An Errand for Mistress
  • Author - Rebecca Bronwyne
  • Rating -   
  • Site Rank - 1355 of 2955
  • Story Codes - F-f, reluctant, analplay, bondage, loving, non-fiction, toys, tricked
  • Post Date - 9/29/2013

Author's Note: My first attempt, so I welcome feedback! Just please be respectful with your criticism!


I. Preparation, Part 1

She sat staring at herself in the visor mirror. Slightly flustered, it was annoying that it took nearly half an hour to get to the store from work. She would be halfway home on the highway by now.

Fucking Boston traffic she thought, and immediately chastised herself for the potty mouth her Mistress punished her for.

She had changed from her business clothing into what she thought her Mistress would want her to wear for this errand in the car. She had purposefully parked two levels lower in the garage today, knowing full well that everyone preferred to park higher, and closer, to the entrance.

The sleeveless cocktail dress clung to her body quite nicely. A bit too nicely. She wasn't young anymore, and even though she was what people termed a "thick chick", she still had curves that some women would die for. She had fussed with the garter belt and stockings earlier that morning, but they imprinted too easily on the mini-dress, so she opted for the stay-up pair she bought for such occasions.

Then there were the heels. Basic black of course, just like her dress. She sighed as she thought about the time she picked them out. The four inch heels were just too, well, spikey (is that even a word?) to walk on easily. But they looked so good! Instead, she went with the three and a half inch heels. At least they helped to show off her calves nicely.

Finally, the Venus Butterfly G-Spot vibrator. Mistress had sent her on her way last night with an order not to orgasm until after she woke up for the day. But, being the sleepy head she is, she was too groggy to do anything about it. The night before had consisted of her reading a story Mistress had sent her a link to. It was rather erotic and had her rubbing herself consistently as she read. But, like a good girl, she didn't come.

So naturally she had to do something about it the next day. The straps for the butterfly were thin, so they didn't show through the mini-dress, and definitely didn't through her business skirt. The heels and stockings were worn to make the change a little easier.

Looking her hair and face over in the mirror, she rolled her eyes and stopped her primping. This isn't really a first date, that's just the way she was told to dress, Now she fingered her public collar before starting to remove it. The simple black velvet "choker" was perfect for every day. She even received a few compliments from co-workers, including one from one of the partners who lamented that it was nice to see some good old world fashion sense for once. If they only knew!

It always felt strange removing the public collar to put on the private one. Almost like a violation, a destruction of trust. But she was thankful that Mistress understood her work situation. She didn't want to end up out of a good paying legal job like the poor college girl who was found out to be the stripper Miranda Wright by night! And how could they have fired her? Couldn't they at least appreciate the sharp wit that came with choosing such a name?

The private collar was a whole other story though. It was chromed steel, an inch and a quarter wide, and even had a ring to attach a leash to. Rebecca usually wore it with the ring to the back so her medium length brown hair could hide it. And to what end? She only wore it in private! But nonetheless, she did it...but not today. Mistress had decreed that it be visible to the front.

And so it was.

Okay, here I go!


II. Decisions, Decisions

She walked timidly into the bookstore at first. She had been in adult stores before, but this time it was a little different. She had a mission. She observed two employees, male and female, both seemed to be young. College students probably, Boston was full of them now after Labor Day. There were two customers she could see immediately, both male. Rebecca immediately went to her right and started perusing the items on display. Not consciously looking for anything yet, she just seemed to be wandering slowly to her left looking over each item.

She heard the approaching footfalls and turned to her right to see the female employee walking toward her and flashing a genuine smile. "Hi! Can I help you look for something?" Her eyes quickly scanned over Rebecca's body, head to toe, in a split second, but her eyes seemed to linger on the collar as they came back up.

Rebecca's eyebrows arched in resignation as she answered 'No, thank you...just looking for now'. "Okay, well let me know if you need anything." was the reply as she once again lingered on the collar before turning away and walking back towards the counter.

One hour she thought, I have to meander in here for one hour? She looked around the store again to take it all in. Well, if she took in everything, including the videos and lingerie that would cover it. She noted yet another male customer. How cliché she thought as she went back to looking over the wall covered with oils, lubes and supposed aphrodisiacs.

