Chapter One — Discovery.

About fifteen or twenty years ago, I used to travel around greater Boston looking for places that would be friendly when I shopped for my women’s wardrobe items.

I was always discreet and usually wore panties, a bra and luscious stockings or pantyhose under my male clothes. I found several Lady Grace stores that were reasonably hospitable to a cross dressing experimenter such as me.

These were several places that were fun to go to, where the women (and occasionally a man) salespeople were friendly and accommodating. But the selection, while definitely womanly, many times was a bit disappointing.

Then one year I found a very special store in Attleborough, Massachusetts. It was primarily a lingerie store. It was very old fashioned, with plenty of vintage garments, and thousands of pairs of pantyhose and real stockings, as I was told on the phone when I called and spoke with the owner, Anita ...

I headed there on a Tuesday morning, with a few things in my briefcase (a pair of flats and a short wig, some lipstick and a little eyeshade)arriving about 9:45 AM. I walked into the store and noticed the saleslady (who turned out to be Anita) was in a deep conversation with a customer who seemed like an old friend … they were laughing and gossiping.

As I walked nearer the counter Anita said to me, “Hello sweetie, go ahead and look around. Pick out as many things as you need to try on and take them to the big dressing area downstairs. There are so many mirrors down there, and some lovely feminine chairs to relax in.”

I was astounded by her vivacious manner of speech. She made me feel so welcome, although I was still a bit timid with the other woman standing there, also smiling at me.

“Oh don’t mind Shirley here,” announced Anita. “She comes in every day, and is a retired, expert fitter and seamstress of these lovely garments. Don’t you feel so pretty being in here?”

I blushed, but nodded … I think I probably gushed.

After looking around for about fifteen minutes I headed down the stairway. When I was at the bottom I turned into a very elegant spacious room and nearly melted away into one of the French colonial chairs.

The lighting was calming. It seemed like a pale blue mist was all around me, yet I could see clearly. There was a chandelier above the dressing area with some very fancy sconces on the walls with candle like bulbs, adding to the pale blue hue.

And while the floor was covered in gorgeous tile, the dressing area was covered in meticulously cared for Persian rug.
There was a lovely table to one side on which I laid my selections; and another on the opposite side. The second one had a crystal decanter and matching set of six lovely wine glasses.

I noticed some hooks behind me on a wall to which I began hanging my men’s clothes on.

Oh how I wished I had brought a pair of heels and another wig … not to mention more makeup.

As I was trying on a glorious full pink satin slip, I heard footsteps and two voices.

“Hello honey, it’s only me and Shirley. I locked the store early today as it seemed you might be the last customer of the day.

I asked, “Really, it’s only about 10:45 AM?”

“It’s been really slow these last few months. Shirley and I just spend hours gossiping the day away.

“We thought you looked so sweet and a little nervous, so we figured we might give you an assist with what you were trying on.

“You know, help you find the appropriate size and assess what fits in your budget. By the way today is a very special day … everything you buy you can take three other items with you … free!”

I was nervous, but soon that was behind me as I realized how lucky I was.

Anita immediately came up behind me and pulled the slip in from behind so it fit my figure more snugly. “My sweetie, you have kept up your girlish figure. But I do think you could use a little waist training. Ever try a real corset on? Not the silly things they have at Victoria’s Secret.”

I said that I had not, but always dreamed of it, to which Shirley gently whispered, “I knew it. He is so, oh I am sorry, SHE is so new to this, aren’t you honey?”

I answered that I had been dressing on and off for several years, but really did not have the experience I figured they were about to expose me to.

“Well the corset fitting will come in due time,” announced Anita.

She then pinned the full slip, lifted my arms to the heavens and pulled it over my shoulders and head, handing it to Shirley, saying, “Here you go sister, get out your needle and threads and get started.” To which both of them burst out giggling.

I meekly protested that I was not sure I could afford the special tailoring and I had yet to decide what I was going to leave with, to which Anita responded, “Honey don’t worry about the cost, a girl needs to make her decisions based on style. And the slip is a winner on your wispy figure.”

What a sales pitch. They were wonderful. And their joy was infectious.

As they chatted away I realized they seemed to have lost at least twenty years between the moments I noticed them at the register and now, here assisting me and having travelled down the stairwell to my little piece of girlie heaven.

I was handed an all-in-one open bottom, almost corset-like crá¨me colored garment and asked to take off my bra so I could try this scrumptious item on. When I hesitated, Anita guessed correctly my embarrassment at not having very developed breasts.

“It seems our guest needs a little more realistic bosom enhancement Shirley. Can you look in those boxes and find her a proper silicone pair of boobies?

