Jessica and Tom 01: The Hunt

"Wow, I had no idea we'd have such an intimate chat tonight, I feel a bit relieved actually. I don't think I've ever admitted that to a woman before, I was so scared it might be seen as a weakness."

"Not at all Tom, like I said some women like the idea of being in the driving seat in a relationship. I'd love to play with the idea when we finally meet if you would like that?"

"Wow yes very much I would." he grinned the relief almost palpable in his voice having unburdened his inner desires and found they didn't frighten off this young vixen.

"Tom I have an early start tomorrow so I need to get off to bed but let's get together again in a few days and chat some more. Maybe we'll find some other kinks we both share." She winked giving him a warm smile.

"Sure I'd love that, will you let me know what works for you?"

"Of course Tom, don't worry I'll be in touch soon." With that she gave him a wave and disconnected the call.

Watching him on her other screen through his hijacked webcam she saw he was already wriggling out of his pants again and his shirt was off. His cock was once again rock hard and he was avidly searching for an appropriate video. To her delight he found a cum eating instruction video almost immediately and began stroking himself as the pretty blond girl teased and taunted about how she was going to make him eat his own jizz.

Before the video was through he was spurting another load of cum onto his belly. His finger delved into the creamy white liquid and he scooped a glob from himself and sniffed it, his nose wrinkled in distaste but he slipped it into his mouth followed by two more sticky scoops as the blonde on screen vigorously encouraged him to slip his load into his mouth and slosh it around like a little cum slut. She could see his world was spinning and he was awash with lust and desire. Just where she wanted him

Unusual shopping trip

Tom's morning had been the same old dull routine of answering mails and fire fighting issues between his staff and unimpressed customers. He was looking forward to some fresh air at lunch. As he pondered what to eat he came to a decision he should go buy something for Jessica so, before he got lunch he'd drop into one of the big high street stores and pick out something nice, not too big but nice.

A few minutes walk found him a the door of one of the large department stores his town had to offer, this one being the higher end of the market. As always the powerful smell of perfume wafted over him as he opened the door, all the brightly lit cosmetics stands being close to the main entrance. A young counter girl approached him as he browsed.

"Can I help at all sir?"

"Erm yeah I guess, I was looking for a small gift for a new friend, she mentioned she was into nice lipsticks but I have no idea what to look for."

"Ok no problem I think we can help, any idea what colour she likes?" she asked cheerfully

"She seems to favour bold reds and burgundies" Tom pointed to a picture at the adjacent stand "a bit like this."

"Ah I know exactly the one for you." she guided him through the forest of glittering brightly lit stands all with very pretty assistants staffing them. They soon arrived at the Armani stand, a striking tall blond was there manning the desk. "This gentleman is looking for the ultimate red lipstick for his new friend." she said gesturing to Tom "Do you think you can you help Helen?"

"I think we have just the thing." She smiled warmly. Turning to Tom she said "do you like this red sir?" she pointed to her own full red lips generously coated in a deep crimson matte colour.

Tom felt completely out of his depth at this point, "erm, wow yes that is nice." he smiled awkwardly.

"It really is the best in the business." she reached into her drawer and pulled out a red and black tube inlaid with a small gold Armani logo. "This is our shade 400, it's divine!" She slipped the stick out of its tube and twisted the stick slowly up. The crimson stick glistened slightly its tip showing wear from her many applications. She slipped it over her lips touching up what he thought were already perfect lips. The colour glided on thick and he felt his cock stir as the lovely blond pouted so he could admire the colour.

"That's ideal I think, I'll take it please." she smiled back at him then picked out a fresh box containing a new lipstick and rang it up on the till. An exorbitant amount for such a small thing but Jessica would love it. He popped the bag into his pocket and asked where the lingerie department was. The blond smiled with her perfect lips and pointed to the escalators

"First floor, turn right, she is a lucky girl this new woman of yours!" She said as he turned to find the next purchase. He went up one floor and as the clamour of perfume dissipated his eyes were confronted with all manner of frilly underthings.

He wandered about and discounted the more trashy minimalist lingerie, his preference was to leave more to the imagination, he liked more vintage lingerie. In the corner a small concession stood out. Around a 50's pinup style model read the words 'What Katy Did!" The lingerie was just right.

