Rob's Initiation

Rob Quinn turned eighteen in the middle of his senior year in high school. A perpetual horndog, he constantly had girls on his mind. Tits, preferably big ones. Pussy. He hadn't gotten any yet, but it was not from a lack of trying.

Sally Smith had been his "steady" for the last two years. She had long blonde hair, blue eyes, a perfect face, and a body that would stop traffic. She was also a virgin, and planned to stay that way until she got married. Rob's mission in life was to get her to change her mind.

He constantly fantasized about her. Getting his eyes, his hands, and his mouth on her luscious breasts. He wondered what her nipples looked like? What color were they? Were they puffy? How big were her areolas? Every time he had tried to cop a feel, she would push his hand away.

At night, he dreamed about her naked body and all the things he would do to it. And all the things she would do to him. He imagined what her pussy looked like. Never having seen one, he didn't know what he'd find if he ever got "down there." Was her pubic hair blonde too? What did it smell like? Taste like? Could he eat it?

Most everything he knew about sex, he got from the other guys in the locker room. They all bragged about their conquests with their girlfriends. He didn't realize most of what he heard was bullshit; he thought he must be the only male virgin in his class.

He knew, from checking out the other guys, that his penis was larger than average. Didn't girls really like a big cock? Sally didn't know that he had a big one, because she'd never seen it.

One time he rubbed it against her when they were dancing, and she pulled away and left a foot of space between them. She wouldn't press her breasts against him when they were dancing either. She did, however, really like kissing and making out. No tongues allowed.

He had to satisfy himself with his good right hand. Which he did, several times a day. He'd stroke himself and imagine it was her hand on his cock. He'd lube it up, roll over on his stomach, and pretend his hand was her pussy.

His favorite product was the Astro Glide that he "borrowed" from his sister Kathleen's bedside table. Kathleen was two years older than Rob and had a collection of vibrators in there too.

Sometimes at night, he could hear a buzzing noise coming from her room, along with moans that got really loud when she came. He imagined watching her use one. He was the Walter Mitty of horny fantasies.

Sometimes, even though he knew it was wrong, he fantasized about Kathleen. She was a stone fox too, with long legs, a terrific ass, and as he knew from checking out her underwear drawer, wore a 34C bra. When she wore one, that is. Her favorite around-the-house attire was a pair of cut-off short shorts and a tee shirt with no bra.

He could tell they were firm, because they hardly moved when she walked. What really drove him crazy was her nipples that were prominently displayed under her shirt. Sometimes, when it was chilly in the house, they really stood out.

One night after going to a movie and a heavy make-out session with Sally, Rob came home and noticed his friend Susie sitting out on her porch swing.

He'd known her since she was five, when the Bakers moved next to the Quinns in the quiet neighborhood where they lived. They had never dated, she was his friend, he never thought of her that way. Susie and Rob could talk about anything, even sex.

He went over and sat next to her on the swing. "What's up, Rob, you look really bummed out?"

He decided to let it all out. "It's about Susie. We've been going steady for two years, and she won't let me do anything but kiss her. She won't even French kiss. I'm probably the only guy in the senior class who's never even felt up a girl."

He knew she had gone with several guys during their years in school, and for the first time wondered about her sexual activities. "How far have you gone with a guy?"

"Well, I've let them feel my boobs, and I've done a hand job," she answered frankly.

"Feel your bare tits?"

"I've never let them do it bare, but I let one guy go under my sweater and feel me over my bra."

Rob had watched her breasts grow over the years, from little buds to a really nice rack. They had to be at least as big as Kathleen's. She was wearing short shorts and a tight tee shirt. All of a sudden, he was looking at her in a new light.

Surprising the shit out of him, she leaned over and pressed her lips to his. They were so soft and supple. Her lips nibbled at his, and without warning, her tongue snaked out into his mouth. He met her tongue with his and their kisses intensified.

They both breathed heavily as they experienced raw passion. His cock became rock hard; her panties were wet. His hand casually slipped off her shoulder and landed on her breast. He waited for her to push it away, but she didn't.

Emboldened, he slid his hand under her tee shirt, up to her lacy bra. He cupped each one, then his fingers traced the swell of her breasts where they spilled over the top of the bra. God, they felt wonderful!

