My First Time as a Girl

Karen Jensen

Two childhood best friends try to take advantage of a Drive-In-Movie deal in the 1950's by having one crossdress, but the night ends up revealing a new side for both boys.  

I met my best friend Jerry on the first day of kindergarten, and like most of the boys we cried when our mothers left us. Our friendship grew and it seemed like we did everything together. I guess in some ways what happened between us may have been inevitable.

We were about to graduate from high school in 1955. We lived in a moderate sized town with two movie theaters and a drive-in. Guys loved to take their dates to the drive-in where they could make out in relative obscurity. They especially liked it when the theater showed horror movies, knowing they would usually scare the girls who often would snuggle up close to their dates when it got really scary.

Jerry wanted to see the doubleheader of Frankenstein and Dracula, which was also at half the price that night for admission, but it was only being shown at the local drive-in. I was not a big fan of horror movies, but was unwilling to tell him they scared me. I simply told him I also wanted to see Dracula because of actress Helen Chandler. The real problem was that you didn’t see two guys going to the drive-in. It was commonly known in our town as the make out spot for couples.

So we were sitting in Jerry’s living room bemoaning our fate. There was no way we would ruin our reputations by going to the drive-in together and have everyone think we were a couple of fudge packers...we were stuck. It was then that Julia, Jerry’s sister walked. She was 21 and studying cosmetology. She was a knockout and I had been in love with her since she started babysitting us when she was 12. I knew that I would never have a chance with her.

“Why the long faces guys?” she asked.

“We really wanted to see Frankenstein and Dracula, but it is only playing at the drive-in.” Jerry responded.

“So go to the drive-in.”

“You know as well as we do that only couples go to the drive-in” Jerry answered.

She got a big shit eating grin on her face and said “So go as a couple.”

“We aren’t homos and we don’t want to get a reputation like that.” I responded.

“It’s not a problem. With the right clothes and a bit of makeup I could transform you into a girl and Jerry would get a reputation of having a hot girlfriend.”

“No way!”

“Wait a minute!” said Jerry. “Didn’t you say you would do anything to see Helen Chandler in Dracula?”

“Yeah, but…….I kind of did…..but, this is ridiculous. I can’t pass as a girl!”

“But what if you could?”

“But I can’t!”

“Don’t be so sure” said Julia. “I’ll bet I can make you into a very pretty girl. Let me fix you up and if you don’t like the way you look, well, at least you tried.”

I shook my head. I wasn’t going to put on a dress just to see a movie.

“At least give it a try” said Jerry. “I’ll forget about the 10 bucks you owe me if you let Julia work her magic.”

“Why can’t you be the girl?” I asked Jerry.

“Well, I’m 6’2” and weigh 210 lbs. You’re what, 5’ 5”?”

“5’ 6” actually.”

“My point exactly” said Jerry. I am way too big and ugly to pass as a girl.”

“Come on, Rob.” said Julia “Come with me and let me see what I can do with you!”

Before I could offer another protest, she grabbed my hand and showing surprising strength, pulled me to my feet and led me towards her bedroom.

“Find something to keep you busy Jerry. This will take while” she called back over her shoulder.

I could not believe I was allowing this to happen. We entered her room and she closed the door. It was the first time I was ever alone with a girl in her bedroom and it was to allow her to transform me into a girl.

“How sick is this?” I asked myself.

Julia told me to stand up straight as she looked me over. She was a beautiful girl. But even she was taller than I was and though I knew her like forever, I was still intimidated by her.

“I have some old clothes that I think will fit you. Now strip!”

“In front of you?”

“Are you wearing boxers?”

“Yes.”

“Well what would I see that I don’t see at the beach?”

“Nothing, I guess.”

I turned my back to her while I stripped down to my boxers. When I finally turned around she looked closely at me and ran her hand over one of my legs.

“Nice and smooth” she said. “At least we won’t have to shave them.

I blushed when she said that. My puberty had been late and I still had no hair on my legs and little under my arms and on my groin.

Then she handed me a pink circle skirt and told me to put it on.

 “I need to see if it fits” she said.

I stepped into the skirt and tried to close it. I could not button it and the zipper went only part way up.

