Heather was a morning person. Every day she rose at dawn to head straight up the spiral staircase from her bedroom to her office in the converted attic. There, as the sun rose, her mind was clearest and she at her most productive. She wrote quickly and steadily. A creature of habit she would not emerge until noon, at which point her workday was done and she could tackle her other job: stay-at-home wife, mother, and volunteer for innumerable causes.
It was spring break. Heather's youngest, Kyle, was eighteen and a senior in high school and her only child still living at home. For Kyle no school meant waking up without an alarm, so he didn't roll out of bed until nearly ten. He had slept in the nude now for several years. Kyle loved to be naked. Normally he dared roam the house in his altogether only when he knew no one else was home. But today he felt daring. He got an erotic charge from the thought of walking in the house naked with his mother just upstairs. Kyle was certain she would be sealed away in her office for another two hours. Confident there was little chance of getting caught Kyle casually walked to the bathroom in the buff.
The sound from the water pipes below let Heather know that her son was finally awake. Her concentration broken, she stood and stretched. The sun shone bright. It was going to be warm today. Heather thought about the fact that in a few short months her baby would be off to college. Work could wait. Heather thought perhaps Kyle would be up to join her for a morning bike ride. A few minutes after she heard the shower stop she headed downstairs. From the bottom of the stairs she could see across the darkened bedroom and down the hallway, drenched in bright sunlight. The bathroom door opened and Kyle entered the hallway. Heather looked, gasped, and froze in place. Kyle was nude.
It had been years since Heather had seen Kyle naked. Of course she had seen him in just his swimsuit the summer before, but those baggy trunks left everything to the imagination. The sight was such a shock that, to Heather, Kyle seemed to move in slow motion. Her eyes went directly to his genitals. His penis hung long, full, and loose. Draped over his scrotum, his two large testicles visible at each side and pushing it out, his penis swayed gently as he walked to his room and out of sight. The sight of her son's penis was etched into Heather's brain. She did not feel lust or desire, but she did feel pride. Pride that she had made that. Pride that her son had grown so large and virile.
Her mind a jumble, Heather backtracked and returned to the attic. She tried to work, but she could not complete more than a sentence before her focus was lost and she saw only her naked son. She went back downstairs, expecting Kyle would be dressed and in the kitchen eating breakfast by now. As she passed his bedroom she looked in and had another shock. Kyle was there, and still naked. He sat at his computer, facing the wall. There was an image of a nude woman on the screen. Kyle's right hand worked the mouse while his left stroked his erection with what Heather recognized as her missing black silk panties.
As quietly as she could Heather crept away downstairs to the kitchen. Heather was not entirely naïve. She had assumed Kyle had been masturbating for several years. Of course it was perfectly natural and he should have no shame about it. But with his door open? And with her panties? Heather sat at the kitchen table feeling quite awkward and debating whether she would have the courage to speak with Kyle about boundaries. With those thoughts came inescapable images. She knew as she sat there, sipping her coffee and staring out the window, upstairs a young man was having an orgasm, ejaculating his seed into her favorite panties.
Heather was disappointed that Kyle had not yet found a girlfriend to do "that" for him. Heather had been concerned about Kyle's shyness for some time. While he was involved in sports and other extracurricular activities, he had few friends and most Friday and Saturday nights he spent at home with a book. He was quite handsome, and that wasn't just a mother's opinion. She had heard it from her friends as well. With a little confidence he could have any woman he desired.
Heather heard footsteps and turned to see for a third time her son completely naked, his spent penis, red and deflated, dangling between his legs. Seeing his mother Kyle gave a yelp and bolted back to his room. Heather knew confrontation was now inevitable. Not being one to procrastinate she headed upstairs. Heather tapped on Kyle's door and he managed to squeak a meek, "Come in."
"Hey, can I talk with you for a minute?" Kyle could manage no reply. "I guess you are feeling a bit embarrassed."
"Mom, I'm really sorry, I thought you were still in your office."
"Kyle, you have nothing to be sorry about, you haven't done anything wrong. I was in my office this morning, but the day was just so beautiful I thought we could take a bike ride. I came down thinking you would be in the kitchen, but saw that you were still in your room." The look of terror that flashed across Kyle's face told Heather that he had just realized that she had seen him earlier as well.
