My first anal was with a guy whose cock wasn't that thick, so it wasn't really painful, even though I was afraid it would be. I enjoy it with small cocks, but I don't do anal with really thick dicks.
I have no desire for even trying it.
I was 17 when Teach introduced me to anal sex. We discussed it and the thought of being fucked in my ass was a big turn on. The process took about a week to 10 Days. It was really worth the time and effort. Trying new things can keep the sexual fires ablaze. Or reignite what has become just a slight wisp of smoke.
I had prepped my body for sex which starts with at least a double enema every time we fucked, which was daily. He started by using 1 finger, which produced an orgasm the first time. When I was comfortable with 1 he went to 2 fingers. Once I was comfortable with 2 he began using a long vibrator that was only about an inch in diameter. Then he fucked my ass with his cock. NOTE: Make sure if you use toys they will not be able to disappear into the depth of your bowls. Then it will become uncomfortable to have to make a trip to the ER for retrieval.
During the weekend of my first gang bang Teach offered me to his fellow biker group. One was nicknamed Horse. His cock was slightly longer than a standard plastic 1 foot ruler and about a 1/4 inch wider. The first night of the 3 day gang bang Horse fucked me in my ass. One of my regular lovers for the last 37 years has an 11.1 X 1.75 inch cock. He fucks my ass a couple times a week. Taking it slow and easy with each step up was a little uncomfortable at first, but not painful.
Once I relaxed and got comfortable with it the orgasms are fantastic and well worth learning the art of anal sex. For those interested I would recommend taking the time to start with something small and build up to a cock or strap on. Also take the time to prep your body and keep it clean. Also use lube if needed it will help to keep it from being painful. Also your ass will close back up shortly after the ass fucking is concluded.
Hubbie thought we had given each other our virginities. He used the same technique Teach had used when we started having anal sex. So I acted like I had never had anal sex before. Hubbie did not find out that he had married a slut until about a year after we were married.
I have recently published my first two stories here on LS. They are titled "My First Gang Bang and Golden Shower" Parts 1 and 2. My stories are based on a real event and told to the best of my memory. Writing them and reminiscing about my first gang bang was very exciting and orgasmic. They are about my 5th lover that I started dating on my 17th birthday. He was one of my high school teachers and 8 years my senior. He was also very educated about sexuality. Teach was responsible for bringing me into the erotic pleasures of "The Lifestyle." During that three day weekend gang bang I had many first and the intensity and length of my orgasms more than doubled.
It's been one hell of an erotic ride that will have lasted 42 years in a few weeks. It is still as erotic today as it was when I was 17.
Brandie
I guess it would be neither one ... I really woud have no interest in being involved (personally) in that.