tagCelebrities & Fan FictionMy Blind Date with Alyssa Milano

My Blind Date with Alyssa Milano


"It's been so long since I got laid!" Alyssa whined, as she poked her fork into a piece of cucumber and bringing it up and into her mouth.

"You could get laid any time you want!" Julia said. "You can go up to any guy and say I'm Alyssa Milano, would you suck my pussy for me please? And he'll do it. You're a total babe!" She carried on, taking a bite of her burger.

"Yeah! But they'll go to the press and say 'Alyssa Milano asked me to give her head' and totally sell me out."

"I wish I could go up to any guy I want and say to him 'Take me now!' I just don't have a smoking hot body like yours."

"That's because I wok out." Alyssa said with a mouthful of lettuce. "And eat healthily." She said pointing at her salad with her fork. "Unlike you. Shovelling burgers into your face whenever you get the chance."

"I do not!" Julia protested and both the girls laughed. "I don't see a shovel any where." Julia wasn't a bad looking girl, she wasn't great looking either, she was in the middle. Everything about her was average. Which made her quite jealous of Alyssa, but they had been good friends for a long time.

"That looks so good!" Alyssa said staring at Julia while she ate.

"You want some?" Julia offered, knowing Alyssa is a vegetarian.

"No! I don't believe in eating flesh. I have to stick to the healthy eating." Alyssa said picking up a tomato with her fork.

"Maybe you wouldn't be sexually frustrated if you ate properly." Julia commented.

"What's eating and sex got to do with each other?"

"Nothing!" Julia said. "But what do you prefer? Sex or chocolate?" She asked trying to prove some kind of point.

"Ohh! That's a hard one!" Alyssa said squinting.

"When's the last time you had chocolate?" Julia asked. Alyssa laughed.

"It's been a while. But even longer since I've gotten laid."

"Well if you want, I could set you up with a friend of mine." Julia suggested.

"Sure! I'm desperate, so I'll try anything. But if he's ugly I think it's fair that you pick up the check."

"You're the famous one who gets a lot of money for being in movies and on TV!" Julia protested.

"You're the one setting me up with an ugly friend of yours."

"He's not ugly!" Julia protested.

"Have you slept with him?" Alyssa asked.

"No." Julia replied.

"Why not? It's cause he's ugly isn't it?" She asked looking at her suspiciously, squinting.

"He's not ugly!"

"You keep saying that." Alyssa said picking up another piece of tomato with her fork. "What does he look like then?"

"He's cute. He's tanned, he looks a little Latin. He's got a ponytail, goatee..."

"Whoa, whoa, whoa! Wait! A goatee? What kind of goatee?"

"Just on his chin. Not around everywhere that he gives you a rash when you kiss."

"Oh! That's good. What else?"

"He's about 5'8" a medium build."

"Medium build? What does that mean? He's fat but not quite fat?" Alyssa asked.

"No. He's not fat, he's not skinny. A bit bigger than skinny, well toned."

"Tone is good." Alyssa cut her off. "I'll go out with your friend. Just set it up. Just don't tell him I'm looking to get laid." Alyssa said as the two carried on eating and talking.

I reached home after a long day at work. I just wanted to relax and chill out. I went over to the fridge and got a bottle of beer and took the cap off with a bottle opener. I walked past the phone on my way towards the couch and noticed that I had a message. I decided to check who it was.

"Hi Kash. It's Julia. Listen, I know we haven't been able to hang out for a while, but I got a friend who's looking to be set up if you're interested. She's really pretty." Yeah right! Girls always say that about other ugly girls. "She hasn't been out with a guy for a while and I was wondering if you're interested. Even if you're not call me. We can catch up."

I sat down and took a sip of beer. I guess I should call her. At least we'd be able to catch up. I picked up the phone and the address book next to it. I looked in the 'J' section for Julia and dialled her number.

"Hey Jules! It's Kash. You called earlier."

"Yeah!" She replied. "I got a friend who's looking to get laid. But she doesn't want to seem desperate so she wants to do the whole dating thing, you know..."

"Make me work for it." I cut her off, taking a sip of beer.

"Exactly! But she doesn't want me to tell you that she wants to get laid."

"I gotcha. She wants to fuck, but she doesn't want me to know." I said drinking some more. "So what she look like?" I asked "Is she fit or is she some ugly fat chick?"

"She is very hot!" Julia replied. "She has a body I wish I had."

"There's nothing wrong with your body! You got quite a good rack on you."

