George, a barista, tries to better his station by applying for a job as as Admin, thinking it is an administrator. Sandy's interview probes his motives in applying for a traditionally feminine job.

Georgie

I had been out of college for 8 months with a huge student loan and no decent job. I had a degree and certificate in early childhood education, but the only job I’d found was as a part-time barista in an office-building coffee bar. I got minimum wage plus a few tips – only enough not to further burden my mother with whom I was still living. It was really a dead end job for me, because everyone knows the only way to get a teaching job is to be a substitute teacher long enough for some principal to notice you and recommend you for full time work – and you can’t substitute if you have to be at work every morning for the morning rush.

Mother loved me, but had told me when I picked my major that early childhood education was not a good economic choice. Now that I was in a bind, I knew she was wondering why I hadn’t listened to her. She never said anything, but when she brought home a DVD of Failure to Launch, the message was pretty obvious.

Of course, I did not date – not because I did not like girls or even meet pretty ones, but because they saw me as a cute a 5’6” 135 pound barista who probably had a boyfriend at home. Not only was I small, I’d let my blond hair grow to shoulder length to cut expenses. Only hunky gay men hit on me. If I were so inclined, I would have been flattered. Instead, I was embarrassed and annoyed.

So was my life when a professionally dressed young woman ordered a latte about 9:30 one morning. She was interviewing to be “an admin” in one of the law firms upstairs. We were the only two in the shop, and so talked until just before her 10:00 appointment. I knew I could be an administrator. I was well organized, had good computer skills and had even taken a couple of business courses before I settled on early childhood education as my major. The salary was much more than the pittance I was making.

The next morning I hand delivered a tailored resume to the law firm’s receptionist, and was rewarded by a call for an interview a few days later.

Sandy

I was very surprised when Sally, our receptionist, told me a man had applied to be my administrative assistant. What she actually said was “a pretty blond boy who's probably gay.” We’re a liberal firm with a proactive equal-opportunity policy. Interviewing a man to be my secretary would reinforce that image. So, even though his resume was weaker than those of the women I’d seen, I had Sally set up an interview.

The idea of a male secretary was strangely appealing. My ex was a macho ass, so the idea of bossing a man roused a side I didn’t know I had. Novel, unprofessional fantasies ran unbidden through my mind. I’d never act on them. I’m scrupulously professional and ethical. Still, one can dream, and my fantasies were very entertaining. Too bad the candidate was probably gay.

When George Myers came into my office, he was everything I’d fantasized: petite, and fine-featured with shoulder length blond hair. He told me about his computer skills and business course work.

“Are you in a relationship? Married, living with someone? Have a boyfriend? I ask because it relates to your potential stability as an employee.”

He blushed, but didn’t take offense. “No, I live at home with my mother. Despite my appearance, I like girls. They just don’t seem to like me back – not like that anyway.”

I asked his major, as it wasn’t on his resume – early childhood education – a traditionally feminine major. Once I’d confirmed his lack of experience, I decided not to hire him. Still, I wanted to know what made him tick. “So, what made decide to apply for a traditionally feminine job?”

“What do you mean?”

“I mean that being an administrative assistant, a secretary, is traditionally a woman’s job – not that that disqualifies you – we are an equal opportunity employer. Still, knowing your attitude is important in deciding how you might fit in here.”

“Oh, I thought the job was being some kind of administrator.”

“Didn’t you read the job description? How did you find out about the position?” He’d met a woman coming for an interview in the coffee bar where he worked and, being desperate for a better job, he decided to apply. He thought “admin” meant administrator. I had to credit him for initiative, if not business savvy.

“So, now that you know, I take it you’re no longer interested?”

“No, I’m still interested. I can’t afford to be hung up on gender stereotypes. I need a better job.”

I don’t know what came over me – maybe my fantasies – but I asked, “And if our dress code required administrative assistants to wear a skirt and blouse – what would you say?”

“Well, I’d have to think about it.”

“So, you aren’t that sure you want the job?” I was being mean, but was intrigued that he hadn’t said “no!” to the possibility.

“Oh I do! If I had to wear a skirt, I guess it would be worth it. I’d just be embarrassed.”

“I’m sure you’d get over it in time.”

