Jessica and Tom 01: The Hunt

"I'd say that box was paid for in full my sweet." Jessica nodded and grinned as the last of her climax ebbed away and they lay together enjoying the after glow of an intense coupling.

Change is afoot

Over the previous few days Tom had practiced with the plugs with varying success. He'd realised early that the small plug was useless and didn't stay in. The medium was the most successful with it staying in place and being just long enough to graze his prostate but annoyingly only if he sat in just the right way. The large plug was proving a challenge, his ass just didn't like the extra girth and he felt he was being reamed apart as it reached its widest point. He'd read that you needed to be patient, relaxed and keep trying.

On the fourth day the large plug slid home, a brief stab of pain made him yelp as the bulbous plug slipped in and his ass closed around the narrow shaft. The sensation was clouding his mind. The tip was pushing right on his prostate and he felt his precum oozing even from his flaccid cock, he even heard a moan escape him. He hesitated to sit but he knew Jessica would be calling soon, he gently sat and felt his weight slowly drive the plug deeper into him. More fluid beaded at the tip of his rapidly hardening cock. Once his weight was fully down, he began to relax feeling his ass pulsing around the invader in time with his pulsing cock.

His email pinged with the meeting invite and he scrambled to pull-up his shorts and pants which only served to move the plug around and further tease his gland. He was shaking with arousal by the time he managed to grasp the mouse and open the mail. It was then he saw the time, he hadn't realised he'd spent almost 10 full minutes getting his pants on and opening a mail, so distracted as he was, by his trembling.

When he opened the call he saw Jessica already there, a first, which made him even more flustered.

"Are you ok Tom? You're usually not tardy for a meeting?"

"Yes yes fine, just a bit..... distracted."

"Oh, what's got you so distracted?"

"Well, I'm currently experiencing the large plug and it's having more of an effect than I had expected."

"You're wearing it now?" He nodded slowly. "Oh, Tom how naughty of you. I bet it feels fabulous being filled like that. I'm impressed you've moved so quickly."

"Well, it was a bit uncomfortable but once it was in, yes well, it's having quite an effect."

Jessicas phone pinged "If it's having an effect, I'm not sure you're going to be crazy about this next bit." she couldn't contain her chuckle when his doorbell chimed.

"Really! For fucks sake!"

"It's a delivery from me." Her chuckle quickly degenerating into a full-blown laugh as he struggled to stand properly with the plug exerting its tip on his magic spot.

"Can you leave it at the door please?" he shouted

"Sorry man I need a signature." Came a muffled response from beyond the door.

Tom shuffled awkwardly across the lounge not daring to stride normally with the toy in place. Sadly, he was out of shot in no time waddling to the door, but she heard the conversation.

"You Ok man?"

"Yes yes, just some bad prawns for lunch." Jessica lost it, her laughter caused tears in her eyes. She franticly grabbed at some tissues to prevent her mascara from running. Her hoots could be heard across the room. She imagined how totally confused the delivery guy must be and how awfully self conscious Tom must be feeling. She heard the door close and soon Tom waddled back into view with a large cardboard box in his hands. Gingerly he sat after placing the box on the desk.

"Don't tell me this is an even bigger toy?"

Jessica tried to stifle her fit of giggles, despite her best efforts the tears had finally made her makeup run and she was doing her best to dab at her face to limit the damage.

"Oh dear I haven't seen such perfect timing in so long, thank you so much that's really tickled me. Note to self, waterproof mascara next time"

"So, what's in the box?"

"Well it's a surprise but you have to earn it."

"I thought I just did."

"Well, it was certainly a good down payment sweetie, but this box is very special and only for sleepy submissives." Tom slumped back a moan briefly percolating as his weight rested him back on the plug still embedded in his tight ass.

"Good boy Tom. Today we're going to go even deeper sweetie, do you remember what floor you're on?"

"Twenty-two mistress."

"Excellent, in your mind you may stand and start to descend the next staircase, 10,9,8...." she continued to deepen his trance, sinking him further into her servitude. The next task would be a potential challenge to him if his masculinity was unrestrained. Soon he reached his thirtieth level and she changed her tac slightly.

