Jessica and Tom 01: The Hunt

Lily stood shaking slightly as Jessica worked her tongue expertly into her. Lily moaned as Jessica hit her spot just right. Jessica withdrew and stood again walking to her desk leaving the beautiful lovely swooning in pleasure. Finding the right drawer in her desk she pulled out a double ended dildo with a leather disc fitted at the mid-point. The disk had hooks and eyes sewn to it. She swaggered back to Lily and sank to her knees again once again slipping her tongue into the redhead. Jessica slipped one end of the dildo into Lily slowly, inch by inch until the leather disc sat against her gaping pussy lips. Slowly she fastened the hooks and eyes of the panties to the corresponding ones on the dildo. The panty fabric would give just enough to allow the dildo to move as Lily thrust.

Jessica stood again and slipped her own panties to the floor then took Lily by the hand guiding her to the desk. Jessica lay back on the desk opening her legs, her garters stretching the tops of her nude stockings. She slid her hand to her wet pussy slipping her finger in and rubbing her clit briefly before grabbing the end of Lily's cock and guiding it into her wet throbbing hole.

"Now darling, my turn to try the prototype." Lily got the idea and applied pressure to her hips slipping the rubber cock deep into Jessica's waiting hole before pulling back. The motion stimulated them both, the movement of the veined cock rubbing against both clits as it slid in and out, the elastic of Lily's panties providing just the right amount of resistance.

A wonderful idea crossed Jessica's devious mind as she reveled in the building orgasm both in herself and on Lily's delicate face. As Lily pulled back the cock Jessica guided it out of her gently and grabbed her phone that was laying on her desk. "Do you have your lipstick sweetie?" She asked Lily

"Always!" Lily smiled as she took the slim gold tube from where she had tucked it in her stocking top. A small mirror popped out of the cover as she slipped the tube out.

"Just do a quick freshen up, I know someone who will really get a kick out of it." As Lily slipped the soft tip over her lips Jessica framed the picture. Her own open legs framing Lily's stunning figure, the rubber cock glistening with her own juices and lily elegantly applying a fresh coat of creamy colour. This would be fun for Tom.

Once she put the lipstick away Jessica pushed Lily onto one of the leather padded benches kissing her softly as she guided her, their creamy lips slipping easily together. Pushing her arms into the metal shackles she restrained the feisty redhead before climbing back onto the dick protruding from her. She straddled Lily and slipped the dick back into her waiting hole beginning a steady rhythm that had Lily moaning and close to orgasm. Leaning forward Jessica kissed Lily passionately as she felt her own climax build, her tempo building with her desire. Lily came first her gasping breaths and high pitched squeals as the dick rode in and out of her giving her peak away. Jessica continued to ride the rubber cock feeling her own special quiver begin. Moaning in tandem with Lily, now well into her second relentless orgasm, Jessica ploughed on feeling her pussy tighten and clench as she finally came. A special bonus as she felt herself squirt her own warm fluids down the shaft of the cock onto her prostrate, restrained fuck bunny.

Slipping herself off the dildo she kissed Lily tenderly thanking her for her Sterling work, kissing her sensitive nipples before releasing her from the bench. "I think your outfit passed muster." giggled Jessica as she caressed the young model's cheek enjoying seeing the smudged makeup all over her face. "I'll see you get a few more opportunities with us soon." As Lily got up and composed herself, Jessica handed her a plush dressing gown and a similar towel before showing her to the large luxurious bathroom adjoining her office. "Take as long as you need sweetie, you should find all you need in there." Lily grinned snatching a final kiss from Jessica as she entered the bathroom.

Jessica slumped into her large office chair allowing her fingers to slip back to her dripping pussy determined not to waste the opportunity of a second cumming. As she came again she imagined what she would tell Tom about her day and what devilish things she might suggest he do in front of her to see if her control was developing as planned.

Testing the water

It had been three days since they had chatted online but messages had been sent back and forth. Since Jessica's teasing messages the day after the last online session the messages were more relaxed and beginning to flow with sexual innuendo and double entendres. To make things a bit more steamy she set Tom a task.

