9 comments/ 68604 views/ 5 favorites Nathan and Lainie Ch. 01 By: Ben_Franklin 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. Nathan and Lainie Ch. 01 She froze. She jumped back so abruptly she stumbled, lost her balance, and found herself sitting on the ottoman. I would have laughed if I wasn't so confused. "What on earth was that?" She giggled. "Stupid question, I know. I'm sorry. I was just really surprised. Your father was very self conscious because his penis was, uh, on the small side. I just assumed... You aren't a big guy and I thought you were... Anyway, I was just surprised." My cock isn't that much bigger than average, but even an average sized penis looks large on a very small frame. Mine was big enough to be completely out of proportion with the rest of me. As a result, I thought I looked grotesque naked. "I'm glad it's not small, but I wish it wasn't quite so big. I look funny naked. I'm like a face with a Cyrano nose, a freak." "I doubt that," She hesitated. "Show me." "Now? Here?" "Please." I was nervous, but delighted by this turn of events. I would have preferred to be watching her take off her clothes, but anybody taking off anything was a giant step in the right direction. Mom's wiggle room was disappearing. I quickly shucked everything except my boxers. I took a deep breath and pulled them down. My cock popped out. It bobbed up and down as I walked towards Lainie, still sitting on the ottoman. I stopped a couple of feet in front of her. "Wow," she said. "Wow. It's beautiful. I mean that." "I don't look weird?" "Maybe a little, but weird isn't always bad. Unusual is a better word. Turn around." I slowly did a turn. "Wow. Teach me something." "What?" "I don't know. Something." "Well I'm very excited right now." My cock was pulsing. "I'm very close to coming. The head is more sensitive than the shaft. Uh--" "Do you like it gentle and slow, or hard and fast?" "Both can be good. Gentle and slow takes longer. When I get to the point I'm at now, it doesn't matter. When I start to come, I like to go slow and hold tight." Lainie peered underneath. "What about your balls? If I held them in my hand, would you come?" "I don't think so. Tickling them can be nice, but it isn't a really sensitive spot." "Good," said Lainie, and she reached out and took them in her hand. I was so surprised, I nearly fell. I had to steady myself by placing a hand on Lainie's shoulder. She rolled them around the palm of hand and hefted them. "Eggs," was all she said. My cock was quivering under her gaze. She noticed that it was leaking. She gently scraped the slit with a nail, and tested the texture by rubbing her fingers together. With the tip of her finger, she smeared the pre-come around the head of my cock. I tried to ignore her by listening to Frank Sinatra croon. "Lubricant," Lainie decided. It was all I could do to nod. She was still holding my balls with her left hand. "Do you mind?" she asked politely, but she didn't wait for an answer. Her right hand slowly reached out and gently ran her hand along my cock, before grasping it just below the head. I gasped and bit my lip. "To dream the impossible dream," sang Frank. "Wow," said Lainie. "It's hot." I couldn't breathe. Wow was the word of the day. "Tell me if I'm not doing this right," she said as she gave my cock a gentle tug. "I'm going for gentle and slow." I lasted three strokes. On the fourth, I erupted. A rope of come rocketed over Mom's shoulder. She squeezed tightly and kept stroking. The second spurt hit her in the chest just above her neckline and disappeared down her dress. The third landed in her lap. The fourth on her knee. I groaned and swayed. The last of my come bubbled over Lainie's hand. She continued to manipulate my cock until I called uncle. "Okay, okay," I said. "It gets really sensitive after I come like that." "That was really neat," said Lainie. "I've never seen anything like it." She released my cock, stood up and gave me a quick kiss. "And that was some first date." She started toward the stairs. "Wait," I said. "Not yet." "Nathan," she said. "I'm covered with your come. It is running down my back for God's sakes. It's inside my bra. My hands are full and I'm trying not to drip on the carpet. Good night." "You're going to masturbate later, aren't you? Let me watch." "Good night, Nathan." Her tone told me that the date was over. I turned off the movie and went to bed. I had to replay the evening's events in my mind – right up to orgasm – twice before I could sleep. Nathan and Lainie Ch. 02 