u/Lean_n_traps

This has been living rent-free in my head for days and I need to share how I fantasise about my first time…

Even though I’m still a total virgin when it comes to being fucked as a proper sissy, I don't want my first time to be gentle one-on-one. I want to go straight to two dominant guys who know exactly how to handle a nervous little sissy 😅

Here's exactly how I imagine it, we arrange everything through messages. They’re both in their late 20s or 30s, tall (way taller than me), toned, with that deep voice and natural alpha energy. They’re dominant and in charge, but also kind and reassuring at the beginning because they know it’s my first time 😇
I book a nice classy hotel. I arrive early, shave everything, do my simple cute makeup (soft pink lips, light blush, mascara, nothing slutty, just feminine and innocent), slip into pretty lingerie, a tight little chastity cage on my clitty, and a cute gem plug in my boipussy. Over it all I wear a feminine night dress with heels that make me feel tiny and vulnerable.

We meet in the lobby bar first. They’re dressed sharp, smell amazing, and immediately make me feel safe but owned. We have a couple of cocktails (just enough to relax, no one gets drunk). They tease me gently, call me “princess” and “good girl,” touch my lower back, and tell me how they’re going to take care of me tonight. My heart is pounding.

Then we go up to my room. Once the door closes, I get shy but try to be brave. I do a clumsy little tease for them (I don’t know how to do this 🫣) slowly unzipping my dress, letting it drop, revealing the lingerie, the cage trapping my excited clitty, and bending over slightly so they can see the shiny plug between my butt cheeks. They love it. They praise me, touch me, tell me how perfect I look.
It starts slow and sensual. Kissing, their big hands all over my body, making me feel small. They take turns using my mouth while the other plays with my plug. Then they bend me over, remove the plug, and start opening me up properly with finger(s) lube, lots of encouragement. One of them slides his veiny cock into my boipussy first while the other feeds me his cock. They’re thick and long and I feel so full and desperate.

From there it escalates into the most depraved sissy threesome I can imagine. They start by rawdogging me on the bed with one thick cock stretching my pussy while the other fills my drooling mouth. I worship them completely, licking and sucking their heavy balls, burying my face between their cheeks to rim their asses like a good little sissy whenever they command 🥵 They praise me for being such a nasty girl while I tongue their holes.

As the heat builds they get rougher and nastier 😈 They take turns pounding my holes deep and hard, pulling out to admire how my I play with my gape and push out a soft, pink prolapse from the relentless fucking… They pass me back and forth like a shared cumrag, making me ride one alpha’s cock reverse cowgirl while I gag on the other’s dick and balls. My caged clitty leaks (pre)cum constantly, dripping all over their bodies and the sheets as they destroy me

The depravity keeps climbing. They double penetrate my stretched boipussy, both cocks forcing their way in together, making me whimper and moan like a bitch in heat. I keep sucking and rimming them between positions, cleaning their sweaty balls and ass while they fist my already ruined hole. I’m a complete sticky, cum-drenched mess, my prolapse still peeking out as they use me nonstop.

When we’re all completely spent, our sweaty bodies collapse on the bed and I fall asleep like that, with my hole still leaking cum and sissy juices.

In the morning I wake up first. My holes are still dripping their cum, my body sore and marked. I feel so used and happy. I slip on a silky nightgown, and quietly go down to the buffet to bring breakfast back for my two men.
When I return to the room the smell hits me like a drug 😵‍💫 pure sex, musk, cum, sweat from the night before. It instantly makes me desperate again. They’re still asleep but their soft cocks are bigger than my clitty was or will ever be… I crawl onto the bed and start gently sucking them, cleaning and worshipping their soft dicks with my mouth.

As they wake up they get rock hard again and turn nasty. Really nasty. They pin me down and fuck me even harder than the night before. Rough, degrading, using me like a total cumdump. No gentleness this time, just pure dominance as they breed me again while I moan like a bitch in heat… At that point I completely surrendered and I’m their sissy whore princess 🥰

God… just typing this out has me leaking in my cage. Is this too much for a first time? Or are there other sissies who fantasize about jumping straight into being shared and ruined by two men?

This has been living rent-free in my head for days and I need to share how I fantasise about my first time…

Even though I’m still a total virgin when it comes to being fucked as a proper sissy, I don't want my first time to be gentle one-on-one. I want to go straight to two dominant guys who know exactly how to handle a nervous little sissy 😅

Here's exactly how I imagine it, we arrange everything through messages. They’re both in their late 20s or 30s, tall (way taller than me), toned, with that deep voice and natural alpha energy. They’re dominant and in charge, but also kind and reassuring at the beginning because they know it’s my first time 😇
I book a nice classy hotel. I arrive early, shave everything, do my simple cute makeup (soft pink lips, light blush, mascara, nothing slutty, just feminine and innocent), slip into pretty lingerie, a tight little chastity cage on my clitty, and a cute gem plug in my boipussy. Over it all I wear a feminine night dress with heels that make me feel tiny and vulnerable.

We meet in the lobby bar first. They’re dressed sharp, smell amazing, and immediately make me feel safe but owned. We have a couple of cocktails (just enough to relax, no one gets drunk). They tease me gently, call me “princess” and “good girl,” touch my lower back, and tell me how they’re going to take care of me tonight. My heart is pounding.

Then we go up to my room. Once the door closes, I get shy but try to be brave. I do a clumsy little tease for them (I don’t know how to do this 🫣) slowly unzipping my dress, letting it drop, revealing the lingerie, the cage trapping my excited clitty, and bending over slightly so they can see the shiny plug between my butt cheeks. They love it. They praise me, touch me, tell me how perfect I look.
It starts slow and sensual. Kissing, their big hands all over my body, making me feel small. They take turns using my mouth while the other plays with my plug. Then they bend me over, remove the plug, and start opening me up properly with finger(s) lube, lots of encouragement. One of them slides his veiny cock into my boipussy first while the other feeds me his cock. They’re thick and long and I feel so full and desperate.

From there it escalates into the most depraved sissy threesome I can imagine. They start by rawdogging me on the bed with one thick cock stretching my pussy while the other fills my drooling mouth. I worship them completely, licking and sucking their heavy balls, burying my face between their cheeks to rim their asses like a good little sissy whenever they command 🥵 They praise me for being such a nasty girl while I tongue their holes.

As the heat builds they get rougher and nastier 😈 They take turns pounding my holes deep and hard, pulling out to admire how my I play with my gape and push out a soft, pink prolapse from the relentless fucking… They pass me back and forth like a shared cumrag, making me ride one alpha’s cock reverse cowgirl while I gag on the other’s dick and balls. My caged clitty leaks (pre)cum constantly, dripping all over their bodies and the sheets as they destroy me

The depravity keeps climbing. They double penetrate my stretched boipussy, both cocks forcing their way in together, making me whimper and moan like a bitch in heat. I keep sucking and rimming them between positions, cleaning their sweaty balls and ass while they fist my already ruined hole. I’m a complete sticky, cum-drenched mess, my prolapse still peeking out as they use me nonstop.

When we’re all completely spent, our sweaty bodies collapse on the bed and I fall asleep like that, with my hole still leaking cum and sissy juices.

In the morning I wake up first. My holes are still dripping their cum, my body sore and marked. I feel so used and happy. I slip on a silky nightgown, and quietly go down to the buffet to bring breakfast back for my two men.
When I return to the room the smell hits me like a drug 😵‍💫 pure sex, musk, cum, sweat from the night before. It instantly makes me desperate again. They’re still asleep but their soft cocks are bigger than my clitty was or will ever be… I crawl onto the bed and start gently sucking them, cleaning and worshipping their soft dicks with my mouth.

As they wake up they get rock hard again and turn nasty. Really nasty. They pin me down and fuck me even harder than the night before. Rough, degrading, using me like a total cumdump. No gentleness this time, just pure dominance as they breed me again while I moan like a bitch in heat… At that point I completely surrendered and I’m their sissy whore princess 🥰

God… just typing this out has me leaking in my cage. Is this too much for a first time? Or are there other sissies who fantasize about jumping straight into being shared and ruined by two men?

Don’t be shameful, we kind of all started with this 🤭

When and what was your first experience with female underwear? Whose were they ? Were you more wanting to wear it or sniff it ? Did you have other experience since or have you ever been caught ?? Tell us all babes 💖

Personally, I remember being quite young like 13 yo, trying a black bodysuit lingerie from my mom and being juste amazed by the feminine beauty in the mirror 🤭