Marty’s Day With the New Neighbor

Guided Masturbation Stories

Marty’s Day With the New Neighbor

from the net, circa 2000. Teenage boy spanked by a neighbor girl till he squirts.

Marty was a rather young and protected 17 year old, primarily due to the lack of a Father in his household. He did well enough in school, but was a loner with only two friends his mother could identify. He had no brothers or sisters, and no extended family in the area. They lived their routine in the suburbs, she going to her professional position downtown and he going off to school each day, returning sometime after 3 for a snack and some cartoons on TV.

He had a room in their house with a view of a neighbor’s house behind theirs, over the fence where their two backyards met. The previous family had moved out, and during this afternoon in July he watched as the new family’s movers deposited furniture and boxes throughout the house, easily seeing in through the uncurtained windows. While munching on his peanut butter and jam sandwich, he was looking into one of the second floor bedroom windows when the Matron of the family pulled a young man by the arm into her bedroom and began scolding him. The window was open, and he could hear the tone of her voice, stern but with a surprising affection. She stopped speaking for a minute, and reached to the young man’s jeans, unfastening them and sliding them down his legs to the knees. She then turned and sat on her bed, beckoning to him. He stepped forward, but instead of bending over her lap, he stood in front of her and pulled his underwear down when she indicated. His cock was prominent, Marty thought he was well endowed at first but then realized that he was becoming more and more erect as she inspected his penis. She held it gently, stroking it’s length, turning it side to side looking it over. Once she was satisfied with the results of her inspection, she motioned for him to lay over her lap. This he did slowly, adjusting his position until he seemed comfortable, and then he was still. She reached over to the bedside table and took out a hairbrush and began to rub it on his now bared and upturned ass. She leaned over to speak to him, gently stroking his hair briefly, then began to swat him with the brush.

Marty couldn’t believe his eyes, of course, he had seen nothing like this. For the first time since this scene began, he looked at the other uncurtained windows, and could see that other members of the family were listening and occasionally looking toward the closed bedroom door, giggling and talking. This was also odd to him, but not as odd as the scene unfolding upstairs. He again looked at the upstairs window.

The punishment was still going on, and although Marty could hear each swat clearly through the open window, the young man didn’t make much noise or protest. Once the woman had finished the hair brushing of his bare bottom, he stood up slowly and stood before her again. Then yet another strange thing happened. The woman again caressed his penis, which was not as erect as before. She continued, and the young man leaned with both hands on the woman’s shoulders, his head dropping down below his shoulders. She was jerking him off Marty realized, then also realized that his own cock was hard and pushing against the fly of his chinos. Suddenly the young man in the window came, and the woman caught his semen in a washcloth that she produced, from where Marty couldn’t tell. By this time Marty was also ready to come, and only held himself in check when his Mother called from downstairs to empty the garbage. For the rest of the afternoon this was all he could think about, and later that night he masturbated in his bed thinking of the scene, coming rather quickly.

The next afternoon, he decided to walk past the front door of his neighbor’s on the way home from school. He had gotten out early, and his mother was away until late that evening at a local conference. He knew his dinner was ready to microwave, his homework was not critical and so he felt rather free and independent. As he approached the house, he was surprised by one of the youngsters he had seen the day before, a pretty brunette who called out to him and invited him up to front porch. He sheepishly accepted, walking up while nearly staring at her. She was wearing short jean cutoffs, a tight spaghetti strap top, and had the figure to show off this way, if a little soft around the edges. She laughed and asked why he was so amazed, and he stammered a bit before answering that he thought she was pretty and was not used to being talked to by pretty girls at school. She laughed again, introduced herself as Ann, learned his name and invited him inside. He couldn’t believe he had said that, so geeky sounding, and he felt his face flush with embarrassment as he stepped inside the house.

When the Mother came in the room, holding hands with the “young” man he had seen from a distance, and introduced him as her husband, he appeared much older if still smaller and shorter than his wife. They seemed very affectionate and loving, and friendly. They introduced themselves as Carole and Arny, Ann’s mother and stepfather. Marty hardly knew what to say, but that didn’t seem to matter for the couple were preoccupied with finishing the move into their new home. They were soon busy in different parts of the house, and Ann and Marty found themselves alone again. Ann had done her part, she explained, so couldn’t they go do something fun? Marty suggested he show her his house next door, and they set out across the back yard, over the fence and into Marty’s house. He showed her all over, finally his room where they sat and ate P.B.J.’s and milk. While they were sitting and talking suddenly Ann grew quiet while looking out the window, then laughing asked

“Marty, did you see Arny getting punished yesterday?”

Marty nearly choked on his sandwich. He was going to lie, but her cheeriness and sweet attitude made him think it would be better not to. He admitted it, but didn’t tell her all that he saw.

“Marty, I hope you don’t think I’m weird, for I’m not and neither are we. It’s just that Arny likes to be dominated by Mother, do you know what that means?”

Marty had an idea what that meant now, but he let Ann explain about her parent’s interest in female domination, and what they do sometimes behind closed doors. After she had finished, there was a strained silence in Marty’s room, and Ann put her plate down on the floor, turning to Marty as they sat on the edge of his bed.

“Have you ever been spanked, Marty?” She asked, looking straight into his eyes.

He drew back, becoming more nervous, stammering, “NO, never!”.

Ann laughed again, and looked down at his trousers, which were showing this bulge of his erection. Marty had not noticed that Ann’s description of spankings had aroused him until that moment, which caused his penis to subside a bit. He shifted uncomfortably as Ann looked into his eyes again.

“I know it arouses you, to hear about spankings, it’s obvious. And you are not a small boy either, Marty, you can’t hide that too easily!”

Marty blushed, but remained where he sat.

“May I touch you there, Marty?” Ann asked, and leaned toward him.

Marty didn’t answer, but neither did he move away. She reached out and touched his knee, which caused him to jump slightly but again he didn’t avoid her. She slid her hand expertly up his leg to the bulge in his trousers, squeezing it gently through the fabric, causing Marty to close his eyes. She stopped, and said, with a slight laugh still in her voice,

“Marty, you have been bad haven’t you?”, to which Marty, his eyes opening only slightly, nodded in agreement.

“You’ve been a peeping Tom, haven’t you?”

He nodded again.

“Well, Marty, I think it’s only proper that you get the spanking you deserve, don’t you?”

Marty knew this was coming, his eyes opened and he barely nodded once more looking into her eyes, his mouth open slightly. Ann told him to stand in front of her.

Slowly, somewhat mechanically, he stood up and moved in front of her. She smiled and reached forward, unbuckling his belt, sliding the leather out of the buckle, fumbled briefly with the button until it came undone, then slowly unzipped his fly while looking up at him. He was watching intently, their eyes met and he saw her smile again. She tugged his trousers down around his calves.

“Marty, pull you underwear down like a good boy.”

He had thought she wouldn’t go this far, and he hesitated with his thumbs under the elastic waistband.

“Marty, pull them down, now” she repeated more sternly.

He obeyed, slowly pulling his underwear down, exposing his good sized penis, stopping about mid-thigh. Ann looked at him for the longest time, making him turn around, telling him to lean forward hands on knees while she examined him. She told him to spread his legs slightly, straining his underwear around his thighs. He was glad that his mother had made a point of showing him how to clean himself there, and how he had always avoided staining his underwear by being careful and clean. She spread his bottom cheeks and probed his anus gently.

“Marty, have you ever been touched here before? Have you ever touched here to arouse yourself?”

His voice caught in his throat as he tried to answer, she said “I’ll take that as a yes, you naughty thing!”, and she gave him a light swat that startled him.

He stood up and she turned him around, discovering his now erect and throbbing penis. She giggled, and began to stroke him like he had seen her Mother had stroke Arny the day before. Marty stood still and closed his eyes while she fondled him.

“I think that’s enough of the inspection for now, young man, take the position over my lap” she said with gentle authority.

He did so, and in leaning over her lap he discovered why Arnie had taken a few moments to do the same, he had to find a place for his erection. Ann obliged by parting her legs, allowing his hardon to slide between her bare legs, just below her jean shorts. She then squeezed her legs together, pinning him in position. She started by rubbing his bare ass slowly, fondling it really, making him part his legs as much as his underwear around his thighs would allow. She then started spanking him slowly at first, then picked up the pace. Every so often she would stop and rub his reddened ass, starting in again with newly discovered energy. Suddenly, almost without warning, Marty began to come, pumping his cock involuntarily between Ann’s legs, squirting hot semen all over the carpet. She stopped spanking him, and helped him up off her lap and then on his back across the bed. Ann lay next to him, gently holding his subsiding erection, using some tissues from beside the bed to soak up the semen. Marty lay with his eyes closed, full of colliding emotions, embarrassment, joy, post orgasmic mellow, the beginnings of feelings of affection for Ann, fear of being caught by Mother. Soon he opened his eyes and looked at Ann, staring into her eyes for a few moments.

“Have you done this to other boys, Ann?” he asked.

“Yes, of course, it’s fun. What do you think of being spanked now?”

“I, well, I guess I liked it, but my butt sure is sore. Have you ever been spanked?”

“Of course, but I generally prefer being dominant, and I have not had a boyfriend spank me, yet.”

She leaned forward and kissed him like he had never been kissed before, for he had not been kissed before fully on the lips by someone who knew how. She then got up, adjusted her shorts and top, and slowly left the room, turning to Marty at the doorway saying

“Let’s do this again sometime, OK naughty boy?”.

Marty got up off the bed and nearly fell over, forgetting that his underwear and trousers were still around his legs, causing Ann to laugh again, watching him stumbling around the bedroom, and his cute bare ass, trying to pull his pants up.


3 thoughts on “Marty’s Day With the New Neighbor”

  1. This story reminds me of when a girl friend caught me in the act and turned me over her knee for 100 spanks when she saw my erection still up she took a tawse and whipped my penis! saying “you naughty boy you can only masturbate if I give you permission!”

  2. Great story and so well told. It really got me so aroused that I wanted to be spanked which I have never wanted before.

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