First time anal play advice (Full Version)

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illstoptheworld -> First time anal play advice (4/3/2007 10:28:32 AM)

Hi Everyone,
So,my friend and I who I play with are dying to try anal play,but we are both first timers. I am dominant and he is submissive, but I know that since it his first time I shouldn't be too forceful, or mean?Or should I?We aren't so much into physical pain,and although the idea of this is something that turns us on a lot, we havent done it yet because he is scared. Since this is his first time and it might hurt a lot, do I need to ask him if he is okay, if i need to be more gentle, or go slower? I feel torn, because I want to be mean to him and call him slut, and have it be very kinky and have him feel completely helpless and owned, but I am just so scared of really hurting him. Is there anything that isn't a strap on or a butt plug that would be good for first timers to expirement with as far as anal play? Does he need to get an enema?Does anyone have any advice?
Thanks:)




AAkasha -> RE: First time anal play advice (4/3/2007 10:36:45 AM)

Go slow. Use a LOT of lubricant.  Communicate a lot. 
Remember, you don't have to be MEAN or NICE. Being a femdom is about thriving and enjoying your role.  Enjoy it outwardly - tell him how much it is turning you on.  Be playfully sadistic.  Get hot about the way he struggles and responds to his torment. Show him how turned on you are - that will keep him motivated.

Don't go straight into the anal play. First him him very hot with teasing and denial.  Keep him bound and helpless, sit on his face, masturbate in front of him, etc.  Do all the things you know will get him really worked up.  Put on latex gloves and lubricate your fingers and loosen him up that way. It's fairly easy, no pressure, and you can practice your humiliating talk then -- tell him he's tight and you like it, tell him he is enjoying it way too much, call him a whore, etc. Whatever feels natural.  Use one finger, then two. 

Once you feel comfortable, add more lube and move on to small dildos or plugs.  Remember, you don't have to do it all at once, all in one evening. Just enjoy yourself - your pleasure is what this all about.  Enjoy the way he reacts, breathes, shivers.

Please share the experience!  Remember, communicate communicate communicate - before, during and after.

Akasha




subbyboy24 -> RE: First time anal play advice (4/3/2007 10:48:25 AM)

AAkasha did an excellent job of giving advice on that topic. When you reach the level of dildos let him control the tempo at first. For example get behind him and make him slide back on it into your hips. This way he can get accustomed to the feeling. As AAkasha said encourage him and tell him what a good whore or slut he is being. Either that or make him ride the dildo, put on a show for you. In a matter of time im sure you will be pounding him. Feel free to write me if you would like to know my experiences in anal play.




hereyesruponyou -> RE: First time anal play advice (4/3/2007 1:37:44 PM)

i suggest you do a search for this on here. there was a great thread about this just a few weeks ago that offered tons of good advice




DianeB269 -> RE: First time anal play advice (4/3/2007 1:59:27 PM)

I sent you a message here on CM.


Diane




michaelOfGeorgia -> RE: First time anal play advice (4/3/2007 2:03:20 PM)

my advice is: just say "NO"

LOL




DianeB269 -> RE: First time anal play advice (4/3/2007 2:08:33 PM)

Try it at least 4 or 5 times before you say yes or no.


Diane




michaelOfGeorgia -> RE: First time anal play advice (4/3/2007 2:09:55 PM)

i always say "NO" to crack...LOL




SLAVEBOY32 -> RE: First time anal play advice (4/3/2007 3:00:37 PM)

First time i did it, i remember looking at the strap on and thinking it was HUGE! lol. we did what everybody suggests, She didnt use her fingers, but graduated me up in size with toys. starting out with thin little vibrator and then moving on to a larger butt plug, which helped alot and was also the most painful of the toys, but still was totally hot and totally bearable. After the plug, i was kind of stretched out at that point i guess? We went on the the strap on and it went in So much easier then i thought it would, i honestly could not beleive it. It was like after the initial stretching with the plug, i just wasn't so tight anymore. It still hurt, it's not like she was just able to shove this thing in me, but it went in a helluva alot easier then i thought it was going to. In less then half an hour we were having full blown strap on anal and we both had a great time.




