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First-Time Anal Sex Stories
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Surprise development

At first anal sex was a definite no with my wife. She made it quite clear from the start and I never bothered raising the issue. One night during some play she was laying on her front as I was fingering her pussy and I leant forward, parted her legs and licked her anus; it just seemed like the right thing to do at the time. As I did this I thought she would either be turned off or make a comment about 'not going there' but instead she responded by pulling herself up on to her knees and bending right over, I licked her anus more and used plenty of saliva as I started to push my tongue further in to her.

After doing this for around 5 mins I took some of the lube I had been using on her pussy and gently rubbed it on to and around her anus, I used plenty of it and slowly and very very gently passed my fingers around her anus sliding them around in the lube and she asked me to carry on in a very turned on and sexy voice. After a while I took a beep breath and really gently started to put ONE finger in her anus, I was waiting for the 'dont do that' but all she did was move herself nearer me and pushing my finger farther inside, I was surprised to say the least but carried on with this, then with more lube and again very slowly I pushed two fingers in.

She started to move herself forward and back on my fingers so I moved them in and out as if I were fucking her, at this point she became super aroused and was moving faster banging her cheeks on my hand, I used my other hand to rub and finger her pussy and she just went wild, pulling at the bed sheets and shouting 'yes yes' and I can't tell you how amazed I was, this continued until she had an orgasm and laid back on the bed, she was bright red with panting, about 2 mins later she was asleep.

The next time we had sex I did the same as before except this time I took the courage to penetrate her and one thing that made her scream 'fuck me fuck me' was having my dick in her ass and my fingers in her pussy, I came so hard in her anus that I was out cold in no time. On the third occasion we had the usual foreplay, some pussy and anal fingering then she broke her own second rule. She gives a great blowjob no problem but I never ever came while she did it. This time she sucked me until I could not hold on any longer and I told her I was going to cum but she just kept sucking until she had the whole lot in her mouth. I have no idea why things suddenly changed like this but let me tell you I ain't complaining.

Winning her over- Jess, Age 25, San Diego

I used to be disgusted about the thought of having anything around let alone in my anus. However, one night my husband gently rub by rosebud while giving me oral sex. I just about went through the roof. It felt so good. Then he asked me if I wanted to try anal sex and I said yes. He made sure that he was really lubed up (we find astroglide works best as it stays slippery without drying). I had my first true orgasm that night. It was incredible. The key was lots of lube, going slow and communication.

Thanks Ernie - Age 35, New Jersey

My first time was when I was in High School. My friend Ernie and I were fooling around on the floor in his den. I always liked him to take me from behind - it felt naughtier and sexier that way. I was about 17 and he surprised me by running an ice cube along my spine and down the crack of my butt. I shivered with anticipation. He put the ice cube aside and began to rub my ass. He didn't ask about anal sex. He could see that I was turned on. He pulled out some lube and lubed up his finger, inserting it into my ass. I moaned with pleasure and pushed back towards him. Soon I could hear him pouring more lube onto his cock. At that point I was so turned on I would have let him do anything!

Soon he placed his cock head at my sphincter and said "it's time." Slowly he pushed forward until the head popped beyond the sphincter. Then he stopped to let me relax. After a few seconds of adjustment I started to slowly push back onto him. It was incredible!!!! He reached around and started to play with my clit - I saw stars and came continuously!!! When he came I could feel him swell and spurt into my ass.

Sadly, we didn't get to repeat that performance. I had a boyfriend after him who wasn't very gentle and I didn't enjoy it much with him, but now I engage in anal sex as a way of having fun with my husband. I thank Ernie for such a great introduction to anal sex. It was incredible!!!

Careful research - UK

I've recently had my first anal sex experience with my long term partner. It's been my fantasy for many years, but I've had medical problems which required surgery in my anus. I've since been too scared to try anything back there.

After my partner mentioned he'd like to try anal sex, I came clean and said I would too, but was scared of ending up back in hospital due to injury. We set about buying toys & lube and did some research. We had a couple of goes, but were disappointed after I chickened out, but I didn't want to give up. My boyfriend said not to try again if I found it too uncomfortable, and I appreciated the pressure being taken off. I found this site and must have read every single story for tips!

We were having sex, and I knew I was ready to try again. The best tip I got was to have him penetrate a bit, wait and relax, then a bit more etc... Deep breathing was also very helpful. He followed my every instruction, and I think a respectful partner is paramount here.

I was amazed it wasn't painful, and there was no blood, which I expected after my previous problems. I had the most intense orgasm, and so did he. He said "you've never made a noise like that before"! In fact, I think I'm a lot more keen on it than he is!
I think anal sex will feature regularly in our future sex life. Thanks to everyone for posting their tips and helping us out!

