Elena invites her friends

Diary Entry - Day 38

Dear Diary,

Today was different. No marathon sessions with Tommy (only 12 loads — 7 in my ass, 5 down my throat). Instead, I met up with my three closest mom friends — Sarah, Mia, and Lauren — for our usual wine and gossip afternoon at Sarah’s house while the kids were at practice.

I don’t know what came over me, but halfway through the second bottle I started bragging. Openly. Shamelessly. I told them everything.

I leaned back on the couch, crossing my legs, and said with a wicked smile:

“You girls have no idea how good it feels to be a total slut for the most disgusting boy in the neighborhood. Tommy — you know, that ugly, fat, sweaty kid who’s in Jake’s class? The one with the pimples and the belly that hangs over his belt? Yeah. That loser gets to use me like a cheap fleshlight every single day.”

Their jaws dropped.

I continued, voice low and excited:

“My sexy MILF mouth and my big, round, married ass belong to him now. I ride him. I slam my own throat on his thick cock until I’m gagging and crying. I bounce my fat ass on him raw, no condom, no lube, letting him dump load after load inside me while I’m doing chores, while my husband is home, while Jake is in the next room. I do all the work because he gets tired so fast. He just sits there panting like a pig while I milk him.”

Mia nearly choked on her wine. “Elena… are you serious? That kid? He’s so gross!”

I laughed. “Exactly. That’s what makes it so fucking hot. A pathetic, ugly nobody gets to turn a hot, fit MILF like me into his personal cum dump. My perfect lips stretched around his cock, my tight asshole gaping because of him. Yesterday I deepthroated him under the dinner table while my husband ate. This morning I rode him in the garage while my husband was ten feet away washing the car. I got caught four times and just made up the dumbest excuses — ‘He’s helping me stretch’ — and they believed me.”

Sarah looked horrified but couldn’t stop staring. “What about Jake? This is his classmate!”

I shrugged, sipping my wine. “It started as a transaction so Jake would stop bullying him. Now? I’m addicted. I crave it. I love how wrong it is. This ugly fat boy owns my holes. He gets to use my sexy body whenever he wants and I thank him for it.”

Lauren was blushing hard. “Elena, this is insane… but kind of hot in a fucked-up way.”

I kept going, getting wet just talking about it:

“I brag to you guys because I need someone to know how filthy I’ve become. A beautiful, married mother of one letting a disgusting loser treat her mouth and ass like disposable fleshlights. He’s not even good at it. He just cums fast and sweats all over me. And I still beg for more.”

They were all shocked. There was a long silence filled with nervous laughter and wide eyes. But none of them said they’d tell my husband or anyone in my family. In fact, they promised to keep my secret.

Sarah whispered, “As long as you’re safe… we won’t say anything.”

Mia added, “Just… don’t get caught for real.”

Lauren smirked a little. “And maybe tell us more next time.”

I felt such a rush admitting it out loud. Telling my respectable mom friends that I’m secretly this depraved only made me hornier. When I got home I immediately dragged Tommy into the bathroom and rode his cock with my ass while telling him how I bragged about him using me.

He came in under a minute.

Diary Entry - Day 39

Dear Diary,

I did something bold today. After yesterday’s wine-fueled bragging session, I invited Sarah, Mia, and Lauren over to my house while Jake was at baseball practice and my husband was at work. Tommy came over as usual.

But this time I didn’t keep him to myself.

I told the girls: “You all seemed so shocked and curious yesterday. Why don’t you join me? It can be our little friends’ activity. A MILF bonding session. Tommy’s ugly cock gets to use all of us. No pressure… but I promise it’s addictive.”

They were stunned at first. Lots of nervous laughter, blushing, and “Elena, you’re crazy!” But none of them left. After two glasses of wine, they all agreed to stay and “watch at first.” That didn’t last long.

We ended up doing 28 loads total today — Tommy was in heaven and completely overwhelmed.

First Group Session (Living Room)

I started by riding Tommy reverse cowgirl on the couch, my big ass bouncing hard on his cock. The girls sat across from us, eyes wide.

“See how I do all the work?” I moaned. “He’s too lazy and out of shape.”

After a few minutes I waved Sarah over. “Come on, just try my ass. It’s still warm.”

Sarah hesitated but eventually hiked up her skirt, sat on Tommy’s cock, and started riding. She was shocked at how thick he was. Mia and Lauren watched, touching themselves. Sarah only lasted a few minutes before she came hard and climbed off, giggling in disbelief.

Session 2-5 (Kitchen Counter)

We moved to the kitchen. I bent over the counter and let Tommy fuck my ass while I made snacks for the girls. Then each of them took a turn. Mia went next — she’s usually so proper — but she was surprisingly vocal, calling Tommy a “disgusting little pervert” while slamming her ass back on him. Lauren, the shyest, needed me to hold her hand while she took her first load in the ass. I whispered encouragement: “Doesn’t it feel filthy knowing an ugly fat boy like him gets to cum inside hot moms like us?”

All four of us took multiple turns. I made sure to get caught by the mailman when I answered the door with Tommy’s cock still in my ass (I just told him I was “trying on new yoga pants”).

Session 6-10 (Master Bedroom)

We all moved to my marital bed. I had Tommy lie down and we took turns riding his face and cock. I encouraged the girls to be rough with him.

I bragged while bouncing: “This pathetic loser gets to use four married MILFs now. Look at him — sweaty, ugly, and lucky as hell.”

The girls loosened up fast. Sarah sat on his face while I rode his cock. Mia and Lauren took turns deepthroating him sloppily when I switched to anal. We laughed and cheered each other on like it was a spa day. Tommy came 10 times in that room alone.

Session 11-15 (Backyard, semi-public)

We took him outside by the pool. Risk level maxed out. Neighbors could see if they looked hard enough. We lined up on all fours on the lounge chairs and let Tommy go down the line, but mostly we rode him ourselves. I got caught by a neighbor walking his dog. I just smiled and waved while Mia was riding Tommy and said, “Group fitness class! Want to join?” The neighbor hurried away.

Each of my friends took multiple loads in both holes. We treated it like a fun game — who could make the ugly boy cum fastest.

Session 16-28 (Final Hour Before Husbands Got Home)

Back inside, we got competitive and sloppy. Double blowjobs, taking turns riding while the others played with his balls or sat on his face. I made the girls practice my excuse-making skills. When my husband texted that he was almost home, we all rushed to finish Tommy off together — four tongues on his cock and balls until he exploded across our faces.

Afterwards, the girls were flushed, leaking, and laughing. They couldn’t believe they’d done it.

Sarah: “I can’t believe I let that disgusting kid cum in me…”

Mia: “This stays between us, right?”

Lauren: “Elena… I think I want to do this again.”

I told them it could be our regular “friends’ activity.” No jealousy. Just sharing Tommy like a toy. He gets to use four hot, married MILFs now instead of just one. And I love being the ringleader — the one who turned respectable moms into secret sluts for the ugliest boy in town.

My husband came home to four well-dressed, perfectly polite women having “book club.” He had no idea four loads of Tommy’s cum were still dripping out of my ass while I kissed him hello.

This is getting completely out of control.

And I’ve never felt more alive.

Diary Entry - Day 52 (20th Wedding Anniversary Trip)

Dear Diary,

Mark and I are at this beautiful oceanfront resort for our 20th anniversary. He surprised me with a fancy suite, rose petals on the bed, candlelit dinners, couples’ massages — the whole romantic package. He’s been so sweet, holding my hand, telling me how much he loves me, how proud he is of the life we’ve built.

And all I can think about is how different it feels compared to what I have with Tommy.

The Comparison

With Mark, everything is safe, predictable, and… polite. Our sex is gentle missionary once every couple of weeks. He kisses me softly, tells me I’m beautiful, finishes in a few minutes, then cuddles. It’s loving. Respectful.

With Tommy? It’s raw, degrading, and constant. That ugly, fat, sweaty classmate of Jake’s uses my mouth and ass like cheap fleshlights. I do all the work — riding him aggressively, **** myself on his cock, milking him dozens of times a day. He barely speaks. He just grunts, sweats, and pumps me full. No romance. No respect. Just pure, filthy utility.

And yet… I’m wetter for Tommy. I cum harder when I’m sneaking him into my married holes while my family is nearby.

Was my life better before Tommy?

I keep asking myself this. Before him, I was the perfect wife and mother. Calm, organized, respected. No constant leaking cum in my panties. No lying through my teeth. No risk of total destruction.

But I was also bored. Sex was routine. My days blended together. Now? I’m alive. Every hour has this dirty secret humming through me. My body feels used and owned in a way Mark never made me feel. I’ve become shameless. Addicted.

I think I was happier before… but I don’t want to go back.

Lifestyle Changes Since Tommy

I barely wear panties anymore. Easier access.

I’ve started dressing sluttier under my normal mom clothes — short skirts, no bra, plugs in my ass when Tommy can’t come over.

I’ve become an expert liar. My excuses flow naturally now.

I’ve dragged my respectable friends into it. Sarah, Mia, and Lauren now regularly join “Tommy sessions” like it’s book club.

My asshole is permanently looser. My throat is trained. I can deepthroat him in under ten seconds.

I cum from anal and degradation almost every time now.

I’ve changed. A lot.

Navigating the Romantic Anniversary While Serving Tommy

I couldn’t go five days without him, so I secretly booked Tommy a cheap room at the same resort (using the “friends’ activity” group chat fund). He’s been sneaking in and out like a rat.

Here’s how today went — our official anniversary:

Morning Romantic Breakfast

Mark fed me strawberries and kissed me across the table. Sweet. Romantic.

Meanwhile, Tommy was under the table in the private beach cabana we rented. I had my sundress spread, sitting on his face while feeding him my asshole. I rode his tongue gently while smiling at my husband. When Tommy’s cock replaced his tongue, I slowly bounced on him under the long tablecloth. Mark thought my soft moans were from the ocean view. Tommy came inside me during the mimosa toast. I kissed Mark deeply right after, with Tommy’s cum leaking out of my ass.

Afternoon Couples’ Massage

Mark and I lay side by side. The masseuses worked on us.

I texted Tommy. He snuck into the private massage hut after the therapists left for a break. While Mark was face-down and relaxed, I rode Tommy reverse cowgirl right next to my husband. I had to stay mostly quiet, biting my lip hard. Every time Mark sighed happily about how nice the trip was, I slammed my ass down harder on Tommy’s cock. He filled me twice before we had to stop.

Evening Romantic Dinner

Candlelight. Wine. Mark gave me a beautiful necklace and told me I was still the most beautiful woman he’d ever seen.

I excused myself to the bathroom twice. Both times Tommy was waiting in the family restroom I’d left unlocked. First time: rough face fucking over the sink, mascara running while I gagged quietly. Second time: bent over the counter, him using my ass while I fixed my makeup. I went back to the table with fresh cum in both holes and kissed Mark, telling him how much I loved him.

Nighttime in the Suite

Mark wanted to make love. We did — slow, gentle, face-to-face. I faked an orgasm.

As soon as he fell asleep (he’s snoring beside me right now), I texted Tommy. He’s in our honeymoon suite bathroom as I write this. I’m sitting on his cock right now, typing slowly while I grind. I’ve already taken four loads from him since Mark passed out. I’m going to ride him all night in the bathroom, then brush my teeth and crawl back into bed with my husband like nothing happened.

Diary Entry - Day 53 (Anniversary Trip - Day 2)

Dear Diary,

Today I met my match. Or rather… my rival decided to crash my filthy little world.

Her name is Vanessa Blake. She’s the queen bee of the PTA, the woman I’ve quietly competed with for years. Perfect body for 42, fake tits she loves to show off, always dressed like she’s going to a photoshoot. Her husband is richer than mine, her son is the star athlete (unlike Jake), and she never misses a chance to subtly brag. We smile at each other at school events but we both know we can’t stand one another.

She’s also staying at this exact resort with her family. Of course she is.

I was in the middle of Session 14 of the day — riding Tommy’s cock in a semi-hidden beach cabana while Mark was out jet-skiing — when she appeared.

She pulled back the curtain like she owned the place.

There I was: sundress bunched around my waist, sweat glistening on my skin, bouncing hard on Tommy’s thick cock reverse cowgirl, my big ass rippling with every drop. Tommy’s fat hands were gripping my hips. My moans were barely muffled.

Vanessa’s eyes went wide, then narrowed with pure jealousy.

“Elena? With… him?” She stared at Tommy like he was a cockroach. “The ugly fat kid who follows your son around like a loser? You’re actually letting that disgusting boy fuck you on your anniversary trip?”

I didn’t stop riding. I slowed down to deep, deliberate grinds and looked her dead in the eye.

“Yes. Every day. Multiple times. He uses me like a fleshlight. And I love it.”

Tommy looked terrified, but I kept him pinned inside me.

Vanessa’s face twisted. She was clearly shocked… but also turned on and bitterly jealous. I could see it in the way her thighs pressed together and her nipples hardened under her designer bikini.

“You always acted so perfect,” she hissed. “Miss Responsible Mom. And here you are, letting some pathetic, sweaty nobody destroy your married holes while your husband is twenty minutes away.”

I smiled, clenching around Tommy’s cock.

“Exactly. And he gets to cum in me more in one day than Mark has in the last six months. Want to watch?”

That’s when the jealousy really spilled out.

Vanessa stepped inside the cabana and let the curtain fall. She didn’t leave. Instead, she sat on the bench across from us, legs crossed, watching me ride.

“I should tell your husband,” she said, but her voice lacked conviction.

“You won’t,” I replied, bouncing harder, making my tits shake. “Because deep down you’re jealous. Your perfect son would never get a woman like me. But my son’s ugly, bullied classmate gets to use my mouth and ass whenever he wants. He owns me more than Mark does.”

Tommy groaned and came inside me right then. I stayed seated on him, letting his cum leak out as I stared at Vanessa.

She was breathing heavier. After a long silence she finally admitted it.

“…I want in.”

She told me she’s been bored with her own husband for years. She’s heard rumors about me from Sarah (who apparently can’t keep her mouth shut completely). Seeing it in person triggered something vicious and competitive in her.

So I made her a deal.

She can join the “friends’ activity” circle… but only if she accepts that Tommy is mine first. She can use him, but I control the schedule.

Vanessa agreed immediately. Too eagerly.

Session 15 (Right there in the cabana)

I made her watch me clean Tommy’s cock with my mouth first. Then I guided her onto him. She tried to act superior, but within thirty seconds she was moaning like a whore, riding him desperately while calling him “you disgusting little pervert.” Tommy came in her ass in under two minutes. She looked furious and satisfied at the same time.

We did two more rounds with her before Mark texted me.

Lifestyle Note

Vanessa is going to be trouble. She’s already talking about “stealing” Tommy from me, about making him prefer her tighter body, about competing over who can take more loads. She’s the jealous rival I didn’t know I needed.

Part of me is nervous.

Another, darker part of me is excited to have competition.

This trip just got a lot more dangerous… and a lot more fun.

Diary Entry - Day 54 (Anniversary Trip - Day 3)

Dear Diary,

Mark is starting to suspect something. It’s subtle for now, but I can feel it. The way he looks at me a little longer, the slight hesitation before he smiles, the way he keeps “casually” asking where I’ve been. After 20 years of marriage, he knows me too well.

