Pops First Time – Chapter One

Tags -- sex, Story, voyeur

Pops has detailed his ‘first’ sexual experience in his ‘diary’ as I call it. Unfortunately he does not remember all the details. He says that a part of his memory was erased when they bypassed his blood vessels.

As luck would have it the women (yes more then 1 – actually four) are all still good family friends and I have been able to interview them to get details and the juicy stuff.

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Pops grew up in a mid-sized town. His family’s house was the third from a corner and the left side of their back yard had a row of bushes that were very tall and very thick. Butted against these bushes was a house where the Mom and her three daughters lived.

The bushes bases were about four feet from the girl’s house and grew about six feet tall. The mom’s bedroom, the two older girl’s bedrooms and the bathroom were all along the back wall of the house and all had full-length windows. The bushes covered the bottom half of the windows.

Pam, who was two years older then Pops, had often wondered how Pops could disappear. He trimmed the bushes and had once dropped the shears behind the bushes. He had discovered a way into the tunnel formed by the bushes and the girl’s house’s back wall.

He had also discovered that the girls did not ever close the curtains or blinds because the bushes blocked the view. But it did not block Pops view. He had ‘spied’ on the girls in their bedrooms and the bathroom and the night he was ‘caught’, he had just discovered that ‘Mom’ as he called her, brought home her current boyfriend from work for a quickie during their supper break. He had been watching them fuck for about two months. He had been spying on the girls for over a year.

He often teased Connie (she was Pops age) that he watched her pubic hair and tits grow.

Mom’s boyfriend (Mom’s is not to be confused with my mother or momtoo – this is the neighbor girl’s mom) was also her boss so sometimes their dinner break would last a couple of hours.

She always told her girls they were just going to lay down for a quick nap. Pam knew what was going on but was happy her mom had a steady boyfriend.

Normally Pops stayed with the girls from after school to 11 pm when Mom got home from work. Sometimes the girls, Pam, Connie and Ann (who is sometimes called Annie and is five or six years younger then Connie) would make dinner and other nights they went to Pops for dinner or to the doctor’s house (more on him later).

Pops was their tutor and sort of baby sitter. As it turned out he tutored Pam and Connie in more then math and English. They both told me his best subject was washing hair and making them cum.

That night, Pam had watched Pops walk the bush row and saw him turn a corner like he was going to their house but when she followed him he had not showed up at the house so she backtracked and found Pops’ secret entrance to the tunnel.

When she peeked around the corner Pops shorts were hanging in the bushes and he was jerking off while peeking in her mother’s room.

She quietly walked up to him and peeked in. She said he never missed a stroke. Just because he had been caught was not going to deny him. She said she watched her mom suck her boyfriend’s dick then she climbed on top.

Pam said she undressed and Pops could not decide what to watch. She backed up against him trapping his cock between them in her butt crack. Pops let go of his dick and she started rubbing her ass up and down on him.

He reached up and cupped her boobs from the back and started playing with them. She told me she came a little when he first started playing with them.

She also told me that she did not allow Pops to touch them again until she was 18. In fact, she does not think Pops saw them bare up close until her 18th birthday. She still let him see them in her bedroom and the bathroom but would not let him touch them. It drove her crazy.

They watched her Mom get put on her back and watched her boyfriend fuck her hard. They were watching from the foot of the bed so they had a good view of their fucking.

Pam said she grabbed one of Pops hands and taught him how to rub her pussy but would not let him stick anything in her.

When the guy came, they came – she said Pops had perfect timing. Pam said Pops shot cum all the way up her back and it felt like the back of her head was drenched with cum.

When her mom started sucking her boyfriend, Pops tried to get her to suck him but she was afraid he would choke her AND she just did not think she would like sucking his dick.

She was amazed when the guy AND Pops both got hard again. Her friends had told her it normally took an hour sometimes. She watched her mom take it doggy style and it gave her an idea.

She got in front of Pops and reached between her legs and grabbed the head of Pops’ dick and pulled it between her legs to straddle it. When she moved forward and back, the head of Pops’ dick would ‘pop’ out between her legs right under her pussy.

She said it was great, his dick rubbed her asshole, pussy and clit and Pops said it felt like he was trapped. She could feel his balls squished right under her ass against the back of her legs.

Pam said Pops only lasted about thirty seconds the first time and she was sure her mom and boyfriend ‘heard’ his cum splat against the side of the house. She had never admitted it before, but whenever Pops was trapped between her legs and came, she always came but she got good at hiding it because it made Pops head too big. I know just what she means.

Pops said he always knew because she would get so wet. Pops also figured out that if he pulled his cock back far enough and sort of angled up, the head of his dick would start to slide into Pam’s honeypot but Pam always moved just right so that he slid past and out the front.

His notes said his favorite time was when Pam was extremely horny and she would reach down and use her fingers to pull Pops’ cock tighter to her pussy. She also would sit down on his cock, which felt even better.

He said she loved it when he spread her ass apart to get more of his cock out the front of her. Sometimes she even reached back and held her ass open and sometimes she bent over to get a different angle. He said he watched her butt hole more then any other part the first two years.

The first night, Pops came four times. Pam says she came more then that. After her Mom took it doggy style, they thought they were done so Pops used his T-shirt to wipe the dried cum off Pam’s back and hair and she put her top on.

Pops had his shirt back on when her Mom sucked her man’s cock again and then rode him. Pam said Pops started jerking off and she got back in front of him and he pushed his dick between her legs and out the front.

She loved how soft the head of his dick was and was rubbing it when her mom came and Pops came. She said she took the full blast in her hand and deflected it all over the front of her top.

Her mom and the boss left and Pam and Pops were trying to figure out how they would get inside their houses to change their clothes before someone saw them.

Pam told Pops to follow her and they went to the Doctor’s back yard and she pushed him into the swimming pool and he dragged her in with him.

Pam said Pops grabbed her ass and pulled her to him. He kissed her full on the lips with tongue and she kissed him back. When his fingers found her pussy she spread her legs and then his other hand found her tits and she pushed him back and did not kiss him again until her 18th birthday.

She confesses that if she had let him kiss her and play with her tits that he could do anything he wanted to her. She would not try to stop him. So she never let him do it again until the night of her 18th birthday.

The first hole Pops put his cock in was an asshole. And it was Pam’s asshole. But they were still learning and had some bad advice.

But I’ll save that for the next chapter. Pam and Pops met almost every night, even during the winter, for the next two years to watch her mother fuck her men.

The first night they got off together, Pops and Pam had just recently celebrated birthdays. Pops was fourteen and Pam was sixteen. It was another two years before Pops got his first piece of ass AND a blowjob. But as Pam tells it, it was not for a lack of trying.