Position for first anal

With wife:

She was on her side and I was behind her. I caressed her clit and pressed my glans very gently against her anus, without any strength or violence. Under my tender stroking, she slowly opened and let my glans penetrate. She then pushed against me a little more and suddenly I was all in. We enjoyed the feeling of this intimate union for a long time without moving, until we slowly began to fuck. I continued to spoil her clit until she reached orgasm. The intense contraction of her anus then also triggers my orgasm.

with a male friend:

He was lying on his back with his feet on my shoulders. So after a careful penetration into his anus I could masturbate his penis in the same rhythm with my movement. He reached his orgasm before me, and I could intensely feel and enjoy the rhythmic contraction of his anus around my shaft. Seconds later I also squirt deep inside him.

With my enemate, I laid on my back to get pegged with a Dick Rambone. She loved invading and controlling my hole with that huge rod of plastic! I loved it too. My hole was Hers, not mine…

I became Her enema sub. Heck, I’d been one since age 5 at the hands of Mom, aunts and female cousins loving every enema, as well as their outgrown clothes my cousins made me wear. I began to love wearing dresses, panties, slips and Maryjanes, and eventually, bras. I became an almost total sissy! But I was still attracted to girls.

Ages later, I found myself an enemate. By then, I had become very experienced with anal toys. We decided that She needed to peg me with my Dick Rambone dildo. That led to her whoring out my hole, in the fertile Toronto area for action. After a previous evening of enemas and pegging, we’d go to a gay bar, with me en femme, to get me fucked, bareback only. Underneath my dress hem, I wore a double bardex nozzle. For every glass of wine I drank, She injected one under the table into my nozzle,getting me good and drunk. After a while, She took me to the women’s’ room to expel, then opened my previously well douched hole for any and all loads, regardless of HIV status. Some I took tummy down on the floor. At that point, it didn’t matter as long as my anal was penetrated.

I loved it taking a cock or a pegging on my back or on my tummy. I am a cock/dildo slut!

My first time was lying on my back with legs over my head, which gave a partner a full control. Needless to say, it was not the greatest experience for the first time, especially considering he had impressive 21 cm tool

And for the first-timers... If you are in good physical form - cowboy position: it will allow you to control both depth and the tempo (and stimulate your prostate if you are male 😉 ). If not - I suppose on all fours would be a good choice

Naked, face down, legs wide apart…. Still my favorite way to get fucked… altho a few pillows under my hips really gives me deeper penetration. Edit… I asked for it my first time and my well hung friend was happy to oblige but had no lube so I suggested butter from his fridge. It worked and I loved it.

Here we are again. This topic keeps coming up again and again. I usualy answer this curiosity , so I am going to drop my two cents in once again.

Position naked arse in the air, face in the dirt age not sure. I know I was not in the double digits yet. My friend, older than me, did the deed, just rammed it up my arse and reamed away . We had found a porn mag in the garbage and were experimenting with sex using it as a guide. We had already tried the blow job out that was great. The bum stuff looked exciting so we tried that too. I liked it a lot. We worked my other hole open eventualy.

Position for a first time. Just be horny as all fuck and want it up the arse . Any position is going to be a stretch; it will feel good if you want it. Not so good if you're tense. Any position is a good position.

It happened in the backseat of a car, my girlfriend was laying flat on her stomach, and I used plenty of Vaseline, that she had in her purse. It was the most delicious experience for both of us. Over 50 years ago, and still fresh in my memory. The vagina isn’t nearly as exciting.

.

1. The first, second, and third times my wife pegged me I was bent over against the bed. After more reading on Zity, we tried spooning and with me on my back with my legs on her shoulders.

2.

The first two times I did anal to my wife we did the doggy position. Many years later, we tried it with her bent over against the bed.

With more reading on Zity, I think cowgirl for her would give her more control on how fast she wants to be entered to reduce the pain. I also think that spooning is very relaxing

My partner and I were cuddling in bed one morning, he was spooning me. I just wiggled my bum into his crotch and it just started from there. So the first time I had anal sex was in the spooning position.

@Millie_Millicent Something like that happened to me a lot time ago - spooning, girl relaxed and it went into the wrong hole, so to speak. I however did not dare continue to ream her without adding lubricant! And then she became tense as I was adding the lubricant.

@Jacana It was a great position for a first time and, like you mention, relaxed.

1- doggy, partner went in slowly, stopped for a few seconds inside, then when I gave the ok continued. Lots of lube ofc

2- doggy or similar, a lot easier to access, to do some fingering before actual penetration and to manage how fast you go in