Malcolm was super happy that one of the prettiest girls in the class wanted to go out with him. However, it was strange that she didn’t want to be seen together with him in public AND she wanted him to do her homework for her. It didn’t take long for him to face the painful truth and feel used. Luckily, mommy was there to make him feel better.
My heart beat with silent excitement. Tanya’s room smelled amazing. She carried her scent and her perfume that she wore on a daily basis. Her bed felt so soft and bouncy, and crazy thoughts ran through my mind. I was wondering if we were going to take it to the next level in a bit.
Tanya and I had only dated for a few weeks. I took her to the movies, for walks in the park, and even bought her some gifts.
Maybe this is how she will deepen our bond… I mean, I didn’t come to her house just to wait for sex. Okay, maybe she expected it, but it wasn’t my only reason. You can’t blame a healthy eighteen year old virgin boy for being a little turned on.
Tonight, I could finally become a man.
The door opened and Tanya entered. She smiled and pushed back a strand of hair.
I smiled. “Hey you.”
He pushed the door behind her until there was a sure, satisfying click.
“So what is going on?”
“I was hoping you could do something for me.”
“Yes?” I asked, trying to contain the anticipation bubbling up inside of me. “You know she would do anything for you.”
She opened her closet and reached in, which she hoped was a good sign.
“I was hoping you could help me with my history dissertation.”
She dropped a stack of folders on the bed.
“Hey, is he okay?” I flipped through the folders and frowned. You have barely started.
“I know, right? Malcolm, baby, you’re the only person who can help me with this,” she said, looking at me with puppy dog eyes. I’m not going to lie, the fabulous dick swapping family foursome in exclusive xxx moment she did that, my resolve crumbled faster than a sandcastle preparing for a tornado. He knew that he essentially shouldn’t be doing all of her homework for her, but… Those eyes.
Her hand closed over my kneecap, giving me a squeeze. “Please?”
I sighed. “Okay, I’ll give you a hand.”
“Great! Oh Malcolm, you have no idea what this means to me. I promised Sandy I’d go to the Furious Boys concert with her this weekend! Now she better think about getting the right outfit.”
“But what about your dissertation?”
“You don’t mind, do you? I mean, if you did it for me just this once, I’ll make it up to you.”
Okay, so I sucked. She gave me her portfolio and while she was partying with her friends this weekend, I had to prepare her dissertation for her. Good thing I’ve already done mine so there will be plenty of naughty paraphrasing and she’s got something ready for class on Monday.
I quickly greeted mom when I got home, determined to finish the project. She asked me if I was going to have dinner with her, but I didn’t even want to waste that precious hour.
I literally burned the midnight oil from Friday to Monday morning.
My mind and body were tired, I was on the verge of total exhaustion. But it was great. It was going to be totally worth it.
I felt like royalty when I walked into class and handed Tanya the entire dissertation.
“There you go, the basic principles and arguments are in line with mine, so you’ll definitely get more than a passing grade.”
She gave me that megawatt smile and took the folder from me. “Thank you Malcolm, you are the best.”
I leaned in to kiss her and she gave me a hug. Her friends looked at us and smiled.
They probably thought we were a cute couple.
“So, uh, how are you going to reward me?” I asked, barely able to contain my smile.
I’ll talk to you after class, okay? You’re going to love what I have in mind.
Constantly looking at the clock was probably one of the dumbest things you could do when you wanted time to pass quickly. And that’s exactly what I did because I was so fucking ecstatic. Oh boy, I was wondering what Tanya had in store for me. I did her a big favor, so her reward would be something substantial. Fortunately, I kept my lucky condom in my wallet.
After what seemed like a million years, classes were finally over. I texted Tanya and she told me to meet her at the bike shed.
Nice. That was one of the notorious connecting spots in the school. It wasn’t exactly romantic, but it will be a memory I will always cherish.
I waved at Tanya as I rounded the corner. She was waiting for me as she promised.
“Hey, Malcolm. Are you ready for your present?”
I licked my lips. My cock stirred at those sweet words. “Y-yes.”
“Close your eyes, first.”
A wide smile crept across my face. “The tensionis killing,” I chuckled.
Then my phone vibrated.
“Okay, you can open them now. Check your email.”
“What is this?”
I checked my emails and she sent me a discount code for a computer game. Five percent off any game over fifty dollars… “Uh, thanks, I guess.”
“I know you like computer games and I couldn’t think of anything better for you,” she said smiling.
I wrapped my arms around her. “ActUsually had a couple of ideas in mind.” I leaned in to kiss her, but she turned her cheek away.
