Mom's My "someone Special"

Author's Note: This's yet another one of those kinda long stories, so I suggest you skip it if you're looking for a quick fix. If I'm not mistaken, this's the Incest/Taboo section of the site, so if you feel the need to tell me why mother and son stories are horrible; please...feel free...to keep it to yourself. I always wanted to say that. Finally, all the characters in this story involved in sexual activities are over the age of eighteen and you must be over that age as well in order to read on. Otherwise, enjoy.

* * * *

Chapter One: The Curse

I couldn't believe it was my final year of high school and I still hadn't gotten laid. That's right, I was a virgin, a nineteen year old virgin at that, and in this day and age that's just embarrassing. What's worse is all my friends had been able to pull it off, or so they all claimed, and they were all a year younger than me. I started attending school a year later than the average student.

Being a virgin at this age didn't come from a lack of trying if that's what you're thinking. Oh no. I actually came close on a few occasions, but ultimately failed each time. For instance, about a year earlier I was at my best friend's big sister's twenty-first birthday party. And what a party it was. The house was packed full of people. There was booze on almost every table you could find. Girls ran around in their bikinis. And music was played by both a band and DJ.

Nate and I didn't gate-crash this event, by the way. Lindsey was pretty cool and had given the two of us permission to be there. Anyway, during the evening I managed to get into a conversation with one of her university friends. Michelle was her name - if memory serves me correct - a tall slender young thing, with dark hair, pale blue eyes, and a deadly smile.

She must've liked what I'd been saying to her. She couldn't seem to stop playing with her hair or flashing me that smile of hers. I'm no pick-up artist, but I knew these were good signs. I didn't know how good, though, because about twenty minutes into our conversation she said something I could never say I saw coming:

"Do you wanna make out?"

I hesitated as if it was a trick question. "Of course."

With a smile she moved closer in on the couch and rested her arms on my shoulders. Then her face moved in and lips merged with mine. I placed my hands on her waist and pulled her closer as her pierced tongue pushed past my lips.

Why can't it always be this easy?

Our tongues dueled inside my mouth for a little while before we made them cross over and play inside hers.

"Wow," she said a couple minutes later. "You're a good kisser. You're actually making me wet."

I'm sure this put a silly looking grin on my face. "I'm glad I could be of service."

She laughed. "Let's go upstairs and find a room."

Grabbing me by the hand, Michelle hopped off the couch and helped me up. I must say, I was shocked with how - for lack of a nicer word - slutty this girl was. But I wasn't complaining and if this was how most of the girls in university were, I couldn't wait to get started. We made our way upstairs and entered the first available room we could find, which also happened to be the hostess's room - hopefully she wouldn't mind.

As soon as the door was closed Michelle had her arms around my neck, boobs squashed against my chest and lips locked with mine in a heartbeat. She almost knocked us over. I couldn't say I was used to her kind of enthusiasm, but I'd be lying if I said I didn't like it. I placed my hands on her small buttocks and made out with her for the next few minutes.

Then she used her chest to push me backwards until the backs of my legs bumped into something. I wasn't sure what it was. Michelle placed her hands on my chest and gave me a hard shove. Suddenly falling backwards gave me a bit of a fright, but to my relief I landed on a bed.

This girl's pretty damn aggressive

.

She hooked her fingers under the hem of her black shirt and pulled it over her head, revealing the lacy black bra she had on. I'm not great at estimating cup sizes, but her boobs looked to be somewhere between B and C cups. Man I couldn't wait to get an eyeful of those puppies. Fortunately I didn't have to wait too long; her next step was to unclasp and let her bra slide down her pale arms.

"Like what you see?" She placed her hands on both sides of her tits and squeezed them together.

"What do you think?" I looked at the bulge in my jeans.

With a smile she crawled on top of me, crushed her boobs on my chest and pressed our lips together. The feeling of her hard nipples poking into my chest caused my cock to twitch as we continued to make out. As she gently bit my lower lip her hand slid its way down my torso and unbuttoned my jeans. Then it found its way into my boxer briefs and took a firm hold of my cock. I couldn't stop myself from groaning into her mouth. The softness of her palm could make a cloud feel insecure.

