An adult stories – Annes Possessions Ch. 07 – Size Matters by DirtBoss,DirtBoss The car with Robin in it pulled into the driveway as the one bringing Altie and Ebron pulled out of the driveway. At 6:00 pm Anne had sent a meeting notification to Tom for he and Steve to be watching the zoom on the phone at 7:30 and the show would probably last about an hour. That would be 7:30 am their time.
Anne sent Altie to get herself and Ebron ready in the visitor’s ensuite at the opposite end of the house. Anne had outfitted the suite with a costume for Altie to wear and a leather body suit with no crotch for Ebron as well as a hood collar combo to keep his identity safe if video was hacked in anyway.
The slaves were hooded except Tee. She wore a ring gag, head harness with blinding pads holding on her Dolly Pardon wig. Anne offered a hood to Robin.
“Shit I got my own paywall just fans account. Please let me cast a copy of it too my phone and I will send you an edit for your approval before I post it.” Robin requested.
Anne placed Tee on the triangle with the top of the triangle in the center of her back. Tee’s wrists and ankles were attached to the outside of the apparatus directly below the peak and pulled tightly. The sides of Tee’s training collar were pulled tight to the center of the apparatus pulling her torso over the point.
A rope through the junction of the hip belt meeting the crotch belt of her chastity belt pulled down on the crotch forcing her hips down on their side of the triangle. Anne had put a 1″ leather pad under Tee’s back so the discomfort was not extreme, just bad. Tee’s inserts were still on two at the beginning of the festivities.
Robin stripped her clothes, giving herself to Anne for the next three hours. Anne inspected her as she did not want Ian to damage the girl in any way. Anne wasn’t as worried about the vagina or anus as Robin had shown Anne pictures of her mounted on a dragon size expander. The girl had shown Anne her free status identification and her age was listed at 26 years old. Her height was 5’5″ and she told Anne that a 30″ belt would fit around her waist.
Anne had Ian help Robin up onto the bondage horse sideways. Ian helped Anne get the center of Robin’s back on the edge of the horse to tie the belt to the floor on that side. Robin’s wrists were tied to the floor at 45-degree angles from her torso and three feet past her head. Anne tied the ankles to eyes even with Robins’s shoulders and four feet out from her hips.
Robin had told Anne that she had taken an enema at 4pm during a break in appointments.
“You get to clean him after each use to get him ready for the next hole. We are going, vagina, anus, throat. It doesn’t matter to me if he is covered in shit going down your throat.” Anne told Robin.
“Do you want me to loosen you up with a fist first or straight to him?” Anne asked after they got Robin in place.
Anne tugged on each of the 8 gauge 2″ rings piercing the girl’s H cup sloppy breasts. She then lifted each breast to distention with the rings.
“Fucking heavy. He is going to want to pull on these udders for leverage I would imagine.
Anne went to the other side of the bench and opened the vaginal folds to find an 8-gauge post behind the clitoris holding the thick hood back from a 1″ long swollen bud. The folds were already glistening. Each labium majora had three eight gauge 2” rings in them. Robin had “Cum Dump” tattooed just above her slit and an arrow on her left inner thigh pointing to her asshole that said, “Insert Here.”
Anne started her phone on Zoom as Altie entered with Ebron crawling on his hands and knees with slobber draining from his ring gag. Anne led them past to the bondage table. She showed Altie how to attach Ebron in an x with his ankles up in the stirrups.
Lori, I want you to teach Altie and Jade how to properly edge a man. What to watch as he is nearing ejaculation. I don’t want Ebron to cum in at least two hours. Altie gets his cage off, and Lori will instruct. Lori, I want them to participate, you don’t get all the fun.” Anne ordered the three.
The phone on its widest angle could view across the room, on the far left was Tee moaning and struggling as much as her bonds would allow on the triangle. In the center of the shot was Ian lubricating his monstrous cock, stroking it while licking the vagina he was about to use. On the right was the two women in hoods and one in a mask with her sliver hair pressed into the back of her tiny head, beginning to stoke and lick the small penis between the tiny man’s legs.
