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First time anal?

  • Thread starterrataver
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Niceguytoo said:
I have been a bottom boy since early on!
A sleepover sounds so naive,who did it?
 
srx said:
A sleepover sounds so naive,who did it?
A school buddy named Dennis he was a year older than me. I didn’t know what butt fucking was until I felt his dick penetrate my ass! Quite a suprise
 
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I have enjoyed anal since I’ve been 18. I’m extremely gaped at this point in my life.
 
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i learned over time.

my first several times were painful. i was at a xxx store getting fucked at a gloryhole. Gloryhole fucks are all the same, fast and furious. at first i used the wrong lube, vaseline and latex do not work well together i am told. it was very painful. i would put two tokens for the video feed in my mouth and bite down on them while the guy hammered my ass. still i really got off on the humiliation of being fucked in the ass by stronger man. i tried different lubes and found that the store brand water based lube worked best for me. so much better.

one night at the same xxx store, i met an old gay man with a absolutely huge cock. he was the biggest i have had in 30+ yrs. he had an average cock head but his very long cock got thicker towards the base. I thought there is no way that thing would go inside me. he took me to a larger booth with no gloryholes. he gently applied lube to my hole and fingered me with only one finger. he put on a condom and got into position behind me. he told me to gently push just as i would when i went to the bathroom. I did as he asked and viola his very large cock slide about one third of the way inside me with ease. he then pulled all the way out and applied more lube. again, he got into position and told me to gently push as he eased inside me once again. this time he must have been about half way inside. he pulled back and told me again to push. i remember his voice was soft and as he moved inside me he would say, "puuuuuuussssssh". everytime he pulled back he would say "yeeesss". when he thrust he would say, "puuuuuussssh". "yeeessss" "puuuusssshhh" "yeeeess" "puuuuusssssh"

in no time he was balls deep in my ass. i remember feeling very full and stretched. Oddly, there was no real pain. i would describe it as a mild to medium burn with an overwhelming feeling of needing to go to the bathroom, meaning have a bowel movement. I told him i felt like i needed to shit and he explained that my body thinks his cock is poop. he told me to just relax and enjoy it.

then he started. he rotated his hips in a circular motion. it felt like he was stirring my insides with his cock. he was deep in my ass and rotating his hips in a circle. i could feel his hands not gripping but pushing down on my hips. he would pull out some before corkscrewing back in. it was the most amazing sensation. he would enter me from different angles. this was very different than the usual straight in and straight out pounding i had been getting there.

i am not sure how long he fucked me. it seemed like a very long time, but also it seemed like it ended to quick. his movements became faster and more intense. his cock seemed to get even thicker and hard as steel. his words were very encouraging telling me, "yeeessss, thats gooood. youre doing great. you feel amazing. thats goood". i thought i may have been making too much noise so i clinched my lips tight, but i could not help moaning with each turn of his corkscrew hips. as he thrust increasingly hard, i began to grunt louder and louder. he said, "yes. yes, thats it. let them know how good it feels. let everyone in the building know how good my cock feels. let them know you are getting the fucking of your life. let go. let go. just let go. yes yes yes". the louder he got that louder i got until i was grunting and saying "yes. oh yes. oh god yes"

i felt his hand push firmly between my shoulder blades forcing my upper body lower and my ass higher. throught my grunts and groans, i heard the unmistakable sound of flesh hitting flesh. slap. slap. slap. he was pounding me. my ass burning like fire. his relentless pounding suddenly stopped and i felt his cock throb inside my tight hole 2, 3, 4, and a long 5th time as he ejeculated into the condom. he held still for only a moment before pulling completely out of my ass. i can not think of an adjective to describe the void i felt in my ass. it just felt empty.

he was right. that was the fucking of my life. i had one other experience that was memoriable but nothing like that night. the night i learned to "puuusssh".
 
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Having a nice size cock fucking my asshole is tge most sensual and erotic feeling there is….much better then a dildo. I just can’t get enough .
 
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"Cumming" as a boy is absolutely NOTHING like having a womanly kind of orgasm from being fucked by a hung, experienced man. If you are on female hormones it is even much better. And when he is verbally and emotionally dominant and knows how to make you really feel like you are his bitch, it is beyond belief.
 
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Tinynlimpcuck said:
Having a nice size cock fucking my asshole is tge most sensual and erotic feeling there is….much better then a dildo. I just can’t get enough .
Nothing like the real thing throw that toy away
 
TimKnowsPlaceMWM said:
"Cumming" as a boy is absolutely NOTHING like having a womanly kind of orgasm from being fucked by a hung, experienced man. If you are on female hormones it is even much better. And when he is verbally and emotionally dominant and knows how to make you really feel like you are his bitch, it is beyond belief.
I have no idea about hormones, but when I am a bitch it makes me squirt uncontrollably every time.
 
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Tinynlimpcuck said:
Having a nice size cock fucking my asshole is tge most sensual and erotic feeling there is….much better then a dildo. I just can’t get enough .
it makes me squirt without any control.
 
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I’ve never done it. I have used my wife’s dildo a couple times. That feeling when my ass finally opens and it goes deep is so amazing
 
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Would love to try it. Not sure how to meet someone in a safe way.
 
samanthaNwilli said:
I have no idea about hormones, but when I am a bitch it makes me squirt uncontrollably every time.
Samantha, darling, if you start using female hormones (under medical supervision only !) to enhance your feminization, you and your sissygasms/orgasms will graduate from bitch level to BITCH LEVEL ! 😍



GDAZqyGaQAA91H9.jpg
 
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rataver said:
Any cucks here who had a dick in their ass? How did it happen? Feeling?
I've only had a few hard cocks in my ass. They have felt great every time though.
 
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TimKnowsPlaceMWM said:
Samantha, darling, if you start using female hormones (under medical supervision only !) to enhance your feminization, you and your sissygasms/orgasms will graduate from bitch level to BITCH LEVEL ! 😍



GDAZqyGaQAA91H9.jpg
Samantha is my wife.
 

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