict going on
inside of me. The sissy in me, which was a brand new thing as you
know, wants to please their Master. There are many different things
that might please a Master. At this very moment it was giving the
best blowjob ever and I was trying my best to do so. But.....the
sissy in me, the NEW sissy in me that was reveling in all these new
feelings of humiliation and servitude and audacious perversion wanted
so badly to suck that big cock down my throat. And I would
eventually; but for right now it was all about pleasing 'Sir' and
things had to build up to the deepthroating so I had to put it off
though I very much wanted to do otherwise.
I wanted to experience the pure thrill of audacious perversion and
degradation, the escalading experiences of straying further and
further away from the old me and embracing the new me. This newfound
degradation and perversion of what I was doing was like a drug to me
and I couldn't get enough. What could be more degrading or perverted
for a man than having another mans cock deeply embedded down your
throat with your nose mashed against his pubic bone? It makes my cock
achingly hard just writing about it. Perhaps only a true sissy can
understand what I'm trying to convey. Oh so delicious!
Don't get me wrong. This is not to say that I wasn't getting off in a
big way giving the best blowjob ever, I was. There's much to be said
about giving your whole attention to a beautiful cock like this. To
worshipping a beautiful cock like this. I was just eager for that
final 'innitiation' if you will of swallowing a cock whole. Right now
though, I was still at the point of licking and kissing and teasing
his cock, teasing both of us. Drawing it out with excruiating
attention to detail.
I finally got around to swallowing his cockhead into my mouth and
thrilled at the feathery softness of his knob as it rubbed against
the roof of my mouth. It teased the back of my throat but I deemed it
not yet time to go further. I eased back a little and swirled my
tongue around and around, circling his bulbous head. I then sucked it
back in to the back of my throat and sucked hard on it, rewarded with
another taste of his delicious precum. I sucked and sucked like a
baby at a nipple hoping I could draw out more precum.
Tim, I mean 'Sir' (how could I put myself on the same level as him
anymore as to call him by his first name when all I was was a little
cockslut sissy bitch? His cockslut sissy bitch.) Anyway, He suddenly
grabbed my head and forced His cock down my throat. I wasn't
expecting it and I gagged. How disappointing. (the gagging part, not
having His cock down my throat) He laughed. I'm sure if I had
swallowed it at my own instigation instead of being surprised I
wouldn't have had any problem. I mean, I wanted it and obviously He
wanted it so all was good. And just maybe, even more degrading than
having a mans cock buried down your throat is to have it been forced
down your throat!
He hadn't actually pushed all of it down my throat but most of it was
there and to show what a sport I was or more to the point, what a
little sissy slut I was, I pushed my face into His crotch, not
stopping until my nose was buried in His pubic hair. Still looking up
through my tangled locks I saw Him smile. There obviously was no more
question of whether I was a sissy faggot cocksucker or not. I had
dove in mouth first and there was no turning back now. Not that I
wanted to. I loved the feeling of being a dirty, shameless little
slut. Nothing compares to the feeling of shameless humiliation and
debauchery. Nothing I've experienced thus far anyway.
Gwen came over, leaned in and kissed her husband passionately as I
continued to deep throat His marvelous cock. "See there Ron..." "Oh.
We can't keep calling you Ron anymore with you wearing womens clothes
and sucking dick so expertly now can we? Let's call you Rhiannon from
now on," she stated. "As I was saying, See Rhiannon, now that you've
accepted who you really are you're so much happier, aren't you?"
There was no doubt about my happiness as I eagerly gobbled His cock.
I tried to mumble agreement around His cock, not willing to pull my
mouth away from my treat. And now, there was no doubt whether I was
being forced into this or a willing participant either.
Suddenly, His hands grabbed my head and pushed me off of His cock. My
mouth remained open, my lips eager to be wrapped around His hard cock
again.
"Now I'm going to fuck that sissy ass mouth of yours faggot," Sir
explained. He pushed me back further and stood up, His cock bobbing
in front of me.
