Jess Ch. 01

Jess looked up at him past the huge cock that dominated her view. She felt frail and subdued by it.

"Turn over," he told her. The firm tone of voice was enough but he pulled the coverlet from under her body spinning her body round. He rolled the cold can over her cheeks and she squealed with feigned protests. He held her down with a hand on her back while she kicked out. She was laughing and cavorting trying to get away.

"Stop it that's cold," she stated the obvious, while making a show of escaping without achieving anything. She felt him spread her legs effectively stopping the thrashing around knowing what was to come. The cold can froze her asshole and she started squealed all over again. The laughter was more from embarrassment than from pain and something unexpected, happiness. It seemed as long as he paid attention to her it wouldn't matter what he did, she would love it.

He lifted her legs and rolled the cold can over her pussy squishing her swelling lips against the can. Jess squirmed less in case he dropped her and she did so want him to enjoy her body. A friend's advice about keeping him happy, doing what he liked to keep him, weighed heavily upon her.

That he could see everything between the legs and was touching it so audaciously left her feeling embarrassed. This feeling inflamed her so she felt hypocritical and this too heated her up. Her pussy was so puffy and open surely he must see how much he aroused her. This was terrible yet she was enjoying the naughtiness so much.

Alan held her on the bed while massaging grease between her cheeks. This time she was aware why he was doing it and became afraid once more. Jess lay perfectly still letting him work the grease over her ass and pussy. She felt a finger swan around the puckered little hole, feeling intense pleasurable sensations.

Why was he doing this to her? Was it because she wasn't on the pill? Must she sacrifice her body and moral standards to keep his interest? Was he taking advantage of her inexperience? The painful ideas meshed with the pain from a bruised bottom. The coldness helped sooth the bruised ass which told her he had experience of this so it wasn't her fault, he liked it. The grease helped too.

She tried to relax this time, knowing she wouldn't be damaged just bruised. A cold finger gently worked its way into her bottom. She breathed deeply trying to relax. It took awhile but he was patient enough to wait.

He felt that little puckered hole relax around a finger so eased another inside. Ever so slowly he managed to push the two fingers in as far as they would go. He had been playing with her clit bringing her breathing up a rate until she panted in rhythm with the exploring fingers. She seemed to be forgetting about the pain and he eased more grease into her hole.

He wanted it so badly it was difficult to refrain from simply jumping her. He wanted to burrow his cock deep inside driving it hard and furiously into that tight hole. Deciding to keep her he would have to be patient and be careful, teaching her how to take him. He was experienced enough to know these feelings weren't love they were driven by passion. It would come to him though. A deeper more serious and intense feeling would overtake him; feelings overflowing with heartache that was love.

Jess felt the head of his cock ease into her asshole. This time it pained less and she hoped the journey upward would be easier too. She wanted his cock in her pussy but was just as fearful of that too. The consequences could be so much more threatening with her whole world collapsing if she became pregnant.

The pain sensitised the passage so that every movement was felt. This time she didn't become as excited. It was more than endurance, more like acceptance, while waiting for him to finish. He collapsed upon her back sated after making use of her body. She didn't mind not experiencing an orgasm this morning and it was surprising how pleased she felt from having served him like this.

He rolled her up into his arms telling her all sorts of nice things, how beautiful she was and such a respectful woman, how considerate. "You know how to look after your man, do you want me to be your man?" he asked.

Her face lit up with pure pleasure. Her heart skipped a beat, continuing to thump hard in her chest. It was difficult to breath. "Yes, Alan, that would be wonderful," she gushed.

She had been pleased enough on finding him still there in the morning, half expecting him to regret their spontaneous tryst and be off before she awoke. That he still wanted her in the morning and was now looking to the future, this was too perfect. Hold on, she was pushing things too far.

"Have you got plans for today? Lets spend it together, getting to know each other," he suggested.

There was nothing more she could possibly want to do yet it felt like an order, or at least something impossible to refuse especially when confronted by such enthusiasm. He was always steady and controlled in the office, though the energy and enthusiasm always shone through becoming infectious to a whole team working with him.