With the Ex - Age 37, San Jose, California

The first time I got anal was when I was married to my otherwise frigid ex-wife, Heather. We were uncharacteristically naked and messing around one warm, lazy Saturday afternoon when I dared to act on a longtime fantasy of mine and started to gently finger her anus while I ate her pussy. She started to respond to my gentle probing much to my surprise and I got a little more aggressive. However, I didn't get my hopes up until she suggested I get some lube. I wasted no time in sprinting for the bathroom where I grabbed some Vaseline - the only lube we had. I leered to myself in the mirror and shot
myself a wink before running back to the bedroom. Imagine my surprise when I found her face down on the bed, her fat ass already in the air. My dream come true! I quickly knelt between her thighs, generously lubed up my engorged prick and her tight asshole and started to ease it in as best I could - I was so hot I was ready to explode. She then said that I shouldn't come in her ass but should pull out instead. "No problem", I said. I didn't mean it but what the hell.

She moaned in pain as I slowly pushed my cock deeper into her and she begged me to finger her clit, but it was out of my reach, so she frantically fingered herself instead. I finally got my thick six and a half inches of meat in her behind and I rested a minute so I could enjoy this ass-fucking as long as possible; I knew it was probably the first and last time she would ever let me enjoy such a delicacy again. I finally responded to her pleas to hurry up and I started to slowly stroke my cock in and out of her. I reveled in the new sensations of her tight virgin ass wrapped around my cock, her sphincter drum-tight, and how good her fat ass felt against my belly, as I ignored her earlier request and proceeded to have the orgasm of my life when I unloaded a tidal wave of semen into her rectum. I did pull out and gave her butt a final courtesy squirt of come, just to show her I did listen to her.

Afterward, as she sat on the toilet, she bitched to me how that was fucking and not making love and I had to agree with her for the first time in our marriage!!!

Beads to begin

I had my first experience with anal sex about thee weeks ago. I was very nervous to try it but my husband was very gentle and took a lot of time getting me ready. For a few weeks before we had been experimenting with each other. Most of the time we would take turns inserting our fingers inside each other and we gradually worked up to him inserting anal beads inside of me. The fist time I use the anal beads I had an amazing orgasm.

The night that we first had anal sex we were fooling around and just enjoying some foreplay. I rolled onto my back and my husband started to put his finger in my bum. It felt really good and he kept saying how much he wanted to be inside me. He put on a lot astroglide and started to rub the tip of his penis on my bum. I wasn't sure if I was going to let him try to go inside, but he asked if he could try and push it in. I told him yes and he got into position and pushed in . It was much smoother than I thought it would be. it felt so amazing and we both had great orgasms.

Highlight of My Sex Life

I'd had anal sex before (with a girlfriend who found vaginal intercourse uncomfortable and actually preferred anal), but it was another girlfriend's anal initiation that really stands out in my memory. I would often finger her asshole as I ate her out or when we fucked. She always seemed to dig it, but I was still surprised how readily she agreed when I suggested we give anal a try. She grabbed some moisturizing lotion to use as lube (which I guess isn't recommended, but we didn't know any better, and no harm seems to have come of it). I began to go down on her -- thinking an orgasm might relax her and make the next part easier -- but she was excited to get to it. She slurped at my dick, finding me rock hard already -- I was excited to get to it, too -- then turned away, presenting her ass.

I lubed her hole with lotion, dipped a finger in, then two, nothing new for us. Then I smoothed some lotion onto my cock and placed the head at her asshole. Leaning into her gently, I slid in with ease. She gasped as my cock stretched her, not a gasp of pain but of pleasure. I withdrew slightly, then slowly slid all the way into her. "Oh my god," she breathed, pushing herself back onto me. We had started with her on hands and knees, me kneeling behind, but gradually wound up with us both kneeling upright and pumping together. I reached around and squeezed her breasts with one hand.

Her nipples were harder than I'd ever felt them. With my other hand I reached down to play with her pussy. I couldn't believe how stimulated she was. Her clit was engorged beyond anything I'd seen before, sticking out like a tiny penis. I dipped my fingers into her sopping slit and stroked her rock-hard clit between a slippery thumb and finger, jacking it off like a little cock as I pumped in and out of her ass. She had always been the most orgasmic sex partner of my experience, but I'd never felt her cum before quite as powerfully as she did then, and we came together, me shooting off deep inside as her sphincter muscle spasmed around my cock.

Collapsing to the bed, breathless, we remained spooned together as I slowly melted inside her. She said she felt incredibly full with my cock up her ass and enjoyed her first time so much she suggested anal again when next we got together. Sadly the repeat performance wasn't anywhere near as magical for either of us. We never tried anal again after that and broke up before long (for other reasons), but I still remember my ex's anal initiation as the #1 highlight of my sex life.

"Bear Down" He Whispered

The first time that I experienced anal sex was with my now ex. He was kind and gentle person, but not in bed. The first time that he brought it up I told him I was unsure and didn't want to get hurt. He promised that he would take care of everything. (hint if using a condom don't use the ribbed kind, the edges maybe painful). 

One night when we were fooling around he mentioned that he wanted to try it.
We had been fooling around for about a half hour before. I was already wet and he was rock hard. He flipped me over on to my front side. (I like to be on all fours with a pillow underneath me) I was starting to have second thoughts when he was starting to lube his cock and my hole up. I was talking dirty to me as he was probing one finger inside of me. Then when he slowly worked in two. This was feeling so good already I was practically begging for the real thing. 

