Helping The Neighbors

It was a Saturday morning and Andy Ransome had a full schedule planned for himself. He grinned at himself in the mirror and mouthed the words: 'The Widows' Club'.

Andy, though still in his teens certainly looked older, at least as though he were college age. He was a big kid, fair haired, like his Mom, Cynthia and also well developed. His adventures with 'the Widows' Club' actually began quite by accident.

There is also one thing about Andy's 'well developed' physical characteristics that was important in his getting involved with this group of women, he was also 'well developed' in his private parts.

(It's just as Kurt Vonnegut said: "You never know who'll get one!")

Well, the truth was that Andy had indeed 'gotten one'. Measurements might be neither her nor there in such a tale as this, though it is usual protocol to mention the figures of the women involved, but Andy sported a good six inch soft penis and when erect it went to better than nine inches and several inches around. So, Kurt Vonnegut would certainly have approved in this case.

The members of 'the Widows' Club' included Andy's Mom, Cynthia, Megan Rooney, and Lily Wooly. They had been, these three ladies, friends almost forever and only became the newly christened 'Widows Club', as their husbands, one after another did indeed pass on. They got together each time a death occurred to be a help to one another and finally, when it was Merv Rooney who died, they became socially inseparable. They played cards together, shopped together, went out for 'girls' nights' together, and had their gigglefests when comparing the sexual inadequacies of their deceased husbands.

Meg Rooney: The Beginning

It was a casual comment from Meg Rooney that actually got Andy involved with them. She was commenting about things that needed doing around the house, when the three of them were together for drinks, and Cindy Ransome offered to have Andy go to her house to see if he could help.

The suggestion was immediately accepted. Among the three of them, Andy was the only child and they all had watched him grow and loved him almost as their own. When Megan accepted the possibility of Andy helping her, both Lily chimed in that she might need his help also.

The stage was set.

Andy was, at that point in his life, in the 'perpetually erect' state that teens go through. It seemed that just about anything and everything would give him a stiffy. He also, from listening to friends, to chatter etc, was aware of his special endowment. But it was his day of aiding Megan Rooney that really started his work helping 'the Widows' Club.'

As his Mom had promised, Andy went to Megan Rooney's to help out. She greeted him with a hug, thanking him profusely for being there. One of the tasks that she had involved getting items down from a high storage area. She had Andy get the ladder out and, at first, went up herself to see about what was stored there.

Almost as soon as she got up the ladder and started to mess around, the stuff in the storage cabinet began to shift.

"Oh dear!" she yelled, and Andy moved up the ladder quickly behind her, as she continued to hold onto the stuff.

On the ladder, as he straightened out the stuff in the cabinet, he was behind Megan and was pressing against her ass.

Of course, he got an erection. He was afraid it was going to happen. Once the stuff in the cabinet was okay, he could feel the softness of her ass beneath him on the ladder and he was erect in no time. What was more, he was sure that, unless she had no sense of feel at all in her butt, she felt his erection poking into her ass also.

He moved off of the ladder as quickly as possible and began his apology:

"Mrs Rooney," he said, red faced and chagrined, "I'm..."

That's as far as he got.

Megan Rooney not only felt his erection poking against her ass cheeks, she also realized how big it was, and she was, for a few seconds, dumb founded. What she did next was produced in her by sheer instinct, without the benefit of thought or any kind of reason.

"Andy, honey," she cooed, as she cut his apology off by planting her lips against his.

He was wide eyed at first but realized quickly what was happening, when she reached between them and grabbed hold of his erection through his shorts.

"Holy shit!" she said, "Darlin', this is all you?"

"Yes, uh, Ma'am," he said, gaining a bit of confidence slowly and then Megan went into further action. She unbuttoned his shorts and had them down and off in a twinkle, followed by his underwear.

Then she saw the magnificence of his erection and before he could do anything or think any further, Megan Rooney, cooing and making throat noises, was on her knees and had his huge dick in her mouth.

He got weak at the knees immediately but a thought crossed his mind and he acted on it. It was, in truth, the beginning for Andy.

"Mrs Rooney," he said, almost desperately. "Stop."

She looked at him and misunderstood what he wanted.

"I'm sorry, honey," she said, "I don't know what came over me."

"No," he said, still panting. "Take your clothes off."

She grinned at him. "You wonderful, bad boy!" she said. "Have you ever seen a naked woman?"

"No!" he said, looking down at her, still in her kneeling position; then changed that to 'Only on the internet!"

"Ah, yes, the modern version of the 'Playboy' experience! Not even your Momma?" she asked, getting up now.

"No," he said.

"Boy," she said, "She'd be a treat to see!"

His response was just to grin.

"I see that you know what I mean!"

"You just sit here and let me do as I'm told!" she said then, as he looked on and grinned like a fool

He grinned then, surprised and happy about how easy this had been.