Little did they know how sexy and naughty he could be! The girls in her office thought he was sexy but if they knew how depraved he was they would be shocked. She still was a little, no a lot. She was surprised at how easily she had given in to him after what he had done to her. That was unfair for she hadn't just let it happen, not fought against it, but enthusiastically joined in. How could she have done those bad things?

They took a taxi for he was too impatient to wait for a bus. The luxury of it left her feeling rich and special. It wasn't that she couldn't afford one it just seemed a frivolous waste of money; but now she was with him. They ate then shopped. At first she couldn't let him buy her clothes but he insisted. At his insistence she hesitantly emerged from a small changing room.

"This is too short, I'm not used to it," she said, looking sheepish. Jess wanted to please him but the light summer dress was too low cut and too short.

"You're not used to the style that's all. Walk around, take a look at something else, you'll soon get to feel comfortable," he told her.

The hesitant walk around the store left her feeling vulnerable but he was there to protect her. At first she quietly looked around expecting others to stare but he was right, no one noticed so she became used to the brief garment. It was a light summer dress and there wasn't much of it to ensure modesty so she would have to be careful. If this was what he wanted then it could become passable.

He paid for the dress as well as some new underwear too. The assistant looked at her with a look between envy and surprise that a boyfriend was troubling to pick her clothes. "Can she use the changing room to slip into these?" he asked. The girl smiled, nodding her head at him as most women did.

Jess felt a moment of jealousy which turned to pride that he had chosen her. It left her feeling more determined to please him, especially as he was paying for the clothes. Instead of changing into a more suitable dress he handed over the underwear. It worried her she might have to wear the little thing to the car.

"Go on, get changed and quickly. We've more to do yet," he cajoled her.

It was even more difficult to leave the changing room this time. The underwear was soft and comfortable but again there was less of it than she was used to. The bra pushed up her breasts but didn't cover them which was naughty in that thin cotton dress. If she wasn't careful too much cleavage would be shown off and even her nipples. The thong cupped her pussy in a purse of soft cotton, but that was all it covered.

Jess felt so awkward standing before him waiting for his approval. All she wanted to do was get home out of sight as soon as possible. If any of her friends saw her dressed like this they would be shocked. The assistant strolled over with a receipt they left at the counter. The young girl looked at Jess with an appraising eye leaving her feeling all the more awkward.

"What do you think?" Alan asked.

Jess wished he hadn't asked, it made her feel as though she were a manikin on display.

"Turn around, show her the dress," Alan commanded.

Before she could stop him he lifted the hem showing off the panties. Jess just stood there stunned.

"Do you think these are suitable?" Alan asked.

"We can't take them back now they've been worn," the assistant stated firmly.

They were ignoring her as though she didn't count, wasn't even there.

"That's OK! I was just wondering if there is anything better to wear under this dress," he asked.

Jess could see he was teasing the young woman, but she didn't seem perturbed. Jess was though. In the changing room this would be embarrassing enough but out in the store before a large mirror it was humiliating. They were both looking at the little thong and the naughty game was attracting the attention of others. A couple of women were wondering what was going on, trying not to be noticed, not staring but sneaking a look.

"Well, she seems to be rather full in that thong so it might become uncomfortable. I'll see what else we have," the assistant casually commented.

Alan gave her the hem to hold up and made her turn around. She closed her eyes when facing the mirror not wanting to see the little thong pulled between her cheeks.

"Here try these. They are the same size but a larger fit over the lips," the assistant said. She sounded like a helpful assistant discussing shoe sizes, not how well the panties fit.

The new thong was handed to her and it was clear she was to change into them right there in the store. She looked meaningfully at Alan pleading to be let out of the dreadful game. With the hem only just covering her thighs it was difficult to modestly change the panties in front of them.

He again lifted the hem for them both to examine the crotch of her panties. "That looks better, though she seems to be outgrowing these too," he chuckled.

