Satisfying Mistress Ch. 02

Literotic asexstories – Satisfying Mistress Ch. 02 by RKHunter,RKHunter
Sunday

My eyes fly open and I find myself staring straight at the ceiling. Turning I see its 5:13am, it’s still dark out. My mind is racing and panic begins to overtake me. Throwing the covers off and leaping out of bed I nearly kill myself as I trip over my clothes that I so clumsily dumped in a pile at my bedside last night.

Down the stairs, flipping on the lights and into the family room I look immediately to the coffee table. Ahhhhh …… a sigh of relief as I see my sex toys Mistress demanded I acquire. I flop onto the couch dropping my arms to my sides and take a deep breath. I had feared that everything that happened yesterday was simply a fantastic dream.

The rest of the day slipped by as any other Sunday might, hit the gym, did some laundry, grocery shopping, paid a few bills, all the typical stuff. No word from Mistress. I had not really expected to hear from her anyway.

Monday

Monday was a holiday, Martin Luther King Day, and I was off work. Getting up fairly early as was common for me I headed to the gym to beat the crowds. I don’t normally work out on Mondays but wasn’t going to pass up the opportunity given a free day to myself.

Arriving home I fired up the computer and signed onto EP. I was very anxious and exciting about receiving my next instructions. Still nothing from her, and although a bit disappointed it was only 9am on Monday morning.

Mistress had not actually told me when she would send my instructions so I was only assuming it would be today. Was her delay intentional? I did think briefly about calling her however I knew I was being completely ridiculous. I could wait, it wouldn’t kill me after all…and in reality I was free, to do as I pleased, no constraints, no rules, no control, no anything. I should be happy of course however I knew better. I need her control. I craved her control. It’s just that simple, damn it!!!

Several more hours pass and thousand or so refreshes of EP and still nothing. I was starting to get a bit … something … not sure how to explain it actually. I wasn’t mad, but I was like come on, why aren’t you contacting me? I was unnerved. Desperate.

It was just then I finally saw a new email come through, it was Mistress! I was so happy!

Clicking open I begin to read …

Dear Sub xxxx,

Well done. You’ve adequately completed the first round of your tasks to my satisfaction and delight.

You purchased the toys with professional assistance from the store associate, a young woman who no doubt relished the chore and no doubt shared the incident and a hearty laugh with her lover, male or female, later that night. You captured the moment and the adventure, especially how you felt . . . nervous yet thrilled and compelled . . . and wrote about it (with a pic. good.) for anyone to see on EP.

You’re well on your way to relief. But not just yet.

Round II will be exponentially more difficult but must be completed to the letter. Because I said so. No whining allowed or I will be ruthless.

The following must be started immediately and continue right through Friday night, Jan. 20. Only then will I allow you relief. Perhaps.

1- You will wear the Rings of Hell starting now. I expect it to be a tight fit. You will wear no underwear throughout the week. No excuses. The timing is with purpose; I know you have presentations and budget meetings and you will be front and center and the focus will be you as your colleagues will have questions and look to you for direction. They may not be looking into your eyes. You will report back to me at regular intervals. You must take a picture tonight to prove to me you have done exactly what I said (wearing the “Gates”) and post that picture to the “Mistress” photo album on EP (and for all to see). Get yourself hard before taking the picture (you know what I like) and remember NO cumming! So be very careful. Oh, as I said before, I want you to keep the “toys”, especially the dildo, on the kitchen table all week. A pleasant reminder of your tasks.

2- You will watch the porn video completely naked Tuesday night. Keep an eye for details because I will have questions. I would like you to think about being part of the video and playing the part of the lead male and, vicariously, think about and enjoy the arousal. You may touch yourself but I suggest avoid the temptation. Keep your phone close by. I may need some live updates. Maybe.

3- On Wednesday as you trudge through your busy day sans underwear with the Gates of Hell tugging, I want you to evaluate all the women with which you come in contact. I would like to know, specifically, which of the group you would like to fuck for pure primal reasons. Put aside brains, character, wit and charm. You’re especially horny this week and I want you to think with your cock. Tell me Wednesday night.

Oh, a nasty, nasty thought just crossed my mind: You would hate it if I sent the girl you select the headless nude picture you have posted on EP. I won’t. Maybe. Send me her email address.

