Mr. Phellps and I agreed to1:00 to 6:00 as my new hours. Once I settled in, there seemed little reason to work longer. I kept up with my old workload, only taking less time to do it. So, things went along pretty much as they had, except that Judy and Diane admitted me to their little circle and I learned to chat, and gossip, in the women’s circle.

Meanwhile, with Sally’s cooperation, I generally finished my housework by 9:00. I loved wearing my dresses at home, but was becoming bored. The morning TV shows held little interest for me, until I found Quilt in a Day. Making and piecing quilt squares is a wonderful creative outlet, and shopping for fabrics became a minor passion. I bought a used sewing machine and spent an hour or two each morning on my new hobby. After a few months I had a collection of place mats, table toppers and bed quilts for every season as well as a huge stash of fabrics.

At the gallery, I’d been working on trying to establish the authenticity of a possible George Catlin which was unsigned and uncatalogued. From time to time, Mr. Phellps trusted me enough to send me to minor estate auctions with a $1000 bidding limit. At one such auction I happened upon a beautiful sketch, a study really, of the very painting I’d been researching. In the corner were the initials “G C.” It would provide the provenance to confirm that our painting was a genuine Catlin.

I placed an opening bid of $50.00, realizing that the value of the sketch was well over my $1000 budget – about $1500, I estimated. I quickly found myself in a bidding war with a minor dealer. He’d been to other auctions with me, and knew that I generally had a $1000 limit. So, he jumped to $1100 for his second bid in an effort to close me out. I pressed on, much to his surprise. Figuring I must really want the sketch, for reasons he could not fathom, he continued bidding – well beyond my $1500 estimate. My final bid was $2100, at which price he let me have it.

When I got back to the gallery, I figured I’d either get a commendation or a reprimand. The worst case was that I’d just bough myself a sketch at an inflated price. Fortunately, Mr. Phellps recognized that the study increased the value of our questionable painting – by $65,000 as it turned out. Instead of a reprimand, I was asked to make a sales presentation to a well-known collector and earned the commission plus a $20,000 bonus. (Judy told me later that the collector was gay and Mr. Phellps thought I might have sex appeal as well as expertise.) The next week, I was promoted to “buyer,” though that only meant that I was sent to more important auctions with a higher bidding limit.

My commission and bonus, with Sally’s earnings, gave us enough for a down payment on a three-bedroom suburban bungalow. One spare bedroom would be Sally’s office and the other my sewing room.

When we moved I wore lady’s jeans and white canvas shoes. Most of the neighbors ignored us, but Dorothy Brown, from across the street, came over to introduce herself, welcome us to the neighborhood and ask if she could help. She’d thought we were a lesbian couple, but when she found out I was a sissy, she was unfazed. Toward evening, she brought us a bottle of wine and a casserole for our first dinner.

Dorothy was single, but quite pregnant. She made her living by selling a variety of goods on Ebay. Sometimes she’d be out on a buying trip, but when she wasn’t, she invited me for morning coffee. Our clatch was rounded out by Bea, an aging feminist with a hippy background, and Juanita, a Guatemalan whom I suspected was undocumented. What we mostly shared was being despised by our largely white evangelical neighbors. With the exception of Juanita, who preferred a low profile, we fought back with with an unending series of liberal yard signs that made our Republican borough look like a Socialist bastion.

At any rate, once we became friends, Dorothy asked if I’d be her birthing partner. I discussed it with Sally, who was quite supportive. So, every Thursday evening, Dorothy and I went to birthing class with about 20 other mothers. One was accompanied by her lesbian partner, the rest by manly males. Of course, I dressed down – in jeans and tees – but my hair, nails and makeup left no doubt that I was a sissy. Many of the men smirked they looked at me, but I ignored them. Dorothy wanted to defend me, but I told her it wasn’t necessary.

Part of the curriculum was an evening on the importance of breastfeeding infants. It was so powerful that Dorothy, who felt nursing would interfere with earning her living, was converted. While the woman lectured on, I imagined what suckling a child would be like. I was quite attracted to the idea. Of course, it was quite impossible. Even if I got breast implants, I’d never lactate.

