Tracy, a young college student with a tragic past connects a free spirited girl with her own struggles who fully accepts him and his more feminine side that he harbors..... they spend one night in the city that they will never forget.
A message from the author: This story is different from most of what I have previously posted. It is a love story with some sex and crossdressing. If you are looking for forced feminization as I usually write, you will be disappointed.
I want to thank Annabelle Brito for reviewing and her suggestions that have greatly improved the story.
This story is a product of my own perverted imagination. It is complete fiction and any resemblance to persons living or dead is pure coincidence. Please leave your comments, good or bad. I try to learn from corrective criticism.
Enjoy!
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My first year of junior college was significant because of one person, Katie. I had always admired Katie from afar. I was too shy to talk to her but I lusted after her. She was pretty, smart, and a little kooky, but I couldn’t get up the nerve to talk to her. You can only imagine my surprise when I saw her approaching me, looking right at me. I looked around to see if anyone else was near that she might be looking at, but I was alone on the bench.
“You’re Tracy, right?” she asked.
“Yes and you are Katie, we have had some classes together.”
“Yeah, I guess so… I often see you staring at me. Why?”
“Ummm… I umm- I guess it’s because I think your beautiful and smart and really funny.”
Katie starred at me for a moment.
“Thank you” she said blushing “No one has ever told me that before.”
“They must have blinders on if they can’t see that.”
“So, why haven’t you ever talked to me or asked me for a date?”
“I’m really shy and I don’t know how to talk to girls.”
“You’re talking to one now or do you think I’m a golden retriever?”
I laughed at her remark.
“Well, if you’re not going to ask I will” she said “will you go out with me and maybe perhaps be my boyfriend.”
“I would love to be your boyfriend, but you really don’t know much about me.”
“I know you are very smart since you recognize my great beauty and intellect and fantastic sense of humor. With those qualities how can I resist finding out more about you.”
“Well, since you put it that way, I would love to. Of course, I will go out with you and hopefully be your boyfriend.”
“So, do you have plans for the rest of the day? If not, I would love to take you out.”
“Well, I was going to spend some time studying for that history test on Monday.”
“Supposing we get takeout and study together?”
“I would like that.”
“Can we study at your house?” she asked.
“Yes, my sister is at work and won’t be home till late.”
“What about your parents?”
“I live only with my sister. It’s a long story and I’ll tell you later.”
“You don’t have to if you don’t want to. I don’t mean to pry.”
“If we’re going to be boyfriend and girlfriend than you should know. It’s part of who I am.”
“I like you already Tracy. I have a feeling we are going to be great couple.”
She gave me a quick peck on the cheek and the most beautiful smile I had ever seen. I think I was in love with her already.
“Ok first order of business. What should we get for takeout?”
“I like most everything what do you want?”
“I asked you first. You choose!”
“How about burritos? There is a Mexican restaurant around the corner from my house that makes great burritos.”
“Then burritos it is. Let’s go!”
“She put her hand in mine and we drove to the restaurant in her car. After picking up the food we went to my house.”
“I’m anxious to see where you live, Tracy”.
“It’s not a big house but it works for Rebecca and me.”
“So, her name is Rebecca. How old is she?”
“She is 32, 12 years older than me. She pretty much raised me since I was 7.”
“What about your parents?”
“They are gone. Can we talk about this later. I will tell you everything.”
“Sure. I didn’t mean to upset you. Not a great way to begin a relationship.”
“You didn’t upset me. I just want to get studying out of the way so we can talk and get to know each other better.”
We reached our house. I let us in. Katie looked around and smiled.
“It’s beautiful. I love it.”
“It’s comfortable for us. Let’s eat and study. Then I will give you the grand tour.”
“Sounds good to me.”
We enjoyed our Burritos and washed them down with cokes. I cleared the table and we went over everything that was on the test. I was so impressed with how much Katie knew. She likes to act a bit off the wall, but she is so intelligent.
“Ok” she said closing her books. “Give me the tour and tell me about Tracy Corwin.”
After the tour we sat on the sofa in the family room.
“My parents were killed in a drive by shooting when I was 6 years old. I was in school at the time. They were what the police called collateral damage; they were in the wrong place at the wrong time.”
I always tear up when I tell the story. Katie wiped my tears away with her finger.
“It’s ok if you don’t want to go on” she said.
“No, I want to. Talking about them keeps them alive for me.”
She hugged me to comfort me and it felt so good.
I took her hand and held it while I continued.
“Rebecca was 18 and the courts said she was unable to care for me so I went into the system. She hired a lawyer and it took a year for her to get me back. She was a mother and father to me and I love and owe her so much. We don’t have any other family. The day she picked me up from foster care for the last time was the happiest day of my life.”
