Helping Out Girlfriend's Sister Ch. 02

This is the second part of the 'Helping out girlfriend's sister' series. You don't really need to have read the first part to follow the story. But you might enjoy the build up a bit better if you decide to go through that one first.

****

I was half asleep. Curled up on my side in bed, drifting off. Exhausted from the day.

Jess, my girlfriend's sister, had left only a few hours earlier. She'd spent the day with me, practising her massage techniques for her professional course, while my girlfriend Jen was at work. She wasn't due back till close to midnight, so it had just been me and Jess all day.

I had fully expected to be just a 'body' for Jess to hone her skills on. What I hadn't expected, was for her to have forced me to help with some other skills.

Ones that left me both mentally and physically drained. 

I tried not to think about her curvy, naked, tattooed body, covered in massage oil as I now laid in bed. Her large, bouncy tits as she shook them in my face. Her big, shapely ass that clapped as she rode me. I couldn't deny that I enjoyed thinking about her. But I immediately felt guilty for what I had allowed to happen to me.

And what I had done later that afternoon.

Yes Jess had been adamant about using me. But I hadn't put up much of a fight to be fair. And my cock had seemed more than willing to oblige her. I knew it was wrong. But God it felt so good.

All these thoughts were getting me hard again. Fuck, what was wrong with me?!

Just then, I felt a hand cup my ass. Giving it a squeeze, it slowly drifted over my hips and rested on my cock. And then started to lazily rub the tip of my head.

"Someone's in a good mood," a familiar voice whispered behind me.

It was Jen. When did she get home and climb into bed? I must have fallen asleep at some point. Maybe the blowjob I had hinted at when she left for work was about to happen? But even as she continued to softly stroke my cock through the fabric of my boxer shorts, before easing it out of the opening and taking it in her hand, my mind went back to earlier that afternoon. After Jess had just ridden me to an oily, wet explosion.

***

Jess was bent over, her ass in the air and my cum dribbling out her pussy, down the top of her thigh. She was rummaging again in her bag. I was still sat on her massage table, my cock semi hard but my balls now empty. I was looking at the glorious sight I'm front of me.

She looked round, her big ass still facing me and saw me looking. She smirked. Then as she was searching in her bag, she shook her ass. Her big ass cheeks wobbled and slapped together, ripples moving with each twerk.

My cock twitched. 

Still shaking her ass, Jess pulled a hand out of her bag and spanked herself. Once. Twice. Three times. I couldn't look away. Each slap sent shockwaves across her cheeks.

My cock twitched again and started to grow.

Jess stood up, in all her tattooed, curvy, naked glory. I had gotten to know some of these tattoos up close and personal. Especially those she didn't usually have on show. As she walked over to me, I realised I hadn't really thought of them as a turn on in general. Plenty of women had them and they didn't really do much for me. But God, I'd never be able to look at Jess's ever again. They were ticking all the right boxes. And stirring all the right sensations.

She towered over me. She reached out and gently caressed my cock. I winced, still sensitive having just cum ten minutes earlier.

"Well, seems someone's ready for round 2," she smiled, slowly jerking my cock.

I moaned in response. After a few more strokes, the worst of the sensitivity was gone. Replaced with my rock hard cock, ready and willing to do whatever Jess asked. Or demanded.

The guilt of what I was doing to Jen though washed over me. I'd never cheated on anyone before. And here I was, doing it for the first time, quite literally, with my girlfriend's sister. I tried to shift away, my cock betraying the shame I was feeling. I knew that nothing could happen again. I had to put a stop to this. I pulled my cock away from her grasp.

"Jess, we can't do that again. It's not fair on Jen," I said, trying not to look at the inked goddess standing in front of me. "What we did was wrong."

Jess grabbed my cock again and smiled. A wicked smile.

"Was it really that wrong?" she purred, slowly stroking me. "You think we just end it here? You get to come inside me and then call it quits?"

She squeezed a little harder and stroked a little faster. 

"You drool over my ass as soon as I walk in here. Get hard while I'm massaging you." She was getting louder with each sentence. Punctuating what she was saying with stiff, hard jerks.

"You take off my clothes. Lick my ass, beg me to fuck you and cum in my pussy? Then say it was all a mistake?"

She squeezed my cock in a vice like grip. All sensuality had now disappeared in her hand job. She was tugging angrily.

