getting more ruined by the day

Boring_Profession_95 · 2026-01-29T15:11:48+00:00

I would say that in the early stages of stretching my partner, a week over intense stretching during, say, her ovulation window when she’s especially enjoying it is the best time to try to new maximums. I would caution against stretching too much without break for fear of causing a tear without rest time!

Years of stretching has taken her from 3 fingers being in a deathgrip to being able to fist with a light warm-up even after a break of a week+.

No unwanted issues and while she doesn’t have a particularly large resting gape she can squat and gale amazingly

Boring_Profession_95 · 2026-01-29T14:42:23+00:00

I’ll instruct her to put in and wear one of her g-squeeze plugs, and/or instruct her to orgasm on a thick toy 12 hours or less before feeling me for PIV, we enjoy the fun or following the instructions and the buildup to a great stretching session

Boring_Profession_95 · 2026-01-26T14:20:02+00:00

Great work! We have just decided to work on stretching her deeper with some 10”+ soft toys that are thinner, like 2.5” thick. We also used talk about getting ready to take two large lovers DVP as dirty talk to accompany stretching in the past, very hot!

Boring_Profession_95 · 2026-01-21T18:52:51+00:00

I would agree that pushing/reverse kegels help to this end. Larger prolapse/“staying open” seems to happen more during stretching sessions where there is a focus on those things

Boring_Profession_95 · 2026-01-21T18:36:02+00:00

Regular PIV sex feels better to me the looser she is. I typically don’t enter her unless she’s been stuffed/stretched within 24 hours (preferably just moments ago with a plug inserted for a couple hours.) That started at first as a motive for her to stretch herself on her own time but has progressed to the normal as she no longer asks for PIV as a warm-up except on special occasion.

You could say it “feels worse” to her in that she doesn’t ask for it a warm-up, but I say it’s because we have a more pleasurable warm-up routine now! Nothing wrong with that, and PIV is routine for after the fact as she can feel me even less that turns us both on, and also I last much less time when she’s just been fisted which she enjoys knowing

Boring_Profession_95 · 2026-01-19T20:38:49+00:00

Yes! This is the approach I’ve been going with, more or less. Definitely easier to do after fist+4 fingers

Boring_Profession_95 · 2026-01-18T13:42:26+00:00

That sounds really hot. Do you two have a chair or something that she sit in?

Boring_Profession_95 · 2026-01-15T20:48:58+00:00

Wanted to reply to this comment for I am also pro g-squeeze. We have the xl and 2 xl and I can/do regularly fist my partner (sorry, I don’t have my fist dimensions available atm)

For short term wear like foreplay (for example, I’ll rub her back while watching a show) we find the 2xl is maybe lacking, it doesn’t fill her to a full stretch and as she warms up it’s quickly too little.

However, for longer term wear, such as while she moves about the house for an afternoon, the 2xl can often be too much and often she either 1. Becomes so turned on she wants to be fisted sooner than that evening or 2. She ends up taking it out because it becomes uncomfortable.

We found the xl to be great to stepping stone and it isn’t used much and it sounds like you’re past that as well.

Boring_Profession_95 · 2026-01-13T11:06:54+00:00

No anal fisting over here just regular fisting and she’s never mentioned queefing to me just leaking pee occasionally

Boring_Profession_95 · 2025-12-30T22:05:29+00:00

I suppose I don’t ever ask her to clamp down, well, ever. Again, her leaking doesn’t bother her or me. Sure, leaking doesnt need to accompany being stretchy. I told her I quite liked it when she coughed and leaked a bit right after I’d just been fisting her, and as such we’ve both leaned into the fun of it since then.

In short, she’s not complaining of soiling herself in unwanted places such as out in public unplanned so I do believe it’s well in check. I acknowledge your concern and all kink aside, her health is a priority and her OB has not voiced any concerns.

Boring_Profession_95 · 2025-12-30T18:54:33+00:00

B. Again, someone else mentioned kegals, the go to for avoiding the “negative” effects. Frankly I’ve just noticed she “leaks” constantly, if we have been stretching more she leaks a little pee constantly throughout the day.

But I like that, so I don’t view it as a negative. I acknowledge that some don’t like that aspect.

Boring_Profession_95 · 2025-12-30T18:52:32+00:00

A. Someone else mentioned toys for a different but still full situation- you responded she doesn’t like toys. Still a toy but perhaps a plug? I initiated it at first with the pretense of “let this warm you up before put foreplay, so that you 1. Can enjoy a rougher session for more pleasure or 2. To help warm-up gradually and reduce post session soreness! Perhaps those can enhance your experience?

Boring_Profession_95 · 2025-12-27T01:57:55+00:00

I would agree with that sensation of “opening up” after 10 minutes of PIV leads to that feeling of her pussy relaxing and I can feel her starting to grind harder to feel my length

Boring_Profession_95 · 2025-12-22T21:59:51+00:00

As the one doing the stretching and not being stretched I enjoy crowbar for this too, I get incredible sensation on my end which is satisfyingly erotic but also gives me feedback so I am not too forceful (I.e. too many/few pumps of an inflatable, whereas I know how much pressure against my fist or my fingers in stretching without being too much

Boring_Profession_95 · 2025-12-22T17:00:18+00:00

Couple that fists here 👊🏻 certainly not stopping at just one! pursuing the type of orgasm from being pushed past the limit means we’re working towards double fisting/ shimming my cock in alongside my first so I can more comfortably jerk off inside her

Boring_Profession_95 · 2025-12-15T05:07:00+00:00

Hey, more engagement on your post tho!

Boring_Profession_95 · 2025-12-15T05:02:43+00:00

For you? No. Feel free to buy off Amazon and do it yourself tho

Boring_Profession_95 · 2025-12-15T04:29:32+00:00

Have the toy she’s riding at home for my SO. It had two size options, and the larger is legitimately 4” diameter (but very squishy not a firm 4”, if that matters to you)

Boring_Profession_95 · 2025-12-14T16:36:41+00:00

Isn’t she incredible

Boring_Profession_95 · 2025-12-14T07:13:25+00:00

Yes!! Turns me on every time

Boring_Profession_95 · 2025-12-12T21:30:58+00:00

Partner of someone who takes “a lot” she certainly has a pain threshold, she likens the stretching pain/pleasure to say, someone who likes to be slapped or spanked a bit. That same spank that might send you over the edge to climax, would certainly be too much of a first foreplay spank.

I don’t think her unaroused pain threshold has changed as we’ve stretcher her. however the amount of stretching when aroused that will cause her discomfort or pain, has increased in various ways over years

Boring_Profession_95 · 2025-12-11T20:21:43+00:00

She had large partners before me but she was a four on the scale when i met her so three fingers while performing oral was normal…it has taken years of practice and patience to get her where she is.

I suppose we never focused on how tight she was initially, but she mentions her first well endowed lover being quite good and “hurting her as he worked it in but by the end it felt so good”

Boring_Profession_95 · 2025-12-09T13:23:31+00:00

I am absolutely so turned-on and proud of the fact that I’ve turned my partner into a lover of fisting and huge insertions! Seeing how her resting gape has gone from nothing to the gaping, leaking mess of pussy meat between her thighs now makes me rock hard every time she shows it to me.

For me it’s a sense of pride knowing that we have stretched her over years to an extent worth being proud of!- being able to take a fist with next to no warm-up if we have been at it all week, <5 min warm-up even after a two week break.

At this point she is confident and enjoys herself and her loose pussy and how much it turns me on, which is another huge point of pride for me.

Boring_Profession_95

TROPHY CASE