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My Teaching Days, Part 3

My Teaching Days, Part 3

Diane, Chad and cheerleader Ashley are watched from across the street
“Miss Taylor, what’s he doing?” Ashley asked, some alarm inher voice. She pointed out the window.

“He’s a little goofy,” I replied. “He often takes off his clothes without closing his drapes. I can close mine or we can just ignore him.”

We were talking about the man in the apartment across the street from my own. I didn’t add that he and I had watched each other masturbate as recently as last week. In some ways, this had become the most regular part of my sex life, if that’s what you’d call it. I had no boyfriend. I’m writing this almost nineteen years later, but back then, recently turned 22, nearing the end of my first year of teaching at a large public school in eastern Pennsylvania, I had a decent start on a career that wouldn’t last, and no start at all on the relationship that would soon lead to marriage and a son.

“What’s his name?” she wondered.

“I have no idea,” I said. He stood near the window and lowered his pants.

It was late enough in the afternoon that the sun had drifted well west, so there was no glare off the glass. I was confident he could see us as clearly as we could see him. He’d never stripped while someone else was in my living room, but then I didn’t get many guests, either. I speculated that Ashley was probably a temptation.

Besides teaching English to bright juniors and seniors, I managed the cheerleading squad. I gave all my girls extra teaching attention when they asked and Ashley was struggling with a subject from early in the school year, similes (easy) and metaphors (not so easy). She knew they’d be on the final next week.

“He knows we’re watching, doesn’t he?” she asked, stretching her arms and thrusting out her breasts.

When I say Ashley’s a temptation, I mean that even in my squad of attractive girls, Ashley stood out. Not quite seventeen, her breasts featured prominently, proudly pushing out her white blouse. The rest of her, by contrast, was on the smallish side, so she looked like what she was, a gymnast with big tits. If that weren’t enough for Mr. Naked Guy, Ashley had what I thought of as California hair, long and fine and bright baby blonde. Her hair tumbled down her back like sunshine.

“I’m sure he knows,” I said, “and he likes the attention.” I could have added, and so do I.

He took off his boxers and stood three feet back from the window, naked.

“Miss Taylor, his cock is hard!”

“Use a simile,” I said, wondering if I should be shielding this girl from adult craziness.

“His cock is as big as a cucumber!”

“Nice one,” I said, “maybe an English cucumber, let’s not give him too much credit. Maybe a fat carrot. Now a metaphor.”

She frowned, thinking, and walked closer to my window as though that would help.

“His balls are like hairy plums!”

“No, that’s another simile, although accurate, I’d say. Remember, with a metaphor, you’re saying it’s literally something else.”

“That’s one big, unfrosted éclair and I’d like to suck all the sweet cream filling out of it.”

“Now you’re just being silly,” I said, slightly shocked.

“OK. OK. Look – he’s wrapping his hand around his hard hose.”

I laughed. “Yes, good, and a bonus for the alliteration. Now . . .”

I was interrupted by the doorbell and, getting up to answer it, said, “Think of another one.”

Chad was at the door. You may have already read about two of our encounters. He’d become my sex life outside of the guy across the street. A sixteen year old junior like Ashley, Chad and I had masturbated each other and more, but his cock never entered my cunt (despite one close call). No man’s did, that was for marriage. Fingers and toys, even fruits and vegetables were fine, but no hard human hoses.

“I’m horny,” Chad said. “You?”

“Shhhh,” I replied. “Ashley’s in the living room.”

I almost sent him away, but I was horny, too. I was always horny. I figured he’d survive seeing Masturbation Guy and maybe the guy would even leave us alone once Chad showed up. In the two months we’d been doing this, Chad had never failed to make me come and Ashley would be leaving soon.

Returning to my tiny living room, I found her on the phone in the adjacent tiny bedroom. She pointed out the window. The Hose had taped a phone number to his window, presumably his, and was talking on his cordless phone and stroking his cock. He saw me and smiled. He took down the sign.

“. . . and that’s Chad with Miss Taylor,” Ashley said into the phone. She giggled. “Yes, you have a nice cock. I compared it to a cucumber. And an éclair. You can ask Miss Taylor.”

Chad was swiveling his head.

