Stepsister Ruins No Nut November

All characters in this story are over the age of 18.

***

My stepsister, Jan, was one of the hottest things in town. Everybody adored her, wanted her, befriended her and hated her.

I loved her and thought she was the perfect sister anyone ever asked for, even when she was a pain in the ass sometimes.

Unbeknownst to her, I always found myself jerking off with her panties or sometimes jerking off while watching her swim in the backyard. She was slim and a bit curvy, her teenage body still smooth and youthful.

We were the same age, and just a few months apart. The events I'm about to narrate happened when we were still in high school.

Our parents had married shortly after they met 7 years ago. It was a match made in heaven. They were both widowed single parents but coming from different situations. Jan's mom lost her husband in the military and my mom died in a car accident. For years, my dad seemed to be unable to get over the nightmare of losing a spouse until he started attending group therapy where he met Jill, Jan's mom.

What followed was a whirlwind romance that climaxed with a wedding less than a year after they met. A few days later, we moved into a five bedroom house in a residential area. The new life with new family was a breathe of fresh air and also an invitation to constant horniness. Both Jill and Jan were an eyeful. I couldn't keep my eyes off both of them. Eventually, we became close enough that I started referring to Janice as Mom and to Jan as sister.

While Jill was the stereotypical milf, Jan was the hot girl with blonde hair who everyone wanted to fuck. I'd surreptitiously jerk off thinking about the day I'd end up balls deep in Jan.

It was on one of those days while I was jerking off when she stormed into the room. Her short shorts and sleeveless top clinging to her body for dear life. Her blonde hair swinging easily on her head.

I was mid jerking off with her panties on my dick. I gasped and stopped mid shaft.

"Give me all my underwear now," she demanded, looking furious.

I quickly threw to her the pieces of underwear I had put on my bed. "I'm sorry, sis," I apologised.

"Don't ever fucking touch them again. I can't fucking deal with you anymore. I've been too patient but it seems you can't stop putting your hands on your dick."

"Look, I'm sorry. I didn't want to..."

"To get caught?" She finished my sentence.

"Yeah. That's one of the things I didn't want."

"I always knew you like to use my panties to jerk off, idiot. You're lucky I haven't told Mom and Dad otherwise you'd be in trouble. But now, I can't have you taking my panties all the fucking time. I need something to wear, you know. At least leave one or two in there."

"Okay, next time I'll make sure-"

"No fucking next time, bro. I've heard enough of being the good sister who let's you use her panties to jerk off. Go steal somebody else's panties."

"Like Mom's panties?"

"Nooo. Jesus! What's wrong with you? It's perverted to steal women's panties."

"Okay," I bullishly agreed. "Now can you go out and let me jerk off in peace?"

"Fine," she replied and her gaze went down to my hard dick. "Nice hard-on, bro."

She took her panties and stormed out. I ended up battering my dick and shooting my cum allover the sheets.

Once I was clear headed, I went to the laundry room where I found Jan washing her panties among her things. She sat on a chair across from the washing machine scrolling on her phone. She looked up and frowned.

"I want to apologise for what you caught me doing. I feel guilty and want to tell you I'm going to stop."

"Don't bother apologizing. I don't really care," she said. Somehow, she looked prettier when she was mad. Thank god I'd just unloaded a load.

"Okay, fine," I replied. "So why are you still angry?"

"Because I know you won't stop."

"Really? How do you know that?"

"Boys have constant sexual urges which you can't resist. We both know that."

"Seriously?"

"Yeah."

"I'm going to participate in No Nut November just to prove you wrong."

"What's No Nut November?"

"It's a yearly challenge for people to go through the whole month of November without cumming at all."

"Hmmm. I bet you can't do it."

"I bet I can."

"Fifty bucks says you can't."

"I'll raise the stakes. A hundred bucks says I can go the whole November without jerking off."

"We shall see about that," she said, sarcastically smiling.

The next day was November 1st. That night, I jerked off and came 3 times before it clocked midnight.

The next two days were normal. I did everything normally. Went to work, hang out with buddies at the bar. I talked my best friend, Jack, into joining me in my No Nut pursuit. We agreed to be each other's police and supporter.

A few days later, I woke up with a raging boner. Jan walked into my room, clad in a very low cut dress. She noticed my hard-on and smiled.

"What are you doing here?" I asked, trying to hide my dick, beneath my blanket.

