Chris's Embarrassing Problem

Warning: The following story has male anal, as well as m/f incest. All characters are fictional, and they and this story are products of my warped and twisted mind. Turn back now if this isn't your cup of tea. The most important thing you can do is vote on this and any other story you read here. I encourage you to do so. If I don't know if you like it or hate it, I have no reason to write a sequel.

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Chris Jacobs was 19 years old, a college freshman, and thoroughly frightened.

Chris was amazingly grateful for his high-speed internet connection - he secretly referred to it as his pipeline to porn. He loved his porn, but lately he'd been having a problem He couldn't always cum though. His dick just didn't respond, and as it got worse, his balls would ache. A good orgasm would clear it, usually, but it had been a week since he'd been able to cum, and his dick would droop halfway through trying from the ache.

This scared him. He shouldn't be impotent at his age. Chris lived with his widowed mom, Rosemarie whom everyone called "Jinx" since her childhood. His mom had explained that she got the nickname because as a child she would almost always know what someone else would say, and blurted it out with them, and "Jinx you owe me a coke" became Jinx.

Chris was mortified with his "shrinking violet" and called his Uncle Larry, his mother's brother in law, who was a urologist. Larry agreed to be quiet unless he found a problem. He examined Chris in his office after hours, and then asked Chris some thoroughly embarrassing questions. Afterward they sat in Larry's office.

"Well Chris, your problem isn't too serious, but it's very rare in a teenager. You told me when you ejaculate, it's usually a lot. Now teens who are virgins generally jerk off like the energizer bunny - they keep going and going. In your case, your randomly losing your erection, and the sperm is building up, which is causing inflammation in your testicles, which them causes you to lose your erection, and its a cycle you need to break."

Chris looked at his uncle in confusion and said "What can I do to help myself Uncle Larry?"

Larry pushed his glasses up, ran a hand through his receding hair and sighed. "Go on amazon and buy yourself a dildo, or a butt plug. Anal stimulation of the prostate will help you maintain your erection, and increase your ejaculations."

He looked at his uncle in abject horror, and exclaimed "Dude! I am not gay!" Larry reassured the teen that even straight men could enjoy anal sex, and it would help him out.

When Chris got home, he went online, and started looking for sex aids. Unsure of what to buy, he went o his order status to see where the video game he ordered was. In the order history, he saw his mom had apparently ordered herself a dildo a few weeks preciously. Chris's mind then started spinning when he realized that his mom would surely see if he ordered a sex aid.

After some serious contemplation, Chris came upon a solution. He'd borrow Jinx's dildo. Jinx was at her job as a Nurse, and wouldn't be home for 2 hours or so. He could go in her room, slip the dildo in, and have an orgasm.

He went into his mom's room with his laptop, and sat on the bed. He looked at the nightstand, and on it was a picture of Jinx, and Steve, his late father who was tragically killed 2 years previously by an IED in Afghanistan. He turned it face down in embarrassment.

He opened the top drawer. Nothing. He opened the bottom drawer - and gasped. Apparently his Mom didn't have a dildo. She had dildos - and lots of them! They were all different colors and shapes. He selected what appeared to be the smallest. It was about 8 inches long, and an inch and a half or three quarters wide.. It was narrower than his own cock, but longer.

He stood up and dropped his basketball shorts. He wasn't wearing underwear. He stepped out of the shorts, and climbed on the bed, holding the dildo. He opened his laptop, and watched some anal porn. He figured that would be a good theme for his 'treatment.'

As usual, he lost his erection a few minutes of stroking. He turned on his side, and grasped the dildo. As he'd seen in the videos, he just tried to shove it in.

"MOTHERFUCKER!!" he yelled, and threw the dildo across the room after a burning pain came from his virginal o-ring.

"I don't care if I never cum again," he mentally grumbled while holding his ass. "I don't know how people can do that shit!"

Later that day, he realized he was going to have to ask his mom for help. And the very thought chilled his bones. He knew she was a medical professional, but these were his balls - a part his mom hadn't seen since his diaper days, and he'd have proffered to keep it that way. He decided to make dinner - not something he did everyday, but often enough that Jinx wouldn't think it odd. It usually put her in a good mood.

