Charlie, William and Anna

I offered to write a story for a friend and she accepted. So this story is dedicated to Anna who was the inspiration for it. I'd also like to thank another friend whose advice has made other stories better than they would otherwise have been.

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This is the story of how two very different men, of different generations, are admirers of Anna and isn't what you might usually think of as romance. But romance comes in various kinds of flavours.

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Anna proceeded to choose the outfit for her next appointment. She had a new client arriving in less than an hour and wanted to look her best. Not that she didn't always look good but this was one of her special clients.

Exactly on time her door bell rang and she glided down the hallway to open her front door. A twenty two year old man, nervously shifting from foot to foot, faced her with an apprehensive expression. She recognised him from his photograph, had talked to him on the phone, but she still inspected him from head to toe. A pleasant face, hiding behind a pair of heavy framed glasses, neither handsome nor ugly, with an unruly mop of curly hair. Average height and what looked like a fit, young body disguised by cargo pants and a baggy jacket.

"Hello, Charlie. Come in."

She took him by the hand and led him down the hallway. It was his first visit to her. He was one of the many young men who entrusted her with the loss of their virginity.

"Please sit down, Charlie," she said, gesturing towards the couch. "Would you like something to drink? Tea? Coffee? A soft drink?"

"Could I have a glass of water, please? My mouth is really very dry."

She returned with the water and sat down next to him.

"A dry mouth? That's not unusual. I'd be surprised if you didn't have a dry mouth."

"It's just that I'm...it's just..."

"You're a little scared," she said, her voice edged with understanding. "Scared that you're going to make a fool of yourself." It was a statement not a question. Anna had seen this with many clients over the years, not just virgins.

He had one hand enclosing the other and she reached over, placing her hand over his, letting him feel her warmth and concern. Lifting his chin she looked him in the eye.

"You're not the first young man wanting to enjoy his first time with me. All I want is to have you leave happy after us having a good time together. We've talked on the phone, but do you have any more questions?"

Charlie shook his head. She stood, took him by the hand, and led him to the bedroom.

"First things first. Let's get you out of those clothes."

Slipping the jacket over his shoulders, she pulled the sleeves over his wrists, and without taking her eyes from his, tossed it onto a nearby chair. His polo shirt was next, pulling it up and over his head. It joined his jacket. The softness of her hands combined with the dryness of his skin as they swirled around his chest, gently rubbing his nipples. She bent and licked one making it wet, wrapped her lips around it, sucking gently, before repeating it with his other nipple. Holding him close, she ran her nails down his back, feeling him shiver with the sensation.

"Did you like that, Charlie?" She murmured in his ear.

"Umm...yes. You surprised me. It was...I'm not sure how to describe it," his mind struggling to understand the reaction of his body.

She sat him down on the edge of the bed and removed his pants. Just as easily slipping his shoes off his feet.

"I'd like you to lie on the bed, please, Charlie. Rest your head on the pillow."

She lay next to him. Caressing his arm, his back, his chest with her hand. He was falling further under her spell as she placed her hand on his cheek and kissed him. At first his mouth was hesitant but he quickly overcame his uncertainty and pressed hard against her.

"Whoa. Whoa, Charlie. Ease off. Don't push. Let our lips join softly. Let the pleasure come easily," she said, in a calm and friendly voice, kissing him again and receiving a much better response. All she wanted to do at this time was get him used to their lips meeting. Tongues would come later. She broke off the kiss and ran her hand through his hair.

"I wonder if you are curly somewhere else, don't tell me. Let me find out for myself," she laughed, putting a finger to his lips and laughing lightly.

He just smiled back at her. The more time passed, the more relaxed he became. Her hand slid down his body, feeling the bulge hidden by his undies.

"Well, that didn't need much searching for, Charlie. I think we can have some fun with what's inside there," she whispered in his ear as she massaged the bulge, feeling it grow in response to her touch.

"Lay still, Charlie, while I see what I can do with what's hidden inside there."

She moved down the bed, pushed his legs apart and rested on her elbow, brushing her hand over his bulge. She inserted two fingers in his waistband and pulled the material down, stretching the elastic and revealing his semi-erection.

