Jimmy was eighteen years old, currently studying photography and film-making.  He owned all the best equipment, from top of the range cameras to video editing software for his laptop.  All funded by his loving, and supportive single mother, Alice.

Alice had gone to town for the day, leaving Jimmy alone in their beautiful home of a small residential neighborhood.  Jimmy had the day off, leaving himself to lounge around the house, listening to music, playing video games, among other things.

Jimmy started to get a bit bored, so made his way to his bedroom.  Sitting on his bed, he pondered what to do with himself.  It was too early to sleep, and besides, he wasn't tired. He did have an idea what could make him a little drowsy though.

He stepped to his wardrobe, reaching to the top shelf, shuffled some items aside and pulled out a magazine titled 'Mature Women' he kept hidden from his mother. He put on some music in the background, before stretching out upon the comfy mattress and started to scan through the magazine. 

Photos inside contained sexual poses of mature women, exposing every inch of their various shapes and sizes.  Jimmy thought how great it would be to be one of these photographers, taking pictures of all these naked women.

As Jimmy continued flicking through the pages of the magazine, he felt his cock begin to harden.  One hand found itself settling upon the crotch of his jeans, where he gave a gentle squeeze, before rubbing across the growing snake that slithered beneath his clothing.

His expanding cock was doing its best to grab his attention, and becoming unbearable.  The sight of these beautiful mature women had aroused him to the point that he felt he had to deal with his growing issue.

He shifted his attention from the magazine to unfastening his jeans, sliding them down his legs, along with his boxer shorts.

His erect cock sprung into action, as if breaking free from its locked cage.  It bounced around in the cool air, performing its victory dance of escaping and roaming free.

His cock was a healthy six inches in length, sometimes a little more on a good day.  Jimmy wrapped his fingers around his erect cock.  The tips of his fingers and thumb just about found each other, due to the girth of his growing cock.

He peeled back the foreskin, exposing the swollen glans of his engorged head. His frenulum still connected his foreskin to his swollen head. An uncut cock.

He turned the page of the magazine, where he stared upon a photograph of a brunette with hanging breasts and large erect nipples that you could hang your hat on.  She was sat upon a chair, legs spread wide, exposing the soft pink flesh of her glistening wet pussy.

Jimmy began stroking himself.  His hand wrapped firmly around the foreskin of his long, thick shaft.  He began jerking himself off, slowly at first.  Up and down, feeling the slight throbbing of his cock beneath his fingers as he stared at the naked pictures.

Unfortunately, Jimmy had forgotten to lock the back door, when a next-door neighbor and his mother's best friend, Chloe, had decided was a good time to pop around to see Alice.  Chloe called to Alice but failed to get a response.  She knew someone was home, as the door was unlocked, so went in to investigate.

Chloe was in her early forties and had blue eyes, a sweet smile, long brunette hair, a voluptuous figure with large breasts and a sweet derriere that shook with every step of her long, shapely pins.

Stepping into the lounge, she called out again, but no response.  She could hear the faint sound of music from upstairs.  She presumed it was probably Jimmy, Alice's son, who she had known for many years now.

She arrived at the top of the stairway, looking down the corridor to see one of the doors ajar, and music erupting from within the room.  She stepped down the hallway, stopping outside the door as she peeked inside.

Her jaw dropped, as she covered her mouth with her hand. Her eyes boggled at the sight before her.  She could see Jimmy, upon the bed, facing away.  His pants were around his ankles, with one hand jerking off his large, erect cock.  Chloe was agape at what she saw.

Chloe stepped to the side, as she tried to regain her composure.  Her instinct told her to go quietly downstairs and leave the house.  Unfortunately, a voice in her head kept nagging away, telling her to take another look at this strapping young man jerking off.

Chloe hadn't been with anyone for a while, since her last husband cheated on her, running away with a woman half her age.  She turned to the door and took another peek through the gap. She smiled, almost let out a soft whisper of a giggle to herself, at what she was looking at.

She couldn't believe she was watching Jimmy, of all people, masturbating.  She'd known him for years and never thought of him in such a way before. 

