I was born Wendell Blair, and abandoned shortly thereafter. I wasn’t any couple’s idea of the boy they wanted, so I was never adopted. I wasn’t abused, but I never felt like I belonged either. So, I just got along dealing with the hand I’d been dealt. After getting an arts degree from Cal State L. A., I worked as a barista near the court house.

It was there that I first saw Shannon. She’d come to pick up an order for the Public Defender’s Office, so I knew she was at the bottom of the totem pole. She didn’t have the looks of a model, but she was cute in a boyish sort of way with short sandy hair, blue eyes and light makeup – usually dressed in a pants suit and oxford blouse. I enjoyed chatting as I finished assembling the PD’s order.

One Monday, she stopped coming in – replaced by a nerdy guy named John. I chatted with him, too, but it wasn’t the same. I missed seeing her enough to be down about it. Then, about 4:00 Friday afternoon, she came in and asked me for a date. It would be an exaggeration to say that my dating life was virtually nil. It was nil. So, I was thrilled to say yes.

Dating Shannon wasn’t easy. Sometimes I’d get a text canceling because she had to fill in for somebody or a hearing had been rescheduled. Other times we’d only get a quick bite together before she had to review case notes. Occasionally, we’d end our evening at her Koreatown apartment for some intimacy. Then one day she unzipped my pants and led me to her bed by my handle. She said she was tired of waiting for me to make my move.

Not long after, she invited me to move in with her. I’d been crashing with some Cal State friends, so I felt like I had a home at last. I offered to pay half the rent, but she said as long as she was making so much more than I was, I should spend my money on other things. I paid the utilities.

Her hours allowed little time for housework, so her place was even messier than where I’d been crashing. I’m kind of a neat freak so I took it on myself to straighten and clean the place. I spent part of my pay buying little things to make our apartment more homey. I learned to sew and made curtains and throw pillows. Shannon never asked me to do any of this, but was very complimentary about my homemaking. When she proposed a year later, she jokingly asked me to be her wife. I blushed a bit, but I can take teasing as well as the next, and told her yes.

Neither of us were churchy, nor did we have a lot of savings, so we got married at City Hall. Shannon wore a cream pants suit (I don’t think she owned a skirt or dress), and I bought a suit. I had no family and she only had her mother, Marilyn. So, we had a simple ceremony with Marilyn and a couple of our work friends. Afterwords, Marilyn took us all to dinner in Chinatown. Her wedding toast included a cryptic remark about Shannon always having been a tomboy.

I’d first met Marilyn when Shannon took me to Sunday dinner at her condo off of Fountain in West Hollywood. She was less than impressed with me, but, still, she was polite and tried to make me feel at home. I supposed that she felt no one was good enough for her only daughter.

Once I’d moved in, we had Marilyn for dinner every Friday night. At first, Shannon ordered takeout, but I wanted to win her mother’s approval, so I started cooking something special for her weekly visits. She enjoyed my meals and even asked for my recipes from time to time. She also noticed how I’d decorated our apartment and gave me compliments on what I’d done.

Shannon had been feeling a bit off before our wedding, but seemed to shake it off. Still, from time to time, I’d see her wince and then tell me it was nothing. Finally, I forced her to see a doctor. Tests and scans followed, then a devastating diagnosis: stage four cancer. Nothing could be done but make her comfortable. I took a leave from work and stayed home to care for her. By the time she died we’d eaten through our meager savings and run up large credit card bills.

After Shannon died, Marilyn kept in touch. She’d call daily to see how I was getting on and came around regularly with carryout meals to share. She had as much reason as I to be depressed, but her ability to function was better than mine. She was simply stronger than I was. I spiraled into a deepening depression. As my work performance fell and absentees rose, I was given another leave of absence and got some free counseling. When I couldn’t pull myself together, I was asked to resign. Of course, my depression was impossible to hide from Marilyn. One Friday she came over with an order of butter chicken to find me unshaven, staring blindly at the dunning notices scattered over the kitchen table.

“Alright, Wendell. Pack your things! Tomorrow I’m taking you to live with me. Do you hear me, Wendell?”

“Yes, Marilyn.” Of course, I was too depressed to pack anything. So, the next day, she came and packed my clothes and personal things, while a couple of day workers moved the rest of our things to a storage locker.

When we got to her condo she showed me the room that was to be mine. It had an en suite bath and fit a bed, bureau, desk and vanity without being crowded. While its decoration was hardly masculine, it was not strikingly feminine either.

