Sometimes The Best Plan Ch. 02

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She reached over and pushed me back down, bending over slightly so I got a good look at her breasts. Whether she did it consciously or not, I noticed the nipples were up and ready again. She laid back down and whispered back, "You've got a one track mind, don't you?"

I snorted. "I guess so. I can't help it."

"Don't let Jan hear you say things like that, that's all."

I laughed, for a couple of reasons. I was back on track. It had not taken much - just paying attention to her and flirting with her, and it was as if this morning had not happened. But if she knew what Jan and I had been talking about. Ha. "Don't let Jan hear you..." Jan was going to get a blow-by-blow report.

Mom was sensitive to the sun, so she got the sunscreen and started rubbing it on her. I leaned over, propping my head on my hand so I could watch her. She knew I was watching her, but didn't say anything. When she had her front done she rolled over and handed me the bottle. "Do my back, would you?"

"With pleasure," I said.

"Not too much pleasure," she giggled. "Just my back."

I put everything I had into it, trying to make putting the sunscreen on her back the most sensual act ever. I looked over, and Jan was at the side of the pool, watching me, with a hungry look on her face. After I finished her back, Mom took the bottle from me and did her legs. I wanted to do them, but didn't say anything. There was going to be time for that, later, I hoped. I had all summer.

"Jan, get out and get some sunscreen on you," Mom said, in her Mom voice. "I don't want you burning. You know that causes skin cancer, right?"

"Mommmm," Jan said in a whining voice. "I'm not a baby anymore."

"No, but you'll always be my baby. Now shut up, and put sunscreen on. You don't want to be a dried up old prune when you're my age."

Mom had decided we'd have pasta for supper, one of my favorites. I stayed in the kitchen with her while Jan was in her room. Mom had changed into a pair of black yoga pants with a white tank top, and looked great. She had her hair pulled back in a pony tail, which emphasized her neck. I had always thought Mom had an elegant neck. So, I told her so.

"Mom, I love your neck. It's elegant."

That got a snort out of her. "Yeah, long necks are the bane of a woman's existence when she gets to be my age. Damned thing hurts all the time."

I was helping her chop tomatoes for the sauce. I stopped and looked at her. "That's the second comment about your age you've made today. I won't have it. You're beautiful. I was telling Jan this morning that I think you're even prettier than you were fifteen years ago. So, stop it. You're as young as you feel."

"Then I'm a hundred," she laughed. "At least."

"Well, I don't think so. I think you're as sexy as all get out." I stopped. Had I gone too far, too fast? Jan had warned me, but my comment had slipped out without thinking.

"Young hormones," Mom said. "Nothing like them." She smiled when she said it, and there those nipples were again, poking right out. "Whew," I thought. "She's not mad. Dodged a bullet on that one."

After dinner, Jan and I stayed in the kitchen to clean up while Mom and Dad went to the family room to watch Jeopardy. Dad had broken out a bottle of red, and they took their glasses with them. As soon as they left the kitchen, Jan grabbed my arm. "You're an artist. You've got her right back in the palm of your hand. Tell me about it."

I recounted our conversation, boring as it was. I told her how I thought I messed up with the sexy comment, but Jan disagreed. "It was in the moment, and it was natural. You did fine. You sent her a message."

Jan and I took wineglasses with us to the family room and settled onto the couch after we filled them. Again the room was chilly, and again Mom got the throw to put over our laps. I was in the middle again, and found myself in a quandary. What should I do? I had my hand on her leg last night, but should I do it again? Mom answered my unspoken question for me as their mystery show opened, reaching under the throw for my hand and placing it on her leg. She looked straight ahead, not showing anything, and kept her hand on mine. I gave a gentle squeeze to her thigh, as a gesture of appreciation, and she squeezed my hand back. It was an unspoken communication, just between the two of us, and it spoke volumes to me.

Before long, Jan's hand snaked onto my other leg, rubbing gently, and Mister Diamond Cutter was back. I had not adjusted myself when I sat down, and it was painfully kinked. As casually as I could, I took my hand from Mom's leg and adjusted myself, then reached quickly over to touch Jan's hand. I put my hand back on Mom's leg, gave a squeeze, and she put her hand back on mine. "Okay, Bud?," she asked softly.

"Oh, yeah. All warm and comfy," I said, and she giggled.

