Helping Out Girlfriend's Sister Ch. 03

This is the third part of 'Helping out girlfriend's sister' series. You don't really need to have read the other two to follow the story, but you might enjoy the build up a bit better if you decide to go through them first.

****

"She told me everything, Dan."

Jen and I were in the kitchen, making brunch. I was on toast duty while Jen was busy making a pot of coffee. The smells filling the room were our typical late Sunday morning / early afternoon routine, just the two of us. We had our backs to each other as we finished our respective tasks. I paused as she had uttered the words I dreaded the most.

"Excuse me?" I gulped, focussing intently on slicing the fresh bread. Fuck. 

Jen's sister, Jess (yep, it can get confusing sometimes when talking about them! What were their parents thinking when it came to names?) had come round to practise her massage techniques on me last week to finish her training course. It had turned into a long session of her groping and fucking me. Not that I had put up much of a fight.

Since then, I hadn't heard anything from Jess. No texts. No messages passed on through Jen. No threats of what she had planned next. I was relieved in one sense but slightly disappointed in another - followed by crushing guilt of what I'd done to my girlfriend. And this see-sawing of emotions had eaten up at me over the past seven days.

"She told me what happened during your session," she explained, stirring the coffee granules in the freshly poured water. She then replaced the lid and strainer and turned round to me. I clumsily dropped the bread into the toaster and stayed facing the wall. Delaying the inevitable.

I felt her hands wraps around my waist. Which surprised me.

"She told me..." she started, as if trying to find the right words. "She told me you got a little... excited. Down here. When she was massaging your legs."

She slid her hands down my stomach and over my crotch. She rubbed my cock through my tracksuit bottoms. What was going on?

"I..." I started, not sure what to say.

Jen giggled and continued to playfully move her hand up and down the growing movement in my trousers.

"It's nothing to be embarrassed about," she reassured me. "I told her it was probably my fault, as I'd given you half a blowjob that morning."

"You what?!" I said a little too loudly.

"Relax," she said softly, continuing to rub my cock through the cotton. "I didn't want her getting an ego trip and thinking you were actually turned on by what she was doing."

She then stopped rubbing.

"You weren't, were you?" she asked.

I snorted. Trying to sound as if the idea was ridiculous. Her sister. The oiled up, tattooed goddess in all her curvy, shapely ass glory. Running her hand up my thigh as I lay on my stomach, grazing my balls and slipping a hand underneath to grab my cock... I snapped back to reality.

"Don't be silly," I said, willing the toast to pop up and distract from this conversation.

Jen started rubbing me again.

"I mean, I wouldn't blame you. She is gorgeous," she said. "And I also wouldn't blame you if her hands started to excite you after I'd had my lips around this."

She squeezed my growing cock gently. Blood now rushing from my head to my groin.

"I mean, so much touching is bound to get some things going. It's only human nature," she continued, rubbing me a little harder. As if to prove her point, my cock was getting harder and harder.

She slowly turned me around and dropped to her knees. Her hands then ran up to my waist and started to tug at my waistband.

"What's going on?" I stupidly asked.

"Well, when she told me how hard you were, I..." she broke off, as she pulled by pants down. As if on cue, my hard cock sprung up and she gasped with a smile on her face. 

"Is it weird to say it kind of, well, turned me on?"

I couldn't believe what I was hearing. Although I doubted she would have been as turned on if she'd known what else had happened. She gently grasped my cock.

"The thought of Jess rubbing your legs and you trying to hide this from her," she said, as she gripped a little harder. "Was it embarrassing?"

I said nothing, too scared to give a response.

"Did you dread her hands sliding up and getting closer? What if she'd accidentally touched it?"

Jen was getting carried away now, as she starting stroking me. The rhythmic motion of her hand jerking my cock caused me to let out a slight moan. 

"I bet you were scared to move, weren't you? Hoping that she'd not ask you to turn over and unleash this on her."

She couldn't have been closer to the truth. But as she carried on jerking me off, flicking her tongue every now and then on the head of my cock, I could tell she was enjoying what she perceived to be my embarrassment. Was she getting off on the power trip? Of me feeling exposed and awkward around her sister?

"If I'd have been there, and saw this making an appearance, I think I would have needed to do something to help you out."

