As a kid in high school, I didn’t have a huge amount of success with the ladies. Although I was fit, and handsome enough, I was way too socially awkward, and self-conscious. That’s why I turned to the internet.
Apart from the obvious pornography, there was a website I found, called ratemycock or something like that, where you can post pictures of your member, and have other users rate it for you. I always wondered whether I had a good dick or not, so I posted a pic, making sure to tense my abs too.
The response I got was crazy. I knew my cock was above average in size, but I got hundreds of comments telling me how much they all wanted my cock, how big it was, how tasty it looked. It sent me wild reading the messages people sent me. I’m straight, so I had to sift through the tirade of gay men, but occasionally a horny woman would send me a message asking for more pics.
One such woman called herself Lily. She sent me a message telling me that her husband’s cock was pathetic compared to mine, and that she wanted to taste it. She sent me nudes of herself, exposing all but her face, and I sent back dick pics, and a video of me masturbating. We got chatting, and I discovered she was in the same city as me. I thought, fuck it. Why not? I’m not an idiot, I know there were risks, but she sent a pic of herself with my username written on a piece of paper. That seemed like good enough proof to me.
We didn’t tell each other anything about ourselves. We made it clear what we wanted. A quick, clean, no strings attached fuck. We arranged to meet in a motel room a few blocks away from where I lived.
The motel was surprisingly decent. I vaguely wondered what my mystery lady did to afford it. I entered, asked for Lily’s room, and was shocked to hear a familiar voice from behind me.
“Tony?”
I spun to see Mrs. Jones, my English teacher, standing in the reception in a long trench coat. Her legs were bare.
“Oh,” I said. “Hi, Mrs Jones.” What was she doing here?
“Are you… Tony?” she asked. Her youthful face was a mix of confusion and intrigue.
“Yes,” I said, confused. She’d known me for years, why was she asking who I was.
“From the website?” she said, and I suddenly realised what was happening.
“Oh,” I said. “Oh god. Lily?”
She nodded, laughing nervously. “That’s me.” Suddenly I couldn’t look at her without seeing that amazing body beneath her coat.
“Well,” said Mrs. Jones. “Shall we go upstairs?”
I stood dumbfounded. Was this really happening? My teacher… surely it was against the rules. But she walked off, swaying her hips, and I was powerless to do anything but follow.
“I loved your pictures,” she said as we climbed the stairs together. “I never would have thought, from you… such a quiet boy. But then, it’s the ones who don’t bark with the most bite.” She opened a door to a room, which had a double bed in it. “Here we are.”
She sat on the bed, and unbuttoned her coat. Underneath she was totally naked, exposing her supple body. She was one of the youngest teachers at the school, at around twenty-fives years old. This showed in her body, unsullied by age. Her breasts, large and plump, were unblemished and perky. Her nipples had grown in size, and were now erect. Her hips curved just enough to drive me wild. Her pussy was clean shaved, not a hint of hair down below. “Your turn,” she said, pointing at my jeans.
I took off my top, revealing my toned torso. Lily smiled and moaned softly at the sight of my musculature. Then, I removed my jeans, to unveil my boxers, strained by the hardness of my cock.
“Wow,” said Lily, kneeling before me. She grabbed it, sending a shiver of pleasure down its length, and sucked it through my boxers, soaking the fabric with her saliva. Soon, she pulled them down, and beheld my rock hard cock.
“Fuck,” she said, in a deep, quavering voice. She set to sucking it, slathering my cock in her saliva, attempting to take all eight inches down her throat and failing, gagging. This was enough to make me cum, as pent up as I had been the last few weeks. I thrust into her mouth, sending a jet of hot cum straight into her throat and mouth. She moaned, sucking harder, milking every last drop of semen from my throbbing cock, licking her lips when she was done.
“Well, Tony,” she said. “You’re very impressive. It looks even bigger in real life.”
“Thanks,” I said, shakily. I could still not quite believe that I was doing this, fucking my real teacher in a motel.
“I’ll give you a second to recover,” she said, laying on the bed. “But after that…” she indicated to her pussy, which she started rubbing, preparing for my entrance.
After a few minutes of watching her pleasure herself, I was ready again. Applying a condom, I whacked my cock on her pussy, teasing her. “No… please,” she moaned. “I need it. Fuck me.”
Smiling, I went to insert, and then backed out, teasing her even more. “Noooo…” she groaned. “Fuck me… please…” I continued to tease her for a few minutes, loving her whimpering moans of desire as she was denied what she needed the most. After a few minutes, however, I entered her quickly, causing a gasp of pleasure to emit from her mouth.
“Oh… holy fucking shit,” she said, as she panted and moaned while I fucked her. She was tight, and felt better than anything I had done before on my own. I pushed into her, feeling her tight pussy rubbing over my cock, breathing in time with her, loving every single moan that escaped her mouth. Before she had been the dominant force, taking charge. Now, she was my bitch, my fucktoy, to do with as I pleased. She lay powerless before me, accepting my cock as a gift.
“Fuck, I’m gonna cum!” she screamed, seemingly unaware of the thin walls of the motel. She orgasmed hard, wailing with pleasure and shaking as the sensation hit her. I kept fucking, bringing her to orgasm again, keeping her in a state of perpetual bliss. Her moans persisted, music to my ears, as I finally felt the orgasm coming for myself. I pushed deeper into her, cumming with a hard moan, disappointed in my primal lust that I couldn’t fill her up with my seed.
“Wow,” she said, as we lay together on the bed. “That was the best I’ve ever been fucked in my life.”
“Me too,” I said.
“We must do this again,” said Lily. I nodded my agreement, playing with her tits idly.
“Oh, and don’t forget you’ve got that assignment on Shakespeare. I want it on my desk by Monday.”
“What if I don’t?” I asked, tweaking a nipple.
“Well, then I’ll have to punish you,” she said, grabbing my cock. “For being a naughty, naughty boy.”
Source: reddit.com/r/eroticliterature/comments/i8xfxu/fm_str8_online_hookup_surprise
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