I have been going to school with my friend Josh’s since sixth grade, but it was not until the ninth grade that he became my best friend. His father, Jim, was Pilipino and had come over some twenty years ago while in the military. After significant financial success, his father had married a cute Rhode Island blonde woman named Ellen and settled down to make a family. I had always noticed Josh’s mother in middle school because all the upperclassmen would make crude jokes about what they would love to do to her. Several times some of the seniors had even had the audacity to tell my friend Jordan that his mother was a complete MILF. However, it was not until the tenth grade that I started to display any sexual feelings towards her. Jordan was fairly wealthy, and we would always go swimming in his pool during the day. His mother, who was extremely kind, would always come out and give us towels when we were dripping wet. I could sometimes tell that she was staring at the way my wet shorts cupped my dick and balls, but I never thought twice about it. She would always smile, make small talk with us and go back in.
However, as I grew up I found myself beginning to watch her more and more. Her highlighted hair, voluptuous makeup and trim body would always catch my eyes. Her breasts were large C’s and she stood about 5’3 or 4. I was always over at Josh’s house, and every opportunity I had I would admire her nice butt or dream about the pussy I could sometimes pressed against her pants. She was 38, and while driving us would sometimes make sex jokes that would make us all laugh (but secretly turn me on like wildfire.) As time progressed I found myself getting bolder and bolder, and while my friend was upstairs I would wander downstairs into his mom’s room. At first I would simply go in and imagine humping the daylight out of her on her huge mattress, but I began to explore the other parts of the room. One day I the top drawer of her dresser to find her panties and bras all tossed together. I immediately reached in a grabbed some, only to find that I was holding on to a Victoria’s secret thong. I inverted it and smelt the cotton that had rubbed up against her pussy. I un zipped my pants and fast as I could, took out my raging boner and rubber the slick silk up and down my dick. All I could think about was taking Ellen and fucking her like a wild animal.
It stayed like this for a while, but as junior year approached I knew it was finally time for me to make a move. Because Josh’s dad Jim had a highly paid job, he was constantly on business trips leaving Ellen me and Josh alone. When I got my license I would drive over all the time to see Jim (and hopefully Ellen too.) One day I drove by and let myself in through their garage. I saw Ellen sitting on the couch and went over to see what she was up to. She told me that Jim was at SAT prep and that he wouldn’t be back for a couple of hours, but that I should stay because she was making hot apple pie for desert. I agreed and headed up to Jim’s room to watch TV. Slowly, yet surely I began to realize that this was the ideal opportunity to finally make my fantasies come true. It took me about half an hour to work up the courage to go downstairs, but I finally told myself “He who hesitates, masturbates” and realized I had been masturbating for too long.
I causally walked down the stairs and sat next to Ellen. This wasn’t uncomfortable for either of us because we were used to sitting together all the time with Jim and watching movies. Sex and the City was on, her favorite show, and she told me that I should watch it with her. I sat next to her, and after smelling her perfume and looking at her breasts pressing against her cashmere sweater I was instantly horny. We watched TV for a few more minutes, and finally I noticed her rubbing her neck. I asked if she was alright and she said that her neck was sore from sleeping last night. I told her that I knew a great massage my last girlfriend had given me and she said that that would be amazing. She got up and I sat down on the back of the couch, spreading my legs and making a place for her she sit. When she sat down I was worried that she would see my huge dick through my pants but she didn’t seem to notice anything. I began massaging her neck and she told me that it felt great. I pushed and caressed and smoothed my thumbs against her neck and slowly down her back. She kept on saying how good it felt and that I was an angel for helping her. However, when I got to her mid back and looked down to see her black thong riding its way up the top of her ass I knew it was time. I moved from the middle of her back to the her sides down from her arm pits and finally, after four years of waiting put my hands on the sides of her breasts. I anticipated her standing up and slapping me in the face, but when nothing happened I continued.