"Thanks!" Julia giggled, if she was here in person, I know she'd be blushing.

"What about the face?" I asked.

"Very beautiful, long dark hair..."

"What does she do?" I cut her off feeling like I heard enough about what she looked like, taking a long sip of beer this time.

"She's in between jobs right now."

"So she's a bum." I said. "At least that shows I'm better off." Julia laughed. "What's so funny?" I asked.

"Nothing!" She said. "She's not a 'bum' she's quite well off."

"Ok." I said. "I'll do it. So what? You call her or...?"

"Well... I don't know when she's free, so you call her tell her you're my friend Kash and arrange a date."

"OK. What's her name?"

"Alyssa." She replied. She left me Alyssa's number, I hung up and dialled Alyssa's number. The phone rang a couple of time's before Alyssa picked up.

"Hello?" She greeted.

"Hi." I said. "I just...er... got a call from Julia..." I was a little unsure as to how to do this.

"Oh! The blind date." Alyssa said instantly knowing why I had called.

"Yeah." I said, feeling a little uneasy, but knowing that a hot dark haired woman was looking to get laid, I was more than happy to deal with the uneasiness.

"So should we set up a place to meet?" She asked.

"We could meet up at a restaurant?" I suggested.

"You know where McDonald's is near the beach?" She asked. McDonald's? I knew she was a bum but at least it'll be cheap I suppose.

"You wanna... go... to McDonald's?" I asked. "You know I'm paying right?"

"No!" She laughed. Her laughter sounded sweet and a little familiar.

"I was gonna say that new restaurant that opened a couple of doors down."

"Oh! I know which place you're talking about! I've been meaning to check it out."

"Same here." Alyssa replied. "So I was thinking we could kill two birds with one stone."

"Cool. So when should we meet?" I asked.

"Dinner? Tomorrow night?" She asked.

"Sounds good." I replied. "Should we meet there or should I..."

"We'll meet there. How does sven sound?" Alyssa asked.

"Sounds good." I replied.

"OK. You call them up and book a seat for two. They're new so they shouldn't be busy. OK?" She asked sounding very cheery.

"Great!" See you then." I said and hung up. That went a lot better than I had expected. It seemed quite pleasant and I think we might actually get along during dinner before we come back here and fuck.

"Hi." I said as I approached the host. "I booked a table for two under the name Kash.

"OK." The host said looking at his book. "Ah yes. Table for two." He said looking at me. "But there's only one of you?"

"I'm meeting someone here and I guess I'm a little early and she's a little late..."

"Ah! Say no more. Right this way sir." He said understanding the situation and led me to the table.

"Would you like a menu or would you like to wait till your lady friend arrives?"

"I'll wait."

"As you wish sir." He said and was off.

I sat there waiting for Alyssa to come, essentially, I could actually be sitting here for hours and not even know that she turned up at all. In fact she could've already come in, decided I was too ugly even for a one night stand and left and I wouldn't even have a clue cause I have no clue what she looks like.

"Kash?" I heard a voice call behind.

"Alyssa?" I said standing up, turning around, extending my hand to greet her and I froze in my tracks. Alyssa chuckled. I checked her out quickly. She was in a low cut black dress that showed off her cleavage and the bottom fell a couple of inches short of her knees , open toed shoes, her dark hair left out going just past her shoulders.

"I take it Julia didn't tell you who I was, did she?" Alyssa chuckled some more, shaking my hand and taking a seat opposite me.

"No wonder Jules laughed when I referred to you as a bum."

"You called me a bum?" Alyssa asked, looking surprised

"She said you were in between jobs, which usually means you don't have a job and that you can't get one."

"I don't know why she wouldn't tell you who I was." Alyssa said.

The waiter came over with menus and as we looked them over. I stared at Alyssa as she looked at the menu. She looked so beautiful. She didn't look like she was wearing make-up, apart from light red lip stick. She looked like she was going for the natural look, but let's face it. Now a days, the natural look isn't natural, women spend hours on their make up to make it look 'natural.'

All of a sudden I remembered something. Julia said that she had a friend who was looking to get laid but not seem desperate. And that's when it hit me. I'm going to sleep with Alyssa Milano! I guess I should start up some chit chat.

"So... what have you been doing since Charmed?" I asked.

"I just finished filming a movie called My girlfriends boyfriend' and I'll be starting the next movie in a couple of weeks."

"What's the next movie called?"

"It's called 'Romantically challenged.' A TV movie." She continued looking at the menu.

