Looking Back at my First Time

by Kelly Davidson

edited by Nelson T.

 

Author’s notes: This was a painful story to write, and I was somewhat reluctant to post it. One of the reasons why is because this story gives the wrong impression about my life. While some may view this event as a wonderful (and unbelievable) experience, it doesn’t have the happiest of endings. I’ve learned that to experience your dreams/fantasies, you have to tell people about yourself, and that’s where the problem lies. How much are you willing to risk? A jilted girlfriend tells your parents that their son likes dressing up in her clothes, or a trusted friend who turns on you when you tell him your secret. I have had many crossdressing fantasies come true, but I paid a steep price for them. My life was filled with teasing/hurtful names, physical attacks, and rejection. An example of the last is the family picture taken after my parents found out I was a ‘horrible’ crossdresser. Everyone is in the picture – except for me. It pains me each time I go home and see it hanging on the wall.

I can recall another time running for my life because a group of neighborhood bullies were chasing me down a water sewer pipe. A trusted friend (or so I thought) had taken me down to the creek claiming he wanted to show me something. This was about a week after I told him my secret. That’s when eight of them step out from behind the trees, screaming that they were going to "kill the faggot’. What I didn’t know was that they had two kids waiting to grab me on the other end of the sewer. Fortunately, I was able to bust pass them and get away. I can still remember to this day the fear I felt, and how I cried afterwards because of their hate for me – not to mention the betrayal from my ex-friend.

Growing up I was a loner who lived in fear, for I never knew when some bully would jump out from behind a bush to beat me up. It happened more then once, simply because I was different. It didn’t matter that I tried to avoid trouble, they always found a reason to pick on me. I was neither good with my fist or my wits, and my mother always found a reason to blame me whenever there was trouble.

There were other events that happened, things I can’t even think about because it’s too damn painful. Some of them were so horrible I simply forgot about them for years – and I’m talking about major events here. So when you read this story, please remember that my life was not a bed of roses. There were some good times, but I paid a price for them.

Anyway, I hope you enjoy the story.

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I remember her giggling as she led me up the stairs to her mother’s room. Her name was Patty Carson; a slender and attractive 18-year-old girl married to my best friend. She was also the biggest tomboy I had ever met – a total opposite of her mother who lived her life in femininity. I had been the best man at their wedding, and I can still remember Patty standing there in front of the justice of the peace wearing a plaid shirt and her faded blue jeans – or ‘wedding jeans’ as she called them. There was no way she was going to be caught wearing a long, fancy wedding gown. I should mention that an unplanned pregnancy had been the reason for the quick ceremony.

A few days before I had told her I was going to work dressed as a girl with some other co-workers. Seeing that she didn’t own a dress, I was hoping to get her help with my makeup. Patty may not have worn skirts or dresses, but she did wear makeup. So when she offered to let me borrow one of her dresses, I was a little taken back. It seems that she did own some feminine clothes (even if she didn’t wear them), and they were hanging in her mother’s closet. I agreed immediately, and we set up a time and date to meet. She promised not to tell her husband anything about what we were going to do.

That morning I walked into the huge master bedroom, wonderfully decorated with a feminine touch. The windows where adorned with frilly, white curtains that matched the deep, shagged rug. On one side of the room was the king-size bed covered with a thick, pink and white quilt. Off to the side was a large, oak wood dresser with 4 large drawers – no doubt packed with feminine delights. There was also a dainty vanity with a large mirror. On top of the vanity were several bottles of nail polish, perfume, and other odds and ends scattered about.

Patty opened the closet door, and I almost gasped in excitement at what I saw. Long, flowing dresses in various feminine patterns; short and sexy skirts in different colors, and rows upon rows of high heel shoes – all begging to be worn. My knees went weak as she started pushing aside the feminine outfits to reach her stuff. It took all my strength not to rush over and touch each item of womanhood. Finally she pulled out a long, pink dress with a high collar decorated in white lace.

"I wore this to the prom," she stated proudly. Frankly, I was a little disappointed in the outfit. True, it was feminine, but not overly so. It had long sleeves and was made out of polyester, not the silky material I had hoped for. Compared to some of the other dresses in her mother’s closet, it was very drab.

"It looks fine," I lied nervously. I didn’t want to raise any suspicions by suggesting I try on something more girlish.

"Good," she smiled, while laying the dress down in a nearby chair. She went over her mother’s dresser, and pulled out a pair of nude pantyhose and a white bra.

"Take off your shirt," Patty ordered, as she turned on the radio. Soft music flooded the room, and I suspected she did this to calm my nerves.

I striped off my shirt, and she proceeded to put the bra around my chest. This embarrassed me a little, but Patty just giggled and stuffed a few socks into the cups. Then she placed the dress over my head and pulled it in place. However, there was a problem when she tried to zip the dress up.

"Too much boobs," she laughed, while removing some of the socks. Her mother was a ‘C’ or ‘D’ cup, while Patty couldn’t have been more then a full ‘A’. After removing some of the padding the dress zipped up just fine.

I put on the wig that I had brought with me – something I told Patty I had borrowed from another friend. It was dark brown with curls in the back that hung slightly past my shoulders. It wasn’t the best wig to wear, but it did make me look passable.

