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The Personal Ad 2 free porn video
THE PERSONAL AD (2)
Erica Wright
Written on 11/09/94
This is not a sequel to "The Personal Ad 1". After re-reading that story I
decided to revisit the concept, and wrote this story almost exactly 10 years
later. Look for that story if you enjoyed this one. I also think it's very
interesting to see how my writing style as well as my fantasies have changed.
This was written as a stand-alone story, but obviously could continue. You
can contact me directly at: [email protected] Enjoy.
"Mid-twenties, passing cross-dresser seeks sensitive, caring man to treat her
like the lady she longs to become. Light bondage a big plus."
I read over the personal ad one last time before sealing the envelope and
dropping it in the mail. It was a huge step, but I could still back out if I got
cold feet.
Peter was the only winner of all the responses, and immediately set my mind
to rest, we spoke on the phone for a few minutes before we agreed to
exchange photographs. I eagerly awaited his package. He was just the kind
of man I wanted to take my virginity. Strong, attractive, mid-thirties. He
called me back a few days later and we agreed to go on a date. Over drinks I
explained how I had done this before but it had never worked out, how the
men I always had met before wanted to fuck me after the first date. He leaned
across the table and kissed me, saying how he could understand their desire
to have sex with me right away, but how he wanted more. We went on a few
more dates never doing anything more than hugging or kissing before he
proposed that we plan a special evening to take our relationship to the next
level. I had been hoping he would say something like that. I smiled and said
yes. He said he'd take care of everything, all I had to do was meet him for
dinner the following Saturday night at his apartment. "Should I come
dressed?" I motioned to my clothes. "It's up to you... however you're
dressed when the night begins, I guarantee you'll be wearing panties by the
end." This first overtly sexual comment caught me by surprise and I blushed.
He smiled and asked If I would like to leave. "You have a lot to think about
over the next week... call me on Friday to confirm our dinner appointment."
We got up and walked out of the restaurant. He walked me to my car and
kissed me again before closing the door.
I agonized the whole week and finally decided that I wasn't going to find
another man like Peter. I called him Friday night and told him yes.
That night, before bed I slipped into a silk teddy. I was so apprehensive I
could barely sleep, tossing and turning the whole night. Peter was all but
guaranteeing a great, satisfying evening, but I was nervous. What if the
experience didn't live up to my expectations?. What if I didn't satisfy Peter?
What if it hurt? What, what, what... finally I fell into a light sleep around
4:00am. I slept until noon, ate a light lunch, and started to get ready. A long
hot bath after shaving and I was ready. I spread moisturizer all over my
body. I stepped into the loose pink panties and pulled them up my long
smooth legs, my penis and hairless testicles felt delicious confined by the soft
fabric. The matching bra and my latex 36B breast forms came next. I brushed
out my long blonde hair and stood up admiring myself in the mirror. The
$300.00 forms had been worth every penny. Unlike the cheap ones I'd had
before they matched my skin tone perfectly, the pert semi-erect nipples were
all too believable. I pulled on the loose fitting sweat bottoms then pulled the
top over my head. My erect nipples protruded slightly, and the top clung
nicely to my full breasts. I applied some light make-up, pulled on my
sneakers and started looking for my keys. The phone rang, I answered it
quickly. It was Peter! Until I heard his voice I had almost forgotten about
where I was going! "Honey... don't bring an overnight bag...I've taken care
of everything..." I stammered a quick "OK" and was about to hang up when
he asked me if I was nervous. Again I stuttered through a "Yes..." "Don't
be... everything is going to be fine, I'm going to treat you like a princess...
my little princess... see you in a few minutes...bye." I hung up. Looked in
the mirror by the door, took a deep breath and left my apartment, and my old
life..
