Alright /adv/, I need actual guidance on this, ik it sounds silly but its not a bait thread or anything, seriously looking for help.
My gf stuck her finger in my ass one time during a blowjob and it was really painful. But ever since ive wanted her to do it again, more often. I would thoroughly enjoy having something in there when i cum, and i know this for a fact.
Problem is, everything is extremely tight, and no amount of "how to have anal sex" or "how to massage your prostate" vids seem to make it any less painful. Also i cant ask her for it anymore because she gets really judgemental about it, i think she loses respect for me as a man/masculine figure when i ask her for it, at least thats the vibe she puts off heavily.
Please guide me into comfortable prostate stimulation/asshole stretching? All i have is a vibrator and some aloe.
Pic related is the object i eventually want to fit in my ass on a regular basis
>>16925639
Ask your mother, she is an expert
>>16925639
Just start getting fucked in the ass and that'll do the trick, seems like you're going down the homofag path anyways.
>>16925639
have more fibre, take some srs shits
Anal expert here. Aloe is not good enough. Invest in a decent water-based lube. Try using much smaller toys first, Bad Dragon makes a series of lube applicators that work well for warmup and beginning play since you already like their stuff.
A good lube can mean the difference for me between getting my pinky in there (painfully) and fitting an 8 inch cock in my ass. Astroglide is good to start, comes in a purple bottle and you can buy it at any drugstore, online, or at Walmart.
Any other questions?
>>16925639
Your girlfriend is probably okay with sticking her finger in your ass during a blow job. Have you tried using actual lube? Giving yourself enemas?
OK the biggest thing here is to relax. Relax your breathing, relax your body, relax your butt. Also the more horny you are for it in your butt, the better.
Lube!!! Use plenty! I recommend sliquid. It's a bit pricey but so worth it. Make sure it's water based if using dildos. Don't be afraid to add more during session.
Go slow! Play with just the outside first. Put small amount of pressure. Stay relaxed. When inserting something, don't worry about stopping for a moment to relax. Once it's more comfortable, build speed slowly. Start with something small, such as your pinky.
Probably best to start alone, so you can get more comfortable before asking your gf again. Good luck!
>>16925649
I habe no physical attraction to men. I find the thought revolting.
>>16925657
This is done already, im pretty empty in there.
>>16925673
None of this shit is available to me at the moment, and Im never gonna have the opportunity to simply drive off and buy myself some ass lube. Is there any better household. Substitute I can use beside aloe?
I have vegetable oil, baby oil, and absolutely nothing water based.
Also, when inserting an object shaped like this, would it be more comfortable with the tip bemt facing towards the back or stomach? I apologize if this doesnt make sense, not sure how else to explain what mean.
>>16925694
Whats the best position to do this in?
Also, what do i do about discomfort/soreness afterwards? Will that fade away in time?
>>16925716
If you use the right lube and something small, you shouldn't be sore or uncomfortable afterwards. If you still are, take it easy for a while and let it heal.
Best position is to lay on your back with knees up high, possibly with pillow under your lower back.
>>16925710
Why can't you go get yourself some lube?
>>16925724
Thanks anon, I'll be back in a bit with a progress report.
>>16925727
I share the car with my gf, we live in the same livingscpace. She secreets enough pussy juice simply by the touch of her clit that lune is utterly unnecessary. it even makes great anal lube for her.
Shes a pro at this, and can push herself onto me down to the base with barely any warmup and zero discomfort.
But shes really judgemental about my interests, so if I took the car out or picked some up on my way home and put it some place, she'd either
>a) Call me a faggot and shame me for being into it
>b) Find out I tried to hide it, assume its a much bigger closet obsession of mine than it really is, suggest i go get help and probably leave.
Either way I just want to stimulate myself more than the typical fap session without being ridiculed. Buying anything specially formulated to slip things in my ass will only complicate my relationship.
http://www.ohjoysextoy.com/buttsex/
>>16925745
Well lube is the best. You really should talk to her about this. But if you're really set on not using it, cheap non-scented or lightly scented conditioner also works. But be careful, because I have heard that it can irritate your skin and things like that.
PS your gf is a beast
>>16925758
Thanks, ill go try it.
