Words with Friends with Benefits

That’s my name! she had written. It was the first thing she’d written after 3 games of Words with Friends with this stranger, but seeing VIOLA on the board was a surprise, and worse, he’d gotten 24 points from it.

I know — I almost missed that word 😛 he had replied. Kind of a cheesy line, but worth a chuckle. Fortunately for her, it was only three turns later that she got to return the favor.

Nice name — thanks for the points! Was the message, sent alongside the extension -TED, creating VIOLATED for 42 points. Ted smirked, and wrote back without making a move-

Yeah, now the board shows how I feel.

* * * * *

That was 3 months ago. They’d started talking in the game chat, about innocent things at first — introductions, jobs, enough to consider each other acquaintances. Soon they switched to another messenger program and got to talking about past relationships. Ted had been in a long-term relationship which was most of his history, Viola had been with a few guys and, feeling comfortable enough on this particular day, shared a few stories that definitively pushed them into being friends — Ted new things about her now that many of her friends she saw daily didn’t know. Talking became flirting, with her sending a selfie and him admiring her shirt, or Ted’s kind words of support bolstering Viola’s confidence before a big meeting at work.

They had their own world, their own in-jokes, their own understanding of one another. One night, Ted a couple glasses of wine in, their flirting got to be explicit — sexual preferences, fantasies, no topic seemed off limit. They found each other matching their desires — was it their true fantasies, or were they crafting them to convince themselves that what they felt happening was a good idea? For Ted, it was real, and this girl seemed to be into, or at least open to, some of his wilder fantasies. Drunk on excitement and/or wine, they decided to meet –they didn’t live too far away from one another, so they laid out a plan — the following Saturday, he would take the train to her city. She would meet him there, and they’d continue on to another city, one where they didn’t know anybody, and they could make their little world their entire focus. Two nights in a hotel — they were not going to leave.

* * * * *

The day came, and Ted was nervous as hell. He chose what he wore carefully — as a bigger guy, he did not want to come across as a slob. Some nice jeans, a polo shirt — something casual but that he thought brought out some of his better features.

Constantly checking his phone as the train pulled into Viola’s station, he messaged her that he was in the last car. His stomach in his throat, he watched the door, and after what seemed to be an endless stream of randos, there she was. Shorter than him, but not notably “short,” her dark hair framed a pretty face, glasses highlighting soft brown eyes that shone when she saw him. She had mentioned that her boobs were big, but he now saw her body in its entirety for the first time, and his cock jumped a little. Her tits were large and fit nicely on her small frame. Her ass was similarly round — feminine and healthy but still fit. She sat next to him, smiling shyly.

“Hi.”

“Hey.” He replied, and they sat for a few minutes in silence as the train rumbled on, unsure what was going to come next. Finally, Ted put his arm around her shoulders, gently, and encouraged her to lean on him as he leaned against the window. Feeling her body, her weight, her warmth — it was everything he had hoped for and more. Shifting his weight slightly so that they were better aligned, he ran his fingers over hers, and they sat on the train for the next 40 minutes her leaning back on him, silent and anxious for what they both knew would happen next.

Their hotel was conveniently next to the train station, and the uninterested clerk at the desk sent them up to room 145 within two minutes of their arrival. They put their bags down, looked at each other — and it clicked. They knew it. It was happening.

A firm embrace, a kiss, a longer kiss — now making out, her glasses pushed on his cheek slightly, but she looked so damn cute in them, he didn’t mind at all. He pulled her onto the bed, on top of him, and playfully gave her a spank as they kissed, her body pressed down onto his and for the first time, she felt his cock’s swollen head through his pants. He placed a finger under her chin as their lips pulled apart for the first time in minutes.

“Take off your shirt. Let me see these magnificent tits.”

Biting her lip, she obliged, her arms crossed to grab the bottom of her shirt and extending as she lifted it over her head. She was proud of them, and knew he liked them. She had picked out a special bra for the day, maroon and a little lacy. As her shirt rose, so did Ted’s eyes, on her stomach, her ribs, and then those tits — he reached up, ran a finger around them, and as Viola’s shirt finally was flung to the side, he put them both in his hands and squeezed — firm, but not wanting to inflict any pain. Only to show how much he had dreamed about this moment. She had loved teasing him with pictures of her wearing low-cut shirts, but now, now they were in his hands. His to caress, to hold, to explore. He pushed them together to create that familiar sight of cleavage, the one he’d jerked off to several times by now. And then, he pulled her back down onto him, kissing her harder, and reached behind to unhook her bra with his left hand, while his right grabbed onto her ass.

As Viola felt her bra undone, she sat up, straddling Ted, removing it from her arms and then half-jokingly threw her hand up across her chest, offering minimal coverage of her newly free tits. “Don’t I get to see your chest?” she asked coyly.

He sat up, quickly pulled off his shirt, and her eyes went to his broad chest. Her hand moved, revealing her perky but small, pink nipples, as she put her hands on his chest and leaned in to kiss him. “ohh… that’s…,” she sighed, and her voice trailed off as she felt his strength and power under her fingertips.

