Nathan and Lainie Ch. 01

1. A Fateful Friday

"Nathan, could I talk to you for a few minutes, please?"

"Sure, Mom," I replied, and put down the book I was reading.

"About sex."

I groaned and rolled my eyes. "I'd rather not."

"I feel badly that we haven't discussed the subject. I'm assuming that you are, ah, inexperienced-"

"Jebus, Mom."

She knew very well that I was "inexperienced." I had never had a girl friend. I had never even had a date. It wasn't that I was bad looking - I take after her - and it wasn't that I was an impossible goof. The problem was that I was only 5'5" tall. The problem was that while I had just turned 18, I looked like I was about 14. The problem was that the last thing any teenage girl wanted was a date with someone who looked like her kid brother. The only thing that kept me from being a total nerd was the fact that I was athletic, an excellent baseball player despite my size. Nevertheless, nothing of a romantic nature was going to happen for me for years. I knew that and Mother knew that.

"Relax, would you? This isn't about the birds and the bees. I just wanted to make sure you don't repeat my mistakes."

"I'm not going to get pregnant, Mom." She was pregnant at 17 when she got married to my father. They had about a week together before he was sent to Lebanon as a marine. He died in a terrorist attack and my Mother was widowed at 18.

"No, but we do have more in common than you might think. I got pregnant the first time your father and I fumbled our way through sex. I let him do it because he was going away for training and it seemed, I don't know, romantic. We got married on his leave because I was pregnant and then off he went. In other words, my own experiences with sex are barely more extensive than yours. If you do have questions, I probably can't help you much."

"So why haven't you dated? You're a great looking woman. You could find someone."

"I guess that's my point. After your father died, I was in pretty much the same situation as you are in today. I was out of the game. Between taking care of you and establishing my career, I stopped thinking about it. By the time I did think about it, it felt like it was too late. I didn't have any confidence."

"It isn't too late even now–"

"I didn't say it was too late. I said it felt like it was too late. I didn't know how I was supposed to act around a man. I still don't. I feel hopelessly inexperienced at everything. I'm happy with the way my life has worked out, but I did miss out on a sex life. I guess that's one of my few regrets.

"Anyway, we are talking about you, not me, and I do want to eventually have grandchildren. I don't want you to end up feeling like it is too late when things do look up for you. I want you to hang in there. To keep trying. To stay confident. You're a great person. It will happen for you sooner or later. I'm worried about you."

Trying what, I wondered. But I said, "Okay, Mom. Is that it? That's what you wanted to talk about?"

"Yep."

...

Nothing more was said, but the conversation niggled at me for the rest of the day. I was certain I was missing something, but I couldn't put my finger on it.

It hit me later that night. First, my mother made sure that I understood that similar insecurities plagued us both. She was as frustrated as I, and she was worried I would end up in her boat ten years down the road. Second, what my mother left unsaid was that there was an obvious, if unconventional, solution to our common problem. Third, my mother was very smart. She could not possibly be oblivious to the obvious solution.

The conclusion? She must be making a suggestion, an offer! I was staggered. I'd never thought of my mother in a sexual way. We had an excellent relationship built around the idea that it was us against the world. We had the usual problems between a parent and teenager when I was younger, but our relationship had evolved into a genuine friendship.

Sex with my mother? Could I imagine it? Yes, I could. I wrapped my hand around my suddenly throbbing cock and slowly began to stroke. Mom was very petit, even shorter than I. She was slim rather than voluptuous, pretty in a girl next door way rather than beautiful. Since she worked at home, she dressed informally and she seldom wore makeup. I had never seen her naked - I'd never seen any live woman naked - but it wasn't hard to conjure up an image.

As soon as I imagined hard nipples on her small breasts, I exploded. It was the sweetest orgasm I had ever given myself. As I lay there gasping, I realized that the ball was in my court. If I did nothing, Mom would assume I thought the idea was distasteful. In that case, we would both pretend nothing had been said and we would carry on. She had hatched a clever way to broach the subject without risking anything.

But what if I was wrong? What if I was reading something that was not there? What if I did something and it horrified her? I ran through the logic again in my mind. I was nearly certain, but nearly certain hardly seemed to be enough considering the stakes.

But the ball was in my court and I was determined that I would return the serve.

