A Shot of Myself

When I was a teenager I spent a lot of time in internet chat rooms talking with people from all over the world. Some I ended up maintaining friendships with for several years, and a few I met in person and developed even deeper friendships. I also had a number of girls that I was sexual with online over this period. This included engaging in cyber sex, role-playing, sharing pictures and occasionally webcam masturbation. In a lot of ways this allowed me to explore my sexuality in a relatively safe environment, and it definitely led to me developing a number of fetishes. One girl, named Alicia, who was roughly my age, had been an online sexual partner of mine for at least a couple of years. I found myself very sexually attracted to her, as she wasn't afraid to initiate things when she was horny, and she had a slightly more dominant side at times. We had exchanged pictures previously, which made me realise just how gorgeous she was with her short blonde hair, slim tanned body and pert breasts. I'd also gone on webcam for her several times, and was treated to her joining me once. At the time, it was probably one of the most erotic experiences I'd had, stroking my cock for this girl while I watched her fingers delving between her thighs and glistening with her juices. This particular time, we had been teasing each other for probably an hour, detailing how we wanted to play with one another. It was typical of our conversations, as we were both constantly horny teenagers. I'd been rubbing my cock through my pants, squeezing the head and milking pre-cum from it. I mentioned how wet I was making my underwear, which prompted her to request that I show her. I didn't need to be asked twice, so I turned my webcam on and quickly checked myself over before I invited her to view me. I asked her if she wanted to see the state I was in, and when she replied yes I stood up, focusing the view of the webcam on my tented sweatpants. Knowing I had her attention, I slipped my pants down to reveal the thick outline of my cock, bulging in my navy, cotton boxer-briefs. There was an obviously darkened patch at the head where the pre-cum had soaked in, and I rubbed down the shaft with thumb and forefinger to squeeze out some more drops. She encouraged me to continue, telling me how wet she was and that she couldn't keep her fingers off her clit. I lowered my underwear slowly, easing it down until the head of my cock sprang out from underneath the waistband, making my cock wobble up and down. Then, grabbing it tightly in my fist, I began to jerk it, tugging down on the skin to expose the slick, pink head. I moved slowly, making sure the webcam got a clear view as my foreskin peeled back to reveal a droplet of my pre-cum as it oozed from the slit. 'Sit down and take it all off.' She wrote to me. I followed the command, kicking my pants and underwear away, stripping my top off and sitting back in the desk chair so the webcam could see everything. I continued stroking my cock, picking up the pace, assuming that she'd want to watch me squirt all over my chest and tummy like I'd done for her previously. I was getting lost in the pleasurable rhythm of it, stroking harder and pushing my hips up against my fist, but would occasionally remember that she was watching me, sitting there at her computer with her hand between her legs. She gave me periodic updates, to the point where she was now fingering herself while I stroked. 'Put a finger in your ass.' Was her next direction. She shared my own anal fetish, and knew I loved to cum while I played with my ass. I sucked on one of the fingers of my free hand, coating it in my saliva, then reached down and slid it up into my ass. It pushed in smoothly, sinking in up to the knuckle with relative ease. It wasn't unheard of for me to use 3 or even 4 fingers in my ass, but I was most comfortable with digging deep inside with 1 or 2. 'Don't you cum yet.' She must have been able to read it in my face, as the finger in my ass had pushed me close to the edge. I held my hand steady on my cock, squeezing it tightly in my fingers to try and ease off. 'Find something you can cum in. I want you to swallow all of your cum.' "Ah...all of it?" I'd tasted my cum before, licking a string of it off my fingers, but I'd never swallowed the whole thing. I wasn't even sure how I'd go about doing it. 'Yes! Get something you can cum in, then drink it all.' I got up out of the chair, rapidly trying to think of something, and when I turned around my eyes fell on the cabinet against the wall. It held an assortment of items that were used infrequently, including wine glasses, ornamental bowls, and small shot glasses. It was the little shot glass that pinged in my brain as the answer. I quickly grabbed one out of the cabinet and came back to hold it up in front of the webcam, seeking her approval. 'Perfect!' I positioned myself back in the chair, head against the headrest, legs splayed out in front of me and my erection poking straight up from my crotch. As I began to stroke myself again, my other hand held the shot glass, ready to position it to catch my load. It wasn't long before I was back at the edge of an intense orgasm, the thought of swallowing my cum for this girl exciting me even more than the finger I'd had in my ass. It would have been obvious to her too, with the speed I was stroking and the way my hips thrust against my fist of their own accord. 'Do it. Cum for me' I jerked my cock as fast as I could and held the shot glass at the head. I could feel that intense throbbing and then I crashed into my orgasm. Cum burst from the pink head, spurting into the shot glass. Rope after rope, matching the pulses of pleasure that exploded through my body I continued to fuck against my fist, gradually slowing, but tightening my hand, milking all of the cum out of the shaft and into the shot glass. By the time I was done it was about two thirds full of my cloudy white juices. 'Drink it.' I brought the shot glass to my lips, looked directly into the webcam, tilted my head back and let my cum flow out of the glass and past my lips. It was warm and salty on my tongue, not exactly unpleasant but strong. I felt so dirty in that moment, my mouth full of my own cum, my cock beginning to soften, my chest and face flushed red with excitement and embarrassment. I drained every last drop from the glass, and then swallowed it in one gulp. 'Mmm fuck that was hot. I'm cumming!' Was her response. We chatted for a little afterwards, and she'd obviously enjoyed the show. She asked me if I liked it, if I'd ever do it again for her. I admitted it was pretty hot, and that if she really wanted I probably would. It was several weeks before the opportunity came again. She came online one day and we began chatting, then she told me she had a friend over. Apparently she'd been talking to her friend about us, and had told her about how she'd watched me swallow my cum, and now her friend wanted to see it too. I'm not sure if it was some disgusted curiosity, or genuine sexual excitement, but if two girls wanted to watch me masturbate on webcam then I was up for that. We got straight down to business, I turned my webcam on, grabbed the glass and removed my clothes. Alicia wasn't as involved this time, although they were both encouraging me to cum for them. I pumped my cock hard and fast and it wasn't long before I emptied myself into the glass again. I brought it to my lips and swallowed it all for them, and they praised my performance. Looking back on it I feel that it was something of a freak show for her friend, but I'd like to imagine that it left a dampness in both their panties that they had to take care of later.