Maybe it was just nerves, but the drive to Peter's seemed to take a lot less
time than usual, before I knew it I was pulling into a spot in front of his
building. Another deep breath and I was up the stairs and knocking on his
door. He answered in a black silk robe and smiled when I hesitated before
entering. He leaned over and kissed me on the cheek whispering,
"Everything is going to be just fine... you've made the right decision. Let me
get you a drink..." He locked the door with a key and placed the key in his
pocket... suddenly I was scared. No one knew where I was... what if he was
a nut! "They could trace our phone calls don't worry, I swear I'm not a
creep..." he held up the key "...this is just to keep us locked in... together.
Why don't you go into the bedroom and get changed, I think I've laid out
appropriate clothes...I'll bring in your drink when you're ready." He patted
me on the butt as I walked past him. I stepped into his bedroom and closed
the door behind me. Could I still back-out? Did I want to? No, Peter was the
man...
I pulled off my clothes and stood in front of the boxes on the bed. I slowly
opened the first. A delicate white lace bra and panty set. The second box: a
matching white garter belt and white silk stockings(I checked the label). The
third box: a white silk skirt. The fourth box: a pair of high gloss, white patent
leather 4" pumps with wide ankle straps, hanging from the straps were 2"
chrome loops. In the bottom of the box I noticed two white leather wrist
cuffs, also with 2" chrome loops. I had said that light bondage would be a
big plus in my advertisement, but Peter and I had never spoken about it! I
looked at myself in the mirror and decided this was my best chance to take the
next step, and that if I didn't follow through I might never get another
chance. My heart was pounding as I quickly got dressed. A few minutes later
I grabbed the door handle with a shaking hand, I looked over my shoulder at
myself in the full length mirror. As far as the mirror was concerned I was a
woman. Now I had to take the last step. I opened the door and sauntered into
the living room, swishing my hips and the silk skirt side to side. I could see
the amazement on Peter's face as he took in my beauty. "You look better than
I could've possibly imagined!" I walked closer and joined him on the couch
my self-confidence growing with each of his stares and stammers of
appreciation. I looked at the Television. A beautiful Transvestite was sucking
off a handsome man, while getting sodomized by a woman with a huge pink
strap on dildo. I felt my cock stirring within my tight lace panties. I looked
over at Peter, the thick tip of his hard penis was sticking out the front of his
robe. He caught me staring. "Is this my drink?" I asked pointing to the table.
Peter stammered "Yes" and I drank it down. Peter shifted, and the next time I
looked over his penis was covered but still obviously rock hard. We watched
the video until the man came all-over the transvestite's pretty face, white
streams of cum streaked down her face as the woman riding her asshole
finally shuddered with an orgasm. The TV spun around and took the rubber
cock between his lips, deep-throating the thick cock. Peter looked over at me.
On the television the man had moved into position and was slowly mounting
the sexy transvestite. Peter turned off the television, and asked me if I wanted
to eat dinner and finish the tape later. "Yes, definitely." I answered "...and
can I have another drink?"
I sat at the table as Peter served dinner. He placed a drink next to me and sat
down. Both of us picked quietly at our meals. I felt Peter staring and looked
up. "You are so beautiful, I really can't concentrate on anything else... do
you want to watch the movie?" I tried not to sound too excited, but failed.
"Yes, I would like that...a lot" I finished my drink and asked for another.
Peter went to mix it while I sat back on the couch. I hit play and the tape
picked-up where we had stopped it. Peter sat down and turned the volume
up. The transvestite was groaning with each long thrust. A few moments later
Peter excused himself, "I'll be back in one minute..." The man on the
Television was on the verge of orgasm, he came with a shudder and pulled
out his cum-spurting cock, spraying cum all over the TV's ass, rubbing it in
with his slowly softening penis. Peter walked in with three oddly shaped
boxes. "I have three more presents for you, this is a special night, I think
they'll help you out..." He laid them on my lap. They were heavy! "I can't
wait." I tore open the first box... four heavy-duty padlocks? I looked up
already knowing what they were for. With a furtive glance at my wrists,
Peter's nervous look confirmed it . He was blushing, I smiled and set aside
the box, digging into the second box with a quick "Thank you." The second
box contained a small white rubber ball, running through the center was a
white cord with a buckle on each end. "You don't have..." Peter stammered.
