Chapter One - California Here I Come!
School was out! More than out, high school was over for me. The prom and the graduation parties had been a blast, but I was looking forward to something even better. It was spring and I was eighteen. Most of the kids my age were happy to be spending the summer vacation with their friends, going to the beach and partying. I knew I'd have a dismal summer if I stayed in town. I hadn't been very popular in high school and, as a result, I had no close friends. I was smaller than almost everyone else and was always being accused of acting like a sissy, so a change of venue very much appealed to me.
My parents had just left to spend the next four months in Europe, and I had been invited to visit my Aunt Susan and her daughter Jill in San Francisco. It was quite an adventure for me as I'd never traveled away from New York state before, and it had been ten years since I'd last seen my aunt and cousin. I was especially looking forward to the trip and my summer with them.
I arrived in early May and Aunt Susan and Jill met me at the airport. Aunt Susan was in her middle thirties and a tall, very attractive brunette with a terrific figure. Jill, at nineteen, was a budding California blonde, beautiful and nicely developed. I couldn't take my eyes off her and had a hard time paying attention to Aunt Susan's family reminiscences on the drive to their home in Marin county. I tried concentrating on the California sights during the brief trip rather than embarrassing myself gawking at Jill.
When we pulled into the driveway, I was astonished at the beauty of the homes in Aunt Susan's neighborhood. Never had I seen such lavish houses before. It dawned on me then that I must have a very wealthy aunt.
Her home was a lovely, newer Victorian style occupying the top of a small knoll with an acre of land surrounding it. The grounds, especially in front of the house, were covered with flowers and trees I'd never seen before. Just behind the house was a swimming pool hidden from the rest of the nearby homes by an eight foot fence. Posh. Definitely posh.
I was given the guest room next to Jill's bedroom and across from Aunt Susan. I supposed it had been recently occupied by Jill or one of her girlfriends as it was decorated in very feminine fashion; ruffled pink curtains, a pink satin spread and flowered wallpaper. Against the wall was a triple dresser with two large mirrors and a makeup table almost covered by a wide variety of cosmetics and perfumes.
I didn't feel I should complain about the decor. After all, I would be a guest for a mere four months. I quickly unpacked my things and went to put them away in the dresser. Much to my surprise, most of the drawers were already filled with lacy lingerie, bras and hose which I assumed belonged to Aunt Susan or Jill. The closet was much the same; lots of dresses, skirts, blouses and many pairs of shoes. I was barely able to squeeze in my pants and jacket.
Just as I'd finished unpacking, Aunt Susan called to come to lunch. She had prepared a fresh fruit salad and some lemonade. "How do you like your room, dear?" she asked as we ate.
I fibbed a bit, trying to be a good guest. "It's fine. I'm sure I'll be comfortable there."
She and Jill exchanged a smiled. "We hope you enjoy your visit with us, honey, and let me know if there's anything you need. We have lots of fun things planned so I know you won't be bored."
I thanked her and, after lunch was over, she suggested that I might need a nap after such a long plane trip. Having experienced jet lag for the first time, I quickly agreed and retired to my new room.
As I dropped off to sleep in the canopied four-poster bed, I heard Susan and Jill whispering outside my door, but couldn't quite make out what they were saying. Just as I fell asleep, I thought I heard Jill laugh and say, "I'm sure she'll make a delightful sister."
I wondered who she was talking about but I was too sleepy to care at that point.
Chapter Two - Video Queen
It was dark when I awoke. I dressed in a tee shirt and shorts and went into the living room, finding Jill alone on the couch watching television. She was dressed only in a semi-transparent blue night gown. It was extremely sexy and a perfect accent to her blonde good looks.
"Hi," she said, "come and watch the movie with me. If you want anything to eat, just help yourself."
"No, thanks, I'm not hungry. Where's Aunt Susan?" I asked, feeling somewhat uncomfortable with the way she was dressed but delighted to be alone with her. This will be one hot summer, I thought, if this is the way she dresses around the house. Not that I had any complaints.
"She went to bed," Jill said. "Sit down and watch if you feel like keeping me company."
