My Favourite Life

October 12, 2006

Anal Sex 101

Filed under: Anal Sex,Sex — myfavouritelife @ 11:53 am
Tags: , , , , , ,

Many people want to know how to go about having anal sex, so I decided to re-date this post. Men want to know so they can fuck their wives and girlfriends in the ass, and the women want to know how to make it more comfortable, if not pleasurable. I have spent much time in practise and have read some books that have been published on the topic. I can tell you there are women who enjoy anal sex and do it because they want it and enjoy it. I am not saying that every woman enjoys it or even that every woman would enjoy it. However, if done right, there is absolutely no reason it should be painful. Here an example of anal sex gone very wrong.

The Ultimate Guide to Anal Sex for Women

Why am writing an article explaining how to have anal sex? Basically, it is because—as I mention above—many people don’t know how to go about it, especially beginners. There are articles available that tell what to do, but some of them contradict others. I point out some of these contradictions. Here is what I know.

About 40% of woman in the US have received anal sex, and about 20% do it regularly. So while these numbers show that less than a majority of women do anal, it also means that of the 120,000,000 adult women in the United States, about 48,000,000 have done anal and 24,000,000 say they do it regularly. These are substantial numbers. The argument that it is an unusual request doesn’t hold much water.

If this is the first time she is receiving anal sex, these steps are even more important. Relax. Start slowly. Take it easy. Follow her cues. When done correctly, anal sex should not be painful—not even a little bit. If she is uncomfortable, you are doing something wrong or moving too fast. Perhaps she isn’t relaxed enough. If she drinks, let her have a glass of wine or whatever suits her fancy—Xanax or Ativan would help, too. Foreplay is even more important for anal sex than for other more typical forms of sex. She may find a little rim job to be pleasing. Start with a massage with oil. You’ll need lots of lubrication. Personally, I prefer Slippery Stuff, though a brand called Wet is fine, too. K-Y works in a pinch. Vaseline causes too much friction. This is the first contradiction to what I have read. Vaseline is a terrible lubricant for anal sex, and it breaks down latex condoms. Don’t use it unless it is the only thing you have available. Saliva would probably work better, but it isn’t that great either. Remember, the ass is not like the vagina. Although it can take a cock, it is not designed to lubricate itself. This is important and why you need to use lots of lube.

She may be tempted to use some numbing agent. I recommend you don’t. It is important that she feels what is going on down there. I can’t say this often enough, if you are doing it right, it won’t hurt, so she won’t need to numb her ass. If her ass is too numb, she might let you shove your cock in her ass before she is ready to receive it. This could cause tearing. If this happens, your chances of screwing her ass again will be a lot less. Take care of her ass, and she will take care of you. Show her you care about her ass. Even if it is for your own selfish reasons, treat her ass with care.

Anal sex can be performed in all the same ways vaginal sex can be performed: missionary, doggie, woman on top. Although woman on top would seem to provide her with the most control over speed and depth of penetration, I have found that—starting out—most woman are averse to impaling themselves on a cock. This leaves missionary and doggie—spooning works, too, but coordination comes into play, so you might want to defer this position until you and she have built up a bit more experience. I really enjoy anal penetration in a missionary position, but I feel the best position for beginners is the standard doggie style position with her head down and her ass in the air, cheeks spread and full and unimpeded access to her asshole.

Grace's Ass

I am rushing. Let me go back a bit. Before you start, you should remember some rules for having anal sex for the first time. I will list them, and then I shall explain them, were necessary.

  1. She should do an enema before starting—a couple of hours in advance is best.
  2. Relax
  3. Go Slow
  4. Use Lots of Lubrication
  5. Wait for her cues
  6. No double dipping

1. Do an Enema

While this is not extremely important, it will help to make the experience less messy, and it will feel better—for both of you. Trust me on this. She should do her enema a couple of hours in advance to clean out the area. Use warm tap water. The advance time is to allow the water to work its way out of her system before you screw her ass. Don’t overdo the enemas. Don’t take more than a couple of enemas a week, even if you have anal sex more often. You may end up stripping your ass of some protective mucous lining.

2. Relax

I mentioned this before. You should be relaxed. It is more important that she is relaxed.

3. Go Slow

Don’t rush. Take your time. Once you have your cock in her ass and get going, she will eventually relax, and you will be able to pick up the pace.

