Halloween 2019

Halloween was on a Thursday and it was a cool day and I had to drive to Dallas for meetings on Friday. My wife could not come with me so she picked out what I was to wear since I was going to be unattended. The night before, we painted each other's fingers and toes: hers in bright red and she chose a bright pink for mine. I woke early Thursday showered and shaved my legs and crotch shaped with a nice landing strip. She chose my vintage Victoria Secrets 2nd Skin Satin matching lavender bra and hi cut panties, garter-belt and beige lace top sheer stockings with a rear seam under my vintage Vanity Fair light pink, nylon and lace trimmed, above the knee full slip; I love the color contrast of this lingerie combo.

She bought a dress very similar to this at a consignment shop a week earlier in her preparations for my day that I had not seen yet and I thought it was for her when I first saw it. She said the temperature was warm enough so I wouldn't need a sweater or jacket which I as happy about. I hated covering my lingerie but when I saw the dress, I didn't want to cover it up. The dress was pleated so I didn't have to tuck myself back which I hate and she know it. I was nervous about wearing all this without her being there with me as was the norm but she insisted I can do this.

She helped me get ready, making sure my seams were straight and my bra and slip straps were adjusted comfortably to accommodate my unattached breast forms. She put minimal make up on me an put bright pink lipstick to match my nails. My wife noticed my slip tenting and said we have to take care of this before I put my dress on and gave me the sweetest blow job then sharing a bit of my love juice with me. She said no wig. I want you to be more of a man in a dress than a man trying to be a woman. She put heavy gel in my hair giving it a shiny curly look.

Satisfied, my wife helped me while I stepped into the dress and zipped me in this heavenly satiny material. I slipped into my beige 2 1/2″ sling back open toe heels, clipped my dangling earrings on, she gave me her pearl necklace and matching bracelet, a beige leather purse with a long gold chain large enough to hold my phone, lipstick and my small 2 shot hand gun just in case. I have my conceal carry permit. My wife told me to go to the hotel bar and meet up with her friend Susie and have fun and she will watch over you. She told me Susie was in an abusive relationship and told me to help her let loose and have fun.

I worked in OKC part of the day and then drove to Dallas dressed up and stopped along the way to pee and get a drink, getting weird looks and a few compliments. I checked into the hotel around 7 and saw that the bar was hopping so I dropped my bags in my room and went down for a drink where I was greeted by different reactions but mostly good. I was approached by a lady wearing a similar dress and said she is Susie while complementing my beautiful dress and heels and lead me to a table with 2 other ladies

After a few drinks and stories and a few pictures and selfies with the ladies, Susie put her hand on my leg and felt my garter belt strap and brought this to the attention of the other ladies and this started our night and they promised to watch out for me. The ladies wanted to dance so we took off our heels and I danced with all 3 ladies and they danced with a few other me. but Susie and I hung out mostly together talking about she said she has not felt this comfortable talking with a man in a long time. When it the music slowed down, I got to dance with each lay alone and they would feel and rub my backside through all the layers of my lingerie and I did to them. The first two ladies wore thongs under their dresses and they each asked about my lingerie and I told them while we ground our crotches together and they loved my silky hard 7+ inches against their wet pussy's. It was Susie who had similar panties to mine and she even committed if we matched. She was kissing my neck as I described what I was wearing under my dress in detail as she squeezed my ass running her hands sliding my slip over my panties. I did the same to her, telling her how sexy she was and how any man would love to lick her thru her silky panties when she reached between and squeezed my untucked, satin covered hard cock and it throbbed in her hands when she moaned into my mouth and said YES, as we kissed. After a few seconds the song ended and we went back to the table to relax, talk and cool off. I didn't want to cross the line further than what I just did.

All the bumping and grinding was great and I was getting me really horny and I know the ladies enjoyed grinding on my untucked hard silky cock. It was late so I kissed each lady good night telling them it was going to take me hours to "wind down" and get out of all these clothes and wash the make-up off and get to sleep, getting another good laugh and a few offers to help me.

I grabbed my purse and swayed happily to elevator and up to my room and started to the process of removing my beautiful dress and I washed my face in my lingerie and heels loving the feeling and reflection of my lavender bra and panties against the pink slip. I opened my over-night bag to find my wife packed my black satin nightgown and matching robe on top and what I was to wear tomorrow with a note. She hoped I had a great night at the bar and her sorority sister Susie had a great time. The note went on to say if I wore the outfit in my overnight home in the car after meetings, she will make it worthwhile when I get home.

As I was taking my slip off, there was a quiet knock at my door so I put my robe and answered the door to see Susie standing there with a smile on her face as she admired my lingerie saying very pretty as she strolled past me into my room and closed the door at the same time my phone rang and it was my wife telling me to take care of her properly and hung up.