Tiffany
By Pamela
My mom and dad got invited to a destination wedding in Hawaii. It’s an adult only affair lasting for a long weekend. They left my older sister Karen in charge of me. I’m twelve and she’s sixteen and mature for her age. Mature in the sense that she takes school seriously and gets good grades as well as the fact that boys are always seeking her out hoping to date her. I guess that has to do with her girl attributes!
I’m a fairly normal boy in the sense that I like playing baseball and soccer. Football not so much. I have to confess that I’ve always liked playing with girls too. Hopscotch and jump rope are fun and I like the way girls think. I like what they talk about. I like listening to them. Since it would cause the guys I know to think of me as being weird, I haven’t exactly shared this other part of myself. I’m happy to have my own private enjoyment in playing with girls – the world doesn’t have to know about it.
I’ve barely begun entering puberty in case you’re wondering. I’m kind of slender and small boned – and my face has a purity and sweetness to it that could possibly be interpreted as being feminine traits. I do keep my hair kind of long – my parents were hippies a long time ago and that fits in with their worldview. Besides, less haircuts less money spent on haircuts.
My parents gave Karen a long list of don’ts for when they’re away. No boys in the house – ever! No girlfriends over in the evening. No parties. House kept clean, and so on and so forth. Karen is trustworthy so this should all work – except for the fact that Karen and her best friend Lisa have made big plans for the weekend. Their boyfriends, Earl, and Marcus, respectively, are to come by for what they hope will be a make out session unlike any one the girls have had before. No parents looking over their shoulders to make them nervous. It’s a dream come true!
You might be wondering about me ratting on my older sister. The fact is that she’s bribing me into keeping my mouth shut and also staying in my room while she and her friends are having their romantic adventure in the living room. Karen assured me that her one transgression will be having boys in the house. One little thing she called it and nothing for me to worry about. She won’t be going to hell for having done this one little mischievous thing. And if she’s not going to hell I won’t be going to hell for taking a bribe.
***
After mom and dad had stepped into their Uber and were whisked away to the airport, Karen answered a hysterical call from Lisa. It turned out that her parents were suddenly called to a destination funeral and she had to babysit her twelve year old sister, Monica, for the weekend.
“All our wonderful plans are destroyed!” Lisa moaned. “You can go on ahead without me. Have fun with Earl!”
“Let’s not give up hope so easily,” Karen said. “Can’t you bring your sister here with you? She can play with my brother, Blake. They’re the same age.”
“You know Monica. She’s a little princess. She’s so bloody feminine. She only plays with girls, hates boys. And not just any girls. She prefers girls that love wearing pretty party dresses and feminine clothes. It drives my mom nuts to have such a girly girl daughter but she is what she is. Monica will certainly refuse to accompany me to a house where she has to play with a boy. She also won’t be happy unless the girl is like herself.”
“I see what you’re saying,” Karen said. She thought for a moment and said, “I have an idea. Let me call you back in an hour and I’ll let you know if this can solve our problem.”
***
Karen went to my room where I was busy looking over my coin collection. “Blake dear, how would you like to earn double what I offered you to keep quiet about my boyfriend coming over?”
“Double? You’re going to do something really bad?”
Karen laughed, “Not at all. It’s just that Lisa is coming over with her younger sister Monica. She’s your age and I’d like for you to play with her while Lisa and I are entertaining our boyfriends.”
“Is there something weird about her?” I asked
“Why do you say that?”
“Paying me to play with her? I don’t see why I wouldn’t be happy playing with her for free.”
“You’re smart, Blake. Yes, the reason I’m offering to pay you to play with her is that Monica only likes to play with girls. She’s not comfortable playing with boys.”
“Then how can I play with her?”
Karen hesitated and finally said in a low voice, “You’d have to pretend to be a girl.”
I wasn’t sure I had heard her correctly. “Me be a girl?”
“Yes.”
“How do I do that? I mean, are you crazy?”
“Bear with me, Blake. If we tell Monica you’re a girl she’s automatically going to think you’re a girl until proven otherwise. I mean she’s not going to be suspicious. So all you have to do is maintain her belief that she’s indeed with another girl.”
“Yeah, but …”
“Let me finish. I’ve seen you playing with the neighborhood girls so I know you do like to play with girls. I’ll get you looking exactly like the kind of girl that Monica likes to play with and all you have to do is imitate her. Do what she does and you’ll have no trouble being the type of girl she wants to play with.”
“You’re actually serious about this?”
“Yes. It means everything to me to have Lisa over here with Earl and Marcus. She and I have been planning this for weeks! Can you find it in your heart and wallet to do a little favor for your big sister?”
“Well, I don’t know.”
“Please, pretty please?”
