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Schooldaze — Part 1

"A high-school cross-dresser is caught in the school after hours by the football team quaterback."

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Author's Notes

"Part 1 of a 3-part Story"

I changed into my schoolgirl outfit in the boys' locker room at school. I had been doing this for years, so I knew there was nobody in the building. I knew I'd have plenty of free time to indulge myself — I had started slowly, just panties under my pants, since I had been a sophomore; but now I was a senior and really knew the school and its rhythms well. As I pulled my wig on and prepared to roam the halls, I looked forward to hearing the clicking of my heels on the clean tile floors. Suddenly I heard the door open!

I all but froze in terror. There's not supposed to be anybody here! I checked every room! I stood there speechless as the Quarterback from our football team — a star senior with good college prospects — rounded the corner of the lockers. When he saw me, his first reaction was to say, "excuse me" and turn away. He stopped, though, and then turned on me. "What are you doing in here?" he demanded. "This is the boys' locker room."

I put on my best femme voice. "I'm... I... I'm kind of lost. You see, I'm new here and..."

"Bullshit! Whose shit have you got there? You going through the lockers looking for something?" he said as he pointed behind me.

I quickly glanced backward and saw my drab clothes all over one of the benches next to my open gym bag. I hadn't put anything away because there wasn't supposed to be anybody here! Oh shit! Now I'm done for!

"Really, I... uh," I stammered. He grabbed me by both arms and pushed me backward until I was past the bench with my drab clothes on it. I had trouble walking backward that fast in my heels and when I stumbled he lifted me effortlessly and continued on his way.

"Stay right here and don't move," he said. He kept one eye on me as he reached down and picked up my pants. "Let's see whose stuff this is," he said as he pulled my wallet from the back pocket. Now I'm truly mortified.

"Well, well, Martin DeBeers' stuff," he said, reading my name off of my driver's license. "You're in deep shit now, sister. Martin is my next-door neighbor. A bit of a scrawny geek but still a good guy. I'm going to have to report this to the office tomorrow morning. Give me your student ID number."

"They... uh... I don't have one yet," I said, my voice quavering.

"Then give me your name," he said brusquely. "C'mon, out with it!"

"Stacey," I said, my voice breathless and barely above a whisper now. "Stacey Wilson. Do we really have to tell the office? I'll be in such trouble at home. Isn't there any way we can avoid this? I didn't take anything, honest."

A sly grin spread slowly across his face. He stepped back from me with his hands on his hips and looked me up and down, studying me hard. He had a reputation for being the first one in school to score with the new girls — those he wanted anyway.

"You're kind of plain in the face, but you have nice legs and a great body. Your lips look especially nice. I love the way that color looks on you," he said.

"Thank you," I said demurely. My mind was racing. Was he really hitting on me? He liked my body? Well, duh, I can make it look as sexy as I want with the right 'equipment.' Could I really weasel my way out of this? Maybe a little flirting might be in order. I didn't know a whole lot about being a girl, but I did know what boys liked. "I never thanked you for catching me when I stumbled back there. You're quite strong."

His grin widened. "I can only think of one thing that could improve the way your lips look," he said, completely ignoring my comments.

"Huh?" was all I managed.

"Your lips would look a lot better wrapped around my cock," he said.

I gaped at him. "What?" I said.

"Quid pro quo," he said with a smug smile on his face. When the hell did this dumb jock learn Latin I thought? He continued. "You suck my dick and I'll forget about reporting this little incident to the office. Simple as that."

I gaped some more. While I enjoyed dressing in girls' clothes I had never thought about doing what girls did with boys. I gulped and stammered something unintelligible.

"I'll take that as a yes," he said. He started to unbutton his Levi's. My eyes widened. "It's the only way out now, sweetheart," he said. More buttons. "Once Little Hank here," he patted the swelling front of his jeans, "gets it in his mind that he's about to poke a pretty young mouth, he just won't take no for an answer."

He pulled his unbuttoned jeans down to his ankles, and as he stood I could clearly see the outline of his swelling cock in his sexy bikini underwear. Sexy, I thought? Did I just look at a guy's underwear and think sexy? My mind was reeling as the sound of his voice broke the silence.

"Touch it. Go on. You know you want to." He stepped closer to me, pushing his pelvis out and bringing the growing bulge in his underwear even closer to me. "C'mon, just give it a little squeeze. Here, like this."

He reached out and took my right hand by the wrist. My arms hung limply at my side. He edged closer and closer until he finally pulled my hand onto his throbbing tool. He wrapped my fingers around his prick and squeezed, making my hand squeeze his prick as well. He groaned.

