One warm spring day, after Cait got home from school, we went for a walk in the woods. I enjoyed letting her get a little ahead so that I could watch her tight ass pumping with each athletic stride. We walked until we came to the nearest lake, then sat on a flat rock, taking our shoes off and cooling our feet in the shallow water.
I sat close enough to feel the side of her thigh against mine, sensing the muscles tense when she splashed her foot out. We talked about nothing, her school gossip, the awful Detroit sports teams, but she seemed kind of distracted, so I asked if something was bugging her.
“No, I’m fine. Well, yeah. Um. Uh, you know I kinda have a thing for Megan.”
“Fuck yeah, who doesn’t? Megan is a stone-cold hottie.”
Caitlin’s best friend, Megan, was tall and slender with shiny black hair that fell to her back like silk. She was more of a girly girl; unlike Cait, she wore makeup and short skirts that showed off her gazelle’s legs, and she also took advantage of her petite breasts by going braless. The two of them would snuggle and cuddle and hold hands in the way girl besties are allowed to do without anyone thinking they’re lesbians, but I knew now that Cait harbored fantasies about Megan. I thought she was pretty sexy too, and when she came over, I always hoped for some ‘innocent’ wrestling with those two lithe and supple bodies.
“Well,” she continued, “I love to hang with her, and she’s cool and affectionate. And sometimes I think I see more than that in her eyes, but maybe that’s just wishful thinking. She does have a boyfriend, at least for the moment, but who knows? I like Megan and I like you too, after all.”
“Gee, thanks. I like you too, baby sister.”
“Anyway, last night I was over at Megan’s and she was all upset about the boyfriend, and I started kneading her shoulders, bending down from behind her and working the knots with my thumbs. And she was like, ‘Ooh, ooh, ahh, that is so good, mmhmm oh god.’ I was so tempted to turn her around and kiss her.”
“Oh, I bet. I’m turned on just hearing about it.”
“But what if it went wrong, and she was like, “Oh no, we’re just friends.” She could tell people at school!”
“No, Megan isn’t that kind of person, she’s a real friend.”
“I guess so, but still, things could be weird, and maybe we could never get them back to how they were.”
Her voice had gotten husky, and I realized that she was starting to cry. Tears ran down her soft cheeks and her lips seemed somehow smudged. I felt so sorry for her, and yet also super aroused. I put an arm around her shoulder and hugged her close. I could feel the side of one boob, but resisted the temptation to fondle it; this didn’t quite seem like the right time.
“Oh, I can see why you’re stressed out; it’s totally scary. But I think you’ll have to trust the signals you’re getting from her, and trust that she’ll be kind if you’re wrong. And remember, you are the lovely amazing Caitlin. Just think, what if I hadn’t worked up the courage to propose that you and I should, uh, you know.”
I could feel her nodding, with her head resting on my neck. We sat there in companionable silence for a minute, and then she hugged me, gave me a kiss on the cheek, and drew apart. I was a bit alarmed until she lay back on the rock, lifted her feet out of the water, and placed them in my lap. I first rubbed her delicate small feet between my hands to warm them, then lifted one to my mouth. I kissed her ankle and instep and sucked and nibbled at her dainty toes, which made her writhe and giggle and squeal with ticklish pleasure: “Eeek! Eeek! Stop or I’ll wet my pants!”
That actually sounded kind of exciting, but I did as I was told. I settled in to probe and knead her feet, pressing my thumb between the balls next to the toes, then using the heel of my hand, taking my time. She sighed and closed her eyes, and said in a near-whisper, “Oh, you know what I like.”
She got so limp and relaxed that I thought she might fall asleep, but after a minute or two I could hear her breathing more heavily. I drew her foot across the bulge in my jeans, and the knowledge of my arousal seemed to turn her on, as her breathing became more like panting. She undid a couple of buttons in her flannel shirt and slipped a hand through to massage her own breast, palpating and pinching the erect nipple.
I started sucking her toes again while continuing to massage her foot, and she opened her eyes and looked deep into mine as her cheeks flushed and her mouth gaped open. It wasn’t long before I heard the now-familiar whimpers of her orgasm; she bucked a little and ground her muscular thighs together, and I felt her toes curl spasmodically over and over, as she came in evident waves of release.
