Training Ch. 05

May 25, 2024 // By:analsex // No Comment

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After Bobby took Bonnie from behind, which was his first ‘doggie’ fucking ever, they didn’t realize it but both of them fell asleep. They had rolled over and as she lay spooning him they held each other. His hand cupping her large firm breast and she had her hand over her hip holding his soft and cum covered cock. The sex had been wild, hard and long and both were completely exhausted.

They stayed asleep until the phone rang. When Bonnie finally answered it, Jane, Bobby’s mom, was on the line. She was wondering when Bobby would be home and if she should fix dinner.

Bonnie asked her: “Would you mind very much if I feed Bobby tonight Jane? We were just finishing up and seemed to have fallen behind. I’ll make sure we both get a good protein meal.”

They both seem too giggled a little and finally Jane said: “Sure, finish up; I’d hate to think you didn’t finish your work Bonnie. Take your time; I’ll be waiting for him later on. I’ll just turn on the TV and watch whatever is on.”

Jane hung up and walked into the master bedroom. She turned on the TV and sat on the edge of the bed. When the pictured came on, Jane could see Bonnie and Bobby in the big master bed. She had watched her son and her best friend over the days that had passed fucking and sucking and enjoy each other’s bodies.

Jane watched and listened as Bonnie make a phone call for a pizza to be delivered and then slip on her robe. She told Bobby: “Stay in the bedroom and please sweetie, stay nude for me.”

She moved to him and began to play with his soft deflated cock. Bobby lay back and watched as Bonnie jerked him off a little and then moved over her mouth over his cock head. She sucked it for a few minutes and then told him: “I better stop and shower before the pizza man gets here. When I’m done you can do the same. I want you clean and fresh for me when I finish sucking you dry after dinner baby.”

She jumped up and went into the shower. Bobby watched her walk swaying her hips as she entered the bathroom. He took his cock in his hand. Jane watched the TV and she watched Bobby slowly stroke his dick as it started to get harder. Jane loved how his recovery powers helped him become hard again so fast. Then she heard Bonnie say: “Oh no Bobby, none of that young man! You wait until we are both clean then I’ll do that for you!”

Bobby started to get up and go to the shower with her but stopped when Bonnie told him: “No Bobby, you stay right on that bed. If you come in here you’ll just cum on me or in me again. Listen for the pizza guy.”

Bobby stopped playing with his cock and lay back closing his eyes while he waited for his sexy lover to finish showering. His mother watched the TV as the camera showed Bobby’s cock growing hard without him even touching it. She wondered what he was thinking! She knew it was most likely of Bonnie but what were they doing? Was she sucking Bobby’s cock, or was he fucking her and in what position Jane wondered?

Before she realized what she was doing her fingers were working on her pussy making it wet and even in more need than usual. She moved the pillows back against the bed and sat against them as she zoomed in and watched her son’s cock sticking up in the air, jumping from time to time.

Jane masturbated to the picture of her son and his magnificent cock as she watched it on the TV and she came very hard in a matter if minutes. She watched and saw that Bobby wasn’t even touching his cock and it looked so hard and thick as it stood straight up in the air. His balls were so tight and so big! She wanted to hold them, and suck on them and make her son cum in her mouth so she could taste him.

She fantasized about riding her son’s cock up and down as she sat on him. She wanted to fuck him anywhere, even in Bonnie’s bed. Jane didn’t care now if that cock belonged to her boy, she really needed to be fucked. She reached for her dido in the night stand and fucked her pussy wildly with it as she climaxed hard again just as Bonnie came back into the room after finishing her shower. She had a bath towel wrapped around her body and one around her hair.

Bonnie made Bobby get up and she went into the bathroom with him. Jane heard her say: “I’m going to make sure you don’t jerk off and cum in here Bobby. I want that big hard cock to stay hard for me later on.”

When they walked out of the bathroom a little while later Jane saw her son’s cock at half mast. Bonnie dropped the towel showing off her very attractive body and Jane watched as Bobby put on his boxer shorts and Bonnie used the robe again but left it opened like she did when no one else but Bobby was around. She turned towards him and Jane watched the TV as Bobby grope Bonnie’s tits and nipples. Then they walked past the camera and as they passed Bonnie winked at it when she knew Bobby wouldn’t notice.

