Gender: Male Age: 24 Location: toronto
Note: As per my other stories, the character names are all changed on the off-chance that there is someone who recognizes any of the descriptions of living arrangements or furniture. If this is the first story of mine that you are reading, I have three stories before this - while the other three stories are not necessary to read, they do help to build up some backstory to where I was in my life at the time. Once again, while the verbal interaction may not be accurate, the physical interaction is to the best of my recollection.
Eleventh grade was incredibly non-descript. I did a lot of the same things I imagine most teenage boys did in the early 2000s in a big city – smoking pot, drinking when I could get my hands on alcohol, and just trying to get action wherever and whenever I could.
I was still carrying on my sexual relationship with Mrs. Curtis, one of the Phys. Ed. Teachers at my school, during the school year, and I have to admit that she was the best fuck I had probably had to that point. By the time I was seventeen and finishing eleventh grade, I had probably slept with around twenty or so different girls and women. I never really thought about why at the time, but thinking back, I have eventually understood that women talk, and the blessing in my pants was something a small number of experienced young women were after. None of them compared to my experiences with Mrs. Curtis, though, not even the threesome I had had with my best friend’s sister and one of her friends. I think a big part of it was the risk of getting caught – we almost always were going at it on school property somewhere, save for the odd time where we met in one of our cars.
Summer had approached entirely too quickly – I spent most of my three months off working for my dad, doing whatever needed to be done around the office. I was essentially the coffee bitch and ended up filling in as the secretary for a month after the one who worked there abruptly quit without reason.
I never was one to look forward to the first day of school, and this year was barely different. The allure of being a senior was moderately enticing, and getting to have a senior’s common area with couches and tables to hang out in before school and during spare periods was pretty relaxing. Other than that, though, I was really not looking forward to the promise of spending most of the nine months learning about stuff that wouldn’t even be relevant to my educational path beyond high school. Above all, however, I was least looking forward to going through another school year without a girlfriend. I had been with a few women multiple times, not really bouncing between women, but sticking with one for a few weeks or a month, and I was genuinely starting to feel like I was missing something.
Sex is always welcome in my life, but most of my guy friends had been going steady with someone for at least half a year at this point, and I was starting to feel like a bit of an extra wheel whenever we’d go places. We would have dinner for five or seven, and most of my guy friends were too busy most of the time. By the time September rolled around, I was feeling pre-emptively dejected about how I would fare as a senior.
As I parked across the street from school on orientation day, picking up my schedule and books, my heart jumped a few beats. There was Emily, my first girlfriend. The girl who had taken my virginity and shared most of my first experiences with the fairer sex.
“Oh my God, Rob!” she screamed as she ran up to me, hugging me tightly like she hadn’t been gone the last eighteen months.
I was at a complete loss for words. This was the girl who meant everything to me. This was the girl I first thought I loved, though in reality, she was just the first female to accept me into her bed, so that probably played a big part in those feelings.
“What are you doing here?” I finally managed to spit out.
“Nice to see you too, Rob,” she rolled her eyes at me. “I convinced my parents to let me finish school at home so I would have an easier time applying to universities. They agreed that it would also be nice if I could graduate with the friends I’ve had for most of my life.”
“I’m so happy to see you, you have no idea,” I was beaming at her.
“Look, I’m on my way home, but let me know if you want to get together,” she proposed.
“Is that ok with your parents? The last time your mom saw me…” I mumbled, remembering the awkward situation that led to Emily being taken out of school in tenth grade.
“Look, Rob, they know I’m turning eighteen in a few months, and they know they can’t stop me from being promiscuous. They really like you do, my dad always thought you were super polite and respectful. Part of the condition for me being allowed to be at school again is that I put school first, but they’re fine with me having a boyfriend – it’s probably better than me sleeping around.”
“I’d love to see you, then. I’ve really missed you, Emily… you have no idea how much.”
Grabbing my hand in hers, she began writing on it, “Here’s my new cell phone number. Text me later, and maybe you can come over for dinner tonight. I’ll try to smooth things out with my mom before you come over!”
I hug her again, and she lifts her head, kissing me lightly on the lips, before running off to catch up to Alexa, her ride home.