"No, I like it..." I really did, the thought of being hog-tied while getting
fucked up the ass was delicious! To tease Peter I winked at him and said "I
only wish it was shaped like a cock..." I put that box aside and started to
open the next one... it was long and skinny. I pulled aside the tissue paper...
a three feet long chrome pipe with loops on each end. I stared at it for a
moment before realizing what it was. The bondage magazines called it a
spreader bar. It attached to a person's ankles, keeping the legs spread for a
spanking or a fucking! I sat back and sighed. "Peter, I'm so hot... this stuff
has really put me over the edge... I want it so bad... I want you so bad... can
we just start... please." "Sure, grab your gifts and let's head for the
bedroom"
Peter guided me into the bedroom and sat me on the edge of his bed. "Put
your hair up in a ponytail" I did quickly. "Hand me your gag honey." I
reached behind myself and handed it to him. "Open your mouth." I did, then
closed it before saying, "I really want to suck your cock... I want to taste
your penis... your cum." "Don't worry Christina... you'll have plenty of
chances." I smiled and opened my mouth happily. He placed the ball in my
mouth and pulled the buckle tight. It was not big enough to be
uncomfortable, but definitely big enough to keep me from speaking, or
screaming. Next he motioned for me to hold my hands out in front of myself.
I did, and with the aid of the leather wrist bands locked my wrists together.
He gently spread my legs and knelt between them. He reached under my skirt
and looped his shaking fingers through the waist band of my panties. I felt as
if there were little sparks everywhere he touched me. He tugged at them and
slowly slid them down my legs. My cock immediately throbbed to its full
height, tenting the silk skirt in my lap, instantly there was a spreading wet
spot from the pre-cum oozing from it. Peter stood up and stepped back. "You
look so sexy..." He leaned forward and again reached under my skirt roughly
grasping my cock. "UP CHRISTINA!" I quickly stood up and he led me the
edge of his bed and instructed me to place my bound hands on the black
tubular frame of his bed. Again he un-locked one of the padlocks and quickly
looped a short length of chain around the frame fastening my wrists to the it.
I noticed the numerous chips in the paint from the previous times he had done
this. Next, he stepped behind me and grasped my hips pulling me backwards
until I was bent at the waist and my torso was horizontal. He pulled the
spreader bar from the box and knelt between my legs. He pulled one leg to
the side and closed a lock between the loops. Next he pulled my other leg out
and fastened the other lock. I was totally immobile. Well, not totally, I could
rock back and forth. Peter climbed onto to the bed and dropped his robe. His
rock hard cock stood straight out from his muscular stomach. The purple
mushroom shaped glans was inches away. "Do you like what you see?" I
shook my head yes. He reached behind and produced a large tube of
lubricant. He squeezed out a dollop and slowly applied it to his cock. Starting
with his glans he slowly moved his hand up and down his veined shaft. After
a moment his cock was covered with a thick sheen of grease. "Do you want
me to fuck you with this... With my thick, hard cock? Slide it up your tight,
virginal ass-hole? Make you feel as much like a woman as a man can feel?
Then FUCK you over and over again until I finally cum... filling your tight
hole with my hot sperm?" I was shaking my head yes repeatedly, groaning
my approval, begging with my eyes. Finally he crawled off the bed and stood
behind me. "You can watch me, us, in that mirror..." He pointed to the left
and I looked over. Peter grabbed the hem of the silk skirt and pulled it up
piling it up on my lower back. He then squeezed out more lubricant and
proceeded to rub it between my cheeks. I was in heaven. Every time one of
his fingers came near my puckered hole I tried to squirm backwards. He
could feel my frustration when after a few minutes he finally asked me. "Do
you want me to stick my finger... fingers up inside you... to loosen you up
for my thick cock?" I shook my head quickly. In a flash he shoved a finger
deep inside me. I felt so violated... but so good! A moment later he asked if I
wanted another finger and I shook my head yes, then another, I said yes to
each one. His fingers were squirming inside me. The sensations from my
hole spiraled out, flooding my body. I broke out in a light sheen of sweat.