She engulfed my cock. Greedily taking it in. My eyes rolled into the back of my head. Fuck me. She ran her lips up and down my shaft, darting her tongue over and around the head of my cock. Tickling the underneath with the tip of her tongue. Just the way she knew I liked.

"What would you have done?" I teased back, after a few minutes, looking down at her.

She widened her eyes and playfully sighed as she continued sucking my cock. She seemed glad that I was playing along. She pulled away and stroked me more.

"I'd have walked over and taken this big, fat cock in my hands. Then started stroking it."

As she said this, she stroked me faster. I moaned in response.

"Then I'd have..."

She greedily went back to sucking to show me. Her mouth went all the way down to my base, as she took my whole length. She gagged a little, spit and drool splurting out and onto my cock. She then stood up, pulled up her silk nightie and leaned her naked ass in to me. My now wet cock slid between her ass cheeks.

"Would you have liked that? In front of Jess?" she playfully asked again, grinding her hips and ass against me. "Would it have made you feel even more awkward?"

She jiggled her ass again, humping me. She leaned forward, leaving just enough of gap for my cock to fall between her thighs and then repositioned herself. As she continued grinding, the head of my cock was now rubbing against her wet pussy lips. I grabbed her hips, and pulled her deeper into my waist. Her ass cheeks spread across my groin. Her asshole resting on the base of my cock.

"It would have been so awkward," I playfully responded. I then started slowly thrusting, my cock sliding against her lips and hitting her clit. "But seeing as you would have been so naughty, I'd have done this."

In one slow movement, I gently bent her over, so her ass was now on full display. I angled me cock and teased her pussy.

"Oh fuck, you naughty boy. Right in front of my sister? You dirty, dirty fucker. Do it. Fuck me in front of Jess."

With her mention of her sister's name and fresh memories of fucking an oiled up Jess on the massage table from last week, I slowly pushed my cock into Jen's pussy. She was so wet, it slid all the way in, and a huge gasp escaping her lips.

"Oh my God!" she exhaled. 

I pulled out slowly and she whimpered, as if disappointed. But then I entered again, and started slowly pumping in and out, gradually building up speed.

"Yes. Yes baby. Fuck my pussy."

I groaned. I could feel myself building up to cum already. It really didn't take long. I ran a hand around her and played with her clit, already lubed up from the spit on my cock and her pussy juices. She spasmed, the electricity from my touch seemingly sending her into another world.

I continued pumping and fingering. My fingers strumming her clit. Each thrust met with a gasp and loud moan. She braced herself again the kitchen counter to give me more stability and I rammed my cock hard into her soaking wet hole. The slaps of groin against groin echoed in the room. Her ass cheeks rippled with each thrust. My balls smacked her clit as I pumped her from behind. I was close to cumming.

"Oh baby, fuck meeeee," moaned Jen, her pussy spasming as she came. Her creamy hole soaking my cock. That began to send me over the edge, and I quickened my pace. Her ass bounced as I thrusted faster and faster. I was reaching the point of no return. I was ready to explode. When...

The doorbell rang. Fuck.

"Babe, we have to stop," said Jen, looking over her shoulder at me.

I was still thrusting. "What?! I'm so close..."

"I know, I know. But it's Jess," she said, a wicked smile appearing on her face.

I stopped in my tracks.

"What? Why is Jess here?"

Jen wriggled away from my throbbing cock, it popping out from her pussy with a wet suction sound. She turned round and took hold of it in her hand.

"She's here for another massage session."

I couldn't believe it. "Are you fucking kidding me?!" I almost shouted, my cock aching for release in her hand.

"Well, I thought seeing as half a blowjob got you all hot and bothered with her last time, I wanted to see what would happen if we started to have sex before the next one," she giggled. "Get you all revved up and ready to go. I'm so excited. I mean, wow. I didn't expect you to make me cum. That was just a wonderful bonus."

"Babe, what the fuck? You can't seriously be ok with me sporting a giant hard on, even before Jess starts anything?"

"He he, I know," she giggled. "But I just love the idea of you being so turned on and not being able to do anything about it." Then as if to herself, "I wonder if you'll cum from her just rubbing your legs. That would be so hot!"

I pulled away.

"I'm not doing this babe. I'm really not comfortable..."