I went into the school and got my schedule, saying hello to some friends on the way and meeting a few of the new faculty members. I grabbed some pre-application forms for university, and made my way to the gym.
Knocking on the door, I poked my head inside to see Mrs. Curtis chatting with some student I didn’t recognize, as well as two older people I imagine where this girl’s parents.
“Oh and this my star athlete, Rob!” Mrs. Curtis said, with sarcasm that this family couldn’t detect.
“Hey, Mrs. Curtis, I didn’t mean to interrupt. I’ll talk to you tomorrow or something,” I tell her, backing out of the room and apologizing to the family.
“No need, young man,” the father addressed me. “We need to get going as it is – Mrs. Curtis, it was nice to meet you, and I look forward to helping you with any lacrosse teams I can!”
“Thank you very much, Mr. Stevens. Have a great day!” She follows them to the door, closing it behind them. She clicks the lock shut, and slowly turns around biting her lip.
“Look, Mrs. Curtis, as much as I’d definitely love to right now, there’s a more important reason I came down to the gym. Emily is back in town, and is finishing school as a senior here.”
“Yes, I heard about that, Rob. Are you going to try to get back together?”
“I think she wants to – I just ran into her across the street, and... I don’t know, I just feel like this is something I should maybe not be doing if I have a steady girlfriend. Especially since you’re the reason she’s been gone.”
“I’m still sorry about that, Rob. I think it’s worked out pretty well for the both of us in the meantime, though. Wouldn’t you agree?”
“Melanie, we both know that what goes on here is fucking incredible. That’s not my concern. I can’t be having sex with you if me and Emily get back together.”
“Are you back together yet?” she asked me, pulling at my cock through my trousers.
“Well, not technically, I guess, but today isn’t really a good day to be doing this sort of thing is it? There could be new students touring the building, or you may get called to go meet someone.”
“So you’re not technically dating again, yet. And judging by Mr. Hard in your pants, he doesn’t seem to think it makes a difference either way.”
“You can’t seriously expect me to keep fucking you the entire school year if I do end up having a serious girlfriend!”
“I don’t expect you to, Rob. Right now, though” she trailed off, dropping to her knees and unzipping my pants.
Grabbing her under the arms, I lifted her back up gazing down into her eyes.
“Mrs. Curtis. I can’t believe I’m going to say this, because what we’ve had has been better than anything else I’ve had, but I don’t think I can do this. I think I might actually have feelings for her, and I can’t just do something like this without feeling bad about it.”
Her hand snaked its way into my pants, circling my hard cock to the best of her ability.
“Look, Rob, I know things are going to have to change. But… maybe we could just have one last time? Right now. I need it, and you obviously need it,” she responds, once again dropping to her knees.
As my head enters her mouth, I look down at her, her eyes locked onto mine, fucking me with them as well as she’s fucking me with her mouth.
“This is the last time, then. You promise?” I ask her, not entirely sure if I even care as the suction feels heavenly.
“We’ll see,” she grins up at me, before taking my cock into her throat.
“Mrs. Curtis to the front desk please, Mrs. Curtis to the front desk.” She’s being paged over the PA system.
“Fucking timing,” she pouts after pulling my cock out of her mouth.
Pulling me by my cock behind her, she drops her pants and leans over the chair, picking up the phone. Looking at me, she tilts her head to ask what I’m waiting for.
Lining up my cock with her pussy, I slide it along, spreading some wetness to make sure it goes in smoothly.
“This is Mrs. Curtis – I’m kind of indisposed at the moment,” she says into the phone, looking back at me and licking her lips. “I realize you need me at the front desk, but I’m having – OW. As I was saying, I’m having some female issues and need a few minutes in my office to compose myself. I will be up as soon as I can, thank you!”
Looking back, she smacks my arm – retaliation for pinching her nipples through her shirt.
“You should probably be wearing a bra then,” I laugh, as I shove my cock into her now soaked pussy.
“Oh fuck, this is what I’ve been missing all summer,” she moans.
I gently ease myself in about halfway, allowing her to reorient herself to my size. Pulling her hair, I grab her neck, and bite hard on her ear.
“There’s no time for this Rob, just FUCK ME already,” she half yells.
I oblige, starting to pump in and out of her hot grasp, grabbing her arm behind her to get a better rhythm going. She squeezes my cock hard with her pussy, obviously meaning that I do really need to make this as fast as possible.
Being that I hadn’t had sex in a few weeks at this point, that was no problem. I fucked her hard and fast, and within five minutes, I was dumping my load in her, panting heavily and leaning on her as my cock kept pulsing.
“You never go soft do you?” she asked. “I wish we had more time, but you’re going to have to take care of that yourself, or just shove it back in your pants for now.”
Grabbing my chin, she pulls me towards herself, kissing me gently. Holding my still sticky cock in her hand, she looks me in the eyes and smiles, knowingly.
“If you get back together with Emily, I want you to know that you can still come visit me as often as you need, Rob. If she’s being a bitch, or not giving you any on the regular, and you need to cum, just come see me. I mean it. You can be as faithful as you want, but you’re seventeen still. You’ve been fucking pretty regularly, and you need to cum a lot from my experiences with you. So, if you ever feel the need, come visit. I’d spread these legs for you any time, sweety.”
With that, she pulled her pants up, but not before dipping a couple fingers in her pussy and bringing them out with both of our juices on them. Savoring the taste, she was still licking them after we had left the room and she was walking towards the stairs.
Later that afternoon, I had texted Emily concerning that evening’s plan, and was told to come over to her house around seven for dinner with her family. I showed up with flowers for Emily’s mother, hoping to lessen the blow of seeing my face for the first time since our incident almost two years ago.
“Hello, Rob, nice to see you!” Emily’s mother greeted me somewhat enthusiastically.
“Hi, it’s very nice to see you. These are for you,” I handed her the flowers.
“Oh they’re beautiful! I’ll go put them in some water – come in, come in!”
Honestly. I felt a little uneasy about this hello. The last time Emily’s mom had seen me, her daughter had my cum on her, and I was still mostly hard, standing completely naked a few feet away from her.
“Hey Rob,” Emily squealed, bounding down the stairs towards me. Jumping into my arms, she hugged me tight for the second time that day. She looked up for a kiss, but I turned away, motioning that her parents were standing right behind her.
“That’s ok, Rob, we know you two haven’t seen each other in a long time.” Her dad was staring at me coldly, despite the approving words he had just offered.
Dinner was relatively uneventful – I was polite as always, and explained that I was excited about my senior year starting the next day. I was lying, but I felt that it would be encouraging for them to know that I was very interested in school, and looking forward to getting into a good university. In reality, I got on the honor roll every year, but I never really put any effort into school. I did homework and paid attention in class, and that sufficed most of the time.
After dinner, Emily and I were still sitting on the back deck, although we had moved a little closer together, and I had my arm around her. We were kissing, and generally just being civil – keeping it decent, just in case anyone came back outside or was watching from a window above – until Emily leaned over and grabbed my cock through my pants whispering how much she had missed it since she’d been gone.
“You know I haven’t even fucked since I’ve been gone, Rob?”
“How could I know that, babe?”
“I missed you both so much,” she giggled.
“I missed you too. I knew I did, but I didn’t really know how much until I saw your face earlier.”
“Aww, that’s so sweet. We’re gonna have such a great year together, I promise,” she cooed in my ear. “You better get going soon, though. It’s getting late for a school night, and I have to at least try to make a good effort for the first day.”
“Alright, I’ll see you tomorrow then. It’s a date,” I winked to her.
Lying in bed that night, I couldn’t sleep. Normally the last night before school, I couldn’t sleep because I was dreading the hell that would be the next nine months of my life. This time, I couldn’t sleep because I was too busy grinning to nobody and thinking about how truly wonderful this year could end up being with Emily back in my life.
The next day, I woke up from just a couple hours of sleep, managing to find my way to school.
As I walked in the side door to the senior’s locker area, I got bear hugged off the ground from behind by my best friend Bill.
“Hey fucker, I heard Emily’s back in town! You gonna pick up where things left off?”
“I think we’re going to try and see how things go ya,” I laughed, as he carried me over to and threw me on the couch.
“What’s your schedule like, dude? Do we have any classes together?”
