This time Mike made sure his door was latched and he sat on his bed and contemplated what just happened. On one hand he was mortally embarrassed that she had caught him jerking off, but on the other hand her reaction had been completely unexpected and very exciting. His cock was still almost fully erect and his mind rolled over how cool it would be if Tori was somehow interested in him. He really wanted to pull out his cock and finish what he had started earlier, but he couldn’t risk getting caught twice and decided to wait until Tori left and his mom was asleep.
As he replayed the encounter with Tori over and over in his mind he was suddenly terrified by the thought that she and his mom were alone downstairs. What if Tori told her what had happened? He knew his mom would not be pleased if she knew he had been caught by her friend and feared the consequences. Nothing about Tori’s reaction led him to believe she would tell his mom, but he still had that fear in the back of his mind.
He idly passed more time at his computer playing war simulation games to take his mind off what had happened and his burning need to jerk off. He seemed to alternate regularly between being excited by thoughts of jerking off while Tori watched and fears that his mom would soon learn what had happened.
He heard excited chattering coming from downstairs as his mom and Tori seemed to be deeply involved in some conversation. It was almost an hour later when he heard noises indicating that Tori was getting ready to leave. Before she left she called upstairs, “Bye Mike, it was great to see you.”
His stomach knotted at the double meaning of her words. Could she really be saying she liked seeing his hard cock? He could only hope. She left a few minutes later and he heard his mom coming down the hall toward her room. She knocked on his door and he called out, “Come in.”
She just leaned her head inside and said, “I’m surprised you are still up.”
“I’ll be going to bed soon,” he said before thinking that he would as soon as he could jerk off and relieve the pent up tension in his cock.
“Well, goodnight,” his mom slurred a little as she spoke. She was drunker than he had seen her in a while. He replied goodnight as she left his room and shut the door behind her.
Mike sat quietly and listened as she moved around. As soon as he was sure she was in bed he pulled his pants down and freed his semi-rigid cock. He lightly wrapped his fingers around his shaft and his mind raced with erotic scenarios from this night that would only ever play out in his mind. He thought about Tori catching him but instead of his stopping he had kept going until he came as she watched. As he replayed the scene she then moved over and replaced his hand with hers before she jerked him to a massive cumshot. The final time he replayed the scene she came over to him and dropped to her knees before sucking him off and taking his cum in her mouth.
His mind continued to replay different scenarios with each one more wild than the previous. Before he knew it he was thinking about what might have happened if both his mom and Tori had caught him. In his mind’s eye his mom wasn’t upset at all and she had helped Tori relieve his pent up excitement.
The next time he replayed the scene Tori wasn’t present at all and it was just his mom who caught him. As his mind played a scene of him shooting a huge load of cum all over his mom’s naked tits he knew he had passed the point of no return. He frantically stroked his cock until it erupted with cum. Mike stroked himself steadily as the heavy cum shot out of his cock and landed on his stomach. Finally the force of his cum shots weakened to the point where the cum oozed out of his cock and ran down over his hand as he continued stoking himself. Only when he was completely spent and his hand and cock were thoroughly smeared with his cum did Mike finally open his eyes and look down at his stomach.
The force of his orgasm surpassed any other that he could remember and he was truly surprised by the amount of cum on his stomach. He didn’t ever remember shooting that volume of cum before and momentarily sat in amazement looking at the many strands of white cum all over him. He finally rolled over and grabbed an old t-shirt off the floor and started to clean himself up.
He then was struck by the familiar feelings of guilt and shame about having had such sexual thoughts about his mom. He knew that much of the intensity of his orgasm was owed to his brief encounter with Tori, but he also knew that what finally unleashed his cum were some very inappropriate thoughts of his mother.
