A Taboo Fantasy Pt. 02

"Family? Like you were attracted to your Mom?"

Fuck.

The one word that I hoped would be glossed over in my rant was the one word that she picked out and questioned. I feared I had taken things a step too far and wanted to frantically back pedal, but I didn't see the point. I had already said it.

"Well, not technically. It started with another family member. An aunt. It's a super long story and I shouldn't have mentioned it. I apologize if it made you uncomfortable." It was a salvage message at best, but I figured it would at least give me the chance to apologize if she were to block me immediately after.

Somewhat shockingly, a reply appeared quickly. "Don't apologize. I just wanted to make sure I understood. I'm heading to the coast for the day to my daughter-in-law's baby shower so I'll be out of touch but I'll text you tomorrow. Thank you for telling me."

While trying to remain positive and assure myself that it wasn't a firm no, I wasn't able to convince myself that "thank you" was a promising response after admitting to having incest fantasies. I tried to save face by quickly leaping into a concerned parental role with my reply.

"Have fun, but be careful! Make sure you wear your mask and wash your hands!" referring to the ever present COVID protocols in 2020.

Her reply would be simple and sweet, but more importantly would in some ways set the stage for all that laid ahead. "You're adorable! Thank you for being concerned, and I promise I'll be careful. It's only a few family members and close friends so it should be fine. You behave yourself today, young man...I don't want to hear of any naughty behavior out of you"

In millennial fashion, I replied the only way I knew how. With the heart eyes emoji.

The day passed as so many others before them had. I got my work done and was on every call I needed to be on, but every free moment was spent bouncing between incest porn, literature, and Kelly's basic profile photos. A strange cocktail to some, but one that intoxicated me to the point of NEEDING to jerk off 3 times that day, something that I hadn't done in years.

That night as I crawled into bed my phone made its familiar ding and I saw a message from Kelly appear. The message was simple and quick, reading, "Just going to bed, turned into a long day. Let's talk tomorrow..."

Attempting to play it cool for the night, I simply said, "I look forward to it! Sleep well! Goodnight"

An unexpected reply followed from Kelly. "Did you behave yourself today?"

My memory bounced back to endless web searches and hours of porn viewed during the day, along with the 3 loads of cum that I had shot while dreaming of this very woman that I was speaking to, and I replied, "Well...I tried to. That's all I can say." It was honest...sort of.

Kelly's final reply that evening left me speechless and is one that I will never forget. The text read, "Awww all that us Mother's ask is that you try. Goodnight!" Accompanying the text was a selfie, clearly taken in the moment. She held the camera slightly overhead while laid in bed to snap the photo, which showed only enough of her face to reveal a slight smirk which set the tone for the remainder of the picture frame. Below her face extended her body, laid out on her bed on her left hip with her right leg rolled over top of the left. She wore only a simple black satin nightie with spaghetti straps that attached at a thin lace trim that traced a deep v into her cleavage while straining to contain her large breasts which were now clearly free from a bra. Her hard nipples pressed against the fabric in such an obvious teasing manner, but one that worked well enough to make my mouth water instantly. The nightie hugged her body tighter than any clothing I'd ever seen her in and revealed the small roll of a belly that seemed to fit her body like a glove before giving way to her full and generous hips. The angle hid most of her backside which would have to be left to the imagination for now, but I was far from disappointed seeing her ample inner thighs emerge from the nightie to show their soft pale flesh before disappearing under her covers.

Without even realizing it, as I stared in awe at the picture sent to me and took it all in, my other hand began stroking my now again swelling cock. In just a few short minutes, Kelly's pic sent me over the edge for the fourth time that day. Exhausted, I fell asleep in my bed still covered in my own cum.

The next day started shamefully as I awoke and felt the need to not only shower immediately, but also get my bed sheets washed. With that immediate fresh start behind me, I dove into work and had the most productive day that I'd had in sometime. At one point in the day I laughed to myself thinking that all I had to do to get ahead at work was jerk off four times each day and my mind wouldn't wander! The mere thought of how sore and mangled my dick would be after keeping up such a routine was enough to turn the joke into a shudder. It was becoming clear that this fantasy was becoming more intense and it needed resolution.