Now the tears were flowing. Katie put her arms around me and hugged me tight until I could stop crying. She took a tissue from her bag and wiped my eyes.
“Are you ok?”
“Yes I am fine.”
“What kind of music do you like” she asked changing the subject.
“Country, Jazz, Pop music mostly. What about you?”
“Classic rock mostly, though I do like country.”
“Ok I’ll put some music on.”
I found some classic rock I hoped she would like and put it on.
“For me” she smiled. “That deserves a reward for which she climbed on my lap, put her arms around my neck and give me a long passionate kiss. That had a predictable reaction from me which she felt on her against her thigh.”
“Does that mean you like me or is that a gun you are packing?” she laughed paraphrasing an old Mae West movie.
“I’m sorry” I said.
“I’m not.” She replied and began unbuttoning my shirt. Before I could stop her she discovered the yellow camisole I was wearing under my shirt.
She stared at it for a moment.
“I’m sorry. If you want to leave, I understand. I started to cry.”
“Why would I want to leave. When I found out my boyfriend has a new exciting side to him?”
“You’re not upset?”
“On the contrary. I am more excited than ever. So, tell me…. are you also wearing panties?”
“Ummm….Yes.”
“Do they match?”
“Yes, I am so embarrassed.”
“No! Don’t be. You don’t need to be ashamed of who you are. Own it. I love you even more. Now stop your crying and remove those pants so I can see my beautiful girly boyfriend,”
When I hesitated, she unbuckled my belt, unbuttoned my jeans and pulled them down exposing my yellow lace trimmed bikini panties that covered my hard-on.
Smiling, She sat on my erection wrapped her arms around me and gave me the most passionate kiss.
“Mmmmm” I moaned.
She bounced up and down and rubbed herself on my erection. The fee of the fabric and the way she rubbed her bum against my cock was driving me into ecstasy.
“If you don’t stop that, I will cum.”
“Well, I don’t want to waste it that way.”
She dropped to her knees and pulled my panties down. She slowly stroked me, keeping me erect but not letting me cum.
“So do you wear only lingerie or do you like to dress up completely?”
“I dress completely as a girl….ahh…”
I couldn’t look at her as I moaned.
“I bet you make a very pretty girl. You have fine features. That with a bit of makeup would bring out your beauty. Hey look at me!”
I looked up aware that I was blushing.”
“I’m sorry Katie but I am embarrassed about it.”
“I don’t want to hear it. You are my boyfriend unless you want me to leave?”
“No, no, please don’t leave?”
“I have no intention of leaving but you need to be proud of yourself and not ashamed of who you are, especially with me. Do you understand?”
“Yes’ I replied.
“Good, do you wear makeup, heels?”
“Yes.”
“Are you a pretty girl?”
“That’s for others to say, Rebecca thinks I am.”
“Oh, she knows?”
“Yes, she helps me.”
“She sounds like a wonderful person and a great sister.”
“She is the best.”
“So how and why did you start dressing like a girl.”
“Well, it was when I was with a foster family. They had 2 girls 8 and 12. I was lonely and sad and wanted to play with them. They told me they only play with girls and if I wanted to play with them, I had to become a girl. They dressed me up when I wanted to play with them. My hair was long and since my foster mom didn’t have much money I didn’t get a haircut when I was living with them. She paid little attention to me. I think she fostered me for the money, but I don’t know that for a fact. I didn’t care much at first about wearing a dress but after awhile I liked the clothes and mostly the attention, they gave me when I was dressed like a girl. I think that is what hooked me.”
“Wow, so your foster sisters helped you discover this side of you?”
“I guess so…when Rebecca finally gained custody of me my foster mom packed a suitcase for me. When we got home and Rebecca opened the suitcase there was a dress and panties on top. I think one of the girls put them in after my stepmom packed it. Rebecca asked me if it were mine. I told her it was and why I wore it. She asked me if I liked wearing dresses. I told her I did. The next day she took me shopping and bought me a dress, some panties, some socks and a pair of Mary Jane shoes. It was a princess dress. She told me that it was ok for me to like girls’ clothing and it would be our secret. No one had to know.”
I was emotional by that time, but I was still rock hard.
“Hey, it’s me and I love you. If you want to be a girl with me, that is cool. I find it exciting. I like to wear different costumes too.”
“I actually wear girls’ clothes all the time at home. I am more comfortable in them and like the way I look.”
“I can not wait to see you all dolled up, but first I have something to tend to.”
