Helping Aunt Karen During COVID Ch. 02

About a week after me and Aunt Karen had our experience, my sister Jen texted me, "Hey, golden boy. Mom and I went to check in on Aunt Karen, and surprisingly, all she would talk about was you cracking her back and giving her a great massage. Be expecting mom to make an appointment. Bye, loser!" Jen's always been jealous of me and feels like I'm the favorite. I could tell by her condescending text that mom and Karen probably praised me to the moon.

I love Jen, she is my sister, but she has no ambition. Works sporadically, essentially living off my parents. Thirty-five years old, never been married, no kids, I can't even remember when the last time she had a decent boyfriend. I am sure that she has been driving my mom and dad nuts since the pandemic started. I'm shocked she hasn't just shown up to try and hang out.

I texted her back, "don't hate just because everyone loves me, lol. Hope you are enjoying isolation with mom and dad!"

Jen's response was immediate, "Whatever, loser! When do I get my massage? It's been six months cooped up with these two miserable fucks! Can I come to hang out at your place for a break? I will be good, promise!"

I felt bad for her, so I told her, "Yeah. Don't be a bitch when you get here."

I called Aunt Karen to ask what she had said about the massage. I was worried Jen would try to trip me up; she's sneaky like that. "Hey, Auntie. Jen texted me talking shit about you telling her about the massage. She's going to be coming over, and as you know, she'll be asking a million questions. I want to make sure our stories match up."

Karen started laughing as she explained everything that she said. "That sneaky little bitch. I was trying to get your mother to call you for a massage. She is pent up and needs to take care of that. I told them that it was awkward being topless with you, but your hands are magic. I specifically told them to make sure they use the warming oils. You realize, women talk differently when we are around each other. I told them I almost had an orgasm when you were rubbing me. I could tell they both were curious. I'm still working on your mother. I think you should fuck her. She needs to get ravaged. You still want me to work on that, right?"

"Yes. The thought of it is exciting to me. When are you coming back over for round two?"

Karen's response shocked me, "Well, not tonight, obviously. Your nosey, bitchy sister is curious, and she won't be leaving. She's another one who needs to get laid. Maybe she'll stop being such a bitch."

About seven, Jen showed up with take-out food and alcohol. I should have figured she'd be drinking. "Hey, loser! Are we going to Netflix and chill, as you did with Aunt Karen?" Jen burst out laughing at her joke. "Mom didn't get it either. You should have seen aunty trying to explain what it meant. Finally, aunty said, it means you hang out and fuck. Mom turned beet red and asked what your reaction was."

"What did Karen say?", I asked.

"She said you were calm, cool, and collected. She and mom both.need to get laid. They should Netflix and chill with someone. Anyway, thanks for letting me come and hang. Want a drink?"

"Yeah, I'll have a beer. No problem, with this pandemic, it's nice to have company." It was nice having company, and Jen wasn't being a pain in the ass. We ate, drank beers and shots of tequila, binge-watching a show.

Before I knew it, it was one in the morning. "Well, sis, I need to head off to bed. You can have the couch; I don't want you driving while you've been drinking."

"SERIOUSLY?" Jen yelled. "Can I at least get a massage? What the fuck Dave! I'll take my shirt off for it." then she burst out in a laugh.

"I won't be any good because I'm buzzed. Plus, I don't feel like setting the table up. I'm not worried about you being topless, it doesn't intimidate me. Kind of hard to do a massage with a top on, idiot." Jen is an idiot, and it was my nickname for her growing up.

Jen was almost in tears when she said, "I'm not asking for Aunt Karen's treatment with the table and everything. I realize no one is going out of their way to do anything special for me. But I don't know why you can't do it here or on the bed. Why does everyone do things for everyone but me? Am I that horrible that no one wants to do anything for me?"

I felt bad for Jen. We do a lot for each other in our family, except when it comes to her. I didn't like to see her upset and understood why she always feels left out. I asked her, "Are you being serious, or are you just drunk and emotional?"

