Play Day for Sara

It doesn’t happen often, but an opportunity opened up for me recently to take a day off to get a
hotel room, get dressed, and entertain men.
So I took it.
When I discovered I would have this day to myself the previous week, I ran the following ad on
craigslist:
“Get ready boys – t4m super horny cd coming to town on Tuesday of next
week. I’ll be hosting at a hotel in midtown. Unlike just about every other t on
here, this isn’t a pay for play proposition (although it could be a pnp
situation). The only currency I want is hard dick.
Safe play only.
Looking to host from 10 AM to 6-7 PM. Will post more details on Monday
after I go shopping. Revealing pics to all serious inquiries.
Fill my holes and let me make you cum.
Everybody wins.”
I followed up with much the same ad with pics when I checked in. During the day, I got over 50
responses. What to do?
As you begin to respond, you soon discover that some are just chatters, and even though “all
day” sounded like forever at the beginning, time becomes a precious commodity when you are
juggling responding to the barrage of incoming e-mails, putting on the finishing touches, and
pleasing yourself with a dildo (such is the life of a sissy).
Cutting to the chase, I had enough men respond who were both desirable and serious that I could
have stayed until the weekend. Having only a day, I did as much as I could.
My first visitor of the day was a construction worker in his mid-30s. He was really nervous, just
standing there. I responded by getting on my knees, unbuckling his belt, and pulling down his
pants. I could see the bulge in his underwear. I gently nibbled his cock a couple of times, pulled
off his underwear, and deep-throated his gorgeous 7 in. rod. In no time it was as hard as steel.
He hurriedly took of all of his clothes while pushing me away. I retreated to the bed. Completely
nude he walked around to the side of the bed I was on and placed his cock inches away from my
face, and I lovingly sucked his shaft and balls. I could feel it throb from time to time, and I thought
he was going to come in my mouth when he said, “Let’s fuck”. I rolled away to make room for
him on the bed, hiked up my skirt and presented my ass. The next thing i felt was him flipping me
over on my back and pulling my hips to the edge of the bed. I put my legs up in the air, he held
my ass firmly in place, and he began fucking me hard. Then, with a strong thrust he buried his
cock in to the hilt, and let go of my ass so he could lean over a bit, and I was able to move my ass
up and down and massage his dick. I felt the tip of his cock as deep inside me as I can take a cock.
He let out a huge moan and I could feel him coming inside the condom. It was a big load.
Now, what happened next and how I reacted to it is one of the sweetest perversions of sissydom.
As soon as he came, his whole demeanor changed. He took off the condom, ran to the
bathroom to clean up, and then quickly put on his clothes to leave. His eyes darted around, he
looked down and said he had to get back to work in an emotionless voice, and he was out the
door and gone. While all this was going on, I laid back on the bed, KY Jelly oozing out of my ass,
watching this frenzy of activity.
When the door shut behind him, I felt a huge rush of excitement knowing that I was just a
discarded fuck toy. I meant no more to him than an artificial vagina. I soaked that feeling in and
loved it.
After some time, I got up, looked in the mirror, and saw I had work to do to freshen up for the
next visitor. When I checked the e-mail again, I had 7 new replies. The search was on for No. 2.
After my construction worker left, and I was preparing for my second caller, I showered and reapplied
make-up, tried a different eyeshadow, and put on another dress. Then, and only then,
did I clean out my ass, so luxuriant and, I confess, demeaning was the squishy sensation I felt
back there. With every step I took I felt the silky wetness in my ass cheeks, and I loved it.
When I got back to my e-mail in earnest, I went through the new messages. There was also a
message from earlier that morning from a 29 year old who sent a picture of his cock only. A new
message from him flashed up to say he was 10 minutes away. Of course I told him to come on.
As I waited, I primped in the mirror and played with different shades of lighting from the curtains.
I had started watching Sissy Dreams 3 and fantasizing about what would come next when I heard
a timid knock on the door. What walked in was a beautiful blond boy much younger than me. He
looked at me and I wasn’t sure if he would bolt given our age difference.
It’s good to remember at times like this that we live with our sissy-ness and feel naturalized to it
in a way that most men who walk through that door don’t. To us it is a delicious but by now
familiar perversion that is central to who we are. To most of them, they are doing something way
beyond merely meeting a woman, or even a gay man, in a hotel room. They are, as Lou Reed
once put it, taking a walk on the wild side, a really wild side.