“And not the cheap ones. How about that Cadillac pair that has adhesive strips? Maybe a ‘c’ cup to make her feel really sexy?”

Shirley could not contain her thrill at being able to assist. “Oh what a lovely girl she is going to be by the time we get done Anita!”

While Shirley was searching for the perfect breast forms, Anita realized my panties were going to need an assist as well to contain what maleness was left in me that afternoon. She tried pulling at my panties with one hand from behind while slipping her other hand gently and carefully down the front to push my obstruction to a flat appearing crotch.

“My, my, what have we here? Got to make this magically disappear, don’t we dear?”

I was a bit embarrassed but Anita quickly put me at ease stating, “Nothing I haven’t dealt with before. We need to fit you for a proper gaff honey. I have several sizes. You would not believe how many other girls like you have been fitted here.”

Anita asked me not to move. “Stay there in your panties and hose dear. I’ll be right back."

Still standing in front of the mirror I loved what was happening to me.

She was back in a moment or two. “Close your pretty eyes”, as she “needed to adjust a few things,” first having me slip my own panties off. I was sure my face was turning purple, but Anita placed both hands on my facial cheeks and planted a very soothing and gentle kiss on my lips and said “please just trust me, I know what I am doing sugar.”

After fitting me very expertly with the gaff, I was shocked when she gave me the green light to open my eyes. My crotch had never looked so feminine!
Shirley was back and as they both marveled at Anita’s handiwork, I was told to step into the prettiest white panties I had ever seen.
Then Anita and Shirley assisted me in stepping into the beautiful corselet, and as they drew it up over my hips and tummy, Shirley expertly attached my new breasts while Anita waited to draw the bra over them.

“Wow,” we all said almost in unison.

“Close your eyes again sweetie. Oh my goodness, whatever is your name girl? We need to address you by a proper name,” continued Anita.

“Well I guess Henrietta would be as close to Henry as I can get,” I answered smiling.

“That is a pretty name,” added Shirley. “And it’s not over used these days like so many other girls’ names.”

“Well Henrietta, you need to close your eyes again, and just stand in front of the mirror sweetie. We’ll be right back.”

While I was waiting I was so tempted to open my eyes to try attaching my thigh high stay up stockings with elastic tops to the garters at the bottom of the corselet. But I had been told to close my eyes, so I tried with my eyes shut.
It seemed like may fairy godmothers were gone for ten minutes. By that time I had three of the garters on my left leg attached, and two on my right leg … one to go, when I heard, “ what a darling. Henrietta wasted no time getting those stockings attached, and with her eyes closed!”

Shirley was truly amazed, as was I.

“Keep those pretty eyes shut sweetie,” ordered Anita.

I then felt a nylon cap slip over my own hair, and then I felt the touch of locks on my shoulders.
“Keep your eyes shut sugar, and lift your left foot, there, now your right foot.” She had slipped my feet into some very comfy heels.

“There you go. See Shirley I knew she was a ladies size 11!”

“Now click your heels together three times saying “There is no place like Anita’s Closet.”

I could not believe my ears as I said, “There is no place like Anita’s Closet … There is no place like Anita’s Closet … There is no place like Anita’s Closet,” all while I clicked those precious heels together.

Then a duet of “Now open your eyes Henrietta!”

The two of them giggled as I slowly opened my eyes.

It was like heaven.

It was still only about 11:45, when Shirley asked me, “Do you need to be anywhere special today or anytime soon?”

“Well I am supposed to meet a few friends for drinks in Framingham later this evening, about 9:30 PM.”

“Oh my goodness that is over nine hours from now. What do you think Shirley, do you have the rest of the day off to prepare Henrietta for her date?” asked Anita.

While my first thought was to protest the notion of getting Henrietta ready for ‘her date,’ I looked in the mirror as Shirley gently covered my shoulders with sheer white wrap, lifting my locks gently as she did … I just gasped as the look on their faces, not to mention the tears rolling over my cheeks created a scene too joyous to dampen with doubt.

I was theirs for the rest of the day.

But I insisted that lunch was on me. “Can we order something to go with the wine, and from some restaurant which will deliver?” I asked.

The only other condition was that I needed to be done by 8:30 PM so I could get to meet my friend by 9:30 PM.
Whatever was I thinking? Even though I had been out en femme before, even out to eat, it had never been with folks I had appeared to as Henry.

Would Henrietta show up to meet Jessie, Maria and Ed?

Why not, she looks beautiful standing here in this lovely lingerie … but what about a dress; a purse; a coat and oh my goodness, a girl needing to make a great first impression … what about jewelry?

“I can see the doubt in your pretty eyes Henrietta. Don’t worry about a thing. You will see men falling off their bar stools before tonight is over!” Anita whispered into my ear.