DrPleasure -> RE: First time anal play advice (4/3/2007 3:14:14 PM)

quote:

ORIGINAL: AAkasha

Go slow. Use a LOT of lubricant.  Communicate a lot. 
Remember, you don't have to be MEAN or NICE. Being a femdom is about thriving and enjoying your role.  Enjoy it outwardly - tell him how much it is turning you on.  Be playfully sadistic.  Get hot about the way he struggles and responds to his torment. Show him how turned on you are - that will keep him motivated.

Don't go straight into the anal play. First him him very hot with teasing and denial.  Keep him bound and helpless, sit on his face, masturbate in front of him, etc.  Do all the things you know will get him really worked up.  Put on latex gloves and lubricate your fingers and loosen him up that way. It's fairly easy, no pressure, and you can practice your humiliating talk then -- tell him he's tight and you like it, tell him he is enjoying it way too much, call him a whore, etc. Whatever feels natural.  Use one finger, then two. 

Once you feel comfortable, add more lube and move on to small dildos or plugs.  Remember, you don't have to do it all at once, all in one evening. Just enjoy yourself - your pleasure is what this all about.  Enjoy the way he reacts, breathes, shivers.

Please share the experience!  Remember, communicate communicate communicate - before, during and after.

Akasha


GODDAMN!!!  My asshole just puckered!!! :)
You are wise Ms. AAkasha. 




MistressRouge -> RE: First time anal play advice (4/3/2007 3:15:49 PM)

I suggest you start very small, and very slowly lol. The worse thing you could do is force it in on first contact, as this can cause damage mentally aswell as physically. Lots & lots of lubricant (spit especially[;)]), and beginning with a latex gloved fore finger is the best to start. I have a selection of strap ons, My smallest (virgin size) is the size of a very small forefinger, which vibrates too.
 
Selection of strap-on/insertable is very important, always go for soft, plyable latex or rubber moulded strap-ons or toys, to ensure comfort and durability.




DrPleasure -> RE: First time anal play advice (4/3/2007 3:30:16 PM)

quote:

ORIGINAL: DianeB269

Try it at least 4 or 5 times before you say yes or no.

Diane


Good point.  It took me about 9 or 10 times until I really started to like it.  I used to beg for it because I found the idea so hot but, I would always scream out my safeword as soon as I was penetrated.  Even with the medium sized ones.  Fingers were okay but dildos were a no no.  So one day, I'm playing with my mistress and she tells me that she plans on fucking me today.  "Okay, I've been through this before," I'm thinking.  Then she pulls out the dildo that she's going to fuck me with.  Longer and thicker than anything she's tried on me before.  Thank god for the safeword.

The next thing she pulls out is a ball gag.  "I'm tired of you getting me all worked up and then letting me down.  You're not calling out your safeword this time," she says.  Then, she ritualistically puts the strap-on on in front of me ties me down and then puts the ball gag in my mouth.  She also did something different which i really liked because it allowed me to maintain my erection which is she put me in cock and ball bondage.  She takes a lot of time loosening me up with her fingers and then slips the large dildo into me, slowly.  She left it in there for a minute or so for me to get used to the sensation.  Then she started moving slowly and increasing speed until eventually she was pounding away.  It got so intense that she would remove the whole thing and shove it back in a few times in between penetrating me deep and grinding away. 

I never felt anything like it and it was by one of the best orgasm I've ever had in my life.  Truly a moment that will last a lifetime. 




DianeB269 -> RE: First time anal play advice (4/3/2007 3:49:48 PM)

quote:

ORIGINAL: DrPleasure

quote:

ORIGINAL: DianeB269

Try it at least 4 or 5 times before you say yes or no.

Diane


Good point.  It took me about 9 or 10 times until I really started to like it.  I used to beg for it because I found the idea so hot but, I would always scream out my safeword as soon as I was penetrated.  Even with the medium sized ones.  Fingers were okay but dildos were a no no.  So one day, I'm playing with my mistress and she tells me that she plans on fucking me today.  "Okay, I've been through this before," I'm thinking.  Then she pulls out the dildo that she's going to fuck me with.  Longer and thicker than anything she's tried on me before.  Thank god for the safeword.

