Fantasies of a Bisexual Shy Couple #19

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On this fantasy I became a sissy maid for her boss.
8.3k words
4.2
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Part 19 of the 21 part series

Updated 06/13/2023
Created 12/06/2022
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During the week, Gabi slept at her female boss's house on Tuesday. She was increasingly naughty and enjoying BDSM sessions with her boss more and more. On Wednesday morning, she sent me a text saying that she was sore all over but that the night had been great, that she had come like crazy, and that she was still really horny and dying to tell me and have sex with me that night. She was horny when she got home, and we had great sex. Her pussy oozed its honey. It was soaked with horny.

She told me how they had had sex, that the boss had asked her to be her little slave at the weekend when she would receive another slave from her, and that she wanted someone to help her with the new girl. She replied that she couldn't, that she already had an appointment on Saturday, but that she would lend me to be the little slave for her boss. I replied, asking if she was really sure about that, and she said yes, that she wasn't jealous of her boss, mainly because I was letting her sleep alone there too. I asked how it would be, and she told me she would see her boss on Thursday and let me know.

On Thursday night, she arrived and told me that the boss had already arranged a session for me in the salon on Saturday afternoon, that she would send some things straight there, that they would prepare me, and that I should go directly to her house afterward. As I now knew the girls in the salon well, I agreed.

On Saturday afternoon, I went to the salon, and they took me to a separate room on the 2nd floor. They did the usual waxing session, but this time it wasn't as painful, my hairs were shorter from last week's session, and they were more affectionate. When they finished, they told me to shower in the bathroom and take the opportunity to clean my ass with an enema that was there. I cleaned up and took a short but very nice shower, feeling the hot water on my smooth skin.

When I returned to the room, the two were waiting for me, both wearing gloves. They told me to lie down on the stretcher and said they would prepare me for my little cock to be "calm". I lay down on the stretcher, and the two came to play with my ass and cock. They lubricated my ass sufficiently with lubricant, and both began to explore it, sticking their fingers in the beginning and increasing the number of fingers until they started sticking their hands in me. They alternated between fucking me with one hand while the other stroked my cock and balls and sucking the head of my cock. They continued this game, making me come three times until they couldn't get any more cum out of my dick. They had already stuck two hands in me and said my ass was very greedy, perhaps the most greedy of all their customers. They took advantage and put a huge plug in my ass, gave my ass good slaps, and sent me to another shower to clean all the lubricant spread over my ass, balls, and dick. I washed quickly and went back to get ready. With the usual practice, they held my now very withered dick behind, securing it with transparent tape.

They opened the bag the boss had sent and started preparing me. Inside there was a pair of prostheses, big breasts a little bigger than the week before but still smaller than Gabi and the boss. They glued the prostheses to my chest using the adhesive and dressed me in a strapless bra, which was pretty packed with those big tits. They also put on micro panties, stockings, and garters and removed the clothes I would wear from the bag. It was a maid's outfit, with very high heels and a little dress with a very short apron. It barely covered my butt. It also had a generous cleavage in the front, leaving part of the bra exposed, with those big breasts even more highlighted. There was also a tiara, which they put on me after putting on makeup and red lipstick. As usual, someone had stopped my car at the back of the salon, and I could get out of the back directly without being noticed, very discreetly.

I went to the boss's house, and at the reception, they asked where I was going. I gave the boss's name and her house number and said that my name was Gabriela and I was from the events company, which would serve the guests that night. They announced it, and I was allowed in. The boss met me at the door and told me to come in. She said I looked really hot and loved seeing me as a maid. She told me to go to the maid's room, sit down and wait and that she would call me when necessary. But she wanted to tease me. She turned on the bedroom TV in a porn movie and, using a remote control, turned on the plug vibrator in my ass. She said I was supposed to sit down without playing with my clit or coming. I had just come a few times in the salon, so I thought it wouldn't be that difficult. But the movie playing had a crossdresser dressed as a maid like I was and being fucked by two cocky males. There was no way not to relate things, and with that vibration of the plug in my ass, my hard-on was coming. But I was an obedient little bitch, and I waited for the boss to call.

