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My Girlfriend’s Sister

Category: Group Sex
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The summer of 2009 was a little bit expensive for me.

Five weddings – complete with overnight hotel stays, wedding gifts, bachelor parties, cash bar – drained my bank account rather quickly.

So when my girlfriend asked if her sister could split a hotel room with us for a hastily-planned sixth wedding of the year for one of their cousins, I was all for it.

My girlfriend, Amanda, was extremely close with her sister Melissa, who was a year younger than us at 24. In the five years I had been dating Amanda, I naturally also grew very close to Melissa. The two of them shared an apartment near mine just outside of Boston.

We all had fun together for the most part. We would go out to dinner, the occasional double date if Melissa had a boyfriend. She even tagged along on a vacation we took to Brazil one summer.

Most of my nights over at Amanda’s house included a little bit of TV watching in the living room with the three of us hanging around and having a snack, and ended with me pounding away at Amanda’s seemingly always-hungry pussy in her bedroom. We fucked every chance we had, and it wasn’t really any kind of secret from her sister. Every so often when I’d go out to get a post-fuck snack or drink of water I’d catch an inquisitive look from Melissa, who obviously knew I had just finished plowing two rooms away.

(If she only knew that when she wasn’t home, Amanda and I boffed on every piece of furniture in the apartment, even her bed.)

Amanda for the most part, couldn’t get enough. She is about 5 foot 3 and a muscular 125 pounds from hours of yoga practice and gym workouts. She had dark brown hair down just past her shoulders, but my favorite feature were her wonderful tits. They were just a bit more than a handful, somewhere in the C-cup range, and they always looked delicious. Even after being with her for 5 years I was always trying to sneak a look down her shirt at those marvelous mammaries. She loves it when I suck on her nipples or grab those gravity-defying beauties while I pump my cock relentlessly into her pussy.

The great tits are a feature Melissa also is blessed to have. I’d been given dirty looks on a number of occasions from both of them for letting my eyes wander into forbidden territory. The sisters looked similar, enough to notice a resemblance, but they weren’t a match by any means. Melissa was about two inches taller and a little bit thinner, although her ass was much more plump, maybe even more spankable, but I had never had the chance to test that one out.

But those tits, they were always begging for my attention. I can’t tell you the amount of times we’d be sitting in their apartment, watching a movie or some dumb-ass show like Sex and the City or Real Housewives of Scripted Beach (Get it?), with my attention completely focused on Melissa’s tits on the next couch over. Our usual seating arrangement allowed me to sit slightly behind Melissa, usually with Amanda’s head resting on my chest or on my arm. So if I was bored of the TV show, I’d stare at those tits unashamedly.

In the few months before the wedding, I had noticed Melissa being a lot nicer to me. She had always been great to me, but it was a little something extra that I noticed when she was clearing my place for me after dinner if we ate in the apartment, or offering to get me something from the kitchen. I never thought much of it, just figured she was in a good place in life, succeeding in her job, maybe just in an all-around good mood.

Was she flirting? I didn’t know, and Amanda never said anything. I did some subtle flirting back now and then. I’d ask her if she lost weight, tell her that her hair looks good like that. Simple things that could pass as friendly, and our happy coexistence continued.

But anyway, to the wedding.

The wedding for their cousin was in southern New Jersey, not far from the Pennsylvania border. On a Friday night after work in October, the three of us put our bags in the trunk of my car and made the over 5-hour drive to our hotel, arriving just shy of midnight with a stop for dinner.

The girls were tired, but I had a coffee around 9 p.m. so I didn’t fall asleep at the wheel and crash the car into a bridge abutment. That would have ruined the entire weekend, after all.

We checked into the hotel and I brought the bags to our room with the girls lazily following behind carrying their dresses and my suit. Being wired, I told them I would go check in with the hotel employee at the front desk and make sure I knew how to get to the church for the wedding the next day.

Melissa said she was going to take a shower before bed, and Amanda said she’d go next.

So down to the lobby I went. I checked on the directions and asked what kind of activities there might be in the area in case we had some time to kill, and headed back upstairs to my hotel room 5 minutes later.

