First, some quick background. My name is Tom and I am 16 years old. My mother, Tiffany, is an extremely attractive 41 year old brunette with C cup tits and an AMAZING body(she is a personal trainer). My father left when I was six months old, and my mom Tiffany never talks about him, only saying he was an alcoholic deadbeat. Because of this, me and my mother have grown extraordinarily close over the years. Since I am an only child, we went on vacations together and I got jobs over the past few summers to help with the bills(money is always tight because my mom wanted us to live in an expensive neighborhood so I could go to a great public school).
Throughout the years Tiffany has had no shortage of guys trying to date her(most of the guys she meets are through her job at the fitness center) but she’s generally gone on a date or two with them and ended things without going into specifics with me. Although it was never discussed, I think she lost interest in many of them when she realized they just wanted to sleep with her.
Despite this, she started going on dates with an ugly, slightly overweight, but extremely wealthy businessman named Michael about two months ago. It was set up as a blind date and I was shocked that she seemed to like him(since she is so gorgeous and he is, uhh NOT). However, one day shortly after they had their third date I came home from school to see my mom in the kitchen making a sandwhich, having just returned from work.
I admit I had trouble NOT looking at my mom in a sexual way, especially after she came home from work, dripping wet from working out with a sports bra/top and tight black workout pants that accentuated her large but extremely firm ass flawlessly. As she bent down at the kitchen counter to grab the bread, her black g-string underwear hiked up ever so slightly above her pants line.
“Does every dude at work see your underwear whenever you bend down to show them an exercise?” I asked jokingly, biting into an apple.
My mom let out a genuine laugh. She wasn’t embarrassed, we had seen each other in more private positions than this many times.
“Hey stud, I gotta talk to you” she said as she began to peel an orange.
“sure mom whats up?” I asked.
“So that guy Michael….I uhh, I like him Tom. So he’s going to come to dinner this Thursday OK?” she asked nervously.
I admit I was a bit shocked but of course, I was happy for her.
“Well mom, if you like him he must really be a special guy, I’m happy for you.”
“Oh sweetie, you don’t know how happy it makes me to hear you say that” she said as she tried to give me a hug but I dodged and said:
“Hey easy sweaty woman!”
That just made her laugh as she started to chase me around, trying to give me a sweaty hug.
Thursday finally rolled around and Michael arrived with not just a dozen red roses, but a small jewelery box.
“oh god Michael you did not have to do this, seriously!” my mom gushed at the dinner table when he presented it to her.
“Well are you gonna sit there or open it,” he said.
My mother opened the jewelery box to find a beautiful Tiffany’s necklace in the shape of a heart.
“A little much for a fourth date isn’t it?” I said, not caring if I sounded rude…this fat tool was just like the others, I thought.
“What did you just say to me?” Michael said with terrifying quietness. An uncomfortable silence filled the room.
“Tom, apologize” my mother said quietly.
“Sorry” I said.
“How old are you?” Michael asked sharply.
“16”
“16 sir. This gift is between your mother and me. I can see your lack of a father figure didn’t help your manners much,” Michael said. I could see my mother considering saying something but she just fiddled with the necklace nervously until Michael said “here baby let me help you with that” and she turned around while he stood up and put the necklace around her neck.
“Honestly Michael, I don’t know what I did to deserve such a beautiful gift,” my mother said, clearly trying to lighten the mood.
“Oh you will” Michael said disgustingly as he took a huge bite off his turkey breast and gave me a mean-spirited grin.
My mom just blushed and looked down at the table.
To say I didn’t like this guy was an understatement.
That night changed everything.
I sat in bed reading, it was still relatively early, only 11:30 or so, when I heard what sounded like fighting or shouting from the end of the hallway in my mom’s bedroom. I knew Michael and her had retired upstairs to ‘watch a movie’ a few hours before, and with the way he had treated me I wouldn’t have been surprised if that ass hole was commiting domestic violence, so I briskly got up and walked towards my mom Tiffany’s bedroom. The sounds were getting louder, but I could start to make out words, at least coming from Michael.
“Ohh god baby that’s right!….yeah! You suck that dick you fucking slut! God you’re a slut, suck it!” Michael practically screamed this at the top of his lungs as I peeked into the half-closed doorway. My mom and Michael were on my mom’s bed. Michale was lying back, butt naked and my mom was nude except for the necklace and a small white G-string, clinging to her skin tightly as Michael aggressively pushed her down onto his dick. Michael had his hands tightly intertwined in my mom’s hair and was really being rough with the blowjob he was getting, shoving her face onto his dick everytime she opened her mouth for air.
“Oh fuck Tiff….that feels so good. Jesus Christ, how did your husband leave you when you suck dick like this,” Michael said in between breaths, he was clearly in pure exctasy mode.
My mother meanwhile, seemed to be in a trance, sucking his dick like her life depended on it, never breaking eye contact with him.
