A 10-Part story about a son's fantasy, a mother's betrayal, and a secret that the two would share.
It had been a few weeks since I had let my Mom know that I knew she was cheating on my father. Though things didn't go smoothly during that first conversation, she ended up being more agreeable than I expected. After a day of crying, she asked me what it was that I wanted exactly, and I was very direct with her; I wanted to have total control of her sex life, and by that I meant I wanted to decide who she fucked and when she would be getting fucked. I offered her a little wiggle room at first ... I told her we could go on Chat Avenue together and I'd let her pursue whatever guy she wanted. I just wanted to see that she was actively pursuing it, and I wanted to be there to watch it.
Most guys closed out the chat immediately as soon as they saw that my Mom was interested in getting fucked in front of her 24 year old son. A few stuck around for a bit, asked questions about why I'd be watching, and entertained the idea until it came time to set up a real meeting. We gave it a shot for a few hours each day when her and I were at home alone, but ultimately we had no luck. To my Mom's credit, she was able to shield my Dad from the fact that the majority of her days were being spent with her son attempting to find guys to have sex with her.
I was starting to get frustrated though, even more so as I could start to tell my Mom was feeling relieved with each passing day. It was obvious that she was simply going through the motions to some degree; she was likely terrified of getting fucked in front of me but even more afraid of betraying the deal we had made. Though we continued to try Chat Avenue, I was ready to extend our search.
I started browsing seedier porn sites without my Mother's knowledge. I had arrived at the point where I didn't really care where the guy came from or how involved she was with finding him, I just wanted some form of control over my Mom. I posted detailed messages about the situation from my own perspective on half a dozen websites to start, and got way more feedback than my Mom did on Chat Avenue. Guys apparently loved hearing from a guy who was the son of a real life mature slut.
Finally, two days before Father's Day, I found our guy ... He was a 37 year old named Jared from Arcadia, FL, a town about an hour north of us. Not that it mattered to me, but he wasn't great looking; based on his profile picture, he was a little overweight and not all that handsome. He said he was willing to meet us at a hotel late Monday morning in Punta Gorda, a halfway point between us, but he just needed some kind of proof that we were legitimate.
Before I went to work the next afternoon, I let my Mom know we had plans on Monday morning. As I expected, she wasn't at all thrilled, but she didn't object too much ... well, not until I told her that she would need to pose for a topless picture while holding a sheet of paper with "Jared" written on it. That was very off-putting for her, but again, I was at the point where I didn't care about her wants or needs or feelings. She gave up that right when she started fucking Dylan behind my father's back.
Reluctantly she took her shirt off and held the piece of paper to the side of her chest and mustered a smile that lasted maybe three seconds. Good enough. I sent the picture along to Jared and he confirmed late on Saturday night that we were good for Monday at 11 am at a Days Inn. We would be meeting him in the parking lot.
Jared's confirmation made for a very odd Father's Day. I don't think my father caught on that there was anything out of the ordinary; my Mom and I both did a reasonable job making things seem as normal as possible around the house in those three weeks since I had confronted her about cheating, and because he was taking on more responsibilities at work, he was becoming more and more distant at home anyway. It was actually odd to have him home all day that Father's Day afternoon.
The next day he would be gone from 8 am until 8 pm, the usual for a Monday, and we'd be out of the house not too long after him. I woke up at around 9 am and my Mom was already in the kitchen putting her make up on. Although she looked good, it was more a "going to the grocery store" looking good than "going to get fucked by a random guy in a hotel room" looking good.
"Heavier on the make-up," I instructed her as I poured myself a glass of water. She didn't say anything, but she listened. She applied her eyeliner and eye shadow and then carefully put on bright red lipstick. "That looks good."
She again didn't say anything. I hated when she did this, but I obviously understood why she did it. For three weeks I had to deal with a prolonged silent treatment at least once a day.
