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Chubby's Memoirs chapter 5

Tags: incest, anal
Stella introduces her best friend to anal sex to satisfy her husband's urge for a tight hole
After leaving our house Mom and I went straight to the airport. The flight was due any moment. We waited in the car before going to the arrival pick up point.

“Thank you, my dear son,” Mom said giving me a kiss on my cheeks.

“Thank you for what, Mom?”

“Thank you for getting rid of my fear of taking in a cock into my cunt.” She kissed me on my cheek again. “Thank you for giving me a great time last night.” She now kissed me on my lips and put her right hand on my cock.

“Mom, please stop playing with my cock. You are giving me an erection.”

“So? Why don’t you fuck your mom in the car right now while waiting?”

“Not in daylight and in public, Mom. Moreover tonight, you have to give Dad his fuck that he has been so eagerly waiting for,” I replied putting my hand on her breast and kissing her lips.

Mom laughed and said, “I was just teasing you, son.”

Passengers started to come out. We went to the pickup point and waited. We saw Dad, Stella and another woman with them. Dad hugged Mom and kissed her tamely on her forehead.

“Don’t I get a welcome hug from my big brother?” Stella said opening her arms for me to hug her.

I hugged her and whispered in her ear, “Wait till you get home. You will get more than a hug."

“Mom, brother, meet my best friend, Kathy. She will be staying with us for a night or two."

"Hello," we wished her.

Kathy was around 40 years old. She was beautiful, slim and average height. Nice, I thought to myself.

We then went home. I forgot to mention that Dad has a butler and a maid to look after our house. Dinner was ready. We all had a small chat at the dinner table. After dinner Dad was eager to retire to his room.

“So, Stella, I think I will call it a night. Your friend will be sleeping in the guest room?” I enquired to find out if she would be alone tonight.

“No brother, she is my date tonight. I hope you are not jealous of what we will be doing tonight,” Stella joked.

“Hush Stella, how can you talk to your brother like that?"

"Don’t worry Kathy we are used to teasing each other. He is a lousy brother, can’t even introduce any of his friends to date me.”

After that they left for their room.

* * *

"Stella, you have a very handsome brother. He is not your natural brother, have you not had any idea to date him or you are already dating him?"

“You mean that I get him to fuck me. No Kathy, that idea never came to my mind. By the way you seem to be showing interest in him. Shall I set him up with you tonight?"

"No, how can I do that? I am a married woman and I love my husband too much to cheat on him,” Kathy replied.

“Good, then get ready for your husband to go out for other women and if he finds someone nice, he may want to divorce you. Then what?" Stella asked.

“Stella, I know you have been fucking around with a lot of men. I want you to do me a favor. Please fuck my husband and please him, for my sake please."

“Look Kathy, you are my best friend. I don’t mind doing you the favor. One fuck will not be enough to keep him with you. He will need it often. I can’t be there as his mistress forever.”

“What do you suggest, Stella?”

Stella picked up her phone. "Hello, brother, can you come to my room now?”

“Stella, why are you calling him? We cannot talk freely in front of him.” There was a knock on the door.

* * *

Stella opened the door and I went in.

“Hello beautiful ladies how are you two getting on with your date?”

“How can a date be complete without the company of a handsome man?” Stella replied.

“You find me handsome? Thank you that is compliment coming from you,” I replied.

“Brother, I did not say that. Kathy said that you are handsome and asked me why I…"

“Shut up Stella, how can you embarrass me like that?” Kathy shouted.

‘What is the joke? Will anyone enlighten me on that?" I asked.

“Stella please don’t," Kathy pleaded

“Kathy you are my best friend, we share all our secrets don’t we? My brother and I are also best of friends and we also share lot of personal things, like me going out dating very often. He is a man and knows what happens on dates. We have joked about it often. We are that close, everything with the exception of what you suggested.”

“What did she suggest?" I asked curiously.

"Kathy suggested that you and I start dating and fucking each other.”

“I said dating only,” interrupted Kathy.” I did not mention anything about fucking."

"Is that not what dating is all about Kathy? It is not like going to church. Most of the times we dated don’t we end up getting fucked,” Stella replied. Kathy was left speechless.