4. Boundaries and Incentives For the next couple of days I had to treat Mom exactly as I had before fateful Friday. She had made that very clear. I knew a single caress, leer, or even a joke could mess everything up. I thought about several ways I might encourage Lainie to show up, but Mom was worried about our relationship and I was determined to show her nothing had changed on that front. I couldn't initiate anything. I had to wait. It wasn't easy because there was a sexual tension in the air. Things had changed and we both knew it. On Wednesday after dinner, I started in on the dishes - it was my turn - while Mom poured herself a cup of coffee and sat at the kitchen table. "So how was school today?" Mom asked. "Okay. Same old, same old, I guess." "Who did you talk to?" "I said hello to a few people." "That's not what I meant. Did you have an actual conversation with anybody?" I was glad my back was to her. I shrugged and washed a dish. "What about you? Did you have an actual conversation with anybody?" "I told you before that this is not about me. I don't want you to end up like me. There is supposed to be more to life than books and baseball." I didn't say anything. She sighed. I scrubbed another dish. Then I heard the flare of a match. I froze for a second. Then I peeked over my shoulder to see Mom lighting a cigarette. To this day, seeing a pretty woman light a cigarette is enough to send a rush of excitement through me. I picked up the pace on the dishes. "Hello, Lainie," I said. "I'm glad you dropped by. I was worried I might not see you again." "When I leave for good, I'll tell you." When? I didn't want to think about that. "But I can't contact you. I need a phone number. Something." "I think not. This is one of my conditions. Lainie decides when things happen and what things happen. She might show up two days in a row or it might be two weeks." "Is that fair? I–" "If you have conditions, let's hear them. You don't have conditions, do you?" "Well, no, but-" "I do. Boundaries, too, but we can discuss them later. If it is any consolation, I definitely want to..." she hesitated, "fuck you. I'm dying to fuck you. I'd sleep with you every night if your mother would let me. But this is about more than sex." My head was spinning. Partly it was the sudden change from Mother to Lainie. Partly it was hearing my mother say the word fuck. Partly it was everything else she said. This is about more than sex? But mostly my head was spinning because Lainie was here and something was going to happen. My cock was bent uncomfortably in my jeans. My mouth was dry. My hands were shaking. I dropped the last dish into the rack, wiped out the sink, and turned around. Lainie was already stubbing out her cigarette. She smiled. "So do you want to play a little?" I managed to nod. "Well, here." She handed me her coffee cup. "Finish your chore. I know you've had your shower, but I'm going to have a nice bath. Oh, and put clean sheets on your bed." I washed the cup with shaking hands and wiped down the table. I left the kitchen and headed down the hall for the linen closet. I stopped in surprise. First, Mother was using the bathroom in the hall rather than the one off her bedroom. Second, the door was wide open. Third, she had removed her blouse and was stepping out of her jeans. Kicking them aside, she bent over to test the water rushing into the tub. Seeing my mother in her bra and panties shouldn't have been much different than seeing her in her bikini, but it was very different. I swallowed a couple of times to get some saliva going and whistled. "Very nice." It was true. Mother was a petit woman who ate well and got lots of exercise. She was in great shape. She turned and looked at herself in the mirror. "You're too kind." She quickly dropped her panties and stepped into the tub. My angle was poor and I barely caught a glimpse of her ass as she stepped out of my sight. "Oops," she said, "I nearly forgot this." Her bra came flying out from behind the door. I reached into the linen closet to grab a couple of sheets, hesitated, and then boldly walked into the bathroom. Unfortunately Lainie was shrouded in bath bubbles but I sat on the toilet anyway. I deliberately - blatantly - reached into my pants and adjusted my hard cock. Lainie giggled. "You're teasing me," I accused. "Of course I'm teasing." She blew away a few bubbles from in front of her chest. Did I imagine a flash of pink nipple? "And the teasing is going to get much worse." "Worse? No fair!" I pretended to pout. "Too bad. It