Need advice on how telling woman i like to be fisted.

[bigtoys420]

Need advice on how telling woman i like to be fisted. 

In short I signed up to bumble, put a pic of myself up and did not say anything about my gender or sexual orientation or the fact that I love playing with my ass. Im bisexual and some what bi gender. I signed up 2 days ago and have been overwhelmed with the number of woman reaching out to me. I just got home from my first date and I had a great time but I know that very few girls will want to be with a guy who likes to be fisted and can take a 16 inch dildo lol. 

My question is when do I break the news that I like having my ass played with? My end goal is a relationship with a woman who will accept and embrace me for who i am. 

Hear are the options i can think of. What are your thoughts??? 

1. Don't tell her until we had sex a few times.

2..tell her right before we have sex for the first time. 

3. Tell her on the first date. 

4. Tell her before the first date. 

[Analfister97]

I didn't tell my girlfriend till 6-7months in and we started fisting her and then she played with my ass and I just kept saying more and we went from there, now we both regularly fist each other a few times a week and have great fun together and she wasn't overly sexually experienced and a very shy person and reserved person

[bigtoys420]

7 hours ago, Analfister97 said:

I didn't tell my girlfriend till 6-7months in and we started fisting her and then she played with my ass and I just kept saying more and we went from there, now we both regularly fist each other a few times a week and have great fun together and she wasn't overly sexually experienced and a very shy person and reserved person

I've though about waiting that long but I feel it would be dishonest to do so. That after 6 months it might devistate the other person to find out i have a secret side to me that I've been hiding from them. 

[Upthebutt]

From experience, dont wait. Its better to be entirely up front from ASAP. If they are completely not into it and not willing to change your mind, and its a mist for you, well you've just wasted all that time. Then your stuck in a relationship that you may or may not enjoy and unable to pursue your kink with your partner or anybody else, unless poly.

 

As to how to do it. Joking as a hint can sometimes help you get an idea at first, but its just better to break the ice and ask what kinks they have and tell them yours.

[bigtoys420]

@Upthebutt I agree being up front is important but when would be the right time? 

I feel if I tell them before we meet i will never get any dates. 

During the first date I might not get a second date. 

Before we have sex they might change their mind. 

After we have sex might be looked at as being dishonest. 

I want to be upfront and honest about it but i feel like im hurting my chances if I do so. 

I like your idea of asking her about her kinks. I guess my best bet is on the first date. Feel the girl out and then make the move ask her about her kinks in bed and wait for her to ask me mine. Be upfront that I'm looking for a girl who is okay with fisting me and see what happens. 

I'm trying to setup another date for tonight and I already have one for tomorrow night. Ill give it a try and report back the results. 

Thanks. 

 

 

 

[Upthebutt]

@bigtoys420

 

When you do it, is up to you. Best to wait until the time is right. You can try surface level questions, but its hard to tell. For example I've heard of conservative, wait til sex folk, who end up getting into pegging together. On the opposite end, I've known open minded hippies who would revolt at anything more than plain vanilla sex. So you can't judge a book by its cover unless you know.

 

Ill be honest, I haven't dated in many years now. However, rejection in general is a part of life. As long as you dont make it seem that your kink is the only shade of your personality I dont see much more happening than rejection. If she does do worse to you then A) you dodged a bullet by her showing her true colours. If you cant trust her with your kinks, would you trust her at your place? B. You've now eleminated a possibility and can get a move on.

 

 

Likely its going to be hard work. Much like finding a needle in a haystack, but as evidenced by other members not impossible. Id try looking at local munches or your local Fetlife.com area. I remember you saying you were in the states, and believe me, you are absolutely spoiled with the number of people available down there each with their own personality and kinks.

 

Just keep in mind, we are all not only our kinks. Humans are dynamic diverse creatures, so make sure to get to know them. Like would you want to spend a relationship with someone who may fist you, but is a cunt to you and your family?

 

As for how, start off small and try and open her up from there. You'd be surprised how some people are open minded. Maybe just dont dive immediately into anal stretching lol. Start off focusing on her. Did she like 50 shades? Yes? Oh so is she into BDSM? Does she prefer things more sensual? Oh has she tried anal? Ask thezs things after you know a bit about her lol.

