Tiffany's Date--A Sissy's Perspective

Tiffany's Date- A Sissy's Perspective

I was sitting in the lunchroom of our school with some of my Astronomy Club pals and trying hard not to stare at the object of all my fantasies, Tiffany Johnson. She was about two years older than me, a senior, and totally oblivious to my existence. She was everything I could ever want in a girl; tall, beautiful, long, dark hair, captivating green eyes, and a fantastic body. But today what I couldn't peel my eyes off of were her two wonderful breasts. She was wearing a snug yellow halter top and I could make out every mouth watering curve of her bosom, not to mention the deep plunging cleavage exposed by the low scoop cut of her top. She seemed ready to burst out of her top at any moment!

She was so incredible and she carried herself in the same way that all hot girls who are aware of it do. She was confident, even cocky, and I knew I didn't have a snowball's chance in hell of getting her to return a greeting in the hall, not that I had the balls to try that, of course. No, I'd sooner lasso the moon than get any attention out of her.

Still, I could watch her and admire her from afar. She was too hot to ignore and I thought she was the sexiest babe in our school. No doubt she would someday be a top paid model but I could always brag that we went to the same school together.

I was glancing at her and trying to be surreptitious about it when I saw her make eye contact with me for a moment. Before I looked away, I thought I caught a flash of anger in her pretty eyes and I tried to concentrate on my lunch instead. I was in mid-sentence with one of my friends when I heard the unmistakable sound of high heels clicking on the tile floor of the cafeteria. To an ardent masturbator such as myself, I was instantly drawn to the sound like a dog to a high pitch whistle. Turning around, I was stunned to see Tiffany walking toward us. She had a very sensuous sway to her, placing one high heeled foot in front of the other like a model on a runway and her curvy hips moved up and down in a perfect harmony.

Nonetheless, I was filled with a dreadful foreboding. Tiffany was known for her dismissive manner towards guys she wasn't interested in and I feared she was coming over to slap me or something. I just about came unglued when she stopped across the table from me and fixed me with her ravishing smile.

"I couldn't help but notice you looking at me," she said in a voice that could have melted lead.

"Oh no-I was-um-I was just-" I babbled nervously. I couldn't believe this hottie was actually talking to me!

"If you like me, why don't you come over after school," she said sweetly, and she slid a piece of paper across the table to me.

Was I on planet Earth? This must be a dream because there was no way the hottest babe in school could be asking me to come over to her place!

I was reasonably sure this was some kind of joke concocted by her and her sexy cheerleader friends and I was hesitant to pick it up and read it. Nonetheless, my friends were looking at me expectantly and I had to do something.

Cautiously, I reached over like I were about to pick up a tarantula, and took the folded piece of paper, afraid to read what it said. But when I did, I could plainly see the address in her perfect feminine handwriting and my jaw dropped open in shock.

I didn't know what to say! I blinked and stared at the note and then up into her gorgeous face.

"Three-thirty, sharp," she said tersely, and I gulped with excitement.

Before I could blurt out a reply, she turned on her heel and sauntered off.

Man, she had a nice set of buns, I thought as I admired her firm derriere within her short, form-hugging gray skirt.

My friends were babbling at me a million miles a minute but I was in another world.

Tiffany Johnson wanted me over at her house!!



Unfortunately, the time Tiffany had specified didn't allow me any leeway to prepare after I got out of school. I would've liked to have gotten her some flowers or something but I didn't want to take a chance of being late. I had just enough time to rush over after getting off the school bus to make it by 3:30.

As I stood quaking with nervousness on her doorstep, I checked my watch and then checked it again. I was right on time so I was hoping to score some points already.

During the last couple of hours of school today, I had been puffed up with pride. I knew that Tiffany only dated college guys and real stud types. Of course, I was the total opposite of that. I was somewhat small, shorter than most guys my age, and kind of geeky, truth be told. My friends could not believe I had been invited over for a date and all of them were green with envy. All except Harold who was the only one to discourage me from going over to see her. He wouldn't explain why but I sensed he knew something that I didn't. Still, I was caught up in the intoxication of pride and puppy love, and wild horses couldn't have prevent me from accepting her offer.

