Sissy Boy Shopping: Getting Laughed at When Buying Makeup.

She’s my bestie, my other half, my ride-or-die!

I have a really strong bond with my buddy James, he identifies as a she. We go everywhere together, the nail salon, mall, spa, massage parlor, etc. She’s ridiculously hairy all over, massively tall, and strong for someone who doesn’t work out, but is a major girly girl! I swear this chick is so much more obsessive with her looks than me, she loves going sissy boy shopping all the time! I really hate when we go to certain places and people’s eyes just fixated on her, but not in a good way. You can tell when people are judgmental, and you can definitely tell when they’re talking about you. Especially when they point.

Jamie has been at my place for a while since her boyfriend has been treating her indifferently lately. We have a girl’s night every night! My boyfriend will be back tonight, so unfortunately, Jamie has to go back to her crappy boyfriend. Before dropping her off, I stopped at CVS Pharmacy to hunt down a sexy shade of red berry Revlon lipstick for her. Apparently, she has had it forever now, it’s almost gone, and can’t find it in any other stores!

Anyways, we’re minding our own business, Jamie takes one end of the makeup aisle, and I take the other. I’m looking under other makeup brands like Maybelline, just in case it’s not actually a Revlon lipstick. It’s so old the brand name has already faded off! I’m heading deep into the bottom section of the Maybelline line, and look over at some older short woman in her mid-50s coming towards Jamie. I hear her ask sternly if she can help with anything. Her gaze is stuck on Jamie, she probably has never seen a sissy boy shopping before.

Sissy boy shopping turns into a freak show.

“Oh, no thank you, we’re just looking,” Jamie said.  Yet, she insists on helping out. Jamie tells her about the shade of lipstick we’re hunting down, and when she does, the lady freezes. She has a dumbfounded look on her face and it takes her a while to come out of it. When she regains consciousness, she gently takes the lipstick from Jamie and begins to look as well. Luckily, I can bring my guard down when I begin to notice her making decent conversation with Jamie and even smiling a bit.

I go back to the hunt. After a few minutes, these two 15-year-old brats pass the aisle, then retrace their steps just to stop and stare at Jamie. They begin to laugh and even point and call out that there’s a sissy boy shopping. I feel the blood in my head begin to boil, Jamie does absolutely nothing! After no success in hunting down her lipstick shade, we begin to head out. She asks me why those girls were laughing, and even asked if it was due to her being a sissy. Since I’m her friend, I must be honest and tell her the truth, yes. She was so down in the dumps I couldn’t just drop her off at her shitty boyfriend’s house!

The negative sissy boy shopping experience gets a whole lot better!

Therefore, I drive towards my house and tell her we’re going to hang out a bit longer. On the drive, I text my sexy buff boyfriend, and ask for a huge favor! I’m letting him know about the situation that just occurred at CVS. Feeling bad for Jamie, I requested him to flirt with her once we get home, tease her, and fuck her while I wait in the living room. He loves me so much and always cares about my feelings, that he accepted! So then, I tell Jamie I have a little surprise waiting for her at home… Once we arrive, I can see Jamie’s whole face light up, when my boyfriend greets her butt naked at the door and asks,  “Are you ready for a ride? I’ll be your mischievous sissy trainer tonight.”

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