u/throw4wayy00

feel free to be as detailed as needed! i want to read them while studying

Today went well, i haven't done anything the last 2 days due to us both being extremely busy and that's okay.

Tomorrow I think I'll enjoy our coffee & conversation as usual, and I'm thinking of just asking her if she thinks any other color of sweat pants would look good (show her the other colors online) or if grey fits me the best. depending on her answer, i want to ask if she thinks the grey is a little distracting/revealing and to "actually" look at them.

I feel like this is a perfect boundary pusher. It makes her have to either hint that she likes it, or completely tell me it's a little too much & I am ready for whatever the answer is.

It gives me a cop out regardless. If she doesn't like it and i'll be able to say something like "oh i'm sorry let me put something else on."

Now, if she says something like no not at all, i'm just going to simply reply with an "oh is that right? are we looking at the same pants? orrr" and keep things funny and lightly flirty or something along those lines.

What does everyone think?

M23 MIL57 *** Go back and read original post if you haven't already! Looking for REAL advice ***

What's good y'all, update #3! It has been a slow but exciting few days. Over the weekend, I read a lot of your guys advice & responses towards my situation.

Since Mother's Day, I had taken a break from flirting to kind of use it as a push-pull tactic. Monday, yesterday, I did my usual routine with her; took the dogs out, made coffee, but this time I did it entirely clothed. We talked for probably 2 hours straight in her room before the wife got up, just about sports bets and other things. I told her how good she's been looking lately and asked if she did anything new to her hair which to my advantage, I already knew she did haha. I told her it looks amazing and that she should do it like that more often.

One thing I did do, which Idk if i told everyone this but i have been liking her old instagram posts recently. When she was showing me her sports bets, I was able to see that she screenshotted the post. Not with my notification, but she just screenshotted it? No clue why.

Now today, Tuesday, I decided to kick it up a notch once again. I got the dogs from my MIL in the morning to take them out like usual, this time wearing a black long sleeve thermal, grey knit pajama pants (veryyyy see through type of grey) and a cock ring to stand out a little more while i was inbetween soft and hard.

Initially, as she opened the door, there was nothing from her I don't think. But when i came back after about 10 minutes, I went and got myself extremely hard before coming back with the dogs and asking what she'd been up to all day.

When I first walked in, I noticed she again, had taken a glipse of the print, this time doing a double take before looking back up. She does this so nonchalantly that you really don't know if she's getting a fix or if she's just swiping her eyes around lol. No verbal reaction, no change in mood, nothing.

As a business woman, she is always at her desk/computer. We continued our regular conversations while she sat down while i hovered to the right of her
with my cock swollen, bulging through my pants.
I was literally inches away from her face for most of this conversation.

We began to talk about sports bets. As i showed her my parlay's for the day, I made sure to go down and show my phone right above my throbbing dick, even bouncing it while she looked down at my phone. Still, no reaction or change in mood of any type.

I kept coming in and out of her room, using different topics of conversation or "refilling" my coffee in order to continue our interaction and I never caught her once staring at me even though it's hard to miss a 7 inch thick cut cock looking straight your direction lol.

I stayed in her room chopping up with her for about 2 hours again, switching from pacing or standing next to her and laying on her bed before leaving to get ready for work with the wife.

I do want to mention is that she gives me her phone to place bets, just hands me it. No watching me, no nothing, just continues what she's doing and trusts that I'm just on that app lol which I THINK is a good sign of trust.

We never had any sort of weird vibes going and if we got silent for a sec it was never awkward until we started talking again. I wanted to make any physical contact that I could, so I helped her adjust her earrings and all I did was say "let me help you with this" and reached for it. She just lets me.

Now the thing is, I know this is a long game to play and I have been increasingly stepping up and trying different spontaneous things daily. I was going to massage her neck once again today, but I just couldn't think of the right setup to lead into it. (As i'm typing this, I just thought of the easiest way I could lol so)

Also, while we are conversating, I am fixing/slightly stroking my cock from the outside. Nothing long, a very short fix, but I do it a few times while inchesssss away from her face.

