I’d hinted about what I was getting my real-life sissy for Christmas for at least two months. I knew it was driving her crazy.
And I loved it.
Finally, the day came when I was taking her Christmas Shopping.
I specifically asked that she wear her nicest man clothes… a suit with leather shoes. Something that would make her so uncomfortable, putting anything female on would be an enormous relief.
I took my sweet girlfriend, dressed to the nines in a black suit and tie, to my favorite restaurant and we had a leisurely six-course meal that took over three hours to complete. It was so much fun to watch her squirm in her suit, knowing that, even as she wore it every single day at work, she wished to be out of it every second. I made sure we had good wine with our meal; we were feeling full of great food and the edges were soft and fuzzy because of the wine.
Christmas Shopping Boutique
I’d hired a limo to take us to where we were going… my girl still didn’t know the destination. Although, I knew she would get the hint rather quickly.
Now, I know lots of folks like shopping at Victoria’s Secret, but my dear sissy is a larger-sized gal and VS doesn’t come near her size, so we went to the boutique I know personally that caters to big… gorgeous… women.
Samantha owns one of my favorite big girl lingerie stores and I could feel my sissy shivering with delight as we crossed the threshold. We walked in and could almost smell the scent of silk, satin and lace panty and bra sets. I’d asked Sam to pick out several items with my instructions towards style and color and she ushered us into her side salon, decorated with beautiful flowers and brocade curtains. Hanging from the elaborate hangers were a bouquet of styles of lingerie: rompers, camis, babydolls, bikini sets, negligees… the whole gamut of under-wear.
In a swirl of soft and sheer fabrics, my sissy girl tried on silk after satin after lace. She looked lovely in so many; our stack of TAKE was far larger than our stack of LEAVE. I giggled at her hard-on and poked at it several times, causing immense (delightful) misery to her trying-to-keep-her-composure Self. I laughed delightedly as she dressed in creamy pinks and purples, all with that cock sticking out the top. She was (appropriately) humiliated. Didn’t keep her down though, did it. laughing
She asked if she could cum while wearing one of the satin and feather creations and I told her NO she could not… she had to hold it until after we got home when she could dress for me and then perform for me. I thought she was going to cum right then! I squeezed the head of her cock hard to keep that jizz from jumping out.
We gathered up our piles of lingerie and I paid for it while my dear girl Sissy sipped champagne. I knew she would thank me properly later. (And I gushed juice in my pussy thinking about it!)
After our Christmas shopping trip, I took my girl to the nail salon where we both got manis and pedis. She still wore her suit, but only she and I knew what was underneath: a cranberry-colored bustier that I tied tight and a pair of matching string bikini panties.
She no longer struggled in her suit.
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