Helping Out Girlfriend's Sister

"Look, it's not that I don't want to, but..."

I was sat on my bed, a towel round my waist, having just gotten out of the shower.

My girlfriend Jen was standing in front of me. Her dark, wet, long hair draped over her right shoulder, her naked body was still glistening from the shower too. She had joined me mid way through washing. The first I was aware she was in there with me was when ax soapy hand reached round my waist and started cleaning my cock with long, wet strokes. Another hand had quickly joined, massaged my balls, to 'make sure the job was done right' in her words.

"Please babe," she pouted, as I snapped back to the bedroom. Her hands were on her hips, giving me full view of her small, perky tits. God she looked good. Her slim figure made them stand out, her nipples staring straight at me.

Now that I thought about it, the shower was probably a build up to her asking this favour.

"It'll just be half an hour. 60 minutes, tops,"

"Isn't it a bit weird though?" I asked. "For you?"

"Why would it be?" Her hands absentmindedly started gliding over her stomach and up to her tits. She knew how to get my attention. The stirring under my towel agreed.

"Your sister. Touching me. While I'm naked!"

She laughed. "You make it sound so seedy. It's a massage. Jess has given me loads. They feel really good. And anyway, you'll have a towel on to hide your modesty." She eyed up the tent that was slowly rising under my current towel "Or at least, I hope," she said with a wink.

I rearranged myself and crossed my legs.

"She just needs to do a few more massages to meet her course requirements. She's almost fully qualified now but is struggling to do these last few bits."

She walked over to me and straddled my lap. Although her tits were on the smaller side, her ass more than made for it. Curves in all the right places, as the cliche would put it. My hands instinctively roamed down there. She rubbed her pussy on the head of cock in response as she sat down. 

"I thought you said it was just one massage," I struggled to say, my cock straining to get out from under the towel.

"Well, maybe one or two sessions," she said, as she ground her hips against me. "Definitely no more than three."

She looked into my eyes before kissing me. Her tits pushing against me and her pussy grinding a little harder. I grabbed her ass, pulling her cheeks apart ever so slightly. Even though I couldn't see, I sensed her asshole wink, which made me all the more harder.

"Please," she whispered as she broke off her kiss.

"Ok," I whispered back, squeezing her ass. She moaned in response, eyes closed, smiling to herself. I went in for a kiss but just as our lips touched, she slowly pulled back. Then smiled and got off my lap 

"Thanks baby," she said, and walked towards our wardrobe to get dressed. "I'll text her this morning."

A little light headed, I just looked at her opened mouthed. My cock was rock hard, and now leaked pre cum into a spot on my towel. I needed release, especially after the shower tease - she'd stopped playing with my cock after a few minutes and started to wash her hair. My attempts of playing with he soapy tits and ass were meet with a playful smack each time.

"Erm, are we not going to...?" I started, nodding to my crotch.

She looked over her shoulder with a mischievous grin. This time, she smacked her ass to let it jiggle, just the way she knew I liked. Then turned round, before kneeling down in front of me. Again, looking into my eyes, she placed a palm on the towel, feeling my cock underneath.

Without breaking eye contact, she pulled the towel down and gasped as my cock sprung up, almost hitting her in the face. She giggled. And then wrapped her fingers around my engorged member.

Slowly, she started to stroke my shaft. Running her thumb over the head with my pre cum. I leaned back, to let out a moan. Then, before I knew, I felt the warm wetness of her mouth envelop me. I let out a second, louder moan in response. She swirled her tongue around the head of my cock, while she slowly ran her fingernails up and down my cock.

The teasing had done its job and I was already getting ready to burst. I wanted it to last longer, to enjoy Jen's lips and tongue around me. Maybe fuck her on our bed, bent over with her ass in the air. But then she ran her free hand over my balls and gently squeezed and I knew it was too late. As she gently scratched the underside place between my balls and ass, and darted her tongue around my cock head, I was almost there. I was about to cum...

Then she stopped.

"Shit, I've got to get ready for work," she said, looking at the clock. "I'm going to be late." She jumped up and walked to the wardrobe and started pulling out clothes.

I whimpered. My balls ached and my cock was covered in so much pre cum and spit, I was in agony. 

"Babe...?" I started, my wet, hard cock pulsing and bobbing up and down.