“I guess I’d get used to it.”

“Well, you’ll be glad to know our dress code requires no such thing. I just wanted to see how much you want the job.”

“Oh, thank goodness. I don’t think I’d look very good in a skirt.”

“I’m sure you’d look lovely.” He blushed. I rose and shook his hand and told him we’d let him know one way or another once we’d decided. Of course, I’d already decided and drafted letters for Sally to send out that afternoon.

Georgie

I arrived on time for my interview, smartly dressed in my graduation suit. As I walked in I saw Ms. Sandra Major, Esq., seated behind a huge desk. She was about 10-12 years my senior with healthy complexion, athletic build and gorgeous figure – way out of my league. When she shook my hand, she was 4-5” taller than me – and in flats. Her short brunette hair, lace blouse and short, floral print skirt gave her an imposing presence.

She was gracious, but as the interview progressed, I felt ever more foolish. First, I had no relevant experience. Second, the job opening wasn’t for an administrator, but an administrative assistant – a secretary. Finally, saying I’d wear a skirt and blouse if the dress code required it was pathetically desperate. To cover my embarrassment I said I wouldn’t look good in a skirt, but she returned a complement: I’d “look lovely.” Sadly, she might be right. No wonder people assume I’m gay.

Two days later I got a very polite letter – it was a pleasure to chat with me, but, despite my impressive qualifications, … I was not surprised. I was almost relieved that I wouldn’t have to work for a woman before whom I’d so embarrassed myself.

Sandy

I didn’t know that Georgie (that is what I called him in my mind) worked in our building until I had to rush to a meeting one morning before my new admin had made coffee. I stopped at the lobby coffee bar and there he was, cute as ever, with his hair in a ponytail. We nodded in recognition, but I only had time to buy my coffee and leave. As I drove to my meeting, my fantasies returned with a vengeance. I decided to return to the coffee bar later and ask him out.

I had my new admin find the name and number of the coffee bar manager. I called her, said I was an attorney, and asked when I could talk to Mr. Myers without interrupting his work.

The next day I wore a new Tom Ford scent, Velvet Orchid, and my “power suit.” We all know that the masculine power suit of the last century is passé. My “power suits” are floral and lace – showing just enough leg and cleavage to distract the weaker sex. At 9:55 I went down to the lobby, ordered a black coffee from Georgie, and told him I wanted to have a word during his break.

I’m not into devious dating games. I started by saying why I had not hired him – he was under-qualified and I’m attracted to him. The last threw him into a tizzy of stunned silence. After waiting for a bit for him to recover, I asked if he liked French food, then if I could take him to dinner Friday. The poor thing could only nod.

Georgie

I was very surprised when, a month later, Ms. Major came into the coffee bar to order a black coffee. She was in a hurry, so we just exchanged smiles and she left. I didn’t expect to see her again any time soon. I was shocked the next day when she came in just before my 10:00 break, ordered coffee and asked if we could chat. I wondered how she knew I’d be on break, but I wasn’t about to look a gift horse in the mouth.

When I joined her, she looked and smelled fabulous. “I want to start by saying that you didn’t have as much experience as the other women I interviewed, but even if you had, I still could not have hired you.”

“Because I’m a man?” I knew that couldn’t be the reason when she lumped me in with “the other women,” but I didn’t know what else to say.

“No, because I’m attracted to you, and I didn’t want you to feel job pressure when I made my advances.”

Her “advances”? As I said, she was way out of my league, so that was the last thing I’d expected. Besides, she’d said I’d look lovely in a skirt. So, she could hardly think I was much of a man. Maybe she was just trying to be nice, then. But now? I sat with my jaw dropped and mouth open until she went on.

“To cut to the chase, do you like French food?”

I closed my mouth and nodded, even though I’d never eaten any.

“Good, then how about dinner at Chez André Friday night?”

I nodded again.

“I’ll pick you up at 7:00. Wear the suit you wore to the interview. I have your phone number and address already. See you Friday.”

She left and I sat stunned until Martha, my manager, came over and shook me to say my break was over.

When I told my mom what happened, she had mixed emotions. She was glad that I was finally starting to date – and a woman. (Despite my protests, she also wondered about my orientation.) On the other hand, she was concerned that Ms. Major would be more experienced and could take advantage of me. Ms. Major anticipated her concerns and called her (not me) the next evening. Mom closed the door for an hour-long woman-to-woman talk.

