your first time with anal sex

Wed, 03/31/2004 - 17:40
Submitted by kemiiyan

can you please share the story of your first time experince sex from the back?...i will please like to know how it went and how you decide to do it..did u guy have problem using the restroom afterwards..did u regret it

Your first time with anal sex

Mon, 04/18/2016 - 15:02

I was 13 and a 17 year old nieghbor who I idolized took me to his basement and showed me a couple of dirty magazines. It didn't take long till he said I'll,show me mine if you show me yours. Things progressed to him says ng I will suck you if you suck me and he went first giving me my first blow job and a came like never before.
After a couple of minutes it was my turn and I started sucking on him like he did to me. He was really hard and a lot bigger than and me after maybe 3-5 minutes of sucking on him he pulled his dick out of my mouth and spun me around on my hands a knees and using my silva on his dick plus spitting in his hand he pushed into me . Wow I started crying for him to stop but he keep pressing till he kind of poped in and I thought I was going to pass out it hurt so much. His parents were not home and no one heard me.
It seemed like forever but it started feeling better and I was hard again as he pumped away. .maybe 3-5 minutes later a could feel him getting bigger and felt him start pulsing and coming in me. That put me over the top and without anyone touch me I came so hard that I hit myself a coupl of times in the face. That was the first and only time a real dick has ever been in me.
I was so sacred that he hurt me because it really hurt going to the bathroom afterwards and I couldn't tell anyone about what happened.

Because of this I missed out on the normal experimenting with boys of my own age. I think I would have found out later when I was 14-16 .
I had several blow jobs from guys in college but never giving one since I was 13
I blocked this out entirely until a old GF stuck her vib in mr while giving me head I came like crazy and over the the next 24 hours the memories came back. He robbed me of my innocence but because of him I love having my ass fucked every so often. And sometimes I think about having a Young man that I knew was clean and had a nice pink 7-8" dick fuck me while I'm fucking or going down on my wife and see i cam fell him cum in me

My first time with anal sex

JessieLu's picture
Tue, 06/30/2009 - 04:13

My first time with anal sex was a masturbation experiment involving a small dildo. I was around thirteen at the time. By the time my first guy came around I was pretty comfortable with sex and he brought up the topic of anal sex. I'd done little things myself but the thought of actually doing that with a guy intrigued me. It was a long-distance fling and I enjoyed my first time(shortly after my eighteenth birthday) being with him. The end of the first night was incredible. We'd talked about it but when he asked me to move into a doggie-style position so he could take me from behind...I wasn't expecting it at all. Most would assume it was a painful experience but aside from the initial discomfort that he immediatly remedied by whispering calming words to me, I wasn't hurt. My first lover wasn't a large man there, but I enjoyed myself and consider myself lucky. He didn't use lube or prepare me so the situation was much better than it could have been. And I never regret it.

I have found since then that I need a slightly longer length than he had to really drive me nuts. Seven or eight inches in and for some reason my entire body goes insane and I end up trying to impale myself. I'm not sure if I should worry or be amused but either way I quite enjoy this practice and don't plan on stopping anytime soon. Vaginal sex IS enjoyable, but I haven't found the right guy to fill that slot just yet, and its just much easier to get off with anal.

I love to tell this story

Mon, 06/29/2009 - 23:02
carlisleorama (not verified)

Because it's so naughty. When I was 21 I had a boyfriend who I was very sexual with, most of my early kinky experimentation happened with him. He loved having sex outside and we were wandering around my house one night in the athletic fields of the nearby high school. We started to get a little lost and ended up on the lawn of some really neat looking building, but it was dark and we couldn't tell what it was. We started to get busy right out there in the open, we were in doggy and he asked me if he could go for my ass. He had wanted to for quite some time, and I had read up on it and knew we needed lube and probably a lot more anal play (I think he had put his finger in my ass, but if he it wasn't like he had really "opened" it up much), but I was caught up in the moment and said sure. Here's the real surprise of where all this going: it didn't hurt at all! It was a little uncomfortable and I wasn't quite ready to experience pleasure from it at that time (just like the first time you have vaginal intercourse, ladies), but there was no pain. I must have been really wet because whatever he got on his dick from my pussy was plenty of lube for the whole 10-15 minutes of anal! Or perhaps he was just gentle enough. I spent the rest of the night farting and apoligizing for it with him laughing and saying he didn't care. I retraced our steps the next day to find where we had been, and it turned out to be the Jewish Community Center. Neither of us are Jewish, but I still think that puts the cap on the naughty evening.

