First Trick

Fiona was 18, it was the summer after she graduated from high school, and she felt on top of the world. She would start university the coming September, the first in her family to pursue a higher education.

She was a friendly, gregarious, cheerful young woman, a good head on her shoulders, confident, and lovely. She had long wavy brown hair down past her waist, brown eyes, weighed about 110 pounds, 5'7" in height. She didn't need or want to use much makeup, she was naturally pretty, and utterly lacked vanity about her appearance. One of her nicest features was her mouth, which was shapely and sensual, with fat moist lips that made every young guy around her yearn to kiss her.

But she was quite reserved about dating. She'd gone on a few friendly dates, mainly with shy young peers who worked up tremendous courage to ask her out. But it never went further than simple friendship, and physically never further than holding hands or a hug. She focussed mainly on her studies, and it had paid off.

But she and her family lived in a troubled neighbourhood. It was one of the poorest neighbourhoods in the country, lots of poverty, broken homes, quite a bit of crime. And a particularly concerning issue for her was the street prostitution which drew many of the young women of the community into its clutches.

Fiona made a point of befriending many different people, and one pattern she had was seeking out friends who might be a bit disadvantaged or needy, feeling that she liked to help them, to be an encouraging support.

She had known her best friends, Maggie and Trudy, for years, but she was very concerned about them this summer. They had dropped out of school, were getting involved in more and more partying, and most concerning of all, they both confided to Fiona that they had started working the street. Fiona tried to persuade them not to, but it was to no avail. The excitement and adventure of hooking had swept over Maggie and Trudy, and they were revelling in their perceived freedom, from all their earnings. They tried to reassure Fiona, telling her that it wasn't so bad, just an easy blow here, or a quick lay there, and they laughed about some of the johns they thought were pathetic, while saying that most of them were really nice guys.

Fiona was so worried about them that she decided to join them on the street, to keep a record of license numbers--just to protect their safety as much as she could.

She did this for a few weeks. Then Maggie persuaded her to join her for a trick in the car, just to sit in the back seat. Fiona felt her presence kept her friend safer. She did this for several weeks, and got a sense for the different types of guys who would cruise.

She was not a judgmental type, and actually felt sorry for the guys she saw picking up her friends. They were mainly lonely guys who had trouble meeting girls, or maybe frustrated middle-aged men with a burned-out sex life at home. But she would never consider prostitution herself.

Greg was instantly attracted to Fiona, seeing her standing on the street. He had seen prostitutes a few times in his life, and when feeling more lonely would occasionally cruise through the neighbourhood late at night. He usually never saw anyone who appealed to him much. But Fiona -- perfection! She seemed young, healthy, pure, with a nice personality, and had an exotic intelligent look.

He stopped to talk to Fiona and her 2 friends. "How much?" he said.

"50 for a blow, 100 for everything" Maggie said.

"What about your friend?"

"Same with Trudy", she said, gesturing towards the girl in the middle.

"No, I'm interested in your other friend"

"Oh, she doesn't work" both girls said right away.

"What's her name?"

They didn't want to say. Fiona stepped up and said "I'm Fiona. I'm sorry but I'm just spotting for my friends."

"I'll give you $1000 just to drive around a talk with you for an hour, Fiona."

"No" she said. "Good-bye" she continued firmly.

He drove away, disappointed.

The next few days Fiona thought a lot about what happened. She had decided long ago that she would not do things just to make money, she would pursue things she truly wanted, and to make a difference in the world. The guy in the car seemed friendly, but a bit sad. And the money would help, she would share it with her friends and family, maybe give some away to a local charity. And just for chatting!

Fiona secretly went out on the street on her own, looking for the guy who made her that offer. She didn't ordinarily adorn herself, but this time she put on a little bit of makeup, some bright red glossy lipstick (the only color she found in the local thrift store), and wore a simple red tee-shirt and a pair of snug shorts. She did have beautiful long legs, though she thought they were much too skinny. She wore some sandals that allowed you to see her feet and toes. The sandals had little silver ribbons on them, that looked very cute but also very cheap. They had in fact cost 50 cents at the thrift store. Most girls' feet are not that enticing to look at, but hers were perfect, soft, delicate, very clean, unblemished, and petite, with graceful perfect arches; she put some cute red nail polish on her toes, which was a nice touch. She had a habit of wiggling her toes a bit as she sat, especially if she was nervous or reflective, and it was very cute, almost intoxicating to watch. She wore a bit of perfume she sprayed on from a department store sampler earlier in the day.

