Mistress Victoria took my continued interest in ass worship to an entirely new level during my last session with Her.
Typically whenever we would meet i would be made to kiss Her backside passionately, including some extended rimming. Her ass is so well rounded and delicious, it never fails to excite me, even when i am not in Her presence.
Mistress has jokingly threatened that sometime She would make it so Her ass wasnt so appealing, just to see how truly dedicated i was. Although the threat would make me shudder, deep down i relished the thought that a Woman so lovely and lady-like could be capable of making me do such vile things.
Mistress Victoria was left as a widow during Her mid-thirties. According to information She hints at now and again, he was apparently a successful businessman, and whether it was insurance or savings, (or both) Mistress had been left with a comfortable nest egg, thank you.
Accustomed as She was to the nicer things in life when he was alive, She truly had an appetite for things that money could and could not buy. Our relationship was one of them.
Victoria enjoyed my willingness to bend to Her will almost as much as me. Sure, She certainly enjoyed the oral servitude i gave Her while She watched TV, talked on the phone, or simply filed Her nails. i existed to give Victoria blow jobs and keep Her house tidy. And keep Her entertained. It seemed to amuse Her to no end that a man would stoop to such seemingly ridiculous levels just to serve a woman, and She never tired of exploring that irony.
Like so many dominant women, Mistress Victoria enjoys controlling me by using sexual release as a tool. Whenever i am in Her presence, i am either naked or in some feminine attire She has selected for me to wear.
Since i generally dont get to cum more than once a week, that makes being erect during that time a cinch. So when Victoria invited me over to serve as a butler for a dinner She was serving to a friend, i wondered what might be in store.
"Be sure to shave thoroughly before you arrive." Mistress had taken to keeping my pubic area and legs shaved, so i knew what She meant.
When i arrived at Mistress Victorias, She had me go directly to Her bedroom, where laid out on the bed for me was a French maids uniform, a black pair of slutty 4 inch pumps with ankle straps, fishnet stockings and a garter belt. I was appalled.
"Isnt this just the best outfit ever!" She exclaimed, barely concealing Her enthusiasm. "And in front of my friend too!"
My face could not disguise my embarrassment, but my weenie betrayed me by standing out hard as a rock as i undressed. It had been over a week since Mistress had permitted my to cum.
"Sarah and I went to college together, and Shes in town for a convention. I told her I had the most delicious surprise for Her, and youre it! Now hurry and get dressed, Ive ordered out for Chinese food. Shell be here in thirty minutes."
Up to this point i had been made to wear panties on occasion, and once a teddy. But this was pushing me further ahead than i ever dreamed, and with a friend of Hers coming over!
"Now hurry or you wont be ready, and then youll be punished."
As fast as possible i slipped into the outfit, the softness of the fabric making me harder still as i stepped into the stockings and garter belt. The maids uniform was shockingly short, a realization that was immediate as soon as it came to rest on my shoulders.
Either Mistress had forgotten to lay out panties or my family jewels were going to be barely covered by the much too-short lacy hem of the uniform. The crack of my ass was clearly exposed as well, and just forget about bending over, even slightly.
To my chagrin, i could see the head of my cock peaking out, drooling a long rope of fluid toward the shiny black pumps i was slipping into.
Stepping somewhat cautiously i went to the kitchen and presented myself to Mistress Victoria. Her arms were folded over Her chest, one hand on Her chin as She leaned against the counter and began to snicker. My face turned beet red.
Victoria looked radiant, even though She was dressed down a bit in black tap pants, a pair of open toed mules, and a silk blouse that was white, unbuttoned low enough to afford me a good look at Her 36D breasts. She had tied the bottom of Her blouse in a knot that exposed Her navel, a sight that always never fails to make me horny. As if that was needed.
"You look stunning, My dear. Turn around, lets see how you look!"
It was as if She were talking to a girl friend at Nordstrom as they shopped. Slowly turning in a clockwise direction, Mistress oohed and aahed at the bizarre site of a man dressed in a slutty maids uniform, doing little else to conceal the fact that he was indeed a male.
"You need a bit more before Sarah gets here for drinks. Follow me".
She lead me into the bathroom where i was told to wait. Returning a moment later i could see She was carrying the "goody bag" of ours, making me think: "Here we go..." "Put your hands on the toilet and spread your legs wide apart."
