Leslie 5

Leslie is a really good friend that I see only once a year or so, because my parents--who are also friends with her parents--live in Corona del Mar, and her parents live in Glendale. Driving from Leslie's house to my house takes almost an hour and a half, depending on the traffic. The problem that night wasn't the traffic, but the fact that my Mom and Dad had each had had a few glasses of wine with dinner, and had decided that it was better to accept the invitation of Leslie's parents to spend the night. My parents were going to sleep in the one guest room, and so I was to either sleep on the living room couch or in Leslie's room on her bunkbed. Leslie seemed happy about the idea of having me sleep in her room, and Leslie's parents surprisingly seemed fine with it too.

You might wonder why Leslie's parents trusted me with their daughter, but the reality was that we were both such good and nerdy "kids," even though we were both 18, that all of the parents seemed okay with it. Perhaps it crossed their minds that we might fool around a little, although probably they dismissed the very idea because so far we'd always been "just friends." And so if they even thought about us fooling around, which doubt, I imagine they thought it would be a good thing.

Leslie and I were both misfits who were not only virgins, but fresh high school grads who had never had a serious romance, or even that much dating experience. This was something our parents once-in-a-while commented on and even made fun of a little.

"Are you sure you don't want me to sleep on the couch?" I said, as I saw Leslie practically beaming at me after the sleepover had been decided on. We were now back in her bedroom behind her closed door, after the conversation with everyone down in the living room.

"Are you kidding?" Leslie said, laughing, "I've got a good looking man sleeping in my room--and my parents don't even care!"

I'm fairly good looking--almost 6 feet tall, dark hair, fine features, and some muscle tone. But I'm just really shy with most people--especially with women my age other than Leslie. Leslie isn't as shy, but to be blunt she's not super cute, at least in a typical way, although I think she's sexy in her own earthy and goofy way. Leslie is as short as I am tall, being only five feet four inches. She has a nice figure, but a little bit of acne and a somewhat plain face. Her hair is neither blond nor brown, but that in-between that's sometimes called dirty dishwater blond.

As she'd earlier told me, there was a rumor going around her high school that she was "Leslie the lesbian," and, as she added, "this was really good for getting dates with girls, but since I'm straight that didn't help with any of the guys that I was after, who completely ignored me as if I were invisible."

Suddenly Leslie said with a mischievous grin, "I'm going to take a selfie of the two of us!"

And without waiting for my answer she got right up next to me, and said "Smile!" and then took a shot of the two of us--and we actually looked quite good together.

"I'm going to send this Jenny--you remember, my really pretty friend," Leslie said, with a hint of jealousy in her voice.

I had a crush on Jenny, but I'm pretty sure almost every guy who ever met her did because she was so beautiful.

And quickly Leslie sent the pic to Jen, and then wrote something to her that I couldn't see. Soon a reply pinged back, and Leslie laughed, and then sent another text.

"What are you laughing about?" I said, laughing too a little, "What's the big deal?"

Leslie whispered conspiratorially, "Jen says that the two of us should definitely play truth or dare--and I agree."

"What?" I said, laughing but not whispering, and adding, "You're kidding, right?"

"Whisper!" Leslie said, "And no, I'm not kidding. We were just talking earlier about how we're both pathetic in that we have very little experience with the opposite sex. Well, this is our chance to fix that, at least a little."

My eyes widened, and now whispering, I said, "What? Are you and Jen crazy? Our parents are right downstairs! In fact they're opening another bottle of wine."

"That's the perfect cover," Leslie whispered back, "And it's pretty easy to hear them if they come up the stairs. I'll lock the door, and if they knock we can pretend we are asleep or something."

I wondering what she was planning, since for so long we'd been only friends, with only a few flirty sparks to hint that it could ever be different.

I whispered, "Well, should we put any limits on it? I mean, any truth and any dare?"

I was now wondering what this night had in store.

"No limits! We're 18-year old virgins who've never done more than kissed someone. Come on, Jeremy. Don't you want to play truth or dare with me, or am I not pretty enough for you? I know I'm not as pretty as Jenny, but...."

Leslie looked exasperated and a little hurt.

I laughed and whispered, "Of course you're pretty!"

When I said this, Leslie suddenly flushed, and looked simultaneously surprised, happy, and bashful.

"You really think I'm pretty?" Leslie whispered, looking me in the eyes with a shy and yet alluring look I'd never seen from her.