4- This is regarding your task on Friday when I take your virginity with the dildo and lube that you purchased. Too bad it’s not a strap-on because I know you live to please Mistress and heighten MY pleasure. I so wanted my fingernails to cut and mark the flesh around your hips and I thrust . . . a badge of honor for you

You’ll receive another email from me on Thursday. Look for it around lunch time. I’ll share an additional task or two then. You’ll be very horny by then, 12 days without relief and ready to doing anything no matter how humiliating. I’m counting on it…

Complete the above to the letter and then we will get to the matter of Friday night when I guide you on webcam.

Your Mistress

I read the email several times, each and every word. Mistress had done well, but not nearly as challenging as I thought it would be. Going through the list in my mind…

…The Gate of Hell as underwear for the week, doable for sure.

…Watching an old school porn video, nothing to it. Porn has never floated my boat anyway.

…Another picture of my hard cock, no problem. Posted on EP… mmmmm … not so great but doable.

…Pick out a woman at work my cock wants to fuck like a slut…fun! Give Mistress her name and email address with threat of sending nude picture of me!!!! Fuck no, that’s not happening!!

…and for the time being, I’ll just ignoring the whole “take my virginity” thing…

Ok … so I have 3 doable tasks and one in which I’m deathly afraid.

All I have to do is figure out how to convince Mistress to switch out the one task that I can’t do and give me a new one. Simple!

I of course begin chuckling to myself. Sure tough guy… why don’t you just pick up that phone and call Mistress and say… HEEEYYYY Mistress, how about we sit down and chat about the tasks you’ve sent me. I think I can agree to three, no changes required, but one of them we need modify a bit.

I mean … I negotiate multi-million dollar contacts every day of the week. I’m the company’s strongest negotiator after all. This should be a walk in the park for me. Mistress is 26 years old. Smart as hell yes, but still young and inexperienced in the negotiation world. Come on… a piece of cake for me.

Again … I start laughing this time out load. Who the hell am I kidding? I can’t negotiate with Mistress. I’m compelled to please her. I will simply die if I disappoint her.

Gates of Hell as undies I can do this for sure. Strip down and grab the Gates of Hell. Seems simple enough to put on, just slip my cock through the 6 rings and then pull the largest ring at the end over my balls to rest at my base.

SHIT!!! No……do not get a hard-on!! *A little erectile dysfunction might be helpful at this moment*. This thing is never going on if I’m hard that’s for damn sure. Ok…walk around…calm down…ok better… slide cock through rings and stretch large ring over balls. Mmmmm… rings don’t stretch, shit this is very hard rubber. How the hell am I suppose to get this over my balls. Mmmmm, maybe try balls first and then cock. Nope, that’s not working either. I wonder if it’s too small for me. Hehehehe, ok dude get over yourself.

Ah, a thought, maybe there are instructions on the packaging. Nope!

Ok, I guess a little man handling (no pun intended) is in order here. Slid cock back through rings, grab sack and pull through end ring…..ouch….. ahhhhh…. success. SHIT!!!… where the hell are my balls? Sack is empty, crap balls are still on wrong side of ring! Fuck!

Ok, found balls in gut, pushing one at a time through the ring. Tight …dam this ring is small! Ok, one through and now two! Success, the Gate of Hell (great name) is now in place!

Mmmmm, this is sort of weird. The leather strap connecting the rings if fairly stiff, it’s sort of holding my cock out, not straight out, but not hanging either.

Sort of reminds me of when Mistress has me lay my cock on her open palm, just to mess with me. Just slightly supporting its weight but not providing any stimulation. That drives me fucking nuts by the way!!!

Ok, let’s trying walking a bit…hehehe, I’m bouncing within this thing it’s sort of stimulating actually.

Mmmmmm….maybe more than a little stimulating, I’m getting hard. I wonder if this is what her pearl thong does for Mistress? I bet it is…nice!

This might be more of a challenge than I expected. I’ve gone 9 days so far without cumming and this thing is going to provide 24 hour a day stimulation, although slight, stimulation just the same. Maybe I underestimated Mistress on this one. How the HELL does she know this stuff!!

I think I’ll get the picture over with now since I’m only going to get more and more horny as the days pass and I can’t take the chance I might cum by accident.

Ok, the first challenge, how to I get rock hard wearing this thing? I can’t stroke myself the rings are in the way. I suppose I can slap myself around a bit and tickle my balls as that normally gets me hard.

