Fantasies of a Bisexual Shy Couple #18

Story Info
On this fantasy we are introduced to BDSM by her boss.
6.4k words
3.92
4.6k
4

Part 18 of the 21 part series

Updated 06/13/2023
Created 12/06/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

After experiencing the cocks of our transvestite friend and our black male and probably having the best orgasms of her life, my wife's boss spent the week saying that she needed to repay the pleasure she received. She wanted to give us a BDSM session in her home to complete the wife and hubby's whore training. She asked Gabi to arrange with our transvestite friend and lover to spend the weekend with us at her house. But to increase our pleasure, we shouldn't have sex all week, either between us or with our lover.

Gabi agreed immediately and asked if she had more instructions (the little bitch was already going crazy imagining what awaited us at the weekend). The boss only said that we were supposed to arrive early on Friday at her house to be prepared and arrange with our male and our transvestite friend for the late afternoon.

During the week, Gabi fulfilled what she had promised her boss, and she didn't have sex with me. She also asked that our black lover did not come to our house any day (I don't think neither she nor I could handle not having sex with him if he was there!) but that he would be fully compensated during the weekend by having a lot of pleasure. I was crazy all week, and I could tell Gabi was climbing the walls too.

I found an excuse not to go to work on Friday, and Gabi and the boss had arranged a "customer visit" together. We went to the boss's house early in the morning and were greeted by her at the door. She was dressed all in black, with a black leather jumpsuit, ankle boots, and high heels, making her look taller. She ushered us in and closed the door behind us.

She turned to us, slapped us very hard on each ass, and ordered us to strip right there. We took off all our clothes, and she told Gabi to collect everything and put it in the closet in the entrance hall, lock it and bring her the key. Gabi obeyed and handed her the key. The boss then said that from then on, we would abide by all her orders and that if we behaved well, we would have our clothes back on Sunday afternoon to go away.

She sent us upstairs to her room. We went upstairs, getting slaps on our asses. She told us to stop in the middle of the stairs and finish climbing the stairs on our fours. I immediately obeyed, but Gabi kept looking at her trying to understand. Because it took some time to get on all fours on the stairs, she took a violent slap on her ass, leaving the very red mark of the boss's fingers on her little ass. She said that any order had to be obeyed immediately, or there would always be consequences. Gabi immediately crouched down and looked at me with a face of astonishment, but at the same time naughty, as if she liked it.

When we got to her room, two gurneys were in the room, and the waxers who had attended us in the salon were there. Gabi had told her about our preparation. At first, I was a little embarrassed to enter the room on all fours, with that big woman bossing us around. But I remembered the waxing session and the wonderful blowjob I had received from one of them, and I relaxed.

We lay down on the stretcher, and they began to prepare us for waxing. They smeared wax on our legs and removed all hair from them. But they weren't being tender and careful like they were in the salon. Apparently, the boss had given them instructions on how to do it. When they finished the legs, the one with Gabi asked her to open her legs to shave her pussy and her ass. She applied the wax and pulled it off, eliciting a loud moan from Gabi. The boss watched closely, and after the wax removed all the hair, she took advantage of Gabi's open legs and gave her a nice suck on her pussy. Gabi started moaning with the suck, but as soon as she started moaning harder, the boss stopped, slapped her pussy, and told her to shower.

Then they turned their attention to me. They shaved my chest, too, always roughly. I got slaps on my breasts from both the boss and the waxers. Then the boss asked them to shave my crotch. They spread the hot wax over the crotch and sac and pulled at once. The boss told me to turn over on my fours in bed so they could shave my ass and asshole. She held my cock while they spread the wax and squeezed hard as they pulled. When they finished, I had a hard-on, with the hot boss holding my cock. But she wasn't jerking off. She was just squeezing my cock. She asked the waxers to get a plug on top of the bed and put it in my ass. The one who had given me the blowjob the other time gave my ass a good lick, leaving it sticky, and was pushing the plug in one go. It was big (not as big as our male's cock or her strap-on, but pretty thick), and it left my ass wide open.