"Oh thank you Sir, thank you," I said, "I can't wait to taste your
delicious cum Sir. Oh please, please, please fuck my face and cum in
my mouth." With that, I leaned in and devoured His cock with my
greedy little mouth. How quickly I had become a nasty, horny little
cock slut.
He grabbed my head between his hands and started to slowly long
stroke my mouth. It felt so deliciously degrading to be His fuck toy.
To be kneeling before a man voluntarily, no, not just voluntarily,
anxiously kneeling before a man having him fuck your face. To be used
by Him however he wanted to use you. I felt so debased and defiled to
have Him using my mouth as His cum slot. I loved it!
His pace grew faster and faster as His cock continued to thrust in
and out of my throat. Breathing became difficult and my breaths came
in gasps as I tried to inhale what I could when His cock allowed and
alternately exhale when I could. The sounds of me choking and gagging
seemed to amuse Sir. He sometimes held His cock in, me gagging around
it and panicing for air. I tried to pull back but He was too strong.
Just when I'd think I was passing out He would pull back laughing and
let me breathe. "You're my little bitch now, fag," he laughed.
This went on a couple more times but it was exciting Him too much and
He gave up on His fun and games and started pounding my mouth with
His cock. Now that He wasn't purposely trying to choke me I relaxed
enough to breathe in for several thrusts and exhale for several, the
air moving when it could.
Just when it was starting to become enjoyable for me again I was
suddenly reminded that this was all about Him as He forced His mighty
cock as deeply as He could down my throat and let loose a torrent of
cum, His hips thrusting and punishing my nose against His pubic bone.
I was so disappointed that I didn't get to taste His cum, to feel
it's hot, salty thickness fill my mouth, to swirl it around in my
mouth like a nasty little whore. My face betrayed my feelings as I
gazed up at my new Master.
When He was done ejaculating He pulled out of my mouth and looked
down at me leering as he said, "Oh, that's right. She wanted to taste
my delicious cum she said."
I looked longingly into His face as He smirked at me, "Fuck you,
bitch! You don't have any say in how or where or when I cum, you
fuckin whore. You want to taste my cum, lick what's left of it off my
cock."
And I did. Eagerly. Greedily. And shamelessly. I didn't care what the
two of them thought. I am a sissy and sissies care about one thing
only. COCK. I licked His cock from one end to the other but mostly
concentrated on His cockhead which is of course where the reward
comes from.
The whole time all of this was taking place Gwen had been recording
it with a camcorder set up on a tripod. I don't know exactly when she
set it up, being a sissy I was so easily distracted by cock that I
didn't notice.
Sir had had enough of me slurping on His cock trying to find more of
His cum to taste and pushed me away. "You want to swallow cum really
badly don't you bitch?" he asked.
"Oh yes Sir. I really do," I replied.
"Good then. Pull out that puny little cock of yours and jack off,
slut." I did as I was told. Funny as it sounds, now is when I became
selfconscious about being recorded. Not when I had just admitted that
I wanted to swallow cum really badly. Not when I had a cock down my
throat as He fucked my face. Not when I was greedily trying to get
every last drop of His cum from His cock.
No. I became embarrassed about being recorded as I knelt there with
my dress pulled up with one hand, the waistband of my panties tucked
down under my balls with my wig still sitting crooked on my head,
pounding my pud. Trust me when I say I was horny beyond belief after
all I had been through tonight. It only took a minute until I was
ready to explode. I didn't know what to do. If I went much further I
was going to shoot off all over and I didn't know how well that was
going to go cumming on someones floor like that. On the other hand I
was just about to that point, no make that, I couldn't stop myself. I
was just too horny to hold back and damn the consequenses I shot my
load right there all over their floor as they watched. And as the
camcorder recorded.
"There ya go cockbreath, there's ya some more cum. You said you
wanted some more cum. Lick your filthy mess off my floor faggot," He
ordered.
"I believe you said you really, really wanted to swallow some more
cum, didn't you Rhiannon?" Gwen piped in checking to make sure the
camera was at the right angle to record everything.
