Cant vote on any of those although I have a thing for freckled red heads... (Ms Regan... yummy) Anyway... Fleshlight is actually the way to go. I have done a few reviews on the toy and its easy to clean (which would be your problem here) and easy to store (problem two with any of those choices). Now I know they are expensive but the material is really durable so it is going to outlast any other of those choices. It is made of safer high quality materials and biggest of all you can store it almost anywhere because it has a built in case. So make him wait... Save up a little bit more and you may find you have a very happy boyfriend. Good luck.

The worst part of any of those toys is the material gets tacky and stuff starts to stick to it and you would rather just throw it away. The Fleshlight has a removable sleeve and you can clean it dry it and powder it to keep the material nice. (If you really want to get nuts let him keep it in the shower so he can use it AND clean it right away if he isn't playing with you!)
So as I said before its the most value for your money.

Oh.. yeah... and the secretary has bought me THREE if that gives you any idea. And if you want to get really crazy, if you wait until halloween they have a zombie fleshlight!!!! (Yeah Im twisted enough to own a zombie fleshlight)

I fell asleep while writing my reply and now I see The-IT-Guy beat me to it in a way! Well, here's what I was writing before I crashed:

@ amazon: Wow, thanks for the link and mentioning this because I have never heard of it before. I can't wait until reviews on it start coming in. I'm glad there are some serious attempts being made to try and develop new male sex toys.

@ davidstyles: Uh, I thought perhaps the pleasure pillow was a joke for April Fool's Day, but I guess it's not. Since you have it...what do you think is so different about it than a regular pillow, or that someone couldn't just make their own?

@ irishlove: I realize a Fleshlight might be more than you can afford, but in case you can get on and your partner likes it enough, I wanted to pass on tip i found in this video review on caring for a Fleshlight. At the end, he explains that you can buy replacements of the hard, outer shell, or the different sleeves separately. So, once you have a Fleshlight, you don't have to buy another whole, expensive unit to replace a damages casing, or to try new styles. Yes, the different styles, with their different external appearances to the entrance, as well as the different internal textures can be bought for MUCH lass than the full price and all you do is place the new sleeve inside your original case. It's a practical, space-saving and money-saving way to try as many of the different Fleshlights as you want. Here's the video telling this info at the end and showing the simple cleaning.