Tommy drops a bomb

Diary Entry - Day 77

Dear Diary,

Tommy dropped a bomb on us yesterday.

During a group session at my house, Mia was in the middle of one of her usual savage degradations — calling him a “pathetic sweaty pig” and a “disgusting loser who doesn’t deserve us” — when Tommy suddenly pushed her off his cock and said:

“Stop. I don’t like that anymore.”

We all froze.

He looked embarrassed but determined, his fat belly rising and falling as he spoke:

“I’m tired of being called ugly and pathetic. Yeah, I know I’m fat. I know I’m not good-looking. But look at me… I’m fucking five hot, married MILFs. Five of you. Regularly. While your husbands have no idea. I’m conquering all of you. I want praise. I want you to tell me how amazing I am for this.”

The room went silent for a few seconds.

Then Sarah started laughing. Not meanly — she was genuinely amused. “Oh my god… our little loser has developed an ego.”

The New Dynamic

We had a quick group discussion (while Tommy was still sitting there with his cock hard and covered in our juices). He was very clear: he doesn’t want degradation anymore. He wants to be worshipped and praised as the “ultimate conqueror” — the fat, ugly kid who managed to claim five beautiful, high-status mothers.

We all agreed to switch. Partly because we don’t want to lose access to him… and partly because the new praise kink is strangely hot in its own way.

Last Night’s Praise Session

We held a special “Conqueror’s Night” to test the new style.

We dressed up in sexy lingerie and heels. Tommy sat on the big couch like a king. One by one, we praised him while servicing his cock:

Elena (me):

I rode him slowly, looking into his eyes. “You’re such a stud, Tommy. Look at you… this big, thick cock owning five married women. You’re better than all our husbands combined. A fat, ugly boy who conquered our pussies and asses. I’m so proud of you, baby.”

Sarah:

While sucking his balls: “You’re incredible. My husband works so hard and makes all that money, but you’re the one who gets to use my body whenever you want. You’re a legend, Tommy. A true conqueror.”

Lauren:

Deepthroating him sloppily: “Mmm, I used to be so shy… and now I crave your cock every day. You did that. You turned five respectable moms into your personal sluts. You’re amazing.”

Vanessa (she struggled the most with this, but tried):

“You’re… surprisingly powerful. A boy like you having five MILFs competing over your cock is actually really impressive. You’ve beaten all our husbands without even trying.”

Mia (the biggest switch):

She sat on his face and moaned, “You own us, King Tommy. This fat, sweaty body has five married women addicted. You’re the alpha in our secret world. We’re all your conquests.”

Tommy was in heaven. He came harder and faster than usual. The praise clearly turned him on massively — he lasted longer and came four times in two hours.

My Thoughts

This new praise dynamic feels different. Instead of using him as a degraded toy, we’re now building him up as this perverted conqueror figure. It’s feeding his ego like crazy. He’s started walking taller, demanding we call him “King Tommy” or “The Conqueror” during sessions.

Vanessa hates it. She loved degrading him. But even she’s playing along because she’s addicted.

I have to admit… telling this ugly fat boy how superior he is while riding him is surprisingly arousing. There’s something deeply humiliating (for us) about praising him for “conquering” us.

He’s not just getting our holes anymore.

He’s getting our worship.

And he’s starting to act like he deserves it.

Diary Entry - Day 79

Dear Diary,

Tommy keeps changing the script on us.

Yesterday, during what was supposed to be another “Conqueror’s Night,” he suddenly got quiet and uncomfortable. After Lauren called him “such a powerful king” while riding him, he stopped her and said:

“…I don’t like this either. It feels fake. Like you’re all making fun of me in a different way.”

We were confused. He took a deep breath and finally told us what he actually wants:

“I just want you to be nice to me. Like… really nice. Motherly. Even when you’re fucking me really rough. Call me sweet names. Stroke my hair. Tell me I’m a good boy. Praise me like a caring mom would, even while you’re **** on my cock or slamming your ass down on it.”

The room went silent again.

This boy is complicated.

The New Dynamic: Gentle Mommy Treatment + Rough Sex

We all agreed immediately. At this point we’re too addicted to risk losing him over his changing moods. So we switched again — this time to a softer, nurturing style.

Last night we had our first proper session under the new rules.

Group Session at My House

We dressed in soft, maternal outfits — sundresses, cardigans, comfortable lingerie that made us look like caring moms rather than sluts.

Tommy lay on my big bed. We surrounded him.

I went first. I straddled him and sank my ass down onto his thick cock in one smooth motion, taking him raw and deep. I started bouncing hard — rough, aggressive, my ass rippling loudly as I rode him. But my voice and touch were completely gentle:

“Aww, that’s my good boy…” I cooed softly, stroking his sweaty hair and cupping his chubby cheek. “You’re doing so well, sweetheart. Mommy’s tight asshole feels good, doesn’t it? You’re such a sweet boy for letting me use you like this.”