Tom’s phone buzzed in, “Just in time for the show. I hope you have Steve where he can see. Can you see Slut Tee on the far left?”
“Yes Mistress, she looks a little uncomfortable.” Tom said.
“She is about to get very uncomfortable. She is going to experience 6 on her inserts for the first time. She felt like five was going to fry her brain, I want to see what she thinks of 6. The vibrations are random along with the pulsing thumps from them. The shocks begin to happen sooner and sooner Keeping her from orgasming until she is being shocked every five seconds then everything shuts off for three minutes and starts over.” Anne told them on the phone then turned Tee up to six hearing a scream from behind the gag in her mouth.
Every couple of minutes you could hear Tee vibrating the entire triangle device on the floor. As time went by, they got closer and closer together. Anne left the phone to record the evening and went to Robin’s head and asked the questions she wanted on record.
“I want this on the recording. What would you like to be called?” Anne asked.
“My channel is known as Size Slut.” Robin answered.
“Size Slut, are you participating at your request?” Anne asked.
“Yes, Mistress.” Robin answered.
“Do you want there to be restrictions on how hard you are used by The Cock?” Anne asked.
“No Mistress I want him to grudge fuck me, pussy, ass, and throat.” Robin explained.
“Have you seen the size of The Cock’s penis?” Anne asked.
“No Mistress and I don’t care.” Robin said, “The bigger the better and I want my guts rearranged and to have to crawl out in the morning.”
“Ok, give her your cock and be as rough as you want.” Anne said.
Before the guests arrived, Anne had told Ian that unless told different, he was expected to be rough on the woman and sexually use his penis to hurt her. If he saw blood, he was to stop but otherwise Anne wanted her to have some bruising to remember this by.
Ian was rock hard, and Anne whispered in his ear, “Start easy but I want to see finger bruising all over this chick’s tits in the morning when she leaves well fucked. You have permission to cum as many times as you would like tonight. There will be a camera running in here for you to shoot every scene with and one sitting on the dresser in the bedroom you are using tonight. Enjoy her.”
Ian pushed the head of his well-greased glans up to her entrance. Anne stood at Robin’s head.
“Remember your safe word is red and if you need a break, it is yellow. If he is in your mouth and you can’t speak, shaking your head side to side is the same as red.” Anne told Robin.
Robin groaned as Ian grabbed each breast with his hands, feeling the stiff nipples and thick rings in the center of his palms and began to push himself into a woman for the first time in seven years. This was the first vagina that had ever accepted his cock without him feeling like it was going to tear. It was very tight but did not feel like it was being damaged accepting his cock.
“Feed her that chocolate monster.” Anne said!
About six inches in Ian started to hit his first major resistance.
Robin’s Dragon dildo was as big around as this cock but only the bottom four inches the rest tapered down to 2 1/2 and to 1 1/2″ at the top and it was only 12″ long. Ian was plowing new ground and Robin hit a peak quickly as she felt muscles being pushed that had never been stretched. The pain was now mixing with her pleasure.
She though he might rip her tits off as he banged away at her insides. Anne watched Robins eyes roll back in her head and she started to convulse. Thinking he was causing the woman physical harm, Ian stopped. Robin started to come around and began begging.
“I was just cumming, don’t stop keep going oh my gawd keep going!” Robin begged and Ian began again earnestly. Ian was deeper into any human than he had ever been before. He could feel her moisture and heat as his balls swung forward and slapped flesh. Robin was in a steady groaning orgasm.
“Permission to cum Mistress!” Ian yelled.
“Permission to cum as many times as you want Slave.” Anne said.
Ian’s first orgasm inside a woman in seven years was painfully satisfying. He watched her lower abdomen and felt it contracting around his pulsing cock. She was flowing with seminal fluids as Ian pulled his cock free with a sloppy sucking sound. Anne’s fist would have easily fit into the hole left in Robin’s gaping pussy when the head of Ian’s cock broke free.
“Use her mouth to clean that and get it hard again to use her asshole.” Anne ordered.
Robin was reentering reality when upside down she saw the largest chocolate colored cock she had seen in her life. It was covered in cream and cum and slime.