turns me on. I like it." She blew at the bubbles again. That was a flash of pink nipple! "Teasing is part of my game. What kind of incentive would we have if I didn't do some teasing?" I didn't like the sound of the word incentive but I was distracted by a smooth leg that emerged from the water. Was that a dark patch between her legs? "You're killing me here. Do you want me to beg?" "I don't think so. Such a poor boy," She said, pretending to be sympathetic. "Go make your bed, get undressed and wait for me there. I promise I'll be quick." "Why don't you get out of the tub first and then you can help me make the bed?" She laughed. "Here's an even better one. Get undressed here and then go make your bed and wait for me." "I could help dry you off." "I could soak in this tub for another hour or two." I shook my head sadly, "So I can't win." "Not now," Lainie agreed. "Get those clothes off." I removed my socks and sneakers. I stood up and peeled off my shirt and dropped my jeans. My cock tented my boxers. I pulled them down and my cock popped out. It was throbbing. It was vibrating. It was leaking copiously. I couldn't be more excited. "Poor boy," said Lainie. "I did that, didn't I" "Yes, you did. I'm going to make the bed. Don't be too long. Please." And with that, I left the bathroom. I didn't really understand the rules of the game at that point, but my complaints rang hollow even to me. Whatever the rules, I wanted to play and I didn't even mind the teasing part. This was fun. Lots of fun. I made the bed and slipped in between the clean sheets. A few minutes later, Mom wandered into my room, still drying her hair with a towel. The bad news was that she was wearing a full length nightgown. The good news was that the nightgown was form fitting and it was obvious she was wearing nothing beneath it. Her nipples were prominent on her small breasts. The gown was so tight her mound was obvious. "You look awesome, Lainie. A little overdressed perhaps, but very, very sexy." "Thank you," she said as she slipped into my bed. She kissed me lightly on the lips and then she kissed me hard. She tasted of toothpaste. "As for the gown, I want to neck for a little bit and I don't trust myself." We kissed again. Again I was overwhelmed by the heat as she melted into me. My cock poked at her. Lainie giggled and reached down between us to adjust it's position. My cock throbbed as soon as she touched it. I bit my tongue to keep from coming. We kissed again. Lainie's tongue pushed past my lips and probed the inside of my mouth. I moaned and pushed back. Our tongues danced. Both of us were panting when we broke the kiss. Lainie's hand snaked down and lightly grasped my penis. It gave a little lurch and I moaned again. My hand reached for her breast as I kissed her again. Her hard nipple burned into my palm through her nightie. I caressed it for a second or two before Lainie released her grip on my cock and removed my hand. She kissed me and said, "You have to earn that." Her hand returned to my penis. Earn it? What did that mean? "No fair," I called. "You're touching me." She immediately released me. "I suppose we should be fair." "Okay, okay. Unfairness isn't such a bad thing." Lainie giggled and her hand returned to my crotch. She caressed my balls. "I need another kiss." I obliged. My hand had a mind of its own and returned to her breast. I squeezed it while rubbing my thumb across the nipple. This time Lainie moaned and allowed me to play for a little longer. I hadn't seen them yet, but I had decided that Lainie had great tits. Again she removed my hand and held it. Again this meant she released my cock. This was a good thing because I was trembling on the edge. "I am so close to coming it hurts," I said. Lainie laughed. "Think about baseball. What did you hit in your last game?" "I was two for three with two walks." "Who pitched?" "Who cares?" I kissed her again and squeezed the hand that was preventing me from returning to her breast. "I don't want to think about baseball." "Poor baby." Lainie leaned away from me so she could look at my cock. "Its beautiful, but it looks so angry. Let's make him more comfortable, shall we?" Lainie let go of my hand and grasped me firmly. I gasped, but remembered to return my hand to her breast. I closed my eyes and the pressure began to build in my balls. "I'm so wet," said Lainie. I released her breast and slid my hand down to cup her pussy. She gasped as my finger found her slit through her nightie. "Are you going to come for me?" she asked as she gently stroked me. "Yes!" I shouted. "Yes! Yes! Yes!" Liftoff. A blast of come ripped through my cock, shot into the air and landed on my chest. Another rope, another and another. Lainie continued to gently rub, her hand now coated with my come. I sighed. She giggled and said, "That was lovely. I love to make you come. I love to see it shoot like that." My finger was still between her legs. It felt slick even through the nightgown. I moved the finger slightly. Lainie let go of my cock and pretended I wasn't slowly diddling her. She tasted my come on her hand. "Mmm." I moved my finger faster. She moaned, but then pushed my hand away. She wiped her hand on her towel and tossed it to me. "Here. Clean yourself up." I sat up and cleaned the come off my chest and cock. What now? "Give me a kiss and then go sit in your computer chair." I did as I instructed. "Keep your bottom firmly planted in that chair." My cock was already stirring. "I won't move," I promised. "And when I'm done, I'll say good night and leave." "When you're done, you're gone." "And not a word about any of this to your mother in the morning." "Not a word," I agreed. "This is all between me and Lainie." She sat up in the bed. She shrugged a shoulder out of her nightgown. Then an arm. The other arm. She held the cloth in front of her breasts. "They're too small," she said apologetically. "I've thought about–" "Don't say it," I said emphatically. "Never. They're perfect just the way they are. Sight unseen I can say that." "You're sweet. I don't know why I feel so nervous." She took a deep breath. "Ta-da." She let the top of her gown go and threw her shoulders back. I was right. They were lovely. Each was about the size of a small orange. The nipples were a delicate pink and very prominent. They pointed up a little. Pert was a word to describe her tits. Perky, even. "Wow," I said. "They're too small," Lainie said again. She cupped them and thumbed her nipples. "But I think I have nice nipples." "No. Yes. I mean no, they are not too small and yes, your nipples are very sexy. Are they always that big?" "No." "So why are they so stiff right now?" "You're not that naive," Lainie answered. "You know perfectly well why they are erect." "I want to hear you say it." I began to stroke my cock. "My nipples are big and stiff and sensitive because I am very excited. I'm so excited, I ache." She nodded at my hand moving slowly on my cock. "That's why." "Do you like to have your nipples sucked." "Oh, yes." "Would you like to have your nipples sucked right now?" "That depends. Can you reach them and keep your butt planted on that chair?" "No." "Well then, there's your answer." I shrugged and grinned. "It was worth a try." Lainie had slipped a hand onto her pussy. She was slowly rubbing herself, making small circles, timing her movements with my slow strokes. It was like dancing. I sped up a little. So did she. I slowed and she followed. "Let me see it." "See what?" Lainie was teasing. She giggled. "Your... your pussy." "Don't you mean my cunt? I think Lainie likes to use dirty words. Just saying the word cunt makes me want to show it to you. Would you like to fuck my cunt with that big cock?" I wasn't falling for that. "I would love to fuck your cunt but my butt is planted." "That's right. So what do you want?" "I want to see it. I want to see your cunt." She quickly lay back on the bed, lifted her hips and whipped off the gown. I got a brief flash of her slit before she popped back into a sitting position. Her knees were together. I could see a dusting of blonde pubic hair, but not much else. But I could smell her. I inhaled deeply. "Delicious," I said. Her scent made my cock harder and my hand move faster. Lainie watched me, her knees still clamped together. She was rolling a nipple between a thumb and a finger. "Now show me a hot cunt. Show me the hottest cunt in town." Lainie shifted back a little on the bed, lifted a foot and placed it on the bed. Her pussy opened up like a plump clamshell. It glistened pink. I could see the slot where I was going to fit my thick cock. I could see her clit, standing tall. I understood why they called it the man in the boat. "Wow," I said. We both laughed. "I thought about shaving it," Lainie said. "Would you like that?" "I like pubic hair. Some anyway. Does having a bald cunt (I was deliberately using the word) appeal to you?" "In a way. It's so slutty, you know?" "Yes." I was stroking my cock again. Lainie was making circles around her clit again. "My cunt is so wet." A long finger