A sissy's first swallow

After weeks of being a sissy, I slowly started accepting what I was becoming and what I was doing. I even slipped out a few times to go hang out at gloryhole locations, sometimes even that old building, at times, no one would participate, show up, etc. Other times people didn't fit what I wanted, such as they were too small, unshaved, etc. But this soon started turning into a habit, to just go. I slowly started accepting that I was a sissy, and before long could live with what I was doing after I was done.

Many sissys have stories to tell, of how they became a sissy, first experience, first swallow, first time anal, first gangbang, stories with mistress' even, but most of these are for later. The second step in any sissy's adventure is the first time they can swallow, completely. Nothing like, shot across the face with a load, and a little lands in there mouth deal, the whole load, in their mouth, swallow.

I had finally worked myself up to post a craigslist ad, for anyone who wanted there dick sucked, and they had to host. My ad was up for a little over a day before I got a response from a man who appeared to be okay with a "sissy" sucking his dick. He said he had only 1 rule, and that was that there was no mess, and I had to swallow.

Now I was not good at this, the first time I ever tried at a gloryhole, I ended up getting the load stuck halfway down my throat and spitting a vast majority of it up in the nearby toilet. I hadn't really tried much after that because it was tough, you can't just suddenly decide to swallow a load, you have to practice.

We agreed to meet after exchanging a few pictures, he was a 5' 11" white dom, perfectly into getting head from a 18yr old sissy. We arranged a date and it was set, I traveled to his house, and if you can't think of a more awkward scenario then meeting someone to suck on a website. He invited me in, and asked if we should get straight to it, he should take me out, or what should occur. I decided to jump straight into it, as I had been working myself up to this all day, preparing on someone who could see me play.

He had never sent a picture of his dick, so I had no idea how big it was until he told me to take his pants off. And when I say "told", it's more like ordered. And I did as I was commanded. I unbuttoned his pants looking at a small bulge. I thought he might have been about 4-5 inches. I slowly unzipped them, and slid them down to his ankles where he stepped out of them, I could see the bulge a bit more clearly now and thought it really may have only been 4-5 inches.

He commanded me to begin rubbing his cock through his boxers, to get him hard first. I slowly raised my hand up and grabbed the absolute base of his cock and began slowly running down until I was reaching through his legs and barely felt the head, then worked back up. I kept doing this until his boxers became a bit more of a tent than anything else. And I realized, I was wrong about size.

He told me to close my eyes, and I did as I was told, yet again. I heard him slip out of his boxers, and I felt his tip touch my forehead and his balls rest on my mouth. I was in almost shock, he said open them and all I could see what his dick on my face, and all I could smell was his genitals resting right below my nose. He was cleanly shaven, and cut. I had an instant turn on, and wanted to finish myself right there. I was about to get to work, when he grabbed his member himself and lifted it up so only his balls were resting on my face, and simply told me to lie back. I dropped right below him and laid below his open legs, he dropped over me, his legs resting over my shoulders and slowly lowered his balls to my mouth again.

He told me to open, and I did it without even thinking. I was in heaven, I loved what he was doing with me. I opened my mouth and felt his hung genitals force there way into my mouth forcing me to breath through my nose, he laid his dick across my face again and told me to lick his balls.

The sweet smell of his genitals, I had a huge hard on right now, and this guy was just teasing me. I began licking his balls while inhaling the aroma of his member. After about 5 minutes of this, and a bit of slobber oozing out of my mouth, he pulled his balls out of my mouth and scooted back just enough to line the tip of his tool to my lips, I took a quick lick, he grabbed his hard cock, lifted it a few inches, and smacked it against my lips. Because of its size, it actually made decent impact. He was probably 8 1/2 - 9 inches (hard).

He continued playing with me a few times, then told me to open up, again, with no hesitation, I opened my mouth, and before I knew it, he had shoved the tip in. I didn't complain though, but he was still in play time, he lifted his tool out, creating a suction cup with a small *pop* sound. Right afterwards he did it again. *pop*, he did this for a few minutes before he forced more than just the head in, he forced a good 3 - 4 inches in and told me it was time.

I adjusted my head a little and began doing what I liked. I slowly suck on the part he gave me as he held the base. I was about to move my hands  up and give him the full experience, but he used his free hand to push them away, then widened his legs more so I couldn't lift my arms. I began wondering how I was ever going to finish him if he never let me work. But I still worked my head on that portion of his cock. He began letting out small grunts and moans. He used the base to pull out the tip and create one last *pop* sound.

He stood up in his original place again, let go of his cock, and told me to get up. I sat back up on my knees, his tool hanging in front of my face, with the tip touching my upper lip. "Begin" he said. And so I did, I used my tongue to lift his cock into my mouth and began taking the head of it for a pleasure ride. I was afraid to use my hands, thinking he might force them away. But I slowly lifted them, placing one on the base and one in the middle and worked it while sucking on the tip.

I looked up at him, and he looked down at me for a quick second before looking up and giving a deep grunt of pleasure. I began quickening my pace, slowly getting faster, wondering if I would ever finish him, but his genitals were still hanging a bit and covered in my slobber. I began taking more his tool in and using less of my hands, I probably got a good 6 inches in before I could feel his cock forcing my gag reflex, as much as I tried to numb it, I couldn't push his whole cock in my mouth with out a slight gag. So I stuck to these 6 inches.

