Hardest Moment For A Newbie Bottom ?

[deine_huendin]

beside a hard and deep fucking later-

what is the greatest challenge, the big point, for a newbie bottom:
1. the moment when the glans opens the sphincter ?
or
2. the moment when he shoves his cock balldeep inside ?

 

[chrisrobin]

Its that moment when his cock goes in, the mushroom head gets past the first muscle band and stretches the ring wide, that moment when you want to stop him entering your anal passage any deeper, when he instant hurt is there.
Thats when he has to count to ten, let the pain subside and let the top take him gently. A virgin fucker who rams his cock in balls deep shows no sympathetic understanding at all. My mentor let me take my time taking his hard cock with rests as I got used to being penetrated, let me rest and acclimatize myself to his length and thickness as each inch went deeper, and, once in, his balls on my buttocks, that's when I had my first fuck. Never worried about not being able to take it after that.

 

[insert_8]

Its that moment when his cock goes in, the mushroom head gets past the first muscle band and stretches the ring wide, that moment when you want to stop him entering your anal passage any deeper, when he instant hurt is there . . . .

For me, that was certainly the most challenging mental part. That's when I KNEW beyond any doubt that I was doing something taboo, but more significantly I was being "taken" by a man, and used for his sexual pleasure the way a man uses a woman.

Physically . . . yes, it hurt. A little more than I expected. I don't think that anybody getting fucked for the first time - man or woman; pussy or ass - can truly relax, and that probably makes it hurt a bit more. I yelped a little, possibly as much from the surprise, as from the actual pain of the huge cock head popping in (for a virgin hole, the cock is always huge, regardless of size). The hurt was a momentary stab, and - to be honest - it was a significant part of the overall first-time experience. It concentrated my attention on what was being done to me. If I could do it over again, I'd want it to hurt at least a little, even a lot.

The guy who got my ass cherry paused when he broke in, but probably not long enough. I think maybe I signaled to him that it was OK to finish the insertion before it actually was OK. Perhaps to show off my macho, the I-can-take-anything attitude that all guys have to some extent. He completed the insertion by splitting my rectum with one firm, smooth stroke. That hurt, in a different way. He may have pushed through a curve in my rectum, but regardless of the details it made me cry a few tears So that moment of completing the insertion was physically the greatest challenge. He noticed, but pretended not to. He fucked with long, deliberate strokes, and I regained control. It was just starting to feel good when he spilled his sperm inside me.

 

[insert_8]

to concede that you worship cocks, that you adore big hairy top alpha men...

I don't worship cocks, and although I prefer that the man who fucks me is "manly" in appearance and actions, mostly I'm attracted to the sensations - both mental and physical - of being fucked by a guy who knows what he's doing.

he will like it more than fucking a girls cunt
because your boi-cunt is so forbidden, so innocent, so tight
more challance, more act of defiance, more fun than fucking a cunt

I don't necessarily think I'm offering something better than a pussy, but I'm offering something different and complementary to a vagina. The taboo factor is part of the mental sensations for both of us, and the tightness is part of the physical pleasure. I do not have a "boi-cunt" - I have an anus, a sphincter, and a rectum. Those parts of me can both give and receive unique pleasurable sensations.

at this moment it is important that he is self-confident,
that he does not hesitate, that he gives you the feeling of confidence
despite the following pain

I don't know if it is "confidence" as much as "determination". Him, knowing that he wants to enter and enjoy me. Me, knowing that I WANT him inside, and want to give him pleasure.

The pain is a very complicated thing. Pain HURTS, and I am NOT into pain per se. But there is a special kind of satisfaction to the pain of being entered and fucked. Some of it is simply the macho thing of showing that I can "take it", but there's much more to it that I don't understand. For me, the discomfort is part of the overall experience. Especially the momentary stab when the erection forces my sphincter to yield.

And this was true several times over when I took it in my ass for the very first time. I'm glad that it hurt, though I would not want to experience intense, nor sustained, pain. I'm glad that I gave out an emphatic "OUCH!" when he broke through. I'm glad that he held me firmly in place even though I was squirming (and repeating "Ouch! Ouch! That hurts!"), until the initial shock passed and I was becoming accustomed to the violation. (He told me afterwards that "Ouch! Ouch! It Hurts!" are the last words of most guys getting their ass cherry popped.)