“Probably just music,” I replied, “unless you decided to stop taking sciences, or I decided to start taking them.
“Well engineering is going to be a bitch to get into, so I’m in if a course has AP available, I’m in it.”
“Have fun, man,” I responded. “I still don’t know why you want to be an engineer, but if you want to, good luck.
Bill had always been an athletic, good-looking guy. He was popular with the ladies, but also with teachers because he always made time from our goofing off to study and do exceedingly well in school.
“What are you doing after school?” Bill asked.
“I have that fucking band tryout.”
“We have to tryout for band now? I thought it was mandatory?”
“No, dude, the student rock band. They need a bassist because Kendra graduated last year,” I reminded him.
“Oh ya, I forgot you were doing that.”
I had started playing bass for fun in the spring of that year. I had always been musical, preferring it to the other fine arts at school, and was always the go to guy for the percussion section in our ensembles. I decided to start playing bass, and had practiced a fair amount – hopefully enough to get the part. My mentor had been nagging me towards the end of my junior year to get more involved at school in order to have more to put on my applications this year – student rock band was my first step.
I was putting my stuff away in my locker when a hand reached around me and covered my eyes. Spinning around, I grabbed the culprit and quickly saw that it was Emily. I pulled her in close and hugged her to me, which was the extent of what we were able to do in school. They had a very strict PDA rule, and a few of the older teachers made sure it was enforced to the nth degree.
“Are you ready for day one, babe?” She teased me.
“Of course, nothing would make my life more complete than another nine months of school,” I answered dully, as the first bell rang, warning us to get to class.
“I have law and history before lunch,” I told Emily, intending to tell her I’d see her during lunch.
“I do too!” She cut me off. “We should try to talk Mr. Halman into letting us go a few minutes early for lunch since it’s the first day back and we have such stressful lives we need to escape from,” she said as we walked towards our first class of the year.
As we walked out of class a few minutes before the lunch bell rang (Emily had worked her charms to get her way, as usual), Emily grabbed my hand and told me to meet her outside immediately so we could go get lunch before all the other people got out of class.
As I walked outside a minute later, her beauty floored me once again. She had taken off her dress shirt, and was wearing a super tight gray tank top with her kilt rolled up so you could see her panties clearly if she bent over.
“Let’s go, already,” she whined, wanting to get off the property as fast as possible.
As we climbed into my awesome minivan, I asked her where she wanted to eat, as there were a number of crappy fast food chains in the area, as well as a mall with a large food court only a few minutes away.
“Let’s go get street meat from the guy near the soccer field,” she told me.
Five minutes later, we pulled into the parking lot of the soccer field that our school leased for the autumn season. We ate our hot dogs, Emily seeming to scarf hers down like she hadn’t eaten in months.
Before I could even finish my hot dog, she grabbed my hand and pulled me back towards my van.
“Babe, I’m still eating,” I told her.
“Well finish up quick, because I have two years worth of horniness to get out of my system and we only have forty minutes until we need to get back to school,” she said, unbuckling my belt and fishing my flaccid member out.
As I finished my hot dog, Emily took off her tank top and unpinned her kilt, letting me see her beautiful figure. She had definitely gained a bit of weight in both of the right places, and was curvier than I remembered. Later she told me she’d finally broken a C cup, and was obviously proud about her curves.
I grabbed her blonde ponytail, and forced her to my quickly hardening cock. As I pulled my pants off, she had already managed to get me hard as a rock, and was fondling my balls at the same time.
She undid her bra and pulled off her panties all the while keeping me in her mouth, albeit sloppily.
“Babe, I hate to stop blowing you, because I think we’ve both missed my blowjobs, but I need you in me now,” she moaned.
I felt a momentary pang of guilt, remembering how she hadn’t had sex in nearly two years, while I was getting regular sex during the school year from the woman who had gotten her sent away in the first place, not to mention the twenty-odd other girls and women I had been inside since she had left.
Emily lay on her back in the middle of my van (I had removed the two bucket seats, so there was only two front seats and a back bench – a trick I had learned for those times when I drank too much and was not afforded the opportunity to sleep inside at whatever party we were at), beckoning me to her with her finger.
