Didnt ask didnt tell – Shemale story

Little different story for the collection: Shemale edition

In my younger days, Saturday Night was either date night or barhopping night. In either case my goal
was to get laid. I was a good-looking guy and often succeeded.
Tonight was a barhopping night. I left my place around ten, and stopped at a few of my favorite
spots. I’d have a drink and if they were slow, I’d move on to another bar, and repeat that until I was
ready to call it a night or found a woman to hook-up with. No rocket science here, I just wanted a
warm pussy to sink my meat into.
As it turns out, it was a slow night at my usual hangouts, so I stopped at a local bar I’d never been to
called ‘Don’t Ask.’ This place was small but busy. The drinks were flowing and the bartender was a bit
older, but she was a knockout.
When Renee served me my first drink, she asked me if I’d ever been in before. I let her know this
was my first time, and told her my name. Hearing that she said, “Well welcome Alex, I’m Renee, and
this one’s on the house.”
Within minutes I new she was a sweetheart. I thanked Renee, and gave her a generous tip. I liked
her.
I accessed the crowd while I sipped on my drink. It was mostly couples, and a half a dozen single
men including myself. I did notice a girl sitting at the far end of the curved bar. It appeared to me that
she was by herself, and she looked super cute from a distance. She quickly peeked my interest.
When Renee walked by, I stopped her and inquired if the girl at the end of the bar was with
someone. She let me know that Lilly always comes in alone, hardly ever talks to anyone, and always
leaves alone.
Hearing that, I had Renee send Lilly a drink. She did, and Lilly waved to thank me.
I waited a couple of minutes, picked up my drink, and then headed for the open bar-stool next to Lilly.
I sat down and introduced myself, and she did the same.
Truth be known, I wasn’t looking for romance, I just wanted to tear her clothes off and get her in bed.
Man was she hot!
Lilly and I chatted, and I expressed to her how I couldn’t understand why she was alone on a
Saturday night. I teased her by saying, “Lilly, have you looked in a mirror lately, you’re a doll!”
Lilly smiled and thanked me for my compliment. She had a pretty face, big boobs, a nice body, and
she was sweet too.
Lilly opened up a little, and started to tell me why not many guys want to date her. She was about to
explain; I stopped her, “I really don’t want to know why. I think you are sweet, a living doll, and I would
love to go out with you.”
Lilly’s body language and facial expression told me everything. I was in. We talked for a while, and
then Renee announced, “Last Call.”
I asked Lilly if she wanted another drink and she declined. I was a little bummed, but then she said,
“Why don’t we have one at your place.”
My cock heard that. I paid our tab and left Renee a nice big tip. She thanked me and winked, and I
knew why she winked – Lilly always left alone. Well not tonight.
Lucky me!
My car was parked right out front. I opened the car door for her, and when she spread her legs
getting in, I noticed she was wearing a pair of black panties under her short pink skirt. They looked
expensive; as did her blouse, skirt, and shoes. Lilly didn’t have any nylons on; she didn’t have to, her
young legs were smooth and shapely.
Then I got to thinking, “Was Lilly a call girl? Nah, if she was she wouldn’t be sitting at a bar and
always leave alone.”
Just before I was about to drive off, Lilly leaned over and kissed me. I kissed her back, and then she
put her hand on my cock. I was getting hard so she stroked it through my pants.
Horny as hell, I unbuttoned a couple of buttons on her blouse, and since Lilly was not wearing a bra,
I got a pretty good look at her ample tits. Nice firm DD’s!
I broke off our kiss and told Lilly, “There will be plenty of time to play once we get to my place. We’ll
be there in ten less than minutes.”
Lilly gave my cock a squeeze and said, “I can’t wait!”
Neither could I.
It didn’t take long to arrive at my place. I pulled my car in the garage, and hit the button to close the
garage door. Once the door was closing, Lilly was all over me, like a woman who was just released
from prison, and hadn’t had a hard cock in her pussy for years. I knew it was going to be a wild night!
