Jessica and Tom 01: The Hunt

"Good night Jessica." he closed the meeting and she watched his hijacked camera as he disappeared for his shower still completely unaware he was wearing bright red lipstick covered in his own cum, his training was progressing surprisingly quickly. Perhaps a real life meeting was what she needed.

As she watched she checked her own company website for the anal toys she would send him, a starter pack, a new prostate massager that allowed app based control of the vibration and movement control and of course lots of lube.

That wasn't the only thing she would be sending though. She opened a new email to Sarah at the salon and began to type.

Hi Sarah

As you know i'm breaking in a new boy toy and he has a thing for playing dress up but no idea on how to apply his makeup. Could you please put together a kit of all the products I should send him and do a set of videos that he can follow to learn the basics. I'd like him to know how to do a nice daily look, a sophisticated going out look and a very naughty slutty look. You know what I like. Put it all in a nice wooden box and let me know when I can pick it up.

I've attached a few pictures of him so you know what you're working with.

Look forward to seeing you soon

Jessica

Her plan was gathering pace and she could see the beginnings of a beautiful hypnotised sissy slave she could toy with for a long time to come. As she deepened his submission so would she deepen the depravity of the things she would introduce him to.

A package arrives

When Tom got home a few days after his last call from Jessica the promised box was waiting with the concierge of his building. The days between had been busy and neither he nor Jessica had managed to get free time to chat beyond the odd message. Jessica had sent a few pictures of her in various outfits on her way to work and Tom had tried to keep pace but the glamour of this woman seemed to know no bounds.

Tom signed for the package and quickly retreated into the elevator thanking his lucky stars Jesica had used plain packaging for the 'gifts' she had sent him. As he got to his apartment his phone pinged with a message.

'No peeking at the contents, see you online at the usual time, I want to see your face when you open the box, Jessica xx!'

Toms face blushed a deep red, knowing only that anal toys were in the box was a recipe for his brain to conjure up all manner of worst case scenarios. Either way he couldn't contain the growing erection in his pants at the thought of seeing Jessica again and telling her the good news about his annual leave approval.

He grabbed a light meal and showered before starting to check his mail for the meeting e-mail which arrived as always at at five minutes to seven. He entered the chat room his stomach churning as he looked at the large box he had left on the desk next to him.

The familiar 'whoomp' sound signified Jessica had arrived and she beamed a dazzling smile with cherry red lips as her camera connected. "Hey Tom, you got it, I'm so excited!"

"Hi Jessica, me too, I think." he looked down at the box with a look of trepidation.

"Don't worry sweetie, you'll thank me I'm sure. Go ahead open the box." she'd arranged the packing very carefully to get his blood pumping. His jaw dropped and his blood ran cold as he opened it and saw the item laid on top. The double ended dildo she had used with Lily lay on top, it's girth was terrifying and it's length even more so. He didn't know it was the one from the photo but it gave Jessica such a buzz to see his fright at the size of the rubber cock.

"Holy Shit Jessica, I said small! This is.... huge!"

Jessica was giggling wildly at his discomfort, "You don't think it's gonna work for you then?" Sarcasm dripped from her word. Finally she decided to give him some respite as he held it in front of him examining the realistic mushroom ends and veined texture dropping in his hands. "I'm joking with you Tom, I had to pull your chain somehow." her giggles subsided. "Put that monster down and lift up the cardboard."

Tom's relief was clear as he gingerly placed the bouncing rubber dick down on his desk then opened the next layer of packaging. "Ok that's kinda more like it." he said pulling out a blister pack of several rubber butt plugs, the bright packaging emblazoned with 'anal starter kit' in cartoon letters.

As he inspected the 3 black butt plugs and one medium sized dildo she continued "I think you'll find the small one is too small but the next one up should be a good starting point. The dildo is for once you are ok with the large. There's some lube in the box too for you."

Tom opened the package and inspected the plug marked 'medium' its soft rubbery feel was pleasant enough. It's narrow tip flared out to about one and a half inches before curving sharply back to a narrow shaft before the flared base. "It's still a bit intimidating, I think I'll start small if that's ok."

"Of course Tom, you must take it at your own pace." Tom reached into the box and found the 3 large bottles of thick lube and placed them on the desk. "I guess I'll need all of this to get this one in." he said pointing to the first gift lying on the desk. She chuckled as her pussy moistened at the thought of riding that very same rubber dildo with the lovely red head only a few days before.