"Look, I know this is awkward for you. It's not like it isn't weird for me too. But this is how things are going to be from now on. We might as well have fun with it, ya know? You get to fuck a bunch of guys that aren't Dad, and I get total control over all of it. That's better than the alternative, right?"
"And what alternative is that Sean?"
"Me telling Dad, him divorcing you, and you being recognized publicly as a disgrace to your family. I don't want to have to do that. And I don't think that's what you want either."
She sat silently for a few moments, and then said something that surprised me.
"Yeah, you're right." I was stunned.
"Good, I'm glad you see it that way. I'm gonna start getting ready. We'll leave at 9:45, cool?"
"Yeah, that's fine," she replied. I started walking out of the kitchen, but she called me. "Hey, Sean?"
"What should I wear?" she asked. I paused for a second to think about it.
"I'll find something for you. It will be laid out on your bed," I told her
I went up to her room and started browsing through her dresser to find something that she'd look sexy in. I decided it would be appropriate and maybe even a little poetic to dress her in the outfit she wore to Publix to meet me; tight white tank top with even tighter blue jeans, plus a pair of heels to slut the outfit up even more. Additionally, I had a plan to make her appear even trashier than she already was.
Five minutes into our drive I stopped at the gas station to fill up my tank, but I also decided to grab her a pack of Misty 120's for old times sake. To my surprise, she immediately objected.
"No way, I'm proud of the fact that I quit smoking. You don't get to control that aspect of my life," she said sternly. I let out a laugh.
"What are you talking about? Apparently you forgot what you did, and the leverage I have over you. I call the shots. And besides, you looks sexy smoking cigarettes. I'm sure Jared will be turned on by it." She gave me a weird look when I said that. I guess that was the first time I ever referred to her as 'sexy'. "Put that electronic cigarette in the glove compartment. You don't need it today."
I held out the pack of cigarettes in my hand in front of her and she begrudgingly grabbed it from me.
"Your father is going to be pissed off at me when he smells it on my breath," she said as she began opening up the pack. "He was the one who suggested I quit and start vaping."
"I'm pretty sure if you can hide the smell of a guys cum on your breath you could do something about the smell of cigarettes."
She took one of the long, thin Misty's out of the pack and put it between her lips. She gave me a dirty look, then motioned down with her head at the lighter in my hand. Instead of handing her the lighter I held it up near the cigarette in between her lips and flicked it a few times until a small flame arose. Her eyes were locked on me; she was giving me a death stare as her cheeks hollowed with the first deep drag she had taken on a real cigarette in 6 months.
She took a few more drags, and even though she wouldn't admit it right then, I knew she was enjoying it. She resented my father for forcing her to quit; she never said as much, but when she made the switch from real cigarettes to the E-cigarette I could tell.
"Sean, why did you say I looked sexy smoking cigarettes," she asked me as she flicked the cigarette butt out of the window.
"Because you do," I said without hesitation. She again went silent for a while, but I knew in some weird way she was actually flattered that I felt this way, because she took another cigarette out of the pack immediately.
We got to the hotel at 10:45 and Jared was sitting in his car waiting for us. When my Mom saw him getting out of his car I could tell she was underwhelmed. She had spent the last couple of months fucking a legitimately good looking 24 year old, and now she was about to slum it with a below average looking 37 year old.
"Light a cigarette," I told her as I got out of the car first and shook hands with him. He was very excited, and much less nervous than I expected he would be. I commented on his calmness and he explained that he had once fucked a woman in front of her husband and he had met them online, so he was not a total stranger to this idea. I motioned to my Mom to exit the car and she did so with her cigarette dangling between her lips.
"Wow, she's even hotter in person," Jared commented. I agreed. She looked incredible; she was becoming the sexy, trashy MILF she was truly destined to be. She walked over to us, threw her cigarette on the ground and crushed it out with her heel.
"Mom, this is Jared. Jared, this is my mom Anna," I said as my Mom extended her hand out to him. They engaged in one of the most awkward handshake's I'd ever seen and we made small talk for maybe 90 seconds before I suggested we go into the room. I had been waiting long enough.
