Wanting More

Jun 032004
 

As long as we do lots of foreplay and my body is prepared, I don’t have a problem with pain during anal penetration. However, after about four inches of cock in my ass, I get abdominal pain that I can’t get past, no matter how relaxed or aroused I am. We’ve tried changing positions, but no matter what, it’s as if there is a road block. This is frustrating for me, and I know that for my husband, who wants his balls to slap my pussy on the downswing, it has to be downright maddening. I asked a girlfriend who’s into anal if she had ever experienced this, and she says that around the seven inch mark, her guy seems to hit a wall. Is it possible that there is a sharp bend that is preventing full penetration? Is there a technique to get around the discomfort I am experiencing? Swing to the left? Swing to the right?

–Wanting More

The first two inches inside the anus is called the anal canal, and the rectum is the area from the anal canal to the colon, which is another five to seven inches. Unlike the vagina, where you’ve got a pretty straight shot from end to end, the rectum is curved. That’s especially important to know when penetrating someone’s ass with anything longer than a finger, and especially with a dildo or vibrator that is firm and inflexible (like one made of hard plastic, clear acrylic, or glass). If you jam something (especially something rock hard) straight inside you can absolutely hit the rectal wall, which does not feel good. As you get more turned on, the rectum expands, and the curves are less pronounced, but they are still present.

So, the “four inch” stopping point you describe could correspond with the first curve of the rectum, when it curves toward the front of the body. Everyone’s internal geography is unique, and it’s possible that your rectum is more curvy than others. I’ve heard people report similar feelings of facing a roadblock inside their asses.

You’ve already tried changing positions, which would be my first suggestion. I suggest that you pick a long, very flexible toy, and, while masturbating, begin exploring your ass with it. Take note of the curve of the rectum, what feels good and what doesn’t, and if you can find your roadblock, or if you develop discomfort. Experiment with moving the toy forward or back inside of you to see if that changes anything. If you can find the trouble spot, see if you can move past it or around it, again, by moving it toward the front of the body or toward the back. If you are still experiencing problems, I suggest you talk to your doctor about it and have a rectal exam.

Pleasure With My Probe

Mar 202004
 

I just started having anal sex with my girlfriend. We did it the first time with lots of lube and I was able to get the entire shaft inside her with little to no pain. She told me that she could feel the fullness but she got no pleasure or pain from it. She said that if I wanted to do it again later it would be no problem since it does not hurt her; however, I would like for her to get some pleasure out of it. I cannot touch her vagina with my fingers because she is very ticklish there. If you have any suggestions, I would appreciate it them.

–Pleasure With My Probe

Bravo to you for realizing that anal sex should be pleasurable for both people involved. My suggestion is that you add some clitoral stimulation to the mix. While you are doing her ass, rub her clit, or, if it’s easier, have her do it herself. You could also use a vibrator for more intense, focused sensation. Many women (me included!) love the combination of clitoral and anal stimulation, and lots of girls say that they don’t experience pleasure from anal penetration without something on their clit.

I’m not sure what to make of your girlfriend’s ticklish pussy. That sounds more psychological than physical to me. Perhaps it’s a reaction to her feeling shy about receiving pleasure; if that’s the case, then you should encourage her to relax and give herself permission to experience being touched and pleasured. Or, it could be that when she’s turned on, her genitals become super-sensitive, and stimulation of any kind feels overwhelming. Then, try softer, more indirect kinds of stimulation, like rubbing her clit from one side, rather than directly on top.

Butt Buffet Boy

Feb 242004
 

My girlfriend has a severe anal sex fetish. She prefers it over vaginal intercourse. Fortunately, I don’t mind it one bit. We’ve done some ass-to-mouth stuff, since we are monogamous and STD-free. I’d like to experiment eating food out of her anus — either food shoved partially into the anus or food that has been completely inserted and then pushed out. I’m wondering what food products would be safe for this, since I don’t want anything to get stuck up there. So I’m looking for something that would be semi-rigid, but would also melt or dissolve if it got lost. I was thinking about things like M&Ms (the non-peanut variety) and other chocolate things, but I can only stomach so much chocolate.

–Butt Buffet Boy

Usually I advise people against sticking food in their ass, since food items are not sex toys and are better left in the kitchen. But you seem pretty invested in this food fantasy, so I’ll suspend my anti-food stance for this response. But before I go there, I just have to say that what you describe is an interesting twist on one of the most taboo desires in the world: scat play. Scat play involves people defecating into other people’s mouths, eating shit, and generally eroticizing it. It sounds to me that you like the idea of stuff coming out of your girlfriend’s ass, even stuff that resembles what typically comes out of our asses (you suggested chocolate, not me), but you want it to be previously undigested.

As long as you take care to insert your chosen edibles just inside the anus and not too far up, there’s no great danger of soft or small foods getting lost. What goes in will inevitably come out. You should avoid foods like jalapeno peppers, seeded breadsticks, and others that are spicy, abrasive, or could break into sharp-edged pieces, which could all irritate the delicate rectal tissue. Also stay away from salami or sausages, since nitrites used for preserving meat aren’t good for you. I’m glad to hear that you’ve both been tested for STDs, but it’s probably still a good idea if your girlfriend has an enema a few hours before your feast, since her ass contains bacteria that may be fine in the lower intestine, but may cause problems if you ingest it.