“Kathy, you don’t have to be embarrassed,” I explained to Kathy,” you know your friend’s nature. Take it as joke. We have no intention of dating. It will be more fun to remain as friends. After all she is my kid sister,” I explained to Kathy.

“You call me a kid. Wait till you hear what my dates have to say about your kid sister.”

“Oh come on, stop your arguments will you both?" said Kathy.

“Brother, Kathy here has got a problem. She and her husband love each other very much.”

“Then what is the problem?" I asked.

“Stella please stop, you don’t have to tell him that? I feel shy. What will he think of me?" pleaded Kathy.

“Shy? Then we will have to do something about that. Brother can you do me a favor?”

“Yes sister what is it? You want me to leave?” I asked.

“Can you for a moment forget that we are brother and sister and that I am present in this room and strip yourself, for my friend to see you naked,” Stella requested.

"What!" Both Kathy and I gasped.

“My friend is shy and once she sees you naked the shyness has to run. Please do it for me brother.”

I looked at Kathy as if asking for her approval.

“Kathy, do you want to find a solution for your problem or do you prefer a divorce? Make up your mind,” Stella said to Kathy.

Kathy was in a confused state of mind, not knowing what to say. She looked at me and slowly nodded her head asking me to go ahead and undress.

I reluctantly undressed. Stella pretended to look away not wanting to see her brother naked.

“Stella, if you want me to see your brother naked, you too must join me to see him naked,” Kathy answered.

“OK, if you insist and if that makes you comfortable I will have a look.” Stella looked at me and said, "Wow, brother you have such a juicy cock. wish my dates had one like that."

"Kathy what do you think of my brother’s cock compared to 6 inches your husband has?”

“I…I…I don’t know what to say. It is not proper what we are doing you know," Kathy protested.

"Come closer to Kathy brother, so that she can have a better look.” The moment I went close to Kathy my cock started to grow.

”Wow, brother, you have an 8 inch cock, much bigger than any cock my dates have had. I wish you were not my brother.”

“Why don’t you take my suggestion and start dating and fu--” Kathy suggested.

“I am sorry I cannot do that with my little sister,” I insisted.

Stella caught Kathy’s hand and made her hold my cock and feel it.

“Does it feel good Kathy? Go on feel and rub it.”

With all this, Kathy began to feel comfortable, with what was happening. She caught my cock and held it tight and looked into my face indicating that she liked it.

“OK, can we now carry on with the problem?" Stella interrupted. "As I mentioned earlier she and her husband love each other very much. But lately he had a frank discussion with her and told her that he's not getting any thrills from fucking her. The reason he said was that her cunt had grown bigger and is very loose. He is not getting the pleasure used to get before."

“He was frank and honest about it and has asked Kathy for her permission to date other ladies, to satisfy him sexually. He loves Kathy so much that he does not want to divorce her. He wants to remain married to her. Kathy wants me to let her husband fuck me. Once or twice will be okay but it cannot go on forever.”

“The real fear is, what will happen, if he finds a woman that can take care of all his needs?”

“Stella stop it. My husband is right. I feel shy to let anyone know that I have a loose cunt. I too do not have any feelings when he fucks me, but I dare not tell him that.”

“Don’t worry Kathy, my brother is going to fuck you tonight to find out if that is true.”

“No, seeing him naked and talking is OK but I will not let your brother fuck me.”

‘OK that is fine with me. Then why should I let your husband fuck me?”

“You are blackmailing me, Stella.”

“A fair exchange is no robbery,” Stella said. “If I make my brother happy, maybe he will introduce me to his friends.Won't you, brother?

“Why not? Now that you have asked me for it, I have someone in my mind. You know who that is, don’t you?" I winked at Stella.

By now Kathy was fully aroused and was willing to do anything.

"Stella, tell your brother to fuck me nice. Make me scream and enjoy myself. I have not had a good fuck for a long time. You know what? The moment I saw your brother at the airport, I did have the urge to be fucked by him."

‘Kathy, do you want me to leave while my brother fucks you? Or…" Stella asked.

“You want to watch me being fucked by your brother do you not? So that you can know how good a fucker he is compared to all those lousy fuckers you told me about.”

“Not that,” Stella replied.

