Girlboy Diary
by Hartford
Day 1
It might never have happened if my aunt hadn't caught me wearing girl clothes at the mall, clothes plus a wig and make up. How she knew it was me is a mystery because I can pass like nobody's business. Hate to brag but it's a fact. Anyway, my aunt followed me, got some still photos and video on her blackberry, and showed it to Mother. I found out six weeks later when I woke up on my first morning home for the summer from college, this very morning, with Mother sitting on the bed holding in her lap what turned out to be my outfit for the day. She had the evidence of my cross dressing, as well, which she happily showed me. Mother had long suspected my secret, which I rarely indulged by the way, and now that she had proof, she was using it. If I wanted to return to college for my senior year, if I wanted my aunt's pics of me not posted on my Facebook wall, and if I wanted or didn't want a few other things of similar life or death import, I would be a girl during the summer, not all the time, necessarily, but all the times that Mother decreed. Was I shocked she would do this to me? Not really. Mother is, well, different.
An hour later I was in the living room being presented to Father. I had been shaved, not that I ever have much shaving to do, washed and dressed in a powder blue mini skirt and pink, collared top that strikingly displayed a really nice pair of falsies Mother had purchased, blonde wig, sandals, and I had on bright red lipstick. My one item of apparel Father couldn't see was a pair of bikini panties.
He looked up from his newspaper.
"Very pretty, Jerry."
"Thank you," I said, softly, in my girl's voice. I have a great girl's voice. "Do you think you could persuade Mother not to continue with this for the whole fucking summer? Like maybe if I did it for a couple of days, that would be enough."
I don't know why I bothered, it was a futile effort. It's not that Mother wears the pants in our family and Father the panties - I was wearing those, rather that Father is a bland, nearly non-existent presence in family matters of any importance. Or was up to then. In that regard I had a surprise coming. But at that point he was the blandest person I knew. He looked me up and down and returned to his paper, without answering.
"Jerry, take the paper away and sit in your father's lap," Mother said, disgustedly. Her disgust was for Father's apparent lack of interest in my girldom not what I had said, which she ignored.
Father put the paper down and gave me his lap. I settled on him, back to, with my legs draped over his, and smoothed my skirt into place.
"This won't do," Mother said, meaning Father's easy chair. She brought a ladder back chair from beside the fireplace, and put it down. "Sit here, the two of you. Jerry, face your father."
In our new arrangement, my bottom had a friendlier introduction to Father's lap. Right away, I was sure I felt a longish bulge I hadn't felt the first time. My tits were the part of me that Father seemed to notice. After studying them, he said, "too bad they're not real."
"Feel them Arty. You'll be amazed," Mother said.
He did. I became a girl with anesthetized felt up tits. Father gave special attention to the nipples, rubbing and squeezing and giving them little pulls in my blouse. The longish bulge at my bottom began to assert itself. I was dumbstruck but strangely turned on. Father either had faked his indifference or it simply took him awhile to get charged up.
"Before this goes any further, let's give Jerry his name," Mother broke in. "Janice (referring to my sixteen year old sister due home any moment from an overnight with her girlfriend) and I still like Mary Lou, which Janice suggested. We like it better than Tiffany."
Father's face hardened. "I want 'Tiffany', damn it!"
I was amazed. I couldn't remember hearing the man say anything so forcefully to anyone, let alone Mother. "Well...," she wavered, "if you feel that way, Arty, all right. He'll be Tiffany."
"So you guys really planned this," I said.
"That's right, we did," he said, firmly but not unkindly. "From now on, when I want you to be Tiffany, or your Mother wants it, you will be Tiffany." The contented expression on his face seemed to say that whatever his and Mother's intentions toward me were they were nothing I hadn't asked for or didn't deserve.
"Mmmmm," I laughed, responding to Father's unexpected display of manliness. I gave his lap a wiggle to show my girlish appreciation. The thing about getting made up as a girl is that you actually feel like one when otherwise you might not. That's why I had crossdressed, loving as I did the feeling it gave me, yet allowing myself only three or four adventures a year for fear of where they might lead.
Father's eyes bulged at my wiggle and so did the living presence in his pants. "Whoa, Tiffany! A girl can get herself in trouble doin that. Daughter or no daughter, she can get herself fucked if she does that!"
My alarm bell went off. This was more than I was ready for. But my bottom wasn't listening and gave another, even firmer wiggle. "Oh!," I squealed, appalled at my behavior.
Father groaned. If he wasn't fully hard he was getting there and the hardness was pushing at me with purpose. I don't know what would have happened if Janice hadn't appeared at that moment but appear she did, and howled with laughter.
"Oh, my God!," she said, finally.
"Janice, stop it. Your father and Tiffany are getting to know each other," Mother said.
"He's going to be 'Tiffany'?"
"Yes. Be quiet."
But the spell, if that's what was, had broken. Father dismissed me from his lap with a gentle push. I felt suddenly ridiculous standing there in front of my younger, if no longer little, sister while she looked at me with her laughing eyes. But Father, though done with me, was not done. His gazed turned on Janice.
"Look here, Janice," he said.
Janice ceased finding anything funny. She looked where directed, in silence.
"Tiffany got him up. Now you can get him down, honey." Again, Father spoke with impressive self assurance. Janice went to him, taking off her jersey. About Janice: medium height for a developed girl, tits medium size, but you wouldn't think of her as medium in other ways, beginning with those very same tits, not big but super nice. Janice is pretty from head to toe, almost always the prettiest girl at the beach, darkish blonde, her face more cute than beautiful but amazingly cute, and now she was going to Father to give him a blow job.