I wasn’t prepared to see tits when I opened the door, but there was Melissa, facing the mirror fiddling with something on the dresser, topless, so that her side was to me and a got an unobstructed profile view of her thin frame and those wonderful tits.

She noticed me come in almost immediately and let out a loud shriek before jumping onto one of the beds and darting beneath the blanket. I just stood there in shock for a few seconds before muttering an apology. The bathroom door was closed, and I could hear the shower running inside, my girlfriend showering just a few feet from where I had seen her sister’s boobs.

I didn’t know what to do, so I just stood for a second, the image of her flat stomach and perky tits burned into my mind.

“Uh, is it safe, to come in yet?” I stupidly asked.

“Yeah, I guess. Can you hand me the sweatshirt on the chair?” Melissa replied.

With my head down and eyes on the carpet so I didn’t embarrass her, I handed her the shirt.

The shower stopped, and while I busied myself unpacking my bag for a minute, Amanda came out of the bathroom wrapped in a towel.

“What was that scream for?” Amanda asked me.

“Uh, well, when I came into the room Melissa wasn’t wearing a shirt,” I replied, figuring it was best to just tell her.

Amanda gave just about the most unexpected response I could imagine. She giggled, then plain burst out laughing.

“Why would you not wear a shirt when there are two other people sharing the room?” she asked her sister in between chuckles.

“I was about to put it on!” Melissa replied. “Plus, I’m not even sure if he saw my boobs.”

Amanda turned to me and raised an eyebrow.

“Well?” she said.

“Yeah,” I said sheepishly. “I saw them. Or just one I guess, it was from the side.”

“Oh well,” Amanda said with a smile, again surprising me. I figured she would be pissed. She had never been the jealous type, but then again I had never seen her sister’s bare chest before. “Let’s get to bed. After you take a shower, smelly.”

She followed me into the bathroom, I assumed to brush her teeth and dry her hair. As I started the water and started undressing, she leaned in and kissed my neck, then brought her lips close to my ear.

“How was it? Did you like seeing her tits?” Amanda asked me.

I gave a blank look. How could any answer possibly turn out well?

“I’m not mad. She’s always had a little crush on you, you know. She probably wanted you to see her naked,” Amanda said, as she pulled me in close and slid her hand over my stomach and chest.

As I let my hands roam her back, down over her tight ass, she dropped her hand to my crotch, suddenly grabbing my cock over my boxer shorts.

I’m smart enough to know that when things are going this well, opening my mouth is the worst idea. So instead I leaned in for a kiss and pressed my tongue into her mouth.

Amanda’s hand snaked its way through the fly in my shorts, gripping my half-hard cock.

As she kneaded my shaft, I took my chance, checking to make sure the door was closed, and took off her towel, revealing her gorgeous body in all its naked, sexy glory.

She dropped to her knees, giving a slow, agonizing tug on my shorts on her way down. My cock was soon swinging freely, up to its full 7 inches. She helped me step out of the underwear then came back up and whispered in my ear.

“Get in the shower. But don’t you dare jerk off, it’ll be worth it when you get to bed.”

What could she have planned? Was she really going to fuck me with her sister there 3 feet away? Or was this a twisted punishment? A blue-ball lesson for accidentally seeing her sister’s tits?

With thoughts of Melissa’s tits in my head, I finished my shower quickly and dried off. With the towel around my waist I went back into the room to fetch a pair of sweatpants from my bag.

I stopped dead in my tracks as soon as I get out of the bathroom.

There standing in front of me was Amanda and Melissa, both topless, and both sporting grins a mile wide. They were wearing nothing but underwear, and the intense horniness I felt all at once was almost too much to take.

“What.. uh.. why.. what’s going.. on?” I could only stutter.

“We figured you’d want to get an actual look at them,” Amanda said. “After all the times we’ve caught you staring at them, that one quick look couldn’t have been enough, right?”

She didn’t wait for an answer, but stepped forward and grabbed my hand and led me into the space between the two beds. She swirled around behind me and wrapped her arms around my waist, facing me toward her delicious sister, wearing nothing but a pair of pink boy-short panties.

After staring for a few seconds, I took a step forward, suddenly aware of the huge tent poking out of the towel around my waist.