She lay there spent for a moment, then knelt next to where I was sitting, giving me a big hug that pressed my face into her wonderful tits.
“Oh Sean, thank you, I feel tons better now. I love my big brother so much!”
It filled me with joy to hear this, to know I had comforted and given pleasure to my beautiful little sister. My hard-on remained unsatisfied, but I was sure its turn would come soon.
That evening Cait went over to Megan’s to study. I wondered if there would be developments, and waited in great suspense for her to get home. Mom and Dad were zoned out in front of the TV, so I intercepted Cait on her return and we sat on the porch steps as fireflies blinked on and off in the gathering night. I took her hand between mine and said:
“So? Any news from girl country?”
“Well...” She made her little uncertain croaking sound and cleared her throat. “So we were going over our biology notes, and Megan sighed and fell silent. I asked what was up, and she said she’d finally broken up with the loser boyfriend. It was for the best, but she felt like she’d wasted so much time when she could have found something better. She looked me in the eye and then quickly down, and I thought she was blushing. My heart was racing like a pro, but I screwed up my courage and leaned across the kitchen table. I cupped her cheeks with both hands, brought her face closer, and gave her a soft kiss on the lips. I started to draw back, worried I had fucked everything up, but she quickly wrapped her arms around my neck and pressed her mouth hard against mine. I could feel her tongue starting to push between my lips, but just then we heard sounds in the hall, and Megan’s little brother Chris walked in. Seeing our flushed faces and embarrassed looks, he teased, ‘Wow, that’s some intense science homework.’
“He got some ice cream and sat down with his own books, so we had to settle for playing footsie under the table.”
“Still, you did it!” I raised a hand for a fist-bump. “What next?”
“She’s coming over Saturday night for a, er, um, sleepover. I almost feel bad for Mom and Dad. If she was a boy, they’d be going ballistic at the thought of him spending the night in my room.”
“If he was a boy and not your brother, that is.”
After dinner on Saturday, I went up to my room to play video games and fantasize about what the girls were getting up to in Cait’s room. I had fond memories of other times Megan had come over and the three of us had played Twister or just horsed around. This time I would have to settle for getting the play-by-play later, and even that thought was pricking my desire. A knock came at the door and Cait surprised me by poking her head in and saying, “Hey, dude, wanna come watch some Netflix with us?”
“Really? Megan won’t mind?”
“Oh no, she’s totally down with it...you must know she likes you. And she knows you like her, considering how excited you get when we rough-house.”
“Ah shit,” I blushed, “I thought I was being so discreet!”
Embarrassment didn’t keep me from leaping at the offer, though.
The girls lay side-by-side on their stomachs on the bed, Megan dressed for success in a silky crimson teddy and Caitlin in her big Kirk Gibson jersey, which rode up sometimes to afford a glimpse of her chaste but alluring little white briefs. I sat with my back against the headboard, where I could see both the TV screen and the hot girls.
They quickly grew more interested in each other than in the movie; Cait turned on her side and stroked Megan’s raven hair, running a hand down her back and letting it rest on the curve of Megan’s ass. They gazed into each other’s eyes, Caitlin’s brilliant blue and Megan’s a mesmerizing green, and spoke intensely in low tones. I muted the TV so that I could hear their conversation.
Cait was asking Megan about her sexual experiences—Megan was seventeen already, and worldly by our standards. Megan explained that sex was part of the trouble with her ex-boyfriend, because he was so selfish and focused only on his own pleasure.
“Wasn’t he any good at going down on you?” asked Caitlin.
“Oh my god, no way would he do that. Oral sex was a one-way street.”
“Oh that’s too bad...I’d miss that.”
“Oh, Miss Virgin? Have you had lots of guys go down on you?”
“No,” said Caitlin, then she made some sputtering sounds and a little squeak before she came out with it. “Just one.”
“Who?? Aw come on, I tell you everything, now you’re holding out on me? What kind of a friend are you?”
“Well, you have to promise to never, never tell anyone, or I’ll have to kill you.”
And so she told Megan. At first I was embarrassed, but it was also a turn-on, and Caitlin said how cool I was and how good I made her feel.
