“Quit being shy and go ask her out,” I said, turning around to follow the girl. I saw her go into a bookstore.
Terrance followed me. Now his gaze was darting around and his cheeks were turning red. “I don’t know. I’m not really looking my best today.”
“Nonsense. You look fine,” I said. I walked him to the bookstore entrance. “Now go.”
“Nah. I’m good,” he said.
“Quit being a pussy.”
“You do it if you think it’s so easy,” he said.
So I shrugged my shoulders and I went into that bookstore. And for the first time in my life, I found it amazingly easy to approach a woman and chat her up. I felt like I knew exactly what to say, because I knew exactly what I would have wanted a guy to say to me. I watched as the girl’s cheeks turned red as I fed her a compliment about her hair, and then I watched as they turned even redder as I fed her another compliment about her shoes. After just three minutes, she was squirming to get her phone number into my phone. I took it, but I didn’t actually plan on contacting her. I gave the number to Terrance and said, “You’d better call her, and you’d better compliment her.”
He looked at me with wide eyes and parted lips. “How did you do that?” he asked.
I shrugged my shoulders. “I don’t know. She’s just a girl,” I said. And that comment didn’t seem to register in his brain. He just kept staring at me with glowing eyes and parted lips.
We continued perusing the mall. Whenever Terrance wasn’t looking, I would find myself staring into women’s clothing stores, admiring the cute dresses and shoes on display. I wished I was at the mall in my feminine guise. I wished I could have slipped into all of those shops to try on all the different outfits. My heart nearly stopped when I walked past the lingerie store and saw a red lace bodysuit that would have fit my body perfectly. I wanted to own it, and I was already planning on getting dolled up so I could come back and buy it.
“What are you looking at?” Terrance asked, catching me half-hypnotized, staring into that lingerie store window.
“Huh? Oh, the model on that poster is just really hot,” I said. The model on the poster was actually quite attractive.
Terrance nodded his head. “Well you look like a creep staring at her like that. C’mon—let’s go meet up with the other guys at the food court.” So we carried onto the food court. And on the way I saw a group of young women, all dressed in the cutest clothes: skirts, tank tops, dresses, leggings, stockings, heels, flats—all clothes I wanted to try on. And I wondered if that was something they did: get together with all of their clothes and play dress up, trying on each others’ wardrobes. That would be fun. I wished I had friends to do that with. I wished that I could be one of those girls, just for one week, so I could experience the female lifestyle.
CHAPTER IX
Believe it or not, Terrance made the call that night, and apparently he stayed up late talking to the little blonde from the bookstore. He told me all about their conversation the next day. “She wants us to meet up with her and her friends at the bowling alley after school,” Terrance said, beaming with excitement despite the fact he got almost no sleep. I couldn’t help but notice him squirming in his seat through every class.
And I was looking forward to the bowling alley as well, even though I hated bowling. What guy isn’t excited to hang out with a group of young women for an afternoon?
My hopes were dashed shortly after the bell rang and I got up to head to my locker so I could grab my coat and head to the bowling alley. “Where do you think you’re going?” Miss Barrett asked as she skirted in front of me, blocking me from leaving her classroom.
“I’ve got plans,” I said, looking into her narrowed eyes. She had that familiar smirk on her face.
“Well you shouldn’t have made plans. You still have a week of detention left, don’t you?”
I opened my mouth but I wasn’t able to respond. I hadn’t forgotten about the detention, but I’d assumed that the charges had been dropped. I thought my amazing performance with my weekend homework had gotten me off the hook. I thought Miss Barrett had lost interest in trying to humiliate me. “Can we just start it again tomorrow? I’m supposed to meet up with some girls,” I said.
And she laughed. “Too bad,” she said. She closed to the door, leaving just her and me in the classroom. “I spent all night last night planning your detention today, so you’re going to entertain me. Now get yourself dolled up—you’ve got twenty minutes.” She pointed to the closet where she had a whole new outfit waiting for me, and a new wig: a short blonde wig with cute little curls.
