Online Endeavor Ch. 01

A day home alone for any 19 year old guy in many cases is very similar; sleeping late and lots of porn. I was still living with my parents while attending community college. The fall semester had just started and I was enjoying my first Thursday of many off thanks to my three day a week class schedule. My girlfriend had just transferred to a four year college to finish her degree out of state, so for the first time in awhile I really had complete freedom.

It was around 10:30 when my cell phone rang. Reluctantly I rolled over to pick it up, forcing out a sleepy, but friendly "good morning" to my girlfriend. I fought falling back to sleep while she talked about her morning class, as well as her new annoying roommate. Before I could get a word in she was off to her next class and I was suddenly wide awake. After climbing out of bed to get my coffee, I headed to my desk and logged on to my computer. Porn had always taken up a large portion of my free time, even when my girlfriend lived just a few blocks away. It was safe to say the habit became worse with her living in another state. Quite frankly this was all relatively innocent until I came across an ad for an adult dating site while looking through videos.

It took a few days of fighting with myself before I caved and made a profile. I felt extremely guilty signing up, but at the same time I couldn't stop it. Once the horniness took over I lost all control. The first few days were overwhelming and at the same time exhilarating. While I didn't see anyone I knew on the site, just knowing there were local people looking for sex was enough to get me all worked up. I spent hours looking through profiles, reading about peoples bedroom fantasies and enjoying all the naughty pictures. It was a whole new rush for me every time I logged on.

The night before I had finally taken the time to fill out the profile. I feared being too specific, worrying somehow my girlfriend would find out, so I kept details very brief. 'College guy looking to make new friends with similar interests. If you like what you see send me a message!' I posted a few shirtless pics with my face blurred hoping I could peak some interest without anyone recognizing me.

Little did I know, my entire day off was about to be consumed by this site. It had been about 8 hours since I filled out the profile and I had already gotten views and messages. Just seeing the notification alerts at the top of the page had my erection already starting to build in my gym shorts. The message simply read 'hey sexy' and was from a 28 year old who lived about 15 minutes away. Her profile pic showed off her beautiful tits. I could feel my cock begin to throb as I started at them. I sent a brief response to her before continuing to explore more profiles.

I stumbled upon the chat feature, which led to hours of sending IM's and impatiently waiting for a response. What started out as a very selective search, quickly turned into a mass sending of messages to all the women within 50 miles. Most conversations were relatively brief and led to nothing, but still left me extremely turned on. A few picture exchanges here and there would occur as well, sadly most weren't free on a Thursday afternoon.

Around 2:00pm my phone rang again scarring me half to death. My girlfriend must have been done with her midday class. I sat nervous, somehow half thinking that she new what I was up to and thats why she was calling. This time however I didn't feel guilty, I was simply excited. As I answered the phone a huge rush came over me. I was throbbing, exchanging nude pics with other women, and now having a conversation with my girlfriend all at once. Still excited about her new classes she talked about her day while I half listened and clicked through more profiles.

She was starting to tell me about her weekend plans when I received another notification. I felt my cock twitch the second I opened the message. It read 'Hello, really like your pics. Are you free at all this afternoon? Let me know if you're interested.' Attached was a picture of her in a blouse and jeans, showing off her curves. Not a perfect body, but damn she was sexy.

"So what are your plans this weekend?" my girlfriend asked.

Again scarring the crap out of me. I had completely missed everything she had said about her plans. It took me a minutes before finally spitting out an answer.

"Just going to relax, maybe get a bit of homework done."

She continued on for a few, I partially listened dropping in a few 'yeah' and 'sounds good' responses in hopes of seeming engaged. The phone call came to and end, I was thrilled I could finally come up with a response to this new woman who was quickly becoming the center of my fantasies.

I could tell from the photo she sent me that she was definitely a bit older. Needless to say I was shocked when I clicked on her profile to see she was 43. At 19 I only had sex with two different people. Both girls from my high school, one my age, and my girlfriend who was a year older. Sex with both of them was always great, they were more experienced than me. Although I hated thinking of them with other guys, I certainly benefited from their skills.