"Tom you are so deep in trance now as you reach the 30th floor you see a lovely Art Deco landing area beautifully furnished with sumptuous leather couches. In the corner is an old-fashioned gated lift, no more stairs for you as you are such a good obedient submissive." Keeping her voice smooth and her tone even. "Go and have a seat in one of those lovely soft couches, feel it wrap around you, hugging you softly. Tom from now on each level you descend by the lift will take you ten times deeper into submission and each level the lift takes you to will look just like this one."

"Tom I want you to listen carefully now, when I say 'obedient submissive' you will be powerless to obey my suggestion even when you are fully awake. It will be very important to you to obey and please me. If i want you to return to your normal behaviour without being totally obedient I'll say 'as you were'. Is that clear in your mind Tom?" He nodded slowly.

"When I say 'tell me the truth' when asking you a question you will be compelled to be totally honest about that answer. When I use either triggers you won't feel weird or odd obeying or telling me the truth. You will feel satisfied and happy knowing you have pleased your mistress, you will forget any truths you tell me using these triggers. Do you understand these triggers Tom?"

"Yes mistress." he mumbled.

"Excellent Tom, I think we'd best try it out so remember which floor you are on and when I snap my fingers you will awaken not remembering anything about this little interlude, not bothered by the 30 minutes you've lost, you'll assume you were just telling me about your day." She snapped and his eyes fluttered open

"God you must be so bored hearing me blather on."

"Nonsense Tom, I like to hear about your life. Tell me the truth Is your cock leaking precum?"

"Yes, quite a lot actually, I think I'm getting a wet spot."

"Good boy" she praised and he smiled "tell me the truth have you ever been made up as a sissy boy?"

"No, never."

"Would you like to?" she deliberately omitted the trigger to see if it was working as she intended.

"Like to what?"

"Tell me the truth, would you like to be dressed up like a girl?"

"Yes I think that would be exciting."

"Me too." she grinned in triumph.

"Tom when we finish this call you'll be a good obedient submissive and open the box, inside you'll find a flash drive with videos on it and a large amount of cosmetics. You will use the coming weekend and follow the whole series of videos following every instruction as if they were my own. You'll do each series in full and take a photo each time and send it to me so I can see your progress. When you decide which is your favourite you'll use the next week to focus on that one and get it perfect before moving to your second favourite to perfect it and then the last one. When you finish each look and you've sent me the photo you'll clean up and put everything away and quickly forget what you just did assuming you were just absently surfing the web or watching Netflix. Do you understand?"

"Of course, it sounds fun."

"Good boy, you'll want to go and buy a nice magnifying makeup mirror too."

"Will do."

"Excellent, well Tom I need to do some work so time to go I'm afraid." his face was crestfallen "Don't be sad, it won't be long till we meet for real and then we'll have some real fun."

"I guess, I can't wait to finally meet you for real."

"Me too Tom, now don't forget what I told you, good night sweetie." she blew him a kiss as he wondered what she meant.

Her pussy as throbbing with desire by the end of the call, she'd successfully got him to be obedient while awake as well as tell her honestly what he was feeling on command. She needed restraint though and tried to calm herself, refraining from pleasuring herself at least for now, she wanted to see the true results of the suggestions before celebrating.

It feels wrong but right

The weekend came before he knew it. He woke early on Saturday and after his coffee and cereal he sat naked at his desk with his new magnifying mirror in front of him and opened the box. Next he inserted the flash drive and opened the first video. Sarah appeared on the screen still radiant despite not having any makeup on, she smiled and introduced herself before describing each item in the box. Once she had familiarised him with the contents, she asked him to open the next video labelled 'daily look'.

Tom opened the next file as instructed and watched as Sarah first explained which items he would need for this look. She explained how to cleanse and exfoliate before starting and asked him to go and do that first which he did then returned. Now she explained how important a good foundation and concealer were, how he should apply each and what areas of his face to pay particular attention to. In no time Tom had managed to apply a reasonable layer of foundation and got a passable complexion.