disappeared and reappeared. Back to the circles, going faster. So was my hand on my cock. The finger disappeared. "Are you going to come again?" "Oh, yes," I gasped. "This is so fucking hot. You're so fucking hot." "Wait for me," Lainie panted. "I'm so close. Are you getting close too?" I grunted. I was right on the edge, but holding back. "Oh, yes, I am getting so close. I'm going to come and then you will squirt and I'm going to come again." Her hand was a blur. "Oh yes." I could feel the come start to rise in my cock. "Yes," said Lainie, "Yes, yes, yes YES! Now! YES!" Her entire body froze and then a shudder ripped through her. When she said now, I had liftoff. "I'm coming," I shouted. "Aaaagh!" came out of Lainie as my hot come splattered on her leg. "Uunngh. Oh God, oh God, oh GOD!" Her body shuddered again, then a second time and a third before she became still. We were both panting. I was drained, exhausted. Mom wasn't in much better shape. After a couple of minutes, Mom rolled off the bed and picked up her nightgown. She stood there naked. I couldn't tear my eyes from her. "Did you enjoy that?" "I had a great time tonight, Lainie. Thanks." "Would you like to do more next time?" "You bet!" More? I was just happy there was going to be a next time. "That's up to you. These are the boundaries for now. The incentive? When I see progress, you get more." "Progress? What do you mean? What do you want from me?" "I want you to get a life. Good night." With that she left the room. I waited a few minutes and headed down the hall to her bedroom. I paused for a few seconds, and then knocked on her door. I stuck my head back in the room. It smelled of her sex. "Good night Mom. I love you." "Good night Nathan. I love you, too." Nathan and Lainie Ch. 03 5. Earning More Like most shy and introverted people, I had learned to be invisible at school even though the fact that I was an excellent student and a good baseball player drew attention to me. Teachers who tried to draw me out in class quickly learned that I didn't want to participate and most let me hide at the back of the room. I did the work and did it well, so they couldn't really complain. People often congratulated me after a good baseball game, but I'd just nod or mutter "Thanks" and hurry on. I loved being part of the baseball team, but none of my teammates were really friends. My nickname was "Shrimp" which made me wince even when it was used affectionately. When opponents razzed me about belonging in Little League, members of my own team thought it was funny, and that hurt. I was one of the top players but I didn't really belong. I didn't really belong anywhere. I spent my day at school hurrying from one class to another, from one quiet nook in the library to another in study hall to another on the back stairs where I usually ate my lunch while reading a book. This is the pattern I had to change. This is the pattern I had an incentive to change. The positive factor – aside from the incentive itself – was that Mother couldn't be expecting a lot. She is basically the same person in the same boat – she works alone at home and has few friends. She is every bit as shy and introverted as I am. She knows she is asking for something difficult. I was fairly certain I would be rewarded for making an effort even if the result was a humiliating experience for me. In fact a humiliating experience might deliver up the best reward from Lainie. Therefore, I decided the way to impress my mother was to (try to) make friends with a girl. A girl friend was not a realistic goal but a friend who was a girl? Why not? I told myself that I could do that. Furthermore, since failure might yield up results as good if not better than success, I might as well swing for the fences. I resolved that I would try to talk to Connie Seabrook. I knew her casually since she was going out with the star of the baseball team. She was in my history class and I often saw her in the library where she worked part time. She was attractive, she was smart, and she had been – before fateful Friday – my favourite masturbatory fantasy. Would having lunch and a conversation with Connie Seabrook qualify as progress? On Thursday, I went to the cafeteria with several opening lines at the ready. Unfortunately (or fortunately) for me, Connie was having lunch with a group of her friends. No way was I joining a group. I was relieved, but also disappointed. When Mother asked me about my day that evening, I shrugged, and she sighed. No Lainie on Thursday night. On Friday, my