“Well, I guess we won’t be going to the movies” I said, feeling relieved.

I removed the skirt and turned to pick up my clothes.

“I thought that might be the case, so we go to plan B” Julia replied.

“What’s that?”

She smiled at me as she handed me an open bottom girdle with 4 garters hanging from the bottom.

“This should shrink your waist enough so you can fit in the skirt but I’m afraid the boxers will have to go.”

“What will I wear?”

She tried hard not to laugh and mostly succeeded as she handed me a pair of pale blue full cut panties with white lace on them.

“Put these on and then pull on the girdle. Call me when you have done that” as she said as she left the room taking my clothes with her.

I tried to tell her I wouldn’t wear the panties but she was gone before I could protest. I stood there for several minutes in only my boxers debating what to do. I thought about the 10 bucks that Jerry promised me and decided that I would let her dress me up and then refuse to go out. After all, I reasoned, there was no way she could make me into a girl. I picked up the panties and stepped into them. They were silky and I could not believe the difference in the feeling between them and my boxers. I instantly had an erection which embarrassed me no end. I was grateful she wasn’t there to see it. Hoping that the girdle would hide my erection I stepped into it and slowly pulled it up to my waist. It was very tight, but I succeeded in getting it on and it did give me a flat front.

The girdle drew in my waist and gave me a somewhat feminine figure, at least from the waist down. For the first time I had a touch of fear that their plan might work. I called to her to come in.

“Very nice” she said. “Let’s get you dressed.”

She took a white bra and wrapped it around my chest. Then she stuffed each of the cups with several pairs of panties. My penis was stiff and solid now as I realized that she was using her own undergarments that she wore close to her intimate parts. She took out a pair of nylon stockings and showed me how to put them on. I succeeded without running them.

“Good girl” she said. “Are you sure you haven’t done this before?”

“Of course not” I replied. “What do you think I am?”

“Don’t be offended, most girls ruin the first pair of nylons they put on. That’s all I meant.”

“OK. I’m sorry I got angry.”

“That’s ok. I know it is hard for you to do this. You are being a real sport. I would have preferred to do this to Jerry, but there is no way I can make him look like a girl.”

Then she gave me a brief kiss on the lips.

I blushed a deep red, but the realization that she thought she could make me look like a girl but not my friend embarrassed me even further.

“Now you need to pull your panties over the garters and let them hang out through the leg holes.”

“Why is that?”

If you have to go to the bathroom, you would have to unhook your stockings if the garters were over your panties.

“I won’t be going to the bathroom” I replied.

“Don’t be so sure” she warned me.

She turned her back to me while I dropped my panties and pulled them over the garters. Then she showed me how to hook the first stocking to a garter and had me do the rest. Feeling the tension in the garters and stockings was highly erotic and caused a considerable discomfort in my groin. I was finding it hard to get erect in the confines of the girdle.

She handed me a white full slip and told me to put it on. It was very lacey and felt really nice as I slipped it on. It made me feel like a real sissy. She explained that the crinolines that I would have to wear under the skirt would be very itchy and the slip would feel much better. I could not understand why putting on girls clothing was affecting me like this.

“Hold your arms up” she said, interrupting my day dreaming.

She slipped two crinolines in succession over my arms and settled them on my waist. They fell several inches below my knees. Then I put my arms into a white blouse with short sleeves and a peter pan collar which she buttoned up the back. Now I really felt trapped in the female clothing realizing the to remove it myself I would have to tear off he blouse.. Then she slipped the skirt on over my head. This time there was no problem zipping it and buttoning it in the back. Obviously the girdle had made the difference. Then she handed me a pair of, you guessed it, pink shoes with no heel. They were a bit tight but I could wear them.

Curiosity got the better of me and I told her I wanted to see what I looked like.

“Not so fast. Let me put makeup on you and a wig and you can see the final product. She draped a towel over her mirror and sat me at the vanity. I won’t bore you with the details, but she worked on my face for what seemed like an hour. All I knew was she worked on my eyes and my whole face before finishing off with pink lipstick that matched my skirt.

It was actually very nice sitting there and having her work on me, even if it made me feel even more like a sissy.

“Now can I look?” I asked.

“No, wait until I get the wig on you and brush it out.”