As her hand worked its way up and down my shaft, I could tell she was no amateur in the tricky art of the hand job. She made great use of the pre-cum my cock emitted and made sure she gave my glans a little extra affection. Her technique was majestic. When she removed her upper lip from my mouth, she got in between my legs, hooked her fingers into my jeans and underwear and pulled them down. I raised my hips and helped her get them around my ankles.

Now on her knees, she retook a hold of my shaft. My heart pounded as I watched her tongue slip from her lips. Then my eyes closed and legs trembled as she lightly circled her tongue around my glans a few times. When she took me into her mouth I couldn't stop myself from groaning. I gently placed a hand on the back of her head as she moved her lips back and forth, only sucking my cockhead as she used her tongue to stroke my slit for what felt like the greatest minute of my life. Then she pushed her head lower and started taking the rest of my erection into her mouth.

She couldn't get the entire length in, but it didn't matter to me. I was still having a great time. Michelle skillfully bobbed her head for the next three minutes or so, making soft moist noises and causing me to moan and groan. I couldn't believe my luck. I was with a beautiful girl who I'd just met and she was giving me head! The level of my excitement was off the charts! It's not like all my weekends turned out like this.

Michelle popped me from her mouth and looked me in the eye. The look of lust in her eyes was in

HD

. She got to her feet, removed her shoes and squeezed her thumbs into her jeans. Then she wiggled her hips and pushed her pants down her long smooth legs. Her black thong went down with her jeans in the process, leaving her completely hairless pussy exposed. I removed my shirt as she stepped out of her pants.

The raven haired beauty then straddled my lap and let her pussy hover a couple inches or so above my waiting cock. I thought I was excited during the blowjob but that didn't compare to the feeling I got from knowing she was going to let me fuck her. I'd finally know what being with a woman was like. But I felt no need to rush and earlier on I'd made myself the mental promise of sucking on those wonderful tits.

I placed my left hand on her hip, moved my face in and sucked her left nipple into my mouth. She moaned as she placed a hand on the back of my head, pushing me harder against her tit. Then my right hand came up and cupped her mound. Boy was she wet. I pushed my middle and index finger past her labia and heard a moan.

But apparently my fingers weren't what she wanted inside her. She placed a hand on my wrist, removed my fingers from her sex and placed her hands on my shoulders. "I'd rather have your cock in there." She smiled as her frame lowered.

I thought the moment I'd been waiting for had finally arrived, but to my utter disappointment the bedroom door swung open, causing the descent of her body to stop and both our heads to turn. "Oh my God!" said Lindsey, with her eyes as wide as tennis balls. "

Michelle,

what're you doing?"

"Ah," Michelle looked at my cock and then back to her friend, "what does it look like?"

"It looks like you're about to have sex with my little brother's friend - in my room."

"Your little brother's friend?" Michelle's head made a quick turn so she could look into my eyes. The look of shock in her own eyes gave me a

horrible

feeling. She turned her attention back to Lindsey. "Really?"

"Yep." Lindsey nodded with a smile. "He's in high school."

"Shit!" Michelle hopped off the bed and picked up her pants and underwear.

"What's wrong?" I asked.

"Sorry, Chris, but I didn't know you were in high school." She stepped into her thong. "And I don't fuck kids."

"I'm not a kid. I'm eighteen."

"That's still a little too young for me. Sorry."

And that's the story of how I got cock-blocked by my best friend's older sister.

*

Then there's the time we decided to throw a party. Actually, it was more like a get-together and it took place at Dean's house, right after school on a Friday. We had a handful of girls in our grade there. There was plenty of food and drinks to go around. And music was played by a phone connected to a large speaker. I remember being a little bored at first, but that was only until I got into a conversation with Rosemary, a black girl who I was in the same math's class as.

Rose also happened to be one of Heather's close friends - the name of my ex. I'd always found Rose to be attractive, and who could blame me? I mean with those shimmering brown eyes, flawless brown skin, and wonderfully shaped derrière. I'd even seen her on a billboard once, modeling for Pond's. She was definitely what one would call "hot". I never bothered trying to hit on her, though. I didn't think I was the kind of guy she was interested in. So it came as a bit of a surprise when she told me she'd always had a small crush on me.

