by Violet on April 18th, 2009

Violet

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Guys- how did you start doing anal play? fingers? toys?

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Answers. 35 helpful answers below.

  • by Rocket on April 20th, 2009

    Rocket

    Yeah that is what I thought... My XIS/O had never had anything done to his back door... I started with giving him oral and switching over to suck on his balls and stroke his cock with my hand... then I worked my way around and began rimming him while stroking his cock... then when his ass was nice and slippery from me licking it, I slipped one finger in and moved it gently... at first he got really ridged... then I stopped moving my finger and just left it in his ass very still... I kept working his cock with my hand and went back to sucking his balls... he relaxed and got back into it... then I started moving my finger just a little... when he climaxed he was so loud... he said it was the best "O" he had ever had... After that he let me do anything I wanted to his ass... toys... multiple fingers, strap on.... he loved it from that day on... the breaking him in phase was the key to him feeling ok with it... he said that after I did that he felt ok about it... good luck....

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  • by Rocket on April 19th, 2009

    Rocket

    Can I tell you how I started anal play with a lover... who had never had it before... or only answers from guys???

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  • by Jonathan on April 19th, 2009

    Jonathan

    Finger only! when receiving head, it is a great sensation & when you ejaculate it feels like you are shooting your cum to the moon. I don't like it all the time though it has to be a really hot & intense session.

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  • by Jimmy on April 19th, 2009

    Jimmy

    we were just being playful one night and the next thing i know i was slipping a finger in and she liked it so we went on from there

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  • by Left hand of SATAN Right hand of God on September 17th, 2009

    Left hand of SATAN Right hand of God

    fingers did'nt use toys 4 a few years

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  • by Mr. Sex ~ The Original Mr. Knowitall on April 26th, 2009

    Mr. Sex ~ The Original Mr. Knowitall

    Finger, maybe tongue or cock. Depends on my mood and how nice her ass looks at the time.

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  • by Outta-here on April 22nd, 2009

    Outta-here

    I start with..."My dear...do you like anal play?...if you do..let me know and I will initiate"...Very polite and unassuming.

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  • by knotcrafter@yahoo.com on April 18th, 2009

    knotcrafter@yahoo.com

    First time? A well-lubed middle finger, entering slowly, retracting and re-entering until there was some relaxation, then one finger became two, repeating the process until I could slide a butt plug in fairly easily. I also rubbed her clit and massaged her breasts to help her relax and take her mind off of just one source of stimulation. Since she was tied and gagged facedown spreadeagled, that also heightened the experience for her, and me. Her climaxes are more intense if I'm inside her and rubbing her clit. And it just keeps getting better.

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  • by blackhart666 on October 22nd, 2009

    blackhart666

    normal a finger why I licking and nibbling her clt

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  • by Rev. Doc Holiday on October 15th, 2009

    Rev. Doc Holiday

    finger, training beads, be wa- it great when the ol prostrate get stimulated- also a good way to prevent prostrate cancer!

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  • by Anonymous on September 29th, 2009

    Anonymous

    1. Watching porn
    2.Experiencing body massages
    3.A female giving you anal play that if you let her do this to you. I believe a lot of males love it but they afraid someone might call them gay by men for letting a female play with their butts. It doesn't make a man gay for letting a female do this to them. Some guys are insecure about their sexuality.

    4. In the early 80s I have read a book sex: girls and guys. It mention sex, masturbation and more. It says males explore their bodies like females do.

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  • by puppydog on September 18th, 2009

    puppydog

    fingers first then toys now very big toys

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  • by Anonymous on September 12th, 2009

    Anonymous

    Some men watch porno getting ideas from what they see or read in a book.

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  • by paul on August 15th, 2009

    paul

    I started with my finger while masturbating of course that makes me cum faster and very intense.

    Then one day I decided to lay on the bad and finger my ass with as many fingers as I could. I stopped at 4,then masturbated to an intense orgasm.

    Then I bought some dildos and butt plugs of various sizes and started to anal masturbate regularly like twice a week.

    Now many years later I stll anal masturbate and wife hepls out sometimes, I or we still do this about 2-3 times a week. The real big ones can really cause an intense anal orgasm.