“Mistress, I need something to protect this monster from my teeth. I think I can take it; I just don’t think I can keep my jaw open far enough without some help,” Robin requested.
“After he gets done in your asshole, I have a remedy that will allow him to use your throat. We are going to reposition you for the use on your throat. Now clean that cock and get it ready for some ass.” Anne told Robin.
Robing started to slurp and lick the large cock as Ian moved it around and allowed her mouth access to the parts. Once it was clean, he pushed into her open mouth until the glans encountered teeth. Robin concentrated her tongue on the bottom and tongue fucking the slit.
Anne was helping by shoving a well-greased 1 1/2″ thick dildo into Robin’s asshole and squirting more lubricant into the hole when she pulled out. She exchanged it for a two-inch thick eight-inch-long dong and continued to do the same.
Ian came to that side of the bondage horse.
“Look, the vagina still has not closed and see how it twitches looking for something to grab a hold of. Have you ever been inside a person’s asshole, Ian?” Anne observed and asked.
“No Mistress, you don’t think I will hurt her?” Ian asked.
“No, it will hurt, and you may even see a little blood, but if she has been using the same toys in her asshole as her vagina, she will be able to take it without damage.” Anne opined.
” This time once the head is passed the anal ring, slam it home as hard as you can, I want some finger bruises on a different part of those tits so grab them sideways instead of over the nipples. Yea like that.” Anne instructed.
Anne began to tug on the clit ring while rubbing the tip of the nerve center with her index finger. In time with the tugging Robin’s hips were fighting the belt and rocking up with the tug. Robin let out an oooohhhh as Ian pushed against her anus. There were so many conflicting inputs hitting Robin’s brain that she could not concentrate on any of them solely.
The pain of her anus being stretched, the pleasure or her clit being rubbed, the pain of her breasts being squeezed and pulled by the giant man with the giant cock. The pleasure of her heavy rings rolling around her erect nipples. Then it hit her like a truck hitting a deer at 70 MPH.
Ian drove his cock to the hilt in Robin’s rectum. Feeling the warm sleeve cover his shaft so rapidly and the soft folds of her rectum envelop his length was amazing. Ian did not notice but Anne did that Robin stopped breathing. Anne was still rubbing on the nub she had stretched now with the ring behind it but was watching the girl’s face. The eyes were rolled back and as Anne counted ten a deep inhale happened before Robin squirted Ian’s midsection.
People call it vaginal squirting, but it is a sudden loss of bladder control and spraying urine while fucking. Robin had just done it all over Ian. He did not notice or did not care with the euphoric feeling of his cock in the slick moisture of Robin’s backside.
“Pull out, I am going to get some more lubricant in there, so she isn’t damaged tonight.” Anne told Ian. Anne took a full handful from the bucket of lubricant.
When Ian pulled out Anne was able to push her hand up to the elbow and rotate lubricant onto the walls of the rectum coming back out.
“Fuck away big man.” Anne ordered and went back to observe Robin and make sure she was ok. “Are you doing, ok?” Anne asked.
“Fuck yes, that was awesome. Oh, my gawd, fuck again, again!” Robin begged.
Ian began to pound away, and Anne decided to go check on Tee. She had been almost a half hour on six and Anne thought she might try seven. Then she got to Tee.
Anne lifted the eye pads in the harness. Tee’s eyes were rolling back in her head. Her body vibrated then would shake a little and vibrate again. Anne figured Tiffany was no more only Slut Tee remained. Anne stopped the inserts but left them in place behind her belt. She would give her a break then release her to spend the evening cleaning Ian from Robin’s orifices. She would put Tee’s wedding photos where Robin and Ian could look at them while they fucked the night away.
Anne stopped to look at what Lori was teaching Altie and Jade. Ebron had a leather wrap around his scrotum that Lori had used to stretch his little testicles down almost an inch and a half. They were dark purple, as was the head of his cock.
“I think going forward if his doctor agrees you should get him some ED meds!” Anne joked.
“That might be a good idea, I am not always going to have these beautiful tits for him to look at or that lovely Chinese body for him to fantasize over.” Altie replied to the joke twisting Lori’s nipple in the process.