I hurried to get ready, my heart suddenly pounding. I was back on the chopping block, fighting for my academic future once again. The outfit was cute: a long black dress that was fitted tight to my body, with a cute white collar, a high waist, and long sleeves. It was a bit preppy, but I liked that about it. The black heels matched perfectly. I decided to go heavy with the eye makeup, using black mascara and black eyeliner and pink eye shadow for contrast. It was one of my favourite looks yet, and I managed to pull it off in just twenty minutes.
Miss Barrett walked around me, inspecting not just my look but also my posture. I made sure to stand with my feet close together, almost touching, and I help my shoulders back like a proper girl. I felt cute and confident and not worried at all that she would find any reason to dock any marks. And she didn’t find any reason. “You look great,” she said. And then I looked back just as she held up her camera to snap a photo.
“What are you doing?” I asked in my male voice.
“What was that? That didn’t sound like your proper voice,” she said with that smirk. She snapped another photo.
I cleared my throat and asked again, this time sounding like Jacqueline. “What are you doing?”
“I’m making sure you won’t go blabbing about this with your friends. What happens in this classroom stays in this classroom—I just want to make sure you agree.” She snapped one more photo. And my stomach turned at the thought of those photos getting out—which was exactly the point. “Today we’re going to do something a little more… fun,” she said. “I picked something special up from the store, just for you.”
I watched as she sauntered over to the closet and pulled out a brown shopping bag. She reached into the bag and pulled out a long black dildo, formed to look like the real thing with veins and a bulbous tip. It almost looked like it was throbbing from my vantage point. Even the suction cup base looked to be alive. “W—What’s that?” I asked, even though I knew.
“Every girl owns a dildo—a girl’s best friend. This is your next best friend. You can keep it.” She wiggled it in the air. It was stiff but rubbery enough that it swayed and jiggled slightly. “But before you go and take it home and hide it under your mattress, I want to show you how to use it.” My heart skipped a beat as she walked over to the wall. She breathed hot air onto the suction cup base and then she mashed it against the tiled back wall of her classroom, at about hip-height. “Come over here.”
I was slow to walk over, my heart a stuttering mess. I looked down at the artificial cock, which was almost the size of my forearm, and not much thinner. “You can feel it,” Miss Barrett said to me.
“Can’t we do something else? Like silent time—let’s just do silent time,” I said.
She laughed. “Reach down and feel it. If you were a real girl, you would want to.”
So I bit my tongue and reached down slowly. I curled my fingers around the fake cock and then I pulled them up the long black length. I could feel all the ridges and bumps and veins and dips. “How does it feel?” she asked.
I took a deep breath. “Big,” I said.
I could feel her smirking now—I didn’t even have to look over. “Good. Now get down on your knees and I’ll teach you how to suck it.”
I actually sunk down to my knees. I couldn’t stop thinking of those pictures she took of me, all dolled up. The thought of my friends seeing those pictures mad
e me shudder—and the thought of my parents seeing them made me nauseous. So I had to play along. I had to satisfy Miss Barrett, even if that meant satisfying a fake cock stuck to the wall.
“First, start with a gentle stroke. Curl your fingers around the cock and gently pull the foreskin back and forth. Yes, good, just like that.” I did as she said. She didn’t seem to mind my trembling hand. “Now after a few strokes, you can tighten your grip just a little bit. You don’t want to get too tight too quickly.” I tightened my grip. The fake skin felt terrifyingly real. And it felt strangely warm, as if there was actually blood pumping in and out of it.
“Like this?” I asked.
“That’s good,” she said. “Try twisting your wrist just slightly with every pull. Good—just like that. That looks really nice.”
My heart was pounding so hard; I was worried I was about to drop dead and the police would find me in a black dress and black heels and makeup and a wig. It was a horrible thought.
“Now get your lips close. You can tease the tip with your nose and lips, but don’t give him the mouth just yet. You want to get him hard, and nothing gets a man harder than teasing.”
So I floated my lips close to the cock while I pumped it. I gently touched it to my nose and then I brushed it down my lips.