Dildos, vibrators of all kinds, some light BDSM paraphernalia. And then it happened again, the footfalls. "Are you sure you don't need some help?" came the friendly voice. Rebecca smiled. It was hard to be annoyed with the girl. She was about the same height, but obviously thin as a rail, the bitch. Not ugly, but not gorgeous, she fell into the same realm as Abraham Lincoln described when he said that God preferred common looking people.

'I'm good for now, thank you though.'

"Okay well like I said if you need help picking something out or have any questions about anything just tell me!"

Both smiled almost in unison 'I will. Thank you again.' As the girl walked away Rebecca was happy to know that part of her errand could be done more easily now. Not really knowing what questions to ask, as Mistress instructed her to do, it was going to be easier now. And thankfully it was the girl and not the guy who approached her! Ever since the divorce, she had been exploring her bisexual impulses online (and that is where she met Mistress). It's not that she was rejecting men forever, she'd just had her lifetime full of cock and now she was looking for something different.

Surprisingly, the hour passed, more or less, uneventful. Customers came and went. Some leered at her like she was a piece of meat in a butcher's display case; others (the young couple) noticed her but paid her no mind. But after the sales girl had left her last, she could see that she and her counterpart were talking. Probably just the usual co-worker banter?

Rebecca lingered in the anal toy section, as that was her task. Get an anal toy of some sort, buy it and ask questions about it, but which one? She'd shopped online before and seen assortments. But this seemed a little overwhelming, a looming wall of lust before her. She wasn't very experienced with anal play, but not for a lack of wanting. Her ex had only anally penetrated her a grand total of 3 times, and only later in the terms of her two pregnancies. She had played with fingers, and even once Mistress had her get her vibrator all the way in during some play. Wow, was that an eye opener!

Time to bite the bullet she mused as she made her way toward the counter. She noticed the male employee meander away as she approached, and there was only one other customer in the store now. That made it easier to talk to the girl! Or was it too easy? Stop being paranoid Becca.


III. The Sales Pitcha

She smirked as Rebecca walked up. "So?" was all she said. Rebecca began to search for the right words smiled shyly and opened her mouth to speak. 'I...I was looking at the anal toys...' her words trailed off. Sheesh, what a wimp! How could this be? Online she was, as Jessie the Body once said, a sexual tyrannosaurus! Mistress often complimented her. But this was different. Real life. Face to face.

The girl made a "don't worry" face and gesture, and then spoke. "Kinda overwhelming isn't it?"

'A bit, yes.'

"Okay well, why anal toys?"

Rebecca immediately blurted out the answer 'It's what my Mistress sent me for.' and immediately her face turned a shade of oh shit why did I just say that!?!?

The girl leaned forward a little and showed a smile that was something between a smirk of sincerity and mischievousness. To which end of that spectrum she wasn't sure. As she flicked the leash ring with a quick finger flip she answered "No kiddin'?"

Rebecca flinched slightly at the gesture, both from the shock value and obvious forwardness of it. But she immediately recomposed herself and just started spilling the beans, so to speak.

'I was told to spend an hour here and then to buy an anal toy, any toy, and then ask questions about it.' Her own candor surprised Rebecca as she was speaking. It didn't seem to affect this girl at all though. She must have seen it all working here!

"Well, are you experienced with anal play?"

'Not really, just some experimenting.' She stopped short of revealing her intrusive forays into anal pleasure.

"It takes some practice, some training, to make it more pleasurable than painful..." Rebecca could swear she had emphasized the word. "...hmmmm." Her eyes narrowed a bit as she was in thought and then walked from behind the counter. "Wait here." It wasn't so much a request as a command. Rebecca nodded and continued looking to the wall behind the counter, slightly embarrassed to look elsewhere, lest someone make eye contact with her!

The girl soon returned. As she moved her way back behind the counter, she placed a box down in front of Rebecca. Anal beads? More like golf balls! She looked up to see the girl with that same half and half smile as before. Only this time, Rebecca was convinced it was closer to mischief.

"Multi-use. Anal or vaginal play. But make sure you wash and sanitize before switching." The words hung in the air, matter-of-factly. She couldn't quite look the girl directly in the eyes, kind of at her cheekbones, the way Uncle Sam's TI's had told her to look when being spoken to by a superior. She shook her head up and down, acknowledging the statement and loosely taking hold of the box in both hands.