Liar, Liar, Ass on Fire?

Feb 102004
 

Have you heard of figging? Do you think it’s safe to do? My submissive and I are headed to a party next week where figging is to be the central theme. Any information you could provide would be very useful.

–Liar, Liar, Ass on Fire?

For readers who may not know what it is, let me begin with a definition. Rumored to have been practiced as early as the Victorian era (they were so kinky!), figging involves sticking a ginger root up someone’s (or your own) ass, and most people I know do it in the context of a BDSM scene. The idea is that the ginger illicits an intense, long-lasting burning sensation in the sensitive, delicate tissue of the rectum. I’ve heard of some Dominants who insert the root into a submissive’s ass before a spanking, paddling, or caning. The longer the root is inside the butt, and the more blood that rushes to the area, the stronger the burning. Plus, any kind of movement — including clenching the sphincter muscle s– increases the fiery feeling.

This is not an activity for anal play novices or people with extra-sensitive behinds. I consider it an internal form of genitorture; if your bottom enjoys sensation play like ice cubes or metholated sports creams on her pussy lips or her anus, figging takes this “torture” one step further. Plus, you should not use creams like Ben Gay or Icy Hot inside the pussy or ass. While some bottoms say that figging feels warm and tingly like the creams, most report that the sensation is ten times more intense.

There are a few safety tips that go along with this practice. You should begin with a fresh, whole ginger piece (also called a hand), and peel off the brown rough skin before slicing a “finger” to use for penetration. Because it obviously does not have a flared base (and therefore could get lost in the ass), select the largest piece you can find, and either carve out your own shape with a base or attach a string to it in order to make it easy to retrieve. After handling a peeled root, you shouldn’t touch your eyes or your slave’s eyes. Some figging fans say that lube can seal in the moisture and prevent it from releasing, thereby defeating the purpose, but you know my stance on lube: you need it! Other than those precautions, as with all perverted activities, use your common sense.

Anal Addict Denied

Nov 082003
 

My girlfriend and I have tried anal sex multiple times, but she doesn’t like it unless I rub her clit. As soon as I stop rubbing it, she says it’s very painful and wants to stop. She is also afraid to try doing certain anal positions. We only do it lying on our sides, facing the same direction. She claims that doggy style hurts too much from our one time of trying it. I am desperate for help!

–Anal Addict Denied

It fascinates me that you consider yourself an “anal addict denied,” because you are, in fact, having anal sex — just not necessarily in the exact way you want to be. If your wife doesn’t like it doggy style, that’s most likely because that position offers the deepest penetration, and it obviously doesn’t work for her; fucking her in “spooning position” — which you say works for you — may mean less deep thrusting for you, but a lot more comfort for her. If you’re simply dying to do it to her doggy style, then I suggest taking more shallow strokes, and seeing if that feels better.

As for your problem that she doesn’t like anal unless you rub her clit, well, what exactly is the problem? Rub her clit! The majority of women need clitoral stimulation in order to orgasm, and most would say it enhances all kinds of penetration. I know lots of women who can’t take anything in their ass without something working their clit; it helps them relax, get aroused, and it just feels great. If rubbing her clit is difficult because of your body position, then let your wife work her own clit while you concentrate on her ass; that way, it’s a win-win situation.

Clueless and Curious

Aug 202003
 

My boyfriend and I decided to try anal sex for the first time. We did it for about 5 or 10 minutes. He loved it. I, however, found it very uncomfortable and painful, and I didn’t have very much fun. Although at one point it almost felt good in a way. I want to try it again (he loves the idea so much), but I want to have fun while doing it. I’ve heard such good things about it. Is there anything we can do to make it more enjoyable for me or get me used to it without the pain?

–Clueless and Curious

First, I want to commend you on remaining curious and open to anal sex even after you had a not-so-memorable first experience. Most women have a negative anal de-flowering and never try it again.

It sounds to me like your husband may have made the most common mistake that I hear about: he rushed the process. Unlike your pussy, the ass is not self-lubricating, so you absolutely need to use lube, and plenty of it. I prefer a thick water-based lube that’s similar in consistency to hair gel; thicker lubricants stay wet longer and have a cushioning effect inside the delicate rectum. And speaking of the delicate rectum, your ass is very sensitive and needs plenty of slow, patient warm up to get it ready for your husband’s cock. That means activities like oral pleasure, gentle penetration with his finger or playing with a small butt plug or dildo to start. He needs to err on the side of caution, especially in the beginning, to get your ass used to having something inside it.

Take your time, and make sure you let him know if you want him to slow down or stop. As you relax (lots of deep breaths help), your ass will, too, and penetration should feel pleasurable, not painful. During this foreplay, experiment with adding other sensations to the mix: many women like (even need) clitoral stimulation in order for anal to feel good. Some like to have vaginal penetration or direct G-spot stimulation at the same time. See what works best for you.

