Balled At My Sissyboy Debut
by Hartford
I turned eighteen in March during my senior year in high school, on the day I became a dick girl, or a sissyboy, whatever the difference is. My transformation began a little after seven on my birthday evening. I was at the computer when Mother pushed open the door to my room. She had a large box that she plunked on my bed.
"What's this?"
"More presents. These are special ones for your secret desire."
My heart jumped to my throat. I had only one secret desire, and in fact had been indulging it when Mother's footsteps sounded in the hall. The computer screen now displayed something quite unlike the pictures from "Sissyboy 3-D" I had been viewing seconds before. Mother nodded at the computer and smiled as though she knew.
"What do you mean?," I said, keeping my voice as calm as I could.
"I mean your desire to suck penises and have them fuck you, dear. You can't fool your mother. And there's no reason you should. I want you to be happy, and if being a queer is what you want, well then it's what I want. I mean there's nothing wrong with it. They even let queers be in the government now. They even let them get married to each other, for goodness sake."
I stopped myself from asking why she thought I was a "queer". What difference did it make? Probably she had tracked my Internet footsteps somehow. Maybe she had found out about my crossdressing in my sister's clothes at the mall, which I had done twice. I was embarrassed, as you would expect, but Mother's apparent sweet acceptance of her son's "queerness" didn't really surprise me. You have to know Mother to understand.
I felt that I needed to clarify one thing. "Mother, I'm not interested in queers. I'm not interested in guys who are gay."
"I know that, dear. You like real boys, or I suppose it's real men, not boys. I know. And why shouldn't you? You are pretty as can be. It's my fault you weren't a girl to begin with."
"It's not your fault."
"Well, we are what we are. You have all the makings of a lovely girl. Except one."
"Except three."
"Oh, don't worry about those. Open your presents."
The box was open at the top. I turned it over and spilled the contents on the bed. There were sexy panties and bras, two teddies, two skirts, cute tops, makeup and creams, two wigs - blonde and auburn, a pair of realistic tits, two realistic dildos, in all a dick girl's treasure chest. Twenty minutes later, I was ready to meet the world in my new self or at least the visitor waiting for me in the living room.
"You look just dreamy, dear. Bob Bard will be thrilled when he sees you."
I blinked at her. "Mr. Bard?"
"He's downstairs. He knows all about our little secret. He's very excited to meet Debbie. Is that name all right? You need another name. Bob loves the name, Debbie. He suggested it."
I was having trouble processing this. "You told Mr. Bard!?"
"I did. You may not have noticed but when Bob is around he can hardly keep his eyes off you. Imagine how it will be when you're a girl! Bob says you have the perfect face and body for a sissyboy, which is the same thing as a dickgirl, I gather."
"It's not exactly the same," I mumbled. My heart was racing.
"Is it close enough?"
"I guess so."
"That's good because I think Bob thinks it is."
"He's downstairs?"
"Yes. Waiting for you."
The other question, shouting in my brain, I was afraid to ask and Mother didn't elaborate.The Bards were our next door neighbors. They had two boys younger than me, big kids like their father; linemen on the high school football team, and a little girl. Mrs. Bard was a teacher at the high school. I actually had fantasized about Mr. Bard, and I had read his stares differently from Mother, as looks of disparagement. I preferred her interpretation.
"Is Mr. Bard gay?," I finally said.
"No. He's like you, dear, except the opposite. He likes sissyboys or dick girls, whatever you want to call them. I don't think that's necessarily gay, is it?"
Mother took my hand and led me from the room. I made her stop at the bathroom for a last look in the mirror because I worried about my lipstick. It was fine. I was fine. I looked like a teenage sex model, of the female variety that is, if you overlooked my chest. Mother said she thought Mr. Bard would prefer my own smooth chest and perky nipples to fake boobs, not that my chest was there to see behind the pink cotton top. The top was buttoned and dipped just below the bottoms of my panties. My legs were bare and I was barefoot. Mother had selected the blonde wig and it framed my made-up face quite nicely, yellow curls falling to my shoulders. I had an idea of my own then, remembering a description of a sissyboy from a story, and as I looked in the mirror I opened the buttons and pulled the top over my shoulders and down far enough to partially immobilize my arms but Now Mr. Bard would see my perky nipples. I was faint with excitement.
Every light was on in the living room. Mr. Bard was on the sofa, wearing a bathrobe. He looked at me. I waited for him to smile or say something. He just looked and blinked a few times.
"Hi, Mr. Bard," I said.
Mr. Bard still didn't smile but he said, "Hello, Debbie. You are the perfect sweet piece of ass I thought you would be."
"Thank you," I mumbled, and glanced around to see Mother's reaction to Mr. Bard's greeting. She looked pleased as punch.
There was another long silence while Mr. Bard continued his staring until I stupidly said in my nervousness, You're wearing a bathrobe."
Mr. Bard's face relaxed and he laughed. "I am indeed, cutie pie. Turn around. Pose for me. Lift up that thing you're wearing so I can see your treats."
I blushed and smiled at him, feeling naughty. "Gee, I thought my nipples could be treats, Mr. Bard."
"Oh, God," he moaned.