Jade was concentrating on watching the muscles at the base of the cock as she stroked it. Ebron concentrated on moaning and trying not to orgasm. Altie threatened to put a ring through the head of his cock if he came before she ordered it tonight.
Anne returned to Robin to find her panting into Ian’s cock as streams of fluids drained from her asshole.
“I have seen that Size Slut is not just a size whore but a pain whore that gets off on the pain of size. I am going to release you to use your throat. I have some teeth guards and a dental gag that you are going to install and operate to get him into your throat. Then every second I am going to strike your back with the 6-foot single tail until you are balls on your chin with him entirely in your throat.” Anne instructed Robin.
Anne began to release Robin by releasing her wrists first. Robin’s hands immediately went and wrapped the cock in her face that she was cleaning.
“Lift her down Ian,” Anne said as she released the belt.
Anne went to Tee who had recovered some since the inserts had been stopped. Anne removed the gag and uncovered Tee’s eyes with the removal of the harness. The wig came with the harness.
“I will release you, your task for the night is to clean Miss Robin while Ian takes his pleasure from her. You will attend the two until I release you in the morning.” Anne told Tee, releasing her bondage on the triangle.
Tee’s body was sore, and her muscles ached everywhere, even the soles of her feet and the palms of her hands ached. Her pussy and asshole felt empty without the pulses and vibrations though.
“Mistress, may I request 2 on my inserts? I feel empty without my Mistress’s touch.” Tee begged.
Anne smiled and inside knew that Tee was hers forever. Anne turned the inserts on three with shocks set at two. Tee moaned as the two angry little devices started back up.
“Get under Miss Robin as she is going to be on her knees for Ian to use her throat. I want you cleaning out what Miss Robin is leaking from her sloppy pussy and asshole now that Ian has loosened them up.” Anne ordered. “Size Slut is going sit on Tee’s face and let her clean you from Ian’s use.”
Anne handed Robin a dental gag that fit in the side of her mouth and went behind the upper and lower teeth, it had an opening ratchet and all Robin had to do to increase her mouth opening. Anne also handed robin upper and lower rubber teeth covers to protect Ian’s cock from her teeth scraping on it if Robin could not get her mouth open far enough.
Ian was stroking his semi-hard member, and it was about 9″ long and three inches across. Robin used the dental gag and installed the teeth covers. She guided the cockhead to her mouth and increased the pressure of the dental gag, further opening her lower jaw. It ached a little and Ian’s cock just fit in the hole. Ian could feel the back of Robin’s throat open and accept the head of his cock.
The warmth of a throat he had never felt. He hardened quickly with the all over warmth, wetness, and squeeze on his cock. Robin quickly squeezed the gag open two notches and felt like her jaw was going to dislocate but the now hardened cock was sliding and out unimpeded. Then Robin felt the first slice of fire near her left shoulder blade.
Anne began to stroke Robin’s back with a single tail after seeing Ian grab the back of the girl’s half shaven head to pull her onto himself harder. By the fifth stroke of the single tail Anne could see the throat bulge having moved down further into the girl’s neck. Tee could feel the increase in fluids now coating her face, becoming available to her cleaning mouth and tongue.
By the tenth stroke Anne could see Robin pulling forward on Ian’s thighs, with tendons standing out on her forearms trying to get the cock deeper, knowing Anne would not stop until the length and girth was inside her body. Each removal of Ian’s cock head from her mouth was followed with bile and slime. The twentieth slash onto Robins back found the crying girl’s face buried on the smooth skin of Ian’s shaved groin.
Robin gurgled and convulsed her throat trying not to vomit from the large thick member now closing off her throat just above her stomach. Ian pulled back giving the girl a gasping breath and buried again getting his third orgasm in an hour and beginning to pump seminal fluids down into her nearby stomach. Tee sucked in the clitoris and received an orgasm on her face from the girl being filled at the time.
Tee was on edge of cumming as well but the sudden electric shock in her groin brought her back to her reality of pleasure with pain. Anne left the three for their night. She wondered how many Ian would take before his night of sex was over and he was locked back up.
