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Old 27th Jan 2008, 12:30 PM   #1
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Default Anal Sex -- I cannot make feel pleasurable

Hi I am going to be 18 next month. My question is concerning - Anal Sex- I have been having issues with how it feels.
Some of the things that are wrong is when I "experiment" it feels very uncomfortable and does not feel like pleasure.

I am very nervous because the guy that I have been talking to we might start getting "physically intimate" he is 22 years older then me and I want to lose my virginity to a guy this time.

When the "Time" comes it will probably be in a few weeks or so, I want to feel good and special.

Does anal sex really feel dis-comforting and only a SELECTIVE number of people enjoy it? Whenever I insert my "finger or two" into my anus with a lot of lubrication it does not feel good at all when inside my ass. (When I move my fingers in n' out, it does not feel good inside) I know that I am doing it right, but It feels like I am taking a horrible dump, and I feel way too full.

Does anal sex truly feel this uncomfortable, I am getting very frustrated. The guy is 40 years old, I am sure he will help me out with this issue.

I really want to have anal sex, but I am afraid..I do not want to stick to only women.
Anal sex is something that I really really want. I consider myself a bottom from all the gay porn I've seen,

Last edited by new18; 27th Jan 2008 at 12:39 PM..
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Old 27th Jan 2008, 01:29 PM   #2
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Default Re: Anal Sex -- I cannot make feel pleasurable

It does NOT feel bad after you spend some serious time practicing. You just have to get into it and try different things. Just keep experimenting and you'll do fine. Bottoming is actually easier once you get the hang of it.
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Old 27th Jan 2008, 02:16 PM   #3
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Default Re: Anal Sex -- I cannot make feel pleasurable

Hes 40? :P .. cool
 
Old 27th Jan 2008, 02:43 PM   #4
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Default Re: Anal Sex -- I cannot make feel pleasurable

Well. From experience, don't expect it to be great the first time, or even the second or third for that matter. It takes time.

The main thing is you have to be comfortable. Not physically, more emotionally, and from your post, I get the vibe that the whole idea is worrying to you. If you don't feel completely ready, don't do it.

I'd also suggest, wait until you find someone that you love

Cheers, and we're here to help!
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Old 27th Jan 2008, 03:12 PM   #5
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Default Re: Anal Sex -- I cannot make feel pleasurable

Eh, you don't HAVE to like it. It doesn't make you a virgin forever, either, you know? I mean, there are differences. Lesbians don't need a boy-part inside them to consider themselves not-virgins.

From the times I felt it, the first few were pretty bad, but I got used to it, you know? But I know people who are gay that don't like the "sex" of it. They just like the emotional aspect to having a same-gender partner.

And now I'm talking too much.
Good luck!
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Old 27th Jan 2008, 04:22 PM   #6
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Default Re: Anal Sex -- I cannot make feel pleasurable

Lol he is 40! The age gap.. its not too weird is it? He IS older then my parents. Lol

Thank you for all your help.
Its just the thing. I WANT TO LIKE IT, but I am afraid..it will end in a disaster. what if I am not cut out for gay sex? What if my body just responds good to females, but not males!!
Eh.

I wish I could be like those guys in the gay porn movies where the TOP is thrusting really hard and it feels/looks good. (Since I am/going to be the bottom)

What about "NUMBING" CREAMS???????????????
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Old 27th Jan 2008, 04:26 PM   #7
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Default Re: Anal Sex -- I cannot make feel pleasurable

i am gay, and i HATE anal sex... i don't even like a finger up there! I find it sssooo uncomfortable that I couldn't bring myself to do it again. Once was enough for me. And I don't want to like it. But different strokes for different folk and all that!

just make sure ur comfortable and trust the person is all i can say. i think the more relaxed u are with them, the more smoothly things will go
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Old 27th Jan 2008, 04:37 PM   #8
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Default Re: Anal Sex -- I cannot make feel pleasurable

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Originally Posted by deeNIreland View Post
i am gay, and i HATE anal sex... i don't even like a finger up there! I find it sssooo uncomfortable that I couldn't bring myself to do it again. Once was enough for me. And I don't want to like it. But different strokes for different folk and all that!

just make sure ur comfortable and trust the person is all i can say. i think the more relaxed u are with them, the more smoothly things will go

THANK YOU for your opinion!! I respect it, its just when I read stuff like "Anal sex shouldn't hurt or anal sex feels good" blah blah blah!! -- At least I can hear a real point of view of someone who can understand it LOL

I think I would be one those people that will never "Enjoy" anal sex, but will do it anyway because the whole idea of getting "done" in the anus really excites me!!