As if sensing where my attention was, Amanda deftly snatched the towel from around my waist, baring my dick for Melissa to see. It was as hard as steel. Those boobs I had been sneaking peeks at for 5 years were right in front of me, and the two girls were encouraging me to take a good look.

“Go ahead, grab them,” Amanda said in a husky voice behind me.

Though stunned, I couldn’t argue with that. I stepped forward slowly, making eye contact briefly with Melissa. Her eyes were reassuring, and her disarming smile gave me the go-ahead I needed.

With shaking hands I reached out and cupped both of those amazing titties from the bottom, hefting their weight before sliding up and palming her nipples. They felt amazing, the forbidden fruit I never thought I’d get anything more than a sideways glance at.

There I was all that time, hoping and praying I’d get a look down her shirt, and now I was holding the beautiful melons with my erection pointing straight at my girlfriend’s sister.

Amanda had taken up her place again behind me and began rubbing her hands all over my body. She rubbed everywhere, getting ever closer to my dick. When she finally reached it, I let out a moan, and it wasn’t long before her right hand was stroking me and her left was cupping my balls while I fondled Melissa’s boobs and pinched her perfect nipples.

“Do you want her to help you out?” Amanda asked me.

I could only moan and nod my head. The two girls made eye contact briefly, and Melissa slowly reached her hand out and stroked the side of my face and my neck. She let her hand trail down, sliding over her sister’s, before reaching the top of my cock.

The touch was amazing. It was just a hand on my dick, but it was exhilarating in so many ways.

As she got closer to me, it was harder to keep caressing her tits, so I hugged her close and let my hands drop to her ass, squeezing and kneading that wonderful butt.

As my fingertips started to slip under the waistband of her panties, Melissa moved away. I immediately thought I wrecked the whole thing by getting greedy. She gave me a smile and slipped her own fingers into the waistband and in a flash those pink shorts were on the hotel room floor. I didn’t get a good look at that moment, but she was clearly shaved bare. She took a step toward me, dropped to her knees and stared straight into my dick.

Amanda released her hold on my dick and took a step around to my side. She pushed me backwards gently, giving me the hint to turn, and sat me on the edge of one of the beds while kneeling on the floor next to her sister.

I could feel Melissa’s breath on my legs as she got closer, and soon I could feel her warmth on my dick.

She looked directly into my eyes and gave my cockhead the lightest kiss. I moaned, and she did it again, this time leaving her lips on my cock a little bit longer. She reached up with her hand and gripped my shaft around the base. As she angled me downward slightly, she took my head into her hot mouth, sucking gently as she swirled my tip with her tongue.

The feeling was incredible. Her tongue was silky, and slowly she slid my cock into her mouth a bit more before taking about 4 inches into her mouth and slowly withdrawing. As her lips left my dick, Amanda leaned in and took my dick into her own mouth. She began bobbing up and down, getting my rod nice and wet.

After a minute she pulled off, letting Melissa move in closer again. She took my cock into her mouth, putting pressure on the bottom of my shaft with her tongue. She was always just a bit on the shy side, but the blowjob she gave me that night was unbelievable. She completely took over, wrapping her hand around the base and occasionally moving it down to fondle my balls. The way she moved her head and used her tongue made it some of the best head I’ve had in my life.

My girlfriend Amanda came and sat next to me on the bed to watch the show – her hot younger sister sucking my dick.

With the expert attention I was receiving, I was getting close to blowing my load.

As my moans increased, Melissa looked up and straight into my eyes. That intimate gesture was all it took.

“I’m going to cum!” I yelled.

Melissa didn’t miss a beat, she took slightly more of my cock into her mouth as the first jet of my cum blasted the roof of her mouth. I pumped shot after shot of cum into her mouth as she kept sliding her lips over my shaft and teasing the underside of my head with her tongue.

After an eternity, my cock stopped pumping cum into Melissa’s mouth, and with a few more bobs she pulled her mouth off me with an obvious mouth full of cum.

