"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."
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 bit.do/momishot 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.
"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.
"So, what do you think?" she asked sheepishly.
"At the risk of this sounding weird, I would say that whoever you allow to see this particular ensemble will be very lucky and very pleased."
"Thanks! It will most likely be nobody though."
"I'm a bit conflicted because I want to be your positive and supportive wingman. But, on the other hand, success in this scenario would involve some dude banging my mom," I jested.
She chuckled, "Yeah I guess this has been a strange conversation what we've been having. Anyways, what time is the movie?
"I think the next showing is in about a half hour so we should probably get going."
"Oh, well then I better get dressed real quick and then we'll head out," she said as she turned around to the outfit that she had laying out on the bed. I hadn't ever really noticed before but, seeing it in her tiny underwear, my mom had a great ass. It might not be as tight as it was when she was younger but it still looked phenomenal. In fact, it made me feel a little uncomfortable how nice I found it.
I got over that weird moment quickly and we got in the car to head to the movie. As we got to the theater, I was surprised to find a very long line for a matinee movie. After a couple of minutes in the line, my mom put her arm around my shoulder and asked, "How does it make you feel to be in a line like this for a Katherine Heigl rom-com?"
I realize that it is a pretty corny thing to say but, whatever, it's my mom so I wrapped my arm around her lower back and said, "At least I have good company!"
She smiled and gave me a kiss on the cheek. I bought the tickets and popcorn before we went into the theater. As the previews came on, I was reminded of exactly what I was in for. They were filled with other upcoming corny rom-coms. After a couple of them, I looked at my mom and gave her a playful eye-rolling which seemed to particularly amuse her. I wouldn't admit this to her, but I actually didn't hate the movie. Part of that probably had to do with the fact that she seemed to love it so much. With knowing how lonely she has been, it made me feel great to see her laugh so much and seem so happy if only for those two hours....or this weekend for that matter.
As the credits started rolling, we walked out of the theater. Seemingly assuming she knew the answer, mom asked, "So what did you think?"
With a grin on my face, I responded, "I cannot believe that, against all odds, the guy and the girl got together in the end. I totally did not see that coming."
She laughed, then followed up with, "I think you liked it though. I saw you laughing a few times."
"It wasn't the worst movie I've ever seen. I'll give you that much."
"So what do you want to do now? Should we go get something to eat?" she asked.
I thought about it for a second and said, "To be honest, I'm actually pretty full from the popcorn. What do you think about grabbing a few drinks somewhere? We could get a small bar snack or something."
"That sounds good to me. I'm pretty full too."
We ended up just going to a pool hall that was nearby. I was about to order the drinks before she stopped me, "No no no. You got the movie, I'll get the drinks. What do you want?"
"I'll just take a beer."
She turned to the bartender and asked, "Can we get a lager pitcher?"
Being that it was still fairly early, we did not have any trouble finding an open pool table. As I saw my mom attempting to do the rack, I realized that I had never seen her play pool before. Judging by where she placed the eight ball in the rack, I assumed that she wouldn't be great. After I missed a shot and it was her turn, my assumption was verified. The way she held the stick made me think that she might never have even seen somebody play the game before. Unsurprisingly, she missed the shot horribly.
I then took my turn. I made two balls before missing. As I saw her awkwardly approaching her next shot, I decided that I'd step in, "Here. Try doing it like this," I tried just showing her with my own pull stick but it didn't seem to take. So, I had to resort to the cliché pool-teaching position behind her. As I was showing her, I got a face full of her hair which smelled really, really good. I'm assuming it was her shampoo that gave off this very soothing vanilla scent. She was now ready for her shot. She lined it up like I showed her. She then displayed a much more smooth looking shooting motion and knocked in he first ball of the game.
"There you go!" I exclaimed. I then offered up a high-five which she happily accepted.
She actually ended up making three balls in a row on that turn. But, showing no mercy, I finished the game up on my next turn. At that point, the big soda from the movie theater and now the beers at the bar finally got the best of me. I told her, "Sorry, I gotta go to the bathroom."
"No worries! I'll be rack it up for the next game," she responded.
I walked into the bathroom that I would say was not the nicest I had ever been in. There were tons of paper towels on the ground and a plethora of horrible things written on the wall. But hey, it was a pool hall bathroom. What did I expect?