As I lay on top of her, and put the tip of my cock in, her long legs wrapped around me, urging me to fuck and fuck hard.
Emily had never been one for ‘making love’, so to speak – she was more interested in just having a good fuck since the first time we had done the deed. I had learned a few things since she’d been gone, however, and started to put them into practice, wondering where her objections might be, if they even existed.
As I drove my hard cock in and out of her incredibly tight pussy, I hunched over and grabbed her tit, biting her nipple hard, causing her to scream in ecstasy. She began to claw at my back, and probably would have drawn blood if I had taken my beater off.
After a few minutes of abusing her nipples, she asked me to fuck her from behind, which I was more than happy to do.
Getting on her knees, I got above her, with my legs in front of hers, and tilted my pelvis back to allow myself to hit against her G-Spot with every thrust. Her pussy walls were soon contracting as she came all over my cock, liquid dribbling out between us in the few spaces that existed.
Pinching her nipple, I grabbed her ponytail and pulled her back, causing her to arch backwards. Taking this opportunity, I bit her neck right above her collarbone, causing a second quick orgasm to erupt juices all over our legs.
“Holy fuck!” She wailed, feeling two years of sexual frustration quickly release during repeated climax.
As I was getting ready to shoot my load somewhere, she had her third orgasm.
“CUM IN ME!” She screamed at me, a departure from her usual preference of face or breasts – probably for the best since we had more classes in the afternoon.
Taking her cue, I unloaded what had to be a dozen strong shots of my semen into her throbbing, hot pussy. It felt like it as never going to end, and she was still quivering from her latest orgasm, as I continued to tease her nipples after my own orgasm had abated.
“Holy fuck, Rob, that was better than anything I remember in my life,” she gasped for air.
Leaning against the back bench seat, I grabbed a towel that was conveniently laying there, and started to wipe the sweat off my face and body.
Before I could wipe my cock off, Emily pushed my hand away, taking it in her mouth once more.
“Oh my God, we taste so good, babe,” she moaned.
In just seconds, I was rock hard again, and she was pushing the bench seat back, and straddling me.
“I don’t know if we have time for more, Emily,” I told her, glancing at my watch.
“I just need to cum once more,” she begged.
“So you want to cum again and I’ll just have a huge erection to hide in my pants for the next twenty minutes?” I laughed at her.
“Shut up and just do it, and I’ll make it up to you after school,” she said.
“I have band tryout after school,” I managed to get out before she clamped a hand over my mouth.
“We’ll figure it out, just fucking let me fuck you,” she yelled at me, getting a bit testy.
Only a couple minutes later, with me tweaking her nipples and slipping my middle finger into her asshole as she rode me, her pussy was contracting on my cock again.
Climbing off after a few minutes of recovery, she started to get dressed, apparently being quite serious that I would just have to worry about my own hard on for a bit.
Somewhat agitated, I managed to pull my pants up, my cock obviously showing throw them, hard as can be, and composed myself, hoping there would be some relief before I had to walk back into school.
As we arrived, there was no one in the yard or on the deck at the school, so we were more than likely late for our afternoon classes. Third class of the day and she already had one tardy – definitely not a good way to impress the parents, but oh well. I was confident she’d make up some bullshit excuse about getting stuck in a long line at Wendy’s or something.
Before we got to the side door, she quickly pulled me close, giving me a kiss and telling me she’d wait for me to finish my tryout so we could finish what I didn’t get to, which put a bit of a smile on my face, but did not help the fact that I was still incredibly hard. Because of the trousers we had to wear at school, as well as my size, it was exceedingly obvious that I had a massive erection.
Fortunately, the locker area and halls seemed empty as I walked in a couple minutes later.
Turning the corner to my locker, I had a sudden sense of dread, as I saw a few teachers standing in between my locker and myself. Trying to quietly walk past without rousing suspicion, one of the teachers noticed I was probably late for class.
“Tardy on the first day, Mr. Stenson, tsk tsk” he scolded me.
“Err… ya, I uhhh…” Lying was obviously not my thing, as I was more concerned with hiding the situation in my pants.
“Don’t worry, Mr. Edinct,” I heard a familiar voice say from out of sight, “I’ll deal with him.”