He whispered to me to bear down, as I did his cock was in line with me and he slowly eased into me. Slowly until he was all the way in. After that he was pumping in and out it was the most natural yet amazing feeling ever. I loved feeling him place all of his weight on me and pump, in and out, in and out then faster and faster until he finally couldn't hold it all in any more. I loved the feeling of him that deep inside of me not to mention all of the hot steamy cum! Hope you have a similar first experience.

Woman on top

My wife had tried anal sex with a previous lover. He never got further than the tip. She said it hurt and she was afraid to try again. We had been dating for only about 2 months and had talked about it, so she finally got curious enough to want to try again.

I knew better than to rely on porno movies for position technique. The woman has to feel safe during anal sex to be able to relax enough to enjoy it. I knew that her on top would accomplish that. She would feel in control and i could stimulate her clitoris and also play with her very sensitive nipples. 

We usually spend 30-45 minutes on foreplay alone, and she gets so damp that she drips from nipple stimulation. She got on top and we had sex for a few minutes, when she reached down and positioned herself for anal penetration.
I didn't thrust, letting her do all the movement. She came harder and faster than she ever had in her entire life. She even told her friends how to do it, and we got feedback, and many thanks. I'm sure their boyfriends and husbands were grateful also.

Now I don't ask for anal sex. she just does it on her own, usually two to three times a month. My best advice is to let her control all of it. Eventually she will want you to nail her there, but until she feels safe and knows there is a pleasurable alternative to sex, it wont happen. Make the first time mind-blowing and the rest will work itself out.                

Making her want it

The first time, I was on my knees, doggy-style, with PLENTY of lubrication applied to both myself and him.  Although I had really wanted to try, I have to admit that I was a bit scared.  To relax me as well as to make me hot for it, he had me lean further into the pillows on the bed so that my head was resting on the pillows.

Then he instructed me to reach behind and spread my ass cheeks for him, which I did.  After doing that, he took his penis in hand and rubbed around my hole until he made me so hot by doing that that I was practically begging him to put it in.  

I helped by pushing back (as if having a bowel movement) and it let the head of his penis get completely in.  He went slowly until he was fully in and then stopped for a moment.  After that moment, he slowly started to withdraw but not completely, again pushing himself back into me, this time a bit faster.  

He kept doing this, each time getting faster than the previous time, working me into a frenzy, and until I could feel myself moving and pushing back against him. 

Needless to say, it wasn't long after that that he climaxed in my ass.  And in him doing it the way that he did and not by force and with plenty of lube, anal sex is something that we have come to enjoy a lot.

Welcome Home

My boyfriend was posted abroad for his job.  He was back for a visit and we had had sex.  We were lying in bed just talking, and I was lying with my back against his chest, with his hand just casually playing with my nipples.  He was getting hard again, and his cock touched my ass.  We both kind of just waited, and I moved so that his cock was right next to my asshole.  He asked me if I was sure and I said yes.  

He slipped on a condom and first pushed his cock into my pussy to get it a bit lubricated.    Then he pressed the tip of his cock against my asshole and gently pushed.  At the same time, he put his hands on the top of my shoulders.  He pushed a bit more, and I said "Yes!".  He pulled out and then, with one hard thrust, thrust his cock deep into my ass.  There was a fleeting second of intense pain which almost immediately gave way to a feeling of fullness.  

We paused again for a second and then he started to fuck my ass, first slowly and then increasingly fast, pulling his cock all the way out and ramming it in again.  It felt so good for both of us - he loved the tightness of my ass, and I loved how big and hard his cock felt.  He came at the same time I did.  Now I love anal sex.

Second Time's the Charm

Anal sex is a great way to have a really hot session. My girl and I started it pretty soon after we got together and haven't stopped. We started when I was eating her out and she was raising her hips into my face. my tongue kinda slipped to her ass and she moaned real loud. Thinking she obviously liked it, I carried on, fingering her clit at the same time. She went wild.

The next session, I did the same thing with the same result. This time as she was nearing her climax, I slipped a lubed (with spit) finger up her butt. She cried out and came straight away.

We were talking after (we love to analyze our sessions) and she said (don't know if this is the same for every girl) that the 'g' spot can be reached either through her vagina or her ass. I suggested we try anal sex next time and she agreed.
The first time was a disaster, we were both pushing too hard I stretched her ass a bit too far (I'm pretty thick) and she asked me to stop.

The next time, we worked up to it slowly and I inched my dick into her ass a bit at a time. When I was finally all the way in, she asked me to keep it inside her and not move for a bit, she breathed deep and I felt her relax around my cock. I started moving in and out real slow, within a few strokes she was getting hotter and wilder.
That was the best night we'd ever had.

Little By Little

I had anal sex for the first time last night with my boyfriend of almost a year.  I had been curious about the act and the cleanliness issue for a while now.  I did some research on the internet and was getting close to being ready.  I started experimenting myself while masturbating I would use a latex glove and insert just the tip of my finger into my anus, then it graduated to a vibrator last week.  