This morning started romantically enough. Mark brought me breakfast in bed and wanted morning sex. We made love slowly. I faked it again. The entire time I was thinking about how Tommy’s thick cock stretches me so much better, how his cum feels leaking out of me for hours.

After Mark went to the gym, I immediately texted Tommy and Vanessa.

Session 18-22 (Private Beach Cabana)

Vanessa showed up first, acting all superior in her tiny bikini. We double-teamed Tommy — I rode his cock while she sat on his face. She kept trying to one-up me, moaning louder, calling him filthier names. “You disgusting fat loser, you’re lucky you even get to taste a superior pussy like mine.” I just laughed and rode him harder.

Then Mark appeared.

He was supposed to be at the gym for at least another hour, but he “decided to surprise me” with flowers. He pulled the cabana curtain open and froze.

There I was — completely naked, bouncing on Tommy’s cock. Vanessa was beside us, topless, squeezing her fake tits while watching. Tommy’s fat body was sweating underneath me.

For a second, time stopped.

Mark’s face went pale. “Elena…? What the fuck is this?”

I didn’t stop riding. I slowed down but kept Tommy buried deep inside me as I looked at my husband.

“Honey… this isn’t what it looks like,” I said breathlessly.

Mark stared. “It looks like you’re fucking that kid from Jake’s class. And with Vanessa? On our anniversary trip?”

I stayed calm, still gently grinding on Tommy’s cock while my mind raced.

“Mark, listen. Tommy has been having a really hard time at school. Jake used to bully him, remember? This is… therapy. Exposure therapy, kind of. I’m helping him build confidence. Vanessa is here because she’s also part of the PTA support group for this. It’s not romantic. It’s just physical. A transaction.”

Vanessa actually played along, giving Mark a sweet smile. “It’s true, Mark. Elena’s been so dedicated. We’re just… helping the boy.”

Mark didn’t fully buy it. I could see the suspicion burning in his eyes. But he also looked confused and embarrassed. He muttered something about needing air and left the cabana without yelling. No explosion. Not yet.

As soon as he was gone, I rode Tommy furiously and came harder than I had in days. Vanessa laughed and called me insane.

Later that afternoon — Poolside

Mark was quiet during lunch. He kept staring at my neck (which had a faint hickey from Tommy) and at how I was walking slightly bow-legged. When he asked why I disappeared for 40 minutes after lunch, I told him I was “getting a quick massage.” He nodded but didn’t look convinced.

Session 23-26 (Hotel Stairwell)

I snuck Tommy and Vanessa into the emergency stairwell. I was bent over the railing taking Tommy in my ass when we heard footsteps. It was Mark again, looking for me. He came up the stairs and saw me — dress around my waist, Tommy’s cock buried in my ass, Vanessa holding my hair like reins.

“Elena…” His voice cracked.

I looked back at him, flushed and sweaty. “Mark, baby, I twisted my ankle earlier. Tommy and Vanessa are helping me stretch it out. The stairwell has good support.”

He stared for a long moment, then turned and walked away without another word. The suspicion is growing. He knows something is very wrong.

Evening

Mark tried to have another romantic dinner, but he was distant. He asked me directly if anything was going on with “that boy.” I lied smoothly, cried a little (fake tears), and told him he was being paranoid because of stress from work. I even guilt-tripped him about not trusting me after 20 years.

It worked… for now.

But later tonight, while Mark was in the shower, I brought Tommy into the balcony of our suite. I rode him standing up, my moans softly floating into the room. When Mark came out, he saw me leaning on the railing in my silk robe. He couldn’t see Tommy behind me, but I’m sure he noticed how I was moving.

“Honey, are you okay?” he asked.

“I’m just… enjoying the ocean breeze,” I moaned, right as Tommy pumped another load into my ass.

I feel guilty. Mark doesn’t deserve to be gaslit like this. But the suspicion in his eyes, the risk of getting fully caught… it’s making everything ten times hotter. Vanessa is loving the drama. She keeps whispering that she’ll steal Tommy if I get caught.

I’m riding a dangerous wave now. My perfect marriage is cracking, and instead of stopping, I’m accelerating.

Part of me wonders if I want to get caught.

Diary Entry - Day 58 (Back Home)

Dear Diary,

The strangest thing happened. After we returned from the anniversary trip, Mark… forgot everything. Or at least he’s acting like he did. He never brought up the cabana, the stairwell, or any of the times he caught me. It’s like his brain deleted the memories out of self-preservation. He’s back to being sweet, affectionate, and completely oblivious.

So I stopped holding back.

I’m now taking Tommy in fully public, crowded places with zero hiding spots. No curtains, no tables, no excuses to leave the room. I just do it in the open and pretend I’m doing something else. The risk is insane. And I’m addicted to it.

Session 1-4: Supermarket (Saturday Morning)

The grocery store was packed. I wore a loose sundress with no panties. Tommy followed me down the busy aisles.

In the cereal aisle, surrounded by families, I bent over the bottom shelf pretending to reach for something. Tommy stepped right behind me and shoved his cock into my ass in one thrust. I stayed bent over, slowly pushing back onto him while reading the nutrition labels out loud. An older woman walked right past us. I smiled at her and said, “These new brands are so confusing, aren’t they?” while Tommy’s fat cock stretched my asshole. He came inside me as I stood up and put the box in the cart.

