Ally and her Sister Pt. 01

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Jeff Dates a Single Mom.
12.3k words
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Part 1 of the 2 part series

Updated 06/08/2023
Created 01/11/2017
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She lived in an apartment complex at the north end of town, what would have been the wrong side of the tracks if there were a railroad. The buildings needed paint, the trash needed picking up, the outdoor lights were in tough shape. It was the kind of place where you worried about who might be waiting in the stairwells at night.

I followed her up the narrow steps to a second floor unit. The door opened with a creak and we stood directly in the living room. A young woman with short blond hair looked up and said hi before she saw me. Sandra grabbed my hand and pulled me close to her side, "Ally, this is my friend, Jeff." There was silence as the woman looked me over.

Sandra asked, "How is Willie?"

Looking down at the book in her lap, Ally said, "He's been good, like he always is." A few seconds later, there was a cry from a back room. Sandra looked at me and smiled, "He hears my voice and wants me to give him some milk." Ally chimed in, "Yeah, he's a regular lunch mouth, he is."

Sandra said, "Jeff, make yourself at home, I'll be right back. There's beer in the fridge."

I looked at Ally and said, "Would you like me to get you something?"

"No, thanks, I have to watch the snacking. I'd have a sip of your beer if that's ok."

I helped myself to a beer, walked back into the living room, and sat on the sofa apart from her. I was surprised to see the TV off and papers next to her. Holding out the beer, I said, "Homework?"

She took a small sip, then a larger one, and handed it back. "Yes, damn it. It's an algebra problem set and I'm not getting it." She looked up at me with large blue eyes under her bangs, "You know any algebra?"

"Some."

She handed me the book and a sheet of quadrille homework paper. "Number 4."

The question involved equations in three variables and wasn't easy. "What course is this for?" I asked as I looked over the partial answer she was working on. There was an exponent error about halfway through that made the result come out wrong.

"I'm taking the hardest courses I can at the community college so maybe I can transfer to Berkeley in a year. My mom and my sister never went to college and that's why they're waiting tables. That's why Sandra let herself get knocked up by that asshole Ralph. She thought he would take care of her and the baby."

She stared at me, unblinking, waiting for some asshole guy comment back.

I shrugged and said quietly, "I think I can show you where you are having trouble with this one," my finger on the line of her homework with the error.

She slid over closer and looked down. "This is a quadratic, not a cubic function. If you change this, then the rest of it is correct."

Ally looked up at me in surprise. "How come you know this stuff? How come somebody smart like you is going out with my sister? Are you just here to give her a roll in the hay?"

I sensed a shadow out of the corner of my eye, but kept looking at Ally and said, laughing, "That's too many questions at once. Your sister is a very nice person and I'm not here to just have sex with her. You seem to have a low opinion of her men friends?"

Ally squinted at me, smiling herself, "You know the saying, 'unlucky in love'? That's my sister. You know what her problem is, she gets lonely and horny and lets the next guy she meets take advantage of her!"

"You think she brought me home just because she was lonely and horny?"

"Well, I don't know anything about you except you are very good looking and you know about my algebra. She's never gone out with anyone like you before, at least that I know about."

Sandra came back into the room, holding Willie unselfconsciously to her breast. "Ally, stop giving Jeff the third degree. He's a wonderful dancer and didn't make any moves on me tonight. And, for your information, he helped me get the dumb old car started the other night at work and asked me nicely if he could have a date."

Sandra sat down with us and handed Willie to me, "Make yourself useful while I change sides." She wiped her leaky nipple, put some tissue into her bra cup, and then let the other side down. It was full and pink and beautiful and leaking. Willie was squirming and about to cry when she took him back and gave him her generous breast. She smiled up at me, "Still happy about dating a single mom?"

I smiled back and leaned over to kiss her cheek. Instead I got her lips, warm and soft. After almost a minute, Ally said, "Hey, no making out in the living room, I'm doing my homework."

I turned and looked into those blue eyes, which were getting to me, and leaned in to kiss Ally too, and also got the lips instead of the cheek. Now Sandra said, "Hey, who's stealing my date?"

Ally pushed her algebra book and papers onto the table, then jumped into my lap, straddling me and pushing me back against the cushions. She put her hands into my hair and kissed me on the lips, holding on for a long time. Before Sandra could complain again, Ally said, rubbing herself on me, "Sis, can we keep this one around? He looks nice, he smells nice, he feels nice, and he helps with homework!"

