Next Door Love

When I was a teen, a kinky neighbor woman paid me to jack off while she watched. She was a pretty, mature lady in her late forties. She eventually had me over several times a week. We would both strip and watch each other masturbating from across her living room. She insisted on having me cum on her tits and face. I loved watching her rub her hairy pussy and massage her tits. I had never had sex with her, but she used her collection of sex toys to help her get off. She did eventually suck my cock and allowed me to suck her clit until she orgasmed many times. I loved every minute of it.

Sometimes, she just wanted to get naked and take a nap with me. I loved cuddling up wit her, tucking my cock between he ass cheeks and holding her big breasts from behind. I could hardly sleep when I was fully erect, but she would doze off easily. I used to jack off looking at her tits, ass and pussy while she slept. She woke up once, while I was jacking off gazing at her beautiful asshole as I held her cheeks open. She asked me what i was doing, and I asked her if I could cum on her ass. She said it was okay so I launched a big wad directly on her tight looking butthole. She jumped as I spurted, and squirmed around as I dragged the head of my cock across her sloppy ass crack.

I asked her if she had ever had anal sex. She said that she never had because she thought it would hurt. There was so much semen deposited in her ass crack that I started running my fingers up and down it and pushed my finger tips against her puckered anus. She seemed to like it, so I slowly started working a finger in her ass. Soon, I had two fingers inside her hole and she was moaning loudly as she fingered her wet pussy. I asked her if I was hurting her and she told me that it felt good. I told her that she was ready for my cock if she wanted to try it. She agreed, and I guided my throbbing cock up against her loosened butthole. The head popped in easily and she was thrilled. I just held it there as her ass quivered and spasmed against my hard intruder. After a minute or so, she said, "Give it to me. I want it all!". I growled as I slowly slid the rest of my cock into her, inch by inch, until my balls rested on her ass cheeks.

I held it there, deeply impaling her. To my surprise, she began to grind on it, in a slow, circular motion. I felt the familiar sensation of another load of semen coming to a boil within my big balls. I warned her that I was about to cum, and she moaned, thrusting her ass back toward me as she groaned "Yes!". Her ass was stretched to fit my cock like a hand in a glove, and it was a perfect fit. I pounded her ass hard, causing a loud slapping sound with every thrust. She was masturbating the whole time I was fucking her ass and she had an intense orgasm. Her butthole spasmed and clenched my cock at the root so hard that it felt like a tight rubber band stretched around it. I kept sliding in and out of her, full-length as her shuddering orgasm subsided. Sometime, during this cooldown, I ejaculated a massive load into her and it was leaking out onto the sheets. She begged me to never pull my cock out of her. We stayed coupled for a long time until my flaccid cock finally popped out her wet, gaping hole.

From that on, she craved anal sex. She always was prepared for me when I arrived, with a squeaky clean enema, lots of lubrication and towels on the bed. She even bought sexy underwear that exposed her waiting butthole to tease me. I introduced her to anal sex and I created a monster!