One morning, after our coffee clatch, I was sewing a quilt for Dorothy’s baby when she called asking me to take her to the hospital immediately. My friend needed me. I grabbed my purse and ran across the street. I only realized what I was wearing when Dorothy said, “That’s a gorgeous dress Charlie.”

I’d never been out of the house in a dress, but it didn’t matter. “Thank you, Dot. Where’s your bag?” I grabbed it and hurried to my Kia.

Dorothy followed, carrying a large towel. Only then did I realized she was bleeding.

I must have broken every traffic law on the books speeding to the emergency entrance. Fortunately, the bleeding had stopped by the time the doctor examined Dorothy; however, she was in labor. While I waited for the doctor to complete her exam I called the gallery to say I wouldn’t be in, and Sally to say what was happening. Eventually, I joined Dorothy in the labor room.

Her labor was six hours. While I coached her breathing and encouraged her, I formed a very strong empathetic bond – almost as if I were having the baby. Finally, Dorothy was taken to the delivery room and I gowned up. She delivered a healthy 6 lb., 7 oz. girl. Indescribable maternal feelings washed over me as I held the baby for a brief time.

After Dorothy was asleep in her room, I went home, exhausted. Sally was waiting with Chinese take out. She greeted me with a warm kiss, slightly surprised that I’d worn a dress out of the house. I ate a few bites, then went to bed.

I slept for 10 hours. When I woke, Sally had already left for court. I dressed for work, but stopped by the hospital for a brief visit. Dorothy had named her baby Charlene after me. As I held Charlene, strange feelings again overwhelmed me. I found myself crying. Embarrassed, I returned the baby and gave Dorothy a kiss on the cheek – as women do – before hurrying off to the gallery.

I visited Dot a couple of times a day, then drove her home. Sally saw how much I cared for her and the baby, and asked “Charlie, are you in love with Dorothy?”

“Yes, but only as a sister – and an auntie to Charlene.”

“I thought so, but I had to ask.”

Once she was home, Dorothy felt a greater sense of urgency about supporting the two of them, and asked me to babysit each morning as she went off in search of goods to sell. Charlene was a wonderful baby, but when she got hungry, she wanted a breast, not the bottles of expressed milk her mother supplied for her. Turning her head from the bottle I offered, she would mouth my nipple though my bodice or blouse. Although it left a wet spot, I allowed her to do it because it comforted her. Still, I was starting to rethink this when, after a week of almost daily babysitting, my nipples became sore and swollen.

Of course, I would change tops before going to work. It was quite a surprise, then, when Judy came in my office and closed the door.

“Charlie, you seemed not to have noticed but you have a bit of a problem.”

“I do?”

“Yes, you have milk stains on your blouse.”

“Milk stains?” I said, looking down. There were two wet patches on my blouse. Thinking I’d forgotten to put on a clean blouse, I blushed. “Oh, when I babysit Charlene, she often mouths me.”

“No, dear, it’s milk. Trust me, I know. The stains have gotten bigger since you came in.”

I opened the top of my blouse and pulled back my cami. A drop of watery milk formed on my nipple and ran down my breast. “Oh my God! How did that happen?”

“You didn’t take anything so you could nurse Charlene?”

“Hell no!” I was in a complete panic. “What am I going to do?”

“Well, when I had your problem, some 20 years ago, I made sure I fed Mary before coming in, and carried extra pads for my nursing bra.”

“I don’t feed Charlene – not like that anyway. And I don’t wear bras.”

“Well, I suppose you could get a breast pump. But, I’m not sure how you can keep your blouse dry if you don’t wear a bra and pads. In any event, you need to go home and change before anyone else sees your little problem.”

I went home and wrapped an ace bandage with some tissues around my chest, but, rather than helping, the pressure forced out more milk. I rewound the now damp bandage very loosely. I measured my chest, and went Target to buy a nursing bra. I hoped to get an A or even an AA, but the smallest cup they came in was B, so I left with two 36-B nursing bras and a box of 100 pads. No one paid special attention to me, so I suppose they thought I was a rather masculine woman.

When I got home and tried on my one of my bras, my flabby chest formed breasts that almost filled the cups. With the pads in place, the cups fit wrinkle free. Looking in the mirror, I no longer saw a sissy, but a plain looking woman who took care of her appearance.

