Hmmm…could this be the one I bought?

I Got Jack A New Strap-On

Well, you know where the whole Jack’s Anal Adventure was leading, didn’t you?  I had told you I was going to re-pop his cherry on his birthday, and that day had finally arrived.  We were heading back to the good ol’ US of A, so we had the whole day at sea.  I’d picked out just the right strap-on to surprise Jack with, since he had been so conscientious with his anal training.  In fact, I picked out two of them!  I started out the morning fingering his ass and massaging his prostate, seeing if those balls had re-filled from the previous night’s ruining session – and they had!  He must have had some sexy dreams!  I think the butt slut thought I was going to take him then and there, but I told him he’d have to wait.

My Sissy Butt Slut

If you read my Fem Fabulous post about making Jack into a panty boi, then you know I teased his slutty outfit.  I decided that if he was going to be a bitch, he should look like one, so I dressed him up in this cute plaid miniskirt, a bra, low cut white blouse, thigh high’s and high-heeled Mary Janes.  Now, he has matching panties to go with the bra, but I decided a pair of crotchless ones were more appropriate.  I told him he looked like the sluttiest sissy bitch I’d ever seen, then had him get on his knees, while I slid my strap-on harness on.  “Now, good sissy bitches give a great blow job before they get fucked!”

Jack Gets Fucked

I got all tingly watching him suck that strap-on – but I had other plans, so once he got it good and wet, I told him to turn around, ass up and head down.  I lubed my cock and his ass, and he said the sweetest thing to me as he felt that cock graze his crinkled hole – “Oh, please Ms. Delia, please fuck me!”  Well, I couldn’t deny him what he asked for so nicely, could I?  I slowly split him open with that cock, burying it to the balls (yes, it has balls!), listening to his gasps and moans while I filled him…and then started drilling him!  With the ridge on the back of that dildo rubbing against my clit, it wasn’t long until I had my first orgasm.  Then I had him get up on the bed on his back, spread his legs, put them up on my shoulders, and slammed into him again.  As my third orgasm was approaching, Jack began moaning he was going to cum.  “Yeah, cum with me, cum just like a bitch while you’re getting fucked!”  Those balls had re-filled, because the biggest load of the week erupted out of his cock as we came together!

After we recovered, I told him I’d bought a whole set of strap-ons…and he’d be a Size Queen in no time!