Sometime later, the intercom in the little room rings, and when I answer it, it's her, saying that she needs my services immediately in the BDSM room. On my way, I would pick up the tray on the kitchen table and bring it to her. On the tray, there were some objects: a huge plug like the one I was using, a rope, some gloves, some clamps that I didn't know what they were for, a small whip that was a rod with a leather strip at the end, and two large jars, one with a lubricant, and the other with oil. I took the tray and immediately went upstairs, feeling like a servant.

The door was closed when I arrived at the room, and I knocked. I heard the boss's voice inside telling me to come in. I quietly opened the door and entered the room. Inside were the boss, our black lover, and our truck driver friend. They were still dressed. The boss was wearing a leather outfit, which had super tight pants on her hot thighs, but with strategic openings in her ass and also in her pussy, but which was not visible because she wore a strap-on that came out through the opening. It was pretty thick, somewhere between our lover's cock and the trucker's cock. It was pretty long too, the same length as our male's cock. Seeing that cock, with the plug vibrating in my ass, made me even hornier.

On the gurney in the center of the room was the slave Gabi had mentioned. She wore a tight-fitting latex suit as well, also with strategic openings in her ass, in her pussy, and in her breasts, which were as big as Gabi's. She also had a latex hood that covered her entire face, with only openings for her mouth and nose. But her mouth had the same gag ball the boss had used on us the week before, covering her mouth, and not allowing her to say anything. She was sitting on the gurney, her arms handcuffed behind her back.

I placed the tray on the table next to the stretcher, as ordered, and asked: do you need anything else? She responded with a soft slap on my ass, saying that not now, that I could go to the corner of the room, kneel, and await her next orders. I went to the indicated corner, knelt on the ground, and waited. That position made me feel the vibration of the plug even more.

The males were sitting on the sofa, next to the stretcher and closely followed the "torture" session. The chief took the rope from the tray and, demonstrating a talent that only constant practice allows, began to tie the little slave, passing the rope around her back and tying her big breasts, passing the rope around them, braiding the rope between them., and returning to the back. Those big tits started to get more pointy towards the front and slightly red from the reduced blood circulation caused by the tightening of the ropes. The nipples were hard, and she moaned softly. She should be enjoying it. When the boss finished tying, she laid the slave on the bed and picked up her candle to start dripping hot wax. As the only parts of her body not covered by latex were her big breasts, pussy, and ass, the boss tied her ankles in a leather anklet, which was attached to ropes that came from the ceiling, one on each side of the room. She pressed a button, and an engine started pulling the ropes, and the slave's legs were lifted, one to each side, leaving them wide open and with the pussy and ass pointed upwards. The slave's position must have been quite uncomfortable, with practically only her shoulders and head resting on the stretcher and suspended by her ankles, leaving her legs wide apart.

The boss lit the candle and waited for a while, creating an atmosphere of tension. I imagined what was going through the slave's head, trapped in that way, not knowing what would come next. After a few minutes, the boss came close to her and began to drip hot wax on her tied breasts. The slave writhed her body with each falling drop. I had already been used like this, and I knew that it wasn't pain but that the high temperature of the wax on the skin caused a powerful feeling of horniness. With their big breasts practically covered in wax, only the hard nipples sticking out, the boss put the candle on the tray, still lit, and took 2 of the clamps from the tray. A chain connected them. She opened each clamp and placed each one over one of the nipples, squeezing them and eliciting a deep groan from the slave. She started to squirm more and took a nice slap on the ass, with the boss telling her to be quiet. Then the boss began to slowly pull the chain that joined the clips, making it stretch and pull the clips and, consequently, the nipples. This movement caused more moans from the slave. The boss then proceeded to alternate licks and bites at the tip of the nipples, close to where the clamps squeezed them. The slave's moans grew louder, especially when she bit. The torture session continued, and the boss again took the candle, and now she started dripping the wax on her pussy and ass, which were wide open and turned upwards. The slave moaned very loudly now.

The boss called me with her finger, without saying anything, and pointed to the males, showing that I should prepare them to fuck the little slave. She made the blowjob sign with her mouth, indicating that I should suck them to make them really hard. I walked up to them and gave my hands, making them stand up. I opened their shirts and belts and lowered their pants and underwear, freeing their cocks. The truck driver's cock was already quite hard, and the drool on the tip indicated how excited he was watching that scene. Our black male's cock was half hard but also drooled at the head, suggesting he was getting aroused too. I held both cocks with my hand and started sucking our black lover's cock. After all, it needed a final little help. I slowly jerked off the truck driver while trying to swallow the black dick. They were both looking at the maid kneeling before them, sucking and jerking off the cocks. I was getting good at the blowjob, and in a few seconds, my lover's cock was very hard, and he was holding me by the head and was fucking my mouth. I loved it, and so did he. He fucked me tenderly but thrusting his cock deep, making me gasp.