Thank you for sharing

tom.penry's picture
Tue, 06/30/2009 - 09:23

What a great story!!!!!!!!!!!

first time anal sex

Mon, 06/29/2009 - 01:30
EVERETT (not verified)

the first time i had anal sex i was seven years oln i am a man know i went to the store with my mom
and had too use the restroom. when i got in there there was only one man i colsed the stall door a
found out it did not lock i did not think much adout it at seven i had a bladder trouble and wore diapers
i stood in front of the shitter and pulled my diaper and shorts down. the man next to me in the outher
stall door see that i wore diapers and ask y so i told the truth the man got up i thought that the man left
the restroom but i was wrong the men forst his way behind me i tryed to stop him but he was too big he told me if i did what he said i would not be heart the man made me leen over and grid the back of
the shitter i did what i was told i heard the man unzip and pull down his shorts i looked back too see
this man spite in his hand and but it on the end of his cock the man moved his cock to my anal opening
and pushed it inside me it heart like hell because he just drove it in this man fucked me till he cum inside me i cryed after he pulled out he made me pull up my diaper 1/2 way and he filled it with his piss then he made me pull it up the rest of the way the man told me not too leve the restroom till he was gone i did what he said i could feel him cum in me and did not like anal sex much thinks

Don Juan's picture
Wed, 03/31/2004 - 18:57
Don Juan

hopefully I with some luck and alcohol my wife will respond! I have had anal with previous partners but she flat out refuses

Re: your first time with anal sex

Wed, 03/31/2004 - 19:53
Anonymous (not verified)

kemiiyan wrote:
can you please share the story of your first time experince sex from the back?...i will please like to know how it went and how you decide to do it..did u guy have problem using the restroom afterwards..did u regret it

the first time my partner and I did have anal sex we had to use some lubrication. I was a little uncomfortable and very nervous, but we took it slow and my man was very in tuned with when I did/didn't like it. I think in a good environment where you both feel comfortable will allow you the ease to try the back way.

Wed, 03/31/2004 - 21:38

I agree. With the right partner, lube, and position, anal sex can be very enjoyable. The secret is you have to relax, and as soon as you tense up, it's gonna hurt. You got to let go, and visualize pleasure...receive it. If he has a big dick, your ass might not be ready for it. Lube is important. Take your time, be in control of the dick, and you do the guiding, not him. The way you can dictate how much dick you have is by being on top. Only fuck what you can fuck, don't try to be an acrobat.

Make sure he wipes his dick off before he sticks it in your pussy...danger!

Sorry! There is no choice of

Fri, 04/14/2017 - 01:32

Sorry! There is no choice of switching from ass to pussy, though of course pussy to ass is possible and desirable too. But after each session of anal penetration, be sure to wash the penis with ample water and soap. Mere wiping will not work.

Fri, 04/02/2004 - 16:01

Ooo, anal sex, first time i had that my boyfriend was trying to dom me and punish me by doing anal, but it backfired cus i liked it. Sometimes I think he likes doing anal a lot more than regular sex. Which is ok but sometimes you just dont want to do it! uhmm, he never had problems with the bathroom btw.
Ive got some suggestions though, use plenty of lube, and the best positions is on your sides spooning, because your relaxed, and missionary with your legs over the guys shoulders. Youd think doggie is the best but it stretches the muscles in your butt.

Fri, 04/02/2004 - 22:42
Kojak Kitty

My first time I was drunk but I loved it. The guy knew how to do it.
I have done it several times there after, it can be great especially with a vibrator up your cunt. :wink:

Sun, 04/04/2004 - 22:57

My 1st time with anal was with a dildo. My boyfriend liked to finger my ass during sex but never went any further. The first time I put that fat rubber friend up there I thought I was in heaven. I think that was the first time I had multiple orgasms while I was masterbating. I love having mybutt filled.My husband now doesn't do it often but when he does it is great. I always thought all guys wanted to do it there but I have actually been with very few guys who liked to do it even once in a while.

Mon, 04/05/2004 - 00:16

my first time trying anal (key word being TRYING) i freaked out and ran to the bathroom before my boy could even get a couple inches in. i thought it felt like pooping, only in reverse.

i'll try it again though.

Mon, 04/05/2004 - 16:57

The first time I had anal sex was with a guy I was in love with. I was drunk and we always had really good sex, but this night I had my period and was so horny I thought I was going to explode. He started playing with my pussy; we were standing up kissing and feeling each other on his wall. He put me up against the wall, turning me around, and he rubbed his dick on my ass. I guess I was so horny that I moved pass the pain real was almost non-existing. I just remembered feeling good and cumming from my ass, which was crazy.