"Oooohhhhh. Yeah, now stroke it a little for me, baby," he said. He started stroking his member with my hand, but after the second stroke he pulled his hand away and my hand continued to stroke him in his underwear. I watched as if it was someone else's hand and not my own, that was stroking our Quarterback's rigid tool.

"Your hand feels good, Stacey," he said between moans. "But Little Hank's not going to settle for a hand job. Why don't you drop my Jockeys and see how good it feels in the flesh? Go ahead, Stacey, Little Hank won't bite."

The more I stroked his cock, the harder it got. It felt warm and throbbed when I squeezed it. I started to feel a little dizzy from all the excitement. "I have to sit down," I said. He turned with me and allowed me to find the bench on my own. My grip on his cock didn't loosen for one instant.

When I looked up I saw the back of my hand and realized that I had unwittingly placed myself at eye level with his crotch. "Well, c'mon, Stacey," he said. "Let's get this material out of your hand's way so you can feel a real piece of hot meat."

It was like I was in a trance. I watched my hands (were those really MY hands?) grab the waistband of his sexy underwear (sexy again?) and take them down his muscular legs to his knees. His cock bobbed free bouncing invitingly mere inches from my mouth. It was quite obvious that despite how long and thick it looked, it was not done growing.

I watched my disembodied hands caress their way back up his thighs. As they drew near his manhood my right hand wrapped its fingers back around the fleshy staff while my left one cupped his balls.

He groaned really loud as I stroked his bare prick and massaged his balls. It continued to grow under my attention, and soon I was holding the biggest cock I had ever seen in my life.

"You like it?" he asked.

"Mmmm hmmm," I heard my 'other' self say out loud. Where was that sound coming from? My throat?

"Kiss Little Hank hello, Stacey. He looks very happy to see you." I continued stroking and squeezing with my right hand. "Let's go, Stacey, get it in your mouth," he said impatiently. Still, I stroked his tool. "Stacey," he snapped, "get my dick in your orifice or we go to the office!"

As I stroked it once more, a large drop of pre-cum surged out and started to run down the shaft. Instinctively I opened my mouth and licked the underside of his pole, catching it on my tongue. After licking the underside I slipped the head between my lips and closed my mouth over it. His moan must have been heard halfway across campus.

The feel of the soft, spongy head between my lips was like an electric shock to my system. Somewhere inside of me, a dam burst and I began sucking his cock like a woman possessed. I couldn't remember who I was or why I was there, but there was a cock in front of me and I wanted to suck it.

Our school's big, studly quarterback was really into getting blown. He had tensed up the instant my tongue touched his cock, but now he relaxed his stance and inched a little closer to me. At first, he rested his hands lightly on the top of my head as my mouth bobbed up and down on his shaft. Then, I felt his hands slide down to cup my breasts.

I paused in mid-bob, keeping his delicious meat in my mouth as I angled my eyes up to look at his face and see his reaction. He looked at me with a questioning glance while his hands continued to feel me up through my blouse and bra. I smiled and went back to work on his pole. My breast forms had passed the 'touch test' with flying colors. I was so glad I had scrimped and saved the extra money for the good ones.

When I felt him fumbling with the top button on my blouse, I nearly panicked. What am I going to do if he gets his hand inside my blouse? And then inside my bra? I had to do something to get his hands away from my tits. Think, Stacey, think!

His cock was pretty long, maybe eight or nine inches. Certainly longer than anything I'd ever had in my virgin mouth at any rate. I took a deep breath and pushed as much of his cock as I could take into my mouth. When he hit the back of my throat my gag reflex kicked in and I retched like I was going to throw up.

"Oh, God yes," he said as I came back up. I went down on him again, and gagged again, and then down on him once more before my gag reflex even subsided. As I felt the head of his cock slip into my throat his hands flew to the back of my head, pushing insistently. I struggled to come up for air and finally succeeded. At least his hands were off of my tits!

"You're sure a fine cocksucker," he said. "I thought you were going to deep-throat me there for a minute. None of the prissy girls in this school ever had the guts to try. Hell, most of them won't even swallow."

I looked up at him again. "I want to feel you in my throat," I said. "I want to swallow all of your cock and feel the hair on your balls tickling my chin."

"Oh my God, Stacey, you must be a real suck slut." I took his rod back into my mouth as he spoke. My answer came with my mouth full of cock.

"Fuck my face," I said. "Fuck my face and dump your cum down my throat." He grabbed the back of my head and all but pulled me onto his cock. I knew that if his head had made it past my gag reflex then the rest would be easy. I just had to concentrate.

My first two attempts met my gag reflex head-on, and I had to withdraw. I took a deep breath, tried to relax, and plunged face-first onto his meaty pole. He cried aloud as every inch of his manhood disappeared into my mouth and his balls met my chin for the first time.