“Good. Now give him a little bit of tongue.”
I stuck out my tongue and gently circled the tip of the artificial cock.
“Do you like that?” she asked.
I nodded my head gently. “Yeah,” I said. There was something strangely fun and exciting about teasing that dildo. My heart was pounding harder than ever before.
“Now suck his tip. Work down the shaft slowly, one inch at a time. Get him as hard as you can before you really start going to town. Remember—it’s all about the tease.” I slipped my lips around the tip and I started to suck. I bobbed my head slightly, sinking that cock deeper and deeper into my mouth. And in a weird way, I thought I could feel it getting harder and harder. Once it was pressed against the back of my throat, it felt rock hard in my mouth. I gagged a little bit, but I kept sucking. And whenever I surfaced for a breath of air, I would use my hand to keep my momentum going. “You’re so good at that.”
I looked up. Miss Barrett was watching me with glowing eyes.
“Do you wish you had the real thing?” she asked.
I nodded my head. I did wish I had the real thing. I wished I could actually make a cock rock hard. I wished I could actually bring a real cock to orgasm, rather than playing pretend.
Miss Barrett looked around. “You’ll have to promise not to tell anyone about this. She reached under her skirt and yanked down her panties. Then she hiked her skirt up, revealing her long, curved cock, which was already half-erect. “Sorry, I got a bit excited watching you go.” Her cheeks were a slight shade of red.
And I was frozen. Months ago, when I started that mean rumour—I was right. Miss Barrett was a tranny. She did have a long cock dangling between her legs, with a cute patch of short pubic hair on her pelvis. She swayed her hips from side to side, letting her cock flap and slap against her thighs. It was my chance to make a real cock hard and to get a real cock off—and it was Miss Barrett’s cock.
“Well? Go on now. Don’t just sit there and make me feel vulnerable,” she said. So I turned away from the big black dildo and I curled my fingers around a real cock. It was so much warmer than the dildo, and much softer, at least at first.
I gently pulled back the foreskin, and this time I wasn’t just playing pretend. I watched as her bulbous tip emerged and throbbed. And then I pulled that foreskin back over her tip. “That feels good,” she said.
I looked up into her eyes and then I pulled my face in to suck her off—but I stopped myself, remembering her tip about teasing. So I just hovered the tip of her cock by my lips. I touched it gently against my top lip, and then I let a little giggle slip as she let a little moan slip. It was working—I was really getting her aroused. “You’re a quick learner,” she said.
I stuck out my tongue and carefully licked her throbbing tip. “I know,” I said with a grin. Her cock was hard now, throbbing intensely in my grip. I squeezed and tugged and made sure she was as hard as I could make her, and then I plunged her into my mouth. Her forty-something-year-old legs trembled. I sucked hard, getting her wet, making the tip of her cock drool a sweet nectar. It tasted good. Her whole cock tasted good, like vanilla and roses. I pressed her girth deep, until my nose was pressed into her soft mane of pubic hair. I gagged a little and then I surfaced for air. I kept the momentum going with my hand.
“I’m very impressed,” she said. “You might just pass this class after all.” She ran her fingers through my hair. And then her whole body shuddered with a pulse of euphoria. She let a little moan slip, and for a second I thought she was about to ejaculate. But it was just another dribble of sweet pre-cum. “Fuck, you’re so good at that.” I kept sucking.
And then I stood up on my heeled feet, keeping that cock in my mouth, bending my body over at a ninety-degree angle. I reached back with my free hand and I hiked up the skirt of my dress. I don’t know what had overcome me, but I needed that big black cock in my ass. I’d never had anything in my ass before, but I couldn’t stop myself.
Miss Barrett’s cock was hard and enormous, curving slightly to the left. I loved the way all of her veins felt, pulsing against my tongue and the insides of my cheeks. I was in heaven. I really felt like a real girl, like the perfect little slut I’d been dreaming of for over a week now.
