My Date with Emily

Considering my first basic kiss from a girl was just a little bit earlier, I wasn't very good at this, but she was trying to move me along quickly. I started following her lead in regard to the kiss and before I knew it I felt her tongue dart past my lips. I hesitated but moved my tongue forward a little in my mouth and they met. I can't say what it was like for Emily, she's obviously done this before but that moment was just electric for me, like a spark in my mouth. This make out session continued for a moment until she broke it and smiled.

"French kissing, that's first base. You've already been grabbing my boobs so that's second base, but just for good measure..."

She climbed up into my lap, forward this time and leaned to bring her breasts inches from my face. "Alright, we'll start with the right one. Put your lips around the pink part, suck a little and flick your tongue around my nipple."

Never in my life had I imagined a girl being so aggressive, but I was liking it. Emily twisted her torso so her right breast was in front of my mouth and I licked my lips so they wouldn't be dry. Strawberry again, from her lip gloss. I leaned forward just enough and started to suckle on her right breast, my tongue reaching out until it felt the nub that was her nipple and I started to lick it like a tootsie pop. I wasn't quite sure if it was right but I closed my eyes and did it. My ministrations must have been having some effect, or at least the actress was humoring me because I thought I heard a small moan escape from her mouth after about 30 seconds. I have no idea how long I suckled on her right breast before she twisted her torso back and pulled it away. Her areola was glistening with my saliva and her nipple looked way harder than the other one.

"Very good, now for the left, however this time, ever so gently I want you to nibble on my nipple with your teeth."

There was a quick "not that hard, there you go," from her as I started to nibble on her left nipple--my excitement had apparently gotten me ahead of myself to start. "Flick your tongue along it too," she commanded, so I continued to nibble with my tongue getting in on the action as well, and this time there was a definite moan from Emily. Based on the increased moans I figured I spent more time with her left nipple than her right as she finally pulled back, both of them rock hard now.

She stepped back off of me and said, "Alright Daniel, here's the deal, I'm not going to have sex with you." This didn't phase me at all, the fact that she'd let me get to second base with her was pretty amazing by itself, and even if I wasn't facing my own death in half a year I'd remember this experience for a lifetime.

"However, I don't think it's fair that I got you all worked up," and at this point she was saying this while looking down at my dress pants, which were straining unlike how I'd ever seen them. "So You've been to first base, and second base, I think we'll call you safe on third before this is all over."

She got back near the chair and dropped to her knees, and once again I pinched myself, cause this clearly had to be a drug induced dream--but no, the pinch hurt. She reached down and finally pulled the thong down her thighs, lifting each knee as she needed to in order to slip it past. "I'm still not going to let you see my pussy, but I'll give you a clear view of my ass. Plus, I want you to have these to remember." And she took the blue thong panties and stuffed them in my pants pocket.

Okay, I'll admit like any guy, while I may not have come to the hotel room tonight expecting this, I sure as hell dreamed something like this could happen, so I jacked-off a lot this morning, like I did every morning. As Emily undid the button on my dress pants and unzipped the fly, I only hoped that I could have some stamina and not cum immediately. I was counting on the fact that I was a loser with girls who had to resort to viewing porn to get off to keep me in the game longer.

She pulled my cock out from my boxers, it was the first time a girl had touched me of course. She looked up at me, smiled, and then bent her head down and started to take it in her mouth--and then it happened. Emily barely had my cockhead in her mouth when I popped. I let out a grunt of pleasure but mostly felt embarrassed. I just leaned my head back and felt my cheeks burn bright red as Emily's mouth remained on my cock.

When my orgasm subsided she looked up and said, "Okay, that was a bit quicker than I expected, although I probably deserved that considering how quickly I've progressed things from you being untouched to getting head." I looked at her and noticed she was looking up at me while she talked. Her hand still held the base of my now-softening cock before I realized that my celebrity crush just swallowed my cum.

"Tell you what, that's not really deserving, so I'm gonna wait till I get you to cum from a proper blowjob," she said, and all of a sudden her mouth was back down on my cock.

My eyes bulged, for the first moment it actually kinda hurt to have her tongue on the head of my cock, but that quickly subsided. Since I was much smaller soft (obviously) Emily took my whole cock in her mouth and started humming and licking. Even though my cock was resisting only because it recently came, I couldn't deny that the girl had skill--well, maybe she didn't, I wouldn't really know, but it felt amazing. Strike that, it felt a-MAZE-ing!

Emily didn't try to look up at me as she tried to bring my cock back to life, she just kept her face buried in my groin working hard at it. All the licking and the humming, and even the faintest rubbing of one bit of it with her teeth finally started to have an effect, and I felt myself hardening. Emily noticed this too as she started to back her mouth off my cock, instead once again taking the base of it in her hand. Once I got back to my normal hardness (I was average so nothing too impressive), she really got to work.

This time she looked at me and said, "Just watch." She started with flicking the head of my cock with her tongue--it felt so different compared to having the middle of her tongue swirling around it. And there was something to be said for her flicking at it while staring into my eyes. She looked down to my cock and wrapped her lips around the head and started going down, only an inch past my head though before she pulled back. Once she had several strokes of this she looked back up into my eyes, watching me watch her.

Knowing I'd never make love to a woman properly, this was definitely the defining moment of the best parts of my life. Emily continued her pattern of pulling off to lick with her tongue and move back into bobbing her head up and down all while looking up at me. For what it was worth, Emily was making love to me with her mouth, and my body tingled in pleasure like it never had before.

As I started to tense up, getting closer Emily doubled down on the whole going down, taking me deeper into her mouth. Finally there was no way I could take much more of Emily's ministrations and I looked down at her, past the bobbing purple hair into a view of her ass that few if any had gotten to see and I once again exploded. I had no idea how much cum was coming out at this point, but I didn't care. Emily, bless her, dutifully waited until I was done before once again removing her mouth from my cock and turning away to grab her pants from the floor. She stood up, using the pants to cover herself until she could put them on and she smiled as she looked at me, completely spent in the chair.

"Third base, but the night's about over."

I looked over at the clock, she was right. She went into the next room real quick, giving me a view of her bare ass while walking away this time and came out with her pants on, sans the panties in my pocket. I realized I was being rude still hanging out and tucked myself away. She grabbed her white shirt and put it on without the blue bra as well, handing that to me and saying, "Gotta have the two piece bonus," with a wink.

I laughed as Emily made a gamer joke. Definitely much cooler than I ever thought she could be (which is saying something). She put the plaid jacket and the scarf back on, "See, no one will notice a thing."

We put her underwear in my actual room I was sleeping in for the night, hidden in the overnight bag I brought. When my cell phone fell out she grabbed it and called a number, her own cell phone in the purse she had by the door (that I hadn't noticed till now) started ringing.

"Now listen, I'm gonna add you to my phone list, and now you have my number. When you do finally land in the hospital I want you to text me, and I'll come visit," she told me before heading back out to slip her heels back on. Standing once again how she did when I first met her a few hours earlier, she smiled and pulled me in for a hug.

"Bye Daniel," she said before kissing my forehead, "I hope this night was everything you hoped for."

And with that Emily Osment grabbed her purse, opened the door and walked out of my suite. Oh man, was it everything I hoped for and more.