Around 5 PM that day Kelly broke my work trance with a "Hey stranger" text. Having not realized that the entire day had gone by, I quickly replied and asked how her day was. She said her day was fine but had been, "worried that the pic I sent last night scared you off. I warned you that I'm not tiny!" I sat, unsure of how to gracefully inform her of the orgasm inducing truth before deciding on an honest depiction of what I saw.

"It was the most stunning sight I've seen in a very long time."

A blushing face emoji was sent in reply, before the conversation turned and carried on with more casual and far less sexually charged topics. While it wasn't as fun of a discussion, Kelly did have an important matter to discuss.

She informed me that during the previous day's baby shower at her daughter-in-law's residence near the coast, one of the guests in attendance got a text during the event from her husband that he had just tested positive for COVID at his workplace and that she should isolate. While the party goer's were all mostly observing COVID social distancing protocols, it was hard for anyone to ignore the hugs that were exchanged by almost everyone as greetings. Despite planning to spend the night there, Kelly drove home that night and was determined to self-isolate for 14 days as a precaution. The more I got to know Kelly, the more I learned about how close she was with her children and grandchildren and how critical her involvement in their daily lives was to her happiness. Fourteen days alone at home was clearly going to be difficult for her, and she was struggling to hide that. I knew it would only serve to benefit me if I provided her with whatever support and comfort I could from a distance. Even if it was just simple texting, I hoped I could help her take her mind off of the isolation.

That night we spent texting talking about old family holiday traditions as Thanksgiving had just passed, and Christmas was soon on the horizon. We enjoyed several laughs as we compared stories of odd relatives and holidays gone wrong in the past, and spent the evening just getting to know each other.

Eventually the night got later and we both decided it was time for bed. After exchanging a few last messages she said, "Goodnight...you really are a sweet boy."

Thursday came and I was up and eagerly working in the morning. I was feeling the pull to get to the relaxation of the weekend, and wanted to get as much work out of the way as possible so that I could use my free time to further dive into my ever growing fetish. Midway through the afternoon my focus was broken by the sound of a text. The message was from Kelly and had a cheerful greeting along with a selfie of herself on her couch, covered with a blanket, with a glass of cabernet in hand. If she was going to be stuck at home, she was determined to make it as fun of a time as she could, particularly since she had retired early a few years prior so she didn't even have work to do from home.

After seeing her cozy arrangements along with her early happy hour, I was happy to see that she was making the most of her situation, but also felt a tinge of jealousy that I couldn't be doing the same. I leaned back in my office chair as I formed the response of, "Glad to see you're enjoying the day. SOME people are busy working! 😉"

Her reply came quick which showed me it was off the cuff, but a true sign of what was on her mind, "Hey! Even an old mommy like me deserves to be able to cut loose sometimes...don't you agree?"

Glad that she couldn't see the enormous smile on my face, I sent back, "Yes, ma'am. Of course I agree."

She replied, "Ma'am? I'm not sure I love that title...can't you come up with something better?"

I told her I'd work on something more fitting while I finished up my work day. I didn't see it then, but she was already aware of the title that she wanted.

Evening arrived and I finally shut down my computer for the day. To celebrate the end of another successful day I poured a healthy amount of Johnnie Walker black over ice and quickly snacked on a peach flavored cannabis gummy. Already feeling the placebo effect from knowing the mood altering substances were on their way to my bloodstream, I wandered into my living room turning on my gas fireplace before falling into my couch. The Thursday night football game was due to start shortly and I was happily settling in for an evening of viewing and relaxing. My mind quickly wandered to Kelly so I sent her a text to ask how her evening was going as it had been several hours since we touched base.

Her reply came simply in the form of a picture of a now empty wine bottle, along with the text, "Whoops!"

"Lol Hopefully you have more stashed away!" I said playfully.

"Don't worry, I've already opened a second bottle. The perks of belonging to wine clubs! I guess you could say Mommy is being bad tonight!"

