From Honor Student to Mom’s Chaste Houseboy

1

Rick, a classmate who bullied me since middle school was exactly the type of guy who made my mom drench her panties — when she’s not going commando that is. He’s three months younger than I am, yet he called me “kid” instead of my name, which irritated me every time I heard it. He was experienced with women and the ways of the street. Everybody knew I was a shy, awkward virgin. Still am, I’m ashamed to say.

It was close to the end of senior year when Rick first saw my mom as she visited our campus. She was shapely and petite, had just turned 38 but looked at least ten years younger, and she kept a flat, toned midriff she was very proud of. She blushed when his eyes devoured her, and I thought she was going to swoon like a giddy twelve year old right there in front of everybody. Normally she wouldn’t have been so shameless about it. I was really pissed, but sort of turned on too. A few weeks later I started hearing rumors that Rick and my mom were having secret quickies.

One day I heard her talking on the phone to somebody named Rick, and later that day I confronted her. When I asked her if she was seeing the Rick I knew from school, she stood even straighter than she was already, stuck her nose up in the air a little and said, “Not that it’s any of your business, but yes, I am.”

I pointed out that he’s still living at home, but she said, “He’s eighteen, that makes him an adult.”

“Mom, do you realize he’s bullied me and made my life hell for years?”

“Oh, come on, Jeremy. You know how some young men are. Stop taking things so seriously. He’s just trying to get you to be a regular guy.”

I didn’t respond. There wasn’t any use. But the weird thing was, I kept thinking about it and later I got so horny I had to go rub one out. Somehow, I was sure that Mom knew. After that day, she invited Rick over whenever she wanted, no longer hiding their relationship from me.

One evening they were pawing each other on the living room sofa, Rick in jeans and a t-shirt which showed off his muscled torso, and Mom in a white thong bikini and heels because Rick loved it when she wore that. I went to my room to do my homework, and Rick’s homework too, on his orders. He told me not to tell my mom or he’d kick my ass the next day at school.

Every time I’d get a good start on homework, Rick or Mom would call me into the living room to bring them something from the kitchen, or to clear the coffee table or some other menial task.

On the third or fourth time Mom called me in, she said, “Jeremy, could you bring us some wine.”

It was clear that Mom already had more than enough. I just stood there for a second watching her and Rick. She was French kissing him, kneeling astride his lap, her back to me. My eyes drifted toward her ass. Even though she was my mom, her ass was so hot, tight and gorgeous — the thong she was wearing showed pretty much everything. I could feel my cock trying to burst through my pants.

I must have stared a little too long, because Rick said, “What’s the matter, kid, haven’t you ever seen two people making out before?”

When she heard him say that, Mom turned around and asked me where the wine was.

Before I could answer, Rick said, “He didn’t go get it yet. He was just standing there staring at your ass, Eve.”

Mom giggled as she said, “Naughty, naughty, Jeremy.”

“Yeah, he’s naughty alright. He’s a perv. He’s still gonna be jackin’ off when he’s ninety.”

“Oh, he’ll be fine. He just doesn’t know how to handle girls yet.”

“Doesn’t know how to handle them? He’s got nothing to handle them with, and he knows it! I’ve seen this kid in the showers. A girl would need tweezers and a magnifying glass just to find it. He probably thought he had three hairs until he peed out of one.”

“You’re terrible, Rick!” Mom said, trying to stifle her laughter.

“Just tellin’ the truth baby, just tellin’ the truth.”

“I’ll get the wine,” I muttered, and hurried out.

I was mad, but I felt my erection throbbing even harder. I hated the fact that I was turned on by this. I brought them the wine and then Rick told me they wouldn’t be needing me anymore and to make sure I finished ALL my homework.

I wasn’t in my room ten minutes before I could hear Mom start to breath heavy, then coo and whine, then moan, and then she let out a desperate, open-throated yell. She noticed she was getting loud, and I could hear her say something about how they needed to keep quiet, although she was the only one making any noise.

I couldn’t resist sneaking to the end of the hallway and taking a peek. By the time I got there, Rick was on top of her, pounding her pussy hard while she clawed his back and closed her legs around his waist. He was buff and tall, and my petite mom looked like a koala wrapped around a huge tree limb. He started pumping faster and Mom opened her legs and held them straight up.

“Don’t forget to pull out this time!” she said.

Rick pushed in as far as he could and froze.

She whimpered, “No, Nooooooo……… you always do that, you bastard.”

She wasn’t too angry though. She was more than happy to let him rest on top of her as she ran a lazy finger through his hair.

It was only as I watched my satiated mom and her spent lover that that I noticed I’d shot my load too. Not like a man, but like a boy — all over my hand. I snuck back to my room as quietly as I could.