She stood up and leaned toward me, pushing her tits near my face as she leaned her head over to Amanda and brought one hand to the side of her sister’s face, tilting her head back slightly. I couldn’t believe my eyes as Melissa leaned in and locked lips with Amanda. She shoved her tongue into Amanda’s mouth, dropping my full load of cum along with it as the sisters began furiously making out. My jaw hit the floor, a million dirty thoughts running through my head as one of my deepest fantasies played out right in front of me.

My girlfriend was swapping my cum with her sister. And they were both into it!

Finally with a big swallow and a moan, Amanda broke the kiss with a huge grin. She turned to me with a wink.

“So, did you like that?” she asked.

“Holy shit!” was all I could muster as the girls giggled.

“Did you two plan that?” I asked them.

“Well, not exactly. She’s had a crush on you for a while,” Amanda told me. “When you saw her tits it turned her on. I was just planning to suck your dick as soon as she fell asleep, but she said she wanted to do it for you since you were so nice and drove us all the way here tonight.”

I looked over at Melissa, who looked embarrassed.

“She improvised that last part. But it was fine by me. She’s a good kisser, it turns out,” Amanda said.

“So, you ready to return the favor?” Melissa asked.

“Really? You’d let me eat you out?” I said.

“It’s only fair. I just sucked your dick didn’t I?”

Her logic was sound. Completely fair. But what would my girlfriend say. I looked over to her and noticed a look indicating she was thinking about it.

She looked back at me. “I guess it’s ok. Plus, he’s pretty good at eating pussy,” Amanda said. “But you have to fuck me after you make her cum.”

Wasting no time, I gently took a hold of Melissa’s arm and brought her to sit on the bed beside me. I brushed the hair away from her face and brought my hand to her neck before leaning in and giving her a kiss on the cheek. I looked into her eyes and brought my lips to hers as we sat side by side, bare naked on the bed. Her lips opened, and I swept my tongue just inside her mouth, feeling for her tongue. She pushed her tongue out to meet mine, and we locked in a French kiss. I brought my left hand to her right breast, gently squeezing the perfect globe as she rubbed her hands over my arms.

Melissa must have been horny. She broke the kiss and leaned back onto the bed, spreading her legs and pulling me on top of her between them. As we continued to kiss I let both hands roam her body. I ran my right hand over her thigh a few times, and shifting my weight I brought my hand to her crotch to finally feel her pussy.

My brief glimpse earlier was right. She was completely hairless. And holy shit was she wet. Before I even pushed a finger between her cunt lips I could feel the juices coming out. I cupped her mound and ran my middle finger between her lips a few times, getting it soaking wet, before pushing it into her pussy.

Melissa let out a low moan as I fucked her hole with my middle finger. As things got really wet I added my index finger and slowly fucked her with two fingers. I leaned farther to the side and looked over to the other bed, where I saw Amanda with a glazed over look on her face reclining on the bed running a hand over her still-covered pussy.

She saw me looking and gave me a smile and a wink, then reached down with both hands and slipped her black thong off her legs. I smiled back as she continued to rub herself, and shifted my attention back to Melissa.

I gave Melissa’s neck two kisses before moving slowly down her body and planting kisses as I approached her soaking slit. I kissed her a few times right on her mound and all over her outer pussy lips, and finally extended my tongue into her pussy.

Her flavor was amazing, and somewhat similar to my girlfriend’s taste. It was not too strong, the kind of pussy flavor you could eat all day long. I tongued her hole up and down, pushing it inside of her and swirling it all over that delicious snatch.

As Melissa’s body began to gyrate slightly and she began to moan more, I moved my tongue up to her clit, flicking across it a few times before gently sucking into her mouth. This prompted an excited “Oh” from her, and I continued to alternately suck on her clit and drag my tongue over it.

Knowing she was getting more and more worked up, I focused all my attention on tonguing her clit. She was moaning more and more now, and with all my saliva and her soaking wet pussy things were getting pretty slippery. I started to work my middle finger into her pussy slowly to finger-fuck her as I continued to work on her clit.

Melissa was now panting heavily and brought her hands to her own tits, squeezing and pinching her nipples as she moaned and panted, the telltale signs she would cum for me soon. She was incredibly hot like that, and my cock was rock hard once again.

I could tell she would cum any second, and started to curl my finger up inside her pussy, feeling for her G spot to finish her off.