“Shut up, stay and watch me being fucked by your brother. I find that idea thrilling.You don’t mind Chubby? We can teach this kid sister of yours a thing or two,” Kathy said becoming bolder.

“I don’t think that will be a good idea Kathy. My sister, watch me fucking you?”

‘Don’t let me change my mind and ask you to fuck her before you fuck me.”

“OK sister you can watch the live tiger show.”

Kathy was all dressed up. Stella went up to her and removed her shirt, then undid her bra. Catching her breasts she said,“Kathy, your breasts are as firm as mine. Come here, brother, and feel them. They are just like your kid sister’s breasts. Feel them and imagine you fondling your kid sister’s breasts."

I went up to Kathy and started to fondle them. Looking at Stella I said, "Kathy you do have very nice and firm breasts, I will miss them."

"Don't worry Chubby, when you miss me you can hold your sister's breast and think of me. Tell her I am not holding your breasts but Kathy's." We all laughed while I kept on fondling Kathy's breasts.

“Ooooofffff …… aaaahhhh it is so nice to have a man fondling my breasts after a long time. Please suck them, Chubby. They have not been sucked for a long time.”

I took her nipples in my fingers, started to rub them slowly for a few minutes. Meanwhile Stella had removed all of Kathy’s clothes from her body and sat on the chair watching me suck her friend’s nipples. I sucked Kathy’s nipples back and forth while she moaned and groaned for about ten minutes. Stella was watching my face enjoying my making love to her friend.

I then moved slowly to her body, rubbing her body which had slight wrinkles. I looked at Stella. She was asking me with sign language how it was. I signaled to her that I was not enjoying it.

I then proceeded to her cunt putting two fingers in. It was too loose. I tried three fingers and then four fingers. Finally she had some feelings and started to move. I started to rub the soft spongy area where mom had really enjoyed. I kept rubbing that area for about fifteen minutes.

That was when she started to moan loudly, enjoying me rubbing her G spot.

“Yes darling that is nice. Fuck me, fuck me hard. Finally I am getting that thrill you used to give me when we were newly married. Yes dear push it harder.”

She did not realize that it was me and not her husband fucking her. Also she did not realize that I was finger fucking her. After some time Kathy started to moan louder and wriggle her body.

Stella signaled me to put my cock in. I did so. My cock went in and I only felt my cock touching vagina walls slightly and there was no grip on my cock. I signaled Stella that her cunt had no contractions to grip my cock.

Kathy suddenly went wilder and started screaming and going wild just like mom and Stella and slowly became soft.

I got up and cleaned myself. Kathy lay there for some time. I sat beside Stella watching Kathy. I then whispered into Stella’s ears,”You owe me a double fuck. I did not get any satisfaction fucking her.”

“What are you two whispering?” Kathy asked. She had recovered.

“Nothing, he was just reporting how great you were. How, Kathy, did you enjoy the fuck?”

“Stella, thank you. It was really satisfying. I had a great time being fucked by your brother. Please bring him with you when you come to meet my husband. While you fuck my husband, I can get fucked by your brother.”

“Thank you, brother, you gave my friend a good fuck that she deserved and will not forget. You can go back to your room and rest. Hope you can sleep well after enjoying fucking my best friend.”

Stella knew I did not enjoy the fuck then what did she mean by sleep well after enjoying fucking her best friend?Was she hinting me to keep awake and that she would visit me when Kathy went to sleep?

I went to my room and waited for her to come. It was a half hour before the door opened and she came. We quickly ran towards each other and hugged for some time. We then sat on the bed.

“Thank you, brother. You really satisfied my friend. She was so happy and relaxed that she went to sleep immediately. So how was it? I thought you were enjoying fucking her.”

"You saw that I had to use four fingers to go into her cunt and it took about fifteen minutes to rub her G spot to arouse her.”

“What is a G spot, brother?”

I kissed her on her lips and laid her on the bed. I then put my fore finger into her cunt about two inches and stopped and started to rub her spongy wall. She immediately responded with pleasure.

“That, my dear sister, is the G spot, which by rubbing for about fifteen to twenty minutes is enough to get a woman wet and ready for penetration.” Meanwhile I kept on rubbing the area.

“I did just that to Kathy and she thought that it was her husband fucking her. She was not aware that it was my four fingers doing the job. I could have even put in my whole hand in and she would not have known.”