4. Use Lots of Lubrication

Again, I recommend Slippery Stuff—lots of it. Lube your cock. Lube her ass. Don’t worry about using too much lube. It is OK to relube her ass as you get going.

5. Wait for her Cues

If she is taking a cock in her ass for the first time—and even thereafter—, listen to her. When she says stop or tells you you are going too fast, follow her cues. The first moments are crucial.

6. No Double Dipping

Once you have fucked her ass, do not put your cock into her pussy or mouth. This is unhygienic. Don’t think that because you saw Taylor Rain or some other chick do it that it is a good idea. It isn’t. If she gets an infection from double dipping, she will be out of order for a while, so even if your motives are only selfish, refrain from the temptation. Here’s a recap. mouth to pussy: OK; pussy to mouth: OK; pussy to ass: OK; mouth to ass: OK; ass to anyplace else: big no no. ‘Nuff said.

Now, where was I? She was laying face down getting a relaxing back massage with oil. You are ready to get started. More importantly, she is ready. Massage her ass. Not so fast! I said her ass, not her asshole. Kneed her ass. Relax her ass. Work the oil. Now you can work the oil down her ass crack, massaging gently. Massage her asshole with your fingers, but don’t try to insert them. Just rub gently with lots of oil. Her ass will accept your finger when it is ready. This is where you need to start using the Slippery Stuff, if you haven’t yet.

Gently apply pressure with a single well lubed finger, working it in small circles around her anus. Make sure your finger nails are trimmed. You don’t want to cut her ass. She won’t be happy, and you won’t be happy. Use latex gloves, if you wish. Eventually, her asshole will start to be relaxed enough to take in your finger. Obviously, if you have done other ass play, this won’t take as long. If she hasn’t taken anything in her ass before, please be patient. As an aside, you might want to stop here and pick up again another day—now that she has an idea of what to expect. Perhaps you could work up over a week or two until you finally go for it. The anticipation would be electric. If not, read on.

Once your finger has penetrated her ass, slowly message her asshole. Feel it’s tightness. Help it to relax. For most guys,you have to work up to something approximating the size of your cock. Hopefully, this will be more than just one finger. After a few minutes, work in a second finger. More lube would be fine, too. Work them in slowly but deeper and deeper to relax and expand her asshole. Don’t worry, her asshole (like yours) is a very elastic muscle. It won’t remain relaxed for long after you are done with sex—perhaps only the next day for a bit. It will be just as tight the next time you fuck it—though she will know better how to relax, so she will be able to exercise more control to be able to accept your cock more easily as she gains experience. This should not be confused with having a loose ass. I know many women worry about this, just as many women worry—especially younger women—that their pussies will somehow stretch out of shape with use. I promise you this is not true. I have been having regular anal sex with the same woman for over ten years, and she is no looser than when we started. My first wife and I had anal sex about twice a month for seven years. Her ass is not going to get looser, though it may take a few hours or overnight to return to its pre-fucked state.

On her cues, work your way up to three or even four fingers. Once she can relax to that point, she will likely be able to take your cock, which will presumably be quite hard by now. Even though she should be relaxed by now—if not her, then her sphincter anyway. Position your cock at the entrance of her ass. I like to prime myself by taking a few strokes in her pussy, but this is optional. Did I mention to use more lube? Gobs of it. I also recommend that she either uses a vibrator on her clit or uses her fingers. If she is like most other women I know, she will have the best orgasms she has ever experienced this way.

My cock is circumcised, so the head is bigger than the rest. Push it in slowly. It is not like a pussy. Listen to her cues. Once you feel the pop of your head being swallowed by her ass, stop and allow her to adjust. If your cock is average or above average in length, her ass will not be used to taking in anything do deep. Again, procede slowly.

It won’t take that long for her as to adjust to your cock. You will feel her ass loosening. Remember the ass is not a pussy, the sensation will be different for both you and her. If if wasn’t different, why would you bother. The pussy sort of engulfs your cock all the way down the shaft, but most of the contact between her ass and your cock is at the opening. This is important because most of the sensation in your cock is based around the head, which won’t get much sensation. The good thing about this is that without so much direct stimulation, you should last a lot longer, which should give you more time to build up to a strong orgasm. Speaking of orgasm, when you are ready to cum, it is a matter of personal preference where to squirt. For me, her ass is the best place. If she or you don’t prefer that, well, pull out and put it where you both agree is OK. She has probably cum at least once along the way. If not, let her get herself off.

