My Sister and Her Friends

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Phantom300
Phantom300
1,338 Followers

A whimper from the couch turned both of our heads as Mandy sucked on the fingers she had just pulled from her bare pussy and rubbed her clit to an orgasm. She had a look of pure lust on her face as she came HARD and squirted in our direction. Wow! I had never seen that before. Lisa laughed softly and stood up, walking over and kissing her friend on the mouth softly before handing me my shorts and telling me I needed to go to bed. I thought about objecting, but the post-orgasm wave of calm had hit me, and I headed to my bedroom. I pulled on some boxers and pulled off my shirt before collapsing on the bed to sleep.

The next morning, I woke up to find I wasn't alone in bed. I was lying on my back, and someone had their head on my chest and my arm around them, with my hand resting on the small of her back. As I came to, I could tell it wasn't Lisa, as the breasts smashed into my torso were of good size. I rubbed the body and knew they were clothed, with at least a shirt on. I sensed I was still shirtless, but I could feel the cotton of my boxers on my hard dick. I sported a serious case of morning wood. That wasn't necessarily a bad thing after last night. Last night's fun replayed in my mind. Holy crap, what a turn of events! My dick throbbed a little as I recounted the blowjob from Lisa and seeing Mandy squirt as she masturbated hard on the floor. Holy crap indeed! A hand started moving along my chest. She stirred beside me. I opened my eyes and saw Heather staring back at me. "Morning bro," she purred.

I shot upright in my bed. She rolled off me and stretched lazily, her shirt riding perilously high up her mid-section. "What are you doing in here?" I asked, startled. Apparently, Mandy had been snoring loudly during the night and Heather couldn't sleep. Then she came in the bedroom to use the bathroom and saw me lying in bed and decided I looked comfortable.

"I mean, we shared a hotel bed on all those family vacations." True. I told her I didn't mind, I was just surprised. She got up and went in the bathroom. Again, I watched her perfect ass sway in some tiny shorts as she did. She looked back at me, closing the door behind her with a grin. Crap. I was busted staring at my sister's ass, this time by my sister herself!

I pulled a shirt on and went out into the den. Lisa was in the recliner and Mandy on the couch, both asleep, and covered with blankets. Oh well, nothing else to see here. I busied myself with making some breakfast and Heather came out to roust the crew. They showered, packed up, and got ready to leave. Again, each giving me a big hug and kiss on the cheek. Lisa winked at me, and Mandy pressed a finger to my lips. I thought I could smell the faintest remnants of her arousal on there, but that could have just been my dick thinking instead.

Once again, things went back to normal for a while. The girls came over a couple times a week now. I graded papers, they did homework or watched movies. Mandy, Lisa and I might exchange a stray glance here and there, but nothing out of the ordinary occurred. They'd go out on occasion, and I had a couple of unsuccessful dates. Life was normal. Typical. Heather would sleep in my bed with me when they stayed over, but nothing even remotely regrettable happened. I was comfortable, she said.

Then they slept over again one Saturday night. I had a date, and they wanted a chick flick marathon. Heather picked out my clothes for the date and the girls all sent me off with a kiss on the cheek. I came in from my date hours later. The date had gone alright, the girl was a grad student, cute and friendly enough, but there was no real chemistry between us. The awkward good night kiss I received told me that would be the end of that. I found my apartment quiet, the girls were all asleep, with Mandy snoring in the recliner, and Lisa on the couch. And Heather... was in my bed. I stripped to my boxers and slid in beside her. It was still a little awkward to me, but she seemed normal with co-sleeping, so I did my best to push incestuous thoughts from my mind.

I woke again to her head on my chest, my arm on the small of her back, this time up under her shirt. Her hand was on the waist of my boxers. Fuck. That realization alone would have made me hard. Add in a sexless date night and some typical morning wood, and I was tenting my boxers severely this morning. Heather stirred after a while, and as she woke up, she ended up dragging her hand down my body and it brushed over my hard dick. There was no mistake, she had to have felt that. Heather didn't say a word. She bid me a typical "Morning bro" and headed into the bathroom as if nothing unusual had just happened. I rose, dressed and once again returned to the kitchen to work on some breakfast. Mandy and Lisa were just as I had seen them last night, all covered up and asleep. Heather emerged with a gorgeous smile. She woke her friends. They ate, packed and left, but not until I got my hugs and cheek kissed.

