The Time My (21F) Got Blackmailed By My Little Brother(18M) {MF | Bro/Sis | Blackmail | Reluctant}

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Part 1

During my second year in college, I was staying at home with my family to save money. This left me living with both of my parents and worst of all, my annoying little brother. College was tough to keep up with my grades because of the workload and amount of invites I got to party or hang with friends. I tried to split my time up evenly for fun and school work but was not very disciplined. My grades were starting to slip early in the semester. By the time spring break was coming up, I was basically failing most of my classes. I knew that I was close to being kicked out by the dean for flunking out. This ruined my spring break plans since I needed to stay home to hide the grades coming in the mail. Luckily my parents worked 9 to 5 on the weekdays so I would be the only responsible one home. My brother would likely be asleep until the afternoon anyway.

The first two days I waited for the mail all morning to make sure I was the first to the envelopes. Both days the mail arrived around 11 am so I knew when to be expecting it to arrive the rest of the week. Three days in I was starting to get worried when none were addressed from my school. Thursday I came down right on time expecting to grab the mail just as it was left in the box. I walked down the stairs and directly to the mailbox outside. When I got out there the box was empty so I looked up and down the street looking to see how close the mailman was to my house. To my surprise, he was pulling his little white truck off the block as if he was finished. I even waited outside a few extra minutes expecting him to come back around. After a little while, I figured that we got no mail today and returned to the house.

Walking back into the house, I was startled by someone else inside. I was shocked to see anyone up but luckily it was just my little brother. Ricky was finishing a bowl of cereal on the couch as I walked past him in the living room. His eyes looked tired but he seemed to be in a good mood. I figured he happened to wake up early today. Before I could make it up the stairs I heard him call my name.

“Jess! What were you doing outside?” He said as I stopped on the first step of the staircase.

“Ohh, nothing just checking the mail since no one else is home to do it today,” I told him as I turned back around to see what he wanted.

“You sure? You looked worried out there when I glanced out the window,” Ricky explained in an odd tone.

“This is just the time it normally comes but I guess it is late today,” I lied to him. My heart rate was going up since I knew I was lying to him. The pressure of failing and lying made me want to just go back to my room.

“Well I will tell you if I see it coming later,” he said with a smirk on his face.

“I am not that worried about it Ricky. We can just get it later tonight or something,” that was the only lie I could think of to keep him from checking for it throughout the day. I did not was to spend all day watching the mailbox to be the first one there.

“You sure? I usually can see him arriving from my computer,” he told me.

“Yea, I am not worried about the mail that much,” I said hoping that would be enough to end the conversation. As I was thinking he said, “You know, I saw you have been looking for the mail a lot this week from my room.”

“What?” My heart felt like it stopped beating for a moment when I heard the news. I never thought about him being able to see the mailbox from his room. “I thought you were sleeping in all spring break up there,” I said hoping he was lying for some reason.

“No, I have been sleeping in the afternoons mostly. That is when my friends stay up gaming at night,” he explained further. I was in shock but still hoped he did not know what I was waiting for.

“I thought I had a little package coming soon but it could be here any day now,” I threw out the first lie that came to mind. That only made Ricky laugh a little on the couch. He placed the now-empty bowl down on the coffee table before leaning back on the couch.

“Stop lying Jessica,” he said before chuckling again. My heart was racing now as I felt that I was being caught lying. “When the mailman pulled up early today I saw you were not out there so I was being a nice guy and grabbed it for you,” Ricky said as he reached behind his back on the couch. He pulled out a stack of envelopes and tossed them on the table by his bowl. “You can have the mail if you take out my bowl,” he bribed.

“Ohh, okay. Sure,” I said before quickly grabbing the mail and the bowl. My tension started to be released as I noticed he was only using the mail to be lazy on the couch. Quickly I walked to the kitchen to put the bowl in the sink so I could check the mail. I flipped through the envelopes but did not see one from the college. A sigh of relief escaped my mouth as I felt I was in the clear.

“There is not little package in there,” he shouted from the living room. I rolled my eyes at his statement as I tossed the mail into the pile on the counter for my parents. Right as my foot touched the first step again, I heard Ricky call for me from the couch.

“Hey, Jess!” His voice was a little louder this time. I turned back to see him still sitting there like a lump.

“What?” I asked in an annoyed tone. I just wanted to get back to my room already.