I know that he got satisfaction feeling my legs kick and scissor, and seeing my face scrunch up in a grimace, and my hands clutching the sheets. (If he hadn't put me on my back in the traditional woman's position, my arms and legs would not have been free to respond that way.) When my tears came, I'm glad he continued his long, deliberate, strokes. And, even though I was embarrassed when I first thought about it, I'm glad I wrapped arms and legs around and clutched him to me as he inseminated me. On the other hand . . . . I'm glad nobody else was there to see me do those "unmanly" things.

 

[insert_8]

That was something I will remember was his shooting his spunk in me after that first fuck . . .

Definitely! I was on my back, a pillow folded under my hips and he was laying out full length on top of me. The pain was mostly gone and it was beginning to feel really good. (Well, actually, it felt good from before ho popped my sphincter, but the good feelings were mixed with the pain.) He was fucking me with long strokes at a moderate tempo. He paused at the end of an out-stroke, then shoved it in forcefully and pressed my body hard under his. I vocalized a little discomfort. I could feel his cock jerking deep inside me, and his body tense against mine. It took a second or two to realize what was happening. When I realized he was cumming inside me, I wrapped arms and legs around him tightly, clutching him to me, feeling the contractions in his body. I couldn't feel the actual squirts, but I wanted to have ALL of his sperm inside me - his wife was going to be frustrated because he had emptied his balls into my rectum.

After he finished twitching he took a couple of strokes and I could tell that the texture had changed inside me. Of course, he was starting to go soft but his cock slid so easily in and out. I asked about that afterwards, and he told me about "anal silky seconds" - a sensation I REALLY want to experience.

 

[insert_8]

also like a whining "NO", a STOP, a "please don't", a "not so deep"
can also mean
do everything, but don't interrupt

In U.S. English there is a subtle difference between "DON'T! STOP!", and "DON'T STOP!!"

When I got my ass cherry popped, I said "Ouch!" as his erection started to apply force to my opening, then "OUCH!" (and a little yelp) as my sphincter was overcome, and "It hurts!" when he popped through and paused. I took a couple of deep breaths, he pushed balls deep with a single, smooth, deliberate, stroke and I began to cry a little.

Afterwards, he told me that most virgins say the same thing: "Ouch!" . . . . "OUCH!!" . . . . "It hurts!". And, once the glans is firmly pressed against the opening, the fuck will continue until the sperm is inside, regardless of almost anything they might say.

 

[chrisrobin]

you lucky guy- that was a fucker with a lot experience and empathy...

yep, good guy and a good teacher taught me to take it in all the right positions so that when I met his buddy for a threesome I wasnt put of by the buddies huge thick long cock - even he introduced his cock to my ass slowly, surely and all the way in.

 

[chrisrobin]

For me, that was certainly the most challenging mental part. That's when I KNEW beyond any doubt that I was doing something taboo, but more significantly I was being "taken" by a man, and used for his sexual pleasure the way a man uses a woman.

Physically . . . yes, it hurt. A little more than I expected. I don't think that anybody getting fucked for the first time - man or woman; pussy or ass - can truly relax, and that probably makes it hurt a bit more. I yelped a little, possibly as much from the surprise, as from the actual pain of the huge cock head popping in (for a virgin hole, the cock is always huge, regardless of size). The hurt was a momentary stab, and - to be honest - it was a significant part of the overall first-time experience. It concentrated my attention on what was being done to me. If I could do it over again, I'd want it to hurt at least a little, even a lot.

The guy who got my ass cherry paused when he broke in, but probably not long enough. I think maybe I signaled to him that it was OK to finish the insertion before it actually was OK. Perhaps to show off my macho, the I-can-take-anything attitude that all guys have to some extent. He completed the insertion by splitting my rectum with one firm, smooth stroke. That hurt, in a different way. He may have pushed through a curve in my rectum, but regardless of the details it made me cry a few tears So that moment of completing the insertion was physically the greatest challenge. He noticed, but pretended not to. He fucked with long, deliberate strokes, and I regained control. It was just starting to feel good when he spilled his sperm inside me.

That was something I will remember was his shooting his spunk in me after that first fuck - spilling it wasn't, shooting it was, those cum pulses shooting through my body bringing me off.

