My Teaching Days, Part 2
Add: 5 August 2015 / 15:57
Someone was knocking hard on the hotel door.
“Miss Taylor!” Loud knock. “Mrs. Lee!” Loud knock. “Miss Taylor!”
Rushing to the door, I barely got my robe tied. I completely neglected to put the chain on first. My big city skills aren’t so good.
As soon as the door was open a foot, Chad pushed past me.
“Sorry, Miss Taylor! Gotta whizz!”
The door to the room sighed and latched shut. I heard the lid slam against the toilet and the sound of pee jetting into the bowl. I actually stuck my head into the room to watch, I have no idea why, although I sometimes wondered what it would be like to hold a penis while peeing. Do you feel the flow? Do you concentrate on aiming? Do you think about masturbating? Back then, thoughts of masturbation absorbed way too much of my mental resources.
I should perhaps clarify, in case you’re not reading this immediately after reading what I wrote previously, that I’m writing about when I was only 21, in my first year of teaching, some nineteen years ago.
A few hours ago, Chad and eleven other students had checked into the hotel, near Little Italy in New York City, chaperoned by Chrissie Lee, Dave Stewart, and me. I taught English at a public high school and was a last minute replacement for one of the journalism advisors. This sort of thing was part of the good fortune and the curse of being one of the few unattached teachers at the school.
All of us except for Dave Stewart had paired up in double rooms on the fourth floor. The school paper would compete at Columbia University for recognition of its journalistic excellence. This three day trip was one of the very few overnight events the school (mostly) paid for. I had enjoyed the two hour bus ride with excitable juniors and seniors and looked forward to our first night in town. Aged sixteen to eighteen, they were giddy with what they imagined as anonymous freedom in a big city.
“Sorry, Miss Taylor,” Chad said, zipping up his pants. “My card wouldn’t open the door and I didn’t think I’d make it all the way to the lobby. I don’t even know if they have restrooms down there. You saved me, thanks.”
This was both awkward and not. Two weeks ago, Chad and I had masturbated each other and more, about which I’ve already written. Even at age 21, I remained committed to my virginity until I got married, however old fashioned that sounded then and sounds sillier today. However, I permitted, even encouraged, anything that didn’t involve penis penetration below my waist.
“You should get on down to dinner,” I said. “You know where it is, just a block up the street. Mr. Stewart and Mrs. Lee are already there and probably everyone else.” I pulled the robe a little tighter.
“I enjoyed what we did at your apartment,” he replied. “I really wanted to come back right away, but my parents have me almost locked down. Except for this trip.”
A huge boundary existed between teachers and students, almost like parents and their kids, and people on opposite sides weren’t supposed to have sex, even if they both thought it an excellent idea. I’d crossed the line once with Chad. If I crossed it again, the boundary would cease to exist. Obviously, another encounter would not be sensible.
On the other hand, masturbating at home alone wasn’t doing much to quench my thirst for intimate contact. It only helped a little when the guy across the street watched me – exhibitionism (and watching him) had become the sexual highlights of the past several months other than the one time with Chad.
What the heck, I thought, Chrissie won’t be back for two hours and who cares if I’m a little late to dinner. They might worry a little about Chad, but probably not enough to actually do anything. I opened my robe, baring my boobs and bald pussy. I put my hand on his jeans and pressed his cock. I kissed him lightly and led him into the room.
Tiny hardly described the room I shared with Chrissie Lee. No more than two feet of space separated the two twin beds. A plain table supported a small TV. There was no dresser. The only place to store clothes, other than leaving them in the suitcases, was in drawers under the bed or, for hanging things, a narrow closet. Hotel-provided robes were a surprise luxury. The room didn’t even provide shampoo.
I started to unbutton Chad’s shirt at the same time he began to get his pants off. We were more eager than coordinated. Dropping my robe left me naked. Chad stripped to his jockeys, which I insisted he leave on so he wouldn’t “accidentally” try to put his cock inside me, like last time. We lay on our sides on the bed sheet, facing each other. Inside his underwear, my hand fondled his cock. He traced my slit.
