Jill regretted letting Beth talk her into going for a drink with her after work. Now, she was stuck in a basement wine bar of a nearby hotel pouring her heart out. Feeling very drunk, Jill was on her fourth glass of wine as her secretary, Beth, continued to grill her, "What is wrong with you? You have been so distracted today."
"Last night, I woke up in a cold sweat worrying about my son. Earlier in he evening, his father had called to belittle me because of how poorly I had raised Vic. After 18 years, he shows up trying to re-connect with his son and Vic rejected him. In spite, the bastard said Vic was socially retarded and shouldn't go away to college. He hasn't seen his son since he was born and now he is offering child rearing guidance."
Jill continued, "I fought back but I had to admit, the bastard was right. I hate him for it. Vic is so shy and awkward. It was my fault because I was responsible for his life and messed it up. After my ex pointed it out, it was so obvious. The raw shock of realizing I had mistreated him kept me awake all night. Beth, worst of all, I forgot his birthday was last Tuesday. What kind of mother forgets her child's birthday?"
"Make it up to him and stop worrying. He'll be fine."
"I would do anything to make it up to him but when I went into his room this morning to apologize, he was already gone."
"Lighten up. You need to get out more and start worrying about yourself instead of Vic. Why aren't you dating anybody? You look like Zooey Deschanel and are the hottest woman in this bar but three guys hit on you tonight and you didn't give them a second thought. What is up? Those guys were so hot, that if they asked me, I would have fucked them in the bathroom without knowing their names but you didn't even bat an eyelash. And you know what, I have worked for you for five years and you never had a boyfriend. What gives, Jill?"
"I am too old for these guys and I am a single mother that needs to take care of her son. I don't have time for dating."
"I call bullshit. First, these young guys would love to sleep with you because you are in better shape than any woman in this bar. Sexier too. Second, your son is going away to college in the spring so he doesn't need you. Anyway, you never spent any time with him while he grew up because you are always at work. Face it, you are a workaholic. At least your son can go to a good college because of it. So, since it cannot be your son or how you look, I'll bet your gay."
Jill ignored Beth's drunken tease and said, "Beth, I'm worried about Vic. I don't know how I missed it but Vic needs serious help. He is so introverted and socially inept. He doesn't talk to girls and spends most of his free time in front of his computer when he isn't out running. I'm worried he will not make it in college and become an outcast. He will be so far away and will not be able to help him."
"Don't worry, Jill. You have a good-looking boy and he will grow out of it. He was a long distance runner in school so he spent most of his time alone so he is a little shy. It's no big deal. He just needs to meet the right woman. If I was his age, I would do him in heart beat."
Ignoring the sudden mental picture of her son in bed with Beth, Jill responded, "I don't think he will grow out of it. When his father left me and disappeared, I was 17. I had to start a career with a new born baby and no education so I left him with my mother while I tried to go to school and make a living."
Jill continued, "My mother barely spoke to me when I was child so it must have been worse for Vic. It took another 13 years before Vic could finally live with me. But even then, between my late hours at work and commuting, I still left Vic alone too much without any support or guidance. I should have stayed home with him."
With a drunken smile, Beth responded, "You worry too much. Get him hooker. That should take care of what he needs. While you are at it, get one for yourself."
Jill smiled back, "You are so bad. I don't know why I haven't fired you."
The cab dropped Jill off at her home very late and she tried to be quiet as she wobbled in the front door while carrying her shoes. Still very intoxicated, she was afraid of stumbling in the dark and tiptoed through the dark house. Too much wine always made her a helpless lush.
After setting down her keys and purse, she started to go through the mail and then walked back to her bedroom. On the way, Jill noticed Vic's door was ajar and the light was still on so she went in to say goodnight to him. When she entered his room, Vic was lying in his bed but scrambled to cover himself. Jill laughed and said, "I have seen all of your bits and pieces before so don't get so frantic."
After a warm and friendly evening of red wine, Jill wanted to share her peaceful glow of affection with her son. Playfully, Jill pushed Vic over and sat on the edge of his small bed, "I saw your light was still on and wanted to say goodnight. What did you do tonight?"