So, Mom knew my dick was hard for her, and she was alright with it. That had to mean something. I started gently rubbing and massaging her thigh. She gave no sign anything was going on, so I took that as consent and began ranging farther afield. I rubbed the inside of her thigh, and then slowly, ever so slowly, moved my hand upward. She still gave no sign. She had taken her hand off mine while I rubbed her thigh, and now she came back, giving my hand a squeeze. I wiggled my little finger, now on her upper thigh no more than a couple of inches from her pussy. Still no sign. Still no rejection.

Maybe I'm wrong, but seems to me there is a natural progression to touching. I've always gone for the ass first. Breasts might come next. The pussy has always been the last thing I'd go for. You touch a woman's pussy right out of the box, and that's disaster waiting to happen. But here I was, with my finger very close to Mom's pussy. That was close to being a violation of the natural order of things. What to do? I had already had my hands on her butt. Going for her breasts now was not possible. What to do? So, I did nothing. I left my hand where it was, while continuing to gently rub my little finger as close to her pussy as I dared.

I was so focused on that little finger that I was oblivious to Jan's hand, until she ran it up my leg and rubbed it across my dick. A credit to my discipline, I didn't jump. I had my left hand on the couch between Jan and me, so I carefully reached up to put it on Jan's hand and encouraged her to rub my dick. She gave a little squeeze to the head of my dick, and then took her hand off my leg.

"Anyone ready for more wine?," she said as she took the throw off her lap and stood up.

"Yes, please," Mom and Dad both said, so Jan filled all our glasses. When she filled mine she looked right in my eyes and smiled.

"Good boy," she said as I held my glass out.

Mom laughed. "Don't be fooled, Jan. He's not as good as you think," and she squeezed my hand when she said it.

Jan sat back down and we all settled in again. I was, as I said, totally focused on that little finger, so close to heaven, so I felt the gentle nudge of Mom's hand on mine. A gentle nudge up, toward her pussy. So now I was back to my quandary, but this time I didn't dwell on it. I slowly inched my hand up until my little and ring fingers were touching Mom's thigh, right next to her pussy. Her breathing had become deep and when I glanced over at her, her eyes were closed. Ever so gently, like I was touching a butterfly's wings, I stroked my little finger across her pussy. Even through the tight yoga pants, I could feel the structure of it. I could feel the lips of her pussy.

She gave an involuntary jump with a gasp and moved to jerk my hand away. I was prepared to beat a hasty retreat, but she held my hand up close to her pussy - not on it, but right next to it. I got it immediately. She would let me get close to the gates of heaven, but would not let me enter them. Yet. But of one thing I could be certain - Mom knew I was going for her pussy. Emboldened, I rubbed a little more aggressively, right beside her pussy. Not much, just enough so there could be no doubt in her mind what I was doing. I knew I mustn't touch her pussy again, so I used my finger to stretch the fabric of her pants to put pressure on it. I must have been right, because she started making slight pushing movements with her hips while her hand pressed mine into her.

Dad stood up, the show over. "Bedtime," he crowed. I took my hand away, but Mom gave it a meaningful squeeze before I did.

"Daddy," Jan whined. "I'm not ready. It's too early to go to bed."

"Get to bed, young lady, before I give you a spanking," he said. "You're still not too big for that, you know."

"Oh, please," Jan purred in a seductive voice, and everyone laughed.

Dad had a funny look on his face but he recovered quickly. "Maybe you are too big, after all," he said, chuckling, and then headed up the stairs. Jan, Mom, and I cleaned up, and then Jan left us alone in the kitchen. She had gone out of the kitchen, but there was a stair tread that always creaked and I hadn't heard it. I knew she was lurking just outside the door, listening to us. Little sneak.

Mom rinsed the wineglasses while I stood behind her, enjoying the view of her ass in those yoga pants. She turned and gave me a hug. I did not replay the actions of the previous night and kept my hands on her waist, and I lowered my head to her neck and gave it a gentle kiss. "I love that elegant neck," I said. "I just love you, Mom."

"Oh, Kev. What are you doing to me?," she whispered in my ear. "You can't get your Mother all worked up like that."

"I just love you, that's all," I replied.

"I love you, too, but not in that way. You know we can't do what you want, don't you? We just can't. I won't let it happen."

I kissed her neck again, and gave it a little nibble this time. "I don't care. I'm happy however you let me love you. Just kissing this neck is enough for me."

I must have said the right thing because she gave me a tight hug. "When did my little boy grow up?" she asked.

I snorted. "When did my Mother become such a MILF?"