I was shocked that my mother would do this to this ugly jerk, but I must admit I was getting oddly turned on by it as well. In an attempt to see more of the action I leaned ever so slightly on the door and it creaked fully open loudly. Michael suddenly looked at me and said “jesus!” as my mom turned her head and immediately sat up in the bed, looking like a deer in the headlights as she tried to shield her exposed breasts from my view.
“God Tom, can’t you knock?!” my mother said with more fear in her voice than anger, still trying and failing to cover her breasts with her hands.
“I…I’m so sorry mom, I thought, I thought you guys were fighting, I heard commotion-“
“Your mother told you we were going to her bedroom for the night and after you hear something loud the first thing you think of is fighting?” Tom said in a relaxed tone, clearly enjoying this akward discomfort far more than my mother or me.
“Sorry, good night” I said as I began to close the door but Tom said:
“Hold on you little pervert. Wanna be a peeping tom? Fine. Come on in”
“No I didn’t mean to I was just-“
“Shut up you lying little brat. I told you to call me sir. You need to be taught some fucking manners, you know that? Now you can start by coming inside and shutting the fucking door behind you.” Michael said angrily.
“Baby, what are you doi-“ my mom started to ask Michael but her interrupted her.
“shut up woman. I’ve already raised three children I know what I’m doing. Now step inside Tom, that’s right, and close the door behind you.” Michael was really enjoying this now, and there seemed to be a fire in his eyes, pure entertainment.
“so you wanna be a peeping ‘Tom’ Tom? That’s fine, you sit down on the edge of the bed and watch your mother suck some dick. OK?!” Michael said sternly.
My mother looked down, clearly embarrassed, but she said nothing.
“Ok” I said quietly. Somehow this whole fucked up situation was really turning me on.
“O.K. Sir goddamnit!” Michael shouted. Not it was Michael’s turn to sit up in bed as anger flashed across his face.
“Tiffany, pass me my belt, your son needs to learn some manners,” said Michael as he started to stand up, apparently to beat me with his belt. But a look of panic flashed across my mother’s face and suddenly she took Michael back into her mouth and furiously started stroking him at the same time as his face softened and he decided to lie back in bed.
“Oh damn…Damn you are entirely too good at that baby. Sit down Tom, watch your mother do what she does best,” Michael said as he wrapped his hands into my mom’s hair again and began to close his eyes with pleasure.
I just stood there nervously, thinking this was both terrifying and HOT beyond words, when Michael’s eyes suddenly shot open and he looked at me.
“Hold on. You’re a 16 year old boy, almost a man Tom. Take off your clothes before you sit down, only fair right?” said Michael, his voice less angry and a bit more fatherly than before. My mom, who had just had her eyes closed, suddenly took the cock briefly out of her mouth and stared at me, surprised by Michael’s order.
“You don’t have a problem with that do you Tiff?” Michael said angrily, annoyed at her break from sucking his dick.
For a moment there was a look of pure terror in my mother’s eyes as she stared at me and this ridiculous situation. Her eyes seemed to say ‘I am so sorry about this’ to me as an uncomfortable three seconds of silence went by. Suddenly she said:
“My two favorite men in the world naked? Sounds great” she said, trying to bring genuine warmth to the comment. As soon as the words left her mouth Michael shoved her head back towards his awaiting penis and she commenced blowing him. I stood there stunned.
This all should have been terrifying for me but for some reason I was finding it EXTREMELY hot. I was only wearing sweatpants, boxers and a t-shirt and I quickly took the t-shirt off and flung it onto the pile of mom and Michael’s clothes next to the bed.
I stayed in pretty solid shape since mom was a personal trainer, and my six pack looked pretty good next to Michael’s fat belly.
“A boy who stays in shape. Good for you. The rest now, before your mom makes me cum” said Michael.
I gulped. The sight of my beautiful mother in nothing but a little white g-string had been enough to get me hard, and I would be humiliated if they noticed, but I saw no alternative. I peeled off my sweatpants and then quickly stepped out of my boxers, my raging boner impossible to ignore.
“Ha! See, now everyone’s having fun. Go on a sit down” said Michael, getting kinder by the second. I sat on the edge of the bed as my mom continued to suck Michael’s dick for what seemed like eternity, but must have only been about two minutes before Michael said”
“baby, your son’s getting bored. You got two hands, use the other!”
My mom wasted no time in gently stroking my penis as she continued to keep up with Michael’s increasingly rough blowjob. Suddenly Michael said “oh fuck, I’m about to cum. SWALLOW IT SLUT” as he started to buck at her mouth insanely. My mother stayed calm as she began gulping down ounces and ounces of his cum, still jacking me off with the other hand. Michael finally let out a groan as he lay back in bed.
“OK”, Michael said. “Not the fun really begins.”
TO BE CONTINUED