"Yes Kyle, I did glance into your bedroom on the way by, and I did see you masturbating. You have nothing to be ashamed of. Your father and I told you during our 'talk' years ago that you should never feel guilty about your sexuality. I've known that you masturbated; I just never had such unequivocal proof. It is not something that you should feel the need to hide. I'm not embarrassed that I saw. But, if it is something you want to do in private, you might want to think about closing your bedroom door."
This sarcastic remark brought a smile from Kyle and the tension was finally broken.
"Do you walk around the house naked often?"
"Yes. I really like it. But I promise I'll stop."
"Well, if you want to stop, that is up to you. You have a beautiful body. You shouldn't be ashamed of it, and I won't be ashamed to see you. If you feel more comfortable naked, that's o.k., but I'm not going to worry about avoiding you when I'm home. So, if you don't want me to see you that way, you need to be more careful."
"O.k." Kyle paused, and Heather could tell he wanted to say something else. Finally he managed to say, "You're not going to tell dad about this are you?"
"Well, I don't think you're giving your dad enough credit. He's pretty open-minded too. But, if you want to keep it between us for now, then o.k. I'm going to go back to the kitchen and fix you breakfast. Be down soon. Wear whatever you want. Or not." Kyle did finally arrive back at the kitchen, fully clothed. They smiled at each other, and Heather was surprised to realize that she was more than a little disappointed.
Heather's sleep was restless that night. In her dream she found herself in the kitchen making Kyle's breakfast. When he arrived he was naked, and something else had changed too. In her dream he was impossibly huge. As she stared his manhood began to fill and harden. With each heartbeat it rose and expanded until finally reaching its fully engorged state. She fell on her knees in front of him and reached a tentative hand out to slowly, softly stroke the shaft. As Kyle caressed her hair she became bolder, tickling the head with her tongue. She then took it into her mouth, stroking the shaft with her right hand and kneading his scrotum with her left. She awoke with a start, panting, and a very wet hand between her legs.
Several weeks earlier, Heather had begun a long distance, cyber friendship with a woman she had met online. At 41 Heather was feeling in the midst of a sexual renaissance. To indulge her recharged sexuality Heather had been exploring erotic stories. Jill was her favorite author and Heather, rather timidly at first, began a correspondence. For Heather, Jill was a revelation. While Heather had an open mind, in practice she was quite conservative. Faithful to her husband for over twenty years it had never occurred to her to seek physical pleasure outside of her marriage. But Jill, an open bisexual, had stirred thoughts and feelings in Heather that aroused and frightened her.
The next night Heather again dreamed of her son. Heather was in her bedroom sitting in the corner of the darkened room. Kyle lay on her bed naked and flaccid, as though waiting for someone. In her dream Heather was about to stand and walk to him when a woman entered the room. It was Jill. A tall and slender brunette, at 45 easily passable for a woman much younger, Jill slowly made her way to the bed. Without a word between them Jill gently petted Kyle, who rose and filled quickly to his full length. Heather instinctively knew that she was witnessing her son's loss of innocence to an older woman, her friend and confidant to whom she had divulged her most intimate secrets and yearnings.
Still without words Jill lay on her back and motioned for Kyle to mount her. He obeyed, climbing between her legs. Jill carefully guided Kyle's penis to her entrance. He paused, unsure whether he had permission to advance. Jill smiled up at him, wrapped her arms around his back and with her legs pulled him inside of her. Heather had been unconsciously stroking herself. But as she saw her son enter her friend, her stroking became more frantic. Her son did not last long and let out a primal yell as he buried himself as deeply into his first lover as he could, releasing blast after blast of his semen. His orgasm pushed Heather over the edge and she spasmed uncontrollably.
Heather awoke to the diminishing quakes of her exquisite little death. Heather recognized the dream as a manifestation of a fantasy she had not allowed herself to consciously acknowledge. She wanted to witness her son's deflowering. And she wanted Jill to do the honor.
Heather had been very careful in her communications with Jill, fearing to give too much personal information. While she trusted Jill, she had heard so much about online dangers she thought discretion the better part of valor. So it was with much trepidation that Heather finally communicated her desire to Jill. After some discussion, Jill agreed to travel to Heather's home, but on one condition. Before she took Kyle, Jill would take Heather.
The day had finally come. Heather had not slept well the night before, racked by fear and second thoughts. She wondered whether what she was about to do would be the greatest experience of her life, or the greatest mistake. Her mouth was dry. Her heart pounded so fiercely she could hear the blood rushing through her ears. Her hands sweated and shook uncontrollably. Finally Jill arrived. Heather opened the door. The photos Jill had sent her had been no hoax. There stood Jill, tall and slender, drop dead gorgeous. Heather stood frozen. Jill finally broke the spell. "Well, are you going to invite me in?"
"I'm so sorry. Of course."
"You seem terrified."
"I'm sorry. I absolutely am."
Jill approached Heather and gave her a friendly hug. Heather was hesitant at first, then finally relaxed and wrapped her arms tightly around her friend.
"O.k., you can let go now."
"Oh goodness, I'm sorry."
"You really need to stop saying that. Just relax."
Jill entered the house and had a look around. They proceeded to the living room to sit and chat about innocuous things. How was her husband's trip going? How has the weather been? How is Jill's latest book coming along? When a long silence interrupted the banality, Jill moved from her chair and sat next to Heather on the sofa. Heather smiled meekly at her and then looked down at her hands. Jill resolved to be gentle . . . this time. She ran her fingers through Heather's hair and caressed and massaged her neck.
Slowly Jill drew her mouth closer to Heather, imperceptibly touching her lips to her ear and breathing deeply her scent. Jill then lightly kissed her way down Heather's cheek to her neck. With that as a distraction, Jill's left hand lightly caressed its way up the inside of Heather's left thigh. "Damn these ridiculous jeans," Jill thought. Heather, aware only of the incredibly soft kisses on her neck, opened her legs without thinking.
Heather's mouth sought out Jill's. Their kisses began quite innocently, but soon their lips parted and their tongues danced. Finally their kiss broke and Heather gasped for air. Only then did she notice the hand between her legs, now firmly rubbing her mound. Heather leaned back, her right hand moving to touch her breast. Jill reached out and seized Heather's wrist. "Oh no, that is for me. You will not touch yourself." Jill pulled at Heather's sweater and Heather quickly lifted it over her head and off. Jill then directed her to remove her bra.
Jill began her kisses at Heather's navel, slowly working her way up her flat stomach, then around her left breast making circle after circle, deliberately avoiding the areola. Heather was in ecstasy and agony, desperately wanting Jill to suck her nipples. Jill watched Heather's face and saw the torture, but would not proceed until Heather begged for it. Finally Heather couldn't take it anymore. "Please, please," she cried. Jill took her nipple in her mouth, sucking it, circling it with her tongue and rapidly flicking it. All the while her left hand continued working Heather's still clad pussy.
Jill's mouth switched to Heather's right breast and played the same torturous game, waiting for Heather's pleading, and upon hearing it, sucking and licking mercilessly. Heather was approaching her peak now. Her breathing became ever more rapid. Her panting became moans, then cries, then a final groan and crying out as the most powerful orgasm of her life broke in waves from her center to every nerve ending in her body.
Heather had momentarily blacked out. She came to, her eyes fluttering open to find Jill's beautiful green eyes smiling at her. "Hey there. How do you feel?"
"Can we go upstairs?"
Heather and Jill stood and walked together upstairs, holding hands. Reaching the bedroom Jill removed Heather's jeans and sopping wet panties. Jill had Heather sit on the edge of the bed while Jill stood in front of her slowly, seductively stripping herself. Heather watched. She had never viewed another woman so sexually. Jill's body was spectacular, lean and tight. Jill stepped between Heather's legs. Heather wrapped her arms around Jill, rubbing her back and ass while alternately kissing her stomach and sucking Jill's large, hard nipples.
Jill climbed onto the bed and spread her legs. Heather knew what she wanted and went straight for Jill's pussy. Heather was overcome with the urge to make Jill come, to give her as much pleasure as she had received. Her hands were everywhere at once, massaging Jill's breasts, stomach, legs and ass. Her tongue alternated between fucking her pussy and licking her clit. Certainly Jill had experienced better. But knowing this was Heather's first time doubled the pleasure and soon her own powerful orgasm shook her. The two lovers curled up together, tired and spent from a night of restless anticipation and a morning of rapturous sex.
After lunch they spent the afternoon in the backyard swimming in Heather's pool, lounging, and scheming. Together they made a plan for that evening.