"Jess, you're hurting..."

"I just came over to get some massage practise in. Pass my course. Start a new career."

She took my balls in her other hand. Then gave them a full on squeeze. I yelped out in pain.

"But you. You got what you wanted and then go to throw me out like a dirty old tissue?"

"It wasn't like that,"

"Fuck. That."

"But you came on to me. I..."

With one last squeeze of my balls, she let go. She tugged hard on my cock and let go of that too. I was relieved to no longer be in pain. But had a feeling it wouldn't last.

"I was going to suggest something fun," she said. "You make me cum in return and really enjoy yourself. But now? Oh boy. Now I'll make you work for it. Stand up and place your hands on the table."

I didn't know what to do. Jess was taller than me. Even more so with me sitting down on the table. And as she'd already shown, she could easily rough handle me if she wanted to. I got the feeling resisting wasn't really an option. I reluctantly got up and turned round. I bent over slightly, resting my hands on the table's surface.

She pushed herself up against me, her tits squeezing into my back and her hips pushing into mine. Her hands came round my front and wandered over me. Across my stomach and down to my cock. She grazed my hardness with her fingernails, tracing a line up and down it.

She went to wrap her fingers around my cock, lightly. Teasing me, it throbbing in the palm of her hand. Even though she'd just brutalised it, my cock was still apparently more than willing to do whatever she wanted. I was too mesmerised to move. As if I was an onlooker, watching what this oiled up, curvy seductress was doing.

"Lie down on the table," she whispered gently into my ear. Then, a little more forcefully: "Now."

I climbed up and lay down on my back. She wandered over to stand above my head. I looked up and saw the underside of her tits, her tattoos highlighted her curves. I could see her nipples poking out. She had a bottle of massage oil and poured some onto her tits and rubbed it in. She glided her hands over her body: her stomach, her thick thighs, her curvy ass. She then finished with a quick play with her pussy and glided her hand in between her ass cheeks. She was now ready with a full body oil rubdown.

With her still oily hands, she ran them over my chest. Circling my nipples, she rubbed my pecs and then before I knew what was going on, she climbed up over me. My arms were pinned underneath as she positioned her pussy and asshole inches from my face. I got up close with the cum still in her pussy, slowly dripping out with each movement. A bit landed on my chin. She then ran a hand down my stomach, towards the base of my cock, which was standing to attention. 

"I'm going to sit on your face now, and your going to make me cum," she said, matter of fact. As if she was telling me she wanted me to go out and buy milk. "The longer you take, the longer I'll stay sat down."

While initially that didn't sound like such a bad idea, I soon realised what she meant. As her wet pussy clamped down on my mouth, her asshole covered my nose. And her ass cheeks sat either side of my face.

With all the oil and cum, she was making it hard to breathe. I tried taking a breath but all I could manage was a few short ones in the sloppy mess.

"If you want me off, you're going to have to start eating me out," she giggled. And with that, she shook her whole ass, smacking my face with her cheeks.

I was struggled to breathe properly, I figured that I better make a start. The faster I got to to work, I thought to myself, the quicker she would get off my face and I'd be able to breathe again.

I opened my mouth and stuck out my tongue out, sliding over her clit. And started lapping at her swollen button. I made my tongue flat, and took long, slow licks. And then switched up with quick, hard prodding. She moaned in response and jiggled her ass again. My nose had slipped and was now rubbing her lips. The top of my nose moving up and down, the oil and my cum making it easier to glide over, as my tongue worked her clit.

She started grinding her hips against my mouth. I stiffened my tongue, concentrating on her clit more. I then probed her wet pussy with my nose. She sighed, a heavy, breathy moan. My cock, still standing to attention, leaked pre cum as her hand just stayed at its base. Even though I couldn't move my arms much, I tried to reach for my cock to give it a quick stroke. She batted me away and she grinded a little harder, my nose going deeper into her wet slit.

"Uh uh," she sighed, referring to me trying to touch myself. I was getting so turned on - and struggling to breathe - that not being able to do anything about it was driving me crazy. 

I then felt a warm wetness enclose around my cock, as she took me in her mouth. She slowly bobbed up and down, my cock finally getting the attention it craved. I raised my hips up slightly but no sooner had I moved, Jess quickly pulled away. Then fully sat up, piling pressure on my face underneath her glorious ass. Her pussy squashing my nose before slipping and pushing right inside her. She let out a satisfying sigh.