"Any questions?" It almost had a twinge of hope attached to the phrase.

Rebecca regarded the box and some thoughts raced through her mind. It had been a few weeks since her collaring (well, her real life one) and she can still remember how her Mistress appreciated the fact that she was willing to purchase collars and actually wear them, let alone to carry out tasks (such as her nightly adorations) in reality. She was suddenly very conscious of the chromed circle around her neck. The girl's words snapped her back to reality in an instant.

"Want to give them a try?"

Rebecca's eyes widened slightly at the suggestion. She quickly blurted out a response. 'Is that allowed?'

The girl declined her head slightly and looked out of the tops of her eyes. "Not exactly. Buuuut, I can always write them off as received damaged in shipping if you don't like them." That smile returned. Definitely mischievous now.

She quickly scanned the store. Where...? But her thought process was cut short, almost as if this enigmatic girl was reading her mind. 'Come with me.'

Rebecca's lips both curled inward, the way a little girl's do when they know they are about to do something they probably shouldn't do.


IV. Preparation, Part 2

As the door opened Rebecca quickly took in the scene. This seemed to be an office. Desk, chair, computer. But it was also like a break room. A TV and white faux leather couch stood out immediately. As did the spray bottle of bleach and paper towels on the floor on the far side of the couch.

The girl began to talk as she fiddled with the DVD player. "Take your time. I'll lock the door behind me, and I'll knock before I come back in." She turned to face Rebecca and saw her eyeing the room. "Relax. It will definitely make things easier!" She offered out her hand. Rebecca instinctively took it and was led over to the couch and seated herself. There was definitely more to this girl than meets the eye.

She turned and walked to the door. Looking back in before closing the door and locking it, Rebecca could see that smirk again. But this time her eyes were a bit more narrowed. Or were they? Her attention turned next to the DVD that was playing. An amateur porn of a rather attractive blonde masturbating. Well at least that will help calm me!

Paranoia (rightly justified) quickly set in, and she got up, checked the door (it was indeed locked as promised) and scanned the room for the usual hiding places for cameras. A few minutes of searching and she was satisfied that she was not being spied on.

Sitting back down on the couch (it was rather comfy) and closing her eyes she reflected on her day since waking. The drive in was accented by the butterfly, working constantly in this mode or that. Mistress allowed to edge, and did so three times during the hour long drive in to work. The butterfly had certainly made it easier to please herself while driving. She had received more than a few stares and honked horns in the past. But now it was discrete. A guilty pleasure.

She slid her hands in the sides of her dress, under the cups of the bra, and began to caress her breasts and tease her nipples. She loved nipple play. They were quite sensitive and the clover clamps Mistress had her purchase had been put to good use from time to time.

Relaxing, she slid her ass down and forward a bit, turning herself so her feet were propped against the opposite arm of the couch and turned to watch the video as she continued to fondle herself. God I need this! she thought. The edging had lasted all day.

She decided to pay tribute to her Mistress by not allowing herself to orgasm for as long as she could stand it. And so far, she could stand a total of 10 edges, 4 of them rather intense. One came while talking on the phone with a client about an upcoming court date. It was all she had in her to repress the urge to vocalize her pleasure. She must have sounded rather taciturn to the client she had mused after the fact.

Content that she was well primed, and enjoying the display on the TV, she hiked the skirt part of her dress up to gain access to herself. The butterfly stared back at her from under the panties. Deciding to take matters into her own hands, she removed the panties and the butterfly. It was rather moist, and she wrapped it in a few paper towels before placing it in her pocketbook, the panties hanging part way in, and part way out.

She settled back and began fingering herself, unconsciously doing the same exact thing as the blonde she was ogling on the TV.

A few minutes of play had convinced her to try the beads now. She opened the box, removed them from their packaging, and noted three packets of lube that were somehow included. She coated the first ball liberally, the whole packet. Holding the string she slid her ass forward more and planted her feet into the couch cushion, toes pushing into the cushioned arm. Raising her hips slightly, her eyes focused on the TV.

