A Tale of Two Sidneys - Cover

A Tale of Two Sidneys

Copyright© 2009 by Ted55

Chapter 4: Just Double Checking

Erotica Sex Story: Chapter 4: Just Double Checking - This is the story of two men; one at the beginning of his sexual life and one closer to the end. Each crosses generational boundaries to fulfill their needs. Not without consequences.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Reluctant   Coercion   Drunk/Drugged   Lesbian   BiSexual   Heterosexual   Slut Wife   Group Sex   Oral Sex   Voyeurism   Big Breasts  

'What have up you been up to!' the question echoed in Julia's head.

She wasn't alarmed that her husband discovered the evidence of her arousal. She knew exactly how to dodge the question and change the subject simultaneously. She took his flaccid member in her hand and said,

"It doesn't look like we're up to too much yet."

Sidney didn't need to look down to acknowledge the sad state of affairs. People not familiar with ED don't understand that it's not a lack of libido or sexual desire; all of those things work fine. It is simply, as the name implies a failure to become erect. Julia played with his squishy soft penis and attempted to get a stroke going but it's difficult to do without the firmness. She resorted to just stimulating the head.

Her touch felt wonderful as it always did. His balls twitched and yearned but his dick firmed up only the tiniest bit. She continued the massage for another few seconds and then with an exaggerated grimace said,

"I'm sorry honey but I missed dinner and now I'm starving ... maybe later," she kissed him on the cheek and exited toward the kitchen.

He was disappointed in himself as he donned a pair of pajama pants. Whenever this happened he always wondered if he'd had his last natural erection. He hadn't gone to any of the ED drugs yet because the thought of priapism scared the life out of him. It wasn't bad enough to take that risk—yet.

'I sure didn't have any trouble getting hard when sweet Melissa was trying to swallow me whole ... and even later at dinner... '

Sid knew that he hadn't gotten a full woody looking at Sophie and stroking Jennifer's ass, but there hadn't been any supporting physical stimulation either. He considered lying down on the bed and seeing if he could get his erectile tissues engorged himself, thinking about little Sophie, or Jenny—maybe both together.

He actually felt that last vision in his cock. it gave a feeble little twitch. He picked up his empty glass and headed for the bar. The decision effectively ensured that his wife's offer of 'later'' wouldn't be tonight.


Sidney Bing was walking to school feeling like a king. It didn't even matter that Missus Brown had treated him like one of her pre-teen sons rather than a lover after she'd fucked him. Now that he'd been relieved of his virginity he felt so grown up.

Was it just yesterday that he'd thought that he was never going to get laid?

Cumming all over Doctor Chapel's wall and floor was embarrassing, but enlightening. It made him realize that he'd been ignoring some magnificent opportunities.

'No more age discrimination ... no sir!'

If a female showed an interest he'd take advantage.

There was still a half an hour before classes started. The school's star quarterback was early because he needed to sort out a glitch in his class schedule. They had him enrolled in Spanish instead of Shop. Not that he wouldn't enjoy learning the sexy language especially from Miz Perez who'd given him a few looks that he now found intriguing, but he saw himself going into engineering and it made sense to develop his hands-on skills first.

"Of course I have room in the garage," Mildred was saying into the phone when he entered the office. "The problem is how do I get it down the stairs?"

She was wearing an expression that Sidney read as frustration. The school's secretary was evidently listening to the person she was speaking to reply when she spied the football player at the counter.

He saw it in her eyes—he now knew that look. Frustration was replaced by something else.

"Look I've got to go," the attractive older woman said into the phone. "Yeah I'll figure something out ... talk to you later."

He'd never noticed before how nicely Missus Stern filled out a sweater. The cream colored ribbed knit material stretched over her rack. The bottom was just above her crotch, or at least where he envisioned it would be under the plaid skirt. She wore a decorative belt on top of the sweater to define her waist. The reaction he'd had to her yesterday came as a surprise which he put down to the Hawaiian disease (Lackanookie) but today he knew better.

'Nothing wrong with that body, ' the adventurous athlete concluded returning to her pretty smiling face.

Mildred felt her nipples tighten and that deep yearning feeling between her legs as she rose and approached the teenaged Adonis.

"Is there anything I can help you with Missus Stern," Sid asked stealing her line.

Mildred got suddenly weak in the knees.

'Oh shit ... he can read my mind!' the absurd thought flashed and was gone.

"Pardon?" the fifty-five year old said, not because she didn't hear, but in order to get clarification.

Correctly interpreting her question he said,

"I couldn't help overhearing what you said on the phone ... about getting something down the stairs. Is it something that you need help with?"

"Well it's just ... uh, you know that my husband passed away last year," she confided.

