Another long story from my archives. Bobby sat on the commode in the plush upstairs bathroom with a thin, well-worn magazine of grainy photographs of nude women in his left hand and his K-Y jelly-lubricated erection in his right.
As he stared at a waist-to-head picture of a particularly sexy brunette with medium sized breasts he slid his jelly-slick hand slowly up and down his hard penis while trying to imagine what it would be like to have this woman sitting live across from him watching him jacking off instead of just staring back at him lifelessly from a piece of paper.
Nonetheless, as he stroked himself that good sensation in his groin continued to build. It wouldn’t be long now before his cock would spew out that marvelous white jism onto the face of this woman who turned him on so much with her sexy sneer. Although it would ruin another couple of pages of the magazine, Bobby just couldn’t seem to help himself; it gave him such a thrill to come on the faces of the women who turned him on.
Today was unusual in that the basketball coach had called off the normal after-school practice and Bobby was able to go home early. He had planned to use the time to catch up on his homework, but when he got home he hadn’t seen his mother’s car in the driveway and figured she must have stayed late at work. Thinking he had the house to himself, he hurried to the upstairs bathroom to relieve himself of the tension that had been building in him because of two incidents earlier in the day.
The first had happened while he was getting dressed for school. He had been passing down the hallway on his way to the bathroom when he happened to glance through the half-opened door of his parents’ bedroom and caught a glimpse of his mother, Norma, clad in only bra and panties as she got dressed for work. Although the glance was only fleeting it was enough to set him on edge.
Norma was a tall, statuesque woman whose most striking features were her long, wavy black hair which cascaded down her back almost to her waist and her equally long full legs. From the time Bobby began to develop sexually he had been attracted to her and her beautiful legs held a special fascination for him.
From time to time he would masturbate while fantasizing what it would be like to be able to fondle and kiss his mother’s legs. He was also extremely curious about her breasts, which appeared to be slightly on the small side. Try as he might, he had yet to see his mother’s bare breasts and this just inflamed his imagination that much more.
The second incident occurred in biology class when Jenny Avarrito had tripped on her way past his desk and landed squarely in his lap. The fall had caught him unawares and as he grabbed her to keep her from sliding to the floor his hand had landed firmly on her beautiful full long tanned leg. From that moment on he hadn’t been able to get the feel of her firm yet soft leg in his hand out of his mind.
So enraptured was he now in his erotic musings as he sat masturbating to the erotic vision of his mother alternating with the feel of Jenny’s leg and the sexy tits and sneer on the face of the woman looking at him from the magazine that he was taken completely by surprise when the bathroom door suddenly opened and there stood his mother staring in amazement at him.
She remained frozen in the doorway with one hand on the doorknob and the other on the jamb for what seemed an eternity, but was probably only a few seconds, her gaze alternating up and down between his eyes and his crotch. Just as suddenly as she had appeared she whispered, “Excuse me, I’m sorry,” and was gone, softly pulling the door closed behind her.
But it was too late. The damage had been done; he’d been caught! “God – what’s going to happen now,” he worried as his cock slowly began to deflate. His libido deflating as well, Bobby decided he had better get cleaned up and go try to do some homework – or something.
And then he remembered that early that morning his mother had hastily told him on her way out the door to work that she was leaving work early to take the car to the garage for maintenance and that she would get a ride home from there. He realized then that she must have been home the entire time even though he hadn’t seen or heard her. Maybe she had been taking a nap or something.
Just as he put the magazine on the floor and was ready to get a washcloth to clean himself off he heard a soft rapping at the door. Then the door opened a crack and his mother stuck her head inside and said, “Is it alright if I come in, Bobby? Please let me come in.”
“Gee, mom, I’ll be out in just a second. Can you wait?”
“Bobby, I want to talk to you – right now,” she said as the door opened wider and she entered. “Please let me come in.”
When she was fully inside, she gently closed the door and turned toward her son who was still seated on the toilet with his pants around his ankles. Looking down on his upturned face she said, “I’m really sorry to disturb you, but I’ve been wanting to talk to you about this for quite some time now. Do you wind?”
“Talk about what, mom?”
“This. You know – you’re doing this. Masturbating.”
“Aw, gee, mom…”
“It’s OK, Bobby. Look – I’ve been meaning to bring the subject up ever since I talked to your father about it, but he’s such a wimp that he just shrugs it off and refuses to discuss it. I’m just a little concerned about you – I’m your mother, you know – and curious also. Can you and I just discuss it?”