Nervous, yet horny, I replied to her message. 'Hey there, love your pics too. I'm free all afternoon, wanna get together?' I left my cell number as well, and about ten minutes later I got a text. We swapped a few more photos and chatted about our interests in the bedroom. She told me she wanted a younger guy who could fuck her hard round after round.

Despite all my efforts I couldn't keep my hand away from my cock. Seeing those words in a text from a sexy older woman drove me wild. I was close to cumming after the first few strokes. Edging myself as the conversation continued, she finally asked 'I know you're less than twenty minutes away, would you like to come over?' I quickly responded 'Yes please, I can be there in ten.' I knew how desperate that probably sounded, but I didn't care, I had to fuck this woman ASAP. 'Here's my address, get here in about an hour. I need a bit of time to get ready.'

I stood in my room naked and throbbing. I grabbed a towel and took a quick shower, the entire time my mind was focused on her. A constant loop of images showing all the naughty things I wanted to do to her played over and over again in my head. I desperately hoped that I could please her, for some reason seeking some sort of sexual validation from a woman I hadn't even met yet. I found the age difference between us so fucking hot, wanting her to use my 19 year old body however she saw fit.

As time to leave came closer I started to get more nervous. I had never met someone off the internet before, and certainly not someone I knew I was going to quickly get naked with. I put the address into my phone once I got in my car, only fifteen minutes and I would be at her door. The short ride felt like forever, my mind was racing, I was so anxious. On and off throughout the drive I could feel my erection start twitching back to life.

Trying to focus on the winding back road I heard my phone ding. 'On your way?' she asked. 'Yes, be there soon.' I replied. My phone dinged again and I swerved badly as I opened it. 'I want you to fuck me like a dog.' I came to a red light three minutes away and just stared at her message. An even bigger rush of excitement filled my body and my cock swelled. The sound of a car horn shook me from my trance and I took off, I was almost embarrassed at how poor my driving skills had been on a fifteen minute trip that took me down roads I had been driving since I was 16.

Finally I had arrived in her neighborhood. The rows of townhouses made an L-shape around the parking lot. I drove through slowly; it was tough to make out the numbers on each house, and of course gps was of no help. After two passes I came across her house.'Just got here, where should I park.' I texted. 'Park anywhere, give me ten minutes before you come to the door, I'm almost ready.

I parked and sat, my eyes glued to the clock. Each minute felt longer than the next. I was of course still horny, but my nerves were getting worse by the second. By the time the ten minutes were up my hands were shaking. For a brief moment I considered putting the keys back in the ignition and getting out of there. I couldn't just leave, I had spent all day online trying to find myself this exact situation. I looked back at her words 'I want a young guy who can fuck me round after round' and 'fuck me like a dog'. That was more than enough motivation, I stepped out of the car, shut the door and walked to her townhouse.

Three knocks later the door began to open. Anxiety flooded over me as she pulled the door back while standing behind it.

"Hello..?" I said nervously.

"Hi. Come in" She replied as she poked her head around the door. "I wanted to make sure it was just you."

Her Arabic accent was thick, and I loved hearing every syllable flick off her tongue. When she stepped away from behind the door I was speechless. She stood just inches away from me, a black corset covered her beautiful tits and and belly, a bit of soft tummy skin showing just above her leopard print thong. Her heels made her just a few inches shorter than me. I could feel my hands starting to shake again as we hugged.

"Can I get you something to drink?" she asked.

"Water would be perfect."

She led me into the kitchen, I stood back while she grabbed a glass and poured water from the tap. My eyes wandered all over her body. Watching her legs and ass as she moved. She wasn't in perfect shape, but still relatively thin, a few extra pounds which in my opinion made her even more sexy. This was a real woman.

First she handed me the glass before stepping back to grab something off the counter.

"Will you take this for me?"

Her hand opened revealing a blue pill. I immediately knew what it was, however remained silent, waiting for her to give some sort of an explanation. I didn't want to end up with an ambulance ride after a four hour erection to be the grand finale of my day.

"If you take it you'll be able to fuck me for hours, make each round last longer."

