My name is Doug and I would like your advice on my situation with my wife Emma. We are both in our late 40's and until recently had a fairly average existence, save for the fact that we chose not to have children. I am a certified public accountant and Emma is co-owner of a local hair and beauty spa. We married in our early thirties and have done reasonably well for ourselves
One day we were watching one of the afternoon talk shows and one of the topics was men who dress in women's clothes. The guest was in male clothing, and after a commercial break walked back on stage completely groomed and dressed in feminine attire. The host and the audience let out a burst of gasps, screeches, groans and whistles. I just turned to Emma and said "what in the world would cause a man to do that? I'd never in a thousand years do that." Emma smiled and squeezed my hand and said, "Honey, don't knock it until you've tried it, in my line of business it's not common to see but it's also not unusual". I let out a a few guffaws as the show progressed. After the show I freshened our drinks while Emma took a powder. Upon her return she took a sip and proceeded to tell me about a long-ago boyfriend.
When she was just starting out in cosmetology school she had a steady boyfriend and their relationship was as much platonic as romantic. She would sometimes use him, rather his longish hair, to try various treatments and styling techniques. Emma grew to enjoy shampooing and setting his mane. And, he grew to like the attention of being pampered and put in curlers. What started as something of a lark then became purposeful and took a turn when her classes in grooming and cosmetics began. To her, he was just being a dear helping out and a good sport. But to him, something clicked when she began to use him for makeup and manicure practice sessions. As Emma told it, over time the relationship became more platonic after she moved and her friend eventually paired up with a woman who not only pampered him but persuaded him to wear feminine attire. Emma stood up at their wedding and they remain long distance friends.
"So, let's have a bit of fun and how about if we try to change your opinion on the subject?" She said tongue-in-cheek. "I could fix you up just fine Doug". She was being whimsical and a little bit flirty. Being a typical man and uninterested I said "what's in it for me?". She purred, held me close, and said "Let's find out soon".
As we finished our dinner two nights later, she requested I go shower and whispered in my ear she'd really appreciate it if I shaved with a fresh blade as tonight was 'the night'. Off I trotted to the bedroom for a shave and a hot steamy shower. When I emerged I found a generous glass of scotch on the rocks sitting on my vanity. All cleaned up and in a fresh pair of shorts and a t-shirt I emerged from the bathroom to find Emma had slightly rearranged the furniture so her makeup table, chair and lighting were strategically positioned aside my reading chair, and I correctly guessed there would be little reading done that night. Taking my hand, she led me to my chair and said, 'Not a word or hesitation out of you for that next hour, agree?". I nodded, took a long sip from my drink and sat back.
Knowing there was no getting out of this I just closed my eyes and sipped my scotch for the next 45 minutes. From my vantage there was no mirror to catch my reflection which was probably a good thing. As she got down to final touches she took my glass away as she didn't want me to smudge her work. With lipstick in her hand, she outlined and filled my lips, and after a couple adjustments pulled out a wand which held a rather gooey looking substance. "Don't worry, it's just lip gloss for a finished look". My face felt odd but in not in a bad way. The creamy lipstick topped with gloss felt nice. She quickly clipped on earrings then reached over to her table. In a matter of moments I was wearing a wig with small bangs and curls that nearly hung to my shoulders. She stepped back carefully looked over my face, and a broad smile beamed across her face as she pronounced "Yes!!!". She turned the mirror my way.
I was quite surprised, actually more astounded at the results. She had given me the full treatment with a minor eyebrow grooming followed by creams, powders, liner, shadow, mascara and lashes. It's not a normal thing for a man to say, but I looked attractive. "See - I told you so, I knew I could doll you up nicely". I didn't need any convincing as I looked very womanly but it didn't really do anything for me. Well, it didn't, until Emma began fussing over me. Somewhere between the triple scotch, her cooing in my ear, and her gentle touches is when I started to get a bit carried away. The next morning, I had a pleasant memory of a wonderful time and and a remembrance of a climax that was off the charts. Down at breakfast, she poured me a cup off coffee while the muffins finished. As the cup filled she said. "See? I told you it could be something else! Let me know if you ever get the urge, I'd love to help you..."
Emma was never overly passionate or physical and as a result our 'encounters' were infrequent. So it wasn't unusual that three weeks went by with no romance since her little experiment. I felt that I couldn't just ask her for a physical favor, so one night in bed I told her I'd really like to repeat the treatment to see if it had the same effect. "I knew you would see it my way. I'll tell you what, if you promise to let me lead and you'll obediently follow, I will see what I can do for you this weekend".
Helga, this is the point where I need your advice. In my mind, Emma really went overboard this past weekend and dressed and groomed every inch of me from the skin out. She removed every hair below my neck and in addition to dressing for each dinner at home that weekend, I slept in a satin nightgown and during the day wore a bra and panty set, nylons, and either slacks and a blouse or an everyday dress. She had purchased me flats for the daytime and for dinner I wore my newly acquired patent pumps which matched my borrowed purse. Did I have fun and pleasure? Yes, and apparently Emma did as well. But, how can I keep some form of balance in my life now that I've had one of the ultimate experiences a man can have?
(What would you advise?)