She saw his car pull up in the distance just past 11 PM. She was on a side street, well away from where other girls worked. It was a new Toyota Camry, nicely washed, bright red. She stepped towards the curb and smiled at his car as it approached.

He slowed down, and pulled over, opening the passenger window.

"Hi Fiona" he said gently. "I've been thinking about you all week."

"Hi." She was having second thoughts.

"I have a thousand bucks on me right now, and it's yours if you just come talk with me for an hour."

He sounded so sweet. The money made her curious, but mainly she decided to get in just to talk to this guy, who seemed nice.

He reached over and opened the car door for her. He noticed the muscle tone in her skinny legs and calves as she stepped in. Like a ballerina.

They drove around for about an hour, in different neighbourhoods, having a friendly conversation. She felt quite at ease. He enjoyed looking at her beautiful face and hair, especially when she would have long, tender eye contact with him as she spoke. They stopped at a drive-in where he bought her a milkshake, and he enjoyed watching her fat sensual lips wrap around the straw, and her cheeks implode as she sucked sweet milky liquid into her belly. And he enjoyed looking at her bare thighs, which were as skinny as his ankles, so skinny that he imagined he could wrap his hands most of the way around them. He enjoyed looking at her feet, which were squirmy and tensing unconsciously, to his delight.

He paid her just before dropping her off. He decided to take a further chance--

"Fiona, I actually have ten thousand dollars cash with me now, and I have a deal for you if you're interested."

"What's the deal, Greg" she asked, using his name for the first time. It occurred to her that if she did have ten thousand dollars, it would take care of all her expenses next year, and allow her to study so much harder.

"It's midnight now, Fiona" he said. "If you agree to stay with me at my house until noon, and to do everything that I ask you to do inside my house, you'll get ten thousand dollars cash right now. I'll give you the whole amount in advance, and I'll trust you completely to keep your word of honour if you agree."

She knew it meant losing her virginity. And who knows what else. In a moment of decisiveness that was partly reckless, partly cautious, totally trusting, but made from a grounded, certain part of herself, Fiona said "Yes. You have my word of honour. I'll do anything you ask me to do until noon tomorrow. And you'll give me ten thousand dollars right now. It's a deal." One thing about Fiona -- her word meant everything. Once she had made a promise, there was virtually nothing that could make her break it.

Greg counted a thick wad of $100 bills, which he retrieved from a sack next to his seat, and gave them to Fiona, as he shook her hand. She put the money in her purse.

They drove a few miles away to a suburb where Greg lived in a modest bungalo. He helped her out of the car, and held her hand as he unlocked the front door of his house.

"My friends and I own this house" he said, "but they're down in the basement now. They're really nice guys."

He turned on the lights in the house and fetched Fiona a glass of water. She looked around curiously. Strangely enough, she wasn't very nervous, even though she had a pretty good idea in her mind about what she and Greg would be doing.

She slipped off her sandals. "Mind if I leave my sandals here?" she said, putting them next to the kitchen table.

"Of course, Fiona. You have such pretty feet."

They faced each other on the kitchen floor. She looked into his eyes, neither smiling nor frowning. She waited for him to decide what he wanted.

"Let's hug" he said. The two of them embraced on the kitchen floor. He gently felt the contours of her body as he hugged her, then he ran his fingers through her beautiful long brown hair. She had a little clip in her hair, and as she took it out, her hair descended down almost to her knees.

He moved to kiss her. She'd kissed a few guys before, only after going on little dates 3 or 4 times first. But she had never used her tongue when kissing. When Greg's tongue thrust into her mouth, she was startled, and said "Mmmphh" but he persisted, until she settled into the kiss, and returned his tongue thrusts with her own. Her lips were the sweetest, fullest, most sensual lips of any girl Greg had ever seen, either in person or in magazines. He licked and sucked on her lips, and she quickly caught on, using her beautiful mouth to massage his.