"I'm just destined to be on TV forever." She added laughing.

I looked down and noticed that she had tattoos on her wrists. There was one of a snake on her right wrist. It went all the way around her wrist like a watch and the snake had it's own tail in its mouth. On her left wrist she had that Hindu symbol, an 'Ohm' I think. I wasn't going to ask her about it, mainly cause people have big difference in opinion when it comes to religion and if we got into that topic, my chance of sleeping with her could go out the window.

"That's not true!" I lied. "What about that movie you did called 'Fear?' That was good."

"I was barely in it. It was big because of Mark Wahlberg and Reese Witherspoon." She answered.

"Hey! Both of those were nobodies at the time, you were Samantha from 'Who's the boss' that carried that movie on your shoulders." Alyssa laughed at that one.

"I can see there's no changing your views on my career." She laughed some more.

"Are you ready to order?" The waiter asked as he approached us.

"Yeah. I'll have the lobster." I replied. Alyssa ordered some kind of salad, I wasn't really paying attention. I was mentally moving the top of her dress to one side and revealing her large, plump breasts.

"Lobster huh?" Alyssa said. "So what do you do?" She then asked.

"I work in an office." I said nodding my head. "I think it has something to do with something." I said, staring at her cleavage, not really concentrating on what I was saying.

"Something to do with something?" She laughed.

"Yeah." I replied, realising how stupid I sounded and laughed. "It's a law firm."

"So you're a lawyer?"

"I guess." I replied.

"A lawyer at a office that may or may not be a law firm that deals with something to do with something." Alyssa repeated and laughed.

"Well it sounds stupid when you say it like that." I laughed.

Alyssa continued to ask me questions about myself as we made conversation.

"Wow! That's some quick service." Alyssa said as she saw the waiter approach us with our food.

We continued to converse whilst we ate, mainly about our careers, not really wanting to reveal too much about ourselves to the other. Once we finished, despite how much more she made than me, I still picked up the tab. I planned to pick up the tab when I arrived and nothing was going to change that.

We headed out to the parking lot. Things started to move a little fast now

"Which one's your car?" I asked.

"I got a lift here. So could you give me a ride?" She asked. This was a good thing because if she drove here, there'd be two cars, she'd probably end up taking her own car back home and I'd go off to my own place and end up not having sex with her.

"Sure!" I replied. "Just give me directions." I added as we got into the car.

"What kind of music do you have?" Alyssa asked.

"Mixture of everything. " I replied. "I have about ten CD's stored in the CD player. Just flick through until you find something you like." Alyssa started to check through the CD's as I pulled out of the parking lot.

"Just keep going straight." She said as she quickly dismissed any CD's that were hip hop or R'n'B. She decided to settle on to the Red hot Chilli Peppers. We carried on talking on the way. She seemed to be a fan of the Chilli's and was singing along to them, so that avoided any questions that she might've asked if there wasn't any music.

"You can't miss my place. You can see it a mile away, it's quite a big ranch." Alyssa said when a guitar solo hit.

"You live on a ranch?" I asked, sounding very surprised.

"Yeah." Alyssa replied. "It's about 40 acres."

"You got animals?"

"I have eight horses!" Alyssa said sounding quite proud. "But there's suppose to be a mountain lion on the loose so I'm quite scared it might try and eat one of them."

"What....? There's a mountain lion out here?" I asked sounding shocked and a little scared. I started to look around to see if I could see it.

"But don't worry, apparently bear urine repels them." Alyssa said.

"Where'd you find bear urine?" I asked.

"I didn't." She laughed.

"There! Over there!" Alyssa said pointing. I pulled up and drove up the dirt road, stopping in front of her house. I wasn't sure if I should make the next move or if I should wait for her to make the move.

"So... this is me." Alyssa said. By the sound of things, she sounded like she wasn't sure either. "You wanna come in for coffee?" Yes! The universal language for you wanna stay the night and fuck?

"Yeah. Sure. Should I leave the car here or..."

"Park it over there." Alyssa pointed to a empty spot next to her car. I quickly moved the car forward and parked perfectly next to her car in one attempt. Alyssa than led me into her house, I walked with her, looking around feeling a little nervous. Not just cause I was going into Alyssa's home for sex but now mainly more due to the fact that I know there's a mountain lion prowling about.

Alyssa opened the front door and keyed in her alarm code, to turn the alarm off. She had her back turned to me as she bent over whilst reaching down to unhook the back of her shoes off her heels. I stood there staring at her perfectly round rump. Seeing as though she was taking her shoes off, I guess I should too.