I think Anal Sex in terms of pleasure feels pretty much the same for everyone. It just depends how you interpret that pleasure - Mentally.


I just wish it would not feel so dis-comforting, can a cup full of lubricant help release the pain? Perhaps more lubrication is needed so the muscles do not rub or contract???
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Old 27th Jan 2008, 04:46 PM   #9
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Default Re: Anal Sex -- I cannot make feel pleasurable

lol, i dont know if it feels the same for everyone... cos i sure didnt like it, and i have a high pain threshold... martial arts and gymnastics doesnt allow u to feel pain! haha! i think, and this might sound gross, that asides from the pain... i felt like i was gonna crap myself.. and its not a nice feeling!

though i am glad that u found my opinion valuable. i dont think lubricant will relieve the pain... just let it slide in and out with more ease. ive read (yes read, never put into practice) that the more u do it, the easier it becomes. but ill take their word for it! i just find it PAINFUL! hope u get something sorted tho dude!
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Old 27th Jan 2008, 04:55 PM   #10
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Default Re: Anal Sex -- I cannot make feel pleasurable

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Originally Posted by deeNIreland View Post
lol, i dont know if it feels the same for everyone... cos i sure didnt like it, and i have a high pain threshold... martial arts and gymnastics doesnt allow u to feel pain! haha! i think, and this might sound gross, that asides from the pain... i felt like i was gonna crap myself.. and its not a nice feeling!

though i am glad that u found my opinion valuable. i dont think lubricant will relieve the pain... just let it slide in and out with more ease. ive read (yes read, never put into practice) that the more u do it, the easier it becomes. but ill take their word for it! i just find it PAINFUL! hope u get something sorted tho dude!
Thanks so much. Did you seriously do Gymnastics??? Because so Did I. I used to be able to the middle splits for 2 days of my whole gymnastic career when I was extra flexible, but now.. cannot. LOL
I am pretty lean and I used to be able to do a Back Bend VERY WELL, and Still can do it simply . (I call it Arch Bridge)

SO thinking if you are flexible your muscles should be flexible EVERYWHERE.


It feels like I want to crap myself, and I cannot tell the difference if I did!! How embarrasing!! During anal intercourse it feels like your taking a shit, what if you did...OMG......
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Old 27th Jan 2008, 05:31 PM   #11
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Default Re: Anal Sex -- I cannot make feel pleasurable

There's info on anal sex in Health and Well Being.

I question the 22 year gap.Are you sure this is the one? Make sure ..
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Old 27th Jan 2008, 05:35 PM   #12
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Default Re: Anal Sex -- I cannot make feel pleasurable

Quote:
Originally Posted by panda View Post
There's info on anal sex in Health and Well Being.

I question the 22 year gap.Are you sure this is the one? Make sure ..

I agree, you say that you're not even 18 yet. I hope he's not trying to use you as some young piece of ass and better yet he gets to pop your cherry? Something comes to mind... statutory rape

I hope you can trust him and make sure to use protection. I think it's safe to assume that he's no virgin.
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Old 27th Jan 2008, 07:42 PM   #13
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Default Re: Anal Sex -- I cannot make feel pleasurable

Quote:
Originally Posted by otc877 View Post
Quote:
Originally Posted by panda View Post
There's info on anal sex in Health and Well Being.

I question the 22 year gap.Are you sure this is the one? Make sure ..

