My Sister and Her Friends

After she drove off, my phone buzzed. Jackpot! A new counselor at the high school I taught at had finally agreed to have a drink with me. We set a date for Friday night. I had asked her out a few times already this semester, but she always gave me a "We'll see." I guess I wore her down. She was a bit older than I and a recent divorcee. She had just moved back in with some extended family. Her name was Claudia, and was very pretty, smart, and quick witted. She had wonderful chestnut-colored hair and a petite frame with a nice size set of tits. Honestly, she looked like a more mature version of my sister, although I couldn't make the connection at the time.

Friday arrived in a hurry and I was just out of the shower, putting on my best slacks when my front door burst open. "Chase, it's me," my sister's voice rang out. Fuck. Why tonight? I walked out to the den shirtless again, and again, she smirked at me. "I came over for some help like you said," she said, showing me her textbook. I explained I had a date tonight. She pouted but seemed to understand. "I never thought about you going out with anyone." I told her it was with the new counselor from school and she smiled.

"You mean you aren't dating old Mr. Barron?" She joked. I promised to help her out any other time, just not tonight. She said she'd come back about noon tomorrow. "As long as that's enough time for your guest to leave," and gave me a wicked grin as she left.

The date went well. Claudia and I talked and laughed together over dinner. Afterwards, we went for a walk in the park. It was a bit chilly out, so she snuggled up against my arm as we made our way around. We made out a little in the car before I took her home. She rubbed my chest and toyed with the waistband of my slacks. I felt her tits through her top. They were nice and round, and much firmer than I expected. She said she'd like to invite me inside, but her family was home. I was a little worked up, but I understood. I told her it was fine. And, really, it was. We had a great first date. Hopefully, it would not be the last. I really wanted to see her again.

I awoke the next morning with a massive case of morning wood. Figuring I had plenty of time until Heather came over, I threw back the blanket and started to rub my cock, thinking about Claudia and how I wanted to go so much further with her the next date. My dick had reached its maximum size and was throbbing hard. I was gently rubbing up and down the shaft and thinking about Claudia when suddenly the face in my thoughts became Heather's. We were making out. I was reaching up her shirt to feel those perfect tits. She was the one fiddling with my belt, reaching for my dick. I couldn't stop myself.

The knocking at the door interrupted my thoughts. Fuck! I was hard and throbbing and about to get to some serious jerking off. Heather was here. I threw on just a pair shorts and opened the front door to find Heather, Lisa and Mandy all standing there.

"Damn Chase, do you ever wear a shirt?" Heather quipped, smiling at me.

"Not that we're complaining," Lisa grinned.

Mandy gave me a wink and Lisa and Heather shared a laugh as they came inside and made themselves comfortable.

Apparently, the dorms were being exterminated, and the girls didn't care for the chemical smell after the rooms were sprayed. Heather told them I wouldn't mind if they came over to hang out while we worked on her history class. Of course, I didn't mind. They were my sister's best friends. And having three sexy beings in my apartment was never a bad thing.

"You guys are welcome here any time," I said. And I meant it.

Lisa chided me, "We aren't guys, dude" and grabbed her small boobs and gave them a heft. I blushed, and they all had another laugh at my expense. Oh well, worse things could happen to me in front of a couple of good-looking women. I gave the girls my Wi-Fi password, then Heather and I made our way to the kitchen table to work. We spent a good ninety minutes going over the build up to the American Revolution and straightening out the dates and names she had problems with. She called for a break and I watched her ass sway as she walked over to the fridge for a bottle of water. I felt eyes on me and looked around to see Mandy standing there, staring at me with a sly grin. Dammit. I was busted. I felt myself blush again. Mandy turned wordlessly and went into the kitchen as well. I joined Lisa in the den, who was scrolling through my Netflix account looking for something to watch.

"Damn Chase, you watch a lot of documentaries and titty movies," Lisa quipped.

"Ooh, speaking of titties, how did the date go last night?" Heather asked, appearing behind me. I said it went well, then gave them the general summary. Mandy asked if I came home blue balled which made all the girls giggle. I admitted I did a little bit, but it wasn't terrible. "I'm sure he, uh, handled things himself later on," Heather joked, and I think I blushed again. She chided me for being embarrassed. Lisa smiled, and Mandy looked away. I assured them I'd be just fine, and hopefully I'd get to see Claudia again very soon. Lisa spoke up and said she hoped I'd get to at least round third base on the next date, which drew another round of laughter at my expense. Then Heather, out of the blue, spoke up, "If not, I'm sure you can call Mandy up. Many a lucky guy in high school got to experience a 'Handy from Mandy' you know."

