Authors note: This story is a gentle exploration of one woman's journey into the dom/sub lifestyle and as such it is as much a romance as it is a BDSM story. I wrote it in collaboration with @RosewoodTulip and would not have been able to write it without her friendship, guidance and encouragement, thanks Rosie x.
Feedback and comments are always welcome, enjoy.
Jilly looked at the screen of questions in front of her. WTF was she doing; did she need this, all the hassle, all the creeps it might attract?
She'd had a number of good relationships, decent fella's who treated her well and genuinely wanted to make a go of it with her, but it was never enough, she always felt there was something missing.
She looked at the screen again. Describe yourself: That was fairly easy, she was intelligent, articulate, independent, she had a naughty, if somewhat quirky sense of humour. She enjoyed nice wine and good food. Describe yourself physically: What to put? She was tempted to write 'never had any complaints' but knew that wouldn't do. Probably best to be honest, 5'5", shoulder length brown hair, have been told I'm pretty, a little heavier than I'd like, big boobs (have always been a hit with the boys). She knew she shouldn't put that last bit in, but it was true and her quirky sense of humour got the better of her, shame the dating website didn't let her put a laughing emoji next to it. Do you want to add a photo: Definitely not.
What are you looking for? This was far more difficult, she really didn't know how to describe it, it was more a feeling than anything else. She looked at the screen, trying to conjure up the words, knowing that this might be the most important bit. She began to type: I'm looking for someone who will respect me, someone who will cherish and protect me, hold me in his arms and tell me everything is ok. Someone who knows his role in life is to care for me. In return he will get someone who knows their role and who will give their love and devotion.
She read it over to herself, she'd planned on writing about a good sense of humour and wanting to have fun, and being tall etc, but the more she read it, the more it seemed right. She added one little bit to the end, Are you the right man?
With almost shaking hands she hit the 'post' button on the screen.
She sat there for an hour awaiting replies. Nothing, just a few notifications that people had read her post. She was tempted to take it down but it was almost her bedtime and she decided to leave it overnight, remove it in the morning.
She awoke early and grabbed her computer along with her coffee, opening up the dating app. She had fifteen replies, wow. She was almost nervous as she clicked on the first one. Typical, 'I want to suck your big tits, send me a picture." The next one, "Do you like titty fucking?" Well she did, but not with this wanker. Most of the rest followed in the same vein, men offering to stick their big dicks up her ass, even asking if she was lactating so she could breast feed them, yuk.
Of the fifteen replies, only one was even literate, not alone non obscene. "Hi, I read your post with interest, I think I understand what you need and I think you can be what I want. If you're interested, you can click on my profile and then reply to this, telling me you're interested."
She re-read it a couple of times, short and sweet with a hint of self assuredness or was it cockiness. She clicked on his profile and was surprised to see a picture, his profile telling her he was forty three, which tallied with his picture. His hair was cut neat and short, the lightest touches of grey at his temples and eyes looking straight back at you, he wasn't smiling and nor could you describe it as a smirk, it was more a confident, 'like what you see' look. She had to admit to herself that she did.
She read the rest of his profile, Describe yourself: 6" Tall, Fit, Self employed. Looking for: You'll know if I contact you. Prick, now that was cocky and it annoyed the fuck out of her. She closed down his profile and sat there thinking. He had reached out to her, so presumably she or someone with a similar profile was what he was looking for. His profile hadn't said much at all about him but his message to her had said he understood what she needed. She wasn't even sure she knew herself what she wanted or needed.
She read his reply to her profile again and found herself replying. "Hi, read your profile, what there was of it. If you like we can chat online and see if we're compatible. Let me know."
She left it at that, short and sweet, like his profile. She was surprised to get a response within ten minutes. "We can chat online but I find it much better to meet in person. I will be in O'Neil's restaurant in town from 1pm to 2pm today. You know from my profile what I look like and I'll be wearing a light grey jumper. I don't know what you look like and don't need to, I believe you when you say you are pretty. If you turn up and change your mind, just walk out, I won't be looking for you and I won't know you've been there. Hope to see you then."
Fuck him, what sort of head case was he? He didn't want to chat but had thrown the ball back into her court, leaving it up to her if she met him. She mightn't have been off that day, but it was already 10.30 so maybe he was presuming she was. She was angry at him for leaving it up to her, for not chatting with her, but found herself wondering what she would wear if she were to meet him. It was an early summers day and she decided on a light, summery dress that showed just a hint of cleavage and a light jacket that she could take off if it was too warm.
She walked past the restaurant twice, trying to act cool, whilst peeping through the window to see if she could see him, she couldn't. Eventually, taking a deep breath to steady herself, she walked in and saw who she thought was probably him sat in a far corner, on a small table by himself. He was looking down at a computer tablet rather than looking for her, which, to her surprise, annoyed her. She knew he'd said he wouldn't, but why wasn't he looking for her?
This was her chance to turn around and forget about this whole crazy idea, her legs felt like jelly as she walked over. He looked up and smiled, friendly and welcoming, no hint of triumphalism or 'I knew you'd come' in his eyes.
