The Ti(M)e I (F)ucked a Former Teacher (Long) | 2016

Throughout high school, as I grew into my body, I grew more confident. I grew about 6 inches (in height, haha) between freshman and senior year, reaching my current height of 6’ 3” the summer before my senior year of high school. That year we got a new choir instructor, I’ll call her Jill. Our previous choir director had been a kind but fairly stoic older man. Jill was young (in her mid 20’s at the time), energetic, funny and, as all the young male students realized right away, quite the bombshell. Blonde and very curvy, with perky boobs and a very big ass to go with long, thick legs. If you looked at her in dark profile, you’d probably guess she was a black porn star or something.

In addition to being attractive, she was also a very cool director that got a lot out of her choir. She often joked with us in class and regaled us with some of her more mild college experiences (we assumed she wasn’t telling us the more wild ones). Despite that, some of the students decided she’d be down to party if we were legal. Despite this, she seemed to be a responsible teacher, never saying or doing anything out of line. A couple of weeks into the fall semester I was browsing facebook and found her profile. I added her (I was already facebook friends with a couple of my teachers so this was no big deal) and sent her a message saying hi. She responded with a friendly hello but at that juncture there wasn’t much to say.

Time passed and we had our holiday concert, which went well. However I noticed Jill (we weren’t on a first name basis yet but anyway) didn’t seem to happy afterwards. Friendly and polite, yes, but not happy. After the concert some of us hung out but I left early, while the night was still young. When I got back to my place I messaged Jill on facebook and inquired about her demeanor after the concert. She said she was fine but she’d been dumped the previous day. I told her she was far too attractive to be dumped by anyone and that she was better off. She said she appreciated the comment but that I shouldn’t be worrying about her attractiveness as I had a girlfriend at the time (who was pretty boring, except for one time which merits its own story). I told her not to worry, as I had just turned 18 and knew how to be discreet, not that I was trying anything, and said she was out of my league anyway. She agreed but noted my charm was just perfect for girls my age. I was worried she’d be offended by my candor that night but in the days and weeks to come she was as cool as ever. This included during the school musical, where, playing a role with a few solos, I got to spend some one on one time with her. We were always quick to joke with one another, and she didn’t get upset when I said something slightly dirty. After awhile I felt really comfortable with her and I think she did with me.

That summer I worked at a local sandwich place and she came by one day, luckily while I was on my break. She sat with me and talked a bit and I mentioned I was planning a party for that coming weekend. She told me to be safe (at this point she knew I’d been drunk/stoned before) which got me thinking. I whispered, “Could you buy me a handle of vodka?” I was still 18 and couldn’t buy alcohol and while it took some convincing she agreed on the condition I told NO ONE where I got it. I said I’d tell everyone I did a “Hey Mister”. I used the opportunity to get her number so we could coordinate when I’d get the booze and pay her.

The day after the party I texted her, thanking her again for being so helpful. She asked if everything went ok and I told her it had, despite me being a little hungover. She said I should have water and an asprin and I told her water and weed would work better. She agreed and said she would have mentioned that but she wanted to at least pretend to be a good role model. Then the moment of truth happened when I had a thought. The party had been at a friends and I was currently at a diner eating breakfast. I didn’t want to smoke at home or on the road so I asked if I could do it at her place. Again, she was hesitant but agreed. She lived alone and no one would be looking for me at her house. It was in a bad neighborhood and I joked that the cops never went around there anyway, and since I was a young black guy I wouldn’t look suspicious in the area. She texted me her address and I found it pretty quickly.

I went in and she gave me a hug. She was wearing thigh length athletic shorts and a wife beater with black bra straps showing. I asked if she wanted to join and she said she did or she wouldn’t have let me come over. She said she hadn’t smoked pot since college and she was also a little hungover and needed a pick-me-up. We sat on her living room couch and talked and smoked until eventually she jokingly asked if there were any juicy hookup stories from the party. I told her a couple of the students who she knew that had gotten together but said I wasn’t so lucky. She mentioned she hadn’t been doing well romantically since her boyfriend dumped her. I said I was sorry and that I was really surprised because she was really hot and seemed to be a lot of fun. She asked what I meant by fun and I laughed and said she knew what I meant. She said she’d had sex with a couple of guys in the month after her breakup but neither was particularly memorable, nor were they boyfriend material. I said it was good to stretch her...legs now and then, which made her laugh. It was at that point I noticed she was looking at my arms (I was wearing a T-shirt with the sleeves cut off) and I did a stretch that kind of showed off my arms and chest, which I’d worked out playing sports through high school. I asked if she was still looking for a boyfriend or if she’d be interested in something more casual. She laughed again, clearly stoned at this point and told me she wasn’t expecting a high school student to be so forward. I mentioned that I wasn’t in high school anymore and then I leaned in to kiss her.

