Mom's My "Someone Special" Pt. 01

I also didn't mind the fact she was twice my age, as the acronym "MILF" was often used while I was on the internet. You can blame that on Mrs. Partridge, my ninth grade science teacher - but I digress. I quickly typed my reply and then after that Jackie and I began IM'ing on a regular basis. We started off by getting to know one another. You know; what we did in our spare time, past relationships, that sort of thing. She also told me about her two kids and job as a chef.

I really liked talking to Jackie. Our conversations just seemed to flow. In fact, I felt so comfortable talking to her I even told her I was still a virgin. Which I thought was a mistake until she told me how much she looked forward to teaching me how to please a woman. After that our conversations took a more sexual turn. I'd stroke my cock and she'd tell me about the amount of fingers she had stuffed in her pussy as we typed out all the dirty details we wanted to do to one another.

I blew my load two to three times a night reading her words, and that only worsened after the role playing game she suggested. It basically involved us typing our way through all different kinds of...let's say; everyday scenarios, and the ultimate goal was to get our character's to hook up. The scenarios may have been a little cheesy and farfetched, but they always got me hard as hell.

"Carrying your hot box of pizza, I walk up to your front door and ring the bell," I typed then waited a few moments for her reply.

"Dressed in my white robe, I open the door, see you and can't help but think: He's a cutie."

"'Hi, ma'am. I've got your pizza here.'"

"'How much is it gonna cost me?'"

"'Fifty bucks.'"

"'Okay. Would you mind waiting in my living room while I get my purse?'"

"'No problem.'"

"I lead you to my living room, where you take a seat on my couch. I tell you I'll be right back and head to my room, where I take the money I owe you out of my purse. But as I do, a naughty idea pops into my head. Here's the thing; I haven't had sex in months. My poor pussy hasn't been stuffed by anything other than my cold dildo.

"And I can't help but think that hunky young man sitting on my couch is the perfect answer to my little problem. With a smile I place my money back into my purse, get out of my robe and into my skimpiest nightie (no panties). Then I head back to the living room, where I say, 'I'm sorry to tell you this, but I don't seem to have enough money for the pizza.'"

I chuckled. "I take one look at what you're wearing and can see where this is going. 'Is that so?'"

"'Uh-huh. Is there any other way I can pay for it?'"

"I examine your sexy body for a few moments. Then I motion you to come and stand in between my legs."

"Mmmmm, my nipples stiffen as I walk up to you and stand exactly where you want me."

"'Are you willing to suck on a stranger's cock just for a pizza?'"

"I nod with a smile."

"'Dose that speak on how hungry or horny you are?'"

"'Both,' I get on my knees, reach into your pants and pull out that wonderful cock of yours before I take it into my mouth."

"'This better be worth the drive here you cock hungry slut.'" Normally I'd never use this kind of language while taking to a lady, but I'd come to learn how much Jackie loved it.

"I pop you from my mouth and say, 'It will be, sir.' I wink then take your cock back into my mouth."

"I like that word, 'sir'. The blowjob isn't bad either."

"I let go of your shaft, brace myself with your cockhead in my mouth and push my head downwards to take you into the back of my throat."

"'Ahhh, at least you know what you're doing, slut.' I place a hand on the back of your head and start moving my hips up and down, jabbing my cockhead into your throat."

"Mmmm, I feel my eyes watering up and want to thank you for the compliment, but I'm too busy taking you into my throat."

"'I wonder what your father would say if he saw you sucking cock like this for food?'"

"I grab your shaft, pop you from my lips and say, 'He probably wouldn't have said anything, sir. He would've just given my ass a good hiding.' I take your cockhead in my mouth and use my tongue to play with it as I suck in your pre-cum."

"'I like the sound of that. Get over the arm of the couch, slut.'"

"'Yes, sir.' I get up and do as I was told."

"I get behind you and rub that nightie covered ass of yours. Then I push your nightie up your hips, exposing your creamy butt cheeks. I use both hands to massage them for a little while, enjoying their soft sensation. Then I pull off my belt and give your ass and nice hard lash."

"'Ouch!' I cry as my pussy saturates. 'That's one, sir.'"

"'Good girl, counting without me having to tell you. But that's not gonna save you from getting spanked...you've been bad.' I give your ass another lash."

"I don't want you to stop spanking me, but I'm too much of a sub to say that out loud. 'That's two, sir.'"