I took off my pants and started rolling the pantyhose up my legs. Patty smiled in amusement as she watched. She seemed to get a real kick out of the fact that a boy would be wearing pantyhose, something so feminine that she wouldn’t wear them.

"Not too bad," she chimed looking up and down at me. There was a free- standing mirror in the corner that I observed myself in. I had to agree that I did look okay.

"Let’s work on your face," she half-giggled while sitting me in the vanity chair. She got down on her knees and carefully applied the foundation, blush, pink eye shadow, mascara, and pink lipstick. When Patty was done she stood back and smiled.

"Wow, you look pretty good," she laughed. "Better than I looked in that dress."

"I find that hard to believe," I joked while standing up. I stared at myself in the mirror while Patty went looking for some shoes. She was able to find a pink pair that actually fit rather well. I turned and looked at myself in the mirror from each angle. I was on cloud nine.

The sound of high heels clicking in the hallway quickly brought me back down to earth. I glanced over at Patty, who seemed just as surprise as I was. I made a move for my clothes but it was too late, Patty’s mother came walking into the room.

"Hi girls," she said casually.

Mrs. Bedford was a lovely lady in her mid-forties. Her hair was honey-blonde and hung just above her shoulders, but was cut in a very feminine style. She was wearing a dark red skirt that hung just above her knees, and a matching jacket. Her blouse was off white with some lace going down the front. It was also rather tight, showing off her large breasts. On her feet she wore a pair of two-inch heels – lovely shoes that screamed out ‘female’. The older woman gave me a big smile, and I quickly looked away.

"Mom," Patty asked in surprise. "What are you doing home? I thought you had to work today."

"We weren’t busy at the store so I volunteered to go home. What are you girls up to?" I could see Mrs. Bedford reflection in the mirror as she carefully checked me out from head to toe. I continued looking away in fright and panic.

"I was just letting, um, Stacy, try on my old prom dress. She was wondering how it would feel to be dressed this way," Patty half-giggled. I almost cursed at her reaction – she was blowing my cover.

"Not ‘another’ tomboy," her mother protested humorously. "What is it about you girls? Would it kill you to wear a dress once in a while?"

"Come on, mom, I wear makeup," Patty countered.

"Yes, well, it wouldn’t hurt for you to put on a dress now and then," she stated. "You too, Stacy – you look real nice in that dress." She stopped talking for a moment, and I could see the puzzlement on her face in the mirror. "Why is your friend looking away from me?"

"Stacy’s just shy," Patty tried to explain. "I put some makeup on her, and she doesn’t think if it looks very good."

Her mother giggled this time. "Come on, Stacy, let me see how bad it is." I found a hand reaching underneath my chin and gently turning it toward her. I looked at her with fear, and she smiled back.

"It’s not so bad – at least not the train wreak you think it is, Stacy." Mrs. Bedford smiled again, and let go of my chin. "Well, if you girls will excuse me, I need to change."

"But I…" I started to protest then stopped. Her mother looked at me strangely.

"Is there a problem?" she asked.

"I…I need to change," I stated in a low voice, which didn’t sound right.

"You can change in the bathroom," she replied, looking at me very carefully now. "Where are your clothes, dear?

I pointed to the pile of clothes near the bed, and she went over to retrieve them. Patty stood there silently with a silly grin on her face. She didn’t know what to do or say to fix the problem, and was having too much fun to care. Her mother picked up my clothes and looked at them.

"These look like boy’s jeans and a belt," she stated. "Why are you wearing boy clothes, Stacy?"

"I um, I…" I stuttered nervously. Mrs. Bedford smiled slightly as if she understood.

"You know, it’s silly for you to leave," she declared. "After all, we’ll all ‘girls’ here, right? Go ahead and change, Stacy, I don’t mind. Here, let me help you with the zipper."

Before she could get behind me, I put my back against the wall. Patty couldn’t take it anymore, and started laughing out loud. Mrs. Bedford was also grinning, and for a moment I thought she was going to start cracking up too.

"Okay, ‘girls’, what’s going on?" she asked humorously.

"Well, Steve has to go to a Halloween party dressed as a girl, and I told him he could borrow one of my dresses," Patty explained.

"You mean your ‘only’ dress," Mrs. Bedford corrected. "So he has to go to this party dressed as a girl, does he?" she questioned.

"Well, it’s something like that," I told her nervously. I was terrified that she would get mad and call my parents.

"Well, why didn’t you say so," Mrs. Bedford said. "I can help you find an outfit to wear, Steve!" She said it in such a way that I knew I was in trouble. Patty seemed to know it too, and began to laugh again.

"You’re not really going to do that, are you mom?" Patty asked with a chuckle. Mrs. Bedford looked at her with a pleasant smile.

"Patty, why don’t you go downstairs and wait for us. We’ll be down in a little bit."

Patty giggled some more as she left. I tried to think of something to say, but frankly I was too afraid to come up with anything. Mrs. Bedford didn’t appear to be angry, but that didn’t mean things would change. She closed the bedroom door and motioned me to take a seat on the bed.