Question: Does anyone have any stories on the first time a guy came in their ass?

Sat, 04/17/2004 - 12:25

My first experience with anal sex was hellish to say the least. I was younger and less experienced than I am now. I had no idea what I was doing and it felt like I was taking a shit. Just awful.

My husband and I will occasionally take part and when we do I love it. But its wasn't like that in the beginning. It is all about how your partner treats you, how you feel, the luberication, and so forth. I am really gald I decided to give it a try with my husband, I've not been disappointed.


Sun, 04/18/2004 - 22:38

I fear anal sex like the plague! I tried it with my last boyfriend, who had a relativley small dick, and before he could get to mid-shaft I FREAKED :shock: out and started crying {because it hurt so bad}. My boyfriend now, who has a FAT nine incher :lol: , is trying real hard to explore my back alley, and I strongly forbid his member from entering my ass. My last boyfriend was a real asshole, and was totaly dominant in every aspect in our relationship. There was no trust, no nothing, as far as I am concerned there should have been no relationship at all. My boyfriend now is my soulmate and the love of my life. I have no doubt in my mind that I will be spending the rest of my life with him. And when I turn him down he always says stuff like .... "you loved him more than me, that is why you let him do it!" :roll: I always assure him that it is not the case, but it always comes up the next time. What should I do?????? Did it hurt so bad the first time because I deep down dispised my ex for controlling me? Or does it always feel like someone is cutting your ass with a dull knife? Any suggestions?? :?

Mon, 04/19/2004 - 09:38

i never thought about it before but when i met a girl i dated for a short wile she asked me to stick it in her ass and to tell you the truth it was great. i couldnt belive a women can take it like that and ask for it to be harder she was very much in control and new what she was doing i felt like a young buy again having sex. man you women are the best thing on this earth espesially if you know what your doing. i know i am a lil off of the topic but if women can just stay in charge and trust me the man will follow.

Aww, Kris!

Mon, 04/19/2004 - 19:30

i hear you on the pain's really too bad that the love of your life can't see that your anus has nothing to do with love! maybe you can get him to try a fat 9-inch dildo up his ass, with you wearing the strap-on harness and thrusting into him while he's bent over!! seriously - your forbidding of his anal exploits has to do with reality...and yeah, in gay porn guys with giant cocks pound other guys up the ass but they're pros, they have elbow grease (an anal lube that's really thick and gooey), and their asses have been well-warmed up. if you really need to show your love then it will take, seriously, a few months most likely, of you working on your anus, with a finger, then two or three, then a small dildo, then larger ones...then the tip of his dick, and so on. if you do put anything in your ass make sure it has what they call a flared handle or base, so the base is wider than the tip that you're putting into your ass.

and remind your boy that you love the hell out of him, that anuses are sensitive and well-made to be 'out' holes but not 'in' holes (thus the pain!!), and that he's all you need...the old guy is history and guilting you about something you did in the past is pretty unfair of him. good luck!

Thu, 04/22/2004 - 13:23

i looooooove anal. my guy friends dont understand how a girl can like taking it up the ass, because theirs no prostate gland, or anything else there for them to hit that would make it pleasureable, but idk how to explain it.... lube it up, bend me over, and put it in... love love LOVE it! :P

moni_leigh's picture
Sat, 04/24/2004 - 09:18

The first time I had anal sex I remember it hurt like hell at first, but once I relaxed I enjoyed it. My hubby wants to try it now, so we bought a butt-plug; I'm going to wear it for awhile before we attempt it. See topic "any advice for first timer?"

Thu, 05/27/2004 - 04:39

my first time i trie anal was when i was 18, he was turkish, i was a little scared when he pushed it in, and i was very nervous,i was getting the feeling of cold water running up my back, made me feel alive. we did get a little messy. and it was a long time before we tried it again, but now its the best! i cannot promote anal sex enough, believe me! :wink: !!! its fantastic

Anal Sex

Fri, 05/28/2004 - 01:28

When I 1st experienced anal fucking, I about cried! It hurts like hell! It sure as hell feels like shit going back up your asshole! When the mood is right and my hormones are flying through the roof, I am always ready for anything - even anal! I am soo horny that I don't feel the pain and just wanna get fucked any which way! Feels great, but I think it's alot more pleasure for my fiance than it is for myself! Good tips, lots of lubing, teasing with the tongue and finger, virbaters are great, dildo's you name it!