Bam The locker room door slammed open. "What the hell is going on in here?" a loud voice demanded. A female's head appeared around the corner of the lockers. Mr. jock-stud was still humping my face but had turned his head to face her. Ms. Callahan — the Terminator. We were in deep shit now, I knew, but my lover's thrusts kept my head facing him. I tried to watch from the corner of my eye.

"What's this all about, Henry?" she asked the Quarterback.

"Well, Ms. Callahan...," he began. I could feel his cock softening rapidly and he had stopped thrusting in and out of my mouth. I noticed that he didn't move to pull out of my mouth either, so I stayed where I was.

"Shut up," she growled. "Who's your little slot tonight?"

"Some new girl. I was just...," Ms. Callahan interrupted him.

"You were just getting your jollies poking her mouth. I wasn't told about any new girl," she stated matter-of-factly. "What's your name, dear?" she asked me, almost sweetly.

"Stacey," I mumbled.

"It's not polite to talk with your mouth full, dear," she said almost demurely. This miss-nice was not her style. I knew all too well how nasty she could be. Henry pulled his limp dick from my mouth.

"Stacey," I said again, louder this time. "Stacey Wilson."

"How is it that nobody told me you were going to be coming here, Stacey?" she asked. "I usually get a roster with all the new girls on it so I can place them in the right PE classes. Can you explain that to me, you little tramp?" There was now a menacing tone in her voice. I knew the sweetness was all an act.

"I'm sorry, Miss... Uh... Miss," I stammered while my mind raced, trying to think of a plausible explanation.

"That's Ms. Callahan, you little slut," she barked. "Stand up! Turn around and face me." I stood meekly and turned around. "Fix your lipstick. You look like a whore."

I reached into my small clutch purse and pulled my tube of lipstick out. I applied it with shaky hands, but still managed to clean myself up a bit.

"Now just what am I going to do with you horny little shits?" she asked. I looked at Henry and he looked back at me. We both knew she wasn't waiting for us to answer, so we remained silent. "Both of you sit down right there and don't either of you move a muscle." She pointed to the bench closest to her.

I immediately clicked my way over to the bench and sat down, crossing my legs. I felt my skirt ride up slightly and I guessed that she could see my stocking tops, but her glare never wavered from Henry. He stood there a moment and then bent over to pull up his underwear and jeans.

"Just what do you think you're doing?" she snapped. "I didn't tell you to get dressed. Now get your ass over here and SIT DOWN." Henry waddled as best as his pants would allow and sat down next to me.

"I want you two to think about a suitable punishment while I go to my office and think about what to do with the pair of you." She stalked out of the locker room like a mad killer on the loose. "And don't either of you move from that spot!" she shouted from the hallway.

I glanced over at Henry and played dumb. "Oh, so you're Henry? The Quarterback?" I said.

"In the flesh," he said, spreading his arms and taking a mock bow. Both of us softly laughed at his joke. It was nervous laughter.

"What do you think she's going to do to us?" I asked innocently. I knew full well how terrible the wrath of the Terminator could be.

"Well, I think you're pretty safe with me," he said confidently as he crossed his arms over his chest. "She might be a bitter old maid but she's a real sports nut and is 100% behind our school's programs. She won't want to see me sidelined at this point in a winning season." Henry grinned.

I felt somewhat better about things, but I needed to sell Henry on who I was supposed to be. "Maybe if this all works out, I can find some way to thank you. Don't you think?" I traced a finger from his right knee up to where his flaccid prick was drooping between his legs. I wrapped my hand around it and gave it a few pulls. "Kind of a shame to see such a fine, proud specimen of a cock all shriveled up like that." I felt it jump in my hand.

"You'd better not," he said suddenly, trying to push my hand away. "If you get me hard again and she comes back and sees it...," he left his warning unfinished as I lowered my face into his lap.

I slurped his limp member into my mouth and sucked on it. I felt a strange sense of enjoyment as I felt it come back to life. He grew to full size quickly, and I kissed the head of his beautiful cock (did I really just think that?) before I began bobbing up and down on his tool once more.

Henry moaned softly while I blew him, not wanting to attract the Terminator too soon. He put one arm around me and started rubbing my ass through my skirt while his other hand cupped as much of my breast as it could. His hand stroking and squeezing my ass felt so good sliding the wool back and forth across my sheer-back panties. He paused when he found the garter straps and he followed one down to my stocking tops. "Hmmmmmmmm," was all he said.

I scarcely believed it when I felt the familiar stirring of my clittie in my panties. I had it tucked neatly away between my legs but I knew I was going to be in trouble soon if this kept up. He didn't have far to go to lift the hem of my short skirt and he was now stroking my pantied ass directly. The feel of my ass in the sheer panties must have done something to him because pretty soon he was bucking his hips and I just knew he was going to blow his load. I pulled off of him and he gave me a questioning look.