My cock hurt it was so hard. Every so often he would stroke my smooth
testicles and light waves of pleasure would wash over me. Next, he relubed
his penis and took a step closer to me. He moved into position and my body
tightened involuntarily. "I'm not ready to hump you, and you're not ready
either, you're not hot enough, hungry enough... woman enough." "I am... I
am... Please!" I mumbled around the gag. He teased me for what seemed like
hours. Repeatedly sliding his cock between my cheeks but never entering me.
I wanted him so badly, that every time his glans came close to my hole I
started to struggle against my binds moving towards him. "Now we're
getting somewhere... now you're hungry... now you really want it, before
you thought you wanted it... can you feel the difference in your heart?"
"Yesss! I can!" I whined around the gag. "Please..." I shook my ass side to
side. "Please... Please take me... Please!" He moved again and I watched
and felt as he placed his red-hot glans between my cheeks... pressing gently
at my anus. "Christina, are you sure you want this? You're turning your back
on your entire life... I'm sure you'll never go back..." "Yes! Yes Peter. I
want you... please?!" He grasped my hips and hesitated. "Once I start you, I
have to finish..." "Yes... please!" Tears had formed and were now running
down my cheeks. I had never wanted something so much before. Peter could
tell and finally he gave me what I wanted. He took a deep breath and shot his
hips forward forcefully, grunting with the exertion. The pain was
astounding. White-hot bolts of agony melted my knees and caused me to
scream wildly around the gag in my mouth. Peter wrapped an arm around my
waist, holding me up. Deeper and deeper he plunged. My cock immediately
wilted, recognizing my betrayal of it with this act. He stopped for a moment.
Tears of frustration were immediately replaced with tears of pain. My light
sweat was quickly replaced with a drenching, dripping sweat. I was sobbing,
gasping for air. "Nothing worth begging for, ever comes easy Christina. This
should hurt. This is your new life!" I had thought he was in me to his hilt,
but I finally looked in the mirror... fully 4 inches remained. My body quaked
as he pushed forward once again. After an agonizing moment I felt his
testicles press against my own. His pubic hair tickled me between my cheeks.
My anus was contracting uncontrollably around the thick base of his cock.
With each contraction the pain decreased slightly. "Concentrate Christina...
concentrate on the sensations... remember each heart-beat. This is your first
time. Ask any woman how her first time was and she'll relate every touch,
every thrust, every moment. Do you remember your first time as a man?
Probably not, but you'll remember this... wont you?" I shook my head yes.
His thick shaft hurt, it really hurt, but it also felt some-how natural. Like this
was how I was meant to be. He slowly pulled back. I wasn't sure if it was
relief that his huge cock was sliding out, but suddenly his cock felt good. He
slid out with a sigh. I shook my head back and forth and tried to speak. His
hard vital cock slid against my soft flaccid penis as he leaned forward. He
unbuckled the gag. I gasped for air. "Do you want this off?" "Yes... please? I
know why you had me wear it, I was screaming insanely a minute ago, and I
would've begged you to stop, but I'll do neither now, I promise." "All right"
He pulled it off and tossed it on the bed. "Are you ready? You have to relax
every muscle, you're so tense, think loose... and I mean that in more ways
than one..." "I'm ready Peter... I really am... take me... please." He smiled
and once again grasped my hips. He moved his penis into position and slid
forward. No doubt the pain was still there, but it was different, we were
working towards something. Towards something good. I concentrated on
breathing while soaking in every ripple and vein of his cock as he slowly
sawed in and out of my loosening asshole. "It doesn't hurt half as much
now... right?" Peter patted me on my cheek as he picked up the pace. "No...