As I walked out of the bathroom, I saw a man that was clearly drunk talking to my mom. Judging by her facial expression and body language, it didn't seem that she was particularly happy to have him there. So, I made my way over to join the conversation. She saw me and looked extremely relieved that I was coming back. She yelled over to me, "Hey, sweetie!"
The guy barely seemed to notice and continued talking to her, "Come on. Let me get you a drink."
Very politely, she said, "I appreciate the offer but I'm here spending time with my son."
"It's just one drink. He'll be fine by himself for a little bit," he snarled.
I decided to step in, "Hey man, she said no."
He turned to me and clearly was not happy. He roared, "I wasn't talking to you."
"Well I'm talking to you because you don't seem to be listening to her. You just need to cut your losses and leave her alone."
After hearing this he gave Ryan a shove and raised his voice even louder, "I don't want to hear another goddamn word come out of your mouth."
"Listen man, you need to just walk away because this won't end well for you," I said. I felt very confident in this situation. First of all, this guy seemed to have hit the bottle pretty hard. Also, and probably more importantly, I am about six foot four and a pretty solid 210 pounds. This guy was not particularly small but he definitely gave up some size to me.
After hearing me say that, he slightly turned to make it look like he was going to walk away but then quickly cocked his right hand and tried to throw a punch. I blocked the blow with my left hand and caught him square in the nose with my right. He went right down to the floor with that one which caused the bartender to run over. He grabbed the drunk man as he tried to get up and come back after me. He began to guide him towards the door and said, "Alright, Frank, get your drunk ass out of here."
The bartender then came back over to us and said, "Sorry about that. Frank can really be an asshole. I know that you weren't causing trouble here but I think it might be in your best interests to get out of here. We often have trouble with Frank and I wouldn't be surprised if he came back in here with some of his cronies."
I cordially replied, "Thanks for the heads up! Have a good one!"
My mom and I got in the car and pulled out to find a new place. She looked over at me and said, "So that was crazy."
"I'm not sure what he thought the best case scenario there. Like did he think that I was going to leave my son to go have sex with him at six o'clock?" she asked.
I replied, "I have no idea. We gotta find a better example of the dating scene for you than that. Are there any cool lounges or pubs around here?"
"Well, we could go to Benny's. It's just a few blocks away."
"Sounds good to me," I said.
As we walked into Benny's, there were a decent number of people in there but it was not too crowded. We walked over and found a small table in the corner. The waitress came over to us almost as soon as we sat down. With a glowing smile, she said, "Hi, welcome to Benny's! Do you guys wanna see a menu?"
I looked over at my mom as we attempted to telepathically tried to discuss this question but was mostly just an exchange of weird facial expressions. Finally, I turned back to the waitress and said, "Can we get a drink and food menu?"
"Absolutely! I'll be right back.
And she was right back. We took turns looking at the food and drink menus. We decided to split some curly fries. I got another beer and she chose a vodka cranberry this time. Since our fries were taking a little while to come out, we got through those first drinks fairly quickly and our waitress promptly brought us another round.
Our fries finally came out and, with it, another round of drinks. The fries were delicious and we knocked them out in what seemed like two minutes. After we finished the next round, the waitress came over and asked, "Are you guys ready for another round?"
My mom took the reins this time, "Yeah that'd be great. But can we also get a shot? Tequila?" she asked while looking at me to seemingly get approval.
I wasn't particularly excited about doing shots of tequila but I faked some enthusiasm, "Let's do it!"
That shot really took me back to college and not exactly fond memories of it. But, my mom seemed to be having fun so it was a small price to pay.
I began to realize that if our true purpose of the night was to get her back out into the dating scene, then me sitting at this table with her would be extremely counterproductive. So, I told her, "None of these guys are going to come up and talk to you while I'm sitting here. I think I should just sit up at the bar for a little while."
She looked a little uneasy. After a moment, she replied, "But I don't even know what to do. It's been three decades since I've had to do this."
"You don't really have to do anything. Trust me, they will come up do you in droves and you just have to be your normal, charming self," I assured her.
"Okay, I'm trusting you," she pleaded.
"You'll be fine."
She gave a brief smile and said, "Okay. Wish me luck."
"You don't need it....but good luck."
With that, I walked over to the bar. As if on cue, a pretty good looking man walked over to her from across the bar. He looked to be slightly younger than her but she looked so good for her age that it wouldn't really matter. I kept an eye on them as I continued to down more beers. Other than one moment about a minute in where she glanced over at me, this guy seemed to be doing a good job of keeping her attention. She played with her long, blond hair and occasionally gave him a playful slap on the arm, along with many of the other tell-tale signs of female flirting. In fact, she talked to him for over an hour. I just watched a basketball game in the meantime.
Eventually, she came over and sat down next to me. Confused, I asked her, "What happened to that guy?"
She responded, "We actually really hit it off. He's a lawyer. He was pretty funny. We actually went to the same high school but he graduated a few years behind me."
"So what's the problem?" I asked.
"Well, he just split up with his wife. It sounds like they're probably going to get divorced but I honestly don't want to get into something so complicated."
"I don't blame you. Was he upset?" I asked.
"Well no but that's because I wussed out. I gave him my number but told him I couldn't go home with him because I was here with you," she confessed.
"Well played. Well I think he left. Why don't you go for round two?"
"I have to go to the bathroom first but I will after that."
Shortly after she left, our waitress walked up to the bar. She looked a little tired, then she noticed me. She asked, "What happened to your date?"
I laught a little at this and replied, "That's actually my mom."
She looked embarrassed and apologized, "Oh I'm sorry!"
"No worries. I'm actually trying to be her wingman tonight," I told her.
"No offence but I don't think she really needs your help. She's got super-MILF status," she told me in a very playful way.
"Believe me, growing up as her son has made me fully aware of that. I guess I'm just here for moral support. My dad died a few years ago and I'm trying to help her get back out there."
"Oh I'm so sorry to hear that! But that's really sweet of you!" she exclaimed.
"I'd love to fully accept that description but I haven't been back to see her for about a year," I admitted.
"Oh yeah? Where do you live?" she asked.
"I live in LA....with my fiancée," I begrudgingly told her.
"Oh, you're engaged? Well that's just my luck. I find a sweet, good looking guy. It only makes sense that you're attached," she said with a somewhat joking frown-face.
"Well if it makes you feel any better, the scumbag inside of me almost kept me from telling you that I'm engaged because of how attractive you are," I told her.
This definitely made her smile. She really seemed mull over what she was going to say next. Eventually she managed, "Well, I don't know how long you're gonna be in town but maybe we can exchange numbers and I can wing-woman for your mom."
"I guess there's nothing wrong with that. I actually think the two of you would really get along."
"Oh yeah? Who knows, she is single. Maybe she could get me to switch teams," she joked.
"You're making my penis very confused. I really like the thought of you being with another woman but that other woman being my mom kinda puts a damper on it," I joked back. I wouldn't say it out loud, but the thought of the two of them together didn't really gross me out all that much. That could probably be chalked up to the fact that she was incredibly hot.
She seemed to be very amused by my penis confusion. She then grabbed my phone and entered her phone number into it. She then said, "I'm calling myself right now but I should probably get back to my tables."
"Well it was nice to meet you," I looked down at my vibrating phone, "Kelly."
Shortly after that, my mom got back from the bathroom. Apparently, she had seen me talking to Kelly, "You looked to be getting pretty flirty with our waitress."
"No, it's not what it looked like."
I hadn't quite noticed earlier but mom had gotten fairly drunk., "You don't have to explain anything to me. I think it's good for you to experience different women before you take the plunge. Marriage is a big commitment and it's best if you have as much information as possible beforehand. A night with a hot little piece of ass like that could be good for you."
I was slightly taken aback to hear these words coming out of her mouth, "I never thought I'd hear you describe someone as a "piece of ass". Maybe I'll try it out. I love Sarah but I'd be lying if said I didn't have any doubts. Kelly, that's the waitresses name by the way, did give me her number. She said that she could probably be a better sidekick for you than I am when you're out looking for guys."
"Oh, well, maybe we should see if she wants to go out with us tomorrow."
"Maybe," I replied.
