Anal Curious advice sought

I'm becoming curious about anal sex with a man. Obviously I'd want to be safe so would want any partner to use a condom but wonder if anyone here has any advice they can give to someone contemplating having anal sex (receiving) for the first time. Should I allow them to do it straight away or do I need 'training' with fingers, toys etc. Should I expect them to use a lubricant before penetration. Should I expect it to hurt the first time.

I have someone in mind who I can trust though we might have to meet at another persons house so it might happen in front of others but I'm prepared for that.

I just feel ready to try this even if only the once.

Personally, I'd get comfortable with dildos first then experiment with a strap on used be a trusted friend or lover. Use plenty of lube, go slow - don't expect instant accommodation.

If you have a comfortable lover, maybe they can be involved to help ease your anxiety.

Thanks jds4med I'll bare that in mind. The person I have thought about is not what I could call a lover and we've not met yet but we've emailed each other for several months now and I'm thinking of asking him if he will consider doing this with me. He's a life model and I know he has received anal before but not sure if he's buggered anyone himself. If he hasn't and doesn't wish to I might ask if he could introduce me to someone who would do this for me and ask him to come along as a friend to help me feel safe and secure.

I've not experienced anal intercourse either, but I will say that it would benefit you to become friendly with enemas - an enema bulb at the minimum - a bag if you decide you enjoy them. Having your bowels cleared is a great step toward exploring anal eroticism. I know it has made playing with toys immensely more enjoyable.

Also, don't be afraid to get messy with the lube - lube is your friend 😃

Thanks ImDoug all advice gratefully received just need to find a partner for this now, not had a reply yet from the person mentioned below so may have to look elsewhere.

Also now considering a blog if this is going to take some time and I need to 'train' with enemas and toys as you suggest. I'll admit also that I'll probably get nervous but excited as the time comes to lose my anal virginity. If I can't find a male to do this I'd certainly consider a female with a strap-on as suggested by Jds4med unless that would be considered too much like cheating.

Good advice from all the posts so far. I would definitely buy a few different sized dildos and just play with them on your own. If you are communicating frequently with your friend and he is agreeable to give it a try, you ought to ask his full erect size. It is a fair question since this will be your first time and he knows that. If you have that information you could purchase a dildo of comparable size. The key measurement is width of his penis. The width is what you will feel and can be painful if you are not ready for it.

Going slow and doing a little anal foreplay (lots of lube) will also get you relaxed and ready. Have your friend start with a finger and then work up to two or three to get you open and relaxed. Even have him massage your prostate which should really get you turned on.

It sounds like you are looking forward to this new adventure. If you take some steps to prepare (enema prior to play, practice with dildos) you will very likely have a very positive experience and that is what you want.

This video was posted on another thread and is quite good for coaching a first timer on how to have anal sex on the receiving side. It's 32 minutes long but worth watching.

http://www.xtube.com/watch.php?v=DqtMu-G540-#.VCT9DfldWa_

Hi ProV1 and thanks for the advice which I will definitely follow and I'll take a look at the video.

Not heard anything from the online friend for several weeks now and I know he has had problems with his email so may have permanently lost contact with him.

Spoke to someone on the phone who wants to examine me tomorrow after work to see how large my anal passage is, he doesn't do anal but says he knows someone who does but they are a cross-dressing dom. I've agreed to the examination and I'll see how many fingers I can take if that's how it's done but that's as far as I've agreed to go for now. I've not agreed to anything else without meeting them and it's not really what I've had in mind.

I'll post an update here after the weekend.

After several years of play, I can take my friend balls deep off the get-go. I'm not very tight and we use lots of lube/

All this after several enemas though. We have known each other for a very long time, so I let him cum inside me if he wants.

Aholestretcher thanks for your contribution. As for me well nothing to report after the weekend as nothing happened. I think the contact was a time waster which is not uncommon on Craigslist and I've still not heard from my other on-line friend. So I'll keep looking on here and perhaps keep an eye on Craigslist for a possible volunteer even if that's just for a fingering and some toy play for my anal cavity.

I would suggest using your fingers and some smaller dildos before jumping right into anal sex. That is fun in and of itself.

I agree with the advice here. You definitely need to consider experimenting yourself and getting used to being penetrated with fingers/dildos. The average man isn't huge so I would suggest some more "normal size" dildos.

Thanks to mbm and bulittman I'm still hoping to find someone to help me with this as that will also get me used to submitting and exposing myself to other males and if I'm ever to receive anal I'll need to do that.

One solution might be to go for colonic irrigation, there is a young Asian lady locally that does this and that would get me used to having my anus penetrated and give me a good clean out at the same time.

