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Your first anal experiment

What was the first thing you experimented with in your anus?

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Well-known Member
Apr 7, 2009
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New York
Ok Guys time for a new poll:001_rolleyes:
This time lets answer about our first experience with experimenting with doing something anal. I am not talking about your first time having anal sex, I am talking about the first time that anything went into your anus that your chose to go in there (medical exams do not count). In your comments you can give details like what the item was, did you use a lube, what did you use, how old were you etc.
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I remember in college, my Junior year, I had a bf who rimmed me. I liked that a lot, so I decided to try adding a finger to my masturbation ritual and oh, boy, did that ever set things off. I'm still working on that stubborn hubby of mine to try anal... he's reluctant. In the meantime, I guess I have that virginity still intact.
My first time was a finger, but not mine. My cousin had just had a football physical, and was eager to show me what had been done to him. At first I was scared, but he calmed me and, since mom wasn't home yet, we tried it out. I was immediately hooked, and never looked back, so to speak! Even though I was only eleven or so, I knew what I liked! I was excited to show my neighbor friend what my cousin had taught me, and it was he who first tried full on anal with me.
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Lady answer here...
The only thing that has been up there is a penis. And no, I didn't enjoy it. After the first time, I took a shower and cried. It was weird. I got a little bit more used to it after that, but still never enjoyed it.
The first thing that ever went up my bum was a penis. And golly did I enjoy it! So now I put all kinds of things in there (mostly body parts and sex toys). The only thing I can say is I was probably too young when I started having anal sex at 14. I wish I would have put it off a bit, but I guess I'm glad I knew what I wanted and liked at a young age and didn't have to spend time being awkward about it.
Anal stimulation was never a part of my j/o routine.

I once lived with a hypersexed roommate 15 years my junior on and off again over a span of 17 years. He was primarily (99%) straight, a womanizer, and could charm the pants off of anybody. On those rare, rare, rare moments when he was horny and needed a fix, we were fooling around in the bed together and he asked me to play with his ass. At the time he was 30 and I was 45 and although I was much older, I was Gay after all. Surely, by 1993 I knew what to do. Since I had never even played with my own ass, he understandably found my attempts unpleasant. Hell, I didn't know what I was doing. He was the one who routinely incorporated ass play while he was jacking off, not me.

So, after my best but most uninformed efforts failed to please him, I decided the next day to fashion my own Dildo The lowly carrot was my first weapon of attack. I purchased two of the fattest and hopefully most stout carrots I could find. As I was fearful of their breaking while inside, I put a condom on it to increase my chances of retrieval, should it break. The last thing I wanted to happen was to find it necessary to visit the ER in my rural hospital and ask them to remove a carrot caught in my ass! LOL

Being that I am a bit "anal-retentive" anyway, but specially when fashioning sex toys, I wanted to make sure no detail too small was left out. Like carving a pumpkin at Halloween, I took my requisite carving skills to fashion the anatomically perfect erect carrot-turned-penis worthy of being prominently displayed in Madame Tussuad's Wax Museum. My efforts were painstaking and the contours of a beautifully carved dickhead with its flared edges and it's pouty, delicately kissable tip were the two design elements essential for this project to see daylight, only upon use to be immediately banished into a tunnel where the sun don't shine! I felt like a sculptor and felt so good about my first efforts, that I fashioned a second one expressly for my roommate to use at his own discretion and to add his own artistic touches.

To make a long story short, it did work but could have worked better if I had some lube available. My whole sexual preferences were oral in nature ONLY, back then. All of this seems today rather sophomoric looking back, doesn't it, but remember the internet was in its infancy and I did not even own a computer back then. The only computers with internet capability I had use of was in my office at school and venturing off into porn-land was strictly forbidden.

In fact it has only been in the last two years after extensive exposure of internet porn, that I have finally developed an interest at age 60. I guess I must be the latest bloomer on record to anal pleasures.

Embarrassed, but truthful,

i enjoy setting a small colony of gerbils free inside my rectum.....

just kidding, i most definately was curious, so i used a hairbrush handle....awkward..
i enjoy setting a small colony of gerbils free inside my rectum.....

just kidding, i most definately was curious, so i used a hairbrush handle....awkward..
Fingers. Followed shortly after by penis.
Haven't tried it here myself...tried to get an ex gf let me do it to her once but she wasn't having it lol
a finger but when condoms were beginning I wondered what it would feel like it. I did a cucumber in a condom could change to a larger size too. A carrot was not fun. Too rigid and sharp point. Got to take a nine inch cucumber easily
Looks like Miss D and I have something in common!!! (YOU be the judge!!):001_tongue::w00t::ohmy: