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
I was confused.
Sarah:?
Olivia: My subs only wear stay-ups, thigh highs, or garter and stockings.
Ohhhhhhh. I wore stay-ups once (hold ups in England, pantyhose are tights in England too in case you are curious), but found them annoying. I also had a garter-belt that I hadn't worn in years. It was a sexy surprise for when I tried to spice up my sex life when I was married, but he just wanted to fuck me and go to sleep. Men.
Sarah: Oh. I have a garter and stockings, but I haven't worn them since who knows when.
Olivia: When was the last time you had sex?
I wanted to joke with this person, but chose not to. I didn't know if she had a sense of humour yet. Truth was I hadn't had sex since coming to America... at least not with a person.
My vibrator on the other hand usually got a daily workout.
Sarah: Over a year.
Olivia: Mission 1.
Sarah:?
Olivia: I will assign you missions to see if you are qualified to continue talking to me and maybe eventually qualify for complete submission to me.
I loved the idea of tasks... I loved finishing them.... Just like I loved scratching things off a checklist or even a grocery list (yes, I was that kind of woman).
Sarah: Um...Ok.
Olivia: Mission 1 - Go and buy a variety of new stockings.
I had already been considering doing just that once I read her nylons expectations.
Sarah: Ok.
Olivia: Now.
(Olivia has left chat)
I was disappointed that she had left chat so abruptly. I was enjoying the conversation and wanted to learn more about her.
Determined to obey her, I stopped pitying myself. I took charge of myself and went shopping.
I bought a whole bunch of thigh high pairs of stockings in a variety of colours: mocha, beige, black, red, and white. I also bought pairs of black, white and tan stockings for my garter-belt.
I wanted to chat with Olivia as soon as I got back home, but Victoria wanted to chat about some bitch (her word) who was bullying her. I advised her to be the stronger woman and turn the other cheek... although when I was a teenager I would have stood up to her. But I didn't want Victoria, already new to an American school, to be ostracized. She was a strong young woman, but still.
Once she went to her bedroom, I got undressed and dressed up in a nightie, with black thigh highs.
January 2, 2008 22:38:38
Sarah: Olivia?
Sarah: You there?
Sarah: I bought some stockings as instructed.
I sat there and stared at the screen, praying a response would come. I felt like a teenager of a previous generation waiting for the phone to ring.
January 2, 2008 23:59:37
Sarah: Olivia?
Sarah: I am wearing a pair right now.
Sarah: A black pair with matching knickers and a nightie.
Sarah: Goodnight.
I ended up reading some online erotica and getting myself off wishing I was the protagonist in the story.
As soon as I got up next morning, I checked for a response and saw none.
I was disappointed.
I sent her a message to explain why I wouldn't be able to come online for a while.
January 3, 2008 08:33:12
Sarah: I have to go to work for a few hours. I should be back by 4.
At work, I turned off silly submissive me and turned on straight, confident businesslike me. It was amazing how easily I could shift from one to another.
Once home, I immediately went to my laptop and logged in.
January 3, 2008 16:12:48
Sarah: I'm back.
Olivia: Hi, slut. Tell me what you bought.
First, I was thrilled she was online.
Second, I was just called a slut by an eighteen-year-old. If a guy at work called me or any other woman a slut I would rip his nuts off. Yet, when this stranger called me one, an instant gush leaked into my panties.
I wanted to make sure she knew I'd completed mission 1.
Sarah: I bought stay-ups or thigh highs, whatever you call them, in mocha (3 pairs), beige (2 pairs), black (3 pairs), red (1 pair), white (2 pairs). I also bought pairs of black, white and tan stockings for my garter-belt.
Olivia: What are you wearing right now?
Sarah: Mocha thigh highs, a black business skirt and blazer and a white blouse.
Olivia: I see. Just a minute.
There was a long pause while I wondered what I had done wrong.
Olivia: Sorry, I am also online with another slave. One that has completed her training.
Sarah:
Olivia: Play your cards right and you too can be my slave.
Sarah:
Olivia: What kind of toys do you own?
Sarah: One vibrator.
Olivia: Really? I guess we know what your next mission is.
Sarah: Get more toys?
Olivia: Of course. You will need a couple more vibrators, a strap-on for me to fuck you with if the time comes, a butt plug and some sort of vibrating toy to wear in your pussy while you are at work.
Sarah: OK.
Olivia: Later. And from now on I expect you naked except for stockings and heels. Is that understood, slut?
Sarah: Yes.
Olivia: Good, you just may be worth my time. Goodnight, I have to go and train another slave.
(Olivia has left chat)
I sighed.