“Remember what I told you before,” I said. “Take your time and no intercourse.”
His mouth found my boob and licked the nipple. I smiled to myself, a teacher about to enjoy the skills she’s passed along to a smart student, and lay back, spreading my legs. I suppose he took his time according to the much faster clock of a teenager. His fingers pressured my pussy before probing. His mouth sucked and licked greedily, then moved lower. A finger found its way into my hole. My clitty felt the deep breath he took before his tongue began lapping at my cunt. A second finger entered my hole. His tongue moved faster. My legs sprawled further apart and . . .
The door to the room snicked open.
“Diane?” Chrissie called, walking into the room. Her mouth fell open and she wobbled, but didn’t say anything for several seconds. Well, I thought, I almost made it through a whole year of teaching.
Chad stopped licking my cunt, but didn’t move. With his ass in the air and his face in my pussy, we must have been a sight.
Her arms folded across her chest, Chrissie looked fairly formidable. Her black hair had been cut short of her shoulders and she wore no jewelry. Black eyes glared at me over a cute nose and full red lips twisted into a frown. She still had a nice figure at forty or so, but she looked soft, with a bit of a tummy. I pulled the sheet up and Chad grabbed an edge for himself - now we looked even guiltier, together under the sheet.
“I came back to see why you’re late, Diane, and to find out if you had any idea where Chad went. I am, apparently, a brilliant detective, having solved both puzzles. I’m at a loss for what to do about it.”
Me, too, I thought. I considered what I knew about Chrissie. Of the gossip and rumors that passed for conversation in the teachers’ lounge, it was believed that Chrissie had marriage issues and hadn’t had sex with her husband in a long time, perhaps years. She might be a little or a lot lesbian, but most female teachers got that, although married ones not so much. She seemed kinda sexless, contradicting the lesbianism. I wasn’t certain women in their forties even cared much about sex, but both Madame Bovary and Cosmopolitan said they did.
I tossed the sheet covering us aside, more of a charge into the unknown than a well-conceived strategy. Putting my hand on Chad’s cock, which had actually lost some of its firmness, I said, “You could watch, if you want.”
Chrissie took a step back and banged into the wall. She bit her lip and seemed to be thinking it over. She was thinking about something, anyway. I put my hand in his underwear and fondled him. His cock hardened quickly. I pulled my hand out and stroked the sides so it would be clearly outlined for her. A damp spot bloomed through the cotton.
“OK,” she said, a tremble in her voice, “but only if I can take pictures.”
Yikes! I totally didn’t see that coming. With pictures, there would be proof that I was a sex-crazed witch. On the other hand, pictures from six feet away would make Chrissie complicit. I wondered what she would do with them. Who would even think of such a thing back before cellphones?
“Fine,” I said.
I kissed Chad on the lips and whispered, “Let’s start over. Just pretend she’s not here.”
That would be hard to do in a room this small. I rolled Chad on to his back and kissed him hard, my boobs pressing into his chest. I gently ground my pussy against his underwear-protected lap. I heard Chrissie pulling things out of the drawer under her bed. I heard a click. The flash of a camera gleamed brightly in Chad’s eyes.
I rolled under Chad, which took some coordinated effort on the twin bed, and pushed down on his shoulders, urging him lower. He repeated the earlier pattern and soon his tongue lapped at my pussy. Chrissie continued to take pictures, which ought to make it clear I wasn’t simply the aggressor.
“Hot in here,” Chrissie said, loading a new canister of film into the camera. “Shit. Twenty four more pictures and I’m out of film.”
Chad continued to lick my cunt. He pulled my labia apart slightly and his tongue found my clitty with only minor movements required from me. I heard Chrissie suck in a breath. The flash went off again.
“Why is his underwear on?” she asked. “He should take it off.”