After that, we both assumed our positions. Again, almost the second that my mom was at the table by herself, another guy came over to talk to her. This guy looked even younger than the first. At first, she didn't really seem to be that interested. None of the signs that I saw with the earlier guy were manifesting this time. However, a few minutes into their conversation, he said something that absolutely made my mom explode with laughter. Once I saw that she was into it, I went back to watching the game.
During a commercial break, I looked back at the table to see how things were going. I was a little nervous to see that there was nobody there. Somewhat frantically, I began to scan the bar. This scare was short-lived though because I located the two of them out on the dancefloor. To my delight, they both seemed to be having a great time.
"Looks like she found one," I heard and turned to find that it came from Kelly.
I answered, "Yep. He might be a little young for her but she looks to be enjoying herself."
"Like I said earlier, your mom is a hottie. She could come out here and take home college guys if she wanted to," Kelly retorted.
"So what's my move here? Do I head home? Let her do her thing?" I asked.
"I would just shoot her a text and see what she wants to do."
Kelly quickly had to run somewhere but I took her advice. I sent my mom a text saying, "What's the gameplan?"
I watched my mom. I saw her phone light up in her purse and, luckily, she saw it too. After she read it, she turned to the guy she was with and said something. They looked to be exchanging numbers, she gave him a peck on the cheek, and then she walked over to me. I asked her, "What's going on?"
She said, "Let's get out of here."
"Are you sure? You guys looked like you were hitting it off."
"Yeah I'm sure. I'm gonna make him work for it," she said with a sly look on her face.
With that exchange, she went back over to the table to grab her coat. Kelly returned to the bar, so I updated her, "She said she's gonna make him work for it."
She laughed and said, "Good for her. I'm sure he will work for it too."
All of a sudden, my mom jumped into the conversation and showed her drunkenness because she was just shy of shouting, "Thank you so much for the great service! Ryan tells me that you might be interested in being my wingwoman."
Apparently very used to people in this state, Kelly didn't miss a beat, "Yeah I'd love to. I guarantee I'd be of more use to you than this guy," shooting me a teasing smirk.
My mom turned to me and said, "I like her," then turned back to Kelly, "What's your name by the way?"
"Well, nice to meet you Kelly. I'm Julia. I sure hope that you can hang out with us tomorrow night," my mom said as she wrapped her arm around my shoulder.
"Well, I'm supposed to work but I'll see what I can do," Kelly responded.
"Sounds great!" mom exclaimed.
I finally jumped back into the conversation, "I think we're gonna get going but I'll get in touch with you tomorrow."
"Alrighty! I'll talk to you tomorrow," she said with a smile and a wink.
With that, we headed out the door with my mom's arm still wrapped around my shoulder which I realized was about as much for support as it was for anything else. She was drunker than I had ever seen her before. I realized that, while I wasn't as bad as her, I also was in absolutely no shape to drive. So, I called a cab to take us home and decided to leave the car there for the night.
When we got home, my mom had to run upstairs to go to the bathroom. We she came out, it looked as though simply standing there was difficult for her to do. In fact, she had to lean up against the wall as she said to me, "I like that girl Kelly. I remember when I used to look like her....young guys like you going after me."
I countered, "Are you kidding me? Guys at that bar were lining up to try to talk to you."
"You're sweet," she said as she seemed to half doze off while leaning up against the wall.
"Why don't we get you to bed," I offered. She latched onto me again as I led her into her bedroom.
Right before we got to the bed, she turned towards me and had my face cupped in both of her hands. She then ran her right hand through my hand as she said, "You always take such good care of me, Jack," she then cupped my face again and gave me a kiss on the lips. Now, this was not a peck on the lips like we've done tons of times before. This was a deep, passionate kiss. Now, I should have been freaking out because my mom called me by my dead father's name and was now kissing me in a very not mother/son way but all I could think about was how soft her lips felt. Without even thinking, I put both of my hands on her nice, firm ass and pulled her in closer to me. We were now exploring each other's mouths with our tongues. My penis was rock hard at this point as it rubbed up against her body. With my hands already on her ass, I picked her up and laid her down on the bed. As we continued kissing, my hand made its way down inside of her pants. Through her panties, I could feel that she was already extremely wet. For some reason, this seemed to snap me back into reality as I realized that I was making out with my mom and was just about to start fingering her. Not only that, she was probably blacked out at this point and I was essentially about to take advantage of her.