"What part of 'No' don't you understand?" she asked, as she grinded her pussy against my face. "This isn't about you."

I tried to respond, but all I could do was muffle a noise. He pussy blocking my mouth from saying anything out loud.

She let out an annoyed sigh and lifted her ass up slightly. I took a big gulp of air, as if coming up from a swim.

"I'm going to slide down a little. I want you to lick and fuck my ass."

I nodded.

"I might return the favour. If you don't move."

With the help of her slick, oiled up body she slid down. Her pussy glided down my face and chest as it unfortunately moved away from me but her ass quickly came into a better view. I was now able to move my arms above me, and grabbed a cheek with each hand. With so much oil, I struggled to spread her ass, my hands slipping with each attempt. As I tried, her cheeks wobbled and her asshole came into view, winking at me, each time.

"Fuck my ass," growled Jess. I obliged. I gave up trying to spread her ass and just first ran my tongue up and down her ass crack, swirling it as I went over her hole. She purred. I turned and kissed an ass cheek, then went back to her hole. I did this a few times before I darted my tongue around her hole and licked it clean of oil. 

"Fuck. Fuck me that's good," she moaned. "Stick your fucking tongue in my ass. Fuck me with it."

I stiffened my tongue and prodded at her soft back entrance. She began to open up and blossom like a flower. I then stuck my tongue in, enjoying it and the response it was getting.

"Oh my fucking god. Yes, yes."

I dove my face into her ass, eager to take everything it had to offer. Her ass cheeks squeezing my face. I slathered her asshole. I flattened my tongue and licked up and down. I kept poking my tongue into a stiff point and jabbing at her hole. I kissed it and sucked.

"My fucking god baby!!! Oh yes. Yes, yes, yes! Keep doing that. Fuck!" Jess practically screamed.

She grabbed my cock and started sucking. The unbelievable sensation was immense. After a few moments, I grunted as her tongue swirling around the head. She took her mouth off, the warm wetness replaced by the cold room air.

"Are you going to cum?" she demanded.

I made an agreeable noise that I hoped indicated that yes I was. The pressure was building up in my balls. I was close.

She quickly slid off me and went to her bag. As she walked back, she had her fist closed around something so I couldn't see.

She climbed back on top, ass and pussy in my face. This time though, she gently placed her ass down on me, so I could resume licking.

She began stroking me quickly. Then suddenly, I felt a tugging and tightness around my cock. Then a few seconds later, more around my balls. Oh god. The sensation felt familiar. Something I hadn't done in a long time. Something back with Jen a few months ago.

Jen.

Fuck, why did I keep forgetting I had a girlfriend. And had been doing unspeakable stuff with her sister? 

"Did you..." I began to ask, in a brief pause.

"What? This?" She asked, as she began stroking my cock again. "Yes, it's a cock ring. One that goes round your balls too."  She laughed as she lightly tapped them. I involuntary winced. "I'm not having you cum until I'm finished. Especially as you've already got to enjoy yourself today."

She started stroking my cock. She tickling my balls as her hand slid down my cock and back up again. Then slammed her ass down on my face. My jaw felt like it was going to dislocate.

"And even then, it depends on how I'm feeling. I might not let you."

She giggled and went back to stroking my cock, her hand twisting as she got to my head. The sensation alone would have been enough to send me over the edge at this point usually. But with my balls tightly bound up, the pressure instead just built up. And my cock, if it was possible, kept getting harder. I needed to cum.

"I need... I can't... It's too..." I gasped in between breaths.

"Well, I guess seeing as you're all warmed up, we can get on with the crescendo," said Jess, as she stopped stroking.

And with that, she slid further down me until her waist was on my hips. I got a view of the back of her and couldn't help comparing it to her sister when she was in a similar position. I was fucked. This couldn't end well.

"Now be a good boy," she said, grabbing hold of my cock. She lifted herself up and eased the tip in, moaning as she did.

"Fuck," she sighed. "You're bigger than before. That cock ring is definitely working."

And with that, she slid down the rest of my throbbing, rock hard cock. After grinding her hips, and driving me wild for a few moments, she began bouncing. Her ass cheeks slapped my thighs, as she gained a good rhythm. Slowly at first, then building up. She gasped with each bounce, her ass cheeks rippling as they smacked against me.

