HornyLittleDevil2026
Pussy Lover
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- Jul 13, 2026
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- 287
The first time you had your asshole caved in, what did you think: never again, definitely again, or every time.
First Time Anal
- Thread starter HornyLittleDevil2026
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shewantsmore
Literotica Guru
- Joined
- Jul 2, 2006
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- 12,853
My 1st time i said to myself hever again but i let it happen again
How do you like it now?
bisissyhusband1
Sissy Wife
- Joined
- Mar 24, 2025
- Posts
- 806
When my wife started pegging me, I couldn’t get enough. Now we do it all the time.
PixieSweet
Experienced
- Joined
- Jul 6, 2026
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- 58
After my first experience, for me it was very much ‘definitely again’
gtnlynn
Really Experienced
- Joined
- Jan 4, 2017
- Posts
- 3,971
My wife's first time was in college when she was having sex with her current fwb. With no warning, he pulled out and rammed his cock into her anus. She screamed in pain and kicked him away. She has never let anybody try anal sex on her since then.
Wonderer67
Optimistic nihilist
- Joined
- Sep 25, 2020
- Posts
- 22,301
I am male, but he was my first experience.
There was a very similar thread on here posted by someone else… but I’ll share the story again.
I was seeing this very fiery, redheaded, Italian woman from South Philly on the mid 90s. She had the attitude and all. We met and there was instant attraction and we started dating, even though we were both seeing other people.
We slept with each other a 5-6 times already, but we were in my apartment having sex (vaginally) and she told me to get some lube. I came back and she was bent over for me and told me to put it in her ass. I did not need to be told twice, as I was always infatuated with anal sex, but my first wife didn’t want it at all.
It was everything I had dreamed of: tight, sensual, a bit taboo and I absolutely loved the look of me opening up her asshole with my thick cock.
Turned out, she loved anal, and it was part of her repertoire. We saw each other all that summer and had anal sex a number of times and in a number of positions. It started my infatuation with it.
There was a very similar thread on here posted by someone else… but I’ll share the story again.
I was seeing this very fiery, redheaded, Italian woman from South Philly on the mid 90s. She had the attitude and all. We met and there was instant attraction and we started dating, even though we were both seeing other people.
We slept with each other a 5-6 times already, but we were in my apartment having sex (vaginally) and she told me to get some lube. I came back and she was bent over for me and told me to put it in her ass. I did not need to be told twice, as I was always infatuated with anal sex, but my first wife didn’t want it at all.
It was everything I had dreamed of: tight, sensual, a bit taboo and I absolutely loved the look of me opening up her asshole with my thick cock.
Turned out, she loved anal, and it was part of her repertoire. We saw each other all that summer and had anal sex a number of times and in a number of positions. It started my infatuation with it.
Wonderer67
Optimistic nihilist
- Joined
- Sep 25, 2020
- Posts
- 22,301
As for having my own ass penetrated, it happened once before I met my wife. And I played with several prostate massage massagers.
But the first time my wife pegged me, was amazing. She got a strap on from a sex store. As she was penetrating me, I had a hands-free orgasm and came all over the place.
She pegs me every so often, and she’s probably pegged me 30-40 times, but I’ve only had a hands-free orgasm that time and one other time.
But the first time my wife pegged me, was amazing. She got a strap on from a sex store. As she was penetrating me, I had a hands-free orgasm and came all over the place.
She pegs me every so often, and she’s probably pegged me 30-40 times, but I’ve only had a hands-free orgasm that time and one other time.
HornyLittleDevil2026
Pussy Lover
- Joined
- Jul 13, 2026
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- 287
Similar thing happened to me with a college girlfriend. Although there was some warning, I was way too aggressive and just rammed it in. She screamed, curled up into the fetal position whimpering, and we never tried it again.
Suckharder55
Really Experienced
- Joined
- Jun 30, 2026
- Posts
- 250
Very young the first time. It was awkward and painful, but I was determined to get it done because I liked the sensation and wanted more
gtnlynn
Really Experienced
- Joined
- Jan 4, 2017
- Posts
- 3,971
The guy who did it to her felt awful. He was just a bit too drunk. They remained friends, and she even talks to him occasionally now, but she never went out with him again.
HornyLittleDevil2026
Pussy Lover
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- Jul 13, 2026
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Yeah, I felt bad too. One for hurting her, and two for not taking it easy so we could actually experience it.
gtnlynn
Really Experienced
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- Jan 4, 2017
- Posts
- 3,971
We learn a lot of useful things in college, not necessarily in the classroom.
StrongMaster7
Literotica Guru
- Joined
- Dec 3, 2004
- Posts
- 2,413
I was shocked, angry, helpless, then aroused so much. All that in maybe two seconds. Loved it after that. Wish I could have it every night that way.
Shaglus_Ziegler
Virgin
- Joined
- Jun 7, 2022
- Posts
- 3,709
It’s quite arousing for me. Crave it sometimes and don’t get it enough!
I am male. I was a newbie on the scene and was with a date. A guy I met at a football game. He was a handsome guy with a lovely cock. He let me suck it for a few minutes. Then he took me to his bed and literally thrust his cock in one long stroke into my virgin ass. My pain didn't matter to him. He said it's the best way. Then he pounded me for a long time and came in my ass
https://realbooru.com//images/48/61/4861acaf8f84974e293daf0739bfaa23.gif
https://realbooru.com//images/48/61/4861acaf8f84974e293daf0739bfaa23.gif
Katiel3036
Newbie
- Joined
- Jul 3, 2024
- Posts
- 543
First thought was owwwhhh, second was, this kinda feels good. 3rd was i freaking love this
Glassnslate
Fun Seeker
- Joined
- Dec 29, 2024
- Posts
- 49
I was in college, I was 19. I was having sex with a guy who was not very experienced. He always wanted to wear condoms the first 10 or 11 times we had sex. One of those nights he wanted to try anal. I was game to try, I had never done it before either. He lubed me up, slid a condom on, and we tried to do it. It just wasn’t gonna work. It was uncomfortable and didn’t feel right, and the condom would not stay on.
Eventually, I got him trained that we were not going to use condoms when we had sex. And about six months later after that first attempt we were at his family cabin. We snuck up there in the middle of the afternoon for some quick fun. We had fucked in a spooning position and he had cum in my pussy. We were barely done and he whispered in my ear “would you like to try anal again?“ without thinking in the heat of the moment I responded “yes”.
As his cock was covered with my pussy juice and his semen, he placed the tip against my ass and started to gently work it in in the spooning position. As he did, he reached forward and started rubbing my clit. All of the sensations drove me absolutely wild. Eventually, he was able to work his cock all the way in, and we laid there in the spooning position and fucked gently for a long time. I don’t know how long it was, but I seemed like I was in perpetual orgasm the whole time.
Glass
Eventually, I got him trained that we were not going to use condoms when we had sex. And about six months later after that first attempt we were at his family cabin. We snuck up there in the middle of the afternoon for some quick fun. We had fucked in a spooning position and he had cum in my pussy. We were barely done and he whispered in my ear “would you like to try anal again?“ without thinking in the heat of the moment I responded “yes”.
As his cock was covered with my pussy juice and his semen, he placed the tip against my ass and started to gently work it in in the spooning position. As he did, he reached forward and started rubbing my clit. All of the sensations drove me absolutely wild. Eventually, he was able to work his cock all the way in, and we laid there in the spooning position and fucked gently for a long time. I don’t know how long it was, but I seemed like I was in perpetual orgasm the whole time.
Glass