I backed away very quickly and she asked, "What's wrong?"
"Nothing! I'm just gonna go to bed."
Not seeming to match my level of anxiety, she said, "Okay. Good night, sweetie."
Freaked out, I immediately ran to my room and jumped on my bed. Luckily, I was drunk enough that I pretty much went right to sleep. Otherwise, I think it would have been a long, sleepless night. However, if I wasn't drunk, the whole situation wouldn't have happened. Right?
The next morning, I woke up at about ten o'clock. I walked out of my room and did not hear any movement in the house. Terrified, I walked up to my mom's room. I gave a soft knock on the door and heard nothing come from the other side. After a few more knocks with no response, I cracked open the door. I could see her laying on the bed. She looked to be deeply, deeply asleep. To be honest, I was pretty relieved because I wasn't quite ready to deal with the situation.
I went down to the kitchen to grab something to eat. bit.do/momishot I also tried watching TV for a little while but I was too antsy to just sit there. I figured I could put that energy to good use by doing some chores around the house. First, I decided to take care of the dishes which had piled up in the sink. After that, I thought it would be a good idea to throw a load of laundry in the washing machine while I worked on other parts of the house. In the laundry room, I found a basket full of dirty clothes. Sitting on top of the pile, I saw a pair of black lace panties. I don't know what came over me but I picked them up and smelled them. The sweet scent of my mom's pussy took me right back to our encounter from the night before. As if instinctual, I did another giant whiff as I pulled my cock out of my pants and began stroking it. Thoughts about her amazing tits, her shapely ass, and her gorgeous, soft lips began running through my mind. I began to imagine what it would feel like for her to wrap those lips around my throbbing cock as I pressed her panties more firmly into my nostrils. Aided by these incredibly taboo fantasies, I was rapidly approaching orgasm. With one last inhale, I blasted a gigantic load all over the basket of dirty clothes. Luckily, I was about to put them in the wash anyways.
After I came, reality seemed to come crashing down on me. As I was loading the clothes into the washing machine, a ton of thoughts were racing through my mind. Did she really think I was my dad? Does she remember what happened at all? Did it only happen because we were drunk? If so, why did I just jerk off to her panties? What does this mean about my relationship with Sarah? What does my interest in Kelly mean about my relationship with Sarah?
Having so many questions and absolutely no answers was causing me a serious amount of anxiety and no amount of housework could diminish it. Over the next few hours, I slowly began to feel a little better mostly because my mom was still passed out in her room. Every now and then I went in to check on her and make sure she was alright. It wasn't until three in the afternoon that she actually woke up. Hearing her say, "Good morning, sweetie" really sent a jolt up my spine though.
I looked up at her and was absolutely shocked by how amazing she looked after waking up from a night of excessive drinking. I guess one of my questions was now answered because I was no longer drunk and my attraction to her was still very much there. Judging by her lack of awkwardness, it seemed as though she might not have remember what happened between us. I responded to her good morning with, "Hey sleepy-head. How are you feeling?"
"I've felt better. I woke up to texts from two different guys whose names I don't recognize. They asked me if I was free tonight so I guess I did alright last night."
"You don't remember at all?" I asked.
"Nope. The last thing I remember is when we took those tequila shots. That was definitely a bad choice."
"That was all you," I teased. I was definitely relieved to hear that she didn't remember. However, I was not totally care-free because I still had to figure out why I did the things I did and felt the way I felt. I'm not sure I will every feel totally comfortable with what happened last night and this morning. In fact, at that very moment, I couldn't stop myself from glancing at her breasts and fantasizing about licking and sucking on them right then and there. Essentially in an attempt to sidetrack myself, I asked her, "So, which one are you gonna go out with?"
"Huh?" I questioned.
"You haven't been home in a year and you're about to head back to LA tomorrow. So, you're going to be my date tonight," she replied. She had no idea how loaded of a statement that was given what happened in her blacked out state.
I figured I'd entertain myself a little so I responded with, "Okay but don't think that just because I agree to go to dinner with you that that means I'm going home with you."
She was a good sport with it, "Oh is that right? Well, I've heard that before. We'll see."