Fri, 05/28/2004 - 19:14

The first time I had anal sex was with a guy that totally did not respect me. And let me tell you, it hurt like hell, like everything was being ripped, it was so awful. But now I am dating a man who loves and respects me, and we tried it for the first time together the other night. He started playing around "back there" with his fingers, then we lubed up and went to it. He was really understanding and said just do what you can, don't push yourself, yadda yadda. After we got going it was awsome, and oddly it didn't really hurt that much. I can't wait to work on perfecting it!! Anal is definatly a must!! :lol:

anal sex

Tue, 07/06/2004 - 23:29

My first time huuuuuurt....we tried again later, and it didnt hurt at all, because i forced myself to relax....but I received no pleasure from it at all.

Thu, 07/08/2004 - 15:35

well.. my very first time was awful.. i hated it and it tottaly killed me with pain that i couldn't walk that well for an hour or so.. so i always refused to do it. then again..that boyfriend was an asshole... my boyfriend now, well..fiance...we did it for valentine's day. he always wanted to do it before hand but i wouldn't let him.. so we started havin` sex, and i got on top..and we kept goin`.. then i just stopped, and stuck it in my ass..and it was greattttttt.. :D and he was totally confused, yet extremly pleasured at the same time...i think it doesn't hurt that much if yer happy with that person.. if the guy doesn't treat you right or whatever the situation may be, then it's gonna hurt.. so just relax, lots of lube, and do it when/how you want to...

Thu, 07/08/2004 - 16:38

Thank you for your honest posts and suggestions. I have another question. My husband and I have tried this a few times, but after a few minutes it hurts too bad. Everytime we try it I can last a little longer and enjoy it more. However, when I call a halt, we resume regular sex. It bothers me that I may get an infection or something from this dual approach. Should my husband wear a condom (which he hates, but would probably do) and then take it off when we switch to regular sex?

Fri, 07/09/2004 - 08:58

the first few times i had anal sex were the best and i was laying on my back. a couple of times we used ky and the other times i used my own wetness. but then my husband came along and tried to cram it up there like it was the black hole or something and i have never let him try again.

Fri, 07/09/2004 - 11:00

katie8078 wrote:
Thank you for your honest posts and suggestions. I have another question. My husband and I have tried this a few times, but after a few minutes it hurts too bad. Everytime we try it I can last a little longer and enjoy it more. However, when I call a halt, we resume regular sex. It bothers me that I may get an infection or something from this dual approach. Should my husband wear a condom (which he hates, but would probably do) and then take it off when we switch to regular sex?

OMG! :shock:
if he's not going to wear a condom, at least have him wash his cock with hot water and antibacterial soap. i know you may think that'll kill the mood, but i think that's better than getting a vaginal infection that'll prevent you from having sex for a long while. a little advice...NEVER go from anal to vaginal/oral sex w/out cleaning the COCK...that goes for toys too. :D

Fri, 07/09/2004 - 12:05

my first time w/anal was painful as hell...i was 17 at the time dating a 27 yr old...i loved him w/all my heart...and i was just happy that he took it slow and was patient...he used lubricant but it still hurt...we did it a few times after that and each time got a lil easier for me to do...i remember one point in our relationship were i had taken his whole dick in my ass:shock: ...i really didn't hurt at all...i had gotten used to it...

Sat, 07/10/2004 - 00:52

I actually did have a couple of tears fall out the first time (and only time a guy's been up there, lol) a guy stuck his cock in my poor little ass, lol. It was the worst pain, and I felt like I was going to poo all over the place when he pulled it out (I did have his jizz running out of me, which sort of felt like poo...this guy must have left a gallon in there, lol). He was a nice enough guy, but that was the last time a guy has done it.
Now, I've had women put things in there since then, and I love that now. A girl I dated for a while had a strap-on cock that she would do me with from time to time, and I let her fuck my ass (very, very gently to start, lol) and it was very cool. :)

Don't double dip

Sun, 07/18/2004 - 01:10

[quoteThank you for your honest posts and suggestions. I have another question. My husband and I have tried this a few times, but after a few minutes it hurts too bad. Everytime we try it I can last a little longer and enjoy it more. However, when I call a halt, we resume regular sex. It bothers me that I may get an infection or something from this dual approach. Should my husband wear a condom (which he hates, but would probably do) and then take it off when we switch to regular sex?]