Much later that night after Rick went home, I finally finished his homework and mine. I headed to take a shower before bed. When I finished, I put a towel around me and walked out of the bathroom. I turned around and there was Mom standing right in front of me, with a glass of red wine in her hand, and wearing a short white robe.

Ever so slightly slurring her words, she said, “Jeremy, you don’t seem to have a problem prying into my business or asking personal questions, so I’m gonna do the same. I just want to know, just curious. Is Rick telling the truth about you, I mean about your size?”

“Mom, Jesus, what do you want me to say?”

“Just tell me, that’s all. Is he right?”

I still don’t know why I did what I did, but I walked over to the hall light and flipped it on, turned and faced her, and dropped the towel.

After staring at my crotch for a second, she burst out laughing.

She put her hand over her mouth and said, “I’m sorry, Jeremy….but….my god…. it’s really small, isn’t it. It’s not much bigger than when you were a toddler!”

She kept trying not to laugh, but she wasn’t very successful.

I was embarrassed as I could be, yet once again I could feel myself getting a full erection.

“Oh, it can actually grow a little bit, I see. Rick’s right, honey ­­– you are a perv,” Mom said, still snickering.

Taking a chance on admitting it, I said, “Yeah, I guess I am. Maybe you ought to put me in a chastity belt.”

“Whoa, hey, I’ve heard of those!” They make them for guys. Ha, maybe you do need one at that!”

“Goodnight mom.”

I went into my room and jacked off again like the perv I am.

2

The end of senior year came and I graduated with honors. Rick graduated too, but just barely. He wouldn’t have if I hadn’t been doing his homework and helping him study. I kept living at home but took a summer job right away, planning to add the income to my college fund. I’d need it when fall rolled around.

Rick didn’t bother looking for work. He lived off his parents, and increasingly off my mom. She worked hard and it bugged me that she “loaned” money to him, but it wasn’t my business. He kept coming over and spending time here, not forgetting to order me around and humiliate me as he had his way with my nympho mom. When I came home from work I spent as much time in my room as possible to avoid him.

One day that summer something happened that changed our lives forever. Mom was in the bathroom when I heard her squeal and say, “OH MY GOD.”

I hurried in and there she was, with her left hand over her mouth, smiling, but at the same time on the verge of tears. I said, “What’s going on?”

It was only then that I noticed the test stick in her hand.

“I’m pregnant, Jeremy!”

She was obviously happy, but trying to pretend she was shocked for my benefit.

“I just don’t know how this could have happened; I’m always really careful.”

“I know mom,” I said, keeping my doubts to myself.

Still trying to hide her joy, Mom rambled on, “No more wine for me, and I’m going to start eating healthier too! I’m glad I’m already fit — and by the way, I’m going to need to borrow a little money from you to re-up my gym membership as well as buy a few things for our little addition to the family. It’s never too soon to start stocking up. Anyway, it’ll all work out for the best, Jeremy. Rick might be a little surprised when I tell him, but he’ll be glad later on. I know him. He just has a little growing up to do, that’s all.”

“Yeah,” I said.

I went into the living room and plopped down in front of the TV. My god, I thought, what was she thinking?

Rick’s reaction must have been pretty bad when she told him. He stopped coming around and left town soon afterward. Mom was moody and irritable, angry one minute, crying the next. I could understand why, but I decided it was best to keep my mouth shut.

It didn’t take too long though for her to lighten up and start focusing on getting ready for “our little addition to the family.” We have only a two bedroom home, so I wasn’t too surprised when she put a crib in the corner of my room and redecorated the walls with ducks and bunnies. I was cool with that. I figured I’d be off to college in the fall anyway.

We argued when she started asking for pretty much my whole check every week to buy a crib, toys, a changing table, a baby monitor, a breast pump, vitamins and health food for herself. She also bought a bunch of books on childcare which she insisted I study along with her. I usually gave in to her requests for money, and I was getting a little worried about my college expenses. I had a tuition scholarship though, and I’d make do somehow.

One evening about about a month or so after Rick disappeared, Mom caught me again as I was stepping out of the shower. She was wearing a black leather S/M bra with matching micro shorts and black stiletto pumps. Her tan skin was flawless, her cleavage deep and her nipples proudly erect and in full view through the holes in her bra. Her bare, taut midriff showed only the slightest bump.

I couldn’t help staring her up and down, and of course I got a hard on.

Mom smiled, shook her head and said, “Poor Baby. Your little pee pee looks so battered, like you’ve been punching the munchkin ten times a day. But look. Gotcha a gift!”

It was only then that I noticed she’d been hiding something behind her back. She smiled and whipped out a chastity belt. I was scared, humiliated and happy all at the same time.

I took a breath and stuttered, “L-L-Looks like a CB 6000S.”

