Mom is Back in Business

"That's fine, mom. I completely understand," Jacks quickly got out. He was disappointed slightly that he would have to wait even that long for his first chance. First chance at what though? He really didn't have a plan past getting on the massage table in front of his mother. How would he escalate the situation. Surely his mother wouldn't dare cross that line on her own. Regardless, this school year would fly by if he could look forward to watching his mother every day after school.

Rinse. Wash. Repeat. That was Jackson's routine for the rest of the week, but it all culminated with his afternoons where he'd watch his mother's masseuse escapades.

After school on Wednesday he rushed home again, but this time he was greeted by his mother in her sports bra. His eyes immediately fell to her bountiful tits, and this time he suspected she may have clocked his eye movement.

"Hey.. mom, shouldn't you be getting ready for your client?" Jacks inquired with much concern.

"Oh, yeah, well no actually," his mother let out disappointedly "the client let me know about five minutes ago that they were held up at work and weren't going to be able to make it."

A lightbulb in Jacks mind turned on and shined so brightly he thought for a moment he might illuminate the whole living room. "Ahh, I'm sorry mom, but I do have an idea," he paused "my back was bothering me so much at school today I could barely sit in my desk. Do you think I could take their slot?" he was so hopeful and excited he could feel his the blood rushing below his waist just at the thought.

His mother contemplated it for a second. "Well, I am already set up.. Sure," She said with a beaming smile. "Why don't you go shower and then come back to the den with a towel. I'll go warm the oil and prepare for you, and we'll see if we can sort this back out."

Jackson rushed to his room and then the shower. His cock was like a rock the entire time he washed himself. He couldn't contain his excitement, but hoped he could reign it in at least momentarily. Once cleaned off he made his way back to the den with only the towel wrapped around his waist.

As he entered the den his mother jested with him. She waved her hand in front of her face like a fan. "Look who's showing off," she boomed. Jackson stood in the door way with the towel draped around him showing off his well defined chest and abdomen. He was active and it showed. He had finally gotten his cock to settle down enough that it wasn't too obvious how excited he was beneath the towel, however, the outline of his slight bulge was surely noticeable to the wandering eye. "Oh stop mom," he replied bashfully and laughed.

His mom laughed "Why don't you lay face-down for now. We'll do the whole kitten caboodle, but let's focus on that back. Where is it bothering you the most?"

Jackson turned around in his towel and pointed to his lower back right above his buttocks. "That's the biggest problem area right now."

Jackson laid face-down as directed by his mother. She briefly adjusted his towel so that it was covering his buttocks and everything else in that area. She lathered her hands with the warmed massage oil and began. She started with his shoulders and it felt amazing. God, mom was good with her hands Jackson thought to himself. He nearly had to stop himself from moaning. "How does that feel baby?" his mother inquired between kneads on his shoulders and now his upper back.

"It feels amazing mom," Jacks replied in a voice that clearly stressed his enjoyment. "I can see why you have so many clients. You're so good at this."

"Aw, thanks Jacks. You're a good client. You have so many muscles on your back. Makes my job easier," she chuckled. Jacks blushed a bit with his face buried in the massage table. "Okay, lets get to the root of the problem," Heather said to Jacks, and as she did her hands glided down towards his lower back repeatedly making contact with the towel. His mother let out a groan eventually and he could feel her grab at the top of the towel.

"I'm going to fold this down just a bit so I can get in there." She folded the towel halfway down his buttocks exposing the top part of his ass. "Nice tush," she joked with Jacks. "Its been a long time since I've seen it," Heather added.

Jackson was now, all of a sudden, feeling bashful. "Well, hopefully there's been some improvement over the years," Jackson chuckled as he said it.

"You always had a cute tush Jacks," his mother giggled "but there's certainly more muscles now," she added as she continued to massage the area where his back met his muscular buttocks. Was his mother flirting with him? She proceeded to massage the problem area, and sometimes Jackson thought, made her way further down towards his ass than needed based on his description of the issue he was having. Whether or not his back was really bothering him his mothers soft hands lathered in oil felt like pure ecstasy. In the refuge of the massage table he could only see his mother's big tits being contained in the dark grey sports bra she was sporting. He wanted to reenact what he saw on the camera so much. His mind drifted to his mother raising the sports bra over her head and letting her massive boobs fall out while her bright red hair lay on top of her cleavage.

He gathered himself long enough to realize he was rock-hard again. It was actually becoming uncomfortable. Fifteen more minutes flew by in what felt like two. "Okay, I think you can turn over now and we'll do some work on the front," she called out taking Jackson from his dream-like state.

