Helping Out Girlfriend's Sister Ch. 04

This is the fourth and final (for now at least) part of 'Helping out girlfriend's sister' series. This is a direct continuation from part 3, unlike the others. So if you want to follow what's going on in the story, you might want to read that part first.

....

"So...?" asked my girlfriend, Jen. She was standing naked in the doorway, her silk nightie now a puddle by her feet as she had slipped it off seconds earlier. She was staring at her sister, Jess. Who, unlike Jen, was still wearing her masseuse uniform (although, rather bunched up around her waist now).

She was lying on the massage table across from me - with a double ended dildo halfway up her wet, glistening pussy. The other half was in my ass, giving me the most pleasurable and painful experience of my life. She started to slowly grind into me again, staring back at my girlfriend. Both of them ignored me.

"So...?" replied Jess. She slowly raised her hand and wrapped her fingers round my throbbing cock. As if daring my girlfriend to stop her. The cock ring that was tight around it had turned it into a solid rod. My balls were painful orbs that bounced with each movement and the slick sound of oil and pre cum filled the silence as she began to slowly jerk me off again, in rhythm with her thrusting. Neither of them broke eye contact.

Jen stood her ground and bit her lip. Then, with her eyes locked on her sister's, she moved her hand to her pussy. Her fingers brushed lightly against her trimmed bush. "You do know you're playing with my cock, right?"

Jess thrusted a little harder. I winced as the dildo shot up further into my ass.

"You've always hated sharing," she replied. She grabbed my cock harder and slipped her hand up and down. She then broke eye contact and looked at my cock her hand. "Anyway, you've not been playing with him right, from what I've heard. These balls need to be emptied." She gave them a squeeze, as if to demonstrate. I squeaked in responce.

Jen, still stood in the doorway, parted her pussy lips to reveal her clit. With a shallow breath, she started to gently rub it. From here, I could see she was already wet. It was like I was in some weird twilight zone. Both women seemingly having a normal conversation while ignoring the fact that I was naked, hard and being used like a sex toy.

"And I've built up all this cum in these balls," continued her sister, as she lay with me. "So I get to enjoy the results.".

Jen continued to finger her sensitive bud as she now looked at my engorged cock in her sister's hand. Her eyes widened with every stroke of her fingers. She strummed herself in time with each jerk of my rod.

"Jen, I'm so sorry. I didn't..." I started to say.

"Shush," she replied, removing her hand and slowly walking over to the table. Jess was working me harder now. My orgasm prevented from exploding in her hand because of the cock ring. My balls felt like they were the size of space hoppers.

Jen stood beside me. My girlfriend. The woman I was meant to be devoted to. But who I'd ultimately been betraying with these sordid massage sessions. Even though, as I kept telling myself, I wasn't entirely in control of any of those sessions. She looked down at my cock, her eyes following her sister's hand as it worked up and down my wet stiffness.

"Have you two fucked yet?" she asked.

"Err," I started to reply. Lying now seemed a waste of time as we were already down the rabbit hole, so the speak. But I still didn't want to say anything to make things worse.

Although, how much worse could they realistically get? Her sister gave me a huge thrust, gasping as the dildo went completely inside her. Her pussy lips were now basically grinding my asshole, we were both so full.

"Now come on, don't lie," she teased, as her hips swayed and wriggled against me. She looked at my girlfriend.

"Does this count? Because if so, three times." she said, with a wicked grin. "If not..." she trailed off, as she squeezed my cock again.

Jen was still staring at my cock. A small smile then crept along her face.

"And how often with the ass fucking?" she asked, watching her sister thrust the dildo in and out. "I mean, I know you like a bit of ass play. But we've never gone this far. I'm a little jealous."

The sound of slick, wet thrusting and jerking was all that could be heard in response to her question. I wasn't sure what to say. Jess thrusted again, to get me to answer.

"This is. The first. Time." said Jess, with a thrust on each sentence. It felt like the whole dildo was going to slide out of her pussy and end up in my ass.

"And the cock ring?" asked Jen, marvelling at the tight rubber rings around my cock and my balls. "You've never worn one with me before."

"Well, I didn't want him to bust so quickly, seeing as you already got him most of the way there this morning," grunted Jen, thrusting her hips and penetrating my ass more. Her tits jiggled with each movement. "He'd be useless if this thing went limp after two minutes."