By then Jane had cum three times thinking of her son’s big cock and what it could do inside her pussy. She laid back and closed her eyes. In seconds she fell asleep with the TV on. Her son would get home later and completely fucked out again. She knew how lucky Bonnie was and she knew soon she too may have his big young cock if the plan worked the two women had developed for her son.

It seemed that each day would start with Bobby and Bonnie painting a room. Then they went to Bonnie’s bedroom, showered and then Bonnie would have him practicing his sexual technique on her body. They especially worked on her pussy practicing his oral skills and making sure he could find that ‘G’ spot and her clit. Jane watched each session and saw how well her son had learned the tricks to being a good lover.

Jane watched Bonnie having more orgasms from Bobby’s mouth and his cock than she ever had even with her dead beat husband. Jane watched them on TV and she too was enjoying the best orgasms of her life.

Each day the two of them would work for a few hours and then Bonnie would turn on the shower and that would be the start of their sexual play by cleaning each other. While Jane couldn’t see that part, both of them would come out of the bathroom nude. Bobby’s cock was always so hard and sticking out in front of him. Sometimes Bonnie would be holding it and pulling her young lover towards the bed. It was like she could hardly wait to begin his training.

They would jump in the bed and there was always a lot of licking and sucking until Bonnie couldn’t stand it any longer and had to have Bobby’s cock in her cunt. He was always ready and they fucked in different positions each day.

Bobby was getting much better at all of it. He especially loved the cowboy and doggie positions. Jane loved that position too. She would see her son’s young hard cock going in and out of Bonnie’s pussy hole as the camera captured everything.

Jane would masturbate slowly as she watched her son practicing his skills as Bonnie direct and trained him. Now Bobby always made Bonnie cum not only with his mouth but with his cock too. He always made his mother Jane cum too but he didn’t know it. They all had many orgasms as hours passed each day.

Jane felt her son was almost ready for the next step. How she had wanted this next step for so long. Almost since the day her husband had died and she walked into the bathroom and caught Bobby masturbating she had been lusting for Bobby. She loved that imagine of him thrusting his cock in his hand, cum flying out the head and Bobby moaning and cumming so hard with he orgasm. Jane had just stood there and watched until he saw her. Embarrassed, he quickly covered up. But, Jane couldn’t get the image of his hard thick cock and all that cum out of her brain.

The plan Bonnie and Jane had developed was working great. Bobby was becoming a very good lover and soon he would experience a number of different women one of which would be his mother. Jane rubbed her cunt again and came so hard it took her breath away.

It had been a month of training for Bobby now and it was almost the end of July and summer was in full swing. Each week, Monday thru Friday Bobby would work in her home for a few house and then the fucking would begin. Each Saturday Bobby would cut the grass and keep the lawn up for both his mother and Bonnie. Sunday would be a day off unless he wanted to come over and see Bonnie which usually happened. She had created a fucking monster.

As he mowed the grass Bonnie would lay out in the sun wearing her smallest bikini and teasing him terribly. After he was finished he would shower in her bathroom and then he would fuck her like a mad man. She would make him undress her and learn how to remove different woman’s clothing. She loved it when he took her and dominated her like he did on most Saturdays.

Also on Saturday they would both spend some time at his house with his mother. The subject would somehow always turn towards sex and the girls he was dating or wanted to date. The women would make his cock as hard as they chatted and teased him. Lots of wine would flow and Bobby would see these two ladies relaxing more and more and not caring about much of anything. They became much freer with their clothes showing Bobby a great deal of their thighs, panties or breasts, especially Bonnie. Sometimes Bonnie would whisper to Bobby telling him: “I’m not wearing panties tonight Bobby, want to see?” When they were alone she would lift her skirt and show him her pussy. Many times Bobby would get Bonnie alone and play with her pussy finger fucking her. Or, he would rub her ass or reach for her breasts. Bonnie would grab his cock on the outside of his slacks and ask if his hard cock was for her? He was always in a state of high arousal

Sometimes his mother would ‘almost’ catch them in the kitchen or in another room. She would actually watch her son feeling up her best friend for a few minutes and then cough or say something before entering the room fully. Bobby would jump and straighten up and try to act like nothing happened. Bonnie would smile at Jane as she straightens her blouse or shirt. They would both see the big budge in Bob’s jeans or shorts

Jane would tease him and shake her finger and tell him he had better be good or Bonnie might take him seriously and rape him! They played this game each time the three were together. Bobby would be embarrassed and Bonnie and Jane would laugh it off. But both women would be wet before the end of the night and Jane would masturbate a long time after Bobby walked Bonnie back to her house where he would get a blow job or fuck her before going back home.

