From Fantasy to Flesh

Finally, he pulled back on her collar making her sit up on her knees, breasts high, back arched. Will stood over her still dressed in his nice suit except for the cock he stroked into her face.

"Princess, I'm going to cum. Do you want it?"

"Yes!"

"Yes what?" Tightening the belt.

"Yes sir! Please!"

With a grunt and a growl, Will shoved his cock back into Sydney's mouth filling it with an eruption of cum. Sydney, like the good girl she was, swallowed every delicious drop. He moaned her name, called her a beautiful princess and worthless cunt, said she was an angel sent from heaven and a slut fit for nothing but sucking his cock and it made her ache with need. She felt the belt loosen and looked up at his smiling face. He reached down pulling her up into his lap as his sat on the couch. He kissed her, tasting himself and felt her arousal.

"Syd, babe, that was amazing." He kissed her nose. "It was better than any chat." He kissed her forehead. "It was better than anything I've ever imagined." He kissed her neck down her chest, giving each hard nipple a lick. "Now will you do me a favor?"

Sydney looked at him, eyebrow arched, thinking she had just done him one hell of a favor. "What's that?"

Will pulled her close against his chest and as he talked, she could hear his voice rumbling in his chest. "I want you to go get on my bed. One, I just want to finally see you there. Two, I want you to show me how wet you are right now. I want to watch you, Syd, as I get undressed."

Sydney knew what he wanted. They had talked about it many times. But the thought of doing something so private, openly, while being watched, made her blush. He kissed the top of her head waiting for her to decide this time. No belts, no collars. Her choice.

After a long moment, she slid out of his lap. She was warm, but could see snow floating down through his apartment window. It was lovely. Without looking down at him, she turned and padded towards his bedroom. She heard him get up and follow her wordlessly. Turning and sitting on the edge of his bed, looking down at her hands in her bare lap, Syd took a deep breath and spread her legs wide.

He was standing across the room, eyes on her, unbuttoning his shirt slowly. In no hurry. Syd picked up her feet and tilted her pelvis, giving him a full view of her bare pussy sprinkled with freckles. Running her fingers lightly up and down her slit, she realized how incredibly wet she was. Her fingers were quickly coated in her juices, and his cum from earlier in the alleyway, as she circled the hard, little nubbin of her clit, sending shock waves up her spine. Will's shirt fell to the floor. Sydney looked up through her dark lashes at him and began slowly pushing a finger deep inside her aching cunt. Will kicked his pants and shoes off just watching her.

Biting her lip, closing her eyes, getting lost, Sydney touched herself the way she had so many time while thinking of Will. She never heard him approach but suddenly, she felt another finger join hers. She slowly opened her eyes to see Will kneeling between her legs, his fingers joining hers as they stroked and circled. Will watched her hands, copying her touches, learning what she liked. Then leaning forward, he kissed the top of her cleft and pushed her shoulders back on the bed.

Sydney laid back and shivered as his tongue and fingers explored her. His mouth was slow and methodical, and all too soon, she felt that pressure building. Arching her hips, she ran her fingers down her stomach to tangle in his hair, pulling his face into her. Fucking his mouth now. A mixture of unintelligible words and whimpers flooded out of her mouth announcing her orgasm. Right at the moment of her pleasure though, his mouth disappeared making her eyes flutter open. Without missing more than a beat, Will was standing up between her knees, positioning his cock at her entrance.

"Cum for me, Sydney." And he slammed home inside her. It was the sound of her name from his mouth that sent her over the edge into ecstasy. Her whole body constricted and her pussy clamped around his cock. He leaned over her, just holding himself inside her spasming cunt, riding the wave of her orgasm.

"Yes, yes...good girl. That's my princess." He cooed into her squeals but as her convulsions subsided, his voiced deepened into a growl. Running his hands up her legs, he pushed her knees to her chest, folding her in half, then using her shoulders for leverage, he began to fuck her with a savagery that revealed the depth of his lust. Still foggy from the earth shattering orgasm, Sydney just watched him in admiration and amazement as he pulled out and then rammed inside her again. Using her body for his pleasure only. Her whole body shook with his thrust, the headboard clattered, and with final thrust and a roar "Fuck!" he came.

