Weekend Coupling Ch. 02

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Introducing Mature Mother to Anal Pleasures.
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Part 2 of the 2 part series

Updated 09/27/2022
Created 12/10/2012
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Two weeks after Madhu and I enjoyed our first afternoon together (see Weekend Coupling) I received a text message: This Sunday OK?

I texted back: OK

I looked forward to initiating Madhu to more sex experiments. Mine was the first cock she had taken in 5 years as her husband was paralysed from waist down. Though married for 24 years, mine was the first cock in her mouth and down her throat and mine was the first tongue in her pussy. She left sated and it seemed she wanted more.

Madhu knocked on the door of my shed the same time as last and I invited her in. She came into my arms and we kissed. Our tongues fought their own battle as I caressed her back and ass. I squeezed her ass cheeks and she moaned in my mouth. We stopped for breath and I helped remove her sari and other garments. Madhu stood naked, her cheeks flushed.

As I looked her up and down, she whispered, "Don't look like this. I feel shy."

I kissed her and pulled her to me by her ass. She felt my hard cock on her mound and gasped. I moved back and put her hand on the belt of my shorts. She understood and unbuckled my shorts and drew it down as she went down on her knees. No underwear. She moaned as she saw my aroused cock. She put her hand on it and stroked it. I held her head and slightly pushed it in. She took my cock in her mouth and started to suck it. Her mouth went in and out.

I held her head and pushed in till my engorged cock hit the back of her throat. She understood what I wanted. She took a deep breath, held my cock, and pushed her mouth in. The tip went a little down her throat. She adjusted her mouth and pushed it in. My cock was in about an inch and a half. The same as last time. She was finding it difficult to breathe, but left my cock in her mouth. Her eyes bulged out and her cheeks were flushed. She was struggling to breathe, but pushed in more. About two inches down her throat. She held it there, choking, her body shaking and her eyes watering. I wanted to pull out but she held on tight to my cock. It was as if she wanted to test her limits.

When I thought that she would pass out, she pulled her head back slightly, allowing passage of little air as she struggled to breathe. Then she pushed her head in again! It seemed as if my cock went in more than last time. She gulped and my cock seemed to strangle. The pressure on it was great. She gulped again and I spurted with a force I never thought I could ever muster. I spurted a good 4 times before she pulled her mouth back and took the remaining juice in her mouth. She struggled to breathe through her nose. Tears ran down her cheeks. She swallowed my come in her mouth and slowly came to breathing normally.

I pulled out of her mouth and clasped her to me. I wiped tears off her cheeks and tenderly kissed her.

"Why, Madhu? Why, baby, did you do this?"

"I wanted to. It was awesome. I was choking and struggling to breathe and I orgasmed. The feeling was so...so...exquisite. Unbelievable. And I knew you wanted to push it down my throat. I wanted to do it for you too."

I kissed her and hugged her.

I took her to bed and held her to me till her breathing was back to normal. Our kissing session took off and we were aroused. I was hard against her and she was moaning and squirming. I put her on her back and entered her. I started to make tender love to her. She whimpered as her passion got out of control. As she was about to come I pulled out. She protested, "Why? Please......."

I turned her on her front, pulled her up by her hips till her ass was up and she was on her knees. I entered from the rear. She cried out, "Oh!" and looked back. I pumped into her and caressed her back. I put my hands under her and held her hanging breasts. I cupped them and squeezed them gently. I continued pumping, and pinching her nipples. She moaned. I pinched harder, knowing that she could stand the pain and torture. I pumped hard and pulled her nipples hard. She moaned loud, "Oh! Goddd! The pain, the pain." I kept the pressure on her nipples and she was sobbing, "Oh! My Godddd! Please....please...the pain is too much." I pressed hard and she screamed.

I let go suddenly and blood rushed into her nipples. The pain was excruciating as the blood rushed in. She kept on moaning till the pain subsided. I pumped and caressed her ass and pulled her ass cheeks apart. Her hole was small, never used by any cock. I had planned to finger her ass and cock it if she agreed. I had kept a small jar of Vaseline next to the pillow. I retrieved the jar, picked a glob with my finger and massaged her ass rim with it. She cried out, "What?"

"Just relax, Madhu. You will enjoy the massage. The feelings will be sensational."

I kept on pumping in her pussy and massaging her ass hole. Soon she relaxed as she became used to my finger there. I pressed a little in and the ball of my finger spread her rim. She felt the pressure and squeezed her rim shut. My finger was in the way. I caressed her back and ass. She was whimpering.

"Madhu, darling, I'm pushing my finger in, OK?"

"Oh! No! It will pain."

"Yes, it may a bit, but afterwards the pleasure will be much. Shall I?"