“Wendell, you smell like a pigsty. I can hardly stand it. Go take a shower, wash you hair, and shave. I’ll put away your things in the mean time. Oh – and be sure to use conditioner on your hair. Call me when your done.”

“Yes, Marilyn.” I didn’t feel like arguing.

While I was in the shower, the clothes I’d worn disappeared – I presumed to be washed. In their place was an orchid colored satin pegnoire. I didn’t have my own robe, so I figured Marilyn had provided me with one of hers. I couldn't find a comb, but there was a brush on the counter, so I used it. My hair became more lustrous with each stroke. When I finished, it was obvious that I’d gone too long without a hair cut. Only my lack of bangs prevented me from looking like a woman.

Walking back into my room, I called out “Marilyn, I’m done!”

She appeared at the door, looking me up and down. “I thought I asked you to shave?”

“I did” I said, somewhat petulantly.

“Then what’s that on your legs and chest?”

“My legs?” I asked, bewildered.

“Yes – those appendages sticking out under your pegnoire,” she said with a sweep of her hand. “And, I suppose you haven’t shaved under your arms, either. … Back you go!” She gave me a gentle push. “And apply lotion after – there’s a bottle by the sink. Call me when you’re really done.”

I suppose that I should have resisted, but I’ve never been very assertive, and it was her house and … Anyway, I shaved as much as I could, save my pubes. I wasn’t that hairy to begin with, so I reckoned that shaving didn’t make a big difference. The lotion was very soothing, but gave me a lilac scent.

Returning to my room, I called her again.

“Well, that looks much better. Put on some underwear, and I’ll see if you missed anything obvious. … By the way, you smell lovely.”

“Thank you,” I mumbled uncertainly. Going to the bureau, I searched for my underwear, but concluded she hadn’t put it way yet, as all I found was a selection of panties. I supposed Shannon had left them behind.

“Well, get on with it!”

“I can’t find my underwear. Where did you put it?”

“In the top drawer, of course.”

“It only has panties.”

“So?”

“They’re not mine.”

“They most certainly are! I bought them for you last night.”

“What?!”

“Must I repeat myself?”

“But, I don’t wear panties.”

“You mean you didn’t wear panties. Now pick a pair and put them on. Full cut ones would be best under your pegnoire. Chop, chop!”

I didn’t know what to do. I looked into the drawer. The panties ranged from hipsters on the left through full cuts in the middle to lacy tap and pettipants on the right. I found a pair of black satiny panties without decoration. Reluctantly, I pulled them up my legs. By the time I got them to my waist, I was painfully erect.

“Okay, off with your pegnoire. Let’s see! … Ah! I see you like them very much. It’s not surprising, but I think you need a bit of privacy. Lay on the bed and have a wank. When you're done wash them out in the sink with cold water and hang them to dry in your bath. Then put on a clean pair and call me. … Did you hear me?”

“Yes, Marilyn.” I was beet red as she waited for me to lay on the bed before leaving. I’d never been told to “have a wank” in my life, but it was exactly what I felt like doing. I ran my hand down feeling how smooth my panties were. “My panties” I thought. What a sissy I was to be aroused by wearing panties. Once I touched myself though my panties I couldn’t stop. In a few seconds my body tensed in a powerful orgasm and my new panties were soaked.

I lay motionless for a few minutes. Then I got disgusted with myself and wanted out of panties. What kind of man was I? I vowed never to wear panties again. I hurried to the bath, stepped out of my panties and washed with a soft cloth. Then I remembered Marilyn’s instructions and washed my panties I put them over the shower curtain rod to dry. The hanging panties made my bath look like a woman’s – or a sissy’s.

Back in my room I needed to put some underwear on. So, I again opened my panty drawer. On the right were the laciest purple tap pants I’d ever seen. I wondered what it would feel like to wear them. Soon I was laying on my bed again, soaking my pretty tap pants. By the time I called Marilyn back, three pair of panties could be seen drying in my bath.

She appeared in a work apron. “Well?” she said.

“Well what?”

“It would be polite to thank me for the panties you so obviously enjoy. You do enjoy wearing them, don’t you?”

“Oh,” I blushed. How could I deny it? “Yes … Thank you very much for my panties.”

“You’re very welcome dear. I’m glad you like them.” she said without a hint of irony. “Things are so much easier when honesty prevails. … Now take off your pegnoire so I can see if you missed any spots shaving.”

I soon stood before her dressed only in beige nylon panties, too drained to be aroused.