I can't believe I'm doing this echoed in her head as she began to push the lubed ball into her anus while bearing down. She could feel the ball widening her opening, making it slightly uncomfortable. As the ball continued to slide inward, the pain increased. It wasn't horrible pain, but it was definitely uncomfortable. Her mouth reflexively opened and she began to moan as she watched the blonde riding a dildo into her ass repeatedly. Then, suddenly, the ball popped in and the relief of the pressure caused her to let a small moan escape from her lips.

Pleased with herself, she immediately lubed the second ball and began to force it in. This time it went with less effort, but still there was resistance. But soon enough, it was inside, and followed by the third lubricated sphere. All three balls filled her anal cavity at once and Rebecca's eyes were wide. Her breathing was escalating. Her hands, now free of their task, immediately went to her pussy: right hand to the clit and mound, left to the labia, just like she always did. Just like she had since she was 11 years old.

Rebecca lost herself in her masturbation. She was conscious that the video ended, but not sure how long it was, or how long it had been off. She only knew she felt very wet, her nipples were the engorged puffy cones they always were, and she was rocking her hips in different directions to get sensations from the anal beads.

There was a soft knock on the door and it snapped her into the now. The familiar voice of the girl stated "I'm coming in." and the door began to unlock. Again, a statement, not a question. She quickly moved inside and closed the door, locking it. As she turned she could see Rebecca mostly laid out on the couch, the balls of her heeled feet still pressed against the arm of the couch. All Rebecca could do was stare back at her. But this time, she made eye contact. And that made the girl smile wickedly as she moved forward and sat on the edge of the couch where there was room.


V. Build up

Rebecca's thighs were being caressed as her legs remained open, the girl looking down and examining the sight. "Nice shaving job. You should really start waxing though." A closer examination, and a raised eyebrow. "I see you got them in?"

'Yes Miss.' The words escaped her mouth without a thought, even though she immediately reflected upon it. The Miss just smiled. She understands what I just implied!

Two fingers began to wiggle slowly back and forth, working their way through the folds of the swollen labia. "Wow, you are really swelled and really wet."

Rebecca immediately went into submissive mode; the tone of the voice was like a mental trigger. "Yes Miss, I'm often very wet, even when not turned on." She instinctively glanced at the panties, and that drew Miss' focus away, but the fingers...the fingers were still tantalizing. "I...I have to wear panty shields every day or else it becomes... messy."

Miss reached down with her free hand and pulled them out of the pocketbook, examined them, saw the soiled panty liner, smiled and placed the panties down on the floor and out of Rebecca's sight. "That's pretty impressive." The fingers meandered their way up to the engorged clitoris, its hood retracted. Rebecca immediately shivered in delight at the sensation of her nails lightly tracing outlines on it.

'Oh GOD!' she blurted out, rather loudly.

Miss pulled her fingers away and looked sternly at Rebecca. "Too loud." And then she began to remove the heels.

Holy shit what have I gotten myself into!? she thought as her eyes followed every deliberate move of Miss'. She can't be older than 25? Probably like 21? I'm like twice her age! The heels removed, she began to slowly remove the stockings. Soft hands started caressing each leg as they worked downward, slowly, firmly. It was starting to really turn Rebecca on even more as she watched Miss watching her.

Both stockings removed, she stood and moved to the side of the couch where Rebecca's head was situated. She tried to follow the walking path, but Miss reached out with a firm hand and held her head so she was looking forward...and down, right into her own shaved and glistening crotch. Then she felt the breath near her left ear as Miss spoke in a whisper.

"I'm going to gag you, just relax." Rebecca felt as though she had no choice (or did she?) and did what she was told. The first stocking was rolled along its length, like a length of rope and held out in front of her face. "Open your mouth, tongue flat." Again, that commanding tone which elicited and immediate reaction. The stocking slid over the top of her tongue, to the corners of her mouth, and then was tied off. Next came the other stocking, wide and flat, also held out for display. "Close your mouth". Rebecca did as she was ordered to do, and the stocking covered her mouth from just below the nose to the bottom of her chin. It was fastened more tightly and Rebecca winced and grunted slightly at the forcefulness. After being tied, Miss stepped around front to examine her handiwork and smiled.

She began to position Rebecca like one would a mannequin, and she was just letting her do it! She was watching, wondering if it was a dream, but knowing that it wasn't. Miss obviously has some experience in this sort of thing, but what will Mistress think? she thought to herself as she realized she had been positioned for her relaxation as well as for easy vaginal access. Wide open, she was now self-conscious about just how wet this had all made her.