What was the move here? He was so stiff. Jackson knew from the video feed that he was much more well-endowed than the clients his mother had had in the days preceding this. If he turned over there would be know hiding his excitement. He tried not to think. He let his body take control and simply flipped over beneath the towel. His mother's tits were right there in his face bound by the sports bra that was straining at every seam. His mothers crimson hair draped over her shoulders and her black yoga pants hugged every curve including her little tummy she often complained about. Sure enough, when he flipped on the table the towel immediately tent poled in the region of his raging erection.

Once in a while the tent would sway as his cock twitched beneath it rapidly pumping blood from other regions of his body through his cock light a lightning rod. Heather had briefly turned to lather more oil on her hands and when she turned back her eyes immediately found Jackson's crotch. To avoid it or act like it wasn't there would be insanity. The height of this particular tent was far too noticeable. Her jaw dropped as her eyes fixated on it and all she could get out was "Oh Jacks..."

Jacks quickly replied, "I'm sorry mom I couldn't help it. The massage felt so good and I was just so relaxed," he let out slightly ashamed. He hoped his mother wasn't upset by his excitement, but he legitimately couldn't help it. His eyes fixated on her sports bra again and with it came a sway of the towel.

"It's okay.. Jackson," she let out slowly "it's actually completely normal and happens a lot during massages. You have nothing to be ashamed of, but it looks uncomfortable. Do you want me to stop?" she asked him sincerely almost concerned.

"I'm okay if you are mom. It feels so good I don't want to stop now." This was the truth. He by no means wanted this to stop right now. His eyes went up and down his mother. Her pale skin looked so soft and inviting. Her curves sent shockwaves through his body all the way to his engorged cock.

"Okay, but if you want me to stop at any time just let me know and we can break," his mother urged him. He nodded in approval and she began to apply her oiled hands to his pectorals. He looked at his mother for any sign that she was disgusted by him and what had unfolded, but to him she just looked flush with red. It was hard for her to hide any signs of blushing with her pale complexion. Every once in a while it seemed as though she was taking a quick glance towards the southern region of the table. Jackson wondered if she was staring at the flagpole beneath the towel. The idea only served to further stimulate him.

Eventually his mother was finished with his torso. She told him she'd finish with his feet and legs. As she made his way to the end of the table her eyes surely lingered on the spot where his penis resided under the towel. She made her way to his calves "You know that's pretty impressive Jacks," she let out. "It's been like that this whole time," she added.

Jacks craned his neck and looked down at his mother who was now at his legs. "I really am sorry mom, but I think it only got worse once I turned over," he said sheepishly.

"Oh?" his mother seemed inquisitive. "Why is that do you think?" she followed up with.

This was definitely a fork in the road moment. Jacks acknowledged that in the moment. This could go very well or very poorly. There literally wasn't enough blood in the right head at this moment to properly consider how to respond and so his mouth went ahead on it's own. "Well, I mean," he stammered "It's just that you are very beautiful and you know the way you are dressed doesn't leave a ton to the imagination." How would this be received? A moment felt like an eternity.

Heather's cheeks were painted red at this point. "Oh, I see," and the words hung in the air for what felt like forever. "What excites you the most?" she followed-up with as she continued to work his legs.

She was pushing the issue. There was no doubt. Jackson thought about how to respond. As he panicked and tried to think of the right response his mothers hands drifted up his thighs. The application of pressure here felt so good, but the proximity to his crotch only further exacerbated the issue at hand. With each stroke she drew closer to his inflated manhood. The last few passovers brought his mothers hand in brief contact with his full testicals. Surely from the right vantage point she could glance and see at least some of the commotion going on under the towel.

"Well," he hesitated "I'm a bit of a boob-guy," he felt stupid saying that aloud to his mother.

She laughed "Yeah, that'll do it. So I guess you're a bit like your dad in some ways.." she trailed off and continued to massage his upper thighs and the last passover brushed against the bottom of his shaft. This sent shockwaves through him. "But you are not completely like you father clearly," she added to her original statement. Jackson looked down his body to his mother who was clearly biting her lip. She pulled her hands away. "How about we finish with a scalp massage then?" she asked of Jackson. This would give him a front row view to her busty chest.

He could barely get the words out, but responded "Uh yeah, that sounds great."

His mother made her way around the table and as she did her forearm bumped against his tent. His cock did not budge. She made her way around and stood over Jackson's head. He could barely see his mother's face unless she craned her neck past her massive tits. She began massaging Jackson's scalp and it felt so good he fought to keep his eyes open, but he also had a view he had long been hoping for and that kept him alert. He could see his mother's hard nipples poking against the fabric of her sports bra.

