My Sister Set Me Up on a Blind Date

Then it struck me - I needed to end the date before I completely lost control again. But I couldn't end the date abruptly as Ashlynne would think she'd done something wrong and freak out. But what if I ended the date in a spectacular but safe manner? She had made me cum already. I decided I should return the favor. We would keep our clothes on. I would show her how her date could make her very happy.

I said softly into Ashlynne's ear, "I'm going to make you feel very good if it's okay with you." No response other than Ashlynne continued to undulate against me. I moved my hands from Ashlynne's tits down her torso. "You can say to stop at any time, and I'm fine with that." When my hands had moved down, Ashlynne had stopped undulating against me. Now, she lay flopped against me, watching my hands move down her body. "You have such a great body and I'm going to explore a little more of it." My right hand went to her crotch while my left hand went a bit further to grab her thigh below her shorts. I rubbed my right hand's middle finger in her cleft, creating a camel toe.

"Do you want me to stop?" I asked.

"No."

"Does this feel good?"

"So far." Ashlynne seemed a little tense, a little scared. She hadn't expected this escalation, but she trusted me.

"Good. I'm going to do this for you and then you'll go inside. All right?"

"All right."

Ashlynne turned her head and kissed me while she pushed her crotch against my hand. We kissed as I slowly pulled my hand up her camel toe while pressing against her. She pushed her crotch against my hand in time with my strokes. Our kisses slowed as I continued rubbing her slit. After a bit, she stopped kissing me and laid back against me. She began taking deep breaths.

"You're so wonderful," I said softly. "I enjoy being with you. I'm so happy being with you. I want to make you happy. I want to show you how much I enjoy being with you. Come for me. Let me make you happy."

I continued rubbing my hand against her cleft. Ashlynne pressed her crotch harder and harder against my hand. Her breath got more ragged and then she was breathing in pants. I kissed her neck gently while I continued rubbing hard against her crotch. Ashlynne said, "Oh!" Then another "Oh!" Then a stream of "Oh! Oh! Oh!" Finally, her whole body shuddered as she clamped her legs on my hand. I held her lightly as her orgasm swept over her.

When Ashlynne recovered, she said, "God, that was great!" She gave me a quick kiss. "Thanks for making me feel so good. I've never come that hard before." Another quick kiss. "But I'm a mess now. My panties are soaked."

"My underwear is a mess from when I came earlier."

"You came earlier?"

"When we were dry humping."

"Mom has a beach towel behind this seat. Let's clean ourselves up."

I reached down and opened the box of emergency supplies Mom kept. I pulled out the beach towel. When I turned back around, Ashlynne had slipped off her shorts and panties and was naked from the waist down. She grabbed one end of the towel and started drying her crotch area. She said, "Take off your shorts and underwear."

I felt torn. I had kept moving the goalposts but had stopped at both of us keeping our clothes on. I didn't want to show my dick to my sister. That was crossing a line that I didn't want to cross.

"Come on," Ashlynne said. "It's not like I haven't seen a boy's dick before."

That was it. It was enough to galvanize me into action. My underwear was very uncomfortable, and I did want to get cleaned up. I took off my shorts and underwear.

"You did make a huge mess," said Ashlynne. "Cum is everywhere." She took the other end of the towel and rubbed it all over my crotch, moving my dick around when it got in the way. I stood upright with one knee on the bench seat and one leg on the floor. Ashlynne turned on the light so she could see better.

"Tonight's been so crazy," she said. "I felt so nervous about holding your hand, and now I'm cleaning your crotch like it's the most natural thing in the world."

"It's a great brother-sister bonding activity."

Ashlynne laughed. "By the way, I lied when I said I'd seen a guy's dick before. I've seen them only in pictures and movies. Yours looks kind of weird in person."

"Thanks!" I said chuckling. "You feel good about tonight?"

"I do. I had a great time, and I learned a lot. I'm hopeful I'll be comfortable and confident on my next date."

"Great!"

Globs seemed to be stuck to each of my crotch hairs. Ashlynne was drying each one with the towel.

"You're such a perfectionist," I said.

"I am. And it makes me miserable at times. I had to get every cheerleading routine perfect. Any mistake, and I was crushed, even if no one noticed. You don't know how many times I cried when I didn't get a 100 on a test or assignment. And as I told you, it made me panic on dates."

"Hopefully on your next date, you'll be able to relax. When things flowed tonight, they were great. You're a very sexy woman."

