Sarah was Trained to be a Girl

Story Info
Sarah is trained to be a girl and meets a girlfriend.
3.8k words
4.4
29.2k
10
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I love to search on-line for sites related to crossdressing, that's how I found Literotica. I've also found sites for 'Men in Panties', videos of crossdressing, girls clothes for men, etc. One time, I was really lucky, I found a site offering a weekend of 'girly training'. We would be taught how to walk, sit and act like a girl. We would be dressed the whole weekend and only go by our girl names. It sounded wonderful.

I gave them a call and the person who answered sounded really friendly and understanding. My voice was clearly male but I was asking about being dressed as a girl. Would I be wearing lingerie? Would my clothes be very girly? Could I do my make-up? It wasn't cheap but, for what they offered, well worth the money. I used my credit card to make a reservation and this would be the only time I would use my male name.

She asked for my vital statistic and preferences in colors and styles. She made it clear that I was expected to dress and behave like a girl for the whole weekend. I could keep the lingerie that she would provide and she would sell me the dresses at cost. I was so excited; I could hardly wait for my weekend to arrive.

On the day, I put on sissy pink panties, girls jeans and a white blouse. I drove over to the address she had given me. It was a really impressive house on the edge of town. It reminded me of a place I had been to once before, I had gone there to visit a Dominatrix. This house had an ornate entrance with steps up to the front-door. I slowly drove around the block a couple of times to 'waste time' and then at the specified time, I went up the steps and rang the doorbell. I was so excited, I could feel my cock getting hard inside my panties.

An attractive lady answered the door and beckoned me into the entrance hall. Three other guys were already waiting there. I looked at them and smiled. I was blushing because, I knew that, they knew why I was there. I guessed we would be having girly fun together. One of them caught my eye. He was a little shorter than me, my age and seemed as excited as I was. He smiled at me and I smiled back.

After two more guys had arrived, the hostess called us to order and laid out the ground rules for our weekend. We were to dress and act like girls for the entire weekend. She would take our male clothes and keep them safe until Monday morning. She would give us girls things to wear. Sexual activity during class time was not allowed but we could do WHATEVER we liked in our own time. I guessed that this was how they stayed legal. The money we paid her only went to training. Anything else would be between consenting adults in private.

First, we were to go up to the bedroom and get ready for our first lesson and then dinner. Her assistant would be there to help us. I wondered why she said, "Bedroom" and not "Bedrooms". I was about to find out. She led us upstairs. The bedroom was large and had three beds in it. Not only would we be dressing in front of each other, we would have to share beds.

She introduced her assistant and left us to get ready. The assistant told us that first, we must pair off. I looked at the guy I had eyed earlier. He smiled and nodded. Then she said that we had to strip, shower and get dressed. My partner and I were the first to prepare, we were even expected to shower together. This was going to be a fun weekend.

She told us to strip and put our clothes in neat piles on the floor. She would collect them later and put them away until Monday morning. We striped right in front of the other four guys. I had deliberately worn really sissy panties, hoping that someone would get to see them. I had not expected five other guys and a girl would be staring at my erection barely contained in very girly panties.

She instructed us to remove all of our body hair except for our heads and our pubic area. She gave us tubes of Nair, hair removing cream, to use. This is my favorite method to remove hair. For me, it does not create razor burn in the way a regular shave does. With the cream you don't rub it in but more paint it on. We paid special attention to our pubic area. We wanted to create nice bikini triangles. We made sure to apply it around each other's balls and butt. All the time the other guys were watching us.

Stark naked, we had to stand there in front of an audience, for several minutes, while the cream did its work. The best way to remove it is a scraper. I have used a plastic knife in the past but a wooden spatula works best.

We were expected to help each other scrape off the hair and cream. I scraped his arms, legs and chest and then he did the same to me. When we had removed most of the cream, we got in the shower. The assistant left the bathroom door open and the shower door was see-though. I knew that the others were watching us, they knew that their turn was about to come. We soaped each other everywhere and used the shower nozzle to rinse off. We paid special attention to washing our cocks and balls. It was so erotic when he held my cock in his hand and sprayed water on it.