 

Finally, use your bisexuality to your advantage. Be up-front about it. For example if you commkt to a monogamous relationship, can you still explore with gentleman? Thats important too. The fact that you are bisexuality will also give enough of a hint that you enjoy butt stuff. Kf shes repulsed by even bisexuality, well i think you've got an answer about what type of person she is. However, if shes willing to listen, see where things go.

Remember too, shes a woman, not a kink dispenser. If you make her feel like one, good fucking luck lol

 

[imsnowman72]

Good question and responses.

 

[FredTheFister]

If a woman who fists you is absolutely what you want you need to find out as early you can. But the better you get to know a woman and the more she likes you, the more likely she is to say yes to the question. 

So if you ask her on date #1 she'll say no, but after a few dates and she really likes you she might be more open to it.

I got married recently and I had decided I didn't want to get married unless it was with a woman who would fist me. I told her after we had been dating for a while and it was clear we were planning a future together. Women I dated before here were not wife material and they never received the info I was into fisting, but I had fun with then nevertheless, just not fisting.

[Punch]

On 3/13/2020 at 7:01 PM, FredTheFister said:

If a woman who fists you is absolutely what you want you need to find out as early you can. But the better you get to know a woman and the more she likes you, the more likely she is to say yes to the question. 

So if you ask her on date #1 she'll say no, but after a few dates and she really likes you she might be more open to it.

I got married recently and I had decided I didn't want to get married unless it was with a woman who would fist me. I told her after we had been dating for a while and it was clear we were planning a future together. Women I dated before here were not wife material and they never received the info I was into fisting, but I had fun with then nevertheless, just not fisting.

We never really planned it in the beginning. We were at the Presidio SF in the early 90's when we met. After building a strong friendship, which is the most important part to me, not knowing was the most important part of it all. We had strong communication so nothing was of limits. We had been out on the town going to various cubs of Lombard, Tenderloin, Castro mainly for cultural experience as that both happen to be our thing being open minded and wanting to learn. Back then SF use to be the shit for night life. Places like the Mother Lode, Mitchel Bros's and various all nude no liquor, partial no liquor, clubs. I've heard it sucks now. So we were at Mitchell Bros and we watched a live stage show of two women going at each other with strapons, pegging the shit out of each other and it was so fucking hot! Now, I've always wanted to dominate a man, but never the right one appeared to me. I new him and trusted this one and on the drive home, so turned on by the show I simply asked in a mater of fact way, how it turned me on and that I wanted to try it. We had no idea what the fuck we were doing.We went to a local shop and got a harness and strapon together, which in itself was a great experience. Being both from medical backgrounds we new or guessed, hygiene and the idea of enemas and cleaning  out was a given.

At first it was like typing with all thumbs. I had no idea and he was excited and terrified at the same time. I actually used a couple fingers and just took the time to get him comfortable which was the hardest part of all. This is 1993 when there was absolutely no info available. We just stumbled through it and had a fucking blast! After about 2-3 weeks from what I remember I slipped my fist in his ass for the first time. I was scared for him and he was terrified cause he clamped down and didn't think I would be able to get my hand out!

Here we are 27 years later and well, you be the judge!

https://xhamster.com/photos/gallery/12280581/297583173

[secretkink]

On 3/15/2020 at 10:24 PM, Punch said:

We never really planned it in the beginning. We were at the Presidio SF in the early 90's when we met. After building a strong friendship, which is the most important part to me, not knowing was the most important part of it all. We had strong communication so nothing was of limits. We had been out on the town going to various cubs of Lombard, Tenderloin, Castro mainly for cultural experience as that both happen to be our thing being open minded and wanting to learn. Back then SF use to be the shit for night life. Places like the Mother Lode, Mitchel Bros's and various all nude no liquor, partial no liquor, clubs. I've heard it sucks now. So we were at Mitchell Bros and we watched a live stage show of two women going at each other with strapons, pegging the shit out of each other and it was so fucking hot! Now, I've always wanted to dominate a man, but never the right one appeared to me. I new him and trusted this one and on the drive home, so turned on by the show I simply asked in a mater of fact way, how it turned me on and that I wanted to try it. We had no idea what the fuck we were doing.We went to a local shop and got a harness and strapon together, which in itself was a great experience. Being both from medical backgrounds we new or guessed, hygiene and the idea of enemas and cleaning  out was a given.

