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i will repeat what everyone else has said.. TAKE IT SLOW!!! and i mean slow.. not 2 or 3 times and expect to take him all the way and have multiple orgasms like the movies lead u to believe... i started with fingers then small toys then bigger toys then i was ready for the real thing.. and all of this was over like a 3 month time span... a guy would slip a finger in every now and then.. a few weeks later tried a small vibrator which was really nice after a couple weeks of practice.. then a bigger vibrator which was really nice after alot of loosening up.. almost a month... then tried the real thing... and i have to agree the best position starting out is spooning.. it still is the easiest for a guy to enter when im in that position.. till im nice and relaxed back there.. then its whatever postion feels best.. but the key is take ur time.. its not gona happen if u rush it.. if u rush it and it doesnt work u probably arent gonna wanna try it again.. but if u take ur time the reward will be great
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