She leaned over and licked my shaft. I had never felt anything so good. Her tongue played with the tip and then she took my whole cock in her mouth. I was so close before she swallowed me that I exploded immediately and Katie swallowed it all.
“Mmmm,” she moaned as she swallowed my sperm.
“That was yummy” she said and kissed me, sticking her tongue in my mouth so I could taste myself.
“I want to pleasure you now.”
“I would love that.”
“I’m so embarrassed. I’ve never been with a girl. I don’t know what to do.”
“It’s ok. I will guide you.”
“Take off my blouse!”
I unbuttoned her blouse and took it off her. She wearing a very pretty black bra.
“Perfect!” she said and leaned over to kiss me. “Now remove my bra! It hooks in the back.”
I fumbled with the hooks but was finally able to undo them. She allowed the straps to slide down her arms and the bra to fall on the floor, exposing her perky breasts.
Smiling at me she says “You’re becoming a pro. Now squeeze my breast and play with my nipple.”
I follow her order and she starts to breathe hard. The more I tickle her nipple the harder she is breathing.
“Squeeze the nipple, hard” she gasps. “Oh my god! That feels so good.”
“Now with your other hand reach under my skirt and take off my panties.”
“Yes ma’am.” I said and did as she told me. Her panties were soaked. I slid them off and tossed them to the side.
“You are doing so well Tracy. Now rub your finger on my pussy.”
She gasped and moaned.
“I am so turned on Tracy! Stick your finger in my pussy and move it around.”
“Oh yes!” I love what you are doing.
She lifted up her legs and placed them on my shoulder leaving her pussy right in front of my face.
“Do you know what I want now?” she asked.
“I think so.”
I leaned over and licked her pussy.
“You got it Tracy”
She smelled and tasted so good.
I slide my tongue inside her and heard her gasp and moan.
“Keep it up baby I love you!”
Her words were like music to my ears and I worked harder to bring her off.
There is a little nub there. That is my clit. Feel it with your thumb but keep licking.
I felt the nub and rubbed it gently.
Katie shrieked and locked my head between her thighs. Her breathing was shallow and rapid. She convulsed once, twice, three times before settling down. She soaked my face with her delicious juices. She put her hand on mine and pulled it away from her pussy.
“Oh Tracy, that was awesome.”
She slid her legs off my shoulders and reached for me. Then she pulled me too her and kissed me almost violently. She darted her tongue in and out of my mouth and pulled my head down to her chest. She laid down on the sofa, and pulled me on top of her. Then she wrapped her hands and legs around me and hugged me tightly.
Catching her breath, she tells me “You are one fantastic lover”.
They were words I loved hearing since I felt like such an amateur having to follow her directions.
“Tracy, I think we work, do you?”
” I do too.”
“Let’s get cleaned up and I want to meet my new girlfriend. How does that sound?
“Are you sure?”
“You bet. What kind of girlfriend would you be if I can’t meet you?”
We got off the sofa and headed to the bathroom. After completely undressing, we jumped in the shower together. We washed each other kissing every few seconds. I thought that if this is what it’s like being in love, I’m all for it.
We dried ourselves. Tracy borrowed a robe so she could get a clean change of clothes from her car.
“I’ll dress in the bathroom. When you come out of your room, I want to meet my new girlfriend! And that is an order miss!” She gave me her winning smile and slapped my ass as she walked away.
Inside my room, I put on white panties and a matching bra. I put on nude panty hose and a short white dress. It was one of my favorites. White Mary Jane shoes with 2-inch heels followed. I brushed my hair into a high pony tail with a white scrunchy. My makeup consisted of foundation, black eyeliner and mascara, pink eyeshadow, pink blush and lipstick. I was happy with the way I looked and hoped Katie would be also.
I took a deep breath and thought to myself “here goes”. I was extremely nervous that she would hate me when she saw me like this in spite of what she had said. I walked into the living room where she was sitting, drinking a coke. I stood before her, waiting for her to look up.
Her eyes popped open when she saw me and said nothing for sever moments.
“Oh my gosh! You are a vision, the vision of an angel. You are so beautiful!”
I swear my heart had stopped waiting for her to say something, prepared for the worst.
“Come here girlfriend and sit by me!”
“That is a beautiful dress! Oh my… you are a beautiful girl, I can’t stop looking at you. I love my new girlfriend.”
“I love you too, Katie. I am so happy you accept this side of me. I could never give it up. It is a big part of me.”
“I would never ask you to give it up. I think I will enjoy it as much as you do so don’t ever apologize for who you are. Ever! Do you hear me girl?”
“I hear you.”
I sat down next to her, smoothing my skirt beneath my butt. She put her arm around my shoulder and pulled me to her.