This was so frustrating.
It was like dating a boy in high school... completely unpredictable.
I went and had a quick shower, made dinner and ended up doing some research for an upcoming trial.
Realizing I was getting too eager, I decided to avoid the internet for a few days, especially since her implication of anal... something I had never been interested in.
That said, a few days later, I ended up in a sex toy store, on the other end of town, the sketchy side, where I ended up spending over four hundred bucks on a variety of sex toys including: a strap-on cock, four new vibrators in different sizes (one called a rabbit, another called Big Buzz (which made me smile), another black one (hey, all girls at some point wonder about black cock) and another smaller one for my purse (not sure I needed one for my purse, but I decided I did), a big black dildo (okay I may be obsessed), a suction cup dildo so I could fuck myself in the shower, a pair of handcuffs (because they were on sale and something I had always fantasized about), a vibrating egg with a remote control, a triple pack of starter butt plugs (although the largest one was way too fucking big for any human) and anal beads (that the nice tattoo covered saleswoman suggested are great for a novice anal girl). I also bought lube, lots of lube.
When I got home, I opened up all the toys, got undressed, except for my thigh highs, grabbed the black dildo, turned on some porn on the big screen TV (Victoria was out of town) and fucked myself to multiple orgasms.
Once I was sexually satisfied, I put all the toys together in a box in my closet and labeled it taxes, just in case my daughter somehow ended up in my closet.
I lasted a week before I was back online and chatting with the teen temptress.
To my surprise she didn't even ask where I had been for a week.
January 10,2008, 20:00:12
Sarah: Hi.
Sarah: Dressed as expected.
Olivia: How would that be?
Sarah: Naked, except my thigh highs and heels.
Which I actually was.
Olivia: Good slut.
Sarah: Thank you.
Olivia: Did you buy a vibrating egg as expected?
Sarah: Yes.
Olivia: Good. Tomorrow I expect you to take the egg you purchased and wear it in your cunt all day at work.
Sarah: But I have a trial.
Olivia: That's no excuse.
(Olivia has left chat)
I sighed.
Had I just offended her again?
It seemed so.
So I quickly apologized.
January 10, 2008, 20:03:19
Sarah: I am so sorry...I will wear the egg as you requested.
Sarah: Please forgive your slut.
Sarah: U own me.
The next night I went online, and desperate to get back in her good books I decided to use the word that shows the ultimate respect: the 'M' word.
January 11, 2008, 18:23:41
Sarah: I am home...
Sarah: Mistress?
Sarah: Please Mistress? I will do anything u command!
These were risky words... both the term 'Mistress' and the phrase 'I will do anything', yet I was desperate.
Olivia: Mistress, I like that. But that is twice now you have questioned my instructions.
Sarah: Twice?
Olivia: Yes, when I asked if you were looking for a Mistress and when you hesitated over putting the egg in your old cunt.
Sarah: Oh, I am so sorry.
Olivia: U need to be punished.
Being a sub, being punished was something I was used to back in college.
Sarah: Yes Mistress.
Olivia: Is your daughter home?
Sarah: No.
Olivia: Good. Go into her room and grab her pillow.
Sarah: OK.
Deciding to actually obey her, I went to Victoria's room and got her pillow. I then returned, unsure of the purpose of grabbing it.
Sarah: Back.
Olivia: Are you dressed as asked?
Sarah: Yes, Mistress.
Olivia: Fuck yourself to an orgasm.
I didn't have any toys nearby, so I moved my hand to my pussy and began rubbing. As I did, I looked at the screen.
Olivia: Imagine u r on your knees pleasing my young, ripe, shaved cunt.
I imagined just that... getting new information about my dream Mistress... her cunt was shaved, just like mine, although I hadn't had a complete Brazilian in years.
Olivia: Imagine I have just exploded my juices all over ur slut face.
God, I needed to eat cunt. It had been so fucking long.
Olivia: Imagine me fucking ur sloppy cunt with my strap-on, ur daughter in the room beside us.
"Oh my God!" I screamed, as I exploded quickly and intensely.
Even as I kept coming, I responded to Olivia.
Sarah: I just came.
Olivia: Rub ur whore cunt all over your daughter's pillowcase.
I couldn't believe that was the order.
Sarah: OMG!
Olivia: NOW!!!
I didn't want to disobey a third time, so I grabbed her pillow from the floor (it must have fallen during my masturbation session) and rubbed it all over my cunt.
Sarah: Yes, Mistress.
Olivia: Dry yourself completely with it!
I kept doing it until my pussy was no longer wet.
Sarah: Done.
