First time anal?

  • Thread starterrataver
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Disco-cuck said:
I was lured back there last week. When I arrive we always kiss and make out like crazy which gets me horny. I then shower and douche deeply, towel dry and we go onto his bed and 69. We then kiss more, then 69 over and over. He then gets out the oil to massage me as a lie there stroking. He slides down and begins to rim me. I am trained to hold my legs up and my ass open as he licks me out. He then stands and slides his cock in. I really went crazy telling him to pound my ass good. We fucked for at least one hour. I was sore for days, but I'm aching to go back again this week for another pounding.
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Part 3 - I went over last Friday morning and got right into it. This time he blindfolded me as soon as I got in. He stripped me down, had me lay on his sofa and got my body massaged and oiled. I was rock hard by the time he started flogging me and spanking me. He then led me into his bedroom and tied my wrists and ankles to his bed. I could her the camera clicking and video being shot while he was throat fucking me and sucking me hard. He finally loosened the leg restraints enough for my knees to come up to my chest and he fucked me until I begged him to stop as I was getting raw. I orgasmed onto my own belly as he pounded my ass. By the time we finished our session we were at 4+ hours. I was exhausted for the rest of the weekend. He sent me pics and video clips which was hot. He's already got a guy lined up to spit roast me next time I'm over.
 
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TimKnowsPlaceMWM said:
i should add that if you are on female hormone regimen, the womanly orgasm will be even more intense ... but even without the female hormones, the prostate is a very sexy and sensitive erogenous zone, that most boys don't ever find out about ... unless they end up in some prison somewhere :p
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I have a massage guy who massages my prostrate! It is so erotic! I never planed to do him but I did!
 
I discover getting butt fucked very early when a school buddy said he “ wanted to show me something”. I lost my ass cherry to him that night and ended up with an ass full of cum! After that I taught my best buddy how to butt fuck me and he fucked my ass every wee for the next five years!
 
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Rockford said:
I discover getting butt fucked very early when a school buddy said he “ wanted to show me something”. I lost my ass cherry to him that night and ended up with an ass full of cum! After that I taught my best buddy how to butt fuck me and he fucked my ass every wee for the next five years!
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Once over that initial hurdle ,taking cock just gets better.
 
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srx said:
Once over that initial hurdle ,taking cock just gets better.
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Yes it does! Once your ass gets broken in it feels for sexy to to get butt fucked!
 
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Good to hear
 
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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.
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Your sissygasm is coming soon
 
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blkallover said:
Your sissygasm is coming soon
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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.
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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.
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I think it must! Being fucked like a girls is a great experience
 
rataver said:
Any cucks here who had a dick in their ass? How did it happen? Feeling?
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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
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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!
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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
 
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