(Completely true story)
I didn't actually put this thing in my ass, my cousin did...
It was a nice spring afternoon and we had his house to ourselves for a few hours until his mom would get home from work. It wasn't unusual for us to have sex, as we'd been experimenting for a few years. Over that time, I'd become the full-time "girl."
While I'd enjoyed topping him when we first began having sex, I was always a bit big for him, and - anyway - I'd increasingly enjoyed the passive role. This day, I played out that fantasy to the max, and experienced the most memorable gay sex I ever had.
Comfortable that we would not be interrupted, I stripped completely, even - for once- including my socks. I then broached a subject I'd been thinking about for weeks: I asked him how he'd like for me to dress up as a real girl. His sister was about my size, and though she's recently moved out she'd left a lot of clothes behind. He did n't show a lot of enthusiasm but said it would be "allright."
Taking that as a "yes" I plunged into her belongings and emerged a few minutes later feeling very girlish. I had on black hose (but not thigh highs, unfortunately), some silky green panties, a dark green silk camisole that was a bit snug, a bra stuffed with socks, and one of their mom's wigs. In retrospect I probably looked rather silly, but I felt sexy as hell. Timidly I opened the door to the room where he waited, and was met by the faintest of grins.He was typically reserved, but the little bulge in his pants told me he liked the result.
We always used his mom's Vaseline for lubricant, but this day called for another step, and this involves the "most insane object" them of this thread.
In his mom's medicine cabinet, there was a tube of Ortho Contraceptive gel, and a plastic applicator. I figured that this would finish the fantasy for me, to have a woman's birth control gel coating my boy pussy to protect me from his sperm. I screwed the tube onto the applicator and squeezed the gel into the applicator until it was full. I then coated the outside of the aplicator with Vaseline and returned to the bedroom.
I instructed him on what I wanted done, then lay face down on his mom's bed as he gently pulled down my silk panties and hose, parted my butt cheeks, wriggled the applicator into my butt and squeezed the gel into my boy pussy.
Minutes later we were deep into our familiar roles, with me on my back near the foot of the bed, and with him standing at the foot with his slender cock buried in me. This time, though, I wrapped my hose-clad legs around his waist and crosed my ankles in the small of his back, pulling him deeply into me, feeling the cock slide gently back and forth into the mix of Ortho gel and Vaseline, and close my eyes. I was easy to imagine myself as a young girl being made love to for the first time.
When he warned me of his nearing climax, I pulled him deep and held him tighly, compromising his ability to thrust but not changing the outcome. As he tensed and began to spurt deeply (well, as deeply as a 4.5 inch cock can go) I only then touched my neglected cock and immediately came with him.