The gears in my head were turning. I knew damn well how turned on I get during sex and she had already gotten me worked up just by standing there in her lingerie. Part of my initial anxiety had stemmed from knowing I might cum too quickly. Even after four months of daily sex with my girlfriend there were still times that happened.

"Sure, why not." I finally replied.

"Good, come with me."

She took my hand and led me to the couch in the living room. We sat down and chatted for a few.

"Are you sure you're nineteen? I don't want to get in any kind of trouble."

"Of course I am, don't I look it?"

"I don't knowwww, you look young" she purred.

Unsure of how to respond I pulled out my drivers license and showed it to her, "see, I'm more than of age."

Suddenly seeming much more relaxed, she leaned back on the couch. "Will you strip for me?" she asked.

"Of course" I said nervously.

I could feel my cock beginning to grow in my jeans as I stood up. I walked a few feet in front of the couch and turned around to face her.

"Slowly" she whispered.

As I started to unbutton my shirt her hands began caressing her body. Rubbing down her chest, stomach, onto her thighs, and back up again. Teasing her sex a little bit more every time. Her eyes met mine as I pulled my shirt the rest of the way off, letting it fall to the floor.

"Yes, moreeeeee" she moaned.

I undid my belt slowly, my cock was now bulging through my jeans. Her hands started to focus their teasing touch almost exclusively on her thighs and under her thong. I could hear her getting more excited as I unzipped and unbuttoned my pants, sliding them down to the floor slowly. There I stood, only in boxers, I could feel my erection throbbing and twitching. I loved knowing that she was watching it and touching herself. My young cock had her complete attention and she could already tell I would do anything she asked of me.

Unable to be across the room from her any longer I started towards the couch. As I got closer she put her hand on my leg, stopping me from moving any further. She swung her legs off the couch, sitting in front of me. Her pretty brown eyes were sizing up every inch of my throbbing sex before they glanced up at me. Placing her hands at my sides, she slid her fingers under my boxers.

"Just playing, no fucking yet" she hissed, as she pulled my boxers down.

I was throbbing like I never had before. Her lips teased around my cock, while her nails grazed up my sides to my lower back. She knew how much she was teasing me, I couldn't help the loud moaning, I was dying for her to finally take even just an inch of me into her mouth. Her hands grabbed my ass and I felt her tongue on my balls, she slid her tongue up the base of my cock and swirled it around the head before wrapping her lips around me. Pushing me forward with her hands, every inch slowly descending deeper into her mouth and down her throat. I shouted and moaned with pleasure; she pushed her hands against me slightly just once more as her lips were already just about touching the base of my cock. She gagged as the last few millimeters pressed inside her.

Those pretty brown eyes looked up at me again, her lips tightened as she slid back up my pulsating nineteen year old cock. I was already close, just with that one stroke down her throat. Never before had I felt anything like that. The fact that I didn't already cum was a miracle. She could tell how close I was, somehow she just knew and there was no way she was going to let me. I had to work for my release.

Her fingernails grazed lightly from my ass back to my sides, teasing and avoiding where she knew I wanted to feel any inkling of her touch. She turned and laid back down on the couch like before. I could feel my pre cum and her saliva still dripping off the tip of my length. As I began to climb on the couch I felt her heel poke into me.

"Remember, only playing."

Obeying her rule, I sat at the opposite end of the couch. Taking her heeled foot in my hand as I kissed up the bottom of her leg. First the left, before moving to the right. Her eyes were closed as I kissed and massaged her lower legs. I could hear her breathing start to intensify as I moved up further, I started to turn soft kisses into deeper ones. I repositioned myself so I could get more leverage (not too mention a better view). Now kneeling on the couch I lowered my head into her inner thighs. My first kiss was placed towards the middle of her left thigh. A loud moan filled the room as I felt her body twitch. After a few more intense kisses, I moved to her right leg. Alternating after every few and giving both legs equal attention.

I loved her moans, each one she let out gave me a bigger rush. I was getting more aroused along with her. Making a sexy 43 year old woman purr felt better than anything I had done in my previous sexual experiences. My limited experience made me that much more eager to please.