Tommy moaned loudly, clearly loving it. His hands grabbed my hips as I slammed down harder.

Sarah crawled beside us and gently kissed his forehead while I kept riding him roughly. “You’re such a good boy, Tommy. Mommy Sarah is so proud of you. Keep filling my friend’s ass, baby.”

Mia, who usually degrades him the hardest, struggled the most but tried. While sitting on his face and grinding her pussy on his mouth, she stroked his belly gently and whispered, “There you go, sweet boy… eat Mommy’s pussy nicely. You’re doing perfect.”

Lauren was the most natural at it. She deepthroated him aggressively, gagging and **** loudly with tears running down her face, but between gasps she kept saying lovingly, “You’re Mommy’s favorite boy… such a brave, good boy for letting me take you so deep.”

Vanessa was the most awkward, but even she managed: “Good boy, Tommy… take what you need from us.”

Every time he got close, we’d all pet him, kiss his face and chest, and encourage him softly:

“Come for Mommy…”

“You’re allowed to cum, sweet boy…”

“Fill Mommy’s ass, baby. You’ve earned it.”

He came six times in under two hours — way more than usual. The combination of rough, filthy sex with tender, motherly affection seemed to break something in him. He was whimpering, almost emotional, clinging to us.

My Reflections

This version feels the strangest yet. We’re still destroying our holes on his cock — riding him like animals, **** ourselves on him, taking him in the riskiest public places — but we’re doing it while babying him, praising him gently, and treating him like a precious boy who needs love.

He especially loves when we call ourselves “Mommy” while he’s balls-deep in our asses.

I’ve noticed he’s started cuddling more afterwards. He wants us to hold him, stroke his back, and tell him he’s a good boy while his cum is still leaking out of us.

This whole thing has become even more twisted. We’re not just his sluts anymore.

We’re his caretakers.

His motherly lovers.

His gentle enablers of depravity.

And somehow… it feels even more dangerous than the degradation or the conqueror praise.

Diary Entry - Day 80

Dear Diary,

Tommy keeps refining exactly what he wants from us. After trying the “Conqueror” praise and then the motherly style, he told us yesterday that the “Mommy” talk felt weird to him too.

What he actually wants is simpler:

He wants us to treat him kindly and warmly — like he’s just a normal kid from our sons’ class. Like a sweet, slightly awkward classmate who we’re being extra nice to. Supportive, friendly, encouraging, but still very affectionate. No “Mommy,” no heavy domination, no over-the-top worship.

Just warm, caring MILFs being gentle and kind to their son’s fat, ugly classmate… while using him for extremely rough sex.

New Dynamic: Kind Classmate Treatment

We tested it last night in a group session at Lauren’s house.

Session Details

Tommy was lying on the couch. We surrounded him, smiling softly like we were helping a shy boy with his homework.

I went first. I straddled him, pulled my skirt up, and sank my ass down onto his thick cock in one smooth motion. I immediately started riding him hard — rough, fast, deep bounces that made my ass clap loudly against his fat thighs. But my voice stayed gentle and caring:

“You’re doing so well, Tommy,” I said sweetly, brushing hair out of his eyes. “Such a good boy for letting me ride you like this. I know it feels really good.”

Sarah knelt beside us, gently stroking his chest while I slammed down on him. “You’re such a nice young man, Tommy. We’re really glad you’re friends with our sons. You can always come to us when you need anything.”

Lauren was the most natural at this new style. While taking his cock down her throat in long, gagging strokes (tears running down her face), she would pull off for air and say softly, “You’re so brave for handling all of us, Tommy. We really appreciate you.”

Even Mia toned down her usual intensity. While grinding her pussy on his face, she gently rubbed his belly and said, “That’s it, Tommy… you’re doing great. Just relax and enjoy yourself.”

Vanessa still struggles with being genuinely nice, but she managed: “You’re… surprisingly fun to be around, Tommy. Keep going. We like having you here.”

Every time he got close, we’d encourage him warmly:

“You can cum whenever you want, sweetie.”

“We’ve got you, Tommy. Just let it all out.”

“You feel really good inside me…”

He came seven times last night. The combination of extremely rough, raw anal and throat fucking paired with gentle, kind, almost nurturing encouragement seems to be exactly what he was looking for.

How We Talk To Him Now

We use his name a lot and speak to him like he’s a polite young classmate.

Lots of gentle touching — stroking his hair, rubbing his back, holding his hand.

Encouraging and positive language: “You’re doing great,” “We enjoy spending time with you,” “You make us feel really good.”