I was still looking up at him, while he was staring up in ecstasy, I could tell he was enjoying it, and so was I to be honest. He looked down at me and realized how much I still had to go, he pulled my hands away, placed them on his thighs, then used his hands to grab the back of my head and begin forcing more and more down my throat.

This wasn't helping my gag reflex, nor my breathing. He would just push my head down on his tool and hold it there for a few seconds, ease me back up, wait a few seconds while I caught my breathe, and repeat. It seemed like forever since he started doing this, and I still couldn't take it all without him forcing me, in which I still choked on it.

He began to realize how much of a gentle sissy I was, and pulled my head off him. "Have you ever been throat fucked before?" he asked. I just looked at him, afraid of not being able to meet his demands, 'No mess'. "No, I haven't." I said to him, looking at his dick swinging in front of me now. "You outta try it, lay back down."

Again, with absolutely no hesitation, I did as I was told. He walked around so he was standing above my head, dropped down. He aligned his huge tool with my mouth and lifted his knees and began supporting himself with his hands. "Are you ready?" I could only nod while thinking about what was about to happen.

He looked down, and began forcing his cock down into my mouth, he began really rough, there was no easy. I began gagging and choking immediately, but he didn't let up. I could feel his cock slam into the back of my throat and then begin its descent down before he pulled up and did it again. My eyes began to water from choking. He didn't let up, but from my perspective, seeing his tool slide in and out of my mouth roughly while his balls slapped my nose repeatedly, I was enjoying it, even if I was choking. He pulled up after about a good 2 minutes of a rough throat fucking and lifted his cock out of my mouth. I began coughing, spitting running out of my mouth and off his cock.

"You all good?" he asked, I didn't care about the choking honestly, I was in heaven right now. So I simply nodded again as I stopped coughing, and he slipped his tool in my mouth and began again. Breaching my throat and then back up. Balls slapping against my nose, it was an experience.

No matter how long he did this, I still couldn't manage to tame my gag reflex. It wouldn't happen. After a good 5-10 minutes of this, I think he decided to carry on. I had slowly realized, especially with his genitals bumping my face repeatedly, that his balls were now tighter than ever, and he would probably be ready soon to finish.

He got up, looked at me with slobber everywhere, got down real quick and used his member to swipe it all into my mouth, I could taste precum, and lots of it. The slamming into the back of my throat made it impossible not too. But he got up again, walked over to the couch, sat down sinking lowly onto the couch and told me to suck him again.

I, myself, got up, got down in front of him, with his legs wide open and took the tip of his penis in my mouth. I used one hand to stroke the base while working the rest with my mouth. I looked directly into his eyes, and he looked at me, working away on his precious cock. He slowly got a small smile to his face as I continued, and I began to feel the pulse in his cock, just faintly at first. He let out a few grunts, and the pulse grew. I was about to pull back but then thought about his rule again. "No mess, have to swallow." I thought, maybe I should pull back and take it all over my face, but before I could finish, his legs wrapped around my head and I felt the pulse reach its maximum.

I felt the first load of his salty cum shoot into my mouth, it hit the back of my throat and I almost choked, I attempted to swallow, but he was pushing my head down on his cock too far, I had no room. The second load shot, splattering in various places of my mouth, all I could taste was his semen, and god I loved it. Boom, third shot, I felt it on my tongue, I stopped stroking him, and let the rest just work its way up. He released his grip around my head and allowed me to pull back. I nearly coughed but tried my hardest to restrain myself. I could feel his salty load on the back of my throat, took one big breathe, and swallowed it whole. It slid down my throat, slower than molasses, it took a few attempts to get it all down.

I had stopped paying attention to him, and was focused on putting this all down. As soon as I was done, I looked up and saw him stroking a little left out for me to lick off his dick. I leaned forward, took the head of his dick in my mouth, slowly pulled back and made a *pop* as I sucked the cum off. I could taste it, and I left it in my mouth for a second, balancing it in the center of my tongue, and took one last swallow.

He was finished, after all that teasing, and playing. I still had a hard rage on, and couldn't think of how I could solve it, but he went in his kitchen, grabbed a small shot glass, and brought it back and held it out to me. He simply said "No messes" and sat back down. I looked at the shot glass, then at his still hard cock, then down at my own. I got up and slowly unzipped my pants, it took only a few strokes before I came in the shot glass.

I held it out to him, but he said "I'm not the sissy." I guess he was right, I examined the glass for a second, rolled my head back and slowly poured the load in my mouth. I handed him the shot glass and he set it next to him on a table.

"You have a few things you need to work on, and explore new things." he told me. I looked at him, and said "I guess, if you have any in mind, what should I improve?"

He examined the shot glass, and said "Practice improving your gag reflex, and maybe go past oral and a handjob. I can tell you liked a lot of the stuff we did."

"I'll try, if that's all I guess I can get going." I said, and parted for the door. I went home a bit of a mess, thank god for a car ride, I got home and cleaned myself up, took a few drinks of water to wash everything down, wiped my eyes a bit, and laid down thinking.

I really enjoyed the experience, and I was happy that it wasn't a few days later that I got an email from him asking if I wanted to go again. But of course, another story.