While having sex last night he was behind me (doggie style) and his penis slipped out from the lubricating, when he was putting it back in, it penetrated just the opening of my asshole.  (I used antibacterial soap to cleanse just the outer parts and the rectum before hand.) I made a noise and he asked what was wrong, I said I was experimenting.  He allowed me to sit there a second then he inserted a little more, then a little more, until he was fully inside me.  

He began pumping slowly until he was going full force.  The feeling was amazing, if he could have reached around and been able to stimulate my clit I would have gone of the Richter scale, but it was too far for him to reach so I did it myself and had a wonderful orgasm (or two).  I would definitely recommend it, just go slow and do your research.  

Younger Woman

The first time I had anal sex was with a woman 25 years younger than me.  We were lying on her waterbed talking about our past sexual experiences when she ask me if I had ever fucked anyone in their ass.  I said no, and she said I could fuck her ass but I first had to kiss her ass. 

 She got on her hands and knees and stuck her beautiful ass in my face.  I started kissing her ass and finally ran my tongue in her asshole.  I kept this up for about 10 minutes while she came twice from my tongue in her ass.  She told me to put two fingers in her asshole which I did and fingerfuck her asshole and she came again.  

She said she was ready for my cock in her ass now so I slowly feed my cock in her asshole.  It was an incredible feeling having never done it before.  As I was fucking her ass she was tell me how good it felt and she loved getting fucked in the ass.  When I told her I was ready to cum she said "Shit yes, fuck my asshole and fill it with cum".  I didn't think I would stop cumming as I filled her asshole with my cum.  We saw each other off and on for the next three years and I would kiss and fuck her asshole sometimes with a dildo in her pussy as she liked two cocks in her at the same time.  I haven't seen her for four years but I will never forget her.

Teenie bopping

My first anal experience was with my boyfriend when I was 17. At the time, he was 19, and we had never tried anal sex before. He had asked to place it in my ass a few times, but I had not felt comfortable with it at the time. This night was different. After a night out (I was sober), we started to fool around and things got very hot. I gave him a blowjob and then he asked me if he could "place it in my ass". I wanted to try it and so I guided him into my ass. It felt sooo good, especially from behind. The feeling of his cock inside me drove me crazy, and ever since then I have wanted to do it again and again and again. I would recommend it to anyone. I did not feel any pain during my first time, but if you do, once you get used to it, the feeling will be tremendous. Try it, it's great!

An older married man

The first guy to do me anally was an older married guy I played with for a while. His wife wouldn't ever do anal for him and he practically begged me to let him in my ass.  I hadn't before (I was only 18 then) but I was ready to try it. He was so sweet about it, going slow, making sure it was alright. Which was good right at the beginning, but after a couple minutes of that, I was like "quit being so nice and just fuck my ass". And he did and it was great. He had the most intense orgasm I've ever felt a man have. Lot of years of built-up anal frustration came out in my butt I think. I got off so much knowing what it meant to him to finally do something he wanted to so badly.

Don't give up

My wife and I have been married for 15 years. We were both raised in religious families and we raise our handful of children like wise. So far I agree with the tips given. The reason I've been fascinated by anal play goes back to horny teenage days when I wanted sex with a woman but didn't dare due to religious beliefs. Instead, I experimented anally with various objects in the shower while I masturbated. With this in mind can you believe I was a virgin when I married my wife 15 years ago?

Try it yourself first with a dildo the same size as your erect cock. You have to be willing to take it, if you're going to give it. You learn a lot about going slow, waiting, and finding your not always in the mood for it, and she will react in like manner. And yes, if you angle that dildo just right on your prostate you can have your own g-spot orgasm even though your cock isn't erect.

Dropping hints. Talking about anal sex. Seeing a few anal porno acts and light fingering got my wife ready. We had been married 4 years when she asked for it. I was so stunned and scared that I lost my erection.  And by the time I found it, she was losing her mood but I went charging in anyway. She was in pain and I was humiliated.

Learn brethren from my mistake! You don't want to ruin your wife's opportunity to enjoy anal sex, let alone your opportunity. I had to wait six more years for her to get horny enough to ask again.

The score came as a result of tonguing and licking her ass. I slowly teased from her pussy to ass. And I mean slowly, over many love making sessions. Finally, I was making love to her asshole like I did when we first kissed. She loved it and started moaning loudly. I made her come like that for weeks before she asked for penetration. Then I made her come with a finger in her ass many times. She was really enjoying this for months as was I.

Then while on vacation we rented a porno with some ass fucking in it. We both go turned on and she asked if I would give it to her in the ass. Fear returned, a flash back to my screw up 6 years earlier. Would I do it again? She got on all fours. I went slow. Once the head of my penis was past the rim, I waited even though my instinct was to push on in. After a 30 seconds or so she began pushing against me, wanting me deeper. It only took about ten thrusts by her against me and she exploded in a hard orgasm. However, she wanted me out immediately even though I hadn't came yet and was totally turned on. Respectfully, I pulled out and washed up and fucked her pussy hard til I came. If I had continued thrusting in her after her arousal left, I'd never have got back in.