“Oh Malcolm. I don’t think I’m ready for that yet.”
“Oh really? I just thought…”
“Oh no, you didn’t expect something sexual in return for helping me, did you? Please don’t tell me that’s what you wanted.”
I swallowed the bile of disappointment. “No, of course not. I wanted to help you because that’s what I do. I’m sorry, I didn’t mean to force anything, I thought we might be ready to take it to the next level, that’s all.”
She pulled out of my arms and smiled. “It’s okay, Malcolm. If it’s okay, I’d like to take things slow. If we rush things, it’ll end up being messy and full of regret, you wouldn’t want that, would you?”
“Of course not.”
“Great. I’m glad we’re on the same page. I’m meeting Sandy now. You don’t have to come, it’ll be boring girlfriend stuff.”
I was glad she left. Damn, the disappointment was crushing. My balls didn’t give a damn about my feelings though. I spent the whole day. No, all fucking weekend fantasizing about what was going to happen and now it didn’t. I didn’t even masturbate, thinking that I wanted his first impression of me to be a good one, that my first cumshot wasn’t pathetic drool.
And now he was failing like a son of a bitch.
I went home with a mix of lust, sadness, and shame coursing through me. Maybe Tanya was right and I was overthinking my penis.
“Hi honey, how was your day?” Mom asked when I passed by the living room.
“Fine,” I said, heading straight upstairs because Mom was always so cheerful and I wasn’t feeling particularly happy at the moment.
I tossed my bag aside and slammed into the bed, staring straight up at the ceiling.
What the hell was he doing?
I wanted to believe that there was something between Tanya and me. But deep down I had the unsettling feeling that it wasn’t meant to be. The weakest, most pathetic part of me wasn’t ready to face that truth yet.
Still, she was so damn pretty. With those full lips and large almond eyes… My penis throbbed with need. Shit, I haven’t jerked off all weekend, and on top of my tantric-level tiredness and expectations, my dick demanded to be satisfied.
I might as well delete one and fucking go to sleep.
I took off all my clothes and got nice and comfortable in my bed. I had a nice collection of videos saved on my phone, and for this particular moment, I started playing one with a cute blonde who is grateful to her huge nerdy classmate for fixing her laptop.
My dick was pretty hard. My balls were filled to the brim with cum, and all I wanted was to relieve them. I grabbed one of my trusty socks and put it on my penis.
“Fuck. Tanya…” I moaned, grabbing my flesh. My shaft throbbed painfully as she milked the cum out of me. I tried to remember Amateur Thai teenager bargirl Poohpea wants euro seeds in doggystyle what her bedroom smelled like. Of a teenage girl with the scent of her, deodorant and other strange smells that a guy like me wasn’t familiar with, but it all smelled distinctly feminine and wonderful. I imagined what it would be like to be on top of her, in her own bed while taking her virginity.
That we gave each other our first times…
“Fuck,” I hissed. My balls tightened. It wasn’t going to take long.
“Honey, I bought you some hot chocolate. You looked a little down, so-“
Mom gasped when she came in – unannounced – with a tray of chocolate and cookies.
Pure terror washed through me. There was no mistaking what she witnessed. I wanted so badly to go back ten minutes ago and decided to masturbate under the covers, but no, I just had to enjoy the feeling of being completely free and naked.
Mom placed the tray on my dresser, quickly pushing aside some manga and DVDs for space. “Sorry, I should have called. Sorry to come in with you.”
She turned and left before she had a chance to speak.
Just when I thought the day couldn’t get any worse, now my mom caught me hitting the meat… I didn’t finish, my adrenaline spiked and panic crushed my libido.
The only thing he could do was go take a piss, come back and at least enjoy the cocoa and the cookies.
She turned me on and before I knew it, I fell asleep.
My dreams were shaken and all jumbled. I dreamed of being horny, frustrated and accused of plagiarizing my history thesis. I asked Tanya toset the record straight, but all he did was act innocent. Then I ran home to mom and she told me that she would reward me for working so hard with a good blowjob.
“Sweetie?” I heard mom’s voice calling me.
I took a deep breath, the tendrils of sleep still gripping me tightly.
“Honey, wake up,” Mom said quietly.
It was still dark and I blinked awake. “Mom? What time is it?”
“Sorry, honey, it’s still late. I wanted to apologize. I shouldn’t have left like this. I was… embarrassed, I guess.”
“Sorry to embarrass you like this, Mom.”
“Not you, honey. It’s perfectly natural what you were doing. I should have been more mature about it. Can we talk you through?”
