Fantasies of a Bisexual Shy Couple #17

Story Info
On this fantasy we play with her boss, our lover and shemale.
4.2k words
4.15
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Part 17 of the 21 part series

Updated 06/13/2023
Created 12/06/2022
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During the week, Gabi told me that her boss didn't stop talking about our weekend, that she loved it, and that on some occasions when they were alone in her office, they exchanged scorching kisses, with the boss feeling her body. But since my little wife doesn't lose opportunities, she also prodded the boss asking what she had thought of her little whore husband and our lover.

The boss said that she had been impressed with the size of our lover's cock, and that she thought it only existed in movies or on vibrators or strap-ons like the ones she used on us. She confessed that seeing both Gabi and me sitting on that cock had made her very excited too. My little wife said that she was delicious, that it was more than expected, that both she and I were bisexual, and that we loved having sex with men and women, and even transvestites, that it was an ideal combination, woman and man in the same body. The boss still didn't know about our transvestite friend, and she was curious, asking more about her. She also asked about our lover and her son, and my wife kept telling her our stories, seeing that she was more and more interested.

The week passed, and the boss asked my wife if she wanted to go home alone, so they could have some time together. But my wife had other plans for the weekend. She said that she had already made arrangements with our lover and our transvestite friend at our house but that if she wanted, she could go too, and they would find a way to be just the two of them together. When she told me, I looked at her naughty face and said: I know you're going to end up being alone with her at some point, but I also know that you're planning to have your boss fucked by our male and also by our transvestite friend, or even by the two together, right, you naughty thing? She laughed and said, who wouldn't want that?

My wife called our transvestite friend, but she had an appointment on Friday, so she could only join us on Saturday and Sunday. Gabi had arranged with the boss to go to our house on Friday, and we would spend the weekend together. Our male already slept most weekdays and all weekends at home and would be with us. I left my wife at the office on Friday morning and went to work. In the middle of the afternoon, I had a waxing session scheduled, and I was going to meet them at home. My wife would go with the boss, stop by her house to pick up some clothes and go to our house.

I got home around six PM, and our male was already there. He had arrived right after work, taken a shower, and was in the living room waiting for us. I went to hug him, and when he smelled the moisturizer they had put on me, he asked if I had gone for waxing and if I was smooth. I replied yes and asked if he wanted to see it. Obviously, he wanted to, so I took off all my clothes in the living room. He placed me on the couch on all fours and started his delicious ass-preparation session, using his tongue and fingers. He loved to suck my smooth little ass and see me wiggling in his fingers. When he was starting to put his big cock in my ass, my wife arrived with her boss and started to tease me, saying that since I had started without them, they would be alone that night, and I would have fun with our male. I looked at him and winked, saying, they think this is a punishment, but we both know better, right? He, with his cock in my ass, just laughed and continued to fuck me.

The two went up, took their things to our room, and went down for something to eat. At that point, our male had already made me come, but he hadn't come yet, because I asked him to control himself and give me all his milk later. We had a quick snack standing up in the kitchen, I still naked, our male only in his underwear, and the two of them as if they had just come from the street. The boss took a few opportunities to run her hand over my ass, saying it was still delicious. Now with greater intimacy, I returned the affection on her huge breasts, saying that if I had breasts like that, our male would drop everything to marry me! We all laughed, but the two went up quickly to our bedroom. Our male and I went into the living room, turned on the TV, and just lay there, me lying on his lap.

Shortly after, we started to hear my little bitch Gabi moaning loudly and the boss slapping her ass. Gabi screamed with lust and asked the boss to fuck harder and faster. The two had left the bedroom door open for us to hear, teasing us. I told our male to go upstairs and take a look, then go to the other room, where we would sleep together. When we got to the room, the boss wore the same black leather corset, stockings, and mid-thigh boots as the last time. But this time, Gabi was handcuffed to the bed of her fours. She had her big breasts tied with a rope that tightened them close to each other. She was blindfolded and fucked by an even giant strap-on than the one used the week before. It was even bigger than our male's cock (not as long, but a little thicker). Gabi was heavily slapped on the ass. Gabi asked for more. The boss fucked her pussy hard and deep and even stuck fingers in her ass, saying she was the best little bitch she knew. The boss saw us in the doorway watching and giggled at us and continued to fuck hard. Gabi didn't know we were watching. The scene excited our male, who began to grope me from behind. I felt the bulge in his underwear grow and pulling him by his cock we went into the next bedroom.

