Jimmy slept lightly, his sleep interrupted by crazy fantasies of the future. School would certainly be different. His junior year was about to start, and he was a completely different person from the sixteen-year-old who had begun the summer. He was no longer a virgin, and he had been having a tumultuous affair with his sexy next-door neighbor, Joanne Smythe. Not only that, but she had tutored him in the intricacies and intimacies of how to please a woman. The culmination of the summer was one night when his parents were away, and he spent an entire night fucking her. She had even allowed him to take her ass.
Many of his friends had lost their virginity, but he knew of none who bragged about having anal sex.
Joanne had gently told him that future meetings would be rare. That was a huge disappointment, of course, but she had prepared him for it and encouraged him to date girls his age, being mindful about safe sex.
"Don't trust anything but a raincoat for your penis, Honey. You don't need to be a father too soon. However, always be respectful to women of all ages. That is the most important lesson.
Joanne had managed to keep their relationship a secret, but she worried at times that his parents had serious doubts that Jimmy was only mowing the lawn. Fran had seemed to imply more must be going on, and she suggested that to her husband, Bill.
"Have you noticed anything different about Jimmy, Bill? He seems to get really excited about working for Joanne."
"And why wouldn't he? She's a knockout. Not that I've noticed personally. But those tatas of hers would make Pavlov's dog salivate. Don't get me wrong, Fran. You've got nice boobs as well. Her's are...well...enormous for her body, I guess."
"That's all you men think about. Big tits. She is well-endowed, I admit. I hope Jimmy is appropriate around her. He likes women with big boobs. It's pretty obvious."
Fran and Bill had an active sex life earlier in their marriage, and since Jimmy was an only child in an open household, secrets were few and far between. Jimmy was honest with his mother about most things, but he swore to secrecy with Joanne. So when his mother asked him to sit down and talk with her, he decided he might need to prevaricate. They would only be white lies.
She told him his dad was on a business trip and would be gone for several days, so they could talk openly without fear of anyone interrupting. This would be between the two of them. She wanted him to feel he could trust her.
Her husband's absence was a lie, however. Fran had discovered he was having an affair with someone at work, and they had separated indefinitely.
Fran was working on a third glass of wine after dinner. She didn't normally drink excessively, but she was nervous about what she was intending to ask as well as trying to drink away her own problems.
They were in the den with the TV on low volume and seated across from one another.
"Honey, tell me the truth. What is going on with you and Mrs. Smythe? Something is, I know. I see the glances you give her. And normally she tells me everything, but lately she seems distant around me."
Jimmy was torn. He didn't want to lie to his mother, but a promise is a promise.
"There's no problem, Mom. It's all good. I'm helping her out, is all."
"You spend so much time there. I know you probably have a crush on her. She is attractive and single. Is that it? Do you have a crush on her? She's old enough to be your mother, you know."
"It's not what you think. Yeah, she is attractive and nice. But I'm working for her. That's all."
Fran knew her son was lying.
"Okay. I'll take you at your word. She would tell me if there was a problem. But I have another question that I have to ask–Honey, this is embarrassing, but I'll just come right out with it. Do you masturbate a lot? I wash your clothes, and your shorts are often stained with, well...you know...semen. And your waste bin is always full of used tissues. It's natural for boys your age, but it seems like you must do it a lot."
"Geez, Mom. What kind of a question is that? Okay, yeah. Sometimes I do, but no more than anyone my age. I try to clean up after. I'm sorry if my shorts are full of cum. Is that the problem?"
Jimmy's indignation was an attempt to cover up his discomfort.
"No, Honey. It's just that you are different lately. You never want to spend time at home. I don't understand. I'm sorry if I embarrassed you. I'm your mother. You can tell me anything, and it's just between us. I wish I could help you feel good about yourself and your family."
She paused and hesitated to go on.
"I know this is an awkward age, and you probably think of Joanne when you masturbate. I know I would if I were a guy. She's very sexy, isn't she? Are you a virgin, Honey? It's okay if you are. I was a virgin until college. Before I met your dad, I had a boyfriend or two. Do you have questions about sex?"
Instantly, Jimmy pictured his mother getting fucked by some college guy. He didn't want to lie, but he didn't have to tell everything.
"I am not a virgin. I'll just say that, but I don't want to talk about it. Okay? It's very personal. And I was careful. No one was hurt or disrespected."
Jimmy's mother didn't know what to say. Her son had never really dated anyone that she knew about. The only woman he had spent any time with was Joanne. Now Fran was really curious about her neighbor. But the conversation ended on that awkward note.