I’m not going to lie, I didn’t want to make the whole conversation awkward with mom, but at the same time I wanted to clear things up. “Yeah I guess.”
She smiled. My dream was barely over and I couldn’t help but notice how hot she looked in her camisole. It was a silky purple thing that fell softly over her body, clinging to her curves. Especially her breasts. Even in the dim light of my room, I could see her big, juicy nipples pushing against the fabric. My cock pulsed in complaint. I didn’t finish earlier and now the slightest stimulation was wreaking havoc down there. Even if it was my own mother.
Don’t get me wrong, mom was beautiful. A total milf, as they say. But she was my mom, that meant she was off limits. However, my dick thought otherwise.
“Come on then, get up. It’s cold.”
She lifted the sheets. I managed to pull some of the fabric between my legs before she caught me with a boner. That would send arguments out the fucking window.
The bed creaked as another person’s extra weight pressed down on it.
“Where were we? Oh yeah. Mommy just wanted to apologize. You’re a grown man now and I need to start respecting your space.”
She was so close to me that she could smell the shampoo on her long hair and the heat that emanated from her body.
“Okay, mom. I just had a bad day. A bad weekend, more like.”
“What is the problem?”
I sighed. And then I mentioned Tanya. Our ‘relationship’ was a secret. He didn’t want people to jump to conclusions and he wanted to take things very slowly. I didn’t question it, I was just happy to be dating one of the most beautiful girls in school.
As soon as I started talking about her, more and more came out like a dam breaking, with water gushing out.
I could have gone into the details a bit, but I told Mom about the dissertation I basically slaved for her over the weekend, and her coldness. Meanwhile, Mom sat next to me, listening intently.
“I guess that’s it,” I told him. “So, for lack of a better way to put it, I’m tired and frustrated. And I guess things aren’t as rosy as I’d hoped.”
Mom looked deep into her thoughts. “I respect her for not wanting to rush into anything. But I don’t agree that she expects you to do her job. But after everything else is considered…I don’t think she likes you that much, honey. I know that’s hard, but That’s my honest assessment.”
I sighed. I had my suspicions, but what mom said made sense. “Well, I guess I wouldn’t have to wait for him to maybe do something with me.”
“You mean, sexually!”
God, the whole sex thing was still awkward to talk to her about. Dad was too busy to talk about the birds and the bees, and his contribution to the whole thing was, “You’ll figure it out, son.”
However, he couldn’t be too angry with him. He worked long hours to keep us afloat. I was not naive about it. Even now, Dad worked night shifts.
“Maybe I’m still immature. I know I’m a man now, but it’s hard to keep my urges in check. It wasn’t nice, waiting to finally have sex for the first time, and now those possibilities seem dashed.”
“Oh honey. Come here, a hug always makes things better.”
Maybe it was his body being so close or talking about things that relaxed me, but he was sporting a severe erection. I was hoping I could finally relieve myself once our talk was over.
“I-I’m fine, mom.”
“You don’t have to be a big man around me,” he laughed at her. Then she jumped up and wrestled and tickled me.
His soft, voluptuous body pressed against mine. Against my erection. Mom’s eyes widened immediately as she realized the situation.
“Sorry, mom. I’m not trying to be gross. Honest.”
“…it’s okay, honey. It’s okay, we can be mature on this. You’ve been extremely repressed. I get it. So, it’s nothing to freak out about.”
Her hand rested on my belly under the covers as if to calm me down, to show that he’s okay with me having a boner. But it only supercharged my desireeither. Mom was a pretty lady. Huge breasts, super nice and… Okay, fuck… I masturbated on top of my mom a few times in my masturbation career.
“No offense, but I do feel a little sorry for you, honey.”
“What do you mean, mom?”
“Just that… You’re eighteen, and you haven’t done anything with a girl yet?”
The heat burned my cheeks. “Y-yeah…”
“I just wish you had more experience now.”
Great, even my own mother was laughing at me.
She looked at me, stroked my belly in slow, deep circles, and continued. “Is there anything mommy can do to help you?”
My cock throbbed. But he knew she didn’t mean it that way. She did? “I don’t think so, Mom. It’s just life. I’m not good with girls and I hope that by the time I get to be with one intimately, I don’t screw it up too much.”
Her hand swept lower, dancing closer to my crotch. My cock pulsed to life. Shit. “Sure you don’t have anything in mind?”
I resisted the urge to flex my hips, to rub my throbbing erection against her.
“I was thinking, Malcolm, maybe I can help you give you those experiences. So when you have sex with a girl, you’re more prepared.”