“You’ve done a remarkably good job for a first try … only a few nicks and a little hair on your back that I’ll help you with.” She took my hand and led me into my bath. As she entered, she felt the panties I’d hung to dry. “This pair is dry, you can put it in your drawer when we’re done.”

“Thank you,” I murmured.

She soon finished shaving my back and applying lotion. “Come along, I have something I think you’ll like.” She took my hand and led me back to my room, where she slid the closet door open. “Isn’t this lovely?” she said, holding up an empire waist dress with elbow length sleeves. It was not quite knee length and purple with densely printed white flowers.

I stared at it.

“Well, what do you think?”

“It looks very nice,” I said politely.

“Go ahead, try it on!”

“Me?”

“Who else is there?”

“But, but … I’m a man.”

“Yes, one who likes wearing panties. We’ve established that. I think you’ll like wearing dresses as well.” She unzipped the back and held it for me to step into. “Go ahead, it won’t bite.”

I knew it wouldn’t go away. What was I supposed to do? I was getting aroused and the dress would hide that, so I put one foot in, then the other. Marilyn helped with the sleeves, then zipped it.

“It looks very becoming … Don’t you think? The color suits you.”

I looked in the mirror on the closet door. The color did suit me.

Marilyn tugged her and there, adjusting the fit. “You have just enough of a bust to fill it out … don’t you agree?”

I looked in the mirror again. My flabby chest, accentuated by the band below my breasts, filled out the bodice. With my long, newly lustrous hair, I looked far more female than male. I couldn’t help but stare and turn to see how I looked.

“It’s okay to like it dear. I bought it for you.”

“Why?”

“Because you need something to cheer you up. A new dress usually helps. … Here, I got you these to go with your dress.” She handed me a pair of white wedge sandals. The heels weren’t very high. They were quire comfortable. “Now come along.”

I followed her through the living room and out a sliding glass door to a balcony with a small table and two chairs. Strategically placed potted plants made it surprisingly private – a nice place for morning coffee before dressing. I sat in one of the chairs while Marilyn produced hair scissors and a rat tailed comb from her apron. She started in the back, evening up the ends. Then, before I could think about it, she combed the front few few inches of my hair forward and cut bangs just above my eyebrows.

Handing me a mirror she said “It’s a nice look for you, don’t you think?”

“If I were a woman!” I said with some pique.

“You’re a sissy dear,” she said without the slightest animosity. “Aren’t you? If you weren’t would you be sitting in panties and a dress?”

It was hard to admit, but she was right. “I guess I must be,” I said hanging my head.

“No need to be upset. It’s just what you are. That’s why I had reservations when Shannon married you. … but it was her business. So I didn’t interfere. I saw the self sacrifice and fortitude you showed during her illness, so I came to love you as my own and not just an in-law – to think of you as my own child. I hope you’ll think of me as a mother. However, if you’re to live with me, I expect honesty. So what are you, dear?”

“A sissy.”

“And a very cute one. As long as you’re here, I expect you dress and behave appropriately. Will you do that?”

“Yes … mother.”

“So, what shall we call you. Clearly, ‘Wendell’ won’t do.”

“I guess not.”

“How about Wendy?”

“Yes, that’s nice. I like it.”

I spent the next weeks learning to be Marilyn’s sissy daughter. There’s a great difference between the flamboyant gestures of a drag queen and the natural grace of a woman. Somehow, feminine grace came naturally to me. The hardest part was making my voice passable. I spent endless hours imitating famous actresses. I decided on Lauren Bacall as my voice model. Her voice was so – well sexy.

It didn’t take long to pass for the occasional stranger who came to the door – delivery and repair men. I became the lady of the house while Marilyn ran her boutique – earning my keep by keeping house. As time went on, I made of game of flirting until I elicited a pass which I demurely rejected. Somehow getting a man to want me was a thrill – even though I didn’t want them. As part of the game I worked on my appearance. A padded bra improved my figure and I became proficient with make up. I shared my little conquests with Marilyn, helping us grow as close as any mother and daughter. She suggested I wear jewelry and pierced my ears. The prettier I got, the more I liked being a sissy.

Once I could pass reliably, Marilyn began taking me out. We shopped, had our hair and make up done, went to dinner, and, occasionally, to bars to flirt. Eventually, she offered me a job in her boutique on Santa Monica. I’d never seen it before, and was quite surprised to find that her clientele was mostly male: cross dressers and trans women buying for themselves, and a few dominant women buying for submissive boyfriends, husbands and occasionally sons. I realized then why Marilyn knew I was a sissy long before I did.

I began by working in the back, doing the books and taking care of the stock. After a few days, I learned to run the register so I could cover for Marilyn when she went out.