“Hi, Chad,” Ashley said. “No way!” she continued, talking to the phone. “She did not.” Long pause. “Bullshit. No, I won’t.” Long pause. The guy with the stiff éclair had stopped stroking and was talking animatedly into the phone. Ashley said, “You are so full of shit . . . OK, deal.”

“Miss Taylor,” she said, “I’m sure I should just hang up, but this is too weird, so . . .“

Ashley glanced at Chad, but finished, “he says you have a bald pussy and he’s watched you, um, play with it, and, well, first, is any of that true?”

I was completely embarrassed even though I’d done nothing shameful. Somehow Ashley’s hearing that Naked Dickhead had watched made it seem abnormal. I considered lying, but I really don’t lie, so I nodded.

“And he says, I’m sure this part is bullshit, that he’s seen you and Chad, um, together? You know, sex?”

OK, that was a problem. I tried to picture when Mr. Cucumber might have seen us and flashed on our first time, when Chad had come on my face, not exactly on purpose. Chad flushed red. My cheeks felt warm.

“It’s not like it sounds,” I said. I guess I lied a little.

“OK, Josh, you’re right,” Ashley said. “I know, I know.”

She held out the phone and I took her place on my bed, holding it at arm’s length.

“What?” I asked her.

“We had a sort of a bet. I told him he was making that shit up. So now, I, um, will be taking off my clothes. I’d say Chad shouldn’t look, but he probably will anyway, and Josh is obviously watching, so, whatever.”

Ashley walked close to the window, but stood back a few feet so she wouldn’t be easily seen from the street below. With her back to us, her blouse and skirt quickly hit the floor. She stood with her arms out straight from her sides, all smooth skin and long hair. Her hair fell only a few inches short of pink panties that cupped her butt tightly.

I spoke into the phone, “Happy now?”

“Well, Diane,” Josh said, “how nice to meet you! Yes, I’m happier, anyway. Ashley has a little more to remove. Maybe she’d like you or Chad to help her?”

“You’re nuts,” I said.

“What’s nuts, Miss Taylor,” Ashley asked. “He doesn’t sound like a bad guy. Strange, maybe.”

“I’m not going to say it.”

Across the way, Josh stroked his cock with one hand and used his finger pointing and head nods to suggest Chad go over to Ashley. He mimed unclasping a bra. He thrust his chest in and out, bouncing breasts he didn’t have.

“You don’t have to do anything, Chad,” I said, curious about what he’d do. “You either, Ashley.”

Three quick steps and Ashley stood in front of Chad, her breasts touching his chest. He looked uncomfortable, despite the grin on his face. She pulled his arms around her so his fingers touched the hooks on her bra. Seconds later, he pulled the straps down her arms and I thought, I taught him that! She returned to the window.

Josh said, “My God, Diane, she’s stunning, almost as attractive as you. Those tits, I’d love to suck those big tits. And her flat abs. Jesus. Tell him to pull down her panties.”

“We don’t have to do what you say,” I said, trying to sound forceful despite wanting the same thing. I was as screwed up as Josh was.

“Just say it, Miss Taylor,” Ashley said submissively. “What did he say?”

“Chad should pull down your panties.”

“Well,” she shrugged, “the deal was naked.”

“What if he lost?” I asked, watching Chad kneeling to slide her panties down to the floor, his face right by her ass, flawless melon halves of pure muscle.

“If he lost, I wouldn’t have to do anything. He would jack off and come on the window.”

“Ashley!” I exclaimed. I put the phone down on the nightstand.

Chad began kissing Ashley, first behind her knees, then her thighs, then her ass. His hand slipped between her legs and even though I couldn’t see past him, I knew he was rubbing her pussy. I also knew he was good at it. I’d expected Ashley to move away, but instead her hands moved to her breasts. They were putting on quite a show for Josh.

“Miss Taylor,” she asked, “what did he mean about you and Chad? Do you guys, like, fuck?”

“No,” I said, “we don’t do that, but, well, we do a lot of other things. Like Chad’s doing now. He rubs my pussy. I give him hand jobs. Like that.”

“Where is Josh going?” Ashley asked, disappointment in her voice.

He had walked away quickly, but immediately returned with two towels he placed on the floor. Then, for some reason, he put his boxers back on. His erection tented out the blue fabric. I moved up next to Ashley to watch him – and to watch Chad’s hand rubbing her.