I couldn’t help myself from laughing and said, “Okay, okay. I can try to do that. But what about mom and dad? They’ll kill us and especially you if they find out.”
“How are they going to find out? You’ll be in the house the whole time. I won’t tell. Will you?”
“No, of course not,” I said.
“Good!”
“I have to dress like a girl?”
“Yes. I have everything you need. Some of my old clothes that I’ve outgrown should fit you perfectly. I have a wonderful party dress and panties, tights, and a training bra.”
“A bra, too?”
“Yes. Girls your age are very sensitive about wearing bras. I’m sure Monica is wearing one and you ought to have one also.”
“Well, whatever. You know best.”
“I love you Blake. You’re the best. One thing is that we’ll call you Tiffany instead of Blake. A pretty girl’s name like that will help cement the illusion.”
“Fine. I’ll be Tiffany!”
***
Karen called Lisa. “I solved the problem!”
“How in the world did you do that?”
“Blake has agreed to be a girl – a girl just like Monica so she’ll be happy to be here.”
“Go on, you’re pulling my leg!”
“No, it’s true. I’m doubling my bribe and I already knew that Blake has no problem playing with girls. I just have to dress him up, work on his hair and maybe a little makeup and he’ll be Tiffany – I’m calling him Tiffany.”
“Fantastic!” Lisa said. “I’ll tell Monica that you have a lovely sister named Tiffany that’s her age.”
“And that Tiffany loves the same sorts of pretty dresses and clothing that Monica does. Tiffany still plays with dolls just like Monica.”
“This just might work,” Lisa said. “Oh how wonderful to be alone with Marcus and no parents around!”
***
After lunch, Karen called me into her bedroom. “We’ve got an hour to turn you into Tiffany. First thing is take off your clothes and put on these panties. I’ll turn my back.”
Karen handed me a pair of pink, cotton panties. I took off my pants and underpants and my shirt. The panties were softer and more delicate than my boy underwear and they didn’t have a pee hole. I stepped into them and pulled them up to my waist. Karen turned around to look me over. “Very good, Tiffany. They fit perfectly. Now hold out your arms in front of you.” I did as she said and she held up a pink bra and put my hands though the straps and up my arms to my shoulders. She went behind me and fastened the bra on.
As I looked down on my chest I noticed that there were a few small red heart appliques on the bra cups. “My God you’re adorable,” Karen said.
“I am?”
“Yes. Your cute body in the panty and bra look just like any girl does at your age. Well, wait a minute, you should also wear the falsies I wore when I was first wearing bras.”
Karen went through a drawer and found two foam falsies that she slid into my bra. “Wow. That’s cool. You’ve got a cute little chest now!”
I looked at my chest again and I was surprised by how nice it was to see that I had small breasts in my bra. Girls seemed to have no end of wondrous things. “I’ve got little breasts now,” I said. “Thanks.”
Karen laughed. “My pleasure. I knew that you’d make a pretty girl, and you certainly do! Now I have white tights for you to wear. I’ll have to help you on with them. Watch how I do it so you can do it by yourself in the future.”
As Karen rolled up each leg of the tights and put my feet in them I asked her, “I’ll be dressing up again like a girl?”
“Probably. Tonight you’re having a sleepover with Monica. Tomorrow morning you’ll have to get dressed again. Then maybe in the future, who knows?”
“I see.”
Once the tights were on Karen said, “You’re all girl Tiffany! This is going so much better than I thought possible!”
“Now a dress?” I asked.
“A slip comes next …”
“A slip?”
Karen showed me the white full length slip she was holding. “This will help smooth your profile in the dress.” She put it on over my head. “Now I’ll do your hair and makeup. Girls put the dress on last so it doesn’t get any powder or rouge on it.”
“There are so many things to being a girl,” I said.
“That’s true,” Karen said. “Girls like to look good. In particular, that means wearing the right bra. If you were a bit older then we might also consider a nice foundation garment for you.”
“I don’t understand.”
“See how my hips are round and shapely? It’s the way girls are. Boys don’t get hips like girls do. And of course boys don’t get breasts like girls do. Between our hips and our breasts, we have thin waists and the curves that go along with that are particularly pleasing to boys. There are many choices of clothing that girls can wear – foundation garments – that help us have nice curves.”
“Like what?”
“Girdles for our hips. Body suits, longline bras, shaping half-slips.”
“Wow, I never knew.”
Karen laughed. “You’re too young for all that. Even I’m too young to need foundation garments. I have a couple of panty girdles, but mom – you should look in her dresser drawer – she’s got all kinds of girdles and other shapers.”