“There is another one you left here on the table by the way,” he said as I froze in place. There was not another one on the table when I walked away.

My mind began to race either way, “Maybe I did forget one. I am a nervous wreck this week. Or is he just messing with me?” I went over to the table to check the last piece of mail assuming I must have left it lying there. When I picked it up my heart stopped again. It sunk to my stomach it felt like.

“You look like you saw a ghost,” he said to me with a grin on his face. The envelope was from my school. That was not even the worst part. Ricky had already opened it. The top of the envelope was sliced open so I knew he must have checked it.

“Why did you open my mail?” It was all I could think to ask in the moment of shock.

“I just wanted to know why it was so important that you waited for the mail for hours,” he told me. His explanation went on, “Honestly, I did not expect to get the great information that you are failing college.”

“Great?” I was speechless so that was all I could get out. His statement had me baffled.

“Well, now I got some dirt on you. You are normally the good one who never got in trouble growing up. I was always getting in trouble and most of the time I know you were the one snitching on me,” Ricky said as he brought back memories before college when I was mean to him. He was right that I would tell my parents about him often but it was to protect him from doing something stupid.

“I-I-I am s-sorry Ricky,” I managed to get that much out. But now I was worried he was going to tell our parents when they got home as revenge. That was the only outcome I could imagine at that moment.

“So you go off to college and finally start living life?” He jokingly asked since he knew I had become more of a free spirit instead of a prude. A part of him was right. In college, I felt freer since I was away from the judgment of my parents so I could party and let loose some.

“I-I-Is that not the point?” I replied as I hoped he could understand we were both adults now since he had just graduated too. Ricky had just turned 18 and I hoped that he was starting to be an adult. Unfortunately, I was proved wrong by his next statement.

“Maybe it is but this may be my only chance for payback so I have to take it,” his smirk showed there was no way I was going to talk myself out of it. He did not give me a chance anyway. He started talking again, “I know you do not want our parents seeing these grades because you can probably get them up before the end of the semester. You know that you would not want to feel that guilt trip mom would put you on either. So I think that means that you owe me big time?”

“Owe you what?” I asked hoping he would just want me to help him with chores around the house or some work he needs to be done. Ricky knows that normally I am much better in school than him so I could easily do his work too.

“I have not thought about it yet but I will let you know later. I need some time to think about the possibilities carefully. For now, you can keep that envelope because I got a picture of it on my phone. Your secret is safe with me,” my evil little brother said as he got up from the couch finally.

I stayed standing in front of the coffee table with the paper in my hands for a few minutes as I tried to think of a way out of all of this. The one thing I knew for sure was that I needed to get my grades up immediately. Finally, when I got the ability to move back, I walked up to my bedroom. I wanted to lay under my covers on the bed but I forced myself to my desk to finally study.

Every couple minutes during studying I had to stop myself from worrying about Ricky possibly just waiting to tell our parents I was failing. I got in almost two hours of studying before he came into my room to interrupt me. My hope was that he had a list of chores in his hand for me to do or something of that nature. He had changed and showered since breakfast.

“I am going out with a couple of friends Jess. We will talk about your bad grades when I get back later,” he said to me while standing in the doorway.

“Umm. When are you coming back?” I asked. It was the only thing that came to my empty mind.

“Probably after dinner or something. Glad to see you are finally studying but it is a little late for the revenge though,” Ricky said as he laughed his way out the door of my bedroom.

For a few minutes, after he left, I could not stop thinking about what he might do while he is gone. He could tell our parents or be going to show it to them at work. They would not be home for a couple of hours so I had no idea. Luckily I convinced myself that I needed to study until they got home. It was the only thing productive I could do to keep my mind off of it. Ricky had me panicking in my room all afternoon while trying to read through a textbook. Most of the time I managed to read between small panic attacks in my room before my parents finally arrived.

First home was my mom. She walked in the door as I started coming down the stairs to greet her. My dad got home just a few minutes later as mom and I were talking about her day. The nervousness made it hard for me to feel out if he had told them already. After talking to them for about 20 minutes I decided that they must still be in the dark about my grades. Ricky must have kept his word which was a relief but surprising, to say the least. The rest of the night I was slightly more relaxed but still worrying as we sat through dinner later. All three of us had a fairly normal conversation before I told them I was heading back to my room to study more. My parents told me it was time for my break from school but I knew I had been taking too many breaks already. I went up to my room right after dinner and studied until Ricky came back home.