"I'm serious, Dave! Is it too much to ask that I be treated like everyone else? You are my brother; do you realize what it's like being locked up in a house with mom and dad for months? IT FUCKING SUCKS! I listened to Aunt Karen say how amazing it was to get a massage from you. I'm sorry I even asked. You don't have to do it out of pity for me. I get it. Thanks a lot."

Suddenly, I wasn't tired anymore and felt like a horrible person. "Look, Jen, I'm sorry, and you are right. You do get forgotten about a lot. I don't do things out of pity or obligation. I didn't realize you wanted a massage. I thought you were fucking with me. So, how about you go in the bedroom, get ready, and I'll be in after I use the bathroom? Then if I'm not as good as Karen said, tomorrow, I'll set everything up and give you the full treatment, deal?"

I handed her a tissue to wipe her tears, which smudged her eye makeup. "Oh, before you answer, I wanted to let you know you look a mess from crying."

This comment got her to laugh through her crying. "Ok, I'll go in the room. No matter how good you do, I will lie and say it sucked just so I can get the full treatment tomorrow."

When I got to my bedroom, Jen was laying in the middle of the bed, stripped down to her thong panties. I told her, "This is more than topless. Are you an idiot?"

I didn't need her to answer the question. I knew she was an idiot. "I want my legs done too. I figured it would be better to just take my yoga pants off now instead of later." Looking at Jen like this was different. Her body was nice and toned. I got lost in thought for a minute staring at her ass in her thong panties. Suddenly, she broke my concentration, "HEY! STOP STARING AT MY ASS AND GET TO WORK!" Jen was cracking up at her smartass comment.

I was embarrassed, "Well, where do you want me to start?"

"HAHA, well, not my ass, obviously. How about my calve, perv. Work your way up." This was the smartass Jen I knew. I was glad she was back to being herself.

I poured the warming oil on both of her legs. I started with deep rubbing on her calves, spreading the oil on her thigs as I moved up. "How am I doing so far?"

"I cannot lie; you are good at this. Now I understand what Aunt Karen was talking about." As Jen said this, she opened her legs wider. I wasn't sure if this was an invitation to explore more of her. So, I poured oil on my hands and started rubbing the inside of her thighs. "Loser, did you rub Aunt Karen there? You're getting a little frisky. I don't think mom could handle a massage from you. Aunt Karen was trying to convince mom to get one. That feels amazing."

I could tell Jen was enjoying the excitement of me being so close to her nether regions. "Yeah, I massaged Aunt Karen like this. Why?" Jen has a big mouth with no ability to keep a secret with anyone. I wanted to know what Karen said to her and our mother while she was vulnerable. I was thinking this massage was going to end soon.

"She told us to make sure you let Dave massage your legs, she almost came when you were rubbing her thighs. That's why I stripped down to my panties, I didn't believe her. Mom asked her if she was naked in front of you, Karen told us no, she was down to her panties." Karen was giving word for word description of the conversation between Karen and mom.

"So, am I as good as she said I was? How did mom react to that?" I wanted all of the information I could get.

"EH, it feels good, but I don't feel like I'm going to cum, if we're being honest. Mom was beet red. Come on, her sister was naked in front of you, talking about how you almost made her cum from rubbing her body. You know mom, she's an uptight prude who needs to get laid. The poor woman probably has never been FUCKED."

I felt like Jen was challenging me, so I started feverishly working the inside of her thighs. "So, you were expecting me to give you a massage that would bring you to the edge of cumin? Do you think mom has ever had an orgasm in her life?"

Jen got feisty, "YEAH LOSER, THAT'S WHAT I WAS EXPECTING! I think you are all hype, the golden boy. Let's see how good you are, loser." Then she started laughing. "And, NO! Mom would have a seizure if she ever came. She wouldn't even know what was happening."

"Well, sis, now I know what you want. Challenge accepted." I know my sister is a drama queen, along with being a pain in the ass to everyone. What I didn't realize; is she came here specifically to see if I could make her cum. I'll be honest I don't think she wanted to have sex. Jen just wanted attention.

