tagTranssexuals & CrossdressersGirlboy Diary Day 02

Girlboy Diary Day 02


When I went to bed that night I wondered how I would feel in the morning when I woke up for the first time to my new world.

It felt great. It felt amazing. And after a couple of minutes it scared me right back into bed. Was I nuts? How could I go on pretending to be a girl? My screwball parents weren't the only people in my life. What was I going to be after college, an airline stewardess? Perhaps at fifty I could become a nun. After a few minutes I calmed down and forced myself to put on the clothes Mother had laid out for me, which included panties and a skirt. Thank you for the wig, Mom. And for not forgetting the lipstick. But when I was dressed and made up and considered myself in the mirror, the excitement kicked in again. I looked like a piece of ass if I did say so. The falsies had been there with the rest of my outfit but I left them. I was conceited enough to think I could pass the sexpot test without them, and in my unhumble opinion I did.

I sashayed into the kitchen, having heard Father's voice, but it wasn't Mother he was talking to. It was Mr. Davis and Junior who lived across the street. Junior was my age. We had been pals on and off since kindergarten. The friendship faded in high school when Junior gravitated to sports and girls while I got into drama and poetry and being a loner, also a loser in Junior's opinion, or so I interpreted it, but in my own opinion as well. Junior took after his Dad in the muscle department. Both were strong looking guys. They looked at me like I had just arrived from Mars. Better make that Venus, I thought, after more fully registering Mr. Davis's expression.

"Jesus!," he said.

"Hey, Jerry. Not bad," Junior said in a relaxed way that didn't exactly go with his gaze.

"Mmmm, nice to see you," I said. I tried using my girl's voice but it flopped. I tried again and this time it was better. "Are you joining us for breakfast?" If I was going to be a girlboy the neighbors might as well know it.

The amazed faces were helping me find my own bearings. Had they been more self assured, I probably wouldn't have done as well. I actually began to feel amused.

"So, you're a fag, huh?" Junior said matter of factly.

"No, Junior, not a fag. Are you a fag?"

He reddened. I saw the muscles tighten in his neck. Mother got up from the table and put a hand on his shoulder.

"What Jerry means is that he's a girl now. His new name is Tiffany, remember?"

"He ain't a girl. I admit he almost looks like one but....he's not? This is a stupid idea. Don't call me a fag again, Jerry. Okay?"

"Okay, Junior. And please don't call me one. What's a stupid idea?"

Mother took Junior by the arm and sat him down, facing away from the table. Mr. Davis seemed to take this as a cue and he sat, too. Father was already at the table with his coffee and newspaper paying no attention to either. I stood and waited, wondering what was going on. Mother began to tell me.

"Mr. Davis and I have been conferring, Tiffany. I told him a couple of weeks ago about your upcoming transformation, seeing as how the Davis's are friends and neighbors and all. I felt they should be forewarned, that is, advised. Ahem. Anyway, after I told them they confided in me that Junior has an issue regarding girls."

"An issue?"

"Yes, an issue. Junior, would you tell Tiffany why you're here."

Junior's eyes were lasers. "I'm a virgin, Jerry. That's the fucking issue."

Mother sighed and shrugged her shoulders. "This is Tiffany, Junior. You must think of him as Tiffany...of her as Tiffany. It will make things much easier. And look how pretty Tiffany is."

"Yeah, he is pretty, gotta say it....Tiffany."

"Thank you, Junior. I'm sorry you're still a virgin. I always thought you were getting girls left and right."

"Never happened, Jerry."

"Mmm hmm. So if I get this completely unbelievable situation I'm finding myself in you and your father have come over so you can have sex with me and lose your virginity. Is that it? Are you people out of your minds!?"

Mr. Davis cleared his throat and smiled. "You're one heck of a treat to the eyes, Tiffany. Can you blame us if you're as desirable as you are."

He was putting on the charm, which I appreciated, but... "I'm sorry, 'us'?"

"That's right, honey. First Junior, then me."