Ahh, this seems to be working…I’m getting harder and harder. A few more slaps and I should be ready to snap a picture. WOW… the rings are getting very tight I’m really filling this thing up.

Oh FUCK…”Houston we have a problem”… I’m gonna cum…SHIT…STOP…STOP…think about something else…….. anything ……………focus………….mowing the lawn, ok, that’s good, mowing the lawn.

FUCK!!! I feel the juices flowing up my cock, DAM, DAM, hold on buddy…don’t do it, don’t cum!!!!

Ahhhhhh, ok I think I’m going to be ok, quick snap the picture as I can’t do this again.

WOW that was close…just precum, nothing more. Mmmm, salty.

Tuesday

Much easier getting the Gate of Hell back on this time (took it off to shower). I’ve got it figured out.

It will be a busy day at the office with final budget presentations. Should be a treat wearing a suit, presenting to the board of directors wearing “Gates of Hell” cock ring as underwear!

What a trip this week is turning into.

Starting to head down stairs after getting dressed it dawns on me that I haven’t worn pants with the Gates of Hell cock ring yet! I spent all day yesterday naked.

This is interesting … it sort of makes my cock bounce against my leg with each step. The leather strap that holds the rings together moves my cock away from my leg and then my steps causes my pant leg to push it back against my leg! Great…this can’t possibly be good all day long.

Surviving the day without cumming, I arrive home and turn up the heat a few degrees and strip down to the birthday suit. TV on and an ice cold beer I settle in for the evening.

At the “appointed time” I slide the DVD into the player and hit play. I’ve been naked for hours so that’s covered. I take off the Gates of Hell so the big guy can play free (per Mistress of course).

The video is old school stuff, at least according to the sales girl at Adam and Eve so this should be a treat.

Right off the bat I can tell. Huge mounds of pubic hair on the girls. That’s nasty! (Sorry to the bush lovers, I don’t mean to offend)

Shit, this guy is huge!!! Holy crap I thought I was big!

Mistress told me I’m in the 99% percentile in cock size. At first I was like how the hell do you know this…well, believe it or not there is a website that shows cock sizes in different parts of the world! Isn’t the internet wonderful …. NO, don’t leave now, check it later.

Back to the movie…

Wait… hold-on a minute, I just received a text…

…It’s Mistress …”I’m with my girl friends at the bar, we need some entertainment, send us text updates every ten minute about the movie and how horny you feel”

GREAT!! So I’ve got three smoking hot girls laughing their asses off at my expense!! I can only imagine what their talking about… Oh well! Mmmmm, on the other hand I bet Sexxx is one of them. I think the girl in the bar is Mistress’ best friend . . . she’s had a few bi experience with. That’s FUCKING HOT.

Anyway, the movie turned out to be fun thanks to the texting and my creative imagination!!

Wednesday

Ahhhh…. the day I get to pick a work fuck buddy …

This is easy I’ve had my eye on this girl since she started this past summer.

She is a graduate of OSU and recently passed her Bar exam. I know Mistress said to only think with my cock, no need to consider personality, intelligence, etc, etc.

But what can I say, even my cock loves to fuck an intelligent hottie!!! Smart sexy girls rock my world!! Yes, I know it’s getting old, but …… yet another thing I love about Mistress …. smart and sexy!!!!

Back to my work fuck buddy ….She’s about 5′ 7″ I’d say, maybe 110 lbs with black hair that comes to mid back. A super sweet tight little ass. She appears to take very good care of herself, nice tone body near as I can tell. Small tits, maybe a B cup, no more and maybe less. She has the body type I LOVE. Thin, tone, small tits … Sweet.

Throw in smart as hell and I’m fucking crazy horny to tap that!!

She is always professionally dressed, pencil shirts mostly during summer, never hose. A thong or nothing girl for sure, never a panty line in sight.

I’ve spent a lot of time with her of late as we are negotiating a contract and she’s writing the language for me as we progress.

Yup …. I’d hike up that little skirt, set her bare ass on the boardroom table, and …. you know.

So, Mistress here you are — [email protected]

Thursday

It was just after 1pm when I pulled into my parking space at the office. I quick check of email on my phone and I notice a new email from Mistress. I’m sure this must be the “other task” she told me I would receive later in the week.

