*** I am NOT a native English speaker and although my English is, by all means, pretty good, it isn't perfect. If the smallest mistake or a not-so-common sentence construction puts you off, I suggest you skip this one. No hard feelings, really, I'm just being honest! But if you think that contents can beat the occasional "we is" (just kidding!), then read on.
On other news, I love feedback. If you like the story, please let me know. If you don't, but can make constructive criticism, let me know also! And if you just feel the need to be harsh, go ahead too, it's your right. I promise I'll not be hash back, it's not worth it. :-)
Last but not least, this is a work of fiction, any resemblance with real people or names is purely a coincidence. ***
It was almost a habit of mine: when I was eighteen/nineteen, I flirted a lot with older women. Now, don't think I was some type of "toy boy", because I wasn't... I was fairly good-looking, but very timid and a little nerdy and, as such, my flirting never, ever have gone beyond that: flirting. Maybe currently it would be easier for me, but it was in the 1990s, where women (especially married ones) were even more judged by society than today.
I'm not saying I would not get the casual smile back or even a few second looks, but if I tried to make any advances (I did try a few times, overcoming my shyness) I was always rebuked, with them changing their behavior and avoiding my stares, discouraging me from even trying to start a conversation.
But perseverance is everything, even when you think it's futile...
It was a normal day like any other and I was on the bus going back home from college and a mother, with her ten-year-old or so son, caught my attention as soon as she entered the bus. She was in her early forties, with black, shoulder-length hair, a little overweight and a pretty common face, not beautiful nor ugly. She was the prototype of the stay-at-home mom, her ring clearly visible on her hand, taking her son back from school and looking ahead to an afternoon of house chores and cooking for the husband. Anyway, as soon as she sat down I changed places, so I could be a little ahead of her in the bus, and started to occasionally look back at her, discreetly but insistently.
She didn't notice at first, probably because she was not a looker and was dressed like someone that gave up the idea of seducing guys on the streets a long time ago. She just kept talking to her son about something, and I was almost giving up any hope when her eyes finally met mine by pure coincidence when she looked ahead to try to see if her stop was coming. As I stared at her, her expression clearly showed that she thought I knew her from somewhere and that she was trying to find out who I was, but as soon as I smiled at her, five seconds later, she blushed hard and looked down.
From then on, every time I looked back I could clearly see that she was well aware of my attention and enjoying it, although she didn't look back. Her artificial behavior gave up she was feeling pretty for the first time in a long time, and her discreet, but noticeable smiles with herself showed how good to be noticed by me made her feel.
Less than five minutes later, though, the bus was arriving at my stop. I couldn't even think of continuing in the bus, as I had lots of things to do at home and my mother was waiting for me, so I reluctantly got up from my seat and walked to the exit door. As soon as I got to the door I looked back and to my - and hers - surprise, she would, too, get off the bus on that stop. She looked clearly uncomfortable, but as she didn't have a choice, she took her son's hand and walked towards me at the same time that the bus stopped.
I got off and started to walk slowly, followed by her, and as took the first right - the street where I lived - she again followed me. She lived in the same street I did! I kept looking back, but she was looking straight ahead, again clearly aware of my stares but not wanting to let me know, and I could see when she entered the second building of the street. Now I was not even trying to be discreet, and I almost turned back to look when she finally, as soon as she entered through the glass door, looked back at me and smiled, feeling "safe" from any attempts I could make to talk to her but at the same time clearly proud of my interest.
All I could do was to watch her going inside, her plump but inviting ass swinging under her dress, until she disappeared inside the building.
From that day on I was obsessed with her. She was the first older woman that gave me any indication that she could, at some point, give in to my advances and so I did what any horny teenager would do: I started to stalk her on the bus stop.