“You make me so happy. Tomorrow, I am going to take my new girlfriend out for the day.”
“I would love that! Sometimes Rebecca and I go out, but she works so much there isn’t much time for that and I am nervous about going out alone. Being your girlfriend is better than anything I have ever donefs.”
“I never had a real girlfriend, but now I do.”
Her lips brushed mine.
“When does Rebecca get home? I’m anxious to meet her.”
“Not for another couple of hours. She works so hard and long hours. I worry about her but she tells me I should not worry; it is her job to worry about me not the other way around but I can’t help it.”
“She sounds like an amazing person. You are so lucky to have her for a sister.”
“Enough about me” I said “I want to hear your story.”
“I warn you it’s not a pretty one.”
“I’m here for you as you are for me!”
“I know that and I appreciate it. Here goes!”
“I left home when I was 16. My folks are part of a religious cult. They believe if you don’t follow their ways, you go to Hell. My brothers and sister drank the Kool-Aid, but I didn’t. I was constantly punished for violating their traditions. I was not a perfect child and some of the things I did were designed to piss them off. I drank, my skirts were too short, my makeup was forbidden, I flirted with boys. It seemed that everything I did was wrong. I still have scars from some of the beatings I took.”
“Oh Katie. I am so sorry.”
She patted my knee.
“It’s ok. No one will ever do that to me again. I’m ok now, especially since we found each other.”
“How did you live?”
“I’m not proud to admit it, but I stole some money from my parents and siblings. I had enough to buy a used car since I thought that would be my home for some time. I was right about that. I got a part time job which helped feed me and maintain the car. Most of my clothes are from thrift shops.”
“I went to school and studied at the library, maintaining good grades. I took self-defense lessons which were free at the community center. About a year after I moved out, I met a boy. He was 18 and on his own. I moved into his apartment, thinking I was in love with him. He turned out to be a real loser. I discovered that he was doing drugs and said good-bye. Again, I’m not proud of it but I took some money from him when he was stoned and passed out.”
“I graduated from high school 3rd in my class and I am on a scholarship at uni. I still don’t have enough to rent an apartment so I live in a car.”
“Aren’t you worried being alone at night?”
“Believe it or not, the city has safe parking in churches and community centers where there are restrooms, showers, and at least one policeman is on duty. We can’t use them before 9:00 PM and have to be out by 6:00 AM.”
“Katie, I had no idea you have had such a rough life. Mine seems like paradise compared to yours.”
“How could you know. I don’t tell people my story because I don’t want their pity, so don’t you pity me, girl!”
“She smiled and I smiled back. I hugged her wanting to take away any pain she has.”
“I’m ok Tracy. It’s not a perfect life but I can manage. Someday I will be on top. I have no doubt about that.”
“I don’t either Katie. You are an amazing girl and I believe you will accomplish whatever you set out to. I love you so much even though we just met.”
“Ok, it is getting a bit heavy. How soon will your sister be home?’
“Pretty soon. Would you like to live here with us? I will ask Rebecca if it’s ok?”
“I don’t want to cause any problems.”
“At least plan on spending tonight here. If you need laundry done, I will do it for you. Anything you want.”
“You’re so sweet. Ok I will stay the night and we will see about anything else. Being together is very inviting.”
We snuggled on the couch kissing and feeling each other. She treated me like a girl and I loved it.
“I hear the garage door opening. Would you mind waiting in my room so I can talk to her first?”
“Ok girlfriend” she gave me a kiss and went to my room.
A couple of minutes later Rebecca walked in. I was waiting for her and hugged her tightly. This was not unusual and she hugged me back and kissed me on the cheek.
“How was your day?” I asked.
“Ok, but happy to be home from a long day. I see you are dressed up fancy today. You look beautiful Tracy. You do make a very pretty girl.”
“Thank you, sis. I have to talk to you.”
“Sounds serious.”
“It is!”
“Ok let me put my bag and brief case down. Shoot!”
“I have a girlfriend and I want you to meet her.”
“What? When?”
“She is in my room, but I need to talk to you first.”
“Oh my gosh! Has she has seen you like this?”
“Yes, I thought it was only right to let her know the whole me.”
“Obviously she accepts this side of you. That alone is a big plus in her favor,” she said. “Let me get a beer and sit with me on the sofa and tell me what you need to. I’m always here for you.”
I told her all about Katie. I told her everything I knew.
“She sounds incredible I can’t wait to meet her.”
“In a moment Rebecca. I have invited her to stay with us so she doesn’t have to live in her car, but obviously you have the final say.”
