Opening Up to Trying Anal

[massbear]

I've been exchanging blow jobs since I was about 9 years old. My best friend and I were "suck buddies" from 9 until around 12 or 13 when his family moved away. I sucked off a few other friends after he moved but upon entering high school I turned my attention to girls. This lasted through college and into my 30s. When my sexless marriage began to fail, I went to a gay bath house to see if I would still be into cock...I was! During that encounter, one guy I was blowing wanted to kiss and fuck. I discovered I was not at all into kissing guys however I was willing to let him fuck me. Unfortunately I was too nervous and he was big so he couldn't really get it in. Even after this encounter, I still considered myself bi-curious and when trolling the web for hook ups I always stated I wasn't into trying anal even though I enjoyed fingers and toys up my ass. I've also had enjoyable experiences rimming. On the rare occasion my wife rimmed me I loved it and I equally liked rimming her, more than eating pussy even. Beyond that, I tried to avoid watching anal scenes in gay porn. As I've gotten older, that's begun to change. I actually enjoy watching it when I jerk off now and I've become more open to giving it another shot. Under the right circumstances, I think I'd like it.

Anyone else have similar anal experiences and thoughts?

[williamg]

I love anal toys... a LOT. But even with my wife fucking me with a strapon (I shouldn't complain right?), I still want to feel a real cock in my ass. I think I would pass out if I had the chance to take a nice cock on my knees while I suck another one. I find myself always ending up caming with another guy online when I have the time.

[NJwood]

I’ve been using two different dildos and have enjoyed it. Tried once with a guy but he was too aggressive and unwilling to slow down to let me get comfortable. I always tell guys that ask I’d be willing to under the right circumstances.

[Riderinthestorm]

I love anal. Had an ex that we would play together with a big double-ended dildo, one end in her pussy and the other in my ass. We had a great time with that. This was, of course, the same ex that encouraged me to find playmates, of either gender, to bring home to play with.

[SilkyHoseLover]

But even with my wife fucking me with a strapon (I shouldn't complain right?), I still want to feel a real cock in my ass.
My wife is also willing to peg me, but I've confided that I would really prefer the 'real thing'. She's ok with that. She understands, because - in her words - "anal sex feels good."

IMO, unless you're using a dual-density dildo with a soft outer layer and a firmer core inside, a toy feels nothing like a real cock. And, of course, the psychological magic of knowing you're getting fucked by a man is delicious, too!

[csreef]

As I get older, my views are changing. I would like to try Anal, but I would have to feel comfortable with either he man, or woman who would give me it.

[NjbiGuy01]

It comes down to time and patience and relaxing....It was explained to me (later in life) that you first need to clean out. Get a Fleet enema at the drug store and flush out completely, which leads me to the next step, which is relaxing and pushing out like your going to poop. It relaxes both sphincters so that you are as loose as possible. I had a friend like you. We played orally and eventually ended up using toys and vegetables and cock in our asses. We worked our way up from a small vibrator (his mom's stuff ! and I never looked at his mom the same way ever again). Small, larger, largest. He was a decently hung Italian, and it took getting used to it for sure, but eventually he was slapping his balls on my ass as I took all 7 or 8 inches of his cock....

You do feel a mix of pain (burning mostly), but mixed with pleasure too. If you relax and don't sweat it and have a patient partner willing to take things an inch at a time, you can get there. I prefer long and thin, but can handle thicker with the right partners. Also, there are lubes (Anal-eaze for example) which have a mild pain relief to them and that can really be helpful for beginners.

[KDaddy23]

I've met guys and we've gotten into a "pattern" of first, sucking each other off at every opportunity and, at some point, exploring anal just seems to be the next thing to engage in and depending how long we've been seeing each other and how much trust has been established. For me, anal is old hat - been there, done that, so it's the other guy looking to give it a try. You've gotten some good advice here already - no need to repeat it - and now you just gotta get your head right to do it! Good luck!