I was enjoying the regular company. Heather and I had gotten closer than ever before. We had actual conversations. I learned about her boyfriends and how far she had gone with each. I came to the realization that my sister was a strong, confident, and yes, sexual woman. Lisa and Mandy would tease me here and there, and they all had a fun sexuality about them that was unmistakable. After one rather bad date, I really considered asking Mandy out. Lisa was dating someone at the time, and Mandy was always a flirt and fun to be around, so why not? But in the end, I chickened out. Why ruin a great thing?

Then 'That Day' happened. I slept in late on a Saturday morning, with no papers to grade or work to do or any real plans for the day. I eventually drug myself out of bed. I was in the shower, mulling over what to do, when I decided I was hungry and wanted food. Without thinking, I stepped out of the shower, dried off, then walked bare-ass naked into the kitchen. It was, after all, my apartment, and something I had done countless times before.

In the kitchen, I froze. Heather stood there in the tiniest of bikini tops and shortest of short shorts. She was opening a bottle of water and her eyes bulged when she saw me. After what was, in all reality, just six or seven seconds, but felt like hours, I covered my dick with my hands and backed out of the kitchen, then dashed to my room. By the time I got there, I was extremely hard. Throbbing hard. I grabbed a pair of boxers and walked back out of the bedroom. Heather was gone. I looked around and saw her keys on the table. She hadn't left. Then I saw her, outside on the small balcony, lying on a towel. Her eyes closed, earbuds in, sunning herself in the sexiest bikini known to man. Small scraps of white material covered her nipples, the rest of her perfect tits exposed for all to see. Thin string connected them together and tied around her neck. The same thin string along her hips and down, keeping another miniscule bit of cloth in place over her labia. The material was so small, the top half of her thin landing strip of pubic hair could be seen. I am talking an obscenely small bikini. I could only assume what the back side looked like.

I stared. I captured that mental image. I memorized every inch of her skin I could see. I knew I would be jerking off to it repeatedly. I was hard, and without realizing it, I had my hand on my dick. Heather had her eyes closed and was moving her head back and forth lightly, mouthing the words to whatever tune filled her head. My sister was stunningly sexy. I went back to my room and pulled my boxers down. I grabbed my dick and started jerking it. Not a light touch, not a tease, I was furiously stroking my cock as fast as I could. I needed to cum. BADLY. I saw the picture of her in my mind. Those perfect tits, the trail of pubic hair peeking out from the bikini bottom covering her pussy. My sister's perfect pussy.

I was close. I hadn't considered what was going to happen. I just wanted to cum. Standing in the middle of my room, I was about to cum all over the floor. I'd have to clean it up later, but I did not care. So close. Then I heard "Chase, are you dressed? I need to pee." Fuuuuuuck.

I pulled my shorts up in time as she creaked the door open. She scooted past me and closed the bathroom door. I groaned softly. I pulled on a t-shirt and left the room. Heather came out after another minute and joined me in the den. "Sorry about earlier big brother." Did she emphasize big? Or was I hearing things? Did she just glance at my crotch? She had wanted to lay out, but there were too many people by the pool. My balcony was small, but private enough where she could wear her 'other' bikini. "I have that red one, but this one I won't wear in public." I understood why. It took all my willpower to look her in the eyes and not stare at her tits. I laughed nervously and told her it was ok. I just didn't know she was there when I had come out of the shower. "I could tell," she giggled. Mandy was visiting family and Lisa doing some research for a paper, so she was all alone.

We chatted for a while, all the while I was seriously distracted by the amount of skin she was showing off to me. Then decided we were hungry. I suggested we go out to eat and she agreed. She went to shower, and I watched that perfect ass again as it walked into my bedroom. I shook my head and then noticed she had turned around as she reached the bedroom door. Damn. She had caught me staring at her ass again. I hoped she wouldn't be freaked out or anything. And my dick was still hard in my boxers. No way she missed that. She showered off the tanning oil and emerged from the bedroom wrapped in just a towel, having left her clothes in the den earlier. Fuck she looked good like that. I had to get a grip on myself.

I went in my room to change. I grabbed some simple khakis and an orange polo shirt. I came out and Heather was in a little flowy sundress, white with a blue floral pattern. It hit her mid-thigh perfectly and her tits practically billowed out the top. In the right light I swore it might be see-through. Holy Fuck. I thought I was going to die. She was simply gorgeous.