Sandra's eyes drilled into Ally, "All right, just for that, you can put Willie down."

She looked at me as she hitched up her nursing bra. "Another beer? Want to

share one? It's good for my milk but bad for my waistline."

I nodded and she got another from the kitchen, then walked up to me, pulled her skirt up around her waist and sat down across my lap. "If Ally can jump into your lap, so can I."

I pulled her into me, kissing her neck and massaging her back. She grabbed my hair and started kissing me as Ally had. "I heard her asking you if all you wanted was a roll in the hay, but I didn't hear the answer."

I silently asked myself, "Are you going to let yourself get tangled up in this family? Is the sex worth it?" A little voice said, "You don't even know whether sex with her is any good."

I kissed her again and said quietly, "I haven't been this hot around a woman in a long time, but if you want me to leave, I will. I'm not sure it's fair to your sister to just disappear in the bedroom."

A face appeared next to mine from behind the sofa. "No, it's definitely not fair to disappear into the bedroom with Sandy. Either you take both of us to bed, or neither of us," she hissed, and then bit my ear.

Sandra looked a combination of startled and angry, then reached behind me and pulled Ally over the back and in between us. She had changed into a nighty with skimpy boy shorts under it, and fought back as the two of us pinned her down. My hand accidentally slid up her thigh into her crotch, which was warm and damp. Sandra noticed, and put her hand in the same place, making sure to rub hard into Ally's mound.

Ally sat up and put her arms around both of us. "Hmmm, this is nice." Then noticing a spot on her sister's blouse, she said, "Sis, you're leaking again," and started to unbutton the blouse. She smiled at me and said, "You and I can help her with her problem."

Sandra jerked back and said, "Ally! You're not going to do that in front of Jeff."

Ally kept on undressing her sister and said back, "Yes I am, and he's going to help."

Her hands working fast, Ally had the blouse and bra off before Sandra could react and quickly latched onto the nearest nipple. I could see the other nipple was also leaking, so leaned in and started gently sucking.

Sandra leaned forward, letting more milk flow, and moaned, "This is so bad."

Ally lifted her head and said, "No it's not. You like it. Admit it." Then she went back to emptying the breast.

I was in heaven, getting my fill of warm, sweet milk right from the source. I had ended up with one arm holding down Ally and the other under her and between Sandra's legs. My fingers were resting lightly on warm pussy. Sandra moved her thighs and my fingers got up into more pussy covered by her briefs. I wondered if I could get around the cloth and into the real thing. Sandra was rubbing on me and still moaning, "Bad, bad, bad."

Now I had a new problem, because Ally grabbed the hand that was around her and pushed it inside the waistband of her shorts. This was serious, two hands and two pussies and warm milk squirting into my eager mouth. I was in overload. Ally was also rubbing her hard behind into my equally hard cock that was still lodged in my jeans.

I abandoned the luscious boob in front of me, sat up and said, "This couch isn't working for three of us. Show me a bed."

Ally had now taken charge. She stood and pulled us up and led down the hall to her room. "We have to be in here, because Willie sleeps in Sandra's room." She pointed to a door and said, "The bathroom's in there if you need it." I did, and when I came back, the two sisters were naked and climbing into the bed, which was an old fashioned double, meaning we would barely fit.

Ally ordered me, "Turn out the light, drop those clothes, and get in here."

Sandra was on her back in the middle, with a towel that Ally handed her over her breasts. Ally said, "They'll stop leaking pretty soon. You don't know all the trouble Willie and I have keeping her empty. Maybe you can help with that chore too if you stay around. Did you like the taste?"

All this practicality was getting to me. I responded with some of my own, "Ally, are you legal?"

Sandra reached over and pulled Ally on top, rubbing her back and curvy butt. "Yes, she's legal, barely. We had an 18th birthday party for her last month. But she's still a virgin despite the brave talk."

Ally broke in, "But I don't want to be. I don't want to have to use my fingers on myself when I hear you with some guy, screaming your head off!" Then she put her head down between Sandra's generous boobs and cried.

I pulled Ally over against me, one hand on her chest and one across her belly, with my erection pressing into her crack.

I whispered in her ear, "Guess what, I'm only having sex tonight with one woman, and it's not you. No cherry popping tonight. But if you're still interested, I'm willing to stick around tomorrow and talk about it."