She’d gone downtown to talk to a supplier when a mother came in with her son. He had long auburn hair and looked to be about 14.

“Hello, I caught Michael here wearing my panties and dresses behind my back. So I’ve brought him to get him his own.”

“Hello, I’m Wendy Blair, and you are?”

“Loraine McKinsey. … Go ahead … tell the Ms. Blair what you want!”

“I don’t want anything, mommy, thank you,” the boy whimpered.

“Well, I think you do, because you want to dress like a girl and I don’t want you wearing my things. So tell Wendy what you like to wear … or I’ll deal with you when we get home.”

“I, I like panties and bras and dresses,” he said in a barely audible whisper.

“Isn’t that lovely for a boy!” His mother glared at him.

“I don’t see anything wrong with it. I’m a boy and I like them as well,” I responded.

“What?!” She turned her glare at me.

“You are? You do?” he asked.

“Yes and yes.”

“But … you’re so pretty.”

“Thank you, Michelle. You’d be even prettier, if your mother helped you. I’m sure she loves you very much and just wants you to be happy.” I could see this wasn’t going the way she’d planned. Getting him girl’s clothes was supposed to be so embarrassing he’d never want to dress again. Still, she was determined to leave with him dressed as a girl. I, on the other hand, wanted it to be a positive experience for both of them.

“You think?” he asked.

“Yes. Now would you like a costume, like a Dorothy of Oz or a Princess Elsa dress? Or something a girl your age would wear? Or, maybe both?”

“Could I have both?” He looked at his mother.

“I don’t know.” She was weakening, and didn’t want to seem prejudiced – at least in front of me.

“Why don’t we let Michelle try a few outfits. Then you can see what you think.”

“I suppose …”

Because of his hair color, I started him with plain white panties, a little padded bra and a Dorothy dress. Before he came out of the dressing room I tied his hair in two bunches with blue ribbons, and put a little lipstick on him. He was thrilled, but still scared what his mother would say.

“Well, isn’t she pretty, mommy?”

I could see that she hadn’t really imagined what he’d look like as a girl, for she looked almost stunned. “Yes, I never imagined. … Do you like looking like that, ah … Michelle?”

“Oh, yes, mommy! I love this dress!”

She looked at the price tag. “It’s not cheap. Would you actually wear it if I got it for you?”

“If you weren’t mad at me mommy.”

“You’re too pretty to be mad at!” She hugged him.

An hour later Michelle helped carry several hundred dollars of merchandise, including ruby slippers, out to his mother’s Beamer. He was happily dressed in a miniskirt, training bra, white blouse and kitten heels. I wondered what would be next for him.

Marilyn was thrilled with my sale, and asked me to work in the front from then on.

The Boutique was next door to a bakery. Georgie, the owner, dressed male, but wore full makeup. I’d often stop in to buy some of his delicious pastries to eat with our morning coffee. He knew Marilyn, and, of course, we became friends as well.

Once I started coming out of my depression, Marilyn began inviting Georgie to dinner. Often, she’d say what a great cook and homemaker I was and what a wonderful wife I’d been to Shannon. I liked the compliments, but still, it was embarrassing. I didn’t even know if liked men.

After dinner, we’d all watch a movie. I liked sitting in the arm chair while Georgie and Marilyn shared the love seat. About the third or fourth time Georgie came over, Marilyn sent me to the kitchen on some pretext. When I came back, she was in the arm chair and I had to share the love seat with Georgie. About half way through the movie, she yawned, said she’d seen it before, and went to bed.

The movie was very romantic and I found myself snuggling against Georgie without thinking about it. He responded by putting his arm around my shoulders, and smiling down at me. It had been a long time since I’d had any physical affection, so I just relaxed – feeling good at being cuddled, without giving it much thought. I was watching one of the most romantic scenes when Georgie lifted my chin and kissed me. He was very gentle. There wasn’t any tongue, just a lingering, romantic kiss.

I knew Georgie was gay, but I didn’t want to be rude, so I didn’t pull away or object. As the movie couple became more intimate, I felt his hand – first on my knee, then slowly moving up my skirt. My heart beat quickened. I thought it was because I was scared and didn’t know what to do, but as his hand crept higher I became increasingly aroused.

“Are you okay with this, sweetie?”

I felt weak and powerless. It had been so long. I just nodded. He kissed me, but more passionately this time – squeezing me through my panties. I tensed and came instantly. “Ohhhh!”

