A Mother's Dilemma Pt. 01

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It was dizzying to think about it. But the more Vivian did think about it, the more she rationalized her next move.

She dressed in a loose white cotton t-shirt and a pair of navy-blue nylon shorts. She deliberately omitted one item of clothing, however: her bra. "Women go braless all the time. Nothing illegal about it. And it's more comfortable as well."

She went into the kitchen and poured herself a glass of white wine. Dinner would be easy--she had a pizza in the freezer, and she would make a big green salad to go with it. She checked the mail and was going through it when William joined her.

"How's pizza sound? And a big salad. We have some gorgeous Romaine--I just need to throw it all together."

"Great! Sounds good. How can I help?"

"No help needed, Honey. Listen, I hope you don't think I was too crude after this afternoon. I didn't mean to flash my breasts at you...I think you know that. But honestly, you're a man now and I think we've made some real progress the last couple of days. I feel much more comfortable around you--I used to walk on eggshells worried I would offend you or something, but you seem to be warming up to me and I'm so happy. In fact, I'm so comfortable I'm not wearing a bra, something I wouldn't have considered. But you've seen my puppies bare anyway. I hope you don't mind...if you do, I'll put one on...but I feel freer this way. Is that bad of me?"

"Of course not. Dress the way you like. You've got a great bod so flaunt it...even if you are my mom. It's no big deal, and technically, you're my stepmom. No law against going braless or going naked for that matter, at least while you are home. I wouldn't go to the store naked if I were you. People might stare."

"Oh, Honey. That means so much to me. Come here!"

William walked over to his mother, and she hugged him a gave him a lipsticked kiss, leaving a red smudge on his mouth. He didn't bother to wipe it off.

After dinner they once again relaxed in the den. Vivian had watched her wine consumption, and William only had water with his dinner, so they were clear headed. Vivian grabbed the remote and accidently jumped to channels in the 900 range where the off-color channels resided. A promo for Vivid, a porn channel flashed on the screen. It showed a busty blonde dressed in a schoolgirl outfit sucking on a huge penis. The male actor apparently playing the role of her father encouraged her sucking while reminding her she needed to finish her homework.

Vivian stared, disgusted at first but then mesmerized by the scene and the possibilities it presented. The trailer was replaced by text and a warning sign flashed on the screen advising that all actors were at least 18 years of age and all scenes conformed to a list of legal requirements.

"I knew this stuff existed, but I've never actually watched it." Vivian was tempted to tell her son about her dancing days but thought better of it and bit her lip. "Do you watch this kind of stuff?"

"No...listen, you probably realize that like most men, I look at a certain amount of porn. It is so accessible, but not this kind of stuff. Regardless, you name it, and you can find it. Seems like nothing is taboo unless it is illegal. No kiddie stuff, of course, but this thing you just saw pushes the boundaries. It's like pretend kiddie porn"

"Is there porn with mothers and their sons as well?"

"Of course. That stuff is hugely popular. Moms and sons--yeah. Although it's pretty phony. Most of the sons look like they're the same age as their moms. Not that I've watched any of it myself," he lied.

"Let's find one. I want to watch one for myself!" Vivian handed William the remote. "Will you do that for me? I'm curious."

Her son shrugged and flashed through the titles on various porn sites: the Playboy Channel, Penthouse, Vivid Entertainment, etc. Finally, he found a number of short videos listed under titles like "Mom's Birthday Present" or "Mom's Date night." They settled on "An X-Rated Birthday Present."

Within minutes, "mom" was in her son's bedroom dressed in a silk robe and wishing her son a happy birthday. The perspective was from the son's point of view and only his legs were visible on the bed as his mother crawled seductively toward him. She pulled down his boxers, found his engorged cock, and slowly stroked it for several minutes before wrapping her lips around it, all to her "son's" surprise and delight.

Vivian watched intently, occasionally looking over at William and giggling nervously or adding color commentary. "Wow, her little boy sure has a big penis. She can barely fit it in her mouth." Later, when mom disrobed and worked her son's cock in her shaved pussy, Vivian added, "Oh, come on. Those big fake boobs don't have a bit of sag to them, and her son looks to be in his late 20's at least so she's not a spring chicken."