Reaching the very top of her inner thighs gave me the first scent of her sex. I took a deep breathe in between kisses and licks. It was very subtle, but extremely arousing. With my hands at her sides I kissed over the fabric of her thong. Her moans grew louder, I started to peel down the now soaking wet leopard thong and then she stopped me. I gazed up at her, my cheek resting on her thigh as she caught her breath.

"Not yet", she sighed.

As she sat up she started to undo her corset. For the first time we kissed. It was deep and passionate, her lips were soft and sweet. Our lips disconnected and her corset fell to the floor. Lovely tits, not as perky as my girlfriends, but much more fun to play with. Before I could really indulge she pulled me away.

"Let's go upstairs."

I climbed off her, briefly observing the mess of clothes that covered her living room. She led the way in her heels and thong up to her bedroom. She stopped in front of her bed and turned around to face me. First she undid her heels, before sliding her thong down to reveal a neatly kept landing strip.

We kissed, slow at first, but the intensity built every second. Sucking and biting at each other lips as her hand moved down to my cock. It was already hard, but her few strokes were all it took to get it throbbing again.

"Lay down on the floor" she said almost pulling me too the ground.

I laid on my back while she started to suck me. She positioned herself above me so her legs were on either side of my head and her sex was right over my face. Close enough to inhale her wonderful aroma, but too far to taste. It was only a few minutes before my cock was ready to erupt. I moaned as she stroked and sucked me faster. All seven inches caressed by her throat.

"I'm so close baby, you're about to make me cum" I moaned.

She took one long, slow stroke all the way back down my cock, followed by a slow stroke back up before releasing me from her lips and standing up. Two more strokes and I would have filled her mouth with a thick load of hot young cum. I wanted to cum so bad, but I also wanted to please her. I didn't dare touch my cock. It needed to be her that set it off. She made her way over to the bed, bending over slowly, like she was getting ready to position herself in doggie. I could see how wet she was, her lips glistened.

I sat up slowly while she got into position. There was no doubt in my mind that if she wrapped me up in her sex for just a few strokes I wouldn't be able to contain myself.

"I think I need a minute" I said.

She shot me a naughty glance before saying, "taste me first."

Kneeling down behind her I was almost unable to contain myself. A few kisses and licks around her pussy and her beautiful ass were all I could manage before sinking my tongue inside her sweet lips. Never having done this in this position threw me off a little bit, she began to work her clit with her fingers while I used my tongue everywhere else. Feeling her start to tense up as her orgasm was approaching got me so aroused. Her moans were loud, much louder than when were on the couch.

"Fuck, I'm fucking cumming!" she screamed.

Her body tensed up, and she pushed back hard onto my tongue as she released. When the orgasm subsided she was still shaking, her head down, as she kneeled on the bed. I kissed her thigh before getting up and laying back on the bed next to her. She leaned over and kissed me, licking up some of her juices off my lips. Her fingers teased my cock ever so slightly. Tracing the length of the base back and fourth. Her teasing slowed and she got up to reposition herself on the bed.

"Come up here and lay on your back" she said as she patted the pillow a few times with her hand.

I did as she asked, and she sat facing me while she stroked my cock lightly. I was already back to throbbing hard, and couldn't wait to see what she had in store. She flipped over, almost putting us in a 69 before crawling towards the opposite end of the bed.

"Have you done this one before?" she asked as she grabbed my cock and starting to ease me inside her.

"No" I moaned.

Her lips teased the tip of my cock before she sat back and took me all the way in. She felt nice and tight around me. The long, deep strokes kept coming and the view was perfect. I leaned forward and spread her cheeks, admiring her sex with my cock sliding in and out. With every stroke I lost more control, I could feel it building as I was pulsating more and more inside her. She had only been riding me for two minutes, but I couldn't hold it any longer.

I grabbed her ass harder and pushed her down on my cock, slightly rougher than she was riding me, but still a slow pace. Once I started to moan I knew I was seconds from release. As she thrust down onto my cock I couldn't hold it an longer. Streams of my hot cum shot inside her. She continued to ride me until she got every last drop between her lips.