Gabi kept moaning and screaming with lust for the next two hours. During that time, I gave our male's black dick a nice suck, and afterward, he spooned me, shoving his huge cock into my ass, kissing the back of my neck, and saying he loved my ass. When I was about to come, I asked him to give me the milk and then stick his cock back in my ass. He came tasty in my mouth, I drank all of his milk, and then he shoved that big cock in my ass again, still cupped. We fell asleep this way, still hearing the moans and screaming from the next room.

The next day he and I woke up early, went down and had breakfast, and went to the backyard to prepare the barbecue. We packed everything up, sat by the swimming pool, had a beer, and waited. A short time later, our transvestite friend arrived, and she came with us to the swimming pool. She said she would take advantage of the sun and improve her sun marks. She put on a micro thong bikini, which barely covered her hot cock, leaving it facing backward between her legs and with that hot ass showing almost everything. She sunbathed topless, showing off her lovely, hard breasts. Our male and I were teasing her, saying she was very hot, to see if we turned her on.

Sometime later, the boss came down, dressed in a nightgown. I went to the kitchen to help her with breakfast and said that we were already at the pool, waiting for her and Gabi to wake up and that she should put on a bikini and have fun with us. I asked about Gabi, and she said that that little whore was still sleeping, that she was exhausted, that she was insatiable, that they had spent most of the night having sex, and that Gabi's ass still had the marks of the hand. Not because she wanted to leave marks but because Gabi asked for stronger slaps while being fucked. We chatted for a while while she had coffee, and then she went upstairs to change. I went back to the pool.

A little while later, the two appear at the kitchen door on their way to the pool. Gabi wore one of her micro bikinis too, black micro panties well tucked into her ass and also tucked into her pussy, and with her big tits on display. The boss was also wearing a white micro bikini, with the panties tucked into her hot ass and her tiny pussy, and the top part that looked like a child's one, barely covering the big hard nipples of her enormous tits. Gabi said that the boss had forgotten her bikini, so she was wearing one of hers, so we should not judge her. But honestly, impossible to do that! They were delicious. They came up to us, and Gabi greeted us with luscious French kisses. The slightly more shy female boss gave me a French kiss and kissed our male on the cheek (he couldn't take his eyes off her tits!). Gabi called her to say hello to our transvestite friend. When she got close, our friend got up from the lounger, where she was face down, and came towards her with her hard breasts also on display. From our previous conversation, her hot dick was hard and starting to be on display, with the head sticking out of her micro bikini top. The boss was admiring that hot body coming, and she looked both at the breasts on display and her dick. When they went to greet, our friend turned her face on purpose, and instead of a kiss on the cheek, they exchanged a peck.

The transvestite praised her body, especially her huge breasts, and told her to enjoy and go topless like her and my wife, asking if she was ashamed of our black lover or me. She replied that we had both seen her big tits before. The transvestite replied: so, what are you waiting for. She started to loosen the bow on the top of the bikini, releasing those delicious big breasts and inviting her to come and sunbathe together. I felt Gabi's hand as if she had agreed with our transvestite friend. The boss lay down on one of the deckchairs, face down, and the shemale offered to put sunscreen on her. She started at her legs and worked her way up, paying special attention to her ass. To apply it to her back, she climbed onto the chaise, sat on her ass, and slowly rubbed suntan lotion over her back. We noticed that she rubbed her hot dick on the boss's ass every time she leaned forward to spread the cream over her back. I, Gabi, and our lover were on the grill counter, and our lover started to get excited with the scene and groped Gabi's ass and mine while we watched the scene.

