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He Wasn't Even A Boy! - Chapter 14
🕑 Added 2025-08-11 15:57:17 +0000 UTCOTHER CHAPTERS | ALL STORY LIST
Disclaimer: All characters depicted in this story are 18 years of age or older at the time of the events described. This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.
Note - This story is a work of fiction. All characters, names, and events are purely imaginary and bear no relation to real people, living or dead. Any resemblance is purely coincidental.
Insert obvious soap opera joke here. But I knew she was touched by what I'd said. Actually, I'd felt that way about her since, forever. It's just that I can share it with her so much more easily now that I'm a girl.
"Mom, if I turn out to be half the woman you are, I'll count myself fortunate. But having said that, it's also my life to live. I know you have my best interests at heart, but I have to be my own ma, person. I'm asking you to accept this.
Running means so much to me. I thought I'd lost it forever, but now, there's a chance I can still find some meaning in it. Please, please understand that." She looked at me closely.
"I know how important it is to you, Stephanie. And I'm proud that you're determined to carry on with it. I'll try... but I'm still going to nag you!" "I can handle it." Another hug, and I headed off to bed. Lord, what a day! As I washed up, brushed, and changed into my sleepshirt, I thought back on it all. Between Arleen, Becky, and my Mom, there'd been enough pathos on display to fill up an entire week of 'Oprah'.
Compared with all that, dealing with my feminine form was almost a breeze. I was already becoming accustomed to the sway of my breasts, the emptiness between my legs, and so forth. Would a girl's emotions prove more challenging than a girl's body? I was beginning to think so.
My body had a surprise in store for me, though. I had trouble falling asleep, so I got up to open the window. Things were a bit stuffy. Then it happened. I felt a strange tingling in my thighs, and then in my nipples.
My breathing and my pulse quickened. I spent a minute trying to calm myself, unsure of what was happening. I leaned against my desk, growing dizzy with sensation.
My muscles suddenly weakened, and I eased slowly to the floor, unable to stand. But I wasn't in pain, far from it. I felt a growing excitement throughout my breasts, now much more intense than even my 'encounter' with Arleen. My nipples became rock hard, and my breath grew ragged.
Suddenly, I felt a tremendous surge through my entire body. I gasped at the new yet strangely familiar sensation.
All my blood seemed to rush to my groin, and I found myself spreading my legs far apart, my hips thrusting into the air, seeking Penetration.
Oh, god, I was having a girl's orgasm! Without willing it, my vagina began to soak clear through my panties as I moaned softly, my hands moving to my breasts. Oh! Just touching my nipples doubled the pleasure building between my legs. Oh yes! More... please... more!
My thighs parted, then closed, then parted again seeking friction, contact anything to fill the emptiness... anything to complete... I was utterly out of control, unable to stop. Still stroking my breasts, it hit me. Ecstasy. Sheer ecstasy. Shuddering, a wave of delight spread through every fiber of my being as my vagina poured out copious amounts of fluid. I felt strange muscles deep inside my new sex contract over and over.
Oh! It's so good, so powerful... oh... oh yes... yes... yessss! Exhausted, the glow still filling me, I tried to catch my breath. Slowly, I managed to regain my feet. I'd practically left a puddle on the floor, which I wiped up then it was time for fresh panties as I weakly made my way back to bed.
What had just happened to me? I knew the obvious: I'd had my first female climax. But how? I wasn't touching myself before it... happened. And even while I was... coming, I wasn't stimulating myself between my legs.
And yet my body reacted with such passion! I felt vulnerable because I hadn't been able to control it. I'd simply fallen to the floor and just. It was like last night's wet dream, only I'd been awake for this one. An involuntary orgasm? I'd never heard of such a thing. As a boy, it took a considerable amount of, attention to produce a result. But was it different for girls? Somehow, I doubted it.
Everything I'd read in Penthouse implied that women had to work hard for their sexual satisfaction. And yet I couldn't deny it had happened to me. God, it had felt soooo good! More intense, more all-encompassing than as a boy. The scariest part was that I could tell I'd just skimmed the surface! There was much more to come... so to speak. Rattled, but weary, I drifted off to sleep.
I woke up in dry panties so at least it hadn't happened again during the night. During my shower, I felt both a physical and a mental desire to explore my vagina, to see if I could get a handle on things.
Yet I remained intimidated by the new sexual anatomy between my legs, so I resisted. I put on a cream-colored blouse and a paisley silk skirt about three inches above the knee.