So I tenderly told him he was beautiful, and in control. I was there for him if he wanted me. The
door was there for him if he didn’t. He let me know his decision when he pulled down his pants
and laid back on the bed.
Though it wasn’t fully erect yet, I could tell this was a bigger penis than the one I’d had earlier. I
began by kneeling between his legs and gently sucking on his balls. I looked up at him as my
tongue gradually made its way up his shaft, swirling around the head of his cock.
Whenever I have the pleasure of sucking a young man’s cock, I’m reminded of why it’s so
wonderful. With an older man, the little blue pill gives him the erection, but not really any more
sensation. You can literally wear your jaws out trying to get them off orally. On the other hand,
the younger man feels everything. You feel him feeling it in countless little body twinges,
involuntary hip undulations, and even the vibration on your tongue of semen stirring within his
shaft. You hear his moans.
I decided to go for the deep throat, but I hit an obstruction before I got the last couple of inches
in. I was at the wrong angle.
No worries. I moved around to his side and rested my head on his chest. I even brought my legs
around in the hope that he would start playing with my ass. Instead, he began sucking my cock.
Not a bad consolation prize.
After a fashion he fell back and stared at the ceiling, and I knew he wasn’t going to fuck me.
That’s ok. I don’t swallow but I love to take a good load in my mouth and I suspected this was
going to be a big one.
I decided to try to take him all the way in again from that angle, and this time it worked. He was
all the way through my mouth and down my throat, which I used to massage the head of his cock.
As I began pulling up, the first thick rope of cum flew though my mouth. I immediately quickened
the pace of my movements on his cock as my mouth filled up and then spilled over with cum. I
buried my face in his groin as I sucked out every last drop. I was thoroughly glazed from the neck
up.
What an incredible, glorious, sensational and delicious mess. When I felt him completely relax I
laid on back on the bed, my head next to his loins, staring at the ceiling, feeling the sticky wetness
all over my face, and little streams of cum dribbling down my cheeks.
After a while he got up and went to the bathroom. He returned with a wet towel and gently
cleaned off my face and neck. Then he kissed me.
The first man made me feel like a gurl. This man made me feel, if only for a fleeting instance, like
a girl.
After a short interlude, he too got up, dressed, and took his leave. And I was again alone.
For a time I just stayed there, flat on my back, looking at the ceiling, torn between a desire for
my next dick and a desire to reflect on what had come before. I took a deep breath and
wondered… after a life of heterosexuality, how did I end up here in this obscure hotel room
inviting strange men over to ravage me? Dressed like a woman? Taking cock like a woman?
Obsessed with make-up and dresses? As turned off as ever to two gay men having sex, but unable
to quell the pit of excitement in my gut from the femininity, such as it was, I brought to these
encounters?
My thoughts returned to my sticky face. Despite the best efforts of my young blond lover, I was
still glazed with cum after he left. The girl quickly changed back to a gurl. I leered over at my
computer…I was hitting my stride. I wanted my next dick.
Before I went to the shower, I checked my Inbox. A handsome black guy in his mid-30s,
professional looking, had written first thing that morning. He had meetings until 2. He had written
to say he was done. I told him I needed about an hour and asked him to pick me up some poppers
on the way over.
I took off all my clothes and stepped into the shower. I let the warm water flow down all over
what I imagined to be the feminine contours of my body. Once I was squeaky clean, I dried off
and sat in front of the mirror again for make-up. Earlier in the day, I’d gone pretty slutty. I opted
this time for something not quite so overdone….more earth tones in the eyeshadow, more
conventional red for lipstick rather than the hot pink, a bit less blush. I was very pleased with the
results, and how used I was getting to applying makeup. It was becoming second nature. The
thought made me feel like I possessed a certain femininity….not inherited from nature, but rather
earned, as if I was being rewarded for my desire to shed my masculinity by this brief incursion
into the world of girl…the hair, the makeup, the panties, the clingy bodycon dress, the hourglass
figure with the aid of a bodyshaper….as if the mother in Mother Nature was saying to me, “Yes
Sara, you may stay and play with us, like us, as one of us, for a short while.”
I was shaken out of my reverie by Derrick’s sharp knock on the door.
I let him in. Just as he appeared in his pictures, he was about 6’3”. He held me close and we
kissed. His body was hard, and I could tell before he took his shirt off that he had one of these
zero fat muscular physiques that are almost impossible to find with white men.