Kyle arrived home from soccer practice just in time for dinner. He entered the kitchen and did a double take. Seated at the table having a glass of wine were the two most beautiful, bikini-clad women he had ever seen in the flesh.
"Hey Kyle, this is my friend Jill. She's going to join us for dinner tonight."
Jill stood, displaying her entire body to the nervous youth. "Hello Kyle, I'm very glad to meet you. Your mother has told me so much about you." Kyle managed to squeak a, "Hello, nice to meet you," before heading upstairs for a quick shower.
"He really is quite handsome. This is going to be fun." Heather could only blush at Jill's excitement.
Kyle soon arrived back in the kitchen. Dinner was quiet. Kyle, shy and reticent, wasn't much for conversation. But while his voice was inactive, his eyes were not. His mother, normally so modest in dress, was as great a distraction as the newcomer. After dinner the women went out on the deck for another glass of wine and Kyle retired to his room for homework. After an hour of distracting small talk, Jill finally broke the ice. It was time to put their plan into action.
Upstairs behind his closed door Kyle scanned his favorite MILF sites and stroked himself. A quiet knock at his door sent him scrambling to close the browser and zip up. "Come in."
"Hey Kyle, I hope I'm not bothering you."
"No Jill, that's o.k. I was just about to quit for the night anyway." Jill looked around the room. It had been ages since she had been in a teenage boy's room. The posters, strewn clothes, and scent took her back, and she felt eighteen again. Jill sat on his bed still dressed only in her bikini. Baggy or not, his shorts could not hide his bulge from her inquisitive eyes.
"You're a very good looking guy Kyle, I bet you have lots of girlfriends."
"Hardly. Girls don't go for the bookish type."
"Well, those high school girls don't know what they're missing. Maybe what you need is an older woman who can appreciate you." Kyle didn't know what to say, sheepishly staring at his feet. Jill moved forward from the bed and knelt next to him, placing one hand on his knee, the other on his shoulder.
"Tell me Kyle, have you ever been with a woman?"
"Um . . .." Kyle trembled and looked at the doorway.
"Don't worry Kyle, your mom isn't going to disturb us. She asked me to come here today to be your first lover. Go ahead, check your phone. I bet you just got a text message." Sure enough, Kyle had a message waiting for him from his mother. "Kyle, I love you so much. Let Jill make you a man tonight."
Jill stood, reached out her hand, and Kyle took it. Jill led him out of his room and down the hall to his parents' room. "Your twin bed isn't up to what I have planned for you." In truth, Kyle's bed would have served the purpose, but it didn't offer a proper vantage point. Standing at the foot of the bed Jill turned Kyle so his back was to the door and undressed him, then herself. Quietly Heather crept passed them to the chaise lounge in the darkened corner. When she sat and looked back Jill was now completely naked and kneeling in front of her son.
For the first time Heather saw his full erection. He was the spitting image of his father in every way. Jill caressed his balls with one hand and kissed her way from the base to the tip. She knew Kyle would have a hair trigger and if she were going to have any fun she would need to get the first ejaculation out of the way. She took the head in her mouth, pressing her tongue to its tender underside, then swirling it around, then quickly bobbing up and down, sucking hard. Within seconds Kyle erupted, a huge load splashing the back of Jill's mouth. She swallowed rapidly, consuming every drop. Kyle's legs were buckling, so Jill pulled him to the bed.
Kyle lay on his back and Jill crawled up, her legs straddling him. She lay down on top of him, his still erect penis flat against her stomach. Kyle for the first time kissed a woman passionately while feeling naked flesh against his, her hard nipples poking into his chest. Heather watched the scene mesmerized. Her left hand reached inside her bikini top to caress her breasts while her right hand casually stroked her pussy.
"Are you ready to be inside of me?" Jill whispered into his ear.
"Yes, oh yes please," Kyle begged her, as his mother had begged her earlier.
Jill reached down and guided his head to her entrance. Sitting up, ready to plunge down over him, she paused tantalizingly. Kyle strained to enter her, but she waited, waited, tormenting him. She could see the sweat beading on his forehead. Finally he looked into her eyes, pleading with her again. "Please," he gasped. Satisfied that she had dominated him, Jill flashed a wicked smile and sunk down, taking his full length.