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Old 09-21-2012, 05:25 PM   #31
me1931
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Well, you asked for ruthless. Tie your big toes together. Stick some form of nipple clamps on, and hang a two pound weight from them. Kneel, and bend over so your ass is sticking out. Whip your ass, and well you are doing that swing from side to side until you cry.
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Old 09-21-2012, 05:29 PM   #32
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smack your ass with a stick till you cry
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Old 09-21-2012, 08:18 PM   #33
Kmdumo
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fuck yourself in the ass with hot sauce as lube until you cry
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Old 09-21-2012, 11:43 PM   #34
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After cumming don't stop stimulating your clit until you cry.
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Old 09-22-2012, 12:06 PM   #35
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Give yourself an enema over and over again (as long as it keeps safe) and don't let it out untill you cry.
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Old 09-22-2012, 12:08 PM   #36
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put nipple clamps on both nipples and twist as far as you can untill you cry
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Old 09-22-2012, 12:08 PM   #37
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put nipple clamps on both nipples and twist as far as you can untill you cry ruthless please as i havnt cryed in years a need a big challenge
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Old 09-22-2012, 12:17 PM   #38
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Alright you want a ruthless one i will give it to you because mine really made me cry out and my nipples still hurt terribly as they were aqlready sensitive from me being almost in my period.

Alright so you have to get toothpaste, a new tube and push the tip inside of your ass squeezing half of it in. then cover with the rest of it your dick using it as lube to masturbate. when you reach your climax keep rubbing the sensitive area as fast as possible. if that doesnt make your cry then lets have you keep the toothpaste there untill you do.
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Old 09-22-2012, 12:58 PM   #39
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Put on your nipple clamps and smack them with your hands until you cry.
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likes: mild pain, spanking, hidden, wedgies, verbal humiliation
interested in: bondage, submission
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Old 09-22-2012, 01:02 PM   #40
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get a ruler and hit your clit with it, getting progressively harder. Don't stop until you cry.
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Old 09-22-2012, 01:06 PM   #41
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Quote:
Originally Posted by moretome View Post
Put on your nipple clamps and smack them with your hands until you cry.
Ah yes i can keep smacking them untill they're red.. but it won't actually make me cry.. sorry..

As for the other person. hit your as very hard with a ruler untill you cry.
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Old 09-22-2012, 01:50 PM   #42
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OK, insert your buttplug. Do not remove it until you cry.... it might take a while...
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Old 09-22-2012, 01:59 PM   #43
intights
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wear a thong and coat the entire front and back with icy hot... then rub yourself, keep reapplying as needed, until you cry.
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Old 09-22-2012, 02:08 PM   #44
SouthAmericanGuy
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Tell someone to verbally abuse you untill you cry.
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Old 09-22-2012, 02:40 PM   #45
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tie a string to ur balls. a long string. then tie one end to each big toe. must be taught. walk around until u cry
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