Helping Tommy

Diary Entry - Day 17

Dear Diary,

God, my ass is sore again. But it's worth it. Little Tommy (that poor, sweaty, overweight boy from my son Jake's class) came by after school today like clockwork. Jake has been such a little shit to him—tripping him in the halls, calling him names, stealing his lunch. I caught Jake and his friends laughing about it last week, and I decided enough was enough. Tommy's mom even called crying. So I made the deal.

It's not sex. It's a transaction. My tight, married hole for his silence and for Jake to lay off. Simple. Efficient. And honestly? It's working. Jake's been nicer this week.

We did it eight times just this afternoon while I multitasked around the house. The family was everywhere.

First round: Tommy slipped in through the side door while I was folding laundry in the living room. Jake was playing video games ten feet away. I bent over the couch like I was reaching for a sock, hiked my sundress up, and let him shove that thick, ugly cock raw into my asshole. No lube. He likes it that way—says it feels "more real." I just kept folding towels, biting my lip, clenching around him as he pumped away like a **** animal. When Jake yelled "Mom, what's for dinner?" I answered in a perfectly normal voice: "Pasta, sweetie. Almost done here." Tommy grunted and flooded my guts with the first load of the day. I stood up, cum trickling down my thigh, and walked to the kitchen like nothing happened.

Second and third: In the kitchen while I chopped vegetables. I spread my legs, leaned on the counter, and let him rail me from behind while I kept slicing carrots. My husband walked in to grab a beer. Tommy froze balls-deep. I smiled sweetly and said, "Oh, Tommy's helping me reach the top shelf. He's such a good boy." Husband just nodded and left. Tommy kept thrusting the whole time, filling me again.

Fourth through seventh: Quick ones in the hallway, bathroom, and laundry room while I moved between chores. I'd bend over, he mounts me, pumps furiously for a few minutes, dumps his cum, and I keep moving. My ass is constantly leaking now. I can feel it squelching when I walk.

Eighth: Right before he left. I was saying goodbye at the front door, waving to Jake's dad who was pulling into the driveway. Tommy got one last brutal anal fuck standing up, my dress covering us, his fat belly slapping against my back. I came hard that time—my legs shaking—while telling my husband through the door, "Traffic was bad, huh honey?"

I don't count this as cheating. It's not romantic. It's not even pleasure for me most of the time (though my body betrays me and I cum anyway). It's just... keeping the peace. Protecting my son from becoming a bully. Tommy gets to empty his balls in my raw asshole 40-50 times a day on average now, and in return Jake leaves him alone. Everyone wins.

My hole is gaping and puffy. I can barely sit. But tomorrow he'll be back before school, during lunch break, after school, and probably sneak in at night while everyone's sleeping. I'll just keep multitasking. Keep making excuses.

"Tommy's just helping me with some heavy lifting."

"Nothing, I just dropped something."

"That's the washing machine making that sound."

I'm getting really good at this.

— Elena, the world's best multitasking mom

Diary Entry - Day 22

Broke my personal record today. 48 loads. Tommy skipped school and basically lived in my ass all day. I cooked breakfast with him inside me. Vacuumed the carpets while he fucked me doggy on the couch (Jake was upstairs). Even took a conference call for my part-time job while sitting on his lap in the home office, his cock buried to the balls in my wrecked hole. I sounded so professional while he pumped cum up my guts.

When my husband came home early and almost caught us in the garage, I just said I was "showing Tommy how to change the oil." He believed it.

Diary Entry - Day 29

Dear Diary,

It's been a full week since I hit that insane 48-load record, and things have shifted. Tommy is getting tired so much faster now. The poor boy is completely out of shape—after just a few minutes of him thrusting, he starts panting like he's about to have a heart attack, his fat belly heaving. So I’ve started doing all the work myself. I ride him. I bounce. I grind. I milk his cock with my asshole like it’s my full-time job now.

