A Son Helps His Mom's Friend

Jake had no idea what he was walking in on when he joyously entered the house, the ladies sat on the sofa legs tucked comfortably under them slowly working on their second bottle of red wine with streaks of newly shed tears drying on their cheeks. They had been lamenting over his mom's friend love life or actually the lack of one; she had divorced from an unhappy marriage some years ago and had struggled since in finding a man, though a few had flirted in and left shortly after.

"Hey ladies," he said happily after entering.

"Oh honey, it's so nice to see you and so nice for you to come home and visit your mom. One could only wish for such a man, such a mensch." His mom's friend said giving him an enormous hug and kiss on his neck. Though just one of his mom's best friend he considered her an aunt as she had been a regular figure in is his life for as long as he could remember.

Jake had not been home in some time, he was forty going on forty one and ran his own company in Florida, however a conference brought him into town and he took advantage to see his mom and go out with some old friends. He was coming home now after spending the evening over cocktails with a few friends.

"What's the matter ladies, you look like you guys have been crying, and it appears that you have also been drinking," he said as he picked up and shook the almost empty second bottle.

His mom looked at him and also got up and gave him a big loving hug, holding him tight not realizing what her breasts pressing into his chest actually did to him. For Jake had harbored a crush on his mom for as long as he could remember and used the thoughts of her voluptuous body as fuel for many a masturbation sessions. He loved and respected his mother and would never do anything to disrespect her but there was nothing that she could ask him that he wouldn't do; and that would be put to the test that evening.

"Oh nothing honey, we are just talking and letting out some pent up tears. Sometimes us ladies have to do that and it doesn't mean that there is anything wrong." She said. "Now go up to your room and leave us be, I'll make you a big breakfast in the morning and we'll catch up."

Jake happily jogged upstairs to his old room and fired up his laptop to check his emails before bed. His room upstairs shared a bathroom with the guestroom and he usually left his bathroom door open. He checked his emails then got ready for bed. After stripping down to nothing and getting into bed he began massaging and gripping his member thinking that jerking off would relax him even more before slumber.

Gripping and pumping his cock with just a slight bit of pre-cum lubricating the tip he closed his eyes in anticipation of his hot cum ready to gush onto his tummy. Suddenly footsteps clumsily began stomping up the stairs.

"Crap," he said aloud as his fantasies died as well as his hardness. His penis slowly faded to flaccid.

His lights were off and he was naked in bed when he heard his mother putting her friend to sleep in the adjacent room.

Then he heard their conversation.

"It's ok honey, you'll get it again." His mother said quietly.

"No, I won't," she protested "I'll never again feel a man inside me," she sobbed "Just plastic and rubber dammit!" mom's friend said too loudly.

The next thing Jake heard sent his manhood sky high.

"Yes, but honey plastic and rubber can be so good. I'll get you a couple of things to help you out tonight and tomorrow we'll try to find you a guy." Jake's pure innocent mom said to Jake's unbelieving ears.

Soon Jake heard the guest bedroom door close and sounds of moaning an vibrating began only 10 feet from his bed separated only by a small bathroom.

Jake tried to close his eyes but the excitement of his surroundings made it impossible, he decided to get up and go downstairs for a nightcap. As he quietly snuck by the room where he knew his mom's friend was in fucking herself he took a quick listen. "Harder, harder, harder" She was saying angrily.

He continued down and was surprised to find his mom solemn still on the couch polishing off the remaining wine. She looked up at him in his boxers and tank top. "Wow," she said "you sure have grown up into a handsome man."

"Thanks' mom" he blushed. "Is she ok? Is there anything I can do?" He said innocently and with sincerity.

His mom patted the couch next to her inviting him to sit down and he obliged. He rested his head on her shoulder and she petted his hair and scratched his neck. The beginning of electricity stirred in his groin and he stole a quick glimpse at her ample cleavage and milky white thighs. They sat like that for a bit just thinking and enjoying their contact.

"Well honey I know you are so helpful but I don't think even you could solve this one." She said glumly. "My friend hasn't had a man in years and sometimes the human body starves for affection".

Jake's mom was shocked with what he said next, so unexpected.

"Mom, I think you know that there is not a thing in the world I wouldn't do for you and if you want me to satisfy your friend I will." Jake said with mock confidence.

"Jake, No that is unheard of! That wouldn't... that couldn't....my goodness." Then she went quiet and walked away confused. She went to the kitchen and paced for a bit then walked upstairs.

Jake went to the bar poured himself a strong drink and started thinking about this surreal strange situation he was contemplating. He was approaching his forty first birthday and the horny woman upstairs was in her mid-sixties, not necessarily pretty but attractive in a librarian sort of way, plus Jake always had a thing for older women.

After about 10 minutes Jake's mom came downstairs suddenly sober and looking a little bewildered. "Honey, come sit with me. I can't believe I'm about to ask you to do this but extreme situations and all. If you could... I mean if you would... She's upstairs and..." His mom put her head into her hands and started to shake her head almost in tears.

"Don't worry mom, I know what she wants and I'm happy to do it. But I'm doing it for you." He got up grabbed his moms face with both hands and gave her a firm kiss on her lips. He opened his lips slightly but his mom pushed him away.

Holy crap he couldn't believe what he was about to do even as he walked up the stairs and went into his room.

First in a trance he went into the bathroom and stripped down to nothing, his cock was firm and standing straight up slightly to the left. As always before sex he cleaned himself firmly and brushed as teeth as well as freshened up with deodorant. He left the bathroom with a small bottle of baby oil.

When he entered the guest room he found his mom's friend face down naked and crying, two vibrators next to her; one 10" monster and another one, a little one the size of a large forefinger.

The only light was a dim light from a nearby night light; he slowly and deliberately put one knee on the bed and straddled her with the other knee. His hard cock laid perfectly on her ass and he leaned into this crying woman pressing his manhood on her behind and started to kiss her on her neck and under her ear. "You are beautiful and I've wanted to do this my whole life." Suddenly she stopped sobbing and he felt her move her ass under the weight of his pelvis.

The baby oil noisily squirted as it jizzed out of the little bottle and dripped down the center line of her back. He started by rubbing it into her shoulders, her arms, her hands, her legs and especially her feet but staying away from all the good parts at first.

"Oh my god, that feels so good. I can't believe I'm making you do this Jake, stop please stop." She sobbed.

"I can't not now. This is what I always wanted, always," He lied.

He rubbed every inch of her body from finger tips to toes and even her face until he could feel her body relax completely. Then he reached for the big vibrator and used it as a massage tool on all of her parts except for the ones it was designed for, he vibrated her ass cheeks and her breasts, her feet, arms and hands. She was in heaven and ready.

Jake took her small breasts in his hands and vigoursly sucked on one nipple while pinching the other. He licked and sucked and pinched until she arched her back sticking her belly straight to the sky saying "Oh my god, that feels so good!" Feeling that she might be ready he slid his hand down to her vigina and very gently slid the tip of his finer into the warm folds and rubbed gently. Yes she was ready, so wet and ready.

He forcibly flipped her over onto her belly and used his knees to separate her legs as wide as he could get them, she fought at first but he firmly pushed her head into the pillow and pushed two fingers as deep as he could them inside of her. She protested no more.

He then kissed his way down to her waiting, wet, hot pussy and used both hands to open her flower as much as possible.

"oooohh" she cried muffled in the pillow as he pushed his tongue in as far as it would reach. Then he licked and bit and licked and sucked as hard as he could both hands up and squeezing her small breasts he sucked her clit, swallowing and licking it went on and on. Sometimes he would stop and slap her open pussy and her ass.

As she panted face down sweaty and hot already have reached orgasm she started to get up to thank him; he pushed her back down and jammed two fingers back into her gaping beautiful hole and finger fucked her hard until he could tell she was back into euphoria. He was going to make sure that this would be something she would remember.

He used both hands to spread her ass cheeks as far as they would go then he put his nose right on her pink clean rose bud of an anus and sniffed in hard. mmmmmmmmmmm it smelled good. he reached up and grabbed her hands bending them back and forcing her to open her ass cheeks as far as they would go. Then he kissed her rosebud kissed it again and again until he finally pushed his tongue deep into her asshole over and over.

Once her body felt that she could not take it anymore he grabbed the large vibrator and began forcibly fucking her over and over with it; soon she was starting to spasm and he knew an orgasm was coming he threw the large vibrator to the floor and grabbed the smaller one, first slowly putting it in her ass then faster over and over. As she was starting to cum he bent down and bit onto her clit and licked her pussy while still fucking her ass hard with the small vibrator.

She screamed and squirted her juices all over his face and he soaked it in and swallowed enjoying the savagery of all of it.

He stood up kissed her on the cheek and thanked her. She was unable to respond verbally but the content smile on her face told him all he needed.

He then went to his room to finish himself off, as he left he noticed that the guest bedroom door closed ever so slightly from a pair of peeping eyes.