Sex With The Chaperone

My parents were divorced pretty early on in their marriage, which left my mother with the bulk of child rearing duties. I rebelled occasionally, of course, but mostly I was a pretty normal kid. I liked sports, putting an engine or a motor on anything, and girls. I wasn't very successful with the opposite sex, so as a result, I spent 99% of my time scheming and dreaming. In the course of this scheming and dreaming I invited some girls to a party at my home the summer before my Senior year in high school when I was 18. My mother was to supervise, but an elderly neighbor woman whom she looked after became ill, and my mother agreed to stay the night with her. To keep an eye on things, she asked her friend Faye to come by, serve some pizza and provide adult supervision. Faye was also divorced, shapely, and a decent looking forty year old woman. She probably would have come by anyway, seeing as how she was close to my mother and enjoyed a good time. I always liked her laugh, but it was her sweet round rear that was her greatest asset, and I spent many hours worshipping it in the most sincere way a teenager knows how. I should tell you also that Faye had an "Innocent" crush on my good friend Tony, a dark, quiet type who was actually kind of shy. I'd heard his name mentioned more than once, and my mother and Faye always smirked on hearing it.

The evening began okay, and some girls actually showed up. I did about as well with them as I usually do, which means I spent a lot of time playing ping-pong. Faye served the pizza, hung out for a while with us and had a beer, then another, then left us alone. An hour or so later one of the girls had to go, then the others followed, then it was just four guys and me.

We bullshitted a bit, then two of them left, leaving Rob, a very good looking guy, Tony and me.

Tony wanted a beer, so we snuck inside to raid the fridge, but Faye appeared. Faye had apparently had another beer, because she was both stern and flirtatious with us. We grudgingly agreed to forego the beer, and settled in on the couch, talking with Faye and watching mindless television. Every so often Tony would get up and pretend to go to the bathroom, by way of the kitchen, and Faye would head him off. They were practically dancing around the kitchen with their arms on each other by the third time, however, and Faye dragged Tony back to the family room by the hand. Conversation soon got more daring, and there was talk about women, sex, who was dating who, and normal teen stuff. Faye was really enjoying it. Helped by the beer, she laughed constantly, and encouraged us to be more bold and pursue the women we lusted after. When the subject got around to kissing, each of us guys all claimed to be the best. And somehow, during her fourth beer, we got Faye to be the judge. We preceded "Scientifically", turning the room lights down and finding a dark scarf to blindfold Faye. I don't mind telling you that at this point I had a raging hard-on. Faye, dressed in a khaki jeans skirt and a top I can't remember, was standing in the center of the room, blindfolded and surrounded by three guys with raging hormones. We put on the same cologne, agreed to wear the same shirt, Faye agreed not to touch us and began.

Rob went first, and he really went at it, holding Faye's head. Faye seemed not to mind, and soon we could see they were even French-kissing. In the midst of this, Rob caressed Faye's back lower and lower until he was almost grabbing Faye's butt. She hardly seemed to care. After one squeal of protest, she grabbed Rob by the butt herself. They broke for air after two minutes or so, then Tony stepped in. It was a repeat performance, but Tony grabbed Faye's ass a lot quicker and winked at us as her skirt rode higher up her ass, exposing nearly all her thighs. He and Faye pushed at each other like lovers, and there was obvious full body contact. They broke off after running out of breath, and Faye said she needed another sip of beer before continuing. We gladly provided it, helping her to finish her fourth can by holding the can to her lips, but not removing it until it was empty. Faye wobbled a moment unsteadily then I took my place and helped steady her.

Unbelievably, this woman who was always so adult and above me, now put her arms around me. I grabbed her soft body and held her to mine, running one hand through her hair and the other across her back and ass. When I met no resistance, both my hands dropped to cup her rear and pull her against me tightly. Our tongues went around and around, then we alternated sucking each other's tongue and lips until we got a signal to stop. Faye practically fell over when we stopped, so I slipped behind her and held her while we loudly debated results. Faye leaned against me and I put my arms around her waist, which meant my stiff dick was forced up against her backside, but she made no complaint. In fact, she agreed to another round of "Tests" if someone got her a different scarf that wasn't wool and hot. I handed her over to Rob and raced for a different scarf from my mother's closet.

Faye put the second scarf on and gamely started a new round, but she was so unsteady on her feet now that she and Rob soon dropped to their knees, then the floor. The two rolled around, mauling each other between breaths for several minutes. When they stopped Faye asked if the lights were out, and we lied and said "Yes". Faye said something about this being "work", but then added that it was nice work if you could get it. I laughed and took my place on the floor beside her.