The hands began to caress her thighs and spread them further open as the head moved down and in. Rebecca watched like a deer in the headlights at 3 AM. And then she felt it. The first real touch of a female tongue in her sweet spot! Her eyes rolled into the back of her head and she totally relaxed, letting out a long, stifled moan. And that seemed to just encourage Miss because she went right to it and Rebecca's mind was suddenly keenly aware, all neurons firing. Oh my fucking God how the hell can she be this skilled!??!


VI. Release

The constant edging all day was taking its toll, she was going to come, and quickly. But Miss suddenly stopped and pulled away. No, please don't stop she pathetically called out in her mind. But once she saw Miss remove her top and saw her tiny A cup breasts with very pointy nipples, she knew it wouldn't be long before she was back in Pleasureland. Population: her.

The orgasm swept over her quickly, without warning, Rebecca tensed and moaned out uncontrollably into the double gag as the tongue and lips danced in, out and across her ever moistening pussy.

But she wasn't letting up! Her mouth opened and Rebecca could feel teeth at the bottom edge of her clit, and a lip over it, the tongue lashing at her relentlessly, combined with the warm, airless suction of the mouth closed on her sex.

The orgasm was still in swing when Miss pulled her slightly forward, so her ass was right on the edge of the couch seat. One moment it was sheer bliss, and then the next it was like a grenade had gone off in the room.

A skillfully pressured thumb on a now over sensitive clitoris, a wildly undulating tongue and a quick pull of the string to pop one bead out and Rebecca thought she was going to die of a heart attack.

Her breathing was out of control, her hands had an iron grip on portions of the couch as she dug her nails in. And just when she thought that was going to be the best thing she ever felt, she was proven wrong.

As best as her very compromised faculties could comprehend, the mouth moved up and closed instantly and tightly on the clit, sucking and flicking the tip of the tongue relentlessly. At the same time two fingers penetrated her vagina, curving upward and inward, the pads of the fingertips frantically rubbing away at the bumpy flesh behind the pubic bone. Rebecca's back arched violently and that's when the pin was pulled: the other hand quickly and firmly pulled both remaining beads out of her ass.

Rebecca's lower body convulsed violently and repeatedly as she began to forcefully squirt her juices right into Miss' face


VII. Aftercare

As best as she could reconstruct while driving home, she totally soaked Miss' face neck, hair, chest and the couch, as well as the small space of the floor in between. Her body spasmed and twitched for minutes afterwards and she didn't really recall it all, but Miss told her that she cradled her in her arms and stroked her hair until it died down to mild twitches in the legs.

She remembers her mouth being so dry, and Miss had given her 20 ounce bottle of water that she downed without stopping, in between the deep breaths she was taking to try and slow her racing heart. She also sort of remembered Miss cleaning her up, covering her in a blanket, putting her heels back on, straightening out her clothing, and placing her things in her pocketbook. But it was all like through a drunken haze.

Her eyes slowly opened and she was alone in the room. Then she sprang up and went for her pocketbook. Fuck! I must have passed out! Quickly, she checked her phone. It was 7:32 PM. Next, she dug for her purse: it was there but it had been compromised. A cash register receipt was sticking out with some cash. Scanning the receipt and then counting the money, there was the proper change for the cost of the beads. The packaging was gone, but there they were, along with her butterfly, washed and dried in her pocketbook. Her stockings were in there also, rolled up neatly. Where are my panti.... Her thought was cut short by the note she saw:

I hope you enjoyed yourself, I certainly did. Your Mistress is lucky to have you. Please give her my humblest apology, you were unresistable!

You paid for the beads (I thought you would want them) and I left the change with it. You can leave out the back door, just look to your right when you leave the room.

If your Mistress allows it and you ever want to come back to test out any other toys, you are welcome to. Just make sure it's Mon-Wed night.

Oh, and the panties? Don't bother looking for them.

She shook her head in amazement. It wasn't a dream, she had it right here in writing. She got up, unlocked the door and followed the instructions that allowed her to exit unseen. Still being the obedient submissive aren't you Becca? Once she made it to her car, she breathed a big sigh...one part relief, one part satisfaction, before she began to make her way home.


The End
The author has indicated there will be no future updates



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