'Hi Tom I thought to make tonight a bit more interesting we could play a little game. Send me a photo of something that gets you really hot and I'll do the same. No peaking until we see each other later. Jess'

Jessica already had the perfect picture in mind, she grinned remembering the spectacular orgasm she'd enjoyed while fucking the lovely Lily in her office. She did wonder what Tom would come up with, hopefully something she could play with. She picked the photo she had taken with Lily and sent it in an email emphasising the no peaking in the subject.

Seven p.m. came around and they both logged onto the video chat. Tom noticeably nervous but smiling. Her email pinged and she saw Tom's picture arrive in her mailbox "oh goodie, I've been looking forward to this all day I hope you chose something saucy Tom" she said smiling at his image. "Shall we open yours first or mine? Or both together?"

"Hi Jessica, Erm, together I guess?"

"Ok, ready?" She asked, seeing him nod and open his email "go" she saw his mouth drop, he didn't know they were her legs but the image down her flat tummy to her waiting snatch and the red headed lovely standing applying her lipstick with a glistening rubber cock hanging from her crotch was quite striking in its own right. Lily exuded dominance in the pose she held, just right for Tom.

She opened Tom's image and smiled as she took in the image of a raven haired dominatrix in a black satin corset, black sheer stockings and knee length black leather lace up boots. At her feet a submissive knelt, naked, looking up in awe of her power. In one hand she held the leash attached to the subs collar, in the other a strapon in a harness. 'My word Tom we are singing from the same hymn sheet today' she thought. She squeaked in delight and she saw Tom blush deeply, 'perfect!'

"I love your picture Tom the woman looks so powerful and in control, what is it that gets you hot about it?"

Tom was now clearly embarrassed and struggling with his inner desire to appear strong whilst also being honest with Jessica. "Errr...." he stammered, "I like her outfit." He finally said weakly.

"I'll admit Tom that is quite a look, I like it, maybe we could try it when we meet." she teased, Tom looked away.

"Sorry Tom, I didn't mean to tease, I genuinely wanted to have a bit of fun and learn something about each other. I can see you're a bit embarrassed so let me explain mine so we can share a bit of the load." she smiled warmly and Tom seemed to perk up a bit.

"Ok so I love this picture because firstly I've dabbled in being bisexual and I've enjoyed sex with another woman more than once. It's different to being with a man, more sensual. The same sex knows where to touch and caress to get the juices flowing so to speak." She looked up thoughtfully "I guess that's the same with guy on guy." she quivered at the thought of forcing guys to fuck each other, how delicious.

Tom was listening intently, her honesty about her sexual adventures having surprised him. He shuffled in his chair rather obviously try to reposition his growing cock. "How many times have you been with women?" He asked

"Oh I don't know, when the mood takes me I guess, I have a few girlfriends who like to play sometimes. Nothing beats a good hard cock but a sensual session with a beautiful woman really is a treat." She knew she was feeding his growing arousal, most men's fantasy is a threesome with two beautiful women, a tool she'd used more than once to seduce men into her service, why not this one too. "Hey maybe we could, you know, have a threesome sometime." she grinned and giggled. Deliberately leaving Tom wondering if she was serious.

"I also love the fact that this red head is a strong woman but looks delicate and feminine. She's making sure she looks fabulous before getting stuck in. Isn't she divine?"

Tom nodded "She is very pretty, I love her outfit too." he chuckled at his weak response.

"So Tom, over to you anything in your picture beyond her outfit that gets your juices flowing?"

"Well as you've been so honest I guess I should be too." She nodded at him smiling trying to encourage him to say what he wanted to say "I guess I kind of like the idea of being dominated by a woman, especially one dressed like that, it's a big turn on. Maybe it's because I spend my days at work being the boss it might be nice not to be for a change, to escape a bit, is that weird?"

"Why would it be weird? Plenty of men like the idea or there wouldn't be so much female dominant porn out there." She replied. "It's also possible that some women like the idea of being in charge for a change in the same way you like the idea of letting go, horses for courses so to speak."

Looking down, not making eye contact, his cheeks burning "I guess. You're not shocked? Not turned off by it?"

"Why would I be turned off? I like the idea to be honest." She didn't just like it, she lived for it but he didn't need to know that just yet. "Do you think I'd look good in that kind of get up?"

"I think you'd look stunning in that outfit but it's a bit presumptuous of me to want to see you in your lingerie isn't it?"

"Not really, there's got to be some sexual attraction, why not make it fun is what I say. If being submissive is something you find interesting I'm ok with that."