I was curious to take a look. That was something I’d have to do when I got the chance. Karen sat me down and brushed my hair so it fell down to either side of my eyes and almost to my chin. Then she did some light makeup on my cheeks. “Would you like lipstick?”
“For my lips?”
“We can make your lips bright red, or pink, or even some weird colors. But I recommend red or pink. Lipstick is fun, you should try it.”
“Okay, I’ll take red lipstick.”
“Good choice.” Karen said. She applied the lipstick to my lips. She went into her closet and came back with a pretty, pink, party dress. “I wore this exactly twice. Once at Easter and then at our cousin’s christening. After that I sprang up and was too tall for it. It should fit you fine.”
Karen lowered the dress over my head as I put my arms in the sleeves. When it was on she zipped up the back. The skirts were a bit starchy and projected out at a high angle. “There’s a lovely crinoline that goes with it.” Karen said. She fetched it and had me step into it and pull it up to my waist. “Lastly are these shoes. They’re not flats but the heels shouldn’t give you any problems.”
I put on the shoes and Karen said, “Unbelievable how well they fit. You’ve got girl feet, Tiffany!”
Karen took my hand and led me to a full length mirror in my mom’s bedroom. My jaw dropped when I saw my reflection. I never would have guessed that I was myself – I was looking at a pretty girl in an even prettier dress whose skirts and crinolines surrounded her waist as if she were wearing an ornate tutu.
Karen laughed victoriously. “Hurrah! Tiffany! My masterpiece of feminine beauty! Monica is going to love playing with you. The two of you will be bookends! The last thing I need to do is fetch my old dollies from the attic. Monica expects you to like playing with dollies.”
“What does that mean?”
“It can be tea parties. They’re always fun. A game I used to like for awhile was where me and my girlfriends pretended to be mommies. We each had a doll baby and dressed them and all that.”
“I guess I could play games like that. I guess it’s a little weird but if that’s what Monica wants I can do it.”
“That’s a great attitude, Tiffany! One other thing is to try to make your voice sound a bit more girly.”
“How do I do that?”
“A breathless quality can help. Try to talk in the higher registers. Let me listen to you.”
I spoke some sentences and Karen gave some advice on improving it. “I think you’ll do fine. Your vocal chords are still those of a prepubescent. A couple of years from now you’ll have a lot harder time sounding female!”
Karen had me walk about the house with her including going up and down the stairs. “Dainty, dainty, dainty,” she emphasized. “Think dainty and you’ll be dainty.” She showed me how to hold my arms in a delicate pose and especially to walk like a girl. “Very good, very good,” she encouraged me. “Perhaps the best thing you can do is imitate Monica. Walk like her, use your hands and arms like she does. Say the same kind of things she says and you’ll be a wonderful girlfriend to her. She and Lisa will be here in a few minutes. Let’s hope it works out!”
***
Ten minutes later the doorbell rang. I shyly stood behind Karen when she opened the door. Monica was shyly hiding behind Lisa as they entered the house. Karen and Lisa hugged and Karen said, “Welcome, Monica! Come meet my sister Tiffany. She’s so excited to meet you!”
Monica and I stood facing each other and I did my best to smile and make her feel welcome. After a few seconds she smiled back at me and said, “Oh God, I love your dress! It’s so pretty!”
Monica was also wearing a pink dress – very much like mine. Hers had some pink bows on it and some lace trim and several layers of crinolines peeking out from under her skirt. Her chest was as developed as mine was. Small breasts that pushed out the pretty fabric. She was holding a shopping bag that I found out later had her nightie, a toothbrush, and her favorite dolls.
I fixated on how Monica talked and moved – just like Karen had told me to do. I saw no trace of her being suspicious of my girlhood. Once that became clear I relaxed and enjoyed being with her. She had a slightly bubbly personality that came out more and more as she settled in. I’m pretty sure that we were both thinking that we were really hitting it off – and that it was so nice to acquire a new friend who had every potential of becoming a very close friend.
“Why don’t you two girls retreat to Tiffany’s room. We’ll call you down when it’s time for dinner,” Karen said.
Monica and I went upstairs to my bedroom. Karen had brought out a bunch of her old dolls and decorations that she used to have in her bedroom. It made my room seem more like that of a girl than a boy. In particular, Karen had found a feminine, pink floral quilt that she had put on my bed.
“What would you like to play?” Monica asked me.
“I’d love for you to introduce me to your dolls.”
“They want to meet you. I’ll make the introductions. Let’s sit down,” Monica said.
I watched as Monica gracefully eased herself down to sit cross legged on the thick carpeted floor taking care to arrange her skirts around her.
I did my best to imitate exactly how she held her arms as she sat and when I was seated I organized my crinolines and skirts the same way she had. When I was done, I felt a jolt of unexpected happiness by my awareness of being part of the tableaux formed by the sea of pink skirts and crinolines arrayed around the two of us.