It’s still just a transaction. Nothing more. But I’ve discovered something new that makes him finish ridiculously fast: the risk. The closer we get to being caught, the harder he cums. So I’ve been pushing it on purpose.

Today alone we did it 42 times, and I handled almost every single one.

Morning, right after my husband left for work: Tommy snuck in through the back. Jake was still eating breakfast in the kitchen. I didn’t even let Tommy move. I pushed him against the wall in the hallway (literally five feet from the kitchen doorway), dropped my robe, and backed my ass onto his cock. I did all the bouncing—deep, wet, sloppy movements—while whispering, “Shhh… Jake’s right there. If you make a sound I’ll stop.” Tommy was trembling. I clenched hard around him and rode him until he pumped the first load of the day deep into my guts. I casually walked back into the kitchen with cum running down my legs and asked Jake if he wanted more orange juice. Normal mom voice and everything.

Mid-morning: While I was on a work Zoom call (camera on, professional blouse up top), I had Tommy sitting on the couch in the living room. I sat reverse cowgirl on him, my skirt covering the connection, and slowly rode him the entire meeting. Every time someone asked me a question, I answered calmly while my asshole swallowed every inch of him. I made sure to bounce harder right when I was speaking. Tommy was terrified and thrilled. He came twice during the call.

Lunch time was wild. Jake and two of his friends were playing video games in the living room. I brought them snacks, then “accidentally” dropped my phone under the coffee table right in front of them. I got on all fours, ass toward Tommy (who was pretending to play with them), and backed up onto him. I fucked myself on his cock in short, quick thrusts while picking up the phone, my face inches from Jake’s sneakers. One of the boys said “Mrs. Elena, your face is really red.” I smiled and said, “Just doing some exercises, honey.” Tommy exploded inside me right then.

Afternoon was non-stop. I rode him in the laundry room with the door half open while folding clothes. I rode him on the stairs while my husband was due home any minute. I even rode him in the garage while Jake was shooting hoops right outside—door cracked open so Tommy could hear the basketball. Every time I heard footsteps or voices, I rode him faster and deeper. The thrill of nearly getting caught makes him cum so hard it’s actually impressive.

By evening I was exhausted but strangely wired. My asshole is swollen, red, and constantly leaking. I’ve lost count of how many loads are inside me. I don’t even wear panties anymore—there’s no point.

I caught myself smiling when I almost got fully caught earlier. My husband walked into the bedroom while I was riding Tommy on the floor beside the bed (we had maybe three seconds). I quickly pulled the bed cover over us, sat down fully on Tommy’s cock, and pretended to be looking for something under the bed.

“Honey? What are you doing?” my husband asked.

“Just… cleaning some dust bunnies. Tommy’s helping me move the bed a little.”

Tommy came violently inside me while I looked my husband right in the eyes.

Diary Entry - Beach Vacation Day 1

Dear Diary,

We arrived at the beach resort this morning. My husband thought it would be a good idea to invite Tommy along for three days as a “peace offering” for Jake’s bullying. Jake wasn’t happy, but I insisted. Of course the real reason is that I can’t go four days without fulfilling my side of the transaction. Tommy’s cock has basically become part of my daily routine now.

I’ve already taken 31 loads in my ass today. I did almost all the work. Here’s how it went:

Session 1 (Airport parking garage, right before boarding the shuttle)

While my husband and Jake were loading the bags, I pushed Tommy behind a thick concrete pillar. I pulled my sundress up, backed onto him, and rode him hard standing up. He was already leaking pre-cum. I whispered, “Hurry, they’re coming back,” and slammed my ass up and down on his thick cock until he unloaded deep inside me. I fixed my dress just as my husband turned the corner.

Session 2-4 (On the shuttle bus to the resort)

I sat on Tommy’s lap the whole ride (40 minutes). My skirt covered us. I slowly rode him in tiny movements the entire time, clenching and grinding. He came three times. Each time I pretended to shift position because the seat was “uncomfortable.” My husband was sitting right next to us.