Later in the frozen section, I dropped to my knees in front of Tommy like I was tying my shoe. I took his cock down my throat and gave him a sloppy, gagging face fuck while other shoppers pushed carts around us. When someone asked if I was okay, I pulled off with spit dripping down my chin and said, “Just fixing my sandal strap. It keeps coming loose.”

He came down my throat while I was thanking a store employee for helping me find almond milk.

Session 5-8: Crowded Park During Jake’s Soccer Game

Dozens of parents watching the game. I sat on the bleachers with Tommy right behind me. I pulled my skirt up just enough and sat on his cock in full view of everyone. I rode him slowly while cheering for Jake.

A mom from the PTA sat right next to me and started chatting. I kept bouncing on Tommy’s cock the entire conversation, my voice only slightly breathy. When Tommy came inside me, I clenched hard and told her, “These benches are so uncomfortable. I keep having to shift around.”

Later I dragged him behind the bleachers (still visible from multiple angles) and deepthroated him aggressively while pretending to look through my purse for sunscreen.

Session 9-12: Mall Food Court (Extremely Crowded)

Hundreds of people around us. I sat on Tommy’s lap at a small table in the middle of the food court. My skirt covered the connection. I rode him hard and fast while eating frozen yogurt, making eye contact with strangers. When a group of teenagers sat at the next table, I didn’t stop. I just leaned forward like I was showing Tommy something on my phone while my asshole milked him.

I came hard while a mother with two kids walked right past us. Tommy filled my ass right as the kid pointed at me and said “Mommy, that lady looks funny.”

Session 13-16: Movie Theater (Matinee, Packed)

Dark but very crowded. I sat on Tommy’s cock in the middle row, riding him slowly during the entire film. The people on both sides of us had no idea. When the lights came on at the end, I stayed seated on him, grinding until he came again while everyone stood up to leave. I told the couple next to us I was “waiting for the crowd to thin out.”

Session 17-20: Church Parking Lot After Sunday Service

Right after mass, in broad daylight. I bent over the trunk of our car pretending to look for something in the back while Tommy fucked my ass from behind. Multiple families were walking past. I waved and smiled at them while getting pounded. When Father Michael walked by and asked how I was, I moaned softly and said, “Just a little back pain from sitting too long in the pews. Tommy’s helping me stretch.”

My Current Lifestyle

I’ve completely stopped trying to hide. I just multitask through my depravity. My excuses have become performance art. Mark still suspects nothing. Jake thinks Tommy is just “around a lot.” My friends (including jealous Vanessa) now sometimes join me in these public sessions when they’re feeling brave.

Tommy still can’t believe his luck. This ugly, fat, pathetic boy gets to use a hot MILF’s mouth and ass in the middle of supermarkets, parks, and churches while I casually chat with strangers.

Diary Entry - Day 62

Dear Diary,

Things have gotten wild since I brought the other moms into Tommy’s world. What started as my private transaction has turned into a full MILF club. I thought I’d be the main one, but these women have surprised me. Each of them has taken it in her own direction. Here’s what’s been happening:

Sarah (The Bold Exhibitionist)

Sarah, my elegant best friend who always seemed so proper, has become the most shameless. She’s started taking Tommy to her husband’s company events. Last week she rode him openly in the back of the conference room during a big presentation. Her husband was onstage speaking while Sarah sat in the last row, bouncing on Tommy’s cock under her elegant dress. When someone turned around, she just smiled and pretended she was doing pelvic floor exercises. She now brags that she’s taken 18 loads in one corporate golf tournament — mostly in the golf cart while other players were right behind them.

She loves getting caught. The other day at the country club she was bent over a table on the patio (in broad daylight) getting anal while pretending to look at a menu. Three waiters saw her. She just said, “Tommy’s teaching me proper posture for tennis.”

Mia (The Humiliator)

Mia has gone full dominant. She treats Tommy like absolute trash and it makes him cum faster than anything. She makes him lie on the floor of her kitchen while she rides his face and cock in front of her cleaning lady. She constantly insults him: “You pathetic, ugly little pig. You’re lucky four hot moms even let you touch them.”

Last weekend she took him to her son’s piano recital. While everyone was watching the kids perform, Mia had Tommy sitting in the back row and sat on his cock reverse cowgirl. She rode him slowly the entire concert, whispering degrading things in his ear. When her husband asked why she was breathing so heavily, she said she was “moved by the music.” She came twice during her own son’s performance.

Lauren (The Shy One Turned Addict)

Sweet, quiet Lauren has changed the most. She used to be the most hesitant, but now she’s obsessed. She’s developed a thing for school-related risks. She’s blown Tommy in the school parking lot during parent-teacher conferences, right between parked cars while other parents walked by.

Two days ago she took him into the school bathroom during a PTA meeting. She locked the stall door but kept talking loudly to another mom outside while she was on her knees deepthroating him. The other mom had no idea Lauren was gagging on fat teenage cock just a few feet away. Lauren told me she came just from the humiliation.