We walked inside my house and shared a quick kiss. I just couldn’t believe how hot Lilly was. She
was blonde and beautiful, and very petite. Lilly was about 5’3” and maybe 130 lbs. She reminded me
of one my favorite singers’ (in her younger days), except Lilly had big tits.
But something was nagging at me. How could this beautiful blonde sit at a bar, and not have every
guy hound her? It just didn’t make any sense… No, she didn’t eat my car, or the bar, and she couldn’t
have been from Mars. There just had to be something…
We were now standing in my kitchen, and I poured us each a glass of wine. As I was pouring, Lilly
kicked her shoes off, unbuttoned the last three buttons on her blouse, and took it off. Her tits were
gorgeous, and her nipples, wow!
When Lilly approached me I handed her a glass of wine. She took a sip, and then placed her glass
on the counter. In an instant, she was on her knees and had my belt undone and my zipper down.
This smoking hot girl had my cock out of my pants and in her mouth faster than any girl I’ve ever been
with. I wasn’t complaining.
I got so hot so fast I didn’t say a word. I just let her suck and suck, and wow, could she suck. Then
she took it out of her mouth and rubbed my cock between her big DD’s, up and down, and up and
down. Damn!
That did it for me. I took her by the hand and we headed for my bedroom.
When we got to my bedroom, I knew that all Lilly was wearing was her skirt and panties. I got naked,
and but she didn’t. Then I figured she wanted me to undress her. That’s cool. Instead, she started
sucking my cock. Hell, she was so good at it, I was not about to say stop.
After a few minutes she stopped sucking me. Once again Lilly wanted to tell me something. I was so
turned on by this woman I told her, “Let’s make love now, we can talk later. I’m sure whatever your
little secret is can wait.”
Lilly said, “Okay Alex, I tried,” and unhooked her skirt, let it hit the floor, and turned sideways to
model her fantastic ass for me, and turned back.
“Alex, are you ready?”
“Yes,” I said, “Let me pull those beautiful panties down for you.”
I knelt down on the floor in front of Lilly with my face planted just inches away from her pussy. I
hooked a finger on each side of her luscious panties and gave them a swift tug down.
In an instant, a hard cock bigger than mine sprang up and hit me on my chin.
Stunned, I looked up at Lilly.
Lilly had this look on her face, and said, “Alex, I tried to tell you a few times.”
“Holy fuck,” I thought. Here I was, about as hot and horny as I’ve ever been; ready to sink my tongue
and my cock into Lilly’s hot pussy. But now, now I have a huge one-eyed monster level with my lips.
Fuck. Fuck. Fuck!
As I knelt there in shock, Lilly’s huge cock was now bobbing up and down, just tempting me to suck
it. Then something happened. Lilly must have sprinkled some magic cock dust on me, because her
huge cock suddenly turned me on.
In my horny as fuck state of mind, there was only one logical decision. I opened my mouth and let
her gorgeous cock in. I sealed my lips around it, and sucked it just like she sucked me. Within
seconds I felt no shame, and enjoyed her huge fuck stick in my mouth.
Having had many blow-jobs, I knew exactly what to do. The question was, should I stay on it and
make Lilly come now, or later. I really got a good suck going and decided to stay on it.
With her big cock sliding in and out of my mouth, I enjoyed looking up at her beautiful face and tits,
and was curious what it was going to feel like to have her cum in my mouth. I figured I’d soon find out.
I’d say I was sucking on Lilly’s cock well over five-minutes when I could feel it harden. I was pumping
my cock as I sucked hers, and I’m sure that watching me pump my cock added to her excitement, it
did mine.
Then I told her, “I want you to cum in my mouth.”
I was amazed how turned on I was with the thought of taking her load. And then it happened, bam,
bam, bam, stream after stream of her hot cum filled my mouth. That got me so fucking hot; I blew my
load all over my carpet. I don’t think I’d ever shot that far before. Damn that felt hot!