The three of us made it up to Jared's room, and he suggested I sit in the corner to watch since that's what the husband of the woman he fucked did. I obliged even though I wasn't a cuckold, and told him that all he had to do was make let her know what he wanted her to do and she would obey. They sat on the bed next to each other and after a little more small talk they started making out. As I had instructed while we were driving, my Mom was doing a great job pretending like she was into this, or maybe she actually was.
Jared laid down on the bed and without instruction from him or I my Mom unbuttoned and unzipped his shorts and then licked her right palm to prepare for stroking his half-hard cock. It didn't take long for Jared to get fully hard, and as soon as he did my Mom made his cock disappear into her mouth and throat just like she did Dylan's.
Jared wasn't nearly as hung as Dylan was, but it was still impressive watching my Mom swallow his entire cock so effortlessly. She would go up and down, up and down, her forehead smacking into the bottom of Jared's stomach each time. Every once in a while she'd take the cock out of her mouth and stroke it in one hand while she started paying special attention to his scrotum. She passionately tongued his ball sack and squeezed both of his balls into her large mouth and started stroking his dick faster. He let out a excited groan when she started.
"That good, man?" I asked from the corner. He let out another groan and gave me a thumbs up. It must have been fantastic, because he barely lasted two minutes once my Mom started sucking him again. Without any warning he busted in her mouth; she kept sucking as he was pumping his seed into her, and she swallowed every drop he deposited into her. He seemed mildly embarrassed he didn't last that long, but he acknowledged that it was the best head he had ever gotten. He said he was excited to fuck her next, but he would need a little bit of time for recuperation. This was fine with my Mom; she excused herself and went outside to smoke. Not only was I ecstatic because I was just ten feet away from her while she sucked a cock, now I had her willingly go outside to smoke cigarettes. After a few minutes of more awkward small talk with Jared, I decided it would be more fun to join her outside.
She was sitting outside of the lobby on a bench and absolutely nobody was around. Not that I actually cared, but she seemed mildly dejected.
"Hey, you alright?" I yelled as I walked through the sliding doors. She looked at me as I walked toward her, but she didn't respond. "You good?" I asked again.
"Yeah, I'm fine," she responded. It was the typical female answer. Every guy knows that 'I'm fine' means she's not fine.
"I know it's weird, but you'll get used to it," I said trying to reassure her. In reality, I had no idea if she'd get used to me watching her have sex with other men. But it turns out, this isn't what she was discouraged about.
"It's not that," she said after a momentary pause. I looked at her waiting for her to telling what it was that was bothering her, but she didn't budge.
"Well, what is it?" I prodded.
"Look, Dylan was really hot. This guy ... he's not at all. If we're going to keep doing this, I want younger, hotter, bigger guys. I would be that the more I enjoy this, the more you'll enjoy this."
I didn't know if that last part would always be true, but I did know that if I could do anything that would at least get her temporarily more involved, I had to do it.
"I get that. That's fair," I replied. She pulled out another cigarette from her pack and lit it.
"I have to admit ... I missed these," she said and giggled. I missed it too. A thick stream of smoke flowed out of her mouth and nose as she laughed. She looked so sexy sucking on that thin Misty 120.
"Yeah, I could tell." I paused for a moment and just watched her take a deep inhale. "You know what, let's get out of here," I said to her.
"Are you serious?" she replied. She was obviously both surprised and delighted.
"Yeah, this guy is boring, and you're right, it will be better for both of us if you are enjoying it. I'll run up, tell him we have a family emergency and that we have to go. Just hang down here, OK?"
I didn't actually care if she enjoyed it or not, but I did think it was important to get on my Mom's good side for the time being. Even though she wasn't into Jared, I could tell she wasn't hating this nearly as much as I or she probably expected. In fact, based on her request to have sex with younger, hotter guys, I believed she actually enjoyed the idea of being able to fuck whoever she wanted, even if I meant that I was there for it.