I agree, you say that you're not even 18 yet. I hope he's not trying to use you as some young piece of ass and better yet he gets to pop your cherry? Something comes to mind... statutory rape

I hope you can trust him and make sure to use protection. I think it's safe to assume that he's no virgin.
I'd agree with you two... you know him better than we do, but just make sure it's really what you want.
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Old 27th Jan 2008, 09:31 PM   #14
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Default Re: Anal Sex -- I cannot make feel pleasurable

Give that older guy a big high five from me, damn is he lucky!
Make sure he's wearing a condom. It can be tempting to have a bare manshaft in you but it most definitely not worth the risk. Having an STD can stop your sex life completely, simply because of the guilt you will feel that you might pass it on. A lot of STDs remain dormant and don't have signs or symptoms for months or years, so him having an imperfection-free Johnson means nothing. If he won;t do it without a condom then don't do it...

As for your anal problems, it is true, perhaps you will never like it... but if you're determined to get railed by this guy then I have a suggestion from my experience when I bought my first dildo.
It was too big and just hurt, providing almost no pleasure, so I decided to backtrack a bit.
After a few weeks I was ready for it and it was amazing. I rarely use it anymore though, as I have become quite attached to the smooth gliding test tubes

Go buy some stuff at walmart or something that has a size you're comfortable with and can smooth glide, just be wary of the material. Then go to Joe Blows XXX store and get a big one if you feel you are ready.



Above is shown the progress you can make, from left to right.
I don't use the 3 on the left, they are just examples.

I hope this helps.
 
Old 27th Jan 2008, 09:58 PM   #15
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Default Re: Anal Sex -- I cannot make feel pleasurable

THANK YOU FOR ALL OF THE WONDERFUl ADVICE. And I think over every single post here.
The critique is all so great.

Info: with the older guy. I am 17 he is 39. So yes a 22 year difference. He has been with 25 guys in his lifetime. (He told me) I met him on-line. I still haven't seen him in person, but he showed me his myspace and I talked to him on the phone.
(I've been talking to him for about 2 weeks now) He seems like a very nice person over the phone and REALLY wants to meet me.





What are your opinions about the age gap, what are your straightforward opinions about the age difference? He does want to have sex WITHOUT a condom, that is what he told me. And he does want to go "ALL the WAY" if you know what I mean.

I am a virgin, never had sexual intercourse through the anus, so I am 100% sure I am clean. (Been with my GF, but we where always careful)
Should I let him, go INTO my body w/o a condom? Isn't the TOP usually more at risk for STD's then the bottom? He does want cu* into my anus that is what I meant with "All the way"

Should I just take a chance? I've heard it is harder to get an STD if you are the "bottom"

Last edited by new18; 27th Jan 2008 at 10:13 PM..
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Old 27th Jan 2008, 10:11 PM   #16
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Default Re: Anal Sex -- I cannot make feel pleasurable

I'm sorry i just get the feeling your doing it wrong....are you really just shoving your fingers in? it should be a very slow process i mean tediously slow espeacially getting ready for it...start with a pinky get it in just a little bit untill you dont feel as tightness then try moving it a little....later try bigger fingers then two fingers, then even a small item does not have to be a toy just not sharp and can insert easilly enough with lube.... i mean you can watch videos and read about how to make anal sex pleasurable to....but my honest opinion dont have sex yet if it's that painful you need to wait untill it's not so painful with your fingers because it will hurt even worse when its a penis going in.... also the fact he has been with 25 guys and wants to do without a condom when he knows its your first time worries me..... how long have you talked to him.....
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Old 27th Jan 2008, 10:18 PM   #17
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Default Re: Anal Sex -- I cannot make feel pleasurable

Quote:
Originally Posted by chrisbrgstrm View Post
I'm sorry i just get the feeling your doing it wrong....are you really just shoving your fingers in? it should be a very slow process i mean tediously slow espeacially getting ready for it...start with a pinky get it in just a little bit untill you dont feel as tightness then try moving it a little....later try bigger fingers then two fingers, then even a small item does not have to be a toy just not sharp and can insert easilly enough with lube.... i mean you can watch videos and read about how to make anal sex pleasurable to....but my honest opinion dont have sex yet if it's that painful you need to wait untill it's not so painful with your fingers because it will hurt even worse when its a penis going in.... also the fact he has been with 25 guys and wants to do without a condom when he knows its your first time worries me..... how long have you talked to him.....
WEll really I started talking to him about two weeks ago. At first he messaged me over another website in November. (It basically said I was 17 and on my profile that I was bisexual and was attracted to older guys) I said hi to him, but then we stopped talking. (So I guess I've known him for two months now?)