“I trust you Tracy but let me meet her and I’ll decide whether or not to give her a trial. From what you have told me I think we will allow her to stay for a while at least. How does that sound?”
“It sounds great. I will get her.”
I went to my room and took Katie’s hand. She was shaking she was so nervous. I told her it would be ok. I led her over to Rebecca. Rebecca stood up, smiled and opened her arms for a hug.
“It is so nice to meet the girl who stole my brother’s heart” she said.
Katie smiled and said “I was so looking forward to meeting you. He told me how you took care of him. You are an amazing person.”
“From what Tracy told me you too are an amazing person. Come let’s sit at the table and talk. Tell me all about you. I’m starving. Are you guys hungry?”
“We had Burritos sis and I bought one for you. Let me heat it. Do you want another beer?”
“You’re an angel Tracy,” Rebecca said. “He will make someone a great wife someday. She said to Katie.”
We all laughed even though it was a standard joke of hers. We talked for some time until we all were tired.
Rebecca and Katie got along great and Rebecca agreed to allow Katie to stay, at least for a few days and then see how things went.
Rebecca got up and started towards her bedroom. She stopped and turned to me.
“Tracy, come with me for a couple of minutes.”
I walked up to her and followed her to her bedroom.
“I think you have a winner there for girlfriend. Finding someone who can accept your crossdressing and even enjoy it is rare. But more than that she really has her shit together. Especially after what she went through. I’m going to the beach for a few days. I will be leaving early tomorrow morning and be back on Monday.
She reached into a drawer on her night table and handed me a pack of condoms.
“Use these!”
“Why do you have these? I asked.
“I may be a sister, but I am not a nun! Now go to your girlfriend.”
“I love you sis,” I said as I hugged her.
“I love you too sis!” she said with a smile
When I returned, Katie was not there. I panicked for a moment until I heard the front door open. She walked in carrying her suitcases.
“If I am going to be staying. I will need clothes. Where should I put these?”
“I’ll make room in my closet.”
“Right, with all your dresses there is no room my sweet girly boyfriend.”
She gave me a soft kiss on my lips.
“You can keep your things in the guest room for now” I replied and grabbed one of the suitcases to carry and almost dropped it. I looked at her in shock.
“I do weight work in the gym” she said with a shy smile as she shrugged her shoulders.”
She picked up the suitcase easily and carried it to the guest room.
“I’ll grab a nightgown and toiletries and be right with you.”
I walked slowly back to my bedroom amazed that she was stronger than me.
We crawled into bed together and hugged. We were both exhausted. She spooned me in bed.
“Good nig-ah”
Katie’s hand had found my penis under my panties and began slowly stroking it.
“Just relax, I’m going to help my girlfriend relax.”
“Ahh..ahh,” I moaned as she slowly masturbated me.
I was lost in ecstasy the way she held me tight and massaged my penis. Katie’s other hand pulled down my panties, I then felt a finger enter my ass.
“Argg…” I orgasmed.
“Shhhhh…..It’s ok,” she said holding me tight as I shuddered. “Just relax now.”
She slowly let go of my penis and retreated her finger from inside my bum.
“Good night Tracy,” she then kissed me on the cheek.
I fell asleep peacefully like that in her arms.
When I awoke the next morning she was not in bed. I got up and saw my French maid’s dress hanging on the door with a note on it.
Tracy, put on this dress with appropriate underwear and shoes and meet me in the dinette!
I smiled. I hoped she would be into some role playing. I showered quickly and dressed in the maid’s dress with black fishnet stockings, lacy white bloomers and attached petticoats that showed beneath the skirt, and black shoes with 2-inch block heels. I did my make up and leaving my shoulder length hair down I put on the little white cap and headed to the dinette wondering exactly what she had in mind.
I was in shocked when I saw her. She was dressed like a man wearing my clothes, actually a rather effeminate man but nonetheless a man.
Keeping a rather straight face ‘he’ said
“Get over here girl!”
“She is into role playing I thought and walked to her.
“Yes sir” I replied, as I hustled over to ‘him’ and curtsied.
“Why is this kitchen not clean” ‘he’ asked in a stern, almost scary voice.
“I’m sorry sir, I was too tired last night.”
“You need to fix me breakfast and make this kitchen spotless.”
“Yes sir, right away.” I said and turned to start his breakfast.
“I’m not through with you yet, girl!” ‘he’ said as ‘he’ grabbed my arm and pulled me towards ‘him’.
I could feel her strength as she pulled me and remembering how she easily carried the heavy suitcase. I have to admit that I felt embarrassed about not being able to pick it up.
“You need to be punished for you negligence girl!”
“Yes sir!”