In no time he was on the bed naked. I remained fully clothed. We kissed for a while longer while
I fondled his rocket. It would be the biggest, and hardest cock I had all day. I gradually made my
way down to it, teasing his chest and then abdomen with my tongue. I then took my first poppers
hit of the day…a long drag I held deep in my lungs.
As I exhaled I immediately felt the poppers’ urgent command to suck. I lay my lily white blond
face on his stomach, and lost myself in the wonders of his black shaft. As I sucked, I thought about
how this really was the ultimate act of intimacy…to give a man your mouth…in such close
proximity to your sense of smell…of sound…of sight. The penis is “with you”, if you will, in a way
that is so much more intimate than when you are fucking. And don’t get me wrong, I love to be
fucked. But when you fuck, the dick is “down there”; often you are on your stomach and you
can’t even see what is happening. When you are sucking a man’s cock, it is “there”, right there,
in sight, sound, smell, and of course the tactile feel of the organ on your tongue, in your throat.
I also think for a sissy the oral experience carries a certain sweet ecstasy because it is the one
thing we can do just like a girl does it. As much as I love anal, and as grateful as I am for the
experience of anal, it is, dear sissies, an approximation of what true girls feel in intercourse. It is
nonetheless what we have, and it is beautiful.
It wasn’t long, though, before Derrick lubed up his fingers and started probing my ass, and my
immediate reaction was an intense desire to let this man’s cock take my ass however he wanted
it.
His only words. “Baby. I think it’s time.”
He stood up and put on a condom. My bodycon dress was up around my waist. I writhed as I
looked up at him…expectantly, lustfully. He reach out for a pillow, and I first thought he was going
to place it under my ass so he could fuck me while I was on my back. Instead, he handed it to me
and said, “Here. You’re going to need to bite this from time to time….turn over.”
I did as I was told, a pillow biting slut with my ass up in the air.
Derrick put lots of lube both inside me and throughout my ass crack and around to my little clitty.
He laid on top of me and rubbed his dick in my crack. My hips thrust up to meet him. In the midst
of one of his downstrokes, his cock effortlessly slipped in my ass. He went into the hilt. It hurt. I
bit my pillow.
At that point I fell into a chasm of sorts where one loses a sense of time and memory gets blurred.
He pounded and pounded. I pressed my sphincter on his dick to get a super tight grip. Before we
had started I asked him to video me being fucked by him. Watching it later, the room was too
dark to see much of anything, but the audio it produced was one of unrestrained off the leash
passion. I was crying, I was moaning, I was begging, occasionally screaming even….I remember
thinking I couldn’t last any longer and simultaneously hoping it never ended, riding a razor sharp
wire that separated pleasure from pain.
Finally, he exited and quickly flipped me over. His condom was gone and his dick was in my face.
He was jacking that magnificent organ to climax. I obediently laid back and opened my mouth
wide. It wasn’t long before he started coming…and coming…and coming. It was on my chest, all
over my neck, in my mouth, in my eyes, in my hair. As his pace slowed, I lovingly took his dick in
my mouth and sucked out the very last drop of his cum while he writhed in pleasure. When I was
done, I looked up, and though all the cum, I smiled.
I don’t know where the words came from, and I still don’t think I fully know what they meant,
but they were out of my mouth before I knew I’d said them.
“I love you, daddy.”
After Derrick left, I realized I only had another hour or so before I had to close up shop. There
were more men than I could ever see or answer begging for a shot. I wrote five of them back and
told them the same thing…that I’d just been ridden hard and hung up wet, and I wasn’t cleaning
up for them. If they wanted to come over, I said, be prepared to find a whore that looks and
smells like a whore.
I wanted to finish the day like that. No more perfume and primping. I wanted the smell of cock
and cum all over me. I wanted the taste of cum in my mouth. I wanted that squishy just fucked
ass. And indeed, when I stood up to walk across the room, I felt fucked like I hadn’t felt all day.
I had two takers. I asked them if they wanted to do a threesome. One could be there in fifteen.
The other in a half hour. Jerry got there first. He was in town on business, he said. He leered at
me and said, ”You really are a cock-slut aren’t you?”
I replied, “If you can think of another reason why I’m in this hotel room in the shape I’m in having
just invited you and one other man to come tag team me, I’m all ears. But yes, I think you had it
right the first time.”
We left the door cracked so the other member of our party could come in and join us when he
arrived.
He pushed me down on the floor against the wall and pulled out his cock. I took a long hit on the
poppers. “Suck it“, he commanded.
