Helping Josh

My brother and I were always close. He was a good brother, a year older than me, and because he was somewhat of a nerd, he always helped me with homework and such.

Josh had never had much luck with girls. He couldn’t string three words together when talking to a girl. Of course, his looks didn’t help. He was bone skinny, red headed, and covered with freckles. Needless to say, at the time he entered his first semester of college, he was still a virgin.

I wasn’t exactly a cheerleader. At five-six and one hundred and forty pounds, I was just an “ordinary” girl. My hips and shoulders were too wide and my face was too plain. Still, my DD cup tits got plenty of attention.

I didn’t have any experience with sex (other than with the vibe my mom had given me) until I began dating Brad during my senior year of high school. After dating him for about six months, I began giving him hand jobs and later blowjobs. I even started letting him play with and kiss my bare tits, and even finger my pussy. After a while, that wasn’t enough for him, and my unwillingness to let him fuck me finally drove us apart.

Josh and I weren’t shy about talking about things like that. Of course, he thought Brad was a fucking idiot. I had to agree with him, but I knew plenty of girls in school who put out, even long before their senior year. I wasn’t opposed to having sex. I just hadn’t found the right boy. Josh expressed that he’d be satisfied with wherever a girl wanted to draw the line. He’d only French kissed one girl, and she’d refused to go out with him again.

That summer though, after my graduation from high school and prior to my starting my first semester at the junior college near our home, Josh came to me with a huge problem.

I knew he’d been on a few dates with Julia, a girl his age. She wasn’t pretty or ‘hot’, but he liked her. On their third date, after going to a movie, they went parking at the lake just outside of town.

Julia let him feel up her tits and then agreed to give him a blowjob. As you can imagine, Josh was all in for that. While relating it to me, his face and neck got really, really red, so I prodded him, “What happened, Josh?”

“She undid my belt and unzipped my pants, but when she reached into my underwear and her fingers touched me, I blew my load. God! I was soooooo embarrassed. How can I ever ask her out again?”

Wow! I didn’t know what to say. Nothing like that had ever happened with Brad. In fact, sometimes I’d get irritated when it took me too long to get him off. Of course, I wasn’t about to tell Josh that. I told him simply, “I’m going to do some research on it. I’ll let you know what I find out.”

* * *

Our parents were at work the next day when I found Josh sulking in the den. “I spent all evening researching your ‘problem’.”

“Yeah, so did I.” He said in a defeated tone. And then he got up and walked over to Dad’s wet bar.

“What are you doing?”

“I’m fixing myself a drink. I have a feeling I’m going to need it for this conversation.”

“You don’t drink.” I scolded him, “But if you’re going to start now, fix me one too.”

I shuddered when I took my first sip of the whiskey and Coke mixture he’d prepared. “That tastes terrible.”

“Yeah, well, it’s not the taste I care about. So go ahead, tell me what you found out.”

“First, that it’s normal for some teenage boys to cum too quickly. Starting soon after puberty, they start masturbating. But, for fear of getting caught, they try to cum as fast as they can. Over a few years of that, they train their bodies to cum quickly. Some do it over a dozen times a day, but the average is closer to two or three times a day. That’s a lot of training. How often do you do it?”

Josh shrugged and stared at the floor in front of him, “On average, three times a day.”

“Then you’re right there in the mainstream of boys your age. There is a technique–”

He interrupted me, “Yeah, I know, the squeeze technique, but there’s a problem with it.”

I took another tentative sip of my drink, shuddered again and said, “I know. It’s more difficult for you to do yourself. It’s better if someone else helps.”

His tone turned hateful, “Yeah, there’s already a line forming at the door.”

Without thinking, I shot back, “I’ll help you.”

He shot his head around and showed me a pitiful look, “Yeah, right!”

I was too far in to back out, “I’m serious. I love you and I want to help you.”

“You’d really do that?” He asked when he realized I was serious.

“You can just close your eyes and pretend I’m someone else—one of the girls you think about when you’re doing it.”