"You really don’t have to go to a party dressed as a girl, do you?" she asked softly, while sitting down next to me.

"Well, no, I…I guess not." The older woman smiled at my nervousness.

"I want you to be honest here, Steve. You like dressing up as a girl, don’t you?"

"No, I don’t," I lied. "I just…wanted to…to…" I swallowed hard as she continued to stare at me with just a tad of concern. I didn’t have to say anything; she knew the truth. I looked down at the ground ashamed. At that moment I wanted to crawl into a hole and disappear forever.

"Please don’t call my parents," I begged softly. "Please."

"I won’t," she promised. "I’m not mad at you, Steve. If you want to know the truth, you had me fooled for a moment. It was only when I heard you talked, added with your strange behavior, that I knew you were a boy."

Mrs. Bedford sighed slightly. "I wish you were a girl, because I would love to dress you up in some of my outfits. Nothing would please me more than to turn a tomboy into a radiant, young woman. Patty won’t even talk to me about dresses, let alone try one on. It’s always been my dream to have a nice, feminine daughter in the family."

"Great," I muttered. "It’s always been my dream to have a mother who would dress me up as one. Life is unfair."

"Yes, and then again…" She stopped and smiled slightly as an idea popped into her head – the same one that was floating around in my head.

"Steve," she asked gently. "Would you be willing to…to be my daughter for a day?"

My mouth went dry when I heard the words. At that point I hadn’t even admitted to her that I liked dressing up as a girl, although I knew she knew. It was all pretty obvious by now.

"I…I don’t know."

‘YOU IDIOT!’ I screamed to myself. ‘Of course you would agree to be her daughter for a day. This was a dream come true. You’re blowing it.’

"Sorry, it was a silly idea," Mrs. Bedford replied. She patted me on the knee and started to get up.

"Wait…I’ll…I’ll do it." My reply sounded more like a frantic plea. I closed my eyes and waited for her to start screaming at me like my mother did. However, no harsh words came out of her mouth. She placed her hand on my back and patted it gently. I found it very comforting.

"Don’t be ashamed, Steve," she said in a low, understanding tone. "I’m…I’m actually going to enjoy this as much as you are. You really do look pretty in that outfit."

"Really?" I asked, still staring at the floor.

She pulled up my chin and smiled. "Really. Now, let’s see what I can find for you to wear."

Mrs. Bedford rose and walked over to her closet. She started searching through her lovely, feminine things for something that would work. I watched in awe as she went through her pretty clothes. Finally she came back holding a black, turtleneck sweater, and a tan, black, and white plaid skirt.

"This should do for starters," Mrs. Bedford smiled. She placed the clothing on the chair and turned to her drawer. From there she pulled out a pair of panties, a white lacy half-slip, and a pair of off-black pantyhose.

"Let me help you out of this dress, Steve – um, I mean Stacy. You don’t mind me calling you Stacy, do you?"

I told her Stacy was fine, since it didn’t sound right calling me Steve. I didn’t have a girl’s name picked out back then (Kelly wouldn’t come into my life for another 10 years). Mrs. Bedford unzipped the dress and started to help pull it off me. I panicked.

‘My panties!’ I said to myself. I had worn a pair of pink panties underneath my clothes, and she was about to see them. I grabbed hold of the dress to stop her.

"What’s wrong?" she asked in concern

"I um…" I couldn’t come up with a good answer. "Well, you see Mrs. Bedford…there’s something I don’t want you to see." I turned bright red with embarrassment.

"Let me guess," she smiled, and placed her hand inside the dress. Before I could do anything, Mrs. Bedford had her hand on the back of my nylon panties. She patted them gently a few times.

"You’re embarrassed about me seeing you in these, right?" I swallowed hard and nodded.

"Don’t be," she reassured me with a smile. "It’s just underwear to me. I guess you won’t need these." She tossed her own panties aside. "Now, let’s get you undressed."

Mrs. Bedford helped me out of the prom dress, and didn’t blink an eye as I stood there in my bra and panties. I took off the other pair of pantyhose and started putting the new pair on. While I was rolling on the other pair, Mrs. Bedford was busy looking in her jewelry case. When I got the pantyhose on, she handed me the lacy slip. I stepped into it, and slowly pulled it up my body

"You look pretty," she observed. "Lets get you dressed in this skirt and sweater now."

She handed me the skirt, which was short and hung a full two inches above my knee. I stepped into it and reached behind to zip it up, but Mrs. Bedford insisted that she do it. I felt her zip the skirt up and tug at it a few times to be sure it was in place. Then she handed me the sweater, and I pulled it over my head.

"Very nice," she smiled. "We need to fix your makeup and add some accessories. If there’s one thing you’re going to learn about being a girl, Stacy, it’s that women love to accessorize."

She sat me down at her vanity table and went to work. Patty had done a pretty good job with my makeup, so she didn’t really do much other than touch it up some. She added some red lipstick, and a little bit more blush to my cheeks. Next she attached several gold chains around my neck, and one for my ankle. She even found a few rings for my fingers, and a small, delicate watch for my wrist.

"I don’t have any clip earrings for you to wear," she stated rather sadly. "We’ll work on that. Let’s see, what else do you need?"