By the time that I heard him open the front door that night, my mind had already been over a million different outcomes for his return. Most of them I was hoping to avoid so I just tried to stay positive until I knew what the little dork was up to. I listened as he walked through the house, up the stairs, and right up to my door. I looked at the clock to see it was nearly midnight already. Being so late, I knew that my parents must have already gone to bed. That made me feel better knowing it was unlikely they would be walking down the hall and possibly hear our discussion. The doorknob turned as I waited for the inevitable blackmail that I was going to be forced into for failing my classes.

“Did you miss me?” Ricky asked with a big grin on his face. I could tell by that look that he had decided on my fate. A part of me hoped that he was going to be unable to decide.

“Not even a little bit you asshole,” I wittily replied as he closed my door and sat down on the edge of my bed. He did not waste a moment making himself comfortable. His shoes were kicked off onto my floor as he laid back on my bed.

“So I thought about how we could handle this most of the night,” he said as his voice trailed off into silence. My anticipation was building to a frustrating level after my long day.

“Just tell me what I have to do Ricky,” I pleaded hoping he would quickly let me know my chore for the next few weeks. Still, that was what I found most likely since he was so lazy. Kevin sat up on the bed in a quick snap of his body.

“You want me to delete evidence of you being a bad girl for once. This is a rare chance for me to see you in trouble for once. Growing up you always gloated about being the good one. I think if you want me to delete the picture I am going to have to make you prove that you are not as stuck up as you act in front of the family. I know you probably are failing these classes because you started drinking or spending too much time with frat boys. Maybe I should tell our parents that too,” Ricky threatened as he ended his annoying monologue.

“How about you keep your mouth shut and mind your business,” I replied as the anger finally got to me. He was getting on my nerves like never before.

“See you can be bad, you can get mad, but yet you never let any of us think you are less than a perfect woman,” he told me as he looked into my eyes with a serious glare.

“You just want me to clean your room and clothes for a while?” I asked trying to hurry him along.

“No that is too simple and I can do that whenever I want. You failed four classes right?” Ricky asked as I began to wonder what he was getting at.

“Yes, four Ricky,” I smugly responded as I showed how annoyed I was becoming.

“Fine. Since you want to be a bitch, then I will just let mom and dad deal with it,” he said knowing I would freak out. The little asshole was right.

“Stop! Do not tell anyone!” I half yelled so I did not wake my parents.

“Then stop being rude,” he said in a sarcastic tone.

“Sorry,” I reluctantly gave my apology to keep him happy and quiet.

“So since you failed FOUR classes. I think you owe me FOUR favors to keep me quiet about each failure you have,” Ricky looked sinister as he mocked me directly to my face.

“How is that even fair? I am not going to be your slave,” I said before thinking about trying to keep him happy.

“Well that is the deal, take it or leave it. I can just go tell our parents if you are not happy,” he said as he pretended to get up to leave.

“Sit back down you jerk. Fine I will do you four little favors but do not get too crazy,” I told him as I watched him sit back on the edge of my bed.

“Good to hear you say that Jess. So should we get the first one out of the way tonight since our parents are asleep?” He asked while looking like he already knew I had to say yes anyway.

“What is the first one?” I said with another sarcastic eye roll to his face.

“As I said, I want to see that you are not the good little princess that our parents think you are. We both know that you have grown out of that in college,” Ricky teased me one last time before giving me my first task, “I want you to take off your shirt to start.”

“What the fuck do you mean take off my shirt? I am your sister you little weirdo,” I blurted out immediately at the unexpected request. My mind started spinning as it tried to understand why my 19-year-old little brother would want me to take off my shirt in front of him.

“I mean you have to take off your shirt or I can just go wake up our parents for this conversation on your failing grades Jessica,” he responded with a tone that made him seem more strict and mature. It was a side of Ricky that I had not seen before.

“Why would you want to see me without a shirt? This is too weird Ricky, you are my little brother,” I said to hopefully get him to realize this was too weird for us to be doing.

“I want to see that you are willing to do bad things besides fail college from partying with the horny frat guys,” he said while leaning back on his palms as he was still sitting on the edge of the bed. Then he attempted to give me a little bit of motivation by saying, “Plus, I have seen you in a bikini plenty of times.”