Yeah, ik. The sad part is I got yer into it, similar to the way she got me into it, except it started as a rimjob and her curiosity blew up. For maybe 4 months straight we had nothing but anal sex, and we eventually agreed upon inviting others into our sex life.
Since then we've been into MFM threesomes, MFMF foursomes, and pic trading with her best friend and her husband. Its been phenomenal, aside from the few double standards
>she wants DP but gets jealous over her best friend getting DP'd
> FMF interactions also make her jealous. Will be fine with them for the moment, but for the next few days I'll be questioned at random on who I enjoy more.
As far as Im concerned, I couldnt ask for a relationship closer to perfection.
when you're putting stuff in, do deep breathing. always push in towards your ass on an "out" breath. go so slow you feel ridiculous. add lube continually because it will dry after a while. play with some other part of yourself during; the more aroused you can keep yourself the easier it will be to do. if you accidentally put yourself in pain but it's tolerable, wait it out rather than yanking the object out of your butt, because it will fade quicker than you might think if you can roll with it.
I honestly like petroleum jelly or thick oils for lube if I'm nervous, out of practice, or using something big. they don't "wear off" very quick.
>>16925921
Thans guys.
Status report:sharpie is comfortably in my butt.. But how do i transition to a bigger object now? Wont pulling it out make me go back to square one?
>>16925921
oh, another tip: if you push an object of reasonable size firmly but gently against your anus and rub it around, breathe deep, contract and release your muscles, use enough lube, and generally get yourself feeling good and turned-on enough, it will "pop" into your butt /of its own accord/ with no intentional insertion necessary.
scary but true: your ass eats things.
>>16925940
Get more aroused and relax more. Don't go for bigger if you don't feel up for it.
>>16925949
>scary but true: your ass eats things
Kek but probably true
>>16925757
>>16925694
Every single goddamn time I come to this board I find at least one thread asking for advice that has already been covered by this comic. I don't even like oh joy sex toy but the more I come here the more it's becoming the webcomic I've recommended, posted or linked the most times. Thankyou for beating me to it this time.
>>16925951
Seriously dont know how i could get more aroused, but entirety mentally up for a full sized object up there
>>16925959
Feel free to call me a retard.. But I cant get an STI from a dildo can I? Like it isnt something thats airborne or highly contagious is it?
>STI man bought drink. Paid with cash.
>you buy food, get his change in return.
>you put STI infected money in your savings bank.
>go about the rest of your day
>fap with that hand and get STI
???
>>16925976
No you cant. I suppose if you shared a dildo with someone it's possible?
>>16925976
Clean your dildos with rubbing alcohol. You can't exactly get a STI from them, but they still need to be clean and disinfected.
>>16925976
Not unless you're creating micro-tears. This is why you should only buy silicon and avoid dildos with mold seams.
YOU my good sir, are in a very weird time in your life.
>>16926014
>>16926044
>>16926080
Thanks, the alcohol wint ruine the silicone?
Its been shared between the 4 of us mentioned in >>16925795, but bodily fluids have been swapled around so much between us that it doesnt matter at that point. We've all been tested, so theres no risk until somebody cheats. Which they have no reason to because of the arrangement we have.
Also, does this qualify me as a faggot? In all seriousness, ive always considered myself to be masculine and 100% straight. Nothings changed, other than that I found that I occasionally (once every other month or so) crave something in my ass. Amd when im ij these phases I fap exclusively to pretty traps.
Still otherwise consider myself 80% straight, but with the pressure put on me by my gf i start to doubt that. I have no interest in men or touching men, its sickening, but i some how find ladydicks to be fine.
This would be more enjoyable for me if i wasnt so concerned with my true orientation
>>16926103
Yeah.. I kind of love it though? Its something that makes me cozy when i think that i only get one shot at this, and im not holding back at all.
>>16926108
No, rubbing alcohol should be okay on silicone. Clean asap after each use, and you can use hot water and soap too. Additionally, you can use a condom on your dildo to make it even easier to clean.
>>16926108
No I'd say you're not gay. Maybe not completely straight though, because traps do have dicks. But sexuality is a weird thing and I don't think you need to define yourself anyway.
>>16926181
Thank you all so much. I got it all the way in
One last question though, when i go really deep, i feel like i have to pee. Is this normal? Should i stop when i feel that?