Since then she and I have been having anal sex 3 times monthly. And now she demands I fuck her like a stud horse. "Fuck me hard damn it!" is a typical line. Now she says, "I like getting fucked up the ass." I'm blown away every time she says it. She is so into it, that I'm afraid she's going to say it in public around our close friends.

A couple of closing tips: Buy one of those remote butterfly units for her. It doesn't have the damned wires to get tangled up in. My wife loves to wear her butterfly on her clitoris and get fucked up the ass after a pussy-to-ass licking. Lastly, my wife enjoys fucking me up the ass with a strapped on dildo. It makes her come faster than anything we do in the bedroom. Maybe it's the power, the view, or the role reversal. Anyway, after 15 years of sex, we both enjoy receiving and giving anal pleasure and hope you find pleasure in it also.

Second time the charm

My first experience with anal was a nightmare.  My ex and I decided to try it and it was a very painful experience.  He didn't stop when I asked him to.  I was totally turned off of it after that. I am single again and after a lot of reading decided to try it last fall.  I met a nice guy who had never done it and wanted to try it.  I was a little hesitant but while we were into a hot and heavy session he was trying to slip it into my pussy and missed and it slipped into my ass.  I guess I was so wet from being horny that it was well lubed up.  Anyway, we were both laying on our side and I found it to be totally comfortable with absolutely no pain at all.  It was really exciting and I even had an orgasm! 

Maybe if you try a different position and try what is comfortable for you it will be as pleasurable as it was for me.

Teen love

My first time was with my girlfriend. At the time she was 16 and in high school. I was 19 and had never even thought about it before. We had just recently started having sex after several months of fooling around. I was laying behind her and for some reason just decided to try and slip it in the backdoor. To my surprise she moaned pretty loud but somewhat quiet. Since her sister was on the other side of the wall. She told me to be nice but she didn't stop me. It was a really good feeling. Super tight and I knew I wouldn't be able to hold the cum back. The only bad thing, it was so tight, the condom ripped and it kinda hurt her butt when it tore. She ended up getting an ass full of cum. It was the best sex i had ever had.

Born again virgins

We have been married for 7 years and we have recently tried anal sex, I guess the 7 year itch. I have been playing around with her bum with my fingers for some time but recently I got up the nerve to try it all the way. 

We like watching porn videos and I had made a point in renting the "better" anal sex videos. I came to the opinion that this is not a uncommon fantasy since it seems that two thirds of the porno videos seem to have some sort of anal sex involved. Anyhow after watching some good anal sex videos my sweety's curiosity got going. 

The first time I tried it was a bit awkward, amature me was trying for the gusto a bit too fast. I did not hurt her but she did complain about feeling a bit uncomfortable, mostly mentally. For me it was a great wonderfully tight feeling, I did not have much time in the saddle that time but my mind was opened up this new wonderful sex. It is a strangely different feeling, instead of a moist becoming wide opening that gets tighter as in a vagina, anal sex is a very tight opening that needs special attention and it gets looser as one gets in deeper, the analogy of a funnel comes to mind. 

Anyway the second time we tried it I well lubed her up and worked my fingers so I could get two fingers in easily . This time my penis went in lickety spit. The most intense feeling is not in deep penetration but inserting only a couple inches. The feeling was extremely intense and I did not last long at all, She did not believe the intense feeling either and we were both glowing for days after. We both came to the conclusion it was like being born again virgins. Although she still has some strange feeling about doing it I have made it known once a month would be a good thing. This is just G-R-E-A-T sex and I am happy to say my sweety has the nicest, tightest ass around

Unexpected delivery

The first time was such a shock to me. Earlier that evening I had been joking around with him and his friends, saying that if he was a good boy, I'd let him fuck me up the ass. I knew he loved to do that, but it was something I had shied away from.

Later that night, he was fucking me doggy style. Because I was so wet, his cock kept slipping out. Every time he re-inserted his cock into my pussy, I'd think, just fuck me up the ass, but I didn't say it out loud.

The next time he slipped out, I felt a little pressure on my asshole, then full insertion.  I yelped from the pleasure and the pain of it. My asshole was a virgin and he is NOT a small-dicked man and he was NOT being overly gentle. He pounded away at my ass as I moaned. We've done it once more since then (standing in the shower). We both look forward to many more times together.

Very special massage

After the video finished, my girlfriend and I sat on the couch making out. I rubbed her breasts through her shirt, pinching and flicking her nipples. She lifted up my shirt and sucked on my nipples, her tongue dancing quickly across them. Then she stopped and said "Take your shirt off and lie down on the couch. Close you eyes. I've got a surprise for you." I did so and she went into the other room to collect some stuff. When she came back with massage oil, she gave me a wonderful backrub, both sensual and therapeutic. 

