Encouragement from mom

The next Afternoon, John was just cleaning up after his third session of the day. It had become a bit more difficult since his mom had forbidden online pornography. He didn’t think it was worth the risk of her finding out he had disobeyed her, so he had to resort to forgoing pornography. He heard his mother calling from downstairs.

“Sweetie, could you come down here for me.” John hurried down to where his mom was waiting in the kitchen. “Honey, I’ve been thinking about what that therapist said yesterday that I should be encouraging you to masturbate more frequently.”

“Um, what about it?” John gingerly replied.

“Well I don’t think you should be masturbating in your room anymore. I need you to be visible so that I can be sure you’re doing it enough and to give you the encouragement you need.” John was taken aback. Sure, it wasn’t the first time he had masturbated around his mom but he wasn’t ready to treat it as normal.

“Alright, sure mom. Was that all?”

“Wait, there’s one more thing. I was speaking with Helen next door about your problem.” John could feel himself start to flush. Helen was the housewife next door who Lilith always gossiped with. She was a bit older than Lilith but she still had a hot body despite not being as busty as his mom was. He could never help but jerk off whenever I caught her sunbathing outside his window. “Don’t worry honey. She won’t tell a soul” she said upon seeing his concern.

“I was telling her about how you weren’t getting any stimulation with our blue-ray player not working. She offered to look through her son’s old things to see if they had anything that could help and she managed to turn up his old VHS collection.” John hadn’t seen a VHS since he was a kid. He was surprised Helen had such old pornography lying around in her house, and more so that she had been keeping her son’s old porn videos in her attic. “Now I know its not the quality you’re used to but its surely better than nothing. I went ahead and set it up with the VHS player she lent me in the living room. I want you to go test it out for me.”

“But mom I just...”

“No buts. I need you to go masturbate for me John.” Her voice was firm, but John could tell she was uncomfortable ordering her son to watch pornography. John resented that this turned him on a little.

“Alright. I’ll go.” John hadn’t quite recovered from his last session but that just meant it would take a bit longer. He went through to the living room to check on the setup. The VHS player wasn’t compatible with their TV so his mom had brought a small CRT TV from somewhere. She had pulled out a small table so the TV was right in front of the couch. Two speakers sat on the arms of the seat. Lilith had gone through a lot of trouble to make this perfect for him.

John had a look through the box of tapes left on the floor and was surprised to find they were all **** porn. With no other choice John opted for a tape simply called ‘Busty Cumslut Moms’ and slipped it in. The tape started in the middle of a scene with a blonde woman on her knees in sexy lace lingerie while giving a young man head. While a little grainy, John could still make out her body in detail.

“Just relax and stroke it nice and firm for me John” Lilith called out from the other room. The scene continued for a few minutes before John started to feel his cock spring back to life. The woman pulled herself off the guys dick and then seductively unclasped her bra, revealing her incredible udders to the camera. As she lowered herself down to rest the man’s member in her bounteous cleavage, John was now too horny to control himself.

“You want to cum on my huge boobs?” the actress asked to the camera.

“Keep it up. Keep stroking until you cum, honey” his mom called from the kitchen.

“Tell me you want to cum on my fat tits son” The voices began to meld into one.

“It’s okay to ejaculate around your mom.” Jon couldn’t tell who was saying what.

“Tell your mom you love fucking her massive jugs.” The actress sounded just like his mother.

“You mom has such a slutty mouth.”

“You’ve lasted so long. Mom’s so proud of you.”

“Don’t you want to bathe me in your cum son?”

It was finally too much for Jon as he could feel himself close to release. “Yes mom. I want to bathe you in my cum. I want to cum in your slutty mouth and on your fat soapy tits.” John shot his load all over the screen, plastering the actress’s cleavage in thick puddles of his seed. It was only then that he looked over and saw his mom once again staring in silence from the doorway.

“I’m glad the tapes worked out for you.”

“No Mom. I wasn’t…”

“It’s alright. Whatever you need to imagine to help you get comfortable… It’s for the sake of your treatment.” With that she quietly left the room. Lilith didn’t say much to John for the rest of the day, only reminding him every hour that he needed to masturbate. John was feeling a little awkward but was looking forward to the next day after school where he could blow off some steam away from his mother. Before he knew it, the time arrived and he rushed down to the DVD store.