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  #1  
Old 10-22-2018
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Default Which celebrity would you lose your virginity to?

We've been discussing "retro" beauties in the "Early Experiences: What Turned You On" and "Divas" thread for a couple of years now.

There is a thread on "Straight Dope" that asks the question "If you could lose your virginity to any celebrity from any time, who would you chose?"

Rule 13 prevents linking to other "boards" but I think it would be more fun to hear from our own members anyway. And yes, she (or he) may be cis or trans.

So, who would it be???
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Old 10-22-2018
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I'm glad you started this thread.

That's a good question and one for which I'll have to give it some thought before I answer.
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Old 10-24-2018
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I need to ponder it too!
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Old 10-24-2018
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I guess I would say Beverly Sills or Carolyn Jones as Marsha Queen of Diamonds, the first ladies I was ever attracted to,
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Old 10-24-2018
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This was really a lot tougher than I thought. But after thinking about it for a while and doing some research, I was able to narrow it down.

Although I've only seen Fall Guy in repeats, she's someone who was popular within my lifetime (unlike many of my "retro" favorites from the 50's, 60's and 70's), someone who was a big TV star during the 80's when there were still only 3 major networks, and someone I got to meet as a little kid. I remember her as being really sweet.

Of course it would have to be Heather Thomas.
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Old 10-24-2018
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It was not easy to decide which cis-women I would choose. Heather Thomas came close, but I went further back in time. My first choice is Jaclyn Smith. My second choice is Donna Douglas and third is Eva Gabor.

Lynda Carter is also high on my list, but I wanted to keep my choices down to three.
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Old 10-24-2018
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The top of my list for transwomen is the incomparably gorgeous Jennifer Paris. Bailey Jay is tied for my first choice. Melzinha is another gorgeous transwoman. She always seems to be happy in every photo and I find that to be quite attractive. The fourth one on my list is Amy.

Naturally there are so many more, such as Miran, and my list could run a lot longer than it is, but I'll stop with what I have here.
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Old 10-24-2018
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Great posts so far! This thread was meant to include both cis and trans women as well as guys (gay or straight). I’ve thought about many transwomen I’d like to have lost my virginity to. But most of them are younger than me. Chanel Santini for example was born in 1998. I was in high school. The fact is that I lost my virginity to my friend Stephen/Stephanie when we were 13. Actually we “lost it” to each other. That was an awesome and wonderful experience and I’m not sure if there’s anyone else I’d rather have lost it to. She was the first person I was really in love with. I lost my virginity to a cis woman when I was 19. She was several years older than me and very attractive. I married my first wife not long after that.

As far as finding a wife or girlfriend who is trans. There are SO many beautiful women on this site and some that I’ve met in real life. I guess it all depends on who, whether I was married or not at the time, and if we hit it off or not. I have been married for the second time since 2011. There were a few years after my divorce when something might have worked out but never did. Maybe my third wife? Nicole Ferri, are you listening?

As for celebrities, in another life, if I could, I would pick Hayley over anyone else. She strikes me as not only beautiful but as a very kind and thoughtful person. Very intelligent and down to earth. Did I say I think she’s also an awesome singer? That should be obvious to anyone who reads my posts. Among “retro” beauties I would of course include Françoise Hardy , Sharon Tate , and of course Farrah . It gets harder as one goes back farther in time but the drawing of the girl on the cover of the 1924 “Film Fun” magazine I posted is gorgeous. Ever since, I’ve wondered if she was supposed to be someone famous or not.

(I want to do a special tribute to Sharon Tate in the Divas thread. As we approach the 50th anniversary of that night, it would be fitting to celebrate her LIFE. I consider her to be one of the most beautiful women to ever live. I almost picked Sharon over Heather by the way.)
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Old 11-03-2018
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Julie Newmar as Catwoman
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Old 11-04-2018
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My choice would be Adrienne Barbeau
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Old 11-08-2018
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Awesome thread! As far as transexual ladies, well, I wrote a story about losing my virginity to these two.....Sierra Ferraro and Sophia Abdullah!
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Old 11-10-2018
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Quote:
Originally Posted by Boner View Post
Awesome thread! As far as transexual ladies, well, I wrote a story about losing my virginity to these two.....Sierra Ferraro and Sophia Abdullah!
Very nice...

You need to write another story about them.
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Old 11-17-2018
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“The Graduate” (1967). Who remembers this movie? Long before most of us were even around. This movie was considered very risqué for its time. Especially when Dustin Hoffman’s character loses his virginity to the older “Mrs. Robinson.” Hoffman’s character, Benjamin Braddock, states, "I will be 21 next week."

In reality, at the time of filming, Dustin Hoffman was actually 29. William Daniels, who plays Hoffman's father, was 39, only 10 years older than Hoffman. Anne Bancroft (“Mrs. Robinson”) was really 35, just six years older than Hoffman.

So, would you want to lose your virginity to “Mrs. Robinson”? I’ve never seen the entire movie but I think she’s kind of hot. I especially like the last picture with Dustin.

(My preference, I'm sure, would have been Katherine Ross. Born in 1940, she’s 27 here.)
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Old 11-18-2018
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Jenna Coleman
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  #15  
Old 11-21-2018
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Quote:
Originally Posted by a9127 View Post
This thread was meant to include both cis and trans women as well as guys (gay or straight). I’ve thought about many transwomen I’d like to have lost my virginity to. But most of them are younger than me. Chanel Santini for example was born in 1998. I was in high school. The fact is that I lost my virginity to my friend Stephen/Stephanie when we were 13...
It's true that most current popular transwomen on this site are much younger than me. However there's one who is about the same age...
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Old 11-21-2018
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Quote:
Originally Posted by a9127 View Post
Very nice...

You need to write another story about them.
I should! Sierra and Sofia Adbullah will always be two of my favorites

I'll never forget the day I found Bob's T-Girl site. I had just discovered Gia Darling a few days before and was looking for pictures of her when I found it. After checking out the previews and seeing Sierra with her motorcycle and in her pink catsuit it was over! I couldn't join fast enough!

Sierra used to have her own site, "Sierra's Fantasies". If I had know it was going to disappear I would have saved every last photo!

I also discovered Sofia thru Bob's site. I've never seen a picture of her cock but it supposed to be huge! I love these sexy candids of her at one of Bob's pool parties
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