When they finished inserting it, the boss paid them and said their job was done, and they could go. She told me to shower as soon as Gabi left the bathroom, but with instructions not to remove the plug or give a handjob. I went to the bathroom, and she told Gabi to get on all fours on the bed. She also received a plug in her ass, but the licking was now from the boss. In the bath, I could hear Gabi moaning with the lick. And then a little scream when the boss stuck a plug just like mine in her ass. He told Gabi to sit on the bed over the plug while I finished my shower.

I dried off quickly when I finished and went back to the bedroom. She told me to sit next to Gabi and feel the plug in me. She took two controls that were on the bedside table, pressed the buttons, and the plugs started to vibrate strongly in our asses. The reaction from Gabi and me was immediate. My cock got hard at the time, and Gabi started moaning hotly. I could see that this excited her a lot. I was also very excited after being sexless all week. Gabi tried to put her hand on her pussy and clit, and was slapped in the face. The boss said that she had not been authorized to do so. But she didn't remove her hand and continued masturbating. The boss slapped her face stronger and stronger, which seemed to turn Gabi on even more. When she wasn't going to stop, the boss using her strength and size, moved her arms and cuffed her hands behind her back. She asked me if I was going to masturbate, and I said no, lowering my eyes. Gabi told the boss that her pussy was on fire and that she needed to come, but the boss laughed and said that not yet, that it was too soon.

The boss took us to the kitchen for something to eat. She prepared a plate for herself. For us, a small plate of fruit so we could stay light and prepared for what was ahead. Gabi was still handcuffed, and I asked the boss if I could put the fruit in her mouth. She said that I was already a perfect little bitch, asking permission for everything, but that Gabi still had to learn to obey, so she would have to take the fruit from the plate with her mouth. Meanwhile, the plugs continued to vibrate in our asses. We ate, me eating the fruit with my hand and Gabi taking the pieces directly from the plate with her mouth.

After the meal, the boss sent us to her room to rest and prepare for the night. She took Gabi's handcuffs off, and we lay in her bed, the plugs still vibrating in our asses. She was in the middle, hugging her two little bitches. She squeezed and gave small slaps on our little asses. We fell asleep in her arms and woke up around four in the afternoon, with the alarm on her cell phone. She told us that we had to prepare as our males would arrive soon. She told us to clean our assholes with enemas to prepare them for the night. Then we should go back to the room to dress. Gabi and I took a shower, removing the plugs from our asses and finally putting them back on after cleaning them. I looked into her face, and I could tell how anxious she was for what lay ahead. I was too, but also a bit apprehensive.

When we returned to the room, on the bed, there were two matching sets of black lingerie, with thong panties and lacy bras, garters, and 7/8 stockings, also black, with lace on top. There were two pairs of shoes with very high heels, two blindfolds, and two leather straps with a big red ball in the center. There was still a brunette wig, short hair, and prostheses to be my breasts. The boss told Gabi to get dressed, and she came to help me. First, she spread an adhesive over the prostheses and glued them to my chest. They were large, not as big as Gabi's big breasts, and obviously smaller than the boss's gigantic breasts. But when I put the bra on, I felt different. For the first time, I felt more female. I put on my stockings and garter belt. She helped me tuck my cock back and then put on the thong panties, which were smaller than the ones I used to wear. We put on our high heels and sat on the bed per her instructions. Our plugs were still in our asses, and she set them to vibrate even harder. She put the wig on me and opened a make-up case on the bed. She did light make-up on me, got a bright red lipstick, and said that was the lipstick that whores should wear. She handed it to Gabi to apply and then came over to put the lipstick on me. The whores were ready.

She took us into the next room (where she had used and abused us the last time). This time there were two beds in the center of the room, like the one she had used with us the other time. She ordered us to climb into the beds, lying on our backs. She tied our hands and set up the leg supports like a gynecological table. She also tied our legs, leaving us open and exposed. Then she put blindfolds over our eyes. After using the leather straps we'd seen, she placed the ball in my mouth and slipped the straps behind my head. The ball forced my mouth to stay open, and I couldn't say anything. I imagined she did the same with Gabi. Then she told us that since we couldn't say anything, we should agree on a password in case someone wanted to stop. And the password would be shaking your head from side to side quickly. She asked if it was clear to us and asked us to nod our heads to confirm. Now we couldn't see anything anymore. We couldn't even speak.