She let go off my cock, and grabbed the sides of the table as she sped up her thrusting. Her thighs squeezed me either side as she gripped me harder.

Jen giggled. She continued to stand there, staring at my cock as it bobbed up and down with the movements. A little bit of pre cum flew off and landed on her stomach.

"Well, we might have something to stop that," she said, wiping my cum off with her finger. She licked it and wandered off to her bedside table. Bending over, her ass and pussy was on full display. I got an eyeful of her glorious pose and couldn't stop staring. I loved it when she bent over like that. And she knew it.

A kick in my ribs brought me back round.

"Excuse me," said Jess, looking at me slightly annoyed that I'd momentarily forgot where I was.

"Don't be jealous, sis," laughed Jen, as she stood up and waved a box of pills at us.

Oh no.

"Is that...?" started Jess, a mischievous grin on her face. She stopped thrusting to try and get a proper look.

"Yep," replied Jen. "We bought some a while back for a naughty weekend away. Do you remember Dan?"

"I thought we'd left them at the hotel?" I said.

"Well, I brought them back home as I've never known you to stay so hard for so long. Jess, he came three times in one hour! And stayed hard the entire night."

Jen looked at me and the rings strained around my cock and balls.

"Three?" she said to herself. Then to my girlfriend, "That's one each," she smiled. "We can fight for the last one!"

I whimpered. Jen wasn't lying about the number of orgasms I'd had. But she didn't mention that I wasn't exactly a willing participant by number three. The head of my cock had felt like I was spitting fire. I couldn't sit comfortably the next day either, my balls, cock and even thighs were so sore. I didn't want that again.

"I'm not taking that again," I started to say, trying for what felt like the hundredth time that day to stand up for myself. Jess flicked my trapped balls and I howled in pain.

Jen put the box back in her draw and walked back. Despite the pain, I was a little relieved. I could tell Jess was disappointed.

Jen came to my side and leaned over me. "Don't worry, you don't have to." She glided her hand to my cock and started pumping. "I already slipped one in your drink earlier."

"What?!"

"I told you I wanted you hard for Jess' massage. So I took this as insurance." She glided her hand up and down my shaft, twisting as she got to the head. She looked up at Jess.

"I'll let you have the first bust, sis," she said, her hand speeding up and down my steel rod. "Seems like you've done most of the work already. You've earned this one."

With that, she stopped jerking me off and slid her hands down to the ring around my shaft. With a slippery movement, she slipped it off tugging my balls in the process.

"Let him have it," she laughed, as she threw it on the floor.

With that, her sister began thrusting again, each thrust diving further up my ass. The dildo bumping and massaging my prostate. Jess' ass cheeks slapping against mine as she took big, deep thrusts now. Grunting away as she did so. Now free, my balls had their familar ache and tightened as their painfully jumped up and down. My cock bobbed with the movement. Just before...

After a day of teasing and delayed orgasms, the pressure on my prostate took me to another level and pushed me over the edge. A warmth ran through my legs and they shook uncontrollably. Another wave ran up my spine. I felt goose pimples appear all over my body as my cock erupted with a powerful force and what felt like gallons of cum shot out. Without a hand around it to control it, cum flew everywhere like water from an unattended hose pipe. It landed all over Jess' pussy, her stomach, my stomach, my balls and even the table. The resulting cream oozing and dribbled as it slid down our oiled bodies.

Oh fuck. That had never happened before. Nobody was even touching my cock. How was that possible? And how had I shot so much? I felt weird. Post-nut shame started to creep in. Jess slowed her thrusts to a gentle rhythm. I could feel my ass clamping down on it as she worked it in and out. I looked away and ended up stared at my girlfriend's waist in front of me. Some stray strands of cum had hit her and were now sliding down her thigh.

"Well, that's never happened before," said my girlfriend, echoing my thoughts. "Now I know how to milk you when you say you've had enough."

Her sister stopped thrusting and slowly withdrew the dildo from her pussy, leaving the other half in my ass.

"How about now then?" she asked my girlfriend, holding it in place in my ass to make sure it didn't pop out. "See if you can make him cum again?"

Jen's eyes lit up. My cock was still hard, the Viagra obviously now doing it's job a little too well. But even though I looked like I was ready to go again, I was very sensitive from what had just happened.

"Can you give me a minute?" I asked, hoping to recover a little bit. Although the look on both women's faces told me what I already knew.

