Tiffany's Date

The following is an excerpt from the story, "The Further Adventures of Baby Bobby-the Strict Nanny"

My name is Tiffany Johnson and I guess I was meant for this job. As a teenager, I always loved to tease and dominate the guys who wanted badly to see what was under my tight, short tops and skirts. I developed early in my youth, quickly moving into a D cup before I was sixteen which hardly went unnoticed by the opposite sex. In addition, I quickly grew in stature from 5'7'' to 6'0' by the time I was a senior in high school. I started to notice a certain attention I was getting from the sissy boys in high school. I think they wanted me to be their mommy but they soon found out that this mommy had a very strong spanking arm.

I thought for those of you who read that paragraph and wondered about what really happened, I would tell a little about one particular time, a very ordinary date, if you will, in which a timid high school boy learned his proper place once and for all.

　

Tiffany's Date
　
　
I don't like it when people stare at my boobs.

I especially don't like it when nerdy, sissy guys stare at them, as if I might deign to let them touch them, or something.

Of course, I understand why people do stare at them. They are large, perfectly round, and hard to miss, especially considering the way I dress. At 38EE, even the girls in school tend to stare at them. But I love wearing revealing clothes, skimpy outfits and snug fitting tops and skirts that showcase my spectacular body. And I don't mind when the good looking, hunky guys look at me, but it annoys me to no end when I catch one of the skinny little wooseys with glasses staring at me. How dare they! Don't they know I wouldn't give them the time of day?

I do my best to make them aware of my feelings by pushing them around whenever they get in my way. I like to cut in front of them in line and watch them pout as I act like they don't even exist. And as if my six feet in stature weren't enough of an intimidation, I like to wear high heels to school to make me tower even more over the wimps who get in my way. I like to give them a rude shove so that they learn their place. And any who show even the slightest trace of backbone by complaining earn themselves a harsh slap in the face. That usually sends them running and I laugh whenever I see it happen.

However, there are some times when the naughty side of me feels the urge to take it a little further.

They other day, in the lunchroom, I was sitting with some of my friends, a group some people would call, "the popular crowd", made up mostly of cheerleaders and burgeoning models.

I was sipping my drink, when I saw two tables over, a nerdy guy, probably a sophomore, trying hard to hide the fact that he was staring at me. Today, I was wearing a clinging halter top over one of my favorite demi-cup push-up bras. The overall effect was quite impressive, if I may say so myself, with every curve of my breasts clearly on display.

At first, I started to get angry. And then, an idea suddenly dawned on me. The thought of it made me giggle and I took a piece of paper from my purse and wrote down my address on a piece of paper. Standing up, I walked slowly over to the wimp's table, my saucy hips swaying seductively. His geeky friends immediately began gibbering amongst themselves as they saw me approaching. With my high heeled sandals clicking audibly on the tiled cafeteria floor, it announced my presence like a loudspeaker to any male nearby.

I watched as the nerd's face grew red--no doubt he was aware that he had been discovered and now he was fearing the embarrassment I was about to unleash on him. Nonetheless, as I came up to the table of these boys, I stood over them and smiled pleasantly.

"I couldn't help but notice you looking at me," I said in my sultry, very feminine voice.

"Oh no-I was-um-I was just-" the nerd stammered frantically.

"If you like me, why don't you come over after school," I said invitingly, as I slid the paper with my address across the table to him.

The nerd looked as if I'd hit him with a two by four. His mouth dropped open and he stared first at the paper and then up at me unbelievingly. For a second, he just stared dumbfounded and then he scrambled to snatch up the note, no doubt thinking it probably said something like 'drop dead nerd', or something similar.

Instead, when he realized it really was my address, he still found himself at a loss for words.

"Three-thirty, sharp," I said crisply, and I turned around and walked away without a further word.

Hushed, urgent, and excited whispering broke out from behind me as his flabbergasted geeky friends tried to grasp at what had just taken place.

I smiled to myself as I saw once again, how easy it was to manipulate the opposite sex.

The sissy arrived at 3:30 on the dot, just as I expected. When I opened the door, he looked flushed and uncertain, and he licked his dry lips nervously.

I was wearing a sexy black bustier that had strings that cinched it up the front, producing a fantastic cleavage and two big mounds where my voluptuous breasts were spilling out of the top. I made sure he wouldn't see my nipples because that is a privilege that I would never grant a sissy like him.

As I stood before him with my hands on my hips, I still had on my short gray skirt from earlier which had the slit up the side. With my four and a half inch heels, the sissy's face was right at the level of my boobs. He gawked at them in awe and tried to articulate some sort of greeting but his voice cracked when he opened his mouth. Intuitively, I could tell he was still a virgin and I merely smiled agreeably down at him as I took his hand and led him inside the house. My parents wouldn't be home until later and in any case, what I wanted to do wouldn't take long.

"Did I surprise you?" I asked the quivering wimp.

