Stepmom Helps Out Pt. 01

To my fans...I pulled my stories for personal reasons but I'm back. I'm going to re-do Part 3 as I rushed it and was never happy with it. Expect it summer 2016!

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Chapter 1

It was well past midnight when I got home from my last date with my now-ex Sarah. I had dropped her off at her house, having resisted the urge to tell her to go to hell and walk home. Getting dumped was bad, but having to drive her home was extra insult. As I pulled into the driveway I shook my head. This was the second time in a year I had been dumped, and for the same reason.

I unlocked the door as quietly as I could, hoping to wake no one. I passed my stepsister Liz's door and then turned the corner. As I did I heard the telltale squeaking of the mattress in my dad and stepmom's room. As usual, they were going at it like crazy. I remembered the first time I realized what the sound was, how erotic it was to realize my dad and stepmom were fucking. Now, hearing them night after night for an hour straight only eroded my confidence more.

I stepped into my room and shut the door. The squeaking bed was barely audible through my air vent, although I knew they were still fucking. I stripped off my clothes and looked at myself in the mirror. I was a fairly good looking guy, and had always had a steady stream of interest from girls. But now, with two girlfriends in a row, I was kicked to the curb, left to wonder if I'd ever get over my 'problem.' I lay down, trying to shake the feelings that washed over me, listening as my dad fucked my stepmom's brains out for another twenty minutes.

The next morning I woke up late. It was Sunday, and my dad was out golfing. I headed downstairs to find Liz eating breakfast with my stepmom Annie. Annie smiled sweetly, her hair disheveled from what I knew was a long night of screwing. Liz smiled at me, a look of glee on her face that I suspected meant trouble. Liz and I weren't close, even though we were the same age and both went to the local college together. Annie fixed me a plate of food and set it on the table. As she did her loose t-shirt fell open and I saw quite a bit of her cleavage. Annie had nice breasts, and I took in as much of them as I dared before looking over at Liz. Her eyes narrowed, clearly having caught me checking out her mom's chest. I knew Liz was insanely jealous of her mom's figure, even though she was pretty in her own right. Both women had blonde hair and bright blue eyes, but while Annie was curvy, Liz was a tennis player with a toned body. I didn't have a 'type', but I thought both women were attractive, and I envied my dad for getting to enjoy Annie on a nightly basis.

"How was your date?" Annie asked sweetly, sitting down to join us. I shrugged, not wanting to get into it, but Liz was ready to pounce.

"Oh, he got dumped," she chimed in.

"Liz!" her mother said.

"It's true," Liz said, her eyes alight with glee, "Sarah told me this morning."

That, I thought, was what I got for dating a friend of Liz's. I said nothing and ate quietly. It was awkward, and I avoided Annie's eyes. Still, she paused, then cleared her throat and tried to smooth over the situation.

"Liz, leave him alone," she said. "Mike, honey, are you alright?"

"Yeah," I said, meeting her eyes. She looked sincere and concerned, unlike her bitchy daughter who was grinning. "I guess it just wasn't going to work out."
"That's not what I heard," Liz said, ready to strike at last. I wondered how much she knew, but before I could tell her to shut up she blurted it out anyway. "Sarah said you can't last more than a minute in the sack!"

"Shut up!" I said. Annie tried to intervene but I got up, dumped my food in the trash, and stormed out of the kitchen. I grabbed my keys and seconds later peeled out of the driveway to the sound of Liz's derisive laughter. I drove around for a while, blaring the radio and trying to convince myself that Liz was full of it. But she wasn't, and that was what had set me off. With both Sarah, and Kristin before her, each time we had gotten down to doing it I would barely get inside them before losing control and coming. I tried everything I could find to delay my climax, but I couldn't. At first each girl was patient, even understanding, but as time went on I could sense increasing frustration, until they each came up with some lame excuse to dump me. And now they were telling their friends, including my stepsister. If I didn't do something about it, I'd be labeled as the "one minute man." But I didn't know what to do about it.

I returned home about an hour later. I was relieved to see Liz's car was gone; I didn't want to deal with her. I entered the house and found Annie sitting on a chair in the living room, waiting for me.

"Hey," she said kindly. "Are you alright?"

