Midnight Fantasies

Fantasies. They are deep. They are dark and dirty. They drive us wild and make us to do things we normally would never do. They make us think what we don't want to think. They often come at midnight, when we are alone, lying in bed. They give us the pleasure we crave. Welcome to Midnight Fantasies. Here we will explore your deepest, darkest fantasies and bring them to life. Today I will show you one of my own dirtiest and oldest fantasies. Are you ready to shock your mind?

MAKING THE GRADE

I was on the verge of failing history. Yes history! I couldn’t believe it myself. How could I let things get so out of control? My parents would kill me! I could not let this happen. I did not want to let my junior year of high school end this way. I was desperate to do anything, stay after school or do extra credit, anything to avoid failing. I decided to go talk with my history teacher, Mr. Dawson, after school. There wasn’t too much time left in the quarter and I wanted to squeeze in as much extra credit as possible. Mr. Dawson was the nicest teacher in school and everyone loved him. I’m sure that if I talked to him, he would offer some sort of help. At this point, I was desperate and would do anything.

My last class was gym. Since it was warm outside, I didn’t bother changing and stayed in my gym clothes, which consisted of black basketball shorts and a red sleeveless shirt. As I walked out, I slipped on some equipment and fell right on my right shoulder. It hurt like hell. My friends helped me up but my shoulder really hurt. Anyway, I got so tied up with my fall and messing around with my friends that I didn’t get to his office until 3:30. To my dismay, he wasn’t there. I did see his secretary though.

“Hey Ms. Jones, have you seen Mr. Dawson?”

“Oh Jay, I’m sorry honey but he doesn’t have any office hours today,” she said.

Shit! I thought. I really needed to see him.

“Oh man, do you know if he is anywhere on campus? I really need to talk with him.”

“Actually, he decided to workout at the fieldhouse today. If you hurry, you may catch him before he finishes up and goes home,” she said.

“Thanks Ms. Jones!” I said relieved. I turned around and ran to the fieldhouse, which was located by the football and baseball fields behind the school. It was basically a full gym with all the necessary equipment and locker rooms. A lot of teachers and students would use it on a daily basis.

It was a nice May afternoon. The sun was shining and the sky was beautiful. Because of this, most of the students and teachers had left and the parking lot was mostly empty. I ran to the fieldhouse and went inside. I walked over to the exercise rooms, looking for Mr. Dawson. I finally found him on a treadmill. As I walked towards him, I noticed how sexy he looked. Something inside of me stirred. I was anxious of being alone with him in the gym. I realized he really was an attractive man. He was in his mid-30s, about 6'2", very muscular, with dark eyes and hair. He was wearing running shorts that went up to his thigh, showing off his hairy, muscular legs and thighs. He also had a tank top that was tight on his body and showed off some of his hairy chest, another feature of his I lusted after. He just looked so hot with sweat running all over him.

“Hey Jay, what brings you around here at this time?” he said.

“Hi Mr. Dawson, I know this is a really strange thing to come all the way here to ask, but I need some help regarding my grade in your class.”

“Ohhh I see, Jay,” he said as lowered the speed on the treadmill.

“As you know, I’m really close to failing and I don’t want that to happen. I wanted to know if there is anything I can do for extra credit so that my grade won’t be so low and I at least pass.”

“Yes Jay, I have realized that you have slacked off lately and I was pretty surprised. You were such a great student early on, what happened?” he asked. As he spoke, I could barely keep my eyes off of his body. He was so hot! His chest had me hypnotized. I loved the V shape of his torso and how it led down to that bulge in his shorts. I wonder how the rest of his body looked. I was just in awe of him. I could feel me cock begin to stir in my shorts. When I realized, he had asked me that question, I quickly snapped out of it and looked up to his face. I think he had noticed because he was looking at me with a funny smile.

“I….I…I’m not sure Mr. Dawson, things just happened I guess,” I managed to say.

He then turned off the treadmill and walked off. He grabbed his towel and wiped his sweat. “Listen, I’m actually finished here but I still need to clean up before I go. Come with me and we’ll talk.”

