Wannabe Sissy Part One The initiation
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Wannabe Sissy Part Two - Charles In Charge free porn video
Charles is my lover. I am his gurl. I will do anything to please him
sexually and he does the same for me (although to be honest, nothing
turns me on more than pleasing him). I told you all in Chapter One how
we met and how Charles swept me off my feet (or at least put my feet in
the air - tee hee). This episode takes place a few months later, after
we had been fucking regularly on a weekly basis since we met. Charles
had always been generous with me, keeping me well supplied with
everything I needed to be a proper crossdressing slut. In return I
drained his nuts whenever, wherever and however he desired. And I was
always happy to do it.
One evening we were watching Netflix, I was dressed to the nines and we
were sitting on the couch cuddling, me idly tugging and caressing his
wonderful stiff cock the way he so likes. Out of the blue he said to me
"Darling, I have some friends you should meet." I was stopped cold and
didn't know what to say. I even stopped stroking his cock I was so
surprised. "Friends?" I muttered. "I think you would like them" he
continued sensing my discomfort. He went on to describe how he would
invite his three friends to play with (essentially gangbang) some of his
previous gurlfriends. "You would like them a lot, they are all very
kind and gentle and fun, especially if you are feeling slutty at all.
Oh, and they all are huge cummers, even bigger than me." He said this
last with a grin.
I admit I had mixed feelings at this point. Part of me had a jealous
streak and didn't want to admit to myself that Charles had other gurls,
even though he had pretty much told me up front. That same part of me
wanted Charles to love me for me, and not just for the fucking. But yet
another part of me was exhilarated at the thought of being a slut and
servicing four men at once. "When would we do this?" I asked somewhat
timidly. "Tomorrow night, if I can arrange it. Otherwise next week one
night." I told him to set it up and I sucked his cock while he called
his friends. After three quick calls he announced that it was all
arranged for tomorrow night at 8pm. I was nervous but relieved that I
wouldn't have to wait too long for it to happen - I was concerned I
would get cold feet the more I thought about it. "What will happen?" I
asked, "will they all fuck me?" We talked at length about what I should
expect, and I felt much better. I would suck all four cocks and then
they would take turns fucking me, except for one, Charles wouldn't say
why, but one of the guys was apparently oral only. Then it would be a
free-for-all before they came on my face bukkake-style.
Needless to say, I didn't sleep well that night, partly from anxiety but
mostly from anticipation. And my productivity at work was well below
par lol. When I got to my hotel the desk clerk flagged me down and told
me that I had received a delivery that they had sent up to my room.
When I got to my room I found a large package from Charles. Inside was
a completely new outfit that he wanted me to wear that night. Matching
panties, bra and stockings and garter belt, all ivory in hue. A nice
new flower-patterned dress and some matching shoes completed the outfit.
There was a cheap wig, one that was nowhere as nice as many of the
others he had given me. He had also included a butt-plug, a metal bulb
with a diamond grid pattern as the handle, which had a note attached
telling me to put it in and be wearing it when they arrived.
I got naked and put some talcum powder all over my now hairless body. I
lubed up the butt plug and slid in into me. Now I set to work on my
makeup, wanting it to be perfect and for me to be the best looking gurl
I could be. I was deliberate and precise doing my mascara, which was
amazing since my heart was racing and my hands were shaking
uncontrollably. After I was happy with my face, I started getting
dressed. It always feels so good to put on the panties and stockings,
because it usually means I am getting laid soon. I was happy with the
dress Charles had chosen - it made me feel sexy and it accentuated my
ass quite nicely. I put on a chain, a couple bracelets and some
earrings to finish the look. I put on the new wig, although I couldn't
for the life of me imagine why Charles sent this ratty thing. Since I
still had some time I put on some press-on nails. I looked in my hotel
room's full-length mirror and was thrilled at how passable I looked -
truly fuckable, I thought. I was dancing around, wiggling my ass in the
mirror when a loud knock on my door almost made my heart jump out of my
mouth.
It was Charles - he came in holding a package, kissed me gently on the
cheek and told me I looked amazing. He said the boys were in the lobby
waiting. He just wanted to make sure I was ready. He phoned them and
told them to come up and I went to the couch and sat, anxious to get
started. It seemed like an extraordinarily long wait but soon Charles
was opening the door letting my new lovers in. I stood to greet them
and let them check me out. I was gratified as to how positively they
responded to their first sight of me. Charles introduced me to them as
April, which is one of his gurl-names for me. The guys were named
Jared, Will and DJ, and each one kissed me when introduced.
I gave them a twirl to let them see me from all angles and one of them
said "You were right, Charles, she is beautiful." Needless to say, this
turned me on like crazy. Charles could tell I was unsure of how to
begin so he had the three guys sit on the couch suggested to me that I
choose one to start. I got on my knees in front of Will, reflexively
choosing the one who was sitting in the middle and began caressing the
front of his jeans. I unzipped his fly and he lifted his hips to pull
off his pants. Out flopped a very nice cock, halfway hard, which I
eagerly took into my mouth. I sucked him, and I felt him expanding
inside my mouth. After about five minutes I heard Charles scolding me
to switch partners, "Everyone wants to play" he remanded. (It's hard,
after all, to keep track of time when you are in your first ever
gangbang).