"Uh, yes, er, I mean, it's just that, well, I'm uh..." he could hardly string three words together that made any sense and his face was flushed.

I began brushing my long, curly brunette hair with my hairbrush, a large oval shaped instrument with a back made of hard, firm oak. As I did so, I arched my back slightly, pushing my impressive chest outwards to further fluster the overwhelmed sissy.

"You like watching me, don't you," I prompted him.

He blushed furiously and I could see that I'd hit a sensitive spot with that remark.

"Well, I um, ya know..." he stammered stupidly.

I looked him deep in the eye as I applied a coat of dark, wine colored lipstick to my full lips, purposely taking my time to tease him with it. He watched me hungrily like a starved dog eyeing a piece of succulent bacon.

"Do you like my breasts?" I suddenly asked him boldly as I smacked my lips together and put away the lipstick.

He swallowed hard as he tried to come up with an appropriate response.

"Uh-huh!" he said, sounding completely geeky in doing so. It was obvious he'd never been with a girl, sexually or otherwise.

"You don't think they're too big, do you?" I asked as I ran my immaculately manicured fingers softly over the curves exposed above my bustier. His eyes watched my hands closely as they stroked the smooth skin and I observed a small bulge forming in the front of his pants.

"Oh no! I think they're just right!" he said, now filled with determination.

I smiled enigmatically and without saying anything further, I moved my hand down to his crotch and gently rubbed his little erection. Even as he blushed beet red, he closed his eyes in ecstasy and I unzipped his fly, lowering his pants to his ankles. He gasped and tried to cover up his underwear, suddenly embarrassed at being so exposed.

With an abruptness that caught him totally off guard, I took a seat on one of the dining room chairs and suddenly yanked him over my lap.

"Wha-what's going on?" he quaked in terror as he found himself staring down at the floor in front of his face.

"I'm going to show you what happens to little sissies who think they can stare at my chest," I snapped, revealing the anger I had been hiding until now.

Before he could say another word, I brought the flat side of my hair brush down on his little round bottom with all my might, delivering a harsh, stinging swat to his cheeks.

SMACKKK!!!

He howled in pain and tried to get up but I was already anticipating his move. I reached over and quickly grabbed his right arm, wrenching it around and pushing it up between his shoulder blades. He squealed with panic and it forced him to put his head back down to relieve the pressure. When he was back in position, I jerked his underwear down and off his butt, leaving his backside bare and ready to be spanked. Already, a bright red oval shape had formed that covered both his round, nubile cheeks and I was determined to add much more color than that.

Holding his arm with my left hand so he couldn't escape, my right grasped the hairbrush firmly and I brought it down with a hard, punishing swat that filled the room with its impact.

SMAACKKK!!!

"OOOOWWW!!!" he cried desperately, his legs kicking helplessly.

Despite the slimness of my arms, I'm quite strong and I used my strength to good effect, wielding the hairbrush with fierce, blistering swats. He gasped for breath as he tried to cope with the assault on his smooth, tender cheeks but his facade of manliness evaporated in an instant. By the third time my hairbrush had smacked his bottom, he was bawling like a two year old. I settled into a determined, calculated rhythm, slapping his quickly reddening fanny and watching as it turned a hot, angry shade of crimson. Before long, he stopped fighting me and he willingly submitted to his punishment although he was still flailing his legs desperately in response to the severe spanking he was receiving. I rewarded his submissiveness by increasing the tempo and severity of the sissy's paddling, giving the little crybaby exactly what he deserved.

After blazing a red inferno on the center of each cheek, I moved outward, slapping the sides with crisp, deliberate blows that made him wail in agony. When the sides had achieved the same degree of color as the center, I returned my attention to the original target, the middle of his seat where his youthful, fleshy cheeks curved most delightfully. My hairbrush swung down again and again, and the poor sissy sobbed and cried like a little girl. Bunching the one fist that he had free, he beat it against the floor in frustration as the tears streamed down his face.

This was the image I wanted to forever sear into his mind: that of a helpless sissy being severely paddled by a superior woman who is in complete control. He would never look at the opposite sex in the same way again.

At last, I stopped spanking him and I set the hairbrush down next to me with an abrupt clatter.

The nerd tried to get up but I rudely forced him back down again with his bent arm.

"Not so fast, Sissy-boy," I warned him and I reached around behind the chair where a jar of vaseline was hidden and waiting for me. Dipped inside, was a nice, thick buttplug that was coated liberally with the sticky lubricant. Taking a dollop in my hand, I pressed it up against his anus which made him struggle once more to get free.

"Spread your legs, or we'll start all over," I told him evenly.

Sobbing pitifully, he did as he was told and I pushed a glob of the vaseline into his hole. Taking the big rubber buttplug, I brought it up and rubbed it against his rosebud, looking for the right angle for penetration. He squirmed and squealed as I began slowly but firmly pushing it in.

"Stop!" he wailed, "Stop! Please! It's too biiiiggg!"