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  • by JoeSchmo6114 on August 14th, 2009

    JoeSchmo6114

    I had read a few brief things about guy's doing thtat so I figured I'd try it out, so I just used a finger one day while I was masturbating.

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  • by endowed - out on August 14th, 2009

    endowed - out

    Are you asking how we start anal play with a woman? She first starts in the shower using the hose from the shower head to shoot water in her butt to clean it out. That alone helps a bunch because I can pretty much stick it in with ease, and I'm talking all the way in. Oh it's so hot just thinking about it. I think I'm going to ask her for some anal sex tonight! Yeah, you got me all worked up for it now.

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  • by Anonymous on August 14th, 2009

    Anonymous

    I never did anything to my ass until I went out with an older woman who taught me the way. After sucking my cock like a pro, she lifted my legs, licked my balls and went right on until she reached my asshole. She ate my ass, fingered it for the first time and then fucked me with a strapon. It was a grand awakening
    into the world of anal pleasure. After she fucked me, it was my turn. My cock was drained and my ass reamed. I ate her pussy, then she flipped over and raised her ass, spreading her cheeks apart. I took the que and I ate her ass, fingered it, then fucked her in the ass(my first anal). I never looked back.

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  • by fallox on August 9th, 2009

    fallox

    When I was a teenager I sometimes masturbated in front of a mirror. Lying on the bed. I started seeing my anus and playing with it as well. Then one day I wondered the feeling of inserting something there... And used a cucumber!

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  • by anallover1977 on July 10th, 2009

    anallover1977

    I started using a finger once a month, then when i worked up enough nerve I bought a dildo, then i bought a vibrator. my favorite toy is this 5inch penis that pumps in my ass streaches out so i can use all 4 fingers in my ass then i masterbate along with the butt plug best orgasim was today it was the 6th time this week i did it love anal sex.

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  • by Anonymous on June 23rd, 2009

    A few weeks ago my G/F's twin sister had asked to use a strap-on with me and my G/F was excited by this and encouraged me to allow her sister to do so. a few days after convincing me they ventured to the store and picked out the strap-on together. I then asked a few questions on how to make it pleasant such as preparation and lube to fully prepare myself. But was told not to so much as use a finger, because she felt it'd be more erotic to be the first to put anything up me. The day of, we decided to have a lot of foreplay and she wanted to make sure I was comfortable. Sometime into the play she left the bed and ventured to the hallway returning in a very sexy outfit equipped with a large strap-on. My skin felt like a thousand needles and chills ran up me all at the same time. It was a huge turn on seeing her approach me she looked so powerful and just absolutely sexy with a little evil grin. I then was instructed to suck on her she slide it into my mouth asserting her dominance but being very respectful also. after thoroughly wetting it a with my mouth I then allowed her to find her way inside me, more difficult then it sounds but she eventually found her way deep inside me (lots of deep breaths and digging my fingers into the bed) the first 15 mins or so hurt a great deal there after it began to feel really good and I began to relax as she reached around and really took me out of this world to be perfectly honest. Other then being sore for the next few days it was probably the sexiest power exchange i've had in my life. Really enjoyable experience.

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  • by subiedrienker..fame in my name on May 12th, 2009

    subiedrienker..fame in my name

    I give kisses an dthen start licking her ass.
    making fast round with my tongue around her hole....
    and then give a few shots further in , with my tongue...
    generally, she pushes my head in and grinds a little....

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  • by Chubbychaser84 on May 10th, 2009

    Chubbychaser84

    Toys and dont laugh but a nice big thick carrot does the work! I did not see the point in anal, it was just painful and felt like I was going to have a big poo. One night a couple of years ago I was a bit bored so I thought I would insert a large sex toy up my arse for the hell of it because to be fair I had never given anal sex a chance and I had an anal orgasm. It was wonderful because I ejactute too quickly with a penile orgasm. With this I could just go on and on and it got me to a higher level than a penile one! My penis was soft because I was too busy thinking about having something large up my arse. It was not a prostrate orgasm and the feeling was all around the inside of the anus. I find toys the best because they are larger than a real penis and you can still get your partner to move the toy for you.

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  • by on vacation on May 2nd, 2009

    on vacation

    My first time was in college. Used to stick my soapy finger up my ass. Very pleasurable.