“Can I, uh, get dressed first?” Bobby asked, feeling a little embarrassed sitting half naked in front of his mother even though his erection had subsided.
“Well… I thought maybe you’d like to, uh, finish what you’d started – before I so rudely interrupted you.”
When her son didn’t answer, she said softly, “It’s OK. You can go ahead. I’d really like you to go ahead and finish it, Bobby.”
“You mean finish doing it? Right now?” He queried, puzzled.
“Uh huh – if you wouldn’t mind, dear.”
“With you here?”
“Sure – if you wouldn’t mind. I’d kind of like to watch you.”
“You’d what!” Bobby said in amazement.
“I’d like to watch you masturbate yourself, Bobby.” His mother said matter-of-factly.
“Aw, mom, it’s bad enough you caught me without you making me do it in front of you,” he said shamefacedly.
“I’m not going to make you do anything you don’t want to Bobby. But I really would like to watch you do it to yourself.”
“Well – gosh, I don’t know whether I could do that or not. I’ve never done it in front of someone before.”
“I understand, son. I guess it might be a little difficult to get yourself excited, given the circumstances – especially with your mother present.” With her hand his mother pointed toward the magazine lying on the floor and said, “But it’s OK if you want to go ahead and look at those pictures – if you think it would help.”
The reference to the magazine made Bobby blush again and he didn’t know quite what to say. Norma, sensing her son’s hesitation, bent down and picked up the magazine. Glancing at the picture that Bobby had been looking at earlier she handed it to him asking, “Is this the picture that you like to look at? Is she the one that turns you on? She’s really got beautiful breasts, doesn’t she?”
Reflexively, Bobby reached out with his hand and took the magazine from her, looking down at the picture. Totally confused by the situation, especially hearing his mother talk this way for the first time in his life, Bobby was at a loss as to how to act, but he felt thoroughly trapped with no way out.
“Well, maybe if you’re not ready yet, we can talk a little, OK?” His mother asked.
“Sure, mom, OK.”
“Would you answer a couple of questions for me?”
“If I can – sure.” Bobby responded hesitantly.
“I’ve known for some time that you’ve been doing it, dear. All the telltale signs are there. I want you to know that I think it’s OK, though, and that it’s normal and nothing to be ashamed of, OK?”
“Uh huh.”
“Have you had sex with a girl yet? I mean real sex – where you have an orgasm?”
“No,” Bobby answered softly, and then added, “not that I haven’t wanted to.”
“Naturally. When you masturbate, do you fantasize about Jenny or Ariel or any of your other girlfriends?”
“Yeah, sometimes.”
“And what do you fantasize about them?”
“You know – what it would be like to be with them, touching them, that kind of stuff?”
“Uh huh, and would you like it if one of them jacked you off? I’m sorry, dear – you do know what jacking off is, don’t you?”
“Sure. It’s what I was doing – masturbating.”
“Does it bother you, Bobby, when I talk dirty like that? You know, use dirty words like jacking off?”
Actually, it was somewhat titillating to hear his mother use that kind of language, but he only replied, “No ma’am, it doesn’t bother me.”
“And would you want one of your girlfriends to do it to you? Jack you off?”
“I guess. Yeah, but I don’t think it would ever happen.”
“And the other times? When you’re not fantasizing about them you look at pictures?”
“Uh, huh,” Bobby was starting to get even more nervous now, wondering whether his mother was going to ask him whether he thought about her while he was doing it. That was an area he wanted to avoid because from time to time he did think about her, wondering what her body looked like totally undressed. He could not ever remember seeing his mother totally naked although now and then he had glimpsed her in various states of undress as he had that morning. He was especially turned on by her legs which were long and full.
Even though his mother was not big-breasted she had enough to make her blouses and sweaters stick out and he was curious about them and what they looked like, especially the nipples which seemed to poke out through her clothes all the time.
Sensing she was getting close to shaky territory, Norma pushed a little harder with her next question. “Is there anything else you think about besides your young girlfriends, Bobby?”
“Well…” And he hesitated a long guilty moment.
“How about me, Bobby. Have you ever thought about me while you masturbated?”
Norma could tell even before he opened his mouth that she had hit the mark. Bobby’s face turned a few shades of darker red as he stammered, “Aw, mom…”
“It’s OK, Bobby. I think it’s natural for a boy your age to be curious about his mother – even sexually. Now tell me the truth have you ever thought about me.”
“Well, sure, I guess. Once in a while,” he admitted shyly.
“And what do you fantasize about me?”