I knew where she got into the bus, as I've seen her entering it, and I knew the school where her son studied by his uniform, so it was not hard to "bump" into her periodically. I couldn't do it every day as my college schedule didn't allow, but two or three times a week our secret ritual took place: I would get into the right bus, well aware that it would be the same bus she would get a few stops ahead; she would then arrive with her son, and I would stare at her more and more lasciviously each day. She, too, started to change, at first in the way she behaved - looking at me briefly from time to time and smiling, making it clear that she knew what was happening - and then starting to dress smartly and to wear make-up, what she didn't do before. The problem is that our trip would end the same way day after day, week after week, with her avoiding me completely as soon as we got off the bus and making clear, by the way she acted, that she didn't want me to talk to her on the street.
It was obvious, after some time, that she really, really liked the attention, that the inner teenager she had inside her wanted to show herself, but that her fear of being seen or that her husband could find out was too much for her. In short, it was a dead end, unless something very different could happen.
And it did.
It was a Saturday, and I wasn't even thinking about her or anything else for that matter. I had left home to go to a friend's house where we would play some games and was absent-mindedly walking to the bus stop when I saw her coming from the opposite direction, alone this time, with lots of grocery bags in her hands. She didn't see me at first, as she was fumbling though her purse apparently looking for her key, and it was only when she turned towards her building entrance that she sensed someone coming on the street. The surprise of seeing me was so big that one of the bags fell from her hands, the oranges and other fruits she was carrying rolling through the floor and giving me the perfect excuse to talk to her.
I immediately started to pick the fruits from the ground and put back inside the empty bag while she just stood there, looking as she didn't know what to do and clearly uncomfortable with my presence. I, too, was so nervous that I was probably red as an apple myself, but I did my best to control myself when I got closer to her and said:
"Hello! Sorry, I didn't mean to startle you."
She didn't reply and looked even more nervous than I was, what made me a little bolder:
"Look, you have too much to carry and I believe this building doesn't have a lift, right? Let me help you carry these up..."
Without waiting for an answer, I took a few more bags from her hands. She looked around, obviously worried that someone could see us, and finally said:
"No, you... I can carry them myself..."
"No way, no reason to do that! We are practically neighbors, it's my duty to help!"
For a moment, I really thought she was going to just take everything back from my hands and go, judging by how nervous and worried she was. But, as I embraced the bags and looked like I wasn't going to give up easily, she probably thought it would be riskier to stay as we were, on the street arguing, than just allowing me to take her bags and go.
After looking around once more, she finally opened the gate and let me in, entering in a hurry right after me and going straight to the stairs. I followed her through the two flights of stairs until her apartment, number 302, and when she opened the door I didn't wait and just entered the kitchen without asking. I was so excited that I didn't even think about what could happen if her husband was at home which, fortunately, he wasn't.
As soon as I put the bags over the kitchen table, she said:
"Thank you. Now, please go..."
"W... Why? What do you mean why?"
I took a deep breath and, risking everything, said:
"Look... I know you know me. And I know that you... Well, that you are happy that I think you're beautiful."
She blushed, looking down, but said:
"I don't know what you're talking about..."
"What's your name?"
She hesitated, but replied:
"Mine is Daniel. Look, Laura... You... You're a beautiful woman. I know I'm just a boy, but I've been thinking about you so much..."
She kept her eyes down, but I could see a smile going through her face before she replied:
"You... You've been thinking... About me?"
"Yes... I... I'm not bumping into you on the bus by chance, you know? I... Please, don't think I'm a freak, but I do it on purpose, so I can see you..."
Laura - now I knew her name - was more and more nervous and clearly battling with herself, her hands rubbing each other. and I took the opportunity to close the door that was still ajar.
"What... What are you doing???"
"You are visibly worried about being seen, aren't you? And judging by the fact that I'm here, I believe your husband and son were not at home. I closed the door so we can talk, but don't worry, if you want me to go, I'll go."
"How... How do you know I'm married?"
She finally looked at me, and I could see how tense she was.
"You're using a ring. And your son, I've seen him with you several times."
"One of them... I... I have another boy. He is twenty-years old. Probably older... Older than you... Oh, my god..."
Looking away once again, she spoke as she was talking with herself, trying to convince herself that she needed to ask me to leave. Sensing the opportunity, I asked bluntly:
"Where are they?"
