Auntie's Panties Ch. 02

Story Info
It's time to play dress up.
2.7k words
4.56
179.7k
39

Part 2 of the 6 part series

Updated 06/09/2023
Created 05/13/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Jake sat in his bath. The heat from the water made the room feel like a sauna. The main mirror was steamed over and Jake could feel perspiration on his brow. His body tingled from the heat. Pores were opening and cleansing. His body was also tingling from the lotion that his Aunt had added to the water. The lotion was intended to remove his body hair. Not that Jake was either hirsute or aware of the actions of the lotion, but Auntie could not have her Jakey covered in ugly man hair.

The door to the bathroom opened and Jake's Auntie entered closing the door behind her to ensure that the temperature in the room did not drop. Her mules making a dull sound across the bathroom floor vinyl. "How are you my sweet? Has all the nasty gone? Let Auntie look?" Jake found himself cupping his balls to protect his innocence. His shoulders hunched almost cowed to his Aunt. Phoebe ran her hand along his right leg from his calf to his groin. "Oh now Jakey, let Auntie check you for nasties." With which she flicked at his hands and they fell away. She ran her hand over his balls and gently squeezed them making Jake him sharply exhale. Phoebe then placed her hand on his cock. It was a semi but twitched and grew at her touch. Phoebe stroked on his cock several times cooing as Jake's hardness came to the full. "We must find a good use for this. Now out you come."

Phoebe held a large bath towel before Jake as he stepped from the bath. His newly hairless body tingled as his movements caught the change of temperature outside of the hot water. Phoebe wrapped the towel around him and braced it at Jake's front as if he had a cleavage. "Well look at you. As fresh as a daisy. Now, wouldn't that be fun if we called you Daisy."

"M...m..mmy name is Jake," he said without a great deal of conviction.

"Hush. If we're going to play proper dress up then you have to have a dress up name. Calling you Jakey when you were younger was one thing. But now......" She paused as she inspected him from head to toe. ".....now that you have matured you must have a proper grown up name. I will call you Daisy and you will only respond to that name. Is that clear Daisy?" Jake stared at his Aunt with tears welling in his eyes. "Did you hear me?" Jake nodded slowly, tears now running down his cheeks. "Good. Now, whenever I call you by your sissy name you will respond with 'Yes Mistress'. Now that you are a fully grown sissy I think that our time as Auntie and nephew is long behind us. Don't you agree Daisy?"

Jake was gently sobbing. He wiped a tear from his face and with his eyes looking to the ground he responded meekly. "Yyyess.....Mistress."

"Good girl. Now take my hand and let's get you sorted out." Phoebe offered Daisy her left hand which Daisy, face still to the ground took as they left the bathroom for the guest room. Once in the guest room Phoebe removed the towel from Daisy and gave him a look over. She twirled her hand and Daisy dutifully turned a full circle. "Wonderful, your body is so smooth with that nasty hair gone. We can't have any unsightliness in our pretty garments." Daisy's eyes remained focused on the floor.

"Now, I have some friends coming over later so we must have you looking your best."

"What people? Wh....," Daisy's questioning ended abruptly as Phoebe slapped his cheek hard.

"Who told you to speak?" Phoebe grabbed Daisy's face roughly by the chin and looked into the eyes of her nephew. "You speak when you are spoken to and at no other times." Phoebe released his chin and Daisy's gaze once more sank to the ground. "Now to work." Phoebe physically moved Daisy towards a chest of drawers where he stood as his Auntie produced a series of garments and placed them on the adjacent bed. Obviously satisfied with her work Phoebe returned her attention to her nephew.

Phoebe began by fastening a white satin garter belt around Daisy's waist, its four tassels hung loosely on Daisy's thighs. The sensation made his cock twitch and he felt an unwanted hardness begin to swell in his cock. Next his Auntie opened a packet from which fell a pair of white gossamer stockings. She pushed Daisy back onto the bed. "Lift your left leg Daisy dear. We never got to play with such complicated things when you were younger so I will help you this time but you must learn how to dress yourself in future and encasing your legs without laddering your garments will take some practice I feel." Daisy's nerves tingled as the feel of the stocking brushed against his newly shaved skin. Phoebe smoothed the silky material along his leg before fastening the stocking tops to the four fastenings. Daisy offered his right leg without any prompting. Phoebe paused and looked at Daisy. His face was eager and his eyes were wide with anticipation. "You're such a good sissy."

With the final stocking attached Phoebe produced a pair of white satin full panties that she slid up Daisy's legs. "Stand." Phoebe said sternly, to which Daisy immediately got to his feet. Phoebe slid the panties up Daisy's thighs and pulled them into place around his buttocks. "This won't do," Phoebe said pointing at the bulge in Daisy's panties. "Do you remember what you have to do Daisy?" Daisy reached inside his panties and slipped his cock between his thighs. "Wonderful!" said Phoebe. She ran her hands over the material covering Daisy's bottom. "Oh yes, I think we shall great fun taking your ass." Daisy looked up at Phoebe with this remark and received another slap across his cheek. "How dare you look upon me. You have no right to look upon your mistress unless instructed. And there will be plenty of instruction to follow including the offering of your ass for fucking. You will not argue. You will not protest. You will come to enjoy your life as our sissy slut. After a short while you will wonder why you ever fussed over such matters. Now where were we?"