“Ummmm, ok,” I said. Did he want me to go in the locker room with him? Oh my god, I thought, what the hell was going on? Will I get to see him change? My cock began to get semi-hard at the thought. I had to use my book bag to cover it up.
He walked up in front of me and put his hands on my shoulders. A chill went through my body as I felt him touch me. I just didn’t know what to do, how to stand, where to even look. My mind was racing. My heart was beating so hard I thought it was going to burst. I even began to sweat. He was barely a foot away from me. I could see his body up close and it got me even more horny.
“Look Jay, I know you are a young kid and all you think about is girls, your friends, partying, and all that. I completely understand because that’s what you should be thinking about at your age. However, if you want to get your scholarship, and get into a good school, you need to prioritize and put your schoolwork first,” he said.
“I know Mr. Dawson,” I said quietly. I had my head down and was looking at my shoes. I was so nervous.
“Look at me Jay,” he said. I looked up at him and stared into his eyes. I just didn’t know what to do. I was gripping my book bag tightly. I could feel tingling in my cock.
“I have seen you since you were a freshman and you are growing into a great young man. I want to see you succeed and you shouldn’t let things get in the way of school,” he said.
“I know,” I responded.
“Alright then, come with me. I’m sure I can find a way to help you with your grade," he said, smiling. He put his arm around my shoulders and we walked together to the locker room! I could not believe it! I was going to see him naked! I didn’t know if I would be able to control myself. My mind just raced, going 100 miles per hour as we made our way to the locker room.
“Uhhhhh, Mr. Dawson, I can wait here while you get ready,” I said, as we approached the entrance to the guys’ locker room.
“That’s alright Jay, you can come along. Didn’t you just get out of gym class? You look like you could use a shower,” he said.
“Well, I don’t know….” I said.
“Come on, we’re both two normal guys. We’ve known each other for a while now. It’s not like we need to be shy, right?”
Needless to say, I was convinced. “You’re right Mr. Dawson, let’s go.”
“Great, follow me. You can put your stuff in my locker right over here,” he said.
I did as he said and put my things in his locker. He then started to undress. I watched as he first removed his shirt, exposing his hairy chest and stomach. I was absolutely hypnotized at the site of him shirtless. He had a strong chest and flat, six pack abs. He really kept in shape.
“You like what you see Jay,” he said. I freaked. I guess I was too obvious in checking him out.
“Ohhh, my bad Mr. Dawson. I just couldn’t help but notice that you keep in pretty good shape. You generally don’t see that with most teachers.”
He laughed. “Very true, Jay. And yeah, I guess I have managed to keep in shape. I just like to feel good about myself.
I then pulled off my shirt and sneakers. “You look pretty good there, yourself Jay.”
I could feel myself blushing. “Thanks, Mr. Dawson.” I then reached up to put my stuff in the locker and I flinched from the pain in my shoulder, a result of the fall.
“What’s wrong Jay?” he asked concerned.
“Oh nothing, I just fell earlier and my shoulder is killing me,” I explained.
“That’s too bad, does it hurt a lot?”
“Yeah.”
He then pulled down his shorts and I noticed that he was wearing a black jockstrap. Oh my god, he looked so sexy. I couldn’t help but look at that bulge and wonder what that trail of hair led to.
“Jay, since you are pretty sore, let me rub your shoulders for you,” he said.
I didn’t even get a chance to object because almost immediately, his hands were rubbing my shoulders. His strong, bare hands felt so good against my bare shoulders. I couldn’t help but let out a soft moan.
“How does that feel?” he whispered softly.
“Ohhhh, that feels so good Mr. Dawson. You’re pretty good at this,” I said.
“Thanks, I’ve never gotten any complaints,” he said. His hands slid down my arms. They were no longer massaging me normally. It was very soft and almost sensual. I felt so nervous, hoping I wouldn't get hard or anything. That would be so embarrassing.
“One second, Jay,” he said.
He then moved in front of me and pulled down his jock! I was right in front of his cock! It was semi hard and he was leaking just a hint of precum. His bush was neatly trimmed. I was in awe of his cock. It was really thick and long. He must get pretty big when hard. This was turning me on so much, my cock started to get hard. I just couldn’t help it anymore. I quickly turned away so he didn’t notice.