2. Service Returned

The next morning I watched Mom closely looking for any sign, anything out of the ordinary. Everything seemed normal for a Saturday. After breakfast, I headed out to the yard to cut the lawn while Mom got the housework caught up. I spent a couple of hours working in the garden. After putting the tools away, I decided that it was now or never. I grabbed a coke from the fridge and found Mom in the living room. My mouth was suddenly dry and I took a swig of my drink.

"Mom, could I talk to you for a few minutes, please?"

"Sure, Nathan," She replied, and put down the book she was reading.

"About sex."

She groaned and rolled her eyes. "Jebus, Nathan."

We laughed and I relaxed a little, but I still needed another swig of coke.

"I've been thinking about our talk yesterday..." My voice trailed off.

"And..." She wasn't looking me in the eye. Her hand were fiddling with the hem of her shorts and I was momentarily distracted by her legs. I watched her pick at an invisible piece of lint. She smoothed an already perfectly smoothed hem. Her obvious discomfort gave me the confidence I needed to push on. I hadn't misread her!

"There is an obvious solution to the problems you raised. You can have what you've missed and I could know what I'm doing when - if - a girl ever does get interested in me. We can build each other's confidence." I paused to take another drink. Mom didn't say anything. The hem of her shorts was fascinating her. "I think you were hoping I would realize you were making a suggestion and that I would pick up the ball and run with it."

Mom took a deep breath and looked me in the eye. "What if I was hoping for that?"

"I'm here, aren't I? We're talking, aren't we? If I wasn't also hoping, I would have ignored it. That was your plan."

"The incest part doesn't bother you at all?"

I shrugged. "Well, the secrecy bothers me a bit. I had planned to run up and down the street shouting 'I got laid!' when it finally happened. I suppose that idea is out the window."

Mom laughed which I took as another good sign. This was all going far better than I imagined. I felt cool and collected even though my heart was pounding. The scene was almost surreal, something that I was watching, something that was happening to someone else. Was it actually going to happen? Right now? I was numb. My mouth was dry again.

"Well, it bothers me." A bucket of cold water hit my fantasy. Uh-oh. I decided to keep my mouth shut and wait for more.

"The fact that it is a taboo isn't it. What worries me is that it would change our relationship and that means it could change for the worse. I don't think I could stand that."

"It could also change for the better," I replied.

"More likely not." On the math, Mom was right. The probabilities say that a good situation is more likely to get worse than better. There were risks that should have concerned me too, but they didn't. The situation was slipping away and I felt a flash of anger.

"So why even bring it up? That changed things!"

"I know," Mom replied, a little sadly. "Part of me was hoping you would miss - or ignore - the hint."

The optimist in me noted that meant at least part of her was glad I hadn't missed or ignored anything. I decided to up the ante.

"I jac- I masturbated while thinking about you last night."

"Really?" Mom looked a little worried, but also a little pleased.

"Really. I'd never done it while fantasizing about you before."

"Well –"

"And I'm going to fantasize about it again no matter what."

"Ooh, a threat," Mom said laughing. "I think a little experience and confidence for you would be a good thing, but I want to go slowly. Leave a little wiggle room and give us - give me anyway - a chance to back away if it feels too uncomfortable."

"Okay." I was reluctant to drop it, but I sensed it wasn't going further right now. She might want to go slow, but I was going to push her as hard as I could. She wanted to have sex with me. I wanted her. It was inevitable, but patience now seemed the best course.

"So where do we go from here?"

"I guess the ball is back in my court. We'll see what happens."

3. First Date

At least Mom didn't keep me waiting long. Later that afternoon, she suggested a date - dinner and a movie. "You go to the movie store and I'll order Chinese." The key word was "date" given that we often did takeout and a movie on a Saturday night.

She was in the shower when I got back with the movie. I took a shower and shaved even though I probably didn't need to use a razor for another week. I dressed in my best shirt and pants. I was shining my shoes when Mom called from the hall. "I've ordered! Dinner in 20 minutes." I slipped on a sports jacket and headed downstairs.

The lights were low. Mom was sitting in her big chair, drinking a glass of wine. "Wow," I said. She looked fabulous in a silky black dress. Her blonde hair was up and she wore makeup. Her legs were crossed. A very high heel dangled from a foot that I wanted to kiss. The girl next door had turned into a hottie. "Wow," I said again.

