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Ask Mistress Samantha

The Editor | Mar 20, 2017

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Dear Mistress Samantha:

I’ve had this issue in the back of my mind for a very long time. I just can’t figure out what to do, so I would really appreciate any feedback from an experienced Mistress such as yourself. Let me explain. I’m a 29 year old , ruggedly handsome male. I’m 6’2″ tall, 226 pounds, very muscular, with dark hair and light blue eyes. I’ve always been considered a “mans man.” I was a jock in High School, dated the prettiest cheerleader, and won a football scholarship to an Ivy League College. I have a twin brother that was anything but “macho!” He was very scrawny, stood 5″9″ tall, with blonde hair and green eyes. To say that we were complete opposites would be an understatement! While in High School he never played sports, nor did he have any dates. He was active in the drama club, and the debate team. His idea of a good time was Chorus practice on Friday nights! Everyone thought he was gay. After he graduated, he received an academic scholarship to Harvard, where he studied law. While attending college, he started working out, got his teeth straightened, and had a nose job. He graduated with honors, and now is a junior partner in a very prestigious law firm. He married a really beautiful woman (also a lawyer,) and has two adorable kids. I can’t really explain what happened, but my first year in College everything began to change. I started crossdressing everyday. I became obsessed with it. I lost interest in women, and started exclusively dating dominant men. Mr. Macho became a little submissive sissy bitch, and I loved it! It seems both my brother, and I had complete transformations, much to my surprise! I finally graduated from College with a business degree, and then I got a really good job. Girls are always hitting on me at work. I constantly turn them down. I tell everyone that I have a girlfriend. Boy, if they only knew my girlfriend had a hairy chest and massive muscles, people would go crazy! Mistress Samantha, I don’t know how to handle a particular situation. My family and co-workers are always asking me to bring my sweetheart to meet them. I told them I would be bringing her to holiday parties. When the holidays are here, what should I do? Yikes!

Mario

San Francisco, Ca.

Dear Mario:

You are in quite a dilemma sweetie! I always believe honesty is the best policy, but I totally get your situation. My first suggestion would be to seriously assess the personality types in your family. Are they modern, open minded, and progressive, or old fashioned, traditional, and unyielding? If narrow minded describes your family, you may never be able to tell them. They probably couldn’t handle it, and it would create total drama. If, on the other hand, they’re open about such things, then tell them when you’re ready. You’ll know when the timing is right, or not. Don’t rush , be sure you thoroughly examine the situation. Don’t feel pushed into making a snap decision because your family is trying to stick their nose in your business! As far as your co- workers are concerned, you owe them nothing. Tell them she went out of town to visit her family for the Holidays. It’s better to keep your private life to yourself at work anyway!

Mario, continue to live your life as you see fit. Explore your fantasies, and find true love. Don’t ever feel guilty, just live your best life, and everything else will surely fall into place. Always follow you instincts, be open to the realm of all possibilities, and ride the waves of the Universe! Be well!

Until next time, blessings, good health, and great sex!

Questions for Ask Mistress Samantha can be mailed to: Mistress Samantha, 8362 Pines Blvd, Suite 433. Pembroke Pines, FL, 33024.

Mistress Samantha is a Lifestyle Mistress who has been actively involved in the Transgender/Crossdressing Community for almost twenty years. She started a successful Adult Phone Service over eighteen years ago. Since then, she’s personally advised, guided and fantasized with literally thousands of members of the Crossdressing, Transsexual, and Sissy Communities. Additionally, she’s a well known Advice Columnist for Transformation Magazine, and Forced Womanhood Magazine. She’s also written for several magazines that are no longer in print, such as Enslaved Sissies And Maids, Bizarre Magazine, Screw Magazine, and She-Male International. Mistress Samantha is now accepting new clients for fantasy phone calls, consultations, lifestyle advice, makeup and wardrobe tips, sissy and slave training, forced feminization, and girl talk. Call her now 954-757-0345. Call now and inquire about her full line of products and services, including etiquette, modeling, and beauty school. 954-757-0345. Call anytime, and feel free to leave a message for Head Mistress Samantha. She will glad to call you back as soon as possible. 954-757-0345. Must be 21. Visa, MC, AMEX, Discover, Check card, prepaid card, and money orders are accepted. Reasonable rates. Discreet billing.