Sidney
08-06-2021, 09:25 AM
I had a very very interesting weekend. I apologize beforehand for the long post but I am so excited and wanted to share As I've stated before I love my accepting and supporting wife. OK, this last week we spent at a casino hotel on the beach because of upgrades being made to our apartment. We packed including my bikini I bought this past spring. Haven't worn it since but still have visible tan lines. Arrived at hotel late afternoon and wife says I bought you a few surprises. She had bought me a wig that sort of matched her hair style, short and almost white hair, her natural color. Also a swimsuit wrap that matched my bikini and a pair of matching strappy sandals and said change and let's go to the pool that we could see from our 11th floor balcony. Jump forward we are at pool under a covered cabana laying in shade on a king size lounge chair sipping our wine. I am tall and slim and tucked tight. I thought I look good, wife said I did. Couldn't swim because of wig but went into pool to cool off and returned to cabana. Now I'm not into men or other women except my wife. She is chuckling and as I dry off she says sit down before I fall over laughing. She says don't look now but that good looking man across the pool was watching you swishing your butt all the way to and from the pool, I think you have an admirer. And chuckles again. Just then a waitress brings us two glasses of wine that we didn't order. We ask and the waitress points to the gentleman acrOSS the pool so we raised our glasses to him and then my wife waves him over. I said what did you do that for. She say he bought us a drink an you've never been hit on and I want to see how you handle it. I think someone is having fun at my expense. My wife offers him a seat on my side by my feet that I have to move over. We explain we are very close friends. We talk awhile and are enjoying ourselves when Samuel asks if we would like to have dinner with him. Sooo what does my wife say "I am really tired BUT IM SURE SIDNEY WOULD LOVE TO". Crap what did she just say. My wife gave me a look that said go ahead so I said YES. My stomach was doing flip flops I had just been asked to dinner by a MAN. As I was getting up he reached out for my hand and helped me up. Another first and gave me kind of a tingle. . Back in the room I asked her what she was doing. She said Sidney had never had a date and said she wanted me to have a good time. Laughing said you know a woman doesn't have to have sex with a man just because he buys her dinner. I was feeling a lot both wanting to and not wanting to. Showered and shaved and wife helped me with wig and cloths. The more I was getting dressed the more I found myself getting excited about my dinner date. My wife picked out black flared dress slacks with white long sleeve silky blouse, nice jewelry wig, makeup, 3 inch black heels thigh highs and all the appropriate undergarments. I looked in mirror and felt good. Wife put her phone number on speed dial on my phone in case I needed her. I really was so nervous and excited. Gave wife a kiss and left to meet Samuel. We met and turned to walk to restaurant and he put his hand in the small of my back to I guess guide. Believe me about this time I was feeling as femine as I ever have in my life. He held my chair to seat me. Found out I could really like to be pampered. Ordered drinks and talked. It was different for me sitting talking to a man dressed. Turns out he wasn't looking for sex, just companionship and a good time. He really made me feel wonderful with his compliments. I will never cheat on my wife but I can enjoy good company and I was enjoying dinner and Samuel. He comes into town once a month on business and want to know if I'll be his date when he is in. Yep I'm feeling great, but a little guilty. I think I'm looking the best I have ever felt. So i said Samuel we need to talk. I explained to him I was somewhere on the transgender spectrum and the woman I was with was my wife. He looked at me and smiled and said maybe your wife would like to go out with us sometime. I look behind him and there is my wife across the dining room with a big grin on her face I wave her over. We all three eat and have a wonderful time. After dinner we went to a lounge for drinks and had a good time. Every once in a while he would reach over and put his hand on mine while talking and it made me feel, well special and wonderful. My wife and I started to end the night and Samuel gave my wife a hug. He then turned to me and gave me a HUG and a kiss on the cheek. I felt like I was on my first date. We split ways with a promise I would meet him dressed next month. My wife and I talked for hours her wanting to know all the things I was feeling. She took my hands and said you really enjoyed yourself didn't you. I said yes I did and thanked her. She grabbed me and kissed me very romanticlly. First kiss with her while I was dressed. The rest of the night can't be repeated here. Sorry. This was a wonderful experience for me and her and I'm sure a lot of conversations in the future. Again sorry for the long post