Phoebe retrieved another garment from the bed. It was a white satin bra which had foam filled cups. She threaded the bra through Daisy's arms and fastened this to his body. The cups protruded slightly from his chest. "Yes, these will do. I think your little body would look wrong with huge breasts."

Daisy felt a further tingle throughout his body which he tried to reject. Old memories of playing 'dress up' were beginning to resurface. Hidden times from his younger days with Auntie Phoebe. Did he ever think it would come to this? 'We're only playing,' he tried to convince himself. "Oh yes," said Phoebe as she stood back looking at her nephew, "you look divine. Now we must find the perfect outfit. Obviously nothing that shows your sissy's cleavage. We must let you grow into that."

Daisy stood in his soft and dainty lingerie, his cock twitching at the feel of the material on his skin. Confusion wracked his mind. Should he try and escape? Not dressed like this. He would wait until his Aunt was asleep and then he would make a run for it. "My dear what are you thinking about? Is your sissy mind wandering?" Phoebe did not wait for a response and Daisy had none to offer. Phoebe held a white chiffon dress before Daisy. It had blue printed flowers within its pattern. Daisy looked at the dress in amazement. When he had played dress up before he had been dressed in party dresses that were for little girls, but this was a proper woman's dress. The chiffon looked so light. His mind raced. He wanted so much to feel the material against his skin. To wear it and to see himself wearing it. 'What am I thinking? This is wrong.' The voice was a little less assertive now however.

"Isn't it a lovely dress? I think it will compliment your figure perfectly." Phoebe unzipped the dress and helped Daisy climb into the chiffon outfit. Daisy felt his senses heighten further as the light material brushed against his skin. The feel of the chiffon as it met his stocking legs melted his willpower even further. "Oh delightful," said Phoebe. She checked her watch. "Timing is everything. We have just over thirty minutes to get you looking very delectable."

"Why? What's hap........?" Daisy's words trailed off as his Aunt landed another slap across his left cheek.

"Were you not told to hold your tongue until told?" Daisy, a tear welling in his eye, looked at his Aunt in confusion. 'Should I answer?' he thought to himself. "That's right my little sissy. Hold your tongue until instructed. Your tongue will be busy enough very soon. Now stop whimpering and sit." His Aunt pointed to a stool adjacent to the vanity table. Daisy turned towards the mirror. "No face me. I will need to see your face if I am to suitably dress it as well. Now stop crying or you will smear my work."

Daisy sat before his Aunt as she fussed at his face with a selection of make up items. His mind hurt from frustration. Frustrated with his ability not to fight back. He was a man, this was not right. But a part of him called on another time when he had been in his Aunt's thrall. A time when she had dressed him in frilly pants and skirts. 'Playing' she called it. And as he got older the playthings had become much more fun, such that in his mid teens the frilly things had been replaced by silken things. He had struggled with the thoughts and images but his Aunt had been so soothing, so knowing, so assuring. His thoughts to reject had been wrong she would tell him, and they would spend hours each dressed in silks and satins just being together. He would help her around the house whilst dressed and enjoy the lighter feel of the garments compared to his normal clothes.

Now sat before his Aunt those old feelings were resurfacing as the feel of the chiffon and the lingerie brushed against his hairless skin. He could feel his cock harden between his legs, straining to free itself from its unnatural position. His emotions continued to battle as he was dragged back to the present by his Aunt placing a wig onto his head. She clapped her hands with obvious joy when she saw the finished article. Daisy remained sat as he Aunt fussed with the contents of box from which she produced a pair of white heeled shoes which she placed on his feet as if he were Cinderella.

"Nothing too much to start with, but we can't have you wearing flats. You need to show off your legs at all times like a good sissy. Take my hands." Daisy did as he was told and stood in his heels the pull of the garter belt on his waist and the extra height from the heels confusing his balance. "Now come look at yourself. I think you will be a very welcome sight to our guests." Daisy held his Aunt's hand as she led him to a full length mirror. The image that looked back at him amazed him. The long blonde hair cascaded over the shoulders of the patterned dress and beneath it sat a well blushed set of high cheekbones and pouting red lips. He looked like the kind of fuck slut he used to enjoy jacking off to when he was younger.

He continued to survey his face as his the front door bell sounded. "Our guests have arrived!" his Aunt exclaimed. "Go down and let them in. I must prepare myself." Daisy stayed motionless. "Do as you are told." Daisy began to move but was verbally stopped by his Aunt. "What do you say when you are given an instruction?" Daisy looked at his Aunt puzzled. "You insolent little slut. I told you, you will respond to my commands with the words 'Yes Mistress'. Is that clear?" Daisy hesitated again. "Y...yyes M.mmistress." The door bell sounded again. "Now answer the door."

"Yes Mistress."

