Cheering Mom Up Ch. 03

I believe the saying goes, "fuck your mom once, shame on her. Fuck her twice, shame on you", or something like that. To be honest with you, I didn't really feel that bad about it. It's not like something that will ever even come up to Kelly and there seemed to be an unspoken agreement that it would be the last time. After all, it wouldn't be long before they were married.

Kelly got home that night and things seemed to get back to normal. We had dinner together. We watched some TV together. We went to bed. They had quite loud sex for about an hour as I was in my room listening and masturbating. So, I guess it might be incorrect to say things went back to normal. Let's call this the new normal.

To be honest, as much as all of this was probably unhealthy behavior, it really seemed to be helping me. When I would hang out with them at night, I would tell them about how I was feeling about the whole situation with Sarah. In those moments, it wasn't my mom who I had just slept with and the women who I almost slept with that is now sleeping with and engaged to her. Instead, it was just two women who cared about me helping me get through a tough time.

Unfortunately, there was a little break in our little therapy sessions when my mom head to head out of town, "I wish I would have known that you were going to be here, Ryan. I wouldn't have committed to this conference. Lord knows I don't want to be there anyways."

"It's okay mom, It's only a couple of days."

Kelly chimed in, "I'll take good care of him! Don't worry, Julia."

"And who's going to take care of you," she asked Kelly as she planted a kiss on her fiancé's lips.

"I suppose Miguel will have to take care of me," she said with a devilish grin on her face.

I'm not always the most observant person but context clues told me Miguel might be one of their toys not meant for children and that I should probably not ask any questions. If the context wasn't enough, the deer in the headlights look they both gave me after Kelly's statement said it all.

"Guys, let's just move on."

"Movie time," my mom said slightly louder than an inside voice due to feeling uncomfortable.

That night went just like the rest of our nights had been. In the morning, my mom got up pretty early as her conference was a three-hour drive away. I set an alarm to try to get up to say good bye to her in the morning. I had become somewhat lazy since I got back home and this was a good two hours earlier than I had normally been getting up. Unfortunately, I ended up missing her. Apparently, Kelly was used to my normal time getting up and wasn't expecting to have anyone moving about the house. I walked out into the kitchen to find her getting her coffee and wearing nothing but a thong and a tiny white tee. She also clearly had no bra on.

"Good morning," I tried to say in the least startling tone possible but I still scared her.

"Jesus! Good morning, Ryan. Shit! Sorry, I wasn't expecting you to be up yet," she muttered as she attempted to cover herself up. It was an admirable attempt but there's no hiding her curves.

I laughed and replied, "You definitely don't need to apologize. I actually think I should be thanking you. This is an amazing way to wake up."

"You naughty little thing. Flirting with your mom's lover," she said with a smirk.

"Honestly, who says lover?"

"You're just jealous. You had a chance but your mom didn't miss hers," she teased.

"Yeah, she's pretty lucky."

"I'm the lucky one. It's too bad you'll never get to experience what it's like to sleep with Julia," she said as she read the uncomfortable look on my face, no doubt misinterpreting why I was uncomfortable, "Sorry. I have a weird sense of humor."

"It's totally fine. I'm just not used to you saying her name so quietly. You're normally screaming it at the top of your lungs," I said and she promptly laughed and punched me. We both finished drinking our coffee.

Eventually, Kelly had to leave for her shift. It was somewhat of a relief because she seemed to become very comfortable being around me in that outfit. Conversely, it was becoming very uncomfortable for me trying to hide how much I enjoyed seeing her in that outfit. She honestly had a similar body type to my mom's but, due to her younger age, it was just a little tighter across the board. That's no disrespect to my mom as she was still in great shape.

Once she left, I found that I was incredibly bored being at the house by myself. It wasn't just because there wasn't anything good on TV and I couldn't find much on Netflix that I really wanted to watch. I honestly just missed hanging out with the two of them. We would have conversations with each other with no TV or any distraction even on in the background. We would just sit together with coffee or wine or whatever and just talk to each other, enjoying each other's company. So, eventually I got stir crazy being at home. I decided to go to the bar and see how Kelly's shift was going.