As I was rubbing the inside of Jen's thighs, I looked up at her face. I could see her eyes were closed, her bottom lip was between her teeth, and her hands were clenching the pillow above her head. I realized that she was full of shit about how good I was doing rubbing her down. One of my hands was moving closer to her ass. While I inched the other hand closer to her pussy. I was trying to be careful not to overstep, Jen has a big mouth, and I didn't want her to be dramatic like she didn't want any of this. I asked, "How am I doing now?"

"OK, don't let it go to your head; you are doing really good. Let me know if you need me to move or anything. OK?"

I knew she was into getting rubbed. I was seeking more information to see how far I was going to go. "If I need to move you, I will move you. Just relax and enjoy. If you get uncomfortable, let me know. OK?"

Jen never opened her eyes or unclenched her grip on the pillow. Her smart-ass answers were gone, along with her naturally loud, confident tone. In an almost whisper, Jen told me, "Dave, I am so comfortable it is ridiculous. I don't want to move, so move me when you need to. Do your thing." I could tell Jen was nervous; I don't think I've ever seen her this way before. She has always been confident, arrogant, and entitled. This was why my family and I have always struggled with her.

I lightly brushed my fingers along Jen's panty-covered slit. When I did this, I felt her body tense up as she bit down on her lip. I was surprised that there was no resistance. I was, expecting her to protest, close her legs, yell at me, but I got nothing. Again, I thought, "Let's see how far I can push this." I repeated, brushing my fingers over her slit every few strokes as my other hand continued with deep massaging her ass cheeks. Jen's body would tense up every time I hit a sweet spot on her. I would wait for the tension to subside and slowly work my way back to those areas. Jen was oblivious to how easy she was making this seduction for me.

The area that Jen really tensed up is when I touched was her upper thigh, ass. Whether I touched, rubbed, or even grazed this area, she would tense up and clench her ass cheeks. I was going to focus on this area, but first, I needed more access. I got off the bed and heard Jen whisper, "Don't go, what are you doing? Where are you going?"

"I thought you fell asleep on me." I lied.

Jen cooed, "No, Dave, that felt so good. I was so relaxed. Get back here."

I liked seeing Jen so vulnerable. "I'm right here. I need to move you a little. Let me know if you get uncomfortable. I'm still buzzed, plus it's two in the morning." I gave a fake chuckle. I was trying to gauge how vulnerable Jen actually was. I started to pull her legs further apart so I could kneel between them to focus more on her sensitive areas.

"Oh, OK. Good, I thought you were giving up on me. I'm still buzzed too. Thank God we don't have to do anything tomorrow. Don't worry about me. I'm super comfy." Jen sounded whiney and seductive at the same time. I found it humorous that she said she was 'still buzzed' too. It seemed like she was lining up an excuse in case things got out of control. I know that is why I said I was 'buzzed'. All I thought at this moment was all bets are off. Time to apply the full-court pressure.

Before I got between Jen's legs, I decided to turn the lights off when I heard Jen say, "Thank you. The lights were driving me crazy." I took all my clothes off and knelt between her legs. Jen was oblivious to me being completely naked. I started rubbing her thighs, moving up to her ass. Once my hands got there, she tensed up, bucking her ass. When she did this, her panty-clad pussy scraped across my rock-hard cock. I froze and thought I was going to cum at that moment.

I asked, "You, OK?"

Jen purred, "Yes. You are really good at this. Keep going, don't worry about me. I'll let you know. Keep going."

I continued my rubbing of her ass and hips, moving down to her thighs. My eyes had adjusted to the darkness as I continued to watch her face for reactions. If Jen thought I was being inappropriate, her face didn't show any sign of it. While rubbing her ass, I decided to pull her ass cheeks open. When I did this, I heard Jen moan. I did it again and pulled the flimsy G-string. There was no protest, so I decided to rip the G-string to get full access. I was careful to not be aggressive doing this. Luckily the material was thin and easily shred. With nothing in my way now, I slightly grazed Jen's bare pussy lips with my fingers. Jen's hips bucked, while a moan slipped through her lips, "mmmnnnffff... oh my God."