"I'm so sorry," she said, pulling her bra and panties on (which weren't exactly helping the situation!) "Can you finish yourself off? I can't be late for work. My boss is just itching to fire me."

I sighed. I guess I could have another shower. I nodded.

"Thanks babe. Now get ready, Jess will be over in a bit to start."

I eyed her suspiciously. "You already told her she could do it, didn't you?" I asked.

She just smiled as she pulled on her trousers. I'd been played. But goddam it, I loved the way her ass looked in those trousers. So I couldn't stay too mad.

****

Later that afternoon, I answered the door to Jess on my doorstep. She had a bag draped over her shoulder, and massage table folded up next to her.

"Thanks so much for helping me out, Dan" she smiled, readjusting her bag. It looked heavy. God knows what was in there. How many bottles of oil and towels did she have?

"No problem, Jess. Happy to help out." I responded. It was a lie and we both knew it. But neither of us acknowledged it. We were both getting something out of it.

Jen had hinted at finishing off what she started tonight,  before heading out the door to work for the day. She worked late on a Saturday, so more than likely I'd not see her until when I would be in bed. I said I wouldn't object to being woken up with a blowjob, just to plant the seed of an idea of how she could repay me. I decided not to jerk off after that. The wait would make it all worthwhile. It meant, however, my cock was twitching at the slightest of things since she left.

"Could you give me a hand with the table?" asked Jess, as she squeezed past me. She turned and her ass (in tight yoga pants) brushed against my crotch. Sending a jolt of electricity down through my cock. I shook my head to gather my thoughts.

"Sure" I said, as I picked it up and brought it inside. "Where do you want to do it?"

Jess blushed. "Why that's a little forward. This isn't that type of massage."

It was my turn to blush. Jess had the habit of making me flustered in her presence. Even though they were close sisters, Jess and Jen couldn't have looked more different. While Jen was shorter than me, slim build with small tits and dark hair, Jess was taller than I was, curvier than Jen and had big tits and blonde hair. And while Jen's body was tatto-free, Jess had a sleeve, a pretty cool throat design and a few more dotted all over her. Jen had told me one night after a few drinks that Jess's tattoos also ran down her side, under her tits and onto her ass. Apparently seeing her naked was a sight to see.

Speaking of which, the only similarity between them was they both had nice big asses. Not that I spent that long looking at Jess's. But after having an up close experience of it just now, it seemed like a family trait.

"I'm kidding, Dan. God you're so easy to wind up" laughed Jess. "Would you be comfortable doing it in your bedroom?"

Her choice of words didn't do much to help the blushing, but I nodded. I guess if I was just going to be just wearing a towel, the bedroom was the most relaxing place to be. I wasn't in the habit of walking around the house naked.

"That sounds like a good idea. Do you want me to do anything in particular?"

"Nope. Just get undressed and lie on your front. With a towel, obviously. I'll do the rest."

She put her bag down in front of me and bent over to rummage through it. Her ass was sticking out and staring right at me. Wow. If it was possible, it was better than Jen's. Who knew you could improve on perfection? As Jess continued to go through her bag, she hummed and swayed side to side. Her ass taunted me. I was hypnotised.

Then, she slowly squatted to look more closely in her bag. I couldn't move. I tried to walk away but my eyes were glued to the shapely softness in front of me. And my cock had noticed too. It started to shift in my pants, as if seeking out Jess's ass. Both her ass cheeks were sculpted in her pants, showing off her curves. If this had been Jen, my hands would have already been wondering all over her ass. Squeezing, spanking, stroking...

After a few more seconds, I snapped out of it and made my excuses to go the bedroom.

"Don't forget the table, silly," called Jess, still looking in her bag, ass out for me to see.

I came back, quickly grabbed the massage table and headed to my room. After setting it up and getting undressed, I hesitated taking my boxer shorts off. I was semi hard. And I worried how Jess would react if she saw me in this state. I desperately tried thinking unsexy thoughts. But my mind kept coming back to Jess's ass, poured into her yoga pants and showing off all her curvy glory.

Suddenly there was a knock at the door.

"Are you decent?" she asked through the door.

I looked down. My semi was now full on hard. Fuck.

"Erm, are you sure I need all my clothes off? Can I keep my underwear on?" I shouted back.

"Well, it's up to you. It's fine but I might get oil all over them. I'm still a little clumsy when it comes to how much I use!"

