Rob's Initiation

"So Peggy," she asked, accepting a mid-afternoon martini, "who's your new boy toy?"

"Sorry to disappoint you, he's my nephew."

"Oh goodie, then, I want him. Yum!"

"Hands off! I promised my sister I'd take good care of him." You betcha, Mary, she thought to herself, I'll take real good care of him.

That evening, Peggy decided she'd join him in the pool. It took her quite awhile to decide which bikini to wear. She wanted just the right effect. Rob did a double, then a triple take, as she sauntered across the deck in three tiny triangles of bright red cloth held together with a couple pieces of string.

The top barely covered her nipples, which, incidentally, poked out prominently. And the bottom left her shapely ass completely bare, the tiny triangle in front almost disappearing between her pussy lips. Rob dove immediately into the pool, hoping she hadn't seen the front of his Speedos sticking straight out. Where he was concerned, she didn't miss a thing.

He heard Peggy splashing into the water behind him, and immediately started swimming laps. On his return trip, he saw the top of her suit floating on top of the water. He retrieved it and swam back in her direction, carefully averting his eyes. When he did look, he could see the vague shape of her breasts beneath the shimmering surface of the water.

She put it back on under the water. Now wasn't quite the time to flash her tits at him, but it would come soon. He swam rapidly back to the far end of the pool and climbed out. Keeping his back to her, he quickly wrapped a towel around himself. Her lips curved into a grin; she hadn't had this much fun teasing a guy since high school. The difference was, she didn't plan on leaving him hanging. Not too long, anyway.

One of his chores was cleaning and maintaining the pool. When he rounded the corner of the house with the leaf skimmer, he saw Peggy sunning herself, lying face down on the chaise. The top of her bikini was on the ground beside her, her gorgeous ass perfectly displayed, as her thong covered nothing.

"Oh, Rob, would you be a dear and rub some sun block on the back of me?" Timidly, he squirted some of the block on his hands, and skimmed them lightly over her back. "Harder, dear, really rub it in." Her skin was so soft, bronzed by the sun.

He applied the sun block to her sides, worrying whether he should go near the sides of her breasts. He did. A pleasure sigh escaped from her throat.

"Do my legs, too, please." She spread them slightly apart. He started at her ankles, then worked his way higher. His hands kneaded her shapely calves, then up her thighs, aware, very aware, that his hands were approaching the crease between her legs and her pussy. His breath was coming in ragged gasps, his loins tingled.

"I guess you'll have to do my butt, too, Rob, I can't reach it myself." He threw caution to the wind as he caressed and kneaded each cheek of her gorgeous ass. God, she feels good. She let out little mewling sounds as his hands reached lower. He was straddling one of her legs, and she could feel his erection pressing into her.

When he finished, he streaked into the bathroom, the sun block still in his hands. He dropped his shorts and spread the lotion all over the head of his cock. He watched in the mirror as he stroked himself into release, coating the glass with his spunk. She was forty. She was his aunt. He wanted her.

Peggy was having a pool party with four of her friends. Rob volunteered to be waiter and bartender. There wasn't a lot to tend, really, because there was a huge pitcher of margaritas, already made, in the fridge. Mostly, he wanted to hang around and check all the women out in their swimwear.

He decided that older women rocked; they were a lot looser than the girls he was used to. He couldn't imagine Sally ever wearing a thong bikini. Well, he could imagine it, but she never would. Just in case, he jerked off three times before the party, and wore a tight jockstrap under his trunks.

Peggy introduced him to the "girls", as she called them, as they came in. He'd already met Sheila, and was really looking forward to checking out her rack in her swimwear. She said "Hi, handsome," as she sashayed in, and pinched him on the butt.

Sarah and Ruth were slender and small breasted. Then there was Margie! She was a little fleshier than the other women, but she had absolutely humongous breasts. He was definitely a big tit man.

Rob came around the corner with the pitcher of margaritas and a tray full of glasses. He stopped dead in his tracks. They were all topless! They first real live tits he'd ever seen. He got a lesson in "gravity and the female breast" at the same time.

He eyes took the women in, one a time. Lying on their backs, Sarah and Ruth appeared to have no breasts at all; they had completely flattened out, all he could see were nipples. Peggy had gentle hills, but Sheila's stood straight up, two large silicone mountain peaks. As they sat up, their breasts took shape again.

Then he focused on Margie. His jaw dropped. Her enormous boobs had slid right off her chest and were nestled in her arm pits. When she sat up to get her drink, Rob thought he could hear the thud when they dropped like two bowling balls into her lap. Maybe he wasn't such a big tit man after all.

Later, Peggy and Rob, headed for the pool for an evening swim. Instead of her bikini, she wore a fluffy terrycloth robe. "I feel like skinny-dipping, care to join me?"

"I, uh, er, um, I-I've never done that before."

"Chicken?"

"No, but, uh, er..."

"Afraid you might get aroused and embarrass yourself? Don't worry, I've seen men with a hard-on before. It's perfectly natural, especially in a young man like yourself." She really wanted to see him erect; she could tell from the bulge in his Speedos that he was well equipped.

She unbelted her robe and let it pool at her feet, her body glowing in the bright moonlight. It was the first nude woman he had ever seen; she was beautiful. Her full breasts stood high and firm on chest (with a little help from the scalpel). Her nether regions were bare, except for a little love triangle high on her mound.

Without another word, Peggy dove into the pool and started swimming toward the other end. When he was sure she couldn't see him, Rob quickly dropped his trunks and hit the water. His progress was slowed a bit, as his giant erection dragged in the water like a sea anchor.

He waited, staying underwater, until she climbed out of the pool, put on her robe, and went back into the house. When his penis finally went limp, he put on a robe and followed her into the house.

She was sitting, still in her robe, on the couch with her legs tucked under her. The lights were dimmed, there was some soft jazz playing on the stereo. There was a plate of brie and crackers and a bottle of wine with two glasses on the coffee table.

"Come, sit over here," Peggy said, patting the couch next to her. She poured two glasses of wine and handed him one. He had never had wine before. Taking a sip, he decided it was pretty good. He finished his glass and she poured him another. Then another. He felt all warm and fuzzy inside, and had a nice little buzz in his head.

They chatted for awhile, then Peggy said, "So, Rob, tell me about your love life. A good looking guy like you must be getting laid all the time."

"Well, actually, I don't have a love life." She was easy to talk to, and he was slightly snockered, so his tongue loosened and he decided to confess all. "I-I've never been laid before."

My God, a virgin, she thought, Oh, this is going to be even better. "So how far have you gone with a girl?"

"Well, I've felt a couple up, over their clothes, and I got a hand job." Then he told her about his disastrous experience with Sally. She tried really hard to suppress her laughter, but it was funny as hell. "I never saw a woman's boobs until yesterday. And I've never felt a bare one at all."

Peggy pulled the top of her robe open and thrust out her chest. "Here, you can feel mine." He hesitated, and she took his hands and placed them on her breasts. God, they felt sooo good. Soft but firm. He ran his hands over them, feeling all the contours, and when he skimmed over her nipples, he felt them stiffen and pooch out.

She tugged on the cord and stripped his robe off him. "You're hung just like your Uncle Jack," she said, running her fingers over his throbbing erection. He wondered how many sisters saw their brother with a hard-on? She dropped to her knees and took his cock in her mouth, licking and sucking with abandon.

He felt that tingle in his balls and, remembering what happened with Sally, tried to pull her head away. "I'm going to come, I'm going to come NOW." She just stroked him harder. He yelled out, and let himself go right into her mouth. She swallowed it all, then licked him clean.

Dropping her own robe, she stood naked before him. He was hard again in an instant. "Make love to me," she implored, lying back on the couch and spreading her legs for him. He climbed on top of her and shoved his cock between her legs. He poked and poked, unable to find her opening. Taking him in her hand, she guided him to the right place, and he entered her.

God, that was better than he ever imagined. All that hot, wet, liquid velvet surrounding him and drawing him in. He rose up and thrust into her. After about three strokes, he emptied himself again. He rolled off, humiliated. "Jeez, I'm so sorry, I didn't mean to pop off like that."

"Don't worry about it, baby, it happens to every young man. Before this summer's over, we'll make a real lover out of you." Then she gave him some exercise lessons, showing him how to squeeze his PC muscles to cut off his premature ejaculation. "Practice those for about a week and we'll try again." He practiced and practiced, jerking off and squeezing, until he could shut off coming at will.

This time, she led him straight into her bedroom, where she had lined the room with flickering candles. Soft music was playing in the background. She undressed him, then ran teasing fingers over his rock hard erection. Dropping her silk robe, she pulled him close and found his mouth with her own.

Tongue met tongue. Her breasts pressed into his chest, his cock ground into her stomach. Her lips danced across his, she nipped his lower lip with her teeth. Both of them abandoned themselves as raw passion overwhelmed them.

She laid down on the king-sized bed and pulled him down with her. "Now we're going to work on foreplay. You can start by fondling my breasts. Feel them, massage them gently, you're not kneading a loaf of bread."

He felt. Touched. Massaged. Sending waves of pleasure throughout her whole body. He felt himself start to erupt, squeezed himself off, his lips curving into a smile at his success.

"Now kiss them, all over." He kissed, then nibbled with his lips. "Use your tongue." Following her specific instructions, he laved her nipples with the soft, flat part of his tongue, then used the hard tip to trace circles around the hard, swollen tips.

"Suck them," she whispered, the words almost lost with the moan caught in her throat. He drew a nipple into his mouth and sucked, then, while in his mouth, flicked his tongue over the peaks. She fisted her hands in his hair, her body went rigid and trembled all over, as she came. "Oh God, that felt good." Rob looked like the cat who swallowed a canary, as he prided himself at producing his first female orgasm.

"Now I'll show you how to perform cunningulus."

"Cunningulus?"

"Eating pussy, as you probably call it."

"Okay, I guess," he said, his nervousness was obvious. He'd heard stories in the locker room. It smelled like a dead fish. Tasted awful. Could he really do it?

She pulled up her knees, spreading the wide apart. "First, a little anatomy lesson." He looked down at her fat, swollen outer lips. He took a deep breath as she spread them apart. He was entranced, then enchanted. So pink. So fragile. Like a beautiful pink rose. She explained all the parts to him, sliding her hood back so that her clit peeked out.

Like she told him, he kissed her inner thighs, across her mons. His lips caressed her puffy outer lips. Kissing. Licking. With his fingers, he spread her apart. She smelled sweet, like the strawberry douche she had washed herself out with, with just a hint of spicy musk. He licked the center of her rose, careful not to damage the petals, drawing each tender lip into his mouth and gently sucking.

His hands massaged her outer lips, opening and closing them, while his tongue sought her warm center. He dipped deep into her vagina, swirling his tongue around the walls, and then up until her found her engorged clit that had come out from its hiding place to greet his hungry mouth. She tasted as good, as exotic, as she smelled.

Kissing. Licking. Sucking. Her hips rose and bucked in tempo with his hungry mouth. She fisted the sheet, then screamed out his name as her whole body shuddered when she came, flooding his mouth with her juices.

"Fuck me, Rob, I want you inside me." This time he didn't stab and fumble. Rising above her, he watched as his cock slipped between her lips, then sank into her until he reached his full depth.

He rose and fell, rose and fell, completely in control, with no chance of coming before he wanted to. She tightened her cunt until she gripped him tightly with a velvet glove. She rose to meet his every thrust, wrapping her legs tightly around his waist. When he felt her quiver beneath him, he relaxed and let his orgasm come with hers.

In the next weeks, they did it in every conceivable way. Cowboy, reverse cowboy, doggy-style. In bed, on the couch, in the pool, on the dining room table, on the floor in the kitchen. He'd gained an amazing degree of self control. He could not only come when he wanted, he could go skinny-dipping without getting a hard-on.

One evening, during dinner, Peggy, with an amused look on her face, said, "Sheila wants you."

"Wants me for what?"

"She wants to fuck you." She could see his eyes narrow, and a Cheshire cat grin spread across his face. He could envision getting his hands on that magnificent rack.

Peggy was out for the evening. Rob and Sheila shared a bottle of wine. She licked her lips as she gazed at him, then asked him to dance to a Kenny G. CD that was playing on the stereo. She held him tight and he could smell her intoxicating perfume. She kissed him deeply, then reached down and fondled his cock. "Oo," she cooed, "a nice big one." Taking him by the hand, she led him to his bedroom.

She quickly stripped off her skirt and blouse, until she was standing there stark naked. Her large breasts stood straight out. After stripping off his clothes, she pushed him back on the bed, straddled him and sank down on his cock. No foreplay. She rode him. And rode him. He reached up and fondled her boobs; they were really hard and didn't move at all when she bounced up and down on him.

When they both came, she sucked him hard and climbed on again. And again. He didn't have to do anything except lie there and let her take her fill. After the third time, he fell asleep, drained. When he woke up in the morning, there were ten hundred dollar bills lying on his night stand.

Slightly disconcerted, he showed the money to Peggy. "What's this for?"

She laughed. "Don't worry about it, dear. She could have spent that much on dinner. Some of these women are loaded. And, by the way, your fame is spreading, Sheila's friend Donna is coming to see you tonight. She'll pay you the same amount."

"But doesn't that make me a prostitute or something?"

"That would be a gigolo, sweetie. Enjoy it while you can." After Donna, there was Angie, then Barb, Emily, and a dozen others whose name he couldn't even remember. Sarah and Ruth, the two small breasted women he met at the pool party, wanted a threesome, and paid him double. He answered an ad in the local paper and bought himself a spiffy mustang convertible.

Summer had ended. Rob and Peggy spent their last night together in bed, ravishing each other. She let out a contented sigh. "You're going to make some girl a wonderful lover. Got anyone special in mind?"

Rob just smiled. He'd been thinking about Susie all summer.