Jess could feel it was true! Her lips were flowering with excitement. It was upsetting to be shown off like this and a complete surprise that she was so excited. She felt numb, retreating from the humiliating situation. He guided her with a firm grip showing off her bare ass to this stranger. He then bent her over! She had meant to do as she was told to please him but this was going too far!

"They look good from the rear, shows off her lovely ass. What do you think?" he asked.

"Nice! The string shouldn't be too tight otherwise they become uncomfortable," she told him. Jess drew in a deep breath of astonishment knowing the soft fingers pulling at the string of cotton between her cheeks weren't his. Instead of standing up and running for cover she stayed bent over, where he had placed her, too frightened to move.

The young woman was fingering her! While pretending to examine the fit of her panties the damn woman was stroking her asshole with a long finger nail. He could see what she was doing but pretending not to notice.

"Are they suitable do you think, no hurry, we can try others if you like," Alan told the assistant.

"She's already very wet. I'd recommend a reinforced gusset, something more absorbent," the young woman commented.

Jess cringed, mortified from having such intimate details of her body discussed so openly with a complete stranger.

Alan knew the young woman well, knowing too she would catch on to the game and play along. He also knew she would appreciate appraising Jess's crotch.

As promised she brought over a pair of sensible knickers. This time there was plenty of room in the crotch for her to delve in without being too obvious. A long finger slid into her pussy lubricating it enough to slide it up her ass. She had taught Alan the technique. She rubbed Jess's clit with a strong thumb while a finger explored her ass.

Jess opened her eyes wide in surprise. When they focused she could see two women openly staring at her from behind a rack of clothes. It was obvious what the young woman was doing to her from the movements of her arm. Her legs became weak and she was terrified to think she might cum right there before everyone.

That dreadful thought held her back. How she could have become so susceptible to these two was a mystery but despite everything she was still unable to move or defend herself. It seemed like an age but eventually the woman pulled sticky fingers from Jess and straightened the panties.

"I can see they're more practical, I'll let her wear them," Alan told the assistant. "We'll take the others too, of course."

The woman took hold of Jess's chin and pushed both fingers into her mouth. Jess stood there slack jawed not knowing what to do. The woman wiped her fingers over her tongue and lips then dried them on the hem of the dress. She took a hold of one breast to pinch an engorged nipple pushing through the thin fabric. The woman watched Jess's face wince in pain but not the slightest sound was heard.

Both nipples stood proud of the dress which she had feared might happen. Alan moved close and embraced her. "You did well pet," he said quietly into her neck while holding her tight.

She had passed a test of some sort but didn't feel victorious, rather the opposite, she felt defeated. If this was the sort of thing he wanted she was out of her depth and should run and hide from him. She also needed to find out why her body was so aroused and why she had capitulated to them so easily.

They went for a coffee where again he was recognised as a regular and yet again Jess became jealous of a woman serving seeing her flirt outrageously. She just hoped there wouldn't be any surprises here. She couldn't relax even when it became evident the ordeal was over. The dress was too short to be sitting on a stool at a high counter and the guys serving could see down its top.

"Come on, we've more shopping to do," he told her.

They walked to an out of the way store with every step further from the car, meaning they would have to walk past far too many people on the way back. As soon as they walked in Jess gave a shudder. Never before had she been into a sex shop. Here too Alan was greeted like an old friend.

Jess stood behind him trying not to be noticed or look at the range of bizarre clothing. As for the equipment it was all too much to take in. The tall imposing woman was dressed in a tight leather outfit decorated with chains meant to be intimidating, and it worked on Jess as it did frighten her.

Not listening to their conversation she clung onto him as they walked over to a cabinet.

"This will fit the bill, or should I say the anus," the woman laughed. Her head went back and shoulders heaved with the laughter.

At the word 'anus' Jess took notice. The cabinet was unlocked and a box handed over to Alan, with her eyes following every movement wondering what it might contain with the distinct feeling it was meant for her.

"As a novice this smaller set will be better. Do you want to fit one now?" the woman asked casually.