She looked back at me and I looked on. She whimpered and nodded. I pushed in. She moaned. I pushed in till the complete middle finger was in her ass. She was whimpering, more from the strange feeling than from the pain. I started pumping my finger in her ass and she moaned. I raised the tempo and she moaned louder. I realised the moaning was because of the pleasure my finger was giving. I pumped my finger fast and she moaned, "Yes! Yes!"

I put more Vaseline on her rim and introduced my index finger to her ass. She cried out, "Oh! God. It is stretching. The pressure is too much."

"Relax baby, soon you will get used to two fingers as well."

I pumped my two fingers and she moaned with pain. I increased the tempo and she whimpered, "Oh! Oh! Oooooh!"

I dilated my fingers and she cried out, "It's paining. It's stretching too much."

I caressed her ass and said, "Yes, baby. Soon you'll get used to this and enjoy the pressure."

I continued the pumping and her whimpering petered out. I wanted to replace my fingers with my cock.

I caressed her ass and said softly, "Do you want to go further, darling Madhu?"

"What's that?" she whispered.

"If you are ready to experience more pleasure, I want to do your ass."

"NO! It will pain too much. Your cock is thick and my ass is small. I don't think it will fit."

"It will pain in the beginning, but you'll start to enjoy it in your ass. Yes, there will be pain, but it will fit."

I let her think while I pumped my fingers and dilated them again. She cried and said, "Ooooh! I can feel the stretch."

"The stretch will be more than this. There will be pain also. After the pain, once you get used to the cock inside, you will enjoy the pleasure." I dilated to stretch her ass so she could know what the cock could do to her ass.

I kept on pumping my fingers as well as my cock in her pussy.

Then she whispered, "OK, do it."

"I'll be gentle, darling Madhu."

"Yes, I know my dear."

I pumped my cock hard and fast and pumped my fingers and dilated them a couple of times more. She whimpered.

I withdrew my cock from her pussy and my fingers from her ass. I applied Vaseline to her rim and pushed some inside her ass with my finger. She moaned. I applied Vaseline to my cock head and the shaft. I let her feel my bulbous tip on her rim. She flinched and moaned in anticipation of the pain to come.

I caressed her ass to relax her and said, "Darling Madhu," and pressed my thick tip past her rim. She whimpered, but did not cry out despite the tremendous stretch. I rested the tip just inside her rim and caressed her ass and back.

I whispered, "Baby," and pushed in gently. She moaned and flexed her ass muscle, gripping my cock hard. I streak of pleasure ran through my cock and it expanded. She felt that and moaned. I caressed her ass again and pushed in slowly till my balls touched her pussy. She whimpered. I started to pull out and push in little by little and she whimpered. My hands on her hips held her and I gently pumped in her ass. She was moaning and I could sense pleasure in her voice. I held her hips tight and slowly increased the tempo in her ass. Her moaning increased and I started to pump fast. She moaned and pushed back with her ass. I released her hips and just kept my hands lightly on her ass while I pumped in.

Then I cupped her pendulous breasts and squeezed them gently. She mewed with pleasure. I held her nipples between my finger and thumb and squeezed gently and then with pressure. She moaned as pain ran through her nipples. I pumped her ass and teased her nipples. I pinched them and she cried out. I pressed them hard as I pounded her ass, and she screamed as pain coursed through them. Then I gently pressed them to assuage the pain. I kept her continuously between pain and ecstasy by pinching her nipples hard and then pressing them gently, and she was whimpering and screaming.

I was reaching a point where release was imminent, so I left her nipples alone, to her relief, and fingered her pussy and clit. She moaned with pleasure as I thumbed her clit and her ass reared into me. I alternately rubbed her clit and her sensitive spot in her pussy and had her ecstatic and maddened as she screamed with pleasure. She orgasmed screaming and I unloaded in her ass. I pumped in four to five times hard and fast as I emptied my balls in her ass.

She collapsed on the bed and my cock plopped out of her ass. She lay inert and I lay on her. She was moaning with passion and I kissed her back and rubbed my spent cock on her ass crack. I turned her over and held her to me. I kissed her and said, "Madhu darling, are you alright?"

She smiled and said, "You were right dear, the pain was much but so was the pleasure. It was an awesome experience. My ass will remain sore for a week."

We went into a clutch and kissed like teenagers. Clutching and grabbing everywhere and our tongues having there own ecstatic battle. My cock grew hard and my sweet Madhu had it in her mouth in a jiffy. She sucked and licked and had me unloading my load in her mouth. She swallowed whatever I dished out and smacked her lips.

"I never imagined I'd love to swallow sperm and I like swallowing yours."

I lay her against me and we relished the pleasure of our love making.

Later, Madhu said, "My dear, once your house is ready and your family moves in, how will we meet? Now that I've found you and experienced the pleasures of sex, I don't ever want to let you go."

"Baby, we can always go to a hotel, but not in this town."

"Yes, my love. That's the best."

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Weekend Coupling Previous Part

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