Arrow of Cupid

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Patti loses her anal virginity to a caring man.
5.7k words
4.62
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25

Part 1 of the 2 part series

Updated 10/17/2022
Created 08/30/2004
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Enzian
Enzian
11 Followers

He rose from his bed and stood in the dark, leaving her asleep in his bed. He looked out his bedroom window onto the street in a reverie of contentment, contemplating the events of the day. He remembered her kisses, remembered him inside her mouth. He remembered the sweetness of her pussy, remembered as she let him take her anal virginity earlier in the afternoon, her fear, her tears and her joy. Standing over her sleeping form, her hair falling across her peaceful face, he leaned and kissed her forehead

________

A month ago, he found her in the park on a Saturday afternoon. She sat on a park bench, in the shade, reading Thomas Pynchon's "V." She looked up at him and smiled. He stopped his bike and took off his glasses.

"I just got finished with Gravity's Rainbow," he said.

"I think I've read all of Pynchon's novels," she replied.

"Did you see the Simpsons episode where Pynchon was teaching Marge to write?"

"Heh. The Harpooned Heart."

"Too funny! ... y'know, I don't usually try to pick up beautiful women in the park, but in your case, I'll make an exception."

They walked across Clark Street, up Lincoln, to Ranalli's. He had a weissbier. She had a salad and ice tea. The August sun beat down on the bustling patio, the kids on rollerblades swished by on the sidewalk, the sounds of the city wrapped around them. A wind blew in off the lake, stirring her skirt around her calves, fluttering the napkins off the table. She leaned over to pick one up, and he saw down her blouse, two pretty little breasts in a pale blue brassiere. She sternly looked up at him, as he rolled his eyes skyward, putting his hands up like Sgt Schultz, "I see no-thing! NO-THINK!"

She laughed in spite of herself. He was charming, intelligent and funny, there has to be something wrong with this guy, she wondered how long it would take her to find out. But for now, in this moment, he was perfect company, a delight. What would he be like in bed? Stop thinking this way. He's just some cute guy on a bike.

They talked about books, and music, a little politics, where they had grown up. She was from Winnetka. He was from coastal Maine. Both had gone to business school, he to University of Chicago, she went to DePaul.

She kissed him when he got back on his bike.

___________

He sent her email.

She sent him voice mail at work.

He sent her flowers.

They talked, and talked, and talked.

They drank coffee all night, and walked along North Avenue Beach.

They went to hear jazz at Joe Segal's Jazz Showcase.

They sneaked kisses in the Lincoln Park Zoo, in front of the zebras.

They fell in love.

__________

They met again at Nookies' Restaurant for Sunday brunch. She wore shorts and a short-sleeved blouse. He wore faded black jeans and a Neil Gaiman Sandman t-shirt. Coffee, a big glass of juice and spinach omelettes, then the reading of the papers, her New York Times, his Chicago Tribune. After he paid the bill, they walked through Old Town, down by the Buddhist temple.

She kissed him again by the chessboards. Suspended in time, she felt a flush of desire, a knot unkinking in her chest, a pang of love strike her. Cupid, the mad god, is not some smiling infant putto from a Valentine's Day card, to fall in love is to be shot through, painfully staggering, dumbstruck. She put her head on his chest and held him, as he stroked her hair, lifted her face to his and kissed her gently on the forehead, on the nose, on the mouth, she opened her mouth to him, their tongues met, tenuous, nervous. Her pussy bloomed, her hands clenched, she stirred.

She is Patti. With an i. She is the sort of nice girl who grew up with her face in a book. Listened to the art-rock bands and Prince while her friends were listening to B96 and the bubble gum boy bands. Couldn't stand the boys in her high school, had a brief fling with a boy in college. When she realized he would never be a good match, she cheerfully dumped him. In B school, she'd met a guy who had really turned her on, but he couldn't make her happy. And dumped him too.

He is Jamie. A good boy, his mother's pride and joy. Bridgton, Maine, on the Atlantic coast, is tough country, and produces tough people, but Jamie was elegant. Every girl liked him, his long eyelashes and perfect mouth, his stringy body in running shorts, his way with words, the strange poems he wrote. His oil paintings he framed in woodshop. His teachers liked him, his odd precise vocabulary.

In short, had he tried to be popular, he could have. Instead, he studied, he ran, he wrote, and he went away to college, far from Bridgton, Maine. A few of the braver girls in high school had taken him in the woods and sucked his cock. Amanda from college had tearfully let him lay her down and fuck her, and she eventually grew to like it, but the relationship did not grow. Four years in the Army, a few nights with bar frauleins and Japanese yoruno-onna hardly counted, he could barely remember their names. He met a few girls in business school getting his MBA, but nothing clicked. Everyone was too busy, or the chemistry wasn't right.

All afternoon, they walked, her hand in his, finally back to his apartment in Old Town. They walked up the two flights of stairs. He fumbled for his keys and opened the door. His cat came out to greet them, a bread colored tomcat. He picked the purring cat up, and scratched his ear.

"Meet Dmitri.," he said. The cat purred. She gingerly petted him.

"Hey, how ya doin', big guy?," she asked. The cat looked at her with imperturbable green eyes, still purring.

She came in, a bit hesitantly, her arms behind her back. Bookshelves lined the walls.

Hanging over a long couch was a painting of a girl dressed in blue, walking on the sea, a cello floating submerged in the water, its bridge above the water, the f holes wriggling below the surface of the water, the girl's face dreamlike, her arms held before her. His computer sat on a flat door in the hallway, a laptop, a hub sprouting a host of USB cables, a sheaf of photographs stacked beside a scanner, his cell phone charging on top of the monitor, a coffee cup beside a graphics tablet. High above, hung from the ceiling, a Chinese lantern lamp with its panes of painted glass and tassels. A good Isfahan carpet in the main room, four Victorian chairs around a circular table, a Victorian armchair, with padded arms, stood in the corner.

"Wow, these are really fine antiques, Jamie."

"Lots of estate sales." he said, opening a bottle of cold pinot grigiot. "Drink wine?"

"Only white"

"What luck. Try this stuff. PG is good for the soul, they say."

She looked around his bookshelves, as he ejected a CD from his changer, and put in Bill Evans Trio, and hit randomize. He pressed play. The room came to life.

"Gloria's Step" she said.

"When I hear this, " he said, "I always see a pretty woman in a good dress, walking rapidly down the street, in a set of good shoes, not high heels. You know, a lot of guys think high heels are sexy, but I can't stand high heels on women. A sadistic orthopedic surgeon must have invented them to induce ankle fractures in rich women."

She laughed. "My worst ankle sprain I was in a pair of my Mom's high heels. Wore them out on the sidewalk, and tripped up. I came in the house, crying, and my Mom was mad at me for breaking the heel."

They sat at his table for a moment. "If I could return to any point in time, I'd go back to Greenwich Village on a hot June evening in 1961, order a glass of wine at the Village Vanguard, and hear Bill Evans and Paul Motian and Scott LaFaro play this live. Scott died in a car accident, not long after this was recorded. Bill Evans never really got over it, and didn't play for almost a year. He grieved for Scott for years. Bill Evans. Heroin's first poster boy."

The song changed.

"This is Jade Dream. Scott LaFaro's tune. Always wonder what could have happened if he'd lived." He sat pensively, his hands together like a Hindu greeting, his elbows on the tabletop. "Makes you wonder. Life is so strange."

She pulled his hands down and kissed his palms. He kissed the top of her head, the smell of her shampoo, the texture of her combed brunette hair, the heat of her hands on his wrists as she held them, the feel of her lips and teeth as she leaned over his hands.

He took her face in his hands, and lifted her to his mouth. He held the back of her head as he kissed her gently, then more forcefully, pulling her to him, her breasts against him, his arm around her waist like a dancer. She sobbed and looked away.

"This is too perfect. Something's got to be wrong with you Jamie. I think I love you. I can't help myself."

And kissed him again, fiercely, pulling herself up to the tips of her toes. He softly bit her ear, her neck, the skin of her shoulder, the hollow of her neck, the upper curve of her breasts.

"Can I undress you?" he asked.

She nodded, dumbly, kicking off her shoes.

He unbuttoned her blouse, kissing her nipples inside her bra, her stomach, her pubis bone, he unbuttoned her shorts, she wriggled out of them, leaving her shuddering in her underwear.

He stood behind her, pulling her back to his chest, put his fingers between her legs, delicate fingers, probing fingers, touching her breasts, leaning her ass into the curve of his body, the crack of her ass felt the bulge of his penis through his pants, her panties sodden, he leaned her forward, putting his third finger into her vagina and touched her clitoris with his heel of his thumb. She pushed back against him, her head against his neck, in bliss. He whispered in her ear, "Oh, what a pretty body she has" and her mouth opened in a shattering orgasm, she leaned forward and staggered, whimpering, as his fingers played her like a classical guitarist's rigid curved fingers, walking her forward a few steps as she came, his middle finger hooked into her, lifting her by her pelvis as she came. She wriggled away from his hooked grip, lay down on the couch, her face red and sweating, her mouth opening and closing as she regained her breath. He brought her glass of wine, she drank half of it in three gulps, thirstily, greedily. She wiped her forehead with her forearm, and grinned unsteadily.