He remembered her limits, and wondered if he could exceed them. When he tried to get his hand under her bra, she pulled it away. She really wanted him to do it, and a lot more, but she was holding off, waiting for the right guy. If they weren't good friends, and he wasn't going steady, he might have been the one. But not now.

Aware of his state of arousal, she reached over, unzipped his pants, and released his swollen penis. "Wow, nice cock, nice big one," she said, and wrapped her hand around it.

It felt wonderful. It was the first hand, other than his own, that ever touched it. She stroked him slowly, up and down the shaft, pausing to run gentle fingers over its head. A long, low growl escaped from his throat, along with his ragged breath.

The tingle began at the soles of his feet. His toes curled, his balls contracted, and the rush spread through his cock as he came. And came. And came some more. "Oh God, Susie, that was totally awesome."

"Glad to help," she said gently, and kissed him lightly on the mouth. She was completely wound up and spent a long time that night with her fingers between her legs.

Rob and Sally's senior prom was coming up soon. Lots of the kids were booking hotel rooms afterwards, but they were not among them. Although her hormones were raging, her parents, and her religious upbringing had drilled keeping her virginity into her head.

Most of her girlfriends had some kind of sexual experience, from going "all the way," to heavy petting, to mutual masturbation. Her friend Julie told her, in all sincerity, "if you want to hold onto a guy, you've got to give him something. If you don't want let him fuck you, at least jerk him off or give him a blow job."

Sally winced at the word "fuck," but thought seriously about what Julie had said. She was, quite naturally, curious. She had no idea what a penis looked like, let alone how it felt. Likewise, she didn't know how to do either a hand job or a blow job. Julie gave her instructions.

At first she thought the idea was disgusting. My God, he pees out of that thing, and I'm supposed to put it in my mouth?

Thinking about it, however, caused a tingling sensation between her legs, but she had do idea what to do about that either. She finally made up her mind.

They next time she and Rob went on a date she told him, "I'm really looking forward to the prom." Then she giggled nervously and whispered in his ear, "I've got something special for you afterwards." He was intrigued.

Sally wore a floor length, strapless gown. It was more modest than most, but at least it showed a little bit of cleavage. If he stood on his tiptoes when they danced, he could peek down the top and get a glimpse of her wired, solid white bra and the swell of her breasts spilling over the top of it.

She held him tightly as they danced, and he could feel her firm breasts pressing against his chest. And didn't back up, at least not much, when she felt his erection against her abdomen. He wondered what her "surprise" was going to be. Jesus, he was horny.

They, as usual, parked a block away from her house, under a canopy of elm trees. That way her parents couldn't see them making out. When they started kissing, Rob was startled when her felt her tongue timidly enter his mouth. He met her with his own, and they did a little tender dance in each other's mouth.

He could feel her heating up, and his passion grew to match hers. Out of nowhere, she took his hand and pressed it against her breast. He cupped, molded, and stroked, marveling at their size and shape. He couldn't feel a whole lot through the fabric of her dress and her rigid bra, so he kind of guessed at where her nipples might be.

She couldn't feel a whole lot through the layers either, but found herself aroused by just the idea. He tried to slide his hand down the front of her dress, but she pulled it away and put it back outside her clothes.

Then, incredulously, he felt her hand unzipping his fly. As she was fumbling with the process, he reached in and pulled it out for her. She let out a gasp and her eyes widened at the sight of her first penis. Half frightened, half titillated she stared at it. So big. So hard. Purple veins lined the shaft, the head look so red and almost angry.

Tentatively, she put her hand around it. So hard, yet soft. So hot and throbbing. She moved her hand, as Julie had instructed her, and felt the skin move with her stroke. She held her breath, closed her eyes, and bent down and took it in her mouth.

Rob was in hog heaven. Nothing in his life had ever felt so good. She bobbed her head up and down about three times and he couldn't contain the rush that overwhelmed him. He shot an enormous load right in her mouth.

Her teeth wounded the head of his cock as she violently pulled away. Her screams were muffled by the gagging and choking. She spit out the volume of semen, then projectile vomited. All over her dress, in her shoes, and all over his pants and his father's car. She jerked open the car door and ran home as fast as she could, leaving her shoes behind on the sidewalk.

