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Thread: Life can be good

  1. #1
    Yendis Sidney's Avatar
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    Life can be good

    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

  2. #2
    Gold Member bridget thronton's Avatar
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    Lovely post thank you for sharing

  3. #3
    Silver Member Debra Russell's Avatar
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    Quite a story - I think we need pictures

  4. #4
    Senior Member Pumped's Avatar
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    Sounds like a great time!

    But be careful if you continue the relationship! You never know where it might lead and the impact on your marriage.

    We need pics!

  5. #5
    Platinum Member
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    Hi Sidney , That was Quite an awesome evening you Had,

    And I am sure the Nitecap must've been extra Special, >Orchid**oo**
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  6. #6
    Aspiring Member Joyce Swindell's Avatar
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    WOW
    I'm not sure about that experience for me! It is exactly something I think my wife would do! It's certainly not something I would seek out, which makes me doubly sure that my wife would push that envelope with me.
    Sounds like it's something you enjoyed and a really great experience and a little bit surprising too!

  7. #7
    Just being true to myself Jolene Robertson's Avatar
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    WoW, What an amazing evening. I can only imagine how you felt by the end of the night. As others have said "Pictures" Please!

  8. #8
    Member Gilly68's Avatar
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    What a wonderful experience for you Sidney, and what an amazing wife you have, she sounds so lovely! So many firsts you experienced on that day! And it sounds like your wife enjoyed it almost as much as you, which is sweet!

    I would love to have an experience like that!

  9. #9
    Member Gi Gondin's Avatar
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    Thanks for sharing Sidney. Congratulations for your wife and you for having such an open, honest and caring relationship.
    It takes a lot of understanding and confidence to live such experiences together.

  10. #10
    Yendis Sidney's Avatar
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    So sorry girls. My loving and accepting wife gives me almost free reigh with a few exceptions, one is no pictures of Sidney on ANY social media including Crossdressers.com. I can live with that.

  11. #11
    Aspiring Member DianeT's Avatar
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    Oh, bummer

  12. #12
    Platinum Member Beverley Sims's Avatar
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    When I was twenty I was set up like that by my girlfriends. They organised a date for me and the poor guy never knew.

    I could have strangled my girlfriends who stayed in the background all night.

    Thank goodness for that. :-)
    Work on your elegance,
    and beauty will follow.

  13. #13
    Junior Member fiona de wilde's Avatar
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    What a great story Sidney, thank you for sharing this. It must have been a wonderful experience!

  14. #14
    Junior Member Teresa.Smith.VA's Avatar
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    Quote Originally Posted by Sidney View Post
    My loving and accepting wife gives me almost free reigh with a few exceptions, one is no pictures of Sidney on ANY social media including Crossdressers.com.
    It's always nice to be able to post pictures to add to great experiences, but I totally support and honor any reason why CDers or wives do not wish to post pictures.

    There are many reasons why members don't post pictures. And, once you make it known that you are unable to share pictures, CD.com members should honor your situation. Being badgered for pictures to support your wonderful experience is no fun.

    Thanks again for sharing this experience that was so lovingly encouraged by your wife. It's so neat when a married, committed couples can enjoy such a trusting and loving relationship.

    I too have a "dream-come-true" wife who has fun pushing every pink hot button she can find to enhance my fantasy of pretending that I am a woman for some period of time... a day, a few days, or even longer when we are traveling. We both have fun pretending that we are "girlfriends."

    Since few couples enjoy your level of trust and love regarding cross dressing in your marriage, sharing the details of your experiences, and your feelings about it is very much appreciated. Thank you.

    I look forward to your next post when you can share how much fun it is to make fantasies come true with the full support of your partner.
    Fact: Some members can never post pictures in their feminine finery to support their stories and experiences. Please be understanding and kind.

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