Several nights after that, she lay awake in bed after drinking most of a bottle of wine by herself when she heard her son arrive home later than usual. He was supposed to be at a movie with friends, but she was suspicious. She heard him getting a drink and decided to check in with him before he went to bed. But just as she entered the kitchen, she heard his bedroom door close. She waited a few moments and then decided to talk with him about his dad.
She knocked on his door lightly.
"Jimmy, can I come in?"
"Sure. What's up?"
She entered and found him in bed. He was naked, at least from the waist up. He sat propped by a pillow with his laptop in front of him. She sat on the edge of the bed and stared at her handsome son for several seconds. She still felt a little tipsy from the wine, but it also emboldened her.
"We need to talk, Honey. I have a confession. I lied to you the other day. Your dad and I are separated."
Jimmy's face fell. "What? Are you kidding? Why?"
As soon as the words came out, she started crying. Through her tears, she explained about his affairs and that they were working through things, but it didn't look good.
Jimmy couldn't believe his ears. He had been so wrapped up in his own issues that he had failed to notice the tension between his parents lately. Now, here was his mother confessing that she had lied to him about what was going on. On top of that, his dad was a cheat.
For the first time, he noticed she was wearing a sheer, silk nightie without a robe, and her nipples poking through the thin material suddenly gave him an erection. Fortunately, his laptop covered it. He closed it and pressed it to his thighs in an attempt to make it go away.
She sat scooted closer so her bare thighs pressed against him..
As she finished with the brief details, she put her face in her hands and sobbed. Jimmy threw his arms around her and embraced her.
"I thought we had a good marriage, but now I realize that there was no love on his part. Just sex. And then not even that."
Jimmy hugged her tightly. What do you say to that? he wondered.
"I love you, Mom. I'm so sorry to hear this."
He tried to comfort her but felt awkward about how to proceed. He kissed her forehead before taking her face in his hands, and after looking her in the eyes for several seconds, he kissed her lips gently. He meant it to be platonic.
The move to her lips startled his mother at first, but then she softened her mouth and let the kiss linger. As her mouth opened slightly, she felt his tongue enter and find her own. It happened so quickly that she panicked slightly. But she didn't stop it. And then she responded with her own tongue in his mouth. It felt so good, and she hadn't been seriously kissed in ages. Their tongues danced in each other's mouths.
Jesus, I'm French-kissing my mom! And she seems to like it. She is a great kisser. God, this is so hot!
After several seconds, Fran broke it off but only said, "Oh, Honey, I'm so stressed. Thank you for the nice kiss. This has been a terrible few weeks. Will you just hold me in your arms for a few minutes?"
"Sure, Mom. I'm so sorry you are going through this. I'm here for you, whatever you need."
She moved his laptop with one hand and set it on the nightstand. Together they slid down and lay in each other's arms. Jimmy tenderly kissed the top of his mother's head as it lay on his chest. He wrapped his arm around her tanned shoulders and squeezed her affectionately. Her eyes were closed, and she was cooing contentedly when, after a few moments, she looked down and noticed a substantial tenting of his sheet, which still covered his lower half.
Holy shit. My son has an erection, and it appears to be huge! Did I do that to him?
Jimmy watched as his mother slowly adjusted her position and casually threw a leg over him and across the protuberance to feel if it was real. Her breasts pressed into his stomach with only a thin layer of silk between them and his bare skin. She moved her leg over his rigid cock and realized it was the real thing. And with her hard nipples pressing into him, it wasn't likely to get any smaller. Moisture formed between her thighs.

Fran had not had sex in several weeks...ever since she confronted her husband about his affair. And even before then, sex was loveless and mechanical with him. The discussion with her son about losing his virginity and frequently masturbating had intensified her thoughts and even her fantasies for the last few days. And now she was scantily dressed and lying in bed with her muscular son, who was sporting a huge erection. Not to mention, he had just slipped his tongue into her mouth in what started as an innocent kiss. And she had kissed him back like a teenager in heat.
She couldn't believe it. She wanted to touch the shape under her leg. Finally, she could stand it no longer.
"Honey, this is nice, snuggling with you. I need this after recent events. Thank you. You feel so good."
As she spoke, she moved her leg to the side and let her hand wander across his chest and slowly toward the head of his cock. It stretched under the sheet most of the way to his exposed belly button. If she moved the sheet a couple of inches, the head of his cock would be visible. As her fingers approached that forbidden fruit, Jimmy watched in amazement and terror.
Jesus, is she going to grab my cock?
His question was soon answered as her hand lightly glided over the head and down his length as if petting it. The sheet was still covering him, however.
"Honey, this looks uncomfortable. Can I help you in any way?"
And just as if she did this every day, his mother peeled the sheet back and exposed his thick, nine-inch cock to the light. She let out a gasp when the fat, circumcised crown first appeared. With the sheet removed, his cock strained to stand at attention.