Mrs. Bedford went to her closet and came back with pair of black, one-inch heels with gold markings. She also had a solid tan jacket that went well with the skirt, and was stylishly cut. When I put it on I felt so complete.

"You still need a purse," Mrs. Bedford said, and went back to her closet again. She pulled out three of them, all black, but of various sizes. Finally she decided on a purse that was of a modest size – big enough to hold all my makeup and then some.

"You look – lovely," she smiled as I slid my feet into her shoes. They were a tad tight, but manageable. "I still need to do something with your hair though.

She picked up a brush and told me to take a seat at the vanity table again. I watched in the mirror as she worked on my wig, bringing out the curls and making it appear more natural.

"The first thing you need to do is learn how to sit properly," Mrs. Bedford told me while she brushed away. "Make sure you cross your legs whenever you sit, either at the knees or ankles."

I lifted my right leg over my left knee, and this seemed to please her greatly. I have to admit it made me feel more like a girl. Not only did I look like a young woman; I was now acting like one too.

"Let’s see, a couple of more things," she expounded after my hair was done. Mrs. Bedford pulled a colorful scarf from one of the vanity drawers and wrapped it around my neck.

Better wear this," she added, while placing a black, stylish hat on top of my head. "It’s cold outside. Okay Stacy, look at yourself in the mirror and tell me what you think."

The mirror revealed a hidden woman inside that I had never seen before. I looked good, even cute. I turned back and forth so I could see myself from all angles.

"I…I can’t believe that is me," I stated in shock. It was my first good look at what kind of girl I would have been if I had been born a female.

"It’s you, dear," Mrs. Bedford told me sweetly. "You’re very pretty."

She seemed to understand how I was feeling, and allowed me to stand there for a few minutes observing my refection. I was on an emotional roller coaster, and I had to fight back the tears. I was beautiful! I was no longer that ugly male person people made fun off. Here I could start a new life, and I found myself wanting to be dressed like this all the time.

"Let’s go downstairs," Mrs. Bedford smiled lovingly, as if she understood. Patty was waiting for us in the living room, and when she saw me all dressed this way she started laughing hysterically.

"Oh man, are you all dolled up," she giggled continuously.

I acted embarrass by her teasing, but inside it didn’t bother me. I was enjoying the idea of being all ‘dolled up’ and having people admire me. I was happy, gloriously happy.

"Ignore my daughter," Mrs. Bedford told me sweetly while pushing me into the room. "She’s just jealous at how pretty you look."

"No I’m not, mom," she giggled. "He looks good – too good. He looks like a real girl."

"That was the point," her mother replied. "You know, I could help you look this way too, Patty. It would really make me happy to find you something to wear."

"No thanks, mom," Patty replied. "You know I don’t like wearing dresses."

"Yes, I know," she stated rather sadly. "I suppose we better take you home now."

"You mean, he’s going with us dressed like that?" she asked a little surprised.

"What’s wrong with the way he’s dressed," her mother answer firmly. "Yes, he’s going out like that. It’ll take too long for him to change back into Steve, so he can do so after we drop you off. Now grab your coat."

Patty snickered some more as she put on her gender-less, gray jacket. Mrs. Bedford went to the closet and pulled out a black, simulated fur coat for me to wear. She held it open so I could place my arms into it. Even though it was a winter coat, it wasn’t very long and didn’t cover the skirt I was wearing. When we stepped outside I could feel the chilly air attacking my legs and rushing up my skirt. I was in heaven.

The trip to Patty’s apartment was uneventful. I sat in the front seat, my cold legs soaking up the warm air from the car heater. Patty giggled at me one more time as she got out, and went inside her apartment. Mrs. Bedford put the car back into drive and drove off – only not in the direction of her house.

"Where…where are we going?" I asked nervously. "Your house is the other way."

"Yes, I know," she smiled, while stopping at a traffic light. "We still need to get you some ear-rings to go with the outfits I’m going to have you try on. I was thinking of the ear ring store at the mall."

"The mall!" I gasped. "I can’t go there dressed like this, Mrs. Bedford."

"Okay, new rules," she told me firmly. "First of all, you will call me mom from now on. You’re my daughter, and you will respect me. Second, you are going into the mall with me. This is as much my fantasy as it is yours. A mother and her lovely daughter out shopping; it’s what I’ve dreamed of doing since Patty was born. Unfortunately, that’s not going to happen with her. However, with you it’s a different story."

"But…but what happens if people find out?" I asked in a scared voice.

"Smile real pretty and they won’t," Mrs. Bedford replied in a matter-of-fact tone. "Let me do all the talking. I can explain that you have laryngitis and can’t talk. If you follow my instructions, no one will know."

I sat there a little frighten by the change in her demeanor. All of the sudden she didn’t appear to be as sweet and understanding as before. My new mother was the one in charge, and I was going to go into the mall whether I wanted to or not. It made me wonder what else she was going to have me do.

There was tension in the car, and she eased up by changing her tone. "Relax Stacy, we’re going to have a great time. Just take deep breaths and remember what I told you."

