Cheering Mom Up

"All holidays are tough but none of them hit quite as hard as Valentine's Day. That's when it really hits me that I'm alone."

I couldn't get those words from my mom out of my head. It had been three years since my father died and, while it was certainly tough on me and my siblings, I believe that it was hardest on my mom.

My parents had a great relationship. Of course, they fought with each other from time to time but it was always clear that they loved each other and they were both very supportive of each other. My sisters and I have all managed to have good, healthy relationships and we probably have our parents to thank for that.

My dad truly was a great guy. Unfortunately, one not so great guy chose to get behind the wheel with a .25 BAC and took him away from us. I was twenty-three at the time and I was living with my girlfriend (now fiancé), Sarah, in Los Angeles. Both of my sisters also live away from our hometown of Denver but, obviously, we all returned home for the service. We all stayed for a few weeks to help mom out get everything under control. But, we all eventually had to go back to our lives, sadly leaving mom alone in Denver. We have other family in Denver but, naturally, nobody could quite fill the void created in my father's absence.

Back to present day, I had just finished a phone call with my mom. We got into a conversation about Valentine's Day because she was curious about what I had planned with Sarah. That eventually led to the aforementioned quote that made my heart sink.

My mom has not dated at all since my father's death. That is not due to a lack of interest in her though. She has had many men ask her out in that span but she seems to have no interest whatsoever in any of them. My father was the love of her life and I don't think she wants to make any attempt to replace him. Despite the fact that her being alone has a lot to do with her own choices, I still can't help but feel terrible for her.

I was pretty much useless for the rest of the day at work. When I got home, it was really comforting to see Sarah. She is one of the most beautiful women I have ever seen but it's her warm personality and friendliness that really made me fall in love with her. I didn't tell her about my conversation with my mom but just being around her that night made me feel better.

Right before we were about go to bed, Sarah turned to me and said, "I have some bad news."

"Uh oh," I replied.

She sighed before coming out with, "My boss wants me to head up to San Francisco this weekend to try to sign this new band. It's the first time he's letting me go as the lead."

"Well that's great! Isn't it?" I asked.

"It's awesome workwise but what about trip to Catalina for Valentine's Day?" she replied.

I was had been very excited about our trip but I tried to hide my disappointment, "We can just cancel it. This is a big opportunity for you. Besides, San Francisco could make for just as romantic a weekend for us."

"It would be but....I can't bring you. They have a strict no significant other policy on business trips after Susan brought her husband to San Diego and tried to expense $2,000 worth of dinners and drinks that involved no clients," she stated with a distressed look on her face.

I smiled, grabbed her hand and told her, "Hey, Valentine's Day is just a day. Catalina will still be there next week. Besides, you know that my phone sex skills are off the charts."

Sarah scoffed, "They're about the same as mine and that's not saying much. Our phone sex is about as awkward as two teenagers soberly losing their virginities together. We might have to stick to dirty pics."

"Fair enough. This actually might be a blessing in disguise. My mom was just telling me today that she tends to feel especially lonely on Valentine's Day without my dad. Maybe I could spend the weekend with her," I suggested.

She perked up at the idea of this, "That would be so sweet! I think that's a great idea....ninety percent because it will make your mom really happy and ten percent because I will feel less guilty about ruining our weekend. Actually, I'll try to make up for it a little bit right now."

She gave me a soft kiss on the lips, then kissed her way slowly down my body until she disappeared beneath the covers. I was hard from the moment she made contact with my cock. Her tongue felt absolutely amazing as it softly and expertly massaged me.

I wanted to see the action so I lifted up the comforter. I found her beautiful eyes staring back at me as she went to town on my dick. As I ran my hand through her soft hair, I attempted to talk to her but all I could get out was several "You"s followed by very satisfied groans.

I started to feel the familiar tingles and jingles so I said, "Babe, I'm gonna cum."

She didn't say a word. She just winked at me and kept going with even more intensity. Within seconds, I finally lost control and blew my ample load into her mouth. Like a champ, she swallowed it, wiped her lips off and crawled up to kiss me. Then, she whispered, "That's just part one. I still have plenty more making up to do."