When you are finished, you will have to clean up. For us, we put down an old sheet just in case the enema wasn’t as effective as it should have been. Wipe up, and take a shower, taking special care to wash her ass and pussy, your cock, under your fingernails, and anything else that might have come in contact with her ass along the way.

There you have it. Of course every experience is different. This isn’t a rote exercise, but if you follow this basic pattern, you will both have a nice anal sex experience. Once you have done this a few times, you can experiment with new positions and possibly anal sex toys—though I am not big into toys, myself. If you have any questions, this is where to find me. If you have anything to add, please feel free to comment. Good luck.

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  1. […] OK, I couldn’t resist. There are many real and perceived dangers of having anal sex. There is a right way to have anal sex and a wrong way. These dangers range from the increased probability of transmitting STDs and e coli to rectal tears, but one of the biggest dangers is described in this story. Of course, I can tell you here and now how to prevent this from happening to you: do not take receptive anal intercourse from a horse! No matter how desperate you might be, don’t do it. Now, I know there are a lot of you out there saying, “It’s my body, and I’ll do what I want. And if I want to get fucked in the ass by a horse, it is my right.” Well, OK, so maybe there aren’t a lot of you, and perhaps none of you. In any case, I don’t recommend having any sex with non-human animals. […]

    Pingback by Dangers of Anal Sex « My Favourite Life — September 14, 2006 @ 8:03 am | Reply

  2. […] Lisa is hot—sort of a Fiona Apple (in her finest hours) look-alike: long, dark hair with full blowjob lips; tall, thin as a rail with no real body fat. As such, she doesn’t have much of an ass, but that doesn’t prevent me from thinking about how nice it would be to bend her over a conference table and deliver an anal memo. She has maybe A – B cup breasts that are perfect on her. […]

    Pingback by Sex in the Workplace « My Favourite Life — September 27, 2006 @ 12:31 pm | Reply

  3. […] I was finally ready to get off—the only choice was how. We had already agreed that anal sex would require a condom. I did fuck her ass that way just because, but I was not going to cum in a condom—not with a pretty mouth right there—and I knew she would swallow. It always takes longer for me to cum when I am butt fucking some chick, and condoms only make matters worse. I must have rode her ass for nearly half an hour until her ass was getting so loose, that I didn’t think I would be able to cum. I decided I had better change my plans if I wanted to get off. I wasn’t very creative about the whole thing, but the good thing about wearing a condom when ass fucking is that you can take it off and continue in another hole—not a good practise otherwise. I took off the condom, fucked her pussy fro a minute or two until I was just about to cum, and then I delivered my load into her—perhaps—unsuspecting mouth. She acted surprised, but she took it all in and of course she swallowed like any good woman would. […]

    Pingback by Swapping Sides « My Favourite Life — September 27, 2006 @ 3:48 pm | Reply

  4. […] Another 20% are interested in anal sex—especially how to do it for the first time or how to get a partner to comply. I do outline how to get started, but you do need to already have a willing partner. I try to outline arguments and defenses women often put forth. […]

    Pingback by 17,000 Views « My Favourite Life — September 27, 2006 @ 5:22 pm | Reply

  5. […] Luckily for me, even though the thought of drinking a glass of cum turns her off, it doesn’t turn her off to swallowing. I know plenty of women who are not into swallowing—or only swallow selectively—, so this is good. According to her, she only swallows when she loves someone, so when she swallows me, it makes me feel special. As I have said before, my first wife refused to swallow cum, but at least (1) she sometimes gave me head, and (2) she let me cum in her mouth. She was more into anal sex, and she mentioned quite often that one benefit was that her ass had no taste buds. Talk about a small miracle. […]

    Pingback by Anoxeria, Bulemia, and Sex « My Favourite Life — September 28, 2006 @ 11:40 am | Reply

  6. […] 13. I enjoy delivering anal sex. […]

    Pingback by 25 Sexual Things About Me « My Favourite Life — October 4, 2006 @ 7:14 am | Reply

  7. […] How come my comments on Annie’s pages don’t show up right away? I guess she could be moderating. Until then, I’ll take the trackback. She posts—though sadly with little detail—about her last attempt at anal sex. Well, hopefully she’ll pay a visit to my Anal Sex 101 post. […]

    Pingback by I’m Confused « My Favourite Life — October 25, 2006 @ 4:37 pm | Reply

