The answer to this question depends entirely on the mindset, interest and subsequent expectations of the individual trying it. Strap-on sex with a dildo can be an incredibly enjoyable and fulfilling experience for some. Others may find it uncomfortable, or to put it lightly - unpleasant.
Ultimately each individual must determine for themselves if enjoyable is in fact the result of attempting it. One of the main draws of using a strap on dildo is the near constant possibility of taking control within the bedroom. Wearers are often able to penetrate their partner in a way that more closely resembles some form of traditional sexual experience; physicality being what it is, this is a large part of its appeal.
Highly empowering feelings of freedom and small to medium scale exploration are typically achieved through this process. Not all individuals are comfortable with taking said control - vulnerability (of any sort) is a real thing, and strapping a dildo to one's waist can trigger these more personal fears. Unfamiliar physical sensations associated with penetration itself can only add to the intimidation factor. Individuals thinking of exploring strap on sex should at least understand that communication and all round trust are key; pre-existing or formed during the act, both partners need to feel safe. Discussing expectations, simple or otherwise, is important.
Lubrication is another small but very real part of making the experience smoother (physically and emotionally). Additional pleasure items can and should be talked about - vibrators, cock rings, anything the two can agree on. Taking the whole experience slowly is the last, but very important part: focus on small, daily type experiences of pleasure. Speed, style, and all that follows, can be as personal as you like.
Take the time to appreciate the different sensations that each of these various motions bring - making the experience more pleasurable is a large part of what I believe true enjoyment consists of. Finally, explore other areas of pleasure; nipples, the clitoris being the prime example, and any other areas the receiving partner is comfortable with. Strap on sex with a dildo can look rather intimidating at first glance, but time, trust and to a point communication, can turn it into a hugely enjoyable experience.
Having sex with a strap on dildo (of any and all forms) is a personal decision; comfortable and stimulating or not, it all comes down to the individual. Many people do enjoy the sensation, some find certain aspects uncomfortable and less satisfying. The 'success' of using a strap on dildo for sex depends entirely on the partners willing themselves to communicate and experiment - angles, speeds, small to more constant pressures all being part of that process.
If a couple is able to properly communicate and push each other (physically and emotionally) to the highest levels of pleasure through the use of the strap on, then I see it as a positive experience. The actual sensation of the strap on itself can be very varied; size, material and shape all play a role. Larger dildos are not always better, pain should never be an option. Silicone is often preferred by more experienced users for smoothness and/or specific stimulation. Shapes can and will lead to different types of pleasure. Communication and/or re-defining what pleasure looks like to each partner is the end goal of all things strap on. Experimentation is and always will be, a part of sex.
Before use, partners should discuss their comfort level for size, material, shape, and any other specific preferences. Ensuring all involved parties are at least partially comfortable is key; the experience itself should be enjoyable. To increase pleasure, experimenting with different angles, speeds, and various (subtle or obvious) levels of pressure is recommended.
Customizing the experience to individual desires is part of this process. It is important to understand that the sensations a strap on dildo produces are quite different from some form of traditional penetration. The dildo will move more - the straps allow for this, natural skin friction being absent. Small or initial sensations may start out weak, and as the body adjusts to a new near-constant texture, they can and will increase. Partners must therefore remain aware of any potential discomfort; switching angles or speeds is a simple but effective way to manage this.
Overall comfortable and stimulating sex with a strap on is completely achievable. Patience and all round communication are the true prerequisites. Finding the 'best' size and/or shape for a couple, experimenting as they go, will take them to a point where having sex with a strap on (to them at least) becomes a positive experience. Pleasure, of all things, is what we are after.
