Back in the late 90's, the internet was really just starting to take off. As a teenager, I found it to be an awesome tool to meet women. Back then, the internet wasn't as user friendly as it is today, so the types that were online were a little technically savy and intelligent -- at least in my experience.

In the course of my adventures, I ended up meeting a 47 year old woman who lived in the next State over. She was a thin redheaded biker type chick. She was rough and touch and liked to be one of the boys. She had maybe an A cup set of tits. Over a few months of chatting with her, I encountered her a number of times during nights she was drinking. So naturally her inhibitions would be lower and she would get quite flirty. I took the chance and proposed that we actually hook up for a FWB arrangement and get rid of my V-Card. She wasted no time in agreeing and made plans within a few weeks to drive down to meet up.

I had the house to myself for a few weeks due to my mother being away for medical treatments. My redhead arrived at my place on a spring afternoon. After having some small talk, we went out to dinner (which she paid for.)  

Naturally, the whole time I was looking at her, I was imagining her naked and with her lips wrapped around my cock. It was pretty exciting to think that I was going to get laid for the first time by a woman that was older than my mother at the time. We went back to my place after dinner and sat around the livingroom engaging in some small talk while she was showing me some of her work she was involved in. Abruptly, she said,

"So, you want to get this started?"

I said, "Sure, where do we begin?"

She replied, "For starters, you can show me your cock."

I unzipped my pants and pulled out my already hard 6.5" cock. She promptly grabbed it and began stroking it softly while moaning under her breath.

She then said, "Let's go get a little bit more comfortable," and lead me to my room.

Once in the room, she began taking her light leather jacket off and peeling off her Levis.  I began stripping as well down to my boxers with my cock hanging out the front flap. She pulled her bra of exposing her tiny little tits and dropped to her knees in front of me and said, "Let me taste that cock."

She squeezed the base of my cock and stroked it upward causing precum to run out of the tip and onto her tongue and lips. She moaned happily as she took the head of my cock into her mouth. I leaned back on my bed as she began to bob on my cock, pausing only to take my balls into her mouth. After a few minutes, she came off the top of my cock head with a popping sound and ordered, "Roll over."

Not sure what to expect, I followed her commands and rolled over onto the bed. She spread my ass cheeks and began teasing around my asshole with her tongue. After a minute or so, I felt her flick my asshole with her wet tongue which caused me to jump a little. She continued to press her tongue against my asshole until it penetrated a little. It felt great and I was pooling precum into the sheet.

She then said to roll over again. She stood up and slid her panties down to reveal a trimmed red bush. She had a nice tattoo on her ass cheek also. She got up on the bed on her knees and straddled over my chest and ordered, "Eat my cunt."

She grabbed me by the hair as she brought her pussy to my face and sat on my face. She was sopping wet and she was painting my face with her pie. She was grinding back and forth with my tongue running between her slit. She'd push her cunt to where she wanted me to eat and tell me to bite or suck it. I must have sucked her cunt for ten minutes when she got up and spun around into a 69 position with her still on top. This gave me what is now my favorite view of a woman. She pressed back against my face and pushed my tongue against her clit while my nose was buried in her cunt. Her puckered little asshole less than an inch away from my eyes. She moaned and groaned as she pressed back against my face. It felt like my teeth were going to break from the pressure being put on my upper jaw!

After a few minutes or grinding, she shifted lower and said, "Eat my asshole." I was a bit nervous about doing that, but not wanting to be a bitch, I ran my tongue from her clit to her asshole. Noticing there was no taste or smell, I enjoyed it and spread her ass cheeks wide as I teased and probed her tight little asshole with my tongue. As I continued to lick her, she continued to grind harder while moaning and groaning. As she got close to cumming, she pulled away and rolled onto the bed and said, "Give me that cock."

Still licking my lips, I asked, "No condom?"

She replied, "You're in luck, I'm too old to have children."  

I crawled on top of her as she fed my cock into her hot wet pussy. I pushed it all the way in. Even though it was my first time, I had minimal trouble keeping it in her as I pumped her. She licked her taste off of my lips and sucked my tongue. After about ten minutes of pumping, I pushed her over the edge of orgasm. She clawed my back and screamed my name loudly as her body violently shook beneath me. After a moments rest, she said, "Let me roll over."

She got up on her knees and I got behind her. Hands on her ass, my cock slide easily into her wet pussy. As I fucked her, I kept watching her ass. I'd spread her ass cheeks and touch her tight little asshole with my thumb. Without asking, I wet my thumb and began working it up her ass. She moaned approvingly, "I haven't had that in a long time."

After a few minutes, my thumb was burried in her shitter as I was pumping her firmly from behind. After ten or fifteen minutes of this, she came again. At this point, she exclaimed that she was done and asked how I would like to cum. I told her, "I want to fuck you up the butt." 

She seemed a little surprised, and said that she had never actually done that all the way. I asked, "Could we try?"

She said yes, but started running down some rules on doing it slow and easy. She got on her knees at the corner of the bed.  I spit on my cock and tried to push it up her ass. It would slip away and end up in her gash. I then held my cock with my thumb out over the tip of my cock. My thumb pressed up her ass and guided my cock in. She kept telling me, "Easy, slow down, fuck it's big," and so on. Once it was most of the way in, I stopped pushing and let her get adjusted to it. She was rubbing her clit while I stood there with my cock shoved up a woman's asshole who was older than my mother. After five minutes or so, she told me to start moving it in and out slowly. The first few strokes caused a lot of moaning and groaning. I thought I was hurting her, but she indicated it was just intense. A few minutes later I was pumping her asshole. She kept moaning my name and yelling, "Fuck me up the ass!" As she began to cum, her asshole clenched up around my cock and made it even tighter than before. I began pumping her ass as hard as I could. All I could hear was gutteral moaning and the sound of my balls slapping against her cunt. This sent me over the edge and I spilled my load deep up her ass. I laid on top of her for a few minutes sweating before pulling my still hard cock out of her now partially gaped asshole. Cum ran freely from her asshole down over her cunt and onto the bed.

It was the start of a very fun weekend with her. Over the course of the weekend, I probably fucked her eight times. We kept hooking up for about five months before I got myself a real girlfriend and she also moved on.