One should never double dip. It is very un sanatary. The anus holds lots of infections bacteria and outting something from your ass into your virgina is a no- no

My first Anal Sex

Mon, 07/19/2004 - 23:32
horns holding halo

I was always curious about anal sex, however i never had a man interested in it...or maybe we just never brought the topic up. Anyway, the guy I am currently dating had asked me what I haven't done that sparked my interest. When I told him "Anal sex" it was almost like he was relieved to hear it. Come to find out, he loves anal sex! One day when we were together, and by together I mean fucking, he reached over to his night stand and pulled out some K-Y Warming liquid. I thought it was sweet that he had it all planned out...everything to make the experience enjoyable for me. He slid his cock in me a little, but made sure to ask if I was ok. With his guidance I had the best experience ever. I am now a TRUE LOVER of anal sex. I would pick it over vaginal any day. I do not regret it and I recommend it to any couple looking to share something incredibly intimate with eachother.

Thu, 07/22/2004 - 23:06

My first time with anal sex was with a guy I was just casually dating. It hurt pretty bad at first because I wasn't relaxed enough and we didn't use enough lube. The next time I tried it we used lots of lube and to go really slow...much better.
I had anal sex a lot with my ex-fiance when we were together. It was very enjoyable. We would do DP a lot (double penetration), with a vibrator in my pussy and him in my ass and me rubbing my clit.....amazing sex that was. :D But bad idea to let him cum in my ass. :shock: I won't even go there. :lol:
Some guys I've dated are freaked out by anal some think it's awesome. I can go with out it, but I do enjoy it when I have it. My butt is usually a little sore the day after though hehee.

tips for good anal

Sat, 07/24/2004 - 13:21

Love it, love it. Can't live without it. Some tips:

- lubrication is key. The ass, unlike the pussy, does not self-lubricate. If you think you're using enough KY, use some more, both on tab a and slot b. :D

- foreplay is also important. Try playing there yourself with a small dildo before you let him in. I love having my partner play with a toy or fingers while he's eating my pussy. The excitement is compounded by the thought that maybe he's looking forward to anal sex and wondering what will happen next.

- position matters. I usually climb on top and sit on him so I can control depth, speed of entry, direction of movement, etc. If your partner is experienced or particularly sensitive to your subtle forms of expression, you may allow him control from the rear. Some men get crazy turned on by the simple sight of you on all fours offering yourself to him. If you've had some success with anal on your own or in another position, try it. But the tightness of the orifice may also end up in air trappage and extreme discomfort, so if it's just not working in that position at that moment, try something different with you in total control.

Some women only orgasm with anal if they are involved in clit play while it's happening. But I can tell you, an anal orgasm is incredibly intense. Anal is a great option for that annoying time of the month. It's also great if you are on the go since that part of the body is, um, accustomed to expelling, and if you just visit the potty afterwards right away and try to push it out, you shouldn't have all the long-term cum leakage problems the pussy has.

One more tip - when you're both done, do get up and take care of business immediately. It's quite embarassing when you try to hold it like gas and the sphincter just won't take it anymore. No matter how sexually confident you are, no woman farts poop-laced cum gracefully.

Have fun!!

Sun, 07/25/2004 - 00:54

My first time(s)...for the guy definitely...I was nervous, not all that into it, just wanted to please, and it just wasn't even remotely pleasant. Not healthy for any situation really. I even remember telling myself that I would never do that again, with anyone. But now, with my current boyfriend, I'm totally into it! I love it. With him, it started slowly. Talking about it on the phone, mentioned in phone sex, a finger in my ass while he was going down on me and one day, with PLENTY (and I mean PA-LEN-TY!) of KY (personal fave), we tried it and boy oh boy! It was fantastic! I love it now. LOVE IT! We go to sex stores for "butt toys" and just have a hell of a time with the whole thing. There's just something about it. It feels great, then there's the whole "forbidden" thing--not everyone is doing it, so it must be "naughty"--a HUGE turn-on. (There are very few forbidden fruits left in our society...)

We've recently discovered, after a year-plus, that I can lay on my back and with my ass slightly more tilted up than with regular legs-around-his-waist-missionary, we can do anal very comforatably facing each other. I might even admit that it's my favorite position. Though, honestly, it depends on the mood. Sometimes, a girl just likes to be ridden...or to ride...or...

(No problems going to the bathroom afterwards.)

As with anything, give it a try if you're interested, but if it's not for you, say so. Everyone wants their partner to be comfortable and happy. He may be disappointed that you're not into it, but he'll get over it. He'll still fantasize about it while jerking off, so he's not totally deprived. :wink: