Stepsister Cures Me

Notes

1. All characters portrayed are adults (18+)

2. Story doesn't involve whips, chains or leather

After an hour of teasing and denial I knew my stepsister Jen couldn't take it anymore, so just as she was about to blurt out the code word, I finally agreed to let her climax. We cuddled together after I unstrapped her and before switching roles so she could return the favor on me, we recounted the origins of our wonderful orgasm control dynamic and how we started engaging in it with each other before even knowing what it was.

Ten years earlier, we had both entered our senior year of high school and though not biological siblings, built a tight emotional bond within the first year of living in the same house. One late October Friday evening I came home and slammed the door, not caring if I startled her. I knew she was home alone because our parents worked at their restaurant each evening and Jen's car was out front.

She came downstairs with a look of frightened concern and asked me what was wrong, but I was too upset and embarrassed to talk at the moment.

"NOTHING. I don't want to talk right now."

You see, being somewhat reclusive, I had never experience real sex with someone, not even close until earlier that evening. I had just blown my chance to score with Becca Sloan, one of the more promiscuous girls in our class. The problem? I was too nervous to get an erection, and no amount of foreplay solved the dilemma. Couldn't bone up enough to even get a condom on. Worse yet, Becca thought it was funny.

I went to my bedroom and closed the door, praying for death to take me away. After about an hour Jen knocked on my door and came in holding her mobile phone, and sat next to me on the bed. She wore red gym shorts and was in her bare feet, her long blonde hair matching her cream-colored T-shirt. She wasn't wearing a bra; she usually didn't around me this time of night, and I couldn't help staring at her nipples.

"I got some texts from Becca Sloan a few minutes ago" she said.

Jen's blank expression said it all: she knew. By now probably everyone knew what had happened. Or maybe I should say had not happened.

"Did she send it to just you or were others copied on it?"

"Yes, just me. And, I texted back that I would brutalize her if she told anyone else. She says she didn't tell anyone and wouldn't. And that she feels bad that she laughed and wants to know if you are okay."

"Just tell her I'm fine."

"Ok, I'll do it right now." She composed the text, hit send and then said "Come here, Max, you need a hug."

Man did I ever, and the hug felt great. I had the hots for Jen and I think she knew it although neither of us had acted on it. We hugged a lot and sometimes I'd pop a boner from it, but not tonight. Jen knew I was a virgin and no doubt realized the devastation I felt.

I kept my face buried on her shoulder and felt her turn her lips to my ear. "I panicked my first time and hated it, but all I had to do was lay there. Guys have it so tough, needing to perform right from the start, the first time."

I nodded in agreement but didn't answer. Kinda liked her whispering to me like this.

"Once you feel how great actually having sex with someone is, this will never happen again. You'll be rock hard from the beginning, trust me."

Again I didn't answer.

"You don't have any physical problems so it's just that you're anxious," she continued.

"How do you know?" I asked.

She let go of me and sat back, and then said, "I've seen you tent up a couple of times. So, you know, it can't be broken or whatever."

"When?"

"Sometimes when we hug I notice it, and then if I come out of the bathroom wearing just a towel. Oh, and also when we hug and I start licking your ear just to goof around. Or when you stare at my nipples, like you're doing now."

I didn't feel a bit embarrassed by her saying this and Jen's face remained expressionless, her blue eyes twinkling. As I said, we were close. We talked a lot, about many topics including sex, although this discussion tonight was venturing a little further out on the branch.

Finally after a few moments, I said, "Yeah, whatever. I guess I should be thankful that it's not because I have a busted package."

Jen smiled. "What you need is the experience of a girl arousing you with her touch. It's a whole different ballpark than beating off – don't be embarrassed, we all do it – because once you feel that and you have an orgasm from her, even just once, you're going to want it so bad each time that you'll get a boner whenever you're with her."

"Yeah," I said, "I'm sure you're right. But I'm not going to be Becca's lab rat, I'm done with her no matter if she apologizes or whatever, and as much action as she gets it's not like she's going to waste time training me."

"I know, I know," said Jen, "I'd feel the same way if I were you. Anyone else you might like to ask out?"

