Strict sissification is not for the weak. It’s always fun to see how far an “alpha male” can fall from his pedestal. This story is all about a friend of mine called Brian. This prior-fuckboy really ticked all the boxes. He has a great job and previously fucked whoever he wanted, including many stories of his sexy topless neighbor. He’d always been a man’s man — obsessed with toys, and the toys just got bigger: trucks and guns and all the fun stuff. That was until he found himself slipping down a rabbit hole of fetishes and kinky roleplay. It all came to light after a house party. I’d invited over a few of my friends for a drinking and game night, completely unaware of how the night would unfold.
By the end of the night, Brian’s true mannerisms started coming out. Every time the girls would joke and talk about a recent hookup and his big dick, he became very invested in the story! After a bit, the party moved to my room. And thus began the dress-up games. Before long, I noticed every time my friends would take an interest in trying on some high heels or doing their makeup, Brian also injected himself into the situation. I started calling him a little sissy bitch just for jokes, but he actually LOVED it. So we spoke a little bit about it once some of my friends had left for the night. And thus began the strict sissification of a prior alpha male, whom I had now renamed Britney.
Britney was so excited to try on all the sexy heels in my closet. Her favorite was a pair of hot pink stiletto heels with glittering ankle straps. She waltzed around in front of the mirror, wearing nothing but heels and a little pink thong. I told her to have some decency! A full strict sissification session has some rules she needs to follow. Her titties needed to be in a matching pushup bra, that way they would poke out even more. She wanted to give into true girliness, so she needed to follow the rules. “One day, you’ll get implants so you have big double-Ds filling that bra in. You’ll LOVE being a bimbo slut!”
I had her practice walking in those heels all night, just so she’d be truly comfortable in them. By the end of it, I’d even taught her how to twerk and shake her ass to all the latest songs. She practiced in the mirror until she could make it clap — her ass cheeks clapping as she twerked. It was like music to my ears. Strict sissification brought out the sluttiest side of her. Not only was she ready and willing to get implants and lip fillers, she wanted to undergo total feminization. Within a few months, there wasn’t a single trace of “Brian” left. She even had her nipples pierced so that they would be constantly perky, and glittering with little crystal studs. She was blossoming into a perfect bimbo!
With all the dressing up and her new wardrobe and body, she started to give in to her cravings. All Britney cared about now was DICK. She needed cock. She craved a big cock to fuck, and a big cock to suck on. There wasn’t a single thought behind those eyes. Every time she fluttered her long, dark, false lashes, all she could think about was cock. Her lip-filler plump lips were perfect for blowjobs, and it was all she daydreamed about. So as a treat for all her progress, I took her for a night out on the town. Step 2 of the strict sissification process: learning how to suck and fuck cock like a well-trained whore!
Are you ready for the next step of your sissification? Call me!
Cross Dressing Friend Hates Boy Clothes So I have this pretty c... Read More
It’s only a matter of time – StrapOn Anal Pegging I... Read More
Adopting a Sissy Son Believe it or not, I met my sissy son because of... Read More
I didn’t know he was a Cross Dressing Bitch! Here is how... Read More
Squirting tiny dick caught dripping on my dirty laundry… Fina... Read More
Sissy loves humiliation, and pet training auditions are tonight!  ... Read More
Draining pockets is the name of the game. You might be a pathet... Read More
Share your Kinky Sex Confessions There comes a day when you nee... Read More
Turning an “alpha” male into the girliest bimbo. St... Read More
It’s NOW or NEVER – Forbidden Erotic Desires Are yo... Read More
I didn’t realise I was dating a sissy panty stealer! I’m oft... Read More
There’s something about a big black cock that puts me in a sharing m... Read More
Sexy and Sultry! Sloane is 🔥
Paige is the best of the best. If you want a submissive housewife, she’s the best. Are you into edging phone sex, she’s the best. Do you want creative and orgasm inducing roleplay, she’s the best. She’s beautiful, intelligent, sexy with an alluring voice. She has my highest recommendation.
Raven was just what I needed. She was so professional and exciting to be with. I always look forward to our session’s and I already can’t wait to call Raven again!
Meghan was fantastic! She provided me with a roleplay that I had never done before and it was very erotic. I will definitely call her again!
Still getting to know Jamie, but our calls have been phenomenal. Jamie has “thrown herself” (I hope she laughs when she reads this) into my fantasy with both care and abandon. She listened to me carefully, ran the role-play exactly as I’d hoped, and then threw in her own totally appropriate and totally wicked ideas to take it up a notch.
There really aren’t many superlatives left for Avalon after so many calls, but perhaps she will appreciate this one. I never understood what a GFE was until I started calling Avalon. She is astonishingly good.
Karina is so attentive and detailed to my needs. She is excellent at listening and gives me the best experience. Call her!!
I love Sloane to the death! She has a great personality and is amazing at what she does!
Sloane is the best! She’s sexy, smart, a great conversationalist, and has a fiendish laugh that is infectious. She’s adaptable and is incredibly imaginative. Talking to Sloane is an experience in itself. You need to call her.
Eden is amazing! Her voice is soft and sweet, she knows just what to say and how to say it. The call was hot, sexy, and steamy. It was the perfect ending to my evening.
Jami made my Friday night! I couldn’t go out to play so she helped me out by providing me with exceptional role play. We agreed on the role play and she provided me with an exceptional experience. I wish I could chat with Jamie every day. She is a huge asset to PSK!
Vivian is Hot! She was a lot of fun to play with!!