She undressed him, pulling his t-shirt up over his head, sucking his nipples, pulling at his belt, pulling it out like a snake. Unbuttoning his jeans, pulling his pants down around his hips, she kissed his penis and licked it delicately, smelling it, holding his balls in her hand. She sat him down in the armchair, pulled off his shoes and pants, and knelt before him.

Gingerly holding his penis in her hands, mysterious thing, touching it gently, smelling his odor, feeling its length, kissing the tip, her small mouth wrapped around his cock, her hands feeling his ass.

Softly licking his frenulum, his hands like rough combs in her hair, tracing her ears, her breasts against his thighs, the warm breath from her nose blowing over his pubic hair. His hips began to move, his ass clenching, as he pushed gently into her mouth.

He came, a rush of bitter semen into her mouth, pumping hot from inside him, his body heaving, juddering, as her lips pursed around his member, her fingers toying with his balls. She swallowed, and licked him.

"Aaagh! Oh, stop, it's so sensitive. Oh, please, Patti." She looked up at him and grinned.

"Serves you right. Making me stand up and walk while I cum, hanging on your fingers. God. It's so kinky."

He went in the bathroom, and turned on the shower. He came out with a fluffy towel, and a bar of soap.

"Wanna wash your pretty body?"

"Only if you get in there with me."

He soaped her body, starting with her neck and back, her breasts, her arms and legs. He washed between her legs. Standing behind her, he put his cock lengthwise between her buttocks, pressing up to her back, sliding up and down the soapy slick cleft, pulling at her nipples as he soaped her. Washing away the soap with the shower head, playing between her pussy lips, almost ticklish, his gentle hands, washing her armpits, she felt exquisitely vulnerable, almost a child.

He knelt down before her in the shower, and put his hands between her thighs, pressing them apart, opening her pussy to him. He inserted the point of his tongue into the Y, touching her clitoris, then spreading her wider, his tongue spread her labia, she felt dizzy as his fingers reached behind her and spread her buttocks, putting his index finger on her anus, delicately touching it. So nasty and clever, touching her ass. She shuddered and came again, sobbing in the shower, her back arched, her face to the ceiling, holding onto the shower rail for dear life.

He got out of the shower, dried himself off, and put on a bathrobe. While she dried herself off, he rummaged around in his closet, and came out with a long Japanese wrap-around robe. He put it around her shoulders, as she combed her hair with his brush.

"Mmmm. So nice. Is it silk?"

"It's a yukata. Pongee. Ki Tsumugi."

"I guess that means it's silk"

"Yeah." He rubbed his hand down the small of her back, over her butt. "Does great things for your ass."

"You like my ass, don't you?"

"It's mighty fine, Patti."

"I noticed you keep feeling at it. Pervert."

"Now, how can I not like your ass? It's just my kind of ass."

"Ooh. Thanks. I think."

"I have plans for your ass."

"No you don't. It's dirty. It has to hurt. One girlfriend of mine told me it almost killed her."

"Nah. Not the way I do it."

"Really?"

"Yeah. " He combed his hair, standing behind her. "The secret is to let the girl run the show. I'm not into pain, giving or getting it. You say stop, I stop."

"Would you, like, really fuck me?"

"Differently. It's not like the porn movies. They don't show you how to get ready. Most of the thrill is just getting you to let me, and your reactions, and how you feel about it. Remember, you're in control. You have to talk to me."

"I've always wondered what it's like."

"You want to do this? Let me do you in the ass? I'm not pressuring you to do this. It's a big step, and you may not like this at all."

"I'd like to try, with you, Jamie. You know how to please me. And you're so gentle. Nobody ever touched me like you do, before. You've got kind hands. You make me want to do new things. Pervert."

