One night after dinner my husband Bill sat quietly while stirring his tea with a perplexing look on his face. I've seen this look on his face dozens of times in our 30 yer marriage, so I beat him to the punch. "What's going on Bill?" "Carol, I have something I want to say but don't know how to say it. Its been on my mind as of late and I feel I must get it out. Truth is I'm not really sure if this is what I want but I've thought so much about it that its time to say something". Well when a fifty-five year old woman hears those words come out of her husband's mouth one of the first thoughts is he wants a divorce. "I'm listening. What is it?" He paused for a few moments, gazed down into his tea and proclaimed, "I want to play dress up and I want you to help me." Taken off guard by the request I asked, "What exactly do you want Bill, to dress up how and for what purpose?" He blurted it all out in rapid succession, "I want dress up in nice women's clothes and look good like women do, and I want you to help me and guide me." And if that wasn't enough he added, "I want you to lead me, like it is your idea, and I want you to train me, then later insist I sometimes wear women's clothes. I want you to assert control of me". It was a good thing I was sitting down when he made his proclamation because at that instant it was like a sledgehammer blow to my head. I thought for a moment and chose not to overreact but to try to get him to open up about this apparent need. So, over the course of a few cups of tea and cookies my dear husband Bill revealed his deep secret to me while I lent an empathetic ear. When he was finished, I took his hand and told him not to worry as this was not the end of the world. I told him I'd need a little time to process this and suggested we retire upstairs for the evening and we'd talk more after work tomorrow.

The following morning Bill headed off to work and I poured myself another cup of coffee and began to process his news. My first thoughts made me silently laugh as I envisioned Bill made to look like a caricature of a women like at Halloween or on a television skit. But his sincerity indicated he didn't want to do this as a gag and he wanted to look good and be immersed in a feminine experience. After thinking on this I came to the conclusion that his out-of-the blue request which initially sounded bizarre did not bother me at all. In fact, it might open an opportunity for me to hold more sway over him and our marriage. I decided to do some online research about men who have such a desire, and I had a most educational afternoon.

That evening after dinner I had the opening to bring up the subject. "Bill, I've thought about what you asked for last evening, and while it isn't something I would have dreamed up, I'm willing to help you provided I make up the rules and you do exactly what I ask of you at all times. There will be no variance or criticism of my plans or demands. If you agree, I'll start planning your introduction to women's grooming, clothing and accessories. Just so you know, on this first experience you'll get all you bargained for, and then some." He contemplated what I said for all of about 2 seconds then agreed and thanked me. "Don't thank me just yet dear, let's see how you do and feel after your introduction." For sure, I had my work cut out for me for the next few days.

The next morning I barged in on Bill right after his shower with my tape measure and got right to work. It was important that I knew exactly what I was working with as his first experience might be his last, so I'd make this experience a doozy he'd never forget. As it turns out I couldn't use any of my things for dressing Bill, but I enjoy shopping and this was a chance to visit all my favorite woman's shops. Over time, I've developed some friendships with sales associates at several of the finer been apparel stores in the area, so I know I could count on their advice and guidance. I readied myself together and was off to enjoy a day of shopping for my dear husband.

My first stop was at Macy's as they carry a wide selection of lingerie and foundation wear. Based on my internet surfing I knew that most men who wanted to play dress up fantasized about satiny, silky bras, panties, and slips with a touch of lace. That of course, was easy to pick out. Where I needed help was in selecting some foundation garments that would help create a more shapely hubby but would also restrict him so he felt the full effect of feminizing attire. My friend Masha in the lingerie section introduced me to the store's shape wear specialist who listened of my plans. While I spoke, her smile went from a reserved smirk to an ear-to-ear grin while she nodded her approval. Phyllis recommended an open bottom girdle and a complementing longline bra for encasing and shaping our subject. After making those selections I went back to Marsha's section where we selected nylons in lieu of the pantyhose just purchased... although the pantyhose might be useful in the coming weeks. With Marsha's help I selected five pairs of hose. Being a true professional, Marsha didn't say a word when I had purchased the lingerie, but when I returned for the larger sized hose, her dimpled smile said it all. "Yes," I pleasantly said, "these as well as the other purchase are for my husband". Attempting to make small talk she asked if was for an event or special occasion, and I replied, "Oh, more of an experiment at my husband's request, so I don't want to disappoint him and will dress him to the nines; I'll show you pictures next time I'm in". Leaving Marsha with an approving yet astounded look upon her face, I ventured into the mall to hunt down the remaining items. The rest of my shopping took longer than expected but by mid afternoon I had all the items that were on my shopping list. My last stop was to Sephora for his makeup, body powder and perfume.

That evening I broached the subject with Bill to give him a heads-up that I had completed my shopping and not to make any plans for the weekend. I think he was half expecting me to ask him if he was really sure about this, but I didn't - I was completely committed now and one way or another I'd make him comply with the original plan. I had taken ownership for this experiment and nothing was going to prevent me from establishing my dominance and fulfilling his fantasy .

Bright and early Saturday morning I arose and made up a breakfast tray and a pot of coffee. By the time I reached the bedroom Bill was stirring so I poured us each a cup of coffee. Over morning chitchat we drank our coffee. "Ready for your fantasy, darling?" "Oh, that, uh sure". He answered. "Good, we're going to make a day of it so we need to get started. We'll be indulging you from the skin out, so I'll get a few things started in the bathroom.