I then returned the favor, rubbing oil on her shoulder and neck. I told her to lie down, and I put oil on my hands and massaged her breasts and belly. She was very excited by this, so I began stroking her now-moist mound. She was going crazy with desire and I was greatly enjoying watching her twist and moan. We were both incredibly turned on. Her moans suddenly stopped, as an orgasm swept over her. She turned over on her hands and knees, saying "Take me in the back. Fuck my ass." This kind of surprised me, since we had only fingered each other before this. I grabbed the bottle of massage oil and poured some on my hands. I rubbed the oil all around her tight rosebud, and then slowly inserted a finger in to help open it up. I then put oil on my hard cock and got into position behind her. 

Ever so slowly, I gently pushed my cockhead into her tight ass, as I didn't want to hurt her. She screamed, "Yes! Give me your dick! Fuck my ass!" I slowly pushed my cock into her, spreading her cheeks wide with my hands. She pushed her ass back against me, and I began stroking in and out of her. She was going wild, moaning and pushing into me. I grabbed her shoulders to help thrust deep within her. Her asshole was so tight and gripping that after only ten or fifteen strokes I came hard inside her, while I kept thrusting. I must have cum for 40 seconds at least. It was one of the most intense orgasms I've ever had. And it was the first time for both of us.

You're never too late - Age 43, Canada

My wife and I were one month shy of our 20th anniversary. I had thought about it for years. Anal stimulation was always part of our foreplay. One "the night" I grabbed some lubricant off the night table and began working it into her. Then I asked her to get on hands and knees. I got behind her and rubbed my cock up and down her backside. Finally, I just pushed in the head and stopped, waiting for her to relax. I wasn't sure how she would react, but after laying very still for several minutes she began to rock back onto me. It was wonderful, now part of our regular lovemaking. better late than never.

Practice makes perfect - Sarah, Age 18, Fayetteville, NC

One time, my boyfriend and I were having sex and he told me that he wanted to put his dick in my ass but I told him that I had never done it and I didn't want to try it at the moment. He said he understood where I was coming from and he didn't pressure me.

The next day, when I was home alone I started thinking about how painful anal sex could be. so i decided that if I wanted to please him, i would have to try. So I ran to the bedroom and took out the K-Y Jelly and lubed up my middle finger. I gently  massaged my asshole, once it was relaxed I slowly inserted my finger into my ass. It felt a little uncomfortable but i did like it. After a few minutes of doing it a decided to try two fingers. After a while 2 fingers wasn't enough. I had to try something bigger. I don't have any dildos so i went to the kitchen and got a banana. I put a condom on it and started fucking my ass with it.

When my boyfriend came home, I was eagerly waiting for him. We started fooling around. I gave him a blow job, and after that I lubed up his cock and  laid him flat on the bed. Then I took his hard dick and guided it towards my asshole. When he felt the tip of his dick around my asshole, he said "what are you doing". I did not reply  continue to stick his dick into my ass. I rode his dick for about 20 minutes until I made him cum inside my ass. I loved he feeling of warm cum in my ass. since then I have become an anal freak

What took so long? - Jewel, Age 43

File me in the "better late than never" category of anal sex. I was 38 and in my second marriage before I ever tried it. I always thought it was a little strange and too "icky" to do it. But after much cajoling, pleading, begging, insisting and suggesting by my hubby, I relented. I was very uncomfortable at the start, but by the time we were finished I was asking myself why the hell I hadn't tried it sooner. I never knew it'd be so good. Now I'm the one doing the suggesting and insisting half the time.

It "feels delightful" - Massachusetts, Age 36

I remember the first time - my boyfriend said, "we're gonna have anal sex" the first weekend we were together.  I thought, "Yeah, right!" My boyfriend and I started going out three years ago and we'd known each other ten years at that point.  I'm not sure how I would have felt if I'd barely known him!

But, I was so curious after that comment!  He promised that it wouldn't hurt and that if it did, he would stop immediately...  He had a store of KY Jelly on hand.  First he licked and sucked me - he made me cum a few times.  And we did have vaginal sex with me coming, and him not. 

I remember him turning me over so that I was lying on my stomach...  he licked my asshole, over and over, while his hands played with my pussy...  it was so yummy...  I knew what we were about to do, so I don't remember actually cumming at that point...  I was just a little too scared.

After awhile, one of hands came 'round to play with my asshole rather than my pussy...  I remember that I was very excited - it felt wonderful to have his mouth and hands at my pussy as well as have his fingers playing near my asshole.  And then, a finger slipped into my ass, so gently  and so slowly, that it felt wonderful, not scary at all.

I know that this felt delightful... 

After I was moaning, and he had succeeded in getting two fingers gently inside my ass, he readjusted so that I was underneath and he on top...  Very gently, he put his lubed cock right at my ass, and still gently, pushed the tip of his cock against it.  I know he was playing with the lube, because I felt the cold liquid lube at my ass where his cock was.

