Sometimes The Best Plan Ch. 03

So it was another night of fitful sleep for me. Getting in Jan's tight pussy was a dream come true, but my real dream was Mom's. I had touched it! She let me touch it. Oh, sure, she didn't give me more than a little taste, but how many guys have gotten that far? When I studied it objectively, as I did in the wee hours when I'd wake up with a raging hard on, there were a lot of pluses on my tally board. Mom knew I wanted her. She let me touch her. She was a knowing, willing participant in what we were doing. As I told her in the kitchen, if I never got any farther than kissing her neck (and touching her pussy), I'd be a happy man. Of course, I wanted more and I was going for more, but time would tell.

In the meantime, there was Jan. No matter how far I got with Mom, there was Jan. She had enjoyed last night as much as I, and I knew there would be more. What a little mink my sister was. She was built like a gymnast with a tight, solid little body, and her face was that of an angel. I envisioned her beautiful face on my dick. I knew it would happen. With Jan, there was no pretense or games - we both knew what we wanted, we had it once, and we would have it again. As I thought about that, I rubbed my dick and then smelled Jan on my hand. Heavenly. I couldn't wait to bury my face in that.

The next morning, I followed the same pattern as before. I heard Jan in the bathroom so I knew she was up, but she stayed upstairs to give me some alone time with Mom in the kitchen after Dad left. I was determined not to screw things up as I had the previous morning, so I made some noise as I entered the kitchen. Mom was sitting at the table with a cup of coffee, and gave me a brilliant smile when I entered. She had a glow about her, a fresh-fucked glow. I walked over to the counter to get my own cup and, as I passed behind her to sit down, bent down and gave her a little kiss on the nape of her neck. She said nothing, but bent her head down and I gave her another.

"Morning, Mom. How did you sleep?"

"Great, Honey. How about you?"

"Oh, okay. Had a little trouble getting to sleep, but like a log after that." When I said that I glanced at her, and she had a little blush on her face. So she knew, or at least suspected, that I heard them going at it. What she didn't know, or even suspect, was that at the same time I was buried to the hilt in Jan's creamy pussy.

After a bit, Jan came in, got her coffee, and sat down. Jan was always a little grumpy in the morning, so we had all learned to walk lightly around her until she got in a better mood. Not this morning, though. Jan was beaming. She, too, had that fresh-fucked look about her. Mom looked at her quizzically, but didn't say anything. Did Mom recognize it on her?

"Did you kids go right to bed last night?"

Jan didn't miss a beat. "Oh, yeah, we were in bed right away."

I saw a cloud of wonder pass across Mom's face, but she didn't say a word. "What are your plans today? It's a beauty. You should get out and do something."

Jan looked outside. "I may try to get nine holes in if I can. Squirt, you want to go with me?"

Jan was a damned good golfer. She had been on the high school golf team, and won every tournament she entered at college. The golf coach had lobbied her hard to join the team, but Jan kept refusing. She said she enjoyed golf and if she got on a competitive team she feared it would take the fun out of it. Dad had encouraged her to go for it, probably looking at the possibilities of a scholarship that would take some of the bite out of having two kids in college at the same time, but Jan stuck to her guns.

I looked at her. "And get humiliated once again?"

"Oh, come on. I'll even let you use the ladies' tees if you want."

"That does it. No way. You go. Enjoy yourself. I'll go with you after you've broken an arm, or something."

Mom laughed. If she had wondered about what we had been up to last night, and except for her look at Jan I had no reason to believe she suspected, our normal sibling bickering must have put her mind at ease. "You kids behave," she said. "Don't make me stop this car."

We all laughed. Yep, we had heard that phrase more than a few times.

After breakfast, the normal quick bowl of cereal this time, Jan announced she was going to do just that - she would change clothes and head for the country club. The country club was Dad's one extravagance, and he loved it. He sold the idea to Mom, years ago, on the notion that Jan and I would enjoy it and it would be a family bonding thing, and I guess it had worked. We had all spent a lot of time there over the years. Jan and Dad with their golf, and Mom and I with tennis.

"Mom, you want to go with her and play a few sets? Feel lucky? Well, do you, punk? Feel lucky?" I did my best Clint imitation.

"Ha! Do you feel lucky? That's the question." Mom was pretty competitive on the tennis court and it had taken me a long time to be able to match her. Now, we were pretty evenly matched and our play was usually close.

"Sure. I'll go if you'll go."

"Okay, then," she said. "It's a date, but I'm not going to be easy on you."

"You can be as hard on me as I'm going to be on you." I said that without thinking, but realized how it sounded when Jan gave a whoop and laughed uproariously. I blushed. "No, I didn't mean it like that," I stammered.

"You can be as hard on me as you can," Mom laughed, and then said to Jan, "And you get your mind out of the gutter, young lady."

"Me? He started it. He's the one who said it."

"Shush," Mom replied. "You two don't get started. Meet down here in thirty?"

One of the reasons I had always enjoyed tennis with Mom was her tennis outfits. Maybe it's because I liked the game so much, but seeing an attractive woman in a tennis outfit was my weakness. Seeing Mom in her tennis outfits was my weakness on steroids. When she came down the stairs, I gave a low whistle. "Not fair. How am I supposed to concentrate on whomping you when you look so good in that?"

Laughing, she said, "You're getting stronger and I'm getting older. I have to work every advantage." I could tell she liked what I had said, and the thing is, it was true. She looked stunning. Her legs and butt were her strong points, and that outfit emphasized them both. Her face, an older version of Jan's, was set off perfectly with her hair tied back in a pony tail. As I told her last night, she was a MILF for sure.

At the club, we agreed that Jan would play nine holes, we would play a couple of sets until Jan was done, then we'd meet for lunch. As she left with her bag for the course, Jan turned back and said, "Good Luck, Junior. Just remember, swing easy and set up your approach shots." Mom laughed. She had no idea what Jan was really referring to, but I knew.

"I'll be your good little student, Jan. I won't go for the kill shot until I have her ready for it."

Mom and I volleyed a bit to loosen up, then spun the racket to see who would serve. Mom won, and I settled in to await her serve. I guess I had forgotten how Mom could rocket a serve. Even if I had remembered, the sight of her reaching up and arching her back, showing those legs and her pert breasts, took my concentration. At any rate, the ball zipped past me without my even moving my racket.

"You gonna play, or just stand there watching me?"

I shook my racket at her. "Given the choice, I'd rather watch you. But just try that again, young lady, and get your ketchup ready 'cause I'm going to make you eat it."

This time she tried to serve to my backhand and faulted. "Ha!," I laughed. "See what I told you? This is going to be easy."

With that, we settled in and got to business. We were, as I said, pretty evenly matched and that's how it went. First one, then the other, would lead. For the last game of the set we were tied at 40-all, and it was Mom's serve. I could see the concentration on her face. She tossed the ball, arched back, and sent a zinger that was just over the line.

"Out!," I shouted. "You only have one more, you know, but don't let the pressure get to you."

"Don't think you can try those mind games on me, Buster," she shouted back. "I know what you're up to."

"Do you? Do you really?," I said,

"Oh, yeah. I know what you want," she said as she arched back for the serve, and then she hit it with so much force she grunted. The ball bounced and came right at my feet. Momentarily distracted by what she had said, I had not gotten properly set. Trying to get moving, I tangled my feet together and fell right back on my ass.

Mom came running around the net. She was laughing her head off. "Not only do I win, but I knocked you on your butt! How's that for an old lady?"

I jumped up and we fell into each other's arms, laughing. I didn't think about what I was going to do, but it seemed natural. I pulled my head back and then kissed her on the lips. She stopped laughing, melted in my arms, and kissed me back. I held her tight against me and flicked my tongue across her lower lip, and she responded in kind. I couldn't believe it. I was standing there french kissing my Mother.

"Hey, you two," came a shout from the sidewalk leading to the courts. "Get a room."

We looked over, and there was Jan, beaming.

"Oh, Jan, I wish you could have seen it," Mom said. "I served it right to his feet and he fell right on his butt. It was perfect."

Jan didn't mention the kiss, and neither did we.

After loading our gear in the car, we linked arms and walked toward the clubhouse. I could not have been happier. I kissed Mom! We hadn't gotten into it deeply, and that was a good thing because what kind of scandal would have ensued over a Mother and her Son being caught making out on the tennis courts, so Jan had probably done us a favor. But she had kissed me back. My Mom, the perfect soccer Mom and teacher, had actually given her son a little tongue.