Lowering his body to her, letting her wrap her legs in his, he nuzzled her neck, kissing each freckle on her chest. They laid like that for a long time, still connected, blissfully nodding in and out of satisfied sleep.

Sydney loved Chicago.

There's something about getting to know someone online, and often knowing them in a much more intimate way than people in their daily lives do, that creates a new reality. A tiny universe where only the two of you exist in your most perfect, most poignant, most hyper sexualized forms. Sure, I may not know that you hate onions, but I know you like it when I graze my teeth over the hollow in your neck. You don't know my mother's name but you know how sensitive my nipples are and that I love to hear your ragged breath in my ear. Together, we create a magical, fantasy land of caresses and pet names and boundary pushing that probably couldn't be sustained in real life. Probably. And when we turn on our PCs, open our laptops or swipe our cell phones it is in fact the same thing as teleporting to a land only you and I have access to enter. The real world of meetings, classes, families, and responsibilities fade and we arrive ideal and perfect in each other's arms.

I always liked the fantasy world. Preferred it. I liked the distance, the ability to turn off when it was too much. So much easier than a real relationship. I wasn't jealous of his real-life lovers. I had no right to be. I had them too. But there is nothing as startling as into a restaurant and looking up to see a face you'd only seen in pictures, seeing a man to whom you'd told countless secrets and who'd with just typed words had pulled from you countless toe-curling orgasms, and seeing that same man laughing with some other girl? It's jolting. You feel a pain you don't deserve to have and a shallow envy the screeches in your mind like a fingernail on a chalkboard.

* * * * *

Sydney strolled through the city streets marveling the tall buildings and the bustling crowds and she loved it in the way only small-town girls can truly love a big city. Her first city, so many firsts this week! Her first big city, her first trip alone, her first flight, her first time meeting a man she'd met online. It was all very exciting and extremely terrifying. Sydney was so glad she'd gone with her gut and came a day earlier than she had told Will just so she could have these moments to herself. She wanted time to calm her nerves and collect herself, time to explore the city and feel herself grow into the woman she was destined to become.

When she had first started chatting with Will, she was a girl pretending to be a woman, a freshman in college who simply had a way with words. He'd complimented her in the most perfect ways and very quickly their chats had become daily and addictive. For months, they had chatted from the most mundane of things (tacos, movies, books) to the most erotic (he wanted to spank her, she wanted to swallow his cum) until finally they had to be together in the flesh. The time worked out perfectly, he was still on vacation the week after Christmas and would be home until New Years and she didn't have to be back at school until the first of the year. She booked a flight, spent her entire savings, lied to her parents and friends and one December day she flew away from sunny Florida and landed in icy Chicago. She had no idea what to expect but she had not expected her life to completely change.

That first night alone, Sydney dressed up in short eggplant colored dress with long sleeves and a coat she had bought just for this trip. She strolled down the streets, stopping in stores she could never afford to shop in and looking in huge windows at the restaurants and bars scattered down the streets. She was getting hungry and wanted a nice meal but felt awkward about eating alone. Strolling to the end of a block, she found a nice Italian place with lots of bar seating. It looked perfect and smelled heavenly. She strolled in and the hostess, a gorgeous dark-haired girl, showed her to an empty seat in the large horse-shoe shaped bar. Syd slid out of her coat and settled at the bar, ordering a drink. She pulled out her phone, smiling at a new message from Will [Tomorrow!] With that one word, so many feelings swirled inside her. Excitement, a little awe at how brave she was, anticipation, hope. [Tomorrow!!] She answered back.

The restaurant was dimly lit and classic Italian music was playing making such a romantic atmosphere. Maybe we can come back here this week. she thought. It was a perfect date night place. The only thing wrong was a girl across the bar with an annoying high-pitched laugh, but Sydney couldn't be mad at that. She was sure the willowy redhead was here on a date too and it certainly sounded like she was having a good time. She peaked across her drink at the couple across the bar, the man had his face tilted towards her, speaking in her ear. He must be teasing her because she would shake her head and giggle loudly.