"I want you to be buried deep in my throat when I take your first creamy load," I explained. "I want to feel your pulsing balls pressed against my chin while you dump your seed in my stomach." I smoothed my blouse and straightened my skirt. I crossed my legs once more and this time his eyes followed the movement. The light in his eyes told me that he was enjoying the view of my stocking tops and garters.

"You're one hot chick, Stacey. We really need to keep in touch after tonight. I'd like to get to know you a lot better." The lust in his eyes was unmistakable. He wanted to fuck me.

"I... I'm still, uh...," I stammered. "I can't, uh... sleep with you, Henry. I just couldn't."

Before we could finish our conversation the door to the locker room opened once more and Ms. Callahan came around to our bench. "Well," she said, "have either of you thought up a suitable punishment?" She was cool and collected now, not in a rage like she had been before. I knew from experience that her calm was even worse than her rage. Now I really was scared.

She looked at each of us individually, searching for an answer to her question in our faces. There was nothing there. "I see," she said curtly. "Very well. I see you two couldn't even behave yourselves for the few minutes I was in my office." Henry and I looked at each other and then up at her. "Don't try that bullshit 'who-me?' look on me," she pointed at me first. "You, you little slut. Your lipstick's all smeared again."

She pointed at Henry next. "Spread your legs and show me your dick," she snapped. Glumly, he complied. "That's what I thought. "Just how do you suppose all that fresh lipstick got all over your cock."

"Well, since neither of you could come up with something, then I guess we'll just have to do things my way." Both Henry and I groaned. "Okay," she said. "Then we can all go to the office right now so I can call your parents to come and get you and we can all see Mr. Rohrer tomorrow."

"No!" Henry and I said in unison. I wasn't so sure about Henry, but I knew I didn't want MY parents called! And I was also sure that getting Mr. Rohrer, the Principal, involved was a bad idea.

She reached around beside the lockers and hefted a large wooden paddle. Her skill with the paddle was legendary. She'd made the biggest and toughest of them cry like babies after just one session with her. She had designed the paddle herself, it was said. She gave detailed drawings to the shop teacher and he crafted it. It was a solid oak plank that, once it had been shaped, had been crisscrossed with a router, making a fiendish waffle-looking surface. At each cross, there was a neatly drilled hole so there would be little air trapped between the board and the offender. It was varnished to a high sheen and it seemed to glow with its own evil light.

"Ordinarily I allow students a little leeway by having their pants between their asses and my paddle. You two won't have that luxury tonight. Bend over and hold on to the end of the bench, Henry," she said. Henry moved as if his limbs had been made of wood. I knew he had tasted her paddle many times over our four years at this school.

"Stacey," she said, "go and bend over the end of this other bench." She pointed and I complied wordlessly. I had never been paddled by any teacher and had learned quickly as a youngster to avoid getting in the kind of trouble that made my parents spank. I was really scared and I'm sure the fear showed on my painted face. Of more concern to me, however, was what would happen when she made me pull my panties down and my clittie bobbed free. She'd said we'd have no mercy tonight.

She stood between us and took a few practice swings of the paddle. The benches were close enough together that she was positioned where she could paddle us both without having to move. She stepped up behind me first. "Pull up your skirt, Stacey," she said, "and drop your panties. I want to see them between your ankles." I pulled my skirt up above my waist, hooked my thumbs into the waistband of my panties, and paused momentarily. She filled the pause.

"A garter belt and stockings, Stacey? And look at those flimsy sheer panties. You've put them on OVER your garter belt? Expecting to need them off in a hurry my dear? You look like such a cheap slut." Henry's head turned to ogle me. "Face front!" she snapped. As his head whipped back around she gave him a half-hearted smack with the paddle. "Keep your panties on, Stacey. That sheer fabric will be no protection for your tender white ass."

"Hey!" Henry protested. "How come she gets to wear panties and I get it bare-bottomed?"

"Did I ask you to speak?" she said menacingly.

"No Ma'am," he said quickly. "It's just that you said..."

"You're absolutely right, Henry. Things should be equal," she said.

"Thank you, Ms. Callahan," he said and he started to reach for his Jockey's.

"Ah-ah-ah," she cautioned him. "I didn't tell you to pull up your underwear." He turned his head to look at her.

"But you said..."

"I said you'd be EQUAL," she intoned. She reached into her pocket and pulled out a pair of red lace panties. She tossed them on the floor near his feet. "Here, put those on."