it doesn't. It still hurts, but its also mixed with something else... longing I
guess. Your cock feels so natural, every time you slide out I feel so empty...
so useless. When your inside me I feel good... it feels so good... really
good." "I'm glad Christina, I'm really happy I could be a part of this for
you... but now comes the hardest part, actually its very easy for me, in fact I
wanted to shoot my load the second I crammed my cock inside you. For you,
its tough, you have to give in, let yourself become the woman you want to
be, it sounds easy, but its not, you have to let another man cum deep inside
you... you have to let another man use you as he would a woman. You have
to want to feel my hot cum boiling inside you..." Goose bumps exploded
over my body at the mention of becoming a woman. I wanted it... I wanted it
more than anything. "Yes Peter... yes... fuck me like a woman... do me."
Peter immediately began humping me furiously. Slamming his hips
repeatedly against my up-turned cheeks. His balls whipped against mine over
and over again. The pain of his intruding member was definitely dissipating.
Replaced by hunger... hunger and longing for his hot sperm... only then
would I be satisfied. I began rocking backwards each time he thrust towards
me. "I knew you could do it, I knew you'd figure it out..." He reached up
and grabbed my pony-tail pulling backwards forcefully. "Yes, ride me... ride
me harder..." His cock was so deep, but I still wanted more. He was just
barely stroking a spot that felt so good. Every time his glans probed as deep
as imaginable the spot seemed to move deeper. I begged for more. "Please
Peter... DEEPER... DEEPER... I know I sound like a cheap whore... but it
feels so good... use your hands... to... spread my... cheeks wider... yes just
like THAT!" He spread my cheeks painfully and pressed deeper. Finally the
spot... finally he was stroking the spot...! As he rode me I thought about all
the men who would never now the ecstasy I was feeling... Did every man
have a spot of their own? I hoped yes, and I wished they would all give in
and let themselves enjoy the sensations. The heat in my abdomen was
building with each stroke. As we neared climax I deteriorated to grunts and
moans of approval. "HARDER and DEEPER yes Peter YES!" My cock
slowly arose... stiff once more. My hairless balls tightened and pulled close,
ready to shoot at any moment.
"PETER YES PETER YESSS RIDE MY FUCKING HOLE I SAID RIDE
ME! YOU FUCKING BASTARD DO IT DO IT. AM I WOMAN ENOUGH
NOW? FUCK MY HOLE. PLEASE?!" Would he ever cum? I thought back
to the one time I had fucked a woman up the ass, she was so tight, and
twitching, I had barely entered her when I exploded. "PLEASE PETER!
PLEASE? I'm Fucking begging for your SPERM, PLEASE? PLEASE
MAKE ME A WOMAN PLEASE? PUMP ME FULL PUMP MY
FUCKING HOLE FULL OF SPERM MAKE ME CUM...PLEASE?!" Once
again I was crying, sobbing actually, he was a machine, how could he last so
long? "Yes, Christina, yes you're almost there bring your man off bring me
off with your tight hole. You know you can I know you can" I was throwing
my hips at him as hard as possible, my legs were bound open, and he was
holding my cheeks apart, what else could I do? The sweat was once again
pouring down. I finally remembered that woman so many years before... she
had convulsed once, tightened involuntarily on my cock and I had cum
uncontrollably, stabbing her convulsing rectum with my throbbing cock over
and over again, each time she clamped down, I would spurt! I knew what I
needed, and I now knew how to get it! "Peter I'm ready, please be ready,
please be ready to shoot your sperm" "Christina, you're not there yet" He
took my sudden calm as submission. I knew better. "Christina, feel my cock,
feel every vein, feel how my glans spreads you wide open CONCENTRATE
YOU BITCH!"
