It'll Give You a Jolly Rogering

I'll begin by saying that, although this isn't my largest anal toy, it is probably the least forgiving, at least for its size. While the silicone is flexible when bent from side to side, it doesn't have a lot of give when compressed. In contrast to some other silicone toys I've tried, the material retains virtually all of its size, if not its shape. That isn't to say that this toy is too large or unwieldy for use, just that consumers who think that a 1 1/4" diameter might be pushing the upper limits of what they can handle would be wise to try a toy that has a little more "give" when compressed. When I first got my hands on the Jolly Jack, I had intended to use it to work my way up to a larger toy. Since then I've found that, because of it's density, the Jolly Jack actually feels larger than one of my toys with a diameter of 1 5/8".

Despite my general aversion to girth or the illusion thereof, I found that the Jolly Jack was great for solo play. The bulbs give a prostate massage, and the toy is long enough for both short and long strokes. However, it is a bit long, dense, and unforgiving for partner play. The bulbs make for a very intense sensation, which can be great when you're in control, but can become uncomfortable if your partner isn't careful. It works out alright for wear as a plug during sex, but I personally found that it went a bit too deep to sit in place as comfortably as some of my other plugs, and made moving around a bit awkward. Likewise, I wouldn't recommend it for extended wear unless you're very experienced and comfortable with a lot of length and girth.

Because of its size and density, I'd say that the Jolly Jack probably isn't the best toy for beginners to anal play. I personally worked up to it with other, smaller toys, and it still feels a bit too bit to be an every day sort of toy for me. Even so, anyone who has had trouble finding his prostate should consider the Jolly Jack: I've had some of my quickest and most intense anal orgasms with it. It also seems like Jolly Jack might create an interesting sensation for a male partner if worn by a female during intercourse, but thus far I haven't had the pleasure of testing my hypothesis.

The Jolly Jack is made of a high-grade silicone, which is smooth and almost velvety to the touch (although not as much as toys like the Billy). It has virtually no smell and no taste. While the narrow "neck" of the toy just above the base does bend quite a bit, the bulbs themselves are incredibly dense, and are less apt to bend. The Jolly Jack is made of a much denser silicone than many of my other toys, which makes it firm and heavy. The texture of the bulbs and the firmness of the silicone make the toy feel a bit larger than it actually is, or at least larger than some of my toys of comparable size. The bulbs create a very intense sensation which can be good if you like a lot of prostate stimulation, but can be unpleasant if you aren't careful. My advice, as always, is to use a lot of water-based lube and start very slowly. (For the uninitiated, I specify water-based lube because silicone lubes can react with silicone toys and ruin them. There are more comprehensive articles on this topic, but the rule of thumb is silicone toys and lubes don't mix.)

As in most of my anal toy reviews, I'm beating the size issue to death because I believe it is the most important factor in choosing an appropriate toy. However, with the Jolly Jack I've discovered that actual size is not as important as perceived size. So in case I haven't made myself clear: the Jolly Jack feels bigger than its measurements might suggest. Like my brain, shoulders, jaw, and boss, my sphincter has a hard time relaxing. Naturally, I often find it difficult to accommodate larger toys. Although the Jolly Jack feels large, I am still able to use and enjoy it. Because of the toy's rigidity and the texture of the bulbs, I find I have to get it on just the right angle (slightly toward my belly, rather than straight in) and take my time in working up to it. In contrast to many plugs, which generally have a narrow tip which gradually expands, the Jack is sort of a blunt battering ram of a probe. This makes it a little tougher to work up to, but the time and effort is worthwhile, as the ribbed bulbs give a prostate massage thus far unrivaled in my collection.

Aesthetically, I don't particularly care for it. The shape itself looks rather menacing, rather than cute, whimsical, or realistic. Moreover, I have the silver version, which sports a sort of marbled two-tone look that comes across as cheap and tacky. The solid colors are much more pleasing to the eye, but the shape is remains utilitarian and intimidating.

The Jolly Jack is a great solo toy, particularly for somebody trying to work his or her way up to larger toys. Because of its rigidity, you may have to work with the Jack for a while before you find an angle or position that works for you. However, the rigidity has some benefits as well. I can't speak to the female experience, but unlike traditionally-shaped plugs, the Jolly Jack's rigid, beaded shape aprovides a very intense prostate massage for male users. In fact, if you're having trouble finding your prostate, I suggest buying the Jolly Jack. It's like a divining rod for your prostate. Or a prostate seeking missile. I still can't say I'm really comfortable with the size of the Jolly Jack, but it makes me orgasm ludicrously and without warning. In fact, the Jolly Jack is the first toy to make me feel as though I weren't in control of my orgasm. I didn't have an orgasm so much as an orgasm was thrust upon me (cue rimshot). I can't speak for all men, but it was a welcome change of pace for me. The downside is that, with a partner, the sensation can be so intense it becomes unpleasant or even painful if your partner isn't careful.

Like most silicone plugs, the Jolly Jack is a low-maintenance toy. As is true of most silicone toys, you don't want to use it with any silicone based lubes, as the resulting chemical reaction could be disastrous. The toy can be washed with hot water and soap, put in a dishwasher, or boiled for sterilization. Note that the Jolly Jack has more crevices than many anal plugs, so you may want to be more thorough about cleaning it (and yourself) before and after using the toy. As with many of my other silicone toys, the Jack has a tendency to collect lint, so be sure to store it somewhere free of lint, hair, and fur, or at least rinse it off before use.