When I got there, I found her behind the bar. She looked up as I walked through the door and said with a big smile, "Hey Ryan! Missed me?"

"Yes, actually."

"Aww, that's sweet! Can I get you a drink?"

"That would be great! Can I just have a whiskey on the rocks?"

"Coming up!"

"So, when did you move behind the bar?" I asked.

"It's been a couple of years now. I'm actually managing the bar now!"

"Oh, that's awesome! Congratulations!"

"Thanks," she said as she prepared to whiskeys, sat one in front of me, grabbed the other and raised it towards me, "cheers."

I met her glass, "Cheers."

It might not have been helpful for her tips, but it was helpful for my boredom that the bar wasn't very crowded. That meant that we were able to spend most of the night just hanging out. Essentially, we got to have that date that we didn't last time.

I found myself feeling a lot of regret for not doing so back then. However, I've never seen my mom happier so I guess it was for the best in the end. She was a very fun, smart, and entertaining woman and I'm glad that my mom found her. That being said, I was getting drunker and drunker and becoming more and more aware of how beautiful and sexy she was. For better or worse, I don't think this attraction was one-sided. Either way, I needed to get these feelings in check because I could never do that to my mom. Putting the sex aside, my mom was truly a great mom and she was in love with this woman. I did my best to behave myself and lead the conversation in less flirtatious directions.

Eventually, we got to closing time at the bar. We could see those who were in the bar attempting to figure out their potential hookup situations. That energy lead to some nervous laughter between Kelly and I. Once everyone cleared out, I helped Kelly in cleaning up the bar and then she eventually drove us home.

Despite the palpable tension between the two of us, we both managed to behave and went to our individual rooms once we got home. But, even though I went to my room, that doesn't mean I was able to get to sleep. I guess my heart was racing a little bit too quickly still to go to sleep. So, I decided to go to the kitchen to make some chamomile tea hoping that would help get me ready to go to sleep.

At first, it certainly seemed to be working. I felt a little calmer. I started reading the newspaper that was sitting there which helped me keep my mind off of things. Despite my efforts, it was all reversed in a second when I heard footsteps coming down the hallway. I looked up and obviously it was Kelly that walked into the kitchen. She was again wearing her typical outfit of a thong and a tiny t-shirt.

I tried to keep the energy playful and not flirty, "Wow we're really making a habit of running into each other like this."

She, however, did not have a look on her face that indicated any level of playfulness. After a few moments, she managed to say, "yes, but this time it isn't really an accident."

Even though I knew what she meant, I asked, "What do you mean?"

"I think you know what I mean. I think you felt it too. We both still have curiosity about this."

I'm terrible in these situations so I kept asking questions that I knew the answer to, "Curiosity about what?"

"Ryan, stop. You know exactly what I'm talking about. I've seen you looking at me. We've both been flirting with each other the entire time that you've been here. It makes sense too. The whole reason that your mom and I got together is because you and I almost got together at one point. You were with Sarah at the time but that doesn't mean that we both weren't into each other. Those feelings don't always just go away."

I could tell she might lose it on me if I kept playing stupid so I asked, "But what are we supposed to do about it? I couldn't do that to my mom and I don't think you would either."

"I would never in a million years want to hurt your mom and I know you wouldn't either. You two obviously both love each other and her and I love each other. However, I think we would be setting ourselves up for some big problems down the road if we don't just address the elephant in the room right now."

My heart was racing again so I reverted back to asking questions with obvious answers, "So, how should we address it?"

"I want you to fuck me."

I had understood what she was getting at but I wasn't prepared for her to blurt it out so bluntly. It caught me off guard and I almost spit out my tea. I looked back up at her and it was clear that she was done talking. She walked toward me and grabbed my hand. She then started walking away and started pulling me with her. I knew I should be telling her no. I knew this was wrong. However, all I could manage to do in that moment was watch her beautiful ass bouncing with every single step she took.

As we went up the steps, I was looking at the glow coming from their room. I was getting more and more nervous as we got closer. However, she stopped before we got there and turned toward me, "We shouldn't go in there. Your room?"

"Whatever you say."