Sydney ordered and people watched at the bar. It was fun to watch others out on dates, chatting with friends, but her eyes kept being drawn back to the couple across the bar in the dark corner. She didn't know why but assumed it was the girl's giggles (Syd was dying to know what was so funny) or that the gentleman she was with (he was quite a bit older, but handsome with glasses and a neat beard) didn't seem as into her as her giggles would let on. He would say something to her and pick up his phone almost completely ignoring her and finally putting it down to return to the conversation. A bit rude, Syd thought picking up her phone to read Will's message [I can't wait to hold you in my arms and then hold your arms over your head as I kiss every inch of your body before fucking you senseless, princess.]

Sydney smiled down at her phone, feeling that familiar tingle and ache between her legs. She tried to think of something equally sexy but settled for the truth. [I can't wait! I'm so wet for you right now.] The waiter slid her lasagna in front of her and she thanked him sweetly, then asked where the restroom was and the waiter pointed across the bar to a little hallway behind the couple she'd been spying on. Sydney grabbed her phone, leaving her purse and coat and walked around the bar towards the restroom, and passing the giggling couple, sneaked a peak as she passed. The girl was trying to talk and eat spaghetti at the same time and the man turned to glance at Sydney and their eyes met. His eyes grew wide in alarm and Sydney seeing him close, knew she could never have mistaken those green eyes fringed with dark lashes anywhere.

Will? Her Will? Will on a date with another girl? Will on a date with an awful annoying girl the day before they were supposed to meet?!

Blood flushed into Sydney's face and she darted for the ladies' room. Slamming the door and locking it behind her, she stared at her shocked face in the mirror. Her brain raced with thoughts almost too quickly to pick them out. What had she been thinking? She, a twenty-year-old college student had flown across the country to meet an older man, who'd seduced her online? What a complete moron. BUT. He technically, never lied. They never said they wouldn't see other people? She didn't own him. What was she going to do?

Her phone started dinging, [Sydney?] [Sydney, are you in Chicago?]

She looked at the messages and rolled her eyes. [Will, go back to you date. She seems WONDERFUL!]

[It's not a date. She's a coworker.] [Please come out of the bathroom. I'm standing in the hall. I look like a creep.] [Why are you already in Chicago??]

Sydney stared at her phone, unsure what to believe. A coworker? Maybe...but at a fancy place like this? Sydney had never been more upset that she had not grabbed her bag on the way to the restroom. She waited, ear pressed to the thick wooden door, until she thought she heard his retreating footsteps and his voice (his sweet sexy voice) speaking to the stupid ginger twat back at their seats. Quickly, she snatched up her phone and darted out of the bathroom. Passing them as quickly as she could, she practically ran up to her seat and plate, motioning for the waiter as she gathered her coat and bag. She saw Will speaking briefly to his date and start making his way towards her.

"Yes ma'am" the waiter sauntered over with a polite smile.

"I'm so sorry. I need to go. Something's come up. Can I get the check?" Her words poured out frantically enough for the waiter to look concerned and walk off to get her check.

"Sydney. Babe." Her stomach turned at his voice behind her. She resisted the tears that begged to fill her eyes. She couldn't believe this dream weekend had all gone so terrible wrong. His large warm hand circled her upper arm as she stood like a statue refusing to look at him instead staring at the tall, thin auburn-haired woman across the bar who had taken out her phone and was scrolling un-bothered. The waiter returned quickly with the check and, before she could even reach for it Will leaned across her pushing his credit card at the water and telling him to ring up all the three meals. The waiter was asking if she wanted her food to go but she just shook her up, snatched up her coat and bolted for the door.

"Sydney! Fuck..." Will called after her but she knew he at least had to wait for his card to leave. She pounded down the sidewalk, not feeling the frigid air, not seeing the faces of the crowd, not knowing where she was going. The embarrassed tears that had threatened in the restaurant finally slid down her face causing her vision to blur enough to make her stop, stepping into a dark alleyway to wipe her eyes and catch her breath. Standing in the shadows, she heard footsteps pounding up the street and finally saw him pass, looking for her. He stopped, looking up the street, across the street, and finally turning to look behind him. And he saw her, standing there in the shadows and he froze.

The moment went on, what felt like forever. A handsome man standing planted on the street forcing people to walk around him as he starred into the alleyway at slightly disheveled girl shivering in a purple dress. Two people getting their first real look at each other. Then the moment passed, and Sydney turned, walking up the alleyway putting distance between them. Will followed, catching up easily and he grabbed her arm first gently, then forcefully, making her stop.