“I still do not think this is a good idea,” I hesitantly said as I thought about the situation I was in at the moment. Ricky was staring into my eyes which made me feel even more uncomfortable in the situation. My voice was shy as I asked, “So if I take off my shirt then I will owe you one less favor?” I could not believe that I was negotiating this with him.

“I said that you needed to start by taking your shirt off,” Ricky reminded me without leaving my eyes with his deep glare.

“Then what?” I asked since it was all I could think of as I began to feel embarrassed. My cheeks were heating up as I could feel myself starting to blush.

“Then we will see how far it needs to be taken for me to feel relieved and know you are just pretending to be a good girl. I mean you are 21 and still act like the good one, even though you are just as wild as I am,” he stated as I noticed him getting impatient on the bed.

“Fine!” I snapped as I reached down to the bottom of the white shirt I was wearing. My fingers grabbed it and yanked it off over my head. The shirt was held in one hand as I used the free hand to push the hair back off my face. His eyes were analyzing every inch of my chest the moment I was uncovered. It made me feel a little insecure as I looked down to see what he was so interested in. Luckily, I had on a bra tonight so my perky 32C cupped breast was still covered.

“See that was not so hard was it?” Ricky asked with an evil smirk on his face.

“No. So this is what you wanted?” I replied hoping he had enough for the night. I just wanted to check off one of the owed favors to get this all over with already.

“It is a part of it. You do not seem to be too embarrassed by taking off your shirt but you probably got used to that at college parties,” he said just to get under my skin.

“Fuck you,” I fired back at him in a moment of rage.

“Not yet,” he said under his breath. I did not know what he exactly meant by it but I heard him mumble it. Then he responded, “Do not get so smart with me. Now take off your shirts.” Ricky was quick to move to the next step.

“My shorts now?” I asked in a high pitch. He was pushing this too far so I had to ask, “Are you trying to get me naked?”

“Just take off the shorts as I said. This is starting to get on my nerves so I might just go get mom up real quick,” Ricky threatened me as he sat up straight on the bed. He was really blackmailing me with the grades, even more than I expected.

“I am not taking any more off though,” I warned as I pushed down my small blue shorts to the floor. With my foot, I tossed them to the edge of my bed. That left me standing in front of my brother in just a matching set of white underwear. The embarrassment was growing exponentially. It was not over insecurities about my body, it was because I was standing in front of my brother. I was in great shape since going to college. Just a 21-year-old brunette that had an athletically toned body. Working out kept me in shape and gave me a nice butt since learning techniques from girls at school.

“You have tightened yourself up since I saw you in the lake last summer. College is doing great things for you I see. Well, maybe not knowledge but still,” he mocked as he checked out my fit body. I could see his eyes going up and down my body in silence.

“Are we done now?” I asked hoping we could go to bed and forget all about the night.

“There is one last thing that needs to be done before I can go to bed,” Ricky said while giving me another one of those creepy grins.

“Need me to tuck you in?” I teased as I stood with my hands on my soft hips.

“Actually I need to deal with this,” he said guiding me to the problem with his eyes. Ricky looked down and I followed the line of sight to the middle of his shorts. I gasped audibly when I saw that he had an imprint of his dick across his thigh. The shorts made it easy to see the full outline of the erection hidden in his shorts.

“Gross Ricky!” I said the moment I saw what was going on. That was not where I expected it to go at all. I thought he was trying to embarrass me, not get off to his sister. I tried to draw the line by saying, “I am not touching that thing.”

“That is not part of favor one. For now, I just need to cum before bed Jess,” he explained as if it was a normal thing for us. His hand moved down to his crotch before starting to grope himself through the shorts.

“You think I want to watch you?” I asked in disgust.

“You can watch if you want but you will sit there if you want me to delete the photo,” he said as his hand unzipped the shorts and pulled the button out of the hole. It seemed like I blinked and my little brother was sitting on my bed in just a pair of black socks and a black shirt from his night out. My eyes avoided looking at his crotch. I did not want to have that visual in my mind.

The feeling of defeat washed over me as I gave into him by simply saying, “Hurry up and finish then.” My eyes were staring at my feet below me as I heard him starting to rub himself. I tried to focus on my little red toenails to block out what was going on. That was working until I heard him spit. It gave me an unwanted visual of my slob brother spitting on his own dick.

“Do you have any lotion?” He asked in a sexual tone while stroking himself.

