Author's note:
This story includes dialogue sent over text.
{This is text sent from a woman}
[This is text sent from a man]
Special thanks to Lit user "Vay" and volunteer editor "Squishy" for their efforts in editing and fine tuning the details of the story.
=========
JENNA
With her eyes closed, Jenna put a middle finger between her lips and sucked on it. She took it deep enough into her mouth to almost touch the back of her throat before she swallowed hard, then pulled it out a little and licked it slowly. She imagined the thin finger was a big fat cock she was pleasuring. Soon afterwards, she removed the imagined dick from her lips and slid it between her naked breasts, over her stomach, and delivered it to her anxious clit. Rubbing with purpose and rhythm, she worked herself slowly and firmly. She slipped her finger, still glistening with her spit and desire, into herself. She felt how her finger slid against her and enjoyed a light tingle from deep within. Her loud and slow exhale filled the otherwise silent bedroom.
Jenna had been masturbating like this for the past twenty minutes or more and was getting close to a big finish, however, she kept pausing to read, and then to type on her phone. These little interruptions served to delay and to add to her pleasure. With great anticipation, she read the message from anonymous chat user, MaxPleasure. She replied quickly, and returned her hands to her body, pinching one of her already erect nipples. The feeling made her arch her back on the bed beneath her as if to expose her breasts to someone, even more than they already would have been, had there been someone else with her.
A moment later, Jenna's phone vibrated with another message. She read it quickly, put her phone down, and then moved to all fours. She laid her chest onto the bed, and put both hands between her thighs. The satin sheets teased her nipples as she slid herself backwards to present her ass to an imaginary man. Thinking of his cock pounding deep into her at just the right angle, she fingered herself with one hand, and rubbed her clit hard and fast with the other. Her breaths came faster and deeper by the second until she could no longer keep her mouth quiet. Pressing her face into the pillow, she let out a loud but muffled scream as her fingers finally brought her to the peak, and beyond. She rocked herself against her hands and rode wave after wave of pleasure for another long half-minute. Jenna collapsed onto her stomach and laid still for a while with her eyes closed, enjoying the dizzying release.
A long while later, Jenna sent one last message before she sat up and gathered her clothes from the floor near the bed and redressed herself. Tidying the bed, she thought to herself how this dirty little secret of hers had become the best part of her workday. Giving herself a quick little orgasm was no big deal, but sexting a total stranger while doing it was a whole new level of naughtiness. She recalled the first time she did this. It was only a few weeks ago. She remembered she had been nervous and giddy with anticipation as she rushed home from work, and made sure that her boyfriend wasn't going to come home early. After sending a simple text asking how his day was, she soon had the answer she needed. She had an hour from the time she and he would arrive. It took planning. It took cunning. It took balls. She smirked to herself over that last thought.
Just a few months ago, Jenna would never have thought she could engage in such "lewd behavior," as her overbearing mother would have called it. Though she was ravenous in spirit, she was quiet and reserved in her actions; the result of a strict home, filled with talk of sin and guilt. Now free from her family, but not her upbringing, she could barely even talk with her boyfriend about sex. She certainly had desires but she would clam up if she ever tried to discuss them and this frustrated her to no end.
BEN
Ben was checking his smart phone every minute or so on this late Tuesday afternoon. He wasn't getting much work done these days because he had been chatting with an anonymous woman who went by the username LitMeGirl. They talked about all sorts of sexy things. They told each other dirty jokes, talked about things they had or hadn't done, and what they would or wouldn't do. She was funny, bold, and had become a true highlight to his day.
He had first encountered her on a web forum while searching for something hot to read one night. They both posted some of the same titles on a topic 'Favorite Reads' and it wasn't long before they moved the conversation from the open forum to a private chat. They began, innocently enough, by sharing their favorite stories and it took off from there, escalating faster than either of them had expected. They had a real chemistry. That was months ago. Nowadays, things were not so innocent. Ben was pretty sure LitMeGirl was touching herself in between his messages again. He wasn't doing the same, since he was at work, but he enjoyed the thought.
The thing with anonymous sexting was that it felt like it was low risk, to him, and probably to his sexting partner. It seemed to him to be a safe way for him to explore and express his desires and see how he felt about various aspects of his sexuality without risking ridicule and embarrassment from his girlfriend; a person he would have to look in the eye the next day.
They agreed that even though it was only online chat they should treat each other with the same respect as though they were meeting in real life. They wanted to keep the conversation lively but never uncomfortable. One thing they never did was send nude pictures of themselves. She had her reasons, and though they were different from his, he had his. They didn't need to justify their reasons, but simply chose to respect each other's. Ben liked that about LitMeGirl. There was a whole Internet full of naked breasts available if that's all he wanted, but he found her remarkably easy to talk to and interesting.
One day, they started talking about various sex acts hypothetically.
{I've never had a threesome, but I might be willing if the mood was right.}
[With another man or a woman?]
{Probably a woman. Maybe a guy, I dunno.}
[That's hot. I'm surprised though. Two men wouldn't be your first choice?]
