Holly Madison details ‘really weird’ group sex nights with Hugh Hefner at the Playboy mansion

May 9, 2026

The “Girls Next Door” alum says the group sex nights were anything but sexy.

https://pagesix.com/2026/05/09/celebrity-news/holly-madison-details-weird-sex-nights-with-hugh-hefner/

Holly Madison details ‘really weird’ group sex nights with Hugh Hefner at the Playboy mansion <body> <h1> Array ( [0] => golly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [1] => bolly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [2] => nolly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [3] => jolly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [4] => uolly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [5] => yolly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [6] => hilly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [7] => hklly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansion [8] => hllly madison details ‘really weird’ group sex nights with hugh hefner 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the playboy mansion [194] => holly madison details ‘really weird’ group s4x nights with hugh hefner at the playboy mansion [195] => holly madison details ‘really weird’ group s3x nights with hugh hefner at the playboy mansion [196] => holly madison details ‘really weird’ group sez nights with hugh hefner at the playboy mansion [197] => holly madison details ‘really weird’ group sec nights with hugh hefner at the playboy mansion [198] => holly madison details ‘really weird’ group sed nights with hugh hefner at the playboy mansion [199] => holly madison details ‘really weird’ group ses nights with hugh hefner at the playboy mansion [200] => holly madison details ‘really weird’ group sex bights with hugh hefner at the playboy mansion [201] => holly madison details ‘really weird’ group sex mights with hugh hefner at the playboy mansion [202] => holly madison details ‘really weird’ group sex jights with hugh hefner at the playboy mansion [203] => holly madison details ‘really weird’ group 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hefner at the playboy mansion [262] => holly madison details ‘really weird’ group sex nights with jugh hefner at the playboy mansion [263] => holly madison details ‘really weird’ group sex nights with uugh hefner at the playboy mansion [264] => holly madison details ‘really weird’ group sex nights with yugh hefner at the playboy mansion [265] => holly madison details ‘really weird’ group sex nights with hygh hefner at the playboy mansion [266] => holly madison details ‘really weird’ group sex nights with hhgh hefner at the playboy mansion [267] => holly madison details ‘really weird’ group sex nights with hjgh hefner at the playboy mansion [268] => holly madison details ‘really weird’ group sex nights with high hefner at the playboy mansion [269] => holly madison details ‘really weird’ group sex nights with h8gh hefner at the playboy mansion [270] => holly madison details ‘really weird’ group sex nights with h7gh hefner at the playboy mansion [271] => holly madison details ‘really weird’ group sex nights with hufh hefner at the playboy mansion [272] => holly madison details ‘really weird’ group sex nights with huvh hefner at the playboy mansion [273] => holly madison details ‘really weird’ group sex nights with hubh hefner at the playboy mansion [274] => holly madison details ‘really weird’ group sex nights with huhh hefner at the playboy mansion [275] => holly madison details ‘really weird’ group sex nights with huyh hefner at the playboy mansion [276] => holly madison details ‘really weird’ group sex nights with huth hefner at the playboy mansion [277] => holly madison details ‘really weird’ group sex nights with hugg hefner at the playboy mansion [278] => holly madison details ‘really weird’ group sex nights with hugb hefner at the playboy mansion [279] => holly madison details ‘really weird’ group sex nights with hugn hefner at the playboy mansion [280] => holly madison details ‘really weird’ group sex nights with hugj hefner at the playboy mansion [281] => holly madison details ‘really weird’ group sex nights with hugu hefner at the playboy mansion [282] => holly madison details ‘really weird’ group sex nights with hugy hefner at the playboy mansion [283] => holly madison details ‘really weird’ group sex nights with hugh gefner at the playboy mansion [284] => holly madison details ‘really weird’ group sex nights with hugh befner at the playboy mansion [285] => holly madison details ‘really weird’ group sex nights with hugh nefner at the playboy mansion [286] => holly madison details ‘really weird’ group sex nights with hugh jefner at the playboy mansion [287] => holly madison details ‘really weird’ group sex nights with hugh uefner at the playboy mansion [288] => holly madison details ‘really weird’ group sex nights with hugh yefner at the playboy mansion [289] => holly madison details ‘really weird’ group sex nights with hugh hwfner at the playboy mansion [290] => holly madison details ‘really weird’ group sex nights with hugh hsfner at the playboy mansion [291] => holly madison details ‘really weird’ group sex nights with hugh hdfner at the playboy mansion [292] => holly madison details ‘really weird’ group sex nights with hugh hrfner at the playboy mansion [293] => holly