We still do all the filthy things — riding him in public, taking him in every hole, multitasking while he’s inside us — but we stay warm and caring the entire time.

Tommy seems the happiest he’s been. He’s less nervous and more relaxed during sessions. Afterwards he likes when we cuddle him and chat casually about school or video games, like we’re just friendly neighborhood moms looking after their son’s classmate.

This version feels the most twisted yet.

We’re five married women in our 40s, letting our sons’ fat, ugly classmate use our mouths and asses as hard as he wants… while we smile at him sweetly and treat him with genuine kindness.

It’s somehow more humiliating than the degradation ever was.

Diary Entry - Day 82

Dear Diary,

Today I took Tommy to the big Victoria’s Secret store at the mall. I told Mark I was going shopping for new underwear. Tommy came along as “Jake’s friend who needed help picking a birthday gift for his mom.” That was my cover story.

The store was fairly crowded — lots of women browsing, a few couples, and sales assistants walking around. Perfect.

We spent almost two hours there, and I took 9 loads from him.

Session 1-3: In the Panties Section

I led Tommy to a quiet corner with racks of lace panties. I picked out several pairs, then bent over pretending to look at the lower shelf. Tommy immediately stepped behind me, lifted my sundress, and pushed his thick cock into my ass.

I stayed bent over, pushing back onto him with firm, deep bounces while holding up different panties like I was comparing them. A sales assistant walked right past us.

I smiled at her warmly and said, “Tommy’s helping me choose. He has good taste, don’t you think?” while my asshole clenched around him. Tommy came inside me during the conversation. I stood up straight, cum already starting to drip down my thigh, and thanked the assistant sweetly.

Session 4-6: Fitting Room Area

The fitting rooms were busy but had a large communal couch outside for waiting partners. I told Tommy to sit down, then I “modeled” for him.

I went into a fitting room, changed into a tiny black lace bodysuit, and came out to show him. While standing right in front of him (in full view of other shoppers), I straddled his lap and sank down onto his cock. I rode him hard — rough, fast movements that made my ass slap against his thighs.

“You’re being so helpful today, Tommy,” I whispered gently, stroking his hair. “Such a good classmate for coming with me. Does this feel nice?”

A woman sitting nearby kept glancing over. I just smiled at her and said, “He’s helping me pick something special for my husband. Boys his age give very honest opinions.” I kept riding him the whole time. Tommy filled my ass twice while I was modeling different pieces.

Session 7: Against the Mirror

I pulled him into one of the larger fitting rooms with me (door not fully closed). I faced the mirror, bent slightly forward, and let him fuck my ass from behind while I tried on bras.

I kept eye contact with myself in the mirror while pushing back onto him roughly. “You’re doing so well, Tommy. I’m really glad you’re here with me,” I said softly, my voice sweet and caring even as my ass took a pounding. Someone tried the door next to us. I just moaned quietly and told Tommy, “It’s okay, sweetie. Just keep going.”

He came deep inside me again.

Session 8-9: Near the Cash Register

While I was paying for everything (I bought him a pair of silk boxers as a gift), I stood close to Tommy and reached behind me under my dress. I guided his cock back into my leaking asshole and slowly rode him while the cashier rang me up.

“You’ve been such a patient young man today,” I told him kindly, gently rubbing his arm. “I really appreciate you spending time with me.”

The cashier smiled at us, thinking I was just being a nice neighbor mom. Tommy pumped his final two loads into me while I signed the receipt.

By the time we left the store, my legs were shaky, my ass was overflowing with cum, and I was walking very carefully. I bought over $400 worth of lingerie — most of it for our future sessions.

On the drive home, Tommy was quiet and happy. I reached over and gently stroked his thigh while driving.

“You were such a good boy today, Tommy. Thank you for coming with me.”

He smiled shyly. I think this gentle, kind treatment really makes him feel safe and wanted — even while I’m letting him destroy my holes in public.

I’m starting to realize how deeply we’ve all fallen into this. I’m taking my son’s ugly, fat classmate lingerie shopping and letting him cum inside me in the middle of a busy store… all while treating him like he’s the sweetest boy in the world.

And I don’t want to stop.

Diary Entry - Day 84

Dear Diary,

After our session today, I decided to ask Tommy more about his school life. We were lying on the couch in the living room (Jake was at baseball practice). I had just finished riding him for the third time that afternoon, my ass still leaking his cum onto the towel I placed beneath us. Instead of getting up right away, I gently stroked his hair and asked him softly, like a caring neighbor mom would:

“Tommy, sweetie… how’s school been going lately? You know, besides everything with Jake and the other boys.”

He seemed surprised I asked. He’s not used to us talking about normal things. But he opened up a bit while I gently played with his soft cock.

