This story is a revision of one of the same title published several years ago. All characters and events are fictional.
"What do you think about Jan?" Ann said as she tossed the damp towel on the floor.
I breathed in the intimate aroma of our post love making. I shrugged against my pillow and glanced at her shadowy form. "What do you mean, what do I think about Jan?"
Ann stretched on her side. Her big tits squeezed together and pressed against me. The comforting heat of her naked body touching my skin always made me smile. Even in the dark. "What do you think about her? You know, do you think she's pretty or sexy or what?"
I snaked an arm under her. Then crushed her body against mine before I patted her ass. "That's a loaded question. She's your sister. Why don't you tell me what I'm supposed to think about her?"
She traced a finger across my chest, circling my nipples. The movement of my hair caused goose bumps to erupt on my arm.
"I want an honest answer. Do you think she's pretty? Would you make love with her if she was willing?" Ann said.
I sunk my fingers into the firm flesh of her ass and held on. I grabbed her wandering fingers as they migrated toward my crotch. I raised an eyebrow at her in the darkness of our starlit bedroom. Unable to clearly see her eyes, I tried in vain to read her face. "What are you talking about?"
"I'm talking about Jan." Ann pulled her fingers free and cupped my balls. She gave them a gentle squeeze. The stirring of arousal sent a familiar twinge from my groin.
She tightened her grip. "Would you do her if she was willing and you had the chance?"
There was no good escape from this conversation. I shook my head. "No. Absolutely not. She's your sister and you are all I can handle."
Ann increased the pressure on my sack slightly. It was firm, not painful, but the threat was there. "That's a lie, Greg. I hate when you lie to me." She released my balls, laid her head on my shoulder, and stroked my cock. Her hand was warm and strong. "I'm trying to get a real answer here, you know?"
I frowned. "Sounds more like you're trying to get me to say something to piss you off, which I don't understand. We just made love, aren't you supposed to be all cuddly and unsatisfied while I fall asleep?"
Ann giggled. "It doesn't hurt to break the routine once in a while. Now answer me, do you think she's sexy enough that you'd do her?"
What did she want from me? I sucked in a deep breath and held it for a moment before letting it out. "Yeah, sure. Jan's pretty and sexy enough. But the real question is, would she be interested in me? The answer to that is a big fat, capital N, no. I don't understand the point of this."
Ann rose and straddled me, grinding her damp pussy against my thickening cock. Her sex was warm and velvet soft. She was trying to manipulate me, but why? What was she getting at? I enjoyed her touch anyway.
Ann put her hands on my shoulders, holding me down. "I happen to know she'd do you in a New York minute."
"Now I know you're just talking shit." I reached to the nightstand and turned on the lamp. Ann's hair normally glistened like a crow's wing. Post sex it was mussed with errant strands poking out at weird angles. Her big tits rose and fell with her breathing and her pink nipples beckoned to me. I engaged her dark eyes. "What's brought all this on?"
Ann smirked. "Jan and I talk you know? A lot more now, seeing Hal is out of her life." Her grinding increased its pressure. My cock grew thick and hard. I held her by the waist, twirled her soft pubic hair with my thumbs, and encouraged her movements.
"Talk about lying. Now I'm supposed to believe you and your sister talk about me as a sex partner. I mean...I figured once in the past few years you'd maybe tell her I was good or bad or whatever, but that'd be about it."
A coy smile decorated Ann's face. "Have you given that sort of information about me to your brothers?"
"No. Of course not. Besides, there's no need to."
"Why's that?" Ann flashed an impish grin.
I shrugged. "There's an old joke that covers it."
Ann raised an eyebrow at me, an unspoken demand that I tell her.
I used my hands to keep her moving. Her sex, slippery, slid across my now fully aroused cock. "Well the joke goes like this. A guy tells his buddy he just had the worst piece of ass in his life. The buddy says, how was it? And the guy says, wonderful."
Ann wrinkled her lips. "That's not funny."
"Maybe not, but it's true." I stroked her silky thighs then cupped her ass. "You see, young lady, a guy figures pussy is going to be great regardless. So, I don't have to say anything to my buddies or my brothers. They assume you're good in bed because you're a woman. Men are simple creatures."
Ann giggled. "Really? So, how was my pussy tonight?"
"Wonderful," I said with a wink.
Ann gave me a playful punch on the shoulder. "Hey. That wasn't nice."
"What? I said it was wonderful." I smiled and pinched her nipples, maybe too hard. Ann let out a yelp and leaned away from me. "Sorry, all this Jan talk is getting me excited."
"I feel that." Ann squirmed down my legs, resting her weight on my thighs and got serious about stroking my cock. "Anyway, I'm worried about Jan. She hasn't been on a date or anything since Hal hit the road. She's been talking like maybe she's lost her confidence. With men, you know? She was married to him for a long time. I think she's depressed or something. It's kind of scary."
"So, you're going to tell her I think she's sexy and that'll give her confidence and cheer her up?" I couldn't stifle a soft groan as she kept stroking me. "You could've told her that without even asking me. You know, a little-white-lie deal?"
Ann shook her head. "No...I was going to ask you to tell her yourself, then seduce her. Have sex with her, you know? Show her she's still desirable."
I grabbed her wrist, halting the pleasant hand-job. "Have you gone nuts? She's your sister. I'm your husband. She wouldn't go with me if I was the last man on earth."
Ann rubbed my pecs with her free hand. "I'd give you both my blessing. She's always liked you, so it should be easy. Afterward you get to brag to your buddies down at the bar that you fucked two sisters and Jan's self-esteem gets a boost. Sounds like a win-win to me."
"You're crazy. Jan's plenty good looking enough to find a guy on her own. She sure as hell doesn't need you offering upβ I don't even know what to call what you're offering. And for the record, I don't brag about my sex life to the guys at the bar."
"Don't you like Jan? Don't you think she's desirable?" Ann pulled her wrist from my grip and returned to stroking me.
"Of course, I like Jan. And she's as hot as any woman. But I'm with you and she knows I'm with you. Even if I agree to try this scheme, she'll never fall for it. She isn't stupid. And even if she did have sex with me, she'd always think you put me up to it. Which is true, so it wouldn't help her self-esteem one iota," I said.
Ann squeezed my cock's shaft, hard. "I think you're wrong."
"Annie, think about it. All of that doesn't take into consideration that for the rest of our lives you'd be wondering if I thought she was better in bed than you. This is a crazy idea. And let's not forget, I'm a man, my psyche is fragile. What if I really try to seduce her and she turns me down? What happens to my confidence and self-esteem?"