Sarah then asked him to take out the first of the eyeshadow pallets she had included, this one was mainly warm browns. Not too showy and glittery but enough to play with. She explained where to apply the colours, how to blend each colour into the next and how to use each of the brushes. Again, Tom made a passable first attempt with only a few mistakes he thought. His eyes now shimmered a light beige in the inner corner as it darkened out to a deep brown in the crease and then lightened again over the eyelid and out to his brow bones.

Sarah had decided to start simple for this look and explained how to do a soft eyeliner with a kohl pencil. With the soft pencil being more forgiving he managed to get a reasonably straight line on his eyelid. Mascara was tricky to avoid clumps transferring onto his eyeshadow but he managed it eventually. He found his cock growing when he took in the transformation that he saw in the mirror.

Sarah then asked him to find the first of the blusher palettes and the large blusher brush. She explained how to load the brush and where to start applying the light colour over his creamy cheeks, just enough to show off a little cheek bone.

Finally, she asked him to find a lipliner pencil and a long clear plastic tube with a long gold metallic lid holding the nude lip colour she had chosen for him. She explained how to line his lips to get the fullest look and no bleeding of the colour. As he unscrewed the lid from the lip colour the gentle perfume caused him to become more aroused, he placed the soft applicator onto his lips as Sarah showed him and as he slipped the colour over his lips he felt his cock grow harder and harder.

Checking in the mirror at the completed look he felt his cock twitch, he surprised himself with the transformation, he looked feminine, sexy even. Pulling out his phone he took several selfies trying to pout in just the right way for Jessica before sending the best one to her by WhatsApp while making another cup of coffee then he got cleaned up and opened the next video.

For the next look Sarah had gone a lot darker. The same process to prepare was used and she went over the use of the foundation and concealer again and he followed the process to the letter once again, this time it went better with a better finish and less caking. To give his face more definition she explained where to put contouring and highlighting powder on his cheeks, brow and chin then how to blend them with a large soft brush. Following this she explained how to make a metallic effect on his cheeks with a bronzer. As the layers of makeup increased so did his arousal, his manhood had been dripping for a while now and hadn't been soft for hours.

For his eyes she asked him to find the next palette, this one more glittery with darker shades of brown and black. In the inner corner she explained how to highlight the inner part of the eye then she explained how to apply the black cream eyeshadow pencil along the lower lid blending it quickly to avoid it drying before it could be smudged into place. She taught him how to load a brush and apply a heavy dark brown into his eye crease before applying a lighter shimmery beige towards the brow before blending them all together to give a smooth shimmery effect. Next, she introduced his first liquid eyeliner and explained how best to apply a small wing to his eyes to give extra definition before having him curl his lashes and apply his mascara.

The soft perfume of the deep crimson lipstick did nothing to reduce his Arousal as he filled in his dark red lined lips to finish his 'evening look'.

Again he pouted and posed for the camera before sending the photos to Jessica now fighting the desire to jerk off. He had a glass of wine before cleaning up and sitting back down for the next phase of the course.

The final look was to be what Jessica had termed a 'slutty look'. Sarah didn't 100% know what she meant but had an idea. Pornstar makeup or at least her version of it.

Once again, he went through the routine for foundation and concealer, this time he felt he'd nailed it. His skin looked smooth and flawless just like Sarah's. Next, she explained how to apply liquid highlighter and contouring colours and showed him where to blend them to make his face even more defined. A liberal use of bronzer across his cheeks really started to make him look very tarty.

The eyes this time were to be much more extravagant. She explained how he needed to start with a mid tone deep shimmery beige in his crease which he followed from the last look but this time it was a more bold colour. The deep fire red she wanted to use came in a very limited pallet and was also a shimmery glittery finish. This was to be packed heavily onto his lower eyelid and then blended up and out to begin a much longer wing. In the outer corner she asked him to apply a little purple to the red to smoke the look a little before applying some very light shimmery powered along his brow bones. Finally she explained how to put the same fiery red halfway along his lower lids to make the colour look more vibrant still.

