Sister's Five Kisses - Cover

Sister's Five Kisses

Copyright© 2022 by Maracorby

Chapter 2

Erotica Sex Story: Chapter 2 - Rowan lost the bet: she owed five kisses to whomever her brother Jamie designated. It was up to him, but there were definitely right and wrong choices.

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   ft/ft   Consensual   Fiction   Brother   Sister   First   Oral Sex   Petting  

Rowan didn’t stay with us the next summer. The official reason was that she was going to archery camp, but that was only for five weeks. The real reason, Rowan hinted in her letters, was her stepdad’s insecurity. Something in the adult world had challenged his sense of manhood, and he’d responded by tightening his grip on what was “his”.

We were fourteen the next time she came to live with us. She was a girl by then. Not a girl like just another kid but with long hair. Rather, a whole different type of creature from us boys - intriguing and ineffable.

Two weeks after her arrival, Rowan, Ben, Teddy and I were loitering in a half-finished construction site. It was clearly meant to be a commercial building of some sort, but little more than the frame was built. There were all sorts of pits, piles of bricks, and unused machines lying around. We were taking turns, propping up cans and throwing rocks at them from a challenging distance.

“Five kiss bet,” Rowan proposed after we’d reset the cans and moved the throwing line back a few feet. “Three throws, three knockdowns.” It was ambitious, but not unreasonable. I was surprised that she was resurrecting her game from so long before, but I figured win or lose, it would make for an interesting week.

“You’re on. Show me what you’ve got,” I told her. She knocked down one can and grazed another.

“I lose,” she said, daring me to administer her punishment.

I pointed at Ben. Instead of walking up and giving him a peck on the lips, she grabbed his sleeve and pulled him off into a private nook. Teddy and I mostly stared at the path they had disappeared into, expecting them to return quickly. As the seconds wore on, the wait became awkward. Eventually, Teddy gave me a look that said whatever was happening in there, he wanted a turn.

It was probably really only two minutes, but it seemed like longer. As Rowan and Ben walked back toward us, Teddy moved around in front of me to remind me that he wanted a turn. When they got close I pointed to Teddy, and then she disappeared with him instead.

I leveled a questioning gaze at Ben.

Ben sized me up, deciding whether he should say anything. He was grinning like an idiot, full of energy. He obviously wanted to tell me. I raised my hands in question.

“Second base!” He bragged.

“You felt up my sister?” I asked. I feigned disbelief, but that was mostly to cover for feelings that I couldn’t make sense of. “No way,” I added.

“I’m serious!” He insisted. “She licked her lips and moved like she was going to kiss me, but then she stopped and took off her glasses. Did you know she has really pretty eyes? So then we kissed, and we kept kissing! We were making out, you know?

He kept talking - I guess to convince me - and for some reason, I kept listening. “She kept moving - like positioning her body - and so, you know, I put my hand on her side - you know, like above her hip? But then she grabbed my hand and moved it up to her tit! Amazing! I mean, she had her clothes on, but still, I got to squeeze them! She took a step back so I could use both hands. She leaned against the wall and I kissed her and squeezed her boobs for like a minute! When we stopped, her shirt was wrinkled.”

Rowan brought Teddy back after about the same amount of time. When I got a chance to interrogate him alone all he would tell me was, “It was a very good kiss.” I was pretty sure he got some boob too.

I was mad and I didn’t really understand why. I guess everyone picked up on that. I didn’t give out any more of Rowan’s “kisses”, and nobody asked, beyond an oblique, “So I heard you made that kissing bet again.” I was sure everyone had heard about what had happened with Ben and Teddy though. Some of the guys tried to get Rowan alone, but she wouldn’t go with them. Ben asked her on a date but she politely refused.

Weeks went on and it was basically forgotten. Then one day Teddy’s dog got hit by a car. He was really broken up. A bunch of us were playing games in Jack’s basement; Teddy was trying to have fun with us, but he just didn’t have the spirit. I told my sister, “I think you should give him a kiss to cheer him up.”

She looked at me like this was something serious. “So, you’re calling in number three, then?”

“Yeah, I guess I am.”

So it was back on. Ben told me he’d give me his bike for the two remaining kisses. I almost hit him.


Kit was the girliest girl in the neighborhood. Her honey hair always hung down in elegant bouncy spirals. I was maybe a little more comfortable with her than the other neighborhood girls: she had been the target of ungentlemanly attention a few times in recent years, so I had gotten in a few scraps as a surrogate big brother. She found me during a neighborhood ice cream social that spanned two blocks. I was under a tree sipping a root beer float. She was in a pretty blue and white dress and she seemed to be going out of her way to keep away from ice cream.

“You’ve still got two of Rowan’s kisses to give away, huh?” She asked.

“Yup,” I said, taking another sip.

She feigned a laugh. “Hey, what do you think she’d say if you told her to kiss someone inappropriate?”

“What, like a creepy old molester?” I asked. “Or a horse?”

“Yeah, like that,” she said nervously.

“I don’t know. I mean, I wouldn’t ever ask her to do something like that,” I explained.

She shook her head. “Right. Of course you wouldn’t. You’re a good brother. You wouldn’t ... make her...” As she spoke she grew increasingly nervous. Her cheeks flushed and she wouldn’t look me in the eye. She seemed to become stuck, unable to say what she was trying so hard to say, but unable to break free.

“Kit?” I said gently. I touched her arm and tried to capture her attention, but she wouldn’t look at me. She wrung her hands, tortured by the question she couldn’t ask.

I took a guess. “I would never ... make her kiss a girl?”

Kit looked at me with vulnerable eyes, biting her lip, shaking, and crying. She nodded.

“I could do that,” I told her soothingly. “I don’t know if she’d agree to it, but I know she’d be understanding about it. Confidential.” Kit’s breathing seemed to even out. “I’ll ask her. Carefully,” I said. “Is that okay with you?”

Kit started crying even more, and she lunged at me into a hug, but she was smiling. I barely had time to move my mug out of her path.

That night at home in Rowan’s bedroom I told her about my conversation with Kit. She listened quietly without judgment like I knew she would. For most of our peers, homosexuals were the punchlines of jokes, but Dad had taught us to see them as real people. A moment later she was in the kitchen dialing up Kit’s house. “Kit? Hey. Jamie made a decision about number four. Do you think I could come over tomorrow?”

Kit found me the following evening in our backyard. Rowan went inside the house when she saw her coming. Kit looked as happy as I’d ever seen her.

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