She left us like that and left the room. I don't know how much time passed, but it felt like an eternity. After some time, we didn't know how long it was, and we heard her coming back through the noise of her heels and voices talking to her. I immediately recognized the voice of our lover and our transvestite friend, but there was a third voice along with it that I didn't recognize. It was strange to be lying on the table, open, exposed to a stranger that didn't know who it was. We couldn't move or speak. The boss increased the speed of the plugs in our asses even more. I imagine that Gabi was crazy horny for what I felt. They vibrated really hard, to the point of making me contort my body with lust. I heard her approaching us. I heard a loud slapping noise and a muffled groan. After a few seconds I feel the same hard slap on my ass. It was a strange sensation. The pain of slaps, and the heat they produced on my skin, turned me on. I understood why Gabi loved being slapped while she was fucked! I groaned in the same muffled way as Gabi.

The slapping session continued. Gabi later told me that she took more slaps on her pussy, and also on her tits. I got slapped on my crotch (my dick was still facing backward, trapped) and on the sides of my chest, as the prostheses wouldn't feel much. After a short pause, I feel warm drippings on my skin. She was again dripping the hot wax from the candles onto us. The vibrator was on full blast on our assholes, and the feel of the wax on our skin drove us both crazy. Gabi moaned faster and faster, even muffled by the gag. Another pause and the boss said she was preparing our next step. After a bit of silence, we heard zippers being lowered and the characteristic noise of cocks being sucked. The boss was sucking their cocks, preparing them to fuck us. Our imaginations ran far, imagining what awaited us.

A few minutes later, and with our mouths watering, imagining those cocks, the boss came up to us and removed the gag but warned us not to say anything, or we would suffer the consequences. Our heads were lowered back the same way as in the previous session. In a few seconds, I feel a cock invade my mouth, and by the size and smell, I know it's our lover's dick. It comes deep in my throat like it tastes, making me gag. Gabi said that she wanted cock right away and wanted to come, but what I heard were some powerful slaps, which she later said were on her pussy, her ass, her tits, and her face. The boss repeated the instruction to be quiet, that little dogs don't speak. We remain tied there. Our transvestite friend says she's going to shut the little bitch up, and she must have stuck her big cock in Gabi's little mouth because then I hear Gabi sucking and gagging on her cock. The boss now says that the little whores are ready for the next phase.

She came and pulled the plugs out of our asses, which was a shame as I loved that plug vibrating at top speed inside me. Her hand lubricated me, telling me it was to relax the ass. Then she does the same with Gabi, also asking her to relax. She told the third person I was ready but that he should go inside me in a single push, and she will do the same with Gabi. As I didn't know who it was, I tried to relax my ass as much as possible, preparing myself for the thrust. I feel a huge head touch my well-lubricated asshole, opened by the plug, and suddenly I'm invaded with everything all at once. The length is not great, but the cock is thicker than our lover's. I immediately recognized the cock of our belly truck driver friend, and I was happy because that cock had given me sensational enjoyment. I continued sucking our lover, with him putting a good part of his dick in my mouth, down to my throat.

The boss told him to fuck me hard and fast and went to Gabi. She told Gabi to relax, and I heard an intense groan from Gabi. The boss started to ask if her ass was well tucked up, and by the sound, she was fucking hard and fast, like the truck driver was fucking my ass. I'm also groaning hotly as my male jammed his cock in my mouth. Gabi also started moaning loudly as she was fucked by the boss. I heard slaps on her body while the boss fucked her, and our transvestite friend inserted her cock in Gabi's mouth. Gabi asked them to fuck her pussy, she wanted to come, and the boss apparently stopped fucking her, and I heard a loud slap on Gabi, who let out a little scream and a moan, saying that she loves slapping her pussy, but prefers a cock. She took another slap, and the boss said she would only play with Gabi's ass today. And asked the truck driver to switch places with her. I feel him get out of my ass and leave an open avenue in me. Our lover came to take his place, and even his cock entered me very quickly. The truck driver must have aimed his dick at Gabi's ass, now moaning in pain as that big head penetrated her. She hadn't given it to him yet, only me, and she didn't know how thick it was. He started to fuck her ass hard, and now Gabi really moaned loudly in pleasure, saying he was destroying his ass.