 

[chrisrobin]

The way this was described made me hard

its the way to do it, chat a guy hard then ease him into your cavities all the way till you feel his pubic hair grazing the cheeks of your ass - then let the fun begin.

 

[chrisrobin]

You have an amazing way with words

you should see my way with cocks!

 

[deleted1345942]

Mentally, for me, was when my first had me on all 4s while he was lubing my ass. No going back at that point. I was both too horny to stop and couldn’t back out.

physically, obviously, when he was pushing it in for the first time. He had me opened up but it still burned.

 

[deine_huendin]

Its that moment when his cock goes in, the mushroom head gets past the first muscle band and stretches the ring wide, that moment when you want to stop him entering your anal passage any deeper, when he instant hurt is there.
Thats when he has to count to ten, let the pain subside and let the top take him gently. A virgin fucker who rams his cock in balls deep shows no sympathetic understanding at all. My mentor let me take my time taking his hard cock with rests as I got used to being penetrated, let me rest and acclimatize myself to his length and thickness as each inch went deeper, and, once in, his balls on my buttocks, that's when I had my first fuck. Never worried about not being able to take it after that.

you lucky guy- that was a fucker with a lot experience and empathy...

 

[chrisrobin]

When they take it out snd shove it all the way in
LIKE WOAHHH CHILL OUT

Well yeh in a sort of way thats what happened. After he'd cum the first time he didnt pull out but stopped inside me, drooped a bit then got harder and that time I did get the hole pounded the whole way and if the first cum was good then the second cumming was brilliant.

 

[deine_huendin]

For me, that was certainly the most challenging mental part. That's when I KNEW beyond any doubt that I was doing something taboo, but more significantly I was being "taken" by a man, and used for his sexual pleasure the way a man uses a woman.

Physically . . . yes, it hurt. A little more than I expected. I don't think that anybody getting fucked for the first time - man or woman; pussy or ass - can truly relax, and that probably makes it hurt a bit more. I yelped a little, possibly as much from the surprise, as from the actual pain of the huge cock head popping in (for a virgin hole, the cock is always huge, regardless of size). The hurt was a momentary stab, and - to be honest - it was a significant part of the overall first-time experience. It concentrated my attention on what was being done to me. If I could do it over again, I'd want it to hurt at least a little, even a lot.

The guy who got my ass cherry paused when he broke in, but probably not long enough. I think maybe I signaled to him that it was OK to finish the insertion before it actually was OK. Perhaps to show off my macho, the I-can-take-anything attitude that all guys have to some extent. He completed the insertion by splitting my rectum with one firm, smooth stroke. That hurt, in a different way. He may have pushed through a curve in my rectum, but regardless of the details it made me cry a few tears So that moment of completing the insertion was physically the greatest challenge. He noticed, but pretended not to. He fucked with long, deliberate strokes, and I regained control. It was just starting to feel good when he spilled his sperm inside me.

yes- at first it is a psychology thing,
to admit that your sex is different to hetero men, but also different to gay
to concede that you worship cocks, that you adore big hairy top alpha men...
and hoping that one of them likes to use u
that he wants to fuck you like a girl,
he will like it more than fucking a girls cunt
because your boi-cunt is so forbidden, so innocent, so tight
more challance, more act of defiance, more fun than fucking a cunt

at this moment it is important that he is self-confident,
that he does not hesitate, that he gives you the feeling of confidence
despite the following pain

 

[insert_8]

deine_huendin said: ↑
I have guys, big and hairy who want to dominate me and fuck my boytight ass but so far not one has mentioned he imagines he's fucking a cunt or that my tight ass is better because its forbidden. The guys that top me do so because I want to be topped, feel a mans cock slip into my anal cavity and fuck me knowing that its my ass, my pleasure and not some alternative to a sloppy cunt. Choosing a top is important to the sex you get and those that think brute force will penetrate my inner sanctum without any reference to my needs doesn't get far. All fucking is two way, bot parties have to enjoy it, both have to know its bum fun not pussy games. One guy I'm seeing from time to time enjoys taking me in so many different positions, he is kind, considerate and gentle and in no way is he thinking as he shoots his cum deep inside me I am there as a substitute for his girl friend.

