Karen's Story

When we left the store, I told her what had happened. She teased me about having made my first conquest and told me I should have given him our phone number.

This time she had a huge laugh when she saw the horrified look on my face. "You can't be serious," I replied. I couldn't date a boy. What would I do if he wanted to kiss me, or worse, if he wanted more? I'd be in big trouble."

"Look, Karen, you're going to spending a lot more time as a girl and if you think you'd like to date, it's certainly fine with me. There's no reason you can't. You can kiss and go as far as you like, as long as you don't drop your panties. Your breasts are not any smaller than a lot of other girls your age. A boy would never know the difference, believe me. As I recall from when I was a teenager, they're so happy to get anywhere at all, they don't even realize what they're doing. So relax and enjoy being a girl, will you please? I won't let you get into situations I don't think you could handle."

I was sure it would take a giant leap for me to adjust to being with a boy, but knew I would eventually like to. "I guess you're right, but I think it'll be a long time before I could date. It's not that I don't want to, but I don't think I could relax enough to enjoy myself. There's so much I need to learn first."

"I'll teach you all you need to know about boys, honey. They're so eager to get you in bed, it makes it a very simple matter to control them. Any girl with brains has no problem at all. I want you to be just like any other girl, that is if you truly want to be."

"Oh, Aunt Jeannie, I do. I really want to be a girl, in every sense of the word. I know you're right about boys, so if you'll teach me, I'll be a very willing student. Do you actually think it's possible for me to date?"

"Karen, you'll not only be able to date, but after I get through teaching you a few tricks, you'll have them eating out of your hand. You're now a beautiful young woman. It'll be easy for us to make you one of the more popular girls in town. Believe me, I know what I'm talking about. Your mother taught me all I know about men and she had a very special knack with them. You may have even inherited her talent."

We continued our shopping, stopping at the discount pharmacy to buy all the necessary feminine things I'd need if I was going to be spending a lot more time as a girl. We bought makeup, nail polish, shampoo, hair spray, big pink hair rollers, perfume and bath powder, a blow dryer, two more boxes of sanitary napkins and six more of the wide elastic sanitary belts. I'd never realized how many different things a girl needed to make herself pretty, but I was learning very fast.

Next we stopped and had a bite to eat at the restaurant in one of the big department stores. We both ordered a crab salad plate and iced tea. Again I had time to practice my ladylike manners. I made sure I kept my legs demurely crossed and tried, as best I could, to copy Aunt Jeannie's other mannerisms.

Jeannie must have noticed my efforts. She reached over and touched my hand. "I see you're being conscious of how you eat. Make sure you take nice little ladylike bites. This is part of your education as a young woman. You've never had the opportunity to learn a lot of things other girls your age have known for years so I'm going to make sure you have a chance to discover them, that is if you want to."

"Oh, yes, please, Aunt Jeannie. I want to be as much a girl as anyone else. I promise to be the best student in the world. I know I've got a lot to learn, especially about boys, so whenever you think I need to know something, please tell me."

"I will, and I'll try to make sure you know all about boys before too long. I've got the feeling you're going to need learn quickly, judging from the looks the boys have been giving you today. You really are a very pretty girl, and I'm not just saying that because you're my niece."

At that I blushed, not knowing how to handle flattery, but loving it all the same.

After we had eaten, I realized that I was in very serious trouble. I had to take a pee. When I finally mentioned it to Jeannie, she just smiled.

"Come with me," she said, smoothly and quite casually. "I have to go myself."

When I realized what she was suggesting, I was horrified. She laughed at the expression on my face and as we walked toward the powder room, and she told me something that was to become quite important to me.

"You're a girl now," she said, "so when nature calls, you'll just have do the same thing the other girls do. You'll learn."

"You can't mean I should use the ladies' bathroom," I stammered. "I'd never be able to walk in there. I'd faint, I know I would. Please, let's just go home before I burst."

"Karen, I've told you at least a dozen times today you can do anything, go anywhere you want. Absolutely no one is going to realize you're not completely female without seeing you in the nude. You've got to stop being so paranoid. Now follow me. I have to go too, so let's just get it over with."