“Miss Taylor said she doesn’t want me to have intercourse with her, even by accident,” Chad said, disappointment in his voice.
“I’m saving myself for marriage,” I added, embarrassed.
“Well that’s just stupid,” Chrissie said. “Do what you want, or don’t do what you don’t want, but he should take off his shorts.”
Chad looked at me like a puppy who’d heard the rattle of the dog biscuit box.
“OK,” I replied, “but only if you take off your clothes, too.”
“You don’t make the rules, young lady.”
“This one I do. If Chad’s going to wave his cock around, you’ll be naked, too.”
For all I knew, she had only been looking for an excuse to take everything off. Whatever the case, she didn’t argue further. We watched her undress. She lay her clothes neatly at the foot of her bed. While she did that, I noticed what looked like the end of a vibrator sticking out from under her pillow.
“What’s this?” I asked, and pulled the pillow away to look.
I discovered a translucent dildo about a foot and a half long with penis shapes at both ends. Had she unpacked it when we arrived or just now while looking for the camera? Chad stared at it, his own cock bobbing free from his jockeys and stiffer than the dildo.
“Can I see that?” he asked. “What’s it for?”
Ah, the innocence of the old days before the Internet. I answered for Chrissie.
“It’s so she can masturbate with another woman,” I said.
Chad blushed almost as deeply as Chrissie, who said, “It’s just for me. But what Diane said is right, that’s how some women use it.”
Chrissie took a picture of Chad’s erection. We’d lost the rhythm of his eating my pussy. I had an idea.
“Chrissie, how would you like a picture of you and Chad posing together?”
“No!” she replied. “What if . . . well, I can’t let anyone see these, anyway. Sure, here, take the camera. Come over here, Chad.”
Chad hesitated, which surprised me. I was touched by his fidelity. I told him, “It’s OK, Chad. I won’t be jealous.”
They looked cute sitting on the bed, side by side. Chrissie’s breasts were slightly larger than mine and very full, much more appealing than I’d expected from how she looked dressed. Unlike me, her pussy had only been waxed.
“Nice,” I said, “but you look like you’re afraid of each other. Chrissie, how about you put your hand on Chad’s thigh?”
She didn’t need a bigger hint. I pretended to fiddle with the camera to give the scene a little time to develop. Looking down at his cock instead of at the camera and me, Chrissie began to masturbate him, one hand under his balls, with an enthusiasm both practiced and too eager, as though she wanted him to come in the next five seconds. Chad leaned into her breast and she fell back on the bed, pulling his cock to her mouth.
Moving around her bed, I took several pictures from different angles. The one I liked best, at first, looked straight up her tummy. Moisture glistened on her bush. Above her breasts, Chad’s balls were clearly visible. His cock disappeared into her mouth. While she sucked him, her legs opened and her hand snaked down between them. In the next picture, Chrissie masturbated while sucking Chad’s dick. Flash.
I watched her hand. It looked like she was finger painting her clitty, drawing broad circles with her fingers together. I hadn’t seen another woman masturbate since college and never someone so old. Resting my elbows between her knees, I snapped a close-up. I angled the camera, centered on Chad’s balls, and clicked, although I suspected the picture would be an incomprehensible jumble of body parts. Then his skinny young ass moved in my direction.
Chad’s stiff cock touched Chrissie’s cunt. I put my hand to my mouth. She reached down and pulled him inside her. I’d never been fucked and I’d never seen other people fuck up close and now here it was. I shook my head to clear it and remembered to take pictures. I got a good one of his ass and balls, with her cunt swallowing his cock. Chrissie’s right eye peeked from between their two bodies. Chad fucked her with enthusiasm, jiggling her breasts and tummy and butt cheeks. I remembered Jamaica Kincaid’s line about men wanting to fuck women who were built like stuffed sofas, although Chrissie was far leaner than that.