Anne walked over to the phone and stopped the recording. Anne turned the video so she could see Tom.
“How is Steve this evening, or your morning?” Anne asked.
“Steve spent last night learning some new skills, he spent two hours in a five-hole glory hole with another cock sucker trying to keep up with the fresh cocks in the holes. When I came back from dinner the establishment gave me the equivalent of $65.00 US for Steve’s two hours. The two had dealt with 120 cocks over the two-hour period.” Tom answered showing Steve bound on the bed in a hogtie.
“I hope you two enjoyed your morning show, now go sell some software.” Anne ordered, turning off the feed.
Anne walked over to see Alita with her husband’s cock in her mouth, she had his balls in her hand crushing them as Anne knew her tongue was rolling across the sensitive head from over an hour of edging from three women. The man was sweating and moaning uncontrollably into his ball gag.
“Jade, you can attend me this evening. Lori you will continue to teach Mistress Alita, she will receive at least two orgasms from you this evening and you will wake her at the designated time as a submissive should wake her Mistress.” Anne demanded taking the naked Jade and clipping a leash to it.
Jade immediately went to the floor on hands and knees following her owner to the bedroom.
Anne woke to the tongue that had pleased her the night before. After morning rituals and cleaning Anne walked behind her crawling slave to the kitchen. Lori was cooking breakfast and Ebron was washing the pans already used in the cooking process.
“Jade will bring me and Mistress Altie coffee on the patio.” Anne said.
“Mistress, Mistress Altie is drinking tea this morning and has a fresh cup.” Lori explained.
Anne went to the poolside and Altie was there in a cute two-piece suit that accentuated nice, flared hips, small pert breasts on pale white skin, offsetting Altie’s dark curly hair. Anne sat across the table from her.
“Lori taught Slave E how to wake me this morning. Then she helped me shave him and reinstall the cage. She then trimmed me so my hair would not creep out the sides of this suit. I was afraid it would show too much but most everyone here is naked except you and I so what is to show?” Altie said and giggled, taking a sip of tea.
“From the décor of your house and the dresses you wear I take it you like things Victorian?” Anne asked.
“Yes, I think it was one of the most beautiful eras of our times.” Altie said.
“I want Jade to take some measurements of Ebron and you and I will go shopping while the slave’s get this house cleaned and ready for your and my night inn. What is your favorite meal? No expense spared.” Anne asked.
“I only had it one time, but it is definitely king crab legs with butter to dip them in.” Altie said.
“That is what we shall have. Let me get things organized the girls will bring your breakfast out shortly.” Anne told Altie and headed back in to rouse Robin, Tee, and Ian. It was almost 7 am and Robin’s car was going to be here at 7:15 so just enough time for her to shower and dress.
Without knocking Anne opened the door to the ensuite to find Tee between Robin’s legs and her working on the head of Ian’s cock. The two came in unison as Anne entered.
“The three of you get showered, Tee you need to hand me the inserts once cleaned, and I will have a fresh pair for you in the kitchen. Ian, you will belt after the shower, the lock is open, and I have the key here,” Anne pointed to between her breasts at a chain. “Robin, your car will be here in fifteen minutes, please do not be late.”
Anne turned and left the three scrambling on her instructions. Anne went and asked Jade, as she returned from serving Altie her breakfast, to measure Ebron for boots and an outfit. She would do the same for Ian once he came out from the shower.
“Jade, you will also lead the yoga this morning and Ebron will join. He can use my mat and hydration cup. You could correct form, posture, and effort. I will also need your measurements along with Tee and Lori, I think we are having a party tonight.
Anne called Bridgette, “Hey, I am sorry, I am going to miss the golf along with Tee, yes that is Tiffany’s new name. Yes, she is now my property until our husbands come back. If you and the other winner want to bring Darci and whoever the other two are to dinner at my house, we are having crab, and the playroom will be open all night. Okay, well than win or lose four for dinner, come by about four and make the bet until midnight for winners to own the losers.”