“You’re a lovely girl, Ashley, you know that,” I said, touching her arm.

“Look, Miss Taylor! Look, Chad!”

Across the way, Josh had been touching his balls through his boxers, his shoulders tight. Now, a dark patch bloomed across the front. From a quarter-sized spot at the end of his dick, the darkness quickly spread down his boxers to his balls before widening toward his hips like an animated ink blot test. Pee flowed down his legs. I watched his eyes roll with relief and his shoulders slumped.

“That is so gross!” Ashley said.

It was certainly strange, but it was oddly compelling and I had no idea why. It reminded me of when I’d watched Chad take a piss in my hotel bathroom. Josh finished, pee dripping from his boxers. He toweled his legs and, holding a towel to his lap, he walked back out of the room. It had been some sort of special display, I guessed, thinking, people are crazy.

“What do you guys want to do?” I asked. Chad had continued to stroke Ashley’s pussy while Josh peed. “Do you want to use my bed? Or just go home? What?”

Chad stood and, one arm around Ashley, put his other arm around me and kissed me on the shoulder

“OK,” I said, my voice rough and my sanity gone, “let’s get on the bed.”

“What about Josh?” Ashley asked.

“We’ll leave the drapes open.”

We stripped off our clothes. Chad paused before talking off his jockeys and looked at me.

“Go head,” I said, “take them off.”

“What?” Ashley asked.

“Sometimes Miss Taylor makes me leave these on. I almost fucked her once by accident and she doesn’t want any accidents.”

“By accident?” Ashley wondered. She was looking at Chad’s hard cock.

“Maybe you had to be there,” I said.

We climbed on to the bed, Chad in the middle and Ashley on the side closest to the window. Mr. Pee was watching us and masturbating.

“Nobody pee in the bed!” I said.

I didn’t get a big laugh, but it relaxed us a little. I put my hand on Chad’s cock and began to stroke it. I wasn’t sure what should happen next and I was the adult supervision. Like she was watching a ping pong match from too close, Ashley’s eyes moved from the guy at the window to my fondling Chad’s cock. She finally decided she was with us, turned on her side with her lovely ass toward the window, and cupped Chad’s balls in her palm.

“Miss Taylor,” Ashley asked, “where do you like it better, cunt or ass or mouth?”

“It’s ’best’, not ‘better’,” I said stupidly, astonished by the question.

“Oh, you said you don’t fuck, so which of the other two is better?” she asked, savoring the word.

“Well, having never done anal, I guess mouth is what’s left,” I replied. I wasn’t going to be intimidated by questions from a sixteen year old. “Really, I like giving hand jobs best. This is such a weird conversation. What about you?”

“Oh, ass for sure. Then mouth, then cunt.”

From the nightstand, where we’d simply left the phone off the hook, we heard a faint voice. Josh must have been shouting for us to hear him at all, “I’m going to come!”

Ashley grabbed the phone and in a breathy voice said, “Come, Josh! We want to see you come! All over the glass! Please!”

We were looking at Josh. With his cock pointed straight at us, come splattered his window. Just as it started to drip, another burst splashed right beside it. We watched Josh continue jacking his cock, but none of the rest made it as far as the window. His shoulders slumped, just like after he’d peed himself. He was apparently finished, and he waved goodbye. He had a lot of cleanup ahead.

“Well,” I said, “that was something.”

“Yeah,” Ashley said. “Something.”

“Do you really like anal sex, Ashley?” I asked.

“Do you have any lube?” she replied.

Nothing embarrassed this girl. I began to formulate a theory that everyone wanted sex, roughly all the time and in the strangest ways, they just need a little nudge to know it was OK. I got some Slippery Stuff out of the nightstand and handed it to her.

“Not me,” she said, “give it to Chad.”

Ashley moved closer to Chad and her breasts grazed his chest. She bent over him and took his cock into her mouth. Her head bobbed several times. Saliva dripped from her mouth when she pulled away.

“You want to fuck me in the ass, Chad?” she asked, wiping her chin with the back of her hand. “Actually, Miss Taylor, why don’t you lube him up?”

We all stared at his cock while I slowly applied the slick gel.

“That feels great, Miss Taylor. I should get some of this!” he said. Realizing what he’d implied, he blushed.