"I feel that way now, but I haven't on other dates." Ashlynne had the area above my dick cleaned up and was working now on the area to the right of my dick. "You know what really scares me? The idea of giving head to a guy. It's a valuable skill to learn. If you know how to do it well, it'll keep your guy satisfied without fucking. No need for birth control. No chance of pregnancy. It's how Mandy convinced you to go out on a second date. When I was riding in the car with Jeffrey after the movie, I thought briefly about giving him head when we got somewhere private. Then I remembered I had no idea of how to do it."

"It's not that hard. You can learn."

"No, I can't. Normally for something like this, I'd watch videos and practice, practice, practice by myself until I had it mastered. Only then would I be comfortable trying it with someone else."

"You can easily find videos where girls give head to a guy."

"I've watched porn at some sleepovers. The other girls who've given head hoot at the oral sex in those videos. They say nobody's dick is that big, and they'd gag on something so huge. They say when they give head, it's nothing like that. So I'm not going to learn how to give head by watching porn." The right side was clean and Ashlynne was working on the left side. "And I'd still need a guy's dick to practice on."

"Well, I could-"

I was tired, it was late, and I had driven a lot. I almost made a big mistake and fortunately caught myself in time.

"You could what?"

"Nothing."

Ashlynne gave me a 'don't give me that shit' look.

"Okay. I could give you some instructions on what to do." That wasn't what I was going to say, but it sounded reasonable.

Ashlynne went back to cleaning me up. She grabbed my dick and lifted it up so she could run the towel over my balls. She asked, "Have you ever given head before?"

"No!"

"Then I'd be better off with instructions from one of my girlfriends."

Ashlynne had accepted my altered line. I felt like I had dodged a bullet.

Ashlynne was apparently satisfied that my balls were clean and moved the towel up into my ass crack. Without so many hairs, she could clean a lot faster. Finally, Ashlynne seemed satisfied. She tossed the towel over the seat back and turned off the light, but she kept her left hand wrapped around my dick.

"Would you?" she asked.

"Would I what?"

"Would you teach me how to give head? That's what you were going to say, wasn't it?"

She had caught me out.

I said, "And I stopped myself because it was a very bad idea. I hope you weren't offended that I'd think of such a thing."

"I wasn't offended. I want to learn." She slowly caressed my dick with her fingers.

"Why not learn from your next boyfriend?" Should I have said first boyfriend?

"Because he'll expect I already know how to give head. And I'll panic because I can't do it right." She dropped her left hand to her side and moved her right hand down to cup my balls. In a sweet voice, she said, "You've made me come but I haven't made you come."

"It's okay. I came earlier." She moved her hand back up to my dick. I was very hard now, and her touch was giving me tingles. I needed to bring this date to an end. "You said you would go in after I made you come."

"I've changed my mind."

"We've done enough for one night."

"There's no night after this. We're both on a blind date with someone we'll never see again."

Ashlynne was playing the entitled princess game, where she expected to get what she wanted and wouldn't take no for an answer.

Or was I playing the entitled princess game? Putting up a fight while knowing that I'd give in because once I did, she'd make it fun. Regardless, I could feel my will to fight crumbling. Her hand softly exploring my dick wasn't helping. I found Ashlynne's combination of assertiveness and innocence irresistible. Who didn't want to teach a gorgeous young woman how to give head?

"When I see you on Monday morning," said Ashlynne, "none of this will have happened. We'll be as we have always been. You won't try to kiss me or touch me, and I won't try to kiss you or touch you. Tonight will be our special secret that we'll never discuss. Why not add a little bit more to it?"

Why not? It wouldn't hurt her, and it is something that would be good for her to know.

"If you're sure you want to do this..."

"I feel safe doing things with you. You've been so patient and haven't pushed me. Just the opposite. I've liked being in control." A little hint of concern crossed her face. "You'll be appreciative even if I screw up, right?"

"I doubt that'll you screw up, and I'll be appreciative of whatever you decide to do."

"Then I'm sure. I know already that I have to swallow. I'm probably not going to like the taste, but not swallowing ruins it for the guy."

"You learned that from your friends?"

"Yes. A few times, girls who don't like the taste have brought up not swallowing to my more experienced friends while I was around. The consensus is that none of the other options will satisfy the guy." She gave me a wicked smile. "And don't ask to come on my face - that's totally disgusting."