"Ok, but I want you to know I'm scared to death," I admitted. "Please let's get in and out of there as fast as we can. From now on, I'm going to make sure I go before we leave the house."

As we entered the powder room I began to tremble and, while I had a smile on my face, it felt like it was pasted there and wasn't working too well. There were several women standing in the outer room, but Jeannie and I ignored them and went into the room where the facilities we needed were. There were several toilets in little stalls with the door that could be pushed closed.

I ran into one of the empty stalls, locking the door securely behind me. I hung my coat and purse on the door hook, then used some paper to clean off the seat. I quickly lifted up my skirt and slid my panties down as far as the tops of my stockings. I carefully sat down, all the time watching the door to be sure no one was spying on me. When I was satisfied that no one was watching, I slipped my cock out from under the sanitary napkin and quickly peed. What a relief!

When I'd finished, I patted myself dry with some paper, then pushed my penis back under the napkin, feeling so much safer with it hidden. I stood up, pulled up my panties, again being thrilled with feeling so feminine. I dropped my slip and skirt back into place after adjusting my stockings.

Finally, I sensed I was gaining some self assurance. I thought about how no one had given me any strange looks all day. On the contrary, all the looks I'd received had been very flattering. I decided Jeannie had been right all along. I'd been silly to doubt my appearance.

As I'd been warm all day wearing my coat inside the mall, I now decided I'd carry it. Before I'd felt too self-conscious to take it off. It was, I decided, time to be brave. I was starting to enjoy myself for the first time that day. I was now a real girl. I knew it, no one else seemed to doubt it, so I might as well enjoy it. What a phenomenal feeling!

I strolled out to the mirrors and checked out my appearance, just as most of the other women there were doing. What a pleasant picture. I loved my feminine reflection. I couldn't remember any time in my life I'd ever felt better.

I fussed a little with my hair, then went and sat in one of the chairs to wait for Jeannie. It was even fun just sitting there, crossing and uncrossing my legs, feeling the slippery smoothness of my stocking clad legs as they rubbed against one another, and it was especially wonderful that there was no longer any ugly bulge to get in the way. How I loved being a girl!

I noticed how nicely the room had been decorated. The walls were papered with soft pink flowers on white background. The carpet and chairs were a light gray. So pretty and so unlike the men's rooms I'd been in.

When Jeannie finally came out, she immediately noticed me sitting there looking like the cat that had eaten the canary. She gave me a radiant smile and, when she's finished washing her hands, we walked out together.

"What's come over you, Karen?" she asked. "You're acting like you own the world now."

"I guess when I had time to think about what you've been telling me, I realized how right you were. No one all day has treated me any differently than they treated you. I just love being a girl and now I think I finally beginning to relax and enjoy being Karen. Thanks for being so helpful, Aunt Jeannie. I want you to know I love you, and I really appreciate all the effort and expense you've gone to. You're the best friend and the best aunt anyone ever had."

I could tell she was pleased. "You're a very good nephew as well. Whoops, I better make that niece in the future." We both laughed at that.

We continued our shopping, buying me all the pretty things that Jeannie had promised. I had such fun picking out a whole new wardrobe. All the pretty lingerie, dresses, jewelry, shoes and hosiery. I was in seventh heaven. I guess the main reason we stopped shopping was that we couldn't carry any more boxes.

By the time we arrived home, I was dying to get into the house and try on all my pretty new things. Jeannie and I carried everything into my bedroom. I couldn't believe all the boxes and bags. It was going to take hours just to put everything away, much less try them on.

Jeannie left me to play and experiment while she went and started dinner. We had a fabulous meal, special because Aunt Jeannie felt this had to be a extraordinary day for me. She let me have wine with dinner and we just sat at the table when we were done, drinking coffee and talking, reliving our day.

"Karen, honey," she said, "this truly was a terrific day. You know, I feel as if you've been a girl all along. I guess I'm more comfortable with you as Karen than I ever was with Chuck. Somehow you never seemed at ease with yourself or with me before. Are you happier now?"