The next thing she pulls out is a ball gag.  "I'm tired of you getting me all worked up and then letting me down.  You're not calling out your safeword this time," she says.  Then, she ritualistically puts the strap-on on in front of me ties me down and then puts the ball gag in my mouth.  She also did something different which i really liked because it allowed me to maintain my erection which is she put me in cock and ball bondage.  She takes a lot of time loosening me up with her fingers and then slips the large dildo into me, slowly.  She left it in there for a minute or so for me to get used to the sensation.  Then she started moving slowly and increasing speed until eventually she was pounding away.  It got so intense that she would remove the whole thing and shove it back in a few times in between penetrating me deep and grinding away. 

I never felt anything like it and it was by one of the best orgasm I've ever had in my life.  Truly a moment that will last a lifetime. 



Now this guy knows how much fun strapon play can be.


Diane




pixelslave -> RE: First time anal play advice (4/3/2007 10:23:44 PM)

quote:

ORIGINAL: illstoptheworld

Hi Everyone,
So,my friend and I who I play with are dying to try anal play,but we are both first timers. I am dominant and he is submissive, but I know that since it his first time I shouldn't be too forceful, or mean?Or should I?We aren't so much into physical pain,and although the idea of this is something that turns us on a lot, we havent done it yet because he is scared. Since this is his first time and it might hurt a lot, do I need to ask him if he is okay, if i need to be more gentle, or go slower? I feel torn, because I want to be mean to him and call him slut, and have it be very kinky and have him feel completely helpless and owned, but I am just so scared of really hurting him. Is there anything that isn't a strap on or a butt plug that would be good for first timers to expirement with as far as anal play? Does he need to get an enema?Does anyone have any advice?
Thanks:)


AAkasha gave you some excellent advice.  Beyond that, there's some additional advice that I'd like to add.  One of the stepped insertables that is graduated with increasingly larger balls/bulbs to progressively stretch the anus over are also very good toys regardless of your level of experience.  They are flexible and begin at about the size of a small finger (LOL! I guess it depends on the size of your hand.).  As others have said, you can never have too much lube, to that end, you might want to get some "depends"; the disposable & absorbent plastic liners you can lay on the bed as the lube will likely drip all over and soak your bed.  They're very convenient and don't allow anything to leak through to the sheets (where a towel will allow that to happen). [;)]
 
The most important thing above all, is that your submissive friend learn to relax and trust you.  The more he relaxes, the easier things will be.  Rubbing his bottom gently may help him to relax and be a silent way of telling him that he can trust you.  If you have him on his hands and knees, you may want to use a few pillows to help support him as it likely is a position that he's not used to.  Maintaining frequent communication with him is very important, for both the feedback and the excitement factor.  Telling him what you're doing will likely help relieve his anxiety and you'll also be able to tell him to relax should you happen to feel him tighten. 
 
What follows is the important part that I'd like to add to what AAkasha said, press into him, or have him press back toward you until he feels things are becoming too tight for him, have him pause, either stay put or pull back a tiny bit while you tell him to breathe and relax.  Once he relaxes a bit, you'll feel it (as will he) and you can then have him push back further and make additional progress for entry.  Every time he feels things tighten, repeat this process to relax his sphincter further.  Not only will he learn to trust you, he'll also learn to trust himself that he can relax and get through those moments without experiencing them as being painful.  Eventually, it will be no big deal for him to open himself to you completely and you should both find the experience enjoyable.
 