Now, as I stood on her porch, my finger shook as it went up to press her doorbell. The first time I missed and I had to mash it with the palm of my hand before I heard the chime inside.

When the door opened, my breath was taken away.

Tiffany towered over me, her big bosom ready to spill out of an unbelievably sexy black bustier. It was laced up the front and I could see the soft curves of her breasts pushing against each other where they were exposed. Above that, her voluptuous melons were displayed in an awe inspiring presentation, her cleavage splitting and curving away from each other. I could see the rise and fall of her chest with each breath she took and I was sure her top was being pushed to the limit.

I wanted to say something but what could I say? My voice was trapped in my throat and my tongue was tied in a knot. I swallowed hard and opened my mouth but I felt like I were choking.

With a disarming smile, Tiffany reached down and took my hand like I were a small child--which incidentally was exactly how I felt--and she led me inside.

"Did I surprise you?" she asked me when she could see I was at a loss for words.

"Uh, yes, er, I mean, it's just that, well, I'm uh..." I stammered. I had never been with a girl alone and Tiffany was no girl. She was all woman and I had serious doubts as to my ability to be able to handle her. As I stared up at her, I blushed red with the intensity of the moment.

I watched as she took a large hairbrush and began running it through her long, silky brown hair. As if she weren't fabulous enough as it was, I noticed that as she did so, her arms being behind her head caused her delicious boobs to be even more prominent than they already were--if that were even possible. I was helpless as I gaped at her, unable to take my eyes off her captivating form.

"You like watching me, don't you," she said in a sultry tone of voice.

I turned a beet red at being caught again.

"Well, I um, ya know..." I rambled. I just couldn't manage to sound like anything but an idiot!

Her pretty eyes bored into me as she took a stick of lipstick and began applying another coat on her full, sensuous lips. She was so freakin’ sexy!

"Do you like my breasts?" she said after she'd smacked her lips together and capped the lipstick.

What was the best way to respond to that question? I found her directness and confidence overwhelming me and I swallowed hard to try and communicate.

"Uh-huh!" I blurt out suddenly. What a fool I was!

"You don't think they're too big, do you?" she said as she stroked the curvy mounds of her breasts that were exposed above the top of her bustier. I noted that she had immaculately manicured nails and my eyes were hypnotized by her erotic teasing movement. My little wiener was straining within my pants at this unbridled display of sexuality.

"Oh no! I think they're just right!" I finally managed to croak.

She smiled sweetly at me and bent over, allowing me to gaze down her top as she softly stroked my imprisoned erection. My face was burning bright red with embarrassment but I was about to explode from her electric touch. Unexpectedly, she quickly unbuttoned my fly and pushed my pants down, exposing my underwear and the small damp spot of pre-cum on the front. I gasped in response and she smiled at me with a strange look while she took a seat on one of the dining room chairs behind her.

All of a sudden, she reached over and grabbed me by the wrist, yanking me over toward her. I lost my balance and fell on her lap face down, and she made a quick adjustment to my torso which left my bottom sticking up in the air. It was all happening too fast and I was suddenly filled with terror.

"Wha-what's going on?" I quaked fearfully.

"I'm going to show you what happens to little sissies who think they can stare at my chest," she snapped at me, her voice taking on an edge.

I bit my lip nervously and squirmed trying to get up but I felt the searing impact of her hairbrush as she brought it down painfully on my rump.

SMACKKK!!!

I bellowed out in surprise and instantly tried to get up off of her lap but she was too quick for me. I felt her grab my right arm and twist it behind my back, making me squeal with pain. She drove it up behind my shoulder blades and I was forced to go back down, leaving my fanny defenseless and at her mercy. I felt her long nail at the small of my back as she jerked my underwear off my bottom and down my legs. I tried to wrench my arm free but her grip was like steel.