I was feeling better, less anxious, incredibly excited and somehow empowered that this hunk of a man who I had thought didn't like me in fact was turned on by me. I turned around as directed and saw Mother. I was taken aback, having forgotten her presence in my excitement. What had she thought of my nipples remark? Nothing critical, apparently. She beamed, and she had acquired our video camera. Seeing me notice it, she said,
"We have pictures of the first time you walked and your first day at school. We should have some of your first time as a sissyboy."
This sparked a question I had been reluctant to ask."What does first time as a sissyboy mean exactly?" I froze as Mother raised her face to the ceiling, which she often does when she's about to say something big.
"Well, for one thing it wouldn't be right if poor Mr. Bard didn't have his aching manhood relieved by the dear thing who is making it ache so."
And if I hoped a blowjob was going to suffice, Mr. Bard coughed and added, "Nor would it be right, Maggie, if a sissyboy didn't get fucked on his birthday."
Mother tittered. "Oh, very true, Arnold. Very true."
With that, Mother suggested that I begin posing, which I did. Considering the dazed state of my brain it was a wonder I could even stand up. However, posing like a sex model was something I had practiced a hundred times or more in the privacy of my fantasy life. I was able to do it by rote, practically. The poses were well received. Mr. Bard's favorite, at least the only one he asked twice for me to repeat, was getting on my hands on knees and wiggling my bottom at him with the shift up out of the way while I looked over my shoulder at him and licked my lips. It was my favorite, too. And the third time I did it, I said, "Mmmm, Mr. Bard, I hope you won't fuck me too, too much." I was pretty hot by then. I had also accepted Mother's partnership, so to speak, in this sissboy venture. I even looked for her approval of the sufficiency of my naughtiness,though Mr. Bard's approval mattered more. When he yanked open his robe, I saw I had it. Big time.
The robe parted right after I made that third little tease.
"I'll decide what's too much or not enough, you sweet bitch," Mr. Bard said, showing me what I was going to be fucked with. It was mesmerizing, plus breath taking, plus dicky hardening and I was hard already.
Mr. Bard grinned. "Fearsome, isn't it?"
I was speechless. Mother said, "Debbie's a brave boy."
I might not have been able to talk but my mouth wasn't helpless. I moved on my knees. Mr. Bard opened his legs for me. Now I looked down on the cock looking up, straight up it was, like a missile on a launching pad. Fearsome was a good word for it. The cock bristled with purpose. The pink head smoothly invited me. Beneath waited the vein bulging shaft, more than my mouth could possibly take, more I realized that any of me could take. But a sissyboy must always do his best. I dipped my head and thus began my first sissyboy assignment, also my first experience of any kind with a cock not my own. I'll rephrase that: a dick that wasn't my own; silly to call my not quite five-incher a cock.
After a few kisses and licks, I opened wide and began to suck. Mmmmm, it was soooo good. What I had been missing! And would be missing still if it weren't for having such a thoughtful mother. I was a natural cocksucker. Mr. Bard told me so afterward. In no time, my head was bobbing like a pro. I felt Mr. Bard's hands hold back my curls so he could watch. Who could blame him? For me, along with the thrill and the knowing came a dread. My fate was sealed. I had been made with the looks and by inclination to be a cock slut and now I was. Thank you, Mother. At least, I would be a slut for straights, I figured. This struck me as better, as well as more exciting, than being an outright "queer".
These thoughts were in the back of my mind as my head went up and down. I was gradually taking in more and more of my slipperly, thick prize. On the down strokes it filled my mouth and pushed into my throat, gagging me, and I let it gag me, I wanted it to gag me, I liked it gagging me. I came up for air so I could go down on it again, sucking at the head, sucking the shaft, sucking the pulsing hardness, sucking and sucking, then making it gag me. It startled me when Mr. Bard let go of my curls and grasped my head to pull me off. I gazed up him, bleary eyed, wondering what was wrong. Nothing was wrong. He was gasping and struggling to hold back his orgasm which he did hold back, in order to fuck me.
He reached for me and turned me over. Mother had thoughtfully put two pillows on the floor. Mr Bard lay me on top of them so that my bottom was raised. I held my breath. I felt Mr. Bard's strong hands on my hips. Then I felt what I was waiting for. The cock divided the crease in my bottom and bumped up against my boycunt where it paused. I stopped seeing as well breathing, squeezing my eyes shut; squeezing my hands together. Mr. Bard's cock was rigid and so was I, from head to toe. The pausing ended. The cock jammed inside me, not far but far enough to make me yell from searing pain. It was a delicious pain. I didn't mind if it would kill me. I imagine only a sissyboy can understand that. The cock went deeper and the pain went deeper, and in a little while the pain began to fade and the pleasure grew and I became lost then and for good.
Mr. Bard fucked me gently at first, until I got used to it, and after that he fucked me hard. Not long, though. He was too worked up to make it last which was kind of too bad but a sissyboy can't complain. I got to like being a sissyboy from being with Mr. Bard, as compared to a dickgirl, I mean. Before Mr. Bard left he asked if he could "see" me again. He asked Mother. She said, "Sure. When would you like him?" Mr. Bard said he would like me the next day but he would have to pace himself, being married and all, plus not being a young guy anymore.
"Well,just call me when you want him again, Arnold," Mother told him. They were talking about Mr. Bard fucking me again and I wasn't even part of the discussion. It gave me a hardon.
(Editors note: This story is a variation on the theme used in 'The Adventures of Julie", part one, which I posted about a year ago.)