Ladyboy sex story #1 with guy

It was the worst day in my life. My girlfriend Ally and I had been
quarreling and rowing for several weeks, we were on the verge of
breaking up. I just wanted her to be happy. I lived my life for her. I
guess I stood no chance to make her smile at me again. We broke up. Ally
said everything was changing and her feelings for me had changed too.
She didn’t love me anymore.
I couldn’t get it. I’d been worshipping her for five years. We’d been
together since I was 18. We were meant for each other. She was my first
girl. I was dreaming of our love to last forever. But… Nothing lasts
forever. It wasn’t fair! I was in despair. I could have never thought
such things could happen to me.
I wasn’t really into drinking. I’d been drinking socially, just a glass
of wine or a bottle of beer. That night was an exception. I wanted to
get wasted. I wanted to lose the reality maybe just for a while. Steve,
my best friend, knew about Ally, so it was he who offered me to go to a
pub and drink some. I agreed, of course. It was 10.30pm. We decided to
drop in some pub.
Neither Steve nor I had ever been in that part of the city before, so it
was sort of a labyrinthine rout for us.
-Hey man, we’re lost! – I told Steve.
-Bullshit. We’re not. We’re just looking for a pub, that’s all, man.
I just couldn’t believe that. Hardly had I decided to go somewhere to
get drunk as we got lost in that damn city!
-Here it is! – Steve exclaimed.
He pointed at the sigh that read “Trance”. He looked at me inquiringly.
It was more like a dance club than a pub. I told Steve about it.
-I don’t know if we should go there at all…. – I added.
-C’mon, there’re bars in clubs too. So, what’s the hell is the
difference? You wanna get drunk, so you shouldn’t care where to do it!
Besides, there must be dozens of hot chicks in there. Maybe we’ll get
some to please us, you know! I’m sure we’ll find girls who’ll be ready
to get some nasty….
I thought about Ally again. It hurt me to think it was all over. Well,
who knows what might happen when you get a bit drunk, I thought.
Anyways, it wasn’t that bad if I fucked some babe. I would be revenged
on her. We parked the car and headed for the club. When I went out of
the car I realized I was damn right about the place. It was a real dance
We got in. Man, the place was…. Loud music, dancing people, hilarious
atmosphere… There were many women there. Many single women. They were
dancing with other girls.
-OK, let’s empty the bar! – I told Steve, taking him by the shoulders. –
It’s high time we forgot about our sorrowful life and about that bitch Ally.
He gave me a slap on the back, and then on my butt. It was just a joke,
don’t worry. There were lots of people in the bar, but we managed to
find two empty seats.
horny ladyboy with dildo in his ass
Sexy ladyboy with dildo in his ass
Hey, I love this place, and I’m thinking about spending the whole night
here, – I said joyfully.
-Just look at the chicks here, – Steve noted, looking around, – it’s
great you’re single again. I bet it’s gonna be a great night tonight!
That made me remember about Ally again. She was so damn beautiful! She
always looked very sexy, and her lingerie was always so arousing, and it
didn’t even matter if we were going to get laid or not. But when we were
having sex, it was really wild and passionate. It was real animal sex.
All her stockings, g-strings, mini skirts, high heels were making me go
crazy. Ally knew how to make me hot. When I didn’t feel like having sex
she put on her stockings, high heels, a tiny skirt, and I became her
love slave.
Steve helped me get back to reality. He punched me in my ribs. I looked
at him first and then at the bartender.
-What will you drink, hon? – She asked me.
She looked like wow. She was a tall girl with emerald green eyes that
seemed to be looking through me. She was very tall, more than 6 feet, I
guess. She was wearing a short dress, it was bright black, it was
glittering. It was made of some fabric that really resembled leather. I
thought she was that tall cuz of high heels she was wearing.
-I don’t know. The strongest thing you have. And make it double. The
same to my friend. – I said.
-Well, sweetie I have something special for you. You’re gonna like it.
It’s my special recipe.