She pulled her tee shirt up and off, discarding it, and then her jeans were pushed down and she stepped out of them. She put her hands up in the air then and turned in a circle for him, wearing her matching yellow panties and bra.

"Ohhhh," he said.

"Gets better!" she said, "Watch!"

The bra went next and then the panties, and Meg Rooney, his Mom's friend, member of their "Widow's Club" was there and naked. He stared, only stared, until she moved and knelt in front of him, taking his cock head into her mouth.

Andy's first conquest of a 'Widows' Club' member had begun.

Meg taught him and was ecstatic with the way he learned to make love.

Meg became a regular for Andy, especially on saturdays.

Lily Wooly: The Perfect Submissive

Andy was on top of the world, when he went on to Mrs Wooly's to do her Saturday work. He was grinning; he was whistling; he'd just gotten laid and Meg had told him that fucking her would be an 'any time he wanted it' kind of adventure. Andy's feet were just barely touching the ground.

That maybe accounts for what he did at Mrs Wooly's, where he got the courage. In fact, truth to be told, he did what he did without even thinking, and it was his run of luck that it turned out so well.

They were in the basement and she wanted to have some stuff cleaned out and sorted.

"Here," she said, "Let me get in here and get these things out."

Lily was wearing a pair of white capris, heeled sandals, and a white tee. Then she bent over and he saw that she was wearing a pair of somewhat darker colored panties.

He couldn't take his eyes off of her ass, shoved up in the air, as it was.

Before he could even think about doing it, as a matter of fact, if he'd thought about it at all, he never would have done it. He slapped her ass.

For him it wasn't an unnatural response. At home, it was one of his games with his Mom to slap her butt now and again, and he came fresh from the conquest of Meg Rooney.

"Mrs. Wooly," he stammered.

He'd realized too late what he'd done, and was ashen faced. Without hesitating but mumbling an apology, he headed for the door and was quickly out on the porch cursing himself roundly.

Lily, for her part, squealed, as soon as her ass was slapped and stood facing him, watching him, with a painful look on her face, head for the door. She moved to the door quickly, and said: "Andy!"

He turned at that point and saw the look on her face. It was somewhere between pain and dreadful longing.

Andy understood in a second! His chagrin turned to a smile, and he went out on a limb: "You like that!"

"Yes," she said quietly.

There was a silence. She broke it: "No one's done that to me in ever so long a time!"

Andy was in charge again. He confidence came surging back, as soon as she said what she said.

He grinned at her, as she kind of danced from one foot to another and waited.

He moved back to the doorway, where she was waiting. She positively launched herself at him for a kiss, as soon as the door was closed. While they kissed and she ground her hips against him, trying to feel the growth of his erection, he grabbed her ass cheeks in his hand.

"Oh, yes," she said.

"Turn, bend!" he said, and was super pleased that she did as he'd ordered, for there was Lily Wooly bending from the waist and looking back at him.

He slapped her ass, hard. She winced and wiggled her ass around a little until he slapped it again.

With confidence he said: "Take your pants off."

She hesitated then, as if weighing whether to do it or not.

"Damn it, woman, do as your told!" he shouted.

This moved her into action and she stood in her rose colored panties almost immediately.

"Tee shirt off!" he barked and she didn't hesitate this time.

Now he had Lily, his Mom's friend, Lily Wooly, a true fox if there ever was one, standing before him wearing only her panties and bra! It was grand and beyond grand!

"You like this, don't you, I mean all of this, not only the spanking?" he asked in a soft voice.

"Yes," she said, her voice tentative and tiny.

He smiled at her.

"Lose the bra," he said.

"Yes, uh, sir," she answered and took her bra off, setting her magnificent breasts free.

He stared for a bit; it seemed to make her nervous.

"You like being spanked?" he asked. Then he added: "Lily, don't lie to me!"

"No, I wouldn't," she said earnestly and then shook her head, saying: "Yes, I do, I like being spanked. George never would; he didn't like what I liked."

"Good," he said, "Get me something to spank you with!"

"Ohhh," she moaned and went right away to fetch something. She came back pretty quickly and was holding a wooden paddle.

"I bought it once but it never got used..." she began.

"Until now," he interrupted.

"Oh, yes," she said, "Until now!"

"Here's how it'll be," Andy said, now totally in charge. "First ten with your panties on and the next ten with your panties off. Any questions?"

"No, I just want to thank you for this," she said.

"Turn, bend!" he said, "Give me a target!"

She did as she was told. The sound of the paddle hitting Lily's lovely ass filled the room. She made inarticulate cries with each stroke of the paddle. Andy started light and warmed up to the task, ending the first ten with hard strokes, which had Lily crying out and beginning to blubber.

"Shall I stop?" he asked.

"Oh, no, sir!" she said, "You said ten without my panties."