My fanny twitched and she brought the hairbrush down again, delivering a blistering swat right in the center.

SMAACKKK!!!

"OOOOWWW!!!" I wailed at the top of my lungs. Frantically, I kicked my legs desperately as my eyes brimmed with tears. This woman could really spank! She had only swatted me twice but I was already ready to start crying. And that's just what I did as she began spanking me in earnest.

Slapping my bare bottom with harsh, penetrating swats, she wielded her hairbrush with devastating results. I sobbed and cried as she brought it down again and again, slapping my cheeks with her pent up anger and resentment. With tears spilling down my cheeks, I could see the solid stance of her glossy black high heeled sandals, supporting my skinny frame as I squirmed and kicked like a little baby.

Eventually, I gave up and I just lay there, hoping to end the terrible spanking sooner. However, rather than reward my submissiveness, she seemed to take it up a notch, smacking my bottom with even greater ferocity. Her attention shifted to the tender sides of my cheeks which she paddled to a blazing inferno before returning once more to the center of my bottom. I kicked desperately and bawled openly as this amazon spanked my punished fanny.

Finally, I heard the wooden hairbrush clatter on the tabletop.

I thought she was finished so I tried to get up but she held me firmly in place.

"Not so fast, Sissy-boy," she warned me gravely.

I felt a sticky glob of vaseline being pushed into my back hole and I squirmed helplessly as I sobbed like a child.

"Spread your legs, or we'll start all over," she ordered me tersely.

What was she going to do now? I asked myself in a state of panic.

Obediently, I spread my legs and I felt her pushing a big rubber object against my reluctant back hole.

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

There was no way that monster was going to go up inside of me and I struggled to free myself. But Tiffany just kept pushing harder and I felt the fat, blunt end of the buttplug pushing it’s way inside me.

"Spread your legs wider you big sissy!" she barked, "This is for your own good!"

I whimpered in defeat as the wide rubber plug slid past my pouting sphincter to lodge itself firmly inside me. I gasped from the feeling of fullness and emasculation and I sobbed with defeat. This busty woman was calling the shots today and there was nothing I could do about it.

As she stood me back upon my wobbly feet, I tried to brush away the tears that were streaming down my cheeks. She grasped my chin in her firm hand like my mom used to when I had been naughty as a child.

"Take the rest of your clothes off. Right now!" she snapped in her demanding tone.

I shivered with fear at what more this knockout might do to me but I was helpless to do anything but submit. With all due haste, I tore my clothes off, still trying to come to grips with this terrible turn of events. When I pulled my undies off, I covered my little pecker with shame, embarrassed to reveal its tiny size. However, Tiffany took advantage of the fact my hands were both occupied and she smacked my bare bottom with the hairbrush in a blistering swat.

"Get into the living room, Sissy!" she ordered me even as I wailed out miserably and grasped my flaming bottom with my hands. Now completely uncovered, my little wiener wiggled foolishly as I practically hopped into the other room, a fresh torrent of tears bursting from my eyes. With blurred vision, I saw what looked like a baby’s layout waiting for me on the floor. Before I could guess the implications of that discovery, Tiffany rudely shoved me onto the ground, positioning my red, stinging bottom on a thick rectangle of white cotton.

As I wiped away the tears from my face, Tiffany bent down and began shaking baby powder all over me, using much more than was necessary. The scent brought back instant memories from when my first grade teacher used to change my diapers during recess. That had been humiliating enough but now that it was being done to me by this buxom babe was almost too much to bear!

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

She didn’t answer immediately as she pulled the thick, but very soft cotton up between my legs, and inserted a big, bunny headed pin through the cloth to secure either side on my waist. I barely had time to register the faint locking sound they made as they were snicked closed.

"Because you're a panty-waist sissy. And it's time you were put in your place," she quipped as she shook out a pair of pink plastic panties.