I can't emphasize the importance of trust and communication between you and your partner enough, if you really want to have a positive experience with him that both of you will look forward to repeating.  With my new Mistress, I quickly learned to trust her a great deal in other areas and was immensely looking forward to engaging in anal play with her.  To be honest, I was more like "her slut in heat" that was just anxiously waiting and about ready to beg her to take me. [;)]  On that particular evening, I was soooo relaxed, that when she inserted a finger, I immediately opened completely to her.  More lube, and I quickly heard her say "two".  More lube was added again, and a moment or two later I heard her say "three".  I was just there on my knees and some pillows, relaxed and not really feeling anything but pleasurable sensations and enjoying the thoughts from knowing what would soon be happening with her for the very first time.  She surprised me when she continued to probe me.  I heard her say "four", and I was soon feeling a bit of a stretch, after which she paused.  I breathed slowly and relaxed, after which she pressed on.  After what seemed like only a moment or two later, she told me she had her hand inside me beyond her knuckles!  It didn't register with me at first what she meant.  At the point when she said "four", she'd tucked her thumb inside the others.  It was the first time I'd ever had a hand inside me and it was her first time for this as well!  She didn't proceed further, as she was sooo hot and turned on from having her hand that far in me, she just couldn't wait to insert her FeelDoe inside me and start thrusting away!  Needless to say, I was equally turned on, and began rythmically meeting her thrusts as our bodies pounded together in unison. [8D]
 
It was absolutely the VERY BEST anal experience in my life to date!  Yet, I also know it's only going to continue to get even better as we spend more time together learning each other's ways! [sm=lol.gif]  
 
In closing, I'd like to thank my new Mistress for this experience and the opportunity to share it.  I believe in my heart, down to the core of my being, that I'm incredibly fortunate to be her new sub! [:)] 
 
 - pixel




MisPandora -> RE: First time anal play advice (4/4/2007 2:57:26 AM)

quote:

ORIGINAL: MistressRouge

I suggest you start very small, and very slowly lol. The worse thing you could do is force it in on first contact, as this can cause damage mentally aswell as physically. Lots & lots of lubricant (spit especially[;)]), and beginning with a latex gloved fore finger is the best to start. I have a selection of strap ons, My smallest (virgin size) is the size of a very small forefinger, which vibrates too.
 
Selection of strap-on/insertable is very important, always go for soft, plyable latex or rubber moulded strap-ons or toys, to ensure comfort and durability.

Let's leave the spit to the boys on Brokeback Mountain?  For a good first time introduction, PLEASE use a commercial lubricant -- and there are plenty of them out there, even available in the grocery stores or feminine hygeine sections of drug stores -- and use 10x what you think you'll need.

Everything you need to know about Bending The Boyfriend Over is here:
http://www.babeland.com/sexinfo/howto/bend_over_boyfriend




MistressRouge -> RE: First time anal play advice (4/4/2007 3:12:57 AM)

I care to differ [:D]

To spit a long trail of spit onto someone asshole, as sub lays bound,  legs a kimber in "missionary position". Minutes before I thrust and shaft them aggressively, looking into their eyes as I spit then insert My first inch.

Much more enjoyable then errrr, 1 minute, lets reach for the lube lol.

I have a selection of different lubricant too, anal "hot cinnamon" hot lube, cold "ice" lube, the anal water based lube's, . The more expensive silicone lube duals as a latex dress aid, and glides like a dream [:D] I recommend it!

Regards,

Mistress Roug'e.

http://mistressrouge.webeden.co.uk/




quote:

ORIGINAL: MisPandora

quote:

ORIGINAL: MistressRouge

I suggest you start very small, and very slowly lol. The worse thing you could do is force it in on first contact, as this can cause damage mentally aswell as physically. Lots & lots of lubricant (spit especially[;)]), and beginning with a latex gloved fore finger is the best to start. I have a selection of strap ons, My smallest (virgin size) is the size of a very small forefinger, which vibrates too.
 
Selection of strap-on/insertable is very important, always go for soft, plyable latex or rubber moulded strap-ons or toys, to ensure comfort and durability.

Let's leave the spit to the boys on Brokeback Mountain?  For a good first time introduction, PLEASE use a commercial lubricant -- and there are plenty of them out there, even available in the grocery stores or feminine hygeine sections of drug stores -- and use 10x what you think you'll need.

