Y90 CTLR RPTED AN AIRSPACE DEV DURING A TFC PERIOD INVOLVING STRONG TAILWINDS BTWN A B757 AND A D328.

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WX WAS VFR; VISIBILITY REDUCED DUE TO HAZE; CONVECTIVE ACTIVITY IN THE AREA; BUILDUPS OF CLOUDS STARTING. BDL WAS LNDG RWY 24/15. STRONG TAILWIND ON THE ARRS FROM THE NW. THE W DEP CTLR STARTED HDOF ON A B757 LNDG BDL RWY 15 NNE; LEAVING 8000 FT. OUR REQUIREMENT IS TO HAND OFF BDL ARRS DSNDING TO 5000 FT; UNLESS COORDINATED. THE B757 CHKED IN ON MY FREQ DSNDING TO 4000 FT. I HEAR THE W DEP CTLR RELEASE AN ACFT OFF WESTOVER AIR RESERVE BASE CLBING TO 5000 FT. THIS WORRIES ME BECAUSE THE B757 THAT W DEP HANDED OFF TO ME; DSNDING TO 4000 FT; CROSSES THE WESTOVER DEP COURSE. THE B757 ASKS ME FOR A TURN TO THE S TO AVOID BUILDUPS OF CLOUDS. THE W DEP CTLR CALLS ME ON THE OVERRIDE ASKING ME IF I WILL TAKE THE HDOF ON THE J328. THE J328 WAS 7 MI W OF THE B757. THE J328 WAS AT 5000 FT AND 50-60 KTS FASTER THAN THE B757. THE B757 WAS DSNDING THROUGH 6300 FT. I TOLD THE W DEP CTLR I WOULD NOT TAKE THE HDOF BECAUSE OF THE SPD DIFFERENCE AND THAT THE B757 WAS HIGHER; CONVERGING AND STILL ABEAM THE J328; AND I WAS WORRIED ABOUT THE ACFT RELEASED OFF WESTOVER. THE W CTLR TURNED THE J328. AT THE SAME TIME; I ASKED THE B757 IF HE NEEDED A VECTOR FOR DSCNT. IT WAS 10 MI NE OF BDL AT 6000 FT. THE PLT SAID NO; HE WOULD JUST SLOW DOWN AND DSND. THE B757 GND SPD DECREASED TO 190 KTS. TAKING INTO ACCOUNT OF THE OVERTAKE OF THE J328 AND THE WAKE CREATED BY THE B757; I FELT IT WAS UNSAFE AND A SIT THAT COULD DEVELOP INTO A LOSS OF SEPARATION. THE GND SPD OVERTAKE REACHED 90 KTS WHEN THE PLT OF THE B757 SAID HE WOULD SLOW TO MAKE THE DSCNT. I ASKED THE SUPVR TO DO A QUALITY ASSURANCE REVIEW OF THE SIT BECAUSE I FELT THE OP WAS UNSAFE. DURING THE REVIEW; IT WAS FOUND THAT THE W DEP CTLR ENTERED MY (BRISTOL) CTLR'S AIRSPACE WITHOUT A HDOF OR COORD. SUPPLEMENTAL INFO FROM ACN 618170: HANDING OFF TFC TO BRISTOL SECTOR ARRIVING BDL. 1ST ACFT; B757; SLOW DSNDING; 2ND ACFT MADE FASTER DSCNT. AFTER BRISTOL ACCEPTED HDOF ON 1ST ACFT; I REALIZED ACFT #2 WAS DSNDING MUCH MORE RAPIDLY AND WAS DSNDING OVER THE RWY 15 SHELF BELONGING TO BRISTOL. I TRIED TO CALL BRISTOL TO TAKE THE HDOF BUT WAS TOO LATE. THE ACFT ENTERED THE SHELF DSNDING TO 5000 FT.