Home Alone: Day 02

Story Info
The sissy boy gets found out.
1.1k words
3.84
112.2k
7

Part 2 of the 2 part series

Updated 08/30/2017
Created 08/09/2008
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

Day 02, The Mistress

It was 12 o'clock in the office, I couldn't wait 5 whole hours before I got home so I decided to take the rest of the week off. After racing home I ripped my clothes off and dived straight into my sisters panty drawer and took out a pink matching g-string and bra with hearts on. The feeling of them on sent my cock rock hard so that it stuck out of the panties.

A quick tug later and I had cum, the splodges of cum spread out in my sisters drawer. With a few quick licks they were gone and I could get down to my self-bondage. After the disaster of not being able to get out last time I learned about a release method of using a key frozen in ice. When the ice melts the key is released and the lock can be opened.

This afternoon I was going to try the frog tie. I bound my left ankle to my left wrist and my right ankle to my right wrist. I then crossed my legs and wrapped a chain around them When the lock was snapped shut I was stuck the key was melting away slowly to my right hand side and I knew I could be stuck here for a number of hours.

I must have been tied like this for a good number of hours before I had a click noise. OH NO that was the front door, who could it be? My mind was racing then it hit me. My mum had left a spare key with my neighbour! I couldn't let her see me like this so I started to try and shuffle behind the couch.

"What have we here then?" Her voice made me stop dead in my tracks I couldn't believe I had been found out. "So this is what you are up to your family is away is it?" I still couldn't answer.

I could feel her standing right behind me, then she spun me around. She was wearing a short black pleated skirt with the long black boots, a white shirt and black jacket. Now I have always fancied this woman she is tall with ample breasts and a ass to die for but I never thought any of the fantasies I had dreamt of would come true.

"So are you going to speak you dirty little sissy boy!"

"I....I ...I" was all I could manage

"I what!? You dirty little man!" Her voice turned nasty as she kicked me on my back. "I hope that you haven't been wearing any of my lingerie while you looked after my house last summer!"

"I'm sorry, your lingerie is just so sexy" I murmured

"Your going to pay for this now, from now one you will address m only as mistress and do exactly as I say or your mom might just find out about this! When you are released you are to walk to my house in the clothes you are wearing now. O and put a wig and some make-up on first though."

I didn't know what had just happened, my head was still spinning the ice finally melted enough to let the key out I released myself and walked about the house. I had two choices one let my mom find out about my fetish or two become my neighbour's sissy boy.

I decided on number two, so with all my courage I strode out of my house with my make-up done and knocked on her door. At first she didn't answer, surely this couldn't be a trick to let all the neighbours see my like this. Then a note came out of the letter box.

It read – Walk around the back, go inside the dog hut and you will find some cuffs, a ring gag and a slave collar. Put these on and wait in the dog house.

What could she have planned for me? I had no idea so walked around the back and did as the note said.

Almost twenty minutes past before mistress came out and dragged me in. She put a metal chain through my collar and told me to stay on my hands and knees. After I had been walked up the stairs to her room I found all her lingerie lying on the floor.

"Pick out each individual bit you have ever worn and bring it downstairs to me." With that she left me to my job. I counted out 7 matching thongs and bras that I had worn and brought them down to her.

"Now then little slut boy this is your new underwear collection, if I find you wearing anything you will be severely punished you hear"

"Yes mistress"

"You will now provide entertainment for me for two hours before my friends get here"

"Friends!" I shrieked.

"Yes friends, but don't worry you will be tied up in my closet with your gag in and and a nice big vibrator bussing up your slave hole! Now bitch I need to pee and I am not walking to the toilet"

Before I could think she had me on my back and was squatting over me.

"Now open up nice and wide and take my piss slut boy!"

And with that a stream of piss was going into my mouth. I was swallowing as fast as I could to stop myself gagging but there was too much and it started overflowing my mouth and onto mistress's floor.

"What have you done slut boy? Now lap that up with your tongue then get on all fours and put that ass of yours in the air" With that she left the room.

When the door re-opened I glanced around and seen my mistress in a latex bra and lng leather boots. But with a strap-on on!

"No mistress please anything but that" I rolled onto my back and felt the worst pain ever as she crashed a whip straight down over my balls and cock.

"Now on your knees slut and take it like the slut that you are!"

It felt like a red hot dagger as she penetrated my ass "Come on sissy boy you will be taking more of this as my slave boy!"

The pain must of got too much for me and I must of passed out because the next thing I remember was being bundled out of her closet while being tied in a ball, and sure enough a pink vibrator was up my ass.

"Now slut go home as I have work now, I will collect you at 3pm tomorrow so be ready"

With that she untied the rope and kicked me out of house.

"3pm slut boy, you had better be ready!"

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousalmost 8 years ago
Sissy wants more

Wow how do i get to be her sissy boy slut slave?

bluesky496bluesky496over 10 years ago

you must write the next chapter soon pleeeeaase,x

Share this Story

READ MORE OF THIS SERIES

Home Alone Series Info

Similar Stories

A Dress Up Party with the Girls Mike gets invited to a girls-only dress up party.in Group Sex
Caught by my Sister Young man caught in his sister's pantiesin Transgender & Crossdressers
New Beginnings Guy is feminized by mothers's assistant.in Transgender & Crossdressers
Lonely Man Becomes a Sissy He becomes a sissy for an online mistress.in Transgender & Crossdressers
Turning Him Into A Whore She turns him into a trick turning whore.in Transgender & Crossdressers
More Stories