He pulled away. "It's time to get undressed now, Fiona." He was getting quite eager and already had his shirt off before he had finished the sentence. He tossed his shirt on the floor. Fiona just stood and watched.

"Take off your clothes" he told her more firmly, and she seemed to snap out of something. She hesitantly started pulling off her tee shirt. Then she took off her little shorts, folding them both neatly on the table.

"Everything" he said.

She blushed as she slowly undid her bra, exposing her 32A breasts. Then she took off her panties, and again set them both on the table neatly. She stood naked on the kitchen floor, her painted toes curling and flexing cutely. She felt much more self-conscious and embarrassed now.

Greg quickly undressed and threw his clothes on a heap next to him. He was 5'10", pale, lots of body hair, thin but flabby, with a bit of a gut hanging out. His 6" cock was stiffly erect, and he couldn't help rubbing it a bit as he admired this naked young goddess in front of him.

He grabbed her roughly and shoved his tongue down her throat as he squirmed his body against hers. His cock found its way between her legs, and it rubbed and poked against her, sometimes getting pretty close to her vagina. A drop or two of pre-cum already smeared against her little tufts of pubic hair, and she could feel the wetness. She was apprehensive but totally compliant, and because of his mouth over hers, her only sounds were muffled grunts.

He pulled her into his brightly-lit bedroom, which was very messy, and stank of dirty laundry. He pushed her backwards on the bed, and stood facing her. She looked a little frightened, but she remembered her commitment and was determined to comply with Greg's wishes until noon.

He rubbed his cock as he admired her from the foot of the bed. "Spread your legs" he said. She complied timidly. Her knees were bent, feet about a foot apart, and she let her knees spread apart, causing her pussy to be exposed for the first time. "Oh, baby" he muttered, rubbing his cock some more. He sat on the bed next to her, and started rubbing his hands over her body, starting with her feet, moving up her twiglike calves, which he could wrap his fingers around completely, up her thighs. One hand started fondling her pubic hair as the other rubbed her belly, then worked up to her breasts. Her breasts were exactly symmetrical, and the large nipples formed secondary cones that protruded substantially from the base.

She was expecting him to keep rubbing her body, but suddently he said "Oh, fuck" and climbed over her. He kissed her forcefully, in such a frenzy that drool dripped down her face as their tongues wrestled.

Without preparing her any further, he positioned his bare cock over her pussy, and after fumbling a bit it found its way to her vaginal opening.

She asked, in a sudden fright, "what about the condom"?

"For ten thousand bucks I want to fuck you without a condom" he said tersely. "I'll pull out".

She hadn't expected this. But once again she complied, remembering her promise. "Ok, but be careful" she said.

"I want you to beg me to fuck you" he said. She didn't quite understand. "Beg me" he said again.

She looked into his eyes. "Fuck me Greg" she said. with sudden boldness. "Please do it. Put your cock in me. Fuck me. Fuck me. Put it in. I don't want a condom. Fuck your bare cock into my cunt. I want you. Bust my cherry." She was getting into it. She saw how her words inflamed his lust.

"OK, Fiona. I'll fuck you". With that he lunged forward, and she gasped. His cock was lodged about half an inch inside her. He lunged again, there was a feeling of something giving way, and his cock sunk to the hilt into her body. She winced in pain, her torso writhed, and her legs went into a spasm, kicking at his legs a bit. She wrapped them around his legs, squirmed with them, trying to find a comfortable position with this new foreign object deep in her body. As her legs moved, her tight cunt rippled around Greg's cock. Finally her feet settled flat on the bed.

"Oh fuck, you are perfect." Greg started slow thrusts into Fiona. Blood from her hymen leaked down onto his bedsheets. She was his first virgin. After a minute, Greg started pounding into her with all his might, but slow, pausing for 5 or 10 seconds after each thrust, with his cock jarring her cervix as he went deep. These thrusts made Fiona cry out, or gasp. A tear trickled down her cheek, from the emotional intensity of the moment. He grabbed her skinny ankles, and pulled them forcefully up, pinning them next to her shoulders, causing his cock to sink even deeper, pushing her cervix so far that she gasped again loudly.