"I give you three more hard lashes."

"And I let out a cry each time and keep counting, 'Three, sir...Four, sir...Five, sir.'"

"Once I get your ass all nice and red, I throw my belt to the floor, take a hold of my cock and press the tip of it against your pussy lips."

"Mmmmmmmm."

"'Tell me how much you want this cock, slut.' I brush my tip up and down your wet lips."

"'Oh yes, I want your cock sooo badly, sir. Please give it to me! I need it!'"

"'Because you're a...'"

"'A cock hungry slut.'"

"I take a hold of your hips, push my own hips forward and drive my cock deep inside of you."

"'Oooooh fuck! Yes, sir! That feels so-so good!'"

"I pull you nightie down your back until your tits are exposed. Then I knead those massive mounds of flesh as I start hammering your cunt."

"'Yes! Yes! Yes! Fuck me good and hard, sir. That's how I like it. Oooooohhh!'"

"I grab onto your hair and pull your head back so I can say this in your ear, 'Take my cock you dirty slut. Take it all.'"

"I love the way you're treating me. 'I'm taking it as best as I can, sir. Keep giving it to me! I'm almost there.'"

"I give your ass five more hard spankings with my hand as I keep driving my hips forward. Then I grab onto your tits again and squeeze your hard nipples."

"'Fuck!' That did the trick. 'I'm cumming, sir! Oh God yes! I'm cummm-aaahhhhh!'"

"I keep squeezing your nipples and fucking you until your noisy orgasm comes to an end."

"'Oh shit! That was...so goooood!'"

"'Where would you like me to cum my new pet?'"

"'Oh God. On my face, sir.'"

"'Then get on your knees, slut.' I pull out of your pussy."

"'Yes, sir.' I hop off the couch, get down on my knees and take a hold of your pussy juice coated cock. Then I point it at my face and stroke it until you blow a huge load all over my face, hitting my nose, cheeks, forehead, chin and lips. But before you can finish unloading, I take your cockhead into my mouth and suck your last few spurts down my throat and into my belly. Then I look up at you and smile, so you can see what you've done."

After reading her last sentence, I found myself at my desk, panting, all sweaty, with a huge load of spunk on my stomach, wishing what we'd typed had really happened. But that's how I felt after every scenario we typed out. I pulled out a few Kleenex tissues, wiped myself off and tossed them into my trashcan. Then I sat back down and continued my chat with Jackie:

"That was a good one."

"I know. You've got me sitting in a puddle over here."

"Lol. You should've seen my stomach a minute ago."

"I wish I had. I would've licked it clean."

Fuck. This woman always knew what to say and it only strengthened my desire to meet her. "So, when do you think I'll finally get the chance to see you?"

"How 'bout this weekend?"

My eyes nearly popped out of my head. "Really? You don't think that's too soon?" I have no idea why I was asking questions.

"Nope. We've been chatting for weeks now and I'm dying to see that cock of yours in the flesh, so I can stick it in between my lips, tits and pussy lips for real."

My cock twitched, even though I'd cum not so long ago. "What about your kids?"

"They stay at their father's place on weekends, so I'll have the house all to myself."

"Then it's a date."

"Great! JJJ Listen, I've gotta run. We'll discuss the details tomorrow."

After we wrapped up the conversation by saying goodnight, I felt dirty - in the literal sense. I was sweaty and smelt of semen and I didn't plan on sleeping like that. I hopped to my feet and headed to my bathroom, where I stripped and entered my shower. As the water splashed my face and cascaded down my body I couldn't get the thought of Jackie out of my mind.

I was finally going to meet her! And after this weekend I would no longer be a nineteen year old virgin. Moreover, most of the guys my age could only dream about the kind of sex I'd have with Jackie. I was so excited I couldn't restrain myself from dancing as I scrubbed my body. As I did I thought I heard the sound of my name being called, but wasn't sure until I heard it again; Mom was definitely calling me. Wondering what she wanted I decided I'd head to her bedroom after I got done.

Fifteen minutes or so later I turned the taps off, stepped out the shower and grabbed a towel. Then I stepped to my sink and brushed my teeth. The curse will soon be lifted. I looked into the mirror on the wall with a smile after rinsing. Once I switched off the bathroom light, I walked down the hallway and entered my bedroom. I found my mom in there. She was sitting at my desk, facing away from me, and was dressed in a white shirt and baby blue pyjama bottoms. What's more, she had her honey blonde hair tied in a ponytail.