Jen took the dildo from her sister as Jess climbed down from the table. She started slowly thrusting it in and out my ass, Jess quickly stripped out of her uniform and kicked it to one side. Her eyes never left what my girlfriend was now doing to me.

"Please," was all I could say as I tried to move out the way. My ass was on fire.

"Hey, no fair," said Jen, as she dribbled more oil over my ass and the didlo. "I catch you with my sister, the least I get to do is this."

"But my cock is...she forced..."

Her sister walked to where my head was. Her ass right next to my head.

"I know how to keep him quiet for a bit," she winked and climbed onto the table facing away from my girlfriend. Grabbing my arms, she scooted backwards as her ass and pussy hovered above my face. I could see where my cum had slid down her stomach and joined the rest on her wet, puffy pussy lips. And just before she sat on my face, a long drop fell into my mouth. I spluttered. "Take a deep breath and hold still," she giggled.

She sat her pussy on my face, her ass cheeks squeezing my face cheeks. The wetness meant she was able to slide around as she grinded her hips, moving her pussy lips all over me. I tried to push her off, but her ass was so covered in oil I couldnt get a grip. I then felt her pull my arms up and place them on her large, soft tits

I was pinned down. My girlfriend fucking my ass and her sister sat on my face. I couldn't move. I could hear both women laugh.

"Start eating my pussy," Jess said playfully, as she grinded on my face. Her pussy lips slid over and around my slightly open mouth. "Stick that tongue deep inside."

I didn't know what to do. Trapped between both women, I wanted out and thought if I at least could obey her orders it would speed things up. Maybe I'd get out and make my escape. I probed her wetness with my tongue, delving inside her pussy and tasting the sweet, tangy juice that was dripping out of her. She let go off my arms and started to rub her clit. I grabbed her thighs and pulled her into me, desperate to finish her off and get her off my face.

My girlfriend, obviously getting an eyeful from her end rammed the dildo further into my ass and grabbed my cock. She built a rhythm of thrusting and jerking in time with her sister's pussy grinding on my face. God she loves to do things in time with what I was happening to me.

My cock was so sensitive after only just coming. But a mixture of the Viagra and the angle of the dildo pushing against my prostate seemed to be building me up to another orgasm. How was that even possible?!

"I want to see a huge load come out all over my face baby," my girlfriend grunted, as I continued to kiss and eat her sister's pussy, who was squeezing her thighs around my head. I thrusted my hips and groaned in response. But after a few minutes, it was clear that wasn't going to happen for a while with my cock still sensitive.

Jen stopped and then said to her sister, "This isnt working. I want to try something else."

"Oh yes?" asked Jess with a mischievous smile in her voice. She grinded her pussy a bit harder into my mouth, my jaw and tongue now aching slightly.

I felt Jen pull the long dildo out my ass, my asshole puckering shut as the last bit came out. Then, a warming suction sensation engulfed my cock, as she took my cock's head in her mouth. With a flick of her tongue around it, she quickly let go. I tried to yelp but her sister's pussy had filled my mouth.

"Dan loves dirty talk," she said, slowly gliding her hand up and down my shaft. "He's always asking me to do it when he needs me to finish him off. I want you to talk dirty to him while I suck his cock. I'd do it, but you know...," she laughed, "I've got my mouth full."

I groaned, knowing that it was bound to happen. I had a weakness for women saying what they wanted to do to me or telling me what they wanted me to do. It was my failsafe every time I was struggling to nut. Damnit, Jen knew everything about me.

Jess giggled. "Of course sis, anything to help out."

Jen went back to sucking my cock, her lips sliding up and down my shaft. I could feel the suction as she moved up and her mouth leave the tip of my cock as she let go. This was followed by light kisses around my head, the worst of my sensitivity now gone.

"You like that?" asked her sister, as she wiggled her pussy around my mouth. "You like your girlfriend sucking your cock while her sister is sat on your face? My sweet pussy lips all over you while she has every inch of you in her mouth?"

With that, Jen suddenly deepthroated me. Her lips reaching the bottom of my cock. I could hear gagging and feel drool slobber all over me.

I grabbed Jess' thighs even harder and involuntary thrusted my hips up into Jen's face. She let go, gasping for air, spit flying all over my lap and inner thighs

"I think it's working!" she gasped, laughing.

"I've only just begun," replied Jess. "Wait till I get really started you dirty boy."