He gently, firmly, pushed with the head of his cock against my ass...  I told him I was scared, and he again promised that he'd stop at any time.  He put his hand near my face, gently stroking, promising that he'd never hurt me.  The fact that he was listening, willing to stop for me, in spite of his own pleasure, helped me to be willing to try the next part...  Gently, firmly, slowly, steadily, he pushed his hard cock against my asshole...  It was slippery, warm, big, exciting...  And it never hurt!  He pushed gently until the head of his cock got past the outer ring.

Halfway in, not all the way in, he murmured gently against my ear, "How are you?  Does it hurt?  Should I stop?"  I murmured back, "I'm fine, it doesn't hurt!  Go slowly, but go inside my ass." 

I loved the feeling once his cock was inside.  I couldn't believe it!  It did not hurt, I felt so full, complete... 

Anal sex is one of our passions.  We have anal sex about one in every three times we make love.  We've been together three years and I come just by anal sex alone or playing with sex toys in my pussy and his cock in my ass....... 

I think our sex life is much fuller because he wasn't afraid  to talk to me about anal sex.  I had always been curious, but until I was with a man who knew what to do (or had read up on it enough so that he BELIEVED he knew what to do!) I was just too scared to really talk about it, never mind try anal sex.  And now it's a "regular" part of our sex life!

Who'd have guessed????

College lessons - Erin, BC, Canada

Well, it was a Sunday night around 3:30 in the morning and my girlfriend and I began to fool around. We had thoroughly discussed anal sex before and as the horny kid that i am I wanted it to be tonight. First I had her lay on her stomach with a comforter balled up underneath her chest so her plump ass was easily accessible. I broke out the KY and put it on my pointer finger. I put my finger in and out of her ass and when it was sliding nice i decided to go for two fingers. I put some more KY on my other finger and slowly slid them in. After both fingers were sliding in and out of her ass for about 3 minutes I decided it was time. I had her suck my cock to get it nice and hard. This only took about 30 seconds. After I was hard I lubed up my cock with some more KY. I got behind her and had her spread her ass cheeks apart. When I was lined up with the hole I slowly pushed in. first half the head then stopped for a bit then a little more then a little more till my cock was in her ass. The whole time starting with the insertion of the fingers i talked to her and it made her more comfortable. After my cock was in the rest was history. 

After five years of marriage

We had been married for 5 years but had never tried anal sex; all we did was vaginal fucking. I got some advice from one of my Internet friends( female ) and I did exactly what she told me. I was fucking my wife as usual when I whispered to her that I wanted to try something new. She did not mind, and she knew what I was going to do since we had talked about it before. I lubed my dick with a generous amount of KY Jelly and lubed her ass also. With my finger I penetrated her ass hole and made some circles for a little while. Then my finger became two, and she was starting to moan and scream. After a little while, I felt her ass relax. 

We were doing it doggie style and I had my dick with my hand and pointed the towards her asshole. I was surprised that she pushed back towards me letting my dick slipping into her ass. I pushed a little further and suddenly my dick head disappeared inside her! She screamed for a while and started to bush back to me until I could not see my dick. That was great. I came inside her and started to go in and out of her ass. nothing better that lubing her ass with my own cum.

Will you be my Valentine? 

My first time was last Valentine's day.  My husband and I decided to do something special so we put up his tent in the  backyard and bought some candles and some drinks to get the mood on.  When we were finally having vaginal sex in one of those cock's slip out of the vagina his cock's head touched my ass and we stopped for a sec.  He told me: Let me try! I was scare I admit it but I do anything for him.  He was very gentle with me so it didn't hurt.  Now we enjoy having anal sex especially when I'm having my period and can't have vaginal sex.  I only put a tampon on and let him fuck my ass.

Patient teacher

My first time was when I was a teenager, dating an older man. Let's get past the controversy and just enjoy the story...

He was incredible -- introduced me to almost everything under the sun.  I was very hesitant at first, but he started orally (rim jobs) then used fingers, then very small dildos, then dildos that gradually got larger, and eventually, his cock was pounding in and out of my very well lubed ass just as fast as in any pussy.  Now, keep in mind, this was all over the course of a year -- no rushing involved..

That advantage now for me, and also for my new husband, is that anal play is practically a FETISH for me -- I can't have FULLY satisfying sex without SOME anal play of some kind....

Keep in mind that not EVERY woman is like that, so don't count on it...however, with patience, understanding, and loving kindness, most women will grow to enjoy some anal activity.

The lighthouse

I have always been this adventurous woman when it came to sex and almost anything else, but anal sex scared me and seemed somewhat forbidden.  I knew so many people who had done it before, but for some reason I remained an anal virgin until I met the right person to trust and I knew I had to try.

My boyfriend and I were out one evening having a few drinks and he told me he had a surprise for me.  We left the bar and he took me to the beach.  As we walked around the beach, things started to heat up as we were touching and deeply kissing each other everywhere!  He took me by the hand and walked me to this beautiful old lighthouse we had seen many times during our visits here.  He looked at me and asked if I wanted to go in.  I was eager to explore all of him and the lighthouse, but was afraid we would get caught.  He said that was part of the thrill and he wanted to show me the thrill of trying new things.