He gingerly approached the counter and a middle aged lady looked up from her stock report. Her rockabilly look was just right for the stall, small ticks of black eyeliner, neutral eyeshadow red lips and a healthy amount of blusher gave her a real pin up look. Her tight ankle length A line dress in a floral satin was sexy but conservative, like a sexy librarian.

"Can I help you sir?"

"Yeah I'd like to get my new friend a garter belt and some stockings for a night out, I have no idea what to get but your stuff seemed more classy than the other stuff." She smiled at him kindly.

"Of course, do you know her measurements?" Tom's blood ran cold,

"Er no, but I guess she's a similar size to me, her waist is obviously a bit more shapely than mine though." they both laughed.

"OK lets see what you like in the garter belts and then we can sort out the stockings." She guided him round to the right rack and held up a few items, the clasps clicking off each other as they swung in the air. "These are our best sellers, nice comfortable satin material with strong straps to hold up even the most determined droopy stocking. This one has 8 straps and this one six, most garters only come with 4 little straps these days and they struggle sometimes."

She handed the two items to Tom who held each up eyeing the garments as if he knew what he was looking for.

"We do them in black and also in a nice dark grey, a deep emerald green, a lovely bridal nude and a feisty red but I think that looks a bit tarty to be honest, its popular with the youngsters I suppose." she pulled out two more items again with straps dangling below. "These are a bit different, not many girdles in use these days, they work a treat but you might be saying the wrong thing to your new friend as people generally use them to keep their tummy in."

"Yes best steer clear of that then till I get the lay of the land. I think the 8 strap one in black for now." He handed her the right hanger and placed the other back on the rack.

"Perfect, stockings are this way, now are you looking for nylon, silk or fishnet?"

"I'll need your guidance on that I think."

"Well these I'm wearing are nylon seamed ones, they are great, no problems washing them, they don't snag too much and they have a lovely lace top." she raised the hem of her dress and playfully showed the top of her stocking, that didn't help Tom's now very tented trousers. "Oh saucy me!" she giggled to herself. "Silk are like the Rolls Royce but they're expensive and you need to get the right fit as they don't stretch to fit like nylons. I think you know what fishnets look like so I wont bore you on that, not my cup of tea normally but fun for a night out."

"I think it'll be nylon then, with the lace tops obviously." nodding in the direction of her legs.

"Great" She picked up a letter sized packed and guided him back to the cash machine. "So the garter belt is adjustable so should work across several sizes of waist. The stockings are a medium to fit a size 7 shoe so that should be about right for your friend, if not just bring them back unopened and we can exchange to the right size." She rang up the total and Tom handed over his card and paid "Have a lovely day sir." She smiled and went back to her stock list as Tom made his way to the door.

As he walked he pulled out his phone and sent a quick message to Jessica. 'Just bought you a little gift, look forward to being able to give it to you in person, Tom.'

'That's so sweet Tom, I love little gifts can't wait to see what you got me.' she replied within a few minutes, she grinned at her phone knowing exactly what the little something was likely to be.

Practice makes perfect

Seven p.m. had become their appointed meeting time and true to form Tom sat patiently waiting for Jessicas invite which arrived as usual about five minutes before. He quickly clicked the link and entered the chat room.

Jessica appeared bang on Seven p.m., Tom gasped at the sight, Jessica had pulled out all the stops to match the woman in his picture the night before. She stood statuesque in front of the camera, hands on her hips. Her pale skin was flawless with a hint of metallic pink running down her cheek bones. Her eyes were ornate with heavy precise winged eyeliner complimented with elaborate Smokey eyeshadow of deep navy blue and dark grays. Her lips the colour of red wine shimmered with a slight gloss, just enough to catch the light and gleam. Thick locks of black curls hung across one shoulder, her breasts were held tightly in a black lace balconette bra sat above a black leather corset, Leather straps cinched her perfect figure into a neat hourglass shape. Eight Thick garter straps held up lace topped sheer stockings which led to a pair of black leather lace up high heeled boots.