“Oh, so you’re familiar with it! I figured as much. I bet you’ve done plenty of ‘research’ online And yes, I ordered an S model. I’m sure you know what S stands for.”

I felt my whole body blush.

Mom said, “Follow me into your bedroom.”

She started walking away and I almost tripped trying to fall in line right behind her. I was more excited than I’d ever been in my life. I watched her sexy but confident stride as she tossed her blonde hair back with one hand while casually dangling her son’s chastity belt with the other.

When we entered my bedroom I saw a clear plastic sheet spread across the floor.

“I’ve been doing a little research myself, and I learned that these things fit better if you’re smooth as a baby. Lie down face up and spread your legs.”

I did as I was told.

Mom kicked off her pumps and sat on the sheet between my legs. She started to touch me but stopped short. She tilted her head and looked my body up and down, as though she were comparing memories of all the male bodies she’d seen to what she saw now. My cock was rock hard and throbbing, bigger than it had ever been, but even at the maximum it was no more than four and a half inches. Mom reached out and ran her hand over my chest, down to my abdomen, and then through my pubic hair. This was the first time anyone had ever come this close to my cock, and I couldn’t help thrusting upward a little.

“Easy, Jeremy,” Mom said.

I closed my eyes and took a deep breath.

I felt Mom lightly brush the underside of my glans. To finally feel a woman’s touch was pure ecstasy, even if that woman was my mother.

In a half clinical, half sensual way, Mom glided her fingers over my shaft and mused, “It’s a shame you’re so small. Too small to please a woman I’m afraid — sorry honey, it’s the truth. But your penis does look cute. And I’m glad I had you circumcised. Rick’s cock was huge, but it was uncut and looked like an anteater.”

I think Mom could sense I was really trying to keep still and not come, so she got to work. She took a pair of scissors from a nearby box and started clipping my “bush” as she called it. Then she lathered me up with warm shaving cream. From the box she pulled out a straight razor and opened it up.

My eyes must have bulged out because she smiled and said, “No need to be scared. It’s just for shaving. I’m not gonna cut anything off.”

Then, as she started scraping away my pubic hair, she continued in a snarky, yet good-humored tone, “But hey, maybe it’s not such a bad idea. I always thought you were meant to be a girl anyway. I was sure I was having a girl when I was pregnant with you — and let’s face it, I wasn’t too far off!”

I was angry, but not enough. I only moaned and tried hard not to thrust upward. Mom stopped shaving and looked toward my face. When my eyes caught hers, she curled her red lips just slightly into a sexy snarl — damn, she looked so hot. At the very same time, she lightly touched the razor’s edge to base of my cock and pulled it slowly across, with no pressure, just hard enough for me to feel it. I shuddered, delirious with lust. I breathed, “Oh mom, I ….I….I….”

So sure of what I meant, Mom said, “I love you too. Now hold still.”

I calmed down as she finished removing what little hair I had left. Then she dried me off and took out a bottle of baby oil. She slathered it all over my cock and balls, and once again I had to try hard to keep from thrusting into her hand. She blotted up the excess oil and told me to get off the floor and stand up.

I stumbled up to my feet and spread my legs.

She tried getting my hard cock into the chastity belt, but finally she said, “Baby, I’m sorry for this, but we can’t wait all night.”

She stepped back and kicked my balls with her bare right foot. It wasn’t a hard kick, but it hurt enough that I lost my erection instantly. While I was still stunned and in pain she put the chastity tube on me and adjusted it. She took the key and hung it around her neck where I watched it nestle into her cleavage. Mom put her hands on her hips and admired her handiwork.

I said, “Ok, what now?”

“Now you begin serving and obeying me.”

“Haven’t I been pretty much doing that for eighteen years already?”

Mom smiled and slapped my face.

“Don’t give me any lip, Jeremy. I kept hoping that someday you’d finally become a real man but….well….we both know that’s not going to happen. You’ll just keep jacking off, like Rick said, waiting for some girl to notice you, which isn’t gonna happen either, baby. And even if you actually managed to bed a girl, you’d have to bribe her to keep her with you. You’re really better off staying with me. You’re already smart, you don’t need college.”

She caressed her midriff as she continued, “And most important of all, it’s becoming obvious that I’m going to need your help around here more than ever in a few months. So just consider this the first day of your official enslavement by the goddess who gave you life in the first place!”

Hearing those stunning words come out of my mom’s pouty, teasing lips while she stood there in black leather made my cock throb with pain as it tried to bust out of its tiny cage. I moaned and started to drip a long string of precum all the way to the floor.

Mom smirked and said, “See what I mean. You love it!

I guess she was right. It’s been two years. I’m still here.

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Squirt30

New to writing but I enjoy stories on femdom, cuckolding and cuckold pregnancy, dominant mother/submissive adult son.