Everything you need to know about Bending The Boyfriend Over is here:
http://www.babeland.com/sexinfo/howto/bend_over_boyfriend




DianeB269 -> RE: First time anal play advice (4/4/2007 6:24:10 AM)

http://www.goodvibes.com/Item--i-1-9-XX-0512--m-17




malloves69 -> RE: First time anal play advice (4/4/2007 10:43:52 AM)

love strapon play and being fisted by my mistress ...smile ...great way to submit to a lady in control and i now gladly bendover for her anytime she wants to take my ass ....yes go slow and communicate ..use lots of lube ...funny but we actually use crisco as a lube ..smile ...when she says its time to bake cookies im on my knees doggy style --lol when she fists me she likes me on my back so she can play with my cock while fisting me ..then once i cum she feeds my cum back to me until i swallow it all ...her 10 in strapon i love the most ...long and thick and she looks great wearing it ..smile ..i always give myself at least 2 enemas so im nice and clean for her to play with ...once her fist is in me and i relax she trys to go deeper to see how much i can take ...call me crazy but it does feel good and i cant believe how much she loves doing it to me ..its like she takes my soul when she is deep inside of me ...gawd knows she already has my heart !!  gladly bending over for her or her friends when she wants to show how well trained i am at serving her ..have fun ...boy i am now hooked ...she calls me her little ass slut and cum slut ...love submitting to her and her desires ..have fun mal




MistressRouge -> RE: First time anal play advice (4/4/2007 10:59:41 AM)

quote:

ORIGINAL: malloves69

love strapon play and being fisted by my mistress ...smile ...great way to submit to a lady in control and i now gladly bendover for her anytime she wants to take my ass ....yes go slow and communicate ..use lots of lube ...funny but we actually use crisco as a lube ..smile ...when she says its time to bake cookies im on my knees doggy style --lol when she fists me she likes me on my back so she can play with my cock while fisting me ..then once i cum she feeds my cum back to me until i swallow it all ...her 10 in strapon i love the most ...long and thick and she looks great wearing it ..smile ..i always give myself at least 2 enemas so im nice and clean for her to play with ...once her fist is in me and i relax she trys to go deeper to see how much i can take ...call me crazy but it does feel good and i cant believe how much she loves doing it to me ..its like she takes my soul when she is deep inside of me ...gawd knows she already has my heart !!  gladly bending over for her or her friends when she wants to show how well trained i am at serving her ..have fun ...boy i am now hooked ...she calls me her little ass slut and cum slut ...love submitting to her and her desires ..have fun mal


What a delightful and perfectly descriptive posting mal, I enjoyed reading it.

I too enjoy recycling slave cum, as I love feeding it back into slave's mouth, to recycle until the next milking. I also enjoy slave splashing their load on fruit and foods also, and feeding it back to them too. A new meaning to: strawberrys & cream lol [:D]

mal you have a wonderful Mistress, lucky you! Fisting is also an  act of infliction I enjoy, on a very well anally trained submissive.[:)]

http://mistressrouge.webeden.co.uk/




malloves69 -> RE: First time anal play advice (4/5/2007 4:42:28 AM)

thank you mistress ...and yes my ass is pretty well trained ..smile ..sometimes i think it has a mind of its own ...took us like 6 times to finally have her fist pop in but once it did i dont know who loved that more ...me or her ...she really gets into doing that and boy do i cum alot when she does that ..smile ...she feeds me back me cum alot also until next time we play ...i think its really special when she allows me to cum inside of her pussy then she sits on my face as we both watch it drip from her into my open -mouth ,,,i think thats very erotic and i gladly lick her pussy clean of the mess that i made ..just like my ass surrenders to her fist my cock surrenders to her pussy ..smile she wants to see me swallow another subs load but so far we havent done that as of yet ..we have done the bi thing because she loves to see the guy on guy action ecspecially with her being the director ...must say a real cock did feel better then her strapon and yes he was wearing a condom when he was doing my ass ..call me crazy but her fisting me does feel good ..smile ...when i cum she says my ass spasms and tightens around her fist ..she says my ass feels nice and warm and smooth inside ..i love when she takes me ...the chemistry we have together i feel is priceless and i trust her completely ...take care ..mal




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