Sandy

I was almost positive that Georgie would tell his mother about our date, and equally sure that she’d be concerned about her precious child dating an older, experienced woman. No doubt Georgie was a momma’s boy, so I needed his mother on my side. At 8:00 I gave her a call. Georgie answered and was excited to hear my voice, but a bit disappointed when I asked to speak to his mother.

When I spoke to Nora, I knew I was right. She was a surprised, but gratified, that he was dating a woman. Still, she couldn’t imagine why a confident woman would be interested in him. She didn’t have specific suspicions, only a vague feeling that I was too good to be true.

I stated by saying how, like most young women, I had been drawn to gorgeous hunks. When I met Ted, I felt he was a dream come true. He’d been a star fullback in college and had a body to die for. He was sweet enough while we were dating, but once we married he became rude, arrogant and unfaithful. As a lawyer I earned more than him and that made him insecure. He reacted by doing his best to sabotage me. When he became physically abusive, I left. Since then, I’ve sworn off men – until I met Georgie.

He was unburdened by gender stereotypes – even open to wearing a skirt if our dress code required it. His openness stirred confusing feelings in me – none of them negative. One idea I’d sorted out was if we had a family, he could be the homemaker, caring for our children. My biological clock was ticking, and I wanted children soon. So I wasn’t toying with her son.

She listened until I finished, then spoke. She didn’t think he’d ever worn women’s clothes, but wasn’t surprised that he’d consider it. He’d never been very manly. Her main concern was that he’d die single and alone. She didn’t want him to have the stress of being gay, but she’d rather he be gay than alone. In fact she’d been seriously considering arranging a date for him with a gay man she knew at work.

She could tell that I was serious about him. I was his first, and perhaps only, real chance at a relationship. She’d be supportive. I thanked her.

Georgie

Before my date, mother insisted on helping me with my hair! She brushed it out, looked at it, and said I needed a bit more flair for an elegant dinner date. Much to my chagrin, she used her curling iron to give the ends an outward flip. I thought I looked femme, but mother insisted it was fine and Ms. Major would like it.

At exactly 7:00, Ms. Major rang the bell. I was still struggling with my tie. My mom answered, introduced herself, and invited her in. When I came into the room, Ms. Major gave me a radiant smile, said I looked “beautiful,” and that she especially liked my hair. I was still a bit embarrassed about it, but her compliments gave me a warm glow, making me glad I’d let mother help.

Ms. Major told me to call her Sandy, took my hand and lead to a blue Beamer parked out front. She opened and held the door while I got in. As we drove to Chez André, she told me how she was attracted to me during the interview and struggled to act professionally. She asked if anything she said made me feel uncomfortable. I told her nothing had. She was glad.

When we arrived, I struggled to release my seat belt. By the time I figured it out, she was holding the passenger door open, offering me a hand. She held my hand till we got to the entrance, then opened that door for me. At the table, the maitre d’ sat me while Sandy sat herself.

“Shouldn’t he have sat you instead of me? And, shouldn’t I be the one opening doors for you?”

“One reason I like you is during your interview you said you aren’t hung up on gender roles. I was married to a macho ass, and I can’t stand that attitude. Since I’m more fit, it’s logical that I open doors. I earn more, so should I pay for our dates. If you were just blowing hot air, tell me now, and I’ll take you home with no hard feelings. Are you OK with me leading, or should I take you home?”

“No, I’m not at all macho. I want you to like me, and you’re right – you are stronger, more experienced and earn more, so it’s natural that you should lead.” I didn’t want our relationship to end before it started. I couldn’t afford to let my male ego, such as it was, to get in the way of my first chance with a woman.

“Good! I like your attitude. Do you know much about French food and wine?”

“No, not really.”

“Then I’ll order for us. Do you trust me?”

“Yes.”

She ordered for both of us, and it was fabulous! The wine was outstanding and I got very mellow. By the time Sandy walked me to my door, I was feeling wonderful.

“Did you have a good time Georgie?”

“Amazing, Sandy. I’m so glad you asked me out.” I wasn’t about to quibble over my new pet name.

