Havana Pooning Tips
In Havana Viejo (Old Havana) there is a hotel called the Igliterra, not too far from the capitol building on the main Prado road. There are plenty jiniteras (part-timers) there, most 5-7s in looks. They will go with you to your room for 1 hour for US$40 for FS SSOG, no DFK, DAT, or even CBJ. Make sure you bring North American condoms and lube as they are not always so prepared.
Note that most hotels will not allow girls in the room (at least when I when I was there in 2001), so I suggest you quickly move to a casa particulare (private room). Try asking the doormen or bartenders for suggestions (semi nice room in a private house, or even a secure and clean 1 BR apartment shouldn't be much more than $20-25 a night in Old Havana).
A better bet is to befriend a Cuban hustler guy, who for $20-40 a night in drinks/food will negotiate a top amateur local in the 7-9 looks range for US$40-50. These guys can also find a private residence that will rent you their room for an hour for $10-20.
Also, all the girls will not walk with you for fear of being arrested so they will require you to hail a cab even for a short 4-6 block drive.
A cheaper option is to join Amigos.com (spanish subsidiary of Adultfriendfinder.com) and meet women you don't have to pay (other than to entertain). Locals didn't use to have access to the internet in Cuba (only tourists), but I have noticed a few Cuban gals on that site recently (I plan to meet some Latinas Calientes - hot latin gals - in Peru in December).
You also may be able to negotiate a lot for any type of bath products (oils, hair gels, lotions, etc.). Nearly every gal tried to coax some items off me and I was not willing to negotiate because I was on a round-the-world tour and needed the supplies I had.
Finally, check out the WorldSexGuide.com / .org for plenty of international details.
The music, dancing, women and culture are amazing there. Enjoy!