We took my car and went to a little bistro just off campus. It had great food and a nice view of the park on what was a perfect sunny afternoon. We talked and laughed. I swear anyone else seeing us would have thought it was a date, and that I was on my way to getting lucky later on. She touched my hand often and flirted innocently, safe with her big brother. We went to see a movie and sat close. I put my arm around her. Not sure why, but it felt good. Comfortable. She certainly didn't seem to mind. She seemed to keep steering the conversation to my love life, or whether I found various celebrities attractive. I replied honestly, then asked her how far her last boyfriend had gotten. She winked and said, "Not far enough." She stuck her tongue out at me and wiggled it seductively, then laughed at my shocked reaction.

We went to a bar away from campus I liked. It was quieter, and more of an older crowd. We had a drink or two, the waitress never attempting to check her ID. Heather was impressed. "All the other bars ID you like crazy." I told her that here the crowd was usually older and quieter, and the alcohol licensing board was much less likely to pay attention to them, compared to the wilder dance clubs in town that catered to the college kids. She licked her lips lightly, and I was mesmerized.

Then, she started to flirt with the waitress, who was a very pretty lady I had noticed many times before. They playfully bantered back and forth every time she came by, and the double entendres they tossed around soon had me very turned on. Heather never struck me as bisexual, so maybe it was just the "college party girl" side of her coming out. I watched as she felt up the waitress's butt and got her boob squeezed in return. The whole thing was so very hot. H. O. T. Hot. Heather winked at me and grinned. We left a hefty tip. My dick was so very hard.

As we walked back to the car, she laughed. "You should have seen your face in there." I admitted to being in shock seeing her act like that. "I couldn't help it, she was sexy." I agreed she was and that the whole scene was arousing. Heather laughed. Playfully. "It didn't bother you seeing your little sister flirting?" I told her at that moment all I saw were two attractive women hitting on each other. "Good to know I can turn a guy on when I want to." Want to? Was she trying to do that to me on purpose? She smiled knowingly, and we got in the car.

Back at my place, I cracked open a beer and offered her one. She declined, and we curled up on the couch to find a movie. She insisted on watching a rom-com I wasn't a fan of, and after all the alcohol we had consumed kicked in, I started to doze off with Heather snuggled up against me. So warm and comfortable. So relaxing. So good.

I awoke about an hour later to a kiss on the cheek. "Time to go to bed sleepy head." She whispered in my ear. I stood and went into the bedroom. Heather followed me in and went into the bathroom. I stripped to my boxers and climbed in bed. I was expecting her to join me, but I wasn't expecting her to do so in a lacy, frilly, short little nightgown that barely went past her butt. She had always worn more modest clothing when she slept in the bed with me. She slid in beside me and put her head back on my chest. I put my arm around her - our normal, comfortable position. I felt her silky nightgown, her hand on my stomach just above my waist. I felt her perfect tits pressed into my body. I couldn't stop it. I got a massive erection. I rubbed her back slowly, and her nightgown worked its way up little by little. I felt her hand slowly inching downwards, so I let mine do the same. I reached the hem of her nightgown partway down her butt cheek and I felt her fingers lightly touch my boxers. Then, I felt flesh. My hand was on her butt. My sister's perfect ass, and I was touching it. I froze, and she gave the softest of sighs and wiggled her hips subtly. I squeezed, and felt her hands opening the fly of my boxers.

I sucked in my breath and held it. Heather seemed to sense this, she lifted her head and looked up at me. That smile. Those eyes. I melted right there. My hand rubbed her ass firmly and she giggled lightly. "You're playing with my butt, big brother," she cooed.

"I am. And I think you like it," was my response.

"Hmmm. I think I like this more," and with that, she touched my hard cock and ran her fingernails lightly along the shaft lightly. Oooh fuck, that felt good.

She pulled her hand away and I froze. Was that too much? Did we go too far? My question was soon answered as she started pulling my boxers down my legs. I lifted my hips and soon they were as far down as she could pull them without moving her body off me. She grasped my dick in her tiny little hand and I thought I might cum then and there. She played with it lightly, feeling along its length, holding my balls in her hand, then giving it good stroke. I tried to work my hand up under her ass to explore further, but my arms would only stretch so far in this position. She whispered "wait," so I contented myself with cupping her ass in my palm and squeezing as she stroked my cock with more determination now. Softer, then harder. Faster, then slower. I swear, almost the exact technique Mandy has used on it. I wondered for a second if they had talked about this or even practiced together. Suddenly, the thought of them naked together hit my mind's eye and I groaned.