"Lift your hips please, Charlie."

She eased his underwear further down, over his knees and feet, tossing it somewhere. Anywhere. Resting on her elbow again she bent, enclosing his tip with her lips, looking him in the eye, closing the distance between them, as he gazed back at her with an adoring smile. Finger and thumb around the base of his cock, wrapping her other fingers around his balls, she took the first two inches into her mouth, gripping him softly, letting him feel her tongue. He propped himself up on his elbows, wanting to get a better view of what she was doing.

"Lay back down," she laughed. "You'll get a perfectly good view laying on your back. Put another pillow under your head."

As the intensity of what she was doing increased, and her mouth swallowed more of him, he began to get the same feeling as when he masturbated. She was ready, having been in this position countless times, and quickly slid a condom over him. Seconds later he began to pulse and he erupted as on many occasions before but never like this. She continued to work him with her hand, her other hand fondling his balls, until he had given everything for her. Removing the condom she replaced it with her mouth, pleasing him as his erection wilted.

She straddled his chest, held him down by his hands, and kissed him with more fervour than before. More passion. She prised his lips apart with hers, slipped inside searching for his tongue, intertwining with him and letting him taste himself. Releasing his hands, she sat up, fondled his nipples, and gazed at a smile that looked as it would be there forever.

She inserted two fingers inside herself, removed them and slowly brought them to her mouth, sucking on them, savouring the taste.

"Where have my fingers been, Charlie?"

"Well...umm...inside your...inside your...vagina."

"Is that how you usually refer to it? When you're talking with your friends? What do you call it then?"

"We call it a...a cunt."

"Well, let's call it a cunt. It's my cunt. And we are both going to enjoy it. Would you like to fuck my cunt?"

"Yes. Please." There was no uncertainty or hesitation in his voice this time.

"We will, Charlie. But first things first. Fucking me is something to look forward to."

She removed her fingers, went to put them in her mouth, teasing him, and then offered them to him.

"Would you like to taste me?"

He nodded his head enthusiastically, opened his mouth, and lifted his head searching. She deliberately made him wait a few seconds before slipping her fingers between his lips, allowing him to eagerly suck her juices.

"Now relax. I want to show you how a woman pleases herself without a man."

She inserted two fingers back into her cunt, moving them forward and backward with a rythmn, imitating the action of the man as he thrusts into her. She stroked her clit with her thumb, the vibration coursing through her body. Reaching under the pillow, she pulled out a Magic Wand, switched it on, and used it to replace her thumb. Taking hold of his hand she wrapped his fingers around the wand.

"Hold it for me. Hold it tight against my clit. Keep it tight."

He did as he was told and watched as she began caressing her breast with her free hand, the invisible connection between her breasts and clit vibrating as she rubbed and squeezed her enlarged nipple. Her cheeks began to move in concert with the rest of her body, her legs clutching and squeezing his sides. He watched in amazement as her entire body shook and screams of delight came from her, her head thrown back as she was lost in the fever. Suddenly she ripped the wand from his fingers, threw it aside, and collapsed. Her head next to his, her elbows on the pillows as she sought to regain control. He lay there in amazement for a few seconds and then hesitantly wrapped his arms around her, enjoying the feeling as their bodies connected.

Eventually she pushed herself up and off his young body, her head beside his on the pillow.

"I see there's been another reaction to my orgasm," she said, a giggle escaping her mouth. She looked towards his cock and, following her gaze, he saw his engorged cock pointing skyward.

"I think someone looks as if he wants to get into the action," she giggled, unable to stop herself.

She reached down, encircled his manhood with her hand, gently masturbating him. Reaching over him she took a shiny packet from the bedside table. Moving down the bed, she took him in her mouth lubricating him ready for her fucking him. Ripping open the packet with her teeth, she covered him, straddling him, holding herself just above him. Reaching down, she placed him at her entrance and slowly slid all the way down, engulfing him completely.

