The Road Not Taken

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Ann Douglas
Ann Douglas
3,179 Followers

Never having double-dated back in high school, Jennifer had never actually seen another woman give head. From what she could see now, Joyce was a first class cocksucker. In a way, she envied her. Back in high school Jennifer had always found the idea of actually taking a guys cock in her mouth a little repulsive. But then again, there was a popular saying among many of the girls - "No one ever got pregnant giving head." How many times over the years had she wished she'd followed that advice.

She watched fascinated as Chris's young manhood exploded into the 18 year old girl's mouth, sending droplets of shiny white cum dripping down her chin. Joyce continued to run her tongue up and down his now milky coated cock, wiping it clean.

The entire spectacle had only lasted a few minutes but the memory had lasted years. She had spackled over the hole the very next day, both to preserve her son's privacy and to remove her own temptation.

"The hole was right about here." Jennifer said to herself as she ran her finger across the wall in the dark.

A smile filled her face as she discovered to her delight that she lacked her husband's home repair skills. Most of the spackle had dried into a fine powder, the rest was easily chipped away with her nails. A few moments later she had fully exposed the small hole.

In hindsight, the image of herself, a full grown woman, sitting in the dark and spying on her tenant might seem ludicrous. But such was the fire that spread from between her legs that she never gave the idea of how embarrassing it would look if caught a moment's thought.

Thankfully, Sally appeared to be one of those people who liked to make love with the lights on and it was very easy to see into the brightly lit room. In fact, the spy hole was situated almost exactly across from the Asian woman's bed, giving Jennifer a perfect view.

And what a view it was. Facing Jennifer was a young woman in her late 20's with short blond hair and green eyes. As she was on all fours, it was hard to guess her height but Jennifer thought she was about as tall as she was. The young woman was wearing the remains of a green teddy.

Kneeling behind her, Sally was dressed in a very attractive and sexy white nightgown. Her breasts were fully exposed, giving Jennifer the clear view of her dark nipples she had been denied during their party last week. Sally had her hands wrapped around Amber's large breasts, playing with them as she pressed her pelvis against the woman beneath her again and again.

Between Sally's legs, almost hidden from view was something Jennifer had never seen before - not even in Jack's porno films. Of course she knew what a strap-on dildo was even without having seen one. It was all but buried in Amber's pussy as Sally pushed and pulled it in and out.

"Oh baby, do it! Do it to me good!" Jennifer heard Amber cry out as she arched her head back. The sound now carried a lot better though the tiny hole. "Fill my pussy with your cock!"

In response, Sally drove forward with a powerful thrust, at the same time pulling Amber's face to her own, pressing their lips together.

"Oh yessss!" Amber purred.

This was too much for Jennifer. She slipped her hand down into her own panties and found her mound so very wet. Never taking her eyes off the two women in front of her, she began to play with her clit.

Ever since she was a teenager, Jennifer has masturbated almost daily. She remembered all the silly names people called it. Flicking the switch, beating the bush and caressing the kitty were her favorites. Yet in all those years, she couldn't remember her finger dancing to have been this pleasurable.

Faster and faster Jennifer moved her fingers, keeping time with the thrusts of Sally's dildo. In her imagination she could put herself in Amber's place, enjoying the hardness of the artificial cock.

Normally, Jennifer liked to close her eyes and drift in the pleasures of masturbation, but not this time. The spectacle before her was just too exciting.

Sliding her free hand beneath the soft material of her nightgown, Jennifer took each breast in hand and rubbed them vigorously. The motion of her fingers felt good to her and always added to the rising tide between her legs. Playing her nimble fingers over her nipples, she quickly brought them to a full hardness.

She ran her tongue across her lips as she pressed her face against the wall, her eye never wavering from her vantage point. Her entire body felt warm as she pushed two fingers up within herself, imagining them to be Sally's strap-on. It'd been months since she'd been this worked up.

Faster and faster she worked her fingers, matching her penetrations with the gasps of Amber's breaths. The older woman was no longer worried about making any noise - not that the two lovers would've heard her if she screamed.

"Oh God, I'm going to cum!" Amber called out as Sally once more planted her toy between her slender legs. "It feels so good."