Bathing went as I had planned, he stood while I slathered on hair remover on his chest, arms, underarms, crotch and legs. When he started to object I cut him off and reminded him he wished me to help him and wanted me to be assertive. OK, then - I would hear no more interruptions from him or there would be unpleasant consequences. Into the shower for a thorough rinse and wash, then into the prepared bubble bath. I picked up my pink razor and touched up his legs and groin, mostly to introduce him to body shaving. I casually mentioned he'd be lathering up and shaving for me from this day on so I hope he was taking notes.

I helped him rinse after the bath and we patted him dry, prior to working in body lotion to his freshly shaven areas. After a dusting with body powder we slipped on his peach satin robe and I led him out to our recliner in the bedroom. I instructed him not to open his eyes and began making changes to his appearance. Eyebrow plucking and shaping was followed by a mask which would take over half an our to dry, so I got busy on a quick manicure to give his nails a lustrous red finish. As I finished up, I realized if this went well we could schedule beautician appointments together in the future - if he wanted assertiveness, he'd get it!

I then peeled off the mask and after a face rinse called him to my makeup table where all my supplies were neatly laid out. He swallowed hard when he saw what was in store for him: liquid foundation and powder, blush, eyeliner, shadow, mascara, and false eyelashes. This was all meticulously applied while explaining the whys and hows. Once the lashes were perfectly adhered, another touch up of mascara blended them in to our previous work. When we finished with these I pulled out the still new in wrapper tube lipstick, liner and lip gloss. While not perfectly matching his nail polish his lips were done in a luscious and glossy coat of femininity that would fascinate and captivate anyone one within a few steps of my dear husband. His first view the new Bill came once we fit the head cap on and secured the longish pageboy wig. I had taken a lock of his hair so I could match his hair color, and that it did. The bangs framed and accented his made-up face while the dangling ends ends swayed and bounced just above his shoulders.

I have to give Bill credit where credit is due, I would think most men would lose their composure or throw a fit, and some would have a breakdown after such preparation. I did detect a little apprehension on his part. Nonetheless we were now in the dressing phase of his womanly transformation, so I led him from the makeup table over to the bed. Now, I know most women experience a wonderful feeling or glow when they see their finery laid out and some slip into a fantasy state imagining what it will be like to wear and be seen in their attire... I wondered what Bill's inner thoughts were at this moment. He knew he was now fully committed and in a matter of minutes his wish would be fulfilled.

Off came the robe and on went the lace trimmed satin panties. I helped him step into his new girdle which proved to be as restrictive as Phyllis had promised. It required Bill to stretch his torso by placing his hands over his head while exhaling simultaneously. Not waiting for him to to regain his composure or protest, I wrapped the longline bra around his chest and secured the clasps, which again required Bill to stretch and exhale. I adjusted the straps and tugged a bit to get both garments into final position. I then slipped his silicone 'falsies' into his bra cups. There! As you probably know when you're properly fitted, the combination of longline bra and open bottom girdle are fortress-like and complement each other while creating a flattering shape - but at the expense of flexibility. Bill was now properly encased and controlled in his new shape-wear. Hardly able to bend, I helped sit him on the edge of the bed. Next to him was a fresh package of nylons which I would roll up his shaven legs and attach to the girdle's garters. Standing again, "My, don't you look lovely, let's remember this moment, shall we?" And I rapidly took a series of snapshots on my cellphone from a few viewpoints. Then I took the beautiful Vanity Fair slip and lowered it over his head, and its slippery form fell into place. His feminine shape was now easy to see. A few more snapshots were in order. I picked up the dress which was made of taffeta and while it was slightly waist it would flatter any mature medium framed gal. A quick inspection then a zip-up, then I lead my hubby into the next restrictive sensations of womanhood.

"There", I said, "almost done" after I had instructed him to attach his clip-on earrings, attach the clasp on his necklace and slid the bracelets onto his wrists. I beamed what must have been a devilish smile as he looked my way. From a shopping bag at the foot of the bed I retrieved and proceeded to open 2 boxes. "I wanted your first time to be special and for you to feel and experience the ultimate, so here you are, wear and use these in good health, dear husband". Out of the shoe box came a glistening pair of black patent high heels, somewhat pointed and with a 'v' vamp and probably a 4.5" heel. These fit right in to my scheme of all-out feminization while restricting his movements to short, tentative movements. I went back to the makeup table, picked up and loaded his makeup bag with the essentials and handed it to him, "You'll need this the rest of the day when you need to touch up your makeup, dear". With this he looked down at his makeup bag and I finished my thought, "You now need a place to keep all your essentials when you are properly attired, so here you go... enjoy". With that I handed him a handbag that perfectly matched his shoes, again in shiny black patent leather. He was quite the sight at this point. Snap! Went the shutter. I'm not sure if it was the restrictive clothing or the shock of frenzied excitement, But he let out a a sigh-like noise and practically collapsed on the bed. Ah, the sense of satisfaction I felt is hard to describe. I basked in the moment knowing Bill got the full experience and I had at last found a way to gain the upper hand in our marriage.

So Helga, that is a long winded account of how I gave my husband his first dress up experience. I didn't mind it as the shopping was enjoyable yet the actual 'doing' him up is hard for me to describe. Amusing, hilarious, empowering, and satisfying describe my feelings.


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