“Wait, why don’t you get more comfortable?” he asked, pointing to my shorts.
“Oh,” I hesitated for a moment. I was starting to get a bit more uncomfortable.
“Come on Jay. I’m nude too. Plus, the massage will feel so much better.”
“”Ok Mr. Dawson, I guess you’re right,” I said. I then pulled down my shorts and underwear. My semi hard cock flopped out in front of me.
“Well, well, well. Look at what you’ve been hiding,” he said.
I blushed. No other guy had ever complimented me or looked at me the way he did right now.
“Seriously, Jay, you really have a great body. I wish I had a body like this at your age! The girls must be all over you!”
I laughed. I was feeling much more at ease. “Thanks Mr. Dawson. I guess I do have my share of fun.”
“I bet you do.”
He then started massaging my back again. Oohh, man, this felt so good. His strong hands then moved up and down my back, squeezing and pushing into my muscles. I let out a faint "mmmmm" as he squeezed into my back, harder and harder. He was breathing heavily, and I was too. I could sense something else was up when he hands moved over my shoulders rubbed my chest. His hands caressed my nipples and I moaned some more. I then was startled when I felt something rubbing against my back. It was his cock! I knew it was. He was rubbing his cock up against my back! I could feel how hard it was and I could the wetness of his precum. He just continued rubbing my chest.
“Ummmm Mr. Dawson, I don’t think we should do this,” I said.
“Shhhhh…just be quiet,” he said. I don’t know why but I listened.
He continued rubbing my chest. He thrusted his hips against my back, causing his cock to rub up against me more. I could feel his precum trickle down my back. My own cock had gotten rock hard. I swallowed hard, completely nervous with what was going on.
“Does it feel good?”
“Yes.” I said.
“Maybe we should talk about that extra credit now,” he whispered into my ear.
“Ok, Mr. Dawson,” I said. “What do you want me to do?”
“I think you already know Jay,” he said.
He stood up and walked over in front of me. His hard cock swayed in front of him. I could see a drop of precum forming at the top.
“ I don’t know Mr. Dawson,” I said innocently, nervous about what he really wanted.
“I want YOU,” he said. His deep brown eyes stared at me intensely. “I want your hot cock in my mouth. I want to suck you off and have your hot teen cum shoot down my throat.
I stood up from the bench. I just couldn’t believe what he just said. “I’m sorry Mr. Dawson, I can’t let you do that.”
“Oh really, well your cock says something else,” he said, pointing at my cock.
“Uhhhhhhh…I…..”
“Listen, let me put it to you this way, you either suck my cock or I fail you. Simple as that.”
I swallowed again. I was totally scared. I really didn’t want to fail. Part of me did want to suck his cock but another part of me wanted to turn around and run away.
“Well?” he asked impatiently.
I figured that it really didn’t make a difference. It was just a blowjob afterall.
“Ok Mr. Dawson, you can suck my cock,” I said.
“There you go,” he said as we walked up to me. “Now you’re going to earn those extra points,” he said, falling to his knees. His hand slid up to my thighs. He started rubbing them intensely, working his way into my inner thigh. I shuddered at how good it felt. His hands moved higher and I felt him slightly brush my balls. I let out a soft moan as he did this. He kept rubbing that area. Then he moved his hands to my ass. This felt so incredible. I let out a louder moan this time so he knew that I was enjoying what he was doing.
My cock was rock hard by now and I felt his hands slightly parting my cheeks and his fingers getting close to my asshole. This was probably the most erotic moment of my life. I felt one of his fingers getting really close to my hole. That freaked me out.
“No Mr. Dawson, not that,” I said as I pulled away.
“Jay, I thought I made myself clear, either you let me have my way with you or I fail you,” he said.
I sighed and walked back to him. He placed his hands on my ass again and spread my cheeks. His finger was right at my hole again. I had to admit that it felt really good. I moaned even louder. He started circling my hole and I shivered at that intense feeling. I could feel some precum oozing out of my cock as his finger started entering my hole.