“Gee, mom, this is really embarrassing…”
“There’s no need to be embarrassed, son – I’m your mother and you can tell me. I’m really curious and I’d like to know. Now tell me what you think about me while you’re playing with yourself.”
“Well, I guess I like your legs a lot, mom. I think about them mostly.”
“Well, I’m very flattered, son,” Norma said reassuringly. “I’m glad you find my legs attractive. I always thought they were a little too fat.”
“Oh, gee, no. They’re really beautiful, mom. I mean it.”
“Tell me – what’s the thing that most turns you on about women? Is it their legs, or rears, or their breasts or what?”
“Breasts, mostly, I guess.”
“Is that what you look at most of the time when you look at those pictures?”
“Uh huh.”
“Do you ever think about my tits, Bobby. Have you ever seen my bare breasts?”
“Uh, no I haven’t,” he stammered honestly, wondering what his mother was getting at now. Norma then suddenly stood and said, “Wait here just a minute, OK – I’ll be right back,” as she opened the bathroom door and turned down the hallway.
A minute later she was back and reseated herself on the edge of the tub. In her hand she held what appeared to Bobby to be a bunch of photographs, but he couldn’t see what they were. Then his mother said, “Bobby, I’d like you to see these, if you want to, but first you have to promise me that you won’t ever tell anyone you’ve seen them, OK? Promise?”
“Sure mom, if you don’t want me to say anything, I won’t,” Bobby said, thinking that maybe his mother had some girly pictures of his father’s or something.
Without saying anything Norma held the photos toward her son. Bobby took them in his dry hand while reaching for a towel to wipe off the K-Y jelly on his other hand. Having done so he then looked down at the top photo and was stunned.
There, in full living color, was a picture of none other than his mother dressed up whorishly like many of the girls in the magazines. She had on sheer black stockings held up by suspenders from a black garter belt and high heels that made her beautiful legs look even longer and fuller. But what attracted his immediate attention was that her upper torso was encased in a partial bra that lifted her breasts and pushed them out while leaving the nipples completely exposed.
He felt his soft cock twitch and began to harden again as he gazed at the magnificently large dark brown areolae and nipples on his mother’s breasts. They were huge – larger than any he had ever seen in a magazine or even imagined existed. And they jutted straight out from her tits tilting slightly upward and outward.
As he continued to stare at that one picture he was aware that his cock was swelling and that it was in plain view of his mother’s sight. Still, he couldn’t seem to remove his eyes from the picture.
When he finally did look up at his mother she had a sexy smile on her face and said in a low, husky voice, “It’s OK, Bobby. You can look at the rest of them, too, if you want.”
“Is this really you, mom?” He asked, somewhat confused and a little embarrassed at being so boldly confronted with his own mother’s sexuality.
“Yes, Bobby, it really is me. But don’t ask how they were taken that’s my secret. Just go ahead and look at them, OK.”
Bobby just nodded his head as he took the second photo. It showed his mother sitting upright on the edge of a straight-backed chair. Her legs were spread and he could now make out a thick black patch of pubic hair between her legs. This inflamed him even more. He had never before considered even remotely the possibility that his mother had a sexual side, but that idea was changing rapidly.
There were about six pictures in all of his mother in various poses and dressed the same in each picture. The last one was somewhat different, however, insomuch as now his mother was sitting spread legged on the edge of the bed and she had one hand holding what appeared to be a large black rubber penis stuck in her cunt while the other hand pulled at one of her big nipples as she leered at the camera with a lust filled expression.
At this point, Bobby became fully erect again and looked apprehensively up at his mother. Norma just smiled and said to him, “Well – I can see that I do turn you on, don’t I?”
As Norma nodded her head toward the picture Bobby was holding she said, “And you ought to be able to see from those pictures that boys aren’t the only ones that play with themselves, either. I’ve been masturbating since I was your age and still do it almost every day – sometimes more than once a day. I love doing it and love watching other people doing it, too. That’s why I want to watch you. Maybe one of these days I’ll even let you watch me jack off if you’d like. But now I can see those pictures have gotten you hard again. Would you like to look at them while you masturbate?”
When Bobby didn’t respond right away she continued, “I’d be glad to have you look at those if you want to. Go ahead, Bobby, it’s alright. You’re hard as a rock. Why don’t you go ahead and jack off your hard penis while you look at those pictures. Here – give me your hand,” and Norma reached out and grasped her son’s hand, the one that he had been using on his cock. Turning the palm up she proceeded to gather a mouthful of saliva and spit it onto his hand.