At that moment, I felt my phone buzzing. I looked and saw that I had a text message from Kelly that read, "Hey Ryan! It was nice meeting you last night! Anyways, I have a friend that is willing to cover my shift if you guys still wanna hang out tonight."
I thought about it for a second before responding. I really liked her. She was insanely hot and she had a really great sense of humor to go along with it. It seemed like a pretty good chance that I could have sex with her and I'm sure it would be amazing. However, I simply could not get my mom out of my head. So, I texted back, "Sorry, my mom is still struggling from last night. I think she's gonna stay in and I'm probably gonna stay with her."
Instantly, I saw the three dots showing that she was already typing. She sent, "Hey, no need to be sorry. You're once again being the sweetest son ever! Definitely hit me up next time you're in town though!"
I sent back, "I'll definitely let you know. Meeting someone as awesome as you last night was definitely a pleasant surprise."
She sent me back a long string of smiley faces. I'm not usually very into using emojis but I simply sent her a wink face in response.
My mom must have noticed me texting, "Who's that?"
"Kelly. She was our waitress last night."
Her eyes lit up at this, "Oh yeah? What does she want?"
"Well, last night you and I talked to her about going out tonight. She was hoping to get someone to take her shift but nobody would."
"That's too bad," she consoled.
Wanting to change the subject, I said, "So where are we going for dinner?"
"I don't really want to go anywhere fancy. There's a steakhouse near the bar that we were at last night that's pretty good."
I replied, "That will actually work out great because I had to leave the car there last night because we were both wasted."
She laughed, "I hope that it doesn't have a boot now."
"Yeah that would suck!"
"Well, I guess I better start getting ready," she decided.
"Good idea. In the meantime, I'll call to have a cab pick us up in a couple of hours."
Again, it took her a very long time to get ready. In fact, despite the fact that I scheduled for the cab to come two hours in advance. We still ended up making him wait about ten minutes before she was ready to go. Luckily, he seemed to be a pretty nice guy. We got to the bar and were very pleased to find no boot and no parking tickets. So, we got in and we drove the short distance to the steakhouse. Thankfully, it wasn't overly crowded so we were sat pretty much right away. Given our environment, we both went with the obvious choice of steaks. As we waited for our steaks, we began to chat, "So, you're gonna have to fill me in on what happened last night."
I obliged, leaving some things out, "Well, it was all downhill for you after you decided to order us two shots of tequila."
"But you still managed to chat up two pretty good looking guys and apparently got both of their numbers. One is currently in the middle of a divorce though," I informed her.
"No thanks. Too messy."
"While you were with them. I actually talked to our waitress, Kelly, for a while. She was pretty cool and you seemed to agree. You wanted me to hook up with her. You actually called her a "hot piece of ass" at one point."
She smirked and replied, "And I stand behind that. Don't get me wrong, I love Sarah but I am worried that you might be settling down too early. And Kelly is a hot little thing. She probably could have taken me home last night if she tried."
"It's funny you say that because she had similar things to say about you."
"Good to know," she joked, "It's too bad she couldn't hang out with us tonight."
"Yeah it is. I don't think I would be into going to a bar again tonight though to be honest."
She agreed, "Same here. I haven't been quite this hungover in a while."
As if on cue, our server arrived with our steaks. They were absolutely delicious. And huge. When we were finished, we both just sat there in silence as we recovered.
"So what now?" I asked.
"Even though I slept for a million years, I'm actually already tired again. What do you say that we just head home and watch a movie or something?"
"I'm cool with that."
After a fight over the check, she eventually let me pay and we got in the car to head home. When we got home, my mom started going through the movies to find one for us. After putting me through a rom-com on Saturday, she decided to make it up to me with an action movie. Simple with a lot of explosions, just the way I like it.
As we sat down on the couch, it was just like Friday night but in reverse. She had her head on my shoulder as she fell asleep several times throughout the movie. As always, her hair smelled amazing. Not only that but the angle she was laying at gave me a perfect view of her cleavage. While this was pretty pleasant, it was a little too pleasant because I could feel my cock starting to get hard. I knew that I just had to make it through the night and then I would be heading home to a crazy sex session with an extremely sex-starved Sarah. So, when I knew mom was asleep, I grabbed the remote and fast forwarded to the end of the movie. I then nudged her to wake her up, "Hey, the movie is over. We should probably get to bed."