A little shorter than before, but after running yesterday's race in that skimpy uniform, I was getting used to showing skin. Arleen was on the bus and she looked happily at me while I took a seat next to her.
We chatted about inconsequential things, the setting was too public to share more personal... matters. But there was no doubting our connection, now.
She did look nice in her peasant blouse and skirt combo, but like yesterday, her pretty body didn't really do very much for me. Instead, I felt sisterly towards her. The good news was: she seemed to be satisfied with that. We exchanged a quick, but sweet hug as we separated for the first bell.
And so began an uneventful set of classes. Oh, sure, my breasts pressed ungainly against the desk whenever I leaned over. I was a little worried about the flimsiness of my skirt. I had to master the 'hair flip' while writing in my notebook. And I couldn't be too careful when it came to keeping my legs crossed. But you know what? I didn't care.
What had seemed awkward at first was slowly but surely becoming second nature. Erin had talked about this at Girl School. The mind does adjust. And more, it was even a little bit fun. There's something special about being a girl, about wearing pretty clothes and feeling feminine.
I had only scratched the surface, so I couldn't say just what it was. But I kind of liked it. And those around me could tell with every passing hour, everyone was treating me exactly as Erin had predicted: as if I'd always been this way.
My skirts, my long tresses, my soft voice, and all the rest were painting a truly girlish picture. People reacted accordingly. I got fewer comments on the 'don't you miss being a boy' theme.
Girls were warming up to me in a purely female way, sharing stories, compliments, gossip. Boys were modifying their behavior, too less cursing when I was around, more playfulness, trying to impress me. It was actually rather sweet. Part of it had to do with the sensuous nature of my body.
I don't mean 'sensuous' as a synonym for sexy, but rather in the classic definition: appealing to the senses. My perception of sight, hearing, smell, and especially touch had heightened dramatically. Every contact against my smooth skin could feel tingly. I was so much more aware of my body and my environment.
My silky skirt and my even silkier panties caressed my hips and legs in an endlessly sumptuous way. I suspect that if a boy were to put on my clothes, he might enjoy the soft material, but his body would not communicate the same physical delight.
That alone was making me act a lot more girly. And everyone was picking up on it. I'd read once that a woman's body is far better built for pleasure than a man's. Up to GB, there'd been no way of objectively verifying that.
But now I knew it to be true. Especially after last night! That orgasm had been incredible. The tingling in the thighs, moving to my breasts... I remembered it so vividly, it was as if it were happening now...
Uh, oh. It WAS happening now! Right here in class! My pulse was racing, my skin was flushed. I could feel the pleasure begin to build. Still distant, but drawing closer.
Oh God! I can't stop it. I can't... I can't do this in front of everyone! I had a horrifying vision of collapsing on the floor, my legs spread wide, my skirt hiked up, my pretty underpants on display for all to see, while I... came. I quickly excused myself, without waiting for the teacher.
Unsteadily, I lurched for the exit and made it to the corridor. Placing one hand against the wall, I started down to the bathroom.
There wasn't much time left. My bra grew tighter as my breasts swelled within it. Dizziness again, I could barely stand.
The insides of my thighs were wet. A glowing feeling was rising from the base of my belly. I realized then I wouldn't make it to the bathroom. The corridor was empt,y but anyone could happen by.
Fortunately, there was an unlocked storeroom. I entered and quickly shut the door. I staggered across the room and fell onto an old couch. Breathing heavily, I couldn't help but stroke my rock-hard nipples poking through my blouse.
Ohhh! It felt so, so nice. Just touching my breasts seemed to triple the delight I felt down below. In amazement, I watched my legs move apart, wider and wider. I tried to bring them together, to stand up.
But I couldn't. Oh... Oh... yes! Without my willing it, my legs spread as far as possible, my paisley skirt raised up, my panties now revealed.
This is what would have happened in front of all the kids, had I not made it here. The ultimate embarrassment.
My body was totally out of control by now. I was helpless to stop the rhythmic thrusting of my hips, up and down, in a feminine simulation of lovemaking. I tried to keep quiet, but my need was too great. Soft, girlish moans filled the small, dusty room as my orgasm began. A wave of thick pleasure crashed over me. Mmm... yesss.
Even more intense than last night! Finally, it ended. Once again, my panties were drenched, the vinyl of the couch shiny where my... juices had spilled. Jesus and I thought coming as a guy was messy!
