Mike aka Sasha is a sexy Sissy Boy that I’ve been playing with for the last few months and she is coming along nicely.
He sort of looks effeminate when she’s Mike so when she’s Sissy Boy Sasha she’s actually passable. I’ve been trying for ages to get her to show the world how hot she is but she’s been too scared; she thinks people will make fun of her or beat her up. I had to show her that she was perfect the way she is and took her out to my favorite bar.
Every lady and Sissy Boy needs to look good so she came over to my place first so we could get ready. She showed up with a couple of dresses and I told her to wear the short blue one. It was tight and would show off her flat stomach and trim waist. It wasn’t too low cut and with the help of a push-up bra. She’d look stacked which would take attention away from the hint of Adam’s Apple and slightly big hands.
I helped her with her makeup. Making her lips a sexy red and using eye shadow to make her eyes pop.
Her wig was wavy brown hair that fell over her shoulders and when she showed me how good she could walk in her heels now I couldn’t believe she had a dick hidden away. Her ass gave a little wiggle and she moved with ease like a perfect Sissy Boy.
She knew how to act sassy and all the guys would be noticing her tonight. She was nervous but I told her to trust me, it was going to be fun. When we got to the bar it was already busy and we had a couple of drinks to loosen up while guys started checking us out. We got a few cheesy pickup lines and a few numbers which I saved for later.
They seemed to be hitting on me more. Probably because I was more confident and outgoing but I wasn’t in the mood to get laid. I wanted Sasha to get the attention tonight so I pretended to head to the bathroom, finding a spot by the wall to watch the show. She looked around the room, trying to make eye contact with people. It only took a minute for a cute guy went over to her and bought her a drink. Flirting with her hard as he smiled and touched her arm.
She flirted back, pressing her body against his and whispering in his ear.
I wondered what she was saying to him because it made him put his hand on her ass and nod towards the door. She hesitated, knowing that if she left with him it was just a matter of time before he found out that she was actually a guy.
I was on edge as I watched them talk a bit more. I’ve been working so hard on her that I didn’t want her to go back in her progress. When she picked up her handbag and started to leave with him I felt so happy and proud; she had done it! My little sissy had just got picked up by a straight guy.
I spent the rest of the night getting friendly with a college boy named Jacob. When Sasha texted me I just had to see how things turned out. She had managed to give him a blow job without him finding out what she was. He was crazy about her. Apparently, she sucks guys off like a pro and they’re seeing each other again tomorrow night.
