The worst and best date of my life! – Sex Stories

The Worst (and BEST) Date of My Life!

Did you ever have one of those dates where you spend hours getting ready, only to have the date be a total disaster?

David was the major hunk in my drama class, smart, charming, and that body just got me going! He was about six foot one, dark brown hair, enough muscles to be handsome but not creepy, and a smile that left a swath of drenched panties in it’s wake. Mine were no exception, and we started to hit it off, and he asked me to go out on Friday night.

My last class was out at two, and major prep time was needed. I had the perfect dress that looked good, but not slutty, the perfect shoes, and I had enough time to make my hair look right. I’m not what anyone would call beautiful, but I’ve been called plenty cute. I’m about five foot seven, a hundred and twenty eight pounds or so, I barely fill a c-cup, but playing volleyball all through high school left me with decent legs and a reasonably toned butt. I’ve always hated my freckles, but I’m happy with the blue eyes and the light brown hair.

“Woo-hoo! Trying to look like a real lady now? Must be some kind of big date?”

This was spoken by my idiot brother, Kyle. A high school junior who was a legend in his own mind. I got plenty of grief from him on dates, my hair, my clothes, and well, everything in my life. Little brothers are so obnoxious.

“For your information Kyle, I’m going out with the best looking guy in my class, and he’s incredibly cool, as well as looking like a male model!”

“Is he bringing his dog?”

“What dog, you jerk?”

“The one that he holds the leash in one hand and his cane in the other?” He said with a smirk, but a prudent duck.

“You are such a geek, Kyle, why couldn’t Mom and Dad have had another girl so I could have a sibling with a brain?” His duck was too early, I waited to throw a pillow at him and caught him square in the face.

He just laughed at me and went into the kitchen.

The doorbell rang a few minutes later and my heart jumped! It was him, he was there, and my god he looked good! A pair of khakis and a black silk shirt, and he looked amazing.

“Hi, Laura!”

It took me a few seconds to get my brain in order.

“Oh, hi David! You look great!”

“Thanks, you look nice too.”

Ouch. I put a lot into this.

“You ready to go?”

“Yeah, just give me a second, oh, David, this is my brother Kyle, Kyle, David.”

They shook hands and were polite to each other, but Kyle didn’t smile at all.

We got in David’s car and headed out. He was taking me to a very nice place for dinner. We got there, and were seated and he started to tell me more about himself. Lots of stuff. I realized he had a pretty high opinion of himself, and I was hoping he was just talking because he was nervous, too. No such luck, he kept going and I started to think he was a jerk, and then he proved it by yelling at our waitress.

“David, you shouldn’t be rude to her, it’s not her fault the kitchen messed up!”

‘Aw, she’s stupid. That’s her fault.”

He was turning out to be a real asshole. Wonderful.

“I’m not into being rude like that to people, it’s better to be pleasant, isn’t it?”

“If you’re stupid, yeah, but if someone’s as stupid as that bitch, I’m not wasting my time.”

“David, are you drunk or something? You’re never like this in class!”

“I had a few, what of it? You offended?”

I put down my knife and fork.

“Yes, I’m offended, and I think I realized you’re a jerk. Get the check and take me home. This date is over.”

“It’s over when I say it’s over.” He sat back in his chair with a smirk.

“No, it’s over now. I’m leaving.” and I got up.

He stood up to block my way.

“It’s not over, you’re just uptight.”

“No, over. Finite. Done. Curtains. Pay up and take me home.”

“Fuck you then, it’s on you! I’m out of here!”

He stormed out of the restaurant and left me with the bill! What an asshole!

I had enough to play the bill but I was pretty upset. When I started crying the manager came over and asked what was wrong and I told him.

“I’m sorry, you seem too nice for that guy, tell you what, I’m gonna take 75% off this one, will that make it easier?”

“Oh, you’re so nice! Thank you! Can you also call me a cab so I can get home?”

I paid up and got in the cab, but then I started crying again. Why was he such a jerk, and why did I fall for him? I was so stupid! I kept beating myself up over it the whole way home and by the time I got there I was a wreck.

I walked in the door and Kyle was watching TV. I expected the worst from him, but he didn’t make fun of me, he didn’t pick on me, he hugged me and told me how sorry he was that David had been an ass. I told him I was going to go change out of my outfit and he said he had to run an errand and maybe we’d order pizza when he got back. I thought that sounded nice.

Half an hour later Kyle came back in, with a grin on his face and some blood on his hand.