How could they be so casual about such an ordeal? In the previous store she had been humiliated now this! On high heels she tottered after him grateful to be leaving the imposing woman behind. Out of the corner of an eye she saw with relief the woman attend to another customer, so at least this one wouldn't be adding to her shame.

At the back of the store he guided her into a changing room. "Slip those panties off, Jess," he told her.

Again it sounded like an order but his use of her name sent a thrill through her body as it always did. Reluctantly she slipped them off and stood rigid with hands to her sides. A quiver of her bottom lip revealed how scared she was.

"Turn around and bend over that chair," he told her.

The touch of his hand on her back was enough to have her bent over. Despite where she was the touch of his fingers on her bottom sensitised her body, arousing an already heated sex. It was astonishing how sexed up she was to his every touch, to every naughty game he played with her.

Feeling grease being rubbed between the cheeks was no longer a surprise or mystery, she knew what was going on and hoped it wouldn't be too painful. The wonderful hand rubbed her mons and lips, seeming to engulf her crotch then fingers pushed easily into a wet pussy. It felt soaking wet, obviously from a whole morning being teased.

He heard her breathing become ragged. Feeling she was ready, from a finger up her ass, he pressed a butt plug at her asshole. He had warmed it so as not to startle, so the sphincter wouldn't contract. As though it were a finger he eased it in.

The butt plug popped in Jess's asshole, still sore from losing her virginity the night before. Her asshole closed around the narrow neck holding it in place. The soft rubber hood nestled between her cheeks so that she wouldn't have too much trouble coping with it, or so he had been told. Walking or even sitting with it in wouldn't be too difficult.

"Hope it isn't too uncomfortable," he said.

"No it's OK," Jess said. Hell! What was she saying! He had just pushed something up her ass. What was she to do now? Thoughts rushed through her head like an express train. Before she could examine one arrived then screeched away in terror. How was she to run from here with this thing up her ass? How was she to get home? That was where she needed to be; at home tucked up in bed away from this nightmare.

Alan put his arms around her and kissed her forehead. "I'm glad to have found you, you're wonderful," he told her.

The great wash of emotion shook her. The faith in him that had been dwindling to nothing was suddenly renewed whole, maybe with even greater passion. Tears welled up in her eyes and he kissed them away.

"Do you want to be with me?" he asked.

"Yes," she mumbled. "Yes I do," she repeated with enthusiasm. It was a surprise to be so unforgiving, to push aside all those reservations that had been building. Even though she was aware of how he affected those around him she was willing to throw away the doubts, to give in to what he wanted.

He pulled at the dress fussing over it as though she could be made presentable in such a little garment. "Take small steps until you get used to it," he told her.

She wondered if anything he did to her would ever be a surprise or abhorrent again. He was patient as she timorously moved through the store. He had an arm around her waist, guiding and supporting her. The other hand held a bag containing the torture instruments and a tube of gel.

He was right. By the time they made it to the car she was somewhat used to the intrusion in her ass. He had lavished the gel on her bottom which eased the soreness as well as making the thing bearable. With every step she was reminded she was his. At least that was what she told herself.

The tricky business of getting into the car then sitting in it had to be faced. He held on easing her in like an infant, with one hand on her head and the other sliding her in. Ever so gently her bottom touched down upon the seat. He held her weight a moment then she felt her cheeks flatten a little and the butt plug push tight up inside her asshole.

She took a deep breath and let it out slowly. It wasn't too painful. Jess could cope with it so again she could keep him happy by doing as he commanded. She wondered how long this would last for she was way out of her depth and expected a demand that went too far. What then, would he give her up?

They toured a supermarket discussing, discovering and picking foods they both liked. She would enjoy cooking for him. On seeing an obviously newly acquainted couple she sighed. Alan and she must look like them, an ordinary couple in the first flush of a relationship, getting to know each other. Did that young woman have a butt plug stuck up her ass? She doubted it. The thought made her feel special; she was doing something exceptional for her lover, proving she was his.