As often happens after I cum, I fell asleep pretty much immediately. The next day at work I decided to call my mom and let her know about my plan to come visit, "Hey mom!"

"Hey sweetie," she exclaimed.

"I have some good news."

"What's that?" she asked.

"I'm gonna come visit you this weekend!"

"Really?! That's great! Wait, what about your trip with Sarah?"

I replied, "She got a promotion at work and has to go to San Francisco for the weekend. She can't bring me because some woman that she worked with tried to have a decadent weekend with her husband on the company's dime."

"Oh Ryan, that stinks! I am selfishly glad though because it means that I get to see you!"

"I'm excited too! It's been so long since I was last home."

"I know! It's been almost a year! You're so busy though and Sarah is such a great girl. I don't blame you at all. Sometimes, things just happen that way," she said.

"Yeah but it shouldn't have taken this long. Anyways, my flight should be getting in around 8 p.m. I also took off Monday so that we can just enjoy the day on Sunday and not have to worry about traveling."

"That sounds perfect! I'll come pick you up then," she responded.

"You don't have to do that. That airport can be crazy. I'll just take a cab."

"Don't be silly! I'll be too excited to wait that long."

I laughed and said, "Okay. I gotta run to a meeting but I'll see you on Friday."

"Bye sweetie!"

I was actually very excited for the trip to see my mom. The next two days at work went incredibly slow. It didn't help at all that Sarah had already left. To help out, Sarah sent a very NSFW photo for me to enjoy in my leisure time. In fact, I enjoyed it the first night she was away. A lot of men would scoff at me jerking off to a picture of my own significant other but, honestly, Sarah is much sexier than anything porn or my imagination has to offer. Long story short, her impressive photography allowed me to approach my destination in a very timely fashion. Unfortunately, right as I was about to arrive, I received a call from my mom. So, I ended up cumming while looking at an image of my mom's face. Not to say that my mom is an unattractive woman but I was certainly not comfortable with that fact. I could not deal with talking to her so recently after cumming, especially since it accidentally happened to her face, so I had to red-button her.

Friday was a fairly busy day at work for me because I needed to leave a little early in order to make it to the airport on time. LAX was a little crowded but the whole process went fairly smoothly. My flight took off on time and we touched down in Denver a few minutes earlier than our ETA. As I came out into the terminal, I found my beautiful mom waiting for me with a giant smile on her face. She ran up to me and gave me a giant hug. The smell of her flowery perfume brought me right back to my childhood. It must have been because I hadn't seen her in such a long time but that hug felt incredibly good and comforting.

As we broke the hug, she took a good look at me and said, "My goodness, you are looking more and more like your father every year.....especially with that beard."

"I'm not the biggest fan of it but Sarah likes it."

"No, I think it looks good. Very handsome. Besides, Sarah is a hot little piece, I would listen to her if I were you."

I laughed and said, "I always do."

We then left the airport and made the conveniently short trip to my mom's house. The house was exactly as I had last seen it. In fact, it hadn't changed much at all since I was a kid which was very comforting. I went to my room to put my bags away. As I walked in, I realized that everything was still the same as it was when I moved away to Los Angeles with Sarah after college. My Fight Club poster was still on the wall. My Playboy magazines were still tucked under the bed. The only difference that there weren't dirty clothes all over the floor. My mom had clearly tidied up a bit in there because I am a horrible slob when it comes to my own bedroom.

I walked downstairs to find my mom watching TV while enjoying a nice glass of red wine. She asked, "Hey sweetie! Do you want a glass?"

"Sure! I'm not driving."

She poured me a fairly sizable glass. I took my first sip and it was absolutely delicious. That isn't surprising though because my mom always had good taste in wine and had the money to enjoy it often. As I sat down, I realized that she was watching Sleepless in Seattle. That seemed quite appropriate given her situation. I would imagine that she identified very much with Tom Hanks' character as he also lost his spouse and had very intense feeling of loneliness. At least for his character, he had his son with him all the time to keep him company. I began to feel guilty how my sisters and I had all sort of gone on with our lives without making a real effort to visit with or even call our mom all that often. With that in mind, I was determined to make this a great weekend for her.