She sauntered to my bedside and dropped down her handbag. "Ooops," she exclaimed, clearly feigning surprise. Then she slowly bent down to pick her handbag as her dress rode up her already visible smooth thighs. I watched in shock as her smooth silk panties came into view. She bent down til her dress rode up and I was clearly seeing her ass and the outline of her hidden pussy.

My dick got harder than I ever felt it. I'd jerked off at least once a day since my early teens. This was going to be a bigger task than I thought. Especially with Jan pulling these seductive stunts to make me fail.

"You like what you see?" She said, as she looked back to see if I was looking at her panties.

"C'mon. This is unfair. You can't do this. It's going to make me jerk off."

"That's the point, bro," she said. "There's money on the line and I made a stupid bet. Can't be losing all that money because you couldn't jerk off. I know you won't make it but the faster it happens, the better for me."

"This is fucked up, Jan." And I stormed out of bed and quickly closed myself in the bathroom.

"C'mon, I know you wanna do it. I can give you my panties." She shouted through the door.

I took off my boxer shorts and held my hard dick. Every impulse in my body told me to just pump it a few times and I'd be cumming and then I could probably lie and tell her I didn't. But I couldn't bring myself to do it. If I had jerked off, it would mean she had won. I went under the shower and took a quick cold one to cool down a bit. I realised Jan was going to make it very difficult to go through the whole month without cumming.

A few days later, we were eating dinner with Mom and Dad. I was sat next to Jan. Mom and Dad were across the table. Jan was clad in a very short dress showcasing her curves and cleavage.

"So how was school, guys?" Dad spoke.

"It was great today," I said.

"It was kinda harder than usual," Jan said, glancing at me seductively.

"Really? What was it?" Mom joined the conversation.

"Well, I kinda felt like everyone was looking at my outfit all day," she replied.

"Can you show us what you mean?" Dad said.

"Honey, don't you think it's inappropriate?" Mom interrupted.

"Hmmm, well if you say so," Dad answered cowardly.

"I don't really care anyway," Jan said before she stood up and her very short red tight dress came into view.

Her dress was so short her panties were almost visible. It also hugged her curvy ass and hips for dear life. It was like she had got a size too small. My dick immediately got hard as a rock. Thank God I didn't run into her at school.

She spun around making sure to give me and Dad an eyeful before she asked us what we thought with it.

"It's great. You shouldn't care what others think about you," Dad said.

"You look beautiful, honey," Mom said. "But you could try to dress more decently in public and like this," she pointed at Jan's dress, "when you're hanging out at a nightclub."

"C'mon, Mom," she pleaded. "You want me to be the prude."

"No, I just mean you can still look as good dressed a little less revealing."

Jan turned to me and spoke. "What do you think, bro?"

"I...I think you look hot," I cleared my throat and tried to act like I wasn't thinking about my stepsister's body.

"Thanks. That's good enough for me," she said while sitting back down to eat.

"Can we talk about something else?" Dad said.

Suddenly, I felt something touching my thigh. I looked down. It was one of Jan's hands. My dick seemed to be stretching toward her hand. I moaned out a little out of reflex.

"What?" Mom asked me.

"Uhhmm. I just bit my tongue, is all."

"Be careful, sweetie."

"I try to," I said.

Then I felt her hand move up brushing against my thigh and then dart across to my wrist. She dragged my hand and put it on her skirt. I stifled another moan. She moved my hand up and down her thigh slowly leading me into her inner thigh. Her smooth soft skin so easy to glide over. I wondered how Dad or Mom would react if they saw what we were doing. Incidentally, they were both hungry and focused on their plates.

She led my hand up her inner thigh, her short skirt rode up a little and suddenly my fingers touched some thin fabric. Her panties.

"Go ahead," she mouthed towards me. I pulled the thin strip aside and ran my fingers over her clit. She gasped and both our parents looked across the table immediately. I withdrew my fingers and decided to focus on my food.

"What is it?" Mom asked.

"I think I bit my tongue too," she said.

"What's going on with you two?" Dad questioned. "We should go see the dentist maybe."

"No, honey, don't overreact," Mom said.

After dinner, I went to Jan's room. She sat on her bed on her phone, now clad in her nightgown. I burst through the door without knocking.

"What the fuck were you thinking?" I blurted out as I closed the door behind me.