She took out a blonde wig in a page boy style which was quite popular at the time. She attached it to my own hair with hair pins, brushed it and finished it off with a pink ribbon on top which matched my skirt.

“One more thing” she said.

She took out a scarf from her dresser, also pink, and tied it around my neck letting it hang to one side.

“Ok Rosie, you may look.”

“Rosie?”

“Trust me; you do not look like a Rob. There is a full length mirror behind the door in my closet. Tell me what you think.”

I was really nervous as I walked to her closet and opened the door. I looked in the mirror and just stared at myself. I was speechless. The blouse was translucent and the outline of my slip and the bra straps were clearly visible. The makeup was very subtle but effective. I looked like my sister, if I had had one. I put my hand to my mouth and the girl in the mirror mimicked me. I looked back at Julia who was smiling at me.

“What do you think?” she asked me.

“I..I..I” was all I could say.

“I told you I would turn you into a pretty girl. Let’s go show Jerry his date for tonight.”

She grabbed my hand and led me into the kitchen, where Jerry was reading one of his girlie magazines. She stopped me just before we got to the kitchen door and told me to wait.

“Jerry!” she said. “Allow me to present Rosie.”

She stepped aside and motioned for me to enter. I swallowed hard, expecting my best friend to burst out in laughter as I entered the kitchen, stopping a few feet in front of him. When he looked at me he jumped to his feet. Then he just stared at me with his mouth and eyes wide open. After a few moments I started feeling very self conscious.

“This isn’t going to work. I’m gonna put on my own clothes and we can figure out what we want to do tonight.”

“No! Stop! It will definitely work. Stay here and I’ll be right back.”

“Wait! I’m not sure if I….” I said as he disappeared.

He returned wearing his jacket and grabbed my hand.

“Let’s go” he said. “We have enough time to get a space and some snacks. It will be my treat, of course.”

He pulled me towards the front door. Julia handed me a pink cardigan and small purse, both of which matched my skirt.

“Remember when you are getting into a car to sit first and swing your legs in while holding down your skirt, or you will flash your panties. When getting out just do the opposite. Oh, and remember, to sit if you use the ladies room” was the last bit of advice she gave me as we were leaving the house”.

Before I could say anything else we were out the door and I heard Julia lock it. I was trapped now. Jerry held onto my hand as we walked to his car. He opened the door for me and held it as I got in, remembering Julia’s advice. I didn’t want him to know I was wearing panties.

It took about twenty minutes for us to reach the theater. Jerry paid for us and at my urging found a spot that was away from other cars.

“Wait here while I get us some snacks” he said and soon disappeared.

He was gone about 10 minutes and I got increasingly nervous as other cars pulled into the spaces near us. Guys in the other cars checked me over despite being with their girlfriends. When the door opened, I jumped in fear. I guess my anxiety from the fear of being discovered had me on edge. 

“Sorry, I didn’t mean to scare you, the line was long. I tried to hurry before the movie started,” he said.

He handed me large soda and a giant bag of popcorn through the window. Then he went around to the other side, and got in the car. He attached the speaker to the window and slid over next to me so our legs touched each other. It was a strange experience for me to be sitting that close to another guy.

“Why are you sitting so close?”

“We are supposed to be boyfriend and girlfriend, remember?”

He reached over and took a handful of popcorn. I set the soda on the floor so I could also eat the popcorn. By the time the first movie started we had finished our sodas and the popcorn. Jerry ate most of it as the girdle was curbing my appetite. He put the empty containers on the floor in the back and we settled down to watch the movies.

At the first appearance of the Frankenstein monster, I jumped and instinctively turned my head towards Jerry to cover my eyes. He reacted by putting his arm around me and pulling me close to him. I was too embarrassed to say anything. He kept me close to him and admittedly it felt good. I knew I should pull away but I was enjoying the feeling. I wondered what we would say to each other later but decided not to worry about it then.

A few minutes later I sensed his turning his head towards me and I looked up at him. He was smiling down at me.

“You are so beautiful” he said.