Heather continued her manipulations, each stroke sending me further and further down the road to orgasm. I wanted to cum so badly, but I didn't want the feeling she was giving me to end. I squeezed her ass now and then, more just to show her I was still engaged in the act, as her stroking had rendered the rest of me motionless. "Ooooh baby," I said aloud.

She took this as a sign to speed up and before I could react, I was cumming. The first shot hit her in the forehead. She squealed but kept jerking. Streams of cum landed on my chest and coated her hand. She slowed to a stop and then pulled herself to her knees and surveyed her handiwork. I looked up and she smiled big at me. "That was a lot of fun. Now you can go to sleep." She walked to the bathroom, and as she did, I watched her nightgown drop down and cover (barely) her ass. I was asleep before she got back into bed.

My dreams went back and forth. I saw a never-ending stream of tits, asses, nipples and pussy. I felt hands and mouths on my dick. I was hard for ages and I was jerked and sucked off by beautiful women over and over and over again. What a feeling that was. Wonderful, warm, and once again, wet...... I realized I was no longer dreaming. I opened my eyes and saw that chestnut hair moving up and down. I felt a mouth and tongue on my hard cock. My sister's mouth. My sister's tongue. Fuuuuuck it was good. Better than any blow job in the history of mankind, I swear. I groaned, and Heather looked up. "Morning bro," she said, then lowered her mouth back to my dick and resumed her work. I touched her hair and she sucked harder. She sighed on my dick. I groaned again.

She shifted her weight and swung her body around to me. She still had on only the thin, silky nightgown, which was now ridden up above her waist. I saw that perfect ass coming towards me, her talented mouth never leaving my cock. She deftly swung a leg over me and I looked up to see a set of pink, puffy, perfect, pussy lips descending towards my face. I stuck my tongue out and licked along them as soon as they were close enough. She moaned on my dick, and I lapped at them with gusto. I was no stranger to eating pussy. I'd like to think I was pretty good at it, having had my face covered in girl cum on several occasions. I dove straight in, determined to make her feel as good as my cock did that very second. She tasted wonderful. Soon, she sat upright, and my tongue buried itself between her lips. I licked and sucked, alternating, reading her body to see what felt good to her. She sat up and put a hand on my chest and bounced a few times, and I felt a wave of warm fluid over my mouth. She stiffened a bit then moaned extremely loud.

I lightened my touch, waiting for her to give me a signal. She did, swinging around and kissing me on the lips. Her tongue swirled around mine, tasting her cum and driving me wild. She stroked my dick a few times and then raised herself up and slid herself onto my waiting cock. Slowly, gently I watched her wet pussy envelop my hard dick. She was so tight, so warm, so fucking HOT. She groaned as each inch slid inside her. She thrust herself down and then raised herself back up. The sensation of her pussy sliding up and down my shaft was electric. I groaned loudly, and she started fucking me harder, riding my dick with a controlled aggression. I reached under her nightgown and touched those perfect tits for the first time, rolling her nipples back and forth, then tugging lightly on each one. She whipped the gown over her head and off, and I gazed upon them, those perfect orbs bouncing softly up and down in my hands as her body moved on my cock. She smiled down at me and licked her lips. I nearly came then. I leaned forward and took one nipple in my mouth. I sucked on it firmly, swirling my tongue around it while I squeezed her other breast. She reached down and started rubbing her clit while she rode me, and her moans became guttural as she hit another orgasm. She trembled and shuddered. I felt the rush in my balls. I whispered, "I'm about to cum."

In a flash, she was off my dick and had it in her mouth. No gentle sucking now, she was nearly fucking my dick with her mouth, up and down, with constant suction. Her juices rolled down my shaft and I exploded in her mouth. She stopped and tongued my dick as I came, load after load. I threw my head back and thrust my hips up, lost in the pleasure. She swallowed again and again before she pulled her mouth off my still hard cock. She looked at me, licked her lips again and smiled. "Holy Fuck. Lisa was right. That was good." I nodded, unable to speak. Her words lost on me for a moment.

Phantom300
Phantom300
1,338 Followers