"Sydney, dammit. Stop. Please!" He spun her around, pushing her against the wall, and pinning her in between his arms. She just looked back, taking every inch of his face in. The furrowed brown, the fierce green eyes, his neat salted beard. He was breathing heavily, controlling his fury, trying to speak calmly. "Syd, baby doll, this...this is NOT how this week was supposed to go. Tamra, the woman in the restaurant, is a coworker. Nothing more. Please listen."

Her bottom lip trembled, she felt more and more ridiculous but she was still hurt. "Will," her voice hoarse, "She clearly likes you. You should go be with her." She put her hands on his chest and pushed, trying to extricate herself.

He rumbled and pushed her back against the wall. "Listen, if I wanted to be in there with her, I would be back there. The only reason I accepted the offer to come out was so I didn't sit around my apartment waiting for tomorrow, when I'd finally...see you." Their eyes met and she believed him. Their faces were so close that she could feel his warm breath tickle her ear and smell a hint of the wine he'd been drinking. She leaned forward and did something she had dreamed for months about doing. She pressed her mouth firmly and finally against his mouth and kissed him. Then pulled her face back to look at him and smiled.

And then, like the slow burning fuse of a firework that had finally reached its end, they ignited. He wrapped his arms around her waist pulling her up to his mouth and she wrapped her arms around his neck. Instantly she felt the hardness of him, pressing into her stomach and she groaned as he kissed her. His hands roamed her body, first groping her tits feeling for the hard nubs of her nipples, then sliding down to her ass and picking her up. She wrapped her legs around his waist as he pressed her into the cold brick wall. Her new dress bunching around her hips.

He kissed her mouth and down her neck, kissing the top of each ivory breast before growling in her ear. "It's not how I wanted it, Syd, but I need you now. Right now!" All she could do was nod and reach down through her legs to touch his erection through his pants. He needed no encouragement and faster than she could believe, he had pulled his cock free and pushed her panties to the side. She was slippery slick already and as the head of his cock pushed into her, she first sighed but then cried out as his slammed deep inside her. All her muscles clenched around him and a delicious pain burned inside her.

"Oh fuck, baby girl your pussy is better than I could have imagined." He groaned in her ear. She loved his filthy mouth. "Mmm, you're so wet, Sydney, but I'm going to make you soo much wetter." He whispered in her ear and thrust inside her. She rocked her hips against him in unison and could only whimper as their bodies blazed bright in a dark alley.

Before long, she felt his hand slide up in her hair and pull her head back. He looked down at her, "I'm going to cum, Sydney. Tell me where you want me to cum."

She didn't even think before she blurted, "Inside me. I want to feel your cum inside my pussy."

And he obliged with a loud groan than turned into a growl, he pounded into her biting her neck and using her body for his pleasure. She felt him lean into her and then a hot, explosion deep inside her pussy.

Slowly coming down, they stayed joined together for a long moment before he let her slide off his cock. Sydney pushed her dress down from around her waist and quickly glanced up and down the alleyway, wondering had then been seen. Will zipped up and gathered her purse and coat from the ground where they'd dropped. He wrapped the coat around her shoulders and used it to pull her close to him again for another kiss.

"I'm sorry, this was not how I intended to have you for the first time." He looked slightly abashed, but she shook her head.

"Actually, this was...kinda perfect. No awkwardness." She smiled widely up at him. "I'm sorry about - you know - Tamra. I'm not normally a jealous person but..."

"I get it." He quieted her. "I would have probably broken the guy's nose if roles were reversed. As they held each other close in a quite alleyway, fat snowflakes started to drift down around them. Sydney looked around in wonder.

Will grumbled and wrapped his arm around her shoulders, "Let's get you back to my apartment and get you warm."

* * * * *

Will's apartment was nice, cozy and decorated in that sparse, functional way that most men usually have. Will rolled her suitcase into the bedroom. They had stopped by her hotel room, retrieved her luggage and cancelled the rest of the week's reservation. Sydney looked around politely as she finally started to warm up. Walking straight for two large bookcases, stacked with books ranging from the classics to Harry Potter and everything in between. She smiled over the well-worn copies remembering all their conversations about books.