She mixed some strange looking drinks that looked like fruit liqueurs.
In a moment I was holding a glass with scarlet liquid in my hand.
-What’s the shit? – Steve said annoyingly.
-Who the fuck cares. Let’s drink.
We gulped that cocktail. It was burning like hell at first, but then it
felt really good.
-WOW, – was all I could say that moment.
My head was very heavy. People and things blurred in my eyes. People and
things had a funny shape. I screwed up my eyes, hoping it would help.
Man, I felt so nice after that cocktail. I looked at Steve. He was
smiling. His eyes were shining.
-I guess it’ll be my favorite one. – He said.
-Yeah, mine too. – I nodded, thinking whether I was looking as stupid as
he was.
We both turned to the bartender. She was looking really pleased.
-So, you like my cocktail, guys?
We both nodded.
-Would like me to repeat it?
How could we say no?!
-Looks like you guys are drunk and can do whatever I want… – She said,
giving us glasses.
Seemed she made them beforehand, knowing we would ask more.
When we were through with the drink, the girl told us to follow her. We
were following her thinking us to be the happiest guys in the world. We
were two happy lucky guys. We weren’t sure what exactly we were lucky
about. The stupid music muffled when we went into the back door. It was
a room, but it was larger than a room. There were mirrors everywhere,
and there were couches by the walls. I saw a hall and other doors. A
woman was lying on one of the couches. The bartender came up to her,
gave her a kiss and whispered something in her ear.
The woman liked Steve. She took him to the hall and opened one of the
side doors. They went in there. Everything happened so fast! I was alone
with a cute bartender. Let’s go to another room to talk in silence, – She suggested, winking
at me playfully.
She was right; the music was too loud there. But I liked the rhythm, I
was shifting from side to side, following it, I was smiling like a real
jerk. What was going on with me? I felt like losing some part of my ego,
following a beautiful bartender into the room.
The girl was much taller than me. I tried to open my eyes wide to see
her better, but my eyelids were too heavy to do it.
-Oh, my mistress, – I was ready to get on my knees in front of that goddess.
She turned to me to answer:
-Yes, I’m your mistress and you belong to me.
She kissed me on the cheek, smiling. I wanted to kiss her lips but she
turned away from my face. When we came into a room, she told me to wait
for her there. She said she would turn on the appropriate music. It was
pretty empty in the room. Empty white walls and a purple carpet on the
floor. A chair was standing in the middle of the room. Man! It was my
first night of a single man and I almost managed to fuck a marvelous
chick! Good for me! I was hot, so I took of my shirt. I let her take
care of the rest of my clothes. And then I got that I didn’t even know
her name. But… on the other hand, I wanted to fuck her and I didn’t have
to know her name to do it.
Well, I was still waiting, but she didn’t show up. I felt uneasy in that
stupid room. Suddenly I heard the music. First it was muffled, then it
got louder and louder. It was made by keyboard instruments. It was like
a choir of angels compared with that music in the club. I felt so
peaceful. But there was something wrong about the music anyway. I got
it. It was accompanied by some strange whispering. It seemed to be the
bartender’s voice, but I couldn’t make out even a single word. I was
enchanted by the music and by the whisper. It was whisper, and whisper
all around me. I was very embarrassed, but couldn’t help swaying from
side to side in the tempo. I was smiling (I couldn’t do anything about
it either!). I was dancing to that fascinating music. I was focused on
the music and on the whisper. I undid my belt and threw it on the floor
as if being a strip tease dancer. I was swaying my butt taking my jeans
off. I threw them on the floor too. Then I took off my pants. I was
totally naked.
Everything was so strange. I looked at the bed standing by the wall. I
hadn’t noticed it before. It was just a bed. But now I saw woman’s
lingerie lying on it.
-Like the most beautiful girl in the world. – I heard the whisper.
-Ally, – I said monotonously.
-You’re Ally now.
-I’m Ally.
-You’re absolutely naked Ally. Where are your clothes?
Seemed the voice was coming from deep in my brains. It was like it was
me asking those questions.