The combination of the long day of work and travel with the several glasses of wine left me feeling very tired. So, as I often did as a child when we watched movies, I rested my head on my mom's shoulder. I started to doze off. When I awoke, I found that my face had drifted down into her left tit which also let me know that she wasn't wearing a bra. The weirdest part about it was that it didn't make me feel all that weird. It was oddly comforting. I guess the cozying up without the sexual implications combined with being in my childhood home brought me back.

She seemed to feel the same way as she said, "This is nice! It feels just like old times. I'm sorry that your weekend with Sarah got messed up but I'm happy you're here." After saying that she ran her fingers through my hair and gave me a nice, soft kiss on my forehead.

"To be honest with you, mom, I'm not really that sorry that my trip got canceled. I'm really happy to get to see you."

I returned the affection with a hug and got another great whiff of her intoxicating perfume. She smelled so good. Not to mention the fact that she still looked phenomenal despite being in her fifties. She clearly would have no problem finding a man. To be totally honest, I wanted that for her. Not that I want someone to, nor do I think anyone could, replace my father, I just want her to be happy and not feel so lonely anymore. So, I asked, "Have you been dating at all?"

She took a second and then responded with, "Not too much. I went on a date with a coworker of Judy's a few months but it wasn't exactly a love connection."

"I don't want to tell you what to do but I think it would be good for you to get back out there."

She replied, "I know but it's hard. I don't think I really know how to be part of the single scene anymore."

"You're not gonna have much trouble at all. The single scene will adjust to you. Believe me, you have no idea how hard it is to grow up as a guy with a hot mom."

This caused her to laugh and question, "Oh, I'm a hot mom, huh?"

"Oh yeah. If you only knew the things my friends said growing up about you and continue to say to this day."

"That's good to know. So, I could still get twenty-somethings?" she asked in a somewhat joking manner.

"No question. In fact, maybe we should go out tomorrow night. I can be your wingman."

"Wouldn't that make you feel uncomfortable?" she wondered.

"Not at all."

"I would like to meet someone. I haven't had sex since your father passed away," she paused after saying this, clearly feeling like she said something that she shouldn't have, "Sorry! That's weird for me to say to you. I think it's the wine."

I laughed and assured her, "Don't worry about it. I get it. Everyone has a need for intimacy."

"I agree but I'll try my best to not get too descriptive for your sake."

"I appreciate that," I said with a grin.

"I think we should go to bed now so that we don't sleep the day away tomorrow."

"Good call. I'll see you in the morning!"

She gave me a hug and a peck on the lips which was customary in our family prior to going to bed. She went to her room and I went to mine. I got to sleep within minutes of laying down on my bed.

The next morning, I woke up feeling slightly hungover. I guess I had a few too many glasses of wine. Luckily, I could smell bacon and eggs being cooked downstairs and that typically does the trick for me. I made my way downstairs and found my mom in the kitchen with a plate already prepared for me on the table.

"Good morning, sweetie!"

"Morning! This looks great, mom."

"Thanks! So what do you wanna do today?" she asked.

"Um....well, do you still wanna go out tonight?"

She responded, "Are you sure that you want to?....it won't be weird for you?"

"No, not at all. Dad's been gone for three years. It would make me feel better knowing that you had someone to spend time with and kept you from feeling lonely."

"And what if this imaginary guy and I REALLY get along?"

"Then I'll throw on my headphones like I did each year on dad's birthday."

She almost had orange juice shooting out of her nose while laughing at this and barely managed to get out, "I'm just going to leave that one alone."

Once she got herself composed again, she asked, "So, what are we going to do until then?"

"We could go see a movie. I think that new Katherine Heigl rom-com is opening today."

"Oh, I really want to see that!"

With a roll of my eyes, I replied, "I figured you would. Believe me, that's the only reason I would consider going to see it."

"Normally, I wouldn't make you go. But, I really want to see it so I'm going to take advantage of your niceness."

"I figured as much."