“I work hard during the week. So, I try to make the most of my weekends. Would you like to spend the day with me tomorrow?”

“I’d love to,” I said – forgetting that I usually cleaned the house for my mom on Saturdays.

“Good! I’ll pick you up at 8:00 for breakfast. Wear shorts. We’ll go for a walk later.” She bent me back and gave me a kiss so deep that I melted and literally came in my pants. I was so embarrassed I rushed inside before she could see the wet spot.

Sandy might not have seen it, but mother surely did. “I see that you had a good time,” she said staring at the front of my trousers. I blushed, not knowing what to say.

“Did she take advantage of you, dear?”

“No, she just kissed me good night, and I … well got excited.”

“Yes, I can see that. Go rinse your things out with cold water and we can discuss your date over breakfast.”

“She invited me out for breakfast – in fact for the day! I hope you don’t mind. I won’t be able to clean the house tomorrow.”

“The house can wait. You can do it during the week, dear. I want you to have a chance to relate to a woman other than me.” I could see her thinking, “or you’ll be living here forever,” but she didn’t say it.

“Thank you, mother.” I rinsed my pants as she told me. Then went to bed. I dreamed that Sandy had hired me, and I wore a skirt and blouse to work.

Sandy

Our date went as well as I had hoped. I was surprised that he'd given the ends of his hair a feminine flip.

I did for him all the things a lady could wish a strong, courteous man to do on a first date. He complained once, but backed off when I gave him the choice of going home or letting me lead. It’s a heady feeling, having a male girlfriend.

I’ll never be cruel to him, but being dominant gave me an erotic tingle all evening. He seemed to relax and enjoy it after his initial pro forma protest. He especially liked the French kiss I gave him at the door. I felt his body arch, a pulse against my thigh, and then he almost swooned. His face was flush and he was quite embarrassed – poor dear. Maybe it was his first time with a woman. When I got home a sticky wet spot on my dress confirmed my suspicion. I hoped to embarrass him more like that in the future.

Georgie

The next day I put on stone poplin shorts and a baggy black tee. When I came out, mother asked if I were going to a funeral or on a date. I didn’t have any brighter shorts – mother said she’d buy me some – but she’d given me a sleeveless purple top she insisted I wear. I’d never wore it because it’s close-fitting and I’m ashamed of my body. I also wore loafers and dark socks because I didn’t have tennis shoes. They didn’t make mother happy, but there was nothing to be done about it.

Sandy appeared promptly at 8:00 and escorted me as before. She and mother must have a psychic bond because she complemented me on my top, but said we needed to do something about my shoes.

The day was overwhelming because Sandy is overwhelming – so decisive. We began with breakfast at a small family restaurant where they knew her. She introduced me as her new friend, Georgie, and ordered me the Nature’s Best Special – a fruit bowl, yogurt, and one slice of multi-grain toast with safflower spread. She had the Farmer’s Plate – two eggs, sausage, home fries and a stack of buttered pancakes. She explained she’d burn the calories off at the gym, while I wouldn’t. If I wanted a bigger breakfast next time, I’d have to join her at the gym.

As we ate, she told me about her broken marriage to Ted, a former football player who must be a real ass. No one had interested her since, until she met me.

“Well, one thing’s for sure – no one will think I was a football player.”

“That’s why you’re so perfect! You’re very pretty, and so far your personality seems to fit mine. You’re not insecure being with a strong and successful woman. My biological clock is ticking. It’s time that I started a family. You’re interested in children. What do you think?”

“You’re way ahead of me. I’m just glad that we’re going out – that you’re interested in me. When I first met you, I thought you’re totally out of my league. I’m like stunned that you even want to go out with me. In fact, I’ve never even gone on a real date before. I escorted my cousin to her school dances a couple of times, but that’s it. Girls never seemed interested in me – at least not before you. Even my mother thinks I might be gay – I’m not – really – but when you don’t date girls, er … women, that’s what people think.

“I do love kids. That’s why I majored in early childhood education – so I could spend time with them. I probably never will because I won’t get a teaching job because working at the coffee bar means I can’t be a substitute, and that’s the key to fulltime teaching.