"Make yourself at home." She said motioning towards the couch. Her whole house was a white, creamy colour. It was very soothing. Alyssa walked off leaving me alone in the living room.

After about a minute of waiting, I decided to go to her in the kitchen. I assumed she was going to put the coffee on to boil and come back, but it looks like she was in the kitchen waiting for it to boil.

I walked into the kitchen and Alyssa had her back turned to the door so she didn't see me come in. It turned out that she was standing there watching the coffee pot boil, leaning against the kitchen counter.

I slowly approached her, expecting her to hear me and turn around, but she was oblivious to my presence. As I approached her, my eyes once again fixated on her thick round rump and the way she was leaning over the counter, sticking her butt out, it looked so tempting.

I walked up behind her, pressing my crotch against her ass and wrapped my arms around her waist. She was startled at first, and stopped leaning forward against the counter, standing up straight. But when she turned her face to see it was me, she was back to normal.

It was almost as if she forgot that I was here and thought that she was alone in her house and thought maybe a stranger came in and started to molest her.

Alyssa seemed a little nervous and slightly twitchy when I touched her. It was obvious why I was here so I decided to stop procrastinating and make the first move. I started to kiss her neck, which caused Alyssa to moan.

"Julia told me exactly why you wanted this date." I whispered into her ear, hoping that this would help advance things along.

"What?!" Alyssa said sounding a little annoyed, moving her head away from my face.

"That slut!" She said looking at me.

"I can't help but think of the word ironic." I joked and it caused her to laugh, placing her hands on mine.

"You shut up!" She said once she stopped laughing, squinting with one eye.

"I would think that would make things easier." I said.

"It sort of does." Alyssa said, nuzzling the back of her head against my neck. "I've been so nervous leading up to the date and even during the date. I was like; How am I gonna get him to have sex with me?"

"Pretty easy really." I replied. "If any female shows a guy a little boob, he'd be like; Oh man! I'm in!"

"You mean like this?" Alyssa asked as she lowered one side of her cleavage to expose one of her tits.

"Yeah, just like that." I said, my voice going low as I reached up with one hand, cupping her boob and gently squeezing it, feeling her nipple get erect and poke out against my palm.

Alyssa pushed her chest out forward, allowing me to caress her large mounds, moving the straps off her shoulders, letting her dress slip down just enough to reveal her large breasts.

I slowly exhaled as I started to rub her large breasts, I couldn't believe that I was actually touching Alyssa Milano's bare breasts. Alyssa turned around and placed her lips on mine, kissing me quite passionately as she used her hands to quickly undo the buttons of my shirt.

As I quickly pulled my shirt off, Alyssa went for my pants, undoing my belt, button and pants, her lips still locked on mine, letting my pants and boxers fall down. She lifted one leg up, wrapping it around my waist, her heel pressed against the back of my thighs.

Alyssa had her body pressed against mine, her erect nipples poking against my chest as we still sucked each others tongues. Her crotch was pressed against my already erect cock and I could feel the softy silkiness of her panties on the tip of my cock.

They felt like they were quite small and when I reached down, I could feel that they were indeed a thong. Which was very practical, I just moved them to the side, using the same hand to hold my cock and push the tip into her waiting cunt.

"Ohhhhhhhh!" Alyssa let out a long moan into my mouth as she released my tongue. I slowly worked my hips forward, getting more of my thick shaft into her woman hood, causing her to wrap her arms around my shoulders tight and pull me close to her.

She quickly lifted her other leg, wrapping that one around my waist too, holding me tight with her legs. I almost lost balance when she did this due to it catching me by surprise.

I started to walk towards the kitchen counter, stepping out of my boxers and pants as she started to kiss around my mouth area. I tried to set her on the kitchen counter, but it was too high for me to set her ass on it and still thrust my cock deep in to her.

So I walked past the counter and into the living room, getting on the couch on my knees and setting her down on to her back, not letting go of her and her not letting go off me as I now lay on top of her, thrusting my hips back and fourth gently.

I pulled my lips away from hers and watched her face groan in pleasure as I worked my fuck stick in and out of her.

She exhaled lightly every time I thrust forward, her pussy feeling unbelievably tight around my dick. I think she was just adjusting to the girth, so I continued at this slow pace until I felt like she could take more.

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byKash_the_priest© 3 comments/ 38491 views/ 26 favorites

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