Challenging

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The upper hand is reversed.
4.9k words
4.53
30.2k
10

Part 1 of the 3 part series

Updated 09/22/2022
Created 01/13/2011
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Bob was at work. This was but a part of the problem. The remainder of the problem was that Bob no longer felt challenged by the job, and with no challenge there was no sense of fulfilment. Bob longed for a challenge. Then she found one.

Let me back up a step; Bob was a Roberta, and not a Robert. Roberta was far too formal and Bobbi was too preppy. She hated names that ended with 'i' and hated even more the people who dotted that i with a heart or a smiley face. So Bob was just Bob and it suited her fine.

The challenge that she found centred round a shy, but very attractive new co-worker Molly. Molly was 21 years old, about 5' 3 with brunette hair just past her shoulders, which was usually in pigtails. She had a firm little body with curves where you wanted them to be. Molly was straight in that she'd never even thought about being with another girl before, but Bob thought she could talk her around. That was the challenge.

Bob and Molly worked together in the admin office of a technology firm that specialised in... something or other that had stuff to do with... Well, Bob didn't really know as that went beyond her remit -- she mainly typed up notes and reports and answered the phone to clients who wanted to upgrade or pay bills, or if there were a product fault, she'd fling the call through to the geeks in the tech department.

Molly's desk was across from Bob's and this allowed them to form a close friendship. Very early on conversations turned to personal lives and from there it was a short step to sex; favourite positions, first times, most darings -- conversations that usually take place over a bottle or three of wine, and not in a office full of people who were listening in with a sense of either disgust or lust.

It was during one of these conversations that Bob asked Molly about her first girl on girl action. Molly didn't answer right away but when she did said; "I've not even thought about that. I mean, I know when a girl is attractive, but I've never found myself being turned on by one."

Bob winked and replied, "Maybe you've just not met the right girl for you yet!" Molly giggled, deflecting the suggestion, and asked about Bob's first time with a girl. Just as she was about to answer, her phone started ringing and the work resumed, the banter forgotten. The conversation was abandoned due to a blitz of phone calls and the day went on.

It had been a very long week and Friday finally arrived; plans were discussed for the weekend. Neither had anything specific planned, but both wanted to have a drink and let their hair down. Molly's complaint was that in her little village there were only two pubs and no atmosphere. This triggered a plan with Bob who offered Molly a space to sleep in her flat near the city centre, but neglected to mention she had no spare room and possibly the shortest couch in the entire county of Yorkshire.

It was settled; Molly would go home, grab her overnight stuff, a bottle of red and get ready at Bob's. What she didn't know is that Bob intended they have a few drinks before she gave 'the tour' (four rooms was hardly a tour!) so Molly couldn't back out and go home. She knew the buses were very infrequent to Molly's village and the taxi fare would be extortionate. Besides, Bob's king-size bed (her only luxury) would give enough room that if Molly really didn't want to go along with Bob's intentions that they could have a side each without having to cling onto the mattress for fear of falling.

Bob walked home with myriad images flickering through her mind; outfits she might wear, outfits she'd like to see Molly wear, toys she might need, music, lighting -- the list went on and on. Until she found her hands rubbing her breasts as she walked down the street -- not something that you can really pass of as an itch, or trying to remove fluff when you have a dreamy look on your flushed face and erect nipples!

She got home and jumped in the shower. She turned around slowly under the hot water, making sure that her entire body was wet -- not just her pussy! First she washed her long auburn hair and then shaved her armpits, legs and pussy, making sure she got the essentials done before her mind ran away with her again.

She rinsed the shaving foam off and picked up the shower gel, squirting a little into her hands and warming it before rubbing it across her breasts; cupping them one at a time, covering them with the soapy foam, massaging them before focussing on her nipples. Bob's nipples had always been very sensitive, and almost as soon as her hands made contact they became erect, channelling pulses of pleasure though her body, triggering the wetness between her legs again, causing her to let out a heavy sigh.

It wasn't long before the images of her plans for the night were once again firing through her mind, and rubbing her nipples was no longer enough. Her right hand slithered down her body, loath to leave her breast, but knowing if it did, greater pleasure was to be had. As her hand slid over her smooth pubis, aided by a layer of bubbles she thought of Molly's tits; large, and perfectly formed, a cleavage it was very easy to stare at for too long, and one that Bob hoped to soon bury her face in.

Bob's fingers curled into her pussy, sliding easily between her lubricated lips and deep into the warmth of her opening. Two fingers worked frantically in and out as her thumb flickered and pressed against her clit. She pushed her back against the wall of the shower cubicle; her legs taut against the far side as she leant her head back to allow the ragged breath to tear from her heaving chest. Her left hand was now pinching her right nipple hard and her body started to spasm under the approach of her orgasm. Hopefully not her only one of the night she thought as her legs gave way beneath her and she slithered to the floor, the hot water still raining upon her, washing away the pent up passion, now released.

Bob pulled herself to her feet, rinsed and turned the shower off before getting out, towelling off and putting on a black thong and her dressing gown. She went over the flat quickly, tidying the kitchen and the living room first before moving to her bedroom. This room was going to require some extra thought. What could be left out to entice, but not frighten? Molly seemed fairly open minded, so Bob figured a couple of pairs of handcuffs on the headboard would be ok. She'd almost expect to see a vibrator, but which one to place on the bedside table? Not Bertha, the largest of Bob's toys, but nor could it be anything too small and feeble. The decision was made, and an 'average' sized 'realistic penis' (except for the fact it was blue) was positioned casually next to the alarm clock.

Next was the wardrobe. She didn't want to seem like she was showing off, but she did have quite a few costumes that she'd like to show Molly, and some very sexy underwear. A black corset on the dressing table and a policewoman's outfit hanging from the wardrobe door should be enough to suggest to Molly what she could become a part of, the possibilities to explore.

Bob now went to the kitchen and got some cheese on toast before cursing herself for creating a mess on her pristine work surface. She wiped up the crumbs and melted cheese before switching on the TV and waiting for 7 o'clock to roll around, and with it bring her challenge.

A little before 7 there was a knock at the door and Bob checked the spy hole. She was delighted to see Molly there with her bags and took a deep breath to calm herself before opening the door. She greeted Molly with a hug and caught herself just before her hand drifted to her arse for a squeeze... Stepping back to let Molly enter, Bob asked if she would like a drink before they started drinking and offered the usual hot and cold beverages. Molly declined and asked for a corkscrew and a couple of glasses instead.

Bob returned from the kitchen moments after the clattering and slamming of several drawers being opened, rummaged through and closed in the search for the corkscrew, which was in the pot with the utensils. In the search Bob's robe had loosened and molly's eyes widened when she saw Bob's nipples peaking out from the towelled sides of the dressing gown. Bob looked at her, then at herself. "Shit! Sorry," she muttered as she put the glasses down and tightened herself up "I hope this doesn't count as your first girl-girl experience -- it's a bit tame!"

Molly admitted it was the first time since school changing rooms since she'd been so close to a naked breast that wasn't her own and apologised for her staring response. "That reminds me" she mused, "you didn't tell me about your first time."

Bob picked up the wine and tried to jam the screw into the top of it, "Well, I was about 14 at the time and me and Becky Watson were having a sleep over, you know the usual, stolen wine from her parents, talking about who we hated and boys." Bob stopped as she realised that the bottle was actually screw-capped, thus rendering her efforts with the corkscrew pointless. She swore again, took the lid off and poured two glasses. Without missing a beat she continued; "Becky had never had a boyfriend but had a big crush on Mark Westlands, one of the sporty types. She was going to the cinema with him the following week and didn't know how to kiss. The long and short of it was that I showed her what I knew and then we just sort of continued, drunk on cheap wine and hormones. It never happened again, but it was a so different than kissing boys, much more gentle, tender even."

Molly picked up her glass and after a thoughtful look said "Some guys are a bit too tongue frenzied aren't they? They seem like they're trying to lick your tonsils!" Bob took a sip of her wine and, changing the tone of conversation for the time being asked if she should put some music on. Molly spotted the CD racks taking up half a wall and took her glass for a browse. She ran her finger along the edges of the CDs and pick out a couple of bands that she knew and handed them to Bob.

"Ah, good choice mademoiselle!" Bob said as she opened the CD tray, first putting in Third Eye Blind's debut album, then Jack Johnson's In Between Dreams. The music started and both women sat on the sofa. Bob looked across at Molly who now had an empty glass. "Thirsty?"