She hit him in the butt with her hairbrush. Laughting, she ran into his bedroom and crouched down behind the bed. He came in, pretended not to know where she was. He got down on the carpet and low-crawled around the corner of the bed. There she was, her butt to his face. He reached out one finger, and poked her ass with his finger, the silk jammed between her buttocks. She shrieked, grabbed her ass and stood up. He backed up, but before he could get to his feet, she had jumped on him, her legs across his waist, trying to pin him down. He rolled over, tipping her on her side, grabbed her and kissed her forehead. She wriggled a bit, trying to get away, but he kissed her mouth, and she moaned, putting her left leg over his body, turning him on his back, crouching over him. Flipping her yukata back, exposing her pussy, she rose on her knees, held his penis, and lowered her pussy onto his thick cock, groaning with pleasure as it rose into her body. Throwing her hair back, she rose on her knees, slowly lifting her body off his cock, sliding back down, the delicious friction, the feeling of her labia crushing down onto his pelvis. He reached up and cupped her breasts, his thumbs and forefingers rolling her nipples back and forth. She ground her pussy on his pubic hair, leaning forward, her elbows on the carpet, kissing him, her tongue in his mouth. He reached up behind her, with both his hands, and delicately touched her tight asshole. She groaned into his mouth, pushing her butt back onto his finger. He held one cheek in each hand, raising and lowering her onto his pole.

"You're the best, Patti " he whispered in her ear. "I love the feel of you, the taste of you, the way you laugh. Everything about you. Don't you ever go away. You're my girl, Patti."

Her mind and pussy opened to him like morning glories turn toward the sun. She could feel the petals opening, the giddy sense of unalloyed happiness, the first morning of summer vacation. The arrows of the mad god, piercing her heart, piercing up into her pussy, piercing her ass. She would do this for him, she would let him open her ass and love her there. She would. She wanted to. She wanted to feel him, to please him, to be his girl. He said so, didn't he? Oh. There's got to be something wrong with him. Maybe assfucking is what's wrong with him. He might be mean. He might hurt me. No he's not going to hurt me. He's perfect. He drives me crazy. He makes me come standing up. I can't stand it. I haven't had this many orgasms with a man in my life.

And she came again, crouched over him, her hair hanging in his face.

She rolled off of him, her neck cramping from her orgasm, her pussy raw from her wild ride, her arms splayed out on the carpet, sweating, twitching, her legs open to the cool air. He turned his head to look at her. She looked at the ceiling, her chest heaving.

"You were fucking tremendous, Jamie."

"Glad to be of service, madam."

"You didn't come"

"My refractory period is long."

"Refractory?"

"It takes me a long time to come twice, half an hour minimum. Some men are like that."

"Oh. Still want to do my butt, you pervert?"

"Pervert Jamie. Comin' up behind you."

"What a terrible pun."

"O-pun your ass, darling."

"Terrible."

"You know you want it. Bad girls always do."

"I'm not a bad girl. They just draw me that way."

"Jessica Rabbit. What she ever saw in Roger Rabbit I'll never know."

"Maybe they fucked like bunnies."

"Yeah right. I'll bet she was playing pat-a-cake with Popeye the Sailor. Or maybe with Dick Tracy."

"Heh, heh, heh... he said Dick."

"Beavis and Butthead. Some intellectual you are."

"Tell me about it, Mister Roger Rabbit pat-a-cake."

He stood her up, and kissed her. He wrapped her in the yukata again, and put on his bathrobe. She came into the bathroom with him, as he opened up the medicine chest.

"What's in there, lover boy?"

"Almond oil, if you must know, Miss Curious About What's In People's Medicine Chest."

"And what do you intend to do with almond oil, Mister Pervert?"

"I intend to lovingly sodomize you, and introduce you to the joys of butt sex, my darling Patti. Nya-hah-hah!"

"You terrify me, sir. What if your schwantz does not fit into my tuchus?"

"How will you ever know, if you do not try? They say every woman has anal sex twice, the second time to see if it was as bad as she remembered it."

"Very funny, Mister. Keep on going like this, and see if I'll bend over for you at all."

"But, darling, consider the joys of depravity, the sheer naughtiness of being gently sodomized by the man you love, your beautiful asshole wrapped around my cock, giving me all of your pretty body, oh the sordid pleasure of butt sex alone will bring you back again and again to this den of iniquity and into my perverted arms."

"You're so bad. What do you want me to do?"

"Take the pillows off the bed, and put one on the armchair."

"Kneel on it. Put this pillow under your head. Are you comfortable?"

She put one knee on the chair, then the other, opening them, the air cooled her pussy. Nervously, she accepted the second pillow, and laid her head down on the top of the armchair, her breath trembling as when she was just a teenager being fucked for the first time. He lifted his yukata over her hips, over her bottom, her knees apart, the air conditioning making her a little cold, and feeling terribly exposed.

He put a very small quantity of almond oil in his hand, and smoothed it over her ass, her thighs, her waist, down toward her bush, between her legs, rubbing it into the skin, like lotion.

Enzian
Enzian
11 Followers
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