At first it was like typing with all thumbs. I had no idea and he was excited and terrified at the same time. I actually used a couple fingers and just took the time to get him comfortable which was the hardest part of all. This is 1993 when there was absolutely no info available. We just stumbled through it and had a fucking blast! After about 2-3 weeks from what I remember I slipped my fist in his ass for the first time. I was scared for him and he was terrified cause he clamped down and didn't think I would be able to get my hand out!

Here we are 27 years later and well, you be the judge!

https://xhamster.com/photos/gallery/12280581/297583173

Love your vids!

Do you like any anal done on yourself?

[elirian]

So,

On 3/13/2020 at 10:48 AM, bigtoys420 said:

@Upthebutt I agree being up front is important but when would be the right time? 

I feel if I tell them before we meet i will never get any dates. 

During the first date I might not get a second date. 

Before we have sex they might change their mind. 

After we have sex might be looked at as being dishonest. 

I want to be upfront and honest about it but i feel like im hurting my chances if I do so. 

I like your idea of asking her about her kinks. I guess my best bet is on the first date. Feel the girl out and then make the move ask her about her kinks in bed and wait for her to ask me mine. Be upfront that I'm looking for a girl who is okay with fisting me and see what happens. 

I'm trying to setup another date for tonight and I already have one for tomorrow night. Ill give it a try and report back the results. 

Thanks. 

 

 

 

so, how much have you talked about some of the other stuff in your original post? Like does she know you're bisexual and also kinda nonbinary/bigender? These are important things that are all related - if you're able to be honest about how you identify sexually (which should should be!) and you find someone who is amenable to that then having a conversation about ass play will definitely be easier. In any case, I think you should wait until after you at least have sex once, but too long after - that will be a great way to start a more in-depth conversation about your sexual interests. Too soon (especially as early as the first date) and you might just come off as a creep - Kinks aren't typically a first date topic in my experience. But shortly after you two actually start developing a sexual relationship seems like the right time to me.

[kcolyrf]

I've been down this avenue a few times and to be honest, it gets easier every time. With my first relationship, I was terrified of saying it and I thought it would be best if I took her out for icecream and stuff. After I was sweating bullets, she broke the ice and asked if there was something on my mind. I told her I needed to tell her something but I wasn't sure I was ready. She was pretty understanding and waited until I decided to lay it all out and tell her what I was into. She laughed at first because she thought I was going to say I had a crippling addiction to drugs or alcohol. After her laughing fit she said that doesn't bother her at all. The relationship lasted quite awhile but ultimately we broke up. 

The next few relationships, I broke the news on our 4th or 5th date. They varied from me just sitting them down after a home cooked meal and telling them about it or just me beginning a conversation about what turns them on. I've only had one person who asked "Does that make you gay or are you bi" She was heavily religious but in the end she turned around. 

With my fiancee, I told her flat out on like our 3rd date and said "I totally understand if you don't get it but it's what feels good to me" She loved that I wasn't trying to hide anything and honestly, it helped build our relationship because I don't feel like I have to hold back now. 

Hope my anecdotes help you out and gives you some perspective. I find it helpful to be honest and upfront without sounding ashamed to work best. 

[Glasg0wR0se]

hmm. I'm pretty bad at talking about things. my partner and I have been together for 10 years plus and we've never had the conversation about what I'm really into.

on the one hand, it's always been something that I have done alone, so that makes it hard to open it up to her. on the other hand,  with this fucking virus shit she's home all the time now. so I've now got like  zero privacy.

part of me thinks it would be cool to have her fist me, but she's done literally no anal of any kind in her life so even if she was 'open to it' she's starting at the beginning and I'm where I am so is it even worth opening the can of beans, risking the rejection and/or massive awkwardness just so she can try it once, be bad at it/hate it and then we're back where we are now...? it's not like she's close-minded or anything... in fact probably anything but, it's there's just so much capacity for it to go wrong.

plus  when something has been a secret for this long... and there have been times when we could have had this conversation... but it seems like either she knows literally nothing or she knows something but has no desire to initiate the conversation... fuck. HELP!