So there I was, dick buried in my mouth to the hilt, mascara streaming down my face, saliva
everywhere, an uncontrollable pit of excitement rising from my stomach. I know what I looked
like. It was almost as if I had an out of body experience. As I looked down from above I was the
slutty truck stop whore who had suck my cock years ago. I was the stripper I had picked up and
banged all night with two other friends back in my mid-thirties. I was every man’s whore. And
that is exactly who and what I wanted to be.
Jerry picked me up and shoved me onto the bed. He laid down beside me and I continued sucking
him.
I hadn’t even heard Sam come in (heck – I’d even forgotten all about him), and I jumped a bit
when I felt an unexpected second pair of hands fondling my little bubble ass. I could tell Jerry was
close to coming. I pulled up, rolled over, and looked at them both with eyes that tried to tell them
they could do anything they wanted to do.
They must have gotten the message. Sam laid on the edge of the bed, his feet over the side, and
said, “Ride me.” Because I really am a cock slut I knew exactly what that meant.
Reverse cowgirl.
I bounced up and down on his dick, while Jerry came around and stuck is dick in my face. So I
could suck Jerry, I quit bouncing and started a slow circular undulating grind on Sam while I
hungrily swallowed Jerry. My pussy was gushing wet. Suddenly, Sam grabbed my hips and
directed them front and back across his groin. That made his dick tease the back end of my
rectum in the most pleasant way, and I aided his movements. I heard him groan, and I felt a
gusher inside me. After he finished, he tossed me off and I laid there on my stomach. Jerry then
hopped on and proceeded to mechanically fuck me. I didn’t care. I was exhausted. I was spent.
There was no more physical pleasure to be derived, just the emotional pleasure of knowing my
sloppy wet boi pussy was being used by another man to come to climax. I was a human fleshlight.
When it was time, he shot his come on my back. I didn’t move.
As Jerry and Sam hurriedly got their clothes back on, Sam said to Jerry, “I can’t believe we just
did that”.
“Yeah.” Jerry replied, “God, look at her.”
I smiled inside….because he’d said “her”. I never even turned over to say goodbye. They never
said goodbye to me. Instead, Sam said to Jerry, “Let’s get the hell out of here.”
And then they were gone.
Cum was dripping out my ass. Cum was dripping off the side of my back. My face was sticky with
drying saliva and pre-cum. My breath smelled like dick. I know my ass smelled that way as well.
My underwear was all torn to shreds. My leopard print bodycon dress was covered in cum stains.
My pussy was sore…comfortably sore…..achingly sore….lustfully sore….I couldn’t decide. I just
know that I loved it.
The light of the day was starting to dim outside. Soon, I’d have to shower and pack and go back
to my other life. Before I did, I tried to make some sense of what it all meant. I recalled at the
beginning of the day, when I first looked in the mirror…how fresh and feminine I felt. I remember
thinking that I wished my dick would just fall off for good, right then and there. I felt a lump of
excitement, quite muted but still there, thinking about the next time. Kind of like the conclusion
of Sissymaker II, when the organ gradually comes back with a muted pulsation while a sissy rides
a dick.
I thought how this had all started in 2004, when on a lark I decided to go to an adult theater to
suck a dick instead of a strip joint ….how it then took me a couple of years to figure out that I was
a bottom….how I used to spend so much time on Ass4All watching Heather Brooke and Amber
Michaels suck and do anal, trying to put myself in their bodies….but still thinking of myself as a
man being fucked by a man.
Of course, like so many, the great transformation came when I discovered Annamalice. A year
into Annamalice, crossdressing was just a fantasy….but then it wasn’t. Meeting men in hotel
rooms dressed up like a woman was a fantasy, but then it wasn’t. Going out dressed like a woman
on out of town trips dressed up like a woman was a fantasy…but then it wasn’t. Having the
courage to present myself with wig and wardrobe at a MAC store for a total makeover, from
which I then proudly walked out to my car and drove to the nearest porno theater and took over
the joint as the reigning theater slut….it was all a fantasy, and then it wasn’t.
The one thing I knew for certain is that I would always be back. Once you’ve done this, it has its
hooks in you… just like it says on Sissymaker, there really is no turning back…it’s just a matter of
where and when you have the chance to indulge your sweet tender precious sissy perversion,
knowing how richer your life is because you’ve lived this, and secure in the knowledge that you
will live it again.