“Ohh my god," I said as his finger entered my virgin hole.
“You like that, don't you Jay?"
“Please stop Mr. Dawson,” I said.
"You know you want it Jay. You know if feels so good,” he said.
He kept going, moving his finger in and out, in and out. His finger was rubbing my inside, sending such pleasure throughout my body. I was surprised that I felt myself almost ready to cum. I was moaning and even moving my hips a bit. Then, he suddenly stopped and pulled his finger out. I was worried about what was coming next.
I looked down and I saw he was rock hard. His cock was huge! It had to be at least 9 inches. He looked up at me and said, “Don’t worry Jay, you’ll get to have some fun with it soon,” he said. He then kissed my thigh very softly. I twitched a little but he grabbed me by the waist and held me tight. He kissed up my thigh, my waist, and my stomach. He then stood up and leaned in right in front of my face.
"Damn, Jay. You are so fucking hot. I promise you will earn all the credit you need." HE grabbed myhead and leaned in to kiss me. I pulled back and he missed. He yanked me close and tried again. Our lips met and he started to kiss. I was surprised by how good it felt. I opened my mouth and let his tongue in. His tongue met mine as we shared a very passionate kiss. We continued to kiss as he grabbed our cocks together in his hand and jerked them off.
Mr. Dawson then broke away and started kissing my neck. He went down with his tongue to my chest and started sucking on my nipple while his hand squeezed the other. I moaned softly. No one had ever touched me like this before and it felt great. He was so good at what he was doing. His mouth was expertly sucking at my nipple first my left, and then the right while his hands squeezed the other.
I moaned some more as he started kissing his was down my abs. I instinctively put my hand son his head and my hands ran through his soft black hair. He got closer and closer to my cock as he reached my pubic area and buried his face in my pubes. He grabbed my cock in his strong hands and looked at me as he started to softly jerk me off. He leaned closer and started to softly kiss it. An intense feeling came over me. I wanted his mouth on my cock badly. I tried pushing his head further down.
His tongue licked right under the head and this felt so awesome. His tongue worked his way up and down my shaft as his hands held on to my thighs. He went down and started sucking on my balls, paying attention to each one. I was moaning so loud, I didn't care if anyone would hear. He continued this for a while, sucking on my balls, licking the shaft. I was in absolute ecstasy and my mind was racing at all the feelings I had. I was moaning and I wanted him so bad.
“You like it, don’t you?” he asked.
“Yes, Mr. Dawson, I love it,” I said.
Then, he pulled my cock deep into his mouth swallowing it whole. The feeling was great. I had never felt a blowjob as intense as this one. I felt a wonderful sensation as his hot mouth sucked my cock over and over. His head bobbed up and down, the wetness of his saliva and my precum dripping down his chin. I really got into it now. I put my hands behind my head and began thrusting my hips, moaning and saying his name over and over. I felt the beginning of an orgasm as he slipped a finger into my ass again. That did it and I started to cum!
I yelled out as my cock burst and shot rope after rope of cum into his mouth. He drank up all of my hot cum. Not one drop went to waste as he licked it all up. The orgasm was so intense I thought it would never end. I had never experienced something like that before. Once he finished, he stood up and kissed me again. I could taste some of my cum on his lips.
"Ohhhh baby. I knew you would love this," he whispered softly into my ear.
"I can’t believe it Mr. Dawson. No girl has ever done it to me that way."
"And that is just the beginning Jay. So far you’ve gone from a D to a C+. I think it’s time for you to move up to a B," he said.
He kissed me again. This time, I didn’t pull away and kissed him back. I placed my hands on his chest and ran my fingers through the hair on his chest. I loved how soft the hair felt on my hands. Then I started running my tongue down his chest, the hair felt so hot on my tongue. I went down to his cock and could smell his manly, musky scent. His cock was so hard and precum was dripping all over it. I licked the glob that had formed on the head. It tasted like mine, nice and sweet and he slightly moaned at this.
