Fantasies of a Bisexual Shy Couple #01

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Our first fantasy is with a transvestite pleasing the couple.
2.5k words
4.26
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Part 1 of the 21 part series

Updated 06/13/2023
Created 12/06/2022
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We are a mature couple, both 50 years old, who have been together for over 30 years, between dating, engagement, and marriage. Here we will use the names of Filipe and Gabriela (changed for obvious reasons). We have children and our everyday life, between home, work, and other obligations.

I (Filipe) will start to report here how this site changed our lives and created fantasies that excited both of us and that we intend to fulfill one day, but always together!

We noticed that our sex life fell into a routine. We tried to escape through our fantasies and on the Internet. One day, while helping her with a problem with her notebook, I noticed that she was accessing erotic stories websites, which I also did when I tried to read about my fantasies.

It was something new, an opportunity for us to start opening up about our fantasies and desires and the grind our marriage was falling into. I suggested we start sending each other the stories that excited us the most.

I, more daring, sent tales of all kinds, mainly the ones that turned me on the most, especially about male ménage (I think the fantasy of 99.9% of men, everyone would love to see their wives/girlfriends having pleasure with another man, but that very few dare to assume). But I also sent stories about transvestites and bisexuals (both men and women). When reading these tales, I always imagined putting ourselves in the characters' places and feeling the same pleasures.

Her responses, always more polite, also began to bring stories with the participation of other people (men, women, and transvestites). Still, they were mainly responses about which she liked more or less among the ones I sent her.

And through her answers, I realized that she also has daring fantasies but is very ashamed to open up. I feel like she is very horny thinking about other people in our bed, but she feels embarrassed to admit it, maybe out of fear of what I might think of her in this sexist and silly society. But honestly, I'm very open to new ideas about sex, and I believe that anything is valid for pleasure between 4 walls, with a consensus from both. There are no limits to pursuing pleasure as long as it doesn't involve violence or something forced.

Our sex was always excellent. I love foreplay, especially to turn her on, with kisses, caresses, my hands, fingers, and tongue all over her body. Even though it's not a perfect body (none of us are, we're an average 45-year-old couple, unlike many here who call themselves or imagine gods!), it always drives me crazy. I love her full breasts, her hot ass, her thighs, her mouth, her neck, and of course, her pussy. Looking at her, dressed or not, will always turn me on. I love to pat her, run my hand over her hot body, all the time. On account of business trips, we sometimes stay away for a few days, and these days we try to satisfy ourselves (masturbation or the use of vibrators in her case), but mainly by having virtual sex via Skype, one showing the body to the other, and enjoying together.

In one of our plays, during foreplay, I started caressing her body, kissing her neck, and talking in her ear about how nice it would be to see another woman doing what I was doing, and I would be closely watching the two of them having sex. I started to run my hand all over her body, kiss her ear, and keep talking about what the other woman would be doing to her body. I started to play with her little clit, and I felt how wet she was, above average, showing me that she was enjoying the fantasy, and it was turning her on a lot.

I continued kissing her delicious, full breasts. I went down through her belly, her navel, reaching her pussy, which I started to suck with affection and delicacy as if it were the other woman sucking her (my friends, here's the tip, they prefer caresses, tongues, and soft sucking than hard sucking on their clits!). Always talking like the other woman would be pleasing her. She kept her eyes closed, still very wet with lust, showing that she imagined a female mouth sucking her hot pussy. I said I would watch the two of them having sex and masturbating, seeing her having pleasure with another partner. After a few minutes, she exploded in sensational orgasm, holding my head tightly between her legs, as she always does when it is terrific.

We continued to have sex, with hot penetration in her pussy, doggy style (her preferred position), and we came together (things that a couple who know each other well can do most of the time). I told her I had enjoyed watching her imagining the situation of another woman pleasuring her and how much it had turned her on (I never saw her so wet). I also told her it had turned me on, too (I also went crazy to see her so wet!). She continued with the shy posture, without saying openly that she liked it, but for her excitement, she didn't even need to say how much it had messed with her imagination!