Then one early Saturday afternoon as Bobby cut the grass, Bonnie yelled to him: “Bobby!! Stop, it’s lunch time.”

She would always serve him lunch and most of the time Bobby would be done or almost done with the grass. He knew after the grass cutting he would go inside Bonnie’s house and shower with her and then they would fuck the rest of the day away.

But today would be different. As he walked towards the table on the patio, he saw his mother. She was standing next to Bonnie with a bikini on!! His mother never wore a bikini, hell she hardly ever wore a bathing suit.

When he got closer he saw her remove the bikini cover and Bobby was amazed to see that his mom had on a bikini just as small as Bonnie’s bikini. Jane’s was red while Bonnie’s was black. Jane said: “Bonnie invited me over for lunch and to lay out in the sun with her Bobby. How do you like my new bathing suit? Bonnie picked it out for me. I hope I didn’t interrupt anything Bobby. Did I?”

As Jane said it she turned around showing her son her body. Bobby was amazed at how beautiful his mother looked in her bikini. “Ah no mom, I’m just surprised that you are wearing a bikini that’s all”, he stuttered.

Bonnie asked: “Doesn’t she look great in it Bobby? Didn’t know your mom was that sexy did you? Well what do you think?”

Bonnie stood next to Jane and Bobby just looked from one MILF to the other. “Well”, she asked again, “Doesn’t she look great in it?”

Bobby looked at his mother again and said: “WOW mom you look…….amazing!! Yes, you look great mom.”

Jane smiled and said: “Well thank you Bobby. I’m very happy you like it. How about the color? You like red Bobby?”

Bobby told her: “Yes, red is a good color for you mom. I mean you look really, really good.”

“As good as me Bobby”, Bonnie laughed as she said it. She knew she was putting Bobby in an embarrassing situation but she wanted to do it.

Bobby said: “Well she is my mom!! But she looks great. Yes, she looks very good.”

Bobby eyed his mother now differently, not like a mom but more like he viewed Bonnie. They were both sexual women! He loved how his mother looked. As Bonnie served lunched Bobby couldn’t take his eyes off of his mother’s body. “When had she become so sexy”, he said to himself?

He looked at her big firm breasts and those long legs and tiny stomach, as good as or maybe even better than Bonnie. As he looked up and down her body again he stopped at her ass and then her breasts. Her breasts looked almost as large as Bonnie’s tits. “When did that happen? When did my mom’s tits grow so big”, he wondered?

He decided that these two ladies were most definitely MILF types. He sat there without his shirt on covered with a light wetness from cutting the grass. His jean shorts showed his lust as he watched each woman move and talk and adjust their bikinis.

The women were noticing his lust. Then Bonnie came over to him and sat on his lap. She smiled into his eyes and said: “WOW Jane he has a really big hard on. I guess he does like the way we look.”

She turned and moved her face real close to his and said: “Now mister, tell me which of us do you like the best?”

Bobby looked at Bonnie and knew if he said the wrong thing he could blow the wonderful sex they were having so he said: “Well she’s my mom so I like her the best Bonnie, but I think you are sexier!”

The two women laughed and both kissed his cheek. Then Bonnie said: “Well then tell us Bobby, which is the better MILF? Which would you rather fuck?”

The word fuck in front of his mother made Bobby blush like hell, but the question made his cock jump. He didn’t answer so Bonnie asked again: “What’s wrong? Cat got your tongue? Or would you like to do both of us?”

He got redder as he looked at one women and then back to the other. Bonnie kept pressing and pressing and finally Bobby said: “Both!! I’d like to have sex with both of you if she wasn’t my mother!”

Bonnie smiled and kissed him hard right on the lips. Jane watched as she felt wetness between her legs. She had heard her son say he would love to fuck her. She didn’t hear the other part of the conversation. She sort of went into a day dream and imagined what it would be like to have Bobby remove her bikini and give her what she needed so badly, a long hard fuck!