"You look very nice, too. Sit. Would you like some wine?" Mom got up and sashayed across the room to pour me a glass. I watched a perfect ass roll away from me and a beautiful woman walk back toward me. When she put my glass down I peered down her dress and caught a flash of the top of a breast. "Wow," I said. Mom returned to her chair.

"Your vocabulary seems limited this evening."

"That's because you look so fucking sexy, Mom."

She sighed, and picked up a package of cigarettes. She lit one and took a deep drag before slowly exhaling. The filter was stained red by her lipstick. Smoke drifted around her. I was shocked.

"Mom! You don't smoke!"

"That's right. Your mother does not smoke. She doesn't dress like this and she doesn't like it when her son calls her fucking sexy. On the other hand, your mom's friend Lainie does smoke, she does dress like this and she gets a little shiver when a handsome fellow like Nathan calls her fucking sexy. Capiche?"

Hearing mom say "fucking sexy" gave me a little shiver. Her name was Elaine, so it wasn't hard to understand. I wasn't stupid. Mom wanted sex to be completely separate from our relationship. "It's very nice to meet you, Lainie."

Lainie smiled. The doorbell rang. Dinner was here.

...

We'd eaten together thousands of times, but this was something completely different. There was a tension in the air that couldn't be ignored, a tension that made both of us feel awkward. We made some small talk about the food while we ate, but there were long periods of silence. Finally, I dropped my chopsticks and pushed away my plate

"That was good," I said, wiping my mouth. "I'm not a very interesting date so far. I don't know what to say."

"Yes, you've been terribly boring," Mom laughed. "You're supposed to be charming me with your wit and your conversational skills."

"I'd ask you to tell me all about Lainie, but I feel like I've lived with her all my life."

"Ha-ha, smart guy. What movie did you rent?"

"That's Entertainment."

"The one with song and dance clips from old movies?"

"Yeah. I knew you liked it and I figured you'd probably be okay with seeing it again."

"It's a great idea. We can even dance."

"It's been a long time." Mom had taught me how to dance years before.

"It's like riding a bicycle."

"Well, we'll see." I cocked my head toward the living room. "Shall we?"

We picked up our glasses and I grabbed the bottle of wine. I loved the way she looked, but in her heels she was taller. I had to look up to make eye contact as I stood aside to let her go first. After a few steps, she stopped so suddenly I almost ran into her back.

"These shoes hurt my feet. On the assumption they've down their job and impressed my date, I'm taking them off."

I felt a rush of affection for her. "I love you, Mom."

"You mean Lainie."

"No, I meant Mom that time."

She smiled at me and then bent over to take off her shoes. I enjoyed the view.

"Nice, Lainie, very nice."

Mom turned around and looked into my eyes.

"Listen up, Buster," She said. "Lainie is new to all this. For all intents and purposes, she is a virgin. She does not put out and she definitely does not put out on the first date. Understood?"

I raised my hands, palms out. "Whatever Lainie says," I said, while thinking "We'll see."

Lainie smiled again and then padded into the living room. I followed.

...

Lainie settled onto the couch while I put the DVD in the machine. This was another good sign because Mom always watched TV from her chair. My heart was pounding and my mouth was dry again. I was determined to push things forward as fast as I could and I sensed that the best route was to keep talking us into the right direction.

"Lainie may not put out, but it looks to me as if she won't mind a little snuggling on the couch."

She laughed and threw a cushion at me. I caught it and carried it back to the couch. I sat down right next to her and kept the cushion in my lap. I'd been hard for the past couple of hours, but my cock was literally humming now. I was getting worried about coming in my pants.

I immediately put my arm around her. She stiffened for a second, but then allowed herself to melt into my embrace. Her head rested on my chest. Her forearm rested lightly on the cushion in my lap and sent a jolt through my cock. I could feel a soft breast pressed against my side. "Wow," I said. "I've never been so excited in my life."

"Shhh," Mom murmured. "The movie is starting."

"We have to tell each other how we are feeling if we are supposed to be teaching each other. And I've never been so excited in my life. You?"

"I feel deliciously wicked. Now shut up and watch Gene Kelly dance."

The movie had zero chance of holding my attention. I had picked this one out because it was a clip show and I wouldn't have to pretend I was following a plot. Watching the dance number did calm me a little though.