I started to send her more lesbian stories, but in her replies (where in some cases, she sends the stories she sought and liked, but most of the time, she comments on the ones I sent), Gabriela began to show that the ones she liked or turned on the most were the who had a transvestite with the couple.

A shemale is something that excites me a lot, too. The figure of a hot transvestite, a woman and a man simultaneously, has always excited me. And I started to explore more because I imagined a hot shemale in our bed, giving her a lot of pleasure with her feminine attributes (breasts, ass, etc.), but also the image of seeing another dick penetrating her hot pussy. At the same time, I watch or get sucked by her. I started talking, in some of our fucks, that I would like to have a hot shemale with us, licking Gabriela's body, and also her sucking the shemale's dick. Of course, this also stirred my imagination, and my participation in this sex would be total. Imagination runs wild, and I see us allowing ourselves everything between the four walls.

I imagine the sex would start between them, where the shemale would slowly remove Gabriela's clothes. It will reveal the sensual lingerie that I would help her dress earlier. I will also have prepared her for this unique session, shaving her hot pussy and leaving her smooth for more pleasure. I imagine her being caressed by the transvestite, having her whole body explored by her hands as they kiss. I would come up behind her, making a nice sandwich with her body between us while the shemale and I caress her lovely body. We play with her nice big tits, her meaty butt, her tight ass, and of course, with her soaked pussy. We would have a triple kiss, our tongues vying for her mouth as we continued the caresses.

Then I would ask her to start undressing the transvestite, removing her clothes and imagining her in very sexy lingerie (I love women in corsets, garters, stockings, and thong panties!). She would also start exploring the transvestite's body, playing with her breasts, sucking them too (I think she's crazy to do that, I love playing with the nipples of her big tits, sucking them!). At that time, I would hug the shemale from behind, changing the sandwich filling.

I'll love to see her start caressing the transvestite still in her panties, trying to explore what she will find there. Watch her lower her panties slowly to see the transvestite's dick appear gradually, not yet fully hard, so she can start sucking it the way she likes, shoving it all into her hot, wet mouth, and feel the cock grows inside it. She sucks, licks and kisses as she does with mine, which drives me crazy!

Then, with a very naughty face, kneeling in front of the transvestite and sucking her tasty cock, she would call me to share that, asking me to help her suck the shemale. Asking me to kneel beside her, hold the transvestite's cock in front of me and ask me to kiss, lick and start sucking the cock along with her. Kissing me with the transvestite's cock between our mouths, our tongues disputing the cock. While one sucks her dick, the other sucks her balls, alternating and sharing the cock and giving the shemale a lot of pleasure. I can already imagine her pussy wet with the situation, and I playing with her clit while we suck together.

Then I would lay them on the bed in a tasty 69 with my naughty wife on top, and I would alternate helping with the blowjobs. First, I would help the shemale to suck her, playing in her ass while the transvestite sucks and licks her hot pussy. Kiss the shemale, taste Gabriela's pussy in her mouth (the taste of her pussy is lovely, sweet, fragrant), and continue to explore her pussy and ass to drive her crazy. I would also help my wife to suck the transvestite's cock, and see her taking great pleasure in being sucked and sharing the dick with her husband.

To start penetration in her, I would put a condom on the transvestite (always a condom, friends!!), and I would start doing a 69 with my wife, she on top, sucking my dick, me sucking her pussy. Then asking the shemale to begin to fuck her in her preferred position, doggy. See, inches from my eyes, the big cock opening her pussy, entering inch by inch, until seeing the balls touch her and start hitting my head too. I would suck my wife's clit and the shemale's dick together, feeling in the dick how wet she would be from being eaten in her favorite position while still sucking my dick, filling her little mouth as she likes it so much.

Feeling her suck my cock harder while the shemale fucks her hard as she likes, and my tongue plays with her cock to make her even more excited until my wife reaches a fantastic orgasm.