I felt my face turn warm and he leaned over and kissed me gently on the lips. He pulled back, continuing to look at me. I am sure he was wondering how I would react. I didn’t know how I should react, but I knew that it felt good. Maybe it was the attention I was getting or the feel of his touch but, I liked it.  I was trying to get hard underneath the girdle. When I didn’t resist he kissed me again. This time it was longer and when I still made no effort to pull back, he gently pried my lips open with his tongue and put it inside mouth. After his tongue explored my mouth and massaged my own tongue, I sucked on his. This was getting me more turned on than I had ever been. I felt his hand reach under my skirt and caress my nylon clad legs. It was so erotic I thought I might cum then and there. He slid his hand up my leg until he encountered my girdle.

I asked myself if I should stop him, but was too far gone to really consider it. He took my hand and laid it on his groin. He was already erect.

“My gosh” I thought  “I was arousing him!”

“Take it out Rosie!” he whispered.

I slowly unzipped his pants and pulled his hard cock out. I didn’t realize how big he was. I leaned over and kissed him again, this time sticking my tongue in his mouth. I gently stroked him and felt him get even harder.

“Suck it Rosie!” he ordered me.

“Could I do this?” I asked myself as I continued to jerk him off.

“Please” he begged.”

I looked into his pleading eyes and could see he really wanted this. I looked around and saw most of the couples were fully focused on their own passions. 

I slid off the seat onto my knees and adjusted my skirts. I leaned over till my face was above his cock. I licked it gently and he gasped.

 “I can’t last long,” he said “Please…. suck it?”

I hesitated for a few moments and froze only hearing moans from the other nearby cars. I don’t know if it was that which encouraged me or the power I was having over Jerry. It was now or never.

I took him into my mouth and began to suck him off. I ran my tongue under his cock and took as much of it as I could into my mouth, nearly reaching his base. I heard his heavy moans, while I sucked on his shaft. True to his word he released his warm seed at the back of my throat. He quickly filled my mouth and I swallowed what I could. It overwhelmed me and I could not swallow all of it, some dripping down my chin and onto my skirt. I had never tasted my own cum so tasting his was a first for me. Though a bit salty, it was not unpleasant. I had made my best friend happy and that was worthwhile.

I came up slowly looking around to see if anyone had seen a hint of what happened between me and Jerry. I saw most of the couples had disappeared in their cars, but no one was paying any attention to us. 

He put his cock away and zipped his pants. Then he helped me onto the seat, put his arms around me and kissed me passionately. The movie had been totally forgotten.

He reached up under my skirts and grabbing the waistband of my girdle, pulled it down. I felt my erection grow in my panties. He then pulled down my panties freeing my tiny erection. After seeing how big he was I felt ashamed of mine. Jerry said nothing about my size. He stroked me a few times until I exploded in his hand.  He surprised me when he licked the semen from his hand. He grabbed some tissues from the glove compartment and wiped me off. I then pulled up my panties and girdle and straightened my skirts. I snuggled up next to him and he held me tightly for the rest of the movie without saying a word.

 “Let’s get out of here” he said before the second movie came on. “We can grab a bite to eat and then go back to my house and play some more. Julia will be late so it will be empty.

I liked the idea of skipping the second movie, but the thought of going someplace to eat scared me. He assured me that it would not be a problem. We would go to a burger joint on the other side of town where we would be unlikely to see anyone we knew. I was still skeptical, but didn’t want the evening to end too soon. We pulled into a parking lot. It was not a place I was familiar with.

“Rosie, do you have a lipstick in your pocket book? You need to fix it”

I checked and found that Julia had indeed left me a lipstick along with some tissues and a sanitary pad. I blushed when I saw the pad and quickly took out the lipstick and closed my pocket book hoping Jerry didn’t see the pad.

I managed to repair my lipstick and waited while he came around to open the door for me. He held out his hand and helped me up from the car. Then he put his arm around my shoulder as we walked into the restaurant. I was really nervous about being in such a public place but I trusted Jerry. When we entered the restaurant I quickly glanced around and did not see anyone I knew.

We found a booth in the back corner. The waitress handed us menus but did not pay particular attention to me. In fact her eyes seemed linger on Jerry. After we ordered I realized I had to pee.

“I have to pee. What do I do?”

“You will have to use the ladies’ room. Just be careful!”

“That’s easy for you to say.”