Meanwhile, our male has already thrust his entire cock inside me, and I felt him touching me deeply, the way I like it. But it seems to have also agreed with the boss because instead of the hot and rhythmic fuck we usually did, he was sticking his cock very deep and hard in me. The boss took the position he was in, inserted the strap-on she was using to fuck Gabi's ass in my mouth and asked me if I was enjoying sucking the cock that was inside my wife's ass. I just answered with a hamm-hamm, and I continued sucking her cock, while our lover fucked me hot. After a while of fucking like this, the boss says it's time for the little whores to get their double penetration. They untied us from the tables without taking off our blindfolds.

I felt our lover pick me up, and I thought he took me to the sofa next to the beds. He sat down, and I sat on his lap, positioning his cock in my ass. It came in hot, and he started massaging my new silicone breasts under my bra. The feeling of your male squeezing and sucking your breasts is very pleasurable, even though I don't feel his tongue. But I could feel how much he was squeezing my tits and how much he was enjoying it. The boss told the transvestite to do the same with Gabi, and I heard her bouncing on the transvestite's cock, and the transvestite saying that her ass was wide open too. The boss told her not to worry because it would soon be tight again. And she told the truck driver to fuck me with our lover, and she should be going to fuck Gabi with the transvestite. The truck driver puts that big head on my ass, and our male opens my ass to help it get in. As it had been the other time, the two of them were gentle until he inserted it together, going slowly for me to get used to them. The first sensation was of pain and that those two cocks would tear me in half. But I was gently swallowing them both, and in a few minutes, I was already wiggling at them. The truck driver held me by the hips, pulling my body towards the cocks, while my male continued squeezing and kissing the big breasts.

Gabi, on the other hand, let out a little cry of pain when the boss penetrated with her strap-on along with the transvestite in her ass, saying that they were tugging her. She said she wanted a DP on her pussy, was dying to come from her pussy, and got another slap on the ass for talking. I thought she was doing it on purpose to get the slaps. She kept talking and kept getting slapped by them, who said they loved to spank foul-mouthed little whores. Meanwhile, my males fucked me hard, and I moaned hotly. I felt the two were close to coming, and the boss asked them to fill my ass with cum. When the two arrived, she asked them not to leave because the other little whore would clean everything up. They took the cocks out of Gabi's ass, who screamed that she wanted to cock, that she wanted to come, and they dragged her to me, slapping her ass. When she was very close, they asked them to take their cocks off of me and forced Gabi's face into my ass, so she could suck all the cum the two left inside me. Gabi sucked everything, like she always does, and swallowed all the cum. When I felt her tongue licking me, I was already close to cumming, since the two cocks were inside me. I ended up cumming a little, still with my cock bent backward. The boss pushed Gabi's head a little so she could clean my clit, still soft and trapped by the tape.

The boss told the two to tie us again to the bed, strapping our arms and legs open upwards. They inserted the plugs in our assholes again and turned them on at maximum speed. The boss told the transvestite they would have fun while Gabi and I just listened to their sex. The boss ran over to our lover and started sucking his cock, saying she was falling in love with that big dick. The transvestite said that she wanted to try the truck driver's very thick cock, and apparently, she also started to suck him. When it was time to fuck, the boss told the transvestite to lie on top of me in a 69 position, so I could suck her cock while the truck driver fucked her ass. She shoved her cock into my mouth and opened up to receive his thick cock. He moaned sweetly, and I knew what it was like to receive that monster inside us. She started shaking her hips back and forth, fucking my mouth when she came forward and burying herself in his cock when she went back. With that monster inside her, she said it was the thickest cock she had ever had, and she started to cum deep in my throat while he was still fucking her.

In the next bed, the boss must have laid on Gabi because she told her to suck hard her clit while our lover fucked her pussy. With each of his dunks, she slaps Gabi's pussy, telling her to suck it right. After a few minutes, she started loudly moaning and slapped Gabi. She and our lover came together, and she, still over Gabi, told her to suck her pussy to clean and came once more on Gabi's tongue. The boss got off her, came to me, and said that since I was a very obedient little whore, she would let me go. She untied me, took off my blindfold, and I confirmed that the cock I felt was really the one from the truck driver. He and our lover came to me, kissed me on the mouth each, and said they still love to fuck my ass together.

12