"Hey, Mom, what's up?" I walked to my closet.

"What's this?" She turned to face me as she pointed at the screen of my PC.

Shit. Did I forget to close the chat I had with Jackie?

Chapter Three: Maternal Intervention

"Huh?"

"Don't play dumb with me, Christopher. Who's this woman you're talking to?"

"Umm, she's a friend...a friend from school."

"Stop lying to me. Her profile says she's thirty-eight, and she's talking about kids and an ex-husband."

"Jeez, Mom, have you ever heard of respecting other people's privacy?" I walked to her and closed the internet window.

"Don't try 'n' flip this on me; you're the one in the wrong here. Okay, you know what, let's not argue about this. I'm not angry with you. I'm just...worried."

The apprehensive look in her eyes confirmed what she said. I sighed. "You don't have to worry, Mom. Nothing-"

"What do you mean I don't have to worry? Of course I do. You don't know who this person is. And you're planning on meeting her this weekend? What if it's some fifty year old man, who plans to do...Lord knows what to you?"

I didn't have a reply. Mom had a point. There was a possibility in that being true. I watched Catfish.

"Why're you doing this, honey? You're a handsome young man. Why're you on the internet trying to get into a relationship with a woman who's nearly forty years old? I'm pretty sure there're plenty of girls your age who'd love to date you."

I let out another sigh as I walked to my bed. I really didn't want to have this conversation with her, but there was no avoiding it. I took a seat and said, "It's complicated."

"What's complicated?"

"The reason why I'm talking to Jackie...that woman on the internet."

"Okay, well...try to explain it to me. I'm not an idiot."

I took a deep breath and cleared my throat. "It's a...it's a sex thing."

"Okay. I figured out that much...from your chat. And I guess our discussion on this matter is long overdue." Mom thought for a moment. "You've reached the legal age now and I know all the guys your age want to experiment...sexually - there's nothing much I can do about that. I'm also pretty sure you know why you should always practice safe sex. But why don't you do that stuff with one of the girls in your school?"

"I tried to, but for some reason...every time I try to get...sexual with a girl I end up messing it up somehow."

"So that's what this is about - you're a virgin?" Her eyebrows rose.

I groaned as my head fell back.

Mom laughed softly. "But there's nothing wrong with being a virgin, hon."

"Yea right."

"I'm serious, Chris." She got up and came to sit beside me. "And besides, you don't want your first time to be with some stranger you met on the internet, you want it to be with someone special - someone you can see yourself spending the rest of your life with."

Oh jeez. Trust my mother to say something that gay. "Okay, honestly, Mom, the world doesn't work that way. These days, if you're not having sex then you're a loser - especially if you're a guy."

She mulled for a moment. "Be that as it may, what does this woman you're talking to have to do with this? Nobody's gonna praise you for sleeping with her."

"It's not about getting people to praise me, Mom. It's..." I'd been trying to avoid saying this throughout the conversation, I didn't want my mom to think I was a goofball, but there was no avoiding it, "it's about my curse." I sighed. "I think if I can sleep with Jackie my curse will go away and I'll stop slipping up every time I try to have sex with a girl."

Mom smiled. She actually looked tempted to laugh. "You know how silly that sounds, don't you, hon?"

I nodded.

"But I get it. Everybody's at least a little superstitious. I wiggle my nose before I get on a plane. And I kinda see why you think sleeping with this woman will help you. It's more of a confidence thing. But I still don't trust her. There're a lot of weird people in this world and a lot of them use the kind of site that you're on. I'm a paralegal. Trust me; I know. So please just be patient, hon. I promise you, it will eventually happen - hopefully with the right girl."

It took a few seconds for me to say, "Fine."

*

Two nights later I was in my room studying. If there was anything I took more seriously than my love life - or lack thereof - it was definitely my school work. I planned on becoming an attorney and I knew the kind of grades required in order to do so. I was no genius, but I knew if I studied hard enough no grade was unreachable. You might wonder why I'd choose to pursue this career path. I mean, with all the flak that lawyers get. And it's not because I wanted to make a lot of money. I wanted to become an attorney because it's what my father did. He was my hero and I aspired to be like him.

