Anal strap-on sex with a female on a male.

I have used anal masturbation since my first sexual relationship 40 years ago.  Since that time I have been involved in two sexual relationships where the woman used her finger or vibrator inserted into my anus while performing a hand job.  The combination was exhilarating at the very least.  During the early years I used fruits and vegetables to insert while masturbating.  With the advent of soft dildos and vibrators I switched to them.

My first dildo/vibe was a 5" model.  It was definately too short and small.  From ther I went all the way up to a 10" dildo/vibe which was too big; it caused my anus to bleed from a small fissure.  Discussing this with my proctologist, she suggested that I allow the fissure to heal by using an mixture to put on my perinium three times a day.  Instead of going all the way down to a 5", I started at the 5" and went up slowly to a 6", 7", 8", and finally a 9".  Overall the 8" was the correct size as far as sensation, pressure, and size. 

I learned that what really excited me the most during anal masturbation was the thickness rather than the length.  So it was difficult finding a dildo/vibe the right length and girth.  I finally found an 8" with a 6.5" circumference.  This was satisfying for me over the time period.  Occasionally I would toy with the idea of the 10".  I realized that I would leave that alone.

Over time, however, I wanted something different.  I saw a porn film where two lesbians were using a strap-on each other in both their vaginas and anuses, but not at the same time.  I realized that if lesbians could do this then so could a man and woman/women.  Since then I have been on a search for the "Holy Grail" of anal sex by finding a woman to experience strap-on sex with me.  It would be much easier looking for the "Holy Grail!"

No luck so far other than "escorts" who wanted $250-$500 for the experience.  The price was prohibitive for me.  That's at least 3 new tennis raquets!  I am still on that search.  When I find what I am looking for, I will report back;-)

I will continue to use anal masturbation with my 8" dildo/vibe and enjoy the moment.  Every once and awhile I still think about the 10" monster I had a few years ago.  If I am slow and delibrate using my 8" first, perhaps I could comfortably enjoy the 10"-er again without tissue problems.  If and when I do that, I will report back on that;-)