It was really happening to me. Femininity had risen up in all its powerful glory and swallowed me whole. I was humbled by this insight. It was as if I had suddenly acquired the ability to see a part of the light spectrum that only girls were allowed to see. This feminine world of pinks and lace and gentleness – the daintiness that Karen talked about – was at its heart as powerful as any male world. It’s just that men are blind to it. But now I was fully immersed in this female domain. The degree of joy I felt at this moment transcended any that I had ever had as a boy. The thought terrified me because I could see that it was a one-way street. There was no going back from these desires and feelings. Even without knowing precisely how my future would unfold I knew that the joy I felt this minute would be forever enticing me to dress up like Tiffany again.
I glanced at Monica, who was busy arranging the two dolls she had brought with her. I could see that being a girl meant living within this world of femininity. It was expected – not surprising. Girls lacked the little sentinel in their mind like I did that watched myself be a girl. If I were to become fully comfortable in the role of Tiffany I’d have to stop being self-conscious. Get rid of the sentinel. Don’t ACT like a girl – just BE a girl.
Monica held up her first doll. It had long blonde hair and red lips and was wearing a wedding gown. “This is Babs. Say hello to Tiffany.” In a funny voice she said, “Hiya Tiffany!”
I laughed and said, “So very nice to meet you Babs. Is today your wedding day?”
“Ouch!” Monica pretended that Babs was crying. “I’ve been left at the altar! Henry, the dear love of my life, hasn’t shown up! It breaks my heart!”
“But Babs, Henry is on his way. He was halfway to the church when he realized that he had forgotten the wedding rings. He had to go back home to fetch them. What a dunce!”
Monica laughed. “Oh, that dumb Henry. I love him anyway!”
“Here he is now!” I took a Ken doll that Karen had given me and had him running into the church.
“Oh my God,” Monica said. “He’s only wearing a swimsuit!”
Monica and I laughed uproariously at the sartorial mismatch between Ken and Babs.
I realized that for a few minutes the sentinel had left my mind completely. I had been for that time period a real girl playing with another girl. This whole experience was so weird. I didn’t know where my emotions were coming from. This free fall toward wanting to be a girl seemed to have come out of nowhere.
We continued playing together for a while. Monica introduced her other doll to me and I found myself making up names for the dolls that Karen had left for me. After an especially funny exchange Monica said, “You’re so much fun Tiffany. I really love playing with you.”
“The same here, Monica. You’re the best!”
Monica reached out her hand and held mine smiling at me. “Boys never play like this. They tease me, they make fun of girls. Then, Lisa says, when they get older they flip completely and they want more than anything to be your friend!”
“That must be true because Karen has so many boys wanting to go out with her!”
“Same with Lisa. What do you think they want to do with their boyfriends tonight?” Monica asked.
“I think Karen wants to kiss her boyfriend Earl. It’s a really big deal for her.”
“Lisa says I’m not ready to know what she and Marcus will be doing. What could that be?”
“I think adults do all kinds of weird things with each other. Karen says we have to stay in our room tonight.”
“We should at least take a peek at them,” Monica said.
I laughed, “Yes, that would be interesting. Find out what they’re doing.”
We giggled together and Monica said, “You must be wearing a bra. I can see that we have about the same size titties.”
I laughed and said, “Yes, it’s a trainer bra.”
“Me too. But …”
“What?”
“I have a secret.”
“A secret?”
“Yes. I’ll share the secret with you because you’re so much fun.”
“Thank you, Monica! Then I’ll have to share a secret with you.”
“I hope you do! My secret is that I’m wearing falsies with my trainer bra.”
“Oh, no, you aren’t!” I said. “I have falsies also!”
“You do?”
“We’re so much alike!” I said.
“So many of the girls at school are wearing bras and I begged my mom to get me my first bra. Instead, she let me wear Lisa’s old trainer bra, which is practically new anyway, since Lisa grew so fast that she barely got to wear it.”
“And I’m wearing one of Karen’s trainer bras,” I said.
“WowWee!” Monica said.
We sat thinking about how much like bookends we were. Same kind of pretty dresses and crinolines. Shoes very similar. And now our underwear and falsies are the same. It was amazing.
Monica stood up and I followed her. “Do you like to twirl?” she asked me.
“Show me,” I said.
“I take ballet lessons and have learned how to do a pirouette.”
“Let me see!”
Monica pirouetted a few times causing her skirts to fly around her. “Come on Tiffany. You can twirl also!”
I stood on my toes and swiveled around quickly. My skirts rose up and flew around me. Monica clapped. “It’s so much fun,” I said when I stopped and my skirts bounced forward and back around me.