Jinx came in the door after a rough day, and a rougher commute, and smiled at the smell of garlic in the air. As her heritage was Italian, she always equated garlic with warm kitchens, good family and good food - love. She walked in the kitchen to find her son with a spoon outstretched. "Taste?" he queried. Jinx happily accepted the jot spoon in her mouth, and smiled in happiness.

"Delicious!" she exclaimed, and hugged the beaming chef. "I just need to go change out of this sweaty scrubs. Will dinner be ready to serve by then?"

"We have about 10 minutes, if you want to take a quick shower" Chris replied.

Jinx entered the master suite, quickly stripped, and entered the glass enclosure, letting the hot water pour over her lithe frame. She grabbed her razor, and quickly scraped off the stubble from her pussy and legs mechanically. She loved being hairless, and hadn't had much time that morning.

She then luxuriated in the steamy shower, rubbing her body with vanilla and coconut body wash, and mused about how she had a damn good body for 38. Muscular, but not grossly so due to good genes, and hard work at her job. Firm 32 D boobs which looked huge on her five foot three inch frame, They were still upturned and perky,

She turned off the water after hearing her son shout that dinner was ready and swiftly toweled off and put on an old Metallica shirt of her husbands and compression shorts, her standard around the house outfit, eschewing underwear as was her custom. She returned to her kitchen, and sat down at the table, happily digging in, and began talking to Chris about her day.

She noticed quickly that her son was not meeting her gaze, and giving one word answers to question. Her spidey sense tingling, she pointed her fork at her son, and asked, "OK - out with it. What's wrong?"

Chris put down his fork, and looked down. After a moment, he looked up at his mom's green eyed gaze, and returned his eyes to his plate. In a quite halting voice, he said "I went to see Uncle Larry today - I have a medical, um...man issue."

His mother paled. She quickly queried, "Well, I'd assume it was with your 'man parts/ considering his specialty. I'm also assuming you were too embarrassed to talk to me, even if I'm your mom who you could tell anything. Are you OK, is it serious?"

Chris took a deep breath, continuing to look at his half eaten dinner. "Uncle Larry says it's not serious yet, but it's uncomfortable for me to discuss, and to experience. When I jerk...um...masturbate, I lose my erection before I can..um..ejaculate."

"Well, I can see why you're embarrassed, but it's not the end of the world. Did Larry give you medication, or a treatment?" she asked her red faced son.

His gazed locked down still, he replied, "He suggested I use an..um..aid to orgasm."

His mother squinted for a moment before softly asking, "An aide as in a person, or a sex aid - like a butt plug or a dildo?"

"The second one," her son quickly answered, "But I...um..borrowed one of yours from your bedside table and that isn't going to happen."

Jinx paled again, realizing her son had seen her toy collection, and released the breath she had unconsciously been holding. "Well, aside from violating my privacy big time, what do you mean by 'that isn't going to happen?' If you need to do it, it's going to happen!" she exclaimed.

"I tried one of your smaller...aids...but it burned like fire" Chris replied.

No stranger to anal play, Jinx replied, "That's not a big deal. You could have been allergic to the toy or lubricant or you simply didn't use enough lubricant."

Chris meekly looked up, and asked "Lubricant? What do you mean..like oil? Do I have to oil my butt?"

"Kind of," Jinx replied. Your butt doesn't really generate much lubricant, except for mucus to help you defecate. You have to use something slippery to get it in, and be very relaxed."

Chris mused about this for several heartbeats, and asked "Mom...you have to help me. I obviously can't do this by myself. You're a nurse, and my mom. I trust you, even if I'm nervous and scared."

Jinx's stern expression softened with her boy's flattery. "I can try to help you, but I am going to need your trust, your love, and your complete obedience, We're both going to see and touch things mothers and adult sons don't normally see or touch, and it's going to be uncomfortable and embarrassing for us both. We're going into a sexual type situation here, but I know you need this. I'm going to try to be less than clinical in my language so you can relax. The swear jar is off the table for the next few days. I'll call Larry later to confirm what's going on, and since tomorrow is Saturday, we'll do it in the afternoon."

After dinner and washing the dishes, Jinx phoned Larry to confirm the issue, and the treatment. Larry assured Jinx she didn't have to worry, if Chris took care of the issue.

After a long night of worry, Chris woke up to a morning wood, and the smell of coffee. He pulled on some basketball shorts, and made his way to the bathroom. Thinking of nasty things like Donald Trump and Rosie O'Donnell having sex, and his boner relaxed, allowing him to pee.

He went downstairs for breakfast, and found is mom sin the same tee and shorts as the previous evening, reading and sipping her coffee while unconsciously twirling the ends of her auburn mane.

Chris reached into the cabinet for Frosted Flakes, when his mother spoke up, "Nope. No cereal. We're going up where no man has gone before, and the less up there, the better. Have some apple sauce or yogurt for breakfast and lunch. I'll need to go get some things that will help, but nothing solid. Have plenty of coffee, as that will act as a laxative."

Despite Chris's mild horror at the upcoming event, he was grateful to his mom. His balls were starting to feel like the time his buddy Eric chopped a fastball back off the plate and hit him in the cup when they played ball years back. He tried distracting himself by playing some 'Call of Duty' online with his friends. He heard his mom go out soon after beginning.

Jinx returned about an hour later, and went into her room. She changed to fresh shorts and a tee, and changed her bed linens, She then lay a pillow about 3 feet from the pillows at the top of the bed, and covered them all with another sheet.

She placed a towel on the butt pillow lump, and another on her nightstand. On the nightstand, she laid out her purchases - an enema kit, a tube of astroglide, a box of condoms, and a small butt plug, as well as a dildo, about 6 inches long and inch and a half wide.

She called Chris to her room. He came strolling in, but froze when he saw her nightstand. Jinx walked through the items, and explained each items use and purpose in clinical terms. Chris was fairly intelligent, and his mom a good teacher, but he still wasn't feeling good about all this. Jinx finished her explaining with "And now let's go to the bathroom so I can give you an enema"

Chris looked at his mother in abject horror. "You're going to give me an enema?" he squeaked.

"As I said yesterday Chris we both may see some things we don't want to. If you think I'm enjoying seeing your bare ass in the air, I'm not - but you need to be clean for this!" she snapped. "Now - get naked," she ordered.

Chris turned away from his mother, and stripped off his tank top and basketball ball shirts, and covered his crotch with his hands. His mom picked up the astroglide and the enema kit, and walked into the master bath. Chris meekly followed, still guarding his crotch like they really were family jewels.

Jinx filled the bag with warm water and hung it in the shower. She the placed a folded towel on the floor, and said "Okay Honey. You want to get down on all fours with your knees on the towel." Chris slowly got in a position, and heard the unmistakable click of the lubricant tube opening. He then felt the slick tube enter his tight hole.

"Now baby your going to have to try to relax. If you can keep relaxed this afternoon, ts going to help with everything we do, You're going to feel the warm water enter you. If it starts to cramp, you're going to rub your belly. If it gets too bad though, just tell me." Jinx explained.

Chris felt the stream begin in his ass. While not unpleasant, he wasn't enamored with the feeling. When he began having some mild discomfort, he rubbed his gut as instructed, stopping his mother soon after.

His mom helped him up, and left the room as he voided and flushed She entered the room, gave a quick puff of air freshener, and repeated the procedure. She then had Chris take a shower.

Chris exited the bathroom with a towel securely wrapping his waist. Jinx took his hand, and with he other hand she removed the towel. Chris covered himself with his free hand.

Jinx sighed, and said. "Chris honey, it's inevitable I'm going to see your cock today. I'm sure you have nothing to be embarrassed about besides your nudity. Heck, I saw your butt crack a minute ago. Let Mr. Happy out, and hop on the bed face up, booty on the pillow."

Chris climbed on the bed and took his position. Jinx noted to herself Mr. Happy was indeed unhappy, but her son appeared to have nothing to be embarrassed about physically. He was about six foot tall, and brown haired. He wasn't grossly muscular or fat, just healthy looking. His pubes had been clipped, and his testicles appeared shaved.

They were also on the larger end of the spectrum that she had seen in her career. His fathers ball sack had also been larger, but not quite as big as Chris's.

Jinx hopped up on the bed, between her nude son and the nightstand. She put on some rubber gloves, put a condom on the dildo, and reached for the lube. "Shit! I left the lube in the bathroom," she said, and went into her bathroom to retrieve it.

She had forgotten to close it, and upon picking it up, she squeezed a large dollop on her white Guns N' Roses tee. With out thinking, she rubbed it in, and then realized her error. She closed the tube, and hand washed the stain, leaving the shirt to dry over the shower rod.

She realized her son would see her boobs, and a slight thrill ran through her. She rationalized not covering herself with a towel by thinking if her son was nude already, her breasts might distract him from his plight.

Picking up the tube, she walked into the bedroom, and got back on the bed. Chris took one look, his eyes about popped out of his head, and Mr. Happy became Mr. Excitement, rapidly growing to about seven inches length, and about two inches thick. Jinx noted he was wider and thicker than Steve had been.

Chris choked out "Mom..your boobs!!"

Jinx smiled, and said, "Relax honey. I told you we're both going to see things today. I'm sure you weren't planning on seeing the gals, but they came to the party. We needed you to get an erection, and this certainly helped."

Chris continued to stare at his mom's rack. They sat high on her chest, and were topped with the puffiest, dusky pink nipples he had seen, in porn or on the two girls he had slept with in the eighteen moths since he lost his cherry. They were astounding to him. He was so enamored, his cock head leaked precum on his now plum colored head,

Jinx guided Chris's knees up, opened the astroglide, and squirted some lube on her son's throbbing pecker as well as the butt plug. It was about three inches in length, maybe an inch and a quarter wide, and she swirled it around. She added some additional lube to her index finger,

"Now Chris, I want you to masturbate yourself. I'm going to loosen you with this plug, and if you still can't cum, we're going to use the dildo, alright?" Jinx asked. Still mesmerized by the twin peaks his mother was sports, Chris began to jerk himself.

As Chris pleasured himself, Jinx lubed his asshole, and gently inserted a finger. Her son hardly seemed to notice, between her tits, and her small hands. She wormed in another finger, and Chris's breathing deepened. He moaned.

"Good, baby," she gently crooned, and exchanged her fingers for the plug. Witch a brief push, it seated firmly in his ass, base against his balloon knot. Chris's frantic masturbation slowed significantly.

"You okay honey?" Jinx asked. Chris took a deep breath, and removed his hand from his softening dick.

"Sorry Mom," he explained, "My balls hurt, and I'm not really liking that thing in my butt. Your fingers were kinda good, but that plug isn't working for me."

Jinx had him push while she removed the plug. "Okay baby we're going to try something else." she said. She made sure both her were lubed, and began to massage her son's balls while fingering his tight hole.

Chris's flagging erection returned, and Jinx encouraged him to jerk off again. She managed to get three fingers in him and he was moaning, but his erection swiftly began to flag again.

Jinx lubed the dildo, and gently pushed it into his ass, and he began to stiffen. He restarted his masturbation, but flagged again. Jinx got up, and returned to the bedside table. She opened her toy drawer, and began rooting around in the bottom drawer.

"I got something for your dad that we never got to use." Jinx explained. "Do you remember that scene in 'Deadpool' when they're having sex during all the holidays? Remember 'International Woman Day'?" As this was a favorite movie of the two, Chris's head jerked up in remembrance as his mom held up a strap on dildo.

It was black, and about eight inches long and roughly an inch and three quarter wide. As Chris watched in disbelief, Jinx rolled a condom on the toy, pulled off her shorts and pulled up the harness. The dildo had a knob that slipped into her pussy with ease, as she had gotten quite wet from watching her son play with his throbbing cock.

She helped the stunned young man turn over and had get on all fours. She climbed up behind him, greased her strap on, and pushed the gleaming head up her son's upturned ass,

"Holy Fuck!" Chris exclaimed. Jinx was consumed by the fog of sex. She basically forgot who she was with, only concentrating on the animalistic rutting she was experiencing.

He tight quim was streaming juice down her legs as she long stroked her son's ass. Chris was moaning feverishly, and bucking into his mother's ersatz dick. With a cry, Chris came, but only ejaculated a small dribble.

Jinx pulled out of her son's ass with a sucking sound and sat back on her haunches. She wiped her sweaty brow, and asked, "Your balls feel better, Baby?" Chris help up his shaking hand, and showed his mother his small spend.

"It felt really good, but I wasn't able to cum so much." he said in a disappointed voice. "No worries, Baby," his mother reassured. "Round two is going to clear you out!"

She had Chris roll over again to his original position. He took a good look at his mom. Her chest was flushed, making her titties look even more enticing. He could see the gleam of his mothers cream on her naked and trembling thighs. His young cock rapidly returned to full tumescence.