"Okay. Sorry I fell asleep," she said.
"Don't worry about it."
We both then got up and started walking up the stairs. She was wearing yoga pants which made her ass look amazing. This wasn't helping me at all in my quest to calm down my penis. She got to her door, I got to mine, and I thought I was home-free. But, then she turned and asked, "Why didn't you hang out with that waitress tonight?"
"She couldn't get anyone to take her shift tonight. I guess everyone was trying to get off for Valentine 's Day."
She walked closer to me and said, "I saw your face when you were texting her. You had this giant grin on your face. It was obvious that you like her and that she wasn't giving you any bad news."
I tried to save it, "Honestly, I wanted to spend the day with you and I didn't want you to feel bad that I wasn't hanging out with her."
Suddenly, she grabbed me and kissed me much like she had the night before. She then pulled away and asked, "Are you sure it wasn't because of our kiss last night? Are you sure that it wasn't because you wanted to fuck your mom?"
I had no idea what to say. All I could manage was, "I uh.."
She continued, "And that your mom wanted to fuck you?"
Again, she grabbed me and kissed me. This time, she slipped the tongue in. When she did that, I backed away at first. She looked at me square in the eyes and said, "It's okay."
Apparently, that was all I needed to hear because, suddenly, I became the aggressive one. We were going at it like high school kids. I lifted her up by her ass and kissed her up against the wall as she wrapped her legs around my body. Once I started kissing her neck, she said to me in panted breaths, "Take me to bed, sweetie!"
"Whatever you say, mom," I said and I subsequently carried her into the bedroom. For some reason, crossing that threshold seemed to slow down the pace. I gently laid her down on the bed. Then, I removed my shirt and my pants.
She looked at me in awe and said, "I haven't seen a tight body like that in thirty years."
I replied, "I hope that I'm lucky enough to be with a woman in thirty years that has a body like yours."
I then slowly started to take off her pants, savoring the sight of every inch of her gorgeous, womanly body. Once I got her pants down to her knees, I started to kiss her inner thigh while I continued to slide them off. This caused her to let out a slight moan. Once I got her pants the whole way off, I looked up at her. She gave me the sexiest little smile and very seductively removed her shirt. She then reached behind her back and removed her bra, revealing her glorious tits. Without hesitation, I crawled up and started sucking on her tits, trying very hard to not think about the fact that I had done this before....when I was a baby.
I gave her one more deep kiss before slowly removing her panties. To be honest, I was expecting to find a bush. On the contrary, it was completely bald. Her pussy was beautiful. Without hesitation, I dove in. Her groans began to grow louder as the speed of my tongue began to increase. When I started to lick her clit, her moans graduated to full out screams. Based on those screams, I could sense that she was getting close. So, I locked into that rhythm and that location. About a minute later, she screamed out, "Fuuuuuuuck yeeeeeeessssss!!!"
She was out of breath but she did that thing where she had a faint laugh in between her panting that let me know that she truly had a powerful and satisfying orgasm. Giving her a look that said "I'm not done", I grabbed her legs and put them up over her head. She held them there comfortably thanks to her frequent yoga sessions. Once she was in that position, I went right back to work. I started out giving her long slow strokes from the bottom of her pussy to the top and back. She seemed to be caught by surprise when I kept going down and began licking her asshole. At first, it seemed like she wasn't so sure about this but, when I started rubbing her clit simultaneously, she got on board in a hurry. While still managing to take care of the task at hand, I stole a look at my mom's face. She had her eyes shut and she was mouthing the words "Oh my god" over and over again. In what seemed like no time, she reached another orgasm and let out a scream that rattled the house.
Mom did not seem to be bothered at all by the fact that my tongue was just in her asshole because she quickly gave me a kiss that was not only passionate but seemed thankful if that makes any sense. She then threw me down on my back and pulled down my boxers. I wasn't expecting much from her orally because she hadn't given a blowjob in I'm assuming at least three years and then she was married for a long time before that so who knows. However, I couldn't have been more wrong. She handled my dick like a porn star. She was moving her tongue around in ways that I honestly couldn't even understand. What surprised me even more was the fact that she was able to deep throat it without too much trouble especially since my dick is at least slightly above average size. I can normally last pretty long but her skills would not allow that in this instance. So, I told her, "I'm about to cum."