No, I am not at all into playing Dominance/Submission games. I don't tolerate guys who want to "pound" me. I expect that some force may be required for the initial entry, but the encounter ends quickly if he tries to "ram" it into me.. I freely offer my ass for our mutual pleasure. As I lay back, push the folded pillow under my hips, spread my thighs and pull my legs back I feel so exposed and vulnerable, knowing that he could seriously hurt me, but trusting him not to.

 

[Johnrina]

Its that moment when his cock goes in, the mushroom head gets past the first muscle band and stretches the ring wide, that moment when you want to stop him entering your anal passage any deeper, when he instant hurt is there.
Thats when he has to count to ten, let the pain subside and let the top take him gently. A virgin fucker who rams his cock in balls deep shows no sympathetic understanding at all. My mentor let me take my time taking his hard cock with rests as I got used to being penetrated, let me rest and acclimatize myself to his length and thickness as each inch went deeper, and, once in, his balls on my buttocks, that's when I had my first fuck. Never worried about not being able to take it after that.

The way this was described made me hard

 

[chrisrobin]

anal virgin here.

my bf and i are long distance for another month (covid traveling wasn't a good idea) and when he finally gets back we are planning to have sex for the first time (25 year late bloomers i guess? we really enjoy oral together.)

honestly im scared (in a good way). we are kind of planning to flip fuck (unless you suggest otherwise - im smaller than him so maybe i should top first for now)??

I just want to be prepared and not like cry my eyeballs out. Without being vulgar, his dick is honestly really thick and its definitely gonna hurt so im looking for any tips to relax, lube, or just general par for the course!

Thank you for this thread! I know I'm emotionally ready for that step, but i dont want to ruin the physical to ruin my first time. I know he's understanding but I want to really get over myself enough to make it special.

If you really are an anal virgin and not just reborn (covid) then maybe just concentrate of what you know you enjoy first then let him lead you up to removing the cherry. My only till would be to relax, take things as the come and don't force the pace, when a cock enters your bum for the first time its going to be something you remember for many many years to come

 

[chrisrobin]

i am in fact an actual virgin. we are so used to doing oral and really enjoying that (and him not being out for the first good chunk of us being together - but yay he is now) so i didn't want to rush him or myself for that matter.

thank you for the advice! im so so so excited and its with someone i love which hopefully will make it better!

When the time comes, and it will, you'll just enjoy that feeling time after time of him squeezing into you body and leaving a fine deposit - hopefully you are not thinking of rubbers! Pasion killers!

 

[chrisrobin]

deine_huendin said: ↑
yes- at first it is a psychology thing,
to admit that your sex is different to hetero men, but also different to gayto concede that you worship cocks, that you adore big hairy top alpha men...and hoping that one of them likes to use u
that he wants to fuck you like a girl,he will like it more than fucking a girls cuntbecause your boi-cunt is so forbidden, so innocent, so tightmore challance, more act of defiance, more fun than fucking a cunt
at this moment it is important that he is self-confident,hat he does not hesitate, that he gives you the feeling of confidence
despite the following pain.
I have guys, big and hairy who want to dominate me and fuck my boytight ass but so far not one has mentioned he imagines he's fucking a cunt or that my tight ass is better because its forbidden. The guys that top me do so because I want to be topped, feel a mans cock slip into my anal cavity and fuck me knowing that its my ass, my pleasure and not some alternative to a sloppy cunt. Choosing a top is important to the sex you get and those that think brute force will penetrate my inner sanctum without any reference to my needs doesn't get far. All fucking is two way, bot parties have to enjoy it, both have to know its bum fun not pussy games. One guy I'm seeing from time to time enjoys taking me in so many different positions, he is kind, considerate and gentle and in no way is he thinking as he shoots his cum deep inside me I am there as a substitute for his girl friend.

 

[deine_huendin]

No, I am not at all into playing Dominance/Submission games. I don't tolerate guys who want to "pound" me. I expect that some force may be required for the initial entry, but the encounter ends quickly if he tries to "ram" it into me.. I freely offer my ass for our mutual pleasure. As I lay back, push the folded pillow under my hips, spread my thighs and pull my legs back I feel so exposed and vulnerable, knowing that he could seriously hurt me, but trusting him not to.

i think my english is too bad to explain it correct..;-(
you are right it is not the bdsm thing- but as you said
one the one hand you like it to get exposed form him, to ready for him
you accept some force getting opend, you like the pain of initial entry...

it is going along the border ? a tightrope...?