I pulled my panties to the side and I wiggled that hard dildo in-between my butt cheeks. It was still slick with my saliva—more than enough to lubricate my hole for penetration. I had to strain as I pushed back. The initial penetration didn’t happen so easily. I was tense and scared and a virgin, but I had to keep pushing. After a minute of careful wriggling, the black tip pushed into my body. I let a little gasp slip out from my lips. It was so thick, stretching me so wide, but I could take it—I had to take it.
“You’re so fucking hot,” Miss Barrett said. “And you’re such a massive slut.”
I loved it when she called me a slut, because I was a slut. I wanted to be fucked. I wanted to dress like a little hoe and I wanted guys to get off in and on me.
I felt that cock sinking deeper into my asshole. It was a tight squeeze, but somehow it kept going in further and further. I moaned and squirmed and my hole puckered—and the whole time I managed to keep Miss Barrett’s massive erection inside of my mouth. I coughed and gagged and tickled her length with my tongue, and then I found my whole body bobbing back and forth, my butt pressing against the wall, over and over.
My own cock was rock hard, out of my panties, aiming up towards my chest, throbbing as if about to burst, about to make a big mess of my little black dress. And my blonde hair was hanging down in front of my face. I’m not sure how my wig wasn’t falling off, seeing as it wasn’t even pinned in. Though it was high quality—probably one of many wigs Miss Barrett owned, back from when she first started to transition.
I wanted to taste Miss Barrett’s cumshot so badly. I wanted to suck every last drop out of her and I wanted to swallow all of it and feel it warming my belly. But first, I had to get her off. I sucked hard and bobbed my head and fondled her ball sack with the hand that wasn’t holding me up from falling over.
Her body was squirming and shuddering and tensing. Her legs were trembling and her cock was as hard as the desk she was leaning her butt against. “You’re going to make me come,” she moaned.
“Good,” I said with a muffled voice. I sucked harder and harder, bobbing my head faster and faster. My own cock was tingling and my asshole was pulsing with warm euphoria. The dildo was pressed right into my sweet spot, right where I wanted it to stay forever. I didn’t want that moment to end, but I knew it was about to end at any second. I couldn’t hold on forever. That euphoria was too strong, about to tip me over the edge. I tried straining and clenching every muscle in my body
, but that only made the euphoria more intense.
I screamed loud, and then a rush of warm cum suddenly gagged me, basting into the back of my throat. I gagged and coughed and managed not to choke somehow. The cum was sweet and salty and a bit battery, but I liked it. I made sure to suck every last drop out from Miss Barrett’s cock before swallowing all of it. The taste lingered on my tongue long afterwards.
And it wasn’t long after Miss Barrett’s heavy cumshot that I blasted a load into the inside of my skirt. My legs trembled and nearly buckled as my erection unloaded my own concoction of warm goo. And my God, it felt amazing.
Miss Barrett stumbled back and I stumbled forward. Suddenly, I felt empty—nothing in my mouth and nothing in my butt. My asshole was still agape from the thick dildo, which I was already planning to play with again as soon as I was home from school.
I was strangely out of breath, even though all I’d been doing was bobbing back and forth while standing up in high heels.
Miss Barrett already had her cock put away. She straightened her dress and cleared her throat. “I think that’s all for today’s detention. I’ll see you tomorrow, Jacqueline.” Her face was dark red, as if she’d suddenly realized what she’d done: face-fucked one of her students. I was eighteen, so it wasn’t illegal or anything, but I was still one of her students.
So I got myself cleaned up in the change room and then I went straight home, without stopping by Miss Barrett’s classroom to say goodbye. I wasn’t sure how to process what had happened. I wasn’t sure if any of it was even real, or just some extremely vivid daydream.
CHAPTER X
It was during my first period class the next day that I started noticing what the other girls in my class were wearing. The girl next to me had the cutest little floral dress on, and the girl next to her was wearing a surprisingly sexy black skirt and black stockings combination. Just in front of me was a girl wearing a loose-fitted tank top with a red bra underneath, which was driving the other guys in my class wild. I was asked to pass a note down from one boy to another, and I decided to read it before passing it along. “Don’t you just want to fuck Monica so hard right now?” the note read.
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