“Call me Mr. Gus, girl. And since you’re merely a servant girl you do not need a name.”
‘He’ easily dragged me across ‘his’ lap. ‘He’ lifted my dress and petticoats and spanked me on my ass! ‘He’ wasn’t hitting me hard, but I felt a bit of humiliation at how easily ‘he’ handled me. On the other hand, I did have a solid erection.
“Now fix me bacon. eggs and coffee and get that kitchen cleaned.”
I fixed ‘him’ breakfast and curtsied when I served it. “He’ ordered me to stand by ‘him’ demurely while ‘he’ at so I could fetch ‘him’ more coffee when he desired. I don’t think I had ever been so turned on as I was then. I cleaned up the kitchen. When ‘he’ finished breakfast I washed the dishes and wiped down the table.
“I am going to inspect the job you did girl and if it is not perfect, there will be consequences.
“Yes Mr. Gus” I replied and curtsied. I realized I really was very nervous. The whole scene seemed so real to me.
“Good job girl” ‘he’ said after finishing his inspection. He even squeezed my ass as ‘he’ walked past me.
I felt a sense of pride but I could not revel in it for long as ‘he’ grabbed my hand and ordered me to follow ‘him’. We went back to my room. ‘He’ ordered me to change the linen on the bed, straighten up the room and clean the bathroom. This was not turning into sexual role playing as I hoped and I was disappointed, hoping that we would end up in bed. On the other hand, I enjoyed wearing the dress and it was erotic the way Katie, or should I say ‘Mr. Gus’ ordered me around.
When I finished my job which took about an hour, ‘Mr. Gus’ gave a cursory inspection and was satisfied. Katie turned to me smiling.
“Did you enjoy the role play Tracy?”
“Oh yes. You were so good. You actually scared me. I was afraid you were going to spank me hard.”
“I won’t ever hurt you.”
“I believe that, but at the time it was so real.”
“Take a nice bubble bath. Then when you get dressed I am going to take my beautiful girlfriend out for brunch and a day she won’t forget.”
“It sounds wonderful!”
She took me in her arms and lavished me with kisses. Feeling my erection, She pushed me onto the bed, lifted my skirt and petticoats. and pulled down my panties causing my erection to pop up. She leaned over me and wasting no time took it into her mouth. It took me all of about 30 seconds to explode into her mouth. She swallowed all or most of it. She crawled up on top of me and kissed me, depositing the last of my semen in my mouth. This would become routine whenever she gave me a blow job.
“Why did you feed me my semen.”
“Because girls need to know what it tastes like.”
She lay on top of me for several minutes while we both recovered. Then she rolled off me and stood up. Pointing me towards the bathroom she slapped my ass and told me to get to it. She would be waiting.
When I returned to the bedroom with a towel wrapped around my chest I saw she had laid out clothes for me, all pink. She laid out a white lacy thong and bra set along with pantyhose. The ultra-short mini sleeve less dress was pink.
She left me pink Mary Jane Shoes with a one inch heel. I dressed quickly but took my time applying my makeup. The dress made me feel very exposed, the lacy underwear underneath and the tight soft dress made me feel like I was wearing nothing.
I wore my hair down and when I was ready I took a good look in my full length mirror. I felt very girly and was happy with my appearance.
I went to Katie and saw that she was still dressed in my clothes. I smiled at her happy to role play boyfriend and girl friend for the day. Acting the aggressor, she took me in her arms and gave me a passionate kiss.
“Call me Gus today” she smiled.
“So where are we going, Gus” I asked.
“It’s a surprise.”
‘He’ grabbed my hand and led me out to ‘his’ car where ‘he’ opened the passenger door and held it for me.
“I could get to like this” I thought.
“Where are we going?” I asked ‘him’ again.
“You’ll see and if you keep asking I will stop the car, and take you across my lap.”
We stopped at the city diner.
“They have the best brunch in town and nothing is too good for my best girlfriend.”
Gus aka Katie took my hand and led me to the restaurant.
“It’s so expensive. You don’t have to do this.”
She put her finger to my lip.
“I want to show you how much I love you and I will. Now just enjoy it.”
“I leaned over and brushed ‘his’ lips with mine.”
We had a fabulous meal. I looked at Katie, and yes it was hard to think of her as a male, and my heart filled with joy.
We got into the car and drove for about an hour north up the coast. The view was beautiful. We got out of the car and holding hands, took a walkway along the edge of the cliff. We stood there for awhile and enjoyed the view.. There were sealions sun bathing on the rocks and whales jumping out of the ocean. I had never seen anything like it. We must have watched them for an hour, holding hands the whole time.