"Lay still and let me give you what you came here for. I want to give you the memorable experience you deserve the first time your cock fucks a cunt."

She began riding him, keeping it slow because she knew that despite him already coming, with his youth it wouldn't take much for him to come again, and she wanted to prolong his pleasure as long as possible. They both smiled as they enjoyed the sensation, gazing at each other until his eyes closed, his shoulders stretched backwards as his chest lifted and his breathing increased. She increased her speed and he gripped the bedclothes, not wanting to release the feeling consuming his body.

As she gripped his cock and moved up and down, shoving his cock as far into her as possible and her cheeks slapping his balls, she used her hands to caress her breasts. He moaned as his climax grew closer, and realising the point of no return had arrived, she placed her hands on his chest for balance and drove him inside her fast and hard. His cock pulsed and she felt him shoot his offering inside her, his body lifting as he pushed upwards as she drove down. Finally his energy had all escaped and he lay still, the only movement being the pulsing of his cock, still gripped inside her, refusing to believe there was nothing left to give.

Eventually two words came from his mouth. "Thank you." A sense of urgency entered his voice. "I never imagined it would feel so good. The feeling was fantastic. I want more. I want to do it again."

"Unfortunately we have run out of time, Charlie. I have another client booked in and arriving shortly. That's the problem of being busy," she smiled with mock modesty, "and I need to get ready for him as I got ready for you."

She led him to the guest bedroom to shower, waited until he was finished and dressed, then walked him to the front door.

"When can I see you again?"

"Anytime you wish, Charlie. Call me, text me, or email, whichever you prefer, and we'll arrange a time."

She held the door open, gave him a peck on the cheek, and as soon as he was over the threshold she closed the door. She would have liked to spend a few minutes discussing the session but they had gone well past his hour. She needed to get ready as quickly as possible because it was very close to her next appointment. With William.

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Anna was the only 'lady of ill repute' that William saw nowadays and their meetings were more infrequent than they used to be and more infrequent than he wanted. Nothing could be done to change that but, if anything, the eagerness and anticipation only made the thrill of seeing her more exciting and enjoyable. He had visited other ladies, both before and after his initial meetings with Anna, but had become disillusioned with their indifferent and bored attitude towards sex. Their only interest being getting as much money as possible for the poor service they provided.

Anna was different. She made him feel as if he was the only man in the world she was interested in. At least for the time they spent together. It didn't matter if it was true or false. He was happy and would settle for an hour of bliss with her anytime. The money was unimportant. He also realised any man, when they were with Anna, would feel they were the most important person in her life at that moment. It was nothing to do with what she did for a living, she was just that type of person. He hadn't seen anyone else for several years and he didn't want to. She notified him when she was going to be in his area, giving him sufficient time to make arrangements, so he had a bullet proof alibi ready. Occasionally, he was able to visit her at her home and today was one of those occasions.

"I've really missed seeing you," he said as he sat on the edge of the chair, removing his shoes and socks.

"Aww, thank you, William. That's very nice of you to say. I've missed seeing you. My regular clients always seem more like friends than clients. Even though it's a business deal doesn't mean you have to be strangers that pass in the night. Although many times that's the way it is and has got to be."

He gazed up at her, seeing a woman who looked, and dressed, like the attractive neighbour all the men in the street wanted to fuck. Particularly when, as now, she was wearing leopard skin stilettos with spiked five inch heels. The attractive lady who would be friendly with her female neighbours even though they knew what their husbands were thinking. Possibly a few of those women would be thinking the same, particularly if they knew she was bi-sexual.

He unbuttoned his shirt, removed the rest of his clothing, and stood feeling the fabric of her dress against his skin.

"I'm aware you're glad to see me," she said, taking hold of him and leading him to the bed. She sat next to him, their bodies touching, sensual even though separated by the fabric, and leaned in to give him a tender kiss that quickly became much more. Their tongues entwined, frantically making up for lost time, clasped in each other's arms, desperate to make love. They collapsed on the bed, her hand on his head, holding him to her, while he pulled up her dress, feeling for her sex.