I asked my partner what name she liked to go by when being a girl. She said that her name was Linda and I introduced myself as Sarah. The space in the shower cubical was a little tight and our cocks kept rubbing together. If the others hadn't been waiting for their turn, I would have played with her cock a lot more.

After getting out, we dried each other with big fluffy pink towels. I guessed that everything our hostess would provide for us would be very girly. We had chosen the middle bed. As an exhibitionist, I wanted an audience for anything that might happen.

When we emerged from the bathroom we found our new clothes laid out on our bed. I had a wonderful pink girls party dress. It was knee length with ruffles at the shoulders and lots of petticoats. Linda's was in the same style but powder blue. The ruffles helped to hide our male shoulders to some extent.

Our lingerie was little more than wisps of see-through lace. A bra, panties, suspender belt and white stockings. As we helped each other dress, our cocks kept touching. Linda did up my bra and suspender belt for me. The second couple were at work in the bathroom but the third couple were watching us intently. I loved pulling my stockings on in front of them. Linda knelt in front of me and fastened the clasps for me. My cock was only inches from her lips. Of course, I did the same for her. I hoped I would get to suck it later.

For shoes, our hostess had provided black pumps. One of her questions when I made my appointment was what size did I wear. I had worn heels on several occasions in the past and could even drive or dance in them but I still had to be careful.

There were three dressing tables in the room, each loaded with make-up. Again, we helped each other. I did my normal style. For the eye shadow, I start with a darker blue in the middle and go for a lighter tone at the outer edges, a little gold glitter across the top and black eye liner top and bottom. For daytime I only do the upper edge but for a strong nighttime look I do the bottom edge as well. I chose a body building mascara. For blush, I use a dab of lipstick on my cheeks and smoothed it in. I prefer this too regular blush and it matches my lip color. The overall effect would have been a little too much for daytime wear but, I thought, it was, suitable for an evening occasion.

We were helping each other and making sure that the lines were clean. This was the first time I got to-do my makeup with the help of another girl. I had had it done a few times professionally but never girl-girl. We asked each other's advice over colors and style.

I added a little Giorgio perfume and earrings. I like long dangly ones that I can feel against my neck when I move my head. To finish, I brushed my hair in the best girls style I could create. It's naturally blond (maybe with just a little help from the bottle, I go from a 9 to a 10) and its shoulder length. Brushed back and in a ponytail I am a guy but with bangs and brushed around my face I am as girly as I can achieve.

When we were all dressed and made-up, we headed back down stairs to rejoin our hostess. She seemed pleased with how we looked. She made a minor adjustment here and there. This included lifting up our dresses to check our lingerie, straitening a stocking or adjusting a suspender strap as needed. We were now six girls ready to adventure forward.

Before dinner our lesson would be to walk around and sit as a girl. We had to walk with one foot delicately places in front of the other and then sit without crashing backwards into the chair. We had to sit up straight and not lean back. Our hands should be demurely held together in our laps. We must never sit with our knees apart but always cross our ankles and tuck them to one side. When talking, we could tip our head slightly to one side but not lean forward and NEVER point with our fingers.

She asked us about our experiences as girls, did we go out dressed, where did we get our clothes and so on. I think she loved the embarrassment she was causing us. Discussing shopping for and then wearing girls panties, with the group listening, was definitely a major turn-on for me at lease. Always remember that I'm an exhibitionist and I love to show-off my girly side.

When dinner was ready, she led us into the dining room. We were told to eat with delicate little bits and to just gently dab our lips with our napkins. We mustn't "wipe" them because that would mess-up our lipstick.

Dinner was light and healthy. Lots of fruit and thinly sliced meets with crunchy French bread and butter. We had to put a pat of butter on the edge of our side plates and only add it to the bread as we needed it, no spreading the whole slice at once.

We could sprinkle pepper on our food, if we wished, but if we wanted salt we must put it in a little pile on the side of the dinner plate. We could dab it onto our food with our knives as we ate.