Facing the wall, Ashley got on her knees and Chad positioned himself between them. Her strongly muscled ass cheeks made me wonder how Chad’s cock could fit between them.

“Miss Taylor, can you put some of that stuff on my asshole?” Ashley asked sweetly.

Now that was something I hadn’t been asked before. Everything stopped for a few seconds while I processed the question. I gripped an ass cheek, my fingertips in her ass crack. I squeezed a little Slippery Stuff into the crack and rubbed it around her asshole.

“In my asshole, please.”

With a dollop more on my finger, I eased it into her asshole, just an inch or so. I wiggled my finger in her. Her asshole was so tight I couldn’t imagine Chad could get inside. I used my slick fingers to jack his cock a few times. I teased him under his balls, but stopped when Ashley took two deep breaths and let each out slowly.

“OK, Chad, not too fast.”

He put the tip of his cock on her asshole and grabbed her hips. He tried to pull her back on his cock. He moved his left leg outside of hers, half standing. Ashley dropped her shoulders to the mattress and spread her legs wider. She reached back and tried to steer his cock. Chad put his other foot beside her and squatted, Ashley’s legs now between his. He leaned forward on his arms. The whole exercise looked awfully uncomfortable.

“Now, push, just a little,” she said.

Chad slid two inches of cock into her. Ashley screamed and stuck her face in the mattress. Chad quickly pulled his cock back out.

“NO!” she cried out. “Put it back. It just hurts so good. I should have told you I might scream a little, but it’s all good. Please! Put it back now!”

I saw motion out of the corner of my eye. Josh was back at his window, watching, naked except for a fresh pair of boxers. I said nothing.

Chad eased his cock into her asshole more slowly than the first time. He paused at three inches, about halfway.

“Go on!” she demanded. “Give it to me! Fuck me in the ass!”

As though he’d just been given a D and was determined to get an A, Chad thrust his cock all the way to his balls. Ashley screamed again. I wondered what could possibly feel good about that.

“YES! Fuck me! Gimmegimmegimme!” she pleaded, the three words running together. “Fuck me like a whore. I’m just a whore and I want your cock in my ass!”

Her hand reached down between her legs to rub her pussy. Feeling mostly left out, I put my hand over hers and she let my fingers take over. I inched closer, now on my knees, too. Reaching between Chad’s legs so his balls touched my wrist, I pushed a finger into her cunt. She was incredibly wet. I added a second finger. I felt Chad’s balls sliding along my skin.

Presumably on purpose, Ashley’s legs flattened on the bed, almost trapping my hand under her. I moved out of the way as Chad lay atop her, his cock buried in her ass, his legs splayed.

“Fuck me harder!” she insisted. “Call me your whore!”

His cock pounded faster. Ashley whimpered. His skin smacked against her ass, almost a slapping sound, again and again.

“Uh, oh,” he said, and slammed his cock into Ashley’s asshole.

She grunted loudly when he rammed her. Each time he strained hard against her ass, I imagined the spurt inside her. When he finished coming, he pulled out and her asshole gaped at me, a surprisingly large hole begging to be filled further.

“Sorry, Ashley,” Chad said. “But that was totally awesome.”

“You came too fast!” she whined.

“Lie on your back, Ashley,” I said, seeking peace.

“But . . .”

“Just do it,” I said, almost sternly. Then it struck me, what she’d said. This was out of my comfort zone, but I added, “You dirty whore! I want you to eat my pussy.”

They both gaped at me, but Ashley and rolled on to her back. I swung around and sat on her face, my pussy on her mouth and my boobs brushing her tummy. She thrust her tongue into my cunt. My face was inches from her pussy.

“You like that, you slut?” I asked. “Eating your teacher’s cunt? Fucking me with your tongue?”

I heard mumbling from between my legs. Having used up all the dirty language I could think of, I licked her pussy. A hand on each thigh, my fingers easing her labia apart, I lapped her clitty. Juice from her pussy, tasting like peaches, dampened my cheeks.

I pushed my face deeper into Ashley’s cunt, pressing hard with the flat part of my tongue against her clitty. I felt her legs twitch. Her mouth sucked at me. I pushed two fingers into her cunt before remembering what she’d said earlier. I pushed a finger into her asshole. It slid in so easily, I added a second finger.

“More,” she said, “gimme more.”

I tentatively put three fingers into her asshole, worried I’d damage her somehow. A muffled cry hummed into my pussy. Her hips jerked at me, urging me on. I continued to lick her swollen nub, but I focused on fucking her ass with my fingers. I pushed them in as deeply as I could, about halfway, and thought briefly of getting out my dildo.

Ashley grunted with every quick thrust of my hand. I squeezed her clitty between my lips. I tried to wiggle my fingers inside her asshole. Her body twisted with her orgasm and she squealed. Her legs gripped my head, then relaxed suddenly. She tried to turn away.

“No more,” she gasped, “no more.”

I climbed off her and saw Mr. Pee stroking his half-hard cock. Chad was lying quietly, his cock hard again just from watching. I was happy, as I always was (and still am) when I make someone come.

“Come over here, Chad,” I said.

In a sort of group hug, we rested together for long minutes, legs and arms wrapped around legs and arms. I idly stroked Chad’s cock, still slightly slippery. I thought about sucking it, then flinched from the image of where it had been.

“What about you, Miss Taylor,” Ashley asked solicitously. “How are you doing? Even Josh got off, but not you.”

“It’s OK,” I said, “it’s not about counting orgasms.” Was that a lie, too?

“What if Chad fucked you in the ass?” she asked. I felt her warm breath on my ear.

“Oh, I couldn’t do that,” I said. “It obviously hurts a lot.”

“No, it doesn’t,” Ashley replied. “There’s pressure, and surprise, I guess, but it’s not painful if you relax. Usually, it’s part of the best ever masturbation. I even got an orgasm from it once.”

I smiled. “Maybe another time. You two should get going.”

“What do you usually do, Chad, with Miss Taylor?” Ashley asked. She hadn’t moved. “Besides, you’re hard again.”

Never talkative, Chad reached between my legs. After all we’d been doing, two fingers slid in easily.

“Don’t you guys kiss?” she asked, whispering into my ear. Her breath had gotten warmer somehow.

“Not really,” I replied, “not serious kissing. I hadn’t thought about it. I just want to make him come. Show him how to make me come.” (That sounded exactly like counting orgasms, didn’t it?)

“That’s not right,” Ashley whispered and the whisper moved from my ear to my lips. She kissed me, her mouth slightly open. I felt her tongue touch my teeth and I opened for her. Her tongue, so recently in my cunt, plunged into my mouth.

My fingers found Ashley’s hard nipple. I rolled it between my fingers, enjoying how her tongue twitched or her lips moved in reaction. My hands cupped her breasts and slid down her sides. Down below, between my legs, Chad used both hands, two fingers inside my cunt, pressing up with the tips, and the fingertips of the other hand sweeping rapidly across my clitty. Ashley squeezed my boob, rolling her palm over my nipple.

I could feel the connection between our lips and my cunt getting stronger, a real sensation of heat flowing from each. The temperature suddenly spiked inside me, near my cunt where the flows merged, and my orgasm crackled. Fiercely aware of Ashley’s lips crushing mine and the flood of orgasmic energy, I was oblivious to everything else, my thrashing legs, my nails digging furrows in Ashley’s back.

They both backed off when I finished. Ashley said, “See, Miss Taylor, kissing is important!”

I smiled into her face, inches from mine, and asked, “How did you get so smart?”

“I am a goddess,” she said, grinning and tossing her hair.

“Nice metaphor,” I said, weakly.

The ebbing of my orgasm had sucked all my other energy with it. I tried and failed to process what it meant that I enjoyed Ashley’s kisses every bit as much as Chad’s attention to my cunt. Beside me, Chad had climbed on top of Ashley and was fucking her enthusiastically. I gripped her hand. She hooked a leg over mine, squeezed me back and seemed more than satisfied with Chad’s use of her door number three. Across the street, I expected to see Mr. Pee masturbating, but there was no one there, only a new smear of goo near where he had ejaculated before.

Now, nineteen years later, I’m still learning about my desires for both men and women. For many years, after my husband and I had stopped doing threesomes, I had no sex except with him. Over the past year, however, women have had new parts to play in my life and I find I’m quite willing to be pulled in that direction. But whether it’s a cock in my cunt or a pussy on my thigh, I remember Ashley and her observation: kissing is important.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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