I replied with a laugh and let her know that based on her COVID drama, she should feel free to do whatever it is she wants for the next two weeks. No worries about what to do or when to be someplace, she was free to simply enjoy her time however she wanted...however many bottles of wine that required.

"Can I ask you a question?" She said broadly which I obviously accepted. "The other day when you told me about your fantasy and you mentioned family members, I asked about if you were attracted to your Mom and you said no. Why is that? Why your Aunt but not your own Mother?"

After reading Kelly's message, I felt a tightening in my stomach. I knew the answer internally, but I wasn't sure how to explain it in a way that would seem logical. Even if I could put some sort of rationalization to it, I knew that I was getting dangerously close to revealing for the first time to anyone that I had seen my Aunt topless years before and that it was the moment that opened my eyes to the entire fantasy.

Seeing no way around it, and feeling strangely liberated to do so, I told Kelly the story of what happened that day in Montana when I saw my Aunt's breasts. I told her about how it fueled my fantasies for years and sent me deep into incest fantasies. However, those were simply that. Fantasies. While I enjoyed reading erotic literature or watching porn relating to other incestual relationships, it was my Aunt who I saw so it was her that I associated with them.

Kelly processed my message and said, "So it's not that you have something against it?"

"Absolutely not!" I replied. "In fact, I think mother/son fantasies are some of the hottest there are...it really is the ultimate taboo. That's incredibly erotic!"

Her prodding about my attraction to my own Mother was starting to add up in my head, and I was hopeful as to where it would lead. Knowing I'd need to treat this situation very delicately but directly, I decided to ask rather than accuse.

"You've asked me several times about the Mom/son topic...what has you so curious?"

The text was marked as read but went unresponded to for ten minutes. I pushed harder.

"Is it something you're interested in?"

Her reply finally came in the form of, "Do you think this makes me a horrible person?"

The mixture of emotions I felt in reading that message were extreme. On one hand, I was incredibly aroused knowing that this mature natural woman had more or less just admitted to me that she had a Mother/son fetish, but my heart also broke for her because of how conflicted she felt about it.

"Absolutely not! I think it's something that's pretty common...maybe more common than you'd ever imagine. It's perfectly natural to wonder about what it would be like to be with those closest to you." I wished that I could see her in person to hug her, but that was the best I could do at the moment.

Several minutes passed without word from her. I followed up with another text, "Please trust me on this. It's our secret. You already have heard about my fantasy so there's no way I could judge you for whatever intrigues you. I'd just really love to hear about it. Will you tell me about your fantasy?"

More time passed before I saw her start typing. On more than one occasion the typing bubble disappeared for a few moments only to return. She was clearly re-reading everything she wrote and being very intentional with every word trying to avoid letting her building wine buzz spill all of her secrets. Finally, the text got sent to me.

"I actually got chills up my spine when you described how you felt about your attraction to your own Mother, as it is so similar to my own situation. My two sons are both handsome men now, both with their own families. I could never imagine trying to actually engage with either one of them sexually...but when I fantasize about the IDEA of them, everything changes. I let my mind escape into the fantasy, but it always remains slightly hazy...I never see the face of either of my boys, but I feel their touch. I feel them grabbing at my body eagerly. I always imagine myself squirming to get away, even if for my own sanity with the thinly veiled lie that I tried to stop it. Everything about their touch feels so wrong and dirty...and it turns me on every time."

I can't say for certain at what point it happened, but by the end of reading Kelly's text I realized that I had slid my free hand down and was gently sliding my fingers along my swelling cock from outside of my pants. Now that I had opened this door into her darkest fantasies, I knew I needed to hear more. Careful not to push too hard, I asked a question that seemed to be passable as a legitimate question for more information.

"You said you feel their touch...what do you feel them doing? Are you clothed as they do this to you? What do you think they're trying to do?"

Without delay now she started replying quickly. Gone were the barriers from before as we had moved on to the loose tongues of wine and whiskey, both diving into topics headfirst that could make even the strongest soul blush.

