Sissy Stepson 10 Stepmother s Sissy
- 4 years ago
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Wannabe Sissy Part One - The Initiation 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).
This is the story of how I met him. I am an older, single man, I am a
road warrior in that I travel for work and spend the full week away from
home, staying in a hotel. I am bisexual, enjoying casual encounters
with men and women. I love to fuck strange pussy, but when I am with a
man my desires are 100% bottom. I have always played with cross-
dressing, but being thick and super masculine looking, I never felt
comfortable sharing it with anyone.
So about two years ago I had just started a long-term assignment in a
midwestern city, and I was in the mood to suck some dick. This was
before the demise of craigslist, and an ad for a cum-hungry cocksucker
hosting in a hotel with easy parking almost guaranteed me a nice
selection of cocks to choose from (or as happened on occasion, a series
of cocks to schedule one after another). I never had a standard CL ad,
always preferring to customize one to how I was feeling at the time. In
this case I noted that I was looking for a heavy cummer for a blow and
go, but I would be open to more (anal) at a later date if we clicked. I
described myself accurately and, on a whim, added the two word phrase
that would change my life forever: sissy wannabe. I feel that way
because when I am with a man I want him to treat me like he would treat
a woman.
I immediately got a few responses, mostly photos of greasy, ugly looking
dicks with a one liner such as "suk dis." I was horny but not desperate,
so I waited unit I did get one that was very sweet and quite articulate
(both a rarity in CL responses). He told me he could cum huge loads
(which was all I really needed to hear) and that he was fascinated by
the term sissy wannabe. We conversed for quite a while on YIM - I told
him I liked to wear panties but I didn't look good. I told him I was
jealous of all the young sissies and traps on the internet who could
look so good in panties. He understood completely - in fact he said
that he "catered to wannabe sissies." He owned a large inventory of
sissy paraphernalia, clothes and lingerie, wigs and makeup, and anything
else the aspiring sissy might need.
I told him I wasn't passable and he didn't seem to care. I speculated
he didn't have anything in my size and he assured me he did. Once I
gave him my stats, he confirmed he had everything I would need. He
explained that he got off initiating sissies and crossdressers. He also
argued that sissies gave the best head (which I already knew in my
heart) and that he wanted to start working with me tonight. Well I was
so nervous and so turned on I didn't know what to do, but I said yes and
it was a good thing he was close to my hotel or I would have chickened
out.
I nearly jumped out of my skin when he knocked on the door of my hotel
room. He was average looking, a very nice smile - trustworthy and
calming in fact. What was notable was that behind him he dragged a
large roller bag, bigger than a carry-on suitcase - almost the size of a
small steamer trunk. We shook hands and he put the trunk on the bed and
opened it for me to see. It was, as he described, an inventory of what
I needed to be transformed. Half of the trunk was filled with three wig
stands and wigs. He pulled them out for me to choose. One was long
blonde and curly - not me at all. The second was long straight and
auburn colored which I really liked, but which didn't really match my
skin tone. The third was dark brunette, shaggy with a length just above
my shoulders. We both agreed that it was the obvious choice.
Next, he took out a makeup case and he gave me a quick lesson, focusing
on my eyes and lips (the reasons for which were pretty obvious to me).
I was actually not unhappy with how it looked on me. I was concerned
when he told me to get naked, as I was a little overweight as well as
hairy. He gave me some thick black stay-up stockings that hid my leg
hair and made my legs look awesome (if I do say so myself). Next was a
bodice, which was both slimming and hid my chest hair, especially when
he inserted two large breast forms in the bodice. I looked at myself in
the mirror and made myself horny - my ass especially looked awesome. To
finish it off he gave me a pair of lace, fingerless gloves, about elbow
length. And can you believe it? He took out a little black dress for
me to wear. It was cheaply made and poor fabric, but it appeared to
never have been worn and it was so exciting for me to put it on for the
first time. He made a few adjustments to my wig and I never thought I
could look so good.