Still, no TRUE reaction from her. I think she's avoiding the elephant(trunk) in the room so she has plausible deniability. Ex: He's just my extremely helpful and well endowed SIL, nothing more than that :)

So look, I think she is liking the attention and the flashing, reasoning being:

- If I made her uncomfortable, I don't think she would let me converse with her for 2+ hours daily.
- She is 57 year old business women, she's not stupid & definitely knows what's going on around her.
- Not once does her mood change around me, it's always the same happy/delighted to talk while she's focused on her work.
- I think she is avoiding doing anything herself because she is waiting for me to make it obvious if that makes sense.

So, I am thinking that tomorrow, I will talk about how she always watches the same show every day & she's always working. I will then tell her "Shh relax your neck" and start to massage her upper neck towards her skull. While i'm doing this, I want to ask, "You know speaking of shows, I just want a yes or no, but have you been enjoying the one I put on for you every morning?" and maybe, if I feel up to it, use my hand to turn her face by her chin and look directly at me. Depending on her response, I will have exactly what I'm looking for.

I know it's bold, but I just have a feeling she needs that extra push in order for the situation to make any progress. I want to create that sexual tension between us and go from there.

Please guys, I NEED advice lol.

Do we think she is liking everything?
& Do we think that I need to be bolder or should I keep playing it safe?

At this point, I just want confirmation.

M23 MIL57

Hello everyone! If you haven't read my first post already, go take a look.

Anyways, it's been 3 days since I posted on here asking for advice. Since then, I have taken a slight break from the flashing and the massages, etc and have just kept it to friendly/flirty banter, dropping small hints here and there.

She said she misses the way I make the coffee in the morning, since I sleep in a little later on the weekdays lol. I've also been going back and forth with her about this french toast she makes, saying she might be adding a lil summ extra and saying she be putting her foot in it lol.

She's been calling me the best SIL lately and I have been loving it, even telling me not to tell her other SIL lol. In which I replied "don't worry, your secret is safe with me🥴😚😂"

She has been acting perfectly fine since the other day and today I decided to make a small move.

I made a small mothers day setup for her, bouquet, candy, card, and mimosa ingredients to share with me her and the wife. When she thanked me, I decided to slip my hand down to her ass slightly grabbing but more or less just placing it there. Again, no reaction, but she definitely felt it. She then made me breakfast and we had friendly banter about her cooking again. She says she's putting a few toes in it, that's why it tastes so good😂🤷🏽‍♂️

Not sure how this will play out but the ball is in her court. Wish me luck and any advice is appreciated🤞🏽

Alright y'all look, 2 things: 1. This is not a fantasy, this is my real life so please, when responding to this please keep in mind that this is currently ongoing. 2. I am seeking advice on how to move forward with this from people who have had success with their MIL and still keep a good relationship with the wifey. I love both my wife and her mom equally and do NOT disregard my wife's needs or pick and choose between the 2 at all. This WILL be slightly long but please bare with me.

Quick backstory, I(23) have been with my wife since I was 15. We have an amazing relationship and just recently got married! Her MIL(56) and I have had the best relationship you could ask for between a SIL and a MIL and damn near raised me. My wife and her mom both share the same body as well as the same traits. Mixed, very curvy in the right places, curly hair, tall, absolute smoke show of a mom and daughter it blows my mind every day. I'm not going to go into crazy detail so we can shift away from the fantasy part of it, this is very real lol. She does have a long term BF, but literally for the last 2 years, they have been off and on fighting and currently they're "okay." Nothing toxic, they just don't see eye to eye on certain things. The reason why they're together is because they run a business and she plans on leaving him the moment there's an opportunity. 

Anyways, I have always had the hots for my MIL and I know she has definitely caught me staring or slightly flirting; as that's just my natural personality. I've lived with her on and off and as of last year, we moved back in with her while we're saving for our own house. I'm always up around 6am, as well as my MIL and we make coffee for eachother in the morning, exchange conversation about work, banter, etc.

So now I'll tell you my progress, a few weeks ago she was scrolling through her camera roll showing me this sports bet she had placed and I caught a perfect, if not the best, glimpse of a pussy pic she had taken. Obviously, that got me extremely horny and I started thinking maybe one day I could give this whole "fantasy/idea" a shot. 

Last week, after our morning little routine together, I just couldn't help but to think of different ways I could shoot my shot subtley and read her energy. I decided to put a cock ring on, get inbetween hard and soft and walk into her room to "ask a question about work" with a perfect print of my long, slightly hard cock pressed against my flowy pants. ** IMPORTANT ** I do have a pretty long thick cut cock, so it's not like i'm flashing a shrimp lol.*** 

Now, for example, these pants you can see the veins, crease of the head, etc through the outside so it was perfect. To sum it up, I asked the question, caught her quickly staring at the bulge and that was that. Good reaction, good energy towards it, and she acted cool about everything but I definitely caught her peepin a little. 