What Tommy told me:

School is still pretty rough for him, even after Jake stopped the direct bullying.

He gets made fun of a lot for his weight. Some kids call him “Tommy Two-Ton” or “The Walking Belly” behind his back.

He eats lunch alone most days in the library because the cafeteria is too intimidating.

He’s failing two classes (Math and History) because he spends so much time thinking about us instead of studying.

He has almost no friends his own age. The only people who are nice to him at school now are a couple of teachers who feel sorry for him.

He admitted he used to jerk off in the bathroom between classes thinking about me before our “transaction” started. Now he sometimes sneaks texts from me during lunch.

He got a little sad talking about it. So I pulled him closer, kissed his forehead gently, and let him suck on my tits while I stroked his hair.

“You’re a good boy, Tommy,” I whispered kindly. “School can be hard, but we’re always here for you. You can come over whenever you need to feel better.”

That cheered him up. He got hard again almost immediately. I rode him slowly for another round while continuing to talk sweetly to him about school.

My Thoughts

Hearing about his lonely school life made me feel a strange mix of pity and arousal. This fat, awkward, ugly boy has no real life outside of video games and getting used by five married mothers. And yet… those same mothers are completely addicted to him.

I told the group chat about our conversation. Sarah wants to help him with his homework next time. Lauren offered to make him lunch sometimes. Even Vanessa said (reluctantly) that she could tutor him in math.

We’re getting deeper into this. We’re not just using his cock anymore.

We’re becoming part of his daily emotional support system too.

I wonder how long it’ll be before one of us gets a call from the school because Tommy’s “nice neighbor moms” are spending too much time with him.

Diary Entry - Day 85

Dear Diary,

After our conversation about school yesterday, I wanted to know more about Tommy as a person. So today, after Jake left for practice, I invited Tommy over. We started in the kitchen, but things quickly moved to the living room couch.

I rode him slowly and deeply while we talked. My hips moved in long, firm circles, taking every inch of his thick cock in my ass, but my voice stayed soft and caring the whole time.

I brushed his sweaty hair back from his forehead and asked gently:

“Tommy, sweetie… what do you like to do for fun? Besides spending time with us, of course.”

He looked a little shy at first, but gradually opened up while I kept riding him at a steady, pleasurable pace.

Tommy’s Hobbies:

Video Games

He’s really into gaming. His favorites right now are Elden Ring, Fortnite, and a mobile game called Genshin Impact. He said he sometimes plays for 6–8 hours straight. He even asked if I would sit on his lap while he plays ranked matches sometime. I smiled and told him, “That sounds nice, Tommy. I’d love to keep you company while you play.”

Anime

He watches a lot of anime — especially action and “ecchi” series. He admitted he has a huge collection of hentai saved on his computer. His current favorite is something called Redo of Healer (I pretended not to know how dark it was). He likes the over-the-top fantasy stuff.

Trading Cards

He collects Pokémon cards and some sports cards (mainly basketball). He gets genuinely excited talking about rare pulls. I told him I’d take him to the card shop sometime if he wants.

Junk Food

Eating is basically a hobby. He loves ordering massive amounts of fast food — especially pizza, fried chicken, and milkshakes. He proudly told me his record is eating an entire large Meat Lover’s pizza while someone was “using him.”

Building Gunpla Models

Surprisingly, he also likes building Gundam plastic models. He has a small collection in his room. He says it helps him relax when he’s stressed.

While he was telling me all this, I started bouncing harder on his cock, my ass slapping loudly against his thighs. Even then, I kept my voice warm and encouraging:

“Those all sound like really fun hobbies, Tommy. I’m glad you have things you enjoy. You’re such a sweet boy with interesting interests.”

He came hard inside me right after I said that.

After he finished, I stayed seated on him, gently stroking his chest while we continued talking. I promised him I would try to support his hobbies more — maybe watch an anime episode with him, or help him organize his card collection.

My Thoughts

The more I learn about him, the more real he becomes. He’s not just a cock attached to a fat body. He’s a lonely, awkward teenage boy with simple hobbies and insecurities.

And yet five married women in their 40s are completely obsessed with him.

There’s something strangely intimate about knowing all these little details while I’m still leaking his cum. I feel like I’m becoming more than just his secret slut.

I’m becoming part of his actual life.

Diary Entry - Day 87

Dear Diary,

I called an emergency meeting with Sarah, Mia, Lauren, and Vanessa yesterday afternoon. We sat in my living room drinking wine while I told them everything Tommy had shared about his lonely school life and simple hobbies.

The reaction was immediate.

Sarah’s eyes softened. “That poor boy… eating lunch alone in the library every day? That’s heartbreaking.”

Lauren looked like she was about to cry. “He’s just a sad, awkward kid. No wonder he’s so attached to us.”