"Beg me to cum inside you" he said.

"Aren't you pulling out?" she asked in a fright.

"No way. I want to give you your first load of cum in your pussy. Beg me for it."

Again she had to rely on her pledge.

"Cum in my pussy" she said. "Blow your load in me", "I want my cunt full of Greg's semen".

With that Greg grunted loudly, and screamed out "FUCK!" as his body tensed up. His whole body focused its energy on pumping semen into Fiona's body. She felt the spray inside her, and each surge made her squirm and buck. After a minute, Greg collapsed on her, spent, and let go of her ankles. His weight on her made it hard for her to breathe. They rolled on their sides, his cock still inside her, and Greg fell asleep. About 10 minutes later she pulled herself off his cock, and felt the mixture of blood and cum leaking out of her. It still stung and ached, but she was relieved to be through her first time.

Greg had awakened when she pulled off, and sat up in the bed. "Thanks, Fiona, you were great. Now if you don't mind I want you to fuck my room-mates."

She was shocked. But she looked at the clock and saw that it was only 2:00 AM. She knew she had made a commitment.

3 other guys were waiting in the living room. They must have heard the action from their basement rooms. She heard Greg go to talk to them and say "Hey, guys, I've got a treat for you..."

All three guys were fat, about 40-50 years old, and covered with dense body hair. They were in the room in an instant, undressing. "Holy shit, Greg, you sure can pick 'em."

The first one plunged on top of Fiona, without a word of introduction, and just humped away for about 30 seconds before groaning and dumping a load of cum into her. He shuffled back into the living room, picking up his half-empty beer bottle on the way out.

The second one positioned his cock over Fiona's head, and stuffed it into her luscious mouth. "Suck and swallow" was all he said. His groin had quite a smell and Fiona had a hard time not gagging. She suckled his fat cock in her mouth for about a minute, before he suddenly shoved it down her throat, again making her almost gag. He did this several times, before pausing to groan, his chubby hands clutched around her head. He fired a massive load of cum into her mouth, and again she almost gagged. Cum leaked out of her mouth, dripping down her neck. He scooped it up with his finger, and popped it back in her mouth after pulling his cock out. "Let me see you swallow" he said. She opened her mouth to show him the load of sticky cum stretching from her tongue to palate, then closed and swallowed it all down. She opened up again to show him her empty mouth. As a finishing touch she sucked and licked a few more drops off his now softened penis. He couldn't help be impressed by this little gesture.

The third man said "I want something special." His cock glistened with some butter from the fridge that he'd smeared on it. Licking the remaining butter off his fingers, he flopped his fat bulk onto the bed, face up, and said, "get on." She climbed on top, both curious and repulsed by his morbidly obese hairy belly. She knew what to do, She started to position his cock into her cunt. But he blocked her hand, and directed his cock backwards an inch, pressing it against her anus.

Before she could react, he pulled her forcefully down, and she gasped loudly with his cock pushing deeply into her ass. She kept gasping afterwards, clearly having some trouble. Greg held her hand and comforted her. She eventually settled into this new posture, and discovered a unique pleasure. Both of them had a euphoric high, they gasped, they bucked, her muscles convulsed, her anus went into a tight spasm, and she ended up with the fat man's cock in her ass for about half an hour before he finally shot a big load into her bowels. Greg was a bit jealous. She actually had her first orgasm with another man, during this encounter. She drifted off into sleep side by side her last partner, the fat man's softening penis still lodged in her rectum. She liked the thought and feeling of her body accepting and embracing the cum from all these men; it gave her a sense of owning them in a way, and nurturing something warm and alive inside her body.

When she woke, it was exactly noon.

Fiona did not continue down the pathway to prostitution. In fact, she went on to become a very successful student, eventually a bold and confident lawyer for a successful firm. She dated regularly, and eventually married, happily. But she maintained a strange continued relationship with the 4 men she'd fucked that night. They had a special kind of friendship, and every few years they would re-enact the events of that evening, before enjoying an elegant brunch the following morning.