Fuck.

"Ok, just give me a minute then."

I took off my boxers and my cock sprung free. To my embarrassment, a little bit of pre cum flung onto the table. I quickly got my towel and laid down on my front on the table, tucking my cock towards my stomach. The door opened before I had the chance to finish putting my towel over me. 

"Oops, sorry," said Jess, walking in the room. She came up to the side and put her bag down. "Don't worry, I didn't see much."

I placed my head in the hole in the table and cringed. She then gently smacked my ass as if to emphasise to the point. I was too shocked to react, and frankly felt a bit vulnerable lying there with just a bit of cloth covering me. I heard her rummage through her bag and pull out what I assumed was the massage oil.

"I've been doing a lot of work on shoulders recently, but I need to focus a bit more on the bottom half. So, are you alright if I start down there on your legs?" she asked, squelching oil between her hands.

Facing the floor, I just mumbled what I hoped was a positive response. Thank God she hasn't asked me to turn over.

I felt two hands start working on my left calf. The pressure was quite nice, to be honest. Her fingers worked their way round and eased a knot I didn't even know I had.

After a few minutes, she stopped and squirted a bit more oil on my leg. A lot more.

"Shit," she said to herself. "Sorry, I got a bit more than I thought."

"Don't worry about it," I tried to reassure her. "I guess you can just keep going until it's all rubbed in."

She started rubbing again, her hands slipping a bit more than before with all the oil. Once or twice, her hands slipped up my thigh. I held my breath as her hands inched upwards with each motion, getting closer to my balls. I swear she grazed them with her oily fingernails a few times.

She returned to my calf but after a bit more rubbing, slipped again, this time landing on top of me and her hand disappearing under my towel. Her hand was on my ass.

"Oh crap, sorry," she said. Although I noticed she was a little slow to move her hand away. As she did, she glided it down my ass cheek, softly scratching it and then down the inside of my thigh. She quickly got to my calf before removing her hand. My cock ached.

"Everything ok back there?" I asked, hoping to distract myself.

"Sorry, I just got oil all over my arms now. And I think a bit on my top."

She paused.

"Could you do me a favour?" she asked, a hint of something in her voice. "I mean, you don't have to if you don't want to but it would help."

"Er, sure," I hesitated. "What do you need?"

"I don't want to get oil on my clothes. And my hands are covered in it. Could you help me take my top and pants off?"

It was my turn to pause. I still had my head in the table hole and my cock hadn't gone down. In fact, the recent touching had left a damp patch against my stomach where my cock was tucked away. I really didn't want to get up and undress my girlfriend's sister in this state.

"Well, I just..." I stammered. I didn't know what to say. I felt Jess walk up to my side and she placed a very oily hand on my thigh. She ran her hand up and stopped just before my balls. I held my breath, not sure what to do.

She then grabbed them and squeezed. I yelped in response. She bent over and put her mouth to my ear.

"Let me put it another way," she whispered. "Take my clothes off. Now."

She punctuated her request by giving my balls another squeeze. Then, with the help of her oil overload, slipped her hand under my stomach and grabbed my cock.

"I knew you liked it. Now help me out of these clothes. I don't want to get them covered in oil."

She let go of me and I turned over. The towel slipped off and I sat on the table with my leaking cock standing to attention. She glanced down with a smile on her face.

"Jen wasn't lying," she said to herself. Then she looked at me and lifted up her arms.

"Take my top off first."

I pulled her top over the head. Her large tits were pulled upwards with the motion and then bounced as they were freed. I now saw her multitude of body tattoos. Down the side of her stomach. Underneath her tits. A thorny rose snaked across her waist and disappeared into her yoga pants. They were all sexy, feminine, arty. Jen was right. Jess certainly looked good naked.

She took her top off me and threw it towards her bag. Her tits bounced again. She stood there for a second or two, as if waiting for something. I imagined her grabbing my hair and pulling my head into her chest, smothering me in her soft, bouncy tits. She turned round.

"Take my yoga pants off."

I hesitated again, not sure what the end game here was. She got impatient.

"I told you, I don't want oil on them. So take your hands, place them on my hips and peel my pants off" she ordered.