Even Mia and Vanessa, who are usually colder, admitted they felt pity for him. Vanessa muttered, “He really is pathetic… but in a way that makes me want to spoil him more.”

We all agreed: we need to take better care of Tommy. And the best way to make him happy is to go even harder on the sex — full speed, raw, loud, filthy depravity in public — while still treating him with gentle kindness and perfect excuses.

New Group Philosophy: “Maximum Pleasure for Tommy”

We decided to push our limits. Louder, sloppier, riskier. Wet squelching sounds be damned. We’ll just become experts at covering it up with sweet voices and believable stories.

Today’s Group Test Run - Crowded Downtown Plaza

We took Tommy to the busy outdoor plaza in the city center (fountains, food trucks, hundreds of people). We wore flowy summer dresses with nothing underneath.

Session 1-3: On a Public Bench

I sat on Tommy’s lap first, facing away from him. I pulled my dress over us slightly and slammed my ass down on his cock at full speed. The wet, loud squelch-squelch-squelch sounds were completely obvious.

A couple walked right past us. I smiled warmly at them while bouncing aggressively.

“Oh Tommy, your back massage technique is so strong today!” I said sweetly. “You’re such a helpful young man.”

The squelching got even louder as I rode him harder. Tommy groaned. I kept bouncing without slowing down until he pumped his first load into me.

Sarah went next. She rode him even more violently, her big ass rippling loudly. The wet sounds echoed. When an old lady stared, Sarah smiled kindly and said, “Tommy’s helping me with my hip exercises. The doctor recommended vigorous movement. He’s such a good boy for helping all of us.”

Session 4-6: Against the Fountain Railing

We bent over the stone railing side by side. Tommy fucked us one after another at full speed from behind. The loud, sloppy anal sounds mixed with the fountain water.

When a group of tourists walked by, Lauren (who was currently getting pounded) turned her head with a sweet smile, voice completely calm:

“Tommy’s showing us a new stretching routine. He’s very talented at it. Would you like him to show you too?”

The tourists smiled awkwardly and kept walking while Tommy railed Lauren’s ass with loud, wet slaps.

Session 7-9: Food Truck Line

We stood in line for tacos. I was in front of Tommy. I reached back, guided him into my ass, and he fucked me standing at full speed while we waited. The squelch-squelch-squelch was unmistakable.

When the man behind us gave us a weird look, I turned and said politely, “Tommy’s helping me fix my posture. I’ve had terrible lower back pain lately. He’s such a considerate classmate.”

Tommy came inside me right as we reached the front of the line. I ordered food normally while cum ran down my legs.

After the Outing

We all took Tommy to get ice cream afterwards and sat with him on a bench, gently stroking his back and hair while cum leaked out of all of us.

Lauren whispered, “We’re going to take good care of you, Tommy. You don’t have to be lonely anymore.”

Mia (trying her best to be gentle): “You deserve to feel good. We’ll make sure of it.”

Vanessa, despite herself: “We’ll keep doing this for you… because you need it.”

Tommy looked genuinely happy. Almost emotional.

We’re now fully committed. The pity we feel for this lonely, fat, ugly boy has only made us more depraved. We’re going to fuck him harder, louder, and in even riskier places — all while treating him like the sweet, unfortunate classmate who finally found kind women who care about him.

I’ve never felt more twisted.

Or more turned on.

Diary Entry - Day 89

Dear Diary,

We’ve all been talking a lot about how to properly take care of Tommy. The sex is only one part of it now. Because we pity him so much — this lonely, awkward, overweight boy who never had real friends or affection — we’ve started doing many other things for him.

What We Do For Tommy (Besides Sex):

1. Feeding Him & Cooking

We take turns cooking for him. Sarah makes him lasagna and cookies. Lauren bakes him fresh brownies. I usually cook big hearty meals — fried chicken, mashed potatoes, mac and cheese — because he loves comfort food. We pack him lunches almost every day with little encouraging notes inside (“Have a good day at school, Tommy. We’re proud of you.”). Mia even brings him protein shakes “to help him get stronger.”

2. Helping With School

Lauren tutors him in English every Tuesday.

I help him with Math.

Mia (surprisingly) tutors him in History and gets very strict but still kind.

We’ve improved his grades from Ds to Bs in just a few weeks. We also write his essays sometimes when he’s overwhelmed.

3. Supporting His Hobbies

Sarah bought him a high-end gaming PC setup.

I take him to the card shop to buy new Pokémon cards.

Lauren watches anime with him (even the perverted ones) and sits on the couch cuddling him while they watch.

Vanessa (reluctantly) bought him a expensive Gunpla model kit.