We climbed in through an open window and walked to the top.  The view was beautiful as we stood leaning against the rail.  His hands reached around me from behind and started to massage my tits as he kissed and sucked on my neck.  I leaned back into him and felt the pressure of his cock against my ass so I started grinding my ass against him and he began to moan. (Actually, it was more of a growl.)  It was at this point that he whispered in my ear, "Do you want to experience the thrill of something new?"  I knew I was ready.  I wanted so much to feel his hot throbbing cock in me...all of me.  I wanted to give him my ass.  I told him to fuck me!

He leaned me forward over the rail.  All I could see was the ocean below us as he raised the skirt of my dress and ripped off my panties.  He was so hungry for this.  He had waited so long.  I felt his fingers go deep into my wet cunt and he was pumping me getting his fingers so creamy.  He took his fingers out and started to massage my asshole.  It was so hot!  I tensed at first because I was scared, but then I felt his fingers slide right in.  "Oh God!"  I screamed.  It was the most intense feeling ever.  He was sliding his fingers in and out of my ass so deep.  He pulled the fingers out and I felt his cock head press against me.  Now, I was really scared but at the same time crazy for him.  He grabbed my hips and plunged deep into me.  I screamed like I never have before as he pumped me against the railing.  His cock felt huge!  There was no pain only pleasure as he fucked my ass.  He pumped me so hard until I felt him start to tense and I told him I wanted him to fill my ass with his cum.  Just hearing me say this made him rip his load deep into my asshole and I came with him.  It was more intense than anything I have ever experienced.

We are still together and anal sex has become a regular part of our sex life.  It is one of the most erotic things we do because we always remember the first time and the power of living for the thrill.

High school hijinks - Mic, twentysomething

The first time I fucked a girl in the ass was in high school. It was a nice early afternoon session of love in the sunshine and nobody to bug us. She didn't take all that much coaxing. I just rubbed the redeye while the other stuff was going on, licking the finger and slid it in. Gently at first rubbing in a circular motion around the rim to get the hole nice and big and willing; that drives 'em wild until they're begging for it. Then slide it up in slowly if it's her first time. Then getting deeper and faster you know the drill. 

She lived with her family in a condo, and she was on all fours in the living room  facing towards the front door about 3 in the afternoon. I'm straddled behind like a true cowboy and she's howling in either pleasure or pain. My cock sliding in and out of her fresh juicy ass and... bam, in walks someone!!! Door was supposed to be locked but in our frenzy to get down and dirty someone must have forgot. It was only her brother so I was lucky. If it was her father walking in on some horndog banging his only daughter's virgin ass then I woulda been sailing over the balcony with a smile on my face and my final load shooting out my cock. So here's my tip: lock the front door

A long weekend - Mindy, Rochester, NY

When my boyfriend first asked me to have anal sex with him, I wasn't too sure I'd like it.  Still, I like to try everything at least once, so, we spent a few evenings reading everything we could about it, bought several brands of lube which we first tried with different sized dildos to see which allowed easier penetration, bought several body oils and scented bath salts and reserved a hotel suite with a Jacuzzi for a long weekend.

At the hotel, we had dinner on the terrace, a bottle and a half of wine and spent a long time just sitting next to each other, totally relaxed.

When we finally went in to the bedroom, Jerry, who seemed a little tense told me that maybe it wasn't a good idea after all, because he was afraid of hurting me.  He's rather well endowed and I knew the thought of his size had crossed both our minds more than a few times, but I wouldn't hear of it. We had talked about wanting to have anal sex together long enough for me to insist we at least try to do it.

We kissed for a while, touched each other all over, undressed each other quietly and then he laid me down on the bed and started licking me all over.  When he started darting his tongue in and out of my anus, I was so worked up, I came within a minute.  It was fantastic!!! 

Although I was already wet enough to be penetrated, Jerry applied a generous amount of lube in and around my anus, while working two fingers in and out of me.  One of the books we had read said that the easiest positions are for the woman to be on her side or on her back.  I always thought that doggie was *the* anal position, but I guess someone else knew better. 

So, I propped myself on a couple of pillows and lay on my side at the edge of the bed while Jerry rubbed more lube on his penis. He gently placed the head at the opening of my anus and ever so slowly eased it in.  He held it there for a second and asked if I was ok, which I was.  So, my ass wasn't exactly used to having something go into it, and it felt a bit strange at first, but it really didn't hurt. I asked him to push a bit more in and he did, pausing from time to time to make sure I wasn't getting ripped apart. When he finally pushed it all the way in, I was moving around and pushing back to take it all in.  It was simply wonderful!!  We spent the rest of the weekend trying out differnt positions and enjoying this new side of our relationship.

It's been a year since our first anal experience and we still don't get enough of it. I now enjoy having him enter me in one (slightly rough) thrust and then pull it all the way out and re-enter me in fast, long strokes.  We still have vaginal sex from time to time, but both of us tend to look forward to our backdoor fun all the time. 

Don't wait....try it out today.  You'll love every second of it!