She never spoke to him again.

******************

Aunt Peggy was coming for the weekend. She was their mother, Mary's, younger sister. All three of the younger Quinns, Rob, Kathleen, and Colleen, loved her. She was childless, and doted on her nieces and nephew. She only came when their father, Mark, was out of town.

Peggy and Mary were best friends, and they talked and laughed until the wee hours. They slept in the same bed, as they did when they were children. Rob and Colleen thought it was "cute." Kathleen had other suspicions.

Rob thought she was hot, at least for an older woman. She had strawberry blonde hair, a pretty face, and a curvy body with nice, high breasts. She wore low-cut tops that showed lots of cleavage.

Peggy and Mary, after sharing a bottle of wine, were undressing for bed. Actually, they were undressing each other, slowly and deliberately. Peggy, at forty, had firm, high breasts without a hint of sag, thanks to her plastic surgeon. She hadn't had any enhancement, her breasts were already full, he just restructured her muscles a bit to take out any droop.

Mary's breasts were somewhat elongated, and at 42, had a bit of middle aged sag. She joked that she wore the same sized bra that she did in high school. "But when I take it off, my nipples are three inches closer to the floor."

They stood naked before each other, then moved together in a passionate embrace. Peggy stroked and fondled her sister's breasts, then lowered her mouth to her nipples and sucked each one in turn. Mary's whole body was aflame, her heart beating like a jackhammer in her chest. A low moan, mingled with her ragged breath, escaped from her throat as she came, her juices running down her thighs.

They fell back on the bed. Mary hovered over her sister, running her lips and tongue over her whole body. When she got to that warm, wet place between her legs, she licked and sucked with wild abandon. Peggy writhed and bucked her hips in tune with the tongue that lapped at her pussy. Reaching her peak, she screamed and came hard. Mary's mouth filled with her spunk.

She moved up her sister's body until they were lined up, vulva to vulva, then they began to grind against each other, tribbing with abandon, clit to clit, until they came together in a shuddering aura of lust and longing. Satisfied and spent, they fell asleep in each other's arms.

Kathleen had been listening outside their door; her suspicions were now confirmed. What she didn't anticipate is how turned on she had become while eavesdropping. Her pussy was soaking wet.

She had never experienced another woman, but the idea titillated her. Sex with her fiancé was less than satisfying. He was crude and fast, taking his own pleasure without concern for hers. She had overheard the slow, lingering, loving way her mother and aunt made love to each other.

Returning to her room, she dropped her robe, and stood in front of her full length mirror, examining her image in the glass. She ran her hands over her full, ripe breasts, feeling all the curves and the lovely uplift. Rolling her nipples between her thumb and forefinger, she watched them harden and pertly stand out. She could reach them with her tongue, which she did, and wished she could suck on them herself.

She caressed her body, from her breasts, down her abdomen, to her pussy. She pushed two fingers as far as they would go into her hot, wet vagina and frigged herself as fast as she could. Wetting her fingers, she rubbed them over her clit, and watched in the mirror as her juices spewed out of her cunt when she came.

Reclining on her bed, she reached into her bedside table for her favorite sex toy, her purple "rabbit." Turning it on she watched as the head of the soft vinyl penis revolved and the silver beads further up the shaft spun around and around.

She was wet enough, and didn't need her AstroGlide. She inserted the vibrator into her vagina, and purred as the head revolved deep inside her, and the beads tantalized her labia. She pressed another button, and the little rubber fingers buzzed against her clitoris.

Rob, passing down the hallway, heard the buzzing, the moaning, and the cries of ecstasy as she exploded in orgasm. He found himself sporting an enormous hard-on that he had to stroke off when he got back to his room. Colleen and her best friend, Nathan, were watching a DVD in her third floor loft, oblivious to what else was going on in the house.

In the morning, they all gathered around the kitchen table, having an after-breakfast cup of coffee and chatting with Aunt Peggy, catching her up on all their activities. School had just ended, and she asked them all what they were going to do.

Kathleen was going to intern in her fiancé's family bank, and Colleen was tutoring students in math at summer school. "What about you, Rob?" she asked.

"I'm still looking," he said dejectedly.