I couldn't think of anything I'd rather do more so I sat next to her on the couch, stealing peeks at her out of the corner of my eye as often as I could without being too obvious. A movie was playing, but I didn't know what it was and, at that point, I really didn't care, that is until I happened to notice some very strange scenes in it.
"What movie are you watching, Jill?" I asked.
"It's a tape my mother brought home today. It's about this guy who dresses up as a girl."
"That's weird," I said, very curious as to why Aunt Susan would let her daughter watch what I assumed was a porn flick.
"No, it isn't," Jill peevishly answered. "Lots of boys like to put on girl's clothes. I think they look very pretty. If this guy in the film is like all the rest of them, it really must give them a big thrill. As far as I'm concerned, there's nothing wrong with it. It doesn't hurt anyone, does it?"
"I guess not," I admitted, as I watched the boy on the screen trying to tuck his very erect cock into a skimpy pair of black lace panties. He finally managed to hide it and, after he put on a matching bra and slip, he was very cute and sexy looking, I must confess. As I watched him transforming his face into that of a girl, I was starting to get that old familiar tingling in my groin. Being able to see through Jill's nightgown didn't exactly cool me off either.
Then I remembered how I'd felt the times I'd tried on some of my mother's clothes. Strangely enough, wearing them had made me feel very good, but I'd sworn off experimenting with women's clothes a few months ago because my mother had come home one afternoon unexpectedly and caught me wearing one of her dresses. I confess I'd panicked. I could only stand there frozen in front of her, unable to move or even talk.
She hadn't been angry with me and said if I wanted to talk about it, she'd try and understand why I wanted to wear women's clothing. The only response I could manage was to run into the bathroom with tears of embarrassment running down my face. I had stripped off her clothes as quickly as possible and I'd never worn her things again since that day.
The next thing I knew, Jill's hand was resting on my arm. Another wave of heat stormed across my groin and I could feel my cock harden.
She must have interpreted my silence as further disapproval. "Don't be a nerd," she teased. "Just watch the tape and I'll bet by the time it's over, you'll think it's great."
"Sure. Whatever." It really didn't matter to me what tape was on. I would have agreed to watch a ballet if I could stay there next to her, and I think she realized it.
We sat there for a while, not saying a word. The movie was getting to both of us. I inched closer to her and she began to stroke my arm, then she moved her hand to my thigh. Moments later, she looked down at my lap.
"You have a hard on," she giggled. "I think this film is turning you on. It gets me steamed up, too. Would you think I was terrible if I asked you to kiss me?"
I could only shake my head, and she leaned forward until our lips were pressed together. A few minutes later and much to my amazement, she dropped the straps on her night gown revealing both her breasts. She was fully developed and they were perfect; firm, ripe and just begging to be touched. Jill took my hand and put it on one. It felt wonderfully soft and warm. I had never felt a girl's breast before and could sense the blood rushing to my face.
"You're embarrassed, aren't you?" Jill giggled again. She was thoroughly enjoying my discomfort. I could tell she really enjoyed teasing me.
To shut her up, I leaned over and kissed her. Just as our tongues were exploring each other's mouths, Aunt Susan came into the room. She looked down at us, her face filled with astonishment.
"What do you two think you're doing?" she asked, a note of displeasure in her voice. "Jill, I'm surprised at you. Both of you go to your rooms and I'll come up in a minute. We're going to have a long talk about this."
I ran up to my room and Susan followed me in moments later. She closed the door and sat on the bed next to me. It seemed to me she was even more angry than she had been in the living room.
"If you're going to be spending the rest of the summer with us," she said, "I going to have to teach you some manners. Take off all your clothes!"
Afraid not to do as she had ordered, I turned my back and quickly slipped out my shirt and shorts. I turned to her wearing only my briefs.
"I said all your clothes, didn't I? Now take those ugly underpants off immediately."
I knew I had little choice so lowered them to my ankles and stepped out of them wondering what kind of punishment she had planned for me. As I slumped down on the bed desperately trying to hide my genitals, I could picture myself being hustled to the airport and dumped on the next available flight home after an angry call to my parents.
"I didn't tell you to sit on the bed, did I?" she snapped at me. "Stand up here in front of me."
I immediately did as she had directed. "No, Aunt Susan. I'm sorry. I'm just kind of embarrassed."