{I don't think so. They'd probably be too rough, all macho and shit. I think with a second woman, things might slow down a bit.}
[Not if I was the guy with two women - lol]
{Yeah-yeah, every man's fantasy, I know. But what about you and yours with another guy? Could you deal with that?}
[Maybe. If she really wanted two guys and he didn't touch me.]
{Aww come on now...}
[If the mood was right ; ) Maybe.]
{Hot!}
Sometimes he would send her links to pictures and videos he liked. She sent fewer links than he did but occasionally she would send him something. They would talk about things in the stories and videos they liked and didn't like.
{Nice video with the cucumber... makes me wanna go grocery shopping.}
[Yeah, that part was pretty hot. I skipped over the part with the celery stalk though.]
{Nasty! LMAO}
[Ever do anything with veggies?]
{I did myself with a carrot once... that was fun.}
[Was it a long fat carrot?]
{Not really. It was fairly normal sized. It was very bumpy though.}
[Dirty!]
{Well, I was washed it in warm water of course.}
[Not what I meant ; ) ]
{I know. But I did put it in my ass. Just to try it on my own terms.}
[Really?]
{Yeah. I've always wondered what it would be like in the butt.}
[You've never taken it up the ass?]
{Been waiting for my bf to do it for a while but he just won't try.}
[Is he just not into it?]
{I dunno. I've never asked. Just can't seem to get the words out}
[That's too bad. For both of you ; ) ]
{I know.}
Several long multi-day chats later, hypothetical talk became more direct. It was almost by accident. Almost.
Ben sent a link to a video. [I would love to have this done to me.]
Jenna tapped the link to see a clip of a woman straddling a man who was tied to a chair. The woman was rubbing her breasts into his face aggressively. It looked like he might not even be able to breathe. His shirt was off and his pants were still on. Jenna watched the short clip and thought about what she might feel in this situation and she liked it. She responded to MaxPleasure.
{Mmm. If you think you could handle me. My breasts are a fair bit bigger than hers. You might just suffocate - Lol.}
[I would sure try. Besides, at least I would die with a smile on my face : D ]
{There wouldn't be much to try if I have you tied up now would there?}
[No, I guess not. Other than trying not to cum right there in my pants - lol]
As the weeks went by, their language had changed as though they were co-authoring a story in real time. They were role playing. They were fairly tame at first.
{I slowly fiddle with my top button and watch your reaction.}
[My eyes fixate on you and my manhood begins to wake up]
{Mmm nice. I bet he's just dying to come out and play. Can I play with him?}
[Soon I'm fiddling with my button until he's free.]
{Oh my, he's beautiful. My eyes are now the ones fixated}
That's where it began. They role played simple situations involving sex in different places and positions. It was fun for both of them and pretty tame. Nowadays, they weren't holding much back anymore. Today was one of those days.
[I'm getting really hard. I want my cock deep in your mouth. Will you do that for me?]
{Glad to. I suck him hard and take you all the way to the back of my mouth.}
[My cock gives you its glistening desire, dripping onto your tongue]
{Yummy. I swallow your little gift, feeling it slip down my throat. Do you like that thought?}
Ben felt his cock growing in his pants under his desk. He was indeed enjoying that thought. As the chat went on, Ben described to LitMeGirl how he would hold her breasts in both hands and pinch her nipples. He would tease her clit with just his tip, before having her bend over for him so he could really drive himself into her; with her head down and her ass up. Her responses were short, affirmative, and were becoming more and more delayed before she finally messaged him {OMG that was great} which confirmed his earlier suspicion that she was indeed masturbating to the messages he was sending her. Ben smiled a smug little grin of accomplishment and tried his best to refocus on his work.
After he finished up his duties for the day, he arrived home a little late. He was worked up from his chat with LitMeGirl, and hoped he might get some with his girlfriend tonight. Through dinner, he kept looking at her and thinking about how he wanted to take her right there at the table. He admired the way her breasts stressed her top and wanted to free them. He also imagined them pressed into the table from him bending her over it. Then he shook his head, pushing the fantasy away. He reminded himself that was probably too sudden, too impulsive, too disruptive, and would probably lead to her complaining about dinner being ruined.
Later on, they watched a movie she had picked out; Runaway Bride, with Julia Roberts and Richard Gere. They laid together on the couch and he cuddled with her from behind. He could see the TV but he wasn't paying much attention to it. With his hand over her, he traced along the curve where her side became her waist and then her hip. It wasn't long before he felt the enviable snuggle boner pressing against his pants. She felt it too and she teased him about it. "Got a thing for Julia Roberts, do you Honey?"
"Not even close, Babe"
Their sex life was OK, but only OK. He couldn't complain too much though because she never stopped him from anything he tried. The trouble was that she never expressed a desire one way or the other. He became nervous and reserved because he took her nonchalant response as disinterest. Ben was afraid to experiment without discussing it first. He worried that someday he might do something she hated and she wouldn't tell him. At best, she would be patronizing him and probably fake an orgasm. At worst, he feared she might be disgusted and not want to try anything new again.