I gulped, I tried not to let it show. Mandy hid her face in embarrassment, ostensibly from the comment and not the fact she had in fact jerked me off the last time they were over. The girls laughed and laughed at my expense, Lisa throwing her head back and arching her back, making her small breasts press against her shirt. Her nipples were clearly on display. Did she ever wear a bra I wondered? Heather smirked at me and announced it was time to get back to work. I agreed.

We continued working on her assignments, including starting a research paper, for another hour. I showed her notes on similar research I had done last year for a class, and she was really excited about using it as a source. We wrapped up and the girls mentioned not wanting to leave right away. Lisa and Mandy were binging a new series on Netflix and they wanted to finish. I didn't mind the company and said they could stay for as long as they liked.

"You think we could all have a beer?" Heather asked.

I consented and sat in the recliner. Heather brought out four longnecks and passed them around. She then joined the other two on the couch. I texted Claudia to see what she had planned for the evening. She did not give me a quick response. Damn. I was hoping to make another date with her. Heather noticed my face buried in my phone, "Hey, no sexting while we're here."

"No such luck," I told her. One of them asked Claudia's name and what she looked like and while I described her, Lisa had already gone and found her IG account.

"Ooooh, she's a hottie Chase," she cooed.

She showed the other two the pictures and Mandy spoke up, "She looks a lot like Heather, you know. The same color hair and eyes, with plenty of boobs as well."

The girls all giggled, and I tried to hide the fact my dick was getting harder. Heather's phone went off, and suddenly they were all talking about some event on campus that they were going to the next day. Thank God. The girls finished their beers and then headed out the door, each giving me a long hug and kiss on the cheek. I pressed a little harder than normal into each hug, feeling Mandy and Heather's breasts against me, as well as Lisa's perky nipples. Damn I was hard. I wondered if they could feel it.

Heather texted me later that night, saying she hoped I was OK with them talking about my date with Claudia and all of that. I replied that it was fine, it had just caught me off guard having a sexually themed chat with my sister and her friends. I did reiterate they were welcome to come by any time they wanted, and that I had enjoyed the company.

Another few weeks went by. I saw Claudia a few more times. And after a few dates, we did start to sleep together. The sex was great, her tits were amazing, her ass begged to be spanked, her pussy surprisingly tight and tasted heavenly, and she gave great head. But... and there's always a but, eventually, there was a problem. And a big one.

One Friday night, Claudia and I were at her place having sex on her couch. She had her face on the cushion and ass pointed up at me as I fucked her from behind, everything according to plan. She was pinching her hard nipples and we both were moaning and calling out little things to each other. Suddenly, without thinking, I said, "Mmmm Heather, this feels so good." Yeah. That was the end of that. Call a girl you're dating the wrong name during sex and see how fast it all screeches to a halt. She got understandably mad. I apologized profusely. I tried to tell her Heather was someone I was no longer involved with. Now, I'm a terrible liar, and she seemed to sense that. She said if even if I wasn't cheating on her, I clearly had feelings for this Heather woman and that she refused to share or play games. I grabbed my clothes and left in a hurry, full of shame.

I don't blame her at all. If I was fucking a girl and she called out another guy's name, I'd be upset too. I came home to an unlocked door. I eased inside and found Mandy and Lisa sitting on my couch staring at the TV. I had given Heather a spare key by this point, but where was she tonight? On a date of her own I soon discovered. "Why are you two here and not out also?" I asked. Apparently, my Wi-Fi was better and the common room at the dorms was too cold. All of which made sense. Not that I cared much at that point.

I plopped down in the recliner and unbuttoned my shirt for comfort. Lisa cooed, "Ooh, are you going to give us a show?" I didn't reply. My bad mood was obvious. Mandy pried further, and I tried to shoot her down. Then Lisa joined in and I eventually relented, telling them part of, but not all, the story of my disastrous night. They both expressed their sympathies, then Lisa perked up, "Well, if you're a bit blue-balled, we could always arrange a 'Handy from Mandy' for you." She laughed, Mandy giggled, and I managed a weak smile.