"Really?"

"Uh-huh." Rose nodded with a smile and took a sip of her drink. "I always wondered why you never spoke to me."

"Umm, if I'm honest, it's probably because I thought you were out of my league."

She laughed. "I think I can let you get away with that excuse."

We continued to chat for a little while longer before I excused myself to use the bathroom. While I was in there, relieving myself, I couldn't stop thinking about Rose. I found it hard to believe she was really interested in me. I also wondered what I was going to do with this information. Ask her out? Try to sleep with her? You know what, maybe I wouldn't do anything at all. No. I had to do something about this. I just wasn't sure what.

Once I finished using the toilet I quickly washed my hands. Then, after I closed the taps, I heard a knock on the door, followed by the sound of my name being called. Before I could answer, the door creaked open and in walked Rose. I was shocked. So shocked I said nothing about this. I could only stand there with my mouth open as she walked up to me with a mischievous twinkle in her eye and subtle smile on her face.

Without a word she wrapped her arms around my neck and pressed her soft lips against my own. For a few moments I honestly didn't know what to do. It was as if all my knowledge in this field had been erased from my mind. I could only stand there as she continued to kiss me. But then my hands came up, grabbed her hips and pulled her closer as I reciprocated the kiss. All of a sudden my brain was functioning.

I leaned back and balanced myself against the sink as I pushed my tongue past her lips. The soft sensation they provided was amazing. The subtle smell of her perfume made my insides tremble. And the fact her front was pressed right against mine had me swelling in my slacks. I had a full-fledged erection within seconds.

I can't believe I'm making out with freakin' Rosemary!

The sound of heavy breathing and smacking lips echoed through the bathroom for the next few minutes. Then my right hand travelled down her hip before it rested on her bare thigh, right under her school skirt, which was patterned like a kilt. I knew where my hand wanted to go next, but I begged myself not to let it.

I need to take this slow! What if she freaks out?

But I couldn't help myself. Driven but lust and alcohol, my hand moved higher up her thigh until it was hidden by her skirt. My heart thudded as I waited for her protest. But to my delight it didn't come. Rose continued making out with me as if my hand was exactly where it was supposed to be. Encouraged my hand moved higher up her thigh, until I felt the soft fabric of her cotton panties.

I thought for sure now she would say something about what I was doing. But Rose remained silent. The climb of my hand continued. Once I felt the waistband of her panties I curled my fingers inside them. Rose pulled me closer and pushed her tongue into my mouth. I now knew for sure she wouldn't say anything about what was going on under her skirt.

I slowly flipped my hand over and pushed it downwards. The sensation of her low-cut pubic hairs grazing my palm caused the mild tremble of my frame. Once I had her pussy cupped in my palm my free hand went around her hip and grasped her right buttock. I pushed my middle and index finger past her tight labia, causing her to gasp. As I worked my digits in and out of her she used her hips to grind her clit into my palm.

I wanted nothing more than to whip out my cock, throw her legs around my waist and fuck her good and hard. But I also knew rushing to get your cock inside a girl carried a high chance of turning her off, and I'd come too close to ending my streak to fuck it up now. I slowly worked my fingers in and out of her for the next few minutes, trying my best to get her to cum as we continued to make out. That didn't happen, though. All I could manage was to get her wetter. Hopefully my cock would do the trick.

I extracted my fingers from her sex then pushed my thumbs inside her waistband.

Please don't resist.

I pushed her panties down her hips. Rose didn't. In fact, she helped me get them around her thighs. My patience had paid off! I placed my hands on her hips, brought her over to the sink and slowly spun her around.

"Please tell me you have a condom."

"I do." I reached into my pocket, pulled out my wallet and withdrew the rubber I kept in there, which I thought would expire before I ever got to use it. And it turns out I was right about that, because once I unwrapped and rolled it down my cock, I said something that had me kicking myself for weeks thereafter. I don't know what possessed me to say it - a lapse in concentration, perhaps. All I know is the words just seemed to tumble out my mouth:

"Heather never let me fuck her while we were together. If only she could see us now."