I was so embarrassed! I got up and ran to my room in tears. I didn’t know what Georgie thought. I didn’t even know what I thought. Was I embarrassed because I let a man give me an orgasm? Or was I embarrassed because I had no staying power? I didn’t know. I just knew I wanted to hide.

I didn’t have any friends I could talk to about what happened, so, the next morning, with much blushing, I talked to Marilyn. After all, I’d agreed to be honest with her while I lived with her. I said how embarrassed I was and that I didn’t know why. I also said I was embarrassed about what I’d done to Georgie – running off and leaving him wondering what he’d done wrong.

Marilyn insisted that I talk to Georgie, as it was unfair to leave him wondering. So, I started there.

“Georgie, I, I had an orgasm …”

“I know, sweetie. It was kind of quick, but the whole point of what I was doing was to make you feel wonderful.”

“Well, it had been a long while and I did … feel wonderful. But, I’d never, ah, felt wonderful with a man before. I didn’t … I don’t know how I feel about feeling wonderful with a man … and also, I was embarrassed because it only took me thirty seconds and that’s … well, rude.”

“Ha, ha. I wouldn’t worry about being rude … I mean … I was kind of flattered to have that effect on you. … and as for being confused about how you feel. I understand. I was very confused growing up. So, not to worry.”

“Thank you, Georgie.”

“So, if you want another chance to see how you feel, I’d like to ask you out. There’s a concert at the Bowl I think you might like.”

“Let me think about it. Can I call you this evening?”

“Sure, sweetie. I’ll be waiting to hear from you.”

I thought about going out with Georgie all day. In the end, I decided that I liked being felt up, but when I imagined it, it was Shannon, and not Georgie, I imagined doing it. So, that evening, I called Georgie and thanked him for asking me out, but told him I hoped to find a lady to be with.

Needless to say, I didn't find a lady to date any time soon. Partly, it was because I was still mourning Shannon and not looking very hard, and partly it was for the more obvious reason that a guy who wears dresses is not every woman’s idea of “the one.”

Michelle and her mother, Ms. McKinsey, came in several times over the next six months. They always called ahead to ask for me. Over the months I saw slight swellings on Michelle’s chest blossom into young teen breasts. Meanwhile her other parts seemed to be getting smaller. Clearly, she was on the road to transition.

In late June Michelle turned up unaccompanied by her mother. Ms. McKinsey had been called at the last minute to show a house in Beverly Hills. In her place, she had recruited Michelle’s cousin Beverly to drive him. Beverly was a tall athletic brunet in shorts, a polo shirt and running shoes.

“Hi, you must be Wendy.” She extended her hand to shake mine. She had a strong grip. “Loraine asked me to bring Michelle to get some sun dresses for a cruise. What can you show us?”

I showed them some cute dresses that Michelle instantly liked. So, it wasn't long until she took an armful to the changing room.

“Actually, I wasn’t entirely truthful, Wendy. I asked Loraine to let me bring Michelle today because I wanted to meet you. I must say you’re as pretty as Michelle keeps saying. You’re her role model, you know.”

“I didn’t, but that’s very flattering to hear.”

“Yes … Well, … I hope you don’t think that I’m weird, but I have this fantasy … about feminine men and … well, I’d like to get to know you better. … If you’re interested … in women … and maybe in me?”

“Well, despite liking to dress, I do like women, … but as you can imagine, not many like me … well, not in that way. So, I’d be a fool not to accept the chance to get to know you better.”

“Good, give me your number and I’ll text you a time and place. … what do you like to do?”

“Well, I bought this delicious cocktail dress and I’d love to wear it someplace.”

“I think I can arrange that … Here’s our sweetie in a dress she’d like us to see …”

Friday of that week, Beverly picked me up in her Lexus, and took me to an exhibit opening at the Getty. We met several lesbian couples, who were very polite, but did not linger once we made our situation clear. I did, however, recognize two couples I knew from the Boutique. One was led by an actress, the other by a lawyer who’d known Shannon. After the opening the six of us went to a club for drinks and a bit of dancing. We danced with each others partners, but that is as far as it went.

On the way home, Beverly asked me if I’d like to park and admire the ocean. I very much did, as she was beautiful and strong, and I longed to be in her arms. It did not take long for her to feel me up, but I asked her to go show so I didn’t have an accident. Suffice it to say I did not feel like running and hiding when we finished.

It was only six weeks later when I moved out of Marilyn’s condo, and into Beverly’s beach house. Now, a year later, I’m her wife and the mother of a pretty baby. Of course, Beverly gave birth to our sweetie, but I’m nursing her as I type this.