Tiffanys Torment
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Tiffany's First Time free porn video
Tiffany's First Time
By Tiffany Trenda
I don't know what it is that is so erotic about dressing up
in women's clothing. I can remember the first time the
thought of doing it passed through my mind. I was reading
one of those 'Dear Abbey' columns where a woman had written
in about her sister dressing up her son in little girl's
clothing when he was bad. Even at that young age of 10 or
so I remember the funny feeling it gave me. I even went as
far as to cut that article out and keep it for quite
awhile. I kept rereading it hoping that there was something
I had missed from the time before or maybe spontaneously
something erotic would appear and would excite me.
Enough about that. I think the first time I ever tried on
girl's clothing was when I was a freshman in high school.
It was late in the afternoon and for one reason or another
I was still at school and was passing through the gym.
Lying by the door of the gym was a small duffel bag with
girl's gym clothes and other random articles. Once I
determined no one was around I swooped up the bag, stuffed
it in my backpack and took it home with me. As soon as I
walked in the front door I said hi and bye to my sister and
mom and ran straight up to my room.
I ran into my room slammed the door behind me and pilled up
all the crap that was on the floor in front of the door. I
doubt it would've stopped anyone who really wanted to get
into the room, but at least it would discourage them. I
tore open the bag, much like a kid at Christmas, anxious to
see what I had found. And for a kid who had masturbated
himself to sleep many of times thinking about dressing as a
woman, this was Christmas.
Inside the bag I first pulled out her gym shorts and shirt.
They weren't anything too flattering, but the shorts were
really short and I knew the shirt was perfect for my little
frame. I then pulled out a sports bra two pairs of panties
and a pair of gym shoes.
I checked to make sure the crap was still pilled up against
the door and then decided to have a little fun. I first
stripped off my outfit and stood in front of the mirror. I
thought I was rather cute, I had a small body with slender
(hairless) legs and what I deemed a damn cute butt. It
wasn't t he typical guy butt, there was a definite
roundness to it with just a little perkiness.
I grabbed the pair of panties and pulled them up my legs
and up and over my little clitty. They clung snugly to my
little ass and other than the slight bulge in the front I
thought I looked damn sexy. I even took a second to turn
around and bend over a bit to check it out. I grabbed the
sports bra and pulled that on over my head. After
struggling for a few trying to figure out which side was
the front I had it in place, minus the breasts of course.
To take care of that I stuffed them just enough with some
socks. I thought about stopping there but I thought it
might be fun to try on the whole outfit.
I grabbed the pair of shorts and pulled them on. They fit a
little tight and they definitely were short. I pulled the
gym shirt over my padded bra and on. I slipped on a pair of
socks I had stolen from my sister with the little frills on
the top. I stopped to admire myself. The shorts were snug
on my body and when I turned around I could see my
pantyline, I wish I had a thong. The top was cute because
it didn't go all the way down so it showed just a bit of my
firm stomach and really accentuated my breasts.
As I watched myself in the mirror dancing and posing in
seductive positions I couldn't help but rub my clitty
through the soft gym shorts and the cute little panties. I
knew that I was going to have to do something about this
because I was already causing a wet spot in my panties.
I jumped up onto the bed and onto my back. I laid there
running my hands up and down my body feeling the soft
clothing and my excited body in them, I rubbed and pinched
my nipples under the bra and started caressing my way down
to my shorts. I pulled them down just a bit and was able to
pull my little clitty out of the sweet panties where I
could play with it. I started slowly stroking it as it grew
even larger in my soft hand. I remember wishing at the time
I was stroking some cute guys cock instead of my own. Even
the thought of that made the precum drip out of my clit.
As I was stroking myself with one hand I let the other hand
wander over my body. I rubbed my little hard nipples and
down my firm soft stomach and began working my way towards
my ass. I had never touched my ass before but the thought
had always been there. As I began lightly touching my cute
tight ass I could feel my orgasm coming. As I stroked my
clit and rubbed my little pink pucker I knew I needed to do
this more often and definitely try this with someone else.