Session 5 (Hotel check-in, behind the luggage cart)

While my husband was at the front desk, I bent over behind a big luggage trolley in the lobby and let Tommy fuck me standing. I did the thrusting, pushing back hard. He filled me again while I smiled and waved at Jake across the lobby.

Session 6-9 (Hotel room, first 30 minutes after arrival)

Our family suite has two bedrooms connected by a living area. While my husband was in the shower, I rode Tommy on the couch in the living room. Jake was in the other room playing on his phone. I bounced aggressively, my tits almost spilling out of my bikini top. He came twice there. Then I quickly moved him to the balcony (curtains half-open) and rode him again while pretending to admire the ocean view. One more load while Jake walked past the balcony door.

Session 10-13 (Beach, under the umbrella)

We set up on the sand. I lay on my stomach on the big towel. Tommy lay behind me, cock inside my ass the whole afternoon. I did all the work — subtle rolling and squeezing of my hips while my husband and Jake were swimming. Every time they came back to the umbrella I froze with him buried to the balls. He came three times under that umbrella. I could feel the cum pooling underneath me in the sand.

Session 14 (Ocean, waist-deep water)

I swam out with Tommy while my family was building a sandcastle. In the water I wrapped my legs around him and rode him aggressively. The waves helped hide the motion. He came fast when a family swam nearby and I had to casually say “Hi!” while his cock twitched inside my asshole.

Session 15-20 (Changing tent on the beach)

I told my husband I needed to change into a different bikini. I pulled Tommy into the small fabric tent with me. For almost an hour I kept going in and out, each time riding him harder and faster. Six loads. I walked out each time with fresh cum dripping down my thighs, smiling innocently.

Session 21-25 (Hotel room before dinner)

Back in the suite. My husband was napping. Jake was on the balcony. I rode Tommy on the floor right beside the bed my husband was sleeping on. Five loads. Every time my husband stirred I rode faster because it made Tommy cum instantly.

Session 26-30 (Dinner at the beachside restaurant)

We had a big table. I sat next to Tommy. Under the long tablecloth I pulled my skirt up, sat on his cock reverse, and slowly rode him during the entire meal. He came five times. I kept normal conversation with my husband while my asshole milked him.

Session 31 (Elevator back to the room)

After dinner, in the glass elevator with another couple inside. I stood in front of Tommy, backed my ass onto him, and rode him standing while we went up 12 floors. He came just as the doors opened.

My asshole is completely wrecked — swollen, red, and leaking constantly. I’m walking funny but blaming it on “too much sun.” Tommy is exhausted, but the risk of getting caught in front of my entire family clearly keeps him going.

Diary Entry - Beach Vacation Day 2

Dear Diary,

Today I decided to switch things up. My asshole needed a break after yesterday’s 31 loads, so I told Tommy we’re doing rough face fucking instead. He was shocked but excited. I’m still doing almost all the work — aggressively taking him down my throat, gagging myself, controlling the pace. I discovered I love how sloppy and degrading it feels, especially when I push the risk of getting caught. The gagging sounds are harder to hide, which makes Tommy cum even faster.

We hit 37 sessions today. Here’s every single one:

Session 1 (Hotel balcony, early morning)

Husband and Jake were still sleeping. I dragged Tommy onto the balcony, dropped to my knees, and **** his thick cock straight down my throat. I face-fucked myself hard, nose buried in his fat pubic hair, gagging loudly. When Jake stirred inside, I kept going deeper, tears running down my face. Tommy exploded down my throat while I looked up at him with watery eyes.

Session 2-4 (Breakfast buffet line)

I stood behind Tommy in the crowded buffet. While everyone was distracted picking food, I quickly knelt, pulled his shorts down behind a tall plant, and slammed my face onto his cock. Three rapid, rough throat-fuckings — each under 30 seconds. I swallowed every drop, stood up, and casually asked my husband if he wanted coffee, cum still on my breath.

