August 2002 Pt. 02

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Exploring her other hole.
3.1k words
4.54
11.7k
5

Part 2 of the 3 part series

Updated 06/11/2023
Created 08/24/2022
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peej88645
peej88645
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Allison and Jack showered in silence, side by side. The morning had been exhausting. She had woken up and gone for her morning run at 6am, fully expecting to have been at work just gone 8am. It was going to be a normal day. It had been anything but normal. And it wasn't even lunchtime.

She didn't especially remember being rude or curt to him in the past. He was a hard worker, and fairly bright. She actually quite liked him. Unbeknownst to him, she had chosen him on several occasions to work alongside. She didn't find him unattractive and enjoyed his company in the evenings when the conversation turned to matters outside the firm and their various client engagements. His interpretation of their working relationship had clearly been very wide of this mark. He'd seen her as terse, sarcastic and arrogant.

The last of his morning's cum was still trickling down her inner thighs as he took a large squirt of shower gel and worked it into her breasts, across her back, and neck as the shower rained down above them both. It was one of those large walk-in showers with a rainforest style shower head. With one thing in mind, for later, he then bent down and turned her around to face the wall, coaxing her to bend over slightly. He massaged the soap suds into her ass, between her cheeks, gently running his fingers and hands into her. He didn't get very far -- not far at all -- until she yelped and flinched.

He did his best to cover every inch of her body. She reciprocated, massaging his cock with one hand and cleaning his back with a sponge held in the other.

After drying off he rang room service, making sure to keep the do not disturb sign on the door after the delivery. Once they had eaten and the plates been collected, they slept for over two hours. At just after midday Jack's erection awoke him. Allison remained asleep, her face pointing away from him. He lifted the covers slightly, trying not to disturb her. Her ass was incredible. He had thought it before when she was dressed but seeing it naked was something else. She was curvy, but strong. The benefits of a very active lifestyle and blessed genetics.

He slipped a hand down onto her buttocks, gently massaging them in turn. Then he extended his middle finger between her cheeks, glancing the entrance to her shaved pussy from the rear. She made a noise like she was waking from her dream and rolled back on to her back.

The blindfold had been a major contributing factor to the morning's events, and it wasn't the same without it. Seeing the new warmth in her eyes and seeing less of the cocky condescension made for a different dynamic.

She rose in silence and stood up. He did the same. Almost instinctively he reached down for the blindfold that had been on the bedroom floor and put it on her. She closed her eyes before it was on, as before putting up no resistance. Tight but not too tight. He was aware that it removed all sight and all light. She was naked in darkness again.

He walked her to the bed and she climbed onto it. She started to lie down, but he raised her stomach up so she was on all fours, just as she had been when he had exited her several hours ago. He had established that she was satisfied with how the morning had panned out, and she knew she could walk out of the door at any time. He had even folded her clothes for her neatly. Apart from her panties which he had kept as a memento of the day.

It didn't seem to be too wild an idea to do what he did next. She wasn't speaking so neither would he.

Gently he squeezed the bottle. It took a while for the liquid to come out. The first small cold dollop landed almost at the bottom of her back, then ran down between her cheeks -- into her asshole and lower down, dripping onto the bed. There was a slight pooling of liquid around her ass and he took the opportunity to work some of the liquid inwards gently using his smallest finger. Not only was she not speaking, he couldn't even hear her breathing. She was completely silent. It was clear in his mind that she rarely got fucked in the traditional way let alone taken up the ass. This would be the first time and he would need to take his time.

He just about had the first 1/3 of his little finger inside her. Almost to the first knuckle, when she moved forwards, pulling away. He poured more of the liquid in, getting closer this time, but not entering her ass. This was going to take a while. It was also worth exploiting her seeming willingness to be fucked again. He could come back to this later.

He turned her round so she was facing him, still on all fours. He put one finger on her lips and she opened her mouth willingly. He pressed his cock in and she began to lick and suck it, cupping his balls expertly at the same time. This was something she had done before. He couldn't imagine it with boring Neil, her fat boyfriend. As she sucked and licked he reached forwards, over her, and tried to spread her ass cheeks from above, teasing her pussy with his fingers, holding it open. This would make another excellent photograph. She lowered her head slightly, allowing him an improved angle and to put one finger fully insider her.

Aside from tasting it on his fingers as he'd fingered her prior to fucking her this morning, he'd never tasted her pussy. He let her suck him for a few more minutes then guided her onto her back. The blindfold remained intact and in place. She spread her legs, allowing her pussy to open up slightly. It was gleaming, as it had been earlier. Soaking wet from arousal. He licked up and down, teasing her. She squirmed on his tongue, spreading her legs wider, writhing on the bed. Occasionally she began to finger herself, then with both hands held her lips apart, begging him to go in further.

He knelt up as she laid on the bed, legs splayed. He fingered her clit with his thumb and she moaned in harmony. Then he decided to try her ass again. He rolled her over and opened her legs, fingering her pussy with two fingers. Earlier this morning she had been wet, but tight. Now she was completely lubricated, relaxed and much easier to enter. He hoped her ass would tell a similar story soon.

He dispensed with the lube and used the ample juices from her pussy to lubricate her hole. Initially she jerked forwards, but soon seemed to have come round to the idea of most of a finger inside her. Her pussy was like a tap, and the sheets looked like there had been a minor spillage, but he made the most of it and in about 15 minutes, via some moaning, hesitation and a little bit of shaking and quivering, he had his index finger fully insider her ass. It was locked tight, gripped hard, but he had felt it expand slightly step by step along the way. It was nowhere near ready for a cock, and wouldn't be for some time, but he decided to use the one piece of apparatus he'd packed at the weekend in case he'd managed to enact the fantasy that had unfolder during this morning's events. A small, but perfectly formed plug -- like a narrow egg with a small ruby-coloured handle at the end. Gently he removed his finger and instead of closing up firmly, as it had been at the outset, there was the smallest of gapes. With more juice applied, this was enough to work with for now. The plug was cold, he could tell that by her reaction, and it must have felt like an alien shape as it entered her. Time for another couple of photographs, he thought.

With no vision due to the blindfold, her remaining senses were working overtime. As the plug inched into her, she wondered what it could be. She'd never had any object inside her like this. Not a finger, not a penis, nor a plug. She could feel it stretching her, at the same time making her pussy tighten even more than it already was. It was an odd sensation and one she never imaged feeling. Once it was in it seemed to stay nicely in place. It wasn't long, but certainly wider than his finger had been. To her pleasant surprise, the next thing she felt was his cock, entering her pussy. It slid in, and seemed to fill her entirely, as she rocked back and forth on it.

Allison was 24 and although she'd had sex before, to men she'd met in clubs and bars, and to her current boyfriend, she'd never really thought too much about it. It wasn't something she fantasised about, and it wasn't something she'd much enjoyed. She'd fucked fewer than 10 guys and had a mixed experience of it. Until now. Jack was dominating her. He'd said that this was to redress the balance, to bring her down a peg or two, and she'd needed it. She was absolutely loving it.

He reached for the camera and took another set of pictures -- these were more like action shots - this time of his cock in, and then halfway in, and then almost out but just about to enter her wet pussy. All the while the plug was sitting inside her ass above, snugly. If he could persuade her to keep it in until the evening then just maybe, he thought.

She knelt up slightly more, allowing him to reach her pendulous tits -- swinging below her as her drove in and out of her. Her body was warm, and she had started to sweat. It felt like he wasn't physically capable of making the most of her on his own. He had never, ever had a sexual experience like this before. Sometimes days would pass without him as much as having a wank, alone in his flat. But this was amazing. He drew her legs together, tightening her snatch nicely as she came for the second time in the day. Her breasts had unlocked another level of sensuousness. Instead of coming inside her, as he had done earlier this morning, he decided to come over her. Withdrawing just in time he shot his load down her glistening back. Some of it reached the ends of her hair. Warm liquid dribbling down her. Yet another "first" for her to tick off the list.

It felt right at this point, as they entered the afternoon, to dispense of the blindfold. It had served its purpose, but they were both adults and had shared more in the last few hours than they had in most of their lifetimes. Showered and dressed, and with the unusual circumstance of not having to do any work at all until tomorrow, they decided to head to the hotel bar and have a few drinks.

It was just as their third cocktail arrived and they began to look at a menu for food, that things began to open up between them.

"I'm sorry if you thought I was standoffish. I wasn't trying to be. I just have to make this job work. I've worked so hard that I don't think I've got time for anything else."

She was right, in a way. The job, the firm, the environment didn't leave a lot of time for distractions and the people who rose to the very top were rarely liked.

"I've read you wrong" he replied with a genuine smile, "I'll take it all back. Anyway, I was thinking - we've worked well together today."

She let out an uncontrollable laugh and spat some of her drink out. She wasn't used to having more than one alcoholic drink at a time, and even then she sometimes went for water. Tonight was fun. He was fun.

"I'm not going to disagree with you, Jack. Today certainly wasn't the day I thought it was going to be. It's been better than I'd imagined. Although, there is one thing I need to ask you."

"Ask away."

"What the fuck is this in my ass? I almost can't sit down..."

"All will be revealed in good time. I promise it's for the best. Worth it for the experience."

The drinks and food flowed, but Jack was ever mindful of the time. They couldn't get too pissed. Not on a Wednesday night. At 11pm he suggested they make a move back to his room.

Affectionately, and semi drunkenly, arm in arm they walked out of the restaurant towards Jack's room. As they turned the corner to the corridor on which his room was, he reached down to feel her ass. Her skirt was a thin, figure-hugging material. She had no knickers on and he could feel the plug as be brushed his hand against it. What a change in a day, he thought to himself.

The curtains were open in the room, and the moon was shining in. He didn't turn on the light, and he didn't reach for the blindfold. This time, he kissed her on her lips and withdrew to look into her eyes. No more condescending, no more sarcasm, and she wasn't at all cocky.

He unzipped her dress and unhooked her bra. She stood naked in front of him -- beautifully lit by the moonlight. She had the best body he had ever seen in real life -- muscular, curved ass and huge firm tits with a beautifully bare pussy.

As she stood in front of him he bent down to his knees and faced her recently-shaved pussy. Her skin was incredibly smooth. He stroked it and put his hands between her thighs. She opened her legs and he worked his tongue between them. As he had found earlier, she was incredibly wet. She must have been getting wet all evening as they'd flirted, and she'd felt the presence of the plug in her ass. This time he was more aggressive and moved his tongue inside her. She gasped and grabbed his head with both hands. This continued for several minutes as she got wetter and wetter, warmer and warmer. It was time to revisit the plug.

He stood up, and turned her round so she was facing the open window. He moved a chair in front of her and bent her over it. She abided without protest. She spread her legs slightly, the ruby handle glistening in the sharp light. He held the handle firmly and began to withdraw the plug slowly. As her asshole stretched, she gasped out loudly and involuntarily. The plug was out and she was gaping more than when he'd used his finger earlier in the day. His plan was working, but there was a lot more to do.

He knelt down again and spread her cheeks with his hands and licked around her ass, whilst entering her pussy with two fingers. This had been a tight enough passage earlier, but now it had opened up and there was room. He continued to lick, circling her asshole. Next, he stretched his tongue out and put his inside her. He could taste the soap from the shower as she squirmed.

If today was a day of feelings she never thought she would feel, the evening was no different. She could feel every contour of his tongue as it entered her gently. It felt like a snake, twisting inside her. This sensation was only brief as he returned to finger her, gathering as much moisture as he could to apply into her ass with his fingers whilst she whimpered with pleasure.

He wasn't going to fuck her standing up so he brought her down on all fours and pulled his jeans to the floor. He took his cock out and smeared it with some of the abundantly available juice from her pussy. Now was the time. He edged it closer to her ass, pressing against it.

The hole that the plug had encouraged to form remained and he reckoned he could almost fit half a finger in there without much protest. But his cock was a lot thicker and fatter than a finger and as he edged it in she began to moan. It was a moan of pain mixed with some pleasure. He got the tip in within 60 seconds but there was so much more to go. She tried to adjust her legs and her position to be more accommodating of it. Once again she brought her head down to the floor, increasing the upward angle of her ass.

"Hold it open" he told her, taking her hands and getting her to spread herself wide, reaching behind. Whilst this helped visually, it didn't make much difference to the enormous tightness of her asshole, gripping the first 1/4 of his cock as he pressed on with the entry.

It took almost 10 minutes of see-sawing in and out and with him intermittently fingering her pussy and firmly massaging her breasts as he slowly made his way in, inch by inch. It was the tightest hole he could imagine and the thought of the tightness just made his cock swell even more as he developed a slow rhythm. He could tell by her breathing that it hurt, but he could tell by the sounds she made that she also loved it. With every stroke, she relaxed slightly.

"That's it, you can relax, I'm fully in."

He was now balls deep in her ass as he began to up the speed of the fucking he was giving her. Still, nothing like as vigorous as a traditional fucking, but still with more movement than was initially comfortable. She moaned, whimpered and seemed to gasp for air as if she were periodically forgetting to breathe.

He wasn't sure if she came. The noises she made in the minute leading up to the end sounded final, but there was nothing more he could do to hold back and he ejaculated. The cum was fired like a shotgun deep into her ass. Even as it stopped swelling, his cock still felt too big to be in her and he waited several minutes before removing it -- backing away gingerly until her removed it entirely. The gaping hole was now a proper hole. He put his hand on the top of her ass, encouraging her to stay still whilst straightening up slightly. Cum oozed out of her ass and dropped straight onto the carpet floor like a stream of lava. Another perfect photo opportunity.

___________________________________end of part 2_____________________________

peej88645
peej88645
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AnonymousAnonymousover 1 year ago

Looping through the platoon of roast chesnuts, the smallest of the frogs ddisposed of the Cortinas rear left shick absorber in the closest volcano.

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