4. Emotional Support

We listen to him when he talks about feeling ugly or lonely. We give him lots of gentle hugs, head pats, and reassurance. After school he often comes straight to one of our houses just to vent. We never judge him. We just smile warmly and tell him he’s a good boy who deserves nice things.

5. Practical Help

We do his laundry sometimes.

We bought him a whole new wardrobe that actually fits him properly.

I drive him to and from school on days when he doesn’t want to take the bus.

Sarah helped him organize his messy room last weekend.

6. Including Him

We’ve started bringing him on “normal” outings — movies, mini-golf, bowling — pretending he’s just a friend of our sons. We treat him kindly in public like he’s under our care.

Group Chat Agreement

We now have an official rule: Every MILF must do at least three non-sexual caring things for Tommy per week. It’s become a competition of who can spoil him the most.

Vanessa still complains sometimes (“Why are we acting like his actual moms?”), but even she bought him new shoes after he mentioned his old ones hurt his feet.

My Thoughts

We started this as a transaction to stop Jake from bullying him. Now we’re basically acting as his secret harem of caretakers. We fuck him senseless in public — loud, raw, squelching, no mercy — but then we feed him, hug him, help him with homework, and tell him how glad we are that he’s in our lives.

The contrast is insane.

We’re ruining our bodies and marriages for him… while also being the kindest people in his sad little world.

He’s starting to depend on us emotionally. And we’re starting to enjoy being needed by him.

I don’t know where this is going anymore.

But none of us want to stop.

Diary Entry - Day 92

Dear Diary,

This whole situation with Tommy is starting to seriously affect our home lives. We’re all feeling the strain, but none of us are willing to stop. If anything, the secrecy is making the sex even more intense.

My Family (Mark & Jake)

Mark:

He’s become extra attentive lately, almost like he can sense something is different. He keeps trying to initiate romantic sex, which feels incredibly vanilla and boring compared to the raw, loud, squelching anal I get from Tommy multiple times a day. I’ve been faking orgasms more than ever.

Last night he asked why I’m “always so tired and distracted.” I lied and said I’ve been helping several kids from Jake’s class with after-school mentoring. He seemed proud of me for being “such a caring mother figure.” The guilt hit me hard for a moment… then Tommy texted me asking if he could come over after dinner, and the guilt disappeared.

Jake:

My son has noticed Tommy is around the house way too much. He asked me yesterday, “Mom, why is Tommy always here? I thought you hated him.” I told him I felt bad about the bullying and that I’m trying to be a good influence. Jake just shrugged and said Tommy seems “less annoying lately.”

The most dangerous part: Jake almost walked in on me riding Tommy in the laundry room two days ago. I had to quickly pull my dress down and claim I was “showing Tommy how to use the new dryer settings.” Jake gave us a weird look but left.

The Other MILFs

Sarah & Richard:

Sarah’s husband is starting to get suspicious about how much time she’s spending “mentoring.” She’s been coming home late with her ass wrecked and leaking. Richard commented that she’s been “walking funny lately.” Sarah just laughed it off and said she started a new intense Pilates class. She’s lying more smoothly now.

Mia & David:

Mia’s husband David is the most suspicious. He’s asked her directly why “that fat kid” is always around. Mia told him they’re doing a community service project. David isn’t fully convinced. Mia says the risk is making her fuck Tommy even harder.

Lauren & Paul:

Paul is still completely clueless and sweet. He actually likes Tommy now and thinks it’s “great that Lauren is so involved with the less popular kids.” He has no idea his innocent wife is getting her throat and ass destroyed daily by that same boy.

Vanessa & Victor:

Vanessa’s husband is the least suspicious because he’s so self-absorbed. But her son has started complaining that “Tommy is always at our house.” Vanessa punished her son by grounding him, then rewarded Tommy by letting him fuck her in the backyard while her family was home.

Overall Group Impact

We’re all becoming better liars. We’re more distant during family dinners because we’re constantly thinking about the next time we can get Tommy inside us. We schedule our family time around Tommy’s availability. Some of us have even started turning down sex with our husbands because we’re too sore or full of Tommy’s cum.

The guilt comes in waves, especially at night. But then we remember how lonely Tommy was before us — eating lunch alone, getting bullied, feeling worthless — and we convince ourselves we’re doing something good for him.

We’re hoping Tommy never gets properly “found out.” We’ve all become experts at making excuses and covering our tracks. But the fear of getting caught is always there… and honestly, it makes everything feel even better.

I don’t know how much longer we can keep this perfect double life going.

Diary Entry - Day 96

Dear Diary,

We had our most insane idea yet during last night’s group chat.

Sarah suggested it first: “What if Tommy’s cum was our only makeup? No foundation, no blush, no mascara — just his loads dried on our faces. We go out like that and act completely normal.”