We pulled into the mall parking lot, and Mrs. Bedford found a spot not far from the entrance. I clumsily lifted my purse onto my shoulder, and found myself getting out of the car against my better judgement. Nervously, I joined Mrs. Bedford at the back of the car, and watched a young lady walk by carrying a bag. She smiled at us in a very normal way and kept walking.

"See," Mrs. Bedford told me, as she grabbed my arm and pulled me toward the mall. "She didn’t see anything out of the ordinary. To her we’re just a couple of girls out shopping. Now relax and be yourself, ‘young lady’."

The sound of our clicking heels seemed to radiate throughout the mall as we walked inside. After removing our coats, Mrs. Bedford led me to a small store that sold earrings and other types of jewelry. The saleslady smiled as my mother started picking out several ‘clipped’ earrings for me to wear.

"You really should get your ears rings pierce, Stacy" she told me as the saleswoman rang up our purchases. The sales lady was around my age and had long, blonde hair. She was wearing an attractive blouse/skirt outfit, and I found myself wondering how I would’ve looked wearing it.

"Come on, Stacy," my new mother said cheerfully as she dragged me out of the store. "Let’s go look at some new purses." And look we did.

Over the next two hours we went from one store to the next, window shopping for clothes, shoes, and other odds and end. I noticed a few people looking at me, mostly young men, but for the most part people paid very little attention. In some ways, I felt disappointed from the lack of attention I was given. On the other hand, knowing that no one was pointing and laughing at me made me feel more relaxed, and allowed me to be myself.

Mrs. Bedford talked continuously about a number of things as we checked out the numerous sales going on. I found myself joining in on the conversation now and then when no one was around; replying back in the best female voice I could muster. We looked at some dresses, and commented on which ones we thought were the prettiest. We cooed at the lovely purses hanging on the stands, and the shinny jewelry in their glass cases. But the part I loved the most was the sound of my heels clicking on the hard floor as I walked. Oh, how wonderful it sounded. However, by lunchtime my feet were killing me.

"Let’s have some lunch," Mrs. Bedford suggested as we passed a sandwich shop. The place was crowded from the lunchtime crowd, and we had to wait in line with other people around us. I felt scared surrounded by other people, and I listened carefully for the dread words of someone saying, "that’s a man in that dress!" No one did, and finally the server called our name.

"Right this way, ladies," she said cheerfully with a smile. I followed her to our table with Mrs. Bedford walking far behind. My heels clicked loudly, and announced my femininity to everyone. We took our seat in the middle of the restaurant and ordered.

"I think there’s someone interested in you," Mrs. Bedford said with amusement.

"Who?" I asked in a panicked tone.

"Just a couple of teenage boys at the next table," she whispered back. "Don’t worry, they look harmless enough. I noticed them checking you out as we came in."

"I hope they don’t come over," I replied nervously in a low whisper.

"They won’t," she smiled. "Relax, you look great, Stacy."

I tried, but it wasn’t easy, especially since I had to go to the bathroom real badly. Finally I couldn’t stand it any longer.

"Mom, I got a problem," I told her.

"What is it?" she asked.

"I need…I need to go."

She stared at me for a moment, and a thin smile appeared on her lips. "Grab your purse and follow me."

We got up together, and she led me to a door with a female figure adorned to it. I balked for a moment when I saw where she was leading me.

"It’s okay," she whispered into my ear. "Just remember to sit down when you go."

She opened the door and pushed me inside. There were already two ladies in the bathroom, one applying makeup and the other washing her hands. Neither of them paid any attention to us. I turned and headed for the closest open stall. I closed the door and went to my business. My fear was forgotten for the moment with the passing relief of emptying my bladder. After I was done, I struggled within the small confines of the bathroom stall to redress myself. I waited until I heard Mrs. Bedford leaving her stall before I exited.

"Wash your hands," she told me just before three more ladies walked into the room. They smiled; one even said hello to us, as they went to their task. I wanted to leave, by my mother insisted that we work on our makeup together. As I applied some more lipstick, one of the ladies exited her stall and started washing her hands in the sink next to me. I kept thinking to myself how wonderful it was to be surrounded by all these beautiful women, and be treated as one of them. The woman tugged on her skirt a few times, gave me a quick, friendly smile, and left without being the wiser to the situation.

After lunch, Mrs. Bedford drove us home. I spent the rest of the afternoon trying on her clothes – and what wonderful clothes she owned. Dresses of every color and style you could imagine. Skirts, both short and long, that matched up perfectly with her stylish blouses. And then there was her underwear, from her lacy half-slips and bras, to her full-slips that came in colors of white, black, red, and blue. All feminine, and all waiting for me to try on. When Mrs. Bedford found an outfit she thought I looked really good in, she would take me downstairs and make me practice walking around in it. Sometimes we would sit and chat for a while over a coke; then we would go back upstairs so I could try on something else. I was in heaven.

As evening approached, she allowed me to pick out the outfit that I had liked the best. That turned out to be a blue and white dress with puffed sleeves, and lace around the hem and collar. It’s kind of hard to describe, but it was the most feminine dress I had ever worn.