Mother cut in at this point to explain that Junior had been talked into fucking me provided that his father fucked me, too. Under no condition would Junior risk becoming the only fag target in the family. "It's so sweet when you think about it dear, because you're a virgin, too, that is Tiffany is, so you and Junior will lose it together. And then you should be broken in at least a little which will make you better able to take Mr. Davis's cock. He has a biggy."

"Does he really? Of course, Mother, you would be fully informed on the subject."

"Don't get smart ass with me, Jerry, Tiffany, both of you, or I'll add your father to the list and when the rubbish men come by, it's Saturday, we'll invite them in for turns."

Mother was blazing, which is the way she gets angry. She's never slightly or moderately angry. The blazing kind is the only kind she knows. I didn't care. I was pretty upset myself, but then I saw it. Mr. Davis had opened his fly and liberated his biggy. It wasn't quite the biggy that Father's is but it was plenty big and more impressive than its size was its form. It was an Adonis cock, positively mouth watering.

"Oh," I said.

Mr. Davis watched me gape. "Guess what it made this way, sweetheart."


"Yes indeedy. Always had a weakness for pretty boy cunts, pardon my French. Don't think I ever saw one better than you, cutie, even in a picture."

"Well...," I blushed. I couldn't wrest my eyes from the missile poised for take off in the man's open fly. If that wasn't enough to prove to me the starch was gone from my resistance, I felt my knees asking permission to find the floor. It's amazing how quick a handsome and ready cock can turn things around for a reluctant girlboy. Mr. Davis read my wicked mind.

"You can have this after you make Junior happy."

I giggled sort of and smiled at Junior, taking note of his lap. He was wearing loose fitting jeans with nothing disturbing the folds. I remembered for some reason when I was ten or eleven playing basketball with Father against Junior and Mr. Davis in the Davis's driveway, if you could call what we did playing basketball. "So you and your Dad are still a team, huh Junior," I said, trying out a grin on him.

"Yeah, a fuck you team, Jerry," he muttered.

"Junior, that attitude isn't going to get you anywhere. I hope this isn't how you are when you try to make a girl." I used my girl's voice on him and I stood in front of him like a girl stands when she is teasing, and it had an effect. Junior looked at me. He blushed.

"I thought you had fake tits that you used," he said, softly.

"I do wear them sometimes. I could put them on for you, Junior. Would you like that?"

Junior swallowed. "I don't know."

"I don't think fake things are what we want right now, Junior. I think we want real things. I have some real things you might like, two actually. And you have one real thing, one pretty great real thing if you'll give him a chance, if you'll let me help you give him a chance. I bet after all this time he would like a chance."

Junior twisted his mouth. He was listening, so I said, "Even if I'm not completely a girl, I'm enough like one that we can pretend. I bet we can pretend with no problem, Junior. I bet we can pretend like anything."

Junior blanched and then he blushed and then he blanched again. He looked around and for a second I thought he was embarrassed at being watched by his Dad and my parents but then I sensed that he wanted them there for support, crazy as that sounds.

He cleared his throat and tried to smile. "Yeh, heh heh, don't expect me to kiss you, Jerry."

"You mean, Tiffany, Junior."

"Yeah, yeah."

"I don't expect it. It might hurt my feelings but I won't expect it if you don't want me to, Junior." I had the voice going to perfection.

"Jesus, I don't want to hurt your feelings, but, I mean..."

I gave him a pout but it ended with a smile. "It's okay, Junior. Maybe I should show you how I look without my skirt on."

I shot a glance at Mr. Davis. Don't think I'd forgotten what he said about me being a cute boy thing, or that I wasn't interested in confirming for him his good judgment. Of course, I had been acutely aware of my audience. They had reminded of when I was in high school and Mr. and Mrs. Davis came over to listen with my parents to me rehearse my declamation of The Gettysburg Address, right here in the kitchen on a Saturday morning just like now, except this was a rather different sort of presentation.

Anyway, Junior nodded his permission for me to ditch the skirt so I unhooked it and let it fall down my legs. I stepped out of my sandals and the skirt and posed in my panties for the two gentlemen who had dropped in to fuck me, and Father if he cared to watch, which he did. Mother watched, too, but I wasn't doing it for her.