luck was better. Connie was eating alone and reading a book. I nearly chickened out, but the thought of Lainie... I went over to her table and set down my tray. "Hi Connie. D-Do you mind if I join you?" My heart was thumping. "Hi Nate. Sure, I guess." She had a puzzled expression on her face. (Did she mean "Sure, I could join her" or "Sure, I mind." I hesitated and sat down.) "What's up?" she asked. "Uh... uh..." (I couldn't remember any of my openings. Not a one.) Her expression turned from curious to suspicious. "You're not hitting on me are you? Because I've already got a boyfrie-" "No, no," I interrupted. "That's the furthest thing from my mind. I wouldn't dream of it." (Geez, that makes it sound like I don't think she is worth hitting on.) "I mean I know you go out with Ken." "So what's up?" "Uh... I'm trying to please my mother." I blurted. (Jesus, where did that come from? What a fiasco this was turning out to be.) Connie lifted an eyebrow. The absurdity of the entire situation struck me and I laughed out loud. Connie looked even more confused. I suddenly relaxed. How could this get worse? I decided to give Connie more or less the truth. "She's worried about me lately. She thinks I'm too much of a loner. Every day she asks me if I talked to anybody interesting. Tonight when she asks, I'll tell her I talked to you. She will be pleased." (And maybe she'll pay off.) "Sandy Struthers," said Connie. "Every time my Dad hears about a teenage suicide he goes haywire. I have to assure him that I'm happy at least twice before he settles down." Sandy Struthers! Sandy was a girl at our school who had killed herself a few weeks before I first met Lainie. Did Mother think that I... "Geez," I said. "I never thought of that. That's the reason she's on my case." And in my bed. Suddenly I felt really badly. It must have shown on my face. "So. Let's please your mother," said Connie with a smile, "How do I qualify as interesting?" "Well, you read for one thing," I tilted my head enough to read the title of her book. "'Zen and the Art of Motorcycle Maintenance' no less." "It isn't really about motorcycles." "I know. I've read it." It turned out we had a lot in common. We both liked books, we both liked baseball, we both liked old movies and we were both raised by single parents. (Connie's mother had died when she was five.) I was sorry when the bell went and lunch hour ended. I think Connie enjoyed herself too. I was walking on air for the rest of the day. Most people wouldn't see it as a big deal, but I was delighted and not only because of Lainie. I'd taken a risk and it wasn't a disaster! I was so pleased with myself that I even volunteered an answer in math class! The only fly in the ointment was Sandy Struthers. Every time I thought of her - which was too often - I'd feel a stab of guilt. "Hi Mom," I shouted when I got home after baseball practice. She was setting the table for dinner. "Hello, dear. Dinner is about fifteen minutes so if you didn't shower after practice, you've got time." I quickly showered. I could hardly wait for dinner. I could hardly wait for after dinner. I'd had an erection on and off all afternoon. I thought about taking care of it in the shower, but I decided to wait. Not only did I have progress to report, I was almost sure I could use that progress to summon Lainie tonight. I came into the kitchen rubbing my hands together. Mom had already dished up. I sat down and started to eat. "So how was your day, dear?" "I had a great day," I replied. "Really?" "Really." I wasn't volunteering anything. Mom hesitated. She knew something was up. Instead of asking about the great day, she came out with her usual question. "Did you talk to anyone interesting today?" "Yes. Yes, I did. I had lunch with a girl I know." Mom's eyebrows shot up. "No! Really?" "Yep," I said smugly. "Who?" Mom leaned forward. "Details. I want details." "I don't think so," I replied. "Guys don't discuss girls with their mother. All I'm saying is that it was nice and that it made me feel really good about myself." She knew perfectly well what I was doing. For the first time, I had some leverage in this game and I was using it. "Well, good for you," she said. "You know, I was planning on a quiet night in front of the television but I think I'll have a shower and disappear for a while." "That sounds like fun," I said. Sandy Struthers. Another stab of guilt. Mom is doing this because she's terrified I'm going to do something I have no intention of doing. I wasn't beyond taking advantage of