I am a female-identified male and am going away for an overnighter with my new boyfriend. He wants me to bring panties, nylons and any other sexy feminine clothes to dress him in. That's cool. I have had fun shopping and telling clerks it is for my boyfriend. He also wants me to buy him a butt plug. I haven't played with toys in awhile and one site alone has 216 choices!!!
Can you insert some wisdom??
-Anally Anonymous
First, I disclaim all responsibility for that pun at the end of Anon's question.
Second, in order to specifically answer your question I'd need a few more facts. For example, has your boyfriend ever played with insertables before? How often and how large? However, since I don't know those things, I'm going to assume that he has no experience with insertable toys, and I'll start with the basics.
I would definitely suggest using a butt plug. These toys are designed with insertion into the ass (and removal) in mind. They come in a variety of shapes and sizes, but I would suggest fairly small and with a narrow, tapered cone shape for a beginner. Make sure that the plug you select has a WIDE, FLANGED BASE. This is very important. You do not want your plug slipping in deeper than you can retrieve it, necessitating a trip to the emergency room.
I can not stress enough another important safety factor. There is NO SUCH THING AS TOO MUCH LUBE. Use as much as you want. Use gallons. Actually, you probably won't need that much. But trust me, this is not an area of your body where you want abrasions. Lack of lubrication can cause tearing. If your partner requests more lube, you give them more lube. Period.
Also, as far as the material goes, I highly recommend silicone. As someone with a latex allergy I can not say enough nice things about silicone toys. Also, they have the advantage of being able to be sterilized, either run through a dishwasher or boiled in a pan on the stove.
Here are a few types of plugs (Please only click the following links if you are 18 or older):
 http://store.babeland.com/dildos-silicone/silk If you would like something with a more "natural" shape to it, the smallest size of the Silk dildo works well for beginners. It also has a broad flat base.
http://store.babeland.com/butt-beads/ripple I like the smallest size of this plug. As with the other two, it is made of silicone. The "ripples" in the design of this plug allow for a very slow and gradual insertion, as well as producing some entertaining sensations.
Now, when beginning play with insertables there are two rules you must remember: 1. As I said before, there is no such thing as too much lube. 2. There is no such thing as going too slow. Take your time.
Beyond this point, things get a bit graphic, so if you're not into it or have a weak stomach, or are of "tender years" so to speak, go no further.
Wearing gloves, I recommend Nitrile, begin by using your fingers to spread lube around and just inside your boyfriend's ass. Carefully insert a finger, paying careful attention to your boyfriend's reactions. Once your boyfriend is comfortable with you touching him around and inside his ass, begin inserting your well-lubed toy. Many books and experts will tell you to "aim for the bellybutton" when inserting things in the rectum. However, I have found through personal experience that this is not the optimal angle for me. Listen to your partner, ask them to tell you how it feels. Too much pressure, not enough? And remember to take it slow. Make sure you can comfortably insert the entire plug/dildo into your partner and that there is enough lube, before beginning any sort of in and out motion with it. The following book will probably offer the two of you more detail than I can here: http://store.babeland.com/books-sex-information/ultimate-guide-to-anal-sex-for-men
Also, please be careful of cross contamination. Toys used in one person's orifices should never be used in another person's orifices. If you are going to be doing this on a regular basis and reciprocating, it would be best for you to each have your own plug to be used exclusively on its owner.
Mr. Strangiato has just reminded me that many men have somewhat, ahem, larger orifices than mine. If the small plug is too small, feel free to step up to the next size up, like a medium. Perhaps bring both a small toy and a medium sized toy with you. Mr. Strangiato feels that showing up on a first date bearing "Plug-zilla" is not only terrifying, but kind of insulting.
I hope that I've been some help to you in the area of butt-play, and I hope that this experience turns out to be everything that you and your boyfriend are looking for.