“That’ll help make you slick again, huh.”
Dumbfounded, Bobby reached down and began to smear his mother’s spit over his solid erection as he looked into her sexy eyes. When it was completely covered he wrapped his hand around it and began to slowly pump it up and down as he looked once again at the super charged picture of his mother fucking herself with the dildo and playing with her nipple.
After a few moments he heard his mother say, “Do you like my tits, Bobby? Now that you’ve seen my bare breasts, don’t you think they’re really nice? I have nice big, sexy nipples don’t I? Actually, I’ve got the biggest nipples I’ve ever seen on a woman and I know they turn men on. Do you like them, Bobby?”
“Oh, god, mom – they’re beautiful, they really are. They’re so big!” Bobby exclaimed in his building excitement.
Then his mother stunned him once again when she asked him, looking deeply into his eyes, “Would you rather see the real thing than look at those pictures, Bobby?”
“What?? You mean…?”
“Yes, Bobby. I do mean. If you’d like, I’ll let you look at my bare breasts while you jack off. Would you like that, huh? You can see it all – my big nipples and all, if you want.”
“Ohhhh, mom…” Was all Bobby could get out as his breathing became ragged and his excitement rose at the thought of his mother showing him her bare tits.
“Well…? Do you want to?”
“God, mom, yes…”
“Yes, what, dear? Tell me what. Tell me what you want to see. I want to hear you say it, Bobby.”
Hesitantly Bobby said, “Please, mom, let me see your breasts. I want to see your bare tits with their big nipples.”
“That’s right,” Norma whispered as she began to unbutton her blouse. “That’s what I’m going to do – right now. I’m going to show you my breasts.” When the blouse was undone she pulled it out of the waist of her slacks, shrugged it off her shoulders and let it fall backwards into the tub.
“And what are you going to do? Tell me what you’re going to do while you look at my bare tits, Bobby.”
Bobby then went almost catatonic as his mother reached behind her to unclasp her bra. His eyes bugged out as the back of the bra fell open, but his mother kept the bra against her bosom with one of her forearms saying, “Come on, Bobby, tell me what you’re going to do while you look at my tits – or I won’t show them to you.”
Bobby was so excited at this point that he could hardly talk. He was almost goggle-eyed as he stared across at his mother’s bosom, but he managed to get out, “Uh, well – I’m going to jack off, mom. I’m going to masturbate while I look at your beautiful tits.”
“And are you going to cum, dear?”
“Oh yes, ma’am. Yes – I’m going to cum.”
“That’s just what I wanted to hear, Bobby. I want you to cum. I want you to cum real hard while you look at my tits and nipples,” Norma said as she then suddenly let her arm drop and the bra fell away from her chest exposing her two magnificent breasts to her son’s gaze. Bobby just sat and stared at his mother. Her tits were even more beautiful than they appeared in the photographs. They stuck straight out and now Bobby could see that the deep dark brown areolae had a pebbled textured and the nipples themselves were longer than they appeared in the pictures.
“Nice, huh, Bobby?” His mother said teasingly. “Doesn’t the sight of my bare tits and nipples really make you want to jack your cock?”
Bobby couldn’t seem to move. He was mesmerized as he sat, his one hand holding his rock-hard prick in a near death grip.
He didn’t actually need to move, though, because when his mother said, “My nipples get even longer and fatter when I play with them,” and reached both hands up and began to pull, twist and tug at the already turgid nipples, Bobby had a spontaneous orgasm right on the spot.
His rigid cock began to spew out jet after jet of thick white jism, the first couple of spurts traversing the short space between them and landing on his mother’s thighs, soaking into the fabric of her slacks.
“Ohhh, Bobby, yessss!” Norma purred, “Yes – oh, shoot out all that lovely cum, son. That’s right, jack your cock, honey. Make it spurt! Jack it off for me, dear!”
Hearing his mother’s exhortations, Bobby then began to frig himself violently causing his cock to renew its spasms sending even thicker cum spewing forth covering his hand and his own thighs.
As the orgasm began to lessen, Bobby’s mother reached over with her hand and gently stroked her son’s face and said, “That was really great. That must have been one of the best orgasms you’ve ever had. Now why don’t you clean yourself up and let’s have dinner. We can talk some more about this as we eat.”
Norma then quickly gathered her blouse and bra and gently disengaged the pictures from Bobby’s grip and departed the bathroom as he just lay back against the toilet seat, eyes scrunched closed, recovering and considering what just happened and what might happen in the future.