Chloe bit her bottom lip.  Watching Jimmy jerking off was beginning to cause her own body to react. Her eyes couldn't turn away from Jimmy's thick, large, erect cock. It looked so hot, that she wondered what it would be like to suck it, or even better, ride Jimmy and make him explode inside her.

Her hand slipped across her large bosoms, hugged tightly beneath her tight top and bra.  She began rubbing her fingers over her nipples, circling around the sensitive areolas.  She was growing more aroused by the minute.

Her hand slipped under her top, where it grasped one of her heavy breasts, squeezing it over and over.  Her other hand slipped over her stomach, towards the hem of her skirt.  Her fingers dipped under the garment, as her hand soon disappeared beneath.

One hand continued to play with her large breasts, squeezing and rubbing her sensitive areolas.  Her other hand found its place to her panties. Her fingers started to rub her crotch, sliding back and forth, causing friction upon her glowing pussy.  She could feel herself getting warmer, and definitely wetter, as she continued to watch Jimmy masturbate.

Jimmy was still stroking away at his uncut cock, unaware that Chloe was watching him from outside his bedroom, pleasuring herself at his expense.  Jimmy stopped suddenly, as Chloe froze. Did he know she was there?

Jimmy leaned forward and turned over, still facing away from the doorway.  He placed the magazine at the far end of the bed, where he grabbed his pillow from the other end.

He squeezed the pillow, so it became long and thinner. He placed it under his body, sliding it beneath his crotch.  A section of it rested between his upper thighs, which he squeezed against the pillow to hold firmly in place.

He began to gently thrust upon the pillow as if fucking someone missionary style. His hard cock rubbed against the soft pillow with each gentle thrust of his hips, accompanied by several gentle groans. The slight friction of his cock, more so his engorged head, sliding back and forth over the pillow appeared to please Jimmy.

Chloe watched in astonishment, as she saw Jimmy's tight little ass cheeks flap up and down, thrusting his hips in a fucking motion of making love to his pillow.  She returned to satisfying her own sexual desires.  Her hand returned to rubbing her breast, while her other rubbed against the fabric of her panties, which by now had grown a slight wet patch from her pussy.

Chloe watched, touching herself, as her face expressed the sexual gratification she was experiencing.  Watching Jimmy hump his pillow, imagining him on top of her, pounding his hard cock deep inside her warm, wet cunt.

She bit her bottom lip, as soft groans slipped through her lips.  Her breathing grew heavier, shorter. Chloe was about to explode; she could feel her body rise in temperature. Her hand pulled from her breasts to cover her mouth, as her other hand rubbed harder upon her panties.

Her body exploded into a fever pitch of electricity.  Her legs turned to jelly, butterflies fluttered in her stomach, while her pussy had now soaked her panties.  Her groans and gasps were held in, thanks to her hand over her mouth.

Finally, she came down from her high, beads of sweat upon her pretty face. Her breathing, while still a little heavier, began to return to normal after a moment.  She pulled her hand from beneath her skirt, where she could see the wetness that had coated her fingers. She dipped her fingers inside her mouth, tasting her own juices, before taking time to compose herself.

Jimmy continued thrusting away at his pillow, bouncing his body on the mattress.  His hips bucked as if fucking a girl.  His ass cheeks glistened from the sweat of his actions.  He was still unaware that Chloe had just had an orgasm outside his bedroom door.

Jimmy was rocking away when he was about to get the surprise of his life.

"Hey, Jimmy, I was wondering if ...!" Chloe called out, as she entered Jimmy's bedroom, pushing the door wider and stepping inside.

"Oh fuck!" Jimmy bellowed as he turned sharply upon his bed, knocking the magazine onto the floor. He grabbed the pillow he was fucking, and quickly covered his hard, erect cock.  His face was bright red, as he looked across to Chloe who had stopped dead.

"Oh my!" Chloe gasped as she covered her mouth with her hand at the sight before her, doing her best performance that deserved an Oscar.  "Oh God, oh I'm sorry, Jimmy; I was just looking for your mother.  I didn't know you were, well ..." Chloe spoke in her best 'surprised' voice.

"She's gone out shopping for the day!" Jimmy spurted out, through his embarrassed look.  He didn't know where to look, or how to act at being caught in his predicament.