Tom stifled a yawn "oh sorry, long day, I'm not finding the conversation boring I promise."

"I know I can see you're stifling more than a yawn." she said looking down at the camera as if she was looking at his crotch. "Poor sleepy submissive." Tom slumped into his chair as the trigger hit him "Tom , can you hear me sweetie?"

"Yes Jessica."

"Good, Tom when I click of my fingers you'll awaken feeling very horny and the arousal will slowly build as we talk. Anything I do that you find sexy will be amplified ten times. When I ask you to jerk off you'll be thrilled and desperate to please me. You'll jack off until I tell you, you may cum but there will be a price. Once you agree to the price you must go through with it. It's your choice if you want to pay the price of cumming but if you don't you'll be unable to cum. Also you must be totally 100% truthful with me anytime you are touching your dick in my presence. Do you understand?"

"Yes Jessica."

"Excellent!" she snapped once and Tom's eyes blinked open "would you like me to dominate you someday Tom?" She asked coyly

"Well, erm, yeah I guess that would be nice." he managed weakly "I mean we get on and you certainly have the look I like so yeah that might be fun, but only if, like, you know, erm, if you want to." She smiled

"Oh Tom, I'd very much like to help you fulfil a fantasy so yeah I'd love to." she pushed her chair back a little and raised the hem of her skirt revealing her stocking tops. She saw him take a sharp intake of breath as he got noticeably harder in his pants. Next she scraped her hair back into a tight pony tail and put in a hair band to hold it. She loved watching him squirm as the arousal built.

"How about right now?" She asked

"I'm sorry right now what?"

"Would you like me to dominate you right now Tom?, would you like to submit to me?" She pulled out her lipstick twisting the tube revealing the dark burgundy red stick within and began to slowly apply it to her lips. Tom was like a deer in headlights his eyes wide, blushing a deep crimson almost visibly shaking with arousal

"Yes Mistress, I would."

"Excellent Tom, I'd like that too. Now why don't you slip those trousers and boxers off for me so I can see what we're working with, do it nice and sexy though, it's all about me now isn't it."

Tom stood and slowly unbuttoned his jeans, trying to strip like he'd seen them do in the movies. Meanwhile she raised her hem up further allowing him to see a glimpse of her panties. As his jeans slid to the floor she could see his cock was raging in his tight boxers. He hooked his fingers round the boxer waist band with his ass facing the camera, a remarkably nice tight ass she thought admiring it as he exposed it from the boxers.

"Now your shirt please Tom, submissives should be naked unless given the privilege of wearing clothes." Tom nodded and slowly unbuttoned his shirt before shrugging it off his shoulders, then quickly removed his undershirt. He now stood naked in front of the camera, cock stood very much to attention, "turn around slowly Tom so I can see my property." he slowly turned allowing her to take in his naked figure.

"Good boy Tom, how does it feel to obey a woman."

"It feels nice, like I have someone looking after me." he replied gingerly

"Of course I'm looking after you my sweet, now take a seat again and why don't you hold your cock in one hand." he sat and wrapped his right hand around his dick.

"Would you like to masturbate for me Tom?"

He squirmed as his cock twitched, "yes, very much."

"Ok Tom why don't you stroke it very slowly but no cumming or I'll be very upset." Tom started to rub his hand slowly up and down his meat. Jessica slid her panties to one side exposing her pussy to both her fingers and Tom's view. She slipped a red nailed finger end into herself caressing her clit softly, relishing the electric like sensations she generated. "So Tom do you like my lipstick?"

"Yes, mistress, it's very sexy, I like the dark red it's very...Seductive."

Jessica increased her rhythm "do you like lipgloss Tom?" Tom nodded, she smiled and slipped her wet finger out of her slit and slid it over her lips leaving a glossy sheen before returning it to her waiting hole. "Have you ever worn lipstick Tom?"

"Yes mistress." he looked confused briefly wondering why he had admitted such a thing so freely but continued slowly rubbing his cock. "Once I tried some of my ex's when she was out but got embarrassed and rubbed it off in case she came home."

Jessica grinned, "Sweetie you don't have to be embarrassed with me, I see you're quite excited there now, is that precum an your tip?"

"Yes mistress." he said nodding a look of determination on his face trying not to leak anything else.