Molly smiled and topped up her glass again and leant back on the couch. "I figure if it's going to be a big night, we might as well start here and save some money."

The music played, the conversation continued and the wine was consumed. After Molly had finished her third glass Bob asked if she wanted to take the tour, such as it was. Molly got up, and sat back down again very quickly as the wine overpowered her sense of equilibrium. Bob smiled to herself as she watched Molly's boobs jiggle from the impact and then offered her a hand. Molly took it and pried herself loose from the couch's grip. Bob showed her the kitchen first, pointed out the essentials, tea, coffee, juice, wine etc and also, where there were crisps and chocolate should they be required.

Next was the bathroom, which Bob ushered Molly into while she provided the audio from the door -- it was rather a small bathroom and a bit cramped for two people to occupy at once. Bob pointed out the make up remover, the mouthwash, toothpaste and spare loo rolls before backing out and leading Molly to the bedroom.

"This is my bedroom," announced Bob, "with my lovely, spacious bed!"

Molly looked around the room and pointed at the cuffs, "Looks like someone's a bit kinky!" Then she stifled a giggle as she spotted the blue dildo next to the bed.

Bob saw what she was looking at and asked, "Have you not got any toys then?" Molly confirmed that she had, but she kept them in the back of a drawer, not where anyone could see them.

"That concludes the tour," Bob announced as Molly continued to look at the vibrator. She looked across at Molly as her fogged mind processed that she was to be sleeping in this flat, but did not have her own room. "Am I sleeping on the couch?" she finally asked, "Because I know I'm only little, but even I couldn't sleep on there."

Bob pointed to the left side of the bed and said, "I thought you could sleep there. I usually take the right -- closer to my electric lover, unless you have any specific preference." Molly let a sly smile slide across her face, "You want to give me my first girly experience don't you, Bob?" Bob didn't answer, afraid that a confirmation would end the friendship and a denial would lose the opportunity. "Well, since you asked me about it, I've thought about it quite a lot. And men generally don't know what they're doing, or at least not what we want them to do. So I thought I'd try and seduce you, which is why I've been drinking so fast." She swilled her glass around to emphasise the point, "Cos I'm very nervous about all of this..."

Bob was amazed that Molly was actually planning to steal her thunder! She thought she had the upper hand on this, and would be corrupting an innocent mind, when all along the mind wanted corruption -- excellent! She put her glass down and took Molly's out of her hand and put it onto the dressing table. She held Molly's hand and pulled her into a embrace. "You have no idea how often I've thought about leading you from the straight and narrow," she whispered as her lips crept across Molly's face to her mouth. Molly gasped as she felt the softness of Bob's lips against her own, the gentle nibbles of her teeth and the silky flicker of her tongue, coating her own lips with saliva.

Molly wrapped her arms around Bob and pulled her closer, kissing her back, matching the passion, letting go of herself and being the moment. Bob stepped back breaking the kiss and had to push Molly's shoulders to maintain the distance for a moment. She looked at Molly, taking in every detail from the way her hair parted off-centre to the two solid nipples beneath her top, to the slight tremble in her legs.

Molly just stared into Bob's eyes with a sense of longing, wanting more of what until recently she hadn't known she had wanted so badly. Bob loosened her robe and let it slide from her shoulders and smiled as some of the wide-eyed wonder returned to Molly's face. She took Molly's hand and guided it to her breast, tracing her nipple with Molly's fingers, brushing the back of her hand across it, biting her lip as the familiar rush of sensation hit her. She reached to the back of Molly's head and pulled it closer, lowering it to her breast. Molly looked up, "What do I do?"

"Whatever feels right," Bob replied.

Molly kissed Bob's nipple, then started kissing around it, covering the petite gland with kisses. Bob wrapped Molly's pigtails around her hands and pulled her closer, forcing her nipple into Molly's mouth. It was taken with eagerness as Molly started to run her tongue across it, from left to right and then from top to bottom. Bob was breathing harder now and was desperate for more, but didn't want this to stop. Molly started to suck the nipple into her mouth, causing Bob to push her away.

With a wounded look she asked, "Did I do something wrong?"