Just the thought of having a man's cock in my hand or near
my little tight ass made me whimper and moan. When I
started to slowly push my finger in my little pucker it was
too much for me and I started orgasming all over my stomach
and hand. I lay there for a few minutes recovering from
what had to be the greatest experience to date.
It became a daily routine for me to come home and put on
the clothes that I had and masturbate myself to orgasm. As
years went on I actually started buying women's clothing. I
would go into stores and pass it off as if I was purchasing
something for a girlfriend then I'd go home and play dress
up for the evening. I even picked up a new name for myself
in costume, Tiffany. I felt it was a sexy name yet very
playful, like me.
It was my senior year right after my 18th birthday when I
had my first experience with another person. I had met Jeff
online. He was a few years older than me, 28, not married
and a fun guy. I don't remember how it was brought up one
night online, but somehow I said I had worn panties before
to high school one day. He told me he thought this was
really sexy and had asked if I had ever done anything else.
After a little poking and prodding he worked out of me some
of the other things I had done and all the little outfits I
had in the back of my closet and all of the toys that I use
on myself and in my little love hole. He told me if I ever
wanted to experiment with a real man he would be into it.
At the time I thought about it and brushed it off. But
after spending a full week wanking myself to the thought
each night, I told him I would.
He offered for us to meet in public one day and have lunch
so that I felt comfortable. I told him I'd rather come over
to his place and watch a movie or something but he'd have
to choose a Friday night when his roommate wasn't going to
be in. We decided on the Friday a week away because he knew
for a fact his roommate wasn't going to be around. I told
him I got off school at 3 and I'd drive over there. He
wasn't going to be home until after work at 5 so he'd leave
the key under the mat for me. This was perfect. I could
tell my mom I was going to be spending the night at one of
my friends houses then I could shoot over to Jeff's and get
all dressed and pretty before he even got home.
I couldn't wait for Friday to come. I sat there all day
staring at the clock praying for 3 to get there. My car was
loaded with all of my clothes and makeup and even a few
toys.
Finally it was three and I was on the road. Jeff's place
was only a 20 minute drive and with his directions it was
no trouble finding. I walked up tot he front porch, lifted
the mat, found the key and let myself in. When I walked in
the front door I was greeted by a small bouquet of flowers
with a note on them reading, "Hey beautiful, I can't wait
to meet you in person. Make yourself comfortable."
I knew there were so many things for me to do with just
over an hour before he got home. I found my way to his
bathroom and jumped into the shower. I soaped my firm
little body up and shaved off any unwanted hair including
just a little trimming around my already hard clitty.
I jumped out of the shower and toweled off and put on some
of my after shower lotion I had bought awhile back. It
smelled so sweet and made me feel like such a sexy little
thing.
As I started to dig through my bag for an outfit I noticed
that Jeff had already bought me some outfits and they were
laid out on the bed for me to pick from. I had a choice of
two skirts, one was black and one was a short red one. I
chose the black one I thought it'd fit better. I then had
three blouses to choose from. I took the blue one in the
middle with white vertical stripes and a white collar. I
thought it would look cute with a pair of girly study
glasses I had brought.
I first grabbed a thong I had brought and pulled it up and
on making sure the thong portion was tight in-between my
soft little cheeks. I put on white thong to match my
panties and filled the C cups with some fake breasts I had
ordered. I was going to put on my garter belt but I thought
it's be sexier to wear the knee-high tights with the little
bows on the top. The last and final touch for my outfit
were the shoes. I had brought a couple of pairs and had
selected the 2-inch heels with the ankle straps. Now for my
face and hair.
I went into Jeff's bathroom with my blonde wig and my bag
of makeup. First I put on some blush, then my eyeshadow and
topped it off with lipstick. I wasn't a huge makeup fan
because with my already feminine looks I really didn't have
to pile it on. My last pieces to put on were my perfume and
the wig. The wig was a gorgeous blonde wig that went down
barely to my shoulders. It was a bit curly and ultra sexy.