But far more unsettling was the knowledge that my body had taken over me completely. I'd surrendered utterly to the pleasure while hardly touching myself. I'd never heard of this happening to anyone boy or girl. Something was wrong.
And I'd better get a handle on it quickly. So far, the kids had been pretty good about accepting my transition.
The reason for that was obvious; I seemed like a normal girl, so I was being treated like one. But if I started having spontaneous orgasms in front of everyone, I'd be on the express line for Freakville.
Fortunately, I'd packed an extra pair of panties in my purse. I quickly changed, trying to wipe down as much as possible. Fresh undies felt sooo good! Still trembling and a bit pale, I headed out of the storeroom. Just as I was closing the door, I heard footsteps behind me.
It was the principal, Mr. Grogan. "Stephanie, what were you doing in there?" Now that was one question I didn't want to answer.
I stammered for a moment. He continued, "And how come you're not in class? Do you have a pass?"
"I... I wasn't feeling well, Mr. Grogan. I was just heading for the bathroom." But I could tell he wasn't buying it.
He eyed me up and down in that creepy way of his. And worse was the image I knew I was presenting. Still breathless, my nipples thrusting against my bra, my clothes and hair mussed, and a faint but undeniable feminine scent in the air.
I looked like a girl who'd just been rousted from the backseat of her boyfriend's car. "Even if that were true, Stephanie, that still doesn't explain what you were doing in the storeroom. I think we'd better discuss your infraction in my office."
Nervously, I followed him to the private entrance for his 'chambers'. He took a seat behind his large oak desk, while I stood uncertainly in front of him, my hands toying with the hem of my skirt. I was still disoriented from my 'moment' and I wasn't thinking clearly.
"Now, Stephanie, I realize you've had a lot of adjustments to make lately. But I can't have students wandering the halls unaccounted for. Especially given that you're a senior. The younger students look up to you; you're expected to set an example."
"I'm sorry, sir. I just wasn't feeling very well."
"That's understandable, but you're still required to report your condition to the teacher and to obtain a hall pass. I can't play favorites here. I'm afraid I'll have to assign you the usual detention."
Oh no! That would mean I wouldn't be able to compete in Friday's track meet. Any student who received detention was ineligible for extracurricular activities for an entire week. I had to get out of this somehow.
"Mr. Grogan, I really am very sorry. I didn't mean to break any rules. Is there anything I could do? Maybe some extra schoolwork or a volunteer project? I'm willing to accept my punishment, but I don't want to miss track." During my bit of pleading, I found myself doing something I'd never imagined: using my feminine wiles.
Of course, I had only a vague idea how to do it, but I tried to project a cute sweetness into my voice, and I looked at him from lowered eyelashes. I had to be careful not to lay it on too thick, the principal was a veteran at dealing with kids.
He'd see right through most acts. He was silent for a few moments, pondering what I'd said. He continued to stare at me, and I could guess what was going through his mind as I stood there. His reputation was clean indeed; it was exemplary.
He was a respected and successful administrator, and no complaints had ever been lodged against him by students or teachers. Nevertheless, I could see it in his eyes, carefully concealed but still there: desire.
For me! "Very well, Stephanie. There may be another solution." He reached into a desk drawer and pulled out a... paddle! It was about two feet long and one wide made of hickory.
"The State of New York no longer authorizes corporal punishment in schools. However, I feel alternative methods of discipline have their place. So, I'll present you with a choice: detention and the end of your track season or this..." he hefted the paddle.
"You're... you want to... spank me?" I said incredulously.
"Your decision, young lady. You have represented this school very well in athletics, so I'm offering you an opportunity to continue to do so. Otherwise..." How could this be happening? And yet I knew I was stuck.
If I refused, my Milford running days were over. Worse yet, I hadn't had the chance to demonstrate to the college scouts what I could do as a girl. No coach was going to offer me a full ride based on yesterday's race alone. If I didn't finish the season, I might not get any scholarships, Title IX or not.
On the other hand, it was quite obvious what Mr. Grogan wanted to satisfy the desire I could see on his face.
Oh, I wasn't worried about sex, per se; neither of us was insane enough for that. But he clearly held the upper hand (so to speak). What could I do? "Al... alright, Mr. Grogan."
"So you are choosing to resolve this matter here and now, just the two of us?" "Ye... yes, sir." "Very well, Stephanie. Please remove your skirt." Shocked, I just stood there for a moment.
"You've got to be kidding," I finally said. He spoke in a calm, measured tone. "Stephanie, corporal punishment does require the infliction of pain. You will not be tortured, but there must be some suffering, else what would be the point?