I chuckled. "I won't." How does a girl give head? "I've not thought a lot about giving head from a girl's point of view before. It's been all about kicking back and enjoying the sensation. Receiving head is great." I paused to gather my thoughts. "Okay. I'd say there are two parts to giving head. The first part is about getting the guy excited."

"Should I take off my shirt and bra?"

I shook my head. "Excited was the wrong word. I should have said 'stimulated'. And as much as I'd love to see your tits, we are in a car visible from the street so I think it's best if you keep your shirt on." This was crazy. The whole night was so fucking crazy. I felt like my head was going to explode. "The second part is about simulating intercourse with your mouth and hand. Your hand is almost as important as your mouth. Let me show you your go-to move for the second part. Sit down." She sat down so that her legs were in the aisle between the middle seats but her upper body was twisted so that she was facing me. I had one knee on the back seat and one foot on the floor. "Put my dick in your mouth." Words I never thought I'd tell my sister.

Ashlynne leaned forward and slipped a few inches of my dick into her mouth.

"Good. Now wrap your hand around my dick. Firmly but not tightly." Ashlynne did. "Good. Now while keeping your lips sealed around my dick, slide your head back. At the same time, slide your hand away from you."

Ashlynne tentatively did that and then took my dick out of her mouth. "Like that?"

"Yes. Then you'll slide your lips back down while moving your hand toward your face."

"Let me try that." Ashlynne took my dick into her mouth again. She slid her mouth slowly up my dick while moving her hand down before reversing the motion.

"Oh yeah, Ashlynne." Her lips moved back up and back down while her hand did the opposite. "That feels so good, Ashlynne." Her lips and hand made a couple more synchronized trips along my dick. "You've got it. Stop doing that now."

"Was I doing it right?"

"For the most part. The area where your hand was should be slick. It'll get uncomfortable after a while if it's not." Ashlynne nodded. "So back to the first part. It's all about stimulating my dick. Really, that whole area. Get the nerve endings excited. Do it in a lot of different ways. Doing the same thing over and over again gets boring. If you gave head by doing only the second part until I came, it would work but I'd be bored. Variety means excitement. You want to get me so excited that when you start the second part, I'll come fairly quick."

Ashlynne nodded her head. "Got it." She studied my dick for a moment. "I wasn't able to get much of you into my mouth. How do those girls in those videos get those big dicks all the way into their mouths?"

"I don't know. Maybe if I had a dick that big I'd know. I'd guess they've learned to suppress their gag reflex. You can research it later if you want. But don't worry about it - I've loved every blow job I've ever gotten."

"Okay. So back to the first part. How do I stimulate you?"

"You were doing a great job while you were trying to convince me to teach you. Go back to doing what you were doing then."

Ashlynne smiled. She was getting a little confident in her abilities. She put her hand so that her fingertips were evenly spaced around my dick and slowly moved her hand up from my base to my crown. "Like that?"

"That was great. You can give little tickles."

"Like this?" she asked as she tickled just under my crown.

"Again, that's great. Do lots of different things. Be creative. But don't use only your hand - use your mouth, too. In fact, you need to get the bottom of my dick wet during part one in preparation for part two."

"How do I do that?"

"You can lick it."

Ashlynne gave my dick a short lick.

"Just like that," I said.

"Did you like that?"

"Very much. You can give it a sloppy kiss."

Ashlynne held my dick up and give it a wet kiss near the base.

"Very good, Ashlynne. You can run your mouth up and down my dick while drooling on it."

Ashlynne smiled and then proceeded to give that a try.

"You're picking this up quick, Ashlynne. I've seen girls in some porn videos spit on it, but I don't find that sexy. What I do find sexy is if you make eye contact while you're stimulating my dick. There's nothing hotter."

Ashlynne licked the underside of my shaft while watching me, then ran her mouth up and down my shaft. She stroked the top of my shaft with her fingers while holding the tip of my dick in a gentle kiss. She continued trying different ways of worshiping my cock while maintaining eye contact most of the time.

"You're great at this, Ashlynne. And you look so fucking sexy." A streetlight provided some light to the car, and my eyes had adjusted enough that I could see Ashlynne pretty well. "Now take me into your mouth." She took my dick into her mouth and looked up to me. "Swirl your tongue around the crown like it's an ice cream cone." She did. "That feels so good. You have a talented tongue, Ashlynne. You can do a couple of the second-part pumps." She slid her lips down my shaft while sliding her hand up, then reversed her lips and hand. After a couple of cycles of that, I said, "Now move on to something else."