She turned around, giving me a hot and wet kiss while squeezing my cock hard. "OK, but I get to stay here while you do Sandy."

Big sister had been taking this all in, saying nothing. Now she reached across and pulled on Ally's nipple, rolling and pinching it. "You are a total minx, you know that?"

It occurred to me that if we got Ally off, that would help the situation. So my fingers found their way down the flat belly and into her sex, which was wet and ready.

Sandra and I took turns kissing her, working on her boobs, and eating her pussy. She came, hard and noisy, then fell back, catching her breath.

After all the buildup, it was time to do something about my problem. I quickly rolled on top of Sandra and slipped into a hot, wet core. She was tight, but wanted me in there and thrust up hard. "Oh yes, more, more, more."

The rhythm was slow at first and quiet, then faster, harder and louder. Finally, Ally reached over and covered Sandy's mouth, saying, "Shhhh, you'll wake up Willy."

I don't know if Sandra even heard that, because she went over the edge and into a tremendous orgasm that shook the bed as she came. And I was right behind, with a fountain of cum painting her insides.

In a minute, Ally was there with a washcloth and a towel, cleaning us up and announcing, "OK, fucking's over for tonight, everyone go to sleep." I pulled Sandra to me and was asleep before my head hit the pillow.

I woke up to little sucking noises. Sandra was on the other side of the bed, feeding Willy and smiling at me. Ally was making banging sounds in the kitchen.

Sandra said, "How do you feel, lover?"

I said, "Like a mascot in a circus."

Sandra frowned, "Is that good or bad."

"Well, if you like the circus, that's good."

"So, do you like our circus?" Willy was finished and put down in his crib in the next room.

I stared at her and pointed to my lap. The generous breasts needed a lick or two. The smiling lips needed a long, hard kiss.

"Oh, oh," I heard behind me as Ally walked in, naked as a bluejay. "Fun and games already?"

"No, I was just saying good morning to your sister."

As I stood up to go to the bathroom, she put the breakfast tray down, walked over, pushed my hard cock down between her legs, and gave me a full body hug. I cupped her behind and pulled her up to meet my lips. Soon there were thrusting tongues, little female moans, and rubbing of pussy on my cock.

"Is this an ok good morning?" she giggled. "When does the fun with me begin?"

"After we have breakfast and after all of us have a serious talk."

We sat on Sandra's bed. Ally folded her legs yoga style, facing me with tits and pussy in plain view.

I sipped my juice, eyeing her unblinkingly until she said, "What?"

I wondered if Ally was getting the message about who was ahead of her in the pecking order. Deciding that things needed to be crystal clear, I pushed Sandra around until her pussy was exposed and then quickly entered and pulled her back across my lap.

Wrapping my hands around a wonderful set of nursing breasts, I bit down lightly on her shoulder. This earned me a hard squeeze on my cock.

I looked at Ally, who was not smiling. "Come here and crawl into Sandra's lap."

Sandra helped by hugging and kissing Ally, who climbed in tight and started wiggling.

"Am I just supposed to sit here while you make my sister feel good?

"We're going to have a talk," I said. "What do you have in the way of boyfriends?"

She stared at me over Sandra's shoulder. I leaned forward and kissed her with a lot of tongue and also thrust up gently into the warm cunt that was making me feel good. Sandra's hands were working on Ally's back, then in her hair. After she finished, Sandra got a kiss too.

Ally's eyes teared up, "I'm not girlfriend material. The boys think I'm too smart. And if they try something on me, they usually get hurt because I've been taking self-defense."

She turned to Sandra, "Sis, let him be a friend to both of us, ok? Just this once, not forever?"

Sandra squeezed me hard and hugged Ally hard.

Sandra said, "This is crazy. One nice guy with a big cock, one horny single mom, one virgin, all in the same bed."

Ally started crying, rocking back and forth in her sister's arms. I put my arms around the two of them, thrusting gently into Sandra and getting squeezed gently in return.

Ally looked up at me, "You know, this is not easy, hugging my sister while she's got you in her. I'm the one who hasn't been getting any sex."

Giving her the third degree isn't helping, I thought. The hostility of last night was gone. Now I had two women in my arms, both of them wanting and needing sex from me to prop up their self esteem. What good would taking Ally's virginity do for her? Maybe it wasn't up to me to decide. She was eighteen, wanted sex, and was making her own decision. I reached in between them, rubbing Ally's small breasts and tweaking her nipples. Then I slowly lifted Sandra out from in front of me and laid her down on the bed.