“So, you’re way ahead of me thinking about starting a family. To me it’s just something I hope will happen one day, but thought never would.”

“Oh Georgie, I’m sorry. You must think I’m really pushing things. I don’t mean to be. It’s just that when I know what I want, I go for it. I’m laying my cards on the table for you. Now you know what I’m looking for and that I’m serious about you. We still need to learn a lot about each other and ourselves, but at least you know what I’m thinking.”

“Sandy, I appreciate you being honest. I’ll try to be too, but sometimes I’m shy or embarrassed. So you’ll need to be patient with me.”

She reached out and held my hand between hers. “I’ll try my best to be patient with you, Georgie.

“To change the subject … one treat I give myself is a weekly facial, manicure and pedi. I really enjoy being pampered. You would too, if you let yourself. I’d like you to come with me, and give it a try.”

This was going to be one of the strangest dates ever, but I couldn’t say no to her. We walked a few doors south to The Chi Salon, where, again, the staff all knew Sandy. “Georgie will have the same as me, but no color, please.”

My face was massaged as I closed my eyes and relaxed. Someone was removing my shoes. When I woke, my face had an invigorating tingle and my nails were shaped and shone with clear lacquer. I should have been embarrassed. Instead, I was amazed how good my nails looked – not masculine or feminine – just beautiful – like they were meant to be from the beginning of time.

Suzie, who’d done my facial, told me that I wouldn’t need to shave for a few days. Was that even possible? Most boys can’t wait till they have to shave, but I always thought it was a pain. It would be a miracle if I could skip shaving.

Apparently, Sandy had stepped out to do a bit of shopping because she came in with a paper bag in hand. “Well?” she asked.

“I feel amazing. Thank you so much.” That earned me a kiss, but a daytime one that didn’t cause the reaction of the previous night.

The next stop was a shoe store where Sandy bought me white sneakers, peds, and laces to match my shirt. I should have felt like a sissy, but I looked too good to feel down on myself. Again, not male or female, just nice to look at. Only the blond fuzz on my legs looked out of place.

As we walked back to her car, I was surprised how comfortable my new shoes were. I was self-conscious about my purple laces, but no one seemed to notice, and I soon forgot about them.

Sandy drove into the mountains to a shaded parking area. She shared some sun block, then slipped on an insulated backpack and led up a narrow trail. I was scared as we approached a treacherous spot where one slip would send me sliding into the canyon below, but she held my hand firmly and I felt safe. After 45 minutes, we arrived at a small waterfall. There we sat on flat rocks and had wine, crusty bread and cheese. I was tired, and fell asleep in the sun – cooled by the drifting mist.

Sandy woke me with a gentle kiss. “Wake up princess.”

I opened my eyes and soon we were kissing passionately. Sandy took my hand and placed it under her top on her bare breast. I had often dreamed of breasts, but had never touched one. Hers was fuller and softer than I had ever imagined, with a large firm nipple. Again, I embarrassed myself by ejaculating in my shorts.

As I did, Sandy hugged me close, saying “It’s OK.” She held me until the glow past, then helped me stand.

“Oh dear, you have another wet spot, princess.”

I blushed.

“After last time, I thought you might need a change,” she said, handing me the paper bag I’d seen earlier. Inside were white scallop-pocket J. Crew shorts with pink polka dots, and white Hanes Her Way panties.

“These are women’s …”

“No gender hang ups, remember? You’ll look darling in them. Or you can parade around with your little accident.” I decided I had no choice but wear them.

“Aren’t you going to turn around?”

“I let you fondle my breast. Now it’s my turn – fair is fair.” She watched as I changed, suggesting that I’d look better if I tucked myself back. “I was right, you do look darling in those. You’ll look better after you shave your legs. How do you feel?”

“Embarrassed.”

“You'll get over that. Just think how cute you look and how much I appreciate you dressing nice for me.”

By the time I got home, I knew I had spent the best day of my life with Sandy.

Sandy

Saturday was when I would see if Georgie would let me feminize his appearance. I ordered him a breakfast appropriate for a weight-conscious young girl, had him participate in my facial and nail regime, and shared a little passion in my favorite forest hideaway.