“Do you want to be a ballet dancer?” I asked Monica.
“Yes, I would, but I think I’m too shy. Being on a stage scares me.”
“I’m the same way. I don’t know how dancers do it.”
“But it’s fun to dance just for the sake of dancing! We can put on a ballet together!”
“Wow, that would be so much fun!”
We put on the music to Swan Lake and Monica and I pretended to be swans dancing to our own silly choreography. We posed together in our dresses and took some selfies using the camera on my laptop. In our last picture, we stood side by side with our arms holding each other’s backs. After the camera clicked, Monica swiveled to face me.
“I don’t know if girls are allowed to kiss other girls but …” Monica said. She put her arms around me and kissed me on the cheek. “I love playing with you Tiffany.”
“I think there’s a name for girls who kiss girls,” I said.
“What is it?”
“I’m not sure,” I said, as I put my arms around Tiffany and kissed her on her cheek. She laughed. She then gave me a peck on my lips. I was surprised and it dawned on me that Monica was letting me know that she seriously wanted to kiss me. Just then I heard Karen calling us down to dinner.
When we came downstairs, Karen asked, “How are you two girls getting along? You’ve been so quiet up there.”
“I love playing with Monica,” I said.
“Tiffany is so much fun,” Monica said. She took my hand and said, “We’re becoming BFF’s!”
“That’s true!” I said.
Lisa joined us and said, “Fabulous, girls. BFF’s! I’m so happy that Monica has found a girl she likes to play with. She’s been so difficult!”
Monica turned to me and said, “My big sister doesn’t approve of girls being pretty like we are!”
“That’s not true! For the umpteenth time let me repeat: Your mom and I say that there’s more to being a girl than wearing pretty dresses and flouncing around!”
“I love to flounce!” Monica said.
“And I do too,” I said.
“Whatever! You two flouncers should wear aprons during dinner. We’re having spaghetti and meatballs and I’d hate for tomato sauce to get on those pretty dresses of yours!” Lisa said.
Karen gave us aprons and tied them behind our backs. Then the four of us sat down for dinner. Karen asked what we were playing upstairs and I told her about meeting Babs and the other dolls, about our twirling, and the other games we played.
“Earl and Marcus are coming over at eight o’clock,” Karen said. “The two of you can say hello to them and then disappear upstairs. You can watch a movie on your laptop or whatever. Take some chips and drinks up with you. Go to sleep when you’re tired. Lisa and I will be making French Toast for breakfast. We’ll wake you if you guys aren’t up.”
“Will the boys be here in the morning” Monica asked.
“No, not at all. They’ll be here no later than midnight!”
Monica and I helped clean up after dinner. Then we sat side by side in the living room with Lisa and Karen waiting for the boys to show up. “You girls are a trip,” Lisa said. "Don’t all those crinolines drive you crazy?”
“Here we go again, Tiffany,” Monica said, rolling her eyes. “I like my crinolines, Lisa. They’re pretty and they make me feel pretty – sort of like I’m a beautiful flower. Tiffany feels the same way.”
“Sure I do. You and Karen are missing out on all the fun!” I said. Karen shook her head in amazement. No doubt she was thinking how weird it was for her little brother to be giving her advice on being the best possible girl!
“I think Tiffany and Monica belong in a different century,” Karen said. “When women’s dresses had huge skirts held out by bustles, and all kinds of doodads decorating them.”
“I personally, would love that,” Monica said.
Just then the doorbell rang.
“The boys!” Lisa said. She and Karen jumped up and went to answer the door.
Earl, Marcus and the two girls greeted each other in the foyer and then came into the living room. The boys were sixteen like the girls and showed the results of puberty gone wild. Bodies that had sprouted in every direction. Testosterone dripping from their pores. Man boys was a good way to describe them.
“These are our little sisters,” Karen said. “Tiffany is my sister and Monica is Lisa’s sister.”
“A pleasure,” Earl said.
“Delighted,” Marcus said.
Monica said, giggling, “It’s wonderful to meet you gentlemen,” and she curtsied holding out her skirts.
I said, “Indeed, it is a divine experience to make your acquaintance,” and I curtsied the same as Monica. She and I laughed.
“They’re so funny,” Earl said.
“Run along upstairs,” Lisa said. Laughing and giggling, Monica and I went back up to my room.
We played with our dolls for a while. After some time it was quiet in the house and we agreed the time had come to take a peek and see what our sisters were up to. We carefully opened the door and crept out onto the landing at the top of the stairs. Then we descended slowly until we could crane our necks and see into the living room.