“Why did you not put in the whole hand? It would have been nice to watch that.” She laughed.

“When you told me to put my cock in I did so. It was like throwing a pail into the well,” I told her.

“So all the bastards I fucked were only trying going in as deep as they could, while the pleasure point is only about 2 inches away. No wonder they could not satisfy me. By the way where did you learn that?”

“My mother, my teacher,” I told her.

“So you managed to find out the secret and fuck her?” Stella asked.

“Yes I managed to. I will tell you all after your friend has gone back. What about you, did you get to fuck your father?”

With a big smile she said, “YES.”

We did not realize that it was over twenty minutes since I had my finger inside her cunt. She was all wet and her jets were shooting her juices from her vaginal walls.

“Brother, I did not see you shooting into her, so I knew you need to relief yourself. That is why I came to give you a relief. Where do you want to shoot? Make your choice into my mouth or the cunt. I will enjoy anyone of the two."

“I think your cunt will do fine, so that we both can relieve ourselves at the same time.” It took me about fifteen minutes before I could shoot into her.

“OK, brother, now what is the solution for Kathy’s problem? I cannot be going to satisfy her husband every now and then.”

“Right, as far as Kathy is concerned, you will have to teach her husband that the pleasure point is 2 inches away not deep in. He should finger fuck to satisfy Kathy,” I explained to Stella.

“What about her husband? How does he get his satisfaction?”

"Yes, Kathy, does have a big cunt. My 8 inch cock also could not fill her cunt so how can 6 inches fill it up?”

“So her husband has to go round looking for young and tight cunts?” Stella asked.

“Not necessary,” I replied. “There is a solution." I poked my finger into Stella’s ass hole.

"Ouch, what are you trying to do?" Stella asked.

“That is the solution. Her husband wants a tight hole well there it is,” I replied.

“Will Kathy agree to it?” Stella asked.

“Does she have a choice? It is that or divorce.”

“OK I will ask Kathy to stay back for another night. No use talking about. She will need to have to have a demonstration. Will you give her a demonstration?"

“No I have not done that at any time. I will not enter her through the back door.”

‘OK then I have no choice but to visit Kathy monthly, fortnightly or even weekly, to keep her husband in check. You will like that brother?”

“You, emotional blackmailer, are too much. Okay for your sake I will force myself to oblige you. What if I find it thrilling? Will she allow me to visit her when I feel like entering the back door?"

“First let’s find out if you enjoy the back door entry. Then we will think about it,” Stella replied.

"You mean you…Will allow me to…?” I inquired.

“It depends on Kathy If she finds it thrilling then I may…Consider but no promise. OK, it is getting late. Wait for tomorrow. Good night.”

The next day Kathy wanted to leave.

“Stella, I have to leave. Don’t forget to pay me a visit as soon as possible as promised.”

"No Kathy, you have to stay back for another night,” Stella told Kathy.

“Is it Chubby or you who want me to stay back for another night?” Kathy inquired.

“What if it was Chubby who wants you to stay? Will you stay?” Stella asked.

"Stella, I was praying that you would ask me to stay back for another night. I so very much want to get fucked by your brother once more. I dared not ask you to stay for another night. Thank you,” Kathy said so excitedly.

“OK we will meet up with Chubby in the afternoon. He has got some solutions for your problems,” Stella told Kathy.

“Stella, you have seen your brother naked and loved watching his 8 inches cock. You even watched him fucking me. Why don’t you…If you permit I will ask him to fuck you today.”

“No, Kathy, we have talked about it and agreed that what may happen, we can even walk around the house naked, touch and feel each other and talk about anything, but no fucking.”

“I don’t know how you two can resist each other, Stella? He is definitely a good fucker.”

Afternoon came and we met in Stella’s room. Kathy came running and hugged me. She then undressed and stood naked in front of us. "Stella, you don’t mind Chubby fucking again do you?"

“No problem, Kathy, but first we have to talk.”

Kathy came over to me and undressed me. She went on her knees, caught my cock into her mouth and started to suck it. She was a woman let loose behaving unashamedly.