At that, I did it. I pushed back and clamped down squeezing as every inch
surged into me. "Yes, Christina, YES!" He reached around and effortlessly
wrapped my cock in the silk skirt with one hand, while squeezing my balls
mercilessly with the other. "Milk my fucking cock, milk it you BITCH" I
came an instant later. My cock spasmed in his tight grasp, pumping the
material wet with cum. With each spurt my rectum tightened around his
pistoning cock. In an instant he came. Suddenly he was grunting, driving his
cock deeper and harder in harsh short thrusts. Then I felt it. His glans seemed
to expand, and then he was pumping uncontrollably. Actually lifting me off
the ground with each thrust. We were cumming together! "You little bitch
take it! You FUCKING bitch... take your man's cum... take every last drop"
I felt the heat of his cum as it pumped into me. He reached between us and
pulled his still slightly spasming cock from me. Immediately I felt his warm
sperm oozing from between my cheeks.
"Un-fucking believable. You're the first little whore to make me loose control
you are unbelievable. You're a fucking natural. That felt so good!" "Peter
you made me feel so helpless natural so normal." I felt his still warm cum
running down my legs. "Can you un-lock me now?" "Christina, we're not
done yet, not by a long-stretch you have so much more to learn, you've just
started" My cock was totally soft, and I was totally satisfied. I felt Peter's
soft cock resting between my sloppy cheeks, so I knew he was satisfied.
"Peter, I want you to teach me more, I do I want to learn more. But aren't we
finished for now I'm all messy" My cum-soaked skirt hung against my leg,
and my stocking-tops were soaked with Peter's cum. "No you're not messy,
you're sexy." He rubbed between my cheeks spreading his sticky cum over
my cheeks. He moved slightly and I felt his cock stiffening. He rubbed it
between my cheeks, without entering. He knelt and I heard a click, then a
loud buzzing. In his hand I saw a absurdly huge vibrating butt-plug. "You're
going to like this trust me" He placed the exaggerated rubber glans at my
stretched anus and proceeded to stuff it in. It was at least 1 inch thicker than
Peter. I groaned and begged him to stop. "Please PETER please STOP!
Noooo!" Totally removed from my aching asshole I felt him press it home.
He quickly looped three small straps around my waist and between my legs.
"Please PLEASE PLEASE PETER NO my hole aches Peter please?" I
whimpered shaking my hips side to side. He buckled and tightened the straps
uncomfortably. He laughed and turned it to high. A bee-hive was loose in my
ass-hole. "Please stop it Please stop it PETER" Through the pain my cock
throbbed back to erection. "Obviously somewhere deep in your subconscious
you like this" "Peter" I gasped "I love being dominated by you but this
hurtsplease?" "You'll get used to it trust me" He crawled unto the bed and
knelt in front of me. His cum streaked penis was inches away. "Remember
when you said that you really wanted to suck my cock? Here's your chance"
He moved close and I pulled back. I could only move a few inches and he
just kept coming. He grasped the back of my head with one hand, and while
holding his cock straight with the other pressed his slimy cock against my
closed lips. "Christina, we could do this the easy way or we could do it the
hard way. I hate to tell you, Either way, you're going to suck my cock." I
briefly struggled against my binds before looking up. "It's good you've come
around. Remember, no biting. As I opened my mouth I planned to say "You
bastard", but only got out "You" before Peter jammed his musky cock
between my lips.
The remainder of the weekend I spent dressed in the most expensive,
exclusive lingerie, tied and bound in various positions. I loved every minute!
I never even went back to my apartment, Peter wouldn't let me. I live with
Peter as his private transvestite sex slave. He wont let me get implants or to
start hormones, he says he loves me just the way I am. I am the main
attraction at parties he throws. I've been gang-banged more times than I can
count. I loved every stroke and spurt. I've learned that there have been many
others, (I've had to watch endless hours of video which only makes me
insanely jealous!). Once Peter considers his slaves "used-up" he throws or
gives them away, (he assures me he's taken care of them with cash, but how
am I to know for sure?) I know I've been with Peter the longest, he says I
work harder. I'm hoping I can keep him.
fin
Madison
- 04.12.2020
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