“On my dresser,” I answered without moving an inch.

“Get it for me, Jess,” he said before giving a little grunt.

“You can get it,” I responded since I did not want to get up and risk seeing anything.

“If I get up then I will have to start over and this will take longer,” he warned as he started rubbing faster. I wanted this to be over already, so I sighed as I stood up from my chair. My eyes stayed on the floor as I walked to get the lotion. Then I took it to him but kept my head turned.

“Give me a few squirts of it,” he said as I held it out for him. My hands moved to give him some lotion before I put it back and sat back down. The worst part was feeling his eyes staring at my ass as I walked around my room. When I sat down he said, “Your ass is looking way better than it used to, even though it is not as wet and tan as it was in the pool.” Ricky must have thought I wanted his compliments. I sat there quietly as I continued looking at my feet. The lotion had made his jerking off much louder as it squished and slapped around.

“Are you almost done?” I impatiently asked him.

“Your questions are not helping but I am not. I know how we can speed this up a little though,” he said as his voice raised in pitch.

“What now Ricky?” I asked knowing it could only get weirder from here.

“Take off your bra. A pair of great tits can always make me bust quickly,” he explained trying to get me on board with his antics. Ricky had another reason for me to do it also, “Besides, I have seen them before.”

“When?” I said as my head instinctively snapped to look him in the eyes. After about three seconds I could see the stroking hand in my peripheral view and swiftly look back to the floor. Luckily, I did not get a good look at his junk.

“When you lost your top in the lake a few years back,” Ricky responded as I remembered the time he was thinking about. Then he went on, “Also a few times when I had to pee and you forgot to lock the bathroom door.” The second one was said in a happier tone as if he was excited to walk in on me. His voice was a little louder as he reminded me, “Not like you have much of a choice anyway if you wanna keep our little secret.”

“You are such a pervert Ricky!” I said while hearing his pace pick up. “Whatever I will but you better not be this creep after tonight,” I said as I reached both hands behind my back. My fingers unclasped my bra as it fell down to my lap. Then I moved it to the floor while feeling his eyes staring at my chest again.

Ricky was practically moaning as he said, “Those 32C boobs have always been perfect, not too big, not too small.” I could not believe what he was saying to me.

“You almost done yet?” I asked to hurry him up. This was going on way too long at that point.

“Getting there,” he grunted out as I heard the noises of his aggressive jerking. I could not believe he was doing all of it in front of his sister. Then he got louder as he grunted out, “Ohh shit!” Without thinking, I looked up to see what happened. It sounded like he messed something up or got hurt.

“Eww, Ricky!” I shrieked when I noticed what happened. His hand was still stroking his shining cock as it launched its last few shots of cum from the throbbing head. My brother’s white load spilled out all over the edge of my bed as he climaxed in front of me. It was not what I wanted to see but now it was going to be stuck in my brain forever. His veiny young cock cumming as he jerked off in front of me was not a memory I needed.

“Sorry Jess,” he said as he wiped the tip off on my blanket beside his large load. Ricky was a little sweaty as he used his shirt to wipe off his forehead I saw him almost fully naked for a moment. For a second I thought about how good he looked but quickly pushed that out of my mind. After getting his shorts back up he told me, “You can mark off one of those favors.”

I sat in my computer chair in only my panties even after he left my room. My eyes did not leave the drying cum all over the edge of my bed. It took me nearly 10 minutes to finally get up and stop thinking about the situation I was just a part of. While I was walking to my bed to remove the blanket, I noticed that I was wetter than I had ever been between my legs. It was easy to feel as I took the cum covered blanket off and threw it to the corner of the room. Then I walked to my door and made sure it was locked. That was the last thing I needed to do before laying down for the night. After the first favor was over, I was left feeling odd about the whole thing. Mainly I was hoping that was the worst of the favors.

For over an hour I tried to fall asleep but to no prevail. Eventually, I had no choice but to masturbate. I could not fall asleep with the burning wetness between my legs. It could only happen after I convinced myself it was natural. That was the most awkward masturbation I had ever had as memories and images of my brother’s dick continued to pop up unwillingly in my head. In the end, I was able to finally get myself to bed after an intense orgasm caused by my fingers. I could tell this was the start of something bad.

Source: reddit.com/r/eroticliterature/comments/mxm36y/the_time_my_21f_got_blackmailed_by_my_little