It was the heat that surprised me. Every place our bodies touched was on fire. It radiated up from between us. It made me dizzy. "Now I know why the adjective hot is applied to sex." I touched Lainies's hair and caressed her neck. She cuddled closer and purred. I was vibrating. Why, oh, why didn't I masturbate in the shower? I thought about it at the time, but stupidly decided it would be better tonight if I didn't.

"Penny for your thoughts," Lainie said.

"No chance. Too embarrassing. They're worth way more than a penny."

"How much?"

"How about a kiss?"

"Just a kiss?"

"That's the price."

"Easy," She said and lifted her head to give me a quick peck on the lips. She giggled.

"I'm not going to dignify that with a response."

"Okay, okay." Lainie sat up - her forearm sent another jolt through my cock as she pushed herself off the cushion still strategically placed in my lap - and looked at me. Her hand caressed my forehead, smoothing out a furrow. Her fingertips floated slowly downward, brushing my eyelids, gliding over my cheeks and lingering to stroke my mouth. She arched her neck and licked her lips like an animal that had just tasted her kill. She leaned her head forward until her slightly parted lips were within a hair of mine and paused for a beat before letting our lips finally lock in a sweet, soft, hot wet kiss. The rush was overwhelming. I was dizzy again. Lainie gave me another little peck and backed her head away.

"How was that?"

"Better," I conceded. "In fact it was first rate. If that was your best shot, I'd call it a winner."

"One more just to show you that it wasn't my best shot." She kissed me again, a little harder, and a little longer. I felt the tip of her tongue in my mouth. More significantly, an urgency was communicated. I wasn't the only one feeling the rush. Lainie was excited too!

"Wow," I said.

"I think I've earned that thought," she said smugly.

"When you offered the penny, you caught me mentally kicking myself because I didn't jack off in the shower this afternoon. I wouldn't be so worried I was going to come in my pants now if I had."

She laughed. "That was dumb. Even I knew better than that."

I was surprised. "You whacked off in the shower before our date?"

"Twice." Giggle.

"Tell me more."

"Oh, I don't think so." She gave me a little kiss. Then another. We hugged. I nibbled on her ear and she gave a little moan. I kissed her again and this time she sucked my tongue deep into her mouth. While our tongues were dancing, my hand brushed against her breast. She caught the offending hand with hers and held it, giving it a little squeeze as we broke the kiss. Anything I said about that would sound like whining, so I just panted for a few seconds before nuzzling her neck.

After several more kisses, Mom let go of my hand, and with a mind of its own, it began to creep back toward its target. Her breasts are small, but then so are my hands. The fit was perfect. A hard nipple burned into my palm through her bra and the thin fabric of her dress. I gave the nipple a little tweak as my tongue continued to explore her mouth. I wasn't sure whether my head or my cock was going to explode first.

Lainie moaned and caught my hand again.

"Aw, Mom," I said, hating the whine in my voice.

"Lainie," she corrected. "And how would you like to have your tittie tweaked?" She gave my nipple a hard twist.

"Ow," I cried. We laughed. "I didn't hurt you," I complained, rubbing my chest.

"No," Lainie acknowledged, "But you were getting ahead of yourself and you forgot who you were with." Fred Astaire and Ginger Rogers were starting a number on the TV. "C'mon," She said, hopping up from the couch and holding out her hand. "Let's dance."

Dance? With little Nathan testing the stitching of my pants? I might have refused if Lainie didn't look so damned good despite dishevelled hair and smeared lipstick. Her nipples were trying to poke through her dress. "You are lovely," I said, and throwing caution to the winds, I tossed the cushion aside and scrambled to my feet.

I held out my arms, setting the frame for the lady, exactly as I had been taught. Lainie stepped into my frame with about a foot between us. "Ready?" I said. She nodded. I caught the beat of the music and I started stiffly steering her around the living room. Within a couple of turns, I had relaxed and we were gliding. "You dance well," Lainie said.

"I had a good teacher." Concentrating on remembering the dance steps had distracted me from the woman in my arms, but when I relaxed, Lainie moved closer and the hand on her back had dropped to her panty line, mere centimetres above the swell of her ass. When she moved closer yet, the blast of heat set my head to spinning again. It poured from her groin. If she moved a hair closer she was going to get poked. We were still melting together. She stiffened on contact, but after a brief hesitation, she continued forward until for a glorious second, her mound was pressed against the length of my penis.