Mrs. Bedford worked carefully on my makeup and jewelry so I looked perfect, and gave me a pair of her white shoes with blue markings to wear. The shoes matched the dress, and she told me that she had purchased them just for this outfit. There was even a white purse and sweater to complete the outfit.

Mrs. Bedford added some blue clips to my hair, and painted my nails red. Then she sent me downstairs so she could change. Almost an hour later she reappeared wearing a stunning, black dress with dark hose, and black, 3-inch heels. My knees went weak when I saw her coming down the steps looking as lovely as any woman could.

"Bet you didn’t know your mother could look so good, did you?" she said happily.

"You’re beautiful," I gasped, my young hormones starting to kick in. She smiled at the compliment and handed me a coat. As we left the house, she explained we were going to a nice restaurant. This time I felt a little at ease about the idea, although the butterflies of being out in public never did go away.

‘David’s house’ was a rather charming and expensive restaurant. It was certainly well above anything I could have afforded at the time. There was a fireplace in the middle of the room, surrounded by sturdy wood tables with candles burning on top of them. Overhead you could hear soft music playing. It was very elegant, and also very romantic. I protested slightly, but Mrs. Bedford smiled and told me this is what she wanted.

The greeter led us to our table, and I felt so special when he held out my chair and pushed it in for me. He handed us a menu, and I taken back at the prices. Mrs. Bedford told me not to worry, that this was her treat and I should get what I wanted. I ended up ordering a bowl of soup and the grill chicken, with a side salad. During dinner Mrs. Bedford talked about herself. I found out she had been divorced for almost two years, after her husband had left her for a younger woman. I also felt a twinge of jealousy as she talked about her current boyfriend. A couple of times I brought something up, but for the most part it was a one sided conversation.

After dinner she drove us home and led me back upstairs to her bedroom. There was almost a sort of nervousness in her demeanor as she sat me on the bed. She gave me a tense smile and said, "Stacy, I…I was wondering if you would try something on for me. I’ve been waiting for this moment for so long…I just don’t know if you can handle it. Can I show you the dress I have in mind?"

I nodded it was okay, and Mrs. Bedford got up and walked over to the closet. From the upper shelve she pulled out a large, brown box tied up in string. She blew off some of the dust and gently set the box on the bed. My eyes were bulging, as I had a pretty good idea what was inside. Slowly she untied the string and lifted off the top. Inside was one of the prettiest dresses I had even seen. It was pure white, with flower lace across the sleeves, waist, and collar. Attached to the back was a large, white bow.

"Are you okay?" Mrs. Bedford asked when she saw the expression on my face. To be honest, I wasn’t sure. My face felt flush, and my body was numb. My biggest, wildest dreams were about to come true. I almost started to cry.

"Stacy, are you okay?" she asked again. I nodded that I was.

"What’s wrong?" she wanted to know, now rather concerned.

"It’s…so…beautiful," I replied, reaching out to touch it. I stopped just before I did.

"It’s okay," she giggled in a relieved manner. "Go ahead, touch it if you want. It was my wedding dress. I always dreamed of my daughter wearing it on her wedding day. Unfortunately, Patty wouldn’t be caught dead in a dress like this. I’m glad you like it."

I swallowed hard as I ran my fingers over the cool, silky skirt that felt so wonderful. I could only imagine how grand it would feel when I put it on.

"I have everything you need," Mrs. Bedford explained as she went back to the closet. "The petticoat, the veil, my white silk gloves. I can’t wait to see you wearing them." Her voice indicated a lot of excitement and emotion in the last sentence.

While I continued to sit there fondling the dress, Mrs. Bedford was busy pulling out the things I would need. The veil had been placed in it’s own box, and Mrs. Bedford meticulously took it out and placed it on the bed. A bulging, white petticoat was carefully thrown across the chair. A pair of white high heel shoes was placed on the floor so I could step into them.

She motioned for me to stand, and I removed all my clothes except for the bra, pantyhose, and panties. Mrs. Bedford placed the petticoat on the floor and told me to step into it. I did as she ordered, but when I bent down to pick it up she stopped me.

"Please, let me have the honor," she insisted. Carefully she lifted it up around my waist and fluffed it out.

As I stood there admiring the look and feel of the silky, fluffy petticoat, Mrs. Bedford opened up a drawer and pulled out a pretty camisole. She placed it over my head and slowly pulled it down.

"Perfect," she smiled. "Take off your wig so we can get the dress on."

Reluctantly I did as she asked. I was slightly embarrassed, because the last thing I wanted to do was appear as a man in drag to her. Mrs. Bedford didn’t pay any attention to the fact. She carefully positioned the dress over my head and slid it down.

"We really need to have two people doing this," she explained as she struggled with it. After a moment or two I felt it being slipped over my body. She tugged on the dress a few times to pull it all the way down then zipped it up. Fortunately the wedding gown fit rather well on me. Mrs. Bedford helped me move forward so I could step into my shoes.

After my wig was put back in place, Mrs. Bedford picked up the veil and placed it on my head. I noticed her hands were shaking as she did so, and when she stepped back to look there were tears in her eyes.

"You look so beautiful," she almost cried.