"I know I'm happier," I answered, quite honestly, "but today has given me so many things to think about. I'm a little scared about the future. Do you know what I mean? If I'm really more female than male, I'm going to have a lot of problems to solve. I'm going to need your help now more than ever."

"You know I'll always be around to help you," she said, "so don't worry. We'll work everything out, you'll see. If you decide you want to be a girl all the time, then we'll simply register you in another school as Karen. That will be easy. I know people who can get any kind of identification we'd need. If you're sure at some point that you'd like to consider a sex change, we'll explore that possibility, too. So why don't you just relax and enjoy being your new self."

"I will," I explained. "It's just that I just need some time to get used to all these changes and to learn more about being a woman. Once I do, I'll have to think more about what the future holds."

"That's the idea. Now scoot. Go and try on the rest of your new clothes. It's already late, so you'll have to hurry if you want to finish before bedtime."

I didn't need any more encouragement. I went to my room and spent the next hour or so trying on the rest of my new outfits, rushing back into the living room and modeling each of them for Aunt Jeannie.

All in all, we had bought six dresses, four sweater and skirt combinations, seven blouses, two pairs of pants, six pairs of shoes, two blazers, a coat, three handbags, five bras, twelve pairs of panties, three full slips, a half slip, a camisole and matching tap panties, a gorgeous pink silk teddy, two garter belts, three nighties, six pairs of pantyhose, four pairs of stockings and all kinds of scarves, jewelry and makeup.

Parading around in front of Jeannie in all my new fashions was, to me, the perfect end to a perfect day. Everything seemed to fit well, except for a skirt which needed shortening. Jeannie told me I should wear short skirts because, when a girl has legs like mine, she should show them.

Gradually I was learning the feminine art of walking in high heels. I was also learning how, with many suggestions from Jeannie, to properly accessorize my outfits. What jewelry for dressy occasions, how to coordinate shoes, or what shade of eye shadow went with each color and style.

The last thing I modeled was my new very sexy peach negligee with matching bikini panties. Jeannie insisted I keep it on.

"Karen, I'm not ever going to let you sleep in anything other than a pretty nightie," she said as I twirled before her. "I always hated those pajamas you used to wear. You look so cute now. Do me a favor and throw out all those pajamas tomorrow."

I went over and gave her a hug. "I will, I promise. I hate them, too. Please don't ever make me wear any of those dumb clothes again. I know I'll be much happier as a girl, you'll see."

She held me in her arms and said softly in my ear, "I already know that. I just love the way you feel in this nightie and your perfume smells so good."

Her hands moved down my back, gently caressing me through the silky fabric until she reached my panties. She slipped her hand inside the waist band, softly kneading my buttocks. Even though I was tired, I immediately became erect under the sanitary pad. I pressed my pubic bone into hers, lightly kissing her on the neck.

"Karen, it's about time you learned more about women. I'm going to give you some first hand experience on how a woman makes love. Give me just a moment to change into my nightgown, then we'll get in my bed. I'll show you how a woman likes her loving. Do you think you're ready for that?"

I just shook my head, letting her know I was willing. I was too excited to talk. We went into her bedroom, turned down the bed and then I got in.

Jeannie slowly undressed, knowing very well that my eyes never left her for a moment. She unzipped her dress and let it fall to the floor. She slid the straps of her slip off her shoulders and let it fall around her ankles. The sight of her in her bra and panties almost made me come. She turned toward me as she reached back to unhook her bra. Her bra slide down her arms and she smiled at me as I stared at her breasts. They were perfect, not too large and perfectly shaped. Her nipples were as erect as my penis. I couldn't wait to touch them.

She walked over to her dresser, wearing only almost transparent pale yellow panties, and got out her nightie. Then she came over to my side of the bed, laying the gown on the bed next to me.

"Karen, I want you to finish getting me ready for bed. Take off my panties for me and then help me get into my nightgown. I think you should pamper me a little tonight. After all, we spent the whole day doing things for you. Now it's my turn."

"Oh, Aunt Jeannie, I always would do anything for you, but after today, I want to spoil you forever. You just tell me what you want and I'll do it, anything at all."