After lunch Bobby took 15 minutes to finish the grass cutting while Bonnie and Jane talked alone. They decided to move Bobby to the next step tonight which would involve other women fucking him on and off over the next couple weeks.

One of them would be Jane but Bobby wouldn’t know it was she until later on. They planned to sit him down and talk with him about it afterwards and tell him why she did it and what she was hoping from him going forward. That was the plan, it didn’t work out exactly as they planned, it would actually work out better.

Jane and Bonnie had planned to tell him all about the way he was trained and why he was trained. Then Jane would tell him she was one of those ladies who had fucked him. They would talk about it for a long time and then she would hope that since it had happened they could do it again. They hoped that Bobby would fuck both women on a regular base.

Jane would hope Bobby would understand that since her husband died she needed a man, needed her son, in more ways than ever. It had been seven years since she had had a man fuck her. She wanted Bobby to be her man, her lover and she would give him anything he wanted in the way of sex. She would do anything he wanted and try anything he liked.

And if Bobby agreed, she would be very happy for him to go to Bonnie and fuck her too. After all he had just said he would fuck both of them so why not let him do it? He pretty much told them both he wanted to fuck them and that he couldn’t decide which one was sexier. So why not let him taste both women and enjoy sex with them?

Bonnie and Jane both were sure Bobby was young enough and strong enough to satisfy both of them and they knew the sex would be good for him too. They were thinking of all the things Bobby would learn from two older sex hunger women. They would make him a great lover.

Jane knew that sooner or later he would find the right girl and he would please her like no other guy his age could do. The two women would be sure to teach him all the tricks and things men should know when they make love to a woman. “Yes it was time for part two of their plan. Bobby deserved them and their skills”, she said to Bonnie.

Bonnie agreed. “The first thing we need to do is get him to let me tie him up and blind fold him, but I don’t think that will to hard to do. Then we can see if he can tell the difference in pussy”, Bonnie laughed as she told Jane.

“Yes, and we’ll get Dhea (pronounced Daya) to fuck him first. I met her at the gym and she is a lovely Asian woman. I’m sure Bobby will find her very attractive. She is around 30 but looks so much younger. She told me she wants to try a white man’s cock and I’m sure I can get her to go along with our plan” Jane told her best friend.

The women kissed goodbye and Jane watched as Bobby put the lawn mower away and went into Bonnie’s house. Jane smiled and said: “So when will you try to blind fold him Bonnie?”

Bonnie said: “Well why don’t you go watch TV and we’ll see if we can do it today right after his shower. Call Dhea and see if she can come over tonight, if so, we’ll get this done tonight. Then the next step will be you Jane. I know you can’t wait. He really is getting very good at all of this. Let’s make it for 6:00 PM. Dhea can meet both of us at my house. Oh and Bobby will be late coming home tonight. I plan to reward him after Dhea leaves!”

Jane went home and called Dhea and she was more than eager to join the plan, especially when Jane told her it was for her young son. She knew Bobby was a big strong young guy and she liked him from the day she met him at the gym. Jane explained that Bonnie was teaching him all about sex. Dhea told Jane: “I may be able to teach him some things too. This should be fun and I’m sure Bobby will be great he’s so cute!”

Jane called Bonnie while Bobby finished the shower. Bonnie got out the silk scarves and waited. She sat on the bed fully nude and smiled.

When Bobby came out of the bathroom he was nude as usual. Bonnie smiled as she watched his cock swing from side to side. She patted the bed and said: “Come and lay with me baby! I want to ask you something.”

Bobby jumped on the bed and lay down next to her as his hand went to her breast. Bobby couldn’t get enough of her tits and was always touching and holding them. She took his cock and began to gently stroke it.

Jane watched them on the TV from her own bedroom. She was lying on her bed and watching and listening as the camera in Bonnie’s room recorded everything. She began to play with her pussy knowing what was coming and what she would see Bobby do to and with her best friend

Bobby watched as his hands made love to Bonnie’s nipples and her hand did the same to his cock. He loved to see and feel Bonnie’s hands on his cock. “So what do you want to talk to me about”, he asked?

“Bonnie kissed him and looked into his eyes all the while not stopping with what she was doing to his cock. Her hands were magical. His cock was hard and thick and throbbing in seconds. She moved her mouth to his ear and said: “I want to tie you up Bobby and then blindfold you and tease you and see how long you can hold off from cumming for me.”

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