“Tracy, come with me. There is more.”
‘He’ led me to a building near the parking lot. He paid to get in.”
“What is this?”
“You will see.”
We got into an elevator and it took us down. I don’t know how far. We got out and saw a spectacular view. There were windows in the walls under the ocean and all kinds of sea creatures were swimming. Some came to look at us while we looked at them. It was one of the most beautiful sights I had ever seen.
“Gus, I love it! You are the best boyfriend ever.”
“Anything for you Tracy, anything at all.”
“You know how to make a girl feel good.”
“I should know” ‘he’ said with a grin causing me to laugh.
“Have you had enough? ‘he’ asked me.
I nodded. We took the elevator up to the ground floor. Once again Gus held the door open for me. ‘He’ got into the driver’s seat and looked at me. I was crying.
“What’s wrong?”
“Nothing, I am so happy I am just overcome with emotion.”
‘He’ reached over and patted my knee.
“The day is not done yet.”
It was getting dark as we headed back to town.
“Hungry?” ‘He asked me.’
“Yes, but let me pay.”
“No girlfriend. This day is on me.”
We stopped at a little café and shared a dish since neither of us were starving after the brunch. I was surprised that Gus carried a sports bag in with ‘him’.
“What is in there?”
‘He’ smiled and said “You will find out later.”
After we finished eating and were enjoying coffee, Gus picked up the bag and headed to the rest room. 15 minutes later Katie emerged carrying the bag and looking spectacular in a teal strapless minidress.
“It was time to say good bye to Gus” she said.
“Aw, I was really falling for ‘him’.”
“Maybe ‘he’ will make another appearance, but not tonight.”
Katie paid the bill and we left the café.
I’m not holding the door for you that was Gus’s deal. I pouted and she laughed and shook her head. Them we went to a mysterious destination, at least it was a mystery for me.
“Wow! Parking is tough here. Their parking lot is too small.” Katie remarked.
She drove around and found a spot a few blocks away. We got out of the car and Katie took my hand.
“I love you Tracy” she said and give me a light kiss on the lips.”
I was on an emotional high the whole day. I grabbed her arm with both hands and leaned my head on her shoulder. We walked the few blocks to a club.
“It’s an under 21 club Tracy. They do not serve alcohol. I was here once with the ‘asshole’ I was living with. I hope you will like it.”
“I’m sure I will.”
We entered and it was like wall-to-wall people with loud music blaring.
“I need to use the ladies’ room” I shouted in her ear.
“Fine, I’ll get us a couple of drinks.”
I weaved my way through the crowd and found the ladies’ room.
“One disadvantage to being a girl” I thought as I got on a line to get in.
I looked longingly at the men’s room which had no line. Fortunately, it moved reasonably fast and in about 5 minutes I was sitting on the toilet relieving myself. I checked my makeup and refreshed my lipstick.
As I exited the ladies’ room a guy approached me.
“Hi, I’m Freddy”
“Tracy here.”
I was very nervous. I had never interacted with boys when in girl mode.
“My buddy and I saw you and your girlfriend enter the club. The two of you are the hottest girls here. My buddy is hitting on your girlfriend now. Let’s dance?”
“Thanks, but no thanks.”
“What?! Am I not good enough for you?”
“It’s not that, my girlfriend and I are together.”
“So are we, so why don’t we make it a foursome?”
“I don’t think so, but thank you for the offer.”
“Why not? I’m a pretty good looking guy. I know how to give girls a good time.”
“I’m here with my girlfriend. Leave me alone.”
I turned and started to head back to meet Katie.
“Come on, only one dance” he said as he grabbed my butt.
“Let go of me!” I said in a loud voice.
A man came over and grabbed him.
“Let’s go little boy” he said “It’s time for you to go home’”
Holding him with his arm behind his back he marched him towards the entrance.
The whole incident got to me and I started to cry. A couple of girls came up to me. One of them handed me a tissue and told me to come with them. They took me back into the ladies’ room and sat me down.
“Hey, don’t let a jerk like that get to you. Is that the first time it’s happened to you?”
“Yes.”
“Some guys are real assholes and they think they are God’s gift to women.”
I finally stopped crying and was composing myself.
“Are you here alone?”
“No, my girlfriend is getting us drinks.”
“Would you like us to walk with you?”
“I think I’ll be ok, but thank you.”
I worked my way back to Katie. She noticed my red eyes immediately.
“You were crying.” It was a statement. “Are you ok?”
“I am now.”
“What happened?”
I told her everything, including the part about his friend hitting on Katie and how frightened I was when he grabbed me. She said nothing, but the look on her face was one of anger. She did calm down and said no one had hit on her.