She gave the bottom of my dick one more lick from the base to the head before she slightly backed away and said, "No you're not. Not yet. You're gonna fuck mommy's brains out."
Believe me, I didn't need to be told twice. I did have a question though, "Do you have any condoms?"
"We don't need one. I got that whole situation taken care of after your sister was born."
She assumed the same position she was in earlier with her legs above her head. This was particularly awesome because not only did it give me great access to her pussy but her legs also pushed her beautiful tits together. While still focusing on this stunning visual, I slid my rock hard cock into her warm and extremely wet pussy. My first strokes were slow and deep as I was simply enjoying how great it felt to be inside her. I happened to look over and see a picture on the nightstand with a frame that says "World's Greatest Mom". For some twisted reason, this turned me on even more and I began to increase the pace of my pumps. She seemed to notice and got more riled up herself. At this point, we were making the headboard bang up against the wall over and over again. I licked my fingers and started rubbing her tits. This compelled her to join in on rubbing her tits and pressing my hand even more firmly into them. As hard as I tried to make it last as long as possible, I could tell that I was rapidly approaching the point of no return. So, again, I told her, "I'm about to come."
She looked right at me with a slight grin and said, "Give me all of it."
As if compelled by that command, I busted a giant load right into my mom. I then laid down in the bed next to her as we were both out of breath. I looked over at her, she simultaneously looked at me and we both just started laughing. We were both then just staring at the ceiling, contemplating the consequences of what just happened. However, I realized that I couldn't take it back now so I just wanted to enjoy this moment in case it was the last time it would ever happen.
Even though there were a million things to be said in the situation, we just laid there in silence. She turned on her side and I cozied up behind her with my arm wrapped around her. This could be a somewhat acceptable mother/son positioning if it weren't for the fact that we were both still totally naked. She didn't seem to mind the fact that my cock was rubbing up against her ass. I certainly didn't mind that her ass was rubbing up against my cock. I gave her a soft kiss on her neck before I said, "Good night, mom."
"Good night, sweetie."
When I woke up, I found myself alone in my mom's bedroom. I got up, put on my boxers and walked down to the kitchen. I saw her sitting at the table with two plates of food, a cup of coffee in her hand, and a blank stare out the window. I broke her trance with, "Good morning, mom!"
"Breakfast looks great!"
"Thanks," she said and then paused to think, "Listen, we need to talk about last night."
Begrudgingly, I said, "I know. For what it's worth, I had a great time."
"So did I....that's the problem," She replied.
I responded, "I get that it's not an ideal situation but I don't think it was a mistake. Standing here right now, I still want you. Last night, I could have gone out with Kelly but I wanted you. I wanted you so badly. I wanted you more than I've ever wanted anyone."
"But this can never work. Mothers just can't date their sons. It would be one thing if you were an only child but what would your sisters think if they found out."
"I think it can work out. We're still mother and son but just a little more intimate."
"A little more intimate? Your tongue was in my asshole last night."
"That's a good point. And as far as Charlotte and Kenna go, I don't think it will be that hard to keep it from them since they don't come around that often."
"Well what does this mean for you and Sarah?" she asked.
"Honestly, I don't know. I think I'll have to play it by ear. To be honest, I don't really want to think about all of these things right now," I said as I started to undo her robe, "We have about twenty minutes before I have to get ready to leave for the airport."
In just those twenty minutes, we absolutely tore that kitchen apart. She even seemed to have developed a new fetish as she requested that I eat her ass out again. To even things out, she actually let me fuck it after I licked it.
The ride to the airport had very little conversation. It was more or less just an exchange of smiles. Once we got there, we were pleased to see that the security check wasn't very crowded. As we were saying good bye, what started out as a good bye peck turned into a full-on make out. Luckily, nobody around us knew just how taboo this action was. However, with the mindset that we were in, we probably wouldn't have paid them any mind even if they did. Eventually, we managed to break away from each other. I gave her one more look before I went into the terminal. She flashed that gorgeous smile of hers and waved. I waved and turned away. I didn't look back again because I knew that I wouldn't be able to leave if I did.
All in all, It was a good Valentine's Day...