I slid out of the booth and started to walk to the ladies’ room.”

“Wait! Don’t forget your purse.”

I grabbed the little pink bag and headed to the bathroom, praying no one was in there. I didn’t see anyone and grabbed the first stall. Remembering Julia’s advice I slipped off my panties, lifted my skirt, petticoats and slip, and sat down. It was a royal pain having to deal with all that clothing. I wondered how girls put up with it all the time. Relief washed over me as I emptied my bladder. Then I had to put myself back together, but somehow I managed. I returned to the table just as the waitress was bringing our food.

We did not chat while we ate which was unusual for us in normal circumstances. This was hardly a normal evening out for us. Then I felt his foot rubbing against my calf.

 “What are you doing?” I asked him.

He just smiled back at me and raised his foot above my knee, lifting my skirts while he did that. I could feel myself trying to get hard under my girdle.

“Please stop!” I begged him.

He could see that I was getting angry and removed his foot. He kept that shit eating grin on his face while we finished our meal. He held my hand as we walked to the car. Before he opened the door he put his arms around me and gave me a passionate kiss. I felt warm all over and was in a daze as I sat down. He waited for me to adjust my skirts before closing the door. I would not have believed it if someone told before we went out but it had been an amazing evening. Though I wouldn’t be sad about getting out of these clothes, I was a bit sorry to see it end.

We went back to Jerry’s house and it appeared to be empty just as Jerry said it would be. Their parents were gone for the weekend so, for the time being, we had the house to ourselves. He led me into his room and told me to wait there. He was gone only a couple of minutes and when he returned he handed me some silky material and told me to put it on. When I unfolded it I found a short purple nightgown with matching panties.

“Are you sure Julia won’t mind?”

“It was in the charity bag. She doesn’t wear it anymore.”

I felt humiliated at having to ask him to unbutton my blouse. Before he let me go he snapped my bra, like we used to do to girls when we were much younger. As I went into the bathroom he told me to leave my bra on. It was a great relief to take off the girdle. When I returned to his bedroom he was already in bed and from the bump I could see in the blanket, he was already erect. My mouth watered at the thought of it.

He pulled back the blanket and motioned for me to get in next to him. He was totally naked. My heart was going 100 miles an hour at what I thought was going to happen. 

Normally when I slept over it was in the top bunk, but obviously this was different. I had never been dressed like a girl before.

He rolled over on top of me and began kissing me. Without the girdle there was nothing holding me back and I was very quickly erect. is kisses were then focused on my sensitive neck. His penis was rubbing against mine through my nightgown. I was afraid I was going to cum right then.

“I am going to fuck you” he said.

A chill went through me and I seemed to be getting harder.

 “Lubricate me with your mouth first” he ordered.

Not waiting for an answer he got onto his knees and straddled my face. His erection was right above my mouth. Submissively, I allowed him to stick it in my mouth.

“Slowly” he commanded “I don’t want to cum just yet.”

I followed his directions and let him use my warm mouth to get his cock good and wet. He climbed off me.

“Get on all fours” he demanded.

I obeyed him. He lifted the skirt of my nightie and pulled my panties down, exposing my ass to him. I felt his finger at my virgin opening and when he inserted it, it was cold and slimy.

“Just some extra lube” he whispered. “I will be gentle.”

He rubbed his cock around my hole before slowly entering me. It felt so huge and I was sure he was too big.  He pushed slowly and stopped, waiting for me to tell him h could continue. It hurt when he entered me and I was sure he wouldn’t fit, but as the pain subsided I found I enjoyed the sensation. He did this several times until he was all in. he waited until the pain dissipated and it felt good to have him inside me.

Then he began to slowly fuck me. I had never felt this hard in my life and found myself pushing back to meet his thrusts, gripping the sheets tightly. I moaned from his repeated humping. His heaving groans and moans were a sign that he was enjoying me. He didn’t last long and I felt him ejaculate inside me. That triggered my own orgasm. I came all over my nightgown as he came inside my ass. It was the best orgasm I had ever had. When he was finished he collapsed on top of me.