"I don't want to talk about it," I said a little too curtly, then stopped. "Sorry, I didn't mean to snap at you."

"Don't be sorry," she said. "Liz was awful to you to suggest that."

I felt my face redden. I sat down across from her. She was wearing running shorts and a t-shirt, and her hair was pulled up a pony tail. She was always working out, trying to keep "old age at bay" as she often said. Still, in her early forties, she looked great. I could see why my dad was so attracted to her. I looked up at Annie. She was always there for me, always ready to listen or give me good advice. I didn't think I could tell her exactly what happened, but I didn't have to—Liz did it for me already.

"She's right," I said, defeated. "I got dumped because of it."

"Surely that Sarah girl isn't that shallow?" Annie said.

"Are you saying there's something worse about me?" I said, again a little rudely. I apologized, and she smiled.

"It's alright, you're upset. I just meant, well, that's a pretty dumb reason to leave someone as great as you."

"Thanks," I said, "but I guess it's been enough for two girls so far. I mean, I can't even believe I'm talking to you about this. But, what if I'm just terrible at it?"

Annie smoothed her hands over her shorts and stood up. She walked around the coffee table and sat next to me. She patted me on the leg and smiled.

"You can last longer and be terrible at it, trust me," she said with a laugh. "Besides, I'm sure you're exaggerating."

"I'm not," I said plaintively. I had always felt close to Annie since she and my dad married ten years beforehand, and my problems just started tumbling out of me. "I'm serious, Liz wasn't kidding."

"Well," Annie said, pausing to reflect on what she was about to say, "this is going to sound weird from your stepmom, but you can learn how to...um, last longer."
I looked up at her hopefully, and she nodded. "It's true. I once had a boyfriend who lasted a minute, maybe less each time. But after a while I taught him how to last longer and then everything was great. Better than great, even."

"Really?" I asked. "But I mean is there a book I can get, or some kind of instructions. Maybe something online. Anything would be helpful."

She shook her head. "Not that I know of. I bet you've already scoured the internet and found nothing useful. It just took some patience, and time." She stood up, bending down to kiss me on the top of the head. "Be patient, it will work out. You just need to find a good teacher."

She walked off, her round ass swaying in the hypnotic way it always did, and I called after her "are you sure I can learn?"

She turned, grinning. "If your dad could learn how, so can you," she said with a wink, and walked upstairs.

I sat downstairs for some time, dumbfounded. If my dad was able to fuck Annie for as long as he did every night, then there was hope for me. I was filled with a sense of possibility, the possibility that the dread I had felt each time I was with a girl would eventually be gone. I was also filled with thoughts of my Annie getting fucked by my dad, the sounds of the bed squeaking and the occasional moan from Annie. If she could teach my dad to do that, then there was hope for me.

Of course, there was one catch. I needed to find someone who could teach me how to last longer. It wasn't a skill I wanted to ask for on a first date. Both Sarah and Kristie had been nice enough about it at first, but neither of them had any bright ideas that could help me. If only I could get Annie to tell me how she taught my dad.

The second I thought it, I realized that Annie could tell me how to last longer, if she wanted to. I mean, she said she taught my dad, but that doesn't mean she couldn't at least explain what she did. She and I had shared frank talks about everything under the sun, including sex, so what was the harm in asking her?

Determined, I headed upstairs. My parents' bedroom had a sitting room off of it overlooking the backyard, and that's where I found her. She was reading a book, and when I knocked on the open door she looked up and set it down on the table next to her.

"What's up?" she asked.

I took a deep breath, and decided to use every ounce of confidence I had. "Annie," I said. "I want you to tell me how you got my dad to last longer. Please."

She paused, a look of genuine surprise on her face, and said gently, "Mike, it's not something I can exactly explain in words. I kind of had to show him how. If I could tell you, I would. But I don't think I can help."

My face fell and she noticed. She immediately added, "I mean, it's not like I could actually show you." She stood up and paced around, looking out the window for a minute before turning to face me. "I wish I could help."

"Well," I said, trying to lighten the mood with a joke, "you could show me, if that would be more effective."

"No," she said flatly, clearly missing my intention at humor. She strode out of the room without a word. Before I could chase after her I heard the front door close. She was gone, leaving me feeling worse than I did that morning.