madison details ‘really weird’ group sex nights with hugh h4fner at the playboy mansion [294] => holly madison details ‘really weird’ group sex nights with hugh h3fner at the playboy mansion [295] => holly madison details ‘really weird’ group sex nights with hugh hedner at the playboy mansion [296] => holly madison details ‘really weird’ group sex nights with hugh hecner at the playboy mansion [297] => holly madison details ‘really weird’ group sex nights with hugh hevner at the playboy mansion [298] => holly madison details ‘really weird’ group sex nights with hugh hegner at the playboy mansion [299] => holly madison details ‘really weird’ group sex nights with hugh hetner at the playboy mansion [300] => holly madison details ‘really weird’ group sex nights with hugh herner at the playboy mansion [301] => holly madison details ‘really weird’ group sex nights with hugh hefber at the playboy mansion [302] => holly madison details ‘really weird’ group sex nights with hugh hefmer at the playboy mansion [303] => holly madison details ‘really weird’ group sex nights with hugh hefjer at the playboy mansion [304] => holly madison details ‘really weird’ group sex nights with hugh hefher at the playboy mansion [305] => holly madison details ‘really weird’ group sex nights with hugh hefher at the playboy mansion [306] => holly madison details ‘really weird’ group sex nights with hugh hefnwr at the playboy mansion [307] => holly madison details ‘really weird’ group sex nights with hugh hefnsr at the playboy mansion [308] => holly madison details ‘really weird’ group sex nights with hugh hefndr at the playboy mansion [309] => holly madison details ‘really weird’ group sex nights with hugh hefnrr at the playboy mansion [310] => holly madison details ‘really weird’ group sex nights with hugh hefn4r at the playboy mansion [311] => holly madison details ‘really weird’ group sex nights with hugh hefn3r at the playboy mansion [312] => holly madison details ‘really weird’ group sex nights with hugh hefnee at the playboy mansion [313] => holly madison details ‘really weird’ group sex nights with hugh hefned at the playboy mansion [314] => holly madison details ‘really weird’ group sex nights with hugh hefnef at the playboy mansion [315] => holly madison details ‘really weird’ group sex nights with hugh hefnet at the playboy mansion [316] => holly madison details ‘really weird’ group sex nights with hugh hefne5 at the playboy mansion [317] => holly madison details ‘really weird’ group sex nights with hugh hefne4 at the playboy mansion [318] => holly madison details ‘really weird’ group sex nights with hugh hefner zt the playboy mansion [319] => holly madison details ‘really weird’ group sex nights with hugh hefner st the playboy mansion [320] => holly madison details ‘really weird’ group sex nights with hugh hefner wt the playboy mansion [321] => holly madison details ‘really weird’ group sex nights with hugh hefner qt the playboy mansion [322] => holly madison details ‘really weird’ group sex nights with hugh hefner ar the playboy mansion [323] => holly madison details ‘really weird’ group sex nights with hugh hefner af the playboy mansion [324] => holly madison details ‘really weird’ group sex nights with hugh hefner ag the playboy mansion [325] => holly madison details ‘really weird’ group sex nights with hugh hefner ay the playboy mansion [326] => holly madison details ‘really weird’ group sex nights with hugh hefner a6 the playboy mansion [327] => holly madison details ‘really weird’ group sex nights with hugh hefner a5 the playboy mansion [328] => holly madison details ‘really weird’ group sex nights with hugh hefner at rhe playboy mansion [329] => holly madison details ‘really weird’ group sex nights with hugh hefner at fhe playboy mansion [330] => holly madison details ‘really weird’ group sex nights with hugh hefner at ghe playboy mansion [331] => holly madison details ‘really weird’ group sex nights with hugh hefner at yhe playboy mansion [332] => holly madison details ‘really weird’ group sex nights with hugh hefner at 6he playboy mansion [333] => holly madison details ‘really weird’ group sex nights with hugh hefner at 5he playboy mansion [334] => holly madison details ‘really weird’ group sex nights with hugh hefner at tge playboy mansion [335] => holly madison details ‘really weird’ group sex nights with hugh hefner at tbe playboy mansion [336] => holly madison details ‘really weird’ group sex nights with hugh hefner at tne playboy mansion [337] => holly madison details ‘really weird’ group sex nights with hugh hefner at tje playboy mansion [338] => holly madison details ‘really weird’ group sex nights with hugh hefner at tue playboy mansion [339] => holly madison details ‘really weird’ group sex nights with hugh hefner at tye playboy mansion [340] => holly madison details ‘really weird’ group sex nights with hugh hefner at thw playboy mansion [341] => holly madison details ‘really weird’ group sex nights with hugh hefner at ths playboy mansion [342] => holly madison details ‘really weird’ group sex nights with hugh hefner at thd playboy mansion [343] => holly madison details ‘really weird’ group sex nights with hugh hefner at thr playboy mansion [344] => holly madison details ‘really weird’ group sex nights with hugh hefner at th4 playboy mansion [345] => holly madison details ‘really weird’ group sex nights with hugh hefner at th3 playboy mansion [346] => holly madison details ‘really weird’ group sex nights with hugh hefner at the olayboy mansion [347] => holly madison details ‘really weird’ group sex nights with hugh hefner at the llayboy mansion [348] => holly madison details ‘really weird’ group sex nights with hugh hefner at the -layboy mansion [349] => holly madison details ‘really weird’ group sex nights with hugh hefner at the 0layboy mansion [350] => holly madison details ‘really weird’ group sex nights with hugh hefner at the pkayboy mansion [351] => holly madison details ‘really weird’ group sex nights with hugh hefner at the ppayboy mansion [352] => holly madison details ‘really weird’ group sex nights with hugh hefner at the poayboy mansion [353] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plzyboy mansion [354] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plsyboy mansion [355] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plwyboy mansion [356] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plqyboy mansion [357] => holly madison details ‘really weird’ group sex nights with hugh hefner at the platboy mansion [358] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plagboy mansion [359] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plahboy mansion [360] => holly madison details ‘really weird’ group sex nights with hugh hefner at the plauboy mansion [361] => holly madison details ‘really weird’ group sex nights with hugh hefner at the pla7boy mansion [362] => holly madison details ‘really weird’ group sex nights with hugh hefner at the pla6boy mansion [363] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playvoy mansion [364] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playnoy mansion [365] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playhoy mansion [366] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playgoy mansion [367] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playgoy mansion [368] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbiy mansion [369] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbky mansion [370] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbly mansion [371] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbpy mansion [372] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playb0y mansion [373] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playb9y mansion [374] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbot mansion [375] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbog mansion [376] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboh mansion [377] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbou mansion [378] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbo7 mansion [379] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playbo6 mansion [380] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy nansion [381] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy kansion [382] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy jansion [383] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy jansion [384] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mznsion [385] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy msnsion [386] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mwnsion [387] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mqnsion [388] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mabsion [389] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mamsion [390] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy majsion [391] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mahsion [392] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mahsion [393] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy manaion [394] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy manzion [395] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy manxion [396] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mandion [397] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy maneion [398] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy manwion [399] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansuon [400] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansjon [401] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy manskon [402] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansoon [403] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mans9on [404] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mans8on [405] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansiin [406] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansikn [407] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansiln [408] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansipn [409] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansi0n [410] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansi9n [411] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansiob [412] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansiom [413] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansioj [414] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansioh [415] => holly madison details ‘really weird’ group sex nights with hugh hefner at the playboy mansioh ) </h1> </body>