"There's no mistake about what they're trying to do. They're always trying to pull my clothes off of me...groping at my breasts as they try to free them from my bra. Sometimes I imagine myself fully clothed in in a nice blouse and a skirt, or sometimes I imagine them catching me just out of the shower and only wearing underwear and a robe. Over time I give in and submit either way...they rip my clothes off of me and bend me over. I can always imagine how their hard cock would feel pressed against my ass with my panties still on. Feeling their strength and power behind me would have me soaking wet."

I couldn't believe what I was reading. I felt like I was living this moment with her and feeling the excitement that she had. From where I sat I knew this was too good to stop now (as I had by then switched to having my hand slid down my pants and gently stroking my cock dry), and I needed to know just how deep her perversion went.

"Once they have you under control and naked, do you imagine them fucking you? Do you imagine your sons cock sliding into you?"

"Of course I do...I am right now." She boldly responded.

"And what do you do when you imagine that?" I said, now obviously hunting for perverse details of how Kelly pleasures herself.

Her reply let me know just how serious she was. A text read, "That's when Mommy fucks herself" and an accompanying picture taken from her point of view. The image looked down over her body as she clearly laid on her back on a couch. Both of her large gorgeous breasts had been pulled out from the tank top she was wearing and were laid out, both drooping to the outside as age took its effect. Below she wore only a pair of pink cotton panties which were made visible by the tummy roll that they covered, and was laying with her legs spread and in the air with the soles of her feet together. Her pink panties had been pulled to the right side, and the unmistakable sight of the end of a dildo was just visible as the majority of it filled her up.

That image sent me over the edge. I was 100% committed to this new fantasy and I was about to burst a load of cum because of it. Knowing that Kelly had been clearly swept up in her buzz and the elation of openly catering to her fantasy, I knew I could push the limits. To say I was turned on by Kelly at this point was an understatement. She was everything that I wanted and here she was, wine drunk and fucking herself for me to see while describing her incestuous mother/son fantasies. My next message would make or break the situation.

"Mommy...I want to fuck your wet pussy."

My phone rang. It was Kelly. I took a deep breath and committed to the role. I answered with, "Hi Mommy...are you being a naughty girl?"

The sounds of her moans were immediate and came as music to my ears. While her words and pictures were of course convincing, hearing her voice brought the reality of the situation to a new level. After a few seconds of moans subsided, she finally managed to say, "I am baby. Mommy is fucking her pussy deep and hard."

"Fuck it harder Mommy"

"Oh god, Son!" Kelly exclaimed, "Oh Son, I want your cock inside of me! Oh baby please fuck Mommy's pussy!"

With a light buzz from my whiskey and edible kicking in, I was able to have a slight numbness to my cock during the build up to this, however once I heard her beg for her Son's cock to fuck her, I was finished. There on my couch I let out four long ropes of cum, somehow managing to mumble "Fuck Mommy I'm cumming!" before slouching into my couch in a post ejaculatory haze, listening to a woman who I've never met build herself to an orgasm on the phone.

Having heard my own orgasm, Kelly's quickly built and she replied to my comment by nearly shouting, "Cum in Mommy's pussy baby! Fill me up! Please fucking fill me up with your cum, Son!"

Several seconds of heavy breathing passed on both ends of the phone. By now, I sat covered in my own cum with plenty more around me to clean up, my phone on speakerphone sitting on the arm of the couch, with the sounds of Kelly catching her breath filling my living room.

As we both came back to reality, I asked a semi-sarcastic question which would be the first non-phone sex comment she would have ever heard truly from my voice.

"How long is this self isolation again?"

Kelly let out a laugh that was enough to translate into a smile on my face. It was a warm and inviting laugh. One that was humble and showed that she truly cared about the person she was with. It could almost be described as maternal.

"Unfortunately I'm supposed to stay here for 14 full days."

"Ouch, that's rough" I said. Curious as to whether this was a fluke of one horny night, or really a situation that held promise as a true role playing scenario, I tried jumping back into the role, which after cumming could feel almost comical. "I was hoping I'd get to meet Mommy sooner than that."