"Yes, I did," he replied and told her to take the panties off.

She did and showed that her ass cheeks were getting very red.

"Position!" he said and she bent from the waist again, grabbing her ankles, and giving him a major target.

His next ten were hard and she was crying at the end but when he was finished, she launched herself at him, and into his arms and was kissing him fervently.

"It's anything you want!" she rasped, "Anything you want for treating me so nicely! Anything!"

Andy was on top of the world, that afternoon making love to the second of his Mom's friends, and getting a blow job from Lily Wooly to finish him off.

The Real Target

Andy made handsome progress with the women of the Widows' Club. Megan and Lily were on his weekly schedule, and their compliance was giving him a great deal of confidence. He finally, after a few weeks, decided that he was ready for the real target. He himself knew that the others were only practice runs, trials, the gathering of skills. His real target all along was his mother, Cynthia.

Cynthia and Andy had lived alone together for a long time, since the early brake up of the marriage with what had been her teen aged sweetheart, who had simply gone away and never came back. Cynthia divorced him for abandonment after a few years. It had always been Cynthia and Andy.

They were, especially she was, rather lax over the years about dress codes, and Andy grew with indelible images of his mother in her underwear impressed on his brain.

It was she, Cynthia, his mother that he wanted most of all, and it was the successes, beginning with the eager Meg, and continuing with the submissive and totally complaint Lily that gave him the confidence to go on with a plan that he'd hatched.

It was a Saturday, when it finally began. Cynthia was a nurse, an ER nurse, and very good at her job. When Andy returned from his 'rounds' with the ladies that morning, he was determined to put his plan into action.

"Mom," he said, as he entered the house.

"There's my man!" she said with a grin, hugging him.

He started to get an erection as soon as they hugged and backed away quickly:

"I'm sweaty!" he said.

She laughed: "Maybe I like sweaty!"

They both giggled at that.

"I hurt my thigh," he said, "Working over at Ms Rooney's."

"Oh," she said, "Okay, you take your shower and then I'll look at it."

He went and showered and then called her. He lay down on the bed in his room and covered his nakedness with a sheet. He was as stiff as he ever remembered being. His full nine inches were rampant, though he was a bit nervous about success.

Cynthia came into the room.

"Okay, let me see, sport," she said.

She went to where the sheet was covering him.

"Which one?" she asked.

"The right one," he said, making it necessary for her to take the sheet off.

"Mom!" he said, bringing concern into his voice.

"Andy Ransome," she said, "There's nothing that you have that I haven't already seen any number of times! I used to bath you naked, as a baby."

"Yes, Ma'am," he said, "Just no foolin' around!"

They both giggled at that and Cynthia moved the sheet and gasped. There was a long silence. She stared at him, at his large erection and he watched her with a smile.

"Ohhhhhhh!" she managed, "Andy! I had no ... no idea!"

He was still smiling at her. But what she did next, before she was even thinking about it, showed him that his plan was certainly going to work: She took his huge erection in her hand, and held it between her fingers.

Andy knew it was time to act. He reached out and grabbed the back of her head and began to move it toward his erection.

Her initial response was to say "NO!" but he noticed that she didn't resist the pressure of his hand on the back of her head.

Her next 'no' came, when her lips touched the head of his erection. Andy was smiling.

"Open your mouth, Mom!" he said.

Her next, and final, 'no' came when she obeyed his command, opened her mouth and began to take the huge head into her mouth.

He had her! He was ecstatic! Elated! Walking on air!

"Mom," he said, and she looked up at him, his enormous cock head filling her mouth, "Suck my cock!"

She mumbled but he insisted that she be clear: "Take it out of your mouth, Mom, and say it to me. Now!"

She obeyed. Cynthia Ransome was a gonner almost as soon as she spied the gigantic erection that Andy was sporting. She held onto his cock and then took it out of her mouth and said: "I'm going to suck your cock, Andy, my Andy."

"On the floor," he ordered, "Kneeling! I want you kneeling."

She moved and did his bidding, ending up on her knees on the floor. She had no will of her own left. Andy knew that. He went to her, smiling, and sure of himself. She looked on almost like a trapped but happy animal.

He surprised her then by hauling her tee shirt up and off.

"Ohhhhhh!" she said, as her bra went next. "Andy!"

She didn't say anything else. Then he had her up and was taking her jeans down and off. He left her wearing a pair of pale, beige bikini panties, and then he pushed on her shoulder and got her on her knees, where he wanted her.

Cynthia struggled, she gagged, she drooled but she got a good portion of his cock into her mouth; she did indeed suck his cock. Her mind, it seemed, was in 'neutral'. She'd never seen Andy this way. She'd never seen him in his 'in charge' mode, although her friends in the 'Widows Club' could have told her about him in that kind of mood but she didn't know that yet.