"How long has this been going on?," I said, jealously.
Janice looked over shoulder and said, "I don't want....him here."
"You mean, Tiffany, dear. All right, fine. "Tell Tiffany he can't watch you suck off Daddy and I'll make him go away before you do him suck off."
Janice made a face at me. "You mean when I make him cum in my mouth and get his cum all over my face so you can take a funny picture of me to show everyone."
I didn't think Mother went quite that far, so I made a face back at my sister and huffed out of the room. At lot of what I did was acting, which I knew but I did it anyway. I went up to my room, half sulking, half laughing, and plopped on the bed where I nursed my confusion and hurt feelings. I did that for quite awhile before opening my laptop. I checked email and facebook, then did what I had come there for. I googled crossdressing and sissyboy sites. Still being in my girl persona seemed to give the experience extra titillation. I was still having fun after a couple of hours, reading stories mainly, but I had a question on my mind, so I closed everything out and went downstairs. Mother was by herself in the kitchen, having a cup of tea.
"Where's Father and Janice?"
"They're about. After you left, your father took Janice out to the station wagon to fuck her."
"Oh, of course. The station wagon."
Mother warned me with a sharp look against being a smart ass. "He enjoys fucking your sister in different places," she said and paused, waiting for more smart ass but I resisted. She softened then and said, "You asked how long, Jerry. A few months is all."
I really didn't care how long he had been fucking Janice, or so I told myself. "You called me Jerry."
"I'll call you Jerry sometimes, sometimes Tiffany, but whatever it is, you're entirely and always, 'Tiffany'. Do not forget it, not for a second."
"Not entirely, Mother."
"Yes, entirely. You have a cunt. Also a dickie but that is an add on. Your important part is your pretty boy cunt."
"Mmmm. Well, thank you for explaining."
"My pleasure, Jerry. Father surprised you, didn't he? You see, your father is enlivened by one thing. Everything else puts him to sleep. He fooled me with his enlivened part. Sex. His great cock, wait till you see...or whatever. Father kept away from Janice as long as the poor man could. Now it's working out perfectly. Janice loves his big cock."
"Uh huh" This was the moment to bring up what had been teasing my dirty mind. "Do you think Father was wondering, you know, just wondering if...if I would give him a blow job? I'm not saying I would, Mother, I'm not saying that AT ALL, I'm just wondering if he was...wondering...about that?"
"Wondering, Jerry, or wanting?"
"Wanting? Mmmm, yes wanting also, if he was...well, wanting me to give him a blow job?"
"Or, possibly your father was wondering if the wanting was on your side, if you wanted to give him a blow job, along with wondering when you would be brave enough to fulfull your hot desire?"
"You think he was wondering...that?"
"Mmmm, are you and I perhaps both wondering about that ourselves, Tiffany? Wondering right now, in fact, at 2:30 in the afternoon, if you might want to get down on your knees in front of Father and suck his big, hard cock until you make it cum in your mouth? Right now, I'm suggesting. A wonder and a want you have that is sooo insistent, so insistent you just know you'll never be able to think about anything else until you go and give your Daddy a blow job, until you suck off that big cock." She spoke in the calmest possible tone, like suggesting that I have a glass of milk.
I stood up in the mini and neatly tucked in my blouse. I was glad I was still my pretty made up self. "Right now?," I mumbled.
"Right now. If he fucked Janice, and we should assume he did, he is still a power house. He definitely hasn't forgotten you, Tiffany."
I found Father in the garage. The station wagon was there instead of in its usual place in the driveway. Father was holding the gasoline can, looking at his lawn mower. I stood in the doorway in my little outfit, giving him something else to look at. He put down the can. I decided to show him more. I lifted my skirt to the edge of my panties and held it there. I made him wait and then I raised the skirt for him. I turned around and wiggled my pantied bottom. Father came and took my arm.
"Let's go inside, Tiffany."
"Not the station wagon?," I teased.
He smiled and led me into the house. He took me to the study. He sat in an oak swivel chair, the chair he uses for his desk, and turned around to face the room, and me. The cock tented his lap by this time, and I mean tented. I almost couldn't get his fly down the way the had zipper stretched. I had planned to ask him if he really did fuck Janice in the station wagon, but I forgot. The cock entranced me. First, going for it, then opening his pants, putting my hand inside, almost fainting from the touch of his cock on my fingers even before it touched them, the thought and only the thought of what I was doing exciting me to the breaking point, then the first actual touch and after the touch, slowly managing to get your hand around it. But the cock wants your mouth, not your hand, demands your mouth, is poised to receive your mouth. You're trembling, your mouth is dry, you're in the very nub of excitement, and you open your mouth and you fill it up with hard, pulsing cock. I rather went blank then, shorted out by a power surge, recovered and sucked cock, and sucked it more, sucked it up and sucked it down, sucking all over, the cock owning the gift of my mouth. My excitement shifted to expectation in the nick of time. The cock swelled against my tongue. It erupted like a volcano erupts. The rest I leave unsaid, except to admit it's possible I love it.
About me: I'm twenty years old, five feet eleven, slender, finely proportioned, boyish hips but an almost girlish waist and almost girlish butt, handsome, refined face that easily transcends to feminine and pretty when made up. As I said, I pass easily, and I pass as a piece of ass. No problem. Even so, I've always been straight, always thought myself straight, in spite of ideal opportunity to be otherwise, except of course in my lonely crossdressing sojourns, and in jackoff dreams. I'm half convinced I'm straight being Tiffany. She likes cock, right? Gotta think about this.
Be back next time.