"No, not yet!" Sally called out as she grabbed the base of her "cock" and pulled it out of the blonde's pussy. "Not yet!"

As fast as she could, Sally rolled Amber over and replaced her "cock" with her mouth. She drove her tongue up inside her lover, covering it with the sweet juices her efforts had brought forth. Her long slender fingers pressed against Amber's ass as she pulled her crotch tight against her face.

It began as a flicker. Then a touch. Finally a long loving caress. She could feel Amber's body react to each stroke as she ran her tongue across her clit over and over.

Amber began to buckle and spasm as Sally increased the intensity of her tongue's attack. She slid her free hand down between her own legs and slid first one, then two and finally three fingers within herself. She quickly matched the tempo of her fingers to that of her tongue.

Sweat ran down the blonde's body as she shook with each new ecstatic jolt. She could feel the rising crest within her and knew that her orgasm was oh so very near.

Sally darted her tongue in and out of Amber's tunnel of love, causing the waves of pleasure cascading up and down the younger girl's body to double. The harder Sally moved her tongue, the faster the waves repeated.

Faster and faster the waves washed over Amber, each bringing her closer to an explosion. Tears ran down her cheeks as she tried to delay the fire within her so that she could enjoy each second.

With a yell, Amber climaxed loud enough that it caused Jennifer to momentarily jump back from her spy hole. Amber's small body shook for endless seconds as she took in every aspect of her rapture.

Sally followed with her own orgasm seconds later as her fingers covered her wetness. A much softer cry was on her lips.

Almost in time with Sally, Jennifer also climaxed with an intensity that she hadn't enjoyed in oh so very long. Her body trembled as her mouth formed a silent O. Her legs and arms grew weak and repeated waves of delight rippled up and down her near naked form.

For long moments after her bodyquake had ceased she just drifted there, listening to the rapid beating of her heart. She always loved to savor the first moments after an orgasm. One of the sad truths of her life these days was that the orgasms she enjoyed by her own hand were much more enjoyable than those produced by her husband. This climax in particular, had been quite memorable to say the least.

Twenty long minutes passed as Jennifer sat there in the dark room, waiting until the lights went out in Sally's apartment. She couldn't believe what she'd done. Yet at the same time she was so glad she'd done it. Never in her life could she have imagined that it could be so exciting to watch two people make love - and two women at that. What was it that they called someone like that, oh yes - a voyeur.

Quietly as she could she made her way back up to her own bedroom. Jack was still dead to the world as she crawled back into their bed. Despite her recent climax, Jennifer was still horny and reached under the thin sheet and stroked Jack's cock. It didn't take long to bring it to a familiar hardness. Despite this she couldn't seem to get him interested.

"Come on Jack." she whispered as she ducked under the sheet and slipped the head of his cock into her mouth.

"If this doesn't wake the dead, nothing will." she thought as she ran her tongue along the underside of his balls.

"Mmmmmmmm." Jack finally stirred as the pleasant feeling finally woke him up.

"Hi honey." Jennifer purred as she let his cock slip from her mouth and climbed on top of him. "I am so, so horny." she said in her sexiest voice.

Before Jack could respond, Jennifer had guided his cock to the entrance of her moist mound and was pressing hard against it.

"Fuck me baby!" Jennifer said as she felt his hardness fill her. "Fuck me hard!"

Jennifer began to move up and down on his cock, enjoying the sensations that grew in intensity with each motion. Bracing her hand against the sides of the bed, Jennifer rose and dropped with an ever increasing frequency. Faster and faster, she pumped, creating a suction that was drawing the life out of his cock.

"Oh Yes...Jennifer!.." Jack called out as he matched her familiar motions.

At the rate she was moving, Jennifer knew that he would cum quickly. Even as a young man, Jack had little self control. A few minutes later she felt his body tensing. Lifting herself higher so that his cock nearly fell out of her, she drove herself down on it with a fury. Up again she raised and then down with the same abandon. Twice more was all it took as she felt the first hot burst erupt inside her.

Finally it was done and her hot, sweat covered body collapsed upon his. Too exhausted to even lift herself, she just laid there, his cock still within her. Eventually it began to shrink to its pre-aroused state and slipped from within her...