“Kathy, Your husband is right. Your cunt is too loose. Even a 10 inch cock will not be able to fill up that hole of yours to thrill you,” Stella told Kathy.

“Then how did Chubby thrill me yesterday. I am dying to feel that thrill now,” Kathy said.

“Listen carefully, Kathy, we will show you how.”

Stella put her fingers into her cunt and told her to just relax and feel her fingers going in slowly. When they were 2 inches in Stella began to rub the spongy area.

“Do you feel anything, Kathy?”

“Yes,” Kathy replied.“ That was the feeling I wanted to feel again .It feels so good.” Stella kept rubbing slowly.

I went up to her upper part of her body and started kissing her all over her face. Kathy’s moans started. I fondled her breast and nipples. I sucked them. About twenty five minutes of Stella fingering her cunt and me kissing her all over, Kathy’s moans became louder.

"Aaaaaaahhhhhh ooooooffff nice, faster, Stella, harder."

Stella began to feel Kathy shooting her juices and her vaginal walls beginning to contract. She signaled me to mount her. I went between her legs and pushed my cock into her cunt. Stella moved away and caught Kathy’s legs and wrapped them around my buttocks. She made her wrap her hands around my body as Kathy was not conscious of what was going on. This was becoming a routine where mom, Stella and now Kathy lock their hands and legs around me, when having an orgasm.

Kathy screamed, wriggled and went on to have her orgasm the second time in two days. She was so very happy. Slowly Kathy became soft and lay relaxed.

“Kathy,you must teach your husband how to rub that spongy area, which I was rubbing all the time. That is the solution to your problem. Now that your problem is solved on how get your orgasm, you must offer him a tight hole,” Stella explained.

“What can I do?" Kathy replied, "Chubby just proved that I have a loose cunt. All I can do is to allow him to have other women, starting with you." she asked Stella.

I poked one finger into her ass hole and told her, “You will have to offer him that hole.”

“No. No that is crazy. It's unnatural,” Kathy objected.

“Well think about it. You want to have your morality or your husband?” Stella asked her. “Even my brother is not willing, but I had to force him to agree,” Stella explained to Kathy.

“What? I have to let your brother fuck me from the behind? Why can’t I ask my husband to do it instead of Chubby?

“Kathy, first you are already comfortable with my brother and want him to fuck you as many times as possible. Two, it will be painful for the first time and you two may abandon the idea. With Chubby and me here, my brother will do his best not to hurt you, so that you can get used to receive your husband’s 6 inches with ease.”

“But Chubby has got 8 inches. He may tear my ass hole.”

“Don’t worry, I will be watching and guiding the whole process personally.”

Reluctantly, Kathy agreed.

Stella made Kathy go on her knees and her arms to support her, pushing her ass hole up. I went on my knees and adjusted my cock to her ass hole. Stella got the bottle of grape seed oil which we had organized earlier and lubricated my cock with her hands, pouring about a tea spoon full into her ass hole.

“Brother, put in one finger and lubricate her ass hole," Stella instructed. I slowly put in one finger.

“Ow, it is so sensitive there,” Kathy spoke.

“Yes,” replied Stella.” It's because your ass hole is still virgin.” She signaled me to put in two fingers. I did so.

“Ouch, it hurts,” complained Kathy. Stella poured more oil into her ass hole. I started to move my fingers in and out as though fucking her cunt.

“Chubby, please it hurts. Aaaaaah, please take your fingers out.”

I took them out.

"See Kathy, if you were with your husband, you two would have abandoned the idea. Did it hurt much?" Stella asked Kathy.

"Not much, as Chubby was kind enough to take his fingers out when I asked him to as soon as it began to hurt," Kathy replied.

"OK, we are going to try again slowly and if it hurts let us know," Stella told Kathy. "Please, you will have to bear a little bit of pain to reach our goal. No pain no gain."

Stella again lubricated my cock and told me to put my cock head in only. I slowly put my cock head on her ass hole and slightly pushed my cock head tip in.

“That is nice and soft," Kathy said. Hearing that, I quickly pushed the whole of my cock head in.

“Slowly, Chubby, or you will tear my ass hole. It is hurting slightly," Kathy informed. I pushed in about one inch and slowly two inches in.

