Place tomatoes, jalapenos, and fennel in a bowl. Season liberally with pepper, salt and the Worchestershire sauce. Coat with olive oil, tossing lightly. Put a few of the tomatoes in the blender and liquefy - this will make it easier to puree the rest of the solids. Add the fennel/tomato/jalapeno mixture to a blender and puree until liquefied. Store in refrigerator up to 6 hours until chilled.
Hint: If you can find them, heirloom tomatoes can really boost the flavor of this drink. Heirloom tomatoes are typically varieties that were grown over 50 years ago, before tomatoes were bred for ease of picking and distribution. Heirlooms tend to be a little more acidic than modern commercial tomatoes, and often the fresh tomato flavor is more pronounced.
Assembling the cocktail:
Rub a cut lemon around the rim of a chilled martini glass. Dip the glass, upside down, in salt or your favorite spice rub. Slice the tip of a red jalapeno pepper vertically and slip over the rim. Place 1 or 2 of the jalapeno ice cubes in each glass, pour chilled bloody maria mixture on top, and top each glass with 1 ounce of lemon vodka. Stir carefully and serve.
Hint: If you don't have lemon vodka, use regular vodka and squeeze a little lemon juice in each glass.
Jalapeno Ice Cubes:
3 jalapeno peppers
1 quart fresh, cold water
4 fresh basil leaves
Remove the tops and stems of the jalapenos and slice. Place the water in a blender and add the jalapenos, seeds and all. Add the lemon to the blender, peel and all. Add the basil, a pinch of salt, and some ground black pepper, to taste. Puree in the blender until everything is incorporated. Strain through a sieve and pour into ice cube trays and freeze overnight until solid.