I ignored his pleas and pushed harder.

"Spread your legs wider you big sissy! This is for your own good!" I commanded him.

He moaned as the buttplug finally eased past his sphincter and disappeared inside him, the rectangular handle the only thing left exposed. He was breathing heavily and still crying but I knew he needed still further humiliation. Standing him up, I looked down into his tear stained face and held his jaw firmly in my hand while he stood on shaking legs.

"Take the rest of your clothes off. Right now!" I ordered him in my authoritative voice.

He crumbled before me and I knew he was completely defeated. No doubt he was frantic to know what was going to happen next but I kept him in the dark. When he had finished and he was covering his pathetic little wiener with his hands, I took advantage of the fact that his bright red bottom was completely defenseless. Picking up the hairbrush, I brought it down with a blistering smack against his stinging rump.

"Get into the living room, Sissy!" I told him.

He howled in torment and practically ran into our spacious living room where I had a few things laid out for him. On the floor, I had arranged a thick set of baby diapers, big enough for him to wear, some safety pins, powder, and of course, plastic panties. I was going to dress this sissy in the most humiliating way possible, and show him what I thought of pansies like him at the same time. I pushed him down on the floor on top of the diapers and began situating him over them while he whimpered from the pain of his punished bottom.

With several good shakes of the baby powder I covered his crotch and up to his chest, giving him the infantile smell of a toddler.

"Why are you doing this to me?" he whined between sobs.

I pulled up first one side of the diapers, then the other, pinning him securely in place with the special locking pins. He'd have to find some way of cutting those off if he ever wanted to remove them again.

"Because you're a panty-waist sissy. And it's time you were put in your place," I told him as I shook out the plastic panties. They were a pink translucent pair with patterns of blocks and rattles decorating it. He grimaced as I snaked them up his skinny nerd legs, brusquely pulling them up and over the thick, bulging diapers. He must have been surprised to find that they fit him so well and I snapped the waistband against him before making sure the diaper was completely tucked in. As a final touch, I snapped shut the tiny lock in back, making sure the panties would be staying right where they were. This sissy was going to be wearing his diapers home whether he liked it or not!

Next, I gathered a peach colored t-shirt with pink edging and feminine frills. He nearly burst into tears when he read the gaily written inscription on the front. It said "I love my diapers" on it, and I smirked as I pulled it down over his head.

With his fat, plastic covered diapers and sissy shirt, he looked every bit, the overgrown baby.

That was when the doorbell rang.

　

"Well, who could that be, Sissykins?" I taunted him.

I saw abject fear all over his face as he looked terrified at the door.

"Better go answer it, unless you'd like to take another trip over my lap," I told him, leaving no doubt in his mind as to what would happen if he refused.

"Please," he pleaded desperately, "please don't make me."

Without a word, I walked over and picked up the hairbrush, fixing him with a severe look.

He probably wet his diapers out of fear because he jumped to his feet in his hurry to get to the door. Between the thickness of his diapers and the fat buttplug stuffed in his ass, he stood with his legs spread apart in a distinctively babyish pose. Biting his lip in angst, he slowly pulled the door open, but only enough to peek through without exposing himself.

That wasn't going to do it for me. I came up from behind him and yanked the door open the rest of the way, revealing his diapered state to my friends who were waiting on the front porch. They immediately burst into laughter as they came inside and took in the ridiculous image before them. The poor sissy reacted predictably enough--I heard a hissing sound and soon a darkened spot appeared in the front of his plastic panties. The pansy was actually wetting his diapers! I burst out laughing myself since I couldn't contain myself anymore.

Tears of shame filled the sissy's eyes as he struggled to take in the humiliation being dished out to him. I imagine nothing could possibly have been worse for the nerdy panty waist than to have four beautiful and sexy girls from his school laughing at him as he wet his diapers like a baby.

Coming up behind him, I squeezed the thick seat of his diapers and I could feel that he'd wet so much that his pee had soaked down between his legs and into the seat of his pampers.

I shook my head at his pathetic display but made no move to change him.

"Ready to go home now?" I asked him.

He nodded abjectly, totally subservient now.

Opening the door, I threw his socks and shoes out into the yard. Turning him in the direction of the open door, I swatted him soundly on his diapered butt with the hairbrush, causing him to stumble outside. Once he was through the threshold, I slammed the door shut, locking him outside while the others laughed themselves silly.

"Have a nice walk home, Sissy!" I called out to him through the door.

I could hear him beating on the door frantically, begging for his clothes and to be let back in.

"Better get lost Sissy, or I'll call your mommy and have her come over and pick you up. You'll have an interesting time explaining your wet diapers to her when she gets here," I told him as I chuckled at his predicament.

The nerd stood for a moment considering his perilous choices before we heard his footsteps quickly retreating down the sidewalk.

I think we laughed until our sides hurt.

That was one sissy who had learned his lesson once and for all.