This story is dedicated to a guy named Jeff, who practically begged me to write it! Sensing he is a closet pussyboi I insisted he put on a pair of panties and admit what a sissy he is. Of course he did this immediately. I can sense a pussybli a mile away! He has been wearing a pair of his sister's silky panties from her undie drwaer and forbidden from stroking himself until this story appears. Spurt well and remember to lick your hand clean, my darling!
I'm a horny eighteen-year-old guy and I really dig pussy! I like the ladies and the ladies like me! What's not to like? I'm young and in great shape, and my olive skin and Mediterranean good looks drive the chicks wild! I've been told I should be a model because of my deep brown eyes, fine features and lush eyelashes. I know how to work it...the ladies can't resist my killer smile and this sweet little pout that I use to my advantage....and they can't get enough of my seven inches of pussy pleasing meat!
So I get a lot of action, big deal! It has all gotten a little boring, and I've started to cruise the internet for something a little more exciting, a little different.
I came across this hot profile for a woman on the internet and we've been chatting and flirting a bit. Turns out her name is Katherine and she's a bit older than me at thirty. I don't mind older chicks - they usually have more experience and this one has a killer photo - nice round tits, not too big, and shapely ass that is really fuckable! She has long red hair and she's quite the flirt!
Our conversations started out innocent enough - the usual get to know you bullshit. Turns out this chick lives about an hour away from me, and she's quite the player! She has been teasing me about being pretty and how she wants me to be her pet. Her pet? That's a first! While I never thought about a chick taking the lead in a relationship I have to admit it's making my cock hard!
I figure, what the hell? I'll hook up with her and get some action and see what she's all about. She was really excited that I accepted her invitation to hook up at her place tonight, and was very specific on what to wear, which kind of turned me on! She told me to wear a pair of super tight jeans, no underwear, a tight T-shirt, no socks and sneakers.
So I'm getting close to her place now, in a nice neighborhood, and I'm throwing a decent size bone down the leg of my tight jeans. That ought to give her an eyeful when she opens the door!
I parked my car in the drive of her tudor style home, and rang the bell. Nothing. I rang it again, feeling kind of stupid and wondering if I was getting stood up, and finally the door opened.
Katherine opened the door part way and invited me inside. She was being discreet because she was wearing this outfit that was just smoking!
Her tits weren't huge, but they looked absolutely perfect bubbling out of the black sequined bra she wore. She also had on a black garter belt with black stockings, and a pair of black panties that matched the bra. This outfit was covered - just barely - with a black lace robe that feel almost to the floor. She was a knockout!
Katherine invited me in and took me by the hand, leading me to the living room.
"Luciano you look absolutely yummy! Be a dear and poor us each some wine won't you? It's there on the minibar."
I poured us each a glass and handed her the flute filled with white wine. She accepted it and said, "You may sit next to me, right here!"
We sat and enjoyed the wine, sharing a bit of small talk. We couldn't keep our eyes off each other.
"Luciano, do you like what you see?"
"Oh yes!"
"Yes, what?"
"It would be best if you called me Mistress! And now I want you to remove your clothing for me!"
This was too much! I wanted something different, so I played along.
"Yes, Mistress!"
I stood before her and started to strip. I could swear her mouth was watering as I removed my T-shirt and she saw my muscled chest. I removed my sneakers and then lowered my jeans. My boner bounced out of my jeans and as I stood naked before her it was hard as a rock, and stiffly arched before me. I used my seductive smile on her and looked into her eyes. I knew I was driving this chick crazy!
"Well aren't you the pretty one! And your cock is so sweet! I've seen bigger you know, as I'm sure you have. I'm sure it's quite adequate for most women...and men, perhaps?"
I felt my dick deflate a little. "No way, I'm no fag!"
Katherine laughed and I saw her start to finger herself through her black panties.
"You're not very hairy, are you, Luciano? Your skin is quite beautiful...almost feminine I would say!"
I didn't know what to say. My once hard dick was now at half-mast and fading fast.
"Don't worry, darling...I like femmy guys! Now come with me so we can have some fun!"
I let the femmy comment slide; I didn't care what she said as long as I got some action. She led me upstairs to her bedroom by the hand. The bedroom was large and extremely feminine, all done up in pinks and floral prints. There was lingerie everywhere!