"There's one more gift in there Tom, one for both of us." She smiled coyly as he reached into the box once again and pulled out an all black expensive looking box. He opened the leather effect box to find an organic looking L- shaped toy about six inches in length on one side and four in the other; accompanied by a small remote. As he took it out the sensation of the soft matte silicone surprised him. It was quite slippery but not so much that it was difficult to hold. The toy was much more firm to the touch than the rubbery plugs.

"Ok this looks kinda interesting."

"It's a Prostate massager Tom, it goes up your butt but it's designed to touch your prostate and stimulate it like we discussed but this is a special model." he was rolling the toy over in his hands as she explained "It's got a remote but it also is able to connect to bluetooth and via that I can control it from here. Just zap the QR code with your phone and we can get the app downloaded."

Tom zapped the code and his phone started to download the app. They chatted about their last few days until the phone pinged indicating the app was ready. He followed Jessicas instructions to set up the device and in no time. "All done so hold the base of the toy and press the on button so I can show you what it does."

Tom held the tactile rubber in his left hand and she tinkered briefly with her phone. The toy buzzed to life the intensity of the vibrations pulsing up and down. "Imagine having this in at work and me being able to turn it on at any time so give you a lovely prostate vibe." she grinned with desire.

"I'm not sure that would be great in a meeting"

"No Tom that's the point, no one would know but you that I was playing with you, see how silent it is!" She was right, it was very discrete and the idea of not knowing when it might come on was quite erotic. "Now for the party piece!" She hit another control on her phone and the whole plug began to move back and forth whilst still vibrating. "This will move in and out and press against your p-spot, after a while you'll be getting a bit damp up front as it squeezes the precum up your shaft and I'm told soon after that a rather tremendous orgasm should follow."

Tom looked at the toy a smile crossing his lips then a frown "You really are a devious one aren't you! I'm not sure about the size but let's start small with the plugs and see where we go from there."

"Of course Tom, its got to be at your pace and must be comfortable. Do you want to try one now?"

"Erm, well I guess no time like the present, but let me go do this in the bathroom, back in a moment." she smiled encouragingly and nodded

"I'll be right here." he left the desk with the butt plugs and disappeared out of shot for a few minutes. She slipped her finger into her panties and deep into her warm slick slit visualising him lubing the plug up before placing the tip against his virgin asshole. Slowly as he applied pressure she imagined his face as the tip slipped slowly into his waiting sphincter, a gasp maybe as it passed into him and his hole grips the narrow bottom shaft of the plug. From the distance she heard a weak moan right on cue as she quickened her pace on her engorged clit.

Tom waddled back to his chair with a pair of tight trunks on and sat back down. "How does it feel Tom?"

"Weird, it slipped in really quickly but wanted to pop straight out again as it's quite slippy, hence the pants." He pointed down at the trim trunks he was once again wearing. "Feels kinda odd but not getting any fireworks going off, should I try the medium?"

"Please do!" She smiled as she continued to strum her special spot. Tom got up and disappeared again so she decided it was a convenient time to enjoy herself a little more. Reaching into her own drawer she pulled out her favourite new toy. The smooth silicone slipped easily between her waiting lips and she gasped as one horn slipped into place just on her g- spot while the other perfectly met her clit. With the remote she started the vibrator and enjoyed the flowing pulses start to build. Once again enjoying the mental image of Tom slipping a plug into his now not so virgin ass.

He returned this time naked and walking a little awkwardly. As he sat back down a moan escaped him as the plug slid against his prostate "Ohhhh!" He exclaimed. She saw the tell tale bead of precum appear on his tip.

"Now I think you're getting it Tom." She gently rotated and moved the vibe in her pussy in a circular motion making sure it hit just the right spots. "Why don't you see what happens when you start to play with yourself."

Tom began to slip his lube covered fingers up and down his shaft. His excitement quickly growing as he watched Jessica build towards he own orgasm he felt the plug slip against his prostate as he instinctively began to grind on the plug in time with his stroking rhythm. Precum dripped from his tip and he moaned.