"Fuck, fuck, fuck. Oh my god. Fuck me harder!" She cried, grabbing her tits and rubbing them as she bounced.

I didn't know if she was going to cum. Or how long she'd take, using me like a real-life sex toy. But the guilt of what I was doing with Jen's sister was being drowned out by the urgent feeling in my cock and my balls that I needed release. I felt like I was going to explode. But not in the good way.

I had to take action. I had to finish this. Even if it meant going from a passive piece of meat to a more active participant.

So I grabbed Jess's hips and began thrusting. With raw, animalistic urges, I started jackhammering her pussy.

"What the fuck do you think you're..." Jess bagan, before enjoying the fucking I was giving her. "Oh my fuck, yes. Yes, yes, yes. Fuck that pussy! Give me all you've got!"

I was banging away. The wet slapping noise with each thrust. The screams of her pleasure. The grunts of my thrusts.

"Is that all you've got?" She screamed, a teasing enjoyment ringing out in her shouting.

I had to finish this. Had to put an end to her games. I stopped suddenly and in a few swift moves, pushed her off me and had her kneeling in front of me on the table. Her ass was in the air and pussy was oozing from the fucking, greedily wanting more.

"What're you waiting for?" she teased, looking over her shoulder at me. She reached under between her legs and played with my swollen balls. "Give me everything."

I angled my throbbing, engorged cock and thrusted into her. She gasped as I entered her. Thanks to the new angle, and the cock ring cutting off circulation, I was bigger and deeper than I'd been before. I had started to loose feeling in my cock, so began thrusting, fucking, just absolutely going for it. She screamed out, still tugging at my trapped balls. I pulled out, just far enough for her to lose grip. And then plunged back into her, all the way to the base of of my cock. She screamed again and my balls slapped against her clit as I reached my end.

I was going a thousand miles an hour, determined to finish her off and make her cum.

"Fuuuuuck meeeeee!" she cried out.

It didn't take long after that. I could feel her pussy spasming, gripping my cock and she cried out in pleasure. As if she was trying to pull the cum out of my cock. Her legs were shaking. Maybe it was her turn to see stars this time?

She put her head on the table, burying it in her arms. I slowed down my thrusts but kept the power. With each slam of my cock, and loud, wet slap of groin against ass, she let out a whimper. 

After a few moments, the whimpers stopped and built up to moans again. She lifted her head up and looked at me again.

"Fuck me, that was good. I guess you're ready to cum now too?" she said breathlessly, a wicked grin on her face. "Although, from that angle you could have taken it off at any stage."

I gave a hard thrust in response. In the heat of things, I'd overlooked that simple fact. She jolted, the air knocked out of her briefly. She then reached under her legs and as I pulled out, with one hand freed me from my restraints. My balls and my cock sprung free.

"Cum for me," she ordered, her eyes rolling into the back of her head as I sped up my thrusting. It didn't take long after everything that had just happened. The sensation had started to return to my cock and with a few more thrusts, I came. Cum shot out of my cock and deep into her pussy for the second time that day.

I collapsed on her. She still had her ass up in the air, so she wiggled it as I was laying on her.

"Not bad for a second time," she giggled.

In my post-cum bliss, I absent-mindedly went to embrace her. Like I always did after sex. But as I moved my arm, she wriggled out from under me and stood up. She looked down at me, as I lay down on my side on the table. My cock flopping against my thigh, cum dribbling out of it. I was eye level with Jess's hips, and could see her swollen pussy lips and more of my cum dripping out of them.

"I'm going to take a shower," she said. As she walked towards the ensuite, I stared at her ass, concentrating on the large floral tattoo on her left cheek. Each step made it jiggle in a glorious, sexy way. Then the guilt I felt the first time started to rise up again, and I turned over to lie on my back.

God I was in trouble.

I heard the water being turned on. Then Jess took her head round the door.

"I think I'm going to need a few more massage practice sessions," she smiled. She then glanced down to the floor next to me. "Oh, and in all the commotion, looks like I forgot about that little surprise."

I leaned over the side of the table and saw a long cylindrical shape poking out of her bag. I looked at her with what must have been a quizzical look on my face.

"Shame," she said. "I'll make sure to give that a go next time."

"What is...?" I started to ask.

"It'll be so much fun," she interrupted. "I've not used my double ended dildo with someone else for a long time."