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Old 08-29-2012, 10:45 AM   #1
SkylarFalling
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Playing with HIS ass

Long term relationship, and we have established that he wants me to play with his ass. That's all cool. I've done just playing, teasing around the entrance while we're doing other things. He seems to enjoy this.
I figure the next sensible option is to see how him taking just the one finger goes.

Any suggestions/experiences from other people on anal with their guy? Advice you would have liked when you first did it? Advice from guys who have done that with inexperienced girls? Neither of us have done this before and I'm more than happy to give it a go and see what happens, but it seems foolish to ignore such a great resource as the members of the Lit forums!

In particular, the first time around do you reckon all fours or lying on his front or on his back is a better idea? He isn't very talkative about which is better, which I'm putting down to being unsure, because he is talkative enough about the fact that he wants me to do it.

Cheers everybody
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Ok, so if you send me a detailed PM about what you're gonna do to me and how many times I'm gonna orgasm and how I'm gonna beg you, I probably won't reply. Send me a PM if you have something to say, y'know, an actual topic of conversation. Dirty PMs with someone I know nothing about don't do anything for me.
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Old 08-29-2012, 03:14 PM   #2
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I have done this before with my wife and I loved it so much she went out and bought me a few dildos and strap ones it feels great just use a lot of lube and be gentle at first and work ur way up but I'm also bi so that may help me more idk but I didn't have a anything that large before until she got the toys for us
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Old 08-29-2012, 04:02 PM   #3
NippleMuncher
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If he's pro-play, then it's really something you have to work out with him. What I would suggest for a first time would be either you kneeling before him, giving him a blowjob while your fingers explore, you can use saliva for light penetration lubricant. Another good position is 69 with him on top, again you have full access to him while you're performing miracles elsewhere.

You might want to look at the "milking a man's cock" thread, to will give you some pointers of how to find the prostate and massage it.

after that, it's really up to the two of you to have an open and honest conversation about what he would like to try/accept into his behind. Toys may be on the horizon, who knows. Good luck, have fun, and don't forget to report back with your experiences.
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Old 08-29-2012, 06:00 PM   #4
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I would suggest a prostate massager. You can get them relatively cheap. Some are pretty small, so it's not intimidating. take it slow and lots of lube. It is an enjoyable experience having that done whilst getting oral. Uh, or so I've heard.
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Old 08-29-2012, 06:09 PM   #5
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Take it from a Bi.

Girl?
Take it slow, in stages.

Guy?
Let r rip!
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Old 08-29-2012, 10:24 PM   #6
rthnck
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Quote:
Originally Posted by Jessica_29 View Post
Take it from a Bi.

Girl?
Take it slow, in stages.

Guy?
Let r rip!
That's been my experience as well which I can't really explain. When my partner and I started ass play she started with a finger, a couple of fingers, a small dildo and then bigger dildos in just a couple of days and it was definitely more pleasurable than uncomfortable. For her on the other hand, it's got to be slow, the timing has to be perfect, the mood just right, plenty of lube. Sigh! I guess it's that Mars/Venus thing. Still fun...
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Old 08-30-2012, 01:06 PM   #7
love_269_girl
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I prefer him on his back so I can see his reactions. Trim your nails and use lube. As long as you are planning this event go ahead get some latex gloves.
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Old 08-30-2012, 07:50 PM   #8
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Take it easy!

My lady enjoys butt play but not to an extreme (internal hemorrhoids). She loves a little kissing and insertion of my tongue gently. I never force it and that makes a big difference. She has begun to reciprocate which I enjoy. Both with her tongue and with her finger. Lube makes a big difference with her finger. It's a process and it's been fun for both of us.
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Old 08-31-2012, 06:59 AM   #9
SkylarFalling
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Thank you.

It went better than I thought, he took two fingers easily. Makes me wonder whether or not he is telling the truth about not doing it himself before! Either way lots and lots of lube seemed to be the main thing. He wanted to be on all fours within about 10 minutes anyway. Got no where so far as finding his prostate is concerned, but I guess I'll just have to do lots of reading and practice.
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Promiscuous Boy/We're one in the same/So we don't gotta play games no more


Ok, so if you send me a detailed PM about what you're gonna do to me and how many times I'm gonna orgasm and how I'm gonna beg you, I probably won't reply. Send me a PM if you have something to say, y'know, an actual topic of conversation. Dirty PMs with someone I know nothing about don't do anything for me.
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Old 08-31-2012, 08:32 PM   #10
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Originally Posted by SkylarFalling View Post
Thank you.

It went better than I thought, he took two fingers easily. Makes me wonder whether or not he is telling the truth about not doing it himself before! Either way lots and lots of lube seemed to be the main thing. He wanted to be on all fours within about 10 minutes anyway. Got no where so far as finding his prostate is concerned, but I guess I'll just have to do lots of reading and practice.
I'm jealous
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Old 01-03-2013, 08:08 PM   #11
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My new girlfriend wanted to play with me anally, so we bought an Aneros. It was an incredible experience for me - massive orgasm. She was so excited that she came just sitting there playing with me and sucking on me. She said the experience was incredibly erotic for her.
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Old 01-03-2013, 08:14 PM   #12
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Originally Posted by SkylarFalling View Post
Thank you.

It went better than I thought, he took two fingers easily. Makes me wonder whether or not he is telling the truth about not doing it himself before! Either way lots and lots of lube seemed to be the main thing. He wanted to be on all fours within about 10 minutes anyway. Got no where so far as finding his prostate is concerned, but I guess I'll just have to do lots of reading and practice.
Glad it's working out for you guys. He may be shy or not sure what feels best or both. Men handle their cocks so much that if he really hasn't played with his ass or let anyone else play with it, then he likely has no idea, because in comparison to his relationship with his cock, his ass is a stranger.

But if he's up for it and you're up for it, I say get a toy and make some screaming sexytimes happen. I've always wanted to use a prostate massager on a guy...
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Old 01-03-2013, 08:27 PM   #13
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My thought was that I've introduced so many erotic and/or kinky things to her, which she absolutely loves, and I get incredibly turned on. Shouldn't she have the same pleasure in taking control and doing things to me that turn her on?
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Old 01-05-2013, 12:13 PM   #14
SkylarFalling
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Sorry I disappeared from here for ages.

I think toys are the next step, because I apparently can't go deep enough with my stubby little fingers. xD
Think I might look for something that is aimed at prostate massaging, 'cos as much fun as we're having I'm still struggling with that part. I have got really little hands though so I dunno how possible it is that my fingers just aren't long enough or I'm not pressing in the right place. I can reach my own cervix when its low though, so who knows. :/
Either way he will become my manslut sooner or later. If we get good at this I'd reeeeally like to have a go with a Feeldoe.
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Promiscuous Boy/I'm calling your name/But you're driving me crazy/The way you're making me wait
Promiscuous Girl/You're teasing me/You know what I want/And I got what you need
Promiscuous Boy/We're one in the same/So we don't gotta play games no more


Ok, so if you send me a detailed PM about what you're gonna do to me and how many times I'm gonna orgasm and how I'm gonna beg you, I probably won't reply. Send me a PM if you have something to say, y'know, an actual topic of conversation. Dirty PMs with someone I know nothing about don't do anything for me.
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Old 02-10-2013, 12:52 PM   #15
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I tried with an ex and while i was giving him a blow job, i licked lubed the area the are and gently put my finger inside his ass. We communicated to make sure he was comfortable and after that we upgraded to toys!!!
Communication is key, just like a girl receiving anal sex you wanna be gentle!
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