"I'm sure that's the last thing she'd want to do tonight," I replied, trying to forget the way it felt last time. My dick betrayed me, and he got hard in a hurry. Damn him.

"Oh, I'm sure she wouldn't mind," Lisa spoke up. Mandy, she just smiled big and looked me in the eyes wordlessly. She had such a flirty smile. I couldn't tell if she was teasing me, or if she really was considering it. Wait. Why was I considering this? And with Lisa here? What kind of fucked up things were my hormones trying to do here? Damn, I was really hard now.

I tried to laugh out loud, but it came out as more of a grunt. Lisa stared at my crotch. "Look Chase, we've known you for forever. You're a great guy and you've had a rough night. You've been helping us out a lot lately. Let us help you out tonight."

"But... I.... What.... What if she finds out?" I stammered.

"Who, Heather? Your sister doesn't need to know, but I'm sure she wouldn't mind," Mandy spoke up for the first time. She seemed so eager. Lisa beckoned me to come sit between them on the couch. I saw myself walk over there, as if I was having an out of body experience. I didn't feel myself move, yet, there I was, crossing the floor between the recliner and the couch. I settled in between them.

Mandy whispered in my ear, "You've had a rough day, lean back and relax." My mind screamed at me to get up. To take control of the situation. To stop this madness. And then, Mandy grabbed the waistband of my slacks. I felt her hand pet my stiffening dick. And my mind lost control. I leaned back in the couch and gave in.

Lisa ran her hand through my hair and held my head to her as if I was a child. Mandy worked my slacks and boxers down to my knees and there I was, totally exposed to my sister's friends. I had known them since they were little girls. They'd grown into beautiful women. How on earth was I going to explain all this to Heather?

That thought vanished as Mandy took hold of my cock. She slowly worked it up and down, mimicking her masterful performance from weeks back. Lisa continued to stroke my hair. "Oh my, you're certainly our 'Big' brother there, Chase. That cock looks so delicious in her hands." Dirty talk from Lisa just added to the sensations. I had pre-cum dribbling down my shaft in seconds. I went from feeling horrible less than an hour ago to the endorphin rush of a lifetime. One sexy woman working my dick while another gave her encouragement and some naughty running commentary. "My, look at how it pulses in your grip Mandy. He's so hard. I can't wait to see it explode."

I rolled my head to the side and slouched down, giving Mandy better access, but also now putting my face at chest level with Lisa. Her small tits were right there, hard nipples trying to pierce her blouse. She noticed my gaze and rubbed my head a little more, then slowly unbuttoned her blouse a little and opened it up, giving me a bird's eye view of her pert breasts. I leaned over a little and licked her nipple swiftly before taking it into my mouth and suckling it. Lisa held my head to her chest tighter and moaned slightly, all the while Mandy was giving my dick the workout of a lifetime. Slower, then faster. Short strokes, then long, frequently licking her palms for just enough lubrication to make it perfect. Mandy looked me in the eye and gave me another sexy smile, and once again, I burst. Cum shot out and landed on my chest, then Mandy pointed my cock at Lisa, and the next two ropes of my seed landed on Lisa's torso. The rest coated my waist and Mandy's fingers. Lisa swirled a finger in the mess I made on her and causally sucked it clean.

"That was nice Chase," Lisa whispered. "We'll have to do that again sometime." The girls got up and went into my room to the bathroom to clean up, while I remained, hunched down on the couch, cum covered dick laying on my leg, wondering what the hell just happened.

The girls emerged and said they'd see me later. I stood and hastily fastened my pants, and each gave me a customary hug and kiss on the cheek, as if everything was normal. I stripped and staggered to bed, managing to sleep better than I had in weeks.

Heather called me the next day to say she had heard about my break up with Claudia and check up on me. She didn't mention anything else, and I hoped Mandy and Lisa hadn't told her the rest of the story. I gave her the Reader's Digest version of events, then asked her about her night. She said her date had gone terribly. He was snobby, rude, and handsy with her and she wasn't going to see the guy again. I tried to be the good brother and told her she'd find someone good for her soon enough. She replied, "I guess no one is going to measure up to you Chase."

I stammered a "What" and she said she knew that I was a great guy and wanted to find someone as good as I was. I told her that I wasn't that great a person and had done plenty of things I would regret in my dating life. She dismissed my statement and changed the subject. Thank God. She has gotten an A on that history paper. I was truly proud of her.