  8. […] My birthday was Friday, but I am only writing now. Number 45. I like to have “different” sex on my birthdays. Lately, I have been in an anal mood, and I expected that is how I would celebrate my birthday. In preparation, my wife shaved her pussy smooth in the morning, as she knows that is always a hit with me. It works every time. I had something to look forward to that afternoon or evening, or so I thought. […]

    Pingback by Birthdays « My Favourite Life — December 12, 2006 @ 1:32 pm | Reply

  9. If double dipping is so wrong how are so many porn stars getting away with it?

    Comment by Double Dip — April 18, 2007 @ 4:58 pm | Reply

  10. LOL. Who says porn stars are brain surgeons?

    Comment by myfavouritelife — April 24, 2007 @ 10:25 am | Reply

  11. can you please e-mail me this artical

    Comment by sene — August 23, 2007 @ 12:56 pm | Reply

  12. […] Anal Sex 101 […]

    Pingback by Best of So Far « My Favourite Life — September 27, 2007 @ 9:38 pm | Reply

  13. […] suppose many seekers end up on the Anal Sex 101 page, and I still feel that page just about sums up the basics. But here, I just want to focus on […]

    Pingback by Painless Anal Sex « My Favourite Life — October 15, 2007 @ 3:53 pm | Reply

  14. SICK

    Comment by Anonymous — October 15, 2007 @ 8:12 pm | Reply

  15. […] of these issues are addressed in my Anal Sex 101 entry, but I will readdress some of them here anyway. There you can read about (1) anal intercourse […]

    Pingback by Search Terms of the Week: Anal Sex « My Favourite Life — December 18, 2007 @ 8:53 am | Reply

  16. I hadn’t tried this yet, but I plan on it. My boyfriend beg me for it, so when I finally tried it I was in so much pain I never wanted to do it again. I don’t really want to say no to him, because sex is to pleasure both, but I don’t deal with pain very well, but you seem to know what your talking about, therefore I will give it one more shot, hopefully it will work and we both can be a little happy about our sex life.

    Comment by none — April 4, 2008 @ 2:51 am | Reply

  17. Anal sex can be painless if the initial penetration is done while both partners are lying on their sides. After a few slow strokes, relaxation is achieved and then any position can be assumed.

    Comment by centsless — April 7, 2008 @ 1:53 pm | Reply

  18. Hi Centsless,

    I can think of no anatomical reason why this would be true, and I haven’t had any better (or worse) experience with this position. Of course, you do say “can be…,” in which case any position “can be…”

    Thanks, MFL

    Comment by myfavouritelife — April 8, 2008 @ 11:13 am | Reply

  19. I am 18 and I started having anal sex with my boyfriend about a month ago. It has been great and we have been doing it maybe four or five times each week. However, last night, he did something different that I was not expecting. After he came inside my ass, he kept his cock inside me for a full minute and then suddenly started to piss deep inside my ass. I immediately felt the warmth of his urine and realized what he was doing. The truth is that I was feeling slutty and actually enjoyed the sensation and the thought of having my boyfriend piss inside my ass without even asking me. I guess I just like to please him and I tend to be very submissive when we have sex. Have any other women (or men) here ever tried this? Is it okay for me to continue letting my boyfriend piss inside my ass? I don’t know of any specific reason to avoid doing this as long as he enjoys it (he does) and I am comfortable with it (which I am). Any risks here that I need to be aware of? Please let me know. Thanks!

    Comment by Jennifer Wieand — July 6, 2008 @ 10:31 pm | Reply

  20. oh hi

    Comment by Anonymous — November 12, 2008 @ 12:37 am | Reply

  21. OMG Jen. I’ve heard of guys urinating right before they hit orgasm as to avoid pregnancy. With the acid or something, I forget, cuz I know “pulling out” totally does not work. But in the butt? I don’t see the purpose. That would disgust me. But so does the thought of a women doing anal when a more comfortable hole is just a little bit more north. Thery’re dangers, and it can hurt, I mean, even a finger in there… The butthole is for pushing something out, soo ohh. And AIDS. I mean you’d have to be careful, condoms, more lube. It just sounds traumatic. But everybody is so positive about it all.