[Glasg0wR0se]

ok, so I was actually hoping there would be some advice for me to consider.

I'm at the end of my tether here. this fucking lockdown means we're stuck in this house together which means I'm not free to play as I would ordinarily do, and there's just no apparent 'in' to any kind of conversation about fisting etc... like we're not even close to talking about it. HELP!

[elirian]

1 hour ago, Glasg0wR0se said:

ok, so I was actually hoping there would be some advice for me to consider.

I'm at the end of my tether here. this fucking lockdown means we're stuck in this house together which means I'm not free to play as I would ordinarily do, and there's just no apparent 'in' to any kind of conversation about fisting etc... like we're not even close to talking about it. HELP!

Honestly, if you've been together for 10 years, she will be probably be more upset that you have kept something from her for so long than she would be offput by the fact that youre into fisting. Have you guys been having sex much/more than usual since the quarantine started? I mean, odds are she's going a little stir crazy too. Maybe start with stuff you both already do and work from there.

[AzFrNick]

Most women are more open sexually these days and they've watched more porn than you'd think. They are aware of the fact that anal is something a lot of people enjoy and that some men and some women enjoy anal fisting.

I would not wait too long, as soon as you realize that she is kinky and open minded.

Give her good sex, make it enjoyable, listen to what she likes and try to give her many orgasms

Also don't forget that the fun is not only in the bed. Show her a good time, go do new things with her, take her to a concert, make her enjoy life with you.

And then bring it up slowly, usually after sex. Explain that you have a kink and make her guess...

[Snickers]

Good luck! I told my woman and she managed to fist me at 3 different occasions. After that she had a breakdown and she was disgusted and told me that she can not accept it anymore while crying.

Edited April 8, 2020 by Snickers

[087john]

On 4/5/2020 at 1:10 AM, Glasg0wR0se said:

ok, so I was actually hoping there would be some advice for me to consider.

I'm at the end of my tether here. this fucking lockdown means we're stuck in this house together which means I'm not free to play as I would ordinarily do, and there's just no apparent 'in' to any kind of conversation about fisting etc... like we're not even close to talking about it. HELP!

Do you keep any other secrets?  I don't want to be a dick but it honestly doesn't sound like a healthy relationship if you have kept quiet about this for 10 years

[Glasg0wR0se]

7 hours ago, 087john said:

Do you keep any other secrets?  I don't want to be a dick but it honestly doesn't sound like a healthy relationship if you have kept quiet about this for 10 years

I guess it's just always been something that I've done alone. I was doing it before we got together and I've never shared it really with any female partner. it's never really been part of any fanstasy that I've ever had to have a woman fist me? in the fantasy it's always a guy. or multiple guys... plus, unless she's hiding an equally secretive fetish fantasy life (which, if she is, makes her just as bad as me), there is nothing that we've ever said or done that would lead me to believe that this was something she was interested in. and while she occasionally puts up with me talking about football or the like, her willingness to engage in things that she does not already like is limited.

I wouldn't say our relationship is unhealthy, but we've got boundaries, or at least I have and I assume she has too... I'm only considering bringing this up now because of this fucking virus. I don't for a second think that telling her would fuck up our relationship or anything, it's more that... right, how do I put this?

1 - she just flat out refuses to do it... we basically pretend like I never brought it up. plausible. but then it's gone. it denies the possibility that we could have at some point arrived at a situation where we tried this or whatever... that possibility, slim though it was, is no longer there.

2 - she agrees to try it... also plausible. she's moderately sexually adventurous I'd say, but all more or less vanilla. no pain. no bondage. ok, light bondage a handful of times, not for years. no s&m of any kind. unless, as I say, she's just elected never to include me in any of it... but yeah, she tries it, she hates it. then what? or she's bad at it. or she's so worried about being bad at it that it's even worse? how to put this, she's not good at being bad at things. we can't play a game that she doesn't think she's good at. why would this be any different?

like, I have to live with this person 24/7 at the moment. I really don't want the cloud of awkwardness that this could potentially bring about. but I can't play like I'm used to and I'm not happy with that.

and do I keep other secrets? of course I do. who doesn't? I mean really. who doesn't keep secrets?