I moved to my bed. Chad’s face was directly over hers and they stared into each other’s eyes. His chest brushed her hard nipples. Chrissie’s neck and breasts flushed the color of sunburn. Leaning the camera and my head to within inches of their grinding hips, I snapped off several photos of Chad’s cock thrusting into her cunt. I put my hand on his ass. I wanted to be part of this.
They’d been fucking for close to a minute when Chad said, “Uh, oh”, just like he did at my home when he came. He rammed into her and I felt his butt clench.
“Come inside me!” Chrissie cried. “Give it all to me! Fuck meeeeeee!”
“Take it out!” I said, bringing up the camera. “Let me see you come!”
He ignored me. I watched his hips try to drive deeper with each spurt.
Chad collapsed over Chrissie. After a long pause, he eased his cock out of her cunt. I was close enough I could see come leaking from her hole.
“Move, Chad, picture,” I said.
He obliged by moving to my bed, drops of come dripping from his cock. I got up close to Chrissie’s pussy and took two pictures of Chad’s come oozing out. I handed Chad the camera. Chrissie’s just-fucked pussy was right in front of me. Gathering up my courage, I licked her pussy, tasting them both.
“Oh, yes, honey!” Chrissie cried out. “Oh, my! Lick me there, lick me there, lick me there!”
One hand either side of her pussy, I held her labia apart and tongued her clitty. She writhed under my mouth. I sucked her swollen nub. I took a deep breath and thrust my tongue into her hole. Her juice and Chad’s come dampened my cheeks. I put two fingers inside her and probed for the g-spot that had to be there. Her cunt was sloppy wet!
Finally confident my fingers were pressing in the right place, my lips returned to her clitty. It seemed bigger than mine, but maybe that was an illusion from being so close. Or maybe she swelled more than I did? I sucked it. I used the flat part of my tongue. She let out a low groan and, gripped by her orgasm, squeezed my head with her thighs. I sucked her until the instant her legs relaxed. I kissed the inside of her thigh and her ass came off the bed.
“Holy shit,” she said.
I kissed the inside of her other thigh and she lurched again.
“You’re killing me,” Chrissie said. “More, gimme more.”
I gave her more kisses, close enough to her cunt to feel the messy wetness, but didn’t dare lick her clitty directly. Crawling up, I gave each nipple a quick suck. She twitched with each. I kissed her on the mouth, my tongue probing past her teeth. She kissed me back urgently. I rubbed my cunt on her leg. I wanted to come, too.
“Diane, that was fucking amazing. I must have had six orgasms. I didn’t know that was possible.”
Chad sat quietly on the bed, his cock semi-hard – I had no idea if it was getting harder or softer, just that it was somewhere in between.
“Chad,” I asked, “why didn’t you take any pictures?”
“I did,” he said, “until the film ran out. You were . . . engrossed.”
I’d never noticed the flashes. What I did notice, though, was how totally unsatisfied I was. Always happy to masturbate for an audience, I straightened up over Chrissie and reached between my legs. I rubbed my cunt slowly, but with some intensity.
Chrissie said, “We can do better than that.”
She held up the double dildo. After making me wait for a minute while she got a plastic bottle of lubricant I doubted was necessary, she squeezed some of the goo onto each end, two quick hand jobs.
“Why do you have this thing, really?” I asked while she helped me get organized.
We sat facing each other, legs outstretched. Putting one of her legs under mine, the other one over, she said, “Truth is, I have a friend in Brooklyn. And, I’m embarrassed to say, while I didn’t expect anything to happen, I planned on fantasizing about you while you slept next to me. You are a very attractive lady.”
“And you are quite a surprise,” I said.
“No more than you and Chad.”
Our pussies were a foot apart. Holding the middle of the dildo, Chrissie pushed my end into my cunt. Two inches. Four inches. When I felt filled, I told her to stop, although I knew from experience I’d be able to take more. She put her end into herself and scooted carefully closer.
“Still a little sensitive,” she said.