    Comment by Anonymous — December 14, 2008 @ 1:31 am | Reply

  22. haha Jen thats the most fucked up thing ive ever heard

    Comment by Liam — April 14, 2009 @ 8:34 am | Reply

  23. Jennifer Wieand, where were you when I was 18? WOW.

    Comment by Reiser — May 22, 2009 @ 2:28 pm | Reply

  24. ok so let my boyfriend fuck me in the ass for the first time and it hurt and i started to cry but we keeped going and it statred to feel a little better but you said that the next time you did it it would feel better…no it felt like i was dieing…why did it feel like that

    Comment by katelyn — July 22, 2009 @ 1:36 pm | Reply

  25. I’m sooo frustrated with anal sex. I like to pride myself with being able to do all the great things a girlfriend and soon to be wife can do. But anal sex has always been a pain in the ass. Its always difficult to relax, to enjoy, and then he loses his wood from hearing me bitch! I have tried toys and to practice relaxing my actual asshole but it feels like he’s pounding sand back there! Should toys be used more regularly, like daily? Or the ass fingering? We just tried analEase and it didnt help either. 😥

    Comment by Want it to work! — August 31, 2009 @ 10:45 pm | Reply

    • pounding sand feeling comes from too little lube. i like silicon based lubes. also try doing it urself first couple of times with a smaller toy or a dildo. then ull be able to relax more. make sure u r in the mood. mastrubate before, come a couple of times. i did that for about half a year before actualy allowing him to put his penis inside there. we use a lot of lube and i let him know as we go to put more if it starts feeling like sand. gotta say that before i used to think ill never ever in my life have anal sex. now i cant live without it! its a complitly different type of orgasm and its SOOOOOO gooood! good luck

      Comment by Anonymous — April 16, 2011 @ 3:46 pm | Reply

  26. I let my boyfriend try anal with me and he’s been really patient. But it really hurts! He always starts slow and I know he really wants to stick his cock all the way in there, but there’s no way I can relax that much. I told him we’d keep trying, but I only get alot of pain out of it.

    Comment by era — September 21, 2009 @ 9:03 pm | Reply

  27. guys all here saying good things. thanks and i learned a lot here:))
    just have fun and make love good luck everyone
    believe me when you fallen in love and doing sex that will be
    this the best website talking about anal sex

    Comment by britney — September 23, 2009 @ 2:19 pm | Reply

  28. take your time. it takes a long time to get a throbbing cock in that space.

    Comment by Anonymous — December 19, 2009 @ 3:28 pm | Reply

  29. i nave never had. can he go Fast? and what are the beat positions?

    Comment by taylorstephanie' — February 27, 2010 @ 12:35 pm | Reply

  30. if you are a woman & really want tot ry anal sex, here’s some tips from a gal who enjoys it…

    1.) never let the guy rush you! it;s your ass, after all. once he’s done, he’s happy. you will have the sore anal sphincter the first few times, you will be the one to shit cum, & you will be the one who has an uncomfortable bowel movement the next day. so don’t rush!

    2.) when you are ready, masturbate. seriously. masturbate while he initially inserts the head of his penis, while simultaneously pushing down on your keiger muscles. (kinda like having a bowel movement) this will relax your external anal ring, allowing him easier entry.

    3.) i usually have to have my guy pull out after 1st penetration, relax a moment, then re-insertto be able to advance the penis the entire length. why? i dunno, i think i need the 1st penetration to loosen up a bit, then i can take it all.

    4.) experiment with different positions.

    5.) too much lube is just as dangerous as not enough. i prefer water based.

    6.) don’t worry if you can;t enjoy it the first time & he does. do not ever “just deal with the pain’ so your partner gets off-what’s good about that for you??? it took me about 8 or 10 tries with different partners to actually enjoy anal. and that was because the guy who did it too me fingered my clit the whole time. the whole entire time his cock was in my ass-so i had explosive orgasms during it.

    7.) just because you enjoy anal one day doesn’t mean you will want it another day. your partner needs to respect that & respect you, as with any sexual relationship.

    good luck, wear condoms if not involved in a monogamous relationship, & have fun!!!