"Just get me undressed and into my gown. I can tell you're still wearing your sanitary belt and pad. You can take them off. We're going to be putting your penis to work shortly, so let it out of its cage."

I got out of bed and stood next to her. My heart was pounding. Although it seemed as if my arms were made of lead, I finally managed to move. She just stood there, smiling. I took hold of the elastic waist band of her panties and slowly slid them down her legs. I knelt in front of her as she stepped out of them.

I looked up to see her vagina a few inches from my face. I moved forward and kissed it, feeling her slit against my lips for the first time. The smell of her sex was addicting. It was all I could do to stand up and put her nightie on her.

My cock was very hard by this time, so I was glad to be able to take it out from under the sanitary napkin. I pulled my panties back up, barely covering my erect penis. The feel of the fragile silky fabric against it sent shivers through me.

I got into bed, letting Jeannie take the lead. She immediately took me in her arms, kissing me and delicately exploring my body. My hands roamed over her. I was amazed at her softness and suppleness. Our bodies pressed together, her hips slowly rocking her mons against me. I took her breast in my hand, feeling the stiff nipple. What wonderful things breasts are. How I wished they were mine!

"Karen, I'm going to make love to you now. I want you do as I tell you, and if there's anything you don't understand, ask me. If there's anything you'd like to try, we'll do it, but not now. Tonight I want to teach you all about my body and yours, how a man pleases a woman and how a woman pleases a man. You're going to have to learn both. Someday you may want to be able to please a man yourself."

With that, she kissed me again, slipping her hand down to stroke my erection through my panties. She had learned earlier how much I loved that. I needed no encouragement to follow suit. I trace her cunt lips with my fingertips, trying to remember her response to each caress. I wanted so badly to turn her on as much as she turned me on.

She finally sensed I was getting too excited. She slipped my panties down, then lowered her head and softly nibbled at the tip of my hard on.

"I want you to get on your back and then just relax. I'm going to get on top of you and put your penis in my vagina. Don't do anything. If we don't go slowly, you'll come right away. That's not what I want. I hope to keep you erect for a long time."

She placed me as she wanted, then straddled my hips. Very slowly she lowered herself on to my cock. As the tip touched her lips, I fought to control myself. It was incredible! When she'd finally inserted it all the way in, all my attempts at control weren't enough. I came and came, the throbbing seeming to concentrate all sensation in my cock and balls.

But fortunately I didn't lose my hard on. She stopped for a few minutes, leaving my cock inside her, and then went right at it again. This time I lasted for ten minutes and Jeannie was able to have several intense orgasms.

"Honey, you're a fast learner," she said. "We'll rest for a few minutes and then I want to teach you how to please a woman orally. It's the best way to make sure a lady enjoys herself, so I want you to be good at it. It's one of my favorite forms of sex. The best part about it is I can get satisfaction from either a man or a woman. I bet you'll learn to love it as much as I do."

By now I was relaxed enough that I felt comfortable asking her a question. "It felt so nice down there, especially when we were making love. Does it tastes as good as it feels?"

Her response was completely honest. "I think it does. I've always loved the taste of a woman's sex and I love how it turns a woman on. I love the way a man tastes, too. Their cum has a salty taste to it. I think you'll learn to like these tastes as much as I do."

Our rest period lasted about five minutes. Jeannie starting licking my soft cock and in no time my erection reappeared. She took of her nightie and taught me how she liked her breasts sucked and massaged. Then she had me slowly kiss my way down until I reached her pubic mound. I spent a few minutes there, then moved straight down to lick her cunt lips. She was right. The taste was super.

She coached me on just how she wanted it done. She told me the names of the different parts of a woman's organs. I'd never even heard of a clitoris before that night, but I was an expert on hers by the time it ended. I loved pleasing her. She'd been so wonderful to me that I was more than willing to reciprocate.

We fell asleep in each other's arms, sleeping like newborn babes. I dreamt all night about being a woman.

What a day for me! My first official day as a girl and my first time making love to another woman. Yes, that's what I said, another woman. By that time I felt very strongly that nature had truly intended me to be a woman and that I probably would think of myself that way for the rest of my life.