Seeing that she seemed upset, I held out my arms out of reaction. I was a little shock to see her actually come forward and hug me. I placed my hands on her back and closed my eyes in joy – in complete joy. I didn’t want this moment to end. Finally it did, and she sniffed a few times and stepped back.

"Let’s get the rest of your things," she said.

Mrs. Bedford added her white gloves and a gold cross necklace to the outfit. After touching up my makeup, she helped me downstairs and got out her sewing kit.

"We’ll need to make some alterations," she explained, while placing some pins in the dress.

A knock at the door interrupted her work, and she rushed around the corner to answer it. I heard someone talking, and then the sound of shoes walking my way. I panicked and thought about running, but the only way out of the room was where the noise was coming from.

Mrs. Bedford appeared in the entrance with another woman about her age. The other woman smiled brightly as she gazed at me.

"Oh my, she’s beautiful, Carol," the woman exclaimed.

A teenage girl, maybe about 13 years old, stuck her head around the corner and looked at me carefully. I smile nervously at her, and she smiled back.

"This is my niece, Stacy. Stacy, this is Mrs. Miller and her daughter, Helen. I’m sorry, Teresa, but Stacy has laryngitis and can’t talk very well."

"Oh, the poor dear," Mrs. Miller replied, while walking up to me. She reached over and pulled the skirt out, then let it drop back down. "It’s a very pretty dress, Carol. I bet you looked as lovely in it as Stacy does."

"Thanks, Teresa. Since you’re here, can you help me for a few minutes?" Mrs. Bedford asked. "I’m trying to pin the skirt up, but it’s so thick it’s very difficult to doing so. I could really use another set of hands."

"Why of course," Mrs. Miller beamed. The two ladies got down on their knees while the teenage girl continued to stare at me with a funny grin. I stood there shivering in my heels as they worked. It was obvious Mrs. Miller didn’t notice anything out of the ordinary, and I felt the girl thought it was kind of funny seeing some stranger standing there in a wedding dress. Still, this did little to relieve my fear of being found out.

Both ladies continued to fuss with the dress as they chatted about various things. The little girl finally got tired of staring at me, and picked up a book to read. After the two ladies got done pinning up my hem, they made me walk around the room a few times so they could see how the dress looked. They made a few more adjustments, then Mrs. Bedford gave them what they had come for and showed them to the door.

"Sorry, Stacy," she grinned mischievously after they had left. "I didn’t know they were coming over, but when they did I just couldn’t resist."

"It’s…it’s okay," I told her. "It just scared the crap out of me."

"I’m sorry," Mrs. Bedford said honestly. "Don’t worry, she didn’t suspect a thing."

My new mother stopped to look at me one more time, as if to get the image of me burned into her mind.

"You really are a good sport, Steve," she smiled. "You’ve made me very happy…I mean that."

"Well, it has been fun for me too," I replied meekly. It was my cue to go change, and I felt sad. That’s when I noticed tears forming in Mrs. Bedford’s eyes again, and she rushed over to hug me. I held on tight, wishing for the moment to never end as she pressed against the stiff, white dress and petticoat.

"Let’s go upstairs," she whispered into my ear.

I thought she meant we were going upstairs so I could change, but that wasn’t what she meant. When we got to her bedroom she immediately went to her dresser drawer, and pulled out someone black and silky.

"One more outfit," she smiled, holding it out to me. "If…if you don’t mind that is."

I held the silky nightgown in my shivering hands. My mouth went dry, and my mind kept asking over and over if the signals I was picking up were true.

"I…I don’t mind," I replied in a shaky voice.

"Let me help you with your dress," she offered.

Mrs. Bedford unzipped the wedding gown and pulled it off me. Then she helped me out of the petticoat and pointed to the master bathroom.

"Change in there," she told me as she handed me the nightgown, and a pair of her own silky panties.

My head was literally spinning as I got undressed and put on her panties. The nightie was short with black lace, and hung just above my knees. It excited me even more knowing Mrs. Bedford had worn this same nightgown to bed several times before. I took off the bra, but kept the wig on so I would have some appearance of being a female. I wasn’t sure what was going to happen next, but somehow I knew (hoped) that Mrs. Bedford wasn’t just interested in seeing how I looked in her nightie

I touched up my lips with some red lipstick that I found on the sink, straighten up the nightie by pulling down on the hem, then slowly opened the door. She was standing there, dressed in a short, blue nightie that was equally as sexy as the one she had given me. I became scared shitless – literally.

"Um, Mrs…Mrs…Bedford," I finally got out.

She smiled at my tenseness, but didn’t say a word. Instead she closed the bedroom door and flicked off the lights. In the dim light coming in from the windows, I could see her strolling towards me. Her hand touched mine, and she led me to the bed. My body was screaming ‘this is it’, but my mind kept wanting to deny what she had in mind. There had been no warning that she was interested in me – or had there been and had I simply missed the signals?

We got in the bed together, and she lay down behind me. Slowly she ran her hand up and down my side. I swallowed hard as I felt the silky nightgown caressing my skin, a definite turn on. The problem was, I didn’t know what to do. I was afraid I would do or say the wrong thing.

"Mrs…Mrs…Bedford." I said in a very nervous voice.

"Call me, Carol," she cooed. "What is it, Steve?"