I stayed on Lilly’s cock, and wanted to get every drop of her precious cum. Once I was satisfied I had
it all, I stood up and showed Lilly her load. Seeing that, Lilly opened her mouth and we kissed for a
while, and then we both swallowed it.
To my surprise, Lilly turned me on more than any woman I’d ever had sex with, and I told her so. I
couldn’t wait for us to share my bed all night.
Lilly and I put on our robes and went downstairs. I poured us both a little more wine, and then we
went and sat in the living room. We started to chat, and Lilly once again tried to explain; I put my
finger over her lips and said, “You don’t have to say a word. I know you intended to be honest with
me, but I didn’t let you. Thank goodness I didn’t.”
Lilly snuggled up and kissed me. We started talking about everything other than her secret. I was
enjoying our wine and conversation when Lilly suddenly changed the subject and said, “Alex, I want
you to cum in my pussy tonight.”
Hearing that, I set my glass of wine down, picked Lilly up like a bride, and carried her to the
bedroom. We took off our robes, pulled down the covers, got in bed, and started to make passionate
love. To me Lilly was the hottest woman in the world. She was a ‘Goddess.’
I kissed her over and over, and told her how beautiful she is. I fondled her breasts, and kissed her
breasts, and sucked on her nipples as if she was feeding me her precious milk. This woman was
exotic and erotic.
Lilly scooted her body down and passionately kissed my cock from top to bottom, and then she
started to suck it. But this time was different; it wasn’t a typical blowjob. With only the head of my cock
in her mouth, I felt her tongue move around ever so slowly, back and forth, and up and down, and
then she penetrated the hole of my penis with her tongue. I’ve never felt such a sensation. I closed
my eyes and imagined it was my tongue licking and loving her pussy.
In a split second, Lilly looked up at me and said, “Alex, your love muscle is ready to penetrate my
pussy. Please fill me with all you love.”
I moved down so I could lick her pussy. Once my face was under her, I loved her super clean scent. I
gently licked her, and Lilly loved it.
I knew just licking her pussy was not going to lube her hole, so I used my tongue to open it up. It
didn’t take long before her pussy was now resting on my mouth with my tongue buried inside of her. I
must have had my tongue moving around inside her for five minutes. I was really getting into it.
I looked at Lilly, pulled her body up on top of mine, and moved my cock around to penetrate her
special pussy. I wanted to stay on my back so I could totally admire her amazing body.
Sensing my preference, Lilly raised her body over my cock as it stood straight up, reached out to
hold my hands, and began to slowly impale her pussy onto my shaft, inch by inch, a little at a time.
Wow was she tight! And, Lilly’s cock was as hard as mine, and she dripped her pre-cum on my
stomach.
What an amazing sight it was to watch Lilly impale herself on my cock until her cock and balls were
resting on my stomach. I can still picture it in slow motion. Fuck was that hot!
Once I was completely inside of her, she moved her sexy hips up and down, and up and down,
making sure the head of my cock stayed in her. I was in awe as I watched my cock appear and
disappear into Lilly’s love canal, over and over, and the sight of her huge cock and big tits towering
over me was so hot!
Fuck, I was totally mesmerized watching her cock and tits move around as she rode my cock; it was
a sight and feeling that I had never experienced before. This was by far the hottest sex I’d ever had. “I
so wanted to cum inside of Lilly!”
As Lilly was riding me, I looked in her eyes, and then she knew I was about to plant my seed in her.
Lilly gracefully moved on to her back, while keeping my cock deep inside of her.
I was now on top of Lilly, and her legs were high in the air, eventually coming to rest on top of my
shoulders. I knew she wanted me to cum inside of her, so I pumped, in and out, and in and out, all the
time feeling her hard cock sandwiched between our stomachs. What an amazing feeling that was!
Lilly looked at me and said, “Give it to me Alex; give me all you’ve got. Pump my pussy full, pump
me, pump me, please…”
Hearing her plea I yelled, “Lilly, I’m cumming, take it, take it all,” and I pumped and pumped, and shot
ropes of cum into her pussy.
