After my son left for college, my husband divorced me, leaving me with a mortgage and other bills that I struggled to pay each month. After graduating from college and getting a good job nearby, my son started helping me whenever I came up short. Before long he decided that - in exchange - he should get a blowjob or a quick fuck whenever he came by. With few options and mounting bills, I agreed.
After my son, Brad, left for college, my husband decided he liked his secretary better than me, and he divorced me. I was caught totally by surprise, because – even at 42 – I was still an attractive blonde, with a nice body and big, natural tits. And, sure – his secretary was much (much) younger, but she wasn’t terribly attractive, and was almost flat-chested……but, then, maybe that was the point. I really didn’t want to give it much thought.
Anyway, I got the house in the settlement, but it came with a mortgage and other bills that I struggled to pay each month. I got a job in a local store, but my paycheck didn’t always cover all of my normal expenses. I always seemed to be a few dollars short.
When my son graduated from college, he got a good-paying job, and he occasionally helped me with my monthly bills. After about a year, or so, he got married and, thankfully, moved only a short distance away, which meant he could stop by on occasion to help me out, which he did frequently.
One time when he stopped by, I was sitting at the kitchen table poring over bills that I knew I couldn’t pay. When he came into the kitchen, he could see my angst and walked up behind my chair and gently rubbed my shoulders, asking, “What’s up, mom? You look really stressed out.”
I pointed to the bills on the table and said, “It’s just more of the same…..I have more bills than money. Do you think you can help me out again this month?”
Brad stepped to the side of my chair and with his hand on my right shoulder, pulled me over against him in a sort-of-hug that had my head resting on torso, just below his naval.
“Don’t worry about it, mom. We’ll figure something out…..but I think we have to change things up a bit.”
Still leaning against his lower torso, I said, “What do you mean? What has to change?”
Brad moved his hand from my shoulder to the side of my head and began gently stroking my hair, while still pulling my head so that it rested against him. “I think we need to come to an arrangement in exchange for all this financial support I’m giving you.”
It didn’t register right away what he was talking about, but when he stopped stroking my hair and slipped his hand inside my shirt, grabbing a handful of boob, it began to sink in. I never wore a bra around the house, so his hand was squarely on my naked breast, kneading and squeezing my 36DD tits.
I don’t know why, but I didn’t pull away from him, I just looked up at him and said, “What the hell are you doing, Brad? I’m your mother!”
With his hand still inside my shirt, massaging my right breast, and finding my nipple with his thumb and forefinger, he said, “I know, mom, but I’ve always had the hots for you….I even used to think of you whenever I jerked off at home before I left for college. Now that I’m helping out so much financially, I think it’s time I got something in return that I’ve wanted for a really long time.”
I couldn’t believe what I was hearing and, with my head still resting against the front of his hips, I became extremely aware of the growing lump down one leg of his loose basketball shorts. His cock was obviously stiffening and pressing against the fabric of his shorts, causing an impressive tent to form against the side of my face. I had no idea his dick was that big! Still, I was struggling with the idea of my son massaging my tits and making sexual suggestions, even as I marveled at the sheer size of his growing shaft. It looked to be about 8” long, and it wasn’t even fully erect yet.
“Well, what type of arrangement do you have in mind?” I asked.
With his right hand still inside my shirt toying with my dangling tits and occasionally pinching my nipples, Brad used his other hand to pull the top of his shorts and boxers down below his nutsack, allowing his nearly erect prick to spring out, swinging back and forth, and gently slapping the side of my face.
“Let’s start with a blowjob, mom.”
I was kind of in shock, but felt like the dye had already been cast, since I was letting him openly fondling my boobs, and I definitely needed help with the bills. I slowly opened my mouth, and Brad eagerly pushed his hips forward, shoving his stiffening rod inside. He began to rock his hips back and forth, sliding his shaft in and out of my mouth as I sucked on his cock and licked the tip of his dick with my tongue.
With one hand still inside my shirt and the other pulling on the back of my head, Brad moaned his obvious pleasure, saying, “Oh my God, mom….that feels amazing. I’ve been dreaming of this moment for close to 10 years. Yeah, just like that…..yeah…..yeah….keep going…..Oooh, God, that feels so good.”
After a few minutes Brad picked up the pace, holding the back of my head and sliding his dick in and out of my mouth faster and faster. Then his breath started to catch and he closed his eyes, murmuring that he was about to cum, before blasting a load of hot, creamy splooge down the back of my throat.
He slowed down his strokes, but kept sliding his slick stiff pole in and out of my mouth for a few more minutes, relishing his orgasm with a silly grin all over his face. I swallowed all the jizzm he blasted down my throat, then gently massaged his balls as he finished emptying his load of cum in my mouth.
I sucked and licked his shaft clean, then gently stroked his softening prick with my hand. I looked up at him with a quizzical look and said, “So what happens next?”
With his shorts still pulled down to his knees, Brad leaned his butt against the edge of the table so I could continue fondling his softening dick, and said, “Now, whenever I come over, I’ll get a blowjob, a handjob, or a quick fuck….anytime I want. In return, I’ll give you $400 every month to help with your bills. Sound good?”
As he said this, he pulled my shirt over my head and tossed it on the floor, allowing my boobs to spring free, wobbling and swaying in front of me. With both hands he started squeezing and slapping my big tits, seeming to enjoy the way they swung back and forth on my chest.
Not really knowing how this would play out, but acknowledging my financial quandary, I agreed to his terms.
Brad played with my boobs for a few more minutes, then pulled his shorts up…his flaccid shaft catching on the elastic waistband and flopping around until he finally tucked it away inside.
The next day I finished my shift at the store around 5 pm, and – as usual – changed into a t-shirt and panties when I got home. I was in the kitchen preparing my dinner when Brad came waltzing in. He had a key to the house, so he never needed to knock.
He said, “Hi, mom.”
With a surprised look on my face I said, “Brad? What are you doing here? You were just here yesterday.”
“Yeah, I know, but I wanted to collect on our new arrangement.”
I watched him walk from the front door to the kitchen as he said this, unzipping his pants as he came, and fishing out his cock with his hand. He let it dangle between his legs as he walked into the kitchen, banging against his thighs with each step. When he got to where I was standing, he quickly pulled my shirt over my head, tossing it aside, and pulled my panties down to my knees. He pushed me back so that my ass was leaning against the counter, and began pulling and squeezing my tits, sucking and pinching the nipples, and running a couple of fingers along my vagina, toying with my pussy lips and rubbing my clitoris.
Still a little surprised to see him, I said, “Wow…I guess we’re going to dive right in…”
He pulled a stiff nipple out of his mouth with a ‘plop’, laughed and said, “You bet.”
I reached between us and found the shaft of his semi-hard pole and began gently stroking it, occasionally just focusing on rubbing the bulbous tip. Brad’s moaned and his dick responded, growing even bigger in my hand.
Brad pulled his fingers from between my legs and showed me how wet they were. “You’ve been waiting for this, haven’t you?” He asked.
I hadn’t really thought about it, but now that he mentioned it….”Yeah, I guess I have been,” I said, with a sly grin. I hadn’t been dating much, and it had been a while since I got well and truly fucked. So, sucking on Brad’s impressive cock the previous day and swallowing a mouthful of cum had really started my juices flowing.
His prick was now fully engorged in my hand. It felt huge….even a little hot….as I continued pumping it with my fist. He started dry humping my bald pussy mound, which was driving both of us crazy. Suddenly he spun me around to face the counter and bent me over so that my pussy was totally exposed and my dangling boobs were swinging freely beneath me.
He used one hand to grab the shaft of his erection and line it up with my dripping vagina. He kicked my legs further apart, then – with a big push from behind – shoved his stiff pole all the way into my cunt. I was soaking wet, so he slid in easily. He immediately began to pound his prick in and out of me in earnest, causing my swaying tits to slap into each other and make ‘clapping’ noises from the force of his thrusts.
My God, it felt good! Brad’s cock was bigger than his father’s, and I could already tell he was much better at putting it to good use when it came to fucking.
Brad had his hands on both of my hips, slamming his dick into me like a piston, when a delicious orgasm coursed through my body. Between grunts from Brad’s thrusts, I moaned out my pleasure.
“Uhnn….Uhnn….Aahhhhh, I’m….cumming….Oh, my God…..That’s…amazing….Uhnn…Uhnn….keep going…..Aaaahhhhh….holy shit, Brad…..keep going……Uhnn…Uhnn…..
I closed my eyes and rested my head on the counter, enjoying my climax, as Brad kept pummeling my pussy with his stiff shaft from behind.
After a few more minutes, I could hear Brad catch his breath, then let out a low moan as he exploded inside me, painting the inside of my cunt with rope after rope of warm, gooey, cum.
Brad pulled his cock out of my pussy until just the head was in me, then slammed it back in as far as it would go, shooting another stream of spunk deep inside my pussy. He did this again, then again….each time slamming back into me, making my body jerk and causing me to grunt from the force of his thrusts.
When he was finally done cumming, he leaned against my back to catch his breath….his stiff prick still deep inside my cunt, and his hands cupping and fondling my dangling tits.
Eventually, his shaft softened and slipped out of my pussy. I grabbed a towel off the counter and wiped between my legs, then squatted down in front of Brad and sucked the head of his cock into my mouth. I cleaned off his shaft with my tongue, then wiped it with the towel, before shoving it back in his pants and pulling up the zipper.
Still naked, I walked him to the front door and asked, “Shouldn’t you be home for dinner by now?”
With his eyes locked on my swaying boobs, he said, “No, I told Carla I was swinging by here to check on you after work, so we’re having a late dinner tonight.”
We shared a mother/son kiss at the door, and – with a final squeeze of each tit – Brad headed home to his wife.
After that day, Brad continued to come by several times a week. He got whatever he wanted.... sometimes it was a quick blowjob by the front door, sometimes it was a leisurely fuck on the sofa, and sometimes it was a forceful fuck with me bent over the counter in the kitchen.
Fortunately, Brad’s wife thought it was a sign of great character and devotion that he would spend so much time checking on his mother and helping out financially. Our ‘arrangement’ is still going on, although Brad finds less and less time to swing by as his family grows. But even now he’ll come by on occasion when his schedule permits and I happily live up to my side of bargain.