-My clothes are on the bed.
I took satin black lacy panties and put them on. When the fabric touched
my dick it got rocky hard in no time. I put on the belt then. Garters
were tickling my hips when walking. It was stockings time. I took one of
them. It was made of nylon, it wasn’t transparent, but there were laces
on the top of it. My original and true ego was fighting with the music
and the whisper. I started puling on the stockings and then sopped.
I’m a man! I thought. Don’t touch the stockings! You’re a man not a
girl! Don’t do that! Girls and gays wear stockings!
The nylon touched my toes.
I’m a MAN!
The stocking got up to the middle of my shank. My dick was rocky hard.
The music was louder now. I burst in tears when I realized that the
music and the whisper killed the man in me.
Am I a man? I’m a GIRL.
I put on the stockings. My huge cock was ripping through them. I was crying.
I’m a G-I-R-L!
-I’m Ally.
-Do you like your outfit, Ally?
-I do.
-You won’t wear man’s clothes any more. Ally, what do you think about
man’s clothes?
-I can’t stand them. I want to wear girl’s things.
-You’re such a nice girl, Ally.
I smiled at my invisible interlocutor. I liked his praise. I fastened
the stockings to the belt. I fully realized what I was doing, but at the
same time I couldn’t stop doing that. I guess it was the cocktail. My
ego’d gone.
When I was through with the stockings I took a black satin bra. When I
put it on, it seemed like I had boobs!
-I want my mistress to see what a beautiful girl is waiting for her. – I
said, taking a short black dress from the bed.
I put it on the floor. Then I took it by the shoulder straps and put it
on. Those were unforgettable sensations. The dress fit me like a glove,
and I really felt like a girl. I remembered how much I used to enjoy
seeing Ally dressing up after our wild sex. I looked down and saw a huge
bulge between my legs. I had to do something about it. I raised my dress
and stuck my hand in the panties. It looked much better soon. I set my
dress right. It was so short! One could see laces of my stockings. I
felt so good wearing it, I’d never felt so free before. Then I saw a box under the bed. I opened it and saw a wig, gel, rouge,
an eye shadow kit and a mirror in there. I started with eye shadows. I
wasn’t sure what exactly I had to do, but the whisper advised me what to
do. I never stopped swaying my butt in the tempo of the fascinating
music when putting on the makeup. I looked in the mirror, it seemed
there was too much make up on my face, and too much of eyeliner. Well,
who cared, anyway! Rouge now. I sucked in my cheeks and put rouge on my
cheek bones. I took the lipstick then. It was of bright red color, the
color of hookers. I couldn’t figure out what the gel was for.
I took the wig out of the box. It was black. The hair was shortly cut. I
put it like a hat. Then I looked in the mirror and set it right for it
to cover my own hair. “I must obey to my mistress,” I thought sitting on
the chair in the middle of the room. The voice told me to cross my legs.
I didn’t wanna do it. My male ego was trying to overcome my female sense
once again.
Don’t do it! That’s the way girls sit! It was telling me.
-I’m a girl. I’m Ally. – I said loudly.
The voice praised me again. OK, my right leg goes over the left one.
