Satisfying Mistress: A Weekend Of Ultimate Excitement & Embarrassment (part 2)

The story is a continuation of  “Satisfying Mistress:  A Weekend of Ultimate Excitement & Embarrassment




Satisfying Mistress, Part 2


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 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 *******! So be very careful. Oh, as I said before, I want you to keep the “toys”, especially the *****, on the kitchen table all week. A pleasant reminder of your tasks.

2- You will watch the **** 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 **** 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 ****. 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 ***** 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 **** video, nothing to it.  **** has never floated my boat anyway.

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

…Pick out a woman at work my **** wants to **** like a ****…fun!  Give Mistress her name and email address with threat of sending nude picture of me!!!!  **** 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.  ***** down and grab the Gates of Hell.   Seems simple enough to put on, just slip my **** through the 6 rings and then pull the largest ring at the end over my balls to rest at my base.

****!!!  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 **** through rings and stretch large ring over balls. Mmmmm… rings don’t stretch, **** this is very hard rubber.  How the hell am I suppose to get this over my balls.  Mmmmm, maybe try balls first and then ****.  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 **** back through rings, grab sack and pull through end ring…..ouch…..  ahhhhh…. success.  ****!!!... where the hell are my balls?  Sack is empty, crap balls are still on wrong side of ring!  ****!

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 **** out, not straight out, but not hanging either.

Sort of reminds me of when Mistress has me lay my **** on her open palm, just to mess with me.  Just slightly supporting its weight but not providing any stimulation.  That drives me ******* 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 ******* 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 *** 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 ****…“Houston we have a problem”… I’m gonna ***…****…STOP…STOP…think about something else…….. anything ……………focus………….mowing the lawn, ok, that’s good, mowing the lawn. 

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

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.



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” **** 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 **** ring yet!  I spent all day yesterday naked.

This is interesting … it sort of makes my **** bounce against my leg with each step.  The leather strap that holds the rings together moves my **** 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 *******, I arrive home and turn up the heat a few degrees and ***** 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)

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

Mistress told me I’m in the 99% percentile in **** size.  At first I was like how the hell do you know this…well, believe it or not there is a website that shows **** 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 ***** 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 ******* HOT.

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



 Ahhhh…. the day I get to pick a work **** 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 ****, no need to consider personality, intelligence, etc, etc.

But what can I say, even my **** loves to **** 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 **** 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 ***.  She appears to take very good care of herself, nice tone body near as I can tell.  Small ****, maybe a B cup, no more and maybe less.  She has the body type I LOVE.  Thin, tone, small **** … Sweet.

Throw in smart as hell and I’m ******* 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 *** on the boardroom table, and .... you know.

So, Mistress here you are –



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 …


 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 –


****!!!!!  Are you kidding me!!.....

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

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


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 ***”. 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 *** 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 *** 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 ***** 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 ***! 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 ***!!  I need to so bad, my balls are about to explode at this point.  A day short of two weeks and teased relentlessly without *******!  Crazy!

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



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…..


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 ***** 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. 

It's taboo and it's unknown. There's a guilty pleasure in that.

Even though you're 700 miles away, I will be there to guide you. I will be there to witness you losing your virginity and, vicariously, take great pleasure in your pleasure, uncertainty and, yes, a bit of pain. After all, isn't pleasure so much better when it is not so easily attained? Yes!

You might want to read Allergic’s story about anal sex before you proceed and before you even read the rest of this email. It's extensive and answers several questions from hygiene to climax, the former equal to or more important than the latter.

I suggest you do the following before you contact me at 10 pm tonight. You need to be comfie and relaxed. If you need to go, take care of business and if you're unsure or uncomfortable with the idea that there may be roadblocks stop off at CVS for a couple of disposable enemas. Good thoughts now. Think about being over the knee of mistress or on all fours while I fill you with a warm, aqueous solution. No, not that. Salt water silly.

Take your shower now. I suggest a hot one. Skin tingly. Clean feeling. Relaxed. That's right, forgot for a second, you're a cold-climate creature. Mistress is still in shorts, tee shirt and sandals with the a/c on. Turn up the heat in your home an extra degree or two.

Get your ***** ready. I should have directed you to get a flesh-colored one instead of a garish color but, then again, you won't be in a position to notice the color. Or care. Get your lube ready.