While I was preparing the males, the boss had cleaned the wax from the slave's body and oiled her big breasts, pussy, and ass, leaving them very shiny. She put on the gloves and, taking the jar of lubricant, began to spread a generous amount on the pussy and ass of the slave, pushing inside with her fingers. Then she took the plug like mine, stuck it at once in the slave's ass, and turned it on. The plug began to vibrate inside her, strong, her body began to squirm more, and the moans increased. She was still suspended by her feet, her pussy exposed. Now the boss started to alternate slaps in the pussy, with rubs in her clit. This seemed to drive the slave even more insane!

Then the boss took the other clamp from the tray and clipped the slave's clit, leaving it well exposed, held by the clamp. She gave a long, slow lick of his tongue to the exposed part of the clit, and the slave girl began to scream, muffled by the ball, with arousal. She took several more hard slaps, both on the ass and pussy, including hitting over the exposed clit and the clamp. The slave writhed with lust, and she was going crazy. The boss then started sticking her fingers in the pussy, and increased the amount, and in a short time, she already had one hand inside the pussy. She thrust her hand deep and twisted her arm to make her hand move inside her pussy. But she did it slowly, to drive the slave even crazier, without simulating penetration. When the slave tried to wiggle, so the hand felt like a penetrating cock, she was slapped on the bottom and told to be quiet, or she would pull her hand away. She'd be quiet for a while, but then she'd bounce back. The boss began to thread the fingers of her other hand around the one already in the pussy, and shortly she had both hands in. She was moving her arms to tease the slave. And then she turned to us to see if the males were ready. She cracked a smile watching her little slut maid manipulating those hard cocks but keeping the males from coming.

She withdrew her hands from her pussy, gave a few more hard slaps on her clit and tits, and lowered her legs, still with the plug stuck in her ass. She was still with her big breasts tied and her arms handcuffed behind her, completely helpless. She asked the males to lift and bring her to one side of the room, where straps dangled from hooks from the ceiling. She slipped one of the straps under her back, between her body and arms, over the strings that tied her big breasts. A second strap was passed under the body at her waist, thus supporting her back and leaving the slave suspended. Her legs were bent upwards, and the anklets that previously lifted her legs onto the gurney were attached to the first strap, leaving her legs bent upwards and backward. Her pussy and ass were completely exposed.

The boss called the truck driver towards the slave's head. She released the gag ball and guided the trucker's cock to her mouth. The cock was huge, and the slave couldn't open her mouth any further, making her moans even more muffled. She went to our lover and, pulling him by the cock, pointed that huge dick to the entrance of the pussy. She placed one hand on our lover's back and, with the other, held the slave's body. With a quick movement of her arms, she made that cock enter deep, in a single thrust, in the pussy. The slave let out a deep groan, her mouth jammed with the truck driver's cock. Then she pushed the male away until he took the cock out of her pussy, crouching in front of him and sucking the cock to taste the soaked pussy. She repeated the scene 3 or 4 times, always jamming the cock hard and deep in the slave, then taking it out and sucking the cock to taste it. The slave squirmed, probably because she was getting crazy with the cocks.

She made the males exchange places after a new thrust in the pussy, and now the slave was sucking the black cock with her own taste. As the cock was a little less thick than the truck driver's (but still huge!), the cock went deeper into her mouth and throat, causing her to choke and drool a lot on the cock. And then she aimed the truck driver's very thick cock at the pussy, to repeat what she had done with the black male. In the first thrust of the thick cock, the slave stiffened her whole body upwards. The movement drove the black man's cock deeper into her throat, and she gagged. The boss held the monster inside her for a few seconds and then withdrew everything, as she had done before. Then she returned to give a single thrust in that pussy, and again removed the entire cock. In the following times, the slave stiffened her body less and moaned more pleasantly, showing that she was enjoying it very much. When she started moaning a lot, the boss told them to stop again and removed the plug from her ass. She could see how open it was.