As we got into my room, she joined me in being nervous. It was as if neither of us knew how to start. I was staring at my mom's fiancé and she was staring at her fiancé's son. Those facts were clearly weighing heavily on both of us in that moment. I figured I'd try to help ease the tension by taking my shirt off. It was the least I could do after she gave me such a great view on the walk to my room. I could see her checking out my body. It seemed as though she liked what she saw. This whole situation felt very much like two high school sweethearts about to lose their virginities to each other. We were both just taking in everything that was going on but had not yet touched each other.

Eventually, she said, "It's been so long since I've been in a bedroom like this with a man."

"How is it so far?"

"It's good. My heart is racing though."

"Mine is too," I admitted.

Hearing that I was nervous too seemed to make her feel a little more at ease. She then took her shirt off, this time wearing a bra. I took a second to just admire her beautiful body. Her curves were almost unfair. Her ass is what gets most of the attention though as it was clear that she had put some time in the gym to sculpt that large but what looked to be firm derriere. She had nice, perky breasts that weren't huge but were by no means small. As I continued my gaze moving up her body, I finally got to her beautiful face and found her eyes locked in on mine. Those eyes! My god! They were the most inviting shade of green I had ever seen and they were doing a great job of absolutely melting me at the moment.

She smiled at me and moved to take her bra off but I stopped her, "Let me."

I moved in close to her and reached around to her back to unclasp her bra, lightly kissing on her neck as I did it. I could hear her lightly moaning each time my lips touched her skin. I then let her bra fall to the floor. As good as her breasts looked in the bra, I wasn't fully prepared for how amazing they looked without it. They were perky and had slightly smaller nipples than I had expected. I could hear and feel her breathing intensify as my tongue began massaging her left nipple, then her right. I then stood upright again and finally kissed her on the lips. This kiss felt similar to the first time I kissed my mom. The butterflies in my stomach were going wild.

It caught me off guard and I backed away for a second, again locking eyes with Kelly. She seemed to be in a similar state of mind. She asked, "Are you okay?"

"Yeah. Are you?"

It almost seemed like she was surprised by her answer, "I am."

Again, we locked lips. Our tongues were now joining the party. Her lips were so soft. Her tongue expertly danced with mine and I was more than willing to let her show the way. Desperate to get my hands on her thick butt, I reached around her and got a handful of each cheek. We stood there making out for a little while. I found myself still feeling nervous about taking the next step. Luckily, she was bolder as she turned around, walked to the bed, laid on the bed, and looked up at me with one of the most enticing smiles I've ever seen. That was all I needed to finally cross that threshold. I removed my pants and joined her in bed.

As I crawled up over her body to kiss her, I could sense that she was still about as nervous about me. However, it felt as though both of our nervousness melted away the second our lips touched again. We were back at it with our tongues going wild. Every now and then, I would work in a neck kiss and she would let out a moan.

In a move I didn't see coming, Kelly pulled a reverse and flipped me over on my back, ending with her straddling me. Given her general disposition, I didn't expect her to take charge in the bedroom but I thoroughly enjoyed experiencing this side of her.

She backed off and looked to my nightstand and smirked, "What's that for?" she asked, indicating the lotion sitting on the table.

"Um," is all I could manage as I had no idea what to say.

She laughed a little as she reached over and dispensed some lotion into her hand. She used both hands to spread the lotion over her whole hand. She went back to kissing me but also reached around behind her and inside my boxers to find my already fully erect dick. I shivered as soon as she made contact. Her hands were so soft and she had just the right touch as she began stroking me. I began to breath heavily as she kissed me. I'm sure my make out game wasn't at its strongest but her hand had me a bit distracted. Since my mouth was proving to be useless at the moment, Kelly took that opportunity to show just how useful her mouth could be. While continuing to maintain eye contact with me, she slowly mad her way down below my waist. She removed my boxers and found my dick to be very excited to see her. She laughed a little at the sight.

"Always makes you feel good when a girl laughs at the sight of your dick."

This made her laugh even harder. In between laughs, she assured me, "I think you know I'm not laughing about the size," she said with a sly grin.