Anne grabbed the sizes from Jade and pulled the group together, including Hebron in the kitchen, as Robin left out the door, holding her lower abdomen and walking tenderly. Anne had seen the dark purple hand bruises covering the girl’s tits. The girls were all in their belts this morning and Anne had a key for each, today she was going to get a gross of locks all keyed the same.
“I will have the store deliver what you will be making and serving for dinner this evening. I am having some friends over, and my expectations are of exemplary service. I will be back by three and we will start getting you dressed for the evening. Jade will be doing yoga instruction this morning. She will have the ability to correct you on form, effort and asana, her direction during yoga is to be followed as if I gave the correction myself. Please have the house and playroom spotless when we return.” Anne instructed and went to get Altie who was dressing after breakfast. The first stop was the sporting goods store for Altie to get some of the things she had seen in the playroom that she wanted to use on Ebron going forward. Some carabineers, climbing ropes that stretched slightly, paracord that had no stretch at all and miscellaneous other securing devices. She also purchased a collapsable, adjustable weight training bench that had the ability to incline in either direction. These items were taken to the apartment above the jewelers.
The two got the stuff upstairs and Anne asked, “Do you mind if I borrow a piece of jewelry for the evening, and I would like you to have a nice necklace with matching bracelets as well.”
“I think that would be fantastic, should I grab a formal dress from my closet and some shoes?” Altie asked.
“No, we are getting new dresses and shoes today.” Anne told her.
The next stop was at the adult emporium, Anne had made a list of items with each of her slaves’ measurements and colors. She took the list to the girl at the counter and asked if the manager or owner was there. A woman in her early fifties stepped from behind a curtain and to the counter. Anne gave her the list and said they would return at two for the items. Handing the woman her card, Anne asked her to call if something was unavailable.
Anne then went to the English Manor Boutique. Altie had never heard of the store, and it was tucked away in a large Victorian house in Coral Springs. The two were met at the door by a small woman in a Victorian dress, corset on the outside, leather boots sticking out from the bottom of her dress with a bustle in the back.
“My name is Marie and is there anyway I can assist the two of you today?” Marie asked.
“Yes, I am Anne, and this is Altie, we have dinner tonight and would like to dress in formal Victorian manner. We need from top to bottom, or bottom to top, as it were.” Anne replied.
“Oh, fabulous, do you want English shifts or are we going French tonight.” Marie asked.
“I think we can forgo the shift and go straight to the corsets. I think we will both wear the corset under our dresses.” Anne said.
Marie had the women undress in the room next to the corset room. She was in the corset room as the two women entered.
“Do we want our waists trimmed or more comfortable?” Marie asked, looking to the more mature Altie. “What is your strap and cup size?”
“I wear a 30B strap and cup. My waist is 21 and I could use a slight trimming.” Altie said to Anne’s surprise.
Anne worked hard on diet, yoga, and golf to keep her 22″ waist and she was not that much bigger than Altie.
“I am a 32C strap and cup, I would like my corset to close at 21 on the waist and I want breast shelves but no cups.” Anne told Marie.
“I would think the same for me,” Altie said, quickly looking at how squished Marie’s breasts looked.
Two hours later were looking at themselves in a tri-mirror that was full length. Anne had convinced Altie to get the 6″ heeled black hook and loop boots with eyes only at the very top for the laces to stay tied. Marie recommended and the women agreed to getting the 3/4 full petticoats. They would have to hold the front of the dress down when they sat or the hoops in the petticoats would cause the bottom of the dress to lift as they sat.
The dresses lay across the rear seat of the Jeep in garment bags. At the Adult Emporium two employees helped Anne get Three pairs of boots and four outfits into the jeep. There were three boxes of accessories with the outfits. The two pulled into the driveway at 3:00 just as Anne’s phone rang.
It was Bridgette asking what the evening dress was so she could tell Bess the other winners and know how their slaves for the night should be dressed. Anne told her that it was a Victorian Formal theme, but they did not need to get anything special. A black evening dress would be fine with heels. Anne explained that their slaves would also be in Victorian period wear. Drinks at 5:30 pm, dinner at 6:30.
Anne entered her home with Altie following. Anne began organizing immediately as it was going to be close for all to be ready by 5:30 for guests.