“And who will you pretend I am?”

“The boy I love very much and want to help.”

* * *

I got up and went into the kitchen. I was back a few seconds later with a roll of paper towels. And then I sat on the sofa and beckoned for him to join me.

“NOW?” He said in a panic.

I forced a giggle, “Do you need another drink first?”

“Hell yes.” And he got up and headed to the wet bar.

I hadn’t finished half of my drink, so I downed the rest of it. After my gagging, coughing and shuddering subsided, I held out my empty glass, “I’ll have another one too.” I did like the way it was making my body tingle.

I had Josh sit on my left, “It’ll be the same as in a car with you in the driver’s seat.” And then my brother shocked me by putting his arm around me and leaning in to kiss my neck.

I wasn’t sure how I felt about the kissing, but he was getting into it, so I didn’t resist, even when he kissed me on the lips. When he pulled back a little, I purred, “This is our third date, so it’s okay if you want to feel me up.”

Josh tentatively reached up and cupped one of my big tits. And then he purred into my ear, “Ummm, I’ve always wanted to do this.”

His admission shocked me, “What? I’ve never even seen you staring at me.”

“Oh, I do, trust me. I’ve always tried to imagine what you look like naked, especially your awesome tits. I think about them all the time when I’m . . . you know.”

I was blown away, “Really? You think about my tits when you’re jacking off?”

“Hell yes.”

I let that soak in for a few seconds before saying, “Then maybe you should see them.”

After a lot of fumbling around, I was sitting naked from the waist up beside my brother. After he’d been fondling my tits for a few minutes, I told him, “You can kiss them.”

His whole body stiffened, “Really?”

“Yes, I’m here for you.” In truth, I was getting a little horny, and the thought of having a mouth on my tits was exciting, even if that mouth did belong to my brother.

While Josh was kissing and licking my nipples, I cooed in his ear, “I’m going to reach over and feel you. Don’t worry if you cum. It’s okay. We have hours before Mom and Dad get home.”

While feeling of my brother’s hard cock through his pants, I was impressed. It felt nice. I tugged at his belt and then unsnapped and unzipped his pants. I was prepared for the fact that he might cum when I wrapped my fingers around his hot cock, but he didn’t. That didn’t happen until I said to him, “Ummm, I love your cock. I’m going to really enjoy sucking it.”

He blurted out, “Oh god!” And his body began convulsing. I tried to use my thumb and two fingers to squeeze it just under its bulbous head, but it was too late, so I settled for simply stroking him off.

My brother was very embarrassed, as one might expect, but I did my best to make him feel better, “It’s okay. It’s our first time, so don’t beat yourself up over it. We’ll do better next time. Now, get out of your clothes. I’ll put them in the washer. They’ll have time to dry before Mom and Dad get home. You can go put on your robe if you want.”

When I got back to the den, Josh was sitting on the sofa in his robe. He had what looked like a fresh drink in his hand. I was still naked from the waist up, “You’d better slow down on that. You don’t want to be drunk when Mom and Dad get home.”

“This is useless.” He said in a somber tone.

I scolded him, “No, it’s not useless. It was our first try. We’ll get better, I promise. You just have to give me a little warning so I can do the squeeze thing.”

He finally let out a little chuckle, “If you’re going to stay like that, we won’t have to wait long.”

Wanting to keep the fragile mood light, I cupped my tits and bounced them up and down, “Oh, you think seeing these babies is going to get you ready sooner?”

“No doubt about it.” He said with a naughty grin.

* * *

After only ten minutes or so, Josh slurred his words when telling me, “We can try again now, if you still want to.”

I giggled, “That was fast.”

He shrugged and stood up. His robe was tented in the front. “How do you want to do it this time?”

I thought about it for a moment and then told him, “Lie down on the couch and let me do all the work. But you know what you’ve got to do this time, right?”

He nodded, “Yes, give you a warning when I feel it happening.”

“No!” I scolded him with my tone. “You have to warn me before you feel it happening, got it?”

“Yes, Ma’am.”

When my brother was in position on the sofa, I didn’t rush. I began stroking his already hard cock very slowly. Actually, I was really enjoying myself. I’d never seen a hard cock so close in broad daylight, and I’d never had the opportunity to just take my time and play with one.

Every now and then, Josh would let out a low moan, but not so much that it made me panic.

And then the worst thing happened that a girl wants when she’s giving a guy a handjob: He passed out cold. “Oh great! That’s just perfect!” I said out loud.

I got up and went to sit in the stuffed chair and sipped what was left of my drink. It wasn’t making me shudder anymore, and it had every nerve in my body tingling . . . and I was fucking horny.

Finally, I got up and went to the laundry room. I moved his clothes to the dryer, and then I returned to the den. I immediately went to the wet bar and mixed myself another drink.

I sat sipping my drink and looking at my naked and sleeping brother. I had to giggle when I saw that his cock was still hard and twitching. “Hell, why not?” I got up and kneeled down beside the sofa. While sipping my drink with one hand, I reached out and slid my fingers around his throbbing cock. His body reacted noticeably.

Not wanting to take a chance on him cumming, I practiced the squeeze technique. With him passed out, I didn’t have to worry about hurting him as I squeezed his cock just under the swollen head. It took longer than I thought, but his hips finally relaxed.

Over the next thirty minutes, I stroked his cock slowly until I’d feel his hips tense and rise up. I’d apply the squeeze until he relaxed again, and then I’d go right back to stroking him.

Half way through my drink, my pussy was flowing generously. I couldn’t resist any longer. I got up and ran to my room, returning a minute later with my vibe. It slid into my drenched pussy easily, and when I turned it on, I’m sure my eyes rolled back.

I could hold it in place with one hand while rubbing my clit with the other. After I’d cum two times, I turned it off and went back to stroking my brother’s cock.

I couldn’t help myself. I moved up and began licking and sucking Josh’s nice hot cock. This was something else I’d never had the opportunity to do—give a blowjob at my own pace. Blowjobs with Brad had always been too rushed with no time to play. I was really enjoying myself. Of course, I did have to apply the squeeze to his cock several times.

I must have been playing with, licking and sucking my brother’s cock for almost an hour when I heard the dryer buzzer sound in the laundry room. Reluctantly, I got up and went to the dryer to get his clothes. Instead of taking them into the den though, I took them straight to his room.

When I got back to the den, I knew I had to get him to his room, but his cock, still throbbing and twitching was just too inviting. I downed the last of my drink, turned my vibe on and put it back into my pussy, and then resumed giving my brother a blowjob. This time, however, I was going to let him cum. I’d done enough ‘training’ for one day.

It didn’t take me long to have him shooting his hot cum into my mouth. I did something else I’d never done. Instead of swallowing my brother’s cum immediately, I kept some of it in my mouth, savoring the taste and texture. I LOVED IT!

But finally it was time to get Josh to his room. It took me a while, but I finally managed to get him to his feet, put his arm around my neck, and help him stumble to his room. I was tempted to just plop him naked down on his bed, but I decided to turn back his covers and wiggle him under them.

Just before leaving him to sleep it off, I pulled back his covers and took his now soft cock into my mouth. I was rewarded with another nice drop of his wonderful cum.

* * *

Mom got home before Dad, and as much as I tried to avoid her, it was useless, “Dorothy Elaine, have you been drinking?”

I knew better than to lie to her, else she’d never trust me. “Yes, Ma’am, but I can explain.”

“I’m listening.”

“Josh, he wanted to talk . . . bad girl problem. I thought a drink might help get him out of his funk, so we had a couple while we talked about it.”

She spun around and stared at me, “Josh has a girlfriend?”

I chuckled, “Yeah, kinda, but he bungled his first attempt at fooling around with her, so who knows now.”

“Oh, what happened?”

“Nothing serious, but it’s got his ego in the tank.”

She showed me a knowing look, “Ahh, he couldn’t get it up, huh?”

I shrugged, “Something like that, but I’m sure he’s going to be okay.”

“I wondered why he was in bed this time of day. Your dad can’t hold his liquor either.” And then she let out a chuckle. “So, you’re okay? You didn’t overdo it?”

“Nah, I’m fine. It didn’t affect me that much, except for making me really horny. After he passed out, I had to go take care of business.”

My mom let out a huge laugh, “Then you’re apple didn’t fall far from the tree either. Alcohol affects me the same way, which should serve as a warning to you if you’re drinking around boys. At least the two of you had the sense to do it at home . . . but don’t tell your dad.”

“He’s going to know when he sees his bottle in the den.”

“Don’t worry, I’ll take care of that before he gets home. I have another bottle in the garage. Just don’t take this as me condoning you and your brother drinking.”

I went over and gave Mom a hug, “Thanks, Mom, you’re the best.”

* * *

Josh slept all night and late the next morning. I finally went to his room and woke him up. I pulled the covers off of him, letting out a giggle when I saw that his cock was hard, “Time to get up, Bro. Go pee and then come to the kitchen. I’m fixing us some breakfast.”

He tried to cover his erect cock, so I scolded him, “Don’t bother. I’ve seen it, remember?”

He rubbed his eyes, “I’m a little fuzzy on the details.”

I decided to tease him a little, “Don’t worry, after you passed out, I gave you a lot of training . . . and I do mean A LOT. And just so you know, that squeeze technique works really well. You didn’t cum for well over an hour.”

His eyes shot open, “Over an . . . you did that?”

“Hey, just cause you passed out was no reason not to start your training. You did GREAT. Oh, and when you come to breakfast, just wear your robe. I don’t want to have to wash your clothes again.”

* * *

I had to laugh when Josh showed up in the kitchen with his robe already tenting in front of him. Not wanting to cut him any slack today, I walked right over to him and opened his robe, and then I immediately reached out and put my fingers around his hard cock. “There’s the cock I got to know so well yesterday after you passed out.”

He shot me a scolding look, “You’re having fun teasing me about passing out, aren’t you?”

I gave his cock a final squeeze and then released it, “Of course, but it’s not like I didn’t have fun too . . . oh, that’s right, you were unconscious when I got myself off with my vibe while playing with your cock.”

My brother’s eyes shot open, “You did . . . that?”

“Yep, it was incredible, sorry you didn’t get to see it. Now, you need to eat and then go take a shower, and NO jacking off. I don’t want you setting back the progress we made yesterday.”

“Yes, Ma’am.”

* * *

“Can I have a drink?” Josh asked me when he was laying naked on the sofa.

“Why, are you nervous?”

“What do you think?”

I chuckled and said, “I’ll tell you what: you can have one just to help you relax, but that’s it. We can’t have Mom coming home and finding you passed out in your bed again. If you pass out today, I’ll just leave you naked on the couch.”

He looked panicked, “She knew I was drinking?”

“Yeah, but I covered your ass. I told her you were having problems with your girlfriend . . . which wasn’t a total lie.” And I flicked his hard cock with my fingers with a giggle.

I went to the garage and found Mom’s spare bottle of whiskey, and made Josh and I each a drink. And then I told him to close his eyes and try to relax.

“I’ll warn you when I’m getting close.” He said meekly.

I chuckled, “No need. I did just fine when you were passed out. I learned how to tell.”

And then I began slowly stroking his nice cock. Sure enough, it was less than a minute when I had to apply the squeeze the first time. When I was sure he was past the urge to cum, I started again.

I had to apply the squeeze to my brother’s cock at least seven or eight times in the first thirty minutes, but only a couple of times over the next thirty minutes. He was definitely getting better all the time.

I was getting really, really horny, so I finally moved down and eased his cock into my mouth. His whole body stiffened and his eyes flew open. I let his cock slide from between my lips, grinned at him, and then cooed, “just lay back and enjoy. I’m going to finish you off.”