I tried to catch Annie later in the evening when she returned, but she resolutely avoided me. By the time Liz and my dad came home I was starting to worry that I had permanently damaged my relationship with my stepmom. Dinner and the rest of the evening was unbearably uncomfortable, and I wasted no time with a lame excuse to head up to bed early. I sat in my room, reading, trying to get my mind off of my problems with girls and now my strained day with my stepmom. I was so wrapped up in my thoughts that I hardly noticed the familiar creaking of my parents' bed across the hall from me.

"Great," I sighed to myself, settling in for another round of my dad slamming into my stepmom. I checked my watch. It was ten-thirty, somewhat early for them. As I read and the steady sounds of fucking came muffled through my air vent, I thought about Annie. She was pissed, that much I could tell. I wondered how I would make it up to her, if I even could. I had clearly crossed a major line with her. Maybe some serious housework would put me back in her good graces. She had wanted my dad to paint the front picket fence. Maybe I could surprise her.

My mind wandered and I stopped thinking about Annie and how I could make it up to her, and just thinking about her. She was always funny, and sweet. But she was also curvy and fit and I could see why my dad was attracted to her. The idea of Annie getting fucked nightly was one that was constantly on my mind, and as the muffled sounds of their coupling continued I found myself getting hard just thinking about her. I was just about to slide my hand down my shorts when the sounds from the air vent stopped. I paused, my fingertips just below my waistband, and listened hard. I looked over at my watch and noted disconsolately that it was eleven twenty. My dad had just fucked Annie for fifty minutes, and I couldn't last fifty seconds. I was about to go ahead and jerk off anyway to relieve my stress a little when there was a knock on my door.

I pulled my hand out of my pants and sat up. I made every effort to conceal my erection before whispering "come in." A second later the door opened and Annie peeked into the room.

"Busy?" she whispered. Her hair was disheveled and she was wearing one of my dad's t-shirts as a nightgown. I shook my head and she entered. I had left the room lights on and as she shut the door I could make out the outline of her underwear and noticed she had no bra on as she turned around. My penis, which had started to soften, was now growing again. I shifted, covering myself a little with a sheet to hide my response.

Annie sat down on the bed next to me. Her long, tanned legs were draped over the edge and she leaned back on her hands. I tried not to stare at her tits, but her nipples were hard and I took as many sneak peeks at them as often as I thought I could get away with.

"This morning," she said after a moment. "When we talked about...your concern. And you asked if I could show you." I started to speak but she stopped me. I looked at her and I could tell she had something on her mind. Her hair was a mess from getting fucked and I realized that she had just gotten fucked hard and was now talking to me calmly. I wondered if my dad came inside her, and if so if it was it slowly dripping out of her. My thoughts were suddenly brought back into focus as she spoke again.

"I don't appreciate your joke," she said calmly. She wasn't angry, I could tell. But Annie was not one to let things lie in silence to creep back up later. "I know you want some help but for god's sake, Mike, I'm your stepmom."

"I know," I said, my voice creaking from the strain of whispering. "That's why I asked. I've always come to you with my problems. And when you said you knew how to help, well how could I not ask? You can't dangle that in front of me and then expect me to accept it quietly."

She paused, thinking it over. "I'll give you that," she said, "I can't blame you for asking. But you know I can't help you like I helped your father. I mean..." she paused, blushing. "It was not merely a tutorial. It was hands on."

She blushed again and looked away, and then started to laugh quietly. I laughed too, although I took her averted gaze as a chance to look at her tits without reproach. When she turned to face me I was a little too slow breaking away from her tits. She looked me over but said nothing about it, and continued talking to me. "So I'm sorry I avoided you all day."

"It's okay," I said, "I'm sorry I upset you."

"At first I was upset, and then I thought about it, and I realized that it was kind of funny. Not your problem, honey, but what you asked. And then, I'll admit, it got me thinking about it."

"Is that why you and dad started going at it earlier than usual?" I asked. She blushed and laughed. We had joked many times about their sex life and she swatted me on the shoulder playfully.

"Well," she said, "I guess I had that coming." She leaned back, stretching, and as she looked down she saw, to my terror, my erection fighting against the sheets. She quickly looked away but I could tell she had seen it. I was about to say something apologetic when she sat up and turned to face me.