A low moan escaped my lips as her fingers gently pushed against my obvious erection. “M-mom…”
“You’re frustrated, honey. I can tell by the way you look at me.
“It’s okay, honey. I don’t care if you feel this way about me. I just don’t want it to ruin you.”
“I don’t think you’ll ruin me, Mom. You’ve always been here for me. I know you wouldn’t do anything to hurt me.”
She smiled. “Mommy just wants to take care of her son, that she feels good.”
As if to prove her point, her fingers wrapped around my cock, grabbing me through my boxers. My cock jerked desperately, happy that she finally had some attention other than my own hand.
“M-mom..!” I yelled.
“Would you like mom to help you drain your balls?”
“God, please, mommy,” I pleaded.
Before I knew it, she pulled the covers back, exposing my erection. She moved, and then the heat of her breath seeped through my underwear, right against my cock.
“Oh my God,” I gasped, and instantly, my hands were on her head. My hips jerked, trying to chase the feel of her, trying to press her sweet mouth against my cock.
She moaned sending vibrations through my boxers and through my aching cock. Masturbating didn’t feel like that. This was something completely different.
I let out another moan, just enjoying the exquisite sensation of Mom’s breath teasing me, driving me insane with desire.
“Please m-mommy,” I begged.
Her shoulder moved, and then her other hand disappeared between her legs, under her shirt.
“Sorry honey, I don’t think I’m ready to go all the way with you. But at least I can help you cum.
Mom rarely used profanity, so the words sounded more taboo to my ears.
The suction around my penis tightened, and I’m sure she pulled out a bit of saliva, moistening my crotch.
“Fuck,” I hissed.
Her hand was on me again, stroking me through my boxers, making my cock so stiff it throbbed painfully against the fabric.
I never felt anything like this before. I needed to come so badly, but I didn’t want it to end.
Her palm brushed against my shaft, up and down in slow, tortuous motions. “Just let mommy take care of everything. Forget about that girl now. It was too much for my virgin cock, pushing me to the breaking point.
“M-mom…” I moaned. She felt so good, but so bad at the same time.
“Are you feeling alright, darling? Do not stop. It’s important to let it all out.”
My balls tightened. I was so close. So fucking close.
“Mom, I’m almost there.”
“Are you going to run? Is my hand going to make you shoot your load? The tip of my penis peeked out above the band of my briefs. Mom seemed obsessed with it, her hand rubbing against me faster and faster.
I swallowed hard, my throat tightening as that familiar sensation in my balls stung. That sweet warning sign.
“I am going to run. Damn, mommy, I’m going to cum,” I groaned.
The sweet touch of her hand suddenly moved away…
…and my cock disappeared into my mother’s mouth.
“Oh, God, Mommy!!!”
She moaned, pulling down my briefs so she could grab my shaft, milking it up and down with her fingers. My toes curled and my finger sank deep into the sheets, completely transfixed by unimaginable pleasure.
Shit, my own mother was sucking my cock… Dawn’s realization was short-lived, though. Between the wet tightness of her mouth, the silky-smooth grip of her fingers, and the desperate need to come, I wasn’t going to last long.
“I’m sorry, mom,” I moaned.
Her moans pulsed through me, and I saw her movements become more active between her legs.A burning need surged through me, and I fought to contain it.
“I’m going to cum…! Mom, I’m going to cum!!!”
My whole body tensed, as if everything was inside me. compacted into a laser focus, ending at the very tip of the cock. My penis swelled in Mom’s mouth and with equal parts horror and pleasure, I ejaculated.
A hot, thick stream of cum shot out, straight into Mom’s mouth. Her eyes widened but her mouth kept a tight seal around my cock.
My cock shuddered and throbbed as another wave of cum poured into it. Her throat moved, swallowing it all.
“I’m sorry, mom,” I yelled, unable to stop the urge to come.
She moaned, but she didn’t let go of me, as if she was determined to drink it all.
My body went weak after I came. And I never came that strong before in my life. Limping, I collapsed onto the bed.
“I didn’t mean to…” I gasped, gasping for air.
She used her thumb to slide the corner of her mouth, then she sucked on it. “Don’t apologize. I said I’d take care of you, and that’s exactly what I did. Now, are you feeling better?”
I nodded. “Better.”
“Fine. Are you tired?”
She leaned down, kissed the top of my head, and smiled. “Rest, honey. Tomorrow is another day.”
I nodded again. There was a lot to process but exhaustion had her grip on me.
Mom said goodnight and turned off my lamp, drowning the room in darkness and I fell asleep.