"None. If you hadn't fixed me up with Becca this wouldn't have even happened. Not that I'm blaming you or anything."

"There are girls who would love to go out with you."

"Sure, the bible belters saving themselves for marriage. You know, or the sick and the dead. Or maybe the hard cores and crack whores with diseases that would penetrate an iron rubber and make my dick look like --" I hesitated, trying to find a way to end the rant and since I was staring at her bare right one, said "like your foot".

Jen laughed. "Yeah, okay, okay, I get it. You're so funny."

"I'm funny, huh. My cock doesn't work right but I'm funny. So at least I got that going for me."

"You're more crazy than funny, but at least you can laugh about all this dysfunctional penis stuff or whatever it's called. Let me sleep on it and maybe we can figure it out."

"Sleep on it, you mean you want to sleep on my limp useless dick?"

Jen sighed at my weak attempt at humor and then said, "Tomorrow's Saturday so between the two of us we should be able to come up with some possible solutions, if not by end of day then on Sunday."

"It's my problem though, so you shouldn't waste your weekend on it."

Jen hugged me again and let out a sigh. "Max, I don't think of it that way. You've had my back so many times in the past year that I'd do almost anything to help you. You're so unbelievably kind and supportive."

With that, we said our goodnights and pecked each other on the cheek. Thus ended the night before what would become one of the most incredible days of my life, a day that would change so many things in a profound manner.

I woke up the next morning and went to Jen's room but she was gone. The whole house was empty. Our parents' restaurant kept them occupied from dusk to dawn on the weekends and then I remembered that Jen was at the school's football game. She was a cheerleader and hated the games, especially on cold mornings like this one, but kept at it because the guidance counselor said it would help her get accepted at more colleges. I think he just liked the way she looked in her uniform but what the heck, the guy was only human.

After my night of little sleep, awakened by nightmares of dying as a virgin and being taunted by classmates, being alone in the house worsened my bitter mood. Jen didn't return until three that afternoon. When she came in and I asked her how the game was, she said "It SUCKED. We got killed as usual. And I froze my nipples off."

"Well, at least there's just one more game," I said as she put her stuff down. "I've been racking my brain trying to think of someone I could ask out, but – "

"Hold that thought," Jen interrupted. "I have an idea but I'm not sure you'll be into it because it's kinda out there, but give me a bit to shower and then come upstairs to my bedroom. I also want to re-read one article I found online last night."

I couldn't imagine what she was talking about. Perhaps a battery-powered dick sucker or something but in my troubled emotional state I would take any suggestions. I waited about thirty minutes and when I heard her finish drying her hair, waited fifteen minutes more.

I went upstairs and knocked on her bedroom door. She had her white bathrobe on, a terrycloth robe with a thick belt around it tied in a loose knot across her waist, the robe reaching a few inches below her knees. I imagined she was nude underneath but that wouldn't be unusual. We often sat together with her wearing just her robe.

I sat down beside her on her bed and said, "So, you have the magic answer to my woes? Can't wait to hear it."

Jen smiled and then blushed, and said "Oh, yeah? Well, you just wait." She paused and stared into my eyes and sighed.

"And?" I asked.

"Okay, here's the deal. I've read a ton of stuff about this and while there are all sorts of crazy suggestions in chat rooms, I found one article that makes some sense."

"My ears are all yours. Go on."

She smiled. "From what I've read, the reason first-timers your age have this problem is that they feel guilty about still being a virgin and want to get past it, but when they go out with a girl and think they're going to go all the way, they start getting nervous right from the start. Even days before the date. And, when they can't perform, it just keeps getting worse each time. Is that sounding like what –"

"Yeah, yeah, slow down. It's familiar all right. That's not too enlightening though. I already know all that." Jen beamed but didn't say anything, so I continued. "And you don't have to even ask. Yes, before the date I worried about it for days, and I wish I'd taken care of this milestone years ago, and yes I got more anxious as the night went on, blah blah blah."

"So," Jen said, "this sex therapist who wrote it says the best way to solve this involves little increments, working with a girlfriend, or maybe a close female friend with a helpful open mind, someone who won't criticize. You go in with both parties knowing that there's not going to be any full-on sex at first, and you just do little stuff each time until the guy gets anxious, and then you add to it until he maintains an erection, and ultimately you're able go all the way and have intercourse. Or, at least until the guy has an orgasm depending on their relationship with one another."