It was embarrassing to go to work dressed like that. As a sissy, I felt honest. Now it seemed as though I were pretending to be a woman. When I told Judy how I felt, she straightened me out.

“Charlie, you are still being honest. You’re dressing as your body is saying you must. It’s not as though you woke up this morning and said ‘I think I’ll wear a bra today.’ Your wearing one because it’s the only reasonable thing to do.”

“I suppose so, but it still doesn’t feel right.”

“You’ll get used to it dear.”

When Sally got home, she was surprised to see me filling out my blouse. When I explained what happened, she was more than sympathetic.

“You look very nice with a bit more figure. The flat chested look didn’t really do justice to your clothes.”

After I cleaned up the dinner dishes, Sally had me sit on her lap. After some passionate kissing, she unfastened my bra. “Time to take these girls out for a test drive.”

At first I felt very awkward, having Sally sucking and tonguing my nipple. Then I felt something I never felt before – having my milk come down. I did not have much, but while Sally suckled at my breast, I had the most indescribably delicious feelings – almost sexual, but still not sexual. Once my milk was gone, Sally took me to bed to complete our love making.

In the morning, Sally asked, “So, are you going to be nursing Charlene now?”

“I don’t know if I should.”

“I don’t see why not. Lot’s of children have wet nurses.”

“Maybe, but they usually aren’t men.”

“I thought you were past that – thinking of yourself as a man.”

I blushed.

“I expect you to discuss this with Dorothy and see what she thinks.”

Full of mixed feelings, I said, “Alright, dear.”

I went to Dororthy’s coffee clatch after my morning housework. There, my new bra was the first topic of conversation. I was among friends who’d shared very intimate details of their lives, so I wasn’t embarrassed to share my tale.

When I finished, Dorothy asked, “Would you like to nurse Charlene?”

That was an embarrassing question, but I summoned the courage to say, “Yes, I’d like to try.” So, I sat with my blouse open, nursing Charlene for a few minutes while the conversation continued with no more interruption than if Dot were nursing the baby. It was a wonderful, maternal feeling. I was sad when my little milk ran out and I handed the baby back to her mother.

With the ice broken, I nursed Charlene at every opportunity, until she was weaned at nine months. Since my nursing opportunities we irregular, I had to use a breast pump to relieve the pressure when I couldn’t nurse. The regular production of milk caused my breasts to grow and toward the end my experience as a wet nurse, I needed C-cup bras.

Once Charlene was weaned my breasts shrunk, but only to small, well-defined Bs. Now there was little point in not wearing dresses out, as even in shorts and a tee, my breasts screamed “female.” Established customers at the gallery knew I was male, but new customers invariably called me “Ms. Hobson.”

As Charlene grew into a toddler, she began calling me “Auntie Char,” and we remained close. Still, I missed having a baby to nurse and tried to persuade Sally to start a family. She was willing in principle, but the time never seemed right. There was always some case or appeal that demanded her time and attention. Also, we seemed to be drifting appart.

Then, one day, Sally said she was pregnant. I was overjoyed. Sally not so much. She was even thinking of having an abortion. I told her that if she had the baby, I’d do all of the child care. As far as she was concerned, it would be “launch and forget.” Reluctantly, she agreed. Shortly after Charlene’s fourth birthday, Sally delivered a 7 pound 4 ounce baby boy. We named him Leslie, after my grandfather.

Not long after, Sally filed for divorce. We parted as friends. She’d fallen in love with Susan at work, and they moved in together. Neither were interested in children, so I got full custody of Leslie.

Meanwhile, Dorothy was having a hard time making ends meet. I persuaded her to sell her house and move in with “Auntie Char.” At first we had a sisterly relation, but in time, our relation blossomed into something more fulfilling. We married a year after my divorce was final. In time we had our own baby, Mary Lu.

Leslie is almost 12 now. He’s his father’s son: he likes to play with his sisters and wear pretty things. It’s entirely his own choice, but he’s much happier now than when Dot and I tried to make a boy of him. Like me, he wants to stay male, albeit a pretty one.