“Yeah baby, suck on your teacher's cock. Take it all in your hot boy mouth."
“But I’ve never done this before,” I said.
“Don’t worry, I’ve seen you in class. You’re a fast learner,” he said as he pushed my head down to his cock.
I grabbed his cock and stuck the head into my mouth. He let out a soft moan and that started getting me hard again. I swirled my tongue all over it as I continued mving his cock deeper into my throat. I gagged a bit, but I quickly got used to it. My head bobbed up and down slowly at first. My tongue was all over his mushroom head. I just couldn’t believe it. I was sucking my teacher’s cock!
"Faster!" he yelled. I started moving faster and faster. All you could here were his moans, my sucking noises and my muffled moans.
He moaned loudly. I put my hands on his ass and rbbed his cheeks. I parted them and found his hole. I started rubbing it with my finger.
“See, you are a fast learner,” he said.
I then felt more confident and stuck my finger all the way in. He let out a loud scream and said, "Oh baby, get ready!"
His body tensed up and then his cock pulsed and released ropes of cum into my mouth. It tasted so awesome! I never had tasted another man’s cum before! He moaned very loudly and thrusted his hips as the cum poured out. There was so much of it that it trickled out of my mouth. So I pulled out and licked up the rest. I really wanted those extra points so I did just like he did and drank it all up with not one drop going to waste.
When he finally finished, he pulled me up to him, taking me in his arms and giving me a very deep, passionate kiss. His arms held me tight around my waist and my body felt so good against his hairy chest. I could feel our heavy breathing subside.
He then asked, "So Jay, you want to go for that A?"
Oh no, I thought, what could he want now. “Uhhh sure Mr. Dawson, what do you have in mind?”
"I want to fuck you," he said rather bluntly.
I pushed him away. “No way! That’s where I draw the line, Mr. Dawson. That’s just too much to ask.”
“Come on Jay, you’ve come this far, I promise to go easy on you. I know you want that A,” he said.
He was right. I wanted the A more than anything. “Fine.”
“Let’s go to the shower,” he said. He grabbed my by the hand and pulled my towards the showers. He turned on the water and waited for it to get warm. We then both got under the showerhead. The water felt so good on my body.
He took my hand and told me to get on all fours. I did as he said and he kneeled behind me as the water fell on our bodies. He then reached to my ass and slid 2 fingers into my hole. It hurt a little but then felt great.
"Ok baby, I'll start with just the head and then slowly work my way in."
He grabbed hold of his hard cock. He guided it to my hole and slowly slid the head in. The pain was incredible as I let out a loud yell. He held my hips and continued sliding in. Half of his cock was in and he asked if I was ok.
"It hurts Mr. Dawson, please stop" I said.
“Don’t worry Jay, it will feel better, besides you want that A right?”
“Yes sir,” I said meekly.
With that, he took his hard, thick cock and slid it all into my no longer virgin ass. I felt his pubes tickle my smooth ass. I screamed as I felt a sharp pain go through my body. Tears came out of my eyes. He massaged my thighs with his hands, telling me not to worry that the pain will stop.
He started slowly thrusting, moving his cock in and out very slowly. The pain continued throughout and I was yelling in pain and squirming. He continued thrusting and groaning, telling me my ass is so nice and tight. After a few thrusts, I was surprised that the pain subsided and I started feeling intense pleasure. My cock got harder and precum started to drip onto the floor.
I really started to like it, yelling at him to go harder and faster. His thrusts increased. They were short and fast. His balls were slapping against mine. I figured out a rhythm that allowed me to meet his thrusts. We were definitely fucking now and both of us were screaming in pleasure.
"I'm cumming baby!" he yelled out and released his hot cum into me. The first spurt triggered my orgasm and I started to cum on the shower floor. It seemed like we were both cumming forever. He eventually softened inside of me and pulled out leaving me with an empty feeling. We both stood up and he kissed me again and held me in his arms. My head was on his shoulder and my hand stroked the wet hair on his chest again.
He then pulled away and said, “Congratulations Jay, you have an A in my class.”