When you asked about anal sex first take a muscle relaxer and use lots of lube and do not try it the first time just let him play with you there using his fingers until you can take him without any pain just using his fingers then progress to let him just try to put the head of it in and no rush on that part also soon you will be craving him to do more using more fingers and putting it in a little farther but have to take your time just a foreplay to sex and not do it until you are ready again just lots of lube astrolube from walmart is great and again just play with your ass until you are comforable taking his fingers then progress from there let me know if this worked this is the way i did with my wife took almost 6 months before she was ready
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