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I thought Henry was going to die on the spot! "But...," he sputtered. "Ms. Calla..." I looked suspiciously at the panties on the floor. They had fallen so that the white cotton crotch was visible. It was very apparent that they were used, and they looked to be about the Terminator's size. What struck me as odd was that she had come 'prepared' with the panties in her pocket.

"No choice now, stud. Pick them up and put them on. I won't tell you again." She swung the paddle a few more times.

With a heavy sigh, Henry sat down on the bench and pulled off his sneakers, followed closely by his jeans and underwear. He stood and gingerly stepped into the panties. As he pulled them up his legs, he was careful not to pull so hard as to tear them. When he was finished he turned around and bent back over the bench, sticking his pantied ass out. The panties were tanga-cut with a seam running down the middle of the back that immediately crawled into the crack of his ass. The lace of the panty ended at the leg holes in a scalloped lace that would leave no panty line. Henry's quick acquiescence made me wonder if there was something more to all of this.

"There, that's better, don't you think?" Ms. Callahan said. "I'm more used to spanking asses in panties anyway. Now, who gets it first? The cocksucking slut or the boy that lured her here to take advantage of her?"

Smack The first blow landed and it didn't hit me. Henry made a sort of 'mmph' sound but did not cry out. "Be sure to count them, Henry," she called.

"One," he said tersely. "I didn't lure her here I just..."

Smack "Shut up, Henry," she said. "I'm paddling you first because I figure a cocksucking slut like this one here is going to get some enjoyment out of this."

"Two," was all Henry said. The Terminator's paddle rose and fell on Henry's ass until I heard him say "Fifteen." I could hear Henry choking back his tears for the last five swats and I was terrified. There was no way I could take fifteen blows from that paddle.

"There now, Henry," she said sweetly. "Doesn't the pain just expunge your guilt — kind of what it must have been like during the Spanish Inquisition don't you think? Don't you just feel invigorated, Henry?"

Henry was silent.

"Stand up and turn around here," she snapped. When he turned around the bulge in the front of his panties was obvious. All this turned him on! My mind raced. Was it the panties or the spanking that had fired him back up? He stood up straight and tall.

"Tsk tsk tsk," she said. "We need to do something about that unsightly lump in your panties." She looked over at me. I snapped my head around to face forward.

"Just what were you looking at?" she screeched at me. She came over and put her mouth to my ear. "I know how afraid you are of this paddle." As she spoke she slid the paddle back and forth across my pantied ass. I could feel every groove in the wood. It felt as if it were radiating heat. She flipped the paddle in the air and caught it by the 'business' end. Roughly she shoved the handle between my legs and pressed upwards. "I also know about your little secret, dearie," she hissed quietly. "One little peep out of your sissy mouth and I'll rip these panties off of you. Imagine how pleased our quarterback will be to find out he's been blown by another guy tonight."

I felt my face flush as she stood back up and walked around behind me. "Henry?"

"Yes Ma'am?"

"Go and stand in front of this little whore."

"Ma'am?"

"How much plainer can I make myself? Go and stand in front of your little blowjob queen." Henry came over to my bench and straddled it right in front of me. His beautiful cock, now imprisoned in sexy red lace, was inches from my oh-so-willing mouth.

"Suck," was all she said. Neither of us had to be told twice. Henry quickly (and very easily I noticed... had he done this before?) pulled the crotch of the panties aside, freeing his swollen tool from the front of the panties. I was as eager to get his cock back in my mouth, as he was to put it there.

My mouth closed around his thick shaft and we moaned in unison. Smack As the initial shock of the pain coursed through me Henry moved his hands to either side of my head and began moving his hips. My mind forgot about the pain flaring out from my backside as he pushed his cock deeper into my mouth.

"I've already corrected her once tonight for talking with her mouth full," the Terminator said. "You'll have to count for her, Henry."

"One," he said. It was hard to miss the sound of lust in his voice. His cock was halfway in my mouth. Smack The force of the blow moved me forward and more of Henry's cock disappeared between my painted lips. "Two." More cock. "Three." Three? I thought. I hadn't felt a third blow. All I could feel was this big fat dick filling my mouth and snaking down my throat. Smack I felt that one! Henry's balls collided with my chin and he all but howled out, "Foooouuurrrrr."

I could feel the heat of the blood rushing to my ass. I wondered how red it was already. But soon Henry pulled back. He slowly started fucking my mouth, pulling out until just the head was left between my lips, and then pushing it all the way back in once more. I felt more swats of the paddle and I had a vague awareness of Henry counting out loud but all I could hear was my heart pounding in my ears. The sensation of having my very first face-fuck was overriding all other concerns at that moment.

Ms. Callahan started timing her swats to Henry's strokes so that each time I was driven onto his cock by the force of the blow. Not that his dick would go any further into my mouth. With each stroke, he buried my chin between his big balls.