After we finished eating breakfast, I offered to do the dishes. We both then started getting ready to go. There was only one shower in the house. I let my mom take the first shower because it always takes her much longer to get ready. While she was in there, I went into the living room to watch some TV. A few minutes in, a book sitting on one of the side tables caught my attention. I grabbed it and realized that it was my mother and father's high school yearbook. I noticed that one page was folded in the corner. I opened it to find a large picture of my parents. They had won "cutest couple". I don't think that they ever told me that they won that but it wasn't surprising because they were a great couple. What did sort of take me aback was how stunning my mom was at that age. I mean, she was an absolute knockout. I guess I shouldn't have been too surprised thought. Even now, north of fifty, she still turns heads wherever we go. I figured that this would be the easiest wingman job ever.

While I was waiting, I figured I'd check in with Sarah. When I called, her voice sounded like she just woke up, "Hello."

"Uh...hey. Did I wake you up?" I asked.

"Yup."

"Sorry! I forgot about the time difference," I apologized.

"No, it's not your fault. I'd normally be up by now but we were out late after the show and the band really seems to enjoy drinking."

"Yikes! That sucks, babe. Do they have another show tonight?"

"Uh huh. After the physical toll they're taking on me, they better sign with us."

I tried to encourage her, "I'm sure they will. I can attest to your persuasiveness."

She laughed and replied, "I'm not sure you want me to use that same persuasiveness here.....unless you're cool with me blowing the whole band."

"Sarah, I don't think you're giving yourself enough credit. Your vagina and ass are also great," I joked.

"It would be much more efficient if I could incorporate all three at the same time."

I laughed very hard at that.

She followed with, "Speaking of which, I really can't wait until we're both back in LA. I miss little Ryan."

"I'd like to reiterate for the thousandth time that I wish you would come up with a nickname for my dick that didn't have the word "little" in it."

She replied, "Oh sorry...I miss huge, gigantic, monstrous Ryan."

"That's more like it."

She paused for a second and said, "You know, I've got some free time. What do think about practicing our phone sex skills."

"I would love to but my mom is about to get out of the shower."

"Even better. Put on speaker phone and let her join us. No lie, if your mom put it on the table, I might have to rethink our relationship.....MILF," she said in what I believe was a joke.

"Hearing stuff like that doesn't even affect me. I've heard way worse from my friends growing up."

"Oh I'm sure," Sarah responded.

"I think I hear her getting out right now. We're about to go out for the day but I'll call you again tomorrow, okay?"

She answered, "Yeah sounds good. I hope you guys have a lot of fun but I can't wait to see you again. Miss you! Love you!"

"I love you too."

I walked upstairs to get my shower and get ready. Being a guy, the whole thing took me about fifteen minutes. I even managed to jerk off real quick to one of my old Playboys after I got worked up talking to Sarah. Afterwards, I went to see how close my mom was to being ready to go. I knocked on the door to her room and she called out, "Come on in."

When I got in there, I realized that she wasn't all that close to being ready because she was still in her robe. She looked a little bit flustered when she said, "I have something kind of weird to ask you."

With a skeptical look, I responded, "I don't really like the sound of that."

"Well, I figure you're old enough to hear this sort of thing. If we're really going to go out tonight and find me a guy, I'm kind of nervous that my......uh......"

"Spit it out."

She finally blurted, "I'm worried that my underwear is too old-fashioned."

I was not really prepared for that. I hesitantly said, "I'm not sure how I can help you with that."

"I know this might make you feel a little uncomfortable but you're the only one here. Can you just take a look and tell me what you think? Like if it is similar to something that Sarah might wear?"

"I want the record to show that I am not totally comfortable with this but I'm going full wingman tonight."

"Okay," as she said that, she hesitantly removed her robe. What I saw totally caught me by surprise. You see, I had never really seen my mom's figure so exposed. Even when we would go to the beach, she would always wear very conservative bathing suits that left a lot up to the imagination. However, what I saw before me was not nearly so conservative. She had matching pink and black panties and bra. They left very little to the imagination. The panties had black think black lace that stretched around her hips with just a small triangle of light pink material with black flowers that covered up her pussy. Her bra had the same design and seemed to be struggling to contain her surprisingly perky tits that I estimated to be C-cups. She was I surprisingly good shape for her age. In fact, it was making me feel a little uncomfortable how impressive I found her body to be. I was glad that I had been sitting down because apparently "little Brett" was not aware that this particular female body belonged to my mom.