Olivia: Go return the pillow to ur daughter's bed.
Sarah: Yes, Mistress.
I was so under her spell, I didn't hesitate.
Sarah: I did it.
Olivia: Good slut. U just may be worthy yet of being my sub slut.
Sarah: Understood.
Olivia: I won't be online for a couple of weeks. I have finals and then my family and I are going skiing up in Canada.
Sarah:
Olivia: While I am gone, I expect u to continue wearing only thigh highs and stop wearing panties completely. Understood?
Those instructions were pretty easy to obey.
Sarah: Yes, Mistress.
Olivia: Good, I also expect u to have a butt plug in ur ass whenever ur daughter is home.
That was a little less easy to agree to, but I obeyed like the submissive I was.
Sarah: Understood.
Olivia: Talk 2 u in a couple of weeks.
(Olivia has left chat)
So for two weeks, I went without underwear, well, minus the days I got my period, as well as wearing thigh highs.
It felt good obeying.
I also discovered the pains and pleasures of anal.
I tried the smallest of the butt plugs and with some lube it easily slid inside me. After half an hour, I was bored and tried the second plug. This one took some effort to insert and cost me some pain.
I needed to practice walking with it in me for when Victoria was home. I had no idea why I felt compelled to obey, it was only online role play, yet I did.
I got used to it, but yelped when I forgot it was in me and sat down... the plug reaching new depths in me.
Victoria asked what was wrong and I lied, saying I had banged my knee.
I also went shopping for sexier clothing. My business attire was black with black with a side of black. I decided I needed some colour, and shorter skirts and higher heels and tighter blouses.
The men at work noticed and my daughter did too. She asked, while I sat at the kitchen table with a butt plug lodged up my arse, "What's with the new attire?"
"You noticed?" I asked.
"Of course," she nodded. "It's quite different from your usual work clothes."
"Someone called me boring and stuffy and it pissed me off, but I realized there was some truth to it," I said.
"Why didn't you just say you're British and we're all a bit stuffy?" she joked.
"I should have," I laughed.
"Well, you look great, Mom," she complimented, which made me feel really good about myself.
Every night I checked to see if Olivia was back, alas every night I was disappointed. It sure didn't stop me though from fucking myself and experimenting with every toy I'd purchased. Usually I imagined being used by Olivia in some way, but on occasion my fantasy was triggered by someone I met that day.
I fucked myself with the wall cock while imagining I was servicing the hot waitress at the 50s diner I often go to.
I used the rabbit, which really had me bouncing, as I imagined Victoria's nerdy friend Becka sneaking into the kitchen and making me service her while Victoria was having a sleepover.
I used the Big Buzz while also inserting anal beads in my arse and imagining being the submissive sandwich of two cheerleaders I saw walking together at the mall (even though they were from a rival school to Victoria's).
That said, I was jubilant when I was getting ready for bed one night and there was a message from Olivia. It was just two words... and I didn't actually chat with her that evening, but I was giddy with excitement for whatever she had in store for me.
January 27, 2008, 21:11:56
Olivia: I'm back.
I won't bore you with the chats that happened for the next couple weeks, but instead I'll share with you some of the many naughty tasks she had me complete.
On the 29th of January:
She had me come at work every two hours and never come twice the same way.
At the 8 o'clock hour I came with my fingers.
At the 10 0'clock hour I used a full Coke bottle (with a plastic cap, not a metal one... I'm not crazy).
At lunch I used a cucumber before slicing it up and using it in my salad (as ordered by Olivia). I'm not going to lie, my pussy garnish is quite yummy.
At the 2 o'clock hour I put the egg inside me and tapped my clit with the end of a stapler.
At the 4 o'clock hour I ground my pussy on the chair rest which was surprisingly pleasurable... leather was definitely a good choice.
Each orgasm was exhilarating, because I was obeying; nerve-wracking because I was at work; and exhausting as each orgasm took more work than the one before it.
On the 30th of January:
I had to cum in a mall bathroom (kind of gross, okay really gross) and smear my cum all over my mouth. Then go and ask for help from at least three girls in different shops.
That wasn't overly bad, although one girl asked what lipstick I used to make my lips so shiny.
Which I answered, lying but enjoying the shock value, 'My girlfriend's lower lips'.
The look on her face was priceless and Olivia was proud of me for saying it.
On the 31st of January:
I tried fisting myself, where I learned I simply wasn't that flexible. I could get four fingers in, but that was the best I could do.
I felt guilty for not being able to complete the task, but to my surprise Olivia simply said that she would fist fuck me herself one day.
That had my cunt gushing even if it was just a hypothetical.