I was beaming and smiling from ear to ear as I checked myself out in the
hotel room's full length mirror. I was definitely a gurl. And I
desperately needed to be treated like one. I smiled at him, my lips red
and shiny with a thick layer of lip gloss. "I look lovely," I said in
my most sultry gurl voice, "How can I ever thank you?" He smiled
knowing exactly what the answer was. "You do look beautiful," he said
as he started opening his belt. Like any self-respecting sissy I
reveled in the compliment and fell to my knees in front of him. I
helped him unzip his jeans and that's when I fell in lust with Charles.
As I said, everything about Charles is average - everything except his
cock, that is. It's not huge, but it is quite big, and it is gorgeous.
It is everything I had hoped for (and never gotten) in all those CL
casual encounters I had enjoyed. A wonderful, swollen head, long veiny
shaft and big shaved balls. I greedily took it into my mouth and moaned
as I felt it grow harder and longer inside. I bobbed my head back and
forth, tasting the musky goodness of his amazing penis. I slid it out
of my mouth to inspect it. It was an awesome cock, rock hard and
throbbing, wet with my saliva and glistening with lip gloss (I told you
I know why he had me put on so much gloss).
I looked up at him to show my appreciation and was amazed to see a look
of ecstasy on his face. "This obviously isn't your first rodeo," he
said, "you are wonderful!" Another complement - this one made me want
to give him the best blowjob he ever had. I wanted to encourage him and
his gorgeous cock to come back. Without responding I took his fat cock
head in my mouth and stimulated it with my lips and tongue. When he
started to groan I slowly moved towards him, sliding his hardness into
my throat. He was gentle, which I like in a man - he let me control the
blowjob rather than grabbing at my head and throat fucking me (which I
despise). For the next 25 minutes I did everything I knew how to make
him cum. I deep throated him, sucked his balls, made sexy sucking and
slurping noises. He was responding with happy sounds but I was so
afraid I wasn't pleasing him. I wanted him to want to come back.
I was convinced I had failed when he pulled his cock out of my mouth and
had me stand up. He had such a serious expression on his face. He put
his hand behind my head and pulled me into a passionate kiss. I kissed
him back, opening my mouth for our tongues to meet. He put both his
hands on my ass cheeks and I thought, "Yes, I am his woman now." He
lifted up the hem of my dress, baring my ass, which he fondled lustily.
"I am so close to cumming, but I wanted to see you like this before I
finally did," he croaked. "You look so sexy."
He kissed me again and guided me to the edge of the bed, where he had me
lie face up. He put his cock head in my mouth and started stroking.
"Do you want it?" he asked. I nodded and whispered "Oh God, yes." I
lovingly caressed his balls and the expression on his face told me he
was ready to cum. I opened my mouth and stuck out my tongue in
anticipation. The first spurt was so thick and strong it caught me by
surprise. It hit my upper lip and dripped into my mouth, that familiar
salty taste I had been craving. He kept stroking but there was a pause
- I thought maybe he was done. After a long moment of uncertainty, he
growled and shot four huge, quick bursts of cum into my mouth. It was
so much that I reflexively swallowed it and was disappointed that I
didn't get to savor it. But he kept stroking and before I knew it I had
a mouthful again. What filled my mouth was probably an average sized
load from all my previous encounters - which was amazing since I had
already swallowed an amount about equal to that size.
I showed him my mouth and played with the cum for him to see. I stroked
his cock and squeezed out a driblet, which I licked off his cock head.
I swallowed with a satisfied smack and he collapsed into the bed next to
me. I still had his cock in my hand (I really didn't want to ever let
go) and he smiled and kissed me tenderly. "Do sissies still give the
best head?" I asked. "Yes," was his immediate response, "and you are
among the best of the best." I kissed him hard. "I could be your woman
for you. I would love for you to fuck me someday." He was a little
taken aback by my forwardness, but he recovered nicely. "How about
tomorrow night?"
I was thrilled - I couldn't wait to have him inside of me. He held me
in his arms like a good man holds a well-fucked woman. Time is hard to
measure in the aftermath of incredible sex, but eventually he got up to
leave. He rolled his trunk and began to put in the hotel room closet.