"Let me get this dress off," she said, standing and turning so he could lower the zipper. She looked like every man's dream in her fuck-me shoes, black fully fashioned nylons with matching suspenders, burgundy panties and a matching bra that was struggling to contain her beautiful, soft and natural breasts. The dark red of her talons, glistening with sparkle, perfectly complemented her lingerie.

He pressed his nose to her neck, inhaling her scent and running his hands over her nylons, feeling the softness of her ass cheeks as his finger sought her sex.

"I want to taste you," said Anna. "Move up the bed, lie back, and let me get to work."

The warmth of her mouth felt so good as she began sucking and caressing it with her tongue, making him desperate for her to swallow him. She opened her lips and slid a couple of inches of him in her mouth, making his nerves tingle. She gradually moved further down until she had consumed almost all of him, and began to work in earnest, gently grazing him with her teeth as she increased the pace.

He began to thrust upwards into her mouth, wanting the feeling to stay, to become more. She held him down, remaining in control, taking him to the brink and then holding him back. Finally relenting, she slipped a condom on with expert hands and within seconds was astride him. He was up to his depth inside her. She squeezed him with her muscles at the same time as gently rocking back and forth. He relaxed, closed his eyes, enjoying the pleasure for which he had been waiting for months. The smooth warmth of her skin, even through the condom, was intoxicating.

He had a glove fetish. She knew that and knew he had been waiting. Underneath the pillow she had hidden silken opera gloves and, unseen by him, slid each of them over her hands, squeezing into the fingers, and pulling them up and over her elbows. The first he knew of it was when she touched his face. His eyes flew open and a smile appeared. Not a word was spoken. He took both her hands in his own, kissing the palm of each, and then letting his skin feel their texture again.

She slid her hands onto his neck, down his chest, coming to rest on his nipples. Twiddling his nipples between her fingers and then suddenly twisting them. Not enough to really hurt but enough to make him jump. She knew he enjoyed having his nipples squeezed and twisted, and could stand a lot more pain, but that wasn't her intent. The grin on his face told her everything she wanted to know and she desperately tried, and failed, to hold back her giggling. He joined her and it sounded like two young children caught doing something naughty.

Still keeping him inside her she rotated around him, leaning back with her hands on his thighs tantalisingly making him stretch to fondle her breasts. She moved forward without releasing him, taking his hands in her own and held them on the pillow above his head. Lowering herself towards him, lips ready to join with his own, she stopped just out of reach. He tried raising his head, seeking her lips but being held down could do little. She slid her tongue along his lips, before engulfing them with her own, pushing into his mouth for their tongues to join.

"I want to 69, please," he said. The first words spoken for several minutes because no words were necessary. Removing the condom, she settled her pussy close to his mouth and once again swallowed him. He reached under her legs, taking each cheek in his hands, pulling her down towards his mouth, delicately penetrating her folds. Anna was very sensitive in that area and it wasn't long before she began to respond. He could tell she had no intention of letting him come, she was going to keep him on the edge, and he was determined to do the same. Time seemed to slow as they pleased each other, feeling the warmth of one body spreading to the other.

Eventually she said, "I'm doing all the work here, you lazy devil. You're just laying on your back enjoying yourself."

"Behave yourself," said William. "You're enjoying yourself as well. Don't try and kid me."

In that instant it wasn't an escort and client having sex, it was two friends being intimate with each other.

"Come lie with me, please," he said, "I want to hold you in my arms for a while."

She removed her opera gloves and selected a pair in red leather that came just above her wrists.

"I bought these yesterday. You can break them in for me."

He took hold of her wrist and, with his other hand, felt the texture of the soft leather. Caressing her fingers and smoothing the leather on the back of her hand and palm.

"I think you made a good choice. They're having a pleasurable effect on me. That's for sure."

They lay, his arm around her shoulder, his hand stroking her silky blonde hair. Her arm was on his chest, her hand stroking his naturally hairless skin, before wandering lower to fondle him and bring him back to life.

"I think it's time I gave these the attention they deserve," he said, his free arm gently feeling her breast. "My lips have waited long enough."