As she undid the straps on my highchair, she thanked Dixie again for taking me and gave her my diaper bag which contained enough for one change.
I didn't go out much in public so it was with trepidation that I did so now. Dixie led me out to her car by the hand and I looked around frantically to see if anyone was looking. For some reason, the crinkle-swish of my plastic panties seemed particularly loud as I walked out into the open. Here I was, walking hand in hand with one of the hottest babes in school and I was wearing a sissy sailor suit and thick diapers. It was so unfair!
Somehow, I made it to the car without being seen and I waited anxiously for her to unlock the door so I could get in. For what seemed like forever, Dixie got her keys out of her purse, unlocked her own door and slipped inside, leaving me to stand out in the open.
A pair of ladies were walking down the sidewalk towards me and I saw them start to look me over. Desperately, I pounded on the side of her car window to let me in but she only ignored me and started the car. I was bent over slightly trying to see what she was doing which only made my big diapered butt look even more noticeable. By now, the ladies were about fifty feet from me and I bit my lip as I debated whether I should run back inside or not. In a frenzied state of panic, I helplessly flooded my diapers as the ladies gave me a strange look. I let out a moan of shame and looked away, fighting back the tears. Finally, I heard the door unlock and as I slid inside, Dixie's mocking laughter filled my ears.
We drove through town for about twenty minutes and despite my shame at being seen by other drivers, I found myself stealing glances at Dixie's profile.
She really had a hot body, and her perky bre ( " at " ) sts filled her tight halter very enticingly. Gazing at her tanned, creamy thighs and flat tummy gave me a hard-on within my wet diapers.
I had never been babysat by Dixie and her silence in the car left me to fantasize about how she would treat me. In my befuddled state, I naively thought she'd flirt with me and I dreamed of cupping her perfect bre ( " at " ) sts in my hands.
When we arrived, Dixie seemed annoyed with me and when she came around to my side of the car, she blocked my path. Without warning, she grabbed my head and roughly jammed my face against her chest. For about three seconds, my nose was buried in her soft cleavage but her embrace was anything but gentle.
Holding me so I couldn't breath, she suddenly pushed me back and slapped me hard in the face.
''There!" she snapped, "I hope you enjoyed it you little pervert, 'cause that's as close as you're ever going to get to the real thing.
“Now quit staring at my boobs!''
With that, she stormed off, leaving me at the sidewalk to gather my wits. Glancing around quickly, I ran to catch up to her as she went up to the door and knocked on it. I thought that was strange because I assumed we were going to her house. Instead, the door opened and a big guy stood inside, towering over me. I vaguely recognized him as one of the studs from the football team, a group of people who were way out of my social circle when I was still in school.
"Hey! I recognize you! You're that pansy ( " at " ) ss that was the teacher's pet all the time, aren't ya?" he blurted out.
I blushed and nodded my head.
"Well I always knew you were a sissy. Looks like your mommy had to put you back in diapers too," he said mockingly.
"Dixie, do we-" I started.
"-That's MS. Dixie to you Sissy-boy," she corrected me.
I cleared my throat and started again.
"Ms. Dixie, do we have to stay here? I wanna go home," I whimpered.
"Yes we do. John's got a BIG surprise for you. Now get inside," she said menacingly. She emphasized her point by slapping my diapered bottom as I stepped in the house.
Not wanting to get in any more trouble, I did as I was told and I saw football trophies and other sports paraphernalia everywhere in John's living room. He was a huge guy, and he was everything that I wasn't: tall, muscular, macho, and attractive to the girls. Now it was painfully obvious how ludicrous my plans had been to ask Dixie out on a date. Even before I was wearing diapers full-time, she would've laughed in my face and probably told me to go play with myself. As I saw her kiss John passionately and rub his swelling crotch, I was embarrassed by the temerity of my fantasies.
"It's time for me to put you in your place," Dixie told me, "get on your knees."