I told Jen, "Hey, I'm going to rub the front of your legs. I'm going to roll you over."

I immediately grabbed one her legs, pulling it up, while she rolled her body onto her back. Jen whispered, "OK. Sounds good."

My hands were still slightly oily, so I did not put any oils on the front of Jen's thighs. I started right at her upper thighs, rubbing the inside of them where I could feel the heat from her pussy. I moved my thumbs to the crease of her thighs and pussy. Jen arched her back, causing her mound to raise, as she moaned, "fuckkkk...ohhhh...fuck." I was done asking her if she was OK. It was three in the morning, and my cock needed relief. I moved my hands up to her stomach. Using my fingertips, to slightly rub from her stomach, moving up to her tits. Again, no protest, just a slight moan, "ahhh..."

I was pinching her nipples while rubbing her tits. Jen arched her head, then her back, causing her hips to rise again. I could feel her pussy right in front of my throbbing cock, as I slowly lunged forward. The tip of my cock was right at her slit. I knew she could feel this as I waited for her to stop us from moving forward. I slowly started rocking in a forward motion as the tip of my cock was slowly, slightly, sneaking past her pussy lips.

I started pushing more of my cock into Jen's soaking wet pussy when she wrapped one of her arms around my neck. She grabbed me by my hair, with her eyes wide open, staring at me with a look of confusion. I was waiting for her to say something as she just continued to stare. I was confused about what to do next. I realize this probably only lasted ten seconds, but it felt like ten hours. I didn't know if I should keep going or stop...

I pushed my cock all the way in slowly, holding it while Jen's hips bucked up. Jen was still holding my head and staring at me when she whispered, "my God, you feel so good. I'm going to cum soon, fuck me please, nice and slow fuck me, please Dave, please fuck me slowly, fuck me please." I slid my cock back, pushing it back up slowly. Keeping my cock in her pussy, slowly grinding Jen, with her pussy clenching around my cock. I felt her orgasm coming, she placed both of her arms around me, pulling me into her. She screamed as she dug her nails down my back ripping through my skin, "WHAT THE FUCK HAVE YOU DONE TO ME! FUCK ME JUST LIKE THAT! PLEASE DON'T STOP! FUCK! FUCK! WHAT ARE YOU DOING TO ME!"

It was noticeable that Jen was exhausted after she came. I continued to fuck her, but I knew I wasn't going to last much longer. Jen told me, "Dave, don't cum in me. Make sure you pull out, please, I'm not kidding, don't cum in me...ahhh...fuck, what are you doing to me? What are we doing? This feels so fucking good...cum in my mouth...let me suck your dick dry...PLEASE!"

I pulled my cock out of Jen's pussy, as she jumped between my legs, engulfing my cock with her mouth. Jen stared at me while she sucked and jerked my cock in her mouth. I exploded while we stared into each other's eyes. Jen was not intimidated and had no shame as she stared at me while swallowing every last bit of cum.

As we were laying there in complete silence, I was a little spooked, so I asked, "Jen, are you OK?"

Jen hesitated before answering, "YES! That was fucking amazing. My pussy is shaking from that orgasm. You have ruined sex for me for the rest of my life. Who the fuck is going to ever get to cum like that?"

I agreed with Jen and wanted to fuck her more. So, I threw the hook out to see if we were going to be fucking more, "Well, we know I can. So you're not completely ruined."

Jen was looking at me teary-eyed, asking me, "So, this wasn't a one-time 'use me' situation?"

I was concerned with the teary-eyed look, "not for me. I would never just 'use you for sex'. I honestly didn't plan on fucking you. You are my sister. But it happened, and we both liked it. So, we should do it more."

"Good, Dave. I want to feel the way you made me feel more. I want to cum like that more. Get some rest, goodnight." With that, Jen kissed me, slipping her tongue in my mouth while she moaned.