Never tried giving my Late Wife "Anal Sex" while she held in an Enema.I think the risk of leakage,and the mess would be a Big Turn OFF?? For both??
However we did do "Anal Sex" while holding in an Enema,but a reverse scenario.She would have me face down on the bed in restraints with a doubled pillow under me to elevate my Ass for a Sound Spanking(Her Way!)with a Leather Strap!
She would have our 4qt Enema Bag hanging next to the bed with 2-3qts in it prior to the Spanking which was going into my vunerable RED WELTED ASS after the Strapping that she loved giving my squirming Ass.Without hesitation SMACK,SMACK,SMACK,SMACK,.....
When she decided my Ass was RED/HOT enough the Spanking would be over,but only when SHE decided! There were times I had tears running down my face due to the PAIN...that turned her on a lot,and after the Strapping was over she would give my stinging RED ASS a soothing cool lotion massage/fingering followed with the Big Enema.
The restraints were always removed for the Enema in case I could'nt take the whole bag,but that never happened for good reason.She would make me lick/tongue her pussy,and Ass while the Enema drained into me.
Here is the Pay Off! When the bag was enmpty she would suck my hard cock breifly,Rremove the Enema nozzle from my FULL ASS, then she would lube my cock,and her Anus...Now she would tell me to give her sweet tight Ass a good Hot Cum Enema balls deep while holding in my ENEMA! Sliding my throbbing hard Cock slowly into her little Sexy Hot Ass then giving her a good deep pondind until we both screamed/erupted into violent Orgasims was Fantastic mmmmm!!
WOW!! The Orgasims were AWESOME!! I never leaked a drop of the Enema,and She loved getting a Hot Cum Enema with me holding in the Enema she just gave me.Spanking me hard,then giving me an Enema made her so HOT!(Me too!!:)
It was always a worth while Trade Out wich we did many times in our AWESOME 20 year marriage. I was so blessed to have her,and miss her dearly.Ours was a "Once in a Life Time" Perfect Marriage,and She was a Very "Special Lady"!
It has been 5 years since she was taken from me by cancer,but she made me promise her that I would find some one else,and not be alone for the rest of my life.I still have a hole in my heart,but I have a lot of love left in my heart for the "Right Lady" if I'm lucky enough to find her?