Jen reached down and fondled my balls. "Please baby, for me."

"I just don't..."

"Just one little massage," she pouted. "She's already seen it. She won't care."

She looked me straight in the eyes. When she saw I wasn't going to give her the answer she wanted, she gave my balls a hard squeeze. I yelped in pain.

"Let me put it this way then," she said, the playfulness and fun suddenly leaving her voice. "I'm not asking. You don't have a choice. You're going to go into our bedroom with Jess and she's going to massage you while these balls and this cock ache for release. And you're going to enjoy it." 

She looked at her hand and my swollen balls in them. "Or at least I'm going to enjoy the thought of you being flustered for the next hour."

The hard look vanished from her face just as quickly as it had arrived and she let go with a cheeky smile. "Fuck. I might even play with myself in the next room."

She began walking out of the kitchen but stopped as she got to the door and looked over her shoulder.

"I'll sweeten the deal. You get through this and you can play with this later."

She lifted up her nightie again and then, bending over slightly, spread her ample ass cheeks. Her cute little asshole was on full display for me. As she stretched her cheeks further, it puckered and winked at me. The soft, fleshy hole looked more and more inviting with each movement.

"Are you serious?" I asked.

"Oh yes. This is all yours if you do as I say."

And with that, she let go of her cheeks. As they slapped together, she spanked herself and walked off to answer the front door. My rock hard cock just stood to attention, my pants around my ankles. Pre cum, spit and pussy juice leaking off my cock.

Fuck, it was going to be a long afternoon.

****

"You told Jen that I got hard while you were massaging me?!"

Jess was bent over the massage table, doing God knows what to its legs. She was wearing what she called her masseuse uniform today. I couldn't help but think it looked just like a low cut minidress. While It hugged her shapely ass and showed off the curves of each cheek, it also rode dangerously high up her thick thighs and tantalisingly low over her bountiful tits. Jen had noticed me looking at Jess's outfit as she walked in and gave me huge, excited smile.

"I know and I bet she loved it. Did she try anything on with you?" she asked, still bent over. I couldn't help look at her curvy ass in her dress, which with each movement, rode a little higher. I caught a glimpse of the lower part of her ass cheeks as she struggled with something. The outline of her left cheek's tattoo poked out and I couldn't quite work out whether she was wearing panties or not.

"Well..." I started, not sure how much to divulge. But seeing as she already knew about the blowjob before she massaged me, and had felt comfortable enough to tell Jen how hard I was during it, I decided to go for. "We were halfway through sex when you turned up."

She stopped doing whatever she was doing with the table and stood up, pulling down the skirt of her dress a little to smooth it out  "Ha, I knew it. I thought I heard something when I was walking up. I thought it was the television!"

She looked me up and down, lingering at the still semi bulge in my trousers. "So she spent her time turning you on to then make you make feel awkward around me? Well, jokes on her." 

"I think she promised I could fuck her ass if I went along with it."

"And you believe her?! Well, if that's what she promised you, I'm sure we can work something out..."

And with that she turned back around and jiggled her ass. Was she implying what I thought she was implying?

"Look Jess, I feel bad about what we've done so far. And yes, Jen's been quite manipulative today, but I don't think we should, you know, carry on what we did."

Jess looked at me, with a look of pity and condescension on her face.

"Oh babe, you think you get a choice? She's got you started, I'm damn well sure going to finish you off."

"But she's in the next room."

"Well, we'll just have to be quiet then. And make use of this."

She pulled out a speaker from her bag, which I assumed connected to her phone.

"I'll play my massage music to drown out any yelps and pleads that you make," she winked.

"Jess, look, I've said no," I said, trying to sound stern. "Now I'm happy to help you practise and put what happened last week behind us. But..."

Jess had walked over during my little speech and was now towered over me front of me. She grabbed my cock through my trousers and squeezed. I stopped mid sentence.

"Look, Dan," she smirked. "Like I said, you don't get a choice in what happens today. It's happening. With Jen in the next room or not."

I immediately had a flashback to what Jen had said and done in the kitchen, moments earlier. What was it with these two sisters? Why did they get off on making me do things I was reluctant to do?

"Now, why don't you take this lovely cock out and lie on the table. I'll leave the room to make it look like I'm giving you some privacy."