We all went silent for a moment… then agreed immediately. The combination of gentle kindness toward Tommy + **** public humiliation was too perfect to resist.

Day 96: “Tommy’s Facial Day”

We all skipped real makeup this morning. Instead, we met at Mia’s house before 9 AM. Tommy was already there, excited and nervous.

We took turns sucking and stroking him until he gave each of us a thick facial. We didn’t wipe anything off. We let it dry naturally on our skin — shiny, crusty, and obvious. Some of us even rubbed it in like expensive moisturizer while smiling sweetly at him and saying, “Thank you, Tommy. You’re so generous.”

Then we went out into the world.

The Public Parade

1. Grocery Store (Morning)

All five of us went shopping together with Tommy. Our faces were clearly covered in dried cum — especially noticeable under the bright lights.

When a store employee stared at us, Lauren smiled kindly and said, “We’re testing a new organic face mask Tommy recommended. It’s all natural and very nourishing. He’s such a helpful boy.”

I bent over in the dairy aisle to grab milk while Sarah rode Tommy quickly behind me. The loud squelching drew attention, but Mia casually explained, “Tommy’s helping Sarah with her posture exercises again. He’s very talented.”

2. Coffee Shop

We sat in the busy outdoor seating area. Our cum-crusted faces were on full display to everyone walking by. Vanessa (who hated this the most) still participated. When a group of young moms from school sat near us, I said cheerfully:

“Tommy helped us try this new skincare routine. It’s a bit sticky at first, but it leaves our skin glowing, don’t you think?”

One woman looked visibly uncomfortable. Sarah just smiled warmly and offered them some of Tommy’s “special homemade moisturizer” (a small bottle we filled with his cum earlier).

3. Parent-Teacher Conference at School

This was the boldest. We attended a scheduled meeting with several teachers and other parents. All five of us had thick, dried layers of Tommy’s cum on our faces and even some in our hair.

When Jake’s English teacher kept staring at my face, I gently touched my cheek and said, “Oh, this? It’s a new collagen treatment Tommy found for us. He’s been doing research on natural beauty remedies. Such a thoughtful young man.”

The teacher nodded awkwardly and continued the meeting. Meanwhile, under the long conference table, Lauren was slowly riding Tommy’s cock while maintaining perfect eye contact with everyone.

4. Park & Mall

We walked around the crowded park and later the mall for almost two hours. People stared. Some whispered. A few took sneaky photos. We just kept smiling and treating Tommy kindly — holding his hand, stroking his back, buying him snacks.

Every time someone looked too long, one of us would say something like:

“It’s a new trend called ‘natural glazing.’ Very popular in Korea.”

“Tommy’s aunt is a dermatologist. She recommended this.”

“It’s actually really good for the skin. You should try it!”

Evening Session

By the time we got home, our faces were flaky and tight. We let Tommy give us fresh loads to “reapply” before we finally washed our faces.

Tommy seemed overwhelmed but incredibly happy. We kept telling him how proud we were of him and how much we appreciated him “helping us look beautiful.”

This might be the most depraved thing we’ve done yet — proudly wearing this ugly boy’s cum all over our faces in public, in front of teachers, neighbors, and strangers, while pretending it’s completely normal.

The pity we feel for him has turned us into absolute monsters of depravity.

And none of us want to go back.

Diary Entry - Day 98

Dear Diary,

Today was intense. We took Tommy out for a “fun afternoon” at the big outdoor shopping district. All five of us were dressed nicely, walking around with him like proud aunties. We had already taken several loads from him — some in our asses, some fresh facials that we wore proudly as “skincare.”

We were crossing the street near the parking lot when it happened.

A black SUV came speeding around the corner, clearly not paying attention. Tommy was a little slow (he’s not the most coordinated) and was still stepping off the curb.

The car almost hit him.

The tires screeched. The driver slammed on the brakes at the last second, stopping just inches from Tommy’s leg. Tommy froze, looking terrified.

Our Reaction

We lost it.

All five of us immediately turned into protective mama bears.

Sarah stepped right in front of the car and slammed her hand on the hood. “Are you fucking blind?! You almost hit him!”

Mia was even more aggressive. She marched up to the driver’s window (a middle-aged man) and started yelling, “You nearly ran over this sweet boy! Do you have any idea how careless you are?! He’s just a kid!”

Lauren immediately pulled Tommy into her arms, hugging him tightly against her chest and stroking his hair. “Oh Tommy, sweetie… are you okay? That was so scary. Come here, baby.”

I stood between the car and Tommy, glaring at the driver. “You should be ashamed of yourself. This is a pedestrian area. Slow the hell down!”

Vanessa, surprisingly the most vicious, actually took a photo of the man’s license plate and said loudly, “I’m reporting you. This boy could have been seriously hurt because of your stupidity.”

