Friends I’ll Never Meet: Sissy Sarah

Meet my newest internet friend, Sarah. Sarah and I met about a month ago when she sent me an email confessing her hidden desire to dress up in ladies clothes, even though she is technically a he. See below:

And then I responded saying ‘Never change! I love you as you are, Sarah! However yes you should probably send me all of those photos ASAP.’ And now here we are. Below is an interview with Sarah about life, love, crossdressing, and why drinking piss is kind of hot.

So when did you become Sarah?
It was about seven years ago, but I have been dressing up in women’s clothes since the age of 14. It began when my sister had a girl from Spain, Maria, staying with us on an exchange visit. One morning Maria left the bathroom wearing the prettiest baby-doll nightie I had ever seen. Then one day when I was home alone, I saw that Maria’s bedroom door was open and her baby-doll nightie was on her bed. There was nothing I could do to stop myself, I stripped naked and put it on. It felt wonderful and I knew instantly that I needed to wear silk, satin, nylon and chiffon more often.

What else turns you on, besides wearing girly clothes?
The hottest thing for me is being teased by a female. Once, while shopping, I saw a very pretty dress and my girlfriend told me to try it on. I was so scared I began to tremble and said no, I can’t do it (even though I wanted to), but she insisted. After I was in the dress my girlfriend marched me towards the window for a better look in full view of the other customers. I was dizzy with embarrassment, but I bought the dress. When we got back to my place we had the wildest sex ever. Another thing I crave from a dominant woman is drinking fine wine. We are both wearing pretty dresses, we have a wine glass each. Her glass contains wine, but mine contains her pee. Yum! Unfortunately this has only happened once.

Do have sex sex as Sarah?
I have not had sex as Sarah often but I did have sex with my wife wearing her nighties. (My wife passed away several years ago and I now live alone.) She knew I liked wearing feminine clothes and that I was highly aroused wearing a bra, stockings and a garter belt. We didn’t do this all the time but I think she got more satisfaction when I was in that state of arousal. Now that I live alone I wear women’s underwear all the time. I don’t have any male underwear at all.

Have you ever been with a guy?
No, I have never been with a man sexually. I have a strong feminine side to my character but I am 100% heterosexual. Having said that if I met you with a gay male friend and you needed pictures of me with a guy and ordered me to have sex with him, then I would. That would be to satisfy you rather than me. If you wanted me to suck his cock and swallow his sperm then I would do it for you.

Thanks, that’s so sweet of you. Have you ever been to a dominatrix? I bet you’d be into it.
Yes I have been with a dom prostitute but I found the experience very impersonal and businesslike. I would prefer to know the girl and have a more intimate understanding of each other’s desires. I just prefer the idea of friendship and sex rather than a business deal.

Well maybe you just need to find a different dom, one you can connect with. I’ve met some amazing ones! So what do you find so erotic about being peed on/drinking piss?
I don’t think anyone could say they like the taste of piss anymore than they could say they like the taste of shit. But this is not the point. The whole point is the erotic humiliation factor, being ordered to satisfy the woman. I really enjoy it and I hope it happens again one day.

Do many of your friends and family know about Sarah?
Very few people are aware of me being Sarah, maybe 3 or 4. None of my group of friends know.

How come you keep it a secret?
I guess it’s because the other side of my character is just as strong and very macho. I think many people in my circle would be very surprised if they knew I was Sarah. I live openly as a manly person who drinks beer and goes to football even though I am wearing frilly panties under my jeans and t-shirt. It’s mostly when I get home that I take off the outer layers and put on a pretty dress or a sexy negligee. I will go out in a see-through chiffon blouse with my bra clearly visible, but it will be covered up with a jacket. Though if you told me to remove my jacket at any time to embarrass me, then I would do it.

So what happens when I put those photos on my blog? What if your friends see them?
I will just die if they find out, but that is what I need. I need to be humiliated. That is so erotic.



12 Replies to “Friends I’ll Never Meet: Sissy Sarah”

  1. I don't even know what to say. He digs it, he's down to earth, so whatever. Unless she likes to go by Sarah, but the vibe I'm getting is they only use male pronouns and names in public? I don't know.

  2. He looks pretty! I love him as Sarah, although he probably wants me to say that he looks horrible and should be ashamed. I won't say that.

  3. Aaah, she looks so pretty, neat and sexy in those baby-doll nighties – not at all like a middle-aged pervy, girly-man. Peak-a-boo, Sarah!

  4. It's really glad to read about the following topic which has enhanced my knowledge regarding topic and plus has given alot of ideas which I can think on.So I would say thank you to the blog owner for providing this amazing information.

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