She pulled out of my arms and slapped my butt. "I know what that means," she said.

"Good," I answered. "Then you know." We both laughed as we turned to the door. I coughed so Jan would have some warning and I heard the stairs squeak as she scampered up them. When Mom and I got to her bedroom door, I stopped her and bent my head down to kiss her neck again. "Just one more," I whispered, and then she went into her bedroom.

I went right to my room and immediately Jan came in through our adjoining bathroom.

"Tell me all about it," she said as she settled onto my bed.

"She had me almost rubbing her pussy," I whispered, still in awe of it. "She let me run my finger across it once. She even encouraged it."

"I thought so," Jan snickered. "I could tell by the look on her face. You're going to get it. I just know you are."

Then we stopped and looked at each other. My room was the closest to Mom's and Dad's, and we could hear the unmistakeable sound of the bed squeaking. We both giggled, covering our mouths to stifle the sound.

"God," Jan said. "You must have had her horny as a billy goat."

"Me? What do you think you did to Dad with that spanking comment? Did you see the look on his face?"

That got us both laughing quietly again and, to the sound of Mom and Dad fucking, we naturally fell into each other's arms. I kissed Jan deeply and she responded eagerly. This time I didn't ask. I peeled her tank top off and in a flash had my mouth on those tits. Jan arched her head back and moaned.

"I'm going to do this just this one time, for now," she said, "but if Mom and Dad get to take the edge off, then so should we." She pushed me onto my back and shucked my pants off. "I saw you adjusting that big boy," she said, as she studied it. "Nice one, Kev."

"Just kiss it for me, Jan."

"Oh, no." She took me in her hand and gently rubbed her thumb across the head of it. "You're going to have to wait for that. This is going to be a quickie. We want to take the edge off, but you have to maintain your competitive spirit. I can't give you everything at once." With that, she pulled her panties off and I saw her pussy for the first time I could remember. It was shaved clean, which was something of a disappointment to me. I don't know why girls started deciding their pussies had to be shaven, but practically every girl I had at college was that way. For a guy who loved a big bush, it was not right.

She was sitting on my chest, so I bent my head forward and kissed her pussy softly. "No, no," she said. "Mama will give you lessons on that when the time is right, but not now." She rose up on her knees and slid down, then lowered herself onto my dick. As soon as I was fully in, she paused and arched back. "Like I said, Nice one, Kev."

Her pussy was as tight as any I had experienced. I told her that, and she squeezed it on my dick. I moaned. I couldn't help it.

"Ssssh," she whispered. "You want to get us caught?"

We were both quiet, and then could hear Mom's bed, still going at it, along with a whispered conversation we couldn't hear well enough to understand. That got another giggle fest going. "God," Jan said. "Mom is fucking you in her mind and Dad is fucking me in his. And we're fucking each other. Can it get more delicious and twisted?"

"Oh, I think so," I said, and then put my hands on Jan's tight ass to get her moving. My big sister was a good fuck, I had to give her that. I couldn't keep my hands off her tits, so the position with her on top was perfect for me. I quickly learned that she was accustomed to being in charge. She came first, and it didn't take long, then I was right behind her. I was ready for another go with another position, maybe doggie style, but Jan stopped me.

"The after sex is as important as the sex, you know. Just snuggle me. Just love me. Besides, that was just to take the edge off. You're on a mission. Remember, Soldier?"

"Oh, I do, Jan. I've always wanted you and I've always loved you, even when I put that bubble gum in your hair."

We laid there for a bit, basking in our afterglow, and then Mom's bed stopped its noise and Jan got up and grabbed her clothes.

"See you in the morning. Gonna be a good day, I think," and then she was gone to her own room.

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13 Comments
mcitylinemcityline4 months ago

This is not only erotic but is also a fun story. This sister is a enjoyable partner for the adventure.

AnonymousAnonymous11 months ago

This is a very old story, so the comment is not needed. The story’s great - love it. However, the Chapo impersonation is forced, not funny, and really takes me out of it. It’s bad.

AnonymousAnonymousover 4 years ago
I completely and fully agree

I don't know why girls started deciding their pussies had to be shaven, For a guy who loves a big bush, it is not right. PUSSIES NEED HAIR!!

ken0001ken0001almost 5 years ago
Oh yes!

I'm loving this, the build up is hot . I hope the story never ends!

DomJ69DomJ69almost 5 years ago
Great Setup

Great idea to have his sister to guide him towards the light. Very erotic.

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