Suddenly her body went stiff and tensed up completely. Melissa’s pussy clamped down on my finger inside her and I continued my assault on her clit. All at once she relaxed and let out a scream as her pussy clenched and unclenched while she had a powerful orgasm. She came for what felt like 5 minutes, moaning over and over again while I kept tonguing her clit and pressing my finger against her G spot.

Finally she began to calm down, and I slowed my work on her clit while slowly sliding my finger in and out of her. As she came down from her orgasm I withdrew my finger and brought my tongue down to her opening to taste more of her delicious pussy juice. She was literally gushing and I coated my face as I lapped up her flavor.

With a last moan Melissa sat up and gave me a smile that said ‘thanks’ before flopping back down on the bed. I sat up and crawled toward her to give her a kiss on the lips.

Just after I planted a smooch, I was knocked over onto my back. Amanda climbed over the two of us and straddled my waist. She leaned down and gave me an aggressive kiss, no doubt tasting her sister’s pussy juice all over my face.

As she sat up I brought my hands to her tits and squeezed.

“Mmmm. My sister’s pussy is pretty good,” Amanda said. “Maybe someday I’ll try some right from the source. But right now I need you to fuck me.”

Melissa had recovered and propped herself up against the headboard of the bed. Hearing that, she moved around behind the two of us as Amanda leaned forward. Melissa reached between our bodies and grabbed my dick, stroking it a few times.

“Yeah that’s it. Get him ready for me so I can fuck that big dick,” Amanda said, leaning to the side. Melissa leaned down and put her mouth over my head, coating it with her spit.

“OK, he’s ready!” Melissa said with a giggle. She held it upright, and Amanda got back into position by hovering her snatch above my cock. She quickly lowered herself, and with her sister holding me in place she impaled herself on my dick. Evidently as she watched me eat out her sister, she got herself ready.

Amanda began to bounce on my cock and I grabbed a hold of her tits. She was furiously fucking me, working herself toward an orgasm as I just enjoyed the ride.

When Amanda gets really horny, she often takes matters into her own hands and just uses my meat to get what she wants. This time was no different, but she was fucking me even harder than usual.

Melissa came and kneeled near me, watching as my dick pistoned in and out of her sister. The expert blowjob I had gotten earlier had me totally in control now as I began to thrust up into her, meeting her halfway and slamming my dick into my girlfriend’s tight box.

“Ohhhhhh your dick feels so good,” Amanda said.
“Yeah baby. Keep fucking me, you’re so tight. Cum for me baby,” I said back to her.

Amanda leaned down over me and stopped bouncing, instead thrusting her hips backwards and forwards with my prick buried up to the hilt inside her.

“Ohh yeah. I’m gonna cum!” Amanda screamed.

With a quick motion, I hugged her tight and flipped us over, clumsily getting on top of her. I began to pound away at her pussy as her hand moved down between us and she began to rub her own clit.

“Ahhhhhhhhhh fuuuuuuck,” Amanda yelled as she began to cum. Her tight pussy clenched around me, trying to draw the cum out of me, but I held on as I continued to pound her through her orgasm.

She began to breathe easier, and I slowed my humping until I was sliding slowly in and out of her dripping snatch.

“Oh my god,” Amanda panted. “You didn’t cum yet? My sister must have given you one hell a blowjob. Why don’t you see if she wants to fuck.”

I looked over at Melissa, who was just staring at us with her mouth partially open.

“Well, do you want to fuck him too?” Amanda asked her sister.

“Holy shit, yes!” Melissa replied. “That was amazing!”

I pulled out of my girlfriend, who laid back and let out a soft moan. Melissa immediately moved toward me and brought her face toward my prick. She lapped up all the pussy juice, moaning as she sucked my cock yet again.

Turning around, Melissa got on her hands and knees beside her sister.

“I’ve never tasted pussy before,” Melissa said to Amanda. “It’s not bad. And I never expected yours to be the first one I tasted.”

Melissa leaned down and give her sister a kiss on the lips before looking back at me.

“Well? You going to fuck me or what?”

I didn’t need any more invitations. I got up on my knees behind her and took my dick into my hand, bringing it right to the entrance of her wonderful pussy, which was still wet from the cunnilingus I had just performed.