He stood up and put his hand out to shake hers, "Hi, I'm Chris, nice to meet you." She'd thought about using a false name but found herself saying, "Hi Chris, I'm Jilly, nice to meet you as well." As he pulled out a chair for her to sit down on.
He sat back down and faced her, the confident, relaxed look on his face in contrast to her own silly grin.
"You weren't lying when you said you were pretty, what would you like to drink?" This might have sounded corny coming from someone else but he made it sound like a natural thing to say.
"Just water will be fine, thanks."
He caught the waiter's eye and got him to bring two glasses of water and to leave the menus. "So Jilly tell me a little about yourself."
"Such as?"
"Well I know why I replied to your ad, but why did you answer back?"
This threw her, it was a strange and unexpected question, although maybe not unreasonable. She found herself babbling trying to answer it. "I don't know really, it's my first time posting an ad on a dating site and I didn't know what to expect. From your reply you seemed to understand what I was saying and..."
The waiter returned and Jilly hadn't even looked at her menu but Chris ordered Veal escalope for both of them, telling her it was really good and to trust him, she just nodded. She was annoyed, more at herself for not saying anything, rather than at Chris for ordering. Was this what she wanted?
They carried on talking or rather she carried on talking, finding Chris to be a good listener and seemingly very interested in whatever she had to say. During a lull in conversation he asked her did she always wear her hair down or did she sometimes wear it tied back. She said it depended and that she had a hair go-go in her bag if he wanted to see it tied back. He nodded and she tied it back.
He looked at her for a moment, "I prefer it, leave it tied back." Jilly couldn't believe this, she was actually blushing and doing this small thing that pleased him left her with butterflies in her stomach, thankfully their food arrived.
He was right, the Veal was really good. Not much was said when they were eating and she began to feel nervous, wondering if things were ok. She needn't have worried, as the waiter took their plates away, the same calm smile was back. They made small talk, him mainly asking things about her and her life, only occasionally saying things about himself.
"I'm going to have to go shortly but would like to meet you again, also now that I've met you I'd like to chat with you online, are you free this evening?"
She was a bit taken aback by how quickly he brought the afternoon to an end but found herself saying that she was free and would like to chat with him later. He pulled out a business card and wrote his Skype details on the back.
'CP business consultants, Chris Peckham MD' She looked at the card a few times as she walked home, googling him as she went. His picture was there and it seemed like a legitimate, successful business. He certainly wasn't hiding who he was.
She got home and found herself looking at the clock, what time would they begin, what should she wear? She looked at herself in the mirror, 'WTF are you doing? You're a strong independent woman, whose business is it what you wear, it's your decision. You need nobody's permission for anything.' As she was saying all this to herself she found herself thinking that she must remember to keep her hair tied back, the irony and stupidity of it all making her smile. She looked at the mirror again, 'Fuck it Jilly, just go for it, embrace it, enjoy it.' She went to her computer and logged onto Skype, finding his profile and messaging him, "Hi, what time do you want to Skype? What shall I wear?" she clicked send before she could change her mind.
His return message was short and sweet, "8pm, same dress as this afternoon." Maybe he was busy at work.
Since the pandemic, Jilly had used Skype all the time for work, so had no problem being in front of the camera, except this time. She spent the whole early evening fretting, trying to get her head around it.
She'd posted on the site for a reason, she wanted something more than other relationships had given her and it seemed like Chris could give her that. He listened to her, he seemed to know what she wanted and needed and what she would thrive on. He could give her that. She didn't know exactly how it would be, but she knew that being in a relationship with Chris would involve giving herself to him, letting him take some control over her life. Was she prepared to do that? Yes she wanted to, could she, she really didn't know.
These uncertainties and questions racked her brain the whole evening, by seven thirty she was a mess, getting frustrated and annoyed at herself, a bit of her own 'fuck it' spirit eventually winning out. She checked her lightly applied make-up again and decided to have a glass of wine.
Whether it was her nerves or some sort of omen she wasn't sure, but she'd only had two sips of her wine when she spilt some of it down herself. She smiled into the mirror at the big red stain above her left boob, 'fucking typical'. She finished the glass and then took off her dress, all the time stood in front of the mirror, enjoying watching the light dress fall from her shoulders and float to the floor.
She looked at her reflection, looked at her body and at her best lacy underwear that she had chosen to wear that day. Maybe it was the glass of wine but she thought 'not bad' as she held her stomach in and pushed her chest out.
It was now seven fifty and she decided on another quick glass of wine, deciding to drink it in her underwear, rather than risking another mishap. She drank it in three wonderful mouthfuls, leaving it in her mouth each time and savoring the taste and texture. She put the glass down and went to her wardrobe.
She flicked through a couple of other summer dresses but eventually settled on a crisp white blouse, putting it on and buttoning it up and then looking at herself in the mirror. It looked good and fitted her well, a sexy thought entering her head 'That'll do'.