Clothing can mitigate the effects of the blow,s hence the need to partially disrobe. Now, you are wearing panties, are you not?"
"Um... yes." I stammered disbelievingly.
"Then that will satisfy the demands of modesty. Hurry up, girl, we don't have all day." Slowly, my hands went to the waistband of my skirt. I couldn't believe what I was about to do. You may not, either, but keep in mind two things.
One of my passions for running. I'd already endured years of pain to get where I was. Two, I was still fuzzy from the orgasm I'd had just five minutes ago. And I couldn't deny the sexual charge that remained.
I slipped out of my silk skirt, folding it carefully and laying it on a table. My face flaming, I stood before my principal wearing just my blouse, bra, and peach- colored panties.
His look had moved from desire to lust as the careful mask slipped a bit. I knew how pretty I was, and in my underwear, I also knew how men would react to my new body.
And he was a man. A very handsome one, I reluctantly noted. "All right, Stephanie, please lie down across my lap." Stunned, I realized he was forcing an intimacy upon us I hadn't anticipated.
But I had to go through with it. I assumed the position. It's difficult to describe the feeling I had next. I was stretched out across Mr. Grogan's firm thighs.
My cute little ass was fully exposed to him, encased only in the flimsiest of nylon panties. I should have been embarrassed, and I was. I should have been nervous, and I was.
But what I shouldn't have been was horny, yet I was. There was something... appealing about having this strong, male presence commanding me. In control of me. I felt a need, deep within me, that was...satisfied being like this. As if it were... right, somehow, for me to submit to him. Because he was a man.
And I was a girl. The first blow came the smack was audible throughout the office. Oh! The pain was sharper than I expected due to my more delicate skin, I suppose.
A second blow produced a feminine gasp from my mouth, while the third brought tears to my eyes. He was keeping his word, though it wasn't brutal or damaging. Just degrading. And yet... and yet it was something else.
Arousing. As the blows rained down, I found my hips moving forward in an effort to escape. This in turn was producing friction, caused by my... girl parts pressing harder against him. Pressing against...
His erection. Oh God! I could feel the hardness of him against the most intimate place on my body. The spanking was driving my groin into his as I lay across his lap. Which could not help but turn both of us on all the more. Only our clothing prevented his penis from touching my vagina. Oh! That thought alone should have cooled my ardor.
But it didn't. Instead, I grew wetter and hotter. So much hotter! My breathing became ragged again as my body was receiving its first true sexual stimulation.
Oh... oh yes... more... Tears were rolling down my face by now. I couldn't say when the spanking had stopped.
He was now gently rubbing my panty-clad butt, the soft nylon transmitting sparks of delight. My nipples felt like two candles burning on my chest. I ached to have them touched. Still stroking me while I lay across his lap, he spoke.
"You are the first GB female I've ever met. But I must say, Stephanie, you do your new sex proud. I wonder if you were always meant to be a girl, you've taken to it quite well. GB may function as a corrective measure, turning boys unsuited for masculinity into the girls they should have been.
Perhaps it's for the best now that you are the girl on the outside, you seemed to have been on the inside. Certainly, you have an affinity for the properly submissive role of a woman." I was barely listening to him.
All I wanted was for him to keep touching me. I turned over on his lap. I could feel his enormous erection pressing against the seat of my pretty underpants. My eyes wet with tears, I met his gaze. I could see the desire on his face - along with... satisfaction. For him, it was not only sexual.
He wanted to show how dominant he was. He had succeeded. Both of us shifted our glance to my body. My blouse had hiked up considerably.
The only covering I had below my belly button was my sheer panties, edged in white lace – and they were sopping wet. The dark triangle of my bush was clearly visible to us both.
And between my legs, we both could see the outline of my vagina, the lips of my vulva creating just a hint of a bulge in my frilly hipster-style underwear. That semblance of a bulge seemed to mock what I once had as a boy - and what he had as a man.
Comments
Nina Schumacker
Now that one was hot and spicy for sure, almost made me have an orgasm just listening to that story while driving down the highway love it, can't wait to hear where this goes but yes the principal should be ashamed of himself.
My Freeze
Wow, Stephanie sure is experiencing all new emotions and have trouble handling them. Maybe he/she shouldn't have left GB school so quickly. Getting very interesting.
Jerry
Um. Just a story. Fictional characters mirroring real people though. I hope that principal accidentally trips on a knife. What a creep.