While she recovers, the shemale and I would explore our bodies, our cocks, our asses, our assholes, getting ready to continue playing. Ask the transvestite to cover my cock with a condom and to be on all fours opening her ass so I can fuck her. Feel my dick entering her slowly until I touch my body on her ass in a complete and deep penetration. The wife, already recovered, would go under the shemale and start sucking her cock, while I moved my cock in and out the shemale's ass. With each thrust of my dick in her ass, I see her dick enter my wife's greedy mouth.

But before we both came, we were going to reverse the position. My wife and the shemale would suck me. I would lie on my back, with them starting from my cock, my balls, until reaching my ass and starting to prepare it for penetration too. The two are sucking, caressing, and beginning to put their fingers in my ass until I feel ready for the shemale cock. Then see my wife lift my legs, leaving my ass exposed, and guide the shemale's cock to my virgin ass (virgin for real cocks, because my wife already plays with her fingers and vibrators on it!!) until I feel her head touch my ass. Feel her forcing and opening my asshole until I receive her cock's head. Then she stopped and let me get used to her dick inside me, then started shoving it to the end, feeling her balls hitting my body.

My wife would be sucking my cock, and watching closely the shemale fucks her hot husband. After sucking a lot, she turns around and sits on my cock, while the transvestite continues to fuck me in my ass. We would make a nice little train, with my wife riding my cock, me sucking her tits, and the shemale fucking me nice in the ass. I would explode in her pussy, leaving her all filled with cum, and making my cock slide even easier inside her.

Given our excitement, we would not stop. I would continue to fuck my wife, but now opening her hot ass and asking the shemale to put it in her lovely tight ass. I would lay my wife on my chest, kiss her a lot, and open her little ass for the transvestite to start putting her cock in a double penetration to drive my wife crazy. I will feel shemale's cock in the ass, squeezing my dick in the pussy, until Gabriela gets both cocks inside her. We would start to fuck her together until we both come inside my wife, me in her hot pussy, and the shemale in her ass (with a condom, of course!).

Then I ask my wife to sit in my face and let me suck her pussy, full of my cum. Licking her pussy clean turns me on and drives her crazy. She usually comes one more time while I do the cleaning.

Then we lay down in the bed, me in the middle with one on each side, and rest together, feeling our bodies touching, our skins touching, and probably this will only lead us to start the party again!

She loves that I finger her ass while I fuck her pussy from behind. I love to feel that I'm filling her with my cock and fingers and hear her moaning. Experience this is definitively her wish and fantasy. I can see the difference in the intensity of her orgasms and moans when I have my finger in her ass. And when I'm fucking her ass, as soon as the cock starts to enter her tight asshole and she plays with her vibrators in her clit, her orgasms come fast and loud.

She is always timid, with difficulty recognizing how much it excites her (but see how she moans or how wet she gets, that is clear and needs no words). I'm slowly awakening the naughty girl inside her, the slut who wants to experience new sensations, who wants to feel pleasure in other ways, but who still has difficulty (or fear) recognizing it. Slowly she's opening up, and I think maturity also makes her feel more confident to tell me what turns her on and what she doesn't like.

I'm still going to convince her to make that fantasy come true, as it's something we both want so badly.

I will continue writing our fantasies here and tell you in detail if we realize them.

Leave your comments here. Gabriela will read along with me, and maybe you guys will make her even more excited to assume she wants to fulfill these fantasies.

Kisses from the couple to all!

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7 Comments
heyrockyheyrockyabout 1 year ago

That’s one of my favorite fantasies as well. Nice start I can’t wait to read the next one.

ShortyMacShortyMacover 1 year ago

Nice story, It’s a fun read just like having a transgendered girl join in your sex life. I hope to read more stories from you in the future. Thanks for sharing…

AnonymousAnonymousover 1 year ago

Well done, looking forward for more of your tales!

DianeRedfernDianeRedfernover 1 year ago

Very hot and wet beginning. I want to read more. Experimentation turns me on.

xoxo,

Di

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