"Alright," she said, "maybe I'm in a good mood because I just got some, or maybe I'm making a huge mistake, but I'm going to help you. A little," she added quickly. "I can give you some pointers, ask some questions, alright?

"Okay," I said, unable to say anything else. I wasn't sure if she was kidding, or if she even meant what I hoped she meant. She stood up, stretching slowly and yawned. Her t-shirt rose up and I could see more and more of her thighs until I finally saw the first glimpse of her pink underwear. Her legs were slightly parted and her underwear was soaked through—I guess dad came inside her. She leaned forward and put her arms on my shoulders, looking me straight in the eye.

"We'll start tomorrow," she said. "And you're going to have to do what I say, how I say it. Okay?" I nodded, and she continued. "You can't tell anyone about this. And you have to answer any questions I ask truthfully."

Again I nodded and she stood up. She put her hands on her hips, and then said "Your dad and Liz will be out most of tomorrow, we can start first thing."

She surprised me and leaned in, kissed me on top of the head, and the started to walk out the door. She stopped halfway, and turned around. "See you in the morning." She stepped into the hall and closed my door. I slid my hand down my pants and started to stroke myself; I came before she even made it across the hallway.

Chapter 2

I woke up early the next day wondering if Annie had been kidding with me as a way to get back at me. I paced my room for a while until I heard one, then two cars leave the driveway. I changed, pausing twice in the mirror for some reason, and headed downstairs.

Annie was waiting for me in the kitchen. She wore tight, black yoga pants and a sports bra, fresh from her morning workout. Her skin glistened and her ample cleavage popped out at me. "In case you are wondering, I was not kidding with you last night. I'm going to give you some pointers."

"Thanks," I said, causing her to giggle.

"I can't believe I'm even talking about this out loud to you," she said. She hopped onto the kitchen counter, her breasts jiggling as she did do. "I'll ask you some questions while you have breakfast."

I fixed myself some food, looking over at her every so often. She looked at me expectantly, but said nothing until I was halfway through my breakfast.

"So, um," she paused, biting her lip. "Does it always happen early? And, is it only with a girl, or do you last longer when you're by yourself."

"Well," I said, blushing. "This is so weird to say out loud to you. Yeah, it's all the time, doesn't matter if it's just me or with a girl." It was mortifying to say that out loud, but at the same time Annie always helped me with my problems so it seemed natural to tell her.

"Okay," she said, relaxing a little. "Anything else about it that's concerning you? You know, like any trouble getting an erection?"

"Oh god, no," I said, and she laughed hard. "Everything seems okay. I mean, as far as I can tell. Do you think it's medical?"

"No," she said. "I think you're probably just too sensitive down there, plus you're probably overthinking things. Your dad was the same way, at first."

"Anyway," she continued, "I'm sure you don't want to talk about your dad." She hopped off the counter, again giving me a show. Her stomach was still flat for a woman her age, and I was pleased by her outfit choice. She sat down on the kitchen table, her legs swaying slowly. "Alright," she said. "I didn't give this a whole lot of thought. I mean, how do you want to start?"

"I hadn't thought about it either," I admitted. "I mean, aside from wondering if you were serious."

"Super serious," she nodded, giggling. "I don't want you to worry about how long you are going to last with a girl. But, um, I guess to start...well I guess maybe you should go ahead and take off your shorts? You know, so I can look at it?"

"Oh," I said. For some reason I hadn't thought she would actually see me naked. I paused, and she laughed, patting her knees gently.

"I mean, I've seen plenty of them," she said. "It's not a big deal to me."

"How many have you seen?" I asked, feigning outrage. She laughed.

"Just shut up and take off your shorts for god's sake, Mike," she said, still laughing hard.

I stood up, my hands trembling. I started to fumble with my shorts and started to take them off. She looked at me encouragingly. I was already hard, and as I took off my shorts my dick sprang out, throbbing and ready. Annie just looked at it for a few moments and said nothing, and then looked up at me.

"Alright," she said matter-of-factly, "let's see what we're dealing with. Go ahead and try to last as long as you can."

"Right now?" I asked, stunned by what she was telling me to do.