"Evening Tom, since you said you bought me a gift i thought I'd give something in return, how do you like my look tonight?"

Tom struggled to get his words out "I, I, wow! I love it." he struggled, she slowly turned giving him a full view of her outfit turning her head to keep her eyes on him the whole time.

"You think this ticks all the boxes for your domination fetish?"

"I don't think you missed a single thing."

She giggled "Oh Tom you are such a flatterer, I couldn't resist a bit of a tease, I got thinking about what we talked about last time and wondered what I could do to titillate you a bit. Either you have a roll of coins in your pocket or I think you're pleased to see me!" They both laughed at the cliche. Tom couldn't help his reaction and she knew damn fine that he couldn't. She hoped that by dressing in the way the woman had in the picture he sent she might get him to be more open about his range of fetishes so she could mold him more to her will. She could compel him to tell her like she had compelled him to go and buy lipstick and lingerie but where was the challenge in that.

She sat down and got comfortable in her chair, "I love the feeling this get up gives me, I feel powerful."

"You could say that." Tom quipped, "Is it comfortable?"

"Tom, nothing a woman wears that looks this fabulous is comfortable but god it feels good! Maybe you should try a corset on and see how it feels?"

"I don't think I have the figure for that sadly."

"Sadly? So you'd like to try?" She teased him

"With you dressed like that I don't think I'd have much choice in the matter, wow you look amazing!"

"So are you going to tell me what you bought me?"

"Well I was hoping we'd wait to give you it in person if you don't mind." Tom awkwardly played with the drawer that contained his days purchases.

"That's fine Tom, I'll look forward to it, now onto the fun stuff. Do you want to talk more about your fetishes? Since I'm dressed to kill I could force it our of you." she said playfully passing her hand up her corset and through her hair.

"What can I tell you?"

"Well in the picture the lady was holding a dildo in a harness, is that something you're curious about?"

he moved awkwardly, another male taboo being prodded but she had been so accepting of his domination fetish he felt he could be honest. "Well yeah, I guess it's something I've thought about. I mean I've watched videos of women doing men but never done it myself."

"Ok, but it's something you're open to. Have you ever done any anal play?" She asked earnestly

"I've fingered myself but never anything beyond that." he admitted.

"Oh Tom you are so missing out. I used to have a boyfriend who was into it and he had the most amazing orgasms when I played with him down there. How about you get a toy to start out. Would you consider that?"

"Yeah I guess."

"So since you got me a gift why don't I get you one too?"

"Ok, but not too big!" He sent his address in the text section of the app.

"So we've established you like the idea of being dominated and possibly being pegged, is there anything else going on in that dirty little mind of yours? Tell Mistress everything!" she grinned

"Well yeah it's sort of related to pegging I guess, I saw a video where the guys junk was in a sort of plastic cage."

"A chastity device, ooo how lovely."

"Yeah that was it but the lady still made him cum without touching his dick, I don't even know if that's possible."

"Yes Tom it's possible, it's called prostate massage or if you go to the extreme prostate milking." She said matter of factly. "You know where your prostate is right?" he nodded, "Ok so usually if someone plays with that in the right way it will hopefully lead to what sometimes gets called the male O."

Tom looked confused "The male O, like as in orgasm?" She nodded

"Correct, think of your prostate like a clit, it's very similar."

"Wow I hadn't realised."

"The best part though is it also is the gland that produces all your cum. If we're looking at domination you can do it 'just right' and make the guy ejaculate without getting to orgasm so he's left desperate to cum but there's nothing left, at that point he'll do pretty much anything to please." she smiled broadly "I'd love to give that a go some day, would you Tom?"

"Sounds quite intense but yeah I guess, I think maybe that's what this video was."

"Sounds like it Tom, thanks for being so honest, I'm liking the honesty a lot. I'm also getting quite into this domination idea. Sleepy submissive." Tom slumped into his seat immediately, eyes closed. "Good submissive, now which level do you see on the card next to your seat?"

"Five Mistress."

"Good boy, now in your mind stand up and walk to the top of the stairs again and let's go a little deeper." she counted down from ten to one, three times, allowing his mind to descend further into her control before asking him to sit again and rest, taking note of the new level he was at.