Ted decided to make his move. They had talked and joked about how he had always wanted to be more commanding, more dominant in his sex life, but never found the confidence to do so. Viola was interested in this, and he knew she would respond. Still, he swallowed hard before he spoke.

“Do you like that? How about when I grab your tits, does that feel good?”

It was not great, as far as dirty talk went, but it was direct, and she did like the attention he was giving to her breasts. “Mmhmm” she uttered, somewhere between a whimper and a word. Her fingers lingered on Ted’s chest as he leaned in, not for a kiss but to put his lips to her ear.

“I’m going to fuck you tonight. I’m going to fuck you from behind, the way you like it, and I’m going to squeeze your tits and fill you with my cock. Viola, I’m going to pound your tight pussy, doggystyle, and I want to hear you moan.”

She couldn’t believe he was speaking to her so bluntly, or vulgarly, but damn did it make her wet. She nodded, not trusting her own voice, and in that moment he had lifted her off the bed by her waist, set her feet down on the floor, and begun unbuttoning her pants. He was just doing it, without asking or offering anything for her. Suddenly, she stood in only her panties, his thumbs already under the waistband and starting to slide them down, and then she was naked, standing in front of him, completely exposed. His eyes were all over her, and she could feel them, she craved them — but she couldn’t make herself look him in the eye.

Ted was finding that he liked Viola a little shy, and now that he had her naked, he ran his hands over her thighs before sliding a finger slowly over her pussy, surprised at how wet she was already. A small circle trailing around her clit drew a moan, and he knew she was his. “Suck my cock.”

Viola didn’t dare question it, and besides, she was curious. She wanted to see it, to feel it, to taste it. She reached down to unbutton his pants, and as she slid them down over the bulge in his boxer briefs, she felt her thighs get even wetter, her pussy literally dripping with excitement. She took his cock in her hands, and gently pulled his underwear down, allowing his shaft to spring up toward her face- it wasn’t enormous, but it was thick, uncut, and it was all because of her.

With a hand on her left breast, Ted stood up, and used his groping hand to guide Viola to the bed, getting her to sit where he had been. As soon as she was there, he placed his cock on her lips, and she eagerly took it in, licking it, sucking on it, feeling him grow inside her mouth.

He groaned, looking down at those soft lips spread around him, her large tits serving as a beautiful background to the best blowjob he’d ever had. Ted placed his hands on her shoulders, and then the back of her head, tentatively. They’d talked about him taking control, but he didn’t want to push things too far their first time.

Viola’s moan echoed around Ted’s cock as his hand touched her head. Yes, she thought, pull me in. Give me that cock and make it fill my mouth. I want you, you know I do, now show me that you want me — show me that I’m yours. She tried to convey that all with her moan, but what got the message through was when she placed her hands on his ass and pulled him toward her.

With her urging, Ted’s hand held her head steady, and he began to thrust, to fuck the face of this beautiful girl who seemed so sweet and proper. As she let out a high-pitched noise of pleasure, he pushed harder, the tip of his cock poking at her throat as she fought her gag reflex — she wanted him to remember this first time, to know that she was serious about him doing what he needed to get off. It was a relief to give herself to him, to let go of every care of the world and devote herself to this throbbing cock between her lips. That was her only focus now.

As his eyes rolled backward, Ted shook his head and made himself focus. He never would have thought he’d be in this situation, but this beautiful girl was deepthroating him while he fucked her lips, moaning and drooling all over his cock. He grasped some hair between his fingers and tugged it gently, getting an immediate response as she doubled down on this blowjob.

“Ohhhh yes, such a fucking good cocksucker.” The words breathed new life into Viola, and she ran her tongue along the bottom of his shaft, moaning as he held her head against his crotch. This cock was filling her entire mouth, and also her mind — she wanted nothing more than to please him, to coax out his warm cum.

“Mgghmrff” she mumbled, drool running down her chin as she looked up to his face, her brown eyes wide. She played it up, slurping and slobbering, and before long his grip on her hair was tightening.

“Fuck yes, ohhhhhh I’m gonna cum,” Ted growled, and he pulled Viola’s head back as he erupted. Hot, white strings burst from his rigid cock and splashed on her glasses, her cheeks, and her nose, some dripping down onto her incredible tits. “Damn do you do look good with my cum on you.”

She blushed, both embarrassed and incredibly turned on. She worked up the courage to look up at him, to actually look at his face for the first time in what seemed like hours. Through strings of his cum, she saw him looking at her caringly, but with an air of triumph. He had claimed her; she was his. They both new it to be true.

Ted offered her a towel to clean up as he put his underwear back on, and when she had cleared her face of his sperm, she sat next to him on the bed. He held her gently, kissed her neck softly, and lay down next to her. As she flopped down, he reached for his phone and showed her the timer app he was opening.

“Two hours. When this goes off, you’re mine again.”