“I bet,” she said, “He’d do it for you too if you ask him nice. He thinks you’re a hottie.”
“Well, so do you, Cait!” I shot back. She turned a little pink, but grinned, and Megan grinned back first at her, and then at me:
“Okay, dude, if you’re up for it, let’s see what you got!”
With that, she sat up and scooted to the head of the bed, where I helped pull off her nightie to reveal her slender pale body. She lay back on the pillows and I bent over her torso, kissing her navel and rubbing my face along her smooth warm belly. I kissed and briefly nibbled at the bony flare of her hip and the little hollow next to it.
I crawled around as she lifted and spread her knees, and buried my face in her neatly-trimmed black thatch, running my hands down from her narrow waist to her hips and butt.
I tasted her wetness as I ran the edge of my tongue along the rim of her labia, then used the tip to stroke up her vulva to her clit. I made room for a hand and inserted a finger to curl around to her G spot, at which she grunted and moaned, digging her long manicured nails into my hair.
“Oh that’s it boy, slow, slow, right there, uh-huh, uh-huh, ahh!”
At that point, I heard wet sounds coming from above and I looked up to see Caitlin’s mouth welded to Megan’s. Caitlin had one hand rubbing circles around one of Megan’s dainty small tits, and muffled moans were coming from both of them. The next time I looked up, Caitlin’s jersey was hiked up and Megan was cupping her crotch with one hand, exploring with her middle fingers while she nuzzled Cait’s full breasts. Cait lifted the jersey off to let Megan batten onto a nipple, and began to talk to her between gasps:
“Oooh, fuck me, fuck me you dirty little bitch, you naughty, naughty girl! Give me what I want, give it to me hard.”
I loved hearing Caitlin, so quiet in real life, talking dirty like a boss.
Just then, Megan’s juices began to gush over my face, dripping down my chin, and she convulsed in a racking orgasm that must have distracted her from Caitlin. When it was over, I rested my head on the tender creamy flesh of her inner thigh and gently kissed the tendon there.
“Wow, Cait was right, you are a cunning linguist. But what are we going to do about that?” She pointed to my raging hard-on.
“Well, last time Caitlin gave me a blowjob, but what I’d really love is to put my money where my mouth was. And you know, when I go down on Cait, she calls out your name; so maybe you could help both of us out at the same time.”
Megan gave me a crooked smile and turned over onto her knees while Caitlin lay back on the pillows and brought Megan’s face up between her thighs. I crept up behind Megan and gazed down at her beautiful heart-shaped ass. I reached down to the gap between her legs and found her, of course, already wet and relaxed as I rubbed my cock-head up and down around her entrance. She said something I couldn’t understand because her face was buried in Caitlin’s muff, but it sounded encouraging, so I slipped my head in. The sight of my dick penetrating that hot pussy, and the feel of my hands gripping her hips almost pushed me over the edge right there, but I managed to hang on. The sensation of her internal heat and the friction as her muscles began to contract around my sensitive penis were exhilarating, and so was the knowledge that this lovely babe wanted me inside her despite my being shy and gawky.
I leaned forward and cupped one of her tits, which were hanging down in little triangles with her hard nipples at the points, jiggling back and forth with each of my thrusts. Then I looked up into Caitlin’s face and saw how flushed her cheeks were, her mouth open, lips trembling, eyes closed. When she opened them, she saw me in my ecstasy and smiled blissfully.
With one hand I grasped Megan’s long black hair and twisted it between my fingers, then gave it little tugs, at which she let out whines of mingled pain and pleasure.
It was hearing Cait’s telltale gasps and whimpers as she approached orgasm that drove me to mine. I held Megan’s hips and thrust deeper and deeper, then shot my load into her with desperation. I collapsed onto my side, pulling her over to me, wrapping my arms around her and pressing a B-cup boob under each hand. Caitlin lay on her other side, bathing her face in kisses, tasting herself on Megan’s porcelain skin.
At that moment we heard a knock on the door, and Mom’s voice asking, “Are you girls all right in there?”
“Oh, yes, we’re just goofing around,” they replied as I dove under the covers. Good thing they were making most of the noise, and not me, or we would have been toast.