"They... They are out. Playing soccer."
"And when are they coming back?"
She hesitated once again, but she looked like she was almost in a dream-like state, not thinking too much, and said:
"Only... Only in the late afternoon. It's in a club, they get lunch there and..."
She stopped talking and I glanced at the wall clock: around noon, what meant we had plenty of time. Despite the nervousness and excitement, I was feeling more and more in control of the situation and, taking a new step, I extended my arm and softly touched her chin, making her look at me again. She complied, and I could see her eyes pleading with me to not go ahead, but I simply couldn't... All those weeks of anticipation, all the times I masturbated myself to orgasm thinking of her, made it impossible.
In a swift movement, I embraced her and kissed her lips hard. She tried to resist pushing me faintly, but soon gave up and returned the kiss, breathing hard and dancing with her tongue inside my mouth. I was taller than her, her head about the height of my chest, what made it easier to me to just put my arms under hers and lift her off the ground, sitting her on the table where the groceries were still lying. I could feel her chest going up and down with her breath, her self-control going away fast, and soon I was exploring her big tits through the fabric of her dress.
My cock was hard as a rock at that point, and I wasn't giving her any chances to back off. If I tried to took her hand and go to the bedroom she would have time to think and I didn't want that, so I simply opened my fly, took my cock off and, after lifting her from the table, pushed her dress up and swiftly tore off her panties in a single push. Her eyes widened, but before she could protest I pushed my body and entered her pussy in a single movement, her abundant fluids making it easy and effortless.
That was my first time, my first pussy, ever.
Still resisting, she tried to say something through our kiss, but as I started to move my body back and forth she lost herself and started moaning, louder and louder, apparently forgetting about the neighbors.
"Ah... Ah... Ooooh... Ahhh..."
I was moments away from coming, but in a giant effort I could postpone it for a few minutes, as hard as it was with her moans echoing on that kitchen, until she finally rewarded my efforts with a trembling, strong orgasm, digging her nails on my back while mumbling:
"Oh, oh, God, I'm... I'm... Ooooooooooohhhhhhhhhhhhhhhh!!"
I then just let myself go and came harder than ever, my cum flowing jet after jet inside her channel while I kissed her passionately until emptying my balls. Soon I was feeling dizzy and with my legs trembling, and sat down on one of the chairs that circled the table, the fog of excitement, lust and desire finally starting to dissipate.
I can't say if it was seconds or minutes after that, but the next thing I remember is Laura saying softly:
"Oh, my god... Oh, my god... What did I do?"
Coming back from wherever I was, I looked at her and she was still sat on the table, her legs open, my cum flowing from her pussy and over her pubic hair. She looked at me, then at herself again, and said, terrified:
"Did you... You... Inside me???"
I didn't know what to say, as it was pretty obvious, and as I didn't reply she finally appeared to regain her composure and, getting off the table and putting her dress back down, said, looking lost:
"I... I'm not... Oh, god, I'm not on the pill... I... Me and my husband, we... We rarely..."
I sincerely wasn't that worried. What was the chance, really? I rose from the chair and embraced her, saying:
"Laura... Calm down. This will not happen..."
She suddenly started to cry, and feeling terribly sorry for her I took her into my arms, not knowing what to do. Still crying, she again started to talk:
"I... I don't know what I'm doing... Oh, God, I... My husband was the only one. I never... Oh, I can't even say the word. I never... cheated on him... Now, what am I going to do??? Oh, I'm so ashamed..."
I caressed her hair, genuinely sorry, and said:
"Laura, honey... Please, don't be like that. Nobody needs to know..."
"I... Oh, if he finds out what will become of me? And my sons... Oh, no, no, he can't!!"
I felt I needed to do something and, taking her hand, guided her through the kitchen door and into the living room, making her seat on the sofa. I then walked back to the kitchen and got some water, taking it back to her. Her eyes were already red and puffy because of her crying as she took the glass from my hands and drank, giving me the chance to speak:
"Laura... Please, be calm. Nobody will know, I promise. Look, I..."
