The first pair of panties I ever wore, I discovered in my cousins drawer. She asked me to grab some batteries from her dresser top drawer. They were indeed there but so were her striped boy shorts. I had been letting my friends grind on my ass to completion for a couple of months now and I wanted to add some new element to it. But it had never crossed my mind to try panties until I saw that flash of pink. Quickly I grabbed them, shoved them in my pocket, and after I handed my cousin the batteries, I excused myself to go to the bathroom. The fabric felt so wonderful. And the way they hugged my hips accentuating my ass made my heart flutter.

My first toy was my freshman year of college. Years of sneaking around with my friends and finally losing my sissy femboy virginity left me insatiable. I was absolutely shaking with nerves as I walked away from the front desk in my dormitory lobby with my package. My secret is safe in my hands. A 9” big white cock. I picked the one from Amazon that reminded me the most of my favorite of my two fwb from high school. Although I will admit that it was indeed bigger than anything I had pleasured myself with before. I almost didn’t bother dressing up. After a soapy bath in my dorm room sink for my toy and a hot 30 minute shower (complete with shaving smooth and mosturizing) I laid in bed on my tummy with my feet in the air pretending I was sucking my friends cock in his room again. With my other hand I touch my smooth warm body. My ass is round and waist is starting to slim from so much walking back and forth to classes. I stop myself short of penetration before I became aware of my neat short haircut and naked male body. After another 30 minutes of getting dressed in a thong from a garage sale, a bra left at my house after Christmas with family, and doing makeup that my best fwb bought for me at a flea market junior year, I returned to my bed. I made quick work of a warm up with an extra large sharpie. Sucking on my toy while shoving that sharpie in my butt reminded me of the threesome I had with my fwbs before we went to our separate colleges. I decided to use the suction cup on the smooth concrete floor. I felt so tight. The pleasure behind the pain persuaded me to keep going. In my mind flashes of riding my fwbs play in a loop. My room. Their rooms. The bus. In a hotel. The bathroom at a tournament. Under the stage at school. In a dugout at the softball field after a football game in 15 degree weather. I could only go halfway until I added more free lube that came with the toy (haha). When I finally sat all the way down on my very first dildo I felt like it pressed the sweet femboy cum out of me. With all my will I had to bury my face in the edge of the bed and hold in my moans of pleasure. My dorm neighbors were always home like me.