"Yes," I said, flushing myself, as I saw how much it meant to her that I thought she was pretty.

Then I whispered, "But, I mean, if the other person dares us to do something stupid, or something that we just can't bring ourselves to do, then we can each of us always just not do it, right?"

"Of course, but the person who backs down will have to live with the shame of failure," Leslie said in a tone that was more serious than joking.

"Okay," I said, smiling and wondering what the hell was actually going to happen.

Leslie walked to her bedroom door and closed and locked it, and then turned around and said, "I'll go first. And I'll take a dare."

She had a rather determined, but also sexy look about her.

"Okay," I whispered, adding after a brief pause, "I dare you to take off your t-shirt."

I wasn't sure if she would or wouldn't, but almost immediately she started a kind of sexy dance strip-tease, swiveling her hips and raising her Star Wars t-shirt up so that I could see her cute innie belly button, and then she winked at me.

"Well, I've got a bra on under this, but just one more dare and...."

And with that she took off her t-shirt, revealing the tops of her medium-sized breasts in a flesh colored but lacy bra.

I stared at Leslie's breasts, even seeing her nipples a tiny bit through the fabric.

Noticing where I was looking, she laughed, and then circled her index fingers around her nipples, and then gently squeezed her breasts together, which made me laugh.

"Wow," I whispered, "your breasts are bigger than I thought for some reason."

"Maybe you should have been paying more attention," she said with a smile, adding "Now it's my turn: truth or dare."

"Truth, I guess," I said.

"Okay," Leslie said, "But next time that means you have to do a dare."

"Fair enough," I said, "What's your question?"

"Do you really want to look at my breasts?"

"Yes," I said, blushing.

She looked happy, and then said, "Why don't you take a picture of me in my bra?"

"Sure!" I said, somewhat amazed.

"It could make for some good memories later, if you know what I mean," Leslie said with a kind of ironic smirk.

"Okay," I said, "Smile beautiful," I said, and as she posed and I took a few pix in of her in her bra.

I was getting worried about this, but the older generation did indeed seem to be drinking their wine and completely ignoring us.

"Dare again," Leslie said, without even waiting to be asked.

I whispered, "Wow. Are we really going to do this? Or are you joking?"

Smirking some more, Leslie said in a flirty way, "Try me and find out."

I whispered even more quietly, "Okay, I dare you to take off your bra."

Leslie smiled, reached behind herself, unclasped her bra, and dropped it to the floor.

"Ta da!" Leslie said, jiggling her very nice and perky breasts with large areolas and pink nipples that had me mesmerized.

And then she added, "I guess I should have done a strip tease or something, but....do you like them."

I said staring at them in awe, "Wow, Leslie, you have amazing breasts!"

Leslie smiled and, looking down at her tits said, "They are pretty nice, aren't they? And they're bigger than Jenny's. Feel!"

And with this took hold of my right hand and placed it on her left breast.

"Oh my god, Leslie," I said as I felt her breast and her nipple, with her hand guiding me to squeeze her. And then she brought my other hand to her other breast, and at this point I groaned a little--"Uh!"--as my cock suddenly strained in my pants into a full erection.

"Oh, I can tell you really like me, Jeremy. I've never heard you grunt like an animal before!"

We both laughed, and then I said, "May I kiss you?"

"No!" she said, laughing too, and then gently and teasingly pushed me away, and then took my hands off of her breasts, and then said, "Wait till your next turn to ask me for a dare if that's what you want to do!"

"Okay," I said, still laughing a little while still staring at her breasts.

"Wow, you really like my boobs!" Leslie laughed again, "I don't think I've ever seen you look so happy. It's almost like you've taken a drug or something. Anyway, truth or dare?"

I'd promised to give a dare, and so that's what I did.

"Take off your pants," Leslie said without hesitation.

"Okay," I said, suddenly getting serious, even though of course I had underwear on. But given that I now had a complete hard-on from staring at Leslie's breasts, I wasn't sure how much they would hide.

But I took off my pants quickly anyway, and then stared down at my black Calvin Klein undies.

And it was completely obvious that I had an erection, and one that was just barely covered.

I looked up to see Leslie staring at my crotch.

"Wow. You really, really like my boobs."

"Sorry," I said, blushing.

"Don't be sorry! I'm flattered. Anyway, for your memory album, if you want, I'll let you take picture of me topless if you promise not to share it with anyone."

"Really?"

"Yeah, really, Jeremy. I think you might even get some extra happiness out of such a pic later."

"You're probably right," I said with another blush, and then I took some pix of Leslie as she posed topless for me, looking for the three pics first sultry, then serious, and then longing.

"Truth or dare, Leslie," I asked.

"You know me--dare!" Leslie said.

At this point I regretted a bit that I'd asked her to kiss me, and that she'd said take that as your next dare--because now I wanted to get her pants off.

But just then I noticed Leslie snapping pix of me with her phone, including what seemed to be a close-up of my undies.

"Hey," I laughed, "what are you doing?"

"Turn about is fair play!"

"Fair enough. Okay, I dare you to let me kiss you on the lips."

"Sure, sailor, come on over!" Leslie said, spreading her arms out for me.

I came over and slowly kissed her, and soon she opened her lips and then we were touching tongues lightly--and it was sweet. And then daring for more I put my right hand on her left breast, and when she didn't take it away, I squeezed her luscious boob gently as we kissed.

But as I did that she reached down her hand to feel my dick.

I broke the kiss as I felt her feeling my erection, and then squeezing it.

"Remember, turn about is fair play!" she said.

"But I haven't felt your--"

"Wait for your next dare for that, mister. Don't worry, I'll let you--if you give a dare to me."

"Okay," I said, but then immediately hesitated--because I was, after all, already in my undies.

But she didn't hesitate, as she stepped back from me she said, "I want you to take off your Calvin Kleins."

I hesitated a bit more, and said, "But Leslie, as you know I'm hard. No one on earth aside from me has ever seen my dick when it's hard before."

"I know you're hard because of me, and so I think I have a right to see what my sexy body has done to your...dick."

"Well, are you really going to show me your..."

"My pussy? Yes, I will. In fact, I'll show it to you first if you want. I'll give you two dares for free for me to take off my pants and my undies--but then you've got to show me right away."

"Okay," I said, wondering if this was really happening. I could hear our parents downstairs, who were still drinking, laughing, and clattering dishes, and seemed to have almost completely forgotten about us. They probably assumed we were playing a video game or watching a movie.

Meanwhile Leslie was already taking off her jeans, but when she got to her purple undies she hesitated too.

"You know, no man has ever seen my snatch either. I hope it doesn't freak you out. I don't shave much, and so my pussy is sort-of hairy. And so you won't really be able to see all that much unless I spread my legs."

"Will you?" I said with awe, looking at her purple undies, which did have a tiny hint of dark blond hair peeking out.

"Oh my god!" Leslie said, and hid her face in her hands, but then added, "Do you want me to...spread my legs for you?"

"Are you kidding?" I said, "I'll do anything for you if you do that for me."

"Okay then, you perv," Leslie said, "I'll spread my legs and show you my pussy lips and my vagina, but only after you show me that boner that you got from just looking at my boobs. Okay, but first the unspread view of moi."

And with that she lowered down her undies, revealing the dark blond triangle of her cunt.

And it wasn't true that I couldn't see much. Although just barely visible in her triangle was a fleshy area that I knew from porn were her pussy lips.

"Wow, Leslie, you're so beautiful," I managed to say as my cock pulsed in my briefs.

"Thanks," Leslie said softly, and blushed, and then added, "Okay, now show me yours."

I realized I had to do it, and so I lowered my briefs, revealing my six and half inch circumcised erection. I saw Leslie staring with almost shock at my slightly veiny cock, which was standing up at almost a 60 degree angle, with it's large pinkish-red mushroom-like head.

"Jeeze! That's even bigger than I thought it would be!" Leslie said in shock, "Fuck!"

"Well, I guess that's what it's for," I tried to laugh.

"Oh my god," she went on, laughing nervously, and then adding "Wow. I think your dick really wants to fuck me."

I was taken aback by her reaction, and said, "Sorry. I'm going to put my underwear and pants back on now."

"No Jeremy!" Leslie said with a smile, "I like it. It was just a surprise, that's all. I've never seen a hard one before. Can I take a picture of it?"

"No way!" I said.

"If you let me, I'll let you take pix of my pussy."

"Okay," I said, "as long as the pictures don't have our faces in them."

"Deal," she said, and then started snapping a few pix of my dick.