She slid closer still and the pink pushed further into her. Chrissie began to thrust her hips at me. The rhythm didn’t come right away, but we found a groove and I smiled to myself with the familiarity of a dildo in my cunt. We leaned on our elbows, watching ourselves.
Back and forth, our hips bouncing, Chrissie did most of the work, her cunt gripping her end of the dildo. Her breasts shook. Following her lead, I squeezed my cunt muscles. Clenching my end, I fucked Chrissie with our cock. I rubbed my clitty. My end of the double-dildo was stationary in my cunt while the other end slid in and out of her. Someone should put balls in the middle of this thing, I thought.
“Oh my god,” Chrissie said, “I think I’m going to come again!”
She squealed and she came, a wholly vaginal orgasm. She finished and pulled her end of the dildo out of her pussy as though she’d had a year’s worth of sex all at once. I quickly grabbed hold of the middle of the double-cock and fucked myself with both hands. God, I felt greedy. Tired of sitting, I slid around and lay next to Chrissie, who had to lie on her side to keep from falling off the bed. She put a hand on my boob.
“Sorry, honey, I’m worn out. You fuck yourself good, though. Doesn’t she, Chad? He’s hard again, Diane, he could fuck you if you wanted.”
“No,” I gasped, although I was tempted after watching them. What was I saving myself for?
Chad stood next to me, near my shoulder. His hard cock stuck straight out and he masturbated. He stared at me. I had just one hand using the dildo, the other on my clitty. Chrissie watched Chad’s cock intently, although looked too tired to do anything with it. I pumped the long slick dildo in and out of my cunt. My fingers swept small fast circles across my clitty. Before I thought to ask Chad to fuck me with the dildo, my orgasm grabbed me.
“Oh! Oh! OH!” Pleasure surged from my clitty through my tummy and chest. “OH, FUCK!”
Chrissie held my eyes as I came. I finally stopped rubbing myself, but didn’t remove the dildo. I pushed it in carefully, pulled it back out slowly, in, out . . .
“Are you going to come, baby?” I asked Chad. “Are you going to come on my boobs?”
“Where do you want to come, Chad?” Chrissie asked. She licked my nipple and I shivered. “Do you want to fuck me again? Come inside my cunt? Was I your first? The first cunt you ever came in?”
His hand moved so quickly it blurred, although I was also still a little dizzy from fucking myself.
“Come on my face, Chad. Like before,” I said. Chrissie looked at me oddly. “Jack off on my face!”
A burst of come surged from his cock, but Chrissie had moved her head as soon as he spoke and opened her mouth. Instead of splashing my boobs, the powerful stream splattered Chrissie’s face, at least half of it entering her mouth. She wrapped her dripping lips around the tip of his cock, and he masturbated whatever was left. Chrissie took her mouth away, her lips compressed. Only the smallest trickle of come remained to dribble down Chad’s hand. Chrissie’s mouth covered mine. Her slippery lips pushed between mine and I opened my mouth for her. Chad’s come seeped from her mouth to mine. Our tongues swirled it between us. And then I did swallow, the first time I’d ever swallowed come on purpose. But it was come mixed with flavors from Chrissie’s cunt and her lips. I loved it.
“We’re really late,” Chad said, pulling his underwear back on over his damp cock.
“Let’s all clean up,” Chrissie said, taking charge, but still with me enough to kiss my nipple, smearing fluids there. “We can join them for dessert, I think. When they ask where we were, well, I’ll think of something by the time we get there.”
“What about the pictures? How do you get pictures like that developed?” I asked.
“This is New York, honey, you can get anything you want.”
“Can I have a copy?” I asked.
Chrissie hesitated, but agreed.
“Me, too, please,” Chad said.
Chrissie and I both shot back at the same time, “No!”
“I probably still can’t get into my room,” Chad noted, pouting.
“We’ll get someone up from the front desk. I’ll call while you get dressed.”
We shooed Chad out to wait by his door down the hall. Chrissie and I figured we could save a minute by showering together, but we were wrong.