I must have tired Georgie out, because he fell asleep after our picnic. Watching him sleeping with his fine features and slightly curled blond hair, I could not help but think of him as sleeping beauty. I woke him with a kiss and called him “Princess.” He didn't object.

He was so pretty sleeping I wanted to be with him, but it was only our second date and the poor dear was a virgin. I didn’t want to scare him off. So, I contented myself with passionate kissing and teaching him to fondle my breasts. As I expected, he could not contain himself. I held him close and told him it was all right as he had his release.

I knew he’d loose control again and need a change, so I’d bought a pair of cute shorts and panties while he was finishing at the salon. I watched him change, and I saw the potential for great bed partner.

I delivered him home about 5:00. Nora greeted us and invited me to stay for a spaghetti dinner. She told Georgie she liked his manicure, and new shorts and shoes. She seemed to enjoy making him blush.

She asked if I wanted some Chablis. When I said yes, Georgie was lead off and returned in a hostess apron with my wine. After that he stayed in the kitchen while Nora joined me with her own wine.

“You do work fast, Sandy. Is he wearing panties as well?”

“Yes, nothing fancy, just white Hanes.”

“I’d thought many times while he was growing up that he might prefer feminine clothes, but it just did not seem right. You know what I mean? But now that he is wearing them, I see a glow about him that I've not seen before. Was it difficult? I mean getting him to have his nails done and wear girl’s things?”

“No, not really. He made a few pro forma protests, but did not put up any real opposition. He even let me call him ‘princess.’ Did you have trouble getting him into the apron?”

“No, it was pretty much like you described. He asked if he really needed to wear it, but when I told him he needed to keep his white shorts clean, he let me tie it on him.

“This is not really what I had imagined for my son, but he seems happy, and you seem very sweet with him. So, I’m glad you came along.” She gave me a motherly hug.

I blushed. “Thank you,” I said sincerely.

“He seems to enjoy being treated like a girl, but be embarrassed by it. We need to work together to help him get over his embarrassment. He’s so pretty, he really should have a chance to take pleasure in it while he’s young. Your complements really help.”

“I agree. I don’t believe in doing things half way. Once I make up my mind, it’s full steam ahead for me. After all, I’ve never had a little girl and so I’ve missed out on a lot. I’m not going to let you have all the fun!” Just then Georgie came out of the kitchen to announce that dinner was ready.

“Thank you, princess,” Nora said.

Georgie

After my date with Sandy even my mother was calling me princess. I have to admit it made me feel special, but, still, it was embarrassing.

Sunday Sandy was busy visiting her family and straightening her apartment, so we did not see each other.

Monday mother suggested that I wear my new shoes. Martha noticed them as well as my new hairstyle and nails. She said they looked good, and that as long as I looked neat and professional, she was all in favor me exploring my “new look.”

Maybe it was because of my new look, or maybe it was because I was so much happier than I’d been, but I noticed a big increase in my tips.

Sandy works long hours during the week, so I only got a few brief texts saying how much she enjoyed our time together, how pretty I was, and how she was looking forward to spending more time with me.

Tuesday morning, mother said, “I found your new panties in the laundry. If you’re going to wear panties, you should try brighter colors and prettier styles.”

I was not sure how to respond, so I said nothing. Mother seemed to take that as agreement.

Wednesday my boxers had been replaced with an assortment of brightly colored cotton bikini, nylon print, and lacy panties. I was too embarrassed to say anything, so I picked out a pair of cranberry cotton panties as the least feminine. They gave me a strange feeling – not sexual excitement, but a confident tingle that I decided was what girls mean by “feeling pretty.” By the time I got to work, I was a bit down because Sandy was not there to see how pretty I was in them.

I was still feeling that way when Sandy came in at 9:55 for join me for my 10:00 break.

“Hi princess,” she said as she came in.

Even though it was embarrassing to be called “princess” in front of Martha, I felt special and happy.

“Nora called to say you decided to wear panties all the time. I took a break from my deposition to tell you that I can’t stop thinking how pretty you must look in them. Do you have a pair on now?”

I nodded.

“What kind?”

“Cranberry bikini ones.”

“I wish I could see how good you look in them. Do you want dinner at my place Friday?”

“I’d love it.”