We chattered away like magpies at lunch. Jan had linked up with one of her old friends from high school, Carol, and her Mother, Elizabeth. Elizabeth had been considered good enough to consider turning pro at one time, and Jan reported that she had beaten Liz by three strokes. As I said, Jan was a good player so we were not surprised, but Liz had a reputation at the club of being a fierce competitor.

"Wow," I said. "You beat Elizabeth? That's pretty hot."

"Oh, yeah," Jan said, rather smugly. "She won't let it go at that, though. We're going to meet again tomorrow. You know she's going to bring her A-game."

"Yep," I said. "She was just toying with you. She'll eat you alive."

Jan laughed and said, "We'll see who eats who."

Jan and Mom then started talking and that allowed my mind to wander. Elizabeth Chandler was a beauty. She was tall, trim, with a mane of thick red hair. Her years of golfing had kept her in good shape. To put it simply, Liz had been the wet dream of many a teenaged boy, and probably many a middle-aged man, at the club. I thought she was even prettier than Carol, and Carol was a stone beauty. I couldn't help but imagine Jan and Liz going at each other. I dismissed the thought as fancy, though. Liz wasn't like that, I was pretty sure. She sure didn't mind flirting with the men at the club, but I had never seen anything that would make me suspect she went the other way, too.

That night at supper, Jan seemed a little out of it. OK, a lot out of it. She was like off in space, or something. Mom, Dad, and I were talking and joking, just like normal. Mom recounted, several times (ahem), my falling on my ass as she hit the winning serve. I noticed she didn't mention our kiss. I caught her looking at me several times, with a look I had not seen before. It wasn't lustful, but more a wistful, look that is hard to describe. I took it as a good sign. But Jan didn't participate. Dad wanted to know all about her golf match, especially how she approached the difficult 16th hole, but she wasn't into it. I teased her about feeling the pressure of meeting Liz the next day and getting her ass handed to her, but she wouldn't bite.

When we went into the family room after dinner, Jan excused herself and said she was going to read in bed for awhile. That put me in an awkward position. I wanted to sit next to Mom so we could play again under the throw, but with Jan not there my sitting so close to her would have looked suspicious. So, I sat at one end of the couch, and Mom sat at the other. I was dying. I kept looking over at her and she would look back, again with that wistful look.

After awhile I couldn't take anymore and I wondered what was up with Jan, so I stood up and stretched. "I think I'll call it an early night, too, since Mom kicked my ass this morning." Dad said goodnight and turned back to the television, and I stood in front of Mom. I wasn't totally hard but there was no doubt it was there and the way I was standing, It was right at Mom's eye level. That was all it took, and I was fully hard. Mom was like a bird before a snake. I could tell that she wanted to look, but she kept her eyes on mine as I told her goodnight. Finally she did it. Her eyes glanced down to my dick, then immediately back up to my eyes.

A slight smile danced across her lips. "Goodnight, Honey. See you in the morning," she said, then I leaned down and kissed her. I was leaning over, and she put her hand behind my head and pulled me in for a tighter kiss. There was no tongue, but since we rarely kissed on the lips, it meant volumes to me. My hard dick and I then turned away, and I went upstairs.

I paused about halfway up. "Mom?"

"Yes, dear?"

"I'd like a replay of today. I need another chance at you, you know. Everything, just like today, except next time I'll win."

She laughed and turned her head toward me. My dick was fully tented in my loose gym pants and there was no way she could miss it. "Okay, Buster, but you'd better be ready for it. Don't ask for something you can't handle."

"Oh, I can handle you, Mom. You just wait." Then I turned and went the rest of the way up the stairs.

I paused, waiting for Mom and Dad to get fully immersed in their show, then gently tapped on Jan's door. "Come on in," she said. She was sitting on her bed and her face was flushed red.

"Jan," I said. "Are you upset because you caught me kissing Mom? I thought you were on board with this."

"Oh, hell, no. I'm proud of you. You're going to get there, I just know it. I'm glad I interrupted you when I did, though, or you would have had your hand all over her ass, right there on the tennis court."

"Then what's the matter with you? What's wrong?"

She sighed. "Liz."

I scoffed. "Don't worry. You'll beat her by at least five strokes tomorrow. Besides, it's just a game. You can demand a rematch if you lose, you know. Stretch it out over the whole summer."

"It's not that. Not that at all," she said, softly.

"Then what?"