"Good boy Tom, I want you to open your eyes but remain a good sleepy submissive. Open your drawer and show me what you bought today."

He reached for the drawer and pulled out the bag containing his purchases. Lifting them out one by one holding them up to the camera so she could see.

"Tom they are lovely, would you please take out the lipstick please?" he opened the box and held it up to the camera, "Excellent choice Tom, a lovely product. Now go and get a mirror please."

He got up and disappeared for a few minutes returning with a small shaving mirror and sat back down. "Excellent Tom, now open up the lipstick and smell how lovely it's feminine fragrance is." He opened the black matte top of the tube and held it under his nose breathing in the scent. "You find it intoxicating don't you Tom?" Now twist the tube a little to allow the tip to come out. Put the tip against the top of your Cupid's bow, just here" she pointed to her own top lip using the wand from her own lipstick. He touched the soft tip to his lip, the colour easily transferring. "Now come down to the middle like this and then do the same on the other side of your Cupid's bow, good boy. See how wonderful that moist colour feels on your lips. Now we need to fill in the rest of your lips so follow what I do, nice and slowly."

She savoured the sensation of watching him paint his lips in a dazed stupor while watching her do the same. "Good boy Tom, now look how fabulous you look with those bright red lips, real cock sucking lips Tom." he smiled knowing he had pleased his mistress. "Tom take out your cock and start to rub it for me, no cumming yet just get yourself good and hard. Look at your lovely red lips and my beautiful burgundy lips. Imagine how wonderful and slippery it would be to kiss, letting our lipsticks mix and smear together. Maybe you could imagine sucking my rubber strapon cock as you worship on your knees before me." His cock was hard in his hand as he stroked, the shaft twitching as he slipped over the tip each time.

" Tom when I tell you to cum I want you to cup your hand and catch your load in your hand just like you did with the glass last time. Make sure you get every drop. Then once you have all of your load I want you to slurp it up into your mouth but don't swallow until I say so. I want to see my dirty little cum slut in all her glory. Do you understand Tom?"

"Yes mistress." he whimpered once again straining against the urge to cum

"Good boy, now cup your hand around the tip." he moved his Idle hand as she suggested just below his tip. "Good boy, now, cum!" he immediately arched his back and his creamy juice spewed into his waiting hand pooling in the palm. "Good boy this makes me so happy." he lifted his palm to his red lips and licked and slurped the cum into his mouth leaving sticky traces on his lips and chin before looking back up to the camera. "Oh Tom that's divine, you are such a good cum slut, open your mouth for me." he opened revealing the pool of cum on his tongue "good boy, now you may swallow your gift from me." he swallowed feeling the warm thick liquid slipping down his throat.

"Tom when I wake you and say goodnight I want you to pop the lipstick back in its box, put the garters and stockings back in the bag in the drawer and then have a nice warm shower making sure you get all that lovely lipstick off. Once you are all clean you'll be very tired and want to go to sleep. You'll forget all about the lipstick and the jacking off and you'll sleep so well, waking up refreshed and ready to face the world. From now until you get your package you are not to jerk off at all I want those balls nice and full for our next meeting."

"Yes mistress" he said blankly

"Good boy Tom." she snapped her fingers and his eyes flickered and he yawned, put the lipsticks lid back on and put it back in the box then put the garter belt, stockings and lipstick in the bag in his drawer. He had no comprehension that he was wearing a deep crimson lipstick slick with his own cum.

"Well Tom, I think it's time to say goodnight, I've so enjoyed speaking as usual."

"Me too, it's been lovely, do you think meeting in real life is going to happen any time soon?"

"I do hope so Tom, do you think you could find a reason to come to me? I need to be here the next few weeks for some product launches where I need to show my face but if you can get here, I'll have no problem giving you all my attention."

"Let me see what I can work out, I have some leave I might be able to cobble onto a business trip with a client near you." he said cheerfully licking the last of the milky liquid from his lips.

"Sounds good let me know dates and we'll sort something out that works for us both, I'll even wear this outfit again if you like." she teased.

"If ever there was an incentive that outfit is it!"

"Ok Tom, time to sign off, sleep well sweetie."