Next came the hardest part. She once again had him find the liquid eyeliner but this time he would need a steady hand, his constant state of arousal didn't help but he would try his best. He drew a long straight wing out from his outer corner almost to the end of his brow then began to fill it back in towards his eyelid. She explained how to apply this liner along his inner lash line to really pop the whites of his eyes then explained how to apply the large ornate false lashes before applying his mascara once again.

His lips were to be a deep burgundy courtesy of an expensive Armani lipstick which glided over his lips like silk. The finish was a glossy wanton look that screamed cocksucker!

The drama of this look both scared and aroused him and he found his hand around his cock and stroking vigorously as he inspected his handiwork. It wasn't long before precum was blossoming from his tip once again and he slipped some onto his finger using it as extra gloss. The thought of sucking another mans cock entered his mind briefly as he reached his peak and he exploded, ribbons of milky fluid spurted into the air some landing on his face and some on the mirror in front of him. Slightly embarrassed he scooped up the jism with his fingers and swallowed what he could before remembering he needed to take pictures for Jessica. Doing his best to touch up where the cum had smudged the makeup he pouted again and took another series of selfies and sent them to Jessica.

With his arousal sated for now he tidied the makeup away into its box and put it in his closet and went for a long shower, washing away the vivid colours from his face.

When he came out of the shower, he started to tidy the house unsure why there was lipstick marks on his wine glass and coffee cup as he'd not had any women in his apartment for months.

For the entire weekend he repeated the cycle of watching the videos and practicing the looks. He'd decided the 'daily look' was a good place to start so practiced this several times to perfect it as he had been instructed. By the end of the weekend, he'd even started to add his own little flairs to the look with deeper colours on the eyes and experimented with the different shades of lipsticks Sarah had included in the box.

As Jessica reviewed the photos her pussy began to drip. Knowing Tom was sat in his home feminising himself without even knowing he was doing it. She imagined him at his desk practicing how to apply makeup and adding his own touches to it was becoming a real turn on for her especially when she considered he likely had a rubber plug in his ass the whole time.

The pornstar look pictures he had sent had stopped her in her tracks, thankfully she was in her limo at the time and her driver was no stranger to her sexual antics. He didn't seem to notice as; behind the dark rear windows she began to rub her clit and moan with desire as the vehicle slipped through the evening city traffic.

Interaction at a distance

It had been several days since their last on line meeting. Jessica had thoroughly enjoyed all the pictures Tom had sent of his various attempts at Sarah's makeup looks. Each one was better and better as he practiced. It was looking more and more like he was accepting his role as a sissy slave without even knowing it.

As Jessica opened the meeting software she found Tom sat eagerly awaiting her with a big grin on his face. "You look like the cat that got the cream" she said as a hello.

"I guess I do, I have good news!"

"Do tell."

"I have been playing with the toys you sent and I am now ok with getting the prostate massager in."

"That's great Tom, I hope you were gentle I wouldn't want you hurting yourself."

"No of course not, I've been practicing most days and I thought I'd give it a go last night and it just sort of happened. It seems easier to use than the large plug to be honest."

"OK well I'm pleased you've managed to work up to it at your own pace."

"So what do we do now? You said it was interactive, so I guessed you'd want to have some fun with it."

A sly grin crossed her glossy pink lips "Well there's an idea. Have you played with any of the settings yourself?"

"No, I thought it was an us thing so wanted to explore it together."

"What a considerate thing to do Tom." She opened her phone and found the app for the toy. "Are you wearing it now?"

"Yes," he nodded eagerly. She pressed a button and his face immediately registered the sensation in his ass as the toy buzzed to life. His mouth opened and a small moan escaped him.

"Well that seems to be working." she pressed another button and increased the vibration a little more. To her delight he began to squirm then grind against the seat. She could see his trousers tented by his raging hard on "you seem a little distracted Tom."

"You could say that. It feels really good."

"Now imagine how much fun it would be if you were out shopping and i just turned this on, or maybe in a work meeting." her pussy moistened at the thought of randomly turning on the toy just to embarrass him in public. His grinding was becoming quite purposeful now as he enjoyed the sensation of the toy buzzing against his engorging p-spot.