Acting annoyed that she was there, Vic responded, "Nothing."
Slightly wounded by his brisk dismissal, Jill replied, "Baby, I am so sorry that I forgot your birthday last week. I promise to make it up to you."
Vic retorted without attempting to reconcile, "Don't worry about it. It's no big deal. "
Jill reached out and softly ran her hand along Vic's jaw line as she stated, "You should be out dating some girl. You are so handsome and I know Sasha from across the street would love to go out with you. Are you dating anybody?"
Exasperated, Vic responded, "Thanks mom, but I am not interested in anybody right now."
Looking around his room, Jill mentioned, "I have somebody painting your bedroom tomorrow so you will need to pull all of your computer stuff away from the wall. Okay?"
"I'll do it tomorrow."
As she thought about the colors for the room, Jill noticed the lotion on the nightstand and said to Vic, "Let me help you since your skin is always so dry."
Vic refused, "Mom, No. Its alright."
Jill insisted, "Don't be silly. I want my baby nice and soft. The girls will like it. I know Sasha will like it."
Rolling his eyes, Vic replied, "Mom, I am not dating anyone."
Ignoring her son's protests, Jill spread the lotion between her hands and then ran them over his nearest shoulder and upper arm. Looking at her son, she marveled that she produced something so big. Jill said, "I am always so surprised how big you are. No one believes a 6 foot two boy came from a 5 foot two me."
While she rubbed the lotion into his skin, she noticed his eyes were focused on her cleavage. Glancing down, she remembered that she had started to unbutton her dress while reading the mail and now her breasts in her black lace bra were on full display.
The bra was cut low enough to display most her breasts. Even more remarkable, her son didn't even hide his lustful interest. She had seen this look from men before and was going to cover up but a dark voice from the back of her mind said, "Don't hide your breasts. Its not hurting anyone and it will make him happy. Let him have a little look."
After thinking about it, Jill felt sorry for her son because he had been reduced to scoping out his mom. It was understandable since he was always alone and his only exposure to women was his mom. Not wanting to make him feel awkward, Jill didn't cover herself and let him continue to ogle her cleavage while she rubbed the lotion into his chest. It was harmless and she knew he had accidentally seen her naked a few times.
While pressing her fingers into his soft skin, Jill noticed the hard muscles in her son's arms and remarked, "Baby, you have been working out some more, haven't you? Your arms seem bigger and your muscles are more defined."
With pride, Vic responded, "Yes, I have been lifting weights down at the gym after work."
His shoulders were so broad, that she couldn't reach across them to apply the rest of the lotion. As Jill stood up and placed one knee on the bed next to his waist, she said, "Let me get your other shoulder, baby."
Still tipsy from the wine, Jill tried to carefully balance herself as she lifted her other leg to straddle his waist. While she leaned over her son, Jill noticed a familiar shape in the sheets and was caught off guard. It was too late but Jill realized the silhouette in the sheet was his cock. Her son's rock hard cock. And she realized that she was going to sit on it.
Unfortunately, she was already in mid air and gravity took over so Jill couldn't stop herself. She couldn't do anything but place her other knee on his far side and sit down. Jill found herself straddling her son's waist with nothing between her son's hard cock and her pussy but his sheet and her thin panties. Thankfully, her dress spread out around her and hid the embarrassing situation.
When she looked again at the box of tissue and lotion, she realized that he must have been masturbating when she had barged into his room without knocking. Then, she looked up into his eyes and saw his panic.
Poor Vic, she didn't want his first encounter with a woman to go horribly wrong. Not wanting to embarrass him any further, she pretended to ignore the situation and act like she didn't notice.
To divert his attention, Jill asked, "Dear, can you squirt more lotion on my hands? You seem so tense and need my help to relax. I will give you a little massage like I did when you were younger."
Jill saw the look on Vic's face turn from horror to bliss as she ignored his excitement. A smile crossed his face as he realized he wasn't caught. He protested, ever so slightly, as she kneaded the muscles in his chest, "Mom, you don't have to do this."
Jill whispered in her cool, smooth voice, "Don't worry about it and let your mom take care of you. Just close your eyes."
As Vic closed his eyes and started to cooperate, Jill tried not to think about Vic's hard cock lodged beneath her by focusing her attention on giving him a great massage. As she focused on plying his tense muscles, she tried to stop her lurid thoughts but she couldn't do it.
She could still feel his hard shaft pressed against her. In her drunken state, Jill wanted to lift up and examine his cock but couldn't without appearing wanton so the rest of her senses took over. From everything she could tell, his erect cock was hot, thick as a tree branch and very long.
With her heightened awareness, she became aware of her bare thighs pressed against his skin. Trying to ignore the sexual energy in the air, Jill hoped that maybe her son's erection would subside soon and she could leave without further drama but it never diminished. As Jill spread the lotion over his skin, she vigorously massaged his well-developed chest and arm muscles.
Continuing with her earlier questioning, Jill said, "Vic, you have fantastic chest muscles. I love your pecs. So firm and defined. When a girl sees these, she is just going to melt. Have you gone swimming with Sasha yet?"
Annoyed, Vic shot back, "Mom, I told you that I am not interested in anybody."
Although she continued to massage her son, she dropped the subject of dating so he wouldn't get upset. As she continued to knead him, Jill noticed something else was wrong.
Vic was clandestinely moving his hips just enough so that his cock was rubbing against her panty clad pussy. At first, Jill thought she was mistaken but then noticed his hips were moving ever so slightly and his cock was definitely rubbing against her clit.
With her son's improper action, it dawned on Jill that Beth might have been right. Maybe she should get her son a hooker. His needs would be taken care of, but on second thought, Jill shuddered at the thought of some meth addict touching her son.
Like a typical man, her son was seeing what he could get by with before she protested. She considered stopping him immediately but then reconsidered it. She decided not to stop because, first, he was a fragile boy and may not recover from the embarrassment if she awkwardly rejected his advance. The shame of making a pass at his own mother would be too much for him.
Second, he needed to get better with people and specifically, women so that he could grow into a fine young man instead of a hermit. Sex was a normal part of growing up but he had been secluded too long to catch up. Third, Jill didn't want her son to learn about sex from a hooker. And last, she was too drunk to stop him.
As she continued to massage her son, she noticed that, even if Vic didn't move, when she moved, her pussy rubbed against her son's shaft. Just a little a first but then without thinking about it, she started massaging him harder while exaggerating her movements to hide his deception. To her amazement, her son's cock seemed to get bigger from all of the friction.
Jill was getting turned on too. Strangely, even though she was still fully dressed, she felt herself getting wet as his huge shaft slid along her pussy. In her excitement, her body reacted instinctively and as mother nature intended.
Her pussy lips swelled and pulled back to allow entry. Her juices started to flow to ease passage into her pussy. Except in this situation, she realized her body was granting access to her son's cock. Jill thought about how odd it was that after all of the interest from other men, it was her own son that ignited her sexual spark.
At first shocked, Jill thought about how long it had been since she had been with somebody sexually. When Vic was five, she had one affair with a married man, her boss, that lasted a couple of years. In the years since then, she hadn't been with anybody else. Her desolate sex life had found an oasis.
A voice from the dark corner of her mind whispered to her, "You need to help him. This is your fault."
Jill silently replied, "I shouldn't."
The dark voice silently shot back, "You must. No one else will help him so you do it. Don't play coy; you know you want to do it. Make the poor boy cum. Just do it."
Jill looked down at her son and evaluated him as if he was a stranger. He was handsome and well built. Young and firm. Very soon, Vic would be gone and no longer hers. Before he left for college, he just needed guidance to be successful in the world. But right now, she knew he needed to cum more than anything else.
Briefly considering how to please her son, Jill needed to get this over without making him feel bad. It was up to her and she came up with a plan. Jill was thankful no one else would ever know what she was going to do next.
With her sweetest voice, Jill asked, "Vic?"
As his hips stopped moving against her, Vic opened his eyes and focused on her cleavage as he replied, "Yes, mom."
Jill held her hands out to him and whispered softly, "Can you get some more lotion for me?"
In a trance like state, he squirted some lotion into her palm and Jill mixed it between her hands. She looked into his eyes and acting like she suddenly remembered something saying, "Now, can help me? I just got this dress dry cleaned and don't want to get any lotion on it. Please help me remove it."
His eyes lit up. Vic didn't hesitate but Jill added, "But since I will only be in my underwear, you have to promise to keep your eyes closed. Can you do that for me?"
Vic spurted out, "I promise". He reached up and started to undo the remaining buttons down the front of her dress. While he fumbled, Jill pulled back her shoulders and straightened her back as Vic undid the next button. Oddly, she wanted to look good for her son. He took his time as he unfastened the last few buttons down to her waist.
Softly, she asked, "Can you pull the dress over my head and put it gently on the ground so it doesn't wrinkle?"
Vic complied without ever taking his eyes off of her. Satisfied that he was a typical male, she didn't remind him about forgetting not to look. Like a starving man looking for food, his eyes traveled over her entire body. Cocking her head back so her son could leer at her without being observed, Jill casually presented herself to him to satisfy his carnal hunger.
Jill was straddling her son in only her matching black panties and bra. The dark lingerie was a stark contrast to her white skin. Normally she wore a thong but luckily, this time, she was wearing lace boy-shorts panties with scalloped edges. Jill liked them because her pale skin looked sexy through the ornamental weave. Also, boy-shorts were the current trend and these modestly covered her ass and rose high on her waist.
But upon turning her head and seeing herself in the mirror over his dresser, Jill reconsidered. Maybe the panties weren't so modest because the lace allowed someone, especially if they ever got close enough to stare, to see her dark trimmed bush through the material. Vic was close enough and her prominent pussy mound drew his eyes to her bush. Jill tried not to think about it.
Her bra matched the panties but exposed generous portions of her large breasts. The bra hooked in the front with a little bow hiding the clasp. She was lucky that her breasts stood straight out on her chest. Looking at the thrill on his face, Jill knew that her son could see through the lacy bra. His eyes were locked on the prize. Placed high on her breasts, her aureoles were small but her nipples always stood out 3/4 inches.
At first she was uncomfortable with her son staring at her nipples but then she relaxed as she convinced herself that he needed the experience. In fact, because of her son's hungry look, she was a little prouder of her breasts. Her son lustily gazed upon her while she continued to knead him.
The entire time her son was staring at Jill, she continued to massage him. When she had finished each arm, she placed his hand down on her thigh. In an automatic response, her son reciprocated and started to caress her thighs. Unexpectedly, her son was touching her like a lover instead of her offspring.
Jill now focused on creating a rhythm to her massage almost like a wave running up a beach. Without ever taking her hands off of Vic, she let her fingers seduce her son. Her hands ran up her son's chest and then down his flat stomach. She had to be careful because she couldn't go too far down. His large cock almost came up to his belly button and although still hidden under the sheets, she could see the head of his cock peeking out between her legs.
As Jill's hands went up his body, her pelvis moved along his cock. As her hands went down to his stomach, her pelvis traveled back down his shaft. Jill maintained this slow pace to show him how to please a woman. Whenever she noticed Vic starting to squirm, she backed off a bit. She wanted him to learn to wait when he was with a woman and that he didn't have to rush.
After five minutes, Jill was getting too horny to continue and decided she needed to end this now before she did something really stupid. She could figure out what to do later. Starting to make her waves speed up, Jill made the massage harder, more intense. She worked her fingers into his muscles while her pelvis was doing magic for Vic as his mouth opened and a low moan escaped his lips. His eyes were rolling back into his head as he struggled beneath her while she mixed pain with his pleasure.
Jill asked, "Do you like your massage?"
Vic looked up and said, "Yes. It is the best one ever. I have never felt so good."
Jill then pulled back hard on his shoulder muscles and ground her pelvis into his cock. She kept repeating these actions and noticed Vic's eyes were closed tight. His hands were grasping her bare thighs to try hold on while she moved on top of him.
Sensing he was getting close to an orgasm, Jill rocked her hips from front to back along the length of his cock without moving the rest of her body and she knew she was successful when she heard her son gasp, "Oh god mom, please stop."