Session 5-8 (Under the beach umbrella)

Lying on my stomach on the towel, I had Tommy sit with a towel over his lap. I spent most of the morning with my head under the towel, aggressively sucking and gagging on him. Four loads. Every time Jake or my husband came back from the water I’d pop off with a wet gasp and pretend I was “looking for my phone.” The gagging noises were barely muffled.

Session 9 (Ocean water, shoulder-deep)

I swam out with Tommy. In the water I wrapped my lips around him and bobbed my head violently underwater, forcing him into my throat. I came up for air only when necessary, coughing and sputtering. He came twice while a group of people swam nearby.

Session 10-14 (Changing tent)

Back in the beach changing tent. I spent nearly an hour on my knees, roughly face-fucking myself on his cock. Five loads. I kept stepping out between rounds pretending to show my husband different bikinis, my voice hoarse and lips swollen.

Session 15 (Hotel elevator)

On the way up to the room after lunch, I pushed Tommy into the corner of the elevator. Two other guests were inside. I dropped down and gave him an extremely sloppy, gagging blowjob, the wet **** sounds echoing. He came down my throat just before the doors opened on our floor. I stood up smiling at the strangers with mascara running.

Session 16-20 (Hotel room while husband napped)

Husband was sleeping in the bedroom. I made Tommy sit on the couch in the living area and spent the next 40 minutes on my knees, brutally forcing his cock down my throat over and over. Five loads. I gagged so loudly at one point that my husband mumbled in his sleep. I just kept going harder.

Session 21-25 (Poolside lounge chairs)

While Jake and his dad were in the pool, I lay on the lounge chair next to Tommy and kept my head in his lap under a towel. I face-fucked him aggressively five times. When Jake called out “Mom, watch this dive!” I lifted my head mid-gag and cheered with a raspy voice, cum dripping from my chin onto my bikini.

Session 26-30 (Dinner at beach restaurant)

Under the table again, but this time full rough face fucking. I spent the entire meal periodically ducking under the long tablecloth, taking him balls-deep and gagging hard. Five loads. My husband asked why my voice was so hoarse. I told him I’d “swallowed some seawater earlier.”

Session 31-34 (Night walk on the beach)

We went for a “family stroll.” Every few minutes I’d pull Tommy behind a rock or palm tree and drop to my knees for a quick, rough throat session. Four loads. At one point my husband and Jake were only twenty feet away calling our names while I was forcing Tommy’s cock down my esophagus.

Session 35-37 (Late night in the suite bathroom)

After everyone went to bed, I locked us in the bathroom. I sat Tommy on the toilet and spent the next 30 minutes aggressively riding his cock with my throat — deep, sloppy, tears streaming. Three final loads. I swallowed every drop, my makeup completely destroyed.

My throat is raw and swollen. My voice is almost gone. I keep coughing up thick globs of cum. I told the family I caught a cold from the ocean breeze.

This face-fucking version feels even riskier and filthier than the anal. I’m getting off on how degraded I feel while still playing perfect wife and mother. Tommy can barely keep up, but the danger makes him cum like crazy.

Diary Entry - Day 36 (First day back home)

Dear Diary,

The vacation is over. We got back this afternoon, and I immediately switched back to anal. My throat is still sore from all the rough face fucking, but my asshole was aching for Tommy’s thick cock again. The deal continues, but something has changed. The risks I took on vacation woke something up in me. Now I’m deliberately choosing much riskier places… and I’m getting caught almost every single time.

I’ve accepted it. I don’t even try to fully hide anymore. The thrill of being seen while Tommy is balls-deep in my ass makes everything more intense. Tommy loves it. He cums harder when we get caught.

