Dressed in all the frillies a boy could imagine, and with a tummy full of cum, I slowly descended the staircase to the sound of laughter and chatter below. Aunt Anna was entertaining someone she wanted me to meet – Darla Dicklet, who I was told is a performer at her nightclub.
I tried to walk very carefully in the short heels that encased my stocking clad feet. It was such a rush to be dressed like this! Having been able to steal away moments dressed in this or that – panties and bra, or a nightie, used to really turn me on, but nothing matched the sensation of being dressed as a young lady from head to toe! The silk panties rubbing against my cock made it super hard, but it was hidden by the ruffles in my petticoat.
I felt pretty.
Sophie followed behind me dutifully as we reached the first floor and went through the entry hall into the doorway of the living room where Auntie and Darla awaited us. I was a bit nervous and I felt Sophie give me a little push in the back of my pretty dress to encourage me to enter the room. There, on the couch, my Aunt sat wearing a sheer purple blouse with the prettiest little adornments of silver colored embroidered flowers. The blouse was exquisite, and the nipples of her lush breasts could be easily discerned. She also wore a lovely gray skirt, along with black stockings and heels.
Darla looked up at me the minute I entered the room and immediately looked over her bejeweled glasses to inspect every detail of my appearance. She was quite an exotic looking woman, with flaming red hair all done up, with delicate ringlets falling on either side of her face. She was heavily made up, with the puffiest lips I have ever seen – plump and shiny red. She was wearing what could only be described as a polyester cat suit of a shimmery blue green fabric. You could see the outline of her breasts, and her nipples through the material. There was a large silver zipper that ran right up from her crotch to the neckline, which was very tight and looked a bit uncomfortable. I could see she was wearing some very exciting electric blue leather boots.
"Well well, what have we here? Who is this sweet young morsel?"
"Darla, this is my niece Jamie from America...you remember I told you she was coming to live with me!"
I nervously went closer to them and lowered my head in embarrassment. How humiliating to be dressed like this in front of strangers!
"How delicious! Don't be so shy, my dear...look up and be proud...you're quite pretty!"
"Yes Maam"
I looked up into Darla's face and her eyes seemed to look deep into my soul. She knew...she had to... I was really a boy under all this girly makeup and these frilly clothes!
My Aunt spoke up, interrupting the connection between us.
"Darla as you can see with your wonderfully trained eye, this lovely young thing is actually a sissy boy underneath. You see my sister felt compelled to send her son to me for his personality disorder. He was arrested in America you see ...for cocksucking! I do believe he sucked off every male that lived in his county!"
I gasped at what she said!
"Aunt, that's not true! I was NOT arrested...and I certainly didn't suck EVERY cock in my county!"
Darla just laughed at my defensive position and ordered me to stand before her. I slowly walked over in my heels and lowered my head in shame and embarrassment. The smell of her perfume was overwhelming!
"So you like men do you? So do I! Tell me, Jamie how do you feel when you have a cock in your mouth?"
"Well, Miss Darla, I feel complete somehow...like I'm doing what I was meant to do, bringing a man pleasure. It excites me so, and makes me feel alive!"
"I see. I know how you feel Jamie...but tell me...how do you feel about dressing up? Do you like this, being girly?"
My Aunt leaned over to carefully watch my response to that question.
"Oh, it's all right I guess."
"Lift your skirt and your petticoats, sissy!"
A hard cock does not lie! My peeny was straining against the smooth seductive silk of the pretty panties. I had been hard every moment since I put them on, despite the fact that Sophie had drained me with her mouth so nicely not that long ago!
My aunt added to my humiliation as Darla looked hungrily at my silken protuberance.
"Darla I must tell you that this is certainly not the first time my little nephew here...or should I say "niece" has been in feminine things! When he was little and I would baby-sit him I always dressed him in little dresses and put bows in his hair, and before long he was playing dress-up with his mummy's things...much to her dismay! He was always rather undeveloped as a male and never really participated in sports I'm afraid. Jamie always had an oral fixation – loving to suck on a breast or his fingers, His little peeny just never seemed to grow – it remained small and sweet. His mother admonished me when I gave him a Barbie and ken doll on his sixth birthday, but I made sure there were always pretty little clothes for him to dress Barbie in, of course I had to throw in some "ken" outfits as well, he was just an unnecessary addition, really just an accessory for her of course...a dickless male for her to dominate!"
Both ladies laughed at that comment and she continued.
