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Introduction:

Rob helps his aunt with a problem

“Hey are sure she’s cool with this? You said that she’s become so anxious she won’t even leave the home, you think she’ll be ok with me living in her house?” Rob was talking with his mom about his new living arrangement. He’d recently gotten the news that moving forward his employer was implementing work from home for all staff. He’d been looking for a reason to break his lease and move out of his crowded apartment for some time and this gave him the motivation he needed. His drive was quickly tempered though, there honestly weren’t that many better places out there. This is when his mom suggested he rent out the basement of her sister Cheryl’s house. Cheryl lived in a pretty great location and from what Rob understood had a big house all to herself.

“Oh, don’t worry. She isn’t that bad, and it’ll be good for her to have someone else in the house. Even agoraphobs need company every now and then.” Rob wasn’t thrilled with the idea of being his Aunt’s therapy dog, but for what was essentially free room and bored he couldn’t say no.

Growing up he had only seen Cheryl a couple of times. Since he moved to the same state as her, he only saw her twice at the holidays. He’d always thought she was a little weird but she was nice enough. When moving day finally came around Rob only saw Cheryl four or five times as he brought his stuff to the basement. He was impressed how despite her obvious issues with people she was still beautiful for her age looked like she kept herself fit. She more or less looked the same as she did the last time Rob had seen her a couple years ago. The first weeks of the new living arrangement were strange but Cheryl quickly took to the fact that Rob was willing to run errands, pick up groceries, and even cook. Rob didn’t mind these chores and he loved having most of the house to himself. Cheryl seemed to only leave her bedroom to go to her study she used as a gym and office.

Around week four Rob stopped seeing her almost all together. She began taking her meals in her rooms, and it seemed like she was avoiding Rob. It got to the point where Rob was only seeing her when he grabbed her shopping lists and dropped off her meals. He was a little concerned but kept it to himself.

One Tuesday morning when Rob dropped off his Aunt’s breakfast she gave him a shopping list with some unusual items on it. Rob had noticed that Cheryl was asking for more fiber in her diet but he wasn’t prepared to see diuretics and an enema on the shopping list. It made him a bit uncomfortable but he knew how worried she was about going out and that he was her only access to the outside.

Around lunch Rob went on a shopping run and grabbed everything on the list. He hated the looks he got in the pharmacy but toughed through it. He returned to the home with two weeks’ worth of groceries, a trunk full of box wine, and the rest of Cheryl’s list. He was a bit sheepish and just left his Aunt’s items outside her door. When Rob went to drop off her dinner the bag from the pharmacy was gone. Neither said anything about it and the week went on as the normal.

The next day Rob assumed whatever Cheryl was going through had been resolved and he put it out of his mind. That Friday Rob was parked on the couch in the living room when he got a text from his Aunt, “Can you bring me a box of the Sauvignon Blanc?”

This wasn’t and odd request, especially for a Friday, so Rob got up off the couch and brought her a fresh box. She answered the door wearing a mask which was normal but she was only in a tightly tied bathrobe, “Thank you Rob, you’re a doll. Can you also actually give me a hand with something else?”

Rob didn’t think anything of it and agreed, he even put on a mask before entering her room. Cheryl walked him to her bathroom where the enema was on the counter. Rob couldn’t see but was sure Cheryl was blushing hard. Rob was uncomfortable by all this but wanted to see where it was actually going. Cheryl put the box of wine on the counter and poured herself a large glass. Using a straw slipped under her mask she polished off the glass. She turned to Rob, “So you probably have guessed but I’ve had some stomach trouble. I tried to do this by myself but it’s very difficult. I wouldn’t ask you to do this if I had any other option.”

Rob’s heart was racing; he knew what she was asking and didn’t know what else he could do. Cheryl was asking him to help her and he couldn’t say no. “Just… just tell me what you need me to do…”

Cheryl cleared her throat and took another big sip of wine. Putting the glass down, she handed Rob some rubber gloves and picked up the enema. “So I tried to put this in by myself but I just can’t”

She was clearly blushing now as she handed the enema to rob. She took a jar of petroleum jelly and opened the lid, “You’ll take that end and place it, and then you pour water in that other side…”

She took another long sip of wine and turned to face the counter and bent over slightly. Rob took a finger load of petroleum jelly and rubbed it around the tip of the enema. Holding the tip as low as he could and trying not to fumble it with the rubber gloves he lifted his Aunt’s robe slightly and brought the tip between her legs.

Rob had seen Cheryl in a swimsuit a few times and he remembered how trim she was for 55. As he looked at her tight athletic ass through the robe and thought about what he was about to do, he got a little hard. He brought the tip up till he hit flesh and then he ran it forward till he slid in. Cheryl let out a yelp “NOT THERE!!!”

Rob yanked the tip down and started again, he was fully erect at this point. He brought the tip well above where her asshole was and ran it forward again, this time hitting his mark. She let out a little squeak. He pushed it in a little but he didn’t have a great grip and he could see Cheryl tensing her ass. He tried to push it in a little deeper when Cheryl grabbed his hand, “I think we can use the water now”

Taking an empty glass Rob began filling the enema bladder with warm water. As he filled it, the water was clearly running down Cheryl’s leg. “I think it’s done, can you please leave”

Cheryl was clearly embarrassed and irritated that this wasn’t working so Rob emptied the bladder in the sink and stepped out, closing the door behind him. He knew this wasn’t done and so he waited in her room. Eventually Cheryl opened the door again, and it was clear to Rob she had downed quite a bit more wine. “I looked online and I think it needs to be placed a little further in, also… also I think it works better if I bend over”

Rob waited till Cheryl turned to go back into the bathroom before standing up, his erection was raging. Cheryl walked in, spread her legs till they were two feet apart and bent over, resting her elbows on the toilet seat. The petroleum jelly had come off the tip in their last attempt so Rob reapplied heavily. “Just make sure it’s all the way in” Cheryl said as she raised the back of her robe. Rob wasn’t expecting this but was amazed by the sight. His Aunt’s ass was as cute and sculpted as he could have imagined but she also had the hairiest pussy he’d ever seen in person. Clearly she had not been trimming for some time. She had a small amount of hair around her ass but by the time it got to the top of her pussy it was so thick he couldn’t see her clit. Trying not to linger at the sight of her asshole and pussy, Rob adjusted and placed the tip of the enema right on her rosebud. Cheryl inhaled slightly and tried to relax. He held it against her hole for a couple seconds as she relaxed more. Once he thought she was loose enough he began to push it in. The first inch went in easily but as Rob tried to push the next three inches in Cheryl began whining under her breath. Cheryl winced and eventually exclaimed “It’s hurting a little, I think you should pull it out”

Rob agreed and pulled in out all the way. “Ok. Just relax and I’ll take it a little slower.” He reapplied petroleum jelly to the tip and began again. He easily pushed and got the first two inches into her, but could see Cheryl tensing her ass. Thinking it might help her relax a little and desperately wanting to fuck, Rob began pulling the tip back and forth working it deeper and deeper into her. Cheryl relaxed as he fucked her with the tip and inch by inch the enema was fully inserted.

Rob grabbed the bladder and began filling it up again. Unlike last time the water wasn’t leaking. Grabbing the top of the bladder he slowly filled his Aunt’s ass. She gave a little yelp when he started but was quiet after that. “Ok, I’ve emptied it out.” Rob said as he squeezed the last bit of water out.

“Now carefully pull it out and leave the room” Cheryl eked out in a shaky voice. Rob began gently pulling the tip out of her. She was tensing her ass to the point where she was shaking a little, trying not to spill a drop. With a wet plop, the enema was removed and Rob was quickly out the door. He waited in her bedroom again as her heard his Aunt scramble with the toilet seat and released her bowels. After a couple minutes of quite he got up to leave. As he was leaving he heard the bathroom door open, “It didn’t quite work. It feels better but I’m not there yet.” Cheryl looked tired and defeated. She was grasping another empty glass of wine and her robe was coming undone and she didn’t seem to care. “I did also read that stretching might help. I mean we’ve already gone this far.”

Rob wasn’t exactly sure what she meant but followed her back into the bathroom. Cheryl was pouring herself another large glass of wine. Once she had downed it she bent over the counter again and lifted he robe exposing her sex. “I read that one or two fingers should do it but that the more it stretches the better” She buried her head in her arms and whimpered a little.

Rob grabbed the jar of petroleum jelly and dipped his right middle finger in it. Positioning himself behind his Aunt he pressed his finger against her asshole. He easily pushed it all the way in. Ignoring Cheryl’s gasps he pulled it all the way out and shoved it all the way in. Her asshole was making a little popping noise. Planting his finger in her as deep as it’d go, he began wiggling it around in a clockwise fashion. This elicited a few more gasps, especially when he was pushing on the wall between her rectum and her pussy. Rob removed his finger completely and dipped his middle and pointer finger into the lube. This time he gently inserted the two fingers into her. She moaned as he pushed all the way in. Soon he was pumping them in and out of her, letting her asshole close every time. Rob could barely contain himself; he wanted to fuck her so badly. He’d played with some chick’s asses before but nothing like this. She had literally given him license to do what he wanted to her hole. He began rubbing both fingers up and down the length of the wall between her pussy and ass. Cheryl began moaning softly. With his fingers all the way inside her he could just barely rub her G-spot from the inside. The first time she bucked her hips slightly Rob knew he’d hit the spot. He began pushing hard and rubbing in circles as Cheryl tightened her ass in rhythm. They both ignored the first outright cry from Cheryl but as the orgasm was building in her she had to try and stop him, “Please, ah god, please, don’t, ah, don’t do this”. Through her pleas she was still moving hips to his rubbing and not moving to stop the action. All of a sudden she clamped down on Rob’s hand with her rectums and let out moan. Rob pulled his fingers out and she sighed and whimpered. Her legs were shaking a bit.

Deciding to ignore the awkward silence Rob took the tip of the enema once more and stuck it in his Aunt. He easily pushed it all the way in. He filled the bladder again. “I think you should squeeze hard to make sure it doesn’t leak.” Cheryl grunted and he saw her ass tense up. Rob squeezed the bladder into her. As he went to pull the enema out, his Aunt mumbled “You can leave after this, I’ll clean up.” Rob pulled the enema out, took off the gloves, and left her room.

Their previous routine continued for a the next couple of days, with Rob bringing Cheryl her meals and them not interacting, but that Thursday when Rob went to drop off Cheryl’s dinner, she was waiting for him. She looked a little different than before. She honestly was just looking healthier. Rob thought on it and he figured she must have run low on wine since with what she had drank Tuesday night she’d probably be empty by now. “He do you need anything? There’s some wine in the fridge.” He asked not really knowing where this all was going.

“No, I decided to slow down a bit with all that.” Cheryl wasn’t making eye contact but it was clear she wanted to ask something. Rob wanted to move things along and decided to force a response “Yeah I know you weren’t feeling too good earlier this week. If you need anything, anything at all, just let me know.”

Cheryl cleared her throat slightly “Although I did feel better Wednesday, I’m still having some problems. I’d do it myself if I could but I need your help again.” Rob’s pants felt tight. He’d jerked off right after the last time and he couldn’t get the image of fingering her ass to completion out of his head. Rob didn’t want to sound too eager, so he took a quick breath and responded “Yeah, anything you need.”

He went to leave but Cheryl stayed at the door. She motioned for him to come in and placed her dinner on her desk. Rob was a little confused because last time she had been in a robe and seemed ready for what was happening. Tonight she was wearing yoga pants and a tee-shirt. Rob could see she wasn’t wearing a bra but he was still excited to see how this was going to go. He followed his Aunt through her room and into the bathroom. The enema, gloves, and petroleum jelly were on the counter again and he didn’t see the box of wine. He was rock hard realizing that his Aunt was going to have him finger her asshole again stone cold sober. With them both in the bathroom Cheryl began undressing. She pulled the tee-shirt off exposing her sagging breast. They still had some perk to them but her age was showing. “I did a bit more research and this article I read said to try to get the enema all the way to the blockage for this to be most effective. So I think we should do a bit more warming up this time.” Rob was only half listening, he was trying to contain his anticipation and not ogle his Aunt too much. She began removing her pants and Rob went to the counter. Now that she was completely naked she grabbed a towel and put it over the toilet seat. She spread he legs and leaned forward, resting her arms and head on the towel. Rob could hardly contain himself.

There Cheryl was, bent over, with her ass and pussy fully exposed, and thanks to this angle he could also see her tits hanging and resting on the towel. Rob noticed immediately that there was a big difference. At some point in the last couple of days Cheryl had taken it upon herself to tidy up a bit. She was still much hairier than he was used to but now it was cut back a little and he could actually see all of her pussy.

Rob took the jar of petroleum jelly and approached her. For all of her exhibitionism he could still see that she was tensing her asshole. He rubbed his finger in the jar and placed it on her asshole. He didn’t push in just yet, he just rubbed the puckered hole, massaging the area around the opening until he could feel her begin to relax. When he thought she was ready he pushed his finger against her hole and in slid in quite easily. Without really trying he had pushed his finger all the way in before Cheryl gasped and tightened. Rob pulled his finger out and reapplied the petroleum jelly. He realized he’d forgotten the gloves but it was already too late for that. With two fingers he returned to her rosebud. He met more resistance this time and had to pump his fingers in and out to gain any ground. Soon though, he had his fingers back in her. She moaned slightly as Rob repeated his act from Tuesday night. Pushing hard and rubbing up against her G spot. Rob kept at it and started to notice a smell he hadn’t the last time he’d done this. He was so close to her pussy and taking a slight lean back he could see that fluid had started to form at her lips. He kept working her through her asshole and she stopped trying to hide her enjoyment. She was moaning loudly in the towels as Rob felt her tighten up and then all at once release. She fell to her knees, Rob’s fingers slipped out of her as she dropped. Rob went to the sink and washed his hands, they looked clean but it was a habit. Cheryl hadn’t moved, but through the towels she said “Ok, so I think we need to keep going a little to make sure it really works this time.” She straightened her legs and returned to her previous position. “If you have anything big, bigger than, bigger than a finger, I think it might be time to use that” Although she stumbled through the words Rob wasn’t going to let this opportunity pass. In seconds his pants had dropped and he had his hard cock out. He grabbed some petroleum jelly and gave his cock a few god rubs. He couldn’t hear his aunt whimper a little as he got behind her, and he saw her ass tighten up again. Similar to before, he took his cock and began to rub it against the outside of her asshole. His precum mixed with the petroleum jelly and pretty soon she was relaxing again.

In a slow and controlled manner he pushed the head of his cock against her hole. She gasped into the towel as he slid just his tip into her. He’d barely gotten in an inch when she tightened again, pushing him out. He reached down with one hand and gently grabbed her hip as he guided is cock into her again. This time he was able to push deeper and when she again tensed up he was able to stand his ground. He pulled back slightly and waited for her to relax again before pushing deeper. He repeated this a few more times till he was all the way in. With his cock securely in her he grabbed her wide hips with both hands and began to fulfill his fantasy. He could hear Cheryl grunt each time he bottomed out in her but otherwise she seemed to be comfortable taking it. With his fixation on this act for most of the week, the feeling of her tight ass gripping his rock hard dick was overpowering. In an embarrassingly short time he could feel his climax building. Too caught up in the moment he released her hits and reached down to grab her breast. They may have been past their prime but her tits were just what he needed. Seconds after getting a hard grip on them he began cumming in her ass.

He stopped pumping his cock into her and just rested for a second. He could feel her ass tighten a bit and now that he was softening she pushed him out of her. As his cock hit the cooler air he came to and released her tits. Stumbling back he looked at her asshole as it slowly leaked out his cum. Muffled slightly due to the towels Cheryl finally broke the silence, “I, I think I’m ready now.”

Rob remembered why he was supposedly here in the first place and pulled up his pants. He went to the counter for the enema. Once the tip was lubed he approached that great ass of hers. He marveled at the site for an instant, relishing the fact that he could see a bit of his seed leaking from her. He positioned himself behind her and pressed the tip against her rosebud. It went in without resistance and he just kept pushing until it was in 10 inches and he hit an obstruction. Using a glass, he again filled the enema, and then Cheryl. Once the enema was emptied he slowly removed the tube from her ass, once more giving her the heads up to clench as he pulled the tip out. He deposited the device on the counter and stepped out to give her some privacy. He waited in her room for a couple of minutes when he heard the toilet flush and the shower start running. He got up to leave when the bathroom door opened again.

Cheryl stood in the doorway. She had put her hair up in a loose bun and was staring at the carpet. She hadn’t put anything on so Rob got to enjoy the full view of her fit but maturing body. It had only been a couple of minutes but Rob felt himself stirring again. Cheryl cleared her throat, “I was going to take a quick shower”, and before Cheryl could finish her sentence Rob was underdressing. She didn’t say another word as he stripped naked and approached the bathroom. His erection had become obvious, and Cheryl sheepishly led the way to the shower. Rob followed her, excited to find out what exactly she had in mind. With both of them in the shower, she took a sponge and began cleaning herself in the warm water, taking extra care with her ass and womanhood. Rob stood in the shower watching her as she finished up. Without saying a word Cheryl switched spots with Rob so he was now mainly in the stream. She lathered soap onto the sponge once more and began rubbing down Rob’s body. Rob wasn’t especially athletic but he kept himself in decent shape. He didn’t have washboard abs, but he had enough definition that you knew they were there. He’d never felt as good about his body as he did as Cheryl rubbed him down with that sponge. She worked slowly and thoroughly cleaning him from his shoulders and working her way down.

When she got to his hips, she skipped down to his calves and began working her way back up. The water running down his body mixed with the delicate work of this woman’s hands was driving Rob to the brink. He needed to get off, he needed her to give him more attention. As she approached his cock she slowed significantly. When she couldn’t avoid it any longer she ran the sponge up along his leg to the bottom of his abs and then down his shaft. Since she wasn’t gripping hard the motion didn’t work to clean him but he did enjoy it. After two more tries like this, Cheryl released a defeated exhale and used her free hand to hold him steady. Now that she was gently rubbing him clean he had to focus hard not to release. When she began cleaning his underside, running the sponge from his balls up to his tip he had to brace against the walls to keep himself steady. She stopped abruptly and stood, wringing out the sponge and placing it on its drying rack. Rob took this moment to rinse the soap from his body.

Without saying a word Cheryl reached around Rob and turned off the shower. She grabbed two towels and passed one to Rob. He was eager to get on to whatever Cheryl was planning, so he hastily dried himself. Cheryl had turned away from Rob and was slowly drying herself off, when she couldn’t delay any longer she hung up her towel and walked out into her bedroom. Rob followed her out and a little fed up with how long this was taking finally resolved to take control. As Cheryl slowly approached the bed Rob grabbed her by the shoulder and spun her around. Without any more warning he held Cheryl’s head in one hand and leaned in to kiss her on her lips. She pushed back at first, but as one of his other hand rested on the small of her back she melted into him and began kissing back. Rob wanted to dive into her, but he knew that he should treat her like the beautiful creature she was. Rob released her head and reached down and gripped the back of her thighs with both hands. Bending his knees slightly he picked her up and held her for a second before leaning forward and depositing her on the edge of the bed. Taking a half step back Rob began kissing her neck as she lay there. Working his way down her body he lingered on her breasts, gripping them and tracing out her areolas with his tongue. Cheryl was letting out little gasps as her nipples hardened. Rob returned to kissing her, but kept his hands on her nipples, kneading them slightly with his fingers.

As he kissed his way down her stomach he could feel her squirming slightly. He approached her hairline and released his grip on her breasts. He couldn’t tell if she was moving in anticipation or in avoidance but either way he gripped her inner highs and pulled on her skin with his thumbs, further revealing her delicate sex. Inhaling her scent, he lowered his face and pushed his tongue through her folds. He found his mark and began circling her hole. Once he felt like he had a good taste of her musk he ran his tongue up through her lips to her inflamed bud. Unlike most of his experiences this week, this was something Rob was familiar with. He began by just slowly lapping at her with his tongue, as her breathing quickened he began flicking her clit side to side with the tip. Cheryl began gently grinding her hips in rhythm with his tongue. Rob alternated techniques to keep up his endurance but he could feel another orgasm building in Cheryl. Her breathing began getting erratic so he licked harder and faster. He felt her reach down and begin pulling his hair, “That’s enough, ah, that’s enough!”

Rob knew she still had a little more in her so he pushed through focusing on her body and breathing, until he legs closed on his head and she began shaking. This wasn’t the gentle quivering he was used to but instead a borderline violent display accompanied by a moan that started strong but petered out to a whimper. Cheryl’s legs relaxed and she went limp.

Now Rob was ready to get his. He stood back up and pulled Cheryl back to the edge of the bed. He leaned forward and slowly pressed himself into her. Her body was more than ready for this and eagerly accepted his penetration. All the anticipation was almost overpowering Rob. He closed his eyes hard as he began pounding into her small frame. She began to make sharp exhales in time with his thrusts and he felt her tighten her velvety slit. This was too much for him and without warning his seed erupted into her. He collapsed onto his forearms and as he was pulling out Cheryl wrapped her legs around him. Taking the hint he stayed in her and instead wrapped one arm under her torso and brought her further onto the bed so he could lay on her without putting too much weight into her.

It was several minutes before their breathing became regular. Cheryl slowly unwrapped her legs from around Rob and released him. He stood and for a second considered leaving, instead he got back on the bed and embraced Cheryl once more.

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