As she left the room, I reluctantly got undressed and took a small towel to cover myself. As I sat on the table, the door opened.

"That was quick..." I started, before turning to look at the door. It was Jen. She looked giddy. This couldn't be good.

"Hey babe," she said, tiptoeing over to me. I was sat with the small towel over my waist, barely covering anything at all. I wasn't sure if Jess had given me such a small one on purpose.

"Jen? What do you want" I asked, even though I worryingly already had an idea.

She reached me and looked down at my towel. Staring at my semi hard cock, she seemed a little disappointed. But then placed her hand on my knee before running it up my leg.

"I just wanted to wish you good luck with your," she paused, "adventure."

Her hand reached under my towel and caressed my cock. She began jerking me off again, it being obvious she wanted me rock hard for when Jess came back in.

I don't know what had gotten into her. It seemed like a fire had been ignited in her and she was determined to burn me alive. She had always been a tease - whether in the shower or stopping midway through a blowjob before rushing off to work - but fuck me, she had taken it up a level today.

She stopped and having seen some of Jess's massage oil on the side, squirted some into her hand. She then went back to jerking me off.

"Now remember baby," she purred, as she slowly worked me up in an oily mess with loud, sloppy noises with each movement, "I want this big cock to be standing at attention at all times during this massage. I'll be next door listening."

"Please Jen, stop..." I pleaded. I couldn't handle anymore groping or games. I was fit to burst and my swollen balls ached so much from being denied my orgasm earlier. 

She leaned in to my ear, ignoring me and whispered: "I'll be playing with myself in the next room. Getting my pussy so fucking wet and creamy for you. And getting my ass ready for this fucking big rod. You just need to be a good boy. Do you understand?"

I tried one last time to stop her but she gripped my cock and twisted, her hand slipping with the oil and shooting off the head of my cock. I almost came there and then.

There was a knock at the door.

"You decent, Dan?" shouted Jess through the door. Jen glanced down at my throbbing, pulsating cock and smirked. She grabbed the towel and arranged it back over me.

"He's ready," shouted back Jen.

Jess walked through the door, taken aback by Jen being there but not surprised. She looked at me, the bulge under my towel and then at Jen. She gave a look as if to say she knew what was going on, but pretended to play innocent.

"Thanks again for helping out, Dan," she said. "I'm almost fully qualified and I'll soon be able to start charging people for these sessions." She gave me a quick wink. "But don't worry you two, I'll always make sure you both get a few freebies from me. After all this extra help!"

Jen ran a finger over my shoulder. I shuddered, her touch sending electricity through my body and down to my cock. I quickly rearranged the towel so I could tuck my stiff cock away without making it obvious how hard I was.

"Oh don't worry, Jess," replied Jen. "Dan's more then happy to help out."

Both women looked down at my cock, hunger in their eyes. I was going to be devoured by both today, that was for sure. The question was, who would do it first?

"That's great," said Jess, as she leaned across me to grab the bottle of oil Jen had just used on me. Her tits pushed against me. I could feel her hard nipples poking my chest. Jen hungrily looked at me, as I tried to focus elsewhere. "So I thought this time Dan," Jess continued, further rubbing her tits into me as she pretended to have trouble reaching the oil, "I could start on your shoulders and then move down? Finish with your lower back."

"Do you need to practise any front massages?" asked Jen, shooting me a wicked grin. "You know, chest or thighs? Have Dan lying on his back for you?"

I cursed Jen under my breath and Jess grinned as she stood back up, brushing her nipples across my chest, oil bottle now in her hands. "Oh, well I hadn't thought about that but it's a great idea. I could always do with more practise in those places."

Jen practically squirmed with excitement next to me. Probably imagining me trying to conceal my rock hard cock when the time came for Jess to massage my front.

"Well, I'll leave you two to it then," she said, as she headed for the door. As she left, she looked me up and down, and then bit her lip. My cock throbbed in response. Damn it, she knew whenever she gave me that look it had an instant reaction in me. She knew all my weak spots.

Jess turned on some soft instrumental music. She then came up to me, her tits eye level with me as they were constrained in her dress.

"Despite what Jen said," she said, her hand absentmindedly wandering over her dress and cleavage, "I think we should start with your back."