She asked the males to change positions again, with the truck driver with his cock stuck in the slave's mouth. She spat on the big head of our black lover's cock, and repeated what she had done with her pussy, but now on the ass. She made the black male enter in a single thrust in her ass. As it was already open by the plug, the impact was not so significant, but as she forced him deep into the slave, her head was pushed against the other cock, and she was now with her ass stuck in the black cock, and with the whole mouth filled by the very thick cock of the other male. After 5 or 6 intense thrusts, interspersed with the cock out of her ass as she had done with the pussy, she ordered them to change places again. She repeated the ritual, but now with a thicker cock. If in the pussy she had tensed her body and moaned loudly, in the ass was more intense. She screamed, muffled by the cock in her mouth. The boss continued with the "torture", forcing the cock to enter the ass all at once and moving out afterward.

Her ass was now really gapped, really open. The boss ordered the males to stop, lower the height of the stretcher, and pull it under the slave, while she put the ball back in her mouth and secured it with the straps behind her head. The boss ordered our black lover to lie on the stretcher with his cock up. His body was only a few inches below the slave's body. The boss leaned the black man's cock on her open ass and pushed her body firmly towards the cock, making it enter the ass deeply. She pulled the slave's body forward and pushed it back with all her might. The slave moaned and screamed, even muffled by the ball in her mouth. The boss ordered the other one to get on the stretcher over the black male, with his dick pointed at her pussy. She pulled her body forward again and pushed back. Now the slave had her pussy and ass broken open at once by the two huge cocks. Her moans got even louder. The boss was very mean to her, and I was grateful that it wasn't Gabi or me in that situation. She continued to fuck the slave, and whenever the moans increased and she got close to coming, the boss stopped the movements. Always with the cocks out of her, harassing the slave even more.

After about 15 minutes of torturing the slave, she asked the males if they wanted to come in that bitch. They said yes, and the boss told them to free her from the ceiling straps. They untied her, who still had her breasts bound by the rope, and handcuffed her hands behind her back. The boss ordered the black man to lie down again and fit the slave's pussy into his enormous cock. As soon as she sat on that cock, the slave started to wiggle as if she wanted to come. She was slapped hard on the ass, leaving fingerprints and saying she would only come when the boss wanted. The boss stood on the stretcher, lowered her hips, pointed her strap-on at the slave's open ass, and jammed her cock. The cock was thick, and the slave had pussy and ass gapped again. The boss held the slave by her shoulders, pulling her body against the two cocks. The slave moaned louder and louder, always muffled by the ball. When she was about to come, the boss again stopped. She wanted to prolong this torture as long as she could. She jammed her entire strap-on into the slave's ass and went right forward, almost sitting on her ass. She looked at the truck driver who was waiting behind and said: you can choose the hole you want and put your big cock with his or mine. I didn't believe the slave would withstand those three monsters inside her!

He approached and aimed his cock at the luscious pussy. He forced it a little, and his cock slipped, apparently easily, since the slave was slick with lust. They began to fuck her hard, and the slave screamed a lot. After a few minutes, and everyone's breathing becoming very labored, the slave almost cumming, the boss turns to the truck driver and says: this whore's life is so easy. Come with me here in her ass, which is tighter than that pussy that is already broken. The slave cried, probably already imagining what she was going to face. He pulled his dick out of the pussy, and pointed to the ass along with the boss. He put his head on the little ring and started to press. The boss and the black lover were standing still, just waiting for the other cock to enter. When the head entered, the slave let out another cry. They waited a few seconds for her to get used to it, and he started to stick his cock again in her ass. Every inch of that monster disappeared inside her, along with the boss's strap-on. When he leaned his body against the body of the slave and the boss, the boss said: I was sure that bitch could handle everything!!! We can now fuck and cum in this bitch!!! And they started to fuck hard her pussy and ass. In the first thrusts, the slave screamed, but in a short time, she began to moan very loudly and wiggle to help with the triple penetration. They fucked the little bitch like that for about 5 minutes, very hard, until the males warned that they were coming. Without taking her strap-on out, the boss ordered them to fill the bitch with cum. Neither male had come yet, and I know how much they came the first time. When they were very close to it, the boss took her strap-on off the slave's ass, came in front of her, and pushed her body against the two cocks firmly. The two came almost together, filling her with cum with the enormous amount they used to come. Their cocks stayed inside her until the last drops came out inside the slave.