With that, Jen took me in her mouth again. And Jess grabbed my head as she rubbed her clit against my nose.

"Tongue fuck my wet cunt, baby," she groaned. "Make me cream all over your face."

I did as I was told and stuck my tongue back in her wet slit. I wanted out of this situation but the dirty talk and the simultaneous blowjob was too much to stop. I rather shamefully wanted more. These mixed feelings of knowing I was being used and abused, but on some level enjoying the sensations, was fucking with my head. I began lapping at her pussy, drinking all her juices and she moaned again.

"That's it baby, right there," she groaned, pulling my hair. "Eat that pussy. I fucking love it when you get me so wet and work that tongue. Grab my ass and smack my cheeks. I want to smother you, you fucking dirty boy.'

I did as I was told and grabbed her ass, one cheek in each hand. But the massage oil made it difficult to get a grip. Every time I tried, my fingertips slipped across and just made her cheeks wobble against my face.

"Come on," teased Jess. "I know you can do better than that." She grinded her pussy harder, right into my mouth, making my tongue dart further up inside her.

I could sense my girlfriend working up and down my cock at the other end. As her sister humped my face, I felt a hand slide up my inner thigh and caress my balls. I felt them tighten in her hand. I inadvertently moaned and Jen made a noise in agreement with her mouth full. She sucked me faster and ran her fingernails lightly over my balls. I could feel myself getting closer to the edge again. God it felt good.

I bucked and pushed Jess' ass into my face, which sent her off balance slightly. As she fell forward, I darted my tongue in and out of her pussy quickly and then grabbed her thighs again to hold her in place.

"Ooh, naughty boy," she teased. "Are you teasing me?" She squeezed her thighs again, my ears ringing as they smooshed up against her soft inner thighs. "Keep doing that, and you're going to make me cum."

Jen let go of my cock and started jerking me off. "Fucking make her cum, baby. Make her cum all over that pretty face of yours."

I knew that both women were nowhere near finished with me, but I wanted to end this soon. So I shook my head from side to side quickly, determined to do anything and everything I could to speed things up. I flattened my tongue and ran it across Jess' clit with each movement of my head. Pussy juice, my cum and massage oil spread all over my face.

"Oh fuck baby, keep doing that. Oh fuck. Yes. Yes. Fuuuuuccckkk."

I circled her clit with my tongue, lapping at her swollen bud. Kissing her pussy lips, I darted my tongue in and out, savouring the soft folds pressed against my face.

Her breathing grew faster and more ragged. My girlfriend sped up jerking me off, flicking her tongue on the tip of my cock. Her sister bucked her hips. Once, twice and on the third time, I was greeted by a warm, wet wave of release from deep inside her pussy. I kept playing with her clit and pussy, lapping up every drop that was coming my way. I could still feel Jen jacking me off and, as she played with my balls, she finally sent me over the edge and I came too. I quickly felt a pair of lips engulf the head of my cock, as if she didn't want to waste a drop either.

I bucked my hips again, hoping to indicate that I was done. But Jen kept sucking and darting her tongue over my sensitive head. Euphoria quickly led to pain, as it was getting too much. I tried to wriggle away, but the oil and her sister sitting on my face gave me few options.

Except one.

Jess was coming down from her orgasm so I decided to play the sisters at their own game. I kept playing with her clit. Not just licking but also sucking as hard as I could. She squealed and tried to move away. But with my girlfriend not giving up on my cock, and Jess unable to get leverage to get down from the table, I held her down by her thighs and kept sucking. She bucked and started to pull my hair. Lightly at first but then a little harder.

"Baby, I'm... I'm... please stop... you're..." she said, a tinge of painic now on her voice.

I smiled inwardly. I was finally getting my own back on these two. Sort of. My girlfriend was still playing with my sensitive cock and it was hell. But I was giving as good as I got.

Or so I thought.

"Dan, you need to stop. I'm... I'm going to..." pleaded Jess, trying to lean back and away from me. "It's too much..." Then, without warning, another flood of warm, wetness drenched my face. This one I wasn't ready for and I coughed and splutterd. It just kept on coming. It felt like I was being waterboarded, there was so much of it.

Jen let go of my cock and looked at both of us. Her sister kept coming, squirting in my mouth and up my nose with her sweetly juices. At least my cock was left alone now. Thank god for small miracles.