Daisy headed from the bedroom. He carefully made his way down the stairs. Although the heels were only two inches he had no confidence in his balance. He saw images on the other side of the front door and paused. He was dressed as a woman, what was he doing answering the door? The door bell sounded again and it made him jump. Fear of what his Aunt might say, or do, made up his mind. Daisy opened the door. Three well attired and statuesque women made their way into the house without invitation. The first navigated her way to the the lounge and the others followed. Daisy slowly closed the front door and made his way toward the sound of animated chatter.

"You must be Daisy. Take our coats." Each of the women removed their coats and handed them to Daisy without seeking his confirmation. As each woman removed their outer layer Daisy caught the authoritative nature of their outfits. Each was dressed in a dark tailored suit with a white silk blouse, the buttons open to reveal their full cleavages. Their skirts ended just above the knee and their seamed black stocking legs sat within six inch black heels. Their make up was stunning and each stared at him as if he were in front of a headmistress. Dismissive and demeaning, he was quite obviously below them in any stature.

"Do you have vodka in this house?" Daisy nodded. "Make us three drinks, now, you little sissy."

Daisy hung up their coats in the hallway and returned to the lounge to make the drinks. The women continued to talk as Daisy knelt beside the sideboard and removed the glasses and alcohol. He was pouring the third drink when the women's conversation ceased. Daisy turned to see his Aunt entering the lounge. Fortunately he was not holding anything in his hands as he was certain he would have dropped it at her image. His Aunt had changed from her house coat into an outfit similar to the other women, although her appearance looked more polished than her guests.

Daisy noticed that the other women had their heads bowed. Phoebe walked towards them as they stood with their hands in front of them. She placed a finger on the chin of the first woman and raised her eyes to meet her own. Phoebe looked at the woman for a moment and then placed her hand under the woman's skirt. The woman let out a sigh as Phoebe removed her finger after a moment. Phoebe waved her glistening finger under the nose of the second woman who did not move.

"You may taste it." In a flash the second woman's mouth was on Phoebe's finger licking it dry. Phoebe removed the finger with a 'popping noise. Phoebe laughed as the second woman's head returned to the floor.

Phoebe moved to the final woman in the line. "I am so pleased to see you here Anna my dear. I think I will enjoy you greatly." Phoebe turned to Daisy and commanded him to make a fourth drink.

"My ladies, may I introduce to you Daisy, our new sissy. She is a virgin. Did you remember to contact Gavin my dear Tania?"

The second woman spoke. "Yes Mistress. I gave him the address and he will be here at 4pm."

"Wonderful, well then whilst we wait," Phoebe said hitching her skirt to reveal a shaved cunt, "Anna can show me how grateful she is for being allowed into my club."

Daisy watched as the third woman moved from her position and knelt before his Aunt before pacing hands on his Aunt's thighs and plunging her face between them and finally her tongue onto his Aunt's clit. Phoebe let out a sigh and a laugh and looking at the stunned Daisy said "Are you getting wet my dear? I hope so, as you will be next."

Daisy's cock was so hard it slipped from between his thighs and stretched beyond the material of his silk panties.

'What does she mean?' he thought to himself.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
AnonymousAnonymousover 1 year ago
Stocking Sissy

I am now living as a women and working at a adult / movie store.I was caught fully made up and dressed sucking on a big black cock.The man who caught me black mailed me after he have pictures of me sucking black cock.He forced me to live as a women dress as a women and have sex as a women.I was forced to work at the book store doing what he told me to do.I now suck all the cocks and swallow their loads.I do ass to mouth anal threesomes and gang bangs.He fucks me every day and i have to suck his black cock and swallow his loads.

AnonymousAnonymousover 4 years ago
Wish I was daisy

I have had similar situations in my sissy fantasies. Yes, I dress to be my wife’s sissy but I cannot get her to make me a sissy maid for her wider group of friends.... maybe one day?

From sillliwilli@gmail.com

AnonymousAnonymousabout 8 years ago
can't wait for the next chapter

This is a real turn on. I'm a sissy who loves servicing my mistresses and her lovers, both male & female. I can't wait to read what happens next.

AnonymousAnonymousalmost 10 years ago
So gorgeous and silky sexy

Love this story so much made my silky covered cockette twitch. Had to milk my clitty and cumm all over my stocking thighs when I re-read the story xxxxxx

DianisDianisalmost 14 years ago
yes yes please continue

can imagine how hard Daisy was inside the panty, mmmmm would love to slip between her legs and relieve that bulge, mmmmm

Di

dianocarter@hotmail.com

ps write me for some hot talk, mmmm

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Feminized By My Mother Ch. 01 Shemale mother makes son a sissy.in Transgender & Crossdressers
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
Sissy Girl Forever Pt. 01 Feminized sissy is trained by loving Mistress.in Transgender & Crossdressers
Being a Sissy for Viv Ch. 01 Pretty panties is all it takes.in Transgender & Crossdressers
Caught by my Sister Young man caught in his sister's pantiesin Transgender & Crossdressers
More Stories