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First time anal?

  • Thread starterrataver
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Laceyfemme said:
For me it was a fairly natural progression when I went from just sucking cock at adult theaters and bookstores, to sometimes meeting men online and inviting them over to my house. About half of them wanted to fuck me and I usually let them. We always used rubbers. I was a frequent user of reasonably large toys, so I was definitely ready and enjoyed it, although I never had a prostate orgasm that way.
Your sissygasm is coming soon
 
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blkallover said:
Your sissygasm is coming soon
Yes, I had my share of sissygasms back in the day with large toys. I used to play that way for hours at a time, crossdressing, watching BBC or cumshot porn, and going through cycles of teasing my clit until I got too close to cumming and had to go soft again.

But prostate play was definitely the most intense part of the experience, better than any clitoral orgasm by far. I would leak all over and have a true hands-free sissygasm about a half or third of the time, usually while staying cumpletely soft. So satisfying, both physically and emotionally.
 
Laceyfemme said:
Yes, I had my share of sissygasms back in the day with large toys. I used to play that way for hours at a time, crossdressing, watching BBC or cumshot porn, and going through cycles of teasing my clit until I got too close to cumming and had to go soft again.

But prostate play was definitely the most intense part of the experience, better than any clitoral orgasm by far. I would leak all over and have a true hands-free sissygasm about a half or third of the time, usually while staying cumpletely soft. So satisfying, both physically and emotionally.
Sometimes i do get a bit stiff when i am being fucked, but you are right ... there is something very special ... and feels so right being fucked like a woman ... when you sissygasm with your clit still limp and squishy ... tho totally tingling. you ... or at least i ... imagine it's c;lose to how a woman must feel when her man fucks her good.
 
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TimKnowsPlaceMWM said:
Sometimes i do get a bit stiff when i am being fucked, but you are right ... there is something very special ... and feels so right being fucked like a woman ... when you sissygasm with your clit still limp and squishy ... tho totally tingling. you ... or at least i ... imagine it's c;lose to how a woman must feel when her man fucks her good.
I think it must! Being fucked like a girls is a great experience
 
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rataver said:
Any cucks here who had a dick in their ass? How did it happen? Feeling?
I got my butt fucked a lot! Love the feeling
 
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Sex with a woman is ok but nothing like the real thing.
 
I had some experiences with my best mate in my early teens which was good fun and only started again in my late 30's. Since my early 20's until now, I've always used toys and have gotten bigger and bigger. I have been catch up with a guy for the past 12 months without my wife knowing and at the start of this year during a catch up, he asked if he could fuck me. He is a good size and was nervous about it being my first time but I knew I could take him. After 5 mins of play, I grabbed his cock and worked it in until he was the whole way in. It was a much better feeling than any toy and having him moving in and out made me cum and not long after, he came in my ass which was the best
 
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Malchow said:
I had some experiences with my best mate in my early teens which was good fun and only started again in my late 30's. Since my early 20's until now, I've always used toys and have gotten bigger and bigger. I have been catch up with a guy for the past 12 months without my wife knowing and at the start of this year during a catch up, he asked if he could fuck me. He is a good size and was nervous about it being my first time but I knew I could take him. After 5 mins of play, I grabbed his cock and worked it in until he was the whole way in. It was a much better feeling than any toy and having him moving in and out made me cum and not long after, he came in my ass which was the best
Hot story! I lost my ass cherry to a school buddy when I was 13! I didn’t even know what butt fucking was til that night! After that I told my best friend and he started fucking my ass regularly! We never told a sole! He fucked me from 7th grade until I left for college! Always bareback. It’s erotic to think about how many gallons of cum my old friend pumped into my ass all those years! He and I are still friends. I talked to him on the phone yesterday. Every time I talk to him I think about how he fucked me so much and wonder if he is thinking the same thing!
 
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Rockford said:
Hot story! I lost my ass cherry to a school buddy when I was 13! I didn’t even know what butt fucking was til that night! After that I told my best friend and he started fucking my ass regularly! We never told a sole! He fucked me from 7th grade until I left for college! Always bareback. It’s erotic to think about how many gallons of cum my old friend pumped into my ass all those years! He and I are still friends. I talked to him on the phone yesterday. Every time I talk to him I think about how he fucked me so much and wonder if he is thinking the same thing!
Great story and you sure were lucky. The friend from my early teens would out his older brother pornos on and once he could see I was hard, would guide me down to his har cock and make me suck it. When he was about to cum, he would climb on top of me and we would rub dicks until he came all over me. He would then jerk me off until I would cum. We did this for about 2 years until he moved away at 14 and we have never seen each other since
 
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You think he is? We never did it or even mentioned it after high school but in 2020 all those years later he said something that makes me think he remembers fucking me well
 
Those create great memories and friendship that last! Me and my J o buddy are still friends alls these years later!
Funny, he was best man at. My wedding!
 
My first time getting but fucked was by a school buddy at a sleep over! I didn’t even know what it was til that night! After he took my cherry I kept doing it all thru school
 
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Rockford said:
My first time getting but fucked was by a school buddy at a sleep over! I didn’t even know what it was til that night! After he took my cherry I kept doing it all thru school
OK,did it hurt much,what was it like?
 
It hire like hell the first time! No lube, I didn’t even know a dick could fit in an ass! I was intimidated by him and just laid there taking it! When I realized the head of his dick was in my ass I was so surprised. He pushed in and out and it hurt! Then all of a sudden his dick started sliding in and out of my ass easier! He had shot a load of slick cum in my ass which lubed me up!
After he came in my ass he rolled off to go to sleep. I remember laying there my ass stinging. From being stretched. It fell like his dick was still in me! I reached back an felt my stretched ass covered with slick cum!
 
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Rockford said:
You think he is? We never did it or even mentioned it after high school but in 2020 all those years later he said something that makes me think he remembers fucking me well
He remembers thats nothing you would forget
 
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