"Yeah I'm so sorry," Sidney consoled.

"Thank you, but it was a blessing. He'd been sick for over a year. I really want to move on with my life but I have these constant reminders around the house," she explained.

"Don't get me wrong ... I loved him, and I guess in a way I always will but I'm too young to stay in mourning the rest of my life. I need to put the things that bring back the memories everyday out of sight."

The quarterback hoped his face was sufficiently empathetic despite the fact that he was having trouble keeping his eyes off the secretary's chest.

"His dresser is still in the bedroom and it's practically the first thing I see every morning. I'd really like to move it into the garage but it's really heavy," Mildred defined her problem.

"I could do that for you," the muscular young man volunteered.

"Oh I couldn't ask you to do that," she replied feeling a new flush at the thought of his rippling muscles.

"It's not a problem ... last year my mom bought a new fridge and I moved the old one into the basement all by myself, so I'm sure I can handle a dresser."

"A fridge ... all by yourself?" Missus Stern said incredulously as the tightness in her nipples increased and she wondered if they might be showing.

"You've been helping students at this school for how many years?" Sid asked rhetorically. "It's about time at least one of them helped you."

She really did want to get the big oak reminder of her dearly departed out of sight—and what harm could it do?

"Well I really would appreciate it," her reserve cracked.

"I can come over right after practice," the boy offered. "Just give me your address."

Her hand was a little shaky writing on the telephone message pad. The thought of having the young hunk in her house, in her bedroom, made her tingle all over.

Taking the little slip of paper from her he thought, 'I wonder if I can convince her to really show her gratitude.'

With his scheduling glitch easily resolved they parted both trying to keep the evening appointment from ruining their concentration on matters at hand.


Melissa wasn't worried that she was going to be late for work but she did have some misgivings about her sexual orientation. The evening with Vickie was thrilling; so much so that it was disturbing.

It was a shame she had to pull the waitress out of her cozy bed to drive back to pick up her car.

Now back in her apartment changing into work clothes the whole thing was replaying in her mind like a video and a very erotic one at that.

Pulling on her cotton everyday panties she felt the unique sensation in her ass. Up until last night the biggest thing that had ever entered her back door was a finger. The toy Vickie used wasn't large but the beaded latex shaft had left a lasting impression.

They'd pleasured each other for hours, then ordered a pizza and sat on the couch eating, drinking wine and catching up. When they finally went to bed again in the wee hours of the morning, they fell asleep in the sixty-nine position.

Without an alarm clock Melissa was surprised she was able to get up and shower on less than four hours sleep. Vickie didn't have to work until eleven but she'd persuaded the blonde to give up her cozy bed and drive her back to Danny's to get her car.

Out of her apartment and back in the car she sleepily drove to her warehouse job—she was going to be late but she didn't care. Today she would give them notice that she was leaving for other employment.

There was a twinge of trepidation at leaving the familiar behind but it was exciting to be embarking on the career she'd chosen four years ago. She should have been focused on that but all she could think about was what a wonderful evening and night she'd shared with her high school classmate.

'I've got to get Chad over as soon as possible to prove that I haven't completely switched teams, ' she thought as she clocked in forty minutes late.

At lunch time she called her ex-boyfriend and still sometimes 'fuck buddy'. There was a time when she thought their relationship might progress but the handsome artist was just too laidback, too willing to settle. He was content to work at the music store during the day and strum his guitar at night, picking up the odd paying gig. He was talented but he had no drive. Melissa on the other hand saw the possibilities for advancement and growth and was willing to do whatever was necessary to realize them.

There wasn't any doubt in either of their minds where the after work drink would lead.


Standing on the deck drinking coffee Sid was pleased that his headache was nearly gone. Looking beyond the end of his yard to the active little stream that separated his property from the sixteenth tee, he once again noticed how the side of the tee deck was undermined. Eventually the side would cave into the stream if it wasn't shorn up.

He'd mentioned it to Carl Peterson, the Course Superintendent, a couple of weeks ago but nothing had been done. The next board meeting wasn't until the end of the month so he made a mental note to address it with Kevin Rockport.

'Too bad I didn't think of it last night when I joined them for dinner.'

Recalling the meal brought little Sophie's image into his mind. The sensation in his loins was a testament to his desires but the lack of any real engorgement was an indictment of his capacity. There was no sense in being disappointed, it was a fact of life.

Julia barely stirred when he kissed her forehead and left.

On the way to the plant he couldn't help thinking about his new cutting machine programmer. He was wondering if when she started in a couple of weeks, he might get the kind of stimulation that seemed to supercede his erectile challenges.

Wheeling the Benz into his parking space he put the fantastic possibilities out of his mind. He had work to do.


Chad had been there a while when she arrived. It was evident from the dent that he'd put in the pitcher of draft. It didn't take long to catch up. Most weeks they spoke on the phone and she'd seen him a month ago around the time she'd applied for the design job at the Dickens' factory.

When she told him she got the job he sounded sincere in his congratulations but Melissa was hearing some regret as well.

A half an hour later they'd polished off the draft and walked out hand in hand. Despite the fact that Chad was a full head taller than the auburn haired beauty, to a casual observer it would have appeared that she was dragging a little boy. Melissa led and Chad, in tow, was a half a step behind. It certainly wasn't reluctance on his part it was just the way their relationship worked. The little tavern was chosen because it was steps from the graduate fashion designer's apartment.

Alone in the elevator Melissa wrapped her arms around her boy-toy's neck and kissed him suggestively. Pressing her bra and scoop necked T shirt clad breasts into his chest and slithering he body against his. She found herself comparing it to the kiss she'd shared with Vickie. It didn't stand up very well which gave her cause for concern.

Keeping his neck in the crook of her left elbow she reached down to stroke the front of his slacks. The cylindrical firmness she encountered put a warm glow in her pussy, which was encouraging.

Inside her apartment she was once again leading him like a child straight to the bedroom. Releasing his hand once they were inside she stripped quickly. There was nothing sexy about her work clothes or her everyday underwear that merited dwelling on.

Dropping to her knees in front of the laidback musician Melissa unfastened his pants and pulled them down along with his underwear with a swift and purposeful jerk. Chad at least took the initiative to pull his shirt over his head. The warm glow between her legs began to tingle at the appearance of his hard cock.

Pulling his hot veiny shaft from its nearly vertical position to horizontal the naked kneeling young woman engulfed the head and began to suck. Her fuck buddy spread his feet wider as she cradled his sack and rolled his heavy nuts around. It felt as though she was trying to suck his balls out through the end of his dick.

The salty hardness in her mouth was familiar and the tingle in her cunt began to pulsate. A moan escaped when Chad reached down and began pulling and twisting her tender nipples.

As he was cupping and squeezing her firm cones Melissa couldn't help weighing the erotic stimulation of his big guitar playing calloused hands against the Vickie's soft little ones. It was very different but seemed to be equally effective.

A moment later he was pulling her to her feet, hugging and kissing as they danced toward her bed. The hard hairiness of his chest contrasted with her memory of her girlfriend's smooth squishy boobs. Falling on the bed she pulled her lover on top of her. The need to have his hot hardness inside had reached an unbearable level.

Chad created separation by straightening his arms on either side of her. She reached between them and wiped his manhood up and down her flooded crease twice before centering him on her opening. Her lower lips wrapped around his stiff cock much the way her mouth had a couple of minutes ago. She heard his sigh as he pushed into her hot depths. Her vaginal muscles tightened on the invader and a big wave of pure pleasure swamped her. There was no comparison to the rubber toy Vickie had penetrated her with, even though it was much bigger.

'Ain't nothin' like the real thing baby... '

She picked up his steady, fairly slow rhythm, thrusting up into his down strokes and twisting her hips as he withdrew. The inward push pulled her labia with it bringing her clit into tantalizingly brief contact with his bumpy upper shaft. As the pace increased so did the depth of his strokes and the pressure on her love button. It was like a cymbal crash superimposed over the steady beat of his fullness sliding in and out of her.

When it came it seemed very sudden. One second she was just enjoying the stuffed feeling punctuated by intermittent thrills and the next she was completely overcome, swamped by a mind blowing explosion.

In the midst of her ecstasy she could feel how hard her clenched pussy had clamped down on his cock and then she felt his spasms begin which seemed to take her even further into the delirium. His weight pressing down on her as he collapsed actually felt good—reassuring somehow.

They lay there both twitching and moaning for a few seconds before he rolled off and lay beside her.

As the post orgasmic bliss began to subside she was thinking,

'Well that proves that I'm not a lesbian ... doesn't it?'

'Maybe I should try it one more time ... just to be sure... '


The quarterback wasn't normally the first one showered and dressed after practice, but today he had a reason to hurry.

He'd already stowed all his books in his locker hoping there wouldn't be time for any homework tonight. Once he crammed his pads into his athletic locker he was on his way to Missus Stern's house to move the dresser. If his reward was to be milk and cookies he hoped they were the kind you ate in bed, not at the kitchen table.