    Comment by roxanne — March 6, 2010 @ 11:55 am | Reply

  31. Hi Guys, I’m a Asian Gay boy. Looking for how to have anal sex, because in my country we unable to find enema, is that any way to clean ass. Kindly advice me on this. Thank u

    Comment by moonboy86 — January 11, 2011 @ 9:54 pm | Reply

  32. I am 17, and I enjoy anal sex with my boyfriend because it gives both of us multiple orgasms. I mean he can cum three or four times in a single session, and I might cum five or six times. The best position for me has been anal missionary where I’m lying on my back and he puts his arms under my knees, rocking my pelvis backward a bit so that my feet go up in the air and his 11-inch cock is able to completely bury itself inside my anus and rectum. Long powerful strokes and popping his cock out and back into my asshole really turns me on. We use saliva, hand lotion, whipped cream, and/or butter as lubricants for anal sex. As for frequency, I have to admit that anal sex is our favorite activity so we usually have anal sex six or seven days a week, and sometimes twice a day. We have had anal sex in bed, on a sofa, in the shower, on the backyard deck, in a swimming pool, on the trunk of my boyfriend’s car, in a public restroom, in a forest late at night against a tree trunk in the pouring rain, and on a church altar late at night when nobody else was around. If the pain of anal sex feels too severe sometimes, I just divert it by asking my boyfriend to either twist or bite my nipples. But, usually, by the time he has gotten his 11 inches all the way up my asshole, it only takes about four or five thrusts at that depth to put me in a completely ecstatic state of mind.

    Comment by sally — January 26, 2011 @ 8:36 am | Reply

    • Lol! 11 inches!

      Comment by Anonymous — August 11, 2013 @ 8:50 am | Reply

  33. I have had anal sex once and it was extremely painful. I am only 22 (F) but have haemmroids. I want to have more anal sex but am worried about doing some serious damage. Advice please!

    Comment by mel — July 21, 2011 @ 6:34 pm | Reply

    • Just… Just don’t.

      Comment by Anonymous — April 6, 2013 @ 8:52 pm | Reply

  34. I tried it once but he kept pulling in and out and it started to hurt.


    Comment by dee — October 19, 2011 @ 12:01 pm | Reply

    • I am 19 and female. I tried anal sex with my boyfriend and was concerned that it might hurt too much, but he used lube and that really helped. We have been having anal sex on a regular basis. He is quite large, but the lube allows him to get completely inside of me. The initial penetration only hurts a moderate amount and only temporarily. Once he gets all of it inside me, he starts to thrust back and forth, and that feels really amazing for him and for me. After just 5 or 10 minutes of thrusting, I am able to relax a bit more as the pain usually has begun to subside a bit. By the 15th minute of thrusting, I begin to have my first orgasm, which is amazing. And then as he continues to thrust for about an hour, I have many more orgasms and he is able to ejaculate several times. I have never had any damage or health issues whatsoever.

      Comment by Kay — April 10, 2017 @ 12:24 pm | Reply

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  38. When I was 16 years old, I went to my high school’s homecoming dance, and afterwards my date drove me to his house for some drinks — rum and Coke. It turned out that his parents were not home as they had gone out of town for the weekend to visit his aunt. We sat on his bed, listened to music, and drank the rum and Coke. I started to feel a bit dizzy and began to lose all inhibition. I was a virgin, but I really had a major crush on my date. We started to French-kiss and things moved very quickly. He started to remove my dress, and I realized it, but I just let him and kissed him some more. He picked up my cue that I wanted him. With my dress, shoes, bra, and panties in a heap on the floor, he stretched me out onto his bed, spread my thighs apart, and began to eat out my pussy. It felt so good, and he was drooling saliva onto it, making me even wetter than I already was. He took off his pants, flipped me over onto my stomach, and placed his cock between my ass cheeks. I could feel the tip of his cock gently touch my anus. I was surprised, but also excited by this. And I really wanted to pleasure him. He asked me in a soft whisper if it was OK to have anal sex so that I wouldn’t get pregnant. I whispered back, simply, “Yes. Anal sex.” That was all he needed to hear. Then, I felt his hard cock slowly push into my anus. I whimpered as I felt his cock stretch my anal sphincter muscle wide, but I bit my lip and focused on listening to his breathing and his moans of pleasure. It actually turned me on to listen to his moans, knowing that he was enjoying himself because of me! His cock penetrated my virgin asshole even deeper, and I could feel the burning pain of having my virgin asshole fucked for the very first time. Soon his entire erect cock was buried inside my rectum, and he began to saw his cock back and forth, gently reaming out my ass, and causing me to moan with a combination of pain and pleasure. My moans clearly excited him, and they seemed to give him license to thrust even harder in and out of my asshole. As I continued to moan louder with increasing pain, he continued to moan louder with increasing pleasure, thrusting his cock all the way up my rectum, and then pulling back out about 90% of the way — before slamming his cock all the way back up my rectum. Over and over again, he fucked my asshole with this technique. My anal chute felt so sore, and yet I could hear in his moans that his pleasure was increasing. Soon, he started to cum deep inside of my ass. I could feel his thick warm semen coating the insides of my ass. It was amazing! He continued to thrust back and forth inside my ass for another 20 minutes, managing to cum inside my rectum a second time. Then, he slowly pulled his cock out of my asshole and lay back on the bed, exhausted. I looked over at him and saw that his cock was still erect, pointing 90 degrees upward towards the ceiling. As I looked closer at his shaft, I realized that it was coated with a light-brownish mixture of liquid smeared across much of the shaft — it was a mix of his cum and my own shit from deep inside my rectum. Without saying a word, I instinctively bent down and took his cock into my mouth — and began to lick and suck on his shaft. I sucked on it so hard that I began to literally clean his cock, and the light-brownish mixture that had been smeared on his shaft was now inside my mouth — and I swallowed it all. I continued to suck on his shaft, forcing my lips all the way to the bottom of his shaft, mashing my lips against his balls, and I bobbed my head up and down, causing him to explode with a major cumload inside of my mouth, which I dutifully swallowed.