When we entered she pulled me close to her and kissed me, forcing her tongue inside my mouth. I sighed and let her do it. This was one aggressive chick! As she kissed me I realized that she was a good four or five inches taller than me, and she ground her beautiful breasts into me as she felt my body. She caressed my back, and then started to stroke my ass. The ladies have told me I have a great ass, and Katherine was digging it as well!
I was lost in her kiss, accepting her tongue pistoning in and out of my mouth, my head back in pleasure when I felt her push a finger into my asshole. Whew, what a feeling!
I squirmed as she dug deeper, but she was holding me so tight I couldn't escape. When she pushed a second finger inside me I tried to break free of her kiss and her embrace but no dice. She was in control! I felt my cock getting hard as she poked at me, and I just accepted what she was doing.
She finally pulled away from me and I was dizzy! She sat on the edge of her bed, her legs spread. and looked deep into my eyes.
"Do you want this body, Luciano?
"Oh yeah!"
"The only way you'll get what you want is to do everything I say...understand?"
"Yes"
'That's "Yes Mistress. You will only address me as Mistress and accept that I am in charge, do you understand and accept?"
"Yes, Mistress"
"Very well. Come with me into the bathroom."
I followed this wild chick into the bathroom. I'd play her game, this was too much!
She stood me before the mirror and told me to remove my pubic hair.
"Shave it off first with the edger on this electric razor, then use shaving cream and this disposable razor. I detest body hair on myself or my lovers!"
Why not? It would grow back. I shaved it off as she watched me do it and coached me. My dick was loving it and it was rock hard by the time we were finished.
"Shave off the few hairs on your chest, and your legs too, sweetie!"
I did it. It was like I was under her spell.
"What a good little boy! You look even younger and more precious without hair! Now come with me and sit down before my makeup table."
Makeup? What the fuck?
"Now wait a minute Katherine, this is going to far!"
She pulled me over to the seat before her dressing table and quickly pulled me over her lap. I was shocked as she took a golden handled hairbrush from the dressing table and started to spank me with it.
"Hey, that hurts! Ow, cut it out!"
"How dare you disobey me and not refer to me as Mistress! I'm going to teach you a lesson!"
"Little boys do as they're told in this house! Do you understand, you hairless little sissy?"
I didn't respond right away. I was trying to figure out how to get out of this predicament but to be honest she was stronger than me and with each slap of that hairbrush on my round bottom my dick jumped and got harder and harder, until it was leaking.
"I asked you a question, you little shit! Are you going to obey me?"
After about the twentieth smack on my sore red bottom I surrendered.
"Alright Mistress, I accept! Please stop, please!!!"
With that she pushed me off her lap onto the floor.
"You ungrateful little sissy, you left pecker tracks on my stockings! Lick them clean!"
With tears in my eyes I leaned close and licked her stockinged thighs, finding the slimy tracks of precum I had left behind during my spanking. I found the taste not that unpleasant, but had to admit this was something I would have never tasted on my own.
Mistress moaned and spread her legs even further apart. I could tell she was sopping wet and I could smell her pussy, which was driving me mad!
"Now get up off the floor and kneel before me!"
I did as I was told, my dick bobbing before me. Mistress took her hand and gave it a good slap!
"Keep that annoying thing out of the way!"
My cock deflated a bit and I wondered what was next in store for me. I didn't have to wait long as she opened a jar of liquid makeup and started to apply it all over my face.
"Yes, this is a good hue for your skin tone I think! Ooh, so pretty! Now for a little blush to put some color in your cheeks!"
With tears in my eyes I let her hold my face and do what she wanted, the fat that she had taken control of me was strangely erotic, and I even found her calling me a sissy to be kind of exciting. I figured I'd have a chance to show her how much of a sissy I was when I got my cock into her pussy and started to make her scream for more!
"Close your eyes, sissy! A pretty bronze color for you eyelids to complement your beautiful skin!"
After she finished she told me to open my eyes and I saw her take a big powder puff and as she told me to close them again she dusted my face with a sweet smelling powder.
"Now make a kissing face so I can apply some lipstick!"
I did as she told me, and my lips were quickly coated with a wine colored lipstick. She held the tube up before my nose to make me smell the lipstick and it was very sensual!"
