Note: I advise reading Babysitting Amanda first, before reading this story.
After that first night, Amanda's mom asked me to babysit more and more often. Soon I was over there several times a week. Amanda, Becky and I fucked constantly while over there, and Amanda and I privately became boyfriend and girlfriend, since she was not much younger than me at all. I cared about her and would have done almost anything she needed or asked.
Amanda came to me one night after the three of us had gone through a thrilling threesome. She told me she was worried about her mom. Her mom, Jane, worked an office job at a market trading firm. Because of her job, Jane was under constant stress. According to Amanda, Jane had not had a boyfriend since soon after Becky was born. Amanda knew her mom masturbated, having spied on her a couple of times. She noticed that poor Jane never got much out of her jilling sessions, and while desperate for male companionship was to worried about her girls to get a boyfriend. Poor Jane, at only 30, was a desperate woman who needed a man to please her badly. Amanda begged for my help. After having slept with Amanda and Becky so many times, I was skilled in getting women off. However, I was uncertain. "You know your mom might not like this idea, I mean I am almost 15 years younger than her". "Becky and I will take care of that" Amanda responded. I was still reluctant. Then Jane nearly ended up in the hospital after a severe stress attack. Out of concern for this family, I agreed to help. The three of us then began to form our plan.
Jane came home one night to find Amanda, Becky and I watching TV. After a brief hello, she went off to take a quick nap. Our plan swung into action. I went to my overnight bag and retrieved some rope, a gag, and a blindfold. The three of us went to Jane's room and slipped in quietly. She was sound asleep. She had already taken off her outer clothing and was left only in her underwear, which made things easy for us. I peeled off her panties while Amanda removed her bra. It was then that I got a good look at Jane for the first time. While I usually didn't care for older women, Jane made my mouth drop open. She was a slender women, with two small, perfect breasts and a pussy to die for. I shook out of my lust and began to tie her legs to the bed post, while Amanda took care of her arms. Meanwhile, Becky applied that gag and blind fold. I checked the knots on the ropes, making sure they were comfortable yet tight enough to keep Jane from moving to stop us as we worked. I stripped to my boxers while Amanda and Becky went naked. When we were all ready, Amanda went over and gently shook her mom's shoulder.
When Jane awoke, she felt a set of lips on her right breast. I could see the shock on her face through the blindfold and gag. Amanda sucked her moms breast, pulling it between her teeth. I felt Jane try to struggle, only to find the bonds far too strong. Becky moved in on her other breast, and soon the two girls were working wonders on Jane, who's apprehension could not withstand the pleasure. I moved in on her pussy. She felt the hot breath on her clit and tried to close her legs, but could not. I touched my tongue to her pussy and she let out an unwilling moan. I went to work on her, having practiced on Becky and Amanda. As my lips propped her outer lips, I felt a shudder travel through her body. I pushed her harder, letting my tongue travel in to lick her inner folds. Jane was soon lost in bliss, well on her way to an orgasm. As she came close to climaxing, I pulled out, patting Amanda and Becky on their sweet young butts. We all stopped, teasing her. I could tell just how badly she now wanted what was coming to her. Amanda went to her mother and removed the blindfold. Jane blinked a few times, then her eyes widened in shock as Amanda leaned over to take her mom's tit into her mouth again. She was now fighting an inner battle between pleasure and decency. Becky and I resumed our places, and she shook in sheer bliss. I knew the battle was almost won. I plunged my tongue deeply into her clit, as Amanda and Becky increased their sucking. Jane was pushed over the edge into in incredible orgasm. Her body shook, out of control, as the orgasm wrecked her. The girls and I pressed on, pushing out every bit of that orgasm. I felt her pussy tense up on her tongue, and felt her cum running down my tongue into my waiting mouth. She had a slightly tart flavor, which I gulped deeply. Not a drop was spilled. With one last thrash and burst of cum, Jane fell still. We pulled away, and Amanda turned to talk to her mother.
"If I take this off, will you yell or scream?" Amanda said, indicating the gag. The submissive look in her mom's eyes gave her the answer. She removed the gag, and her mom breathed deeply. "What the hell is going on?" she said quietly, not daring to yell. She gave my an accuseing look. I shrugged my shoulders and indicated Amanda. "It was my idea mom. We've been so worried about you for a long time. We knew how badly you needed sex, and I begged Jake here to help." Amanda said lovingly. Jane was shocked. We told her the whole story, and she was quiet the entire time. The girls kept there hands on her breasts while I massaged her pussy. At the end, she sighed. "I never thought my two little angels.....would be like me." Jane revealed that she had loved the idea of sex at an early age, and had slept with a variety of men. Nothing negative happened until Amanda came along. The dad stayed long enough for Becky, then fled. "I haven't had sex since. Its been so hard, the reason why is because I love you two too much to risk it." "Its ok mommy, Amanda said. "We WANT to sleep with Jake. If you think he's a good pussy eater, you should feel his dick in you!' Becky laughed in agreement. Jane was apprehensive, but knew she had lost. "Ok, I'll give it a try. But take this crap off of me!" We untied the ropes willingly. Jane flexed herself. "Can I at least go to the restroom?" We relented, but no one bothered putting clothes on.
She went into the restroom, leaving the door open for us to watch. We crowded in for a closer look. As we watched, a golden stream of piss shot from her pussy to the toilet. It was a fascinating sight for someone who had not seen it before.
When Jane finished, we returned to her bedroom. She laid on the bed. Amanda and Becky moved in first, and soon the they both had found a tit. Jane buried herself in Amanda's sweet young pussy. The sight of this lesbian threesome hardened my cock instantly. I moved in on Jane's pussy and began to finger her. Her hole was surprisingly tight after years of no sex. I got 4 fingers in, and she moaned into Amanda's pussy. I slipped the head of my cock in and slowly moved forward. Jane's pussy gripped my cock tightly as I buried myself up to the hilt. She gasped as the last few inches of my member disappeared into her. When she was ready, I pulled out, then slammed back in. She screamed in pleasure into Amanda's pussy. The vibration sent Amanda crazy, and she shot towards orgasm. Becky's ass was soon in my face, and I fingered her pussy with one hand while holding myself steady with the other. I fucked Jane faster and harder. Her pussy tightened on my cock, sending my pleasure sky high. All the girls were now screaming in pleasure. I moaned as I felt the familiar bubbling in my balls.
Amanda came first, spilling cum all over her moms face. That set Jane off. She thrust herself onto my brick, sending my balls slapping on her ass. I came as well, shooting rope after rope into her. Becky came last, her little girl cum dripping all over my fingers as she screamed in please. We brought each other down from orgasm, as passionate, moaning foursome. With a wet plop, I eased myself out of Jane and helped Becky get down. Amanda collapsed onto the bed, and we lay there together. Becky and Amanda fell asleep on either side of me. Jane slept behind Amanda. The bed was soaked with cum, but we were to tired to move.
After several hours of sleep Jane and I woke up. We talked for some time. Considering her own craving for sex at her daughters age, she understood my position. She patted my cock and I massaged her pussy as we talked. We fucked again before the girls woke up. That day, we must have fucked a dozen times. Twice a week I came over and enjoyed nice little threesomes with the girls, then their mom when she came home. We kept each other satisfied for a long time.