The transvestite asked the boss to turn around so she could pass the sunscreen to the other side. When she turned around, her nipples were very hard, showing that she was enjoying the situation. Our friend started to put cream on her legs again, and it went up her thighs, and her hands massaged mainly the inner thighs. When she was getting close to her pussy, she mounted the boss again. She began to apply the lotion to her face, asking her to keep her eyes closed. As she spread the cream, leaning over her, she continued to rub her cock in her crotch. She went down the neck and reached her breasts. She applied sunscreen, massaging the entire chest, but always ending at the nipples, pulling and twisting slightly. She continued rubbing sunscreen for a long time, and now the boss was already making mouths and faces, still with her eyes closed, enjoying the moment. When I look to the side, Gabi is already kneeling and sucking our male, who still doesn't take his eyes off the scene on the deckchair, perhaps jealous of the transvestite for taking advantage of those big breasts of that hot blonde.

Our friend worked her way down the boss's belly, always returning to her breasts and teasing her nipples. When she finished, she lay face down on the side chair and asked the boss to reciprocate, now applying sunscreen. The scene was incredible. The boss started the same way, with her legs, then straddled her butt to apply the lotion to her back. She also rubbed the transvestite's hot ass while spreading the cream. When she finished, she asked her to turn around. The transvestite's dick was even harder, and an even bigger part was outside her panties. She started by dabbing the cream on her thighs, then straddling her again to apply the sunscreen to her face and body. But now her pussy was very close to that cock, only separated by the little fabric of the bikinis. She passed the protector over her face and used it the same way on our friend's breasts. She has little nipples on her breasts, but they got hard all the same.

Meanwhile, the boss was already wiggling on her cock, rubbing herself, demonstrating her excitement. When she went down the belly and reached the cock, she said she would have to lower her panties to spread the protector on her cock. We could see where her pussy had been, as the transvestite's panties had been wet with the boss's juices. She lowered her panties and, holding that hard cock, ran sunscreen all over it. But she kept jerking off and staring at the cock. The transvestite said it was delicious, that she should continue, and that she could use the cock however she wanted. By then, Gabi was already being fucked by our male leaning over the counter and giving me a handjob. The boss looked at that and must have thought, fuck it, I'll enjoy it too!

She started sucking our friend's cock, trying to swallow everything, showing how much it had excited her. Our friend pulled her aside, lowered her panties, and asked her to climb over her in a nice 69. In a few minutes, our friend's experienced tongue made the boss really excited while she was still sucking and jerking her cock. Then she asked her to sit on her cock again, still not fitting in, but rubbing her luscious clit over the cock. The boss sat on her and began to move her hips back and forth, rubbing her clit over the entire length of that dick. She started to moan deliciously while the transvestite sucked her enormous breasts like our male, with licks, nibbles, and strong suck on the big nipples.

She was increasing the rhythm of her hips, and we could see how much her pussy was soaking the transvestite's cock. She came hard and laid down on our friend's breasts. The shemale was hugging and caressing her body while kissing her mouth, saying that she was very hot but that now she had made her cock very hard, and she needed to come too. She asked her to fit in his cock, continued wiggling because her next orgasm would be even better, and went back to sucking her tits. The boss raised her hips a little, our friend pointed her dick upwards, and the boss sat down on that cock, bigger than mine. I could see that she really wasn't used to giving her pussy, because she said it was a very big cock and wouldn't take it.

Gabi came on our male's cock, and he now used the lubrication of her pussy to put the cock in my ass. Gabi went to the girls to help her boss. She asked her to relax, and sit down slowly, to get used to it. She said her dick was big but really hot. And our lover's dick was even bigger, and she would liked it even more. Our male now had his cock all stuck in my ass, and was making very smooth, deep movements. He wasn't just doing the head in my asshole ring, as we both loved. I think so he could control himself and not come right away.

With Gabi's guidance, the boss was slowly sitting on that cock, while Gabi and our friend caressed her big breasts and ass. After some effort, she had the cock all stuck in her pussy, and she said she felt it hitting his uterus! Our transvestite friend pulled her to lie down on her chest and offered her nipples for her to suck. She started sucking the transvestite's hot breasts while she got used to the cock in her pussy. She slowly began twitching and enjoying that dick in and out of her pussy. She was already starting to moan tasty, showing how much she was learning to like a real cock. She was soon riding our friend's dick furiously and saying how nice it was to feel her pussy fulfilled. Gabi held her big breasts, teasing the nipples as the boss had done to her. The transvestite gently slapped her ass, encouraging her to continue jumping on the cock.