Two weeks ago he sended me many messages, so we just started talking again. I gave him my number, he called me and said he really wants to meet me.
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Old 27th Jan 2008, 10:19 PM   #18
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Default Re: Anal Sex -- I cannot make feel pleasurable

The whole situation doesn't sound good to me. The age gap's big, it's true, but you've never even met him in person? That's kind of...not a good idea at all. I mean, I don't necessarily know the whole situation, but it sounds a bit fishy. It makes me worry.

And everyone in sex is at risk for STDs, top or bottom. If you don't know this guy, DEFINITELY make him use a condom. If he won't, it's really not worth the risk. 25 guys gives him plenty of opportunities to have gotten an STD that he could give to you. And then he wants to not use a condom? That definitely worries me.

It kind of sounds like you're rushing into things, if you ask me. I personally would advise you to just wait a little longer, you know, find the right guy. Who you know in person. And can trust 100%. But that's just my opinion.
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Old 27th Jan 2008, 10:25 PM   #19
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Default Re: Anal Sex -- I cannot make feel pleasurable

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Originally Posted by Arioch8688 View Post
The whole situation doesn't sound good to me. The age gap's big, it's true, but you've never even met him in person? That's kind of...not a good idea at all. I mean, I don't necessarily know the whole situation, but it sounds a bit fishy. It makes me worry.

And everyone in sex is at risk for STDs, top or bottom. If you don't know this guy, DEFINITELY make him use a condom. If he won't, it's really not worth the risk. 25 guys gives him plenty of opportunities to have gotten an STD that he could give to you. And then he wants to not use a condom? That definitely worries me.

It kind of sounds like you're rushing into things, if you ask me. I personally would advise you to just wait a little longer, you know, find the right guy. Who you know in person. And can trust 100%. But that's just my opinion.
Your opinion has a lot of merit, Maybe I am just naive? I have always been headstrong and had an opinionated mentality. I really want to have sex, but ugh this is so confusing. I am freaking 17 years old, going to be 18 next month and have not even kissed a guy yet.


You guys are allowed to make judgments of this and I WANT YOU TO!!, I just want to get to know my sexuality better, and I am tired of waiting.

Losing your virginity to a guy is different then losing to a girl. Does this sound strange? He did tell me he loves really young guys, and I guess I fit his criteria? I've asked him how many younger guys has he been with, he did not tell me.

I sended pictures of my face (and a body shot) to him, And thats when said he was really attracted to me ,, That is when he started asking for my phone number, saying he wants to meet me in person ,When I talked to him on the phone he seemed nice, He had a soothing,calm voice.

Last edited by new18; 27th Jan 2008 at 10:34 PM..
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Old 27th Jan 2008, 10:47 PM   #20
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Default Re: Anal Sex -- I cannot make feel pleasurable

Well heres your wakeup call. Forget this older guy. He wants to *um inside of you without a condom... This man obviously doesn't care about you or your future, forget him. FORGET HIM. Don't feel obligated to do anything he says, and I would recommend blocking him.

When I was younger and naive I had unprotected sex. No *umming into the bum mind you, but unprotected nonetheless. From only 2 people I picked up the STD HPV (human papillomavirus). Mind you this std doesn't harm me but it can harm women IE cervical cancer. It also comes with annoying warts that I have to use a cream for ><. When I had my first boyfriend I was so afraid of spreading it to him that we never actually had sex, even though we both wanted to. I got my first few warts about 6 months to 2 years from contact, luckily I hadn't had sex with anyone else and spread it along. There is no cure for HPV and no one knows when it goes away or if it'll ever go away for some people. I was very very lucky that I didn't get HIV too, just tested negative a few days ago. Imagine where I would be at that point...

Theres plenty of people out there just like you, you just need to find them. Honestly I think the internet is fine for meeting people, though I prefer to do it in person. I wouldn't mind getting a few PMs on here, though that's not why I'm here so I'm not going to pursue that.

Also I wouldn't recommend bridging over 10 years from your age.
Why is it that you're into older guys, might I ask?
 
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