You know how you can be so horny it's unbelievable and then as soon
as you get your nut you aren't the least bit horny? Well, that's
always been the case for me and it's left me standing there in mini
skirts and other such womens clothing feeling like a perverted fool.
Not this time! Sure, I wasn't as deleriously horny as I had been a
couple of minutes ago but I was still a horny little dog and the
thought of eating my own cum excited me. Oh don't act like you don't
understand. You've wanted to eat your cum only to lose the desire
just as soon as you get your nut. We all have.
Even more exciting was that I was being forced to do it and better
still, it was going to be recorded. I didn't care at that time, I was
still that horny. I was really embracing this sissy thing.
I turned to face the camera and dipped what cum was dripping from my
dick onto my fingertip and brought it to my mouth. I had said I
wanted more cum and I was going to prove it just like a good sissy
would. I smiled into the camera and sucked my finger into my mouth. I
then looked at Gwen, smiled and then leaned down and licked up the
first drop of my cum from the floor. I didn't just lick it and move
on either, I licked until it was all gone before moving to the next
drop. Or puddle to be more exact. There I languished in the sweet
dessert before crawling to the next and the next and the next until
I'd made sure there was no more cum to lick up.
Sometimes the grit from the floor got licked up too but I didn't
care, I'm just a perverted little sissy and the important thing is
that I got all of the cum I could. When it was all gone I looked up
at Sir with a devilish grin. My look said it all.
"No way you little pervert. You've had enough of this cock for
tonight. My wife is itching for some of this sweet meat tonight too,
you little fag," and with a waving motion of His arm he indicated
that he was done with me and said that I should get the fuck out now.
Earlier in the evening He had called me a fag and it had pissed me
off. Now I liked hearing it. Now I liked the thought of being a
little sissy faggot. Now I was proud of it. Wow!!! Now I felt
grateful to Sir and Gwen for leading me down this path and I knew
that I still hadn't truly paid my debt of gratitude to either of them
for that.
"Sir, with all due respect I know that you want to fuck your wife and
that she deserves a good fucking with your marvelous dick but I don't
feel like I've truly shown my appreciation yet for all that You've
done for me," Sir had seated Himself back in His throne. He hadn't
bothered to pull His clothes back up, they still remained around His
ankles. "If You would go get onto Your bed, I'd like to finish
showing my appreciation."
"I said you've had enough cock for one night faggot."
"Oh no Sir, that's not what I mean at all, Sir. Please let me finish
showing my appreciation," I pleaded.
Gwen said, "Go on dear, you did say that she wasn't appreciative
enough. All of her begging is getting me off and watching her 'do
you' has me so very horny. I'm going to fuck you down later, I
promise I'll make it worth the wait. I want to see her 'thank you'
just a little bit more."
I had crawled back over to be kneeling in front of Sir so when He
stood, I finished removing His pants and underwear. Gwen removed His
shirt while He stood there and then He walked off to their bedroom. I
of course crawled after them.
"Sir, if You would roll over on Your belly please," I asked. He did
as I requested and Gwen sat on the edge watching intently to see what
I was about. Sir probably thought that I was going to give Him a back
massage or something but that's not what I had in mind. I needed to
do this final thing. This final initiation into sissyhood. Besides, I
really hadn't shown my full gratitude for all He'd done. That could
take years for me to repay!
I leaned down and gently kissed His asshole before nibbling some of
the hairs surrounding it into my mouth and gently pulling before
releasing them only to kiss his asshole again and then repeat the
hair maneuver. Now I was a True sissy. Now I was in sissy heaven!
Gwen sighed as I kissed His ass and then her hand darted under her
robe and feverishly started working on her clit. My tongue traveled
the length of Sirs ass crack and back, stopping at His asshole again.
And just as I started licking His ass in earnest Gwen moaned loadly
as her hips started bucking, the bed bouncing with her orgasm.
"First you two want to start drinking without me and then you want to
cum without me, it's just not fair," she complained as her body
bucked and thrusted in the throes of orgasm.
I continued licking His ass for all I was worth. Certainly, the only
thing more degrading than having a mans cock down your throat is to
worship his ass with your tongue.
HOW DELICIOUS!