"It's not real," William added. "It's just porn, Vivian. But this is what people obviously like to watch."

The scene soon ended with mom taking her son's climax on her perfect breasts. Vivian got up to get a glass of wine--she felt she needed one after watching that, and when she returned, another one had started. This one was obviously older and depicted another beautiful and buxom woman bidding her son good night as he watched tv. She decides to take a long hot bath before going to bed, masturbating in the tub. The son, meanwhile, is spying on her in the bath and playing with his cock. When she finally goes to bed in her silk sheets and falls asleep, her son joins her, and she wakes up as he is performing cunnilingus on her perfectly trimmed pussy. Within seconds they are in each other's arms and soon copulating like there is no tomorrow. The scene ends with the obligatory cum shot over the mother's chest and face.

"Now I have to admit, William, I find that kind of hot. This is romantic--at least compared to the previous one. It looks like true love between those two and not just sex. What do you think?"

"Not to be a bore again, but this is just porn. It's not real and you have to consider the audience. I don't think this is geared for middle aged women although women watch porn as well. But what do I know? Anyway, I do agree that this one is pretty hot. The filming and editing make it that way. Kind of dreamy. If anything, it is somewhat artfully done as opposed to the typical wham/bam/thank you ma'am approach."

While William knew little about actual relationships and the complications of intimacy from his own experience, he was an expert on porn like many of his age. He grew up with it, thanks to the internet. Sleazy skin mags and porn shops had all but disappeared only to be replaced by open-source porn available to anyone who could turn on a computer and read. Check the age box showing you are at least 18 and the world of porn awaits--for free.

Vivian was amazed by these revelations. Despite being involved in the "sex business" at an early age, she was a novice when it came to how invasive it had become since then. And William was more than willing to talk about it now that she had opened the door to a frank discussion. He began to see his stepmother in a different light. And not just because of her own sexuality, but because she was so down to earth with him and genuinely listened to what he had to say. She seemed completely open minded about sex.

Vivian had mixed feeling about what she had seen. She was certainly no prude, but the "skin trade" had progressed well beyond what she had imagined. She had literally shown her naked body to thousands of adults when younger--mostly men obviously--but it ended there. Just relatively harmless stripping. Now, it seemed, nothing was off limits except for kiddie porn even though there must obviously be a large illegal market for even that.

"What has this world become? Is nothing sacred anymore, William?" But even as she asked the question, she realized that she couldn't rule out a sexual encounter similar to what she had watched. She was clearly turned on to a degree by both videos, but the second one had caused an indefinable yearning. The mother and son in the video had an unspoken connection beyond erotic. Vivian suddenly felt like this was what was missing from her life, especially since the death of her husband.

She knew that she didn't love William the same way she had loved his father, but she felt there was more to their relationship than just a stepmother/stepson connection. She realized he not only had his father's good looks, but an understated intelligence and sense of humor as well. Of course, much of this was lost in the fact that he was most likely horny 24/7, and as far as she knew, inexperienced in love. Vivian guessed that William was a virgin based on what she knew about the few girls he had ever dated or spent time with.

Shyness and reservation were not qualities that Vivian possessed. She tended to just come right out say things. She had always been open and honest and, overall, it had served her well.

"William, can I ask you something personal? I'm asking not as a mother, but as a friend, I guess. Ok, well, maybe a mother, too. Here goes...." She paused in thought. "I'll just say it. Are you a virgin? Have you ever had sex with a woman...or...geez...even a man, I guess? Don't answer if that makes you too uncomfortable. But I have a reason to ask which I'll explain later."

William turned crimson. He nervously fidgeted for a few seconds before looking up and answering.

"Well, I guess it depends on your definition, but to be completely honest. Yes. I have never had sex with a woman...a female. AND I'm not gay. I have no interest in men if that's what you were thinking."

"No, no...I didn't think you were gay, but I realized that definitions of sexuality are changing these days, so that was an afterthought. I guess my point is that this kind of internet/cable sex has changed the way we interact with one another. And I don't know if its necessarily good or bad. It is what it is. Anyway, William. Thank you for being such a wonderful son. I'm only beginning to appreciate how smart and wonderful you are. And thank you for putting up with me. I can only imagine how hard it is to lose both your mother and your father. And then get a replacement mother all of a sudden. You are one tough cookie, Honey."