After a few minutes of riding and moaning very tasty, saying that she loved being fucked by the transvestite, Gabi slapped her ass, saying that now she was ready to be fucked by the biggest dick there. Gabi, the transvestite, and our lover all laughed, and he immediately took his cock from my ass and went towards them. Apparently, the three of them had already arranged everything! Gabi told the boss to get on all fours on the other lounge chair and slipped under her to suck her clit, pulling the boss's head against her pussy. They started a delicious 69, and our lover approached from behind the blonde, pointing his huge cock at her pussy. Gabi held the cock and guided it, while still sucking her lips and clit. Our male leaned the cock's head against the pussy and slowly began to push his monster into the blonde. She stuck her face in Gabi's pussy. When the big head entered her pussy, she screamed, saying he was ripping her pussy apart, but it was wonderful. Our male gently pushed his cock into her, and the boss groaned with pleasure. And she only had less than half of his cock stuck in. When he put the whole cock in, she was already wiggling in Gabi's face, who was still sucking her clit, and asked him to fuck her because she loved to be fucked by huge cocks. She didn't even suck Gabi's pussy anymore. She just moaned loudly and asked to be fucked hard.

I had my ass opened by the male, but without a cock. Our transvestite friend had a hard cock without a hole to stick it in. We looked at each other, and she made a sign with her finger calling me. I mounted her with my back to her to watch the scene better. I sat my ass at once on that hot cock. As I had our male stuck in me before, my ass was already wide open, and her cock entered me super easy. She complained to our black lover that fucking anything after him was badass, as he left everything really stretched. He told her not to be jealous, that later he would fuck her ass too. Gabi got out from under the boss so they could move better and came to our side. She watched me riding the transvestite, and started jerking off my dick, saying she was the only one not taking advantage. Since my cock was already hard, and with her jacking, it got even harder, I told her to enjoy it too. I stopped riding for a while, with the transvestite's hot cock all stuck in my ass, and Gabi was standing over me. She was crouching down, looking for my cock, and started to sit on it. As she was also super wet from fucking our lover and watching her boss gets fucked, my cock got in at once. I asked her to stay still without my dick completely stuck in her pussy, and I went back to riding the transvestite's cock. When I went up, I stuck my dick fully in her pussy. When I went down, I stuck the transvestite's cock in my ass.

I increased the pace, and soon I was ready to come. I let Gabi and our friend know, and they said they were ready too. Gabi was the first to come and sit on my cock, forcing my hips against the transvestite's cock. With the deep thrust rubbing against my prostate, I also came inside Gabi. Our friend hadn't come yet, and she asked where I wanted her milk. Gabi quickly replied that she wanted it in my ass to suck it later. She got off me, and I kept riding more until the shemale filled my ass with her hot, thick cum.

On the lounger next to her, the blonde had already come four times, and our male was still pumping hard in her pussy. She was moaning deliciously. He also asked if she was ready for him to come, and she said yes, that she would love to feel the same rush of cum I had the week before. He increased the pace and came hard inside her pussy. As always, he came liters of cum, and filled her pussy! The transvestite had filled my ass with hot cum, and I was now on my fours on the lounger. Gabi was licking my ass to suck the cum, and milking my cock. In a few seconds, I came again, with her tongue stuck in my ass, which was now clean. Gabi had sucked all of our friend's cum from my ass.

The blonde was slumped over the chaise longue with her eyes closed. A smile betrayed how much she had enjoyed it. Gabi pulled me along so we could clean up the blonde together. We opened her legs that oozed cum from our male and started cleaning her thighs and going up to her pussy. She put her hands on our heads, caressing us while we collected all that cum from our male in our mouths, licking her pussy together, sucking her clit. When she was clean, we went up her body. Gabi went to kiss her mouth first, exchanging a hot tongue kiss and passing the thick cum into her mouth. I went to suck her big nipples and release the thick cum on her tits. The transvestite came to us too, and she and I started to spread all that cum on her enormous breasts while we sucked her nipples. She and Gabi were still kissing, sharing our male cum.

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