Chapter 3

Ann’s period didn’t arrive the next week either. She also wasn’t ‘helping’ me anymore. She continued jogging, which had the unfortunate effect of making her look more attractive while she would have nothing to do with me sexually. We hung out, but she made it clear that we were just brother and sister again.

One night I went to her door but this time when I heard her crying I knew she was actually crying. I went back to my room.

Meanwhile, I had been unable to masturbate to completion, I was so worried about Ann’s seeming pregnancy and where it left us. Even my favorite fantasy with Michelle seemed like a silly dream compared to the reality I had become used to.

“You okay, Andy?” Mom asked me at breakfast. I adjusted myself in my seat again. I couldn’t tell her that my balls were so ‘blue’ that I couldn’t sit still, so I just gave her a noncommittal grunt.

My mother came to my room one night after lights-out and sat on my bed. “Your teacher called to tell us you’ve really fallen behind. You wanna tell me what’s going on?”

I shook my head and lay back.

My mother’s eyes flicked to my persistent erection under the sheets. “I think I know what’s wrong ... your father had a similar problem when I was far along in my pregnancy and had no interest in sex. You haven’t been masturbating?”

“Mom!”

“Well?”

My cheeks warmed up and I shook my head.

“You have to let it out or it’ll hurt, Andy. Those little sperm factories between your legs got used to high output with Ann ... you can’t just stop ‘cold turkey’. Do you need some inspiration? Your Dad could buy you some adult magazines.”

My cheeks felt like they were on fire. My mother using Ann’s keyword, ‘inspiration’, plus talking about sex and being pregnant had an odd effect on me. My eyes shifted to her tight-fitting blouse and she noticed.

She shrugged her shoulders back, pushing her chest out a little. “Maybe ... maybe your old Mom can help?” She unfastened two buttons, revealing some cleavage and a little of her yellow bra.

“You’re ... you’re not old, Mom.” It was true ... if I didn’t know that my mother was in her mid-thirties, it would have been hard to determine her true age. She could have been Ann’s older sister, really, though with makeup on she was actually prettier.

I could see her cheeks redden. “What a charmer ... no wonder Ann couldn’t keep her hands off of you.”

At the mention of my sister again, my face darkened. Mom noticed. She unfastened her blouse entirely and pulled it off. “How’s that? You think you can work with this?”

I stared at my mother’s bra-clad breasts. They were pale and full ... when I was a baby I had suckled on those. My hand unconsciously moved down between my legs.

“I’ll leave you to it, then.” She got up and headed toward the door.

“Wait.”

She turned, one eyebrow arched.

“Can you ... take off the bra?”

She stepped back. “This already went farther than I planned. Are you saying my cleavage isn’t enough?” She eyed my tenting covers again.

“I ... I got to see Ann’s bare boobs all the time.”

She tapped her lips. “That’s true. Okay, I’ll do it if you show me what you have under there.”

I didn’t question that ... in a flash, the covers were off and my turgid erection was out in the cool night air.

Mom knelt down at the side of my bed, her eyes locked on it. “I think you’re bigger than your father,” she muttered, casually licking her lips. “Well, a deal’s a deal.” She reached back, unfastened the clip, and reached forward to catch the bra before it fell.

I heard a moan and realized it had come from me. Mom gave a small smile and slowly lowered the undergarment, revealing her large breasts. Like Ann’s, they were topped by dollar coin-sized pale areolas, but Mom’s nipples were thicker. I wondered if that was because of the breastfeeding ... would Ann’s look like that one day?

“We good? Or should I stick around for a few minutes?” She gave her boobs a little shimmy.

I moved my hand down and started stroking as I watched my mother’s breasts jiggle. Mom couldn’t seem to take her eyes off of my erection. I noted that her areolas seemed to be getting kind of ... crinkly?

“Oh!” I gasped, and then I was cumming. The first burst arced up and splashed down onto my chest, then another and another, gradually reducing to a trickle that spilled onto my hand.

“Goddamn, no wonder she’s knocked up,” Mom commented. Then she realized what she had said and shook her head before getting to her feet. “Alright, Andy,” she said as she put her bra back on, “hopefully this gives you something to remember for the future.” She shrugged into her blouse and took one last look at the large puddle of semen on my chest. I saw the tip of her tongue slip out to wet her lips again. “I expect you to get all that missing schoolwork turned in quickly. Good night.” Then she was gone.