We had a really nice white wine and, again, she instructed us how to sip on it in the way a girl would. No gulping, just a little sip at a time and putting the glass back down between each sip. We had to sit up straight and keep our ankles crossed slightly off to one side.

The whole experience was making me feel so like a real girl. Well, I was a real girl in my mind. I was lucky, I had been brought up in a traditional family and most of these rules applied to good male behavior as well.

After dinner, we were told to go back to our bedroom and make special care to remove our make-up. There would be night cream waiting for us. Our night clothes were now laid out on our beds. We each had see-through baby-doll nighties in pastel colors. Once again, our panties were just wisps of lace. After we were changed, all of our cocks stood out over the tops of them. For me it was perfect. Being dressed like that in front of five other girls all equally dressed.

We climbed into our beds. They were big enough to be comfortable but narrow enough to force us to touch each other. I put my arms around Linda's shoulders and pulled her against me. We kissed with our cocks rubbing together. I slid my hand down her back and stroked across her panties. When I gave her cock a squeeze, she giggled. I could hear that the others were 'playing' too.

I pushed the bedspread down to get to Linda's cock. I leaned over her and kissed its head. It jumped as I ran my tongue around the head. Her hand was holding my cock. It was wonderful sucking her cock with four other girls doing the same thing beside us.

She was uncut and so I ran my tongue around her foreskin. I stroked her shaft and balls with my fingertips. I loved feeling her skin against my skin. Two lesbians making out together and loving every moment of it. The fact that we could be seen made it even more exciting. We had left the lights on, I guess we all knew what was going to happen and wanted to be seen acting as little sluts.

We kept taking glances to either side to see what they were up-to. I saw them glancing at us too. One girl gave me a smile when she saw a cock deep in my throat. It wasn't the first time I had been seen giving head but it was the first time they were doing more than just watch.

I slowly slid my lips down her shaft and rapped my hand around the base. With my other hand I played with her balls and public hair. I love feeling fingers running through mine and I did the same to her. She seemed to enjoy it and pushed my head down on her cock. From either side of us came slurping sounds as our roommates got down to business as well.

When I could tell that she was getting close, I pulled my mouth away and just slowly stroked her cock. I wanted to make it last for as long as possible for the enjoyment of us both. She started to soften and so I took her back into my mouth. This time, I knew she wanted to cum. She filled my mouth with her wonderful cum. I moved up and French kissed her, she could taste her own cum in my mouth.

When she had recovered a little, she moved down and gave me a wonderful blow job. This time I got to taste my cum in her mouth. Just French kissing her and combined with a taste of cum made my cock semi-hard again.

We went to sleep snuggled together. Our cocks touching and our hands inside each other's nighties. It was a wonderful start to the weekend. After all, we had been told that we could do whatever we liked in our free time and I was going to take every advantage that I could.

In the morning, we washed, shaved, got dressed and did our make-up again. When we were all ready, we went down stairs to find breakfast. It was a good continental breakfast. Our teacher evidently did not want us to get fat and sleepy.

Back in the classroom, we had a lesson on doing our nails. We had to do one of our own hands and then the other hand of our partner. The teacher had a good selection of colors and I chose my normal bright red. These days, some 'ordinary' guys wear dark polish but I wanted mine to shout out 'GIRL'.

Linda did a really good job on my hand. I suspected that she had done it before. Our hostess came around to inspect our work and correct minor mistakes with a qutip and polish remover.

Afterwards, she gave us a lecture about 'good nail care' and what kinds of food to choose and what to avoid. Moisturizing cream was a must for every night before going to bed, especially, if we had used nail polish remover that day.

The lecture moved to skin and hair care in general. For our faces, the musts were twice daily washing with a mild soap and warm water and then face cream. For our hands, when we did the washing-up we must always wear rubber gloves. Hand cream was a must when we had finished.

For our hair the extra cost of good quality shampoo and conditioner was well worth the money. We must brush it several times a day to help the natural oil to get to the ends. Even if we wanted to let it grow, having the last half-inch cut off on a regular basis would actually help it to grow.