"You should be after what I saw. Now I want you to lay down on my lap. You behaved like a naughty child tonight so I'm going to have to treat you like one."
I started to object but she cut me off instantly. "Not another word out of you. On my lap! Now!"
Meekly, I did as I was told. As my penis touched her nightgown I was horrified to feel it getting hard. What would my aunt think of me?
But, much to my relief, Aunt Susan either didn't notice or she didn't care. I felt and heard her hand as it struck my cheeks, not once but more than ten times. By then, I was almost in tears.
Thankfully, she stopped and ordered me to sit next to her on the bed. She looked at me and asked what had occurred to get me so excited that I'd tried to take advantage of her daughter.
I told her about the boy in the film who had dressed up in girl's clothing, and I admitted it had aroused me a lot. I apologized to her for touching Jill, but she just smiled and told me it was only natural to be curious about the opposite sex. I was sitting there naked, feeling quite helpless but still erect.
"If you're so excited you can't control yourself, then I guess I'd rather have you feeling my breasts instead of Jill's. After all, she is still young," Susan said. "Here, take one in your hand and feel how nice and soft it is."
She took my hand and put inside the top of her sheer black nightgown. Her breasts were much fuller than Jill's and her nipples were as hard as my cock. As I tentatively caressed her, she started to breath heavily, then she reached down and touched my penis causing it to harden even more.
"You seem so mature down here, dear," she said. "I think I'm going to kiss it. Would you like that?"
I could only nod, so, Susan knelt in front of me and then took my erection in her mouth and began to run her tongue all over it. I had never been so excited and hard before. In less than a minute, I exploded into her mouth. I poured out my discharge and she swallowed all of it! Suddenly, it occurred to me that having my sperm in her mouth might make her even angrier, but I was wrong.
"How was that, dear?" she asked, smiling up at me.
I was too frightened to reply for a moment or two but finally managed to find my tongue. "I'm sorry, Aunt Susan. That won't make you sick, will it?"
"No, my dear, that's what I was hoping you'd do. It tastes like cream and I think it's good for me. Now go to sleep and we'll talk about your stay here in the morning. I left some night things for you in the top dresser drawer. Put them on and go to sleep. Good night."
She left me, sitting on the edge of the bed, still trembling. When I heard her walking down the hall, I got up and looked in the drawer for my pajamas, but they were gone. The only thing in there was a lacy pink nylon nightie and a pair of pink bikini panties. I was searching for my pajamas when she came back into the room.
"Is anything wrong, dear?" she asked.
"I can't seem to find my pajamas," I said. "I know I put them in here before I took my nap."
She just smiled and handed me the baby dolls and bikinis. "You'll be much more comfortable in this nightie and panties, and you'll look so much prettier in them, dear. Now put then on!"
Hearing the steely edge in her voice, I knew she meant what she'd said. Reluctantly, I stepped into the wispy panties and pulled them up to my waist. They barely covered my maleness. Aunt Susan assisted me when I had trouble putting on the nightie, then she led me over in front of the mirror.
"Just take a look at yourself and you'll know I was right. You look so pretty in pink!" she said as she kissed me on the cheek. "You have a very feminine body, dear. Tomorrow morning, we must see if we can help you take full advantage of it."
"What do you mean?" I was shocked. At five foot six inches tall and 115 pounds, I knew I was no linebacker, but I never had my body called feminine before.
"Jill and I have some fun planned for you," she replied. "She's always wanted a sister to share with and I've always wanted another daughter, so we've both decided you are going to be the new girl in the house."
I was beyond speech after receiving that bit of devastating news. "Was what I did with Jill that bad?"
"No, it has nothing to do with the way you and Jill behaved this evening. We decided to convert you into a girl just after we heard you were coming to stay with us. I'm sure once you try it and get used to it, you'll like it," she said reassuringly, "and you will get used to it because I insist you do everything I tell you to do from now on. I've had enough poor behavior from you for one evening. You'll do exactly as I say and dress as my daughter or I'll have to call your parents. You're to be a pretty young girl for the whole summer. Is that clear?"