I reluctantly moved my hands and put them on either side of her waist. And slowly pulled her yoga pants down. Her round, curvy ass slowly revealed itself. And a large floral tattoo on her left ass cheek also came into view. It covered most of her ass cheek. But she soon bent over, giving me full view of her pussy as I pulled her pants further down. In the soft light, I could see she was glistening. Which only made my cock twitch even more.

As I got to her ankles, I bent closer to help get them over her feet. But as I did so, she pushed her ass back and smothered my face with it. I got a face full of her wet pussy. And my nose jabbed at her asshole. After a second or two, she shook her ass. Making her ass cheeks smack my face. I gasped and involuntary stuck my tongue out. Which disappeared into her inviting pussy. It was her turn to gasp, before pulling away.

She turned round. She glanced down at my cock, slick and wet with so much pre cum and oil from her actions earlier.

"Thanks. Now get back on the table, I need to finish this session."

I slowly turned back to lie down. Part relieved, part disappointed. As I did, I realised I didn't have my towel. Although, seeing as we were both naked now, there didn't seem to be much point in covering up.

Jess placed her hands on my thigh and slid them up. She was putting the bare minimum of effort into massaging me now. She slid her hands up to my ass and started squeezing me. 

"Erm Jess, I think we should..."

She smacked me hard in response. And then grabbed my balls again. She started massaging then before reaching underneath me to grab my cock. 

I gasped again. She squeezed again in response. Then started slowly jerking me off. There was so much oil everywhere that each wonderful stroke was hightened.

"Jess, I don't think..." I started to say, and tried to get up. With her other hand, she forcefully pushed me down again and started jerking me even harder. 

Her other hand cradled my balls. Both hands working me up into a stupor. I could feel an orgasm building up and suddenly worried about cumming from what Jess was doing.

I tried to move again. But again, Jess removed one hand from my balls and pushed me down. She stopped jerking me off and leaned into my ear.

"Don't move"

Her voice was more forceful than it usually was. It had more authority. And for some reason, my body agreed with her. I stayed still as she climbed on top of me, so she was sat on top of my legs.

"What are you doing Jess?" I asked in a bit of a panic. I couldn't pull my head out of the table hole and I couldn't move with her on top of me.

"Jess?"

I felt her pour more oil over my legs and ass. Then her hands on my legs again, rubbing up and down, then rubbing her thighs and back to mine.

"Don't worry. I've got you," she said. Her hands wondered up my inner thighs. But instead of my balls or cock, she started hovering around my ass. My asshole.

"Erm, Jess. Can we...?"

Before I finished, she started circling my hole with her finger. I didn't want to admit it, but God it felt good. And I reluctantly moaned in response. She lightly tapped, making my asshole wink. As if ready to invite whatever she has in mind. She let out a soft moan too.

"I saw you looking at my ass before, as I was looking in my bag. Time I took a closer look at yours."

And with that, she slowly pushed an oiled up finger into my asshole. I saw stars. The pleasure ripped through me as she slowly started moving her finger in and out. I ground my hips, pushing my cock back and forth against the table.

"Ooh, you like that?" she asked, fingering me faster. "You like me playing with your ass?"

I groaned in response, thrusting harder against her hand. In return, he started going even faster. After a while, she entered another finger. Two now we're in my ass, pumping away as the build up of cum started dripping out of my cock. I think she could sense I was about to cum, as she stopped abruptly.

"Turn over," she ordered.

I quickly complied, no longer concerned about what state my cock was in. It sprung up towards her, as she lifted herself up to allow me to turn over. She then sat down on my thighs, my cock between her legs. 

"You don't get to cum until I've at least tried this out for myself," she said, grabbing my cock and stroking it. First, long, slow strokes and then rapid jerks. She then lifted herself up and slowly sat down on my cock. Her warm, wet pussy gripped me as she got comfortable. I was helpless.

"Fuck," she exhaled, as she took me all in. I began to slowly thrust but she quickly slapped my chest. "Don't fucking move."

She grinded her hips into me. My hands instinctively moved to her ass, as I grabbed a handful of cheek in each hand. I slowly pulled them apart, just like I had earlier that morning. Her tits wobbled and moved in a way I wasn't used to with Jen.

Jen.

Fuck. What the fuck was I doing? I had to put a stop to this. I let go of her ass cheeks. They clapped together with a silky, oily slap. Jess giggled.

"Jess, we can't do this. What about Jen? Think about her."