Mrs. Curtis got up from a chair that was facing the other way in the senior lounge area, and told me to get my books for the next class and that I would be there momentarily after she had a word with me after the merits of being on time.
“Just follow me to my office, and I will write up your tardiness and you can be on your way,” she told me, walking away before I even grabbed my books.
Grabbing my books, I jogged to catch up to her, my still hard penis pushing against the restraint of my pants. I knew this was not going to be a pleasant interaction. Walking into the gym office, Mrs. Curtis shut the door behind me.
Sitting down at her desk, she starts writing on a piece of paper. Looking up at me, she asks why I’m late.
“I lost track of time is all. I was out for lunch,” I explain.
“It must have been a very exciting lunch,” Mrs. Curtis laughed.
“You’re hard as a rock, and the way Emily looked when she walked in, you two probably spent the whole time fucking!”
“Well… uhhhh,” I stammered, unsure of what to say.
“It’s ok, I understand you young people, especially with what she gets to use,” she says, a twinkle in her eye as she stares at my groin. “I just can’t believe you’re still hard – you last longer than even I know, apparently.”
“Well she didn’t quite let me finish because we were going to be way late,” I managed to find my voice again.
“She left you all hard with nothing to do?”
“Well, we did fuck, and I came, but she started again, and came, and then we had to get back to school,” I described the last fifteen minutes.
“It’s a shame to let a nice hard cock go to waste… why don’t you come over here, Rob, and let me help you? The offer still stands, of course.”
“I don’t think that’s a great idea. Is it ok if you just write that tardy slip and I’ll get to class?”
“That’s fine with me. You don’t need a tardy slip, though. I’ll just explain that you were helping me do something and I needed you to stay a bit late. It’s going to be awfully embarrassing walking into your class with that tent in your pants, though,” she laughed at me.
“Well if it’s alright, maybe we can wait here for a couple minutes until things subside?”
“If you think you can stop from staying hard in here, be my guest,” she says as she leans back in her chair and spreads her legs, rubbing her hand on her pussy through her pants. “Don’t mind me, Rob. I can wait for a while,” she says slipping her hand inside her pants.
“Oh fuck,” I whisper to myself, realizing what’s about to happen.
After a minute passes, she asks if I’m ready to go, obviously phrasing the double entendre.
Closing her eyes, she starts to moan softly, and my cock starts to hurt from the pressure of the pants as well as the need to cum. Conceding defeat, I pull my cock out and start to stroke it.
Mrs. Curtis opens her eyes and wheels the chair over, taking the tip in her mouth – one day with my girlfriend again and I’m already the worst boyfriend on Earth.
“Mmmm,” she moans over my cock. “She tastes good, Rob,” she grins at me. “I don’t think we have time to really get into this, so let me just take care of you quickly, sweety,” she says and quickly devours my cock.
Moments later, I was cumming for the second time in the last half hour, and feeling guilty.
The rest of the afternoon was pretty boring, but my audition for the bass player in the student rock band went great, and I ended up getting the part on the spot. As I walked out of the audition, I headed to my locker to grab my bag, and to look for Emily, as she was probably expecting a ride home. It took me ten minutes, but I finally tracked her down in the library, doing some homework while she waited.
As we got into the van, she leaned over, and started to rub my cock through my pants, which I quickly stopped.
“I’m not feeling too well, Em – I think that street meat isn’t sitting very well with me,” I told her, which was a lie. I was still a little irritated with what had happened during our lunchtime tryst, as well as mad at myself for allowing Mrs. Curtis to manipulate me so easily. “I’m just gonna drop you off and head home, if that’s ok?”
“Of course, babe, I hope you feel better. I feel fine though, so maybe you’re just unlucky.”
“Must be something like that, ya,” I muttered, as I concentrated on navigating the rush-hour traffic.
One day in, and I could already tell that this year would be just as long as any other.
Author Note: If I get positive comments I'll consider continuing to write about my adventures in sex. This is not to force people to vote positive and leave good comments, but I'm not going to keep spending my time doing it if people aren't enjoying them. Also, I realize it's been like 2 or 3 years or something since my last story, and I apologize - life has been messy for a while now.
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