Below is a story that we at Crossdresser.com received from one of our customers about how Sam's girlfriend found out that he liked to cross-dress. Please share your stories about your cross dressing experiences by leaving a comment.
I had been dating Melissa for about 9 months and it was going great. Melissa and I had a numerous common interests; we had been away on a vacation together and even meet each others families. Well that was until one night when Melissa and her girlfriends went to a charity drag queen bingo event and discovered me…..her cross dressing boyfriend “Samantha”.
Let me back up a bit and give you the details to what happened. I was glancing through one of those throw away papers and came across an ad looking for volunteer drag queens to perform at a charity event. I thought to myself this is my chance to try out my alter ego “Samantha” not too far of stretch from my own name of Sam.
I called the number and spoke with Neil who was the organizer. He explained to me that a local club was hosting drag queen bingo to raise money for AIDS research and they needed additional volunteers dressed in drag to help. Neil told me that is was a ton of fun and the only real skills you need is to be friendly. All I would be doing would be walking around selling bingo cards, tickets for door prizes and encouraging people to bid on the silent auctions items. Neil said that the year before they had raised over $25,000 so he knew they would need more help this year as they already had sold 1800 tickets to the event. He asked me to email me a few pictures of me dressed in drag and he would then send me all the details. After talking to Neil, I decided to send him my cross dressing pics and volunteer at the event.
It was all set and Neil said that my transformation from male to female was flawless but now what to do about Melissa? I had worked out my schedule at work to be available for this. No traveling that week. What was I going to tell her? Melissa honey I have something to tell you…I am a cross dressing. Did not think that would go over so well….or what if tried this you need to know that I love to cross dress and wear satin panties for men; I hope you don’t have a problem with this babe? What was I to do?
The Friday night of the charity drag queen event turned out not to be a problem as Melissa told me earlier in that week she had plans to go out with some of the girls from work. I was off the hook for now of having to tell Melissa that I loved to strap on a set of silicone breast forms or that I had closet full of cross dressing clothes and heels for men that she no idea about.
The night of the event I came home and started gathering my stuff that I had hidden around my place:
beard cover, make up, wig, false eye lashes, gaff, stockings, shoes. I sat down in front of the mirror and just started getting dressed into “Samantha” when I was all done I looked at myself in the mirror and thought I really look hot!.
I arrived at the event and all the other drag queens are talking about how they get a lot of their cross dressing items from Crossdresser.com. So I chimed in and said me too. We all started sharing tips about how to use the cross dressing gaffs to get a perfectly flat crotch and how heels for men hurt after several hours and how do women wear them all the time. it was like I was one of girls it was so fun but the event was starting time to go work the floor.
The event was packed. I was walking around asking people to bid on spa package and having fun with it. Then all of a sudden I turn around and there was Melissa and her friends. First Melissa looked at me kinda like a deer in headlights and then all of sudden she says “Sam”? I said “yes” and Melissa said “you are even hotter as girl” and plants a long hard wet kiss on me. Needless to say she messed up my lipstick and I had to go touch it up. I asked Melissa if she was mad that I did not tell her and she said “mad no way are you now my perfect partner both male and female”.
Over the next few weeks Melissa and I went out with me dressed as Samantha and it was just incredible. I showed Melissa my closet of cross dressing clothes she said to me “I now I know why you were only able to give me a drawer at your place as your closets were full”. Melissa even helps me with my makeup and wig selections it certainly has brought us closer as a couple as Melissa loves Samantha as much as Sam. For all of you cross dresser's out their don’t keep it a secret. Let your inner cross dressing diva out!
I had been dating Melissa for about 9 months and it was going great. Melissa and I had a numerous common interests; we had been away on a vacation together and even meet each others families. Well that was until one night when Melissa and her girlfriends went to a charity drag queen bingo event and discovered me…..her cross dressing boyfriend “Samantha”.
Let me back up a bit and give you the details to what happened. I was glancing through one of those throw away papers and came across an ad looking for volunteer drag queens to perform at a charity event. I thought to myself this is my chance to try out my alter ego “Samantha” not too far of stretch from my own name of Sam.
I called the number and spoke with Neil who was the organizer. He explained to me that a local club was hosting drag queen bingo to raise money for AIDS research and they needed additional volunteers dressed in drag to help. Neil told me that is was a ton of fun and the only real skills you need is to be friendly. All I would be doing would be walking around selling bingo cards, tickets for door prizes and encouraging people to bid on the silent auctions items. Neil said that the year before they had raised over $25,000 so he knew they would need more help this year as they already had sold 1800 tickets to the event. He asked me to email me a few pictures of me dressed in drag and he would then send me all the details. After talking to Neil, I decided to send him my cross dressing pics and volunteer at the event.
It was all set and Neil said that my transformation from male to female was flawless but now what to do about Melissa? I had worked out my schedule at work to be available for this. No traveling that week. What was I going to tell her? Melissa honey I have something to tell you…I am a cross dressing. Did not think that would go over so well….or what if tried this you need to know that I love to cross dress and wear satin panties for men; I hope you don’t have a problem with this babe? What was I to do?
The Friday night of the charity drag queen event turned out not to be a problem as Melissa told me earlier in that week she had plans to go out with some of the girls from work. I was off the hook for now of having to tell Melissa that I loved to strap on a set of silicone breast forms or that I had closet full of cross dressing clothes and heels for men that she no idea about.
The night of the event I came home and started gathering my stuff that I had hidden around my place:
beard cover, make up, wig, false eye lashes, gaff, stockings, shoes. I sat down in front of the mirror and just started getting dressed into “Samantha” when I was all done I looked at myself in the mirror and thought I really look hot!.
I arrived at the event and all the other drag queens are talking about how they get a lot of their cross dressing items from Crossdresser.com. So I chimed in and said me too. We all started sharing tips about how to use the cross dressing gaffs to get a perfectly flat crotch and how heels for men hurt after several hours and how do women wear them all the time. it was like I was one of girls it was so fun but the event was starting time to go work the floor.
The event was packed. I was walking around asking people to bid on spa package and having fun with it. Then all of a sudden I turn around and there was Melissa and her friends. First Melissa looked at me kinda like a deer in headlights and then all of sudden she says “Sam”? I said “yes” and Melissa said “you are even hotter as girl” and plants a long hard wet kiss on me. Needless to say she messed up my lipstick and I had to go touch it up. I asked Melissa if she was mad that I did not tell her and she said “mad no way are you now my perfect partner both male and female”.
Over the next few weeks Melissa and I went out with me dressed as Samantha and it was just incredible. I showed Melissa my closet of cross dressing clothes she said to me “I now I know why you were only able to give me a drawer at your place as your closets were full”. Melissa even helps me with my makeup and wig selections it certainly has brought us closer as a couple as Melissa loves Samantha as much as Sam. For all of you cross dresser's out their don’t keep it a secret. Let your inner cross dressing diva out! 
3 comments:
Really you are both looking so beautiful…
I loved your details of dresing and telling your wife and liking you as a woman and helping you be a better woman.
Let's see........
Courage..........check
Motivation.......check
Purpose..........check
Melissa.......Hmmm....Melissa?......Melissa?..have you see..n
I wish there were more Melissa's
luuuuuuuckkky
Jazmen J
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