"I’m…I’m kind of ne…new to this. I mean, I want to but…but…"

"You’re a virgin, aren’t you?" she stated softly, without any harshness to the words.

"Yes, I’m…I’m afraid so."

"Rollover and look at me," she said. I did, and could see the gentleness and concern in her eyes from the little light in the room. "It’s okay, Steve." She brushed her hand over my forehead in a loving manner. "We don’t have to do anything if you don’t want too."

"It’s not that," I sputtered out. "I’m just afraid that…that you may not en…enjoy…" I didn’t finish the sentence. God, I was acting like such an idiot, and blowing the moment big time.

"Steve," she replied gently. "Don’t worry about it. This isn’t a contest, and I’m not going to grade you afterwards. There always has to be a first time." She kissed me on the lips, and things started to heat up. "Now, just relax and let me teach you."

I would love to brag and say that my first time was wonderful, and I preformed like any young stud my age. The truth was, I felt clumsy and awkward at times. However, Mrs. Bedford was very patient with me, and that night I became a man. It’s kind of ironic that I was wearing one of the most feminine things a woman wears at the time.

Our second time was better, although not as enjoyable for me. Early in the morning, before the sun had even come up, she woke me, and told me to take a shower and get dressed. Her attitude was different, and I related that to my performance last night. I cursed myself for being so uninformed at pleasing a woman in bed, but I was about to get another lesson in life. When I came out of the bathroom she was sitting in her chair smoking a cigarette. A long, flannel robe had replaced her sexy nightgown.

"Steve, sit down please."

From her tone I knew this wasn’t going to be good, and I looked her with sad eyes. "I’m sorry," I told her.

"For what?" she asked in surprise.

"For last night. For not being…being very...good." I felt my self-esteem and ego draining away.

"Steve," she smiled slightly. "Last night was special for me; very, very special – and you were ‘wonderful’. If there’s anyone who should be sorry, it’s me. What I did last night was give into my desires, and that was wrong. I should have been stronger."

"I…I don’t understand. If you enjoyed what we did why…"

"Because it was wrong," she interrupted me. "You’re only 19, and I’m…well I’m old enough to be your mother. What you did by pretending to be my daughter made me feel so happy – complete. As a result, I wanted to get even closer to you – and that was wrong of me."

"But…but age shouldn’t matter with…with love." I stopped and wondered if that was true. Was it really love, or something else I had been searching for? Wasn’t it acceptance that I had found here? I wasn’t sure, and Mrs. Bedford wasn’t going to allow me to find out.

"You’ll understand one day," she stated sadly. "Please, don’t take this the wrong way, Steve; and please don’t be hurt by what I’m about to say next. Last night meant a lot. I mean that, Steve – I really do. But I can’t see you again. Please, never come back here again."

"Never?" I asked with tears in my eyes.

"I’m sorry, Steve, I know this hurts. One day you’ll find that right woman to spend the rest of your life with. I know you don’t want to believe this, but I’m not her. We can’t go on, and we shouldn’t try. Now please, just go."

I nodded, trying hard to hold back my tears. "Can I hug you just one more time?"

She hesitated for a moment, but then stood and held out her arms. I fell into those arms and embraced her tightly.

"One day you will find someone who’ll make you forget all about me," she whispered.

"I will never forget you," I whimpered back – and I never did.

I walked outside into the cold, morning air and got into my car. It was just after 5am, and with no placer better to go, I drove to my favorite spot. It was a lonely road next to some active railroad tracks. I arrived just in time to see a Norfolk and Southern freight train roared by pulling a load of auto parts. Like life, it was passing me by at a fast clip.

Something snapped inside me when I thought of that. I got very angry, and started yelling and screaming at the top of my lungs. I pounded the steering wheel with my fist in anger, cursing God for making me this way. Why had he seen fit to make me an unsure and lonely crossdresser, that no one supported or loved? WHY? It was so damn fucking unfair! There were people who were far worse than I was, and they had LIVES! They had people who LOVED them! I wasn’t a bad person, so why was I treated like SHIT all the time? Why was I so ALONE? I put my head against the steering wheel and bawled my eyes out.

There would be more nights like this, as my slide to the bottom would continue for six more years. Only when I touched bottom, when I could find no hope or reason to go on, would I find my life and a reason to live through Jesus Christ. Of course, that’s another story.

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Epilog: I never saw Mrs. Bedford again. Patty and my friend eventually got a divorce a couple of years later, and my relationship with them quickly tapered off until finally I lost contact with both of them. I often sit and wonder what happened to them, and if they’re both happy now.

Mrs. Bedford would be close to seventy today. The last time I drove by her house it had been sold to someone else. I wonder if she’s alive, and if she thinks of me from time to time. I guess its wishful thinking on my part.

In many ways this memory has been painful to relive, yet it’s also been a cleansing of my heart to write. I now understand what Mrs. Bedford was saying almost 25 years later. How I wish she hadn’t been right, but in the end she had done the right thing. She had ended something before it got any bigger, and messier. She had saved me from more pain and heartache. For that I will always be grateful.

 

 

 

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© 2001 by Kelly Davidson. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.