"What about your stuff?" I asked. "You need it for tomorrow, darling -
can you be dressed and ready by eight?" I assured him that I could and
spent the next hour watching videos on how to apply makeup.
I was basically worthless at work the next day, just waiting to get back
to my room and start getting ready. The day was finally over and I
hustled back to my room, stopping first to get what I needed to prepare
myself. The first thing I did was get naked and thoroughly clean my ass
- I wanted this to be a wonderful experience for Charles. I did my
makeup and with only a few minor do-overs, I thought it looked as good
as last night, maybe even a little better. I am so horny I am shaking
and Charles is late, I am convinced he is not coming, when I hear the
knock on the door. I let him in and kissed him - and the way he kissed
me back I could tell he was happy to see me.
I noticed he had a bag with him, which I eyed suspiciously. He smiled
sheepishly and apologized for not having these yesterday. He pulled out
a pair of stiletto heels. "I had no idea of your size - I guessed today
after checking you out last night." "They're so sexy," I squealed. He
laughed as I put them on. "They're called fuck-me shoes." "Perfect," I
giggle as I parade around wiggling my ass at Charles. "I also picked up
some other things you might like," he said. He emptied the contents of
the bag on the table. A couple of pairs of sexy panties, just my size,
a gorgeous lace bra, some false eyelashes, fake press-on nails, and
assorted make up accessories. I looked at him, confused. "For next
time," he grinned. I smiled and nodded. I placed my hand on the
growing bulge in his pants. "Let's go to bed."
I shimmied out of my dress, keeping my heels on as I love how they
accentuate my rump. I help Charles get undressed - last night he really
only had his pants off. Tonight, I want him fully naked as we make
love. His naked body is actually quite attractive, more muscular that
It seemed last night. I lay him on the bed and give him light,
feathering strokes from his balls to his cock head. He shivers at the
sensation. I climb on the bed, knees near his shoulders and begin
sucking that wonderful cock. He rests his hand on my bare ass, gently
rubbing at my hole with his fingertip. I suck him lovingly, but not as
vigorously as the previous evening. I certainly don't want him to cum
before we make love.
Turns out there was nothing to worry about. He sat up and got off the
bed, his impressive cock hard and ready. He took the condom from the
bed table, where I had left it for him, and rolled it down his long
shaft. I got on my knees, ass up for him. He took the lube and applied
it generously to my waiting hole. He rubbed his head against it and
asked, "Ready, darling?" My body trembles every time he calls me
darling. I said simply, "Yes." I still remember the first time he
penetrated me, his fat cock head pressing against my resisting, hole
momentarily, then popping itself in satisfyingly. I moaned, "Yesssss,"
and he gently started fucking me, each thrust deeper than the last,
until he was unable to go any deeper. I felt that I was a woman and I
was being made love to. He gently took hold of my hips and pulled me
onto his cock with each thrust. He groaned and panted as he picked up
steam, the rhythm of his thrusting made my hanging cock flop in the
wind. He pulled out and lay on his back, inviting me to ride him. I
was more than happy to straddle him and slide him inside me again. I
grind into his cock, leaning back so I could more easily bounce on him.
I rode him so hard I thought I was going to pass out from holding my
breath. Charles is such a gentleman he put me on my back and entered me
missionary style. I had my arms around him, pulling him closer to me.
We kissed and he made love to me so gently I never wanted it to end. He
pulled out, tore off the condom and filled my mouth with his musky load.
Over the following weeks and months, we fucked often, usually at least
two nights a week. Charles was very generous, always bringing me some
new clothes or accessories, and I grew as a woman. I became quite
proficient at applying my make up, I moisturized my face to minimize the
five o'clock shadow, and I began shaving my body before our meetings. I
even lost weight in order to appear more feminine. We fucked in in
every position possible. One time I got him so hot he came in his
condom before he could give it to me. To show him how committed I am to
him I sucked his load out of the condom. We even became quasi-exclusive
and got regularly tested so he could fuck me bareback. Although I loved
savoring his huge loads, I let him creampie my ass from time to time.
Virginia
- 12.01.2021
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