When my dick slid out of her mouth, Ashlynne said, "I'm enjoying this. I didn't think giving head would be this much fun. Or exciting." She gave me a devilish grin before sliding her lips down my cock.

I could feel another load rapidly building up. Her mouth and hand were in constant motion while she gave me the sultriest looks I had ever seen. She was the hottest girl I had ever been with.

"Let's finish this, Ashlynne."

She took my dick in her mouth and wrapped her right hand around my shaft, then established a quick rhythm of bobbing her head up and down my dick. I began thrusting my hips slightly in time, lightly fucking her mouth. I started panting, and, in short order, I was about to explode.

"Here it comes, Ashlynne." I blasted a load down her throat. Having come once, it wasn't so big that it overwhelmed her. She kept up the bobbing as I fired spurt after spurt.

"Slow down, Ashlynne. Slower. I'm overly sensitive right now. Stop."

I pulled her up so that we were face-to-face, then hugged her and kissed her. "That was awesome, Ashlynne. Any guy in the world would have been delighted with that blow job. You're a tremendous learner." Ashlynne beamed. "How was it for you?"

"Great! I enjoyed doing it, though I almost gagged when you came. I didn't care for the taste, but it wasn't awful like some girls say. I definitely want to do it again."

We were in a tight space in the back of the minivan. I turned Ashlynne so that I was standing in the aisle between the two middle seats.

"Sit down, Ashlynne."

As she sat down, I knelt. Ashlynne was still naked from the waist down from when she had slipped off her wet panties.

"What are you going to do?" she asked.

"I'm going to show my appreciation for a great blow job."

I knew I should have ended the date after the blow job. Ashlynne would have accepted ending it there. We certainly didn't need to do another act of brother-sister sex.

I put Ashlynne's legs on my shoulders then pulled her ass to the edge of the bench seat. I spread her legs so that her feet were on the middle seats. Her legs were lightly tanned, but her crotch area was lily white. It made her seem even more virginal. Her pussy was right in front of me. I leaned forward and separated her pussy lips with my tongue before licking upward.

"Oh my god!" said Ashlynne.

My brain said I shouldn't do this, but my heart said that I should. Maybe that was because of all the years where I expected my girlfriend to suck me off, and I refused to eat her out in return. Mandy had banged it into my head the importance of reciprocating, and I knew now that I was an asshole then. I didn't want my sister to think it was okay for the guy to not return the favor.

I dropped my tongue down to Ashlynne's hole, and she was sopping again. Or still. I lapped up a huge amount of fluid. Moving on, I worked up and down Ashlynne's pussy lips while she ran her fingers through my hair and moaned. I made my way up to her clit and then moved my tongue very gently back and forth as I made a slow circle around her clit.

"You're going to make me come again, Todd."

"That's the point."

Maybe I was doing this because I just wanted to eat my sister out. Once we crossed over the oral sex line, why not explore her body with my tongue? I knew that if I didn't, I'd regret letting the opportunity pass. I loved her taste. I loved holding her firm body in my hands. I loved hearing her little pants of pleasure. I loved making her happy. I loved everything we had done tonight, even dealing with the crazy, entitled princess. I wanted to make Ashlynne come one more time.

I went back to working my tongue up and down her whole slit to get all of nerve endings excited. I enjoyed licking up her nectar. I thought about finger-fucking her, but I didn't want to tear her hymeneal tissue. Hymens were the second most interesting topic in my human sexuality class. As she had used tampons and had apparently masturbated, she may not have a lot of hymeneal tissue left.

"Oh, Todd." Pant. Pant. Pant. "Feels so good!"

Based on her sighs and moans, I felt that she was ready for me to get down to the business of making her come. I focused on her clit, making circles around it while making small up-and-down wiggles with my tongue.

"My god, Todd!"

Ashlynne wiggled slowly in the seat as I continued lashing her clit, her arms flopping around. As she had come once already, it was taking a lot of work to get her to come again. Eventually, my work was rewarded with heavy pants. I redoubled my efforts. Again, I wished I could mix things up by finger-fucking her. My jaw and tongue were getting a little tired, but I never slackened my pace. I steadily pushed her toward that mountain top. She dropped her hands by her side and lay passively as I brought her to the brink of another orgasm.