Ally looked at my wet, hard cock pointing up at her. "Is that for me?" she asked.

I pulled her in closer and whispered, "If you want it, you can have it."

My fingers were feeling around in her pussy, finding her clit and working down further. She was wet, very wet.

She kissed me urgently. This was not the defiant, taunting girl of last night. This was an almost woman, not sure what to do with a guy who was treating her so nice, wondering if I would disappear the second I was done screwing. I lay back with her on top of me, shaking. Sandra reached over and rubbed Ally's back and the hard curve of her butt.

"You don't have to do this right now, Jeff isn't about to disappear, are you?"

I looked hard at Sandra, wondering if a giant trap was being sprung. Have I just become the live in boyfriend, lover, substitute dad, and provider?

Ally popped her head up and said, "If you don't take my cherry right now, when are we going to do it?"

I tossed her in the direction of her sister, swatting the beautiful ass as it went by.

We laughed. I leaned over and used hands and lips on all the nice parts of the sisters. The moment was passing. It was time for a shower. I went to get up, but got pulled back down between the girls.

Sandra kissed me and said, seriously, "You're making us feel bad. We've never had a sexy guy be nice to us and not mind Willie. It's ok if you just leave, we'll understand."

Ally wasn't so understanding, climbing back on top of me. "Please Jeff, just stay around today. We'll cook for you. We'll clean up the mess. I'll even vacuum!" She rubbed her pussy on my cock, which was hard all over again.

I took a deep breath. "OK, here's the deal. I have to take care of some things this morning for a couple of hours while you work on this place. When I come back, we'll go out for lunch and some shopping. We'll get some DVDs and some groceries and come back here for a movie and a special dinner. I'll cook, and you have to promise not to complain about my food."

Before she could say anything, I flipped over and took Ally's pussy into my mouth, my hands kneading her butt and my tongue working her over vigorously.

"OK, yes, that's great, please don't stop, oh, oh, you're going to make me come."

Sandra arranged herself over Ally's head with her breasts in her face and her lips pulling at Ally's stiff nipples.

Ally was building up to a big orgasm, with both of us working on her. Now is the time to do her, I thought, when she's not expecting it and not tense. I stepped up my licking and it wasn't long before the teenager was having her first big come with a guy. My cock was iron hard as I moved up over her body, found her entrance with my tip and pushed slowly inside.

Sandra watched me slide into Ally and smiled in approval. It was time to get this over.

Ally stiffened up and then relaxed back into the bed, spreading her legs and pulling her knees up. "Oh yes, please do me."

I pushed firmly into the teenage twat that was already squeezing me. I talked dirty to her. "God, Ally, you're squeezing me to death. Where'd you learn to be such a slut? I'm going to have to talk to Sandra about your loose behavior."

She was very turned on, humping at me and crying for more. Sandra and I kissed and she mouthed, "keep going" at me.

I picked up the pace, driving Ally to orgasm. I wasn't far behind. We came almost together, kissing and gasping. Her strong young body turned us over and she sat up, eyes wet.

"I'm not letting you go, ever. I don't care what my dumb sister says."

Sandra got her in an armlock and kissed all over. Ally's dripping pussy was pushed in my face and Sandra sat on my still hard cock.

While my tongue worked in her, Ally leaned back against Sandra and said, "What if we offered him both of us? Any time he wants."

I pulled them down alongside. "Will Willie behave if we have a nap?"

I came back slowly. One warm body was still pressed to me. The other one, fresh from the shower and smelling lovely, was sitting on the edge of the bed, smiling at me. She leaned down and whispered, "That was such a nice way not to be a virgin anymore."

We kissed tenderly and she said, "I'm in love with you."

I thought about putting her over my knee and pounding some sense into the fine body, but decided that could wait. I got an arm around my date from last night and walked us to the shower. From behind, Ally said, "I'll do something about the bed."

Sandra made Ally get some clothes on, but let her sit in my lap while brunch was produced. Willie was in his carrier at the end of the table, still sleeping.

Ally was chattering away to me in a quiet voice. "That was so nice. I can't believe it. I'm tingling all over. How will I ever find a boyfriend of my own like you? Why don't you have a steady girlfriend? I think Sandra is going to beat me for spoiling her date..."