As for my “relationship” with Tommy… it’s still supposed to be just a transaction. He stops getting bullied by Jake, and in return he gets to empty his balls in me whenever he wants. But after weeks of this, it’s become something else. He’s still the same ugly, fat, sweaty boy — socially awkward, bad breath, terrible stamina. Yet he’s the only person who gets to use my married asshole like a fleshlight multiple times a day. I’ve started calling him “my little secret” in my head. I do all the work, I ride him, I milk him, I push the risks… and he just sits there panting and cumming. It’s strangely empowering and humiliating at the same time. I don’t love him. I barely even like him. But I’m addicted to what this does to me.

Here’s how today went. I got caught every single time.

Session 1

Right after we unpacked, Tommy snuck in through the back door. I pushed him into the kitchen pantry while Jake was in the living room playing games. I rode him standing, dress hiked up, bouncing hard. My husband walked in for a snack and saw us immediately — Tommy’s hands on my hips, my ass swallowing his cock.

I didn’t stop riding. I just looked at my husband calmly and said, “Tommy’s helping me reach the top shelf again. He’s taller than he looks.” My husband blinked, muttered “okay,” and walked out. Tommy flooded my guts while I kept eye contact with the closing door.

Session 2

Living room, ten minutes later. Jake was on the couch. I made Tommy sit on the armchair and sat on his cock reverse cowgirl, skirt covering us. I rode him openly. Jake turned around mid-session and saw my hips moving.

“Mom… what are you doing?”

I smiled sweetly, still bouncing, “Just stretching my back, sweetie. Sitting on the plane messed it up. Tommy’s letting me use him as a chair.” Jake looked confused but accepted it and went back to his game. Tommy came instantly.

Session 3

Bathroom. Door wide open. I was bent over the sink, riding Tommy hard from behind when my husband walked past. Full view.

“Honey, are you okay?” he asked.

I moaned softly and answered, “Yeah… just… constipation from the trip. Tommy’s giving me a… back massage to help me push.” The excuse was ridiculous, but my husband just said “Take it easy” and kept walking. Tommy pumped another load into me.

Session 4-7

Four times in the garage while my husband was washing the car outside. Each time he came in for tools or to grab something, he caught me riding Tommy on the workbench, on the hood, against the wall. Every single time I had a new excuse:

“Checking the tire pressure.”

“Tommy’s learning how to change wiper fluid.”

“Yoga pose.”

He believed all of them. Or pretended to.

Session 8

Dining room during family dinner prep. I was setting the table while riding Tommy sitting on a chair. Jake walked in, then my husband. Both saw everything.

I kept grinding slowly and said cheerfully, “Tommy’s teaching me a new core workout. You boys should try it sometime.” They both left the room awkwardly. Tommy came so hard he nearly passed out.

Session 9-12

Late evening sessions while everyone was home. Once in the hallway, once on the stairs, once in the laundry room with the door open, and once in our master bedroom while my husband was in the shower. Caught every time. My excuses are getting smoother and more shameless:

“Just helping Tommy with his posture.”

“He has a bad cramp, I’m stretching him out.”

“The washing machine is broken, I’m holding it steady.”

By the end of the night I had taken 19 loads total. My asshole is a gaping, cum-filled wreck. I’m leaking constantly and can barely walk straight. I told the family I pulled a muscle at the beach.

Diary Entry - Day 37 (Face Fucking Day)

Dear Diary,

After yesterday’s extremely risky anal marathon, I decided to switch back to rough face fucking again for today. My asshole is too sore and swollen to take another pounding, but my throat still feels eager. I told Tommy this morning: “Today you’re only using my mouth. And I’m doing all the work.” He just nodded, already breathing heavy.

I made it even riskier than last time. I’m deliberately getting caught more often. The moment someone sees me gagging on his fat cock, my pussy throbs. Tommy cums almost instantly when we’re busted. I still pretend it’s all part of the “transaction,” but I’m lying. I crave this now.

We reached 34 loads down my throat today. Here’s every single session:

Session 1-3 (Morning kitchen, right after husband left for work)

Jake was eating cereal at the table. I pulled Tommy behind the kitchen island, dropped to my knees and started aggressively face-fucking myself — loud, sloppy, gagging hard. Jake stood up to put his bowl in the sink and saw me with Tommy’s cock buried down my throat, mascara already running.