She paused and looked at me, awaiting my reaction.

"And?" I asked once more.

"That way, you know it's like I said yesterday, the guy experiences how great real sex feels, so the anxiety gets replaced by anticipation. Makes sense, doesn't it?"

"Yeah, that does make sense," I answered. There's still a problem though."

"You don't have a partner yet."

"Right. That's a minor complication to say the least so while I appreciate that you looked into all this for me, aren't we right where we left off last night? Oh, and I'm not going to Becca or any --"

"Well," Jen said, "that's why I said my idea is a bit 'out there'."

"Huh?"

"Bear with me," Jen said, then stretched her arms out in front of her, yawned as if anxious and arched her back so that it made a cracking noise. Her boobs looked spectacular when she did that, and sometimes when she was nervous – like now – she did it to take my eyes away from hers.

"Okay," she continued while looking at the floor. "We're not true siblings. But we still shouldn't have sex, because that would be weird, depending on how you define the word 'sex'. To me, 'sex' means going all the way, or making someone come."

I thought to myself, "No WAY, she's not going to suggest that we —"

"So." She looked up at me, then away, and sighed between breaths. "I can't believe I'm going to say this." She paused again.

"Say, um, say what?" I asked.

"You'd think after a hot shower and running a hair dryer that I wouldn't still be freezing," she said, clutching her arms across her chest with a shiver, looking up at me.

"Huh?"

"Ok fine, enough, enough," she said, her gaze returning to the floor. "I'll just say it: I could be your close female friend. Like a surrogate". She let out a huge breath and then looked up at me with anticipation.

I was stunned. She had actually said it. I responded by saying, "You're kidding. Right?"

"Look, I said the idea was out there so don't make me feel like an—"

"No no, it's not that at all it's –"

"It's up to you", she said, her eyes dampening.

"Wow", I said, and reached for her, hugging her close. Her robe parted so that her thighs were partially exposed.

"I care about you," she whispered, trembling a bit, her forehead pressed tightly against my shoulder. "And I hate seeing you struggle. Plus, as you know, I don't have a boyfriend right now so why not?"

"You'd really do this?" I asked. My pulse raced with excitement but I also felt a tinge of anxiety of the sort preceding my date with Becca.

She said "Yes," and my heart almost exploded. Then she sat back and said, "A couple of conditions, though. You have to understand that there's none of the all-the-way stuff so that has to be clear. And no one can ever know about this."

"Sure. Um. Of course," I stammered. "When do we start?"

"Well, we're alone at least five more hours so why not right now?"

I began trembling but not from being cold, and we hugged again. This was by far the most tantalizing concept I could have ever dreamed up. All the same, in the midst of hearing it I had this fear erupt regarding what I would do if my still-limp penis failed to rise to the occasion with Jen.

"You're sure about this?" I asked.

"Yeah, but one more thing: no kissing. It's too personal, weird and all that. Maybe on the cheek but no mouth. No intercourse, no coming, no kissing."

I nodded in agreement and we both looked at each other as if neither quite knew what to do. Then she shifted over to me and we clutched each other again.

"Are you hard now?" she asked whispering, her hands massaging my back underneath my shirt as I nuzzled her hair with my nose.

"No."

"God, this is SO weird," she said as she sighed.

I didn't respond.

"Do you want to be hard?" she asked, followed by a nervous giggle.

"Why are you laughing? I hope you aren't playing some kind of trick with this."

"Would never, never ever. You have to trust me," she said, scooting back. She continued, "And, if we're going to do this we should get down to business. So you might as well take your pants off and all that."

I studied her and not seeing a hint of deceit in her eyes, concluded that she was indeed serious. She wasn't kidding. I got up, stood in front of her and unbuckled my jeans and let them drop.

She sat there staring at my crotch, perhaps expecting a bulge in my underwear from a massive erection – one that didn't exist. I was limp as a fish.