Lunch was again a light meal but we always felt satisfied. Of course, with the excitement of what I was wearing and doing, I would have been content with anything. After lunch we had a lecture on make-up. How to hide our male features and bring out our female aspects. Not to put bright make-up on a feature better hidden but to save the bright high-lights for our most girly features. We could use foundation but should not plaster it on, just enough to give us clear looking skin.

Dinner was a re-run of the previous evening. Very good but not so filling that we would feel sleepy. After dinner, we watched a video about 'passing". Tips and tricks for being out in public as a girl. How to carry our purses, bags, coats etc. A low, soft voice would help to hide our male sound. In most situations, we should expect to have doors held open for us and to go first. We must not look surprised but treat it as normal, after-all, we were girls.

If we were being taken out to dinner, then expect to have our chair pulled out for us and the menu handed to us. We must not appear surprised if our copy of the menu did not have prices. At the end, we should wait until our host helped pullout our chair. If we needed to use the restroom then we MUST always remember to use the Women's.

Before we retired to bed, our hostess said that tomorrow would be a little different but she wouldn't explain how.

Back in our room we all got ready for bed. The other four had decided to swap partners but Linda and I wanted to stay together. This time, Linda and I stayed on top of the bed-covers. We started to get naughty immediately. We deep kissed and pushed our cocks together. I wrapped my hand around Linda's and masturbated it. I loved feeling it harden as our tongues met.

We were even more intense tonight. We 69'ed for a while and then I sucked her off. I let her cum leak onto my lips and I made her lick it off. The feel of her tongue on my lips was so erotic. When it was my turn, she made me cum with my cock right down her throat. With her tongue pressed against my underside, she could feel each squirt of cum firing down her throat.

We laid back on the bed and watched our roommates finishing each other off. Six happy girls ready for sleep and the next day of training.

The next morning we found a different set of clothes laid out for us. We had Mary-Jane shoes with white ankle socks. Navy blue cotton panties and white bras. Our dresses had been replaced with red pinafore dresses. The skirt part was pleated and the top had straps over our shoulders. They were all the same and I guessed that we were to be school girls together wearing regulation uniforms.

For day-time wear we were told to keep our make-up very light. We should use just enough to make us look like school girls.

I realized that since we were in 'school', we should dress appropriately. I loved the pleated dress around my legs. It was shorter than my party dress and so I had to be careful not to let my panties show. I did feel Linda's panties under her dress when we were done. She giggled just like a real school girl when I stroked her cock.

Over breakfast, our hostess outlined what we would be doing. We were going for a walk and then stop for lunch. We did not have to walk in line but we should stay together and walk in pairs holding hands. Some of the girls seemed a bit nervous about being seen in public dressed as a girl but for me going out dressed was second nature.

I assumed that our hostess had done this with classes before and the places she would take us had seen girls like us before.

We had a nice stroll through a park and I held hands with Linda. We stopped for lunch at an outdoor café. A couple of tables had already been pushed together for us. Of course, we used our girly manors while eating. If we needed to use the restroom we had to use the ladies. When I needed to go I took Linda's hand and we went together. We checked each others make-up and kissed a little before returning to our table.

Using the Ladies-room was quite normal for me but it was probably the first time for some of the girls.

When we got back to the house, we had a little free time before dinner. We just walked around the house dressed as school-girls and enjoying every minute of our experience. After dinner we went back to our room for more fun. Our hostess said that our male clothes would be there in the morning and she had nail polish remover for anyone who wanted it. I kept my nails red. Linda and I had really got along together and we agreed to meet again.

In the morning, our hostess gave us one final piece of advice. We must always believe that we were girls. This would cover any minor mistakes we might make. We must never act as if we had been 'caught' but to just pout and look down.

Linda and I bought our party and schoolgirl dresses. We had had so much fun we agreed to meet again soon and continue our studies of being a girl. I expected that we would be doing a lot more than just study when we were together.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
Man of the House Step-mom-to-be gets BIG surprise from step-daughter-to-be.in Transgender & Crossdressers
Rite of Passage Young boy turns 18, shemale sister turns him out.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
More Stories