So, probably like many here, my first attempts at anal were abandoned due to it seeming impossible/painful. Thankfully the internet was at hand to guide me.

I did start with fingers (thumb to be specific) and a variety of small objects. As a teen I wouldn't have dared purchase a toy, don't think it ever crossed my mind.

So anyway, the first time i had anal sex was with a friend. I used some body lotion I had handy, lube is definitely more recommended, but anyway I inserted one finger, then two and did the scissor opening motion to slowly stretch myself. I had him lie on his back, this is almost always my preferred position to start off with. Reason is that I'm mostly in control of how far and fast he enters me, other is I find it easier to concentrate on relaxing back there and even 'pushing' as though you are on the toilet.

Anyway, with that in a matter of moments he was well and truly balls deep inside me and went from there.

I hadn't encountered enemas or dildos or anything, just took my time, prepared and relaxed. Once its in and you're relaxed there's really only enjoyment to be had, lots and lots of enjoyment.

Nethingonce thanks for relating your personal experience, as soon as something happens if it ever does I'll put a full account on here good or bad.

I arranged to go for a full-body including prostate massage yesterday (Monday) but he turned out to be another Craigslist timewaster who although arranging the appointment before the weekend, on the day didn't answer either of my two text messages requesting the address.

So I've decided to give up on this project at least for the time being and probably altogether.

There isn't much I can add to what advice has already been given, except to say "Don't give up." You would miss something that is at once gratifying and can lead to other experiences of equal intensity. The enemas and toys will help, but I found that a series of butt plugs were what helped me to relax. Start small and leave them in for as long as you can to get comfortable with. Go larger exponentially. I believe You will find the experience enlightening, and could possibly lead you to your goal. At any rate, good luck, I wish you success.

...on the day didn't answer either of my two text messages requesting the address....

maybe they don't answer texts and they want you to telephone.

Switchablesusie - one instruction I was given when making the arrangement was that I was never to phone him only to ever text.

Gape - I'm sure you're right about toys and butt plugs but if it isn't going to lead to an actual meeting with anyone then I wouldn't feel I'd achieved my ambition. I've been a member on this site for several years now and only ever once been contacted by someone who claimed to be local and wanted a 'daddy' but after I accepted and put a few different ideas across from on-line only to actual meetings and exchanging a few emails the contact suddenly disappeared with explanation.

I've enjoyed writing a few stories for this site and certainly enjoyed reading plenty so might just concentrate on that side.

Thanks to you all

John C

First, make sure the man you've decided to experience your first m/m anal sex is someone who is also wanting to try it. Trust, and remember your the only one in control of this experience. Best practice the levels of discomfort versus the incredible satisfaction of anal sex with a inflatable butt plug. It gives you enough stretch to receiving his member with easier entrance. It stretches your anal sphincter muscle. Avoid anal strictures by using generously plenty of lubricant. (PJur) the BEST anal lubricant. Condoms, stay away from flavor types. Take your time and enjoy.

Don't give up your search. I would also be interested in trying this too.

Best of luck

Hi All,

Thanks for the encouragement both posted here and in private messages, as it's Christmas I'll not be on here too much during the holidays so I'll wish you all a happy holiday I just wish you weren't all overseas I'd be able to invite you all to an anal party so we cold all have some fun and you'd all be able to help, guide and perhaps some of you 'enjoy me' as I experience my first anal play.

ORGY AT JOHN'S HOUSE!

ORGY AT JOHN'S HOUSE!

IN!!!

Sounds fun

Suds N Buds thanks for your additional advice but unfortunately it doesn't look like privacy will be an option. Just as I was about to give up on this quest the person that I mentioned at the start of this thread got in touch again and said he'd like to help me achieve this but hasn't got a place of his own where we can meet.

He's going to ask a couple of other people he's met if we can meet me at their places. One is an older gay male that he visits who he thinks might be willing to have me at his home and the other is a couple of male dominants who have a dungeon.

The first option with the older gay male sounds better to me but I've been told he'll probably want to invite a friend or two to watch the fun.

Not the best of situations for you 😢

Beggars can't be choosers as they say if the price I have to pay is to do this in front of a few strangers then I think that's the price I'll have to pay, just so long as nobody is filming me stripping and doing this then I'll go through with it. I might not object to a few photo's being taken as souvenirs by the audience so long as my face isn't shown but that would be my limit.

All the best to you on your anal quest John; I'm in the same boat as you wanting to make my anus "non-virginal" after all these years!

Hi Watertrain,

Seem to be getting plenty of encouragement and advice and if that's you in the photo I think someone's really going to enjoy taking your anal virginity!