My second round began almost leisurely, but then I pulled Faye on top of me. She didn't miss a beat. We continued our kissing while my hands caressed her butt and pulled her skirt so high that I felt bare skin and the edge of her panties. With the fervor of a madman, I skipped my hand across that pantie-covered ass and pulled her tight against me. There was no resistance! One of my mother's close friends was letting me touch her! I was in heaven. My kisses were secondary now, and I slipped my hand beneath Faye's panties and felt her hot cheeks. That caused a shift in Faye's position, which made it hard to hold her ass, so I stopped kissing and got up.

Faye asked for a glass of water before continuing, which we quickly provided. After finishing the water she asked us again about the lights. We lied again. She also made us promise to keep this "Contest" to ouselves, which we agreed to, of course. Then Faye called for "Contestant Number Three".

I think she knew it was Tony, and this time was pure passion. Tony had Faye on her back and one hand up under her blouse in about twenty seconds, and pulled up her skirt with the other hand. Rob and I looked at each other with eyes wide and silently took up positions close by. Amazed, we watched and listened as the groaning couple mauled each other. Rob strained to get a look at Faye's breasts. I scooted around on the floor until I had a perfectly breathtaking view of pinkish middle-aged panty crotch tightly pulled against a full mound. I held my breath at this incredible visual treat, silently cheering as each flop of her knee separated her legs to expose more panty-covered pussy, then sighing in disappointment as they closed.

Rob joined me on the floor a moment later, silently whistling at the sight of this middle-aged woman's exposed crotch. Minutes passed while she and Tony got more passionate. It was obvious the contest was over, but what now?

Rob and I took matters into our own hands and began rubbing the nearest foot. Faye jumped for a second, then moaned in ecstasy as two hands massaged each foot. Being teenagers, we didn't spend long on the feet, and soon began working our way up Faye's legs. In a few short minutes we were massaging soft forty-two year-old thigh so close together that we had to take turns. Meanwhile, Tony had shifted position and was straddling Faye lightly. I heard a zipper and froze in shock as Tony seemed to pull out his dick. Unbelieving, I watched as his butt shifted and he apparently reached down to put his penis within reach of Faye's mouth. This was too much. It COULDN'T be happening. I was stunned, so stunned I actually shook my head like they do in books to clear the cobwebs of whatever. Nothing changed, though, except the wet sounds of oral sex.

Rob and I went for broke now, using our fingertips to tease Faye through her panties. Neither one of us was immediately so bold as to reach inside and stroke wet pussy, so we traced the slot between her folds and rubbed Faye at different speeds in different ways. Faye strained and shook, but with each of us on a leg, there wasn't much she could do. She wasn't trying to buck us off anyway. At least I don't think she was. She was just crazed with lust.

I couldn't hold back for long, though. I crooked a finger beneath the legband of her panties and slowly reached in. I felt wet pubic hair first, then a half inch later found some incredibly slippery and warm labia. Where her labia ended and her pussy began was a mystery to me, I just caressed anything that was soft. Then Rob and I each tugged on Faye's panties and quickly took them down her legs and off. An odor of sweet womanhood greeted us, me for only the second time in my life. Rob beat me to the punch and had a finger in Faye's pussy before I could toss Faye's damp panties aside. He had Faye bucking wildly in seconds, and within a minute she came, rising up on her knees, moaning and gasping in blissful agony. Tony turned and gave us a thumbs up with a big smile.

I wasn't sure what to do next, but I didn't want to relinquish my place or my hold on a nude woman, so I returned to massaging thigh and pussy, then began licking Faye's inner thighs.

My only experience with oral sex was all too brief, so I figured to make this experience last a little longer. My real target was Faye's pussy and I quickly found it. I kissed and slurped and sucked everything that was wet and feminine. Faye moaned, then Tony moaned, then Rob gave me a thumbs up himself and retreated. It wasn't very comfortable, but I was so intently focused on my tangy target that I hardly gave it a thought. Soon my labors had the desired effect. Faye's legs shook and she made a series of delirious noises before spasm after spasm made her body alternately rigid and liquid.

Was that ever fun! I wasn't sure what to do next, and I didn't know what to say to anyone, so I went to the bathroom and completed my own orgasm. My sperm rocketed out my stiffened dick and landed on the wall above the sink. More sperm streamed into the sink, then still more dribbled out on the cold white marble. I took a few breaths and stared at myself in the mirror. Wow!

Who was I now? Was I any different than I was a few hours ago? Older? More mature? More manly? All that and more, I concluded, lifting my head for the most flattering angle and staring back at the grinning face before me in the mirror.

Amazingly, there were no real repercussions to this wild indiscretion. Faye and Mom remain friends to this day. I had to listen to some remorseful and slightly accusatory words from Faye a couple days later, but that was nothing. I deserved them. Far worse for me was her refusal to even flirt with me when we were alone in the following years. My ego wanted more. I wanted to sink my manhood between those sweet and tasty pussy lips. It never happened. Anyway, we converted the house into a duplex and mom has her own side now--the new one. I still have the old side, and a room with a great memory.