I could tell Mistress sat down on Her vanity seat behind me, and She rustled through the bag for a moment. Her fingers lubricated my highly exposed asshole, and a second later She pushed a dildo into my ass.
This dildo was exceptional in the fact that it was nearly 8 inched long, very thick, but tapered on the base like a butt plug. Whenever She had made me wear it in the past, i got a bit light-headed because it was so big. But never was i made to wear it and walk around!
"Mistress, may i ask You a question?"
"Am i to wear panties or something to hold this in? What if it drops out?"
Pausing for moment She responded, "No. you are to hold it in on your own. If it drops out, believe me, Sarah and I will find another place for you to hold it." She slid it in and out several times, plunging it to the hilt, then pulling it out quickly until just the over-sized head was inside. "Yuck", She said at one point, "you had best keep this icky thing inside. When was the last time you took a shit? I better rig this up to where you wont stain My carpet if you drop it."
As my hands held the sides of the toilet, Mistress Victoria fastened a ball parachute to my dangling nut sack, then ran a string from the chute and tied it around the base of the dildo.
"There", she said, patting my ass cheeks with open palms. "If that filthy thing decides to plop out, it wont stain my carpet."
"Thank You, Mistress" i said, wondering what i should be so thankful about.
"Now before you go, one last little item." Mistress quickly snapped an adjustable cock ring behind my balls and around my cock, "just to make life interesting for you this evening".
I stood up and as i looked at my reflection in the bathroom mirror, it was plain to see the chains from the parachute, my engorged cock poking from beneath the lace, and without having to check, the base of the fake penis protruding from between my ass cheeks. Mistress softly stroked me as She whispered in my ear: "Dont you just love being My little plaything?"
Later on, after i had opened a bottle of wine for Mistress and tended a few last-minute details, a knock came on the door. Without asking, i walked as best i could in the wobbly heels and, taking a deep breath, i opened the door wide. Before me stood a very pretty woman, blonde haired, blue eyed, and with an athletes figure.
She wore a miniskirt that was a cream color and a sleeveless blouse that stretched across Her well-proportioned breasts. They looked larger than Victorias, but i knew it was not proper to gaze at them. She looked shocked at the sight before Her, and i felt extremely embarrassed, and could say nothing.
Mistress came from behind me and stepped in front of me and hugged Her old friend. The two of them carried on briefly before turning their attention to me as They closed the door.
"What the fuck is this?" exclaimed Sarah as the two Women looked at me as though they were looking at a new car.
"Surprise!", said Mistress, "Remember how we used to torment boys in school? Well, this is just a refinement of our old tricks. Sarah, meet "plaything".
I was aghast, but what could i do? I quickly knelt at Sarahs feet and kissed them. She was wearing low pumps without any hose, and as my tongue touched Her shoes i could smell the rich scent of leather. Also, the walking and bending over had caused the dildo to slip a bit, and i reached around to push it back in.
"Stop that!" yelled Mistress when She saw what i was doing. With that She slapped my ass with her hand a good ten times, leaving it with a stinging sensation and the dildo still a bit further out than when i had answered the door. "Slaves are such a chore to deal with. Come in and tell me about you and what all has happened since I last saw you!"
The two Women left me there kneeling, and over Her shoulder i heard Victoria tell me to pour another glass of wine for Sarah.
The evening progressed as the two friends chatted while i poured wine and knelt before them, knees apart, my ass resting on my spiked heel shoes, as Mistress had instructed. In this position i could not keep a tight grip, as it were, on the lubricated dildo. The more i got up and knelt down, the further i could feel it slipping out.
i dared not reach back again, as Mistress and Sarah periodically lifted my uniform to see how things were "progressing", as Mistress put it. Finally, whenever i knelt before them, i was to place a small towel beneath me, indicating it was not if, but when, the dildo dropped free.
It wasnt too fun earlier in the evening when the delivery man came and i had to pay him. The looks he gave me were really embarrassing. The two ladies ate while i stood nearby at attention, pouring wine, water, or retrieving dishes. They laughed when they made me eat several red peppers from the spicy dishes, and i was permitted to eat what was left from a dog dish in the kitchen.
The two of them had big laughs which grew louder as the night wore on, and they started on the third bottle of cabernet.