"Yes, Aunt Susan," I answered obediently, knowing it would do no good to argue. Also, I have to admit I was more than a little thrilled by the idea and, remembering how turned on I'd been watching the boy on the tape, I decided it would be unwise to voice any objections. I thought about it for a minute more, then looked at Susan and asked, "But what will happen to me after I go back home, Aunt Susan? What will my mother and father think?"
"Don't worry about that now, dear. If you enjoy it as much as I'm sure you will, you can come back every summer and be my daughter, but probably you'll want to go home and continue to live as a young lady. You do look more like a girl than a boy. I've always thought so, ever since you were a baby. Did you know your mother and father were hoping for a girl?"
That was news to me but, as I was a bit beyond speech, I just shook my head.
"Maybe they really had one and never realized it," she continued. "You look so much cuter in that nightie. You know, I think it would be nice if you also smelled like a girl."
She took a bottle of perfume from the dressing table and sprayed me with it several times. As the flowery aroma filled my nostrils, I was astonished to find that not only didn't I hate it, I actually liked it!
"Ummm, I was right. That does smell marvelous," she said. "Now it's time for you to go to sleep."
She kissed me and tucked me in bed, then left. I tried but couldn't fall asleep. I was not only excited and apprehensive about tomorrow, but I could still feel the touch of her lips on my penis. The nylon gown felt so soft and silky against my skin and the smell of the perfume thrilled me. What would the next day bring and what would happen to me, I wondered?
As I fantasized about the possibilities, my penis got hard again and poked against the nylon panties. I reached under the covers and began to rub it. Visualizing myself in a dress wearing heels and makeup, I came for the second time that night, this time in my panties. I hoped Susan wouldn't be too angry and punish me. I quickly took them off and hide them beneath the mattress, then found a dry pair in the second dresser drawer. I slipped into them and got back into bed. Soon I was asleep.
Chapter Three - The Secret's Out!
The next morning Susan came into my room and uncovered me. "Good morning, dear. I hope you slept well. I want you to get up now and come down for breakfast soon," she said. "Make sure you keep your pretty nightie and panties on. I want Jill to see how cute you look!"
Thankfully, she didn't notice I was wearing different panties when she pulled down the covers. As soon as she left my room, I hopped out of bed, brushed my teeth in the adjoining bathroom and ran a brush through my hair. As I was very self-conscious about being Jill seeing me in a nightie, I had to summon up all my nerve before going downstairs.
Jill was already dressed and in the dining room. When she saw my in my nightgown, she exclaimed, "Oh, you look so darling in that! I'm so happy I finally have a sister. Eat your breakfast as fast as you can and then I want to help mother get you ready for shopping this afternoon."
As I gulped down my eggs, toast and tea I was wondering what Jill had meant about getting me ready for shopping. No one had told me a thing about a shopping trip and I certainly didn't need any help getting dressed.
When I finished eating, Aunt Susan instructed me to take my dishes to the kitchen and then go upstairs and bathe. When I was done, I was to wait for her in my bathroom.
I went and found a bubble bath already drawn for me. I got in and scrubbed myself, then soaked for a few minutes, enjoying the perfumed hot water. As I was just about to get out of the tub, Susan came in. She made sure I was clean and then, much to my horror, made me stand in the tub while she shaved my legs and underarms. As I'd never had any chest hair, the small patch covering my pubic area was all I had left. She helped me out of the tub, dried me off, then took me to my room.
"Sit in front of the mirror, dear," she commanded me. "I'm sure you remember what I told you last night about our making you into a girl, don't you?"
"I guess so," I bashfully replied. "Do I have to be a girl for the whole summer? Won't Jill and everyone else think I'm weird?"
"Yes, you do, and don't complain so much. Your mother told me how much you loved wearing her pretty things, so you can stop acting like it's the end of the world. I know you'll be happy as soon as you get used to the idea and see how lovely you look. No one will think you're weird, I promise you. Now, admit it. Aren't you pleased to be you're finally going to be your real feminine self?"
I knew then it was no use denying it. I would spend every minute of the next four months as her daughter. She knew my terrible secret and I was relieved she didn't dislike me for being different. I was thankful but still somewhat unhappy that my mother had told anyone about discovering me in her dress. My whole body was tingling with anticipation. I realized I was actually looking forward to exploring what had always been my deepest, darkest desire.