I lost my virginity to my girlfriend my senior year of high school, but it didn’t include any penetration. When she tried to finger me, she got up to her first knuckle and it hurt. We didn’t try that again.
At the beginning of my freshman year of college, I had a boyfriend. I was his first kiss, first everything. We had a fairly active sexual relationship without penetrative sex, with hands and mouths and grinding. Eventually he was the first man to be inside me. Our few times having penetrative sex largely involved him laying back while I slowly, and with much trepidation and lubricant, worked my way, centimetre by centimetre, down his thick shaft. It was sex, and we cared for each other and trusted each other deeply, but it was nowhere near a fuck.
During this same time frame I met another man through a leadership opportunity I took. He was 22, Hispanic, brilliant and adventurous, and seriously sexually experienced. Think… Big Kahuna from Gidget and you pretty much have his nature and our dynamic. I quickly became infatuated with him. He saw my ambition and took a liking to me and we struck up a working quasi-romantic relationship. Obvious power dynamic and innate life experience differences aside, it was great. But the fact that I was seventeen kept getting in the way. He was a smart man and didn’t want to be accused of any impropriety. We would go on adventures in the middle of the night around campus, in the woods and on the beach, to galas and dockyards and tiny restaurants, but always careful of our closeness.
A few months later my eighteenth birthday rolled around and I went out for a celebratory dinner with him and some friends. When we returned to my room I made it quite clear that my roommate was to depart immediately so I could claim “my legal right to fuck.” (A real quote.) She did, and the fun began.
I had obtained several condoms and packets of lube from the clinic and thought myself very prepared. As he and I made out on my bed, tightly wrapped in each other’s arms, I mentioned that I would need lube because I wouldn’t be able to take him otherwise. He leaned in close to my ear and said, “You won’t need it when I’m done with you.”
I took this as a personal affront to my own bodily sovereignty and responded with, “Do you think you know my body better than me?” He gave me a textbook crooked grin, pushed me down on the duvet, and put himself between my legs.
He ate me out like it was his job, only pausing to tease my entrance with the tips of his calloused fingers but never entering even when I pleaded with him to do so. After an unknown period of time elapsed, he performed several actions seemingly instantaneously.
He got up, rolled me over and half off the side of the bed, put on a condom, grabbed my hips, and fucked me from behind in one sharp stroke.
I screamed, reaching back and grabbing his thigh in response. But by the time he thrust in again, the pain was gone and I started to feel that the place he was hitting inside me was some form of bliss I had never experienced. Then I began screaming again, but this time they were moans interspersed with his name and other expletives and exclamations. It was at this point that I discovered my affection for being fucked from behind.
He continued here for a while longer, then pushed me back onto the bed and entered me in missionary, holding my legs back against my torso. I had never been in any of these positions before, except for maybe some clothed naive teasing and grinding from past boys. I must have been making enough racket to wake the dead, but every new touch and thrust and movement was my first time experiencing it.
After more positions on the bed he tried to pull me into a standing position. This faired poorly as my legs gave out quickly underneath me. Our bodies compromised and I ended up in the shower holding to the wall for dear life as he held me up on his cock with his strong arms.
That night we slept in my bed together, curled into each other tightly now that no law could keep us apart.
Source: reddit.com/r/gonewildstories/comments/ibw2f6/fm_my_first_true_fucking