"Slave!" called Mistress, "fix us some dessert! We want ice cream with chocolate on it!."
As i delivered the dessert, Sarah, now very comfortable with the scene being played, suggested i get my own dessert as well.
Mistress had me reach up under Her skirt and pull Her thong off, then stick my head between Her legs and begin to eat her.
Sarahs heels were on the side of the couch, exposing her pussy to me, and i eagerly licked and probed Her for the next twenty minutes. After She orgasmed the second time, Mistress decided it was time for some entertainment.
Grabbing an ottoman, they made me bend at the waist and place my elbows on it while keeping my ass high in the air and my legs reasonably straight. To do this, i had to spread my legs very far apart, and when i bent my knees i could feel the dildo slide a bit further.
The whole evening it felt i was taking one long shit, and it was all i could do to not force the damn thing out, providing me with relief but presenting me with a new problem. At this point it occurred to me to go ahead with the inevitable: let the fiendish device escape, and take what was sure to come anyway. With the slightest of effort, i squeezed a bit and felt a pressure on my balls as the dildo hung between my legs.
Mistress Victoria and Sarah stood behind me and made crude remarks about my inability
to behave, and Mistress stated i needed to learn that She indeed carried through with her
"Slave, take the dildo off the chute, please", She said as though She were telling me to remove a dish from the table.
Standing now in a kind of squat position, i removed the string from the chute and held the really foul looking dildo before me like a fisherman with a trophy bass.
Mistress Victoria looked at me squarely in the face, holding her hand out. i tenderly handed her the string as the dildo turned slowly, the tip and sides of it streaked with brown.
"Plaything, Im going to take this into the bathroom and hang it up. you will have the opportunity to redeem yourself by submitting to a test. If you fail, then you will have a penalty to pay. If you succeed, then I will permit you to cum. Are you ready for the test?
"Yes, Mistress, as You wish."
"Lie on your back." As i settled onto the floor Mistress had Sarah come over and straddle my face, facing my feet. She slowly squatted down until her bare bottom was nearly touching my mouth. Her hands then reached around and spread her beautiful ass cheeks wide apart, and with that She lowered herself until Her anus touched my mouth.
"A taste test, slave. If you are such a devoted plaything, I trust youll be able to tell the difference between the two of us. Well even give you a break by allowing you to see which asshole youre licking before we blindfold you. Dont let me down", She warned in an ominous tone. The two women laughed in a sinister way as my tongue began to slowly circle the tight pink ring one way, then the next.
"Lick the rim, thats it" Sarah instructed. "Now, nice long strokes. Thats it. Good."
Sarahs anus clamped onto my tongue as I probed her inside, and then it would slip out. After a few minutes of this they changed places.
Mistress Victoria had me repeat what I had done to Sarah, only this time she had me stick my tongue inside her all the way and hold it.
Hands began to pinch my nipples and then lightly fondle my cock. All I could do was moan into Mistress asshole, something she seemed to enjoy.
"Okay, taste testing is over. Its time to play. First though we need to blindfold you."
A mask I had purchased for Mistress was slipped over my head, covering my eyes, making my world pitch black. I could hear the two women whispering, and then I sensed a bottom near my mouth. I stuck out my tongue and it touched an asshole. I was surprised when it was withdrawn from me and the two ladies apparently changed spots.
Every 10 or fifteen seconds they switched. After each woman had been tongued maybe 10 times each, Mistress Victoria announced "Okay, tell me whose asshole this one is."
My mouth by now was dry and al my nose could smell was the distinctive aroma that an anus exudes. I honestly could not tell who was sitting on me, and when she lifted off me after a moment, I was told to give my answer.
"Mistress Victoria" I said, unsure of my answer.
The blindfold was removed and there above me was Sarahs bottom. My heart sank.
Mistress Victoria led me into the bathroom and, after tying my hands behind my back, she showed me the shit-stained dildo hanging by a string from the shower curtain rod. In my heels it was right at eye-level.
"You have exactly five minutes to make that thing clean as a whistle. If you do that, well let you rinse your mouth and then let you cum. Fail, and youll be in for a most unpleasant night.
With that they turned out the light and with an open mouth I began to try to put a lip-lock on the end of the twirling dildo.
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