M20P PLT CONCERNED ABOUT LNDG JYO ARPT; WITHIN IAD CLASS B WITHOUT OBTAINING A PRIOR IFR CLRNC.

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FILED TWO IFR FLT PLANS ROUND TRIP FROM LEESBURG (KJYO) TO PRINCETON (39N); ON DUATS; DEPARTING JYO AND 39N. LEAVING KJYO; DULLES (KIAD) CLRNC DELIVERY COULDN'T FIND MY IFR FLT PLAN; SAID IT WASN'T IN THE COMPUTER. I CALLED FSS ON MY CELL PHONE RE-FILED IFR. THEN PICKED UP CLRNC AND FLEW IFR TO 39N. ON RTN LEG; COULDN'T RAISE NY APCH ON THE GND AT 39N. DEPARTED VFR; CALLED NY APCH TO PICKUP IFR CLRNC IN THE AIR. THEY HANDED ME OFF TO PHILADELPHIA APCH; SAID TO GET IT FROM THEM. PHILLY APCH COULDN'T FIND MY CLRNC IN THE COMPUTER; INSTEAD CLRED ME THRU THE PHILLY CLASS B; VFR AT 6500 FT; GAVE ME A ROUTING TO MY DEST ARPT. MY INTENT AT THAT POINT WAS TO STAY VFR UNTIL I WAS IN THE BALTIMORE/WASHINGTON AREA; THEN AIR-FILE IFR TO ENTER THE DULLES ENHANCED CLASS B AIRSPACE (KJYO IS INSIDE THAT AIRSPACE; AND AN IFR CLRNC IS CURRENTLY REQUIRED TO ENTER THE ENHANCED CLASS B); AS THAT WOULD BE SIMPLER THAN NEGOTIATING AN ENTIRE IFR ROUTE CLRNC WITH PHILLY APCH. PHILLY APCH HANDED ME OFF TO BALTIMORE APCH; WHO HANDED ME OFF TO DULLES APCH. NOTHING WAS SAID ABOUT MY FLT STATUS. ON HANDOFF TO DULLES APCH; I CONFIRMED THAT I WAS CLRED INTO THE CLASS B. DULLES APCH DID NOT INQUIRE WX I WAS ELIGIBLE TO ENTER THE AIRSPACE WITHOUT AN IFR CLRNC. DULLES APCH VECTORED ME TOWARD KJYO; THEN WHEN I SAW THE ARPT (4-5 MI OUT); I CALLED; SAID; 'ARPT INSIGHT; CANCEL IFR.' DULLES RESPONDED; 'YOU AREN'T IFR;' TO WHICH I REPLIED; 'OH; YES; OK.' DULLES THEN SAID; 'RADAR SVC TERMINATED; SQUAWK 1200; FREQ CHANGE APPROVED.' I LANDED AT KJYO. DURING THE DRIVE HOME; I REALIZED THAT I HAD FORGOTTEN TO AIR-FILE IFR BEFORE ENTERING THE DULLES ENHANCED CLASS B AIRSPACE. I ALSO LATER CHECKED MY LOGBOOK AND FOUND THAT I HAD NOT HAD THREE NIGHT LANDINGS WITHIN THE PAST 90 DAYS; AS REQUIRED SINCE THIS FLT BEGAN IN DAYLIGHT BUT ENDED AT NIGHT. I HAD INTENDED TO GET A 'POP-UP' IFR CLRNC PRIOR TO ENTERING THE DULLES ENHANCED CLASS B AIRSPACE; BUT OVERLOOKED IT BECAUSE I WAS ALREADY TALKING TO ATC; WAS ON AN ASSIGNED ROUTING; ALT AND SQUAWK CODE; AND IT FELT LIKE I WAS ALREADY IFR; IT SIMPY DIDN'T OCCUR TO ME AT THE TIME THAT I NEEDED TO GET THE IFR CLRNC. REGARDING THE NIGHT LANDING CURRENCY; I THOUGHT I WAS CURRENT AND FAILED TO CHECK MY LOGBOOK TO VERIFY THAT FACT.