Sure enough, less than a minute later, he was spewing his awesome cum into my mouth. When he was drained, I told him, “Now, I need to go take care of myself. You can watch if you promise to be quiet and just watch.”

“Hell yeah!”

Two minutes later, I was naked on my bed, knees in the air, vibe in my pussy, and my fingers working frantically on my clit. Josh was standing in the door to my room, his eyes bugging out. When I saw the look on his face, I came hard.

* * *

After watching me get myself off, my brother was ready for another round of ‘training’, but I made him wait. I did, however, stay nude while I fixed us a snack.

Josh’s cock didn’t disappoint. It stayed throbbing hard the whole time. So later, when I was ready for another round, he was ready and willing.

This time, probably because he’d already cum once, I didn’t have to use the squeeze on him nearly as often, and those times didn’t come until I was sucking him.

After getting him off the second time, I let him sit on my bed beside me and suck on my tits while I used my vibe on my pussy and clit. He wanted to go down on me, but I didn’t want to let him do that . . . YET!

* * *

For the next two weeks, I got my brother off at least three times a day, each time lasting for an hour or more. It was really difficult for him to resist jacking off on the weekends when our parents were home, but he managed.

The only accident happened during our first session on a Monday morning after he’d had to abstain all weekend. He came the minute I touched his hard cock.

Reluctantly, after three weeks, I knew I had to wean him off of my doing everything for him. I started making him jack off with me watching. I admonished him to go slow, enjoy it, and make it last as long as he could.

After the first couple of times, I began masturbating myself while he jacked off.

I did eventually let my brother eat my pussy. The first time wasn’t all that special. When I finally gave him permission, he crawled between my legs and kissed my pussy a couple of times, and then he immediately began trying to thrust his tongue into me.

I had to give him a lot of instructions, even though I had no experience with it. “No, no, just lick me for a little while.”

After that, he came to rely on my instructions. That was as difficult for me as it was for him, but I knew what I wanted at any particular moment, so I just tried to relate it to him.

Sometimes I needed him to tease my pussy with his tongue, but other times, I needed him to be more aggressive and suck my clit between his lips and flick it with his tongue.

He finally caught on and seemed to know what I needed.

Even when I let him eat my pussy, I wouldn’t give him a blowjob and finish him off until he’d been jacking off for over thirty minutes. I did love sucking him after all, and I really loved his cum.

One time, when he was eating my pussy, and doing a particularly great job, I lost control, “God! Get up here and fuck me.”

My brother’s whole body tensed. He looked up at me, “Really?”

“Yes” I gasped, “I need to feel your cock inside me.”

When he finally moved up over me and positioned his cock at my opening, I reached down and guided it into me. And when his cock finally slid past my resistance, I screamed out, “God yes! That’s it, fuck your slut sister’s pussy.”

And he did.

When I felt him shoot his hot cum inside me the first time, I was hooked on that feeling.

We didn’t do that regularly, but sometimes when he was eating my pussy, I’d just get carried away and beg him to fuck me. Of course, I didn’t have to beg much.

* * *

When it was time for me to start college and Josh to go back to college, our times together without our parents around was severely reduced. We both still lived at home though, so we did sneak in a “session” now and then.

Josh eventually got a girlfriend, and according to him, she really appreciated all the hard work I’d done with him, even though she didn’t know more than the results.

I resumed dating as well. I wasn’t a slut, but I wasn’t a prude either. I enjoyed sex with three boys over the next year. However, sex with them wasn’t the same as with Josh. There was nothing wrong with their cocks, but none of the three were any good at eating pussy.

I wasn’t able to just “play” with them like I could with my brother. I really enjoyed our laid back, teasing, joking, easy sexual relationship. And their cum wasn’t nearly as tasty.

Josh and I made a pact that we’d continue our fun even if one or both of us got married. We even got matching tattoos on our ankles. They were just simple doves, but we knew what they meant, a symbol of our pact.

* * *

The End

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