Vanessa (The Jealous Rival)

Vanessa is the most competitive. She’s been trying to “steal” Tommy from me. She texts him directly now and tries to arrange secret sessions. Yesterday she took him to the gym and rode him in the women’s sauna while other women were changing. She made him cum inside her three times, then walked out with his cum running down her legs, smiling at everyone.

She keeps score. She bragged that she took 14 loads in one day — one more than my record at the time. We’re basically in a silent war over who can be the biggest slut for this ugly boy.

Group Adventures

We’ve also started doing things together again. Last Tuesday all five of us (me, Sarah, Mia, Lauren, and Vanessa) took Tommy to the crowded public library. We sat in a big circle of study tables and took turns riding him and sucking him under the table while students and other moms studied around us. We treated it like a game — whoever made him cum fastest won a point. Vanessa won. I’m still bitter about it.

My Thoughts

Watching my respectable, married friends turn into depraved cock addicts for the same pathetic, fat, ugly boy has been strangely thrilling. We all still pretend to be perfect mothers in public. We go to book clubs, soccer games, and charity events like nothing’s changed.

But behind the scenes we’re competing over who can take Tommy in the riskiest places, who can swallow the most loads, who can come up with the most creative excuses when caught.

Mark still acts like he remembers nothing from the trip. Jake has no clue. And Tommy… he just sits there sweaty and overwhelmed while four or five hot MILFs fight over his cock.

I created a monster.

And I’m loving every second of it.

Diary Entry - Day 63

Dear Diary,

Sarah came over for coffee this morning and gave me every filthy detail of what she did at her husband’s big corporate retreat last week. I’m honestly impressed — and a little jealous. She has taken exhibitionism to a whole new level.

Sarah’s Corporate Event Adventure

It was the annual company leadership summit at a luxury hotel. Her husband, Richard, was one of the keynote speakers. Over 200 executives, managers, and their spouses filled the grand ballroom for the main presentation.

Sarah wore a sophisticated navy blue business dress — elegant, modest from the front, but short enough in the back for easy access. No panties, of course.

She brought Tommy as her “intern helper” for the day. She even made him wear a cheap suit that barely fit his fat frame. The contrast was ridiculous: beautiful, poised Sarah with this ugly, sweaty teenage boy.

Session 1-3: During Richard’s Keynote Speech

Sarah saved seats in the very back row, far right corner. The lights were dimmed for the presentation. As soon as Richard stepped on stage and started speaking, Sarah pulled Tommy close.

She hiked her dress up, sat on his lap, and slowly sank down onto his thick cock, taking him raw in her ass. Then she started riding him — slow, deep, and controlled at first.

Richard was on stage talking about “integrity and leadership” while his wife was bouncing on a disgusting fat boy’s cock just 40 feet away.

Sarah told me she made eye contact with Richard several times and smiled sweetly while grinding in circles. Tommy was panting heavily behind her. When the applause got loud, she rode him harder, using the noise to cover the wet slapping sounds.

She came twice during the 45-minute speech. Tommy pumped three loads into her ass without ever leaving her. Every time someone in the row in front turned their head, Sarah would casually adjust her posture and say things like, “These chairs are so stiff, aren’t they?” while her asshole clenched around Tommy’s cock.

Session 4-6: Networking Cocktail Hour

After the speech, everyone moved to the cocktail area. Sarah didn’t even clean up. She walked around with Tommy’s cum leaking down her thighs, smiling and chatting with executives’ wives.

At one point she pulled Tommy behind a tall floral arrangement (still completely visible from multiple angles) and bent over slightly, pretending to admire the flowers. Tommy entered her ass again and she pushed back onto him while holding a glass of champagne and talking to two other women.

When one of them asked what Tommy was doing, Sarah laughed lightly and said, “Oh, he’s my assistant. He’s helping me with my lower back pain — terrible sciatica. These corporate events really take a toll.”

She stayed bent over, getting fucked, for a full ten minutes while making small talk.

Session 7-9: During the Panel Discussion

Later, Richard was on a panel onstage. Sarah sat in the front row this time — maximum risk.

She had Tommy sit beside her. She draped her blazer over her lap, pulled his cock out, and stroked him openly under the blazer while the panel discussed “work-life balance.” Then she turned slightly, lifted one leg, and guided him back into her ass.

She rode him gently but steadily during the entire 50-minute panel, right in front of her husband and 200 people. When the moderator asked Richard a question about family priorities, Sarah clenched hard and came on Tommy’s cock while her husband answered.

A man sitting two seats away definitely noticed something. He kept glancing. Sarah just smiled at him and whispered, “Sorry, I have to keep moving or my back locks up.”

Final Session: Elevator Ride Back to Their Room

After the event ended, Sarah, Richard, and Tommy got into a crowded elevator together. Sarah positioned herself in front of Tommy, backed her ass onto his cock, and rode him standing up the entire ride while making conversation with her husband.

“Yes honey, you were wonderful today,” she said sweetly while Tommy quietly pumped his final load into her.

Richard never suspected a thing.

Sarah told me she felt like a goddess the entire day — a respected corporate wife secretly turning her husband’s important event into her personal depraved playground. She said the thrill of riding Tommy while Richard was being celebrated onstage was better than any orgasm she’s had in years.