“Katie, I want to go home.”
“Sure thing. This was a bad idea anyway.”
“No, it was a good idea. You couldn’t know what was going to happen.”
She took my hand and led me out of the club. I was scared walking the few blocks towards the car. About a block from the car we saw Freddy walking towards us.
“Well, well, well, you did have a girlfriend.”
Katie stepped in front of me.
“Get lost!”
“Oh, a feisty one. Maybe I will do you first.”
Katie looked him over and smiled at him.
“Maybe I would like that” she said.
“Katie!” I yelled to her.
“Well then, come to me baby” he said as he grabbed her left arm and swung her into his body.
Everything happened so fast it took me time to process. As he swung her around and into him, Katie jammed her right elbow into his gut causing him to bend over and hold it, releasing her. She then gave him her elbow in the nose and I swear I heard it break which caused him to fall on the ground, crying.
“If you ever even look at my girlfriend I will castrate you! If I ever hear of any girl being harassed around her I will come looking for you and castrate you. Do you understand?”
“Yes” he responded crying like a baby on the pavement.
“Let’s go sweetie” she said.
She grabbed my hand and we walked to the car.
We were quiet as she started the car and we headed home.
“Oh Katie, you were so awesome.”
“She turned towards me and smiled. I was, wasn’t I?”
“How did you do that?”
“Living on the street you need to learn to take care of yourself. I took classes in self defense. He wasn’t the first guy I had to fend off.
“I am so turned on now.”
“I will take care of you when we get home.” she told me.
“I can hardly wait.”
“Did you enjoy today, my love.”
“It was magical. “
She smiled and continued driving. As soon as we entered the house we started tearing each other’s clothes off, leaving them scattered on the floor from the front door to my bedroom.
Katie pushed me on the bed and smothered me with kisses, biting my shoulders and neck. Katie rode me so hard that I began moaning like a girl naturally as she pounded her pussy on me.
Our love making didn’t last long, but it was intense. Then we laid there for awhile in each other’s arms recovering.
“You have such a cool sister Tracy; it was very kind of her to leave us those rubbers.”
“Yeah…she is very cool, you are too,” I said breathing heavy after an incredible orgasm.
“I don’t know about you, Tracy, but I need a drink.”
She meant she needed a coke and we put on our nightgowns and went into the kitchen. We sat silently for awhile just gazing into each other’s eyes.
“If we are to be together Tracy, there are going to be rules.”
“Rules?’
“Yes, and I am going to make them. Any objections?”
This girl turned me on in so many ways.
“None!”
“Good. The first one is you are not allowed to wear anything masculine. You will wear dresses and skirts exclusively unless you have my permission otherwise.”
She stopped to see my reaction.
“What about school I can’t wear a dress to school.”
“You will wear a dress on Monday and go to administration and tell them you are transitioning. Your name is unisex so the paper work should be minimal. You will start low dose female hormones so your breasts and curves can develop but be able to get and maintain erections and please me that way. Viagra or Cialis can help with that. Under no circumstances will you have your banana and its apricots removed. They belong to me. Any questions?”
I shook my head. She turned me on so with just her words.
“Since I am clearly the dominant one in this relationship I will make any rules I deem necessary and you will obey them.”
“I will obey you with love” was my response.
“If I see any disobedience on your part expect to be across my lap.”
She looked at me to see my reaction. I thought I would orgasm without touching myself.
“That’s it for now.”
“Oh, one other thing, you will learn to service my banana, or rather Mr. Gus’s banana.”
“What do you mean?”
She smiled at me “You will find out when the time comes, now come sit on my lap.”
“Oh Katie, I love you so.”
We kissed for several minutes before going back to the bedroom for another round.
Epilog: 6 Years Later
Katie and I got married after graduation. WE both wear wedding dresses. I am legally a female though I retain my banana and apricots as Katie calls them. I work as an Executive Assistant. At Katie’s insistence I own no pants or any men’s clothing. I haven’t worn pants since that fateful night 6 years ago.
Katie graduated top of the class, was valedictorian and went to law school. She also graduated top of her class there. She works for a children’s aid organization to prevent child suffering like she went through. I am so proud of her. We are more in love than ever.
Rebecca married the man of her dreams and has a little girl of 3 and a boy of 1. Katie and I are aunts and we love our niece and nephew.
One more thing to tell and our tale ends. Occasionally, Gus makes an appearance; usually when I have done something wrong. Then I suffer the indignity of laying across ‘his’ lap and then servicing ‘his’ banana and apricots. Let’s just say we have a very healthy sex life. My life could not have turned out better.
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