Patient in Paris

Aug 142003
 

My partner likes anal sex very much, she has had plenty of experience and we practice it regularly. But, despite extended warm up sessions, a lot of lube and communication, she cannot accommodate my penis every time. I am always very gentle and caring. I know that even with the same partner each day is unique and different even if the mood and environment is the same. The situation is even more frustrating for me (and probably for her too) as we have often to stop after the tip of my cock has gotten inside her. It’s almost like some sort of reflex in her body just “rejects” me. What is the best way to achieve full anal sphincter relaxation, allowing an easy and guaranteed penis insertion?

–Patient in Paris

There are no guarantees in life, especially with matters of the heart and ass. It sounds to me like your partner’s body still isn’t relaxed enough which is why her ass is rejecting you. A surefire solution is to increase the amount of foreplay. I suggest more warm up with fingers and toys, plus you should add clitoral stimulation to the mix. Using a vibrator, your hand, or hers to manually stimulate her clit while you play with her ass can increase her arousal and help her rectum expand for penetration.

Once you first get inside her, don’t make any sudden moves. Stay put and give her a chance to adjust to the feeling before you start moving in and out. When she feels relaxed, then start with gentle thrusting, and let her call the shots in terms of speed and depth. Take your time, listen to her body, and don’t put so much pressure on yourself and her to make it happen every time.

Frustrated in Germany

Aug 022003
 

My husband and I have been experimenting with anal sex for a number of months now. We’ve had good experiences with butt plugs, anal beads, and other toys, but when it comes to anal intercourse, there’s always a problem. The initial penetration itself usually goes really well, but for some reason I can’t manage to have sex for any length of time at all. I mean, seriously, three or four thrusts, and I have to stop. It feels almost like there’s a second ring of muscle, farther inside that my husband is hitting when we have sex. Once he gets all the way inside, it’s fine, but when we start moving, he slips out past that ring again, and it hurts when he comes back through it. Am I imagining things, or is that really there?

Most of the time, if I lay still and concentrate, I can manage to relax everything enough for him to get off, but the second I stop focusing and start enjoying myself, everything tightens up again. It feels so wonderful having him inside my ass, I don’t want this to be something we have to give up because we can’t make it work. What do I do?

–Frustrated in Germany

You are not imagining things. What you’re describing makes perfect sense, anatomically. There are two sets of sphincter muscles, the external sphincters and the internal sphincters. For some people, these two rings of muscles are quite close together, but for others, they are farther apart. Both sets of muscles need to relax completely in order for anal penetration to be comfortable and pleasurable. They are like the “gatekeepers” to the ass, and penetration can be painful if you are nervous or tense.

You are doing the right thing by concentrating on relaxing, it’s critical to your enjoyment. You and your husband should experiment first with different positions; as you try several different ones, you can change the angle of insertion, the depth of penetration, and when he’s hitting that inner ring. He also needs to try more shallow thrusts, so that he doesn’t consistently pull out too far, which is obviously painful for you. I think your problem can definitely be solved with some creativity in positions and taking it slower.

Silky Bum Rag Virgin

Jul 212003
 

I recently heard of a kind of anal play called “the silky bum rag” and am curious to find out more about it. None of my pervy friends have never heard of it or tried it. From what I’ve heard, a cloth, silk scarf, or handkerchief is slowly and sensuously inserted anally, and pulled out at the point of orgasm. My girlfriend and I both want to try this. Have you ever done anything similar? If so, what is it like and can you give us any pointers?

–Silky Bum Rag Virgin

Just when I think I have heard, read, seen, and experienced all there is to experience in the world of anal play, I get a letter like yours! I have not heard of “the silky bum rag,” but that doesn’t mean it’s not happening out there. My initial thought is that a piece of fabric is not going to feel like much sliding inside your ass or once it’s in there; it doesn’t have enough weight or size to it to create an intense sensation. However, I can see the appeal of it coming out when you are about to climax. Like a string of anal beads (although a completely different texture, of course), a soft scarf being pulled out of your ass could be extremely pleasurable. My one caution is that the scarf should be long enough so that it never goes all the way inside. Keep enough fabric outside the body to hang onto, so it doesn’t get lost in your ass.

Gushing Girl

Jul 132003
 

My boyfriend and I love anal sex. When he penetrates me, I come and squirt all over the place. It’s not pee, but I definitely soak the bed. We both love it, but is this normal or am I special?

–Gushing Girl

Congratulations — it sounds like you are a female ejaculator! Many women have the ability to ejaculate either through direct or indirect stimulation of the G-spot, also known as the urethral sponge. The urethral sponge sits around the urethra, and its paraurethral glands produce ejaculatory fluid which can comes out of the urethra (which is why many people mistake it for urine). You can definitely achieve indirect G-spot stimulation through anal penetration, especially during certain positions which angle the body toward that all important spot, like doggie style with your head down and ass in the air. You and your guy have obviously found the magic spot, so keep on doing what you’re doing. Women who ejaculate often soak the bed, so I suggest you put down a towel or an absorbent bed pad before you get going.

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