She’s already planning to bring Tommy to the next company Christmas party.

Hearing her stories made me so wet that I immediately called Tommy over and rode him on my kitchen counter while she watched and gave me tips.

These women are completely corrupted now.

And I’m so proud.

Diary Entry - Day 65

Dear Diary,

I’ve been thinking a lot lately about the full reality of my “relationship” with Tommy. It’s not just my holes anymore. It evolved into something more complicated. I provide him with way more than my mouth and ass. And he actually has a few hobbies besides pumping his cum into me.

What I Give Tommy (Besides My Holes)

Full “Maternal” Care

I basically act as his secret second mother. I cook him big meals almost every day — fried chicken, burgers, pasta — because he’s always hungry. I pack him lunches for school with little notes that say filthy things on the inside. I do his laundry sometimes (especially the ones stained with my juices). I even bought him new clothes that actually fit his fat body so he doesn’t look quite as pathetic in public.

Money and Gifts

I give him a weekly “allowance” — $150 cash. I also buy him expensive gaming stuff, new sneakers, and snacks. Last week I got him a top-of-the-line gaming chair because he complained his old one hurt his back when I ride him for long sessions.

School & Social Protection

I make sure Jake and his friends never bully him again. I even **** Jake to apologize publicly and now Jake has to be “nice” to Tommy at school. I help Tommy with his homework (he’s terrible at math and English). I write his essays sometimes.

Emotional Validation

This is the weirdest part. Tommy is deeply insecure. After he cums, he sometimes gets sad and talks about how no girl his age will ever want him. I stroke his hair and tell him how lucky he is that a hot, married MILF like me lets him use her however he wants. I feed his ego by bragging about how much better his cock feels than my husband’s.

Access to My Friends

He now has four other hot moms (Sarah, Mia, Lauren, Vanessa) who also let him use them. That’s a huge ego boost for him.

Tommy’s Other Hobbies (Besides Using My Holes)

He’s still a stereotypical loser teenage boy, just with way more confidence now:

Video Games

He’s obsessed with Fortnite, Call of Duty, and some weird anime fighting games. He can play for 8+ hours straight. Sometimes I ride him slowly while he plays ranked matches with his headset on. He actually gets better at games when his cock is inside me — it relaxes him.

Junk Food & Snacking

Eating is basically a hobby for him. He loves ordering Uber Eats while I’m bouncing on him. His favorite is eating a whole large pizza while I’m doing all the work on his cock.

Anime & Hentai

He watches a ton of anime, especially the perverted ones. He makes me cosplay sometimes — I’ve worn a slutty schoolgirl outfit and a maid costume for him. He says I’m better than any hentai girl because I’m real.

Collecting Trading Cards

He collects Pokémon and sports cards. I bought him some expensive rare cards as a reward when he lasted longer than 5 minutes inside me.

Watching Porn

Before me he jerked off 5-6 times a day to MILF and public humiliation porn. Now he barely watches it because he has the real thing, but he still likes showing me the videos he used to cum to and making me recreate them.

My Thoughts

Sometimes I look at him — this sweaty, overweight, unattractive boy sitting on my couch playing video games while I cook for him — and I wonder how the hell I got here. I’m a 42-year-old married mother acting as his personal chef, sugar mommy, therapist, bully-protector, and fucktoy all at once.

He doesn’t love me. I don’t love him.

But I’ve become completely essential to his pathetic little life, and he’s become essential to my depraved one.

Tomorrow Sarah wants to take him to another one of her husband’s corporate events. I might go watch.

Diary Entry - Day 68

Dear Diary,

The “Tommy MILF Club” has developed its own complex group dynamic. What started as me sharing him with my friends has turned into a full-blown secret society with its own rules, rivalries, personalities, and rituals. Here’s how it really works now:

The Power Structure

Me (Elena): The Founder and unofficial Queen. I control the main schedule and decide when group sessions happen. The others have to ask me first if they want Tommy on certain days. I love this role — it makes me feel powerful while still being his primary slut.

Vanessa: The Challenger. She’s constantly trying to undermine my authority. She wants to be the new favorite and often tries to arrange secret one-on-one sessions with Tommy behind my back. We have an ongoing cold war.

Sarah: The Wild Card. She doesn’t care about hierarchy. She just wants maximum thrill and exposure. She’s usually the one pushing for the craziest public group activities.

Mia: The Enforcer. She’s the most dominant with Tommy. During group sessions she often directs the others and degrades him the hardest. Everyone respects (and fears) her intensity.

Lauren: The Sweetheart / Mediator. She’s the peacemaker. She gets nervous when tensions rise between me and Vanessa. She’s also become the biggest cum addict of all of us.

Typical Group Session Dynamic

We usually meet 2-3 times a week when our husbands and kids are occupied.

Last Saturday we had a big group session at Mia’s large basement while her husband was away on a golf trip.

How it played out:

We made Tommy sit naked on the couch like a king (a very sweaty, ugly king). Then we took turns in a rotation:

Riding Order — We drew cards to decide who rides his cock first. I went first as the leader. While I rode him, Mia sat on his face and made him eat her ass. Sarah and Lauren took turns sucking his balls and kissing me.