The driver looked completely stunned. He tried to apologize, but we weren’t having it. We surrounded Tommy like a protective shield, all of us touching him, comforting him, and fussing over him while still glaring at the stranger.

The man eventually drove off looking shaken. Good.

Aftermath

We immediately took Tommy to a nearby bench. All five of us crowded around him, pampering him heavily.

I sat on his lap right there in public (my skirt covering us) and slowly sank down onto his cock while stroking his face. “You’re safe now, Tommy. That was so scary, but you’re such a brave boy.”

Sarah kissed his cheek gently. “We’ll always protect you, sweetie.”

While I rode him with long, deep strokes (the wet squelching clearly audible), Lauren fed him ice cream and Mia rubbed his belly comfortingly. Vanessa, for once, was soft and stroked his arm.

The adrenaline from the near-miss made us feral. I rode him harder than usual, my ass slamming down loudly in the middle of the busy plaza. When people stared at the obvious wet sounds, Sarah smiled sweetly and said, “Tommy got startled by a car earlier. We’re helping him calm down with some breathing exercises.”

Tommy came inside me twice in quick succession while we all comforted him. After he finished, we took turns kissing his forehead and telling him how important he is to us.

That incident made something very clear to all of us: Tommy has become ours. The idea of him getting hurt triggered something primal in every single one of us. We would have torn that driver apart if he had actually hit him.

We’re no longer just using him for sex and pity.

We’ve become genuinely possessive of this fat, awkward, lonely boy.

And that possessiveness is only making our depravity worse.

Diary Entry - Day 100

Dear Diary,

We decided to retire the “Tommy’s cum as makeup” experiment after a few close calls and one very awkward conversation with a teacher who asked if we had “skin conditions.” It was getting too risky and honestly a bit uncomfortable after a full day of flaking.

So we’ve gone back to swallowing… but we’ve made it much more intense and intimate.

New Rules:

All loads must be swallowed (no more facials).

We now gurgle, chew, and play with his cum in our mouths before swallowing.

We’ve added mouth-to-mouth sharing (snowballing) between us — passing his load from one MILF’s mouth to another.

We told Tommy about the change while gently stroking him. He seemed relieved. He likes watching us play with his cum more than seeing it on our faces.

Today’s Group Session – Mall Food Court

We took Tommy to the crowded mall food court for lunch. After eating, we found a large table somewhat in the open and began.

Session 1-4: Under the Table

I started by deepthroating Tommy aggressively under the table. When he came, I kept his load in my mouth. I didn’t swallow right away.

Instead, I pulled Sarah down for a long, sloppy kiss. We passed the thick cum back and forth between our mouths, gurgling loudly and chewing it playfully. The wet, obscene sounds were audible even above the food court noise.

When a family of four sat at the next table, Lauren smiled sweetly at them and said, “We’re trying some new chewing gum Tommy recommended. It’s very… creamy.”

I then passed the cum to Mia. She gargled it loudly, showing Tommy the white mess in her open mouth before kissing Vanessa deeply. Vanessa, still a bit **** but committed, chewed it slowly and visibly before swallowing with an exaggerated gulp.

We took turns like this for four loads. Every time Tommy came, we shared his cum between all five of us — gurgling, swishing, chewing, and passing it mouth-to-mouth like a perverted game.

Session 5-7: Standing in Line at the Drink Store

We stood in a tight circle while waiting for smoothies. I dropped down quickly, sucked Tommy off, and took the load. I stood up, cupped Lauren’s face, and snowballed it into her mouth. She gargled it loudly, then passed it to Sarah while we all smiled and chatted normally.

When the barista asked if everything was okay (because of the suspicious wet sounds), Mia answered calmly while still holding cum in her mouth:

“Everything’s perfect. Tommy is such a good boy for coming out with us today.”

Evening at My House

We got much filthier in private. We made Tommy sit on the couch while we knelt in front of him. After every load, we would:

Hold it in our mouths and gurgle it loudly so Tommy could hear.

Chew it slowly like it was candy.

Pass it around in long, sloppy chains of kissing — sometimes all five of us sharing one load in a circle.

Lauren has become especially good at this. She’ll fill her mouth, then kiss me deeply, pushing the warm cum into my mouth while gently stroking my cheek and saying, “Here you go, Tommy’s gift for you.”

Tommy loves this new version. He says watching us play with his cum like this while still being so kind to him makes him feel really special.

We’ve officially stopped the facial makeup. Swallowing, gurgling, chewing, and sharing feels even more depraved and intimate. We’re still treating him like the sweet, awkward classmate who needs our care… while turning his cum into our favorite shared treat.

The pity we feel for him has completely warped us.