The Shopping Sissy
My favorite sissy calls involve a shopping sissy. That of course requires a cell phone with a really good connection, the ability to selfie during sales, and the courage to do it. I can list the experiences I have had with this but that would take a novel, so the most memorable fun experiences will be discussed.
Last was sissy Stacie, an apprehensive gurl who took weeks to get out and simply buy an outfit for shopping. I took her into Forever 21 at a local mall. The music was loud but I told her to find a sales person to help her find a girlie shirt, straight stretch jeans, and black ballet flats. A purse the color of the blouse which was a pink button down was ordered. A pink skinny belt with glitter, and pink socks. A selfie of her dressed up bod is posted on my blog. She sounds cute and I’m sure she is. After that experience she was more confident and proud she did that assignment for me! I was proud and happy too. After that she had a do it at home assignment which was orgasm denial for three days since she discussed she wanted to be in a pink chastity cage. We had to test it out because she was a daily stroker.
The most memorable of all shopping trips was a random sissy at Target in Hollywood. This sissy used her video on her phone so I had the pleasure of watching most of it. The cam was hidden for many views for obvious reasons. This involved me choosing things on the rack, shoes, and a purse. Panties of course, all floral. This required asking sales girls where she could find this and that. This is always required of course. All things were gathered, and in the cam I could see girls looking at her and laughing because she was dressed in her shopping dress and kitten heel open back shoes. All floral…lol.
In the women’s dressing room, she checked in with her items and passed because she was really passable. Her voice was a bit iffy but nothing was said. When she took her dress off in the dressing room, she showed me her pink lacy panties with a metal chastity device under. She had a pink bra to match. At this point she was dressing in the silly 80’s dress I had her pick out. The battery needed a recharge so we had about five minutes to finish the assignment. She dressed and posed for me, headed out to the checkout with dress on and explained to checkout she wanted to wear her new dress. The checkout girl smiled and the cam was very low now. The phone died.
About 20 minutes later she called back from the car with a good charge and asked if she could jerk off for me now and eat it. I said of course, that was what we agreed. What a great session.
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I loved having you advise me on the phone of what to get! I can’t wait to do it again
My pleasure sissy stacey, I can’t wait to see the dress you choose. You have such good taste!
I want to start doing this, but I’m city I live in everyone knows me:( it would have to be out of town. I want my friend to do this but she said I’ve spent to much money:( this is needed and best for me. She asked outside of tennis what do I do for fun and I told her I dress in women’s clothes/makeup/lipstick to relax. It’s all I want as I don’t care nor do I want to be in relationship as it’s to much work drama and emotion being in one. I’m to old to have girlfriends. Just want to do this one time. Having her have me try on dresses/makeup/lipstick would be hot!! Just don’t this this will happen as it’s wishful thinking?
Well Paulina, it sounds as if you have a whole fleet of Mistress mentors who would be willing to do exactly that with you, here at LDW! Obviously Princess Brittany is one of them!
And if you can’t do it in your home town, why not make a day trip out of it? A special occasion, where you can go just far enough away for discretion?
Though from the sound of it, you’ve told plenty of women in your hometown about your girly tastes, and, you know, word gets around . . . I don’t know that many people would be surprised if they saw you at the mall . . .
I would suggest just go out of town to a mall , save your money to shop, and yeah, a relationship forget it.
Your right Ms Rachel. Once I get back from overseas trip I’m going to do this. Once August is done,after Labor Day it’s time to. At my age most women are married with kids and girls I play tennis with have put me in friend zone. This means I’m not boyfriend material anymore and I’m fine with this. I’m hoping friend who took pictures of me with her phone dressed up as a girl wants to take day and go out out of town to do this. She’s selling women’s clothes and I’m going to buy them from her. She asked if I dressed up for therapeutic reasons and I said yes. At very least if she wants to go on shopping trip I can go dressed up and see if she wants to help me pick out lipsticks/makeup and try them on me/hold her purse and shopping bags. This is who I am and become.
Kudos to you, Paulina, and I’m sure W/e all look forward to hearing about the field report when you return from this trip, when it happens!