“Oh, god, it hurts, please take it out.” Kathy was in tears. I took my cock out. She turned round and lay on her back.“No, I cannot go through with it. It hurts too much."

“You see, Kathy, if it was your husband he would have agreed not to continue. We have the whole of the afternoon and night.We are going to keep trying until we get all of it in without any pain. Rest for a while and we will try again. You have to be brave and bear the pain.”

Stella slowly started to poke her two fingers into her ass and push it in and out, slowly the third finger. Kathy was beginning to feel comfortable with this and enjoying it.

"Shall we try again, Kathy? Try to bear the pain as much as you can tolerate."

"Yes," Kathy replied. "I am beginning to like your fingers in my ass."

Kathy was asked to get into position again. I put in more oil into her ass hole and pushed my cock head in slowly. She did not complain I then pushed in two inches Kathy complained that it hurt but not as much as earlier. While she was talking I pushed in at least 5 inches.

“Slowly, Chubby, it's beginning to hurt slightly.” I then pushed the whole of my 8 inches in. Kathy screamed loudly.

“What is it Kathy?” Stella asked and signaled me to press her breasts and nipples hard and give her pain there too. I did so.

“It is painful please tell Chubby to take his cock out immediately,” Kathy pleaded.

“Where does it hurt, Kathy?” Kathy was not sure. "Is it the ass hole that hurts more or the breast?" Stella inquired.

“Chubby, stop pushing in more. Just leave it there for a while, will you? This much pain I can tolerate but if you push in more then it might hurt."

"Kathy, when it stops hurting let me know so that we can try to go in a little bit more OK?" Stella told Kathy.

“OK, Stella, but if it hurts you must ask Chubby to take it out.”

After a while Kathy began to move her buttocks to feel my cock. She was beginning to enjoy all of my cock inside her but she was not aware that the whole of it was inside.

“Stella, I am beginning to feel comfortable and loving Chubby’s cock halfway in. I think we can try another inch in. I should be able bear the pain.”

“What? Another inch in Kathy? You have already taken the whole of his 8 inches in you.”

“Oh god, what a tight fit. I can feel the whole of Chubby’s cock in me. Come on start pumping. What are you waiting for?"

I slowly started pumping her until I shot into her. When it was over, Stella asked Kathy how it was.

"Me? I really loved it. It was even better than being fucked in the cunt. Chubby, did you enjoy it my dear?" she asked me.

"Kathy, fucking your ass was just like fucking a virgin. So tight. Thank you I enjoyed it," I told her. "I hope I don't become addicted to the back door entry. Where do I find another woman who will give me the thrill you just gave me?" I replied looking at Stella with a wink.

"Hey, you dummy, you just fucked a virgin ass. It has not even been fingered by any of my dates or even my husband. Oh, Stella, you should try it with your brother, not as a fuck but training. You will not regret it. I can help you like you helped me."

"Don't worry Kathy, I have lots of men who have been begging me to let them try my ass hole. In fact, I promised one of them that should I want to try the back door entry I will go to him only," Stella replied smiling at me. "I am sure he will be very happy when I invite him through the back door."

"OOwww my ass hurts a bit, Stella," Kathy complained.

"Don't worry, Kathy, have a rest now. It will be OK by evening."

Night came; Stella called her brother to their room.

“Brother, I need you to do a test run on her back door again to see if the passage is clear or not before we send her back home.”

I looked at both of them, puzzled.

“Well, young man, don’t worry, you can fuck me until you tire out, as it is going to be a while before we meet again. I will tolerate any pain you give me.”

Actually, I, too, was keen to make the back door entry again as I did enjoy it. It was smooth sailing in when I gave her the full dosage so that she would remember me for a long time to come. After it was over we started to make the next move.

“Stella, I need you to visit me next week to teach my husband what and how to do it. OK? I want to present you to him as his birthday gift. Pleaseeeee bring Chubby along to keep me company while you are busy with my husband.”

All agreed and Kathy left the next day.

To be continued…

Please make your comments to guide my future episodes, especially suggestions on how Stella can seduce her father in their hotel room.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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Posted 04 Dec 2012 15:38
Excellent. Well written on giving help to his sister's friend. Took her ass cherry and satisfied her G Spot. Let Them do a day together after her friend goes home. "V=5++++."

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