If you lack experience in this area or have never engaged in anal sex before, it may seem daunting. This is likely due to two concerns that you may have heard: firstly, fear of defecation, and secondly, the possibility of experiencing pain. Although both outcomes are possible, there are measures you can take to significantly reduce or completely eliminate the likelihood of these exaggerated concerns.

PREPARING FOR ANAL SEX:
It is important to prepare yourself in order to ensure a pleasurable and comfortable anal sex experience. I suggest utilizing the following three preparatory tactics, which I refer to as the "Three D's" of anal preparation:

DIET:
Proper preparation for receptive anal intercourse begins with your diet. If you maintain a fiber-rich diet, douching (the second step) should only take a few minutes, and some individuals may not even need to douche at all. By consuming ample fiber and water, your stool forms into a smooth, unified mass, resulting in less leftover waste in the rectum - the area where the penis makes contact.

To adopt a diet conducive to douching, try incorporating more fruits, vegetables, legumes, leafy greens, whole grains, and unprocessed bran into your meals, while limiting your intake of dairy and greasy red meats. You may also find it helpful to add fiber pills or supplements to your diet, as these can provide a particularly effective means of increasing your fiber intake, which is especially beneficial for those engaging in bottoming.

DOUCHING:
While not absolutely necessary, douching can be a helpful measure for ensuring that your rectum is as empty as possible for anal sex. While it is impossible to guarantee a completely mess-free experience, dieting and douching are both effective methods for reducing the likelihood of any undesirable effects.

To douche, start by filling a small bulb with warm water (as warm water can help prevent cramping). Next, gently insert the tip of the bulb into your anus and squeeze it gently. Allow the fluid to rest in your rectum for a few seconds before releasing it into the toilet. Repeat this process until the water runs clear.

If you have the time, it is advisable to douche roughly 30 minutes to an hour before engaging in intercourse, to ensure that there is no remaining fluid since your rectum contains various twists, turns, and folds that the water must pass through.

DILATING:
Dilating can be an essential step in preparing your body for anal sex, as it helps to acclimate your sphincter muscle to the experience. Since the sphincter is typically closed, it benefits from exercise to perform at its best.

To dilate, begin by generously applying lube to your anus as well as a toy of manageable size, such as the RAPER-RCT, and insert it into the anus for approximately five seconds. Then, remove the toy and repeat the process ten times. Another option, which may be more feasible for some, is to insert and wear a butt plug for a period of time. Keep in mind, however, that this will not exercise your sphincter in the same manner as active play.

OPTIMAL POSITIONS FOR BEGINNERS

TUCKED MISSIONARY

One of the benefits of the Missionary position for anal sex is that it allows both partners to face each other, which allows for clear communication via both verbal and nonverbal cues. This way, the recipient can express their feelings about the experience, whether they are enjoying it, uncomfortable, or uncertain.

The Tucked modification is an advantageous position for beginners, as it lifts the knees towards the chest, which allows for a more open body position, ensuring greater comfort for the bottom, with improved access for the top. Additionally, it may be more comfortable for the bottom to rest their legs on the top’s shoulders. Some may also find it useful to use a pillow to elevate the buttocks for added comfort.

RECEIVER ON TOP

The Receiver On Top position, also known as Cowboy/Cowgirl, can be a great option for beginners, as it gives the bottom partner greater control of the experience. This is important, as the bottom position can leave them feeling vulnerable. During initial entry, it's essential for the bottom to take their time and angle their pelvis in a way that's comfortable to them, gradually determining the depth of insertion.

For this position, the top partner should lie on their back while the bottom straddles them, allowing the bottom to take the lead. Initially, the bottom should sit on the tip of the penis and engage their sphincter muscles until they fully relax. If there's any discomfort, taking a break and trying again is recommended. It may take multiple attempts, up to three or four times, for the penis to be fully inserted, so patience is essential. Once the penis is fully inserted, the bottom can lean their torso forward, backward, and side to side to find their optimal pleasure spot.

ON YOUR STOMACH

This position is an ideal way to help the bottom partner relax while giving them a pillow to moan lustfully into. To get into position, the bottom should lie on their belly with a firm pillow under their stomach, which elevates the buttocks and offers the hips some wiggle room to determine a comfortable depth. For a tighter embrace, the legs can be brought together, while spreading the legs apart can alleviate any discomfort.

The top partner can access the bottom's anus by either straddling their bum vertically or lying on top of them to get closer contact. With their partner in position, the top partner can employ various techniques such as kissing the bottom's neck, massaging their shoulders, or tracing down their back with their fingertips to help the bottom relax.

SPOONING POSITION

In this position, the bottom partner assumes the "little spoon" position, while the top partner is the "big spoon", with both partners lying on their sides. This arrangement allows for intimate and close contact between the partners.

To make entry easier, the bottom partner should place a pillow between their legs and bend their upper leg at the knee and hip. This position allows both partners to take control, move their hips forward and back when necessary, which makes it an ideal choice for beginners. Additionally, this position offers the bottom partner the freedom to play with their genitals manually or with a vibrator.

DOGGY

One of the most popular positions in any anal sex guide is Doggystyle, which is preferred by many. Part of its appeal is the various ways it can be modified to suit different preferences. For instance, bringing the knees closer together provides a tighter fit, while arching the back and resting on the elbows creates a more comfortable experience.

The best thing about Doggystyle is that it provides ample space for both partners to explore and experiment. If things become too intense, the partners can choose to engage in shallower penetration. Moreover, this position provides the bottom partner easier access to stimulate their genitals, which as mentioned earlier, can facilitate relaxation and make penetration more comfortable.

CHAIR STRADDLE

Tucked Missionary is a highly intimate position that combines the face-to-face contact of the classic Missionary with the assertiveness of the Receiver On Top position. The top partner sits down while the bottom partner settles onto their lap, facing towards or away from them, depending on personal preference.

This position grants complete hip mobility, and if the bottom partner is tall enough, they can use their legs to hop up and down on the penis at a pace and depth that is comfortable for them. Additionally, this position provides unhindered access to the genitals, facilitating a well-rounded and pleasurable experience.

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