Once I exploded Lilly also exploded, and the feeling of her hard cock pulsating and shooting cum
between us was unbelievably hot!
I collapsed next to her, and we cuddled up for a while.
About a half hour later, I suggested we take a shower, and again asked Lilly to spend the night.
“Alex, I may never leave,” she said.
When I woke up Sunday morning, Lilly was not in bed. I got up, took a quick leak, and went looking
for her. I was really hoping she didn’t leave. I was now calling out her name, and then I heard her say,
“Alex, I’m in the kitchen. I made us coffee.”
Yep, there she was. Lilly had made a pot of coffee and was sitting at the table. I gave her a kiss, and
got a cup. We sat and chatted for a bit, and I told her how much I enjoyed last night. I was crazy
about her, and asked Lilly to spend the rest of the day with me.
I made us breakfast, and then we ate, and talked. We had our robes on, untied. I looked at Lilly, and
the way the sun shined on her open robe, it accentuated her perfect tits and huge cock. As far as I
was concerned, she was neither a man nor a woman, she was mine.
When we finished eating, Lilly and I went into the living room. We sat on the sofa and began to hug
and kiss, and then Lilly stood up, reached for my hand, and had me follow her to the bedroom.
While we were walking she took off her robe. What a fantastic ass she had!
When I got in bed, Lilly got on top of me. We kissed a little, and Lilly went right for my cock. She had
me hard in seconds, stroking it and sucking it, and then she deep-throated me. Fuck. What a hot
lover she was.
For the next twenty-minutes we played. I sucked her, she sucked me, I played with her incredible tits,
and needless to say our cocks were now hard and oozing with pre-cum. Then, in a flash, she moved
her body down. I thought she was going to suck me again, but instead, she put my legs on her
shoulder and lifted them up.
Lilly’s hard cock was now pointed directly at my ass-hole. Game-changer!
“Do I draw the line here, or was I willing to let Lilly fuck my virgin ass?”
Suddenly, I wanted to feel what it’s like to be fucked by Lilly’s one-eyed monster, to feel the
sensation of having her cock move back and forth inside of me, in and out, fast and slow, over and
over and over, and then have it spit gobs of cum in my ass.
“Fuck me Lilly,” I said.
Without Lilly even touching her rock hard cock, she prodding and lubing my hole with her pre-cum. I
have to say, just feeling her cock near my hole almost made me cum. Then, her cock was in, not far,
but it was in. Holy fuck what a feeling!
For the next few minutes she prodded my ass with her love muscle, in and out, inch-by-inch, and a
little deeper each time. Once she was all the way inside me, Lilly looked at me and mouthed, “Alex, I
Love You!”
Hearing that, I told Lilly I loved her too, as she pumped my ass with the look of love in her eyes, and
then seeded my ass with her love.
Turns out that Lilly and I hit it off and fell madly in love with each other. I rented out my house and
moved in with her, and retired at the ripe young age of thirty. Lilly insisted.
Funny, Lilly only lived two blocks away from me, and was a very rich girl. Her Grandparents were
very wealthy, and set up a trust fund for her that would last the average person four lifetimes. They
knew Lilly was different, but she was also their favorite grandchild. I could see why.
One night right after we made passionate love, and we always made passionate love, Lilly
announced she was planning on completing her transformation to become a woman.
I sat up, looked at her and said, “Lilly, what are you talking about?”
“I was thinking about having my cock cut off, and have them make me a pussy.”
“Don’t you dare,” I said. “I love your cock!”
Lilly never brought up that idea again.
One more thing, Renee always reserves the two seats at the end of the ‘Don’t Ask’ bar for us every
Saturday night. Yep, Renee is Lilly’s mom.
Thisfictional story was written by Alex Foremen and shall not be copied or re-produced.

By AlexForemen

2 thoughts on “Didnt ask didnt tell – Shemale story

Leave a Reply

Your email address will not be published.