2 comments/ 15968 views/ 3 favorites Satisfying Mistress Ch. 01 By: RKHunter It had been a long day of budget meetings and nothing was coming together as planned which seemed to be pare for the course this year. Walking past my admin Kathy with a sour glance and one of those "this sucks" looks on my face and into my office I dropped my stack of folders on the desk and flopped into my chair. I glumly listened to voice mail messages and scanned a long list of new work emails as I finished the last of my now ice cold coffee. I hadn't yet noticed the "new" email indicator on my iPad which sat next to me on the desk... Not feeling like doing anything after such a discouraging morning, I found myself leaning back in my chair staring into space getting more and more pissed with every passing second; I'd surely be spending the holiday weekend at the office. I was out of time and budget presentations would begin on Tuesday whether I was ready or not. My wife was still at our vacation home in Florida so not that big a deal I tried to tell myself, but shit, I had plans to go to the Boat & Camping show maybe the pistol range and certainly to watch football until my eyes were bloodshot! Yup, the perfect weekend to relax... and now all that was out the window. Resigned to my situation I reached for a pad of paper and begin creating my weekend "to do" list. It was then I noticed your email. Although pleased as I knew it was from you, I was also a bit surprised. You used an email account we normally only use for chat. An email account I've never shared with anyone but you. No matter, at least a ray of sunshine in an otherwise crappy day. I always love hearing from you. You have been my Mistress for just the past three months. We met on EP after I posted a story about wishing to have my orgasms controlled by a stranger. You had commented on the story, a weird mix of comment and question rolled into one. I could tell you were curious and poking around a bit to see what my response would be. A lot of course has happened since that day. We became friends and even hot passionate lovers during a recent visit to your home that found us fucking in your pool within an hour of my arrival. Your "man-toy" for the day you called me. All that however was behind us now, I was back in Ohio and you were in Florida. Our normal day to day worlds limit our D/s play to online and communications. Mostly via email and chat exchanges, although on occasion we would speak on the phone. Although you are the D in our relationship, every once and a while when you feel the need ..."to be taken ... to be treated like a cock slave ... to let your inner slut out" you tell me, we have switched roles. Those are the times you need to hear my voice ... commanding you to your knees as I push my meaty cock past your lips and down your throat until you gag ... commanding you to spread your legs wider so I can drill your pussy hard over and over ... and finally bending you over so I can finish by stretching your tight little ass until you scream ... leaving you with my cum dripping from every hole ... completely used, smelling of my juices. ... But I digress. Greatly. Opening your email I begin reading ... Sub *******, To fulfill Mistress's weekend requests, a field trip must be first taken to the Adam & Eve retail store at the Sawmill Center. You will purchase the following items and enlist the help of one of the female store associates. You need to get it right. The activities I have planned for the merchandise will be described in an ensuing email that will come to you later this evening or perhaps we will discuss them in greater detail. I want you to hand this email to the store associate. No need to apologize or feel the least bit embarrassed. They're used to assisting slaves and subs that must complete a number of personal tasks for their Mistresses. You will purchase the following. If the item is not available (I'm looking at the online catalog), ask the store expert to recommend something similar: - The DVD "70s Porn", a compilation of low budget goodies . . . the cream of the crop at the time. If not available, we're looking for unpolished porn, which marks the time period I believe. - The "Rings of Hell" product. Not sure if they have but something similar that will ensnare your raging cock will suffice. The rings are connected in ascending size order with the first one, I believe, anchored below your scrotum. You have my permission to discuss your cock size with the helpful store associate. - On page one of adamandeve.com, a short-time free offer is the "Waterproof Delight" vibrator, a "beginner's" 5.5" device for which I have very special plans to use on you. If that's unavailable, surely there's something similar to purchase. You may not get anything smaller. Larger is in fact better. You know exactly how we are going to use this so keep that in mind. - Purchase a lube that is best for anal use. Again, the expert will gladly make a recommendation. To My Pleasure, Mistress I sit stunned as I finish... You have never told me to do anything like this before. All of your tasks to this point have been low key and very private, just between us. Just simple denial, masturbation and some role play