"You seem to be dripping there Tom, just like me. Be a good boy and make sure you don't waste a drop." his finger slid instinctively to the tip and scooped the salty sweet liquid from it before licking the finger clean, his subliminal programming not even needing him to be in trance to want to obey her. His whole body began to shake as he reached the edge of his climax.

"Cum for me sweetie!" he exploded, ribbons of cum spilled from his cock as it jerked and twitched, the plug forcing the cum out as his ass clenched in time with his orgasm. He moaned deeply as he surrendered to his first anal orgasm as she felt her own crash over her.

As she opened her eyes from her climax she was thrilled to see him scooping finger loads of cum hungrily into his mouth without her having to remind him . His cock still twitching and expelling pearls of creamy cum, his body continuing to shake as the waves of pleasure subsided.

"I think we might have a convert to anal play." she teased as he caught his breath.

"Wow! that was unexpected."

"Wasn't it."

"What now?"

"Well I guess now I get you to forget it all." she said with a sigh, "I have to let you work up to the next phase on your own and this was a bit ahead of schedule."

"I don't understand?" He cocked his head quizzically

"You won't for a while yet sweetie at least until we meet."

"Oh about that, I got my leave and client visit sorted out. I'm planning to come to your part of the world in about 4 weeks."

"Perfect, we should be right on schedule by then my sleepy submissive." Tom slumped back in his chair eyes snapping closed. "Now sweetie, you'll remember opening the package and having an earnest chat about your curiosity of anal play and what all the toys are for. You won't recall using any of the toys or cumming for me so extravagantly nor my rather self indulgent display. When I wake you you'll send me the dates of your visit, clean up the toys you've used and put them neatly back in the packaging. From tomorrow you'll start to experiment with the plugs when you jerk off until you can comfortably fit in the prostate massager. Do you understand Tom?"

"Yes mistress."

"Good boy, now when we say good night you'll accomplish your tasks, shower and have a wonderful nights sleep." snap went her fingers and he flickered awake.

"I'll just send you the dates by email so we can make a plan, I guess you know good places to eat and drink?"

"Yes Tom I have a few in mind which should work. Lovely, I just got the message now, I can't wait to finally meet you we're going to have so much fun."

"Me too, I really feel we're getting a connection, I'm looking forward to seeing you in the flesh."

"Time to say goodnight Tom, speak soon." She blew him a kiss and signed off. Four weeks left her a little time at least to get him fully conditioned.

Tom turned off his computer and gathered the toys together and went to the bathroom. He extracted the medium sized plug and washed it thoroughly along with the small one before replacing them in the package and sealing it up again then Put all the boxes back into the large box they had come in before jumping in the shower.

You can learn anything on the internet

Morning came spearing through the gap in her blinds Jessica squinted at the intrusion but it was time to get her ass out of bed if she was to get her plan completed. She checked her phone and was pleased to see a message from Sarah asking her to pop by the salon as her gift box was ready. Perfect timing.

The driver dropped her outside the nondescript mirrored door of the salon and she entered without knocking. Sarah was in the office working on an email. Her platinum blond hair was tied in a loose ponytail her makeup impeccable as you'd expect with someone in her line of work. Her delicate pink lips smiled as she saw Jessica enter. She stood up and grabbed a smooth wooden box about the size of a wine box from her desk.

"How does this look work for you?" She asked brushing her hand over her perfect face. Her sky blue eyes were complimented with a shimmering creamy silver towards the inside and out to darker shades of brown. Her full lashes flicked as she blinked revealing the fine eyeliner along her lid. Her cheeks glowed a glorious bronze and shimmered in the light from the makeup mirror, her almost nude pink lips glistened subtly but just enough to scream 'classy'.

"Love it" Jessica exclaimed as she air kissed her friend. "Did you include it in his course?"

"That's why I'm wearing it, I've just finished the last video for him. It's his subtle day look, not tarty but it would still look good wrapped around a nice cock." She giggled as she handed the flash drive to Jessica along with the box. "Everything he needs is in here and the videos are on the drive."

Jessica sat the box on the counter and opened the polished wood lid, inside was a plethora of products. Ornately packaged eye shadow palettes, lipsticks, glosses, creams and foundations along with a set of professional brushes. "Perfect," she smiled "I think I owe you one." Jessica leaned in and kissed Sarah gently. Sarah responded eagerly, slipping her tongue into Jessica's mouth and her soft hands onto her pert rump.