Two setup options, and I'm already regretting not flying out to personally orchestrate the entire process:  on your bed or on a very comfortable rug or mat on the bathroom floor. I mention the bathroom floor because you might want to position the mirror so you can watch yourself getting ******. . .  that is if you can keep your eyes open from the pleasure.

Here's the thing. There are, I believe, several rectal muscles in play that are not quite used to a semi-rigid artificial **** pushing its way past. You won't force anything but you will apply gentle yet constant pressure. Don't think with your **** . . .  plunging in and out. You're going one way because if you pull out the muscles will seek their original position. Muscle memory.

All fours now with your knees exaggerated inward. Head lowered. Oh, I hope you're not on that expensive Egyptian Cotton comforter. Your wife will kill you. Be safe. You're on sheets now or the beach towel positioned correctly. Not sure about lube stain. The *** stains will come out in the wash.

Squeeze a very healthy amount . . .  now double it . . . onto three fingers and work it around your rectal opening (no I'm not going to say "*******", silly), slightly in, more in, all the way in. Gently but with authority. Those are key words and a key thought that will be repeated. All around. Imagine those fingers are long and soft. My hand.

Squeeze lots more on your hand and apply it to the *****. It's entire length. Use the same method you would use when you **********. Remember that? Lots. Think for a second. It's not your ****. You would normally be on the receiving end. It's going up your ***.

Now, brace yourself with your left hand and rest your head on the bed, knees as forward as you can, hold the ***** at the very base, and put the head by your rectal opening. You will only get a half an inch before you will face resistance . . .  your first obstacle. Remember, constant but gentle pressure . . .  push. . . let the rectal muscles relax . . . maybe pull out a tenth of an inch but push back immediately. It may be a minute or two or more before more length slides in. Gently. Next obstacle. Push back against the head. A little harder.

Got it? Don't stop until you have taken the entire length. Hold it in. Be still for a moment. You enjoy being filled. You enjoy that you have pleased your mistress. You enjoy what you have accomplished.

Only now may you seek relief. It will be a tiny challenge but your left hand may be used.

First say, "I love you Mistress."


I find myself speechless …not in shock, but in happiness.

I read the words again and again.

My task may be clear, but what’s even clearer to me is how you feel about me.  You care for me, more than you might wish.  More than maybe you should.

I read your words and I feel you within me, I feel you around me, and I feel holding me.  I feel special.

I look at the clock on my PC and wait…




My screen comes to life as you sign onto webcam at exactly 10:00pm as I knew you would.

You are stunning….you’ve done your hair, your make-up and are even wearing earrings.  You look like your heading out on the town, but I know it’s just for me.

I hear your voice…

“I’m here for you Hon...feel my hand, the warmth of my skin against yours…I’ll be here next to you tonight for as long as you wish…your doing this for me and that pleases me and I know pleases you as well.  Go slow, we have all night...”

I feel safe as you are here with me, next to me and holding my hand … I will do this for you… I will please you, for it’s what I crave to do … I do love you Mistress.

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7 Responses Jan 22, 2012

Wonderful story, wonderful Mistress. I envy you.

This was again amazing, it had me laughing, and it had me excited. You are an unbelievable story teller!! Hats off to both of you!!

Howdy Homenudie. You account has me very aroused and I actually slowly undressed myself nd found pleasure in each and every word. Still, as I type, I find that I want to be with your Mistress and on my knees before her and seeing to her ultimate pleasures.

AWESOME!! Really well written too! How cool that you found a whole other side to your nature too.

This has been quite an adventure reading these stories... I enjoy learning more about you every time I sit here and read them... To be honest you know I'm totally a sub and love to be dominated so to read this from a man being a sub.... it is interesting and I thoroughly enjoyed even if at first I didn't think I'd like it. It must be truly exciting to have all these instructions you must follow... in fact I'm jealous I wish I had a master that would do this kind of thing to me.

This was expertly written - very humorous and erotic at the same time. Thank you for sharing with us. I am envious of your ability to be so open, so free with everything. Now let's see if there is a part 3 . . .

And you will, of course, share that as well?

I hereby request a continuation of this story, with all due respect. I feel that as a reader I have unanswered questions.

Wow. I'm feeling so many emotions simultaneously. There is real beauty in this story homenudie <3