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.
“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!
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.”
Want some more sissy boy fun?
I made Clint my sissy bitch! Clint has always been different re... Read More
Kiss My Ass I’ll Do Yours If You Do Mine You Sexy Thing K... Read More
My secret sissy boyfriend! I’m often asked whether I prefer... Read More
Are you looking for someone who accepts you as you are? If so,... Read More
Pantyhose Fetish Jack had a stockings and pantyhose fetish for years a... Read More
Panty licker knickers sniffer… I know you do it. You ca... Read More
I Didn’t Know He Wanted Some Neighbor Pegging Sex See I h... Read More
He became a Partition Propositioner before my eyes… Hello... Read More
Universe Alpha Centauri –Dance under the rule and era of your Go... Read More
Showing off the goods The door opened and Jim was greeted by an... Read More
Turning Gay For Mistress – Could It Happen? Hello, bloggi... Read More
As I looked at my new sissy slave, all dressed up in the sluttiest out... Read More
Tremendous customer service and professionalism. Aileen took the time and interest to start getting to know me. Just a delight to have a conversation with, aside from her sexy voice.
I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
I had a great time with my two beautiful and sexy ladies Carmen and Kayla. It has been a while since we played together. It was definitely worth the wait!
Ariel is truly amazing. Her voice is seductive and she really knows how to bring out the dirtiest version of me, hehe!!
Aileen is hot as they cum. She really knows what she is doing and is always the most satisfying!
WOW, I had an absolutely wonderful and memorable call with Jade! She listened to the role play that I wanted to work through with her and she was beyond perfect. She was able to step into her role as my milf neighbor growing up and really made my phone sex fantasy come to life! I can’t wait till I am working out of town again and have another chance to call her as I have other role plays to do with her.
Joey OUTSHINES everybody!! She is the ABSOLUTE PERFECT combination of everything. Sweetness ✔️, Compassion ✔️, Sincerity ✔️, Intelligence ✔️. And her Sexiness. . . OMG!!! Joey makes my life AMAZING!!!
Bailee was super enthusiastic and rolled right into playing out the fantasy I had. She is phenomenal.
Amber is kind and understanding of my needs. She would make a good friend!
This was only my second call with Addison, and I am already addicted to her sexy voice. She knows exactly how to command and control me. Love the way she takes me all the way to the edge, before she gives me the hands off command. Looking forward to obeying her more often.
Vanessa is simply amazing. She can be so precious or be so fucking wicked. Her oral skills are insane. She will make your cock cum, cum and cum again. If you want a spicy and wicked good time, Call Vanessa!!
Had a super hot call with Gracie! Her voice sounds so innocent and seductive at the same time. She is so sexy and we always conclude with an explosive finish.