Drained, Jack quickly fell back asleep, leaving Jennifer to ponder what she had done. It'd been years since they'd fucked in the middle of the night. In fact it'd been months since they'd fucked at all.

It had been sex, pure and simple. Jack had been nothing more than a warm blooded dildo used for her pleasure. Truth be told, Jennifer knew she would have traded it in a moment for the lifeless hard rubber one that Sally had worn, as long as the young Asian woman was attached to the other end of it...

It was that thought that filled Jennifer's mind as she finally drifted off to sleep.

The next Friday morning came quickly and with it Sally and Jennifer's morning coffee. It was hard for Jennifer to keep her mind on the more mundane topics of discussion. All she could see when she looked at Sally was the image of her half naked, screwing the life out of that blonde woman. Four times that week, Jennifer had masturbated to that memory and each climax had been as rewarding as the original.

"Do you have any plans for tomorrow night?" Jennifer asked as casually as she could, trying not to sound too interested in the answer.

"Why yes, I was planning to go out with a friend." Sally replied as she sipped her coffee. "Why?"

"Oh no reason, I just thought if you had no plans we might watch a movie on cable or something." Jennifer explained. "No big deal, maybe another night."

"Sure, why not." Sally said.

The moment Sally said she was going out, Jennifer knew that it would be with that blonde again. Silently she hoped they would find their way once again back to Sally's apartment, because if they did, she knew she would be there also. The temptation was too hard to resist.

During the week, Sally had left the keys to the basement apartment with Jennifer because the exterminator was coming by. The older woman had taken the opportunity to check on the peep hole from the other side. To her relief, it was practically invisible. The hole was part of a small piece of chipped wallboard where a wall light had been installed. When the wall light was on, you couldn't look directly at the hole from Sally's side. Jennifer had eliminated the possibility of light from the utility room sided by covering that hole with a small piece of tape.

Jennifer stared at the ceiling as she waited for the clock to reach twelve. She assumed that Sally would be home at the same time as last week. The brunette was too excited to sleep and she ignored Jack's snoring as she ran her finger up and down the slit in her mound. Finally she couldn't wait any longer and got up. Following the same pattern as last week, she made her way to the utility room.

Carefully she removed the tape and saw that the basement apartment was still dark. A small frown of disappointment filled her face. Did they go somewhere else? Perhaps the blonde's home?

"I'm here, might as well give it a little time." Jennifer thought to herself as she got comfortable.

She'd fixed up that corner of the utility room earlier in the week, making a little platform out of some heavy wooden boxes and topping it with one of the boy's old bean bag chairs. It gave her a comfortable place to sit.

It was almost too comfortable as once she'd sat there a while, Jennifer fell asleep. It was only the sound of voices through the wall that woke her up. Sally was finally home.

Excitedly, Jennifer pressed her eye against her spy hole. Yes, it was Sally, and she was in much the same state of undress that she'd been the week before. The Chinese woman was kneeling on the bed, straddling another woman whose face was pressed between Sally's legs. It was obvious from the look of contentment on her face and the soft moans from Sally's lips that the partially obscured woman had her tongue up and within Sally's pussy.

"This is so exciting." Jennifer thought as she slowly caressed her own pussy, imagining the feel of a willing tongue on it. "Come on Amber." she silently added. "Do it to us!"

It wasn't until both Sally and Jennifer had their first mini-climax that the woman beneath Sally climbed out from under her lower and Jennifer got a good look at her face.

"That's not Amber." Jennifer started to exclaim out loud, catching herself only at the last moment.

Sure enough, the woman in Sally's bed wasn't the same blonde that had been there a week before. She was just as blonde but her hair was long, stretching down to her waist. The light was bright enough for Jennifer to see that unlike Amber, this new love had blue eyes. Finally, it was obvious that this blonde was in her mid-thirties. Listening carefully, Jennifer heard Sally call out her name. It was Susan.

The night ended much as it had the week before, with Jennifer sharing Sally and Susan's climax. The only change was that when she went back upstairs, Jennifer was more willing to stop at the bathroom and satisfy herself with her vibrator rather than try to repeat last weeks late night fuck with Jack. The final result was the same with fewer problems. Seven days quickly passed and during them Jennifer's thoughts turned many times to the question of who she would find with Sally when she looked though the hole on Saturday night. At least once a day she masturbated to the images of the last two weekends and the anticipation of what was to come. She no longer cared that Jack had started working later than he normally did and that she slept alone more and more. It just gave her more time to think of Sally.