I pulled off with a wet pop and said casually, “Tommy’s helping me fix a stuck drawer down here. My hands are full.” Jake just said “Okay…” and left. I immediately slammed my face back down and took three loads in quick succession.

Session 4-7 (Living room while Jake played video games)

I sat Tommy on the couch and spent the next 30 minutes with my head in his lap under a blanket, brutally throat-fucking him. Jake was right next to us. Every few minutes Jake would glance over when he heard the wet gagging sounds. I got caught four separate times. Each time I’d lift my head, strings of spit connecting my lips to Tommy’s cock, and say things like:

“Tommy has a sore neck. I’m doing a special massage.”

Or “He swallowed a bug, I’m helping him cough it up.”

Jake believed every ridiculous excuse. Tommy fed me four thick loads.

Session 8 (Front porch, mid-morning)

Delivery guy was dropping off a package. I had Tommy standing against the wall and was on my knees giving him a violent, noisy throat fucking when the guy walked up. He saw everything. I didn’t stop. I just looked at the delivery man with watery eyes and said hoarsely, “He’s my son’s friend. He’s upset about school… I’m comforting him.” The guy left the package awkwardly. Tommy came down my throat while the delivery man was still watching.

Session 9-13 (Grocery store run)

I took Tommy with me to the supermarket. In five different aisles I dropped to my knees behind shelves or in the walk-in cooler and roughly **** his cock down my throat. Got caught by other shoppers twice. Once by the store manager. My excuses were smooth:

“Just helping him find something he dropped.”

“He has low blood sugar, I’m giving him candy.”

I swallowed five loads between the produce and frozen section.

Session 14-18 (Back home, afternoon chores)

While doing laundry, vacuuming, and cleaning, I kept pulling Tommy into rooms and slamming my face onto him. Got caught by my husband when he came home early — I was on my knees in the hallway, gagging loudly.

“Honey?” he asked.

I pulled off, spit dripping from my chin: “Tommy’s teaching me a breathing exercise for my yoga. It’s very intense.”

My husband just nodded and went to change. Five more loads down my already raw throat.

Session 19-24 (During Jake’s friends visiting)

Jake had three friends over. I served them snacks while periodically dragging Tommy to the bathroom or around corners for rough face fucking. I got caught three times by the boys. Each time I smiled with swollen lips and said:

“Tommy’s helping me move some heavy boxes.”

Or “We’re practicing for a school play.”

Six loads total. My voice was completely gone by this point.

Session 25-30 (Family dinner)

Under the table again. I spent most of the meal on my knees between Tommy’s legs, aggressively deepthroating him while my husband and Jake ate right above me. I got caught twice when they dropped utensils. Both times I came up with spit and cum on my face and said:

“Just picking up a napkin that fell.”

My husband looked suspicious but stayed quiet. Six thick loads swallowed during steak and potatoes.

Session 31-34 (Late night, master bedroom)

After everyone went to bed, I brought Tommy into our bedroom while my husband slept. I rode his cock with my throat for almost an hour — rough, sloppy, tears pouring down my face. Four final loads. My husband woke up once and saw me. I just whispered “Bad dream. Tommy’s comforting me,” and kept sucking until he fell back asleep.

My throat is destroyed. I sound like I’ve been screaming for days. My makeup is ruined, my jaw hurts, and I keep burping up the taste of Tommy’s cum. He barely had to thrust today — I did everything. I used him like a toy.

Our “relationship” is completely twisted now. He’s still ugly, still fat, still pathetic in every way… but he owns my holes. I serve him. I **** myself for him. I risk my marriage and family reputation for him. And the more I do it, the more I need it.

I told him tomorrow we’re going back to anal. Even riskier.

I’m no longer the mother I used to be.