There, in very dim light, Earl was sitting on the sofa, with his legs spread apart. Karen was sitting sideways at his feet and leaning in. It was hard to make out exactly what she was doing but her head was bobbing around erratically. Earl seemed to be quietly moaning.
On the far side of the room they saw Lisa on her hands and knees. She didn’t seem to be wearing any clothes. On his knees behind her was Marcus who was leaning over her back and rhythmically moving his hips back and forth.
Monica and I looked at each other and sneaked back into the bedroom. “What are they doing?” I asked. “It looks so weird.”
“I can’t imagine,” Monica said. “What’s between a boy’s legs that your sister would be playing with or whatever.”
“Boys have a penis,” I said. “Do you think my sister was doing something with it?”
“That seems really weird to me,” Monica said. “I don’t know. But what about Lisa? Why was she facing away from Marcus and why would he climb on her back.”
“I took wrestling in gym class last year,” I said. “It looks to me like they were starting a match. But I never heard of boys and girls wrestling with each other. And why are they nude?”
“All I can say is that Lisa gives me such a hard time about me wearing pretty dresses and being what she calls a girly girl, while she wrestles boys!”
We both laughed uproariously. We sat down next to each other on the end of the bed, and then Monica climbed further up the bed and lay down taking care to organize her skirts and crinolines. I joined her and we lay on our sides and faced each other.
“This is a happy time,” Monica said. “The girls I mainly play with aren’t dressed as dreamily as you are. I think that they’ve outgrown playing with dollies and only half-heartedly do it to make me happy. But you’re like me!”
I smiled at Monica and put my hand on her waist and leaned in. “I guess we can be bad girls and kiss!” Monica laughed and I gave her a little kiss on the lips like she had done to me before. The next thing I knew, Monica put her hand on my waist and leaned in and kissed me on the lips for a full minute before she separated from me. Now we pulled ourselves tightly against each other, wrapped our arms around each other and began kissing and kissing each other.
After ten minutes or so, Monica said, “I’m so happy Tiffany. You know I once overheard Lisa and her girlfriend talking about kissing. She said that kissing is best when people put their tongue in the other person's mouth.”
“Really?” I said. “That sounds so – I don’t know – kind of crazy and exotic?”
“Do you want to try that?”
“Sure!” I said.
This time as we kissed Monica poked her tongue into my mouth. As it slid deeper in I felt a desire to suck on it. There we were: her tongue in my mouth and my lips and tongue gently feeding on it. After a while, our tongues wrestled against each other and then she began sucking on my tongue. I can’t describe the happiness that poured through me. To be so intimate with another human being opened up realms of feelings that had been entirely unknown to me before.
I lost track of how long we kissed but eventually Monica whispered to me, “Let’s put on our nighties and snuggle up under the covers!”
We got up and unzipped each other’s dresses, then hung them up carefully in the closet. We lay our crinolines carefully on a chair. Karen had strategically removed my boy clothes from the bedroom so as not to raise suspicion. My closet and drawers were filled with a smattering of her old clothes that were meant for me to wear.
After we each abluted in the bathroom, we put on our nighties. Of course our gowns had an excess of filmy pink fabric decorated with ribbons and lace. “Aren’t we beautiful!” Monica said.
“Indeed!”
We climbed into bed together and situated a laptop between us so we could watch an episode of the Babysitters Club. Eventually we drifted off to sleep. Sometime in the middle of the night I was awakened by Monica kissing me and gently sliding her hand along my body.
“I’m sorry Tiffany. I woke to go pee and I had such a passion to kiss you again!”
I laughed, “You’re so funny. I’m always happy to kiss you.”
We kissed a while longer and then sleep overcame us again. We awoke in the morning to Karen telling us breakfast was in fifteen minutes. I put on my bra and falsies and then put on a shirt, skirt, and knee high socks. Monica was wearing jeans and a shirt and we joined Lisa and Karen for breakfast.
When we were done eating, Lisa and Monica went home. They’d be back later in the afternoon. Apparently, Earl and Marcus would return for a repeat of the previous night activities.
***
When Karen and I were alone she asked me how it had gone with Monica. “You two seemed to really hit it off.”
“We’re so similar in every way,” I said.
“That was so obvious to Lisa and me. The two of you together are adorable in your dresses. You have a natural acting ability to come across as such a pretty girl.”
“I don’t think I was acting, Karen. I like being Tiffany. I like being a girl. I think I prefer being a girl rather than a boy. I’m pretty sure that I’d like to always be Tiffany.” Saying these words and realizing the futility of my wish caused me to choke up and shed some tears.
“Oh my God, you’re crying.”
“Because I can’t be a girl,” I sobbed. “Mom and dad won’t let me, will they?”
“Holy cow, Blake. You’ve really gone that far?”
