A Little Shopping Trip

Hmm, well I had a really fun time tonight. It started out being not a great day because I was suppose to have a shopping trip appointment with a gentleman tonight and he cancled on me. So I was a little down and sad about that, but in talking with another sub, he decided he wanted to take me on a shopping trip himself and have a session with me. So I of course accepted.

I met this guy at the local Outlet Mall and there we started shopping for some clothes... for him. He wanted a Lady Domme to help him pick out and force him to buy some lady clothes for him to wear. So we went into a few stores. First we went into Calvin Klein and looked at a few things but I was not that impressed. We also checked out a couple other places such as Ralph Lauren and Tommy before finally going into Victoria Secrets. I am sure I made him very humiliated as I held up panties and bras right to him to see how they would look against him. I did hear a few snickers from a few ladies and men around us. My subby was 100% sure they were snickering right at him. I also held up a few shirts and nighties to him. When a sales lady came up to ask if she could help us, I looked right at her and told her that I was looking to buy my naughty boy here some ladies panties and female items so he could wear them. She just smiled and said she would be glad to help.

So with her help we were able to find 5 pairs of panties, 2 bras and 1 nightie for him and took them up to buy. She laughed when I told him to get his credit card out and commented that she thought I was buying them. I smiled right at her and said, I am buying them. With his money. She laughed and finished the sale.

Next of course we needed some shoes. So we went to a few shoe stores and found him a very nice pair of black heels. Finally we went to Claires where we got him some jewerly. He also bought me a few cute outfits for myself. Which I just love.

We stopped at a Walgreens on the way to his hotel and picked up some lipstick, finger nail polish and other make up as well as pantyhose. Back at his hotel room I made him model all the different panties for me as well as the bras and nightie. I picked the panties and bra I liked best and had him sit down. Where I pulled out a wig from my bag and put it on him. I painted his finger nails and did his make up with the finishing touches of adding a necklace around his neck. I then pulled out a skirt and top I had brought with me and had him put those on. Which he did. Finally the pantyhose and heels. I had him walk back and forth for me to practice walking on heels. Then I had him.. well I should say her now huh, since I did turn him into a very nice female. I had her bend over the bed and I pulled up her skirt and pulled down the panty hose and panties to her knees. I proceeded to spank her for not thanking me for helping pick out her clothes and items. And for not thanking me for doing her make up so very well. After spanking her I pulled out a brand new dildo, upwrapped it, put a condom on it and lube. She wiggled her behind at me, which I smacked again and told her to hold still. She did. I put the dildo onto my strap on belt and slowly slid it into her. A little bit at a time. She had never had any thing like a dildo, butt or real cock in her ass before. So I had to be slow and gentle. After awhile she adjusted and I was able to get the whole thing into her and fill her up like she needed to be. I started moving faster and faster. Giving her the real fucking she begged for. I made her grab the cock in front of her and start playing with it, stroking it as I pushed my strap on in harder and faster and she begged for more. She matched her hand strokes to my pounding and when she exploded and came (after begging and pleading me) she shook a little bit from the the pleasure. I removed the strap on, pulled up her panties and her pantyhose and pulled up her skirt and told her what a very good girl she was for me. Then had her curl up under the blankets for a little bit. Where she fell asleep.

What a wonderful night. I love play mates.

Now though I am a little bit tired and have a headache so I must get some sleep. For I have a long day tomorrow. Good night All!