Junior approved. I could tell by the way he swallowed and by his ears turning red. He and Mr. Davis spoke to each other about my legs and my thighs and my bottom in the silk panties and about my smooth skin and about the fact, as they saw it, that if it weren't for the lump at the front of my panties I could pass as a model in a Victoria Secret catalogue. It seemed an opportune moment for my panties to join their friends. I sighed so Junior and Mr. Davis would hear it and then, while they watched, I worked the panties down my girlish legs and away they went. My dick was half hard, and there it was. I watched Junior and Mr. Davis consider it.

"Dick girls are a joy to behold, Junior, when they're like her," Mr. Davis said, winning whatever parts of my heart remained for him to win.

Junior only nodded, but his pants were doing more. They were steadily tenting. Oh, my.

I figured I should strike while the iron was hot, as they say. I wasn't sure what Junior's problem was with girls but I had a suspicion. If his approach was like his approach to most things, he would have been the proverbial bull in a china shop. And gotten nowhere probably, maybe not even with himself. I wondered if he had ever taken the time to get himself worked up like he was worked up then. He had been reticent with me only because he didn't want to be here, but now he did want to be here. Was I piece of ass or what!? That's not to say Junior was completely won over. He stared at me like he was trying to put it together. How could I be this way and have a cock sticking out in the middle of the picture, like a mustache on Nicole Kidman. But he seemed to making progress. Before we were done I wanted him to have his father's perspective: that Tiffany was a joy to behold.

I posed some more, maybe thirty seconds worth, putting my hands on my hips as I swiveled my ass and smiled, one last little show for Junior. Then I softly suggested his cock might have a better time if it left the confines of the jeans. Junior bit his lip, looked around, took a deep breath, and undid his pants. When they were around his ankles, I bent down and removed them. Mother reached across the table and tapped Junior on the shoulder. She passed him a tube and Junior coated his cock, and there it was, poised in his lap, glistening its invitation. I took my own deep breath, braced my hands on Junior's shoulders, and lowered myself. Junior held his cock for me, directing it, and in it came, nice and smooth, not far but far enough for me to see stars with my eyes closed. I kept myself where I was, getting up my nerve, feeling the cock inside me, oh man!, but Junior wasn't waiting. He gripped me at the waist and pulled down at the same time that he pushed up. Uh huh, that's what Junior did. I heard myself gasp. It didn't feel so good, it felt like something you might read about in the history of the Spanish Inquisition. Then it felt better, then it felt a lot better, then a lot, lot better. I have no idea of the time. I was in a different zone. When I opened my eyes and saw the kitchen and the people in it going up and down, whoops that was me going up and down, not them, I was seriously in my element. Mother had a video camera in front of her face. I chose not to look at my deflowerer or at my stiffy jouncing in front of him. I kept my head turned. But I couldn't help hearing Junior's impassioned sounds and it was wonderful knowing I was the cause of them.

"Look at his eyes, look at the way he's panting!," or something like that, I heard Mr. Davis say. I didn't know if he meant Junior or me.

I thought I was going to have an orgasm but before that event could get its act together Junior had his, a major eruption no less. The geyser might have jettisoned me all by itself if Junior hadn't assisted. Either he forgot someone else was involved in the enterprise or he didn't care because he thrashed about with arms and legs and dispatched me. My abused but humming backside hit the tile floor just before Junior's last gushes rained down. Mother hurried over with the camera.

Well, that's about it. Mr. Davis decided to reserve his turn for another day. His son's accomplishment and the show we had put on were enough for him for one morning, he said. Mother thought it a wise decision all things, including tender me, considered. Junior was proud of himself. I half expected him to have mixed feelings at best toward me as he got himself wiped off and dressed. But he was sweet. And as he went out the screen door following his Dad he looked back at me and grinned the kind of grin that said let's do that again. My return look was non-committal. I had come on to him as hot to trot after warming up to the situation, and hot to trot I had been, but now he was not to presume I was just an easy romp in the hay. We girlboys can be so flighty.

See you next time.

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