High Heels, Christine, and…Cocks? Pt. 03

After what seemed like a painfully long dinner where I endured my dad and his girlfriend, Christine giggling and making sausage jokes unendingly - Christine said, "Your dad and I are going out dancing for a while tonight. Wanna go?"

"Thanks, no. You guys go on ahead. I'll hang out and watch a movie," I responded, uneasily.

I cleared the table as they went upstairs to get ready. As I was finishing up, they came downstairs dressed up and ready for a night out. I couldn't help but take all of Christine in and saw she was wearing the red patent leather heels that I had cum in earlier that evening...the ones I didn't even clean up after.

"I just love these heels. What do you think, Steven," she coyly said as she spin around letting her short skirt fly up showing her lace top nylons.

"Yeah, they're fine..." I said, weakly.

"Really? Just fine?" my dad chimed in.

"I mean, yeah, you look great. Now you kids get out of here and have some fun. And don't be too late." Again deflecting my discomfort with humor.

After what seemed like forever, they closed the front door behind them. I felt like I could breathe again. I fetched a cold soda and flaked out on the couch. I tried getting my mind off Christine. Every movie I started to watch just couldn't keep my attention. I kept thinking of how this whole thing was going to work. Was Christine going to want or expect sexual service from me on the sly now? Even worse, did she plan on telling my dad? Oh god, don't tell my dad! All this uncertainty and worry really had me on edge.

I ventured up stairs to my room and found a shoebox in the middle of my bed with "Steven" written across the top. "What now?" I said out loud. I opened the box and found a large pair of black patent leather platform heels. A note inside read, "Try them. I think you'll like how they feel."

I had never thought that I'd have a pair of sexy pumps that I could actually wear. As expected, my sweatpants tented as I started to get hard, just thinking about it. Knowing I was alone in the house, I sat on the edge of my bed and pulled the first shoe on to my right foot. Right away I noticed a slippery wetness in the sole as I slipped it on.

Shit! She had cum in them before they left the house. A little "gift" for me.

Truth be told, I liked it. Kind of a lot. Thinking that I was going to wear a pair of hot heels that were full of Christine's cum was definitely getting me hot.

I put both heels on and tried standing and found myself quite wobbly. I went to my iPad and pulled up a search of "sexy women walking in heels". I started getting a feel for it quickly. I started moving my hips sensually, which helped me keep my balance even better. "So that's why they walk that way." I thought.

Then I figured I still had plenty private time and made my way to Chrstine's stocking drawer. I found a pair similar to what she was wearing that night. Slipping the stockings on felt very exciting and taboo. Now I was fully turned on as I slid into my new heels.

Knowing that I would be on the security camera if I was in front of her closet, I sashayed over and started stroking myself gently. I thought of Christine's body, with all of her softness as well as her hardness. I was liking flaunting this newly discovered sexual side of myself. I stroked my cock faster now. "Oh, yes, Christine. Fuck my ass. Fuck me hard, all the way in." I said out loud. I was drawn to a pair of over-the-knee bright pink boots. I grabbed them and held them up to my face. Surprisingly, they were not leather but a very soft, slick rubber.

OMG! The aroma was intoxicating. I began rubbing my dick against them and nearly shot my load right then. I pulled away because I wanted to really enjoy this heavenly time masturbating, wearing stockings and heels. I started to rub myself between the silky rubber calves of her boots but felt something in one. Reaching down in, I found a large rubber dildo with a suction cup at the non-business end. Another note was attached from Christine, "Stuff this up your ass and think of me. Love, C."

I had entered a whole different world of turn-ons I barely knew I had or was avoiding at the very least.

I licked the end of the dildo as I stroked myself against the smooth rubber boot. I looked right into the wall mounted camera and took as much of it down my throat as I could, slightly choking.

"You wanna see me fuck myself with it?" I asked, knowing that Christine would see my display.

I spit on the end of the phallus and began rimming my asshole with it. I stuck it onto the hardwood floor, pointing straight up and lowered myself down to this large anal intruder. After I got it started, it felt somewhat shameful, sexy, hot, and very, very good.

I let the dildo fill me as rode my cock against her rubber boots. "I'm going to cover them with my cum, Christine. Cum with me..."

The shine made from my constant flow of pre-cum made her boots slick and warm. The rubber dick was sinking into my ass deeper and deeper as I fucked myself with it.

"I can't wait to have your hard dick up my ass again." I panted. With that thought, I came raging all over her pink rubber boots and onto the floor. It's like I couldn't stop and gush after gush of my hot spunk shot everywhere. I sat down, filling my ass fully with her second "gift" and surged the last drop of seed into the bottom of her boot.

I pulled myself up just as I heard the front door open. "We're home. Are you awake?" I heard as my dad and Christine started up the stairs.

Part 4 is coming soon.