I pushed into her pussy from behind, slowly inching into her incredibly tight hole. Her burning hot body was squeezing my dick so tight I had to close my eyes and try not to cum right then.

When I got about half way into her I stopped and withdrew slightly before going forward once again. She eased her knees apart and arched her back to accept my full 7 inches.

“Oh my god. His cock is amazing,” Melissa said to her sister, who giggled.

“Why do you think I’ve kept him around for 5 years?” Amanda replied.

I began to plunge in and out of Melissa, remembering every dirty thought I’ve had about her in all those times I’ve snuck a peek down her shirt or watched her prance around the house with no bra.

This was a dirty fantasy of mine, and I was going to enjoy every second of it.

I looked down and watched my dick slice through her beautiful pussy lips as her puckered asshole winked at me. I grabbed both of Melissa’s hips and began to fuck her for all I was worth, pounding against her ass and drawing shrieks of pleasure out of her.

I started to moan myself, but I was getting tired.

“I gotta switch. Ride me,” I said as I pulled out and laid on my back. Melissa straddled me in the same position her sister had moments earlier. She reached back and positioned my dick against her pussy and all at once slid down my rod, completely burying me inside her. Melissa started to ride me, and I still couldn’t believe how this night had turned out.

When I thought about driving through three states to go to a wedding, I had no idea it would end with me fucking my girlfriend and her sister.

They were both amazing, and just when I thought it couldn’t get any better, Amanda sat up and brought one leg over me and straddled my face, facing her sister. She lowered her pussy toward my tongue, and I was happy to begin eating her out. The two sisters leaned into each other, each cupping the other’s head and locking lips. The started to make out, both girls moaning as Melissa rode my dick and I flicked my tongue across Amanda’s clit.

Suddenly Melissa sat back a little bit and started bouncing even faster on top of me.

“I’m gonna cum! Oh keep fucking me!” she screamed as I thrust my hips up to meet her on each stroke.

“Yeah! Keep going!” Amanda said, approaching her own orgasm on my face.

Both girls came at the same time, with a crescendo of screams and moans as one girl came on my tongue and the other came on my cock.

I was almost there, and as Melissa’s orgasm subsided she leaned to the side and slipped off me, collapsing onto her back with a sigh. Amanda leaned forward and took me into her mouth in a 69 position. She continued to moan as she tasted her sister’s pussy again on my dick.

It was too much for me, and I finally began to cum for the second time that night, this time in Amanda’s mouth. My dick jerked in her mouth and blasted shot after shot of cum onto her waiting tongue.

After so much excitement, it was a powerful, draining cum. I nearly blacked out. I don’t know how long we stayed like that, with my dick oozing cum into my girlfriend’s mouth, but as she finally started to ease off me I came around again. Amanda got off me and turned around, hovering over her sister.

Once again, the two girls shared my cum, kissing as they tasted my load. With cum on their chins they finally broke their kiss and laid back, all three of us in a row panting and basking in the glow of an incredible fuck session.

“Wow.” I said.

I was tired. I looked over at the clock. It was 2:40 a.m.

“Let’s go to sleep,” Amanda said. “Get in the middle, stud.”

We shifted around, and both girls snuggled up to me, one on each side. Melissa reached over and turned off the bedside lamp, and I pulled the blankets of the bed over us. We fell asleep within minutes, and didn’t wake up until 10:30 the next morning.

I’ll spare you all the long details, but the morning went way better than I thought it would. Both girls were practically glowing. They both said it was the best sex they’ve ever had, and they had no regrets about sharing me for a night.

We went to the wedding that day and had a fantastic time. The thing I was most surprised about was that it was never awkward between the three of us.

It has only been a week and we’ve all been pretty busy with work so it’s too soon to tell if I’ll ever get the chance to fuck them both again, but I can keep hoping, right? Amanda hasn’t said anything about it, but she’s been as happy as can be this week so far. Maybe sometime soon I’ll have another story to share about how I fucked my girlfriend’s sister, but until then, I’ll have the wonderful memory of a naked night between two hot girls in a New Jersey hotel room.

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