PRESENT DAY! This week, well, the past 3 days I've tried different things. 

On Monday, I chose to wear my (damn near see through lmaoo) gray robe with no boxers, cock ring to give even more of a bulge, and a shirt. I left the front basically split in the middle so it could flash here and there at certain angles. There were multiple instances where I would walk in to talk to her hard, or bend over and pet our dogs knowing damn well my dick was swinging. I hadn't fully caught her looking, but i know for a fact she saw it at least 2-3 times. No weird shift in energy, no nothing, all smiles from her still, probably even more so, but she's too smart to not notice. Wife woke up, so I ended up throwing on those grey sweats again. My final move before I went to work was that I had told her i wanted to shave my beard and that I needed some opinions on what I should do. I used AI to help put different beard styles like a goatee or just the mustache on me and put them in order along with a dick pic in between them. We swiped through them together, asking her if she thinks i'd look best with something new or to keep the old stuff. Every time I swiped over the picture of my cock, I would wait like half a second and then go to the next one. I also saw some body language of her basically gasping at it, but then would turn to me and analyze my face to see what facial hair would look best lol so literally no change in energy, more of just an appreciation you know?

Now look, ever since last week, I always greet her with my dick hard in my sweats or no boxers under the robe. I love it and I feel like she does too. Every day.

Wednesday : She is a business woman, and is always sitting on one of those chairs that fixes your posture all day. I had asked her if her back ever hurts & she said no actually not really. I grabbed her shoulders and started rubbing them, dick pressed into her back which i know she felt. I kept massaging, talking to her, and started to go towards the front of her shoulders, towards the middle of her neck, right above her tits, basically cleavage area. I moved to her back and teased her bra straps off to the side slightly No reaction, she just let me, never said anything like what are you doing? no nothing lol. She did look up at her TV for the time and said "Look what time it is already, we all have to get going soon" which was the truth, but i'm unsure if that was her saying like okay this is enough you know? There was no shift in energy at all, same demeanor the entire time.

Now fast forward to Thursday (Today): Like I said, greeting was the usual, no boxers, robe undone, just a shirt. This time, when we got coffee I decided to warm up some food for breakfast and sit down, legs spread open, cock slapped to the chair, cock ring on. She got coffee, conversated, and headed to do her regular work ... no reaction as well, same positive and joyful conversation as usual. Now, we had talked for hours in her room while the wifey was asleep, about various topics & I threw in compliments where I could.  When i initially walked in, I had positioned my sweats right where my bush is showing (yes it is trimmed and shaped, it looks great lol) and she never said a word. I even stretched right next to her face to make sure she saw, same thing, no reaction. Some of them were me saying that all her sweet treats go to the right places, that she needs someone obsessed with her, to provide for her, and that she don't have to worry about her ice cream addiction because she looks amazing lol. Each compliment she said "Well thank youuu☺️" and slightly laughed. I even was saying that her daughter and then I added herself as well, are wayyyy too pretty to work in which she also replied with almost like a flattered "Thank you" you know? Also I want to add that I am alwayssss shifting my focus from her eyes, to her tits, lips, or her ass, and then back up to her eyes mid convo. Towards the end, I tried to get her to help pick some photos of me for an instagram post, which i planned on doing the same thing as i did last time with the dick pics, but she had said that she was the worst with outfits and it would be better to ask the wife. At first, I thought this was clear rejection, but as the day went on, she asked me if i told the wife to help pick the photos yet, WHILE the wife was there, and i said no and she explained to the wife that i had told her about that. We all started laughing about how she said she's the worst and to ask my wife instead. I played it off because it's the truth, I am trying to make a post lol, but not really. My MIL seemed very clueless about the fact that I might throw in another dick pic. 

Now, If there is ANY advice on the next step, I would love to hear from people with success in this area. 

Do you guys think she is digging the attention or no? 

Why do you think she has no reaction, but isn't complaining or changing the mood, like at ALL? 

What else should I try?

A massage again and this time actually go for her tits? 

Any advice that is useful is appreciated!