"Step into my office, I'm sure we can come up with a payment plan." Sarah guided Jessica by the hand to a door next to the office which lead into a dimly lit room. Jessica grinned with anticipation.

Sarah slinked into the dim room, a plush satin covered bed sat in the centre of the room, ornate wrought iron formed the head and foot boards, large metal eyelets were fitted over the structure and draped through them lay fat silk ropes. Sarah lounged into a leather Chesterfield, still guiding Jessica by the hand. Jessica stooped to kiss Sarah as she was guided to her knees in front of her. Their passionate kiss continued for some time, both enjoying the sensuous touch and smell of the other their arousal growing in unison.

Sarah broke the kiss and began to unbutton her beauticians tunic dress, the fabric falling to one side revealing her large breasts held inside a sheer lace bra. Jessica took the hint and began to kiss down her neck leaving subtle lip. Sarah arched her back as goosebumps formed from the sensation of her warm breath on her sensitive skin. Working her way down to her cleavage Jessica left delicate lip prints as she kissed.

Sarah released the bra allowing her tits their freedom and Jessica immediately latched onto her hard nipple, nuzzling and sucking it relentlessly before moving to the other. Sarah unbuttoned the tunic further until it was completely open, the black cotton fabric falling away to reveal her perfect figure clad now in only nude lace topped hold ups, her pussy glistening with excitement. Jessica continued her downward exploration lowering her head to be level with Sarah's sweet smelling sex. Without invitation she slipped her tongue into the warm folds of her pussy lips and soon found the throbbing clit within, the welcome invasion causing Sarah to gasp, then moan.

Sarah knew Jessica rarely submitted to anyone but when it happened it was something to relish. The building heat from below being fanned by her client's talented tongue caused her hips to start to grind into Jessica and her hands held her head just where she wanted it.

Her dripping sex needed more, Sarah stood and had Jessica stand. Slipping her hand to her side Sarah slid the zipper of Jessicas tight blue dress down then slipped it off her shoulders allowing it to fall to the floor. Jessica's panties were wet with desire, her breasts heaving in their lace prison, her deep red lips slick with Sarah's arousal. Slipping her hand behind she freed Jessicas breasts and slowly slid her panties over her pert ass allowing both garments to land in the same pile as her dress. Taking her by the hand Sarah guided her naked charge to the bed, lying her delicately on the black satin sheets.

With thick soft black leather cuffs she bound her tightly in place then reached into a drawer in the nearby pedestal. Grinning she slid a leather strap around Jessicas head slipping the attached rubber gag into her supple lips before fastening the buckle. The other side of the rubber gag was a 10 inch veined black cock which she intended to ride vigorously. Straddling Jessicas head reverse cowgirl she guided the phallus into herself inch by glorious inch feeling the ridges and veins rub on her clit as it went deeper.

Once it was buried deep into her slit she began to grind up and down building her ecstasy. She lowered her head into Jessicas waiting mound her musky scent only adding to the arousal as she slipped her tongue into her friend while thrusting on the cock gag. She relished her friends moaning and trembling as she toyed with her clit while her own orgasm became imminent. Her slit trembled and she screamed with release feeling her juice flow down the shaft and onto pretty Jessica's face.

Sliding the rubber cock gag from her pussy "I'm not done with you yet young lady!". Under the gag Jessica tried to grin, her eyes wide with desire now. Sarah slipped the gag from her mouth but left her restrained as she once again reached into the pedestal next to the bed, the rattling of the metal buckles filled Jessica with joy as she saw the strapon in Sarah's hands. A small plug stuck up inside the harness to stimulate the already glowing wearer. The dong on the front was a good 10 inches and adorned with multiple ridges and nubs, of which she felt every one as Sarah slipped it teasingly into her waiting snatch.

Sarah began to pump and thrust into her prone friends sex, fucking her harder and harder egged on by Jessicas now incessant moans and cries of desire. It didn't take long before Jessicas back was arching, her arms and legs pulling hard against the leather restrains, her face drawn in sexual pleasure as she came. Her spasms subsiding, Sarah kissed her friend tenderly as she caressed her restrained body as she withdrew the strapon, enjoying the twitches of ecstasy that came with being at someone else's mercy.