I begin to read …

Sub XXXX,

In 56 hours, you will lose your virginity to me.

There is no turning back.

It is a bit of a taboo subject, of course, for most folks. Not for me though. There are insinuations and connotations of it being dirty and being gay. We’ll work through it because you trust me.

I’ll gather my thoughts and write to you how to do it from my perspective of having had anal sex before. Because there are muscles that clench, it’s pretty much similar each time.

Right now I want you to think about asking permission to lose your virginity from someone on EP . . a single person. I want you to write the note any way you choose but you must clearly state that “Mistress plans on taking my “other” virginity on Friday night but I must obtain permission from another party. She will not take me unless one other person says it’s ok.” Explain to the person that your note to them will be read by Mistress. Your note should be sent today or tonight.

Mistress —

FUCK!!!!! Are you kidding me!!…..

I can’t do this! Fuckkkkkkkkkkkkk…………….

Ok, calm down XXXX, I tell myself, just calm down…

Think…

Who could I ask…

I need someone that won’t be offended…

Someone that would be willing to help….

Someone that won’t make “too much” fun of me…

Scanning though list of friends…

And again….

Got it!!!

I know who I’m going to ask, now back to work.

Getting home, I write my “permission needed” email and hit send. My stomach is doing back flips with nerves excitement.

homenudie to JenniferSometimes Jan 19, 2012 5:41 PM (posted with permission)

Although I’m very embarrassed to ask you this, I’m wondering if you might be willing to do me a huge favor. My Mistress has told me I need to reach out to one of my EP friends and tell them about an upcoming task that I will be required to complete and to ask them for their help.

I know you read my story “Satisfying Mistress: A Weekend of Ultimate Excitement & Embarrassment”. Well this task is part of that continuing journey.

If you’re not comfortable with this or would rather not help, I completely understand, please stop reading and delete this email. Just let me know.

Given you’re still reading I guess your open to helping.

So let me explain….

This Friday evening my Mistress has told me that I must allow her to take my “other” virginity… “to give her my ass”. I have never done or even contemplated such an act, but I will of course do as she instructs.

Once I have completed my task I will finally be allowed to cum after 14 days of denial.

I will be very honest with you, I am worried. I look at the vibrator she had me to purchase and cannot image that thing being inside me. My only real comfort comes in knowing that she didn’t have any problem taking me in her ass and I’m much larger. She has also assured me that she will walk me through how to relax my muscles so it will be comfortable. I’m hoping she right!

So here’s the favor I need ….Mistress has told me that I need to receive the permission of an EP friend before I will be allowed to complete my task. I need your permission to give my virginity to my Mistress.

So here I go … May I please use the dildo I purchased at Adam & Eve to take my “other” virginity?

JenniferSometimes to Homenudie Jan 19, 2012 6:57 PM (posted with permission)

You are such a bad boy! I think you sort of like the idea of this 6.5-inch vibe in your ass! Because you need it. You know you do! Your mistress is in charge, and that’s the way it should be.

I would say I envy you, but that wouldn’t be appropriate. So I’ll just say, JenniferSometimes heartily gives you permission. Grab a hold of that big boy bend over and accept your fate!

Outstanding I think!!!! Oh, Mistress with be so pleased with me!!!

Forwarding email to Mistress …

Within a few minutes receiving a response,

Bravo, honey.

Nothing more…. Mmmmm sort of thought I might score more points. Oh well, I did it.

My list complete!!!! I’m a day away from the final prize and finally being allowed to cum!! I need to so bad, my balls are about to explode at this point. A day short of two weeks and teased relentlessly without cumming! Crazy!

I just need to wait for my instructions for tomorrow night.

Friday

Waking I head down stairs, fire up the coffee maker and scan work emails just like ever morning

I assume I’ll receive an email from Mistress around mid day so am not even thinking about checking gmail and head to the gym.

Returning from the gym I fire up my computer and open gmail. To my surprise I actually already received my email from Mistress!!!! Awesome! What a way to start the morning…

I begin reading…..

Sub XXXX,

I’m going to explain this as best as I can having experience with all kinds of penetration “toys” and anal sex with a “live” partner. As you said, the dildo is starting to look good because you’re so horny. Consider all the factors:

You’re doing this for me and to please me, your mistress. My pleasure is your pleasure. And trust me, it’s overwhelming for me knowing that you’re surrendering your virginity. For me.