She seemed quite interested, and finally put her phone down and said, "May I touch it?"

"Yes. If I get to touch yours too."

Leslie reached out and took hold of my shaft near my head, and it pulsed slightly as she did it.

"Wow! A live snake!" she said in surprise, adding "It's warmer that I expected. It still seems weird to me to put an erection in my mouth."

"Yeah," I said, "I mean the idea of licking your pussy seems kind of weird too, but I'll admit that when you took off your clothes I thought about it."

"Really, you thought about licking my pussy!" Leslie said, with even more surprise, and blushed.

Then she said, "Well, let me at least kiss your dick. Jen will totally make fun of me if I don't at least do that."

Leslie bent down to kiss the top of my head, and then suddenly at the last second seemingly changed her mind, opened her mouth wide, and put my whole head inside and started gently sucking on it.

It was amazing feeling her wet and warm mouth sucking on my cock head.

"Oh my god Leslie! Oh Leslie! Ohhh Leslie. That feels so good!"

But then as soon as it had started it stopped, as Leslie suddenly took her mouth off of my cock.

"Well, I can tell you really liked that. I've never heard you say my name that way before. Having a cock in my mouth was weird, but not as weird as I thought it would be. Okay, your turn! Let me get on my bed and we'll see if you're as brave as I am."

Leslie got on her bed with her legs together, propping up my pillows behind her back so she was sitting up.

And then she said as she saw me looking at her beautiful nude form, "I still can't believe I'm showing my best male friend myself nude. We've known each other for so long. This is so weird!"

I smiled as I looked at her and said "Well, it may be weird, but I think this also just became the best day of my whole life. I mean, it definitely is--you've made this the best day of my whole life so far."

"Really?" Leslie said with a smile and a laugh, and then added, "Yeah. I can see that. In fact, you know what, I trust you. If you want to right now you can take a picture of all of me, even with my face, to help save the memory."

"Thanks, Leslie," I said, and took a few.

Then I got up on the bed and said, "Well, now we get to see how brave we both are."

"I know," Leslie said, hiding her face in her hands for a second, and then adding, "I can't believe I said I'd spread my legs for you. I'm not sure I can do it now."

"Would it maybe help if I did it--slowly? Or would that make it even weirder?"

"Yeah, that might help. Let's see."

"Let's start with gently massaging and tickling the feet of the beautiful goddess."

I started massaging one of Leslie's feet, and she said, "Mmmm, that feels good. Although I know you're just calling me a goddess so you can see my pussy."

"And kiss it."

"Yes," Leslie said with a smile, and then added, "and lick my clitoris too. Remember that I put your whole cock head in my mouth."

"I haven't forgotten," I said, as I moved from massaging her feet to her lower legs, and in doing so so started slowly separating her legs.

After doing some more gentle massages up to the knees on both sides, I separated her legs some more, and by this time I could see Leslie's pussy lips, and even her moist opening, and then I lay down between her legs and started gently kissing Leslie's thighs--first a couple of kisses on one side and then a couple of kisses on the other."

"As you can tell, we're now switching to kissing the beautiful thighs of the goddess."

"Do you really think I'm beautiful?" Leslie said.

"Stunning," I said as I kept kissing.

"What would you say is my most beautiful feature?"

"Your pussy," I said, glancing up at my goal.

"You horny man," Leslie said, smiling, but then she started playfully petting her own pussy and beckoning me closer, saying, "You're almost there. I know that for most guys a woman's pussy is the ultimate. They just can't get enough. Are you going to lick me?"

"Yes," I said, as I had now kissed my way to her smooth inner thighs and the start of her bush.

As I was now inches away, I sensed that her scent was sweet and slightly musky. But just as Leslie felt almost a bit overwhelmed my my cock, for a few seconds I felt almost the same way about her spread and aroused sex. But throwing caution to the wind I started kissing and gently nestling into Leslie's pussy, and then I started gently licking her slit. Her womanly scent was intoxicating, and I realized right away I was enjoying it.

"Do you like it? Oh Jeremy!" Leslie said softly.

"I love it," I said, and then kept gently kissing and licking.

"Here," Leslie said, and with her hand on her upper pussy she raised her hood so that her clitoris was visible, and then she added, "would you kiss and lick my clit?"

"Yes," I said, and then holding one of my hands sort of like she did I raised her hood, and started very gently kissing and licking Leslie's clit.