As I finished my last touches I heard a car pull into the
driveway. I quickly ran over tot he window and peered out.
Not only did Jeff look great, but he looked even better in
person then in pictures.
I wanted to meet him at the door but due to the heels I
only made it half way down the stairs before he walked in.
when he walked through the door my jaw almost dropped at
how handsome he was. I think he felt the same way because
all he got out was, wow!
I had originally thought he and I would watch a movie or
something where I could build up the anticipation, but I
knew that wasn't needed. What I needed at that moment was
his cock. He started coming up the stairs and I down and we
met at the landing. He put his arms around my small waist
and pulled me into him our lips met and I swear I saw
stars. As he pulled me into him I could feel his hard cock
pressing into my stomach and it kinda scared me by it's
size.
We broke the kiss and he said, "Do you want to go up
stairs"? I bit my lip nodded, and let him hold my hand as
he walked me up to his room.
I followed him into his room and towards his large bed. He
sat me down and sat next to me. He leaned towards me and we
began kissing again. This time Jeff's hands started
caressing my body in slow soft strokes. He ran his hand
down over my chest across my tummy and then down my legs.
As he began working his way up my leg and under the skirt I
reached down and stopped him before he got to far, then I
looked at him coyly in the eyes and said, "Now now, there
will be plenty of time for that, let me do something that
I've been thinking about since we first started talking."
With that I slid down between his parted legs onto my
knees. Looking him dead in the eyes I started undoing his
belt and then button and zipper on his slacks. When I got
down to his boxers I leaned forward and placed a light kiss
on the shaft of his cock pressing firmly against them. This
caused him to let out a low moan. As I slowly inched down
his boxers I thought back to the number of times I sat in
my bed deep throating that rubber cock I had wishing that
it could've been real. Now I had a real cock right in front
of me and it was all mine.
As the head emerged from the boxers I placed a kiss right
on the tip. I already could taste the precum seeping out,
and I liked it. I pulled the boxers all the way down and
most of the way off then returned to his sexy love stick. I
planted another firm kiss on the tip and then slowly ran my
tongue down the shaft to his tight ball and back up. I
continued doing this until I was afraid he was going to
come all over his stomach and not in my sweet mouth.
I wrapped my hands around the shaft and held it straight up
for my wanting mouth. I pressed my lips against the head,
but this time I parted my lips and allowed the head to slip
in. Oh my gosh it was warm, firm but yet soft to the touch,
nothing like the rubber one I thought to myself. I allowed
his firm cock to move past my moist red lips and over the
top of my soft tongue to the back of my throat where I held
him for a second, I then started working my way back up to
where I just held the tip in-between my lips. I knew what I
wanted, I wanted his love juices in my mouth and I wanted
to taste my reward so bad I would do anything for it. I
lowered my head back down and then up again. I reached my
hand up and cupped his balls feeling how firm and full they
were. Up and down on his cock, with my soft red lips
stretched as far as they would go. I only wish I could've
seen myself in a mirror or something. In my high heels,
knee high tights, skirt and sexy top.
Jeff let out moan and I could tell by how tight his balls
were, he was about to cum. I took the tip of his cock into
my mouth and ran my little wet tongue frantically across
the top while I used my hand to jerk on the shaft. I needed
my girlie reward; I wanted to taste the reward all good
girls deserve. Jeff let out one final moan and I got what I
wanted. I felt the cum bursting out of his cock into my
waiting mouth. I let out a moan but was muffled by the huge
cock in-between my young lips. As he unloaded every bit of
love from his cock I swallowed it all. The taste was
amazing and I knew at that moment this is what I wanted and
I knew I was addicted.
Jeff pulled my head off of his cock with a "pop". And
basically lifted my small body on to the bed. He laid me on
my back and climbed on top of me. Our tongues became
intertwined and I could feel his cock growing larger
against my stomach.
I'm going to run, but thanks for reading. My email address:
[email protected]
Send me a letter and tell me if I should finish this story.
Bye Tiffany
Kaidence
- 17.04.2021
- 13
- 0