a mistake, but I couldn't let her stay terrified about an imaginary problem. Mom tried to tease some information out of me while we finished dinner, but I would not bite. We finished dinner. "But before you go for your shower, I have to talk to you about Sandy Struthers." Her head snapped around. "I think one of the reasons we are playing this game is that you are worried about nothing. Nothing. Do you hear me?" She nodded. "No matter how depressed or lonely I get, I would never do that. I could never leave you like that or hurt you like that. Never. Do you understand me?" She nodded. "Thank you." She stared into space for more than a minute, long enough to make me wonder whether I'd blown it with Lainie. Finally, she smiled. "I guess I'm lucky that a deal is a deal. Now I'm sure you are going to volunteer to take my turn at the dishes for me." I quickly nodded. I wasn't the only one with leverage. I didn't care. I quickly cleaned up the kitchen and sat down to wait. I was shaking with anticipation. My cock was hard, diamond cutting hard. Mom was taking her time. Finally, I heard her call me from her bedroom. She was lying on her bed, wearing her full length nightgown again and smoking a cigarette. My cock throbbed. "Hello Lainie." She stubbed out the cigarette. "Hi, Nathan. I hear you had an adventure today." I nodded. "So lose those shorts and your shirt and get over here." I quickly shucked my clothes and snuggled in beside her. She gave me a kiss and lightly grasped my cock. I went for her breast and caressed the hard nipple through her gown. She didn't try to stop me so I was already ahead of the game. "One day I'd like to see your breasts when the nipples aren't like this," I said. "And for a change, I'd like to see your cock when it was soft, but we can't have everything," Lainie replied laughing. "Now. Details. I want details." I began to tell her the story but she interrupted me almost immediately. "Connie Seabrook? Ken's girlfriend? She's a babe! You devil, you!" She squeezed my cock. I tried to ignore that and went on with the story. Another interruption. "You mentioned me?" "I didn't mean to – it just popped out." When I went on to mention Connie's Sandy Struthers theory, Lainie's hand stopped her slow massage. "She's perceptive isn't she?" "She's very smart," I replied. I went on with the story, but she couldn't stop interrupting. "Zen and the Art of Motorcycle Maintenance?" I sighed. "Yes. Do you want to hear the rest of this tonight? Shut that pretty mouth..." I gave it a kiss, "and let me finish." She released my cock and drew her hand across her mouth, zipping it closed. Her thumb – which had been slowly rubbing the head of my cock - was slick with my precum. She licked at it and then slowly sucked the entire thumb into her mouth and then slowly pulled it out. My cock gave another lurch before her hand found it again. She did keep quiet until I told her about Connie liking classic movies. "We even discussed whether it was perverted to lust after dead actors. I told her that I thought Barbara Stanwyk was sooo sexy." "You did not. What did she say?" "She said her Dad still had the hots for Marilyn so I couldn't be all that bad." "Then what?" "Then the bell rang. We had to go to class." Mom clapped her hands. "I'm amazed. You did great. I suppose you think you did well enough to earn a reward." She gave my cock a little squeeze. While I was telling my story I hardly noticed her fingers dancing on my shaft, but now I was acutely aware of how close I was to coming. "If you keep that up, it is going to be too late to reward anybody." Lainie immediately stopped. "The obvious next step in our adventure is oral sex. I'll tell you what. You get to choose. Do you want to give or receive?" "Give," I said immediately. Her hand went back to slowly stroking my cock again. "Darn it," Lainie said and slid down the bed a foot. "Are you sure? I could slip down another foot or so... I so much want to learn how to give a proper blowjob." She took her thumb and sucked it back into her mouth. "Mmmmm..." It was too much for me. "Too late," I groaned and exploded. Come shot up between us and hit her in the chin. Lainie quickly went back to my cock and began to squeeze and wring it dry. Another spasm, another, and then another. The front of Lainie's nightgown was soaked. I groaned with each squeeze while Lainie giggled. She hopped out of bed, peeled off the nightgown and hopped back. For the first time, Lainie snuggled up against me naked. Her nipples were burning into my