Unlocking his bicycle gave him a twinge of shame. He'd saved nearly enough for a car but he couldn't touch it until his college expenses were assured. The savings from his road construction job the last two years might be needed to supplement the fund his mom and dad had tucked away. He knew that he'd attracted the attention of some scouts last year, particularly in the Championship game. If he could just play well enough this year to get a scholarship then he'd be able to get some wheels. In the meantime it was two wheels and leg power. Day dreaming about his college scholarship opportunities he almost missed the turn onto the school secretary's street.

His prurient reason for offering his services to move furniture was forced way to the back of his mind until she opened the door.

"Oh I wasn't expecting you quite so soon," Mildred said standing in her silk dressing gown surrounded by the alluring fragrance of her bubble bath.

Sid's eyes went automatically to her chest and saw the unmistakable evidence of erect nipples poking against the thin green material. His package responded with a thrilling twitch and he forced his eyes back up to the older woman's face.

'Do all these old dollies have housecoats like that?' he wondered, recalling the session with his neighbor.

"I came over right after practice ... is it too early?" the quarterback explained noticing the cryptic smile of the secretary's full lips.

"No ... No it's fine I just haven't had a chance to get dressed," she lied holding the door open wide.

"Come on in," she invited. "I always find a nice hot bath after work relaxes me and makes me feel ready for the evening."

Sidney entered the immaculate home and the very feminine scent grew much stronger. The teenager couldn't help wondering what she needed to be ready for.

"Follow me, and I'll show you where the dresser is," she said turning toward the stairs.

"I really appreciate this," she said gratefully over her shoulder.

The back view wasn't bad either. He noticed how the tightly synched gown clung to and accentuated the rise of a surprisingly firm looking butt. The tightening sensation between his legs was premature.

"I took everything out including the drawers to make it lighter," she informed standing beside the heavy oak frame.

Sid scanned the five foot high piece of furniture for a second but his eyes drifted over to the school secretary's frame of their own accord. At the door when he arrived he'd noticed her nipples but they'd grown—a lot! The projections in the green silk that molded to her breasts now looked as long as the first joint of his baby finger. He knew that he shouldn't be staring at her chest but he was powerless to take his eyes off the inadvertent display of her charms.

Mildred was only too well aware of her condition. Her nips had begun to tingle and itch the moment she'd heard the door bell. Now they were positively buzzing as if each one contained a large bumble bee, and they were about the right size to do that. She couldn't miss where the football player's gaze was fixed and his attention agitated the bees.

"Oh my..." she sighed crossing her arms over her boobs.

"I'm really not used to having handsome young men in my bedroom, and I should never be receiving visitors dressed this way ... this is quite embarrassing!"

Sid found her shamed blush added to his excitement.

"There's no need for you to be embarrassed," he consoled.

"You have a beautiful body, and you should be proud of it," the grid-iron hero complimented happy that he had skipped the phrase, 'for your age.'

"Oh God but I'm so old ... do you really think so?" she jumped from the deprecating remark to the request for reassurance with barely a pause.

"Well it's not as if I've actually seen your body..." the teenaged athlete qualified, now blushing himself. "From what I've—"

"Would you like to?" Mildred interjected lowering her hands to the neatly tied sash.

She was amazed at how bold she'd become as the wave of excitement caused all of her nerve endings to tingle.

Sid's dick jumped and, if he hadn't been here before, he thought he would have probably dropped the ball. The pass was right in his hands—all he had to do was squeeze it.

"Yes... yes I would," he replied emphatically surprising himself with the confidence in his voice.

Mildred hesitated a moment fingering the knot.

'There's still time to turn around ... there's no harm done yet, but if I—'

Her fingers were operating without full authority unfastening the only thing holding her gown closed. The turmoil in her brain caused by her conservative persona was battling her sexual desires but seemed to have released muscle control to her baser more primal instincts.

Not only did she release the sash but she pulled the sides of the silk dressing gown open fully revealing her underlying nakedness. The similarity of the sensual rush that passed through both of them was ironic.

Sidney's dick surged against his confining clothes and electric like pulses invaded Mildred's pussy. The pure lust in the teenager's eyes amplified the older woman's arousal.

Her breasts weren't as big as Missus Brown's but middle age caused them to droop more. His eyes focused on the amazing long red dugs poking out of the smallish areolas. His cock jerked again and he quickly scanned down to her full 'V' shaped bush.

'Oh my god it's unbelievable how easy older women are!'

'I've been trying to get into my girlfriend's pants for over two years and never even got a peek ... the doctor woke me up to the possibilities ... now I feel like a kid in a candy store after hours.'

Tentatively he reached out to touch the school secretary's tits. His hands were moving too slowly so Mildred grabbed them and mashed them against her breasts. Holding the slightly floppy boobs he gingerly thumbed her nipples which felt even bigger than they looked.

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