She smiled wickedly. "Don't you get it? This is revenge for using my panties and dumping them after."

"I told you I won't do it again but you keep tempting me. I'm your fucking brother."

"Well, hmmm, not technically," she said. "And that means I can do whatever the fuck I want with you."

"This is fucked up, Jan."

"As fucked up as using my panties?"

"Fuck you," I said before storming out of her room.

I heard her laugh at me as I entered my room.

I looked at the calendar. It was only November 9th so I had a full three weeks to deal with her tempting me. It suddenly seemed like a long time.

I decided to keep avoiding her everywhere. If I woke up and early and left for school and then worked in the evening til late, I'd not have to run into her.

The next day, I woke up early only to realise Jan was standing by my bedside holding a pair of black lace panties.

"What the-" Before I could finish my sentence, she stuffed the panties into my mouth and ran out of my room. I took the panties and put them on my bedside table. My dick was already rising seeing them so near my bed. The need to burst a nut was very alluring.

I just quickly jumped into the shower but still after ten minutes of cold water on my body, my dick was still rock hard. I started to think I wasn't going to last.

I went to school normally and then went to work. Mom called me asking where I was. I told her I'm on my way. By the time I arrived at home, it was coming to 11pm.

The next few days went on like this. At school, we were in different classes and there was no reason to meet and whenever we would be within distance of each other, I'd quickly dart away, unnoticed.

One day, I came back late and went straight into my room. At some point, I decided to go take a shower. I pulled the curtains and took my time getting rid of the tiredness.

When I was done, I climbed out naked with a swinging hard dick. I was now getting accustomed to the almost constant hardness I had to endure. Just as I cleaned off, Jan walked into the room. She had a night robe around her. She gasped in surprise at seeing my dick. The strap around her waist pulled slightly apart and I could see her tits. They were sexy.

She quickly moved across the room and placed her hands around my dick. I moaned a little and pushed her hands away.

"Hey, stop it. What on earth is wrong with you?" I said.

She giggled and said, "Can I touch it?"

"No, you can't," I replied. But she went ahead and touched my dick while I tried to stay away from her.

"It's okay. You don't have to touch yourself. I can do it for you," she said, stroking my shaft. I moaned softly.

"No, I can't cum now," I resisted.

"You can't cum just by yourself. But another person can help you out. Besides, we both know you want to," she said, still stroking my dick. She showed me her tits and moved my hands to them. I touched her nipples and pulled and tweaked them. Her robe fell to the ground, revealing her completely nude body. Her pussy had a few blonde hairs around it. I moved one hand down and started rubbing her clit. She moaned and shuddered. I pushed two fingers into her pussy and fucked her.

She kept stroking my dick and using her saliva as lube.

"I can't do this," I protested, feeling a bit of precum coating her painted nails. "This is incest."

"Who the fuck really cares?" She tried to distract me by stroking my cock faster.

I moaned louder. She kissed my neck, as I realised I was close.

"I'm close," she muttered. "Keep fucking my pussy with your fingers. Fuck me just like that. Keep pulling on my nipples."

I did as I was told. I fingerfucked her pussy while rubbing on her clit and twisting and biting her nipples. She let out a muffled scream. The next thing I knew, she was convulsing like a mad woman as her warm cum sprayed onto my fingers. She lost control of herself and seemed to curl around my fingers, mumbling unclear words.

I raised my hand to show her my cum covered hand. She giggled and went back to stroking my dick.

"I'm sorry I'm about to ruin your challenge," she said breathlessly. "But I owe you an earth shattering orgasm."

"I'll take the loss. It's a mystery I lasted this long," I said.

She stroked my shaft mercilessly as her other hand dropped to my cum-full balls to massage them. "Are you close?"

"Yes."

"Do you want to cum for your step sister?"

"Fuck yeah."

"Okay," she said calmly, her tone shifting suddenly. Then she released my dick and balls, covered her body and started backing away.

"What are you doing?" I asked in surprise.

"Waiting for you to cum."

"That's not how it works."

"I'm done touching you. Your dick is hard. Now, you need to cum or else you'll lose it. The only option is to jerk off and ruin your own No Nut challenge. And also lose the bet to me."

"What? So you did all this just to make me fail my challenge?"

"Duhh!" She exclaimed like it was obvious what she was doing.

"I already accepted to lose the challenge as you jerked me off."