"Okay, maybe I should go then!" Chloe stated as she turned to leave.

"No, stop!" Jimmy called out, causing Chloe to stop in her tracks and turn back.  "I mean.  You're not gonna tell my mom about this, are you? She'd probably freak out!" he said, looking deeply worried and concerned about his behavior, while still covering his hardened cock with his pillow.

"There's nothing to be embarrassed about, Jimmy; everyone masturbates," Chloe informed Jimmy, although it didn't appear to ease his tensions.

"Please, she'd be so embarrassed to be around you again if she knew. It'd be all my fault!" Jimmy spoke, rubbing the side of his head, showing worry.

Chloe stepped further into the room, closer to the bed.  Jimmy was truly nervous, almost shaking in his skin.  Chloe grabbed his computer chair, wheeled it across from his desk and placed it near the bed, where she sat down upon it.

"It's perfectly natural for young men your age to be experimenting," she spoke, as her eyes took notice of the magazine on the floor.  "What kind of thing are you masturbating over?" she asked, as she reached down and picked up the magazine.

Chloe was a little taken back as she looked at the front page - especially the title,  'Mature Women' - which showed several pictures of women over the age of forty on display.  She opened it up to explore several of the pages within, showing women exposing their naked bodies for all to see, leaving nothing to the imagination.

"So, you like the older women, do you, Jimmy?" she asked, with a glint of a wicked smile.

Jimmy didn't know how to react. His insides were running around like someone had lit some TNT and everyone was trying to find the quickest way to escape.

"Some beautiful women in this magazine!" Chloe informed Jimmy.

Jimmy was surprised at her words.  Was Chloe a lesbian? he thought to himself. He'd never seen her with a man, only hanging around his mother a lot. Wait; she and his mother couldn't be ... no, surely not? The thought made him feel a little ill, more at the thought of his naked mother.

"You know, I used to do a bit of modeling when I was younger," she added.

Jimmy never saw her as a model, although he did think she was pretty enough.  He also thought she was still quite pretty, and that she appeared to be comfortable in her body, judging by the types of clothing she often wore. Short skirts. Loose blouses showing off her deep cleavage.

"I tell you what ..." Chloe began to say, as she closed the magazine and placed it down again, "... it's been a while since I've seen a guy do what you're doing.  If you finish what you started, then I'll not tell your mother about what happened today!" she finished.

Jimmy's eyes widened; his jaw dropped.  "You mean, you want me to  ..." he began to say, yet was unable to finish the sentence due to his complete shock at what she appeared to be asking of him.

"Yes, Jimmy.  If you let me watch you jerk off, then I'll not tell your mother. Do we have a deal?" she asked him.

A cold silence filled the room.  Jimmy was conflicted.  While he didn't want his mother to know what went down, he didn't know if he could jerk off in front of Chloe.

"I don't know if I can.  I mean, I've never ... done it before in front of anyone!" he told her.

"You won't know unless you try.  Besides, I've already seen your cock when I walked in, and if you want to know a secret, you have a nice cock, Jimmy," she informed him.  "Don't be scared of showing it to me," she added.

Hearing Chloe tell him that she liked his cock aroused him so much that he could feel his cock brushing against the pillow pressed against it. It was doing its best to pull away and seek attention from the one who said it was nice.

A little reluctantly, yet with some excitement rushing through his body, Jimmy began to pull the pillow away from his body.  His cock sprang back into action as he sat there on the bed, standing to attention like the good soldier he was, still fully erect and rock hard.  His engorged head glistened at the pre-cum that had seeped out.

"Wow, you have a really beautiful cock, Jimmy," Chloe told him, trying to offer some comfort and reassurance that what was happening wasn't wrong in any form.

"Thank you!" Jimmy heard himself say to her, without even thinking of saying it.

"Why don't you lay back on the bed, and start stroking yourself for me.  I'd really like to see that, Jimmy!" Chloe said, with a slight eagerness to her sultry voice.

Jimmy, anxiously, moved his pillow to the end as he turned and rested back upon his bed.  Staring up at the ceiling, his hand moved across to his erect cock as he wrapped his fingers around the thick shaft.  He slowly, yet finally began to stroke himself off.  He was already half-way there, despite being interrupted.