We kissed deeply, cottonmouth and all until she finally started to move her hands up my arms and onto my chest. I took her cue and placed my left hand on her thigh and my right on the back of her head, running my fingers through her hair. After awhile she pulled away and said that this felt wrong but she needed it. I told her I didn’t think it felt wrong at all, and I gently pulled her hair back, giving me access to her neck which I began kissing gently, but eventually started to suck and nibble. She moaned, softly at first but then, as I moved my hand under her shirt and to her breast, she got louder. I knew she had a nice singing voice but she’d never sounded more lovely to me than she did right then. She pushed me away and said we should go to her bedroom. I followed her, pulling off my shirt as we went up the stairs.

As we entered her room I grabbed her from behind and playfully tugged at the waistband of her shorts. She giggled and told me to sit on the bed. I obliged, and watched as she turned around, facing away from me, and made a show of pulling off her shorts. Having long legs it was a delightful tease, and I couldn’t help but start to rub myself through my jeans as she revealed lacy black panties. She turned around and saw me playing with myself. She took off her tank and said that my dick wasn’t going to do me any good in my pants. I started to stand but she stopped me and gently pushed me back on the bed. She undid my button and zipper and helped me pull them off, throwing them over her shoulder. I had a very obvious bulge in my boxers and she traced it with her fingers, continuing the tease. She said she didn’t remember any dicks like that from her high school days. I said she should let me jog her memory. With that, she pulled down my boxers and my dick sprung out. She smiled and looked up at me while she began to lick the head, not yet using her hands. She then started licking down, and then back up, the shaft, first one side, then the next. Eventually she started to gently tug my balls and she put her mouth on the head of my cock, sucking gently. This got me to moan and when I started to buck my hips she moaned in reply. She then started to bob her head up and down on me, which led me to grab a fistfull of her hair. I tested her by pushing her head down further and she gagged but didn’t push back, instead trying to deepthroat the whole thing. After a few pushes, she got down to the base and came up for air, calling me a bad boy once she caught her breath. She said I was lucky she liked it rough.

After a few more minutes of great head, she stood up and said it was my turn. She stood up and sat on the bed. I kneeled between her legs and pulled down her panties, revealing her shaved pussy. I kissed the inside of her thigh, and made my way down to her wetness, starting by licking up and down her slit, and then sucking gently on her clit. I grabbed her hips for stability and started to alternate between licking and sucking her clit. I put my left index finger into her pussy, followed by another until I was stroking her g-spot. At this points her moans have reached the height of their volume and I want to make her scream. I start to increase the pace at which I was fingering her. I could feel her start to shake as she let out a loud screech as she came, pushing me away. I laughed as she laid there, breathing hard, recovering. I told her she still hadn’t made me come and she looked back at me and smiled. I laid on the bed beside her and she asked if I had a condom. I told her they were in my wallet (I brought them to the party, just in case). She retrieved the condom and rolled it down my cock. She then straddled me and took off her bra before grabbing me and slowly pushing herself down my dick, moaning softly as she did. She began to rock back and forth, slowly at first but then she began to pick up speed. I grabbed her hips to help guide her. I could tell she was starting to feel the pleasure as she closed her eyes and let her head fall back, beginning to moan louder. As she got close she leaned forward, tits swinging beautifully just above my head and I leaned up to put one of her nipples in my mouth. This pushed her over the edge again and this time she grabbed my shoulders and dug her nails into me, trying not to scream. This hurt, but I knew I had to keep fucking her. I flipped her on her back and took the lead, letting her wrap her legs around me while I fucked her. I put my arms underneath her, using one to grab her shoulder for more depth when fucking her and the other hand to pull her hair. This gave me the opportunity to hear her better, which turned me on to no end. As I started to get close I sensed she was going to come again, and so I held it for as long as I could. Sure enough, the sexiness of the screams she let out after her third orgasm was enough to put me over the edge as well, and I moaned loudly as I finished in the condom.

I didn’t pull out after I came, instead kissing her lips and neck. She said she hadn’t cum like that in quite awhile. I told her She was welcome to more if she wanted it. We had sex twice more that day and even more during the summer.