"Eighteen," Henry said. My mind was staggering. Eighteen? Had I really taken eighteen swats of that vicious paddle? Henry's hips moved faster now and before that thought was even finished the count had grown to twenty-one.

"Twenty-five," Henry said with finality. At that last count, his cock was buried balls-deep in my throat and he left it there. Now that the action had stopped I felt the fire burning on my ass. I thought I could feel the rising welts from the evil criss-cross design growing.

"What a nice red ass," the Terminator said. 'Twenty-five. Wow. I haven't had a student here in years that could take that many licks without crying like a baby. How's it feel, Stacey, dear?" she said as she poked my ass with her finger.

Henry pulled his cock out but left it close to my mouth. It just hung there, dripping pre-cum and my saliva. It was still as hard as nails.

"It hurts, Ms," I managed. "It hurts real bad." Henry slid his cock back in my mouth.

"Maybe I have some cream that will make it feel a little bit better," she said. She reached into her pocket and pulled out a half-used tube of first aid cream. As she gently pulled my panties down to the bottom of my ass-cheeks Henry buried his bone in my mouth and began fucking my face once more.

Ms. Callahan applied the cream generously and then began spreading it around with her hands. I was thankful that she had left my panties half-on. I did not relish the thought of Henry finding out I was not a girl. I felt the soothing cream reducing the burning sensation as she smeared it all over. I barely jumped when she ran a soothing hand down into the crack of my ass. She squeezed another dollop of the stuff right between my ass-cheeks and started working it in with her one hand.

I froze when I felt her first tentative probe of my puckered hole. Henry didn't seem to notice or care and kept sawing his rod in and out of my mouth. She pressed hard with one finger until my rosebud gave way and she slid in up to her second knuckle. It wasn’t a foreign feeling — I had used my own fingers and even a small vibrator 'borrowed' from a friend's sister to penetrate myself before. Her finger felt so good and I moaned around Henry's cock and tried to push backward against her hand.

"Well, well," she said with a sultry edge to her voice. "Looks like our little suck-slut is just aching to have her little hole filled too." Henry chuckled.

"Give her what she wants, Ms. Callahan," he said, "what she needs." It didn't immediately register with me what he had just said, but when it finally hit me, he pulled his cock from my mouth as I turned my head. Ms. Callahan, the Terminator, had turned her back to me and was pulling down her sweatpants. When they reached her ankles she unzipped the ends and stepped free of them. As she slowly turned toward me I saw my very first strap-on dildo.

It looked almost obscene hanging there between her legs. It was long, probably ten inches or more. It was shiny black and covered with bulging veins. It had a large mushroom-shaped head and a neatly formed set of balls nestled against the leather harness that held it firmly in place. She pulled her shirt over her head and I watched, mesmerized, as the big black dildo danced with each movement. She was wearing a black leather bustier under it and it barely held her tits in place. It was then that I noticed she was wearing black stay-up stockings as well.

She stroked her dildo almost casually with one hand while the other squeezed more of the cream onto her thick pole. She grinned with a wicked laugh dancing in her eyes. "Stacey," she said as she stepped closer to me. "I'd like you to meet someone. This," she shook the dildo for emphasis as her smile widened, "is the Terminator."

My mouth suddenly felt dry and I had trouble swallowing. I made some gurgling noises and shook my head no as she grabbed my hips and held them firmly. "It...," I gasped, "too... it... too big."

"Just relax, Stacey," she assured me. "It always hurts a little your first time. Just ask Henry, Miss DeBeers." I was shocked at hearing my last name. My mouth gaped open as I turned to look up at Henry.

Henry immediately filled my open mouth with his prick and I, as I had so far this night, sucked it straight into my throat without hesitation. "It's okay, Martin," he said. "We've known all along, Ms. Callahan and I. We set this whole thing up. I've been wearing her panties and getting fucked in the ass by her dildo for a while now. In fact, I come in early every day just to change into panties that she leaves for me in my locker." He kept up a steady rhythm going in and out of my mouth as he talked.

"I started watching you closely when my mom started complaining about her frilly things disappearing from the clothesline," he continued. "After I saw you sneaking into our backyard one night I watched as you pulled one of my mom's bras down from the end closest to your house and ran like hell." I felt 'the Terminator' sliding between my cheeks and the ridge of the bulbous head rubbing back and forth against my asshole. Henry kept humping my face.

"Then I started watching your house really close, keeping an eye on what you did when your parents weren't home. You leave too many gaps in your blinds when you get dressed up, Martin," he chuckled. "Anyway, so once I saw you with a wig and breast forms I knew you had a lot more than a passing infatuation with wearing women's underwear. So I told Ms. Callahan one day that I was tired of not getting to get off during our little sessions and she told me that if I could find another guy for her to fuck in the ass, then she'd let me have the other end."