Chloe watched with eager eyes, despite already watching him masturbate from outside his bedroom; this time, she got a front-row seat to the performance.  She licked her lips at what she saw.  This strapping young man, stroking his hard cock for her. She knew she had control over him, and could possibly make him do anything he wanted her to.

"You see, Jimmy?  I told you it would be okay.  I bet it feels nice to have a woman watch you masturbate?" Chloe asked.

"It's kind of weird, a little, but I guess it feels nice," he replied.

"Have you ever thought of me when you jerked off?" she started saying, "It's okay if you have; I don't mind.  It kind of makes me feel special," she finished saying.

Jimmy was unsure of how to respond.  Was this a trick question to catch him out, about what a perverted young man he was?  Still, he answered her question.

"Hmm, I have a couple of times, yes.  I'm sorry!" he uttered.

"Mmm, I bet you really enjoyed the idea of seeing me naked, didn't you?" she continued on.

"Kind of, yes!" he snapped back.

"Let me tell you, I look so much better than the girls in this magazine.  Maybe one day, I'll show you for real," she said with a smile.

Jimmy's eyes lit up at the thought.  Was Chloe trying to seduce him? He didn't know, as he'd never been seduced before, or been with a woman, for the matter of fact. He was still a virgin and very inexperienced around women.

"Stroke that big hard cock a little faster for me, sweetie!" Chloe spoke, in her soft, sultry tone.

Jimmy picked up his pace a little.  His hand bounced up and down faster, grasping the thick shaft tighter.  He could feel himself drawing closer to the point of no return.  His breathing grew heavier.

"You're getting close, aren't you, sweetie? I can tell by your reactions," Chloe spoke.  "Go faster for me. I want to watch you cum for me, Jimmy!" she said.

Jimmy did as she asked, shifting to another speed.  His hand stroked and jerked his thick, hard cock.  His hips bucked a little.  His cock thrust between the grasp of his hold, where his knuckles rubbed against the underside of his swollen head.

"Cum for me, Jimmy.  Give me all that sticky seed you have," Chloe told him, urging him to explode for her so she could see him cum.

"Oh fuck!" Jimmy gasped out as his body began to shake.  His hips bucked hard.  His cock forced its way through the tight grasp of his grip.  His engorged head swelled tighter, glistening in the light shining through the window.

"Oh wow!" Chloe gasped as she saw Jimmy begin to cum for her.

Jimmy's body quivered as a wave of thick, white, salty cum spewed from the slit of his swollen glans.  It flew an inch or more into the air, before splashing down upon his body.  Jimmy's face spoke volumes: his eyes tightly closed, his mouth agape, almost gasping for air into his lungs.

His hips bucked again, and again, accompanied with a second stringy stream of warm, sticky substance, followed by a third, but not as long, white mess ejaculating from his hard cock.

It began to drip down his erect cock, slipping across the hand wrapped tightly around his thick shaft.  Some formed a small pool of white seed at the base of his cock, dripping over his swelling ball sack.

Jimmy tried to regain his breath, finally opening his eyes to come to the realization of what just happened. He had just masturbated and cum in front of a woman.  He felt a slight glow of accomplishment at his achievement, while a sense of dread also hit him.

"That was wonderful, Jimmy. I didn't know you were so good at it," Chloe said as she rose from her seat and approached Jimmy.

Jimmy couldn't move; his body was spent. His legs felt like jelly; his insides felt like they were running around in circles. His body was sticky and sweaty. All he could do was lie silently and see what Chloe did.

Chloe stopped at the side of his bed, where she leaned forward. She brushed a piece of hair from his sweaty head and gave him a soft peck of a kiss upon his forehead.  "Let's do this again sometime, sweetie," she said, before stepping away.

Jimmy turned his head to watch her leave. His anxiety picked up again. He grew worried, yet a little exhilarated at what just transpired.

"Don't worry, Jimmy.  Your secret is safe with me!" she called back, leaving the room.

Was that it?  Or was there more to cum?! he thought to himself.
 

To be continued ...