“What happened? Are you OK?”

“Sis, I’m fine, David on the other hand is not a happy guy.”

“What did you do?”

“I recognized him, he lives in the same apartments that Jeff and his Dad do. I went over, knocked, he opened, and he got a face full of knuckles. He’s taller than me, but I picked up a bit of mean playing rugby. Three straight shots and he was not interested in continuing. I split three knuckles though. You got some bandaids and maybe some neosporin?”

“You…defended me?”

“Yeah, the guy’s an asshole. Nobody treats my sister like that and gets away with it.”

I just hugged him tight with affection for the first time, since, well, forever. He was a pretty cool brother.

“Tell you what, sis, you put that nice dress back on, and I’m taking you out for dinner. Let me just change.” I thought that was incredibly sweet for my little brother, so I ran back up and changed. We came down at the same time, and he’d borrowed one of Dad’s jackets, but he looked good, and I knew he wasn’t going to be a dick to me.

He took me to nice place and we had a great dinner, they had a band playing, and I loved to dance, but I figured it would freak him out to have to dance with me. I was surprised when he offered his hand and led me onto the floor. He was actually a pretty good dancer! Very smooth, knew his stuff and led me expertly. I had to compliment him on it.

“Thanks, you’re pretty good yourself. I’m just stunned that the guy blew a chance to spend the night with a beautiful girl like you.”

I blushed at that.

“I’m not beautiful, but thanks for saying it.”

He looked me in the eyes.

“Sis, I meant what I said. You’re stunning. A nice dinner, dancing with you in his arms? Hell, I feel pretty lucky to be here with you myself. I know I kid you a lot, but take my word for it, you’re the prettiest girl here, and that’s the truth.”

With that he spun me, but as I came back to him, I felt so good that I just kissed him. On the lips. I thought he’d leap away screaming but he didn’t, he just held his arms around me, and enjoyed it.

“Wow, I’m so sorry Kyle, I didn’t mean to embarrass you like that. Let’s sit this one out.”

He looked at me and smiled.

“Who’s embarrassed now? Not me, when I get kissed by the prettiest girl in the place, I’m usually a pretty happy guy.” He’d said it again. Did he really think I was that pretty?

We kept dancing, and in his arms, I realized he did think it and believed it. I started to get an idea, but wasn’t sure if it would work.

We danced two more songs and then sat back down.

“You are just being so cool to me, thanks little brother.”

He gave me a grin . “Aw, I had to grow up eventually. It just pissed me off that he was such an asshole. I could tell you really wanted to have a nice time tonight. I just hope I’m a decent substitute.”

“You’re doing great in my book. I’ll be back in a second”

I had to use the ladies room, but the band had stopped for a few minutes to adjust some equipment and I quickly had a few words with the singer. A quick trip to the facilities, and I was back at my table.

The band started up again, he again offered his hand to me, and we started dancing again. He was smooth, charming and very sweet. My idea started to really sound fun, I just wondered if I had the guts, and he wasn’t going to totally go nuts.

The band went into the super slow romantic song I’d requested, and I just gave him a shy smile and put my arms around his neck. His hands stayed at a very polite lower back, but I wanted them a bit further, so I reached back and slid them further so he was caressing my butt. He gave me a raised eyebrow, but didn’t seem to have an issue with it. We swayed to the song for another minute and then I took my chance and kissed him as passionately as I could.

He hesitated for a second but then kissed back. He wasn’t exactly going all out, but he was enjoying himself, and then he responded with a bit of tongue and a whole flood of feelings came over me. I was into him! Even better he seemed to be into me! Part of me said it wasn’t a good idea, but part of me said why not, so as we sat back down I kissed him again, and again he was enjoying himself. He pulled away a minute later.

“Um, this is all good, but I don’t know if…uh….”

“You don’t want to keep going?”

He shook his head.

“It’s not that, I’m just not sure if the restaurant is the place for it, you know?”

Oh boy, my heart jumped at that.

“Then we need to find…somewhere else, don’t we?”

“We do, now let ME get the check like a gentleman should and we’ll see where we go from here.”

I offered to pay, because Dad gave me a pretty good allowance in school, but he insisted.

“Look, I only work 18 hours a week at the warehouse, but I get paid OK, and I’m not exactly throwing it all away on the other hot women, you know? Let me get it, because you deserve to be treated right.”

I was the aggressive one and I pushed him up against the car to kiss him. Our tongues were now flying as we tasted each other deeply, and I loved it. He wasn’t pushy, he wasn’t grabbing at me like some guys did, he was just letting me set the tone, and I got hotter and hotter.

“We really should find someplace else.”

He held my chin in his hand.

“You sure about this, Laura?”

Wow. He almost never used my name.

“Yes, I somehow know it’s just going to be tonight, but you’ve been so sweet, and I just need this.”

“Okay then, but if you want to bail out, say the word. I’m not going to pressure you at all.”

Why did this great guy have to be my brother? I’d kill for a boyfriend like this.

We went to a park outside of town, found a secluded spot, and he pulled some blankets out of the trunk. He set them up, and we got back to kissing.

He was incredibly sexy, but very gentle with me, and his fingers eventually slipped the straps on my dress down.

He kissed his way to my bra, and unsnapped it with his teeth, and let it fall as he started to kiss and lick my breasts.

“Oh wow, you are so incredibly hot, your body is amazing” he murmured as he took my nipple in his mouth to suck it. He gently sucked it and bit it softly with his lips, and it felt so good, so good that I could feel myself getting a bit moist.

He pulled up for a second to take his shirt off, and I slid the rest of the dress off, I wanted him so badly. He took my other nipple and began to lick around it to tease me, and I caught my breath.

“Don’t tease me so…”

He only let out a quiet chuckle and bit down on it, as another bit of dampness began to wet my panties. He was being incredibly hot, and I knew I wanted him so bad. He started to run his fingers all over as he followed them with kisses and eventually he stopped at the waistband of my very wet panties. He slipped his fingers under and began to pull them off. I lifted myself so he could remove them and then I spread my legs, waiting for his kisses to continue.

He traced his fingers downwards and slowly ran them along my lips and ever so slightly penetrated me with a fingertip. Then he put his lips upon mine and slid his tongue in between them. I couldn’t control myself and gasped as a bit of wetness squirted across his mouth. He only let out a soft grunt of satisfaction and began to explore me with his mouth. Up and down my labia with his tongue and lips pulling one then the other in between his lips to suck them and lick them. Then he would slide his tongue deeply into me, and lick me so sweetly, stopping as he reached the top of my pussy to flick his tongue on my clit.

This wasn’t just good, this was the best cunnilingus I’d ever had! This gentle lover was making me feel like no one ever had.

He would leave my vagina for a moment to kiss all around me, the inside of my thighs, and nuzzle my trimmed strip of pubic hair and then he would gently blow on the whole area which got me quivering with ecstasy.

“OOOhhh that is so good, don’t stop!”

“No intentions of it.” he murmured as he drove his tongue deep inside of me again, and I gasped in pleasure again as another squirt let loose, but if anything, it made him even more passionate as he would intensify his strokes and kisses, driving me further to waves of bliss.

Then he turned his efforts fully on my clitoris, and I let out a squeal of delight as he did. He sucked it as deeply as he could and his fingers would stroke my lips as he did, and then he’d flick his tongue on my clit, and after three of them, I erupted in an incredible orgasm!

I knew I was wetter than I’d ever been but he made little soft noises that told me was enjoying every second of it. He licked me all over as I came and then my second orgasm shot through my body like a lightning bolt, I tried to keep quiet on the first, but no go as I screamed out in pure joy!

“OOoooooohhhhhh god! Oooooohh yessss! “ as I thrust my hips forward and he just buried his face in me and kept licking and sucking!

I held him for a few moments between my legs, but then I collapsed backwards onto the blankets. He lay there for a moment sliently, and I felt a twinge of fear. Did that freak him out, was that too much?

His head rose and in the moonlight I could see it glisten with my juices. His grin went ear to ear as he stuck his tongue out at me.

“That was quite a thrill, I had no idea you got that kind of wet though.”

“Kyle, I never have before, sweety, that was the best I have ever had, thank you so much…..”

He pulled himself up next to me to kiss me again.

“No problem, although it wasn’t exactly a rough experience for me…..you tasted so sweet. Here, see?”

We kissed deeply again and I tasted my juices on him and it was really erotic. I felt so good, so satisfied, but I didn’t want to be the only one. I tried to reach down to undo his jeans, but he stopped me.

“This is all about you, Laura, not me.”

“But I want to taste you the way you tasted me.”

“You don’t have to, give us a few more minutes, and we’ll go on, but I’m enjoying just holding you.”

I was enjoying being held.

We just cuddled and kissed each other softly for about ten minutes and I knew I still wanted more.

“Kyle, you’re going to…