"I need you to jerk off to prove that to me. That way, you lose the bet and we can't have any loopholes-"

"Fuck this," I snapped and rushed past her to my room with a relentless hard dick.

I Googled and realized the No Nut November challenge prohibited cumming but didn't stop one from actually jerking off or having someone else bring you close to orgasm. Only the orgasm was off limits. I decided not to let Jan have the last laugh on this. I wouldn't let her have her way and win this bet. Not in a million years.

I got my Play Station and started playing Fallout. Within a few minutes, I had a flaccid penis.

Jan started walking around the house in bikinis that barely covered her pussy. I could see the short blonde hairs around her pussy and when she bent down, I could see the lips of her pussy slightly showing. Mom kept imploring her to not show more skin. But Mom didn't know she was desperate to win a bet. I wondered what was getting her obsessed with a small bet. Why would she go to great lengths to ruin my No Nut November challenge? I didn't have a clear answer to that.

"Honey, you want some cookies?" Mom called from the kitchen, one Saturday afternoon as I sat on the couch watching football. It was November 28th. I was proud of how long I lasted.

"No, thanks, Mom," I replied as I noticed Jan entering through the door in her yoga pants. She was definitely from the yoga studio down the street.

Trying to stay away from Jan, I asked her if she'd seen Dad outside. She said yes.

"I'll go talk to him now," I said.

She smiled at me and quickly found her place next to me. "Why have you been avoiding me?" She asked, smiling.

"Well, for one, you want to make me cum all the time and I don't want to," I answered.

"You want to but you don't want to admit it."

"Why are you so invested in ruining the challenge for me?"

"Because it's fun," she admitted, running her fingers on my now erect jean-covered cock.

"You realise how fucked up this is, right?"

"Oh please. Get a grip of yourself."

"This is fucking incest," I shouted.

"What's going on there?" I heard Mom shout from the kitchen.

"Nothing. It's totally fine," Jan shouted back.

Jan stood and moved between my legs and then slowly lowered her ass onto my groin area.

"Stop it. C'mon, we are basically siblings," I resisted but my pleas fell on deaf ears.

She giggled as she rubbed her sexy ass on my cock. If I wasn't hard before, now it was way worse. My ability to resist her sexual advances was very weak after going through several days without cumming. I knew now it was very hard to resist temptation anymore. Besides, I had held on for so long.

Jan gave me a lapdance, her ass covered in yoga pants grinding in sensual motions allover my cock. She held onto my knees for balance.

"We both know you want this but you keep putting yourself through this meaningless self torture. For what? Some macho challenge to keep your hands away from your dick? Pleeeaaaseee!"

She kept grinding her ass allover my groin. I moaned loudly. I wasn't sure if Mom heard me but I was definitely on the edge.

"C'mon, open up your pants. Your dick might snap out if you don't let it," she said seductively.

Like a robot obeying instructions, I allowed my hands to pull the button away and run the zipper down. In the moment, I couldn't resist touching her perfect ass for a second. She used her hands to pull my jeans down to my mid thigh.

I gasped and protested. "What are you doing? Do you know we could get caught naked?"

"That's part of the thrill, bro," she said. Any fear or resistance I had quickly evaporated when she pulled her yoga pants down. I watched in shock and disbelief as her wet pussy came into view. She didn't have any panties on. I ran my fingers along her pussy slit and she shuddered from the touch. My hard dick stood up straight waiting to take it's chance.

Jan grabbed my dick and ran the tip along the lining of her pussy. We both moaned, feeling the intense sexual energy in the moment. I'd give anything just to push into her pussy and cum.

She slowly bent back and allowed her pussy to engulf my dick. I let out a heavy sigh, the tightness taking me by surprise. I knew it wasn't going to take long before I was shooting my cum deep into her.

Jan started bouncing on my dick up and down. I sat back and enjoyed the fine look of her ass as my dick drowned into her pussy. Soon, sounds of her ass smacking into my legs got louder as she picked up momentum. My dick got coated with her white cream which accumulated at the root of my cock.

I felt myself rising to the climax. I pushed my body upwards to meet her down thrusts. I cried out and pulled her down on my dick as I shot my cum deep into her pussy. She tried to pull herself away but I held on til I shot all the cum. It took several seconds, what seemed like an eternity, before I finished. She pulled away and the cum flowed out of her pussy in thick trails going down her legs.