I felt Ms. Callahan line up the head of her big rubber dick with my virgin asshole. She began to steadily push. I felt my hole slowly give way to her insistent pressure. As the very tip of the head was making its way inside of me, Henry pulled almost out of my mouth — leaving me a good four inches to suck on. He leaned forward to watch my deflowering as he continued.

"Well, I figured that although Ms. Callahan has fucked a lot of guys in the ass here at school and even made a few of them wear her panties, I'd never get another guy to even consider sucking my dick. And then, there you were. I saw you one night while your parents were at a movie or dinner or something. I'd watched you get dressed in some of my mom's lingerie and stuff and put your own clothes on over them.

After your parents left, you ripped off your boy clothes and immediately put on your wig and added your breast forms. Then you got into this skirt and blouse and put on your high heels. I watched you kneel next to your bed and suck that little vibrator. You bobbed your head up and down on it and sucked it like it was a dick. Then you hiked up your skirt, pulled your panties down, and proceeded to fuck yourself in the ass with the vibe."

"Get ready, Stacey," Ms. Callahan said. "Here comes the hardest part — the extra-wide head!" It was then I realized that she hadn't put it inside of me yet, but instead had been pushing just the very tip in and out of my hole. She grabbed my hips and pulled me toward her as she pushed hard. I know I screamed around Henry's cock; I know that I felt like she was tearing me in two. It hurt really badly at first but then it subsided quickly.

She gave me a few short strokes at first and then held me still with about two inches inside of me, giving my tight ass time to adjust to the intrusion. I had certainly never had anything so huge back there before! Henry gasped audibly when the dildo's head went in, but now he resumed his little story.

"I stood there, wearing nothing but a pair of Ms. Callahan's panties, and watched you fuck yourself with the vibrator while I jacked off. Pretty soon you rolled over on your back, spread your legs wide, and kept plunging the vibe in and out with one hand while the other one stroked your dick. I kept pace with your strokes and when I saw you start to come I came too. You scooped up your jizz one fingerful at a time until you fed yourself the whole load. I went to bed all sticky and satisfied."

Ms. Callahan said, "I think that's enough history for one night, Henry. I think this little slut is as ready as she's going to get." With that she lunged forward, shoving her dildo inside of me partway. She took a minute to reposition her feet, then pulled back a bit and shoved forward again. As I felt more of the dildo slide inside of me, Henry straightened and resumed stroking in and out of my mouth. Ms. Callahan started fucking me then, her strokes driving the dildo deeper and deeper into me. Soon she and Henry fell into a steady rhythm and I was getting fucked at both ends.

"I knew you'd be a dirty little slut," Ms. Callahan said. "I knew it the minute I saw you in your too-short skirt with Henry's dick buried balls-deep in your mouth. I said to myself, now here's a girl who likes it in both ends; here's a girl who needs two dicks at a time to keep her satisfied."

I managed a brief "mmm-hmmm" around Henry's cock. She was really thrusting hard into me with each sentence, punctuating her little speech with quick jabs.

"Except that you're not a girl, are you?" she continued. "You're a little cock-sucking sissy instead. You like to dress all sluttish and hang around in boys' bathrooms looking for cock to suck. Don't you? You need the feel of that hard flesh in your mouth, the hot cum spurting from it and hitting the back of your throat. You love to taste the cum as it fills your mouth before you swallow every drop. You're nothing more than a cock-sucking sissy cum-slut!"

My moans grew louder and louder at Ms. Callahan's accusations. I'd never been fucked like this or sucked a cock before, but her ranting had a kernel of truth to it. She was describing the girl I had always fantasized about being — and in very graphic and accurate detail!

Henry's grip on my head got tighter and he suddenly stood stock-still. Ms. Callahan's thrusts kept pushing and pulling me on and off his cock until he finally cried out.

"I'm going to cum! I'm... oh... Stacey... oh, oh, oh... unnnnnng hhhhhhh." Ms. Callahan drove deep into me and held me there, my chin pressed tightly between Henry's balls and his cock down my throat. I felt his balls spasm and twitch as he dumped his load into my throat. He moaned and pulled back until just the tip of his cock was in my mouth. He was still coming and I felt my mouth start to fill with his salty seed. I tried to swallow and gulp as much of it down as possible, but some of it leaked from the corners of my mouth and ran down to form a big jiggly drop on my chin.

It was so bitter and salty — it tasted like my own cum, but then again it tasted completely different too. I couldn't believe how much I loved it! I greedily sucked his cock all the way back into my mouth, trying to get the last few drops of his cum. I felt him shrinking and growing softer, and still, I sucked him — suckling him like a calf to its mother.