Bob, shook her head, "I just can't keep my hands of you any longer!" She took hold of the front of Molly's shirt and tore it open, staring at the fantastic breasts in front of her, the very ones she had been thinking about when she came in the shower. She kissed Molly's neck and this time let her hand roam to her arse, kneading her firm, round buttocks as her mouth worked down from Molly's neck to her cleavage. Molly was a step ahead, and as Bob was reaching to unfasten her bra, Molly dropped it to the floor.

Bob looked into her eyes and pushed her back onto the bed with a grunt of need. Molly pushed herself up the bed so her head was on the pillows as Bob took off her thong and stood there naked before her. Molly bit her lip and said, "We're really going to do this aren't we?" Bob nodded. She climbed between Molly's legs and took hold of her right hand pushing it towards the headboard before snapping it into the cuff. She did the same on the left before settling back on top of Molly. "If you want to stop, say so, but I'm going to try my damnedest to make sure you have no reason to want that. Do you understand?" Molly nodded.

Bob gave her a kiss on the lips before working her way across her cheek, down her neck across her chest and finally to her breast. She sat up and looked down at them, cupping them both together, then as she imagined earlier, buried her face in them. She wanted to feel Molly's warm flesh against her face, the soft skin on her cheeks. She pulled back slightly and started to kiss them; small kisses at first, but soon more passionate ones, which turn to licks. Molly was looking down at Bob, watching as her colleague, friend, lover(?) paid such love and attention to her breasts, not once was she caused to wince by an enthusiastic, but misguided nibble. She wrapped her hands in the chains of her restraints and let out a groan as Bob sucked her nipple for the first time.

Bob knew that Molly was now hooked, there was very little chance of her wanting to stop. She sat up from her position between Molly's breasts and slid further between her legs. She unfastened the button and zip on Molly's skirt and pulled it down her legs, resisting the urge to leave it around her knees and focus on her pussy. She pulled it off, dropping it on the floor and sat on her haunches, surveying the sight before her. A voluptuous but petite brunette cuffed to her bed, erect nipples and damp panties, moaning softly to herself with a pleading look in her eyes -- what more could she ask for?

She knelt on the floor and rubbed her hands up Molly's legs, reaching close to her pussy, feeling her trying to push her desire towards Bob's fingers, but not able to reach. Bob then curled her fingertips slightly and ran her nails down the inside of Molly's thighs. Back up, scratch down, back up scratch down... Molly was whimpering, rocking in her restrains, desperate for more, yearning to be touched.

Bob reached up Molly's panties, gently rubbing her hand over the dampness of her friend's crotch before reaching between her legs and hooking and finger into the material and pulling them down, leaving Molly completely naked and vulnerable. Their eyes met, and a low, barely audible "please..." escaped Molly's lips.

Bob pulled herself up the bed and lay next to Molly again, kissing her face, her neck, her eyelids; all the while her right hand was caressing her body, smoothing circles over her chest, stomach, hips -- teasing Molly, but never giving enough to satisfy her. Bob stopped kissing and looked Molly in the eyes as she slid her hand across from Molly's hip to her mound and started rubbing in increasing circles, creeping closer and closer to her pussy.

Molly bit her lip as she could feel the foreign fingers approaching her clit, waiting, so patiently waiting for the contact she yearned for; her juices were trickling down her thighs, her nipples erect to a point of near pain... Then she felt it; Bob's fingertips brushed against her clit, electricity ran up her spine and she bit a little harder on her lip to stifle the yelp. Bob smiled and ended her circling and concentrated on the source of Molly's current pleasure.

She ran her fingers across Molly's button and massaged it between her finger and thumb, rolling it between them. She didn't stay there long, as she ran her hand between Molly's thighs, curling her fingers into the brunette's pussy as she had done to herself in the shower. Molly was very wet, but still very tight; Bob pushed one finger in, felt the warmth and wetness of Molly's pussy and worked another finger in. she twisted her wrist, to help loosen her a little before slowly sliding her fingers in and out of her.

Molly was groaning and writhing as she approached a plateau of pleasure she was previously unaware of; even on her own she'd never been touched so knowingly. She held out a few more seconds before her back arched off the bed, her head tossed from side to side and her voice found itself in a series of moans and expletives.

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