With a tear in her eye, Vivian hugged her stepson and then kissed him, first on the forehead and then on the mouth.

"I'm getting sentimental now. I'd better go to bed before I do something I might regret. But thanks for listening to me. I love you, William."

William returned her hug but didn't know what to say. Instead, he kissed his mother on the lips and smiled. "You're welcome, Vivian. My dad was lucky to find you...and so am I. Anyway, sweet dreams."

William grabbed the remote. "Want to watch any more porn?" He smiled. He would never have imagined sitting and watching porn with his mother on the same day that he had fondled her huge tits. And all of it seemed so innocent. Who would have thunk it?

"I'll pass, Sweetie. G'night. I'll see you in the morning. Sweet dreams." Vivian blew him a kiss as she headed toward her room. He shut off the tv and followed her. It had been a long day.

Around 2 a.m. both Vivian and William awoke with a start. A loud explosion that only later turned out to be a nearby car backfiring caused both of them to waken and subsequently struggle to get back to sleep.

Vivian's brain was spinning, and her dreams were a mix of the videos she had seen confabulated with her own life. At one point she was in bed with her father and later she was in bed with her mother and father. As dreams go, it was anxiety provoking and she was happy to wake up.

William simply dreamed of fucking his stepmother. It was not appreciably different than many other dreams that he had previously had. His cock was comfortably swollen when he awoke. He lay in bed fantasizing about Vivian and listening for more explosions. But they never came.

But all that followed was silence. As he started to drift of, he thought he sensed movement in the room, and he realized that someone was slipping under the covers next to him. Before he could react, he felt a pair of lips kissing his neck, his ears, and his face. He turned and his mother placed her lips on his and her tongue met his. He started to talk but was shushed.

"Shhh. Just relax and enjoy this. I couldn't sleep and all I could think about was that you were lying here alone, a virgin. I want to be your first, William. If this is too weird, say so, but I think you want this as badly as me. I'm going to fuck you, Honey. I'm going to let you have your way with me. You don't need to look at any dirty movies tonight, Sweetie. I'm going to show you what the real thing feels like."

Vivian kneeled astride him and reached over and switched William's table lamp on his nightstand. "There. That's better. I want you to be able to see everything."

His mother was dressed in only the t-shirt she had worn earlier. Her nipples poked out from the thin material, begging to be sucked. Vivian raised her arms over her head. "Help me get this off, Honey. I won't need any clothing."

William lifted the hem over her head with his long arms and discarded the cotton shirt. His mother was now completely naked, her large breasts hanging in his face as she kneeled on top of him. "Go ahead and play with my nipples, Honey. They are super sensitive, but I love to have them kissed and sucked, even pulled. Ummm...I bet you're not wearing any shorts! And I can feel your big cock poking me in the butt." She flipped the covers off and reached behind her to discover that he, in fact, was naked. She grabbed his penis and slowly stroked it behind her back. "Oh, Honey. You are so big and hard. In a few moments I'm going to let you put your big prick in my pussy and I'm going to let you fuck me until you shoot all your hot cum in me. But let me know if you think you are going to cum first, Sweetie. Don't worry if you have to cum. We're going to be at this for a while."

William was beyond delirious. This was better than his dreams. His mother's incredible body was highlighted by lamplight shadows. He caressed her ass, thighs, and the smooth skin of her back with both hands as he reached up and licked and kissed her nipples in turn. He doubted he would last long under the conditions, and suddenly he realized he was going to cum.

"Oh, shit, Vivian. Sorry! I can't hold it. I'm going to cum. Oh, FUCKKKK."

"That's ok, Honey. Go ahead and cum." Vivian raised her ass off of her son and slid back. She reached between her legs, grabbed his cock at the base, and squeezed it tightly to stem the eruption momentarily. She quickly placed the head in her cunt and released it once it was seated in her. She slid down on it until her he was buried in her. She could feel his cock throbbing.

William grunted as a huge wad of cum squirted into her pussy.

"There you are, Baby, in your mother's cunt. Go ahead and fill me with your cream. This is only the first one. Before we're through you're going to cum several more times." Vivian had never used coarse language during sex before, but she correctly reasoned that it would only intensify her son's experience to hear his mother talking this way.

She slid her pussy up and down his pulsing prick. His sperm and her cunt juice mingled and lubricated her vagina, and she easily took all of his length with no pain. William's cock was decent sized and even though she had not had a chance to warm up first, it filled her pussy nicely. As his orgasm subsided, Vivian squeezed her vaginal muscles and rotated her hips in tight circles until every last drop was inside her. She hadn't felt a penis shoot inside her for months, and she had forgotten how wonderful it was. When she felt his cock begin to shrink inside her, spent, she raised her ass so that he slid out and her labia relaxed to their normal state.

"How was that, Sweetie? Don't worry, there's more to come. That was just a preview. You just need to rest up for a while. Men your age are resilient. I'm guessing before we're done, I'll be sore, but I'm looking forward to it. Now just cuddle with me while we get our second wind.

She leaned forward and kissed him; her tits mashed into his chest.

"I was lying in bed, tossing and turning and all I could think about was that video of a mother and her son. I know this is weird, but it feels so right. You are a young man with an overactive sex drive if I've pegged you correctly, and I'm a middle-aged woman with needs. Why not kill two birds, hmmm? I'm here for you as long as you'd like. I just hope I don't disgust you."

"Disgust me? You are all I think about, Vivian. I've felt guilty for so long thinking about something like this. This is my dream come true. You are so sexy...and it's not like we are blood related, but either way--I don't care what the rules are about these things. Thank you for this. I am anything but disgusted."

He kissed a ripe nipple before kissing his mother's mouth and face.

Vivian smiled and then an idea flashed across her face.

"Those videos gave me an idea. Would you like me to suck your cock to see if I can get it hard again? I'm not giving away any secrets, but if you'd like that, I'll treat you to an early birthday present."

William nearly passed out at the thought of his mother with his cock in her mouth. He moaned a "yes" as she slid down and looking directly into his brown eyes as he craned his neck to watch, she kissed and licked the shaft before grabbing it and holding it in front of her face.

"I don't think it's going to take much. The power of youth. You're already getting stiff again, but just to be sure...."

Vivian wrapped her lips around the glans and sucked on just the head before lowering her head and burying the shaft inside her mouth until her nose and lips were in contact with his stomach. She slowly slid off until just the head was between her lips, but his cock rapidly grew so that she could no longer take all of it without gagging.

She continued like this for several minutes, stroking and sucking, until his cock was once again at rigid attention.

"Do you like to watch your mother suck your penis? I bet you never knew your mom did such things, did you? You have a beautiful cock, and it looks like you are enjoying it. Look how thick and hard you are getting. I've got an idea of another place you'd like to put this...would you like to put it in my pussy? This time you'll really enjoy it, and we'll make this one last longer."

Vivian slid up and raised her ass so that his cock nestled in the crack between her plump butt cheeks. She masturbated him with her ass for several seconds, all the time looking into his eyes except when she bent down to kiss him.

"Are you ready for another ride, Sweetie?"

She reached back and placed his saliva covered prick between her thighs so that the fat head of his cock was visible under her patch of pubic hair. She lowered her pussy and rubbed it back and forth between her labia. Their lips met and again in a sloppy, passionate kiss as she continued to stroke his shaft with her vaginal lips. All he wanted was to put his prick back inside his mother.

"Ohhh, Honey. I think this is enough foreplay. Ready for round 2?"

Vivian raised her ass to let his stiff cock rise at an angle. Without using her hands, she worked her ass backward until she felt his cockhead spear her labia slightly. Once it seemed safely in her, she pushed against it so that he slid easily into her.

"There we go! Home again. I think you are even bigger than before, Honey. You're going to last much longer this time, Trust me. Ohhh, right there. I knew you would be a good lover. Did you ever think you would be fucking your mother? Hmmm? Neither did I, but I'm glad we're doing this. You're fucking me so good, William. Nice and slow, we don't need to be in a hurry, do we. We have as long as you'd like."