She sighed sensually and I moved to the front of her breasts. She asked if this was part of the massage and I told her of course it was. She smiled and let me continue. I cup her perky C's and pushed my tong against the back of her neck. By this time she was staring to squirm a little, the first indication that a girl is getting wet. I played with her nipples outside of her shirt and started licking the back of her neck. My dick felt like it was on fire, and I began to inadvertently undulate my hips a little. Finally she burst out “Colin, I know we shouldn’t be doing this, but you’re almost grown now and I have been wanting this for so long.” With that she put up her arms and let me slide the sweater over her shoulders. I continued to suck the side her neck while at the same time firmly massaging her breasts. Slowly I traced a line down her belly my right hand, tingling her stomach and making her lean her head back in pleasure. When I finally got to the crevice between her two legs I started to rub the clothes area with increasing intensity. She instantly began to squirm some more and I continued to lick and suck her lower neck. When she could take it no longer she undid her bra clasp in the front and let her breasts fall down. I was mesmerized and ready for action. I picked her up and put her down so I was facing her from the front. I cupped one breast, shocked that my wildest dream was coming true, and leaned over to take her tit into my mouth. I sucked it and rolled by tongue over it faster and faster, and she began to moan with delight. Her hand quickly slid down into her pants and I could tell she was playing with her pussy. I sucked as I had never sucked on anything before, switching from tit to tit every so often. When both her pink nipples were standing completely erect I knew it was time to move on. I slid her tight black pants off and traced a trail with my tongue from her tits to her belly button and finally to the top of her black panties. She looked down at me with that mature perfection and my cock felt like it was going to explode. I pulled my shirt off because I was getting hot, and then grasp the two side strings of her thong and yanked them down. Staring me in the face was a perfectly shaven pussy with an erotic heat emanating from it. There was the faintest stubble from when she last shaved, but it felt amazing when I rubbed my hand around the area. I continued to tease her, massaging the area until she told me to eat her pussy before she went crazy. Sticking out my tongue, I opened my mouth and took her whole mound into my mouth.
My tongue went up and down her slippery slit and a gush of juice filled my mouth. I nosily slurped it down and found her clit and started to nibble it. She was writhing in passion and I took two fingers and slid them into her cunt. It was hot and slimy, and I could feel little bumps which made me even hornier. I kept eating her pussy with a fury and unbuttoned my pants and slid them off. I lifted her butt and legs up a little licked my finger and began to go reached back to her butt hole. She gasped but made to effort to stop my as I gnawed at her pussy and made circular pushing motions on her tight star. She began to reach for the gigantic tent in my pants and pushed my dick through, but I told her not quite yet and spun her over. My two hands smacked her butt checks, spread them apart and again she gasped. I got some spit my mouth (which was easy from all the juices running all over the place) and bent down to suck her pinched asshole. It tasted different than her pussy, but a better in my opinion. I licked and slurped and poked and prodded her asshole until all you could hear was the squishing and her constant moaning. I put two fingers in, felt around the inside of what was now another wet hole and dropped my boxers. I spun her around again and finally, after years of waiting plunged my bulging penis into her waiting pussy. To say that it was the most erotic, wet, slimy and tight experience of my life would be a total understanding. I pushed my dick in an out time and time again until I was ramming her with the force of a rhino. The whole couch shook and pussy juice and pre cum splattered all over the place. I continued this outrageous fuck for what seemed hours, our bodies sweating and humping in the same motion. I bent forward and took her tit into my mouth and sucked until it was fully erect again.
After a few more minutes of this I pulled out, sloshed my hand in the pool of juices all over our bodies and put two fingers into her asshole again. She let out a long moan and I began to rub my dick with her pussy juice. When I was sure it was well lubricated, I lifted her butt up and slowly inserted my dick into the dark hole. It was so tight that it felt like pushing my dick into a fist, but it was wet enough that I finally got it all the way in. Only my balls were showing, and my whole penis was surrounded by her hot, gooey, throbbing asshole. I pushed in and out and her moans were like music to my ears. It was so tight that I thought my dick would get squeezed off, but it slowly began to loosen and except the foreign member. I established a pace and plunged again and again until I started to drip sweat. I felt the pressure building up, and grabbed both her boobs with my wet hands and smeared the liquid until her tits were shining. I started pounding her ass faster and faster, and at last the force in my dick erupted load after load after load of steamy cum into her ass. We were groaning together in complete ecstasy, and I reached down, smothered my fingers in the mixture of juices and spread it all over her stomach and pussy. She grabbed my dick, and while panting, gave me a wicked smile and said “We gotta do this more often.”