"Soon he was rifling through her panties and things, playing dress up, wanting to be like his mommy, and when he began to spurt his little sissy goo he was leaving telltale signs all over my poor sister's underwear! She was horrified, and confided in me. It was all I could do to suppress my laughter and delight in what I knew would come to pass. Small dicked, fatherless boys are already predisposed to a life of submission and domination, aren't they my dear? And Jamie here has so much potential! That is why she was sent to me, her mother thinks I am trying to work her out of this phase, when in fact I am doing the exact opposite!"
Darla laughed uproariously, almost in a masculine tone, and she put her hand on my little lump!
"Jamie sweetie, don't be embarrassed! You are a unique and lovely creature, and I can tell from the way your sissyclit is jerking around and leaking that you enjoy all of this! My, it's really quite lovely, isn't it?"
I gasped as Darla leaned in close and began to lick the outline of my cock through my panties. The feeling of wet silk was fantastic! With both her hands she pulled down my panties just low enough to expose my cock and balls, and then she leaned in further to take me into her mouth!
I thought Sophie was talented, but she could not compare to the talented mouth of Darla Dicklet! I looked over to see my Aunt, her legs spread and her fingers in her moist cunt.
I can't describe the wonderful feelings that went through me as Darla expertly sucked me. Her mouth was incredible! She had my entire length in her mouth, yet the whole while her tongue kept circling and licking the head, savoring my juices. She stroked my balls with her long red fingernails and I sensed myself getting ready to cum! The whole experience, being dressed in such a pretty and frilly manner, delicately holding up my skirt and petticoat with both hands and having the mouth of a beautiful and talented cocksucker wrapped around my pole was just too much, and with a squeal I began to cum!
Darla began to moan, and swallowed every drop! I became weak and a bit dizzy, and when she finished draining me she pulled my panties back up over my spent cock and gave me a smile.
"Annie darling, I hope you don't mind, but I just had to have a taste of this lovely's sissy goo!"
"Not at all, Darla. I understand your need for cum, even if it's not from a real man!"
As I lowered my skirts back into place Darla stood before me and leaned over to kiss me. I could taste my cum on her lips, and I really like the taste of my lipstick on hers! I heard a snapping of fingers and looked over to see Sophie on her knees crawling between my Aunt's legs, and burying her submissive face into my Aunt's pussy. Aunt Anna continued to watch Darla and I intently, obviously quite aroused.
As Darla kissed me she took my hand in hers and began to lower the zipper on her amazing jumpsuit! I was so excited as it lowered all the way down between her legs. I knew her luscious breasts were fully displayed, but my eyes were closed, still in a passionate kiss! When the zipper got low enough I gasped as I felt a rigid cock pop out!
Darla was a she male! She took my hand and wrapped it around her cock and I began to feel it! It was SO nice! I guessed it to be about six inches long, uncut, and it was literally throbbing in my hand!
I wanted it SO bad! I broke away from her kiss and slowly lowered myself before her, stopping to kiss and suck on her pretty nipples! If these were man-made, and they must be, they were magnificent! Darla leaned her head back and moaned loudly! Her titties were nice but that's not what truly interested me – I wanted her cock! I'm a cocksucker, and that's what matters to me!
I dropped to my knees and held the shaft of her sticky cock, rubbing it all over my face. I looked over to see my aunt, a twisted grin on her face as she watched intently. I could hear Sophie making loud slurping noises as she fed on her Mistress pussy.
I looked right into my Aunt's eyes. When I first took Darla's cockhead between my lips, Auntie blew me a big kiss! The cock tasted so hot and sticky and musky...I loved it! I pulled back the skin to expose the purplish head and Darla gasped as I took just the head into my mouth. Darla had shown me her skills, and now it was my chance to reciprocate. I sucked on just the head for a bit, and as she tried to push it deeper I resisted, looking up into her face to see her smile. She got my message – this was my show! I then began working my way down the shaft, using my tongue to apply pressure to the pulsing vein on the bottom of the shaft!
The slurps and moans of our lovemaking were interrupted by a loud "ahem" and the smell of sweet cigar smoke. I looked up from Darla's crotch to see the imposing figure of a man watching, no...inspecting us!
He was a tall and solidly built man, with ebony skin and a short buzzed haircut! He was wearing a military outfit of khaki and I could tell from the adornments above his pocket and on his shoulders that he was a man of some military stature. From my vantage point on my knees in the sissiest of outfits and with the hot cock of Darla Dicklet in my hungry mouth, I could see the long outline of a hardening cock straining against his khakis! My Aunt was the first one to speak up.
"Colonel! How nice of you to join us!"
He just snorted and grabbed his hard-on through his pants.
"Carry on ladies!"