Expert: Master Shadow - 7/4/2009

Question
QUESTION: Hi. Me and my girlfriend are curious as to why I enjoy and feel the need to dress as a woman even to the point I have a womans name for those times. Also what is the safest cleanest way to prepare for and conduct anal play on me with her using a strap on cock. What also would be the best size? Thank you miss.

ANSWER: A light enema would clean you out, and prepare you for anal play with your Mistress. Use something easy on the system. There are many brands out there to choose from, so finding one that is easy on your stomach shouldn't be a problem.

As to the actual act, start out with plenty of lube, and use a lube shooter, or similar product to get the lube inside, where it does the most good. Have Her start with Her fingers(No long nails!!), carefully, so as to not tear you, or cut you with fingernails. Go slowly, and use a circular massage pattern when She opens you up. Patience, and understanding are necessary for this. Have Her add fingers one at a time as you start to stretch. There should be no pain when doing this, as it will cause you to tighten up, and you'll have to start over.

Once She has you where She can get at least three fingers into you, it's time to introduce the strapon. Once again, use plenty of lube, and at any point, if it gets too painful, stop, and give it  time. Remember, there are two sphincters in the rectum, and time needs to be given to loosen the inner sphincter as well.

As for size, start out small, and work your way up. Use whatever fits comfortably, although there may be a slight bit of discomfort, if it hurts too much, neither of Y/you will enjoy the experience. Remember, patience pays off!


Have fun, play safe, and enjoy!!! Hope this helps!


        
         SINcerely in Leather,
         Master Shadow.


---------- FOLLOW-UP ----------

QUESTION: Thank you for your answer. One more question. What's the best position for me (male) to be penetrated by my girlfriend with a strap on? Me on my back? Me riding? Or what?

Answer
Doggie style would be preferable, in my opinion, and offer the most ease of control between the two of you during this time of "exploration" LOL

Be well, play safe, and have fun!


         SINcerely in Leather,
         Master Shadow.