"Now stay there on your knees where you belong while I get something!"
Mistress returned with a shoulder length auburn colored wig, which she fit on my head. I gulped, and wondered as she combed it out on my head what I looked like. I must look ridiculous!
"Stand, sissy!"
I stood up but from the way she positioned me I could not see into the mirror at the table. She fastened a pink garter belt around my waist and then got down on her knees to roll some sheer stockings up my legs. Down on her knees like that my cock was in her face and I thought she might kiss it or suck it, but she ignored it, other than giving it another slap!
The stockings were soon fastened and I realized how sensual they felt on my now smooth legs. She made me slip into a pair of white high heels that felt incredibly awkward.
As I tried to stand in them she had me lift my arms and she slipped an incredibly feminine nightie over my head. It was pink and sheer, with little rosebuds all over it. When it was pulled down into place I could feel the white lace around my shoulders and my cock poked at the sensual fabric. I felt silly, but so alive!
Mistress then walked me over to the mirror, slowly so I would not trip in my heels. The vision I saw took my breath away! The makeup she had applied looked perfect, and the coloring suited my face. The wig was actually very near to my own hair color and fell softly on my shoulders.
If it weren't for the lack of tits and the fact that my boner was poking at the front of the nightie, which teased it mercilessly, I would look like a very pretty girl. I could see through the sheer fabric of the nightie my lack of any pubic hair and it was rather exciting. As I moved and posed before the mirror the nightie rubbed against my nipples and I swear they were like little hard ons themselves.
As I stood there admiring how I looked Mistress had returned to the edge of the bed, where she sat' her legs spread and her panties removed.
"Stop admiring yourself, you little whore, and get over here on your knees where you belong!"
I carefully walked over before her, dropped to my knees and stood wide-eyed at the magnificence that was her pussy. It was shaved, and pink...and HOT!
"Lick it, sissy!"
I leaned over with lust and licked between her legs, long slurping licks and I made love to her. I sucked and nibbled on her clit and she leaned her head back to moan. She reached down and pinched my nipples so hard through the nightie I thought I would pass out!
"Oh yes, what a good pussy eater!"
I continued to work on her hot cunt, and soon she was writhing and wrapping her legs around my face, pulling it closer and deeper into her. I felt her shake and groan and she came. She came yet again and I was so happy that I pleased her!
"I suppose you want to fuck now, don't you sissy?
"Yes, Mistress!"
My cock was bone hard and leaking all over the pretty nightie.
"Then close your eyes and wait until I'm ready."
I stood there with my aching boner as I heard her moving about the room, anticipating putting my cock into that sloppy pussy of hers and fucking her senseless!
The sexual tension in the air was thick as I felt her push aside my hair and kiss my neck from the back. She grabbed my cock and started stroking it through the sensuous material of the nightie.
"Are you ready slave, ready to fuck?"
"Oh yes, Mistress!"
"Good, so am I!"
I jumped when I felt the slick dildo push into my hole! With a few quick shoves she must have buried that big thing four or five inches deep inside my ass! My cock quickly shrunk from the shock and she continued to hold it tight for leverage as she fucked further into my hole.
Mistress then shoved me toward the bed, and in the wobbly heels I lost my balance and fell down on it face first. She stayed with me, and the dildo was still inside me a bit.
I squirmed against her but was helpless as she pushed it in, all the way and I moaned!
"You did say you wanted to fuck, didn't you slave?"
"Yes Mistress, but I wanted to fuck you!"
"Don't be silly! I only let real men fuck me. Smooth obedient sissies like you are the ones getting fucked in this house! Now spread your legs wider and open your hole up for me!"
I moaned as the thrust turned from pain to pleasure. She was relentless, and her dildo fucked me relentlessly. She alternated between deep in and out strokes and short jabs. I was soon shaking with lust and I could feel my cock again hard as a rock beneath me. As she thrust in and out of me I felt my cock shoot - great gobs of cum spewed out underneath me without it even being touched.
Ignoring my orgasm Mistress continued fucking me until I was shaking and almost incoherent. I would never be the same after this night. I knew I could never again be satisfied with standard vanilla sex with a woman. Mistress had created a new sexual being, a submissive obedient sissy named Luciano...or should I say Luciana?