"What?" Rose looked over her shoulder. The scowl she wore made me realise the mistake I'd made.

"Sorry. I didn't mean it like that."

"

Oh.

Then how did you mean it, Chris?"

"Ummm." For a few seconds I was lost for words. What did I mean by that? "Nothing."

"Ppppssshhh, yea right." She pulled her underwear back up. "You're probably not even interested in me, are you? You're just tryna fuck me to get back at Heather for dumping you. She's what this is really about, isn't she?"

"No, come on, Rose. It's not like that."

"Yea, I bet." Her eyes rolled. "Thanks for letting me know how much of an asshole you are before this went any further." She brushed past me and walked out the bathroom.

"Fuck my life."

And that's the story of how I shot myself in the foot. I would go through a couple more times of how I almost lost my virginity, but I think you get the point - I couldn't seem to get it done. As a result of all my failed attempts, I started to think I was cursed. I knew I was just being superstitious, but that didn't stop me from thinking I'd become the real life forty year old virgin, and it scared the crap out of me. But that only lasted until the night this story really began.

Chapter Two: The Woman Online

Sitting on the couch I watched one of my favorite shows on TV at the time - Guy Code. If you're unfamiliar with it, it was basically a lifestyle program that discussed all the unwritten rules that come with being a man. Anyway, during this particular episode one of the topics the cast discussed was "online dating", and the general consensus was there was no longer a stigma attached to it. It was supposedly no longer only being done by really desperate people and psychopaths.

I found this to be interesting. But what really got my attention was a story told by one of the cast members. He told us about this roommate of his, who basically used to use online dating sites as a way to sleep with a bunch of women. Every week he'd bring a girl to their apartment, fuck her and move on to the next one. Which didn't sound like something I wanted to do, but it got me thinking.

Back when I was a little younger I used to love playing football, or soccer, and in every team I was a part of I used to play in the centre forward role. Which, in case you're not into the sport, is the position of the player who's responsible for scoring a good deal of the team's goals, and at the beginning of every season I used to struggle to score any. But as soon as I got that first one in, I couldn't seem to stop scoring thereafter.

I was probably being superstitious again, but maybe, just maybe, if I could sleep with one girl that would open the floodgates and my curse would be lifted. And this online dating idea seemed to be the easiest way to get the snowball rolling. Well, either that or a prostitute. But I wasn't that desperate and wouldn't have been able to forgive myself if I lost my virginity to a hooker. A fuck buddy - I could live with that.

When I got to my room I switched on my PC, went onto the internet and did a Google search for "online dating sites". I wasn't interested in joining any of the sites which came up. They seemed too formal and I assumed the type of people on them were looking for real relationships, not somebody to hook up with. I did a search for "horny local girls" next and found a bunch of sites which catered for horny individuals such as myself.

After selecting one with a nice enough design, I paid my three month membership fees, entered most of the details the site asked for and uploaded a picture of myself. A feeling of nervousness and excitement rings a bell as I sent out messages to a few of the twenty-something year olds who lived in my district. Sadly not one of them got back to me. I knew because they were attractive they probably received tons of messages a day and couldn't possibly get back to them all.

What's more, they'd probably already found the guy they were looking for. But even with this reasoning, I couldn't help feeling disheartened. But then, after my profile picture got approved, I received a couple of messages a day from women who liked what they saw on my account. The problem with these women, however, was none of them lived anywhere near where I did. So I didn't even bother trying to establish a relationship with them. I was starting to have my doubts about this online dating thing. But then I received a message from a woman named Jackie:

"Hey there, young stuff. If you're looking for a good time and a woman who knows her way around the bedroom, you know where to find me."

Jackie was in her late thirties and lived only a couple neighborhoods away from me. From her profile picture I could tell she wasn't one of the most attractive women you can find. But you couldn't call her ugly either. I'd call her...above average. She had long jet-black hair, what looked like grey eyes and a

huge

pair of tits - I believe they were triple Fs. I could also tell she was slightly heavier than the average woman, but this didn't bother me. I actually like curvy women.