After a little hesitation, Jan looked me in the eyes. "I bent over to tee my ball and when I looked at her, I saw her eyes. They had the look, Kev. She had been checking my butt, and she had the look.

I was slow on the uptake. "What look?"

Jan patted the bed beside her and I sat down.

"THE look. Hot red-haired Liz wants to jump my bones. I'm sure of it."

I gasped. Holy-three-hundred-yard-drive! I gasped. "Liz? Carol's Mom?"

"Oh, yeah. Carol won't be there tomorrow, and it's going to be a big day, I'm thinking."

"But how do you know? What's THE look?"

Jan tried to explain the unexplainable. "It's hard to explain. Between women it's different than between men. When you want a woman, you look at her in a certain way and if she returns that look, you know you're in. But between women, it's more subtle because there's much more risk. As a man, if you give a sultry look to a woman and she doesn't want it, she just turns away. No harm, no foul. But a woman won't give that look to another woman unless she's almost certain it will be accepted. The last thing a woman like Liz wants is for word to get out that she's hitting on women. In our club? She's be ruined. It's a shame, but it's reality."

"Are you sure it was that look?"

"Of course I'm not a hundred percent certain, but remember, I've played this game before. She made eye contact with me and held it. She might have been trying to psych me out, I don't know. Maybe she has repressed desire, and has never acted on it. Maybe nothing comes of it. But it's definitely in the realm of possibility. I'll see tomorrow." Jan was as hot as a rocket, I could tell. She had on another tank top, and her nipples were like little stones.

"So what will you do?"

"Well, one of the advantages of being a woman is that we can say things. Like, you wouldn't tell another guy that his haircut looks very sexy on him, would you?"

I laughed. "Not bloody likely," I said with an exaggerated British accent.

"Well, that's too bad. As I said to you before, you need to open your mind. I've read that everyone is bisexual in varying degrees. I believe that women, given our nurturing nature, tend to be more likely to be bi. I know when I was struggling with it I tried to deny my desire for another girl. When I opened up to the possibility, it was mind-blowing."

"Yeah," I said, repeating an old joke, "It doubles your chance for a date on Saturday night."

"Oh, you have no idea. But back to what I was saying. A woman can compliment another woman, even in slightly sexual terms, and we think nothing of it - unless we're open to it, and that's the foot in the door. We can even say to another woman, 'You have beautiful breasts.' If she's open to it, that can be the start of something beautiful. If she's not open to it, she still takes the compliment the way she thinks it was intended."

"Oh, God, Jan. Is that what you're going to do? Holy Shit. Please. Oh, please. You're going to have to tell me all about this."

"I will, I promise. But what about Mom? You guys were going at it, weren't you?"

I grinned. "It just came in the moment. She beat me and was so happy about it that we hugged, and then kissed. It was hot. She even gave me a little tongue. Not a lot, just a tease, but Wow!" Then I told her about what had just happened when I told Mom goodnight.

Jan grinned back at me. "I think tomorrow may be a big day for both of us. Now get to bed. I need to be rested and ready."

The next morning, Jan was already dressed for golf when she came down. She had on her own tennis outfit and, damn, she looked good.

Mom looked at her. "You playing tennis or golf?"

"I want to get some sun on my legs and it's likely to be hot today, anyway. What do you think?" She twirled around.

I chimed in. "If you were playing with me, there would be a lot of wood action, I can tell you that."

That got a guffaw from both of them. "She's your sister, Kevin," Mom laughed.

"But still," I said, laughing myself. "A man can only take so much."

Jan ate quickly. "I'm supposed to meet Liz for a 10:00 AM tee time. After I beat her I'll probably make her buy me lunch, so don't look for me until suppertime. You kids going to be okay on your own?"

I was standing at the sink rinsing my bowl and Mom came over to link her arm in mine. "Oh, I think we kids will do fine. Who knows what we'll get up to?"

I choked a little bit and then laughed with her. "Oh, yeah. Who knows?"

I went outside with Jan to help load her golf bag in the car. "Good luck, Jan. I can't wait to hear about it."

She squeezed my arm. "Good luck to you. I can't wait to hear about it, too. I think Mom's giving you signals, young man. Go softly, but go with a purpose. You're not a little boy, remember. You're a man on a mission."

Jan drove off, waving merrily, and I turned to go in the house.