“I’ll pick you up at 7:00. Wear something pretty. It will just be us, so you needn’t feel embarrassed. Bye.” She gave me a quick kiss that left me feeling dreamy.

I felt so like a girl the rest of the day, wondering what I could wear for my date. When I got home I was still feeling dreamy. I told mother what happened and that I did not know what to wear. She had me change into my polka dot shorts and a loose top she lent me.

“That’s not going to work. Go shave your legs and underarms.” It was a very sissy thing to do, but I wanted to look as pretty as possible for Sandy. When I dressed again, Mother darkened my blond brows with a light brown pencil and added lip gloss. I looked like a girl. Still, I was nervous.

We went to Macy’s. I almost didn’t get out of the car. Mother led me to the Junior’s department. I got no strange looks on the way so I relaxed a bit.

Mother decided that we should look for a blouse first, as it was most like men’s wear. I found a fuchsia satin blouse with a pointed collar that buttoned up the front like a man’s shirt. I loved it, but the front sagged, so it didn’t hang right. Since it was a Junior’s size, it was not tailored for a big bust, but no bust just did not work.

“Do you really like it, Georgie?”

“Yes, but I can’t wear it. I’m too flat chested.”

“That can be fixed.”

“Mother! I’m not wearing a bra.”

“Why not, you wear panties.”

“Well, I don’t have anything to put in one.”

“That is exactly why you, and a lot of other girls, need one. Come on, we’ll see what you like,” she said, taking my hand and heading to the lingerie department. I could have resisted, but it would make a scene.

“Perfect,” she said, handing me a padded push-up almost the same shade of fuchsia as the blouse I was still holding. “Go try it on. Do you want me to help?”

“No, I can do it myself,” I said, somewhat annoyed.

“How do you know, have you worn one before?” Now I was really blushing, and left for the changing room before I was further embarrassed. It took me a long time before I got the hang of it, but eventually I hooked the bra in back. “Let me see.” I opened the door so she could look in. She pushed and pulled my chest flab until I actually had a little cleavage. “You look fabulous! We should get some more in the same style, but different colors.”

“I don’t even need one!”

“Now try your blouse.”

“Yes, mother.”

“Doesn’t that look better?”

In the mirror was a girl I’d like to go out with. Maybe she could improve her hair and makeup, but she still turned me on. I was glad I’d tucked myself back, otherwise I’d have a tent in the front of my shorts.

“You stay here, I’ll pay for your bras and blouse then you can wear them while we look for the rest of your outfit.”

Mother wanted me to look at skirts, but I wasn’t ready to wear one, and I didn’t know if Sandy would like me in one.

“If she likes you in panties, she’ll love you in a skirt.”

“Do you really think so?” I remembered her interview question and my dream, and almost agreed to look at skirts. Then I remembered I was a man, and decided that women’s pants were as far as I would go.

Mother found a beautiful black crepe pair with a wide leg, but they were too long.

“They’re meant to be worn with heels.”

“I’d look silly in heels.”

“You would not. They’d make your legs look great.”

“I don’t think I could balance on them. I’m not very athletic.”

“They don’t have to be stilettos. You could wear block heels. They’d make you taller – easier for Sandy to kiss.” I blushed, but the idea appeal to me.

“OK, we can look, as long as they’re not too feminine.” We found a pair of loafers with 1-½” block heals on sale. The slacks looked fabulous when I wore them. Once I’d gotten them it was not hard for Mother to persuade me to get a pair of wedge heel sandals to wear with my shorts. I dreaded seeing my credit card bill, but the thought of how pretty I'd look for Sandy made it worthwhile.

On the way home we passed a Ross, and mother insisted that we look. I was wearing my new blouse, shorts and wedge sandals. I had no resistance left when mother showed me a floral print skirt that picked up the color of my blouse. When I tried it on and did a twirl, I had to have it.

I would have bought more, but I could not afford another thing. I felt like a very pretty sissy, but that felt great. I wore the skirt home.

When we got back in the car, mother gave me a shoulder bag that matched my new loafers. She was crying.

“I’m sorry I’m such a disappointment. I know I’m not the kind of son that would make a mother proud.”

“Oh, but you do! I am just crying because I did not act on my impulses to buy you pretty clothes when you were younger. … You’re so beautiful!”