I wanted her mouth so badly and it was pretty clear she knew that. She took her time and teased me. There were a few light brushes of her tongue and thigh kisses as she played with me a little with her hand. After what felt like an eternity, she finally took me in her mouth and it felt just as amazing as I was anticipating. Again, I was loving how this somewhat shy girl truly came out of her shell in the bedroom. She was doing work on me that would have a porn star taking notes. She was sliding her mouth up and down with ease while simultaneously performing magic with her tongue. In addition to that, her lotioned up hand was making sure my balls were also being taken care of. She was doing such incredible work down there that I struggled to get my brain to function enough that I could think of things to keep me from exploding. Baseball. Spiders. Donald Trump in a speedo. It wasn't working. She was breaking through my inner thoughts and apparently she could tell, "Oh, no you don't. You're going to fuck me so let's let that thing calm down."

After she said this, she crawled up and sat on my face. I quickly learned that she was already quite wet. The moisture of her pussy was now coating my face but I didn't mind in the slightest. I just laid their and enjoyed the moment. I didn't even need to work that hard because I wasn't eating her pussy as much as she was just riding my face. She was sliding over my tongue and more and more into it with each gyration of her hips. To be honest, I was getting short of breath but I was okay with it because I decided I'd be at peace with it if this was the way that I died, being smothered by Kelly's beautiful pussy and plump ass cheeks. She seemed to be considering the same thing, causing her to back off my face for a bit and ask, "Are you okay? I got carried away and forgot that you have to breathe."

"I'm great! I'd rather help you cum than breathe to be honest."

Apparently, this was all she needed to hear because she hopped right back onto my face and began grinding even more enthusiastically than she was before. Her body started to tremble more and her breaths started to turn to heavy panting so I could tell she was moving in the right direction. I wanted to send the message that we were in this together and I wanted her to feel as good as possible so I reached with both hands and grabbed her ass and pulled her in towards me, causing her pussy to press even more firmly against my tongue and face. In this moment, she let out a noise that I hadn't even heard during her marathon sessions with my mom. I suppose I would describe it as a squeal? Regardless, it was a sound of pleasure and I was very excited to hear it. We were in the home stretch and she was riding me with absolutely no abandon. Finally, I heard her let out a loud moan as I could feel even more moisture running over my face. Kelly wiped off my face before kissing me deeply.

"I want you inside of me."

I kissed her and said, "You don't need to tell me twice."

She grinned as she moved towards the end of the bed, put her face down into the mattress and her ass up, presenting her ass and pussy to me in the most inviting view I could imagine. I began getting to work. I grabbed her hips just to get a little more power with my thrusts. It honestly surprised me how tight she was but I know it felt unbelievably good to be inside of her.

However, I didn't get to experience it for that long. I suppose Kelly and I just got so lost in the moment that we didn't hear the door open. We didn't hear the luggage hit the floor. But, we did hear my mom say, "Well, it looks like you two are getting along."

Kelly pushed me off of her and looked up at my mom with a mortified and ashamed look on her face, "Julia, this isn't what it looks like!"

My mom questioned this obvious lie, "It's not?"

"Okay, it is what it looks like but it was...we didn't...I'm really sorry," Kelly said as she began to cry.

My mom smirked a little as she walked over to us. She sat down on the bed between us as she began to comfort Kelly. She rubbed her back as she gave her a loving kiss on the cheek, which led to a passionate kiss on the lips. Finally, my mom said, "It's really okay."

"Really?" Kelly replied incredulously.

"Yes really."

She planted one more kiss on Kelly before leaning back and smiling at this girl she clearly loved very much. Kelly smiled back and it appeared as though a weight had been lifted off of her shoulders. However, what happened next was something she definitely wasn't expecting. My mom shifted her attention to me as she leaned over and gave me a very unmotherly kiss. Her tongue made its way into my mouth as I noticed the shock overtaking Kelly's face. That being said, I'm sure that my face looked relatively similar. I had fantasized about having these two women in my bad. Sure. But, I never expected my mom to take that from fantasy into reality and letting anyone in on some of our secrets. Nonetheless, here we were. She eventually broke the kiss and looked back at Kelly.