abaya:
I only briefly went over my experience having my girlfriend use a strap-on on me on this thread, so I'll go a little further.
Basically, I told her one day that I was curious to know what it might feel like using a strap-on, since she discovered quite quickly that stroking my scrotum and pernium got me unbelievably turned on (Guys who aren't very adventurous should try this out, seriously), and of course my orgasms are out of this world when combined with her efforts.
She was a little hesitant in using a toy on me. In fact, she still is. I'll tell you why shortly.
We went to the adult store and bought your basic strap-on. Nothing fancy, no brand names. The harness isn't even that great, but it holds the strap-on in place. Whether or not it is tight to my girlfriend's body, the harness tends to move around a lot so she can't relax and just thrust in and out -- she has to hold it and think about it constantly.
We decided to have me try it on my back at first. I did not want to have her behind me, slip, and injure me (very possible, so everyone be careful how much force you use).
We lubricated the strap-on, and I put some lube around my anus. In my opinion lube is more important around the orifice (any) than inside. I'm not sure I can't explain it well, but perhaps you can think about why. Obviously you don't want it to be rough.
The most difficult part for us was definitely getting it past the sphincter. We spent a few minutes testing the waters so to speak before I asked her just to get it over with and push with a bit more force than she had been using. I must admit at this point I felt very silly with my legs up in the air and the roles reversed. You gotta be very courageous to go through that and have a willing partner. At this point I did feel akward, now having some idea what it means to have homosexual sex.
It all seemed one-sided for obvious reasons. She told me that it would be OK to do this, but before, during and after she mentioned that she gained almost no physical pleasure out of the experience, except perhaps to gain a feeling of power over me. It was nice to feel submissive, but that is not my cup of tea 100% of the time.
I asked her to go faster, slower or completely depending on how I felt. Good communication here was the key. She got a little adventurous and started to play her power game on me, which I think turned us both on a bit. She even stroked my penis with some lube which felt fantastic.
Eventually it did start to feel so good that I asked her to keep going further, and adding more lubrication as neccessary. One thing that will always surprise me is how little lube goes a long way. Eventually if I remember, at one point she had the entire thing inside of me... 8 or 9 inches, which felt amazing. I think my stomach flew out of my penis when I had an orgasm, wow. Wow.
My girlfriend then just kept slowly stroking herself (heh) in and out of me for a minute or two and withdrew. This was difficult as I didn't want to just yank it out (and no one else should either). I just dealt with the pain as best i could trying to relax all the muscles I could. It feels like a BM but a little worse since the lub does dry up a bit.
After she withdrew, I went to the washroom and cleaned up and after about 5 minutes or so I felt "normal" again.
I did enjoy it. And that's where my girlfriend's opinion comes into play. She thought that if I enjoyed it so much that I might start playing for the other team. It may be enjoyable, but that's just not something that I feel I'm going to do. It wasn't about me being curious at all... it was about role-reversal. So she's a little hesitant to try it again, but I've reassured her that that isn't the case. It only happens occasionally, and we love each other dearly and get turned on when we know we're pleasuring the other person, so I don't think we're going to give this up any time soon.
I'll say a few other things.
1. You can choose to do this or not. For you straight guys, you don't know what you're missing. Physically and emotionally (My gf and I have a better relationship and communicate better
in part because of it). It does not make you gay at all.
2. Use lots of lube. Lots. And when I say lots, I mean lots.
3. Tell her what you want. If she is starting to hurt you, slow down or stop.
4. I forgot to say we put a condom on the strap-on. It makes for easy clean-up (and the strap-on won't have any funky odours afterwards).
5. DO NOT use the "anal cream" that sex stores sell. It may numb the pain, but it also makes your body less reactive if something BAD is happening (say, you go WAY too far or you start to tear your rectum!).
6. With regard to 5., GO SLOW.
7. Just like laying on a bed of nails is easier than laying on one nail, if you have your partner stroke you or take your attention away with another method, the distant pain you feel in your rectum won't feel as bad.