I quailed as I beheld the babyish looking vinyl panties being pulled up my skinny legs. They were decorated with blocks and rattles and I knew they were meant for a baby girls. Here I was, sixteen years old, being put back into diapers and plastic panties by the woman of my dreams and I was completely helpless to do anything about it! I whimpered with shame as she tugged them up past my knees, working them over the bulging, bulky diapers she’d pinned on me.

Roughly pushing me over my side, I felt her pulling something within the elastic waistband of the plastic panties tight, and then I heard the distinct sound of a lock being closed. With a smug look of satisfaction on her pretty face she stared down at me with a challenging demeanor as if to say ‘try and get those off now’. It made me want to cry!

But then she picked up a peach colored t-shirt that was lined on its edges with frilly ruffles, pulling it over my head while I sat there dumbfounded. It barely reached my waist and when my head poked through the top, I looked down and read with shock the inscription written in gaily childish letters across the front:

I love my diapers


And just then, the doorbell rang.

　

With my mouth hanging open, I turned to Tiffany, unable to move.

"Well, who could that be, Sissykins?" she said tauntingly.

I gulped hard in a compete state of panic, still trying to come to grips with what was happening.

"Better go answer it, unless you'd like to take another trip over my lap," she said with her smug, confident look.

My bottom was still blazing from the fierce spanking she’d given me moments ago. I was terrified at the prospect of going across her skirted lap again.

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

Without another word, she suddenly stood up and walked over to where she’d left her hairbrush, picking it up and looking back at me evenly. Realizing she was deadly serious, I gulped hard and jumped to my feet, desperate to avoid that terrible instrument of punishment. As I did, I could feel the fat buttplug making its presence known and it forced me to waddle even more than I would have normally from the thickness of the bulk of the diapers between my legs.

Maybe it was just a solicitor, I reasoned to myself as I trundled toward the door. If I could just open the doorway enough to peek out and get rid of them, maybe I could still escape here with a shred of my pride.

Pulling open the large ornate door just a crack and keeping the shameful words on my toddler top hidden, I looked out to receive another shock. There on the doorstep were three hot cheerleaders from my school, still dressed in their sexy and very revealing outfits, staring back at me with knowing smiles on their beautiful faces.

Just then, I felt the door being pulled open from behind me and I gasped with terror as I stood in my sissyish state before them. They took one look at the fat diapers I was wearing, encased in babyish pink plastic nursery print panties and the girlish t-shirt I was wearing, and they burst into gales of laughter. I was so shocked and mortified that without even realizing it, a stream of pee burst out from me, soaking the front of my diapers.

Even Tiffany erupted in laughter and the girls pointed at my diapers, falling against each other as they rolled with amusement. I could only hang my head in shame as I drank full from my cup of humiliation. A tear rolled down my face and my shoulders shook miserably.

It was at that moment when I felt Tiffany reach down and squeeze the thick seat of my baby pants, confirming the fact that I’d wet myself.

She shook her pretty head and looked at me knowingly with obvious disgust.

"Ready to go home now?" she asked me.

I nodded abjectly, completely defeated and broken by this beautiful woman.

With a smirk on her face, she reached down and threw my socks and shoes out the still open front door onto the lawn. Looking up at her in surprise, my mouth opened as I tried to understand what she had in mind. With rude abruptness, she turned me in the direction facing outside and swatted my thickly padded bottom with her hairbrush, sending me headlong onto her lawn past her giggling friends. I fell on my hands and knees just as I heard the heavy wooden door slam shut behind me. Seized with panic, I bolted back up and began pounding on the door, frantic to get back inside.

"Have a nice walk home, Sissy!" I heard her called out to me through the closed door.

I pleaded for her to let me in or at least give me my clothes back but the only response I heard was their mocking laughter and teasing remarks.

"Better get lost Sissy," she warned me from behind the locked door, "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 felt my eyes filling with tears as the full weight of my predicament crashed down upon me. I was dressed like a sissy baby girl in wet diapers and there was no way these women were going to give in to let me have my clothes back. I sobbed with defeat as I finally gave up and started the long, humiliating walk back home.