His mother craned her head again and would have made eye-contact with Jackson if his gaze wasn't fixated on his mothers chest. "So, you like mommy's big tits, huh?" she questioned.

The words shocked Jackson. The way with which they were said drew that primal feeling out of Jackson. "Yes, mom. They are amazing," he responded earnestly. In almost a flash his mother took her hands from his head and like he had seen in the days leading up to this on camera ripped her sports bra up and over her head. They fell and for a second seemed like they would fall nearly directly into Jackson's face.

"Mmm, that's much better," his mother let out before adding "you can touch them if you want." This is the moment Jacks was waiting for. Beneath his mother both his hands reached up grabbing handfuls of his mother's big soft breasts. He massaged them in his hands pushed them together and squeezing her erect nipples between his fingers. She softly moaned in response. "Oh baby, that feels so good," Heather called out. Underneath the towel Jackson's cock was responding in accordance with frequent twitches. "Hold on baby," she said softly to Jackson. Heather came around to Jackson's side. Her big breasts bounced with even the slightest step. Her hand grabbed the towel at the center of the tent. "My god Jackson, you're huge!" she gasped. "It has to be uncomfortable under there. Want to lose the towel?" she asked smirking in his direction.

Again, Jackson nodded his approval and Heather pulled the straining towel directly up. Jackson's throbbing cock was now revealed to his mother. A large vein ran up the side nearly the size of an electrical cord all the way to his bright red tip which was now glistening with his pre-cum.

Heather nearly fell backward. "Wow honey, you're cock is gorgeous." She was now standing equidistant between her son's head and his cock beside him. Her oiled finger traced the bottom of cock from base to tip sending shivers up Jackson's spine. Soon her fingers completely enveloped her son's cock. "It's so thick," she said in a sweet and sultry voice and glancing at him. "Is this okay?" she asked as she began to pump his big thick cock mechanically.

"Yes mom. That feels amazing," he let out. He couldn't believe this was actually happening. He had hoped and dreamed, but didn't think it was actually a possibility. Jackson leaned upward and began to kiss his mom's breasts licking and sucking at every square inch he could get to. He took her nipple in his mouth and lightly nibbled at it eliciting a big moan from his mother. Meanwhile her second hand joined the other wrapped around her son's meaty manhood pumping in unison. Her hands twisted up and down his long shaft until reaching his balls and then continued their journey back upward to his swollen head.

"You look about ready to pop baby. Are you going to cum for mommy?" she asked in a voice that in-fact nearly made Jackson ejaculate on the spot.

"Yes mom I won't last much longer," he said weakly. She stopped immediately. Her hand pushed him down flat on the table momentarily. Her other hand guided his legs so that he was situated perpendicular on the table with his feet hanging off the side.

"I want you to cum on mommy's big tits. Would you like that, baby?" she asked biting her lip and staring into Jackson's green eyes. Jackson had his mother's eyes and he stared back into her piercing green eyes nodded in agreement. He leaned up as his mother got into a half-squat pulling her massive tits together and sliding her son's hard cock between her oily chest. She teased him by shaking her large tits on his pulsating shaft before beginning bringing them back together and beginning to move up and down the length of Jackson. His cock disappeared into her massive cleavage. Only the head of his cock became visible briefly on each pump despite how endowed he was. It didn't compare to the blessings his mother had hanging from her chest. His mother stared into his eyes as she moaned ever so softly "Your big hard cock feels amazing between my tits baby. I want you to cum for me."

Jackson couldn't take it any longer. "I'm going to cum mom!" he cried out. She licked her lips in response which sent him over the edge. He shot rope after rope. The first rope hit his mother directly in her neck, but she repositioned so that his cock rest against her right breast. The head of his cock was pinned against her rock-hard nipple and she pushed it against the bottom of his cock milking each drop out on to her nipple and areola.

He came for what seemed like a full minute while Heather urged him on, "Yes baby come on. Give it all to me."

When the last drop came out Heather moaned and place her lips on the tip while staring up at her son. She sucked lightly withdrawing the most stubborn drops of cum from his cock while Jackson moaned in response. Once the ecstasy faded it was back to reality. A line had been crossed today. The evidence of that crossed-line was painted all over his mother's chest. Jackson wasn't sure what to say to his mom other than, "That was amazing mom."

There was a long pause. His mom finally responded. "You are amazing baby. I love you." Her eyes which had just been filled with lust were now filled with endearing love. Jackson wasn't sure where they went from here, but he was excited.

"I love you too, mom."