The girls started coming over most weekends, with no real incidents. One might be off on a date, or another away in a study group, but for the most part, all three were at my place a lot. Heather had convinced me to let them keep some toiletries in the bathroom, and they frequently used my place as the jumping off point for a night out dancing. They even tried to get me to tag along a few times. You might think I'd jump at the chance to hit the club with three hot women at my side, but I just couldn't. It would be too awkward to go out with my sister and her friends. I didn't know how I'd handle them looking as hot as they always did, and, worse, seeing other guys hitting on them.

They were getting ready one Friday night, when I noticed from the kitchen table, where I was grading papers, that they hadn't closed the door to the bedroom but about two thirds of the way. As they went back and forth to the bathroom, I would get occasional flashes of scantily clad flesh. It was wonderfully distracting. I felt my dick twitching. I tried to concentrate on my work, but it was a difficult task. I looked up once after someone cried out "Fuck" and saw Heather, my baby sister, standing directly in my view, perfectly naked. Her head was looking away, but I saw her in all her natural glory. Her perfect tits, pink nipples begging to be sucked, tight little tummy and the little landing strip of pubic hair that led to her pussy. My sister's pussy. I got rock hard immediately and dropped my head down to stare at the papers. I looked up again and she was gone from sight and the door was closed. I prayed she didn't see me staring and yet at the same time prayed I could see her naked once again.

Then suddenly, the bedroom door swung open and Lisa strode out in a short robe, her long legs looking ever so inviting. She grinned at me and headed to the fridge. She grabbed a bottle of water, then, positioning herself so she couldn't be seen from the bedroom, slowly opened the robe and showed me her naked body. Her small breasts jutting out, nipples hard as diamonds. She had well-defined abs and an all over tan. She reached down and ran her finger along the slit of her clean-shaven pussy for just a few seconds, then winked at me, closed her robe, and took her water back into the bedroom. I picked my jaw up off the floor and tried to grade papers, but all I could do was replay the images in my mind; Lisa naked, Heather naked, and Mandy's 'Handy' from a few weeks ago. Fuck! I was going crazy. I needed to cum.

I figured I'd just jerk off as soon as they left and get things over with. I mean, that's what any other guy in my shoes would do, right? The girls came out of the room dressed, all looking sexy as hell. They lined up to hug and kiss me good-bye. When Mandy's turn came, she squeezed my crotch and whispered, "Save it for later." What the Hell?

I tried to watch a ballgame on TV, distracted the entire time. I decided to wait up for them to get back. Well, I tried to anyway, but I dozed off in the recliner about 12:30 am. I never heard the girls as they came in. I woke to another wonderful, warm sensation on my dick. I was wearing shorts and a t-shirt when I fell asleep, but now the shorts had vanished. This felt different. The wonderful, warm sensation was also very, very... wet. I opened my eyes to see a head of blonde hair bobbing up and down on my cock. Lisa's tongue working its magic along my shaft as she sucked and kissed it. Ooooh my. She was sucking my dick. Lisa was sucking my dick. I looked around and gathered my bearings. I was in the den, still in the recliner. I saw Heather asleep on the couch, curled up and facing away from us, her cute little, skirt-covered ass pointed at me. Mandy was lying on the floor below her, leaning up against the couch, watching us intently. She had her skirt pulled up and her panties, the same pink ones from weeks ago, pulled down to her ankles. Her legs spread wide, she rubbed her visibly wet pussy while she watched her friend give me a wonderful blow job.

And what a blow job it was. Lisa used her hands to massage my balls and stroke the shaft. She sucked hard, then gently, bringing me to the edge a couple times before backing off and easing up. She gazed in my eyes and ran her tongue over my cock head. I looked over again and Mandy was fingering her pussy frantically with one hand, while rapidly rubbing her clit with the other hand in such a blur. Lisa continued to suck me off, and I whispered to her that I was about to cum. She pulled her mouth up and stroked my cock a few times. I saw her hard little nipples pointing directly at me. She was topless. I came in short bursts, coating her bare breasts with sticky cum. Those nipples stood at attention and begged to be touched, but all I could think about was the feeling of my release. As I caught my breath, Lisa rubbed cum into her boobs, softy playing with her nipples at the same time.