chest. I kissed her on the lips and on the neck while I played with her breast. My other hand slipped down her body through her pubic hair. I kissed my way down to her breast. "This isn't oral sex," Lainie gasped, as my fingers danced around her slit. It was slick. "I'm a beginner," I said. Besides, it wasn't altruism that drove my choice. I would love to get a blowjob, but more than anything, I wanted to explore her body. "And I'm using my mouth." I sucked on her nipple. I released her right breast and leaned over to inhale her left one. When I did my cock – it was hard again – poked her in the leg. She reached down and squeezed it. I paused "You'll tell me if I'm not doing this right?" "You're doing fine." I cupped her plump mound and pressed. Mom moaned. When a finger felt a bump, Lainie gasped again and said "Oh my." The finger continued to probe until it suddenly slipped inside her. It was surrounded by warmth and wetness. "Oh my," said Lainie again as I felt her cunt clench my finger. Leaving the finger where it was, I slid down the bed - Lainie had to reluctantly release my cock - and peered closely at her pussy. It was beautiful. I slowly pulled my finger out and pushed it back in. Her cunt throbbed around the digit. I pulled it out again. Lainie was making little whimpering noises. "Spread your legs a little more," I said. Lainie immediately complied. The smell was indescribable. "Pheromones," I thought. I bent my head and kissed her cunt lips. Lainie whispered, "Please..." I took my tongue and licked her pussy from bottom to top. "Oh my," said Lainie. I did it again, stopping this time to probe her insides. She tasted as good as she smelled. Lainie groaned. I licked and nibbled at her clit. "Yes," said Lainie, "Right there. Oh my." I returned to the bottom and started up again. "I'm fucking her with my tongue," I thought as I pushed it in and out. Back up to her clit. "Don't stop, please don't stop," cried Lainie. I started to move down again, but Lainie grabbed my head with both hands and held my tongue in place on her clit. She moaned as it danced over her bump. My face was soaked. Lainie's hips were beginning to buck against my face. "I'm... going... to... come!" I sucked her entire clit into my mouth. "OOHH! MY! GOODNESS!" A violent shudder ripped through her. My face was mashed against her cunt. I sucked harder. Another shudder was nearly as violent. A third. A fourth smaller orgasm rippled. I couldn't breathe. My nose was bent uncomfortably against her pubic bone. Her hands were pulling at my hair and her thighs were trying to crack my head like a nutcracker cracks a nut. Suddenly she relaxed and I could breathe again. I crawled up between her legs and kissed her. My cock was rock hard, of course, and it dragged through her wetness. Lainie grabbed it and laid it - safely - on top of her mound. She licked my face. "So nice," said Lainie. "Did you like doing that?" "I've never had so much fun in my life," I said. I started to move. The shaft of my cock was gliding over her wet cunt. "Careful now," murmured Lainie as I tried to "accidentally" draw back and find the right spot. I ignored her. "I could just put the tip in," I begged. "No," Lainie said firmly. "Roll over." We reversed positions. Lainie kissed me on the lips and sat up. Her cunt lips were wrapped around my shaft. The head of my cock peeked out from between her legs. She drew back and my cock nearly disappeared. I could feel the head bump over her clit. When it did Lainie gave a sharp intake of breath. She slowly moved forward again. Back. Forward. I began to move in the same rhythm. Lainie went faster. My balls began to boil. Lainie sensed I was getting close. She raised herself off my cock, grabbed it, and started to frantically frig her clit with it. "A second, give me a second," she said. But the sight of the fat helmet rubbing against her little man... Her tits were bouncing because she was bouncing... It was all too much. It felt like I was turned inside out. Her clit disappeared under a flood of my hot white cream. "OH MY!" squealed Lainie and she came hard. I was still spraying come everywhere. When it slowed to a dribble, Lainie released my cock and collapsed onto my chest. She kissed me on the nose. "That was great. Thank you." She heaved herself off the bed. "I'm having another shower. This is a messy business." "Thanks, Lainie. See you soon, I hope." "You do realize that it will take more than another lunch conversation to..." She let her sentence trail off. "I figured," I replied.