"Good that means you are getting close, but you aren't to cum unless I specifically allow you." Tom nodded as he shivered slightly with arousal. "Why don't you take that precum on your finger and rub it on your lips, it'll be just like lipgloss, you can imagine wearing a lovely hot pink can't you?" He nodded again then nervously took the drip of clear fluid onto his finger and slid it across his lips.

"Wow Tom that looks amazing, that hot pink lipgloss really suits you." she giggled as he went back to stroking his breathing becoming laboured as he strained to contain his orgasm. "Tom stop stroking for me. Now we need to talk about payment and reward, just leave your hand on that lovely cock though."

Tom stopped stroking but left his hand on his dick as she asked. "So Tom, if I let you cum you are getting such a nice reward but there's nothing there for me as I'm so far away so I would like you to pay in another way, a little task for you as a tribute to your mistress for being so kind, do you think that's fair?" He nodded "good boy, now it's going to be your choice so listen carefully. If I say you may cum then you have my permission to cum but I want you to catch your cum in that empty glass on your desk and then I want to watch you drink it down and swallow it. Alternatively we can stop and you won't need to pay me any tribute but you won't get to cum, do you understand the terms of the bargain?"

"Yes mistress." he sat confused, shaking on the edge of orgasm, an almost impossible choice for him to take. She continued to play with her own sex, a slight moan from her only added to his own arousal "if I am permitted to cum I must then eat my own cum or not cum at all."

"That's right Tom, a mistress must have a tribute if she gives her sub permission to cum, and it looks like you are so close now it would be a shame to waste it." she teased.

"Ok mistress, I'll try." he finally said

"No Tom, just like Yoda would say, do or do not, there is no try. You will do this one little thing for me won't you Tom? I'd so like to see you eat your cum it might even get me off." she moaned again as her orgasm built enjoying the Hobson's choice she had given him and his inevitable resistance.

"Ok i'll do it!" he finally answered

"Oh I'm so pleased Tom, I bet you are so so close, it won't take too long so, grab the glass and put it over your tip and then you can start rubbing again, we don't want to lose a single drop. You have my permission to cum"

Tom did as he was told like a good little slave, he placed his tip in the glass and then began to rub while holding the glass in place with his other hand. His shaking grew as he quickly reached his peak. She saw his balls twitch and his back arch as he blew his load into the glass. As his orgasm diminished he gazed into the glass holding the warm white goo.

"Now Tom make sure you get the last drop from the tip and put the glass to your lips." he scooped the last drop with the lip of the glass and put it to his lips. "Bottoms up!" she said and he began to tip the glass. She saw the white cream slip into his mouth and he made a face as it slid over his tongue. "Now swallow Tom." she saw him swallow, "there that wasn't so bad was it?" Her climax washed over her the deliciousness of her control tipping her over the edge and into ecstasy.

As her orgasm abated she slid her finger from her pussy and slid her hem back down a little "very nice Tom, didn't it feel good to be controlled, to do something to please a dominant woman?"

"Yes mistress." he said smiling his cock already back to attention.

"Sleepy submissive." she said gently and he slipped back under her spell slumping back in his seat his face blanking. "You've been such a good boy Tom, I've very much enjoyed playing with you. When I wake you you will remember having a an intimate conversation with me, but you won't recall jacking yourself off in front of me or the fact that you ate your own cum but you will recall discussing it. Tomorrow when you are on your lunch break I'd like you to go to a nice department store and get a lovely lipstick, in a colour you really like. If asked it's for your girlfriend as a gift. Then you will go to another department and buy some lovely stockings and a nice garter belt. When you get home you'll pop it all the drawer of your desk and we'll delve deeper into your fetishes next time. Do you understand?"

"Yes mistress." he replied quietly

"Good boy, now when you wake up you'll want to jack off again but only once we've parted company. When you do cum, you'll be curious about the taste of your cum and you'll at the very least taste it but I'd very much like it if you swallowed the whole load like you did for me just now. It would make me very happy if you began eating all of your cum when you jack off. Because you know it will please me you'll be eager to try to do what I ask. Now be a good boy and put your pants and shirt back on." Tom pulled his pants up and buckled his belt then pulled his shirt back on without opening his eyes, once he was dressed she clicked her fingers and he was once again awake.