He felt weird and perverted having such lustful feelings about his mom, but the reality was that this wasn’t the first time he had felt that way. It first started a little over a year ago during his senior year in high school when some of his friends started talking about hot older women. They started discussing a few teachers they would fuck before one of his friends said, “Shit Mike, what about your mom? I’d totally do her.” Mike had been shocked as he had never thought of her as anything other than mom, but the rest of his friends quickly agreed with the comment. A couple of them went to her for their haircuts and started talking about how, if they kept their hands on the ends of the armrests during the haircuts, she would rub her crotch against their hands. They also talked about how she would let her big tits press against their backs as she cut their hair and would rub her tits against them as she moved.
Mike had protested to their observations and conversation and finally had persuaded the group to change subjects and move on. None of his friends had brought the subject up since and Mike figured, and hoped, they had forgotten about it. However brief the conversation, it had stuck in Mike’s mind and he couldn’t shake the idea that his friends thought his mom was hot and wanted to fuck her.
It wasn’t until his next haircut with her that things started to change for Mike. She had cut his hair about once a month for his whole life and he never thought anything of it until this particular time. He wasn’t sure why but he kept his arms and hands on the ends of the armrests as his friends had described. Perhaps he was secretly hoping that nothing would happen and he could put the whole silly issue out of his head.
That wasn’t to be as it wasn’t too long after she started cutting his hair that she rubbed the crotch of her tight jeans back and forth against his hand. Mike became immediately aroused despite his feelings of guilt at feeling this way about his mom. In his excited condition he had a heightened sensitivity to her touch and movements. Just as his friends said he felt her big, soft tits pressing into his back as she cut the back of his hair and she brushed her tits against his arms as she moved around on his sides.
By the time he had finished that haircut he had to concentrate hard to control his hard on until he got home from the salon and could wildly jerk off. He felt extremely guilty thinking about his mom that way, but as a horny 18 year old he couldn’t deny that she had just rubbed her crotch and tits against him.
From that day on, almost in spite of himself, he would find his mind wandering to thoughts of her as he jerked off. At first the memories of her soft tits brushing against his arm were more than enough to bring about a climax to his sessions. However, his mind soon started to create more and more lurid scenes with her where she did far more than simply brush against him while cutting his hair. She had soon become a fairly regular player in his jerk off fantasies and before too long he had imagined fucking and sucking her in about every position he could imagine.
Despite the regularity of these thoughts Mike was always racked with guilt immediately after he finished cumming. He knew it was wrong and probably more than a little sick and perverted to feel like he did, but when he grew excited he couldn’t help but let his mind wander to visions of her. Ultimately, he learned to deal with the guilt that came as a result.
In later haircuts he concluded that she didn’t do any of the crotch or tit rubbing intentionally. Wendy was pretty short at only 5′ 2″ tall and she often had to lean, stretch, or stand on her tip toes to give her haircuts. Mike realized it was when she was leaning and reaching that she usually brushed against him and figured that she probably was unaware she even was doing it. Still, that didn’t stop him from feeling a charge of excitement whenever her crotch or big tits rubbed up against him during his subsequent haircuts. Some of Mike’s most intense masturbation sessions would take place as soon as he could get home from these haircuts.
Wendy was now only 37 years old and she worked hard to keep herself in shape. She worked out regularly and watched what she ate. Through as objective eyes as he could use, Mike came to realize just how hot his mom was for a woman her age. Most of the time he was able to acknowledge that fact simply as an observation in his mind and think nothing more of it. It was at times when he felt particularly excited or pent up that he found his mind turned these observations of her into something much more lustful.
The feeling of release he felt after having finally been able to finish jerking off was so intense that Mike fell into a deep sleep almost as soon as he finished wiping the last of his cum off his stomach with his t-shirt.
The next week passed normally with Mike very much looking forward to his haircut late in the week. Not only would it give him a cheap thrill at the expense of his mom but he also hoped to have the chance to see Tori again. He knew it was all just silly fantasy on his part, but there was a small part of him that couldn’t stop thinking that there might be a small part of her interested in him.