Eyes wide with glee, she stared at the thick appendage and smiled.
"Oh, my lord. Jimmy. You have a beautiful, big penis. You are absolutely huge, Honey. Did I do this to you? My goodness, no wonder you have to masturbate frequently. I hope this is okay, but I HAVE to touch it. I AM your mother, and I used to put diapers on you, but my, how you've grown. I had no idea."
And with those words, he watched as she placed her fingers around his girth and lifted the appendage carefully as if it were a museum piece.
"No wonder Joanne likes you so much. She confessed to me yesterday that she seduced you."
"What? She told you. We promised to keep it a secret!"
Instantly, his cock softened in her hand with the idea that he had been discovered.
"No, she didn't tell me, silly, but you just did. I KNEW you were spending more time than necessary with her."
"Mom! That's not fair. Yes, she is the first. And I love her for it! She was wonderful. I can't believe you did that."
"Don't worry, Honey. I'm sure it was a fantastic experience, and I won't say a word. She is a lovely woman. But look! This big flower stalk is wilted with our frank talk. Sorry. I didn't mean to deflate you. My gosh, though. It's still huge."
The fleshy, tubular shape in her hand no longer pointed to the ceiling. It hung slightly limp, yet several inches still extended beyond her fist.
"Would you like it if I made it hard again and gave you some relief? I'd be happy to do that. You look like you are in pain. I can only imagine how frustrating it must be to have your big balls full of semen and no place to put it. You probably get tired of doing this yourself all the time. Maybe Joanne does this for you, hmmm? Honey, why don't you let me make it up to you and make you feel good?"
Jimmy seemed to nod approval, but he was also about to pass out as he stared at his mother's small hand, slowly stroking him back to life. He had fantasized about a moment like this many times, and now it was happening in cinematic color. His mother didn't wait for an answer. She expertly stroked him and rubbed the precum that leaked out of him around the plum-sized helmet.
"Am I doing it okay? Do you want me to keep going?"
"Oh, yes. Please. That feels so good, Mom."
His mother kissed him, and then squeezed and slid her hand steadily up and down her son's prodigious length, her eyes glued to the fat missile in her grip. A combination of the wine and her libido had taken over her brain. Her own desires overrode any guilt about what she was doing. Secretly, she wanted to give her son more than a handjob. Her thighs became wet with her dirty thoughts.
She threw out a feeler for the future.
"I don't think your father and I are going to get back together. I may have to rely on you for help around here, at least temporarily. You are now the man of the house. Would you be able to do that? You know–chores and such. Like the way you help Joanne. Can I rely on you, Jimmy?"
Her son lay there, his eyes glued to his mother's hand as she stroked him to a rock-hard erection. He prayed he would remember this moment forever–the image of his mother smiling sweetly as if this were a normal occurrence, like reading a bedtime story.
"Sure, Mom. Anything you need. Just ask."
"Wow, Honey. Look at that. Your big penis is nice and stiff again and already starting to leak. Do you like your mom rubbing you this way? I love making you feel good, Sweetie."
Jimmy was encouraged by her sweet smile. He couldn't believe how calm she was as she stroked him. He decided to take a risk. He never used profanity around his mother, but the words bypassed his brain.
"Oh, fuck, Mom, that feels wonderful. Is it okay if I see your tits? That really gets me off. You have nice tits, Mom."
"Oh, I guess so, Honey. As long as we've come this far, I suppose I can show you my old-lady boobs. You used to love to suck on them. They're not as big as Joanne's, but your father loved them. That is before he found a twenty-four-year-old secretary with a packed bra."
She removed her shoulder straps and let her nightie drop, first hanging up on her nipples, and then falling and collecting around her waist. Her tits were cone-shaped and came to distinct points with large, puffy areolae that covered the ends completely like two pink marshmallows. They cantilevered out from her chest with little hint of any sagging, like two headlights.
Fran's stroking and pressure on Jimmy's cock increased. He was getting close, she could tell.
"You probably don't remember when you used to suck on Mommy's boobs? You couldn't get enough of them. Back then, they were swollen with milk. Here, let me cradle your head, and you can nurse on them while I stroke your penis. It is so thick. Who would have guessed you would become such a big boy? I used to talk baby talk to you when you nursed, and you loved it."
She positioned herself so Jimmy could feast on her breasts. She tenderly kissed his forehead and whispered to him.
"Go ahead and squeeze them if you want, Baby. Momma loves her tits suckled and fondled. They're firm for my age, aren't they? Like a couple of fleshy torpedoes. I don't always wear a bra, and they do just fine."
"Oh, fuck, Mom....