"Here, step out of your jeans and lie down beside me", she said, patting the bed. After I did so she said, "Let me have a look." My heart fluttered as she pulled at my underwear waistband and bent forward to peek. She then started removing them and I helped by propping my knees up. Her robe parted and now I could see her thighs almost all the way up.

With my underwear gone, being naked in front of her excited me, all of me except for one part, and you already guessed which one. "Just relax," she said as she curled up beside me and placed the side of her face against my chin. My thoughts raced, especially about disappointing her when she was trying to help me, interrupted by her asking "Maybe you could kinda sit up a bit?"

I did so while keeping my legs straight out in front of me, and she scooted over sitting Indian style with her legs crossed, alternately looking at my eyes and my flaccid cock. "Looks like we have to take this to the next level," she said. Then she draped her thigh across my lap and looked up to see how I reacted.

Still nothing. She nuzzled up next to me nibbled on my ear, then licked around the outside of it. She knew how much I loved that, the warm wet feel of her tongue and the sound of her breathing. But, thanks to my continued anxiety I remained limp.

"What did the good doctor say to do at this point?" I asked.

"Well, they didn't include any play-by-play instructions. So. I guess we'll have to improvise."

She bent forward for a closer inspection of my penis, and picked a piece of bathrobe fuzz off it with her fingertips. The upper part of her robe opened enough as she did so that I could see her entire right breast.

"I thought you froze them off at the game," I said.

"Huh?"

"Your nipples."

"Oh," she laughed clutching her robe back together. "Wait, maybe if you see them that will help. Here, knock yourself out."

She turned her head to the side and held her robe open, exposing the most beautiful breasts imaginable. Aside from glimpses of them in the past of the down blouse variety, I'd never seen the entire display like this, and they were sensational. I stared in pleasure as her nipples hardened before me, and then she closed her robe and looked back at my penis.

"Still nothing", she said. "Man."

"I wish I had the –"

"Shh," she said, and again slid down next to me. "I'm going to try something else, something that might get you going."

"Like what?"

"A little role-playing thing, make believe. Like this". She moved closer to me. "Guess what", she whispered, her lips brushing my ear. "Do you know how close my pussy is to your dick right now?"

She had never talked dirty to me before. I liked it, and I mumbled "okay" as my penis started coming to life.

"It's so, so close. Less than a foot I bet, and if your cock was hard it could just about reach it. And guess what else. My pussy is absolutely soaked right now, and if you weren't my stepbrother I'd be fucking your brains out in seconds."

She pulled away and looked at me for a few seconds, blushing a bit while studying my face, and we both smiled. Then she looked down at what now was my massive hard on. "Wow, you like that sexy talk. That's the secret."

"Yeah, it worked that time", I answered, trembling with excitement. "But, Becca tried that approach too, and it didn't do anything. So it's not like you cured me with just a few sentences."

"Fine," she said. "We'll keep going, but remember the rules. By the way, I suspected you were big based on the bulges but – um – yeah. It is."

She pulled us close and put her lips next to my ear again, her body pressed against my side, and whispered, "I'm going to touch you now. Are you okay with that?"

I was nodding yes before she had finished.

She continued to whisper in my ear, "I can't tell you how many times I've brought myself to an orgasm thinking about how hot you are. Now don't get nervous." Then she reached down and rubbed my inner thigh, slowly working her way up, and just as she was about to reach my scrotum, she stopped, turned her head and looked down at my erection, which was now throbbing. "Maybe it's best if we let you calm down first," she said. "The increment thing, the approach we are supposed to use. I think you're suitably turned on for this part of it."

"Fine", I shrugged, faking indifference as best possible, though my heaving chest told the truth. We sat in silence, but with her being nude underneath her bathrobe and me exposed, there was no way my erection was going to subside.

"Let's cover you up and then start fresh in a bit," she said as she gathered part of the bedspread and draped it over me. "Tell me when I should check."

She laid back on her side of the bed facing away from me and started playing some sort of game on her mobile phone. I couldn't wait for my dick to shrink so I could feel her touch it, and with great concentration I focused on other things. It took what seemed like hours for it to soften up, during which we exchanged a few glances in which I conveyed "it's still hard" without speaking. Finally, it went soft and I told her, "Hate to interrupt your game, but I think you can check now."