When I awoke the next morning I wondered if the whole evening had been a dream. I looked around and realized I was in Jerry’s bed with his arm draped over me. He was snoring, more than likely tired from last night. My ass was sore and my panties were still around my knees. I had to take a wicked piss. I slipped out from under his arm without waking him and headed for the bathroom. Without thinking about it I sat, though it would hardly have been necessary in Jerry’s house.

As I came out of the bathroom Julia was coming in. She smiled at me.

“Looks like someone enjoyed herself last night” she said staring at the semen stains on my nightgown.

“It’s alright” she said as she saw the horrified look I had.

She took me in her arms and hugged me.

“Let me fix your makeup so you’re pretty for your boyfriend when he wakes up. Wait in my room while I pee.”

I went into her room and sat on the bed. I realized I was walking funny, an indicator that it was a passionate night for both of us. She walked in and had me sit at her vanity. I started to cry.

 “What is going on Julia? I’m so confused.” I asked her.

She sat on her bed and motioned for me to sit next to her. She hugged me until the tears stopped.

“Did you enjoy last night?”

“Yes, that is what is so confusing.”

“I heard everything from the next room. My date cancelled, so I was in my room studying when you and my brother got home” she said. “It’s okay, I’m happy for you two.”

I stayed silent looking at the floor. 

“You and Jerry have been best friends forever, right?”

I nodded.

“Well, I would have hoped Jerry would tell you, but I guess it is up to me. He is a homosexual or perhaps bisexual. He is attracted to other boys, particularly when they are dressed up as girls. But he loves you. The girlie magazines he has are not girls, but men dressed up as women. Last night was his idea. I am sorry for the part I played, but he is my brother and I love him dearly. I didn’t think you would be hurt by dressing you as a girl, maybe just a bit embarrassed. He thought that if you looked like a pretty girl it would be natural for him to make an advance on you. If you rejected his advance he would have just laughed it off. Obviously you didn’t reject him.”

“No, I liked it. So does this make me a homo also?”

“Only you can answer that.”

We sat there in silence for a few moments.

“So, what do you want me to do? Should I turn you back into the pretty girl you were last night or help you to become Rob again? Your clothes are here in my closet or should I make you pretty again for Jerry”.

I hesitated for a minute or so. I realized I could walk away and last night would just be a pleasant memory.

Finally I said “Make me pretty!”

She smiled at me and hugged me. First she removed the old makeup which was smudged and then reapplied it. It took less time than it had the previous evening since, as she told me, she had a better idea of what she wanted to do. She combed and brushed my wig and pronounced me ready to meet my boyfriend. I stood up to leave but she stopped me.

“Wait, take off your nightie and I will give you a clean one.”

She opened a drawer in her dresser and handed me a light green nightgown with a matching pair of panties. This time I didn’t worry about her being in the room as I slipped off my semen stained nightie and panties, and put on the clean ones. I thanked her and hugged her. She told me she was leaving soon for work, which would give me and Jerry some privacy. I returned to Jerry’s room where he was still sleeping.

I pulled back the covers and crawled in next to him. I took his cock in my hand and gently stroked it. He groaned but didn’t appear to wake up. I leaned over and took him in my mouth. I rolled my tongue over the head of his cock and that woke him up.

“Don’t stop!” he said.

I released him from my mouth and moved up to kiss him. My tongue invaded his mouth and he sucked on it. I withdrew my tongue.

“I won’t” I said.

Then I resumed sucking him until he ejaculated. I swallowed every drop and licked him clean.

We finally got out of bed and showered together, where we brought each other off using our hands. Reluctantly I had to return to being Rob since I was expected at home. But I left my boxers there. Underneath my pants I wore pair of full cut lemon colored panties, courtesy of Julia.

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Author's Note

I want to thank Annabelle Brito for reviewing and making suggestions that I believe have greatly improved the story.

This story is complete fiction and any resemblance to persons living or dead is pure coincidence. I hope you enjoy it. Please leave your comments, good or bad. I try to learn from constructive criticism , or, if you prefer you may email me at kjensen0611@gmail.com.

I apologize in advance to any gay persons reading this story. I have used language that is derogatory to gays, but it was the popular vernacular of the time. I would never think of using this kind of language in my real life. If you will be offended by it, please do not read the story.

If there is enough interest, I may consider writing a sequel.