-=-=-=-

"Oh Sally, tes seins sont si magnifiques. J'adore les sucer." said the small long haired brunette who was sucking eagerly at Sally's breasts.

"C'est l'attention de ta langue merveilleusee Marie-Josee, qui fait ressortir leur veritable beaute." Sally replied as she gently stroked the side of her lover's face.

From her hidden view, Sally could easily hear the words of love but her own limited high school French was two decades behind her. The most she could make out was that the girl's name was Marie. She was a small woman, 25 years old and only 4'11" in height. What she lacked in stature she more than made up in passion.

As she had the two weeks before, Jennifer shared in that passion.

-=-=-=-

"Who will it be tonight?" Jennifer thought as she made herself comfortable in the beanbag chair. "The suspense is killing me."

She didn't have long to wait, and the answer wasn't who but how many. Sally was laying across the bed, her head nestled between the ample breasts of a plump, dark skinned Philippine woman. Jennifer guessed she must've weighed about 160 lbs., but was nevertheless an extremely sexy woman. Her breasts were at least 44D and rested on each side of Sally's head.

Across both women's feet lay another Asian woman in her early 20's. As pale skinned as the first was dark, she had small rounded breasts and a tiny black patch between her legs. In her hand she held a small white vibrator, which at the moment was half buried in Sally's pussy.

-=-=-=-

"Oh my God!" Jennifer gasped as she took in the appearance of the blonde propped against the headboard of the large bed, her wet pussy growing wetter under the gentle caress of Sally's tongue. "She's adorable." added the 38 year old as she admired the small firm breasts that bounced up and down as the girl met each stroke of Sally's tongue with a thrust of her own.

The girl was 5'3" with a very youthful face. All the girl was wearing was a bright red bra, pulled down to expose her mounds. The matching panties were somewhere on the floor. Her skin was tanned from head to toe, evidence that she liked to sunbath nude.

The girl had a familiar look to her. Jennifer knew she had never met her before, but there was something about her. Then it came to her. The girl was almost a dead ringer for an actress that had appeared on a sitcom when Jennifer was younger. The Bradley Group or something like that. She couldn't remember the actress' name but she remembered that all the teenage boys in the neighborhood had been hot for her. Jennifer remembered overhearing her older brother tell one of his friends that she was the girl they most wanted to fuck.

The girl was obviously not that actress, or even a teenager, but the resemblance was exciting to Jennifer, even more so as she buried three fingers within her cunt, frantically rubbing her clit. -=-=-=-

Five weeks, six different lovers - it was too much for Jennifer to fully absorb. Her whole world now seemed to revolve around that small utility room and the visions of delight just beyond it. That she was invading the privacy of others no longer came into play. All she knew was that nothing in her life had caused such a reaction within her. In her dreams, she became the women in Sally's bed - the object of her considerable lust.

The following week, Sally had a small cold and decided to stay home alone over the weekend. Jennifer couldn't believe the deep sense of disappointment she had felt over that. The Saturday nights they unknowingly shared were becoming an all consuming obsession.

-=-=-=-

Jennifer's face paled at the sight that greeted her eyes a short week later. She had heard about such things but neither understood them or ever thought she would. Sally was face down on her bed, her hands and arms tightly bound together by thin white cord. A small black gag filled her mouth, the center of which held a tiny red ball. Her legs were spread wide apart, chained to a thin wooden pole that kept them that way.

"Take it bitch!" the salt and pepper haired woman said as she held on to the strap on cock between her legs and pressed it against the gap between Sally's cheeks. "You know you want it."

Dressed in a leather outfit that left her large breasts hanging free, the 50 year old woman pushed harder until the head of her rubber cock began to disappear into Sally's wet pussy. The Chinese woman bucked up and down as her captor pushed inch after inch inside of her.

"Oh baby, you know you love it" Rose Marie said as she slid the full length into her helpless captive.

Ann Douglas
Ann Douglas
3,179 Followers