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  • by scumoftheearth on May 1st, 2009

    scumoftheearth

    Well one day we were in bed together when for some reason the alarm clock went off. It was on the other side of the bed so I crawled over her to get it. Obvioulsly I was on all fours and she just sat up and started licking my ass all over. She asked if I liked it, and I did so she kept it up. Rubbing my balls and my cock too. Before too long she slid her finger inside of me. I didn't know what to do at first. I thought to myself "this feels great. Does this make me gay?" Obviously it doesn't. Now when ever she goes down on me she includes the ass in some way. It's great.

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  • by 08Busa on April 28th, 2009

    08Busa

    She wanted to try something different so I said give me your worste.

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  • by kiwisoccer on April 26th, 2009

    kiwisoccer

    Havent tried it yet but always willing to give most things a go ;)
    Might have to see what sexinfo101 has to say about it!

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  • by love_master on April 20th, 2009

    love_master

    i'm straight male, i started trying a finger but wasn't working for me so i wen't to toys they did a little better. then i went to my gf finger and that did the trick.

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  • by Curtis on April 19th, 2009

    Curtis

    Can't tell you, depends on the situation. Sometimes with toys, sometimes licking, sometimes right away in.

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  • by new2thegame808 on March 30th, 2010

    new2thegame808

    i enjoy it very much wile i get oral and my ass licked i want to have a finger or two in me!!!! that just makes it so much more pleasurable and eager to try new things!!!!!!!!

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  • by swiggletree on March 21st, 2010

    swiggletree

    I use dildos now ; ) how about yourself?

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  • by dadof3andhusbnd on June 18th, 2010

    dadof3andhusbnd

    i was curious one day when i was jacking off. i stuck a few fingers in but didnt get very deep so i used the handle to a toilet brush with some lube on it that was to thin and kinda hurt so i used the handle to a hairbrush. that felt very good and gave me one of the most intence orgasms of my life. now that im married my wife uses a strap on when we do anal play

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  • by flasher on September 21st, 2011

    flasher

    I started by shoving a finger in my ass while I was jerking off. It felt so good I went to the adult toy store and bought a vibrating dildo.
    The first time I bought a dildo I was really embarrassed. I've bought about a dozen so far, and I'm no longer shy about it. It's erotic to think that the sales clerk, male or female, or the person next to me at the checkout is thinking that I love it up the ass, because I do!

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  • by headGivers on September 29th, 2009

    headGivers

    fingers while watching gay porn

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  • by swiggletree on March 21st, 2010

    swiggletree

    I was about 14 and l was watching porn and they were doing vaginal and the girl was faking it BADLY. THEN he started doing her backdoor and her face said it all, at first her face looked like she was off on a distant planet then quite a while into it she got really moany (real sounding) and started talking real fast in spanish. After that l realized that if anal plunging did that to that initially bored latina, then imagine what it would feel like! So l got a some petroleum jelly and smeared it all over a flashlight and put it in. It was difficult and hurting too much and i couldnt thrust it in and out (being my first time) so i decided to stroke and get it over with and see what would happen while doing this and l was rewarded with a great orgasm. After that flashlight debacle i switched to a candle and found i could thrust it alot faster. Im 24 now and im not gay and l currently anally masturbate about twice a month, alot less than l used to.

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  • by Anonymous on March 29th, 2011

    Anonymous

    I started fingering my anus soon after I started masturbating at age twelve (I'm in my forties now). I was fascinated with looking at my ass in the large mirror we had in the bathroom. I made a couple dildos out of skinny tree branches that I whittled down, sanded, and varnished. It was fun to lube up and plunge them in and out while jerking off. Then in college, I had a girlfriend fifteen years older than me who had a thing about men's asses. She often turned me over on my stomach so she could finger my anus, with her hand between her legs to make it seem that she had a penis. This was before strap-on dildos were well-known or commonly available. Years later I told her about my obsession with women taking men with strap-ons, saying if we had one back in the day, I would have let her f**k me up the a*s. "LET me?" she scoffed. "I would have INSISTED on it."
    I have never experienced a strap-on or even a dildo in a woman's hand, but I use plugs and toys on myself. And my wife goes down on my bottom (analingus) and fingers me to my heart's content. Not only are the orgasms incredible, but the emotional experience is deeply gratifying.
    --WD

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