type stuff, like stripping and photographing myself in the restroom. You of course know all my fantasies ... one of which is to be sexually embarrassed and humiliated. You had months ago forced me to share them all, even the deepest darkest ones. And I had done as instructed. I always do. Could I really do this I think and actually go through with it? This time would be different. If you say I must, than I will as I would never let you down. My heart is racing although I'm not sure if I'm having a panic attack or am just super excited. I'm simultaneously filled with emotion and fear. I'm a senior executive at one of the largest employers in the area, I live in this town and know a lot of people. What if someone sees me ... what if the sales associate knows me ... what if she moonlights in our customer service department ... what if she is the daughter of one of my employees ... what would I do then ... would I still go through with it? I'm clearly panicking I think ... however if I'm panicking why is my cock getting so hard? Calming myself down a bit I remember it's only Thursday and I have two days to figure out what to do. To come up with a plan, to decide if I can go through with this or not. And just then I see another email from you come through ... For an instant I think, maybe it will say .... JUST KIDDING SWEETIE! Just wanted to get-the-blood flowing. And although much of me wanted to see those words, there was another part of me continuing to grow in my pants that hoped I would not. Opening the email I realize quickly that my cock would not be disappointed, however I was completely mortified by what I read ... Sorry my sub, but I forgot to tell you in the earlier email ... ... be sure to keep good mental notes about your experiences and how you feel performing for me this weekend. You will write story about your weekend adventures that you will then post on EP. Sharing ALL of the details with your friends. I'm guessing that will be very humiliating for you. Think about this for me while looking at the items you must purchase... ... think about what I'll make you do with them. Think about how embarrassed you'll be as you perform for me. Maybe I'll have you set up a video chat so I can watch. Mmmmm ...my younger sister is in town, maybe we'll both watch. Would you like that? Would you be embarrassed? Think about sitting there after finishing your story for EP and hitting submit. Think about all of your EP friends reading your story. Think about their shock. Think about sharing with the world what I demanded from 700 miles away. Just think about that for the next couple days ..... I was thinking about it alright. And even though I was sure it would be the most embarrassing and humiliating thing I may ever experience, my cock was ROCK HARD! Not a surprise I guess given it is my fantasy after all, I shared it with you, and you are now simply forcing me to turn my fantasy into reality .... This is after all what I crave ... Shutting down my computer and grabbing my coat I head to the restaurant for dinner with some business partners ... tomorrow will be another day ... and more importantly a day closer to completing my task. Friday morning ... I'm at work very early as I have a "weekends worth" of work to get finished. My weekend plans have changed a bunch since getting your email. All for the good of course and I'm still very excited. And although I'm making good headway I also find myself struggling to remain focused. I begin reflecting a bit on my situation ... ... sitting in my office, turning to the left and looking through the floor to ceiling glass wall that forms one side of the office I see my staff. Turning to my right and out the window I enjoy a lake view that is coveted by the select few that have offices in the executive wing. I sit behind a large mahogany desk in my high-back leather executive chair and am equipped with the finest of all office electronics and any other implement I could ever need. I have a full time assistant that caters to my every whim, even down to ensuring my newspaper is always on my desk and open to the proper page before I arrive. I have significant power and authority within the organization. I am the go to person, the person that always gets the last word, the person that no one in their right mind would ever challenge. The person that is never told what or how to do anything, and if you ever tried a bloodbath would certainly ensue, and I would without question be the last man standing. When I say jump, the only question is ... how high sir? I reflect on this for one obvious reason ... ...tomorrow a young lady in her mid 20's will tell me to do things that I can't even make myself do. And I know that I will not only do what she tells me, when she tells me, and how she tells me, I also know I would beg her to allow me to do so. How can one person be both these people, the power hungry executive and at the same time an eager little submissive to a woman my daughters age? The answer of course is simple ... ... you are allowing me to be who I am ... and I am both of these people. I receive thrill and satisfaction from both. The difference being that the powerful executive is admired by others, put on a pedestal for others to worship. How can I possibly step off that pedestal and into this world you are about to ask me to enter ... ... how can I possibly share the completely humiliating acts you will most certain require me to perform with my EP friends. To share not only the acts but also how they made me feel. I guess I'll find out soon enough. I have few options really. If I refuse you will no longer be my Mistress. That's been the rule since day one, and I have come to need you more than I ever thought I would. You are an important part of my life and I have come to care deeply for you. I'm sure we would still be great friends if I failed, but I need more than that from my Mistress. I need you to control me. Putting the finishing touches on my budgets I pass them to Kathy to clean-up for next week's meetings. Grabbing my coat and wishing everyone a great weekend I head for the car and the closest bar, I need a drink in a bad way. I'm now less than 18 hour from starting my assignment ... ... I expect it could be a long night. Saturday 10:49am ... I pull into the parking lot at Millsaw Center shopping plaza and drive slowly past the front of the Adam & Eve store trying to see who might be working. At the same time I'm checking cars in the parking lot to see if I recognize any of them. The shopping center has several stores in addition to Adam & Eve including a Mexican food mart, a furniture rental place and a health food store. The Adam & Eve store has large windows so it is easy to see inside, however the counter where the sale associate would most likely be standing is hidden from view. I drive through several more times before pulling into a space out front. My hands are starting to sweat as I read your email for the 100th time. The paper shaking so much I can barely make out the words. I need to calm down. I can't hand this to the sales girl and be shaking like a fucking leaf. Just as I'm about to get out of the car a middle age couple walks into the store. She's a shorter lady, sort of heavy set and he's big burly guy wearing a Carhart jacket, looks like a small mountain actually. Shit, how can I walk in now, what if the sales associate laughs, what if she shows them the email? FUCK, FUCK, FUCK ... what the hell do I do!!! I'm clearly panicking now ... I can so totally tell ... there's no movement in the pants ... if anything the big guy is retreating up into my balls. Ok, 10 deep breaths, calm down ****, you'll be ok I tell myself...and again. Regaining my composer I pull up your picture on my phone, the one I took of you sitting outside the Key**** Bistro. You're amazingly beautiful and so confident, you give me strength. I will not fail you! Fuck whoever is in there, I don't give a dam!!! I walk through the door with a renewed commitment and confidence. I scan the store quickly and notice only the couple I saw earlier and the sales associate. She's in her early 20's with a slight Asian look, maybe 5' 2' with long black hair, super nice smile and very thin. She is quite attractive and I would most certainly fuck her given the chance. She welcomed me and asked if she could help me find anything. That would be wonderful I said and told her I had a list of things I needed to pick up. Unfolding the email and setting it on the counter in front of her, she immediately picks it up and starting scanning for the items. I could tell she was not reading from the beginning just scanning for the "list". She starts reading the items and descriptions you had provided out loud. Finishing, her eyes bounced back to the top and I could tell she reads the subject line. My guess is she got to the bottom and noticed your Mistress signature and that peaked her curiosity. "Feel free to look around a bit as I look these items up on the computer", she said. I'm thinking shit! She's keeping the email and will most certainly read every word. I could feel my cock stirring in my pants. It was a rush for sure! The store was divided into sections with lots sexy play cloths. Not really what I would call lingerie, it was more like "fun and games" cloths. Like a stripper might wear or the horny house wife doing a pole dance for her hubby in the bedroom. There were also several displays of full nylon body suits, like pantyhose except that covered the entire body minus the head. Someone with a pantyhose fetish would go nuts over this stuff! Most of the cloths were for women however there was some guy stuff, mostly funny boxers, and man thongs. Glancing back at the sales associate, she was busy reading the email and then jumping back to the computer. A few minutes later getting up and heading my way. ******* she said, referring to me by name. SHIT!!! .... I forgot to delete my name!! At least it was just my first name! My heart starts racing ... Let's start with the videos she said, I'm not sure we have anything that's true 70's but it sounds like she's looking for something more naturally vs. staged. Do you think that's right? she asked. Yes, that sounds right I say. Something less polished. I totally get it she says, some of this stuff (pointing to the wall of videos) is so predictable, you know exactly what's gonna happen. I like some mystery myself or it gets so boring. I'm thinking, I cannot fucking believe I'm talking to this young women about our porn preferences. It was so fucking HOT! We could have just as easily been talking about our favorite meals. It was so natural, like nothing big. Totally crazy! Picking the movie she checks the list again and we move to the cock ring section. It was like I had a sex shop personal shopper. Her name tag read Romance Consultant. How cool is that. She explains all the different styles as she refers back to the list. Your friend (referring to you) is asking for the Rings of Fire, and although we don't have that, we do have these which are similar. Going on to explaining how they fit on the cock and what their designed to do. Again, I am in fucking shocked at how natural this conversation was with her. She told me that she understands ... that when I do finally cum (yes she said cum) it will be super strong!!! FUCK!! I cannot believe she just said that ... I'm starting to feel like we're have verbal sex Moving onto the "waterproof delight" vibrator ... ...this is where things get completely out of control. She takes me to the butt plug section and starts reading the sizes off the package. I know you need something that is at least 5.5 inches she says. I ask if these vibrate. No she says, going back to the list and rereading. Having a confused look on her face, she takes me to another section. I can see immediately we are in the wrong section again. Mmmm how do I tell her, mind racing again... I find us looking at g-spot vibrators. I didn't even know they made such a thing! It's like a small egg vibrator on the end of a stick that a woman would stick up their pussy providing more complete stimulation of the clit I guess. Not sure actually and could not bring myself to ask. It's clear I need to help her at this point ... as she confused. What about regular pussy vibrators I say ... yes, I did go there and call them a pussy vibrator. Oh, we have lots of those she says...I thought you wanted something anal. I realize I'm going to need to share more as she's not connecting the dots yet. I do want something that can be used anally, but it also needs to vibrate I say. Got it she says, and starts showing me these cock shaped vibrators. She goes on to say, I don't have much experience with anal toys personally, but I'm told this one is great. Do you think she'd like this one? Mind racing again... do I take the easy way out, or come clean. I'm thinking about Mistress and my task, come clean, it's the only option. Well I say, it's actually for me, you wish to take me anally I tell her ... ... finally the light bulb goes off in her head, she finally gets it!! Ah she says, sorry I assumed it was for your Mistress (yes she said Mistress) now I totally know she had read the email in detail. Totally HOT, I'm thinking ... Ok she says, so we need something flexible that's at least 5.5 inches in length right? Yes I say. After showing me several options and what she likes about each, I pick one that seems to fit the need best. It's a bit larger at 6.5 inches but I'm guessing Mistress will be ok with that! She however has a somewhat concerned look on her face. She asks me how big I have taken in the past. I told her that actually this would be my first time ... that I was a virgin. She told me that the one I picked might be a big large for a beginner. I'm concerned of course, but nothing else seemed to be better. I tell her that it will be fine. Ok, no problem she says, just go slow and use plenty of lube. FUCK, FUCK, FUCK ... I am so embarrassed we are talking about this I think ... All my toys selected we had back to the counter, I pay and thank her so much for all her help and then had for the car. It was a totally crazy experience actually. Not nearly as bad as I thought it might be, so natural in many ways ... Getting back into the car, firing up the iPad and send you an email describing what I have purchased for your pleasure ... I'm hoping you will be proud of me ... I head home and wait for my further instructions...what will you make me do with my new toys, who will I tell.... Satisfying Mistress Ch. 02 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 -- Lexi.XXXXXX@XXXXXXXXXXXX.com 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. Satisfying Mistress Ch. 02 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 dildo 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 fucked. . . 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 cock pushing its way past. You won't force anything but you will apply gentle yet constant pressure. Don't think with your cock . . . 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 cum 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 "asshole", 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 dildo. It's entire length. Use the same method you would use when you masturbate. Remember that? Lots. Think for a second. It's not your cock. You would normally be on the receiving end. It's going up your ass. Now, brace yourself with your left hand and rest your head on the bed, knees as forward as you can, hold the dildo 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... 9:57pm 9:58pm 9:59pm 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.