[elirian]

On 4/8/2020 at 10:25 PM, Glasg0wR0se said:

I guess it's just always been something that I've done alone. I was doing it before we got together and I've never shared it really with any female partner. it's never really been part of any fanstasy that I've ever had to have a woman fist me? in the fantasy it's always a guy. or multiple guys... plus, unless she's hiding an equally secretive fetish fantasy life (which, if she is, makes her just as bad as me), there is nothing that we've ever said or done that would lead me to believe that this was something she was interested in. and while she occasionally puts up with me talking about football or the like, her willingness to engage in things that she does not already like is limited.

I wouldn't say our relationship is unhealthy, but we've got boundaries, or at least I have and I assume she has too... I'm only considering bringing this up now because of this fucking virus. I don't for a second think that telling her would fuck up our relationship or anything, it's more that... right, how do I put this?

1 - she just flat out refuses to do it... we basically pretend like I never brought it up. plausible. but then it's gone. it denies the possibility that we could have at some point arrived at a situation where we tried this or whatever... that possibility, slim though it was, is no longer there.

2 - she agrees to try it... also plausible. she's moderately sexually adventurous I'd say, but all more or less vanilla. no pain. no bondage. ok, light bondage a handful of times, not for years. no s&m of any kind. unless, as I say, she's just elected never to include me in any of it... but yeah, she tries it, she hates it. then what? or she's bad at it. or she's so worried about being bad at it that it's even worse? how to put this, she's not good at being bad at things. we can't play a game that she doesn't think she's good at. why would this be any different?

like, I have to live with this person 24/7 at the moment. I really don't want the cloud of awkwardness that this could potentially bring about. but I can't play like I'm used to and I'm not happy with that.

and do I keep other secrets? of course I do. who doesn't? I mean really. who doesn't keep secrets?

Think about it this way: If you talk to her about it, she will likely be pretty mad that you kept something like this from her for so many years, but it would certainly be better than if she caught you or found one of your toys or lube or whatever. Sure, you're taking a risk that she'd maybe be grossed out or not interested, but on the other hand, she might be willing to give it a try. And as far as her being bad at it goes, just be encouraging and try to get her into it. Hell, if you talk about how good it feels you she might even take some interest in trying anal herself. It might not be the dudes in your fantasy (ps maybe you should also have a conversation about being bi/at least bicurious with your wife, seems like something you shouldn't keep covered up), but it's at least an improvement.

[Glasg0wR0se]

3 hours ago, elirian said:

if she caught you or found one of your toys or lube or whatever

ok, so let me tell you where we're at. there have been a handful of occasions when I have forgotten to put something away. I've never consciously pushed the issue, but there have been opportunities for this to be made into a thing and it never has. not once. so, either she's seen the lube/toy/poppers, whatever... and just ignored it? or what? she's just a fucking blind person and I'm only noticing this now? she's seen shit lying around, for sure. we even had a conversation very early on in our relationship where I mentioned that I might be into her fucking me with a strap on. I rememer this. no follow up. not in 10+ years. she is clearly not interested in this. if this was something that she wanted to explore, she'd have done that by now.

this is not some gigantic secret that I'm keeping from her. this is a box in our bedroom, not particularly hidden, not locked or anything... and either she's waited til I'm not around and had a good old rummage around, or she hasn't. if she's looked through it, then I know for sure that she wants nothing to do with any of this shit. and if she just never thought to look then that's the level of curiousity that I'm dealing with... think about that?

4 hours ago, elirian said:

she might even take some interest in trying anal herself

you know what? maybe you've met this person. but I've not met the person you're talking about here. I've seen my partner experience a lot of different feelings and whatnot, I've never seen her think for a second that she would do this.

[benhoward]

perhaps the lock down is the perfect time to try the strap on approach again? find an article online about it and bring it up that way? there's plenty of women's magazines that talk about pegging.

use the extra time together to your advantage and explore new things. the chances are she'll have something she wants to try but was too afraid to ask too