Dad was killed six years earlier, on the night of my grandmother's birthday. While taking her out for dinner as an extra present, some drunken idiot slammed into them. The hit sent them flying off the road and down an embankment, causing the car they were in to flip over a few times. Granny ended up in the hospital for a couple of weeks, but Dad wasn't so lucky. The head injury he received was too severe. The guy in the other car got out unscathed to add insult to injury, but received a three year jail sentence.

Dad's passing was tough on the entire family. I remember crying, throwing stuff around and punching walls for weeks. But the person my father's death affected the most was my older sister, Kirsten. She mourned as long as everybody else did, if not then more, but it didn't stop there with her. She began drinking, partying and arguing with Mom way more than she normally did. There was even a time we had to bail her out of jail for public intoxication and indecency.

She was out of control and ended up dropping out of high school. Mom did everything in her power to get her to go back, but my sister refused to comply. She's a waitress slash bartender now and lives on the other side of town with her boyfriend, Craig. I check up on her every now and then and she seems to be doing alright.

Sis' downward spiral broke our mother's heart, though, and I think it added extra incentive to me wanting to become a better student. I didn't want Mom to be disappointed in both her children. The only positive thing to come out of Dad's death was the insurance money. It meant we got to keep our house and that my education would be taken care of. Mom didn't make a lot of money as a paralegal. But she didn't need to. We were comfortable.

I flipped a page in my history book. I'd also been thinking about the whole Jackie situation. I'll admit it; I still wanted to meet her pretty badly. I'd given Mom my word I wouldn't, but I was seriously starting to think I was going to go back on it. I was convinced Jackie was really who she said she was. But still, I couldn't help thinking Mom might be right; I could really be talking to some cunning predator.

Maybe I should video chat with Jackie before I meet up with her...Yea. I nodded. Why didn't I think of that before? I heard a knock on my door and once I answered Mom came walking in. "Hey, hon. Do you have a minute to talk?"

"Sure." I swivelled my chair. "What do you wanna talk about?"

"Well," she took a seat on my bed, "I've been thinking about the problem you told me about the other night and I think I've come up with a solution that can help you."

I stared at her for a few seconds then nodded. "Oookkkaaayyy."

"You know my friend Rochelle, right?"

How could I forget her? She was without a doubt my mother's hottest friend and honestly one of the most beautiful women I'd ever seen, which includes the people on TV. She had long blood red hair. A dark pair of green eyes, with a splash of brown in her left...or was it her right? Her mildly bronze skin didn't carry a single blemish. And her body should only be described as "magnificent".

She was blessed with a perfectly symmetrical hourglass figure. She had a pair of breasts that brought the image of two coconuts perched in a tree on some tropical island to mind. There wasn't the slightest hint of sag to them and couldn't be called too big or too small. Their size suited her body to a tee. But I'm willing to bet my house she'd undergone breast augmentation surgery.

Rochelle also had spectacular round ass, and a gorgeous pair of legs that looked capable of kicking a football right across the length of a field. She was one sexy woman. And I couldn't think of a single thing wrong with her. Except, maybe she wore a little too much makeup. But now I'm just nit-picking. It's pretty obvious I spent a little bit of time fantasising about this woman, but why was my mom bringing her up?

"Yea." I nodded.

"Well, about a year ago she told me what a strapping young man she thought you'd become and even admitted she wouldn't mind sleeping with you."

I was shocked. I thought my odds in sleeping with Rochelle were as good as trying to get a suntan in Antarctica. I leaned forward and listened to Mom with meerkat ears.

"I told her to keep her paws off you. I know how much of a man-eater she can be. But because of the scare you gave me the other night, and because I've got this sneaky feeling you still plan on meeting that woman, I decided to meet up with Rochelle today and asked her if she was still interested in you."

"And," I leaned forward even more, "what did she say?"

"She said she still is." She nodded. "I'm not gonna lie, I'm not crazy about this whole idea. But I figured, better the devil you know. So, are you interested?"

I'm I interested? Is she serious? "Yea," I said, with a slight shrug, trying not to look too excited. "But how exactly is this gonna work?"

"Good question. It's not like she wants you to just show up at her house, pick her up and take her to her bedroom. Girls don't work that way. Even if the main goal is sex, there still needs to be at least a little bit of romance involved. So here's the deal, you'll take her out on a date this weekend and if all goes well...she'll make you a happy man."