“And what’s going to happen if Monica finds out I’m a boy? It will ruin everything! She’ll hate me. She’ll be mad that I wasn’t honest.” I resumed crying.
“Have you fallen in love with her?” Karen asked.
“We kissed each other. Neither of us have ever been so happy.”
“Kissed? Wow! So Monica is okay with being a lesbian?”
“Lesbian? Is that when two girls kiss? I thought that there was a word for girls like that.”
“Yes. Girls that like to kiss each other are called lesbians.”
“We talked about that. We weren’t sure if it was okay for girls to kiss each other, but we liked doing it so much that we did it anyway.”
“I had no idea that the two of you would hit it off this well,” Karen said. “It’s really my fault that you’re in this jam. If worse comes to worse and she finds out you’re a boy, I’ll do my best to see if I can convince her to remain your friend.”
“Thank you,” I said.
***
When Monica returned we put on our dresses and sat side by side in the living room alternating kissing and chatting. We were oblivious to Lisa and Karen as they came and went. At one point I said, “Karen said that girls who kiss each other are called lesbians.”
“Oh, so that’s the word. We’re lesbians!” Monica said.
“Is that okay with you?”
“I don’t know if my parents would be mad at me for being a lesbian,” Monica said. “What would your parents think?”
“Good question,” I said. That was like wondering whether or not my parents approved of me flying into space on my bicycle - it wasn't ever going to happen.
“It’s all kind of weird. I don’t know if I’m a lesbian or not,” Monica said. “I always thought that one day I’d meet a nice boy and he’d become my boyfriend.”
“Me too.” I could see that my deceit was taking me further and further into lying. I felt guilty about that. I wondered if I should risk everything and let Monica know I was a boy. That would clear my conscience. Continuing to lie was only going to make it so much worse when Monica eventually found out that I was a boy all along.
All afternoon I pondered when I should say something and how I should say it. I dreaded her reaction. Her tears, her anger, her hurt. Her disappointment in me that I’d take a bribe to trick her into thinking she had made a new girlfriend.
Karen and Lisa served us a dinner of pizza that was delivered to the house. Afterwards we went back upstairs. About eight o’clock we heard Earl and Marcus arriving and then a big commotion as our sisters greeted them. After a while it was quiet again downstairs and Monica and I resumed our kissing. I don’t know what came over me but I knew that this was the time for Monica to learn the truth about me.
While we kissed I moved my hand up inside her crinolines along her naked thigh until I reached her panty. Monica stopped kissing me and said, “That feels so good. I’m going to do that to you too.”
“That would be nice,” I said.
I felt Monica’s hand go along my thigh and up toward my panty. Our hands were now just touching the hems of our panties. I told myself that this was do or die! I inched my hand up until it was resting on the front of Monica’s panty just between her legs. I heard her giggle and her hand moved up and I froze when I sensed her puzzled fingers pushing against the bulge of my small penis. I told myself over and over again that this was what I wanted. This was what I had to do.
“What is that?” Monica said, her voice perturbed. “I don’t know what I’m feeling.”
“I’m so sorry Monica …”
“Sorry?”
Monica got up and lifted up my skirts and crinolines until my panties were exposed. She could plainly see the bulge of my penis. “Take off your panties,” she said with a quavering voice.
I reached down to them and wiggled out of them.
“Is that thing a … a what? ..a penis? Is that what a penis looks like?”
“I’m sorry, Monica …”
“Are you a boy? You’re a boy! Oh, my God!”
Monica stared at me with a strange look on her face.
“I realized that it was unfair of me …”
Monica didn’t seem to be listening to me. She suddenly turned and ran out of the bedroom and downstairs, yelling “Lisa, Lisa!” I followed behind her. In a flash she was in the living room. “Lisa! Did you know that Tiffany is a boy?”
Though the light was dim in the living room, we could plainly see that Lisa was on her knees with Marcus’s man-sized, erect, penis in her mouth preventing her from saying anything. On the opposite side of the room, Earl’s penis seemed to be lodged inside my sister. I suddenly had the insight that it must be her vagina that he had entered.
Lisa frantically got Marcus’s cock out of her mouth and screamed, “What the effing Monica! I told you to stay upstairs!”
Marcus and Earl grabbed their clothing and while trying to conceal their penises comically dashed out of the living room to hide in the kitchen.
Ignoring her sister’s remark, Monica said, “Tiffany is a boy! Tiffany is a boy!”
“I know …” Lisa started to say and then stopped and said, “What? He’s a boy?”
“Yes! He’s a boy! A real boy pretending to be Tiffany!” Monica turned to Karen and said, “Did you know that your sister is a boy?”