I felt Jared's hand on my head gently guiding me to him, so I slid over
as he smiled and undid the drawstring of his shorts, pulling them down.
I immediately noticed that his cock was not circumcised, and it was
really fat. I haven't had much experience with uncut guys and am never
sure if they need to be treated differently. It soon became clear that
I was doing an acceptable job, based on his moaning wriggling and
groaning. Now I realize that Will is hard and waiting and DJ hasn't
begun so I need to pick up the pace a little bit. I move over to DJ and
feel the front of his pants. Something feels wrong but I am not sure
what. I open his fly and struggle to pull out his cock. When I finally
get it out, I realize that he must be the "oral only" guy. His cock is
massive. It is so long it seems to have a knuckle in it. His cock head
is the biggest I've ever seen, and I can barely fit it into my mouth.
The other guys laugh at my struggles handling this monster cock, but DJ
just puts his hand gently on my head and gives me words of
encouragement. This is when I realize they manipulated me so that I
took DJ last, while thinking it was my own idea.
Again, time is hard to measure when you have a huge cock in your mouth
but eventually Charles taps my shoulder and helps me to my feet. The
guys are now getting undressed and Charles suggests I do as well. I
look at the abundance of beautiful hard cock at my disposal and make a
show of wiggling my ass out of my dress. DJ had climbed onto the bed
and sat with his back against the headboard, tugging and stroking his
massive cock. Jared and Will took me by the hands and led me to the
bed, where I resumed sucking DJ with my ass in the air invitingly. I
felt six hands caressing my ass, which I had forgotten was currently
plugged. "I'm going to replace this" Charles declared as he slowly
pulled the butt plug from my ass. I moaned as he penetrated me, and I
took DJ as deep into my mouth as I could, thus completing my first
official spit-roasting.
Peripherally, I saw Will and Jared rolling condoms up their stiff shafts
while I felt Charles pull out and come sit next to DJ. I took him in my
mouth while stroking DJ with my hand. Jared and Will took turns
breeding me while I took good care of Charles and DJ on the other end.
The night went on, in many different positions but always with a cock in
my ass and one in my mouth, often with one in each hand.
Gradually, the boys' moaning and panting increased to the point where I
knew our play date was coming to a head (pun intended?). Will and Jared
peeled off their rubbers and Charles positioned me on my back with my
head resting over the foot of the bed. He lifted my hips and slid
inside of me as my three new friends stood around me jerking themselves
lustily. DJ placed his swollen cock head against my cheek and exploded
spurt after spurt of red hot cum onto my face. Jared came next,
unloading his fat, uncut cock onto me, blinding one eye with a fat
dollop of his sticky jizz. I reached up to tickle Will's big balls and
he immediately responded by pasting my forehead. Charles pulled out and
straddled my chest, jerking off until he blew his load on my neck, chin
and lips. I was quietly reveling in my situation when Charles rolled
over and grabbed my cell and started taking pictures. All the boys
rested their cocks on my face for a series of group portraits - which
are in my private collection and are only shared between me and Charles
when we are reminiscing about our adventures.
While the boys were dressing, Charles, ever the gentleman, helped me to
my feet and walked with me into the bathroom. I started laughing when I
saw myself in the mirror. My face was just covered in viscous sperm,
one eye almost glued shut and a rivulet of semen running down my neck.
At least I now knew why I was wearing such a ratty wig - it, like my
face, was irretrievably drenched in cum. It was clearly unsalvageable;
thus it was designed to be disposable. The boys, now dressed, thanked
me for a good time, thanked Charles for the introduction and left.
Charles took off my wig and tossed it into a small trash bag, confirming
my suspicion that it was meant of a single use only.
"You need to clean up" Charles said as he opened the shower stall and
started the water. I didn't expect him to stay, but he got in and
invited me to join him. After washing the goo off of my face, he kissed
me lustily. With the hot water washing over our bodies he wrapped his
arms around me and told me he was proud of me tonight. We held that
embrace for a long time.
I was wondering why Charles had not gotten dressed after we had dried
off, but I wasn't complaining since I really liked looking at his great
naked body. I hesitated, not sure why he was still around, as he
usually left fairly quickly after we made love. Instead, he handed me
the package he had brought when he arrived. I was a bag with a wrapped
box in side - a gift for me? He motioned for me to open it, so I tore
off the wrapping paper without hesitation. I looked inside, and I
immediately knew what I had - wrapped in tissue paper was an elegant,
satin bridal peignoir set. "Put it on, darling," Charles said. I was
shuddering as I slipped it on over my head. The satin felt so sensual
as it slid down my shaved body.
My mind was reeling as to the meaning of the gift when Charles took my
hand and led me to the bed. He pulled back the sheets and climbed in,
patting the mattress next to him, indicating I should join him. I
climbed in but the look on my face betrayed my confusion. He laughed,
pulled me close and kissed me. "I was thinking I might stay the night,
if that's OK with you." I wrapped my leg around him and pulled him
close - no other answer seemed necessary. Charles had never expressed
interest in sleeping with me and I was thrilled. His hands were all
over my body, the satin fabric shifting under his strong grasp. I fell
asleep in his arms and when the alarm went off I gave him a great
blowjob. What better way to encourage him to sleep over, right?
Pansy
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