A few days later, I caught sight of Mom doing some gardening. She was wearing some capri jeans and a flowery top that pulled up a bit as she bent down to pull weeds. For a woman who had birthed two kids, she was looking good.

But I hadn’t found my Mom attractive before Ann had started up with me. Now that I was hot for my sister, who was still cold toward me, and with Mom looking so much like an older version of her daughter, it seemed that my preferences had evolved.

She noticed me looking and gave me a wave and a pretty smile. I waved back.

Almost a week after Mom ‘inspired me’, she joined me at bedtime again, this time wearing a flowing skirt. “I hear you’ve turned things around at school, Andy, so I’m here to help again.” She unbuttoned her blouse.

“Does Dad know you’re here?”

“Mm hm ... he’s with your sister right now.”

“Oh?”

Mom pulled off her blouse to reveal that she wasn’t wearing a bra underneath so I was looking at her pale, ripe breasts again. “She’s having trouble sleeping so he’s been giving her massages.”

“Um ... can I have a massage too? I’ve been working out with Dad’s weights again, heavier ones now, and my arms and shoulders are sore.”

“Hmm ... okay, turn over.”

I did so and she pulled back the covers to reveal my bare ass. She paused only a moment before I felt her legs on either side of my hips and she sat down just behind my buttcheeks. I could feel her bare legs on mine, so she must have billowed out her skirt before settling down. Then her warm hands were rubbing my shoulders.

“Mm...” I moaned. Mom seemed to be pretty good at that. As her fingers dug under my shoulder blades I could feel myself relaxing ... well, other than that one part of my body that was now trapped under my stomach and rubbing against the cotton of my sheets as my mother shook the bed with her efforts. As she moved her hands to my upper arms I asked, “My pecs too?”

She stood up. “Turn over.” I did so quickly and beheld my topless mother looking down at me, her face rosy pink, before she settled back down, not realizing that put her crotch right above mine. She quickly hopped back, startled by the intimate contact, and then looked down at what appeared to be her own erection tenting the light fabric of her skirt as it settled back around her legs. She snickered. “Well, that’s not right.” She leaned forward and began rubbing my chest. Over the last few weeks, my weight training had made my chest more defined, and when I wasn’t staring at Mom’s breasts swinging back and forth with her efforts, I noticed that she kept glancing down and nibbling her lower lip. This continued as she moved back to rubbing my arms. When she was done, she sat back and looked down at my cock poking up between her legs. She thought for a moment, took it in hand, and then started stroking it. “I’ve always wondered what it would be like to have one of these,” she revealed as she masturbated ‘her’ dick.

When I started to thrust up into her hand, she stopped and dismounted. “You good?” she asked, and in answer I stroked my cock furiously until I groaned and painted my chest white.

She was moving to leave when I asked, “Mom? Can I get a kiss goodnight?”

She seemed distracted but came and gave me a peck on the cheek. I was pretty sure her hand touched my puddle of cum as she did so, but then she quickly headed back upstairs.

She came back a couple nights later in a blouse and capris. “Massage time!” she sing-songed as she pulled my sheets back, revealing my erection that had porked up in record time at the sight of her, a prettier, more mature version of my sister. She blushed. “Turn over.”

I did so and she clambered astride my buttocks again. However, she immediately dismounted and removed her pants. “These aren’t very stretchy,” she explained as she sat back down to massage my back, her lower half clad only in her white panties.

“Mom? Aren’t you gonna take off your top?”

“No, my boobs are feeling kind of sensitive tonight ... is that okay?”

I nodded as her fingers dug into my tired muscles. Soon, she had me turn over to massage my chest, but as she settled astride my hips she didn’t move back. In fact, as she rubbed my pecs, I could feel her panty-covered crotch rubbing along my length, barely at first, but as she moved to my arms she was definitely sliding back and forth along it. Her eyes were closed and I saw her nibbling her lower lip again. It was too much for me.

“Mom, I’m gonna...”

She continued moving upon me and then I was cumming. “UHH! Mom!”

Her eyes snapped open and she was off of me in a flash. The rest of my orgasm spurted onto my chest and stomach, but the initial blast...