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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i can’t wait until You go shopping with neelia! 😉
Yes, yes! Will be SO much fun!!
Wow!!! I would’ve been so hard if we gone shopping! Just to have that happen to me would be such a thrill & turnon! Just to be with you doing that to me. What a lucky sissy!
Love that, Petey!!! Would LOVE to see you hard getting all dressed up. 🙂
Oh I love sissy dress up shopping trips!
Aren’t they awesome? How lucky are we?!
Ms Cindy/Ms Brighton/Ms Audrey & Ms Fiona want me to go shopping with them. I told them I don’t want to fight the crowds and I wouldn’t be any good. Also they have me wearing leggings/boots with girls turtle neck sweater with bra/panty underneath. What will everyone think? They want to go shopping for body con sheath dresses and said I need to wear them???? everytime we’ve gone shopping I always get hard and I soak my boy shorts. I’m afraid this will happen again. They said they are going to have me hold the dresses they pick out and have me try them on then get complete makeover at Victoria’s Secret. Everyone will know that I’m really a guy turned into a cream puff. With 4 hot mistress plus you and others in outnumbered and over powered.
Petey, don’t be so self-deprecating! They wouldn’t ask you/order you to go shopping with them if they didn’t think you would be safe and have a good time. They would surely watch out for your safety (mental as well as physical).
You might really have a good time!
With them along with you calling me Petey it makes me feel so weak/soft/submissive & feminine which I’ve become.It’s just that when we go I’ll be wearing leggings with knee high boots with girlish sweater along with matching bra/panty set. Yes I’ll be with 4 hot women! They will for sure look out for me. Just being with the 4 of then will be great fun. I won’t have in say with what they want me to do. Everytime we go I always smell girlish as they have sprayed me in perfumes along with soft, girlish smooth smelling skin. I just feel so weak/submissive and feminine in which they have turned me into.
Now this sounds like a shopping trip I could really enjoy. So different from shopping with one of my GFs. Shopping with a sissy friend pays back great dividends. Just to be there to see the joy on their faces, when they get to model – each and every potential purchase.
Then off to High Tea!
Isn’t funny how a sweet sissy can feel comfort with those sexy frilly things on under her suit?! Fantastic blog post Mistress Daphne! What a joy it must be to be your sissy. Shopping and champagne?! I love how you ladies role while shopping for lingerie together.
xoxox Mistress Tabetha
I love that you had her wearing a corset and panties under her suit, making all that wiggling and squirming well worth it! I’m sure you had fun watching your sissy girl try on all those frilly things, and I would have loved to see the look on her face as she gushed with delight, and begged you to let her cum. 😉
Ms Daphne! This is awesome! I love that you made her wear that awful suit to the dinner…such torture before the pleasure! This was such a sweet surprise for your sissy. I know she was really grateful later. 😉 Your description of the shopping was so masterful I felt like I was there! Really great post!