Degradation Circle — While one woman rides him, the others stand around and roast him. Mia is especially vicious: “Look at this pathetic fat loser. Four hot married moms fighting over your worthless cock.” Vanessa always tries to one-up her with crueler insults.

Competition Games

Who can make him cum the fastest (we time it)

Who can take the deepest anal without flinching

Who can deepthroat him the sloppiest while maintaining eye contact

“Cum Swap” — whoever gets a load has to share it with another girl by kissing

Sarah won the “riskiest position” contest when she rode him reverse cowgirl while bent over Mia’s husband’s pool table, with the curtains open.

Rivalries & Tension

The biggest tension is between me and Vanessa. She keeps score obsessively. Last week she texted the group chat: “I took 19 loads this week. Beat that, Elena ”

I responded by organizing an emergency group session the next day and making sure I got 9 loads while she only got 4. Petty? Yes. Satisfying? Extremely.

Mia and Sarah are more neutral but they enjoy watching me and Vanessa compete. They’ll deliberately praise one of us to make the other jealous.

Lauren usually tries to calm things down, but she gets so turned on by the competitive energy that she ends up riding Tommy the hardest during these fights.

Group Rules We’ve Established

Tommy is not allowed to message any of us first — he must wait for us to contact him.

No one is allowed to have him for more than 24 hours straight without telling the group.

All pregnancies are immediately terminated (we all got IUDs just in case).

When one of us gets caught, the others help create alibis.

Monthly “Tommy Slut Awards” — categories like Most Loads, Riskiest Location, Best Excuse, Filthiest Act.

The Emotional Side

Strangely, we’ve all grown closer. After particularly intense sessions we sit together, leaking cum, drinking wine and laughing about how depraved we’ve become. We talk about our boring marriages, our stresses, and how Tommy — this ugly, fat, pathetic boy — has become our shared escape and obsession.

We all know this is completely fucked up.

We all know we should stop.

But none of us want to.

We’ve created our own little filthy sisterhood. And Tommy, the unlikely center of it all, just sits there eating snacks and getting his cock worshipped by five married MILFs who used to be respectable.

I wonder how long we can keep this going before something breaks.

Diary Entry - Day 72

Dear Diary,

Last night we held our first official Monthly Tommy Slut Awards.

We turned it into a whole event at Sarah’s house while her husband was away on a business trip. We decorated the living room with cheap plastic trophies we bought from a party store, lit some candles, and wore our sluttiest outfits. Tommy sat on the “throne” (a big armchair) completely naked, eating pizza like a king while five dressed-up MILFs competed for his attention.

It was ridiculous, hilarious, and unbelievably arousing.

The Tommy Slut Awards 2026

Host: Mia (she was the most savage commentator)

Categories & Winners:

1. Most Loads Taken

Winner: Vanessa (27 loads)

Vanessa looked extremely smug. She bragged that she snuck Tommy into her walk-in closet three times while her husband was home watching TV. She even showed us the tally marks she kept on her phone. I came in second with 24. I’m still bitter about it.

2. Riskiest Location

Winner: Sarah

Sarah won for riding Tommy during her husband’s corporate keynote speech in front of 200 people. She played a short video (no faces) of her bouncing subtly while her husband was on stage. We all clapped. Even I had to admit it was legendary.

3. Best Excuse When Caught

Winner: Me (Elena)

My stairwell excuse to Mark (“It’s physical therapy for my ankle”) during the anniversary trip took the prize. The girls made me re-enact it while sitting on Tommy’s cock. I won a “Golden Excuse Trophy” (a cheap plastic cup with glitter on it).

4. Filthiest Act

Winner: Mia

Mia destroyed everyone with her story of making Tommy cum in her ass, then pushing the cum out into a wine glass and drinking it in front of her cleaning lady while pretending it was “a new protein shake.” She even did a demonstration for us last night. Tommy came just from watching her retell it.

5. Most Improved Slut

Winner: Lauren

Sweet little Lauren went from shy and hesitant to a complete cum-hungry whore in just a few weeks. She cried happy tears when she won. Her acceptance speech involved her deepthroating Tommy on stage while thanking us for “corrupting her.”

6. Best Degradation

Winner: Mia (again)

Her verbal **** is on another level. She has entire monologues about how Tommy is a “disgusting, sweaty, pig-nosed loser who doesn’t deserve to breathe the same air as us, let alone fuck us.”

7. Wildcard “Most Pathetic Moment”

Winner: Tommy (we made him accept this one)

For the time he came in his pants just from watching all five of us line up on all fours in Mia’s basement.

The After-Party

After the awards, we had a “Champions Ride.” Each winner got to ride Tommy for two minutes while the rest of us cheered and degraded him. Vanessa went last and tried to steal extra time, which caused a small catfight between her and me (we ended up making out aggressively on top of him).

By the end of the night, Tommy had unloaded 11 more times across all of us. We were all leaking, exhausted, and laughing like schoolgirls.

This whole awards thing is so stupid and depraved… but it’s become one of my favorite parts of this new life. It turns our filth into a competition and a bonding experience. We’re no longer just individual sluts — we’re a team of competitive, married cock addicts obsessed with the same ugly boy.

Next month I’m aiming to sweep the awards.

Vanessa is going down.