“Yes, I’m sorry Monica,” Karen said. “The truth is that I knew you wouldn’t play with boys so I had my brother dress up as Tiffany.”
Monica turned to me and said, “Why did you dress up as a girl? Why were you willing to do it?”
I stared at Monica. The last thing on earth I wanted to do was break her heart. My eyes watered up and I felt a sob forming in my throat. “It’s just …” I collapsed onto the sofa weeping.
“I bribed him,” Karen interjected. “It’s entirely my fault. I came down hard on him to agree to be Tiffany. It was terribly wrong of me to set this up and I’m sorry. Please don’t be mad at Tiffany, I didn’t give him a chance to say no.”
My tears flowed at the hurt I’d given Monica and the knowledge that she’d never want to see me again. “I’m so sorry,” I wailed.
“Are you all crazy?” Monica said, turning to look at each of us in turn. “Why should I be mad? Tiffany didn’t know me when she agreed to be Tiffany – so I don’t feel like she wanted to trick me personally.”
“But …” Lisa said.
Monica walked over and sat down next to me on the sofa. “My poor Tiffany. I’m not mad at you. I don’t know why everyone is acting so guilty. You may be a boy because you have that thing, but you know and I know that you are definitely a girl. You couldn’t fake that. No, no, no. You’re a girl through and through!”
“But Monica,” Lisa said, “You were the one running down the stairs shouting “Lisa, Lisa!”
“That’s because I was so happy that Tiffany is a boy. I wanted to share the news with you. What’s that word? Lesbian? You said mom and dad would have a hard time if I was a lesbian. But Tiffany is a boy, so I can’t be a lesbian!”
“You’re serious? You’re actually happy Tiffany is a boy?” Karen asked, incredulously.
“I don’t think I was meant to be a lesbian,” Monica said.
“But like you said, Tiffany acts and behaves like a girl,” Lisa said, “so that sort of makes you one. Doesn’t it?”
“Maybe, but mom and dad won’t get upset. That’s what I want,” Monica said. “Tiffany is the only kind of boy I could ever want. A boy who loves to wear pretty dresses and play dollies with me and likes to kiss me.” Monica gently ran her fingers through my hair comforting me.
“This is great then,” Lisa said. “Tiffany, I mean Blake, Blake is Tiffany’s boy name, can be your boyfriend. Mom and dad will be happy and they don’t have to know that Blake is also Tiffany.”
“Will it bother you that I can’t always wear dresses when we play together?” I asked.
“Can you tell your parents you want to dress like Tiffany?” Monica said.
“What would mom and dad say if I told them I want to be a girl?” I asked Karen.
“Don’t be ridiculous, Blake,” Karen said. “They’ll freak out. Besides, they might figure out that I helped you.”
“Well, while I would love for you to be Tiffany and wearing pretty dresses, I’ll still be happy to play with you as Blake. We’ll still be BFF’s!”
“I hate to break up this love fest,” Lisa said, “but Karen and I have to take care of poor Marcus and Earl.”
“The two of you lovebirds should sashay back to your bedroom and don’t come down again!” Karen said. “Also, forget everything you might have seen down here!”
“Like why were you …” Monica said.
“Goodbye!” Lisa said.
***
Back in my bedroom Monica and I lay on the bed together holding each other. Monica said, “I was so touched when you were crying. It broke my heart to see you so sad.”
“It broke my heart that I wasn’t truthful with you.”
“But you purposefully led me to touch your penis so I would know the truth. That was brave of you!”
“Thank you, Monica. You’re so kind!”
Monica laughed. “Speaking of penises, did you see those things on the boys!”
“Oh my God, yes! I didn’t know that they get like that,” I said.
“And my sister had it in her mouth!” Monica said. “I don’t get that at all. Why would one do that?”
“I don’t know,” I said. “Boys have penises and girls have vaginas. I think Earl was putting his penis in my sister.”
“You’re right,” Monica said. “I guess I’d only heard a little about that but now I can see that this is what boys and girls do.”
“It’s how babies come about, isn’t it?” I said.
“Yeah, that makes sense. Will your sister have a baby?”
“I don’t know.”
We fell silent until Monica said, “I liked what we were doing when I discovered that you’re a boy!”
I laughed. “I liked that also.”
We lay down and my hand once again felt its way up Monica’s leg, underneath her many crinolines of her pretty dress and found her panties. Then I felt her hand making the same journey underneath my skirts. Monica’s fingers explored inside my panties while I did the same inside of hers.
“I guess I can see that my bump likes to be touched," I said. It was true. I was feeling pleasure not exactly in my penis but rather deep inside my loins.
“Let’s continue and see where this leads!” Monica said.
“Good idea.”
The End