"Oh great! I'm looking for someone to work for me this summer. I have landscaping to do, some maintenance and painting, and a whole bunch of other chores that need doing. I'll pay you twelve dollars and hour, plus room and board of course."

"Wow, that would be great. Thanks, Aunt Peggy." Twelve dollars an hour was a fortune to him, he had been expecting to earn minimum wage, if he could even find a job. If he saved enough, he could buy a car to drive to the community college he would be attending in the fall.

Peggy lived in a rambling one story house on a fifteen acre lot in a wooded area, about two hours out of town. The house was all redwood and glass, with enormous decks overlooking the valley and the river below. There was a large swimming pool in the back that would provide a refreshing finish to a long day's work. He was a hard worker, and would definitely give her her money's worth.

He started early the first morning, digging up the soil along her walkway where she wanted a low hedge. Nearing noon, the sun rose high and hot in the sky. Peggy watched as he peeled off his shirt, the sweat glistening on his body. He stood 6'2", was well muscled, including six pack abs.

She watched as he swung the pick and spaded the earth. Jesus, what a hunk, she thought to herself. Her eyes narrowed into a feline countenance and her lips curved into a slight smile. It sure would be fun to seduce him. She could teach him a lot. But she'd need to go slow. After all it was a long summer. A long, hot summer?

Peggy had never married. After college, she worked as a computer programmer for a large multi-national corporation. After ten years, she opened her own business, developing industry-specific software programs. Her company took off and she recently sold it to another large corporation for twenty million dollars.

She, since she started college, she lived with her bachelor brother, Jack. There were whispers among some family members that their relationship was more than brother and sister. Jack taught physics at the university, and was on a summer hiatus in Paris, leaving Peggy alone in the house.

Rob knocked off at 4:30, having put in a good eight hours. He was shining with sweat, his muscles all pumped up after a hard day's work. "Why don't you take a shower and then have a dip in the pool before dinner. You look hot." Peggy had more than one definition for hot.

When he finished his shower, he pulled on the Speedos that he wore on his high school swim team. Even flaccid, Peggy noticed that he had quite a bulge in the spandex. She licked her lips.

After they'd finished their dinner, she moved behind his chair and began to massage his shoulders, digging her fingers deep into his muscles. "Ahh, that feels really good, Aunt Peggy."

"Let's drop the Aunt, just call me Peggy." She continued her ministrations. There was a lot more of him that she wanted to get her hands on, but she could be patient; one step at a time.

They moved into the living room to watch a movie, sitting on opposite ends of her long couch. She was wearing an old pair of jeans with frayed knees and a loose fitting tee shirt. Rob couldn't help ogling her chest when he discovered she wasn't wearing a bra. She caught him staring at her protruding nipples, and at the thought, they stiffened with her arousal.

Her dog, Goofy, a shaggy haired mixed breed, streaked into the room and flopped down at her feet, thumping his tail on the floor. When she bent over to scratch his ears, her shirt pulled away from her body, and he got a flash of the upper part of her breasts. No nip-slip, but enough to make his penis harden. Peggy's eyes narrowed as she took in the rise in his pants.

It rained the next day and they moved their chores indoors. Peggy dragged a stepladder into the center of the room; she wanted to dust off the blades on a ceiling fan. "Hold the ladder steady for me, Please."

She was wearing a pair of shorts, and he noted what great legs she had, long, and well toned. When she reached the top of the ladder, Rob could see up the legs of her shorts. Wow! she was wearing a thong. From his position behind her, he could see both cheeks of her ass, with tiny ribbon of fabric disappearing in the cleft. He scooched around to the front, and he could see the tiny triangle pulled up between the lips of her pussy. A perfect camel toe. She watched him looking at her, and her panties moistened.

Peggy's friend, Sheila, came to visit that afternoon. It had stopped raining, and Rob got back to his landscaping tasks. He checked her out as she came down the walk. Platinum blonde hair, full lips, dressed in a skin-tight mini skirt and a low cut top that showed lots of cleavage.

Swinging hips, nice ass, and a magnificent rack. He didn't know about the silicone implants, tummy tuck, liposuction, other nips and tucks, and hours with a personal trainer that kept her looking that way. She got a good look at him, too, and started to drool.