"Wha-what for?" I asked, fearing something was about to happen that I wouldn't like.
John whipped off his gym shorts revealing a tight pair of underwear that clung to his monstrous hard-on. He was stroking it and looking at me strangely.
"If I tell you to do something, you'd better do it without question...or maybe I should tell your nanny that you were a bad boy today?" she said with a wicked smile.
"No Ms. Dixie, please don't!" I quailed as I dropped to my knees.
With obvious admiration, Dixie pulled John's underwear slowly down his big muscular legs with her manicured red nails, exposing the biggest coc-k I had ever seen in my life. It sprung to attention like a battering ram and my heart began to pound in my chest.
With a few steps, he stood before me, looking down at me with his coc-k mere inches from my face.
"Time to learn what it really means to be a sissy, Bobby," Dixie told me in a throaty tone of voice, "you thought being a sissy just meant wearing diapers and dresses but now you're going to find out the true meaning. Take his coc-k in your mouth."
I gulped hard and looked up at her pleadingly. I was still a virgin and hadn't even kissed a girl before besides my mom; this was just too much for me.
"I can't!" I quaked fearfully.
"Yes you can, just lick your lips and suc-k on it like it was your baby bottle," she said impatiently.
John's coc-k stood proudly before me, huge in every respect. The head was reddish-purple and the shaft, which looked like it would take both my hands to span, was thick and covered with veins. It was so different from my own little pecker that was maybe two and a half inches when hard. This one was like a baseball bat!
"Oh...I don't think...I mean-I," I whimpered pathetically.
Without waiting, John simply rammed it into my mouth, shoving it all the way in until I gagged. I squealed with the meaty invasion and he pulled it out only enough to allow me catch my breath. Grasping my head, he guided me up and down until he had established a rhythm for me. Obediently, I kept it up, not knowing what else to do and before long, I was using my tongue to lick the sensitive underside of his coc-k. It tasted slightly salty and I smelled his musky cologne from his crotch. In order for me to keep my balance, I found it necessary to grab his thighs, and when I did, it was a lot easier to steady myself. By now, I was slobbering pretty good and his massive coc-k was filling my mouth completely, stretching my cheeks to accommodate him.
After five minutes of steady pumping, I felt his thighs tense up and I knew he was about to c-um. I figured he'd pull it out and blow his wad on the floor but instead, he held my head tighter, forcing his coc-k deep into my throat. I felt his already gigantic phallus swell in my mouth and then suddenly, with a roar of satisfaction, he exploded, pouring a huge quantity of warm, creamy semen into my mouth and making me gag. Reflexively, I swallowed his load but more just kept coming out. I swallowed again, the salty taste of his c-um all over my mouth and I wanted desperately for him to remove his coc-k but he just held it there and continued to fill my mouth with c-um. I couldn't believe how much he had and I lost track of how many times I swallowed his load before he at last pulled his still erect member from my lips.
I was still in a daze as I gasped for air and semen dribbled down my chin. Dixie quickly grabbed one of my pacifiers out of the diaper bag, wiped the c-um off my chin with it, and popped it back in my mouth. My jaw was sore from being stretched open so far and a slick coating still covered the inside of my mouth.
I had never been so humiliated in all my life. Tears of shame filled my eyes and I kept them downcast, unable to face the girl that I had formally held such high aspirations for. I had been in denial for the last year, thinking there might still be hope that she would be interested in me but now those hopes were dashed. Here, I had waited all my life for my first sexual experience, always assuming it would be with a girl, and I ended up down on my knees, suc-king the coc-k of a big football stud and then swallowing all his c-um. Even if by some miracle, my mommy ever decided to potty train me, there was no way I'd ever be able to show my face at my old high school again. I'd be known as the sissy coc-k suc-ker, unworthy of a girl.
Tears of frustration trickled down my face and I chewed on the c-um covered pacifier, angry with the unfairness of life.