Ms. Callahan didn't lose her grip on me, but Henry pulled away and removed his cock from my hungry mouth. I moaned my frustration at the loss of his beautiful prick and my tongue chased after it until it was well out of reach. He came and stood next to me, almost hip-to-hip with Ms. Callahan. She released my hips and bent over slightly. I felt her hands inside my blouse, and then inside my bra. She pulled on my nipples and twisted them cruelly between tugs.

"The next time you suck a cock I'd better not see one drop of the load escape your mouth," she said. She was still slowly humping my ass as she played with my nipples. "I have a pair of very nasty nipple clamps waiting for you if you do. Do you understand?"

I nodded my assent. "Speak up, girl," she snapped. "Your mouth isn't full of cock now; you can talk."

"Yes, Ms. Callahan," I said.

"You know something? I think maybe you need some more practice. That must be it. Would you like to suck some more cock, Stacey?"

"Yes, ma'am," I said.

"Yes ma'am what?" she asked, punctuating every word with a hard, deep thrust of her dildo.

"Yes ma'am, I'd like to suck Henry's cock again."

"Who said anything about Henry?" she screeched. "I asked you if you wanted to suck some more cock!"

"I do, Ms. Callahan! I do!" I said. With Henry's cum drying on my chin and the strap-on dildo filling my ass, my emotions were running away with the moment. "I want to suck some more cock!"

"Why, Stacey? Tell me why you want to suck some more cock." She rolled my now-sore nipples gently between her thumb and index finger.

"I...," I stammered. "It was so... I mean it felt so good to... I just..."

"Stacey," she said sweetly. Up went my caution flag. There was her sweet side again! "Did you like the way Henry's cock felt in your mouth?"

"Yes."

"Did you like how good it felt when his cock went all the way down your throat?"

"Oh, yes!"

"Did you feel all hot and sexy every time his balls hit your chin while he fucked your face?"

"Mmmmm hmmmm."

"What about his cum? Did it taste good? Did you like it?"

"Yes, ma'am. Kind of bitter but good."

"How did it make you feel when his first mighty spurt hit the back of your throat? How did you feel when he kept coming and coming and filled your mouth with all his spunk?"

"Oh, Ms. Callahan... I felt so sexy. That I could give him so much pleasure with my mouth and then he rewarded me by letting me swallow it all."

"But how did it make you feel, Stacey? How did you FEEL?"

"It made me feel like a real girl. The kind of girl guys like to take to the movies and sit in the back row with. You know, the kind of girl all the guys like because she's not just a tease. The kind of girl that gives blowjobs."

“So let me ask you my question again, Stacey. Would you like to suck some more cock?"

"More than anything, Ms. Callahan," I knew my face was turning beet-red as I laid my soul bare. "I want another beautiful, hard, hot cock. I want to feel the spongy head against the roof of my mouth for the first time. I want to hear him groan as I take his entire length down my throat for the first time. I want a heavy pair of cum-filled balls slapping against my chin while I get face-fucked. I want another mouthful of hot, spermy cum to savor and swallow. I want it, Ms. Callahan... No, I NEED it!"

I watched a smile spread slowly across her face. Henry just stood there staring at me with disbelief. "I kind of thought you might decide that, honey," Ms. Callahan said. "That's why I invited a few more friends over for our little 'get-to-know-you' party tonight."

I heard the locker room door open and feet shuffling on the cement floor. As the first person rounded the lockers, Ms. Callahan said, "Stacey, I want you to meet the senior squad of the varsity football team."

As they came into view, I immediately saw that each of them was wearing a pair of red panties — some lacey and frilly, some plain satin, some a bit of both. Every one of them had a nice stiff cock tenting out the front. Some of them had big wet spots in the front from leaking precum.

"I always dress them in red panties," Ms. Callahan explained. "They're all such whores. Guys, this is Stacey. She'd like — no, she NEEDS to suck your cocks."

As I turned my head to face forward, a big black guy stepped up first. It was Beau, our star running back. He pulled his satin panties to the side and let his cock and balls swing free. He looked huge, and his dark, purple head looked so inviting. I closed my eyes as my lips closed over the head and I took him in my mouth. He groaned as his cock snaked its way down my throat.

Ms. Callahan resumed fucking my ass, pounding her strap-on dildo as deep as it would go each and every time. A line was forming behind the guy who currently had his cock in my mouth. I saw row after row of stiff cocks in red panties, all of them waiting for their turn in my mouth and stroking themselves through the panties in the meantime.

It was going to be a long, filling night!

Published 
Written by Stacey_tv2
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