    Comment by Katherine — December 12, 2014 @ 1:37 pm | Reply

  39. I am a 16-year-old girl and I recently went to the senior prom with my boyfriend, who is 17. After the prom, we went to a party at the house of a mutual friend. Our friend’s parents were out of town that weekend, so it was only teenagers at the party, and my boyfriend and I found a basement bedroom with a door lock, so we snuck into there to make out. Quickly, we were both nude and he asked me if I was willing to have sex because he knew I was a virgin. He started to fuck me vaginally and then, without saying a word, he pulled his cock out of my pussy and pressed it against my anus. I did not object or resist in any way, but simply went with the flow, although I have to admit that I was not expecting anal sex. Still, I was surprised at how the intensity of anal sex really turned me on. The only lube, if you could call it that, was the moisture from my pussy. He has a large cock, but he was able to work it all the way up my asshole like “balls deep,” and then he was able to thrust it back and forth inside of my asshole. It did hurt, but it also felt warm, and he obviously found it extremely pleasurable for him, and as the thrusting intensified, it actually felt good for me, too. I let him fuck me anally for 45 minutes, and during that time he managed to cum inside of my ass a total of three times. It was amazing!

    Comment by Kayla — May 27, 2016 @ 9:08 am | Reply

    • I am a sophomore at a college in Lakeland, Florida, and my boyfriend introduced me to anal sex about a year ago. I trust him and I am submissive by nature. That first time, he was licking my pussy and then his tongue wandered onto my anus, which felt amazing. He drooled saliva onto my anus as I started to moan, and as he pushed his tongue into my asshole, he asked me if I was willing to try anal sex. I whispered, “yes.” We didn’t have any lube, but he drooled so much saliva onto my anus, and after using his tongue and fingers to probe my rectum, he got me feeling very wet and relaxed down there. He put the tip of his cock against my anus, and it quickly slid into my asshole. I was so excited and a bit scared at the same time. I could feel my asshole stretching wide, and I felt the warmth of his cock as it filled my rectum. It felt amazing. He started to thrust back and forth, and although I felt some pain at first, the friction felt good and I was feeling hornier. I started to moan while he fucked my ass, and he said that my moaning turned him on. So, he fucked me anally for about 20 minutes, but really hard. It was all I could do to catch my breath and my thighs were shaking as I felt dizzy. It was so intense and he was really reaming me out. He managed to cum inside of my rectum, which felt soothing to me. When he pulled his cock out of my ass, it was covered with a light brown mixture of liquid — his cum and my feces. I don’t know why, but I instinctively started to lick his shaft clean, sucking and swallowing the mixture — it felt taboo and slutty, but I was happy to do it. He grabbed my head and began thrusting his cock in my mouth. His cock quickly got hard again and the tip penetrated my throat. I gasped for air and gagged a bit, but I continued to suck on his shaft as the tip of his cock pushed deeper into my throat. And then he was able to cum inside my throat. I swallowed his entire load, which I was surprised that I could do. Since that night, we have been having anal sex on a regular basis.

      Comment by Melissa — May 29, 2018 @ 5:54 pm | Reply

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