I didn't know what to say anymore, and as she was looking very lonely and fragile, I sat at her side and, taking the glass from her hands and putting it over a small center table, embraced her and repeated my previous gesture, pushing her chin up and making her look at me.
"Psttt... Be calm... You're even prettier when you're crying, but I don't want you to be sad..."
My compliment made her smile through her sadness, and I again kissed her lips, this time softly. She didn't resist this time, kissing me back and completely giving herself to me while embracing me, apparently forgetting about her guilt, at least momentarily.
We kissed like a couple of teenagers for a while, but soon our breathes started to accelerate again. Without saying anything, I broke the kiss for a moment and took off my shirt in one movement, immediately seeing how she admired my young, firm chest and arms without even thinking. I then took her hand, rose from the sofa, and guided her through the corridor, trying to find her bedroom.
"No! I mean... Not... Not in my bed, please..."
"But... But then, where?"
She thought for a moment and said:
As soon as we entered the room, I could see by the decoration that it was her older son's room, He had a double bed and, as we went there and before kissing me again, she said while looking down:
"D... Daniel, isn't it? Look, I don't want you to think I'm some... Some easy woman."
"I... This is not something... Well, as I said, my husband was the only one before... Oh, God, before you... It seems so unreal!"
For a third time I made her look at me and said:
"Laura, I don't. I... Look, you can trust me. Nobody will ever know about us, never. You're safe, ok?"
She appeared to relax a little, but continued to try to justify herself:
"My... My husband, he... He lost interest so long ago, he never... When I said we rarely have... sex, I was not being completely honest. We haven't had sex for... Oh, why am I telling you this? For years now. And I... Oh, I feel so lonely..."
I kissed her again, and at the same time started to open the zipper in the back of her dress. Defeated, she allowed me to open it and let it fall, but then crossed her arms in front of her chest and said, shyly:
"You're... You're so young and fit and I'm... I'm fat... You must think I'm ugly..."
She was a little overwheight... Well, she was a forty-something old woman with two kids and a neglecting husband, it wasn't a surprise! But even so, she was a real sight for a teenage boy: no panties - it was somewhere on the kitchen floor - and large breasts, a plump ass that I still couldn't see but soon would, and without any sex for years.
"You're beautiful. Please, take off your bra for me..."
She smiled and, without looking up, took them off, hesitantly putting her arms to her sides. Her breasts were large, a little saggy, with big, brown areolas and hard nipples just asking to be sucked. No, she wasn't a looker nor a Playboy centerfold (it was the nineties, remember?) but to me, at that point, she was my utmost desire.
I couldn't wait anymore, so I took off my clothes as fast as I could while she watched with hungry eyes and, then, gently pushed her onto her back and over the bed before starting to eagerly suck her tits.
"Ooooh... Oh, yes, like that... Oooh, it's been so long... Like that, my... My boy..."
She calling "my boy" made me even crazier, and if I had a dozen mouths I would have sucked everything at the same time... As I had only one, I took my time sucking one tit, then the other, and then slowly descended to her hairy, inviting pussy that, at that point, was like a river of fluids. Remembering that my cum was probably still there, I stopped short of the pussy itself and started to lick her clitoris while massaging her two tits with my hands, making her go crazy in no time. Laura was soon trashing around the bed, pressing both hands over my head and saying:
"Oh, lick me, my boy... Oh, it's been so, so long... Yes, yes, like this... Ohhh... Oh... I'm going... I'm going to cum agaaaaaaain!!"
She screamed this time, loudly and without any restraints, giving herself completely and making me proud of myself, until after a few moments, her orgasm fading, she let go of my head and said, still catching her breath:
"Daniel... Come here..."
My cock was almost exploding, and I promptly climbed on the bed. She stared at me with glazed eyes and said:
"Come here, over me... Put your legs on either side... Yes, like this..."
She guided me to put my cock between her tits and, using a pillow, put her head in an angle where she could suck the tip at the same time. She then used her hands to get some of the juice from her soaked pussy and spread it over my cock and her tits, finally pressing them together over my cock.