Right? OK. It was an incredible sensation when my nylon covered legs touched each other. I was sitting on my rocky hard dick. It was a bit painful, but I sort of liked the feeling too. -Why are you so thirsty? – The voice asked me then. -I don’t know. But I’m really thirsty. – I licked my lips. Suddenly the music stopped! The door flung open. A woman came into the room. Then the door slapped shut. My guest looked like a teen. Her light hair was cut short. She had the same hairdo as I did. She was wearing a tight white top. I could see her checkered mini short skirt, and white stockings. The girl was on the verge of break down. -I’m thirsty! I’m dying! Help me! – Tears were flowing down her face. I was damn thirsty myself. I wanted to console the girl, so I hugged her close, pressing her tight to my body. I felt much better without the music, at least it seemed to me so. I knew I had to find water to give it to the girl. Shy desperately needed my help. I just had to do it. I asked her name. -Steve, – she said. STEVE????!!!!! -What? – I cried out, pushing her away. – Steve? Why are wearing these things? What the fuck is going on… -Who are you anyway? – She asked me in return. – I don’t know you. -What do you mean you don’t know me? I’m your friend! -Wait, if you really are, then why are you dressed up like a real gay?! I didn’t know what to say. I looked down. The music was turned on again. I looked up at the girl, she was crying. -What now? – I was getting annoyed. – C’mon, don’t cry. Tell me your real name. -Sue, -She said, sobbing. – I’m really thirsty. Will you help me? -I’m Ally, and I’m thirsty too. We started dancing to the music. My hands got under her skirt, I was caressing her buttocks under her satin panties. My head felt dizzy, I kissed her. Her lips were so sweet! I finally realized how I could help her. We both got on our knees, then I lay on my right side, and she lay on her left one. My face was right by her hips. I was rubbing my face against her nylon covered hips. I raised her skirt and saw her white panties with a huge bulge in the front. I set her dick free. The music made me feel even thirstier. felt Sue’s lips on my dickhead. I did the same. I liked the taste of her lubrication. I was vigorously licking her cock. Sue took my shaft in her mouth, sucking it like a lolly. I was doing the same with her. The pecker was getting deeper and deeper in my mouth. “I like it,” I thought, fondling her stem. A huge gob of cum filled my mouth. I liked it, it was so hot and thick. I came too. Sue was trying to milk me to the last drop. I was sucking her too. I don’t know for how long it all lasted, but suddenly the music stopped again. The door flung open. It was my mistress! My bartender! She took Sue by the hair and kicked her out of the room. Then she turned to me. -The door isn’t locked. You can go if you want. I couldn’t go. -OH, my mistress, I wanna please you… – I fell on my knees, crying, holding her knees tight. She kicked me aside and slapped me across the face.
Fucking gay. You wanna be a girl. OK, I’ll take care of you then. She took me by the hands and tossed me to the bed. Then she raised my dress and pulled off my panties. -You loved sucking dicks, but I’m gonna own you now. – She slapped me across my butt. -Yes, mistress, own my butt. The bartender raised her leather skirt. Her panties were swelled. She pulled them down a bit, and I saw a huge cock. I couldn’t even imagine that my mistress was a man! The stem was 9 inches long and 3 inches thick. I gave up. I badly wanted to feel that huge shaft in my asshole. I was begging her to fuck me. -Take me mistress! Please. She took that gel from the box and lubricated her gorgeous dick with it. I felt the dickhead touch my buttock. It made me sigh. -Before I fuck you, nobody, I want you to know something. The drug added to the cocktail doesn’t affect you anymore. So. It’s your own will. It was your own will when you were sucking Sue. You were doing what you wanted to. Sue wanted it too, that’s why YOU DID WHAT YOU DID! -AHhhh, – I cried out when she entered my hole. I couldn’t stand the pain, I was crying. The bartender never stopped ramming into me. My hole was too small for such a huge knob. Tears were flowing down my cheeks, I was moaning quietly like a real slut. Oh! She entered even deeper. The pain became duller. Another inch of her hot flesh got in my virgin butt. When her dick was all in my butt, she started drilling me. Back and forth. She was thrusting in my flesh with all her might. I’d never felt so good before. I was licking my lip covered lips, smiling. My mistress was wildly screwing me. Ally must have felt the same when having sex with me, I thought suddenly. -I’m Ally! – I kept on crying. The bartender was smiling, never stopping owning my butt. I wanted the drill to last forever. But all of a sudden my mistress started trembling. Her hot semen filled my rectum. When she took her flaccid dick out of my hole, thick liquid started flowing down my legs. I felt a sudden pang in my ass. -I love my mistress, – I whispered before falling asleep. It was early morning when I woke up. Steve and I were sleeping by the club. We were on the street. We were wearing our ordinary clothes. I woke him up and we headed for the car.