This is probably a huge understatement, but the year two thousand and ten was a real game changer for me. How? Well, you see, I've never seen that much written on how someone becomes a sissy. Maybe not so much on how it happens, but the why of it? And in so doing, discovering you like it? What I mean is, I didn't decide to do it for my own sake. Not at first. I did it for who I was with, and the results surprised me as much as him. I'll try and tell you what happened as best I can, but all I have to go on is how it went for me and how it was series of discoveries. For us both.
At that time, though, I didn't even know what it was called. I know now that in sexual circles a sissy is a male with a preference for feminization yet doesn't persist with being feminine 24 - 7. It's pretty much that simple. What's more, there are those who can be passably sexy without the use of hormones, and that was me. What gets left out is the psychology behind it, and porn would have you believe it's simply because they like to suck dick and get fucked. That the sissy sets out with this goal in mind alone. They're gay first, and sexy second. I don't know about anyone else, but it was reversed in me. Still, I felt I was more heterosexual than anything, and yet curious enough to try things, and it was then that everything else fell into place.
I mean, of course you have the impulse to try things beforehand with a man and finding you like it. There's always a starting point. It's not like someone forced me to do what I did at gunpoint. You have to want to try little things first. Those private little thoughts we all have hidden away somewhere in our minds. With me, I found out I liked pleasuring someone first, and the sissy part came second.
Wait a second, that doesn't add up. If you were able to look passably sexy, how could your never realize that about yourself? Spoiler alert. I knew. Of course I knew. You just don't have a light bulb pop up above your head one day and go Hey, you know what? I think I'm sexy!
I knew my looks. Who wouldn't know their own body? I knew what people thought of it. Me being a guy and all, I was never spared any consideration in regards to comments, so of course it had been pointed out to me before that my body was feminine. To be honest, though, until the day I owned it, none of my history there had been very pleasant. For me, there was no easy embracing of the fact I had the canvas. My past made it harder, in fact, considering everything that was to come, and there was more reluctance than exuberance when the day came.
But I tried it, symbolically 'stepping into' my body and the rest was history.
So this little memoir is how it went for me, and this is me trying to write it all down for you. How I found out I liked being a pleasure giver first, and a sissy second, but in the end, it didn't even matter. I loved it all.
BECOMING DANA
(Base on true events)
To start simply, in my late twenties I had a coworker turned roommate that happened to share my love of movies. He was the same age as me. We were actually fairly good pals that easily became friends, and being roommates seemed more than reasonable when the circumstances came up. Reading that back to myself, it sounds just like the cheesy set up for a sex story, doesn't it? One day my roommate was showering with the door open and I saw his huge nine inch cock swinging between his legs and then blah blah blah. That stuff is crap. Such writing is a poorly scripted, lukewarm attempt to make something believable and represents nothing of the real word. It doesn't happen like what you read. No kidding, right? The fact is, because now is a good time to say so, the course of events written here took over two years to happen, and then even more time after that before it became what it was. But don't worry, I'll summarize. It didn't happen over night, but it did happen, though on the day he moved in, I never had the slightest notion it would.
With my new friend, the one odd thing I felt from the start was how there was always this little off-center feeling somewhere in the background between us. Something where we didn't really act like classical friends. Not in the sense we carried on with a bunch of friendly insults, bullshit stories and drunken carousing. No, I guess we were rather quiet on the whole. I just attributed this to the manner of how we became friends and the interests we shared. We didn't party much, and had somewhat low-key lifestyles. By lifestyles I mean activity. For all intents and purposes, we were as basically hetero as they came in the beginning.
Honest.
It was only later I was to find out what this little off-center feeling was and how it was a catalyst for something greater.
Anyway, eventually, when it comes to being movie nuts, porn is going to enter into the equation at some point. Do all guy friends discuss porn? I'm not sure on that one, either, but it was as simple as finding his other binder of DVD's that eventually led to plenty of laughter over the horrible acting and cheesy stories. We even watched one. And, as you may have guessed, that led to some infrequent viewing sessions where not just the bad acting itself was gone over, but everything else as well.
This is where for the first time we started sharing private matters. We hit on the types of porn we liked and ran with it. Tits and turn-ons, styles and smiles, women and wow factors...babes, boobs and baubles. All of it. We started refining our tastes that way, and we slowly started adding to his collection.
What would you have me say by way of explaining what was to come? Like I said, from that moment on, and up to the moment he had his dick showing, would be a stretch of time that would take way more room here than anyone would care to read. Again, it didn't happen over night, but it did happen. We had been roommates for over a year by then. Yep, that's right, we can skip an entire year before we even talked about porn, but now though, we were watching it together.
The truth is, he had only inadvertently exposed himself. He didn't do it on purpose. He was wearing boxers and was sacked out on his back on the sofa (this great big L shaped monster we had struggled into the apartment piece by piece which neatly separated living room from kitchen) and the leg of his shorts just road up unnoticed. Understandable, really, since his dick was pretty much working it's way out on it's own, so it just lay there on his thigh semi-hard. He wasn't massive, but he was noticeable.
And I noticed.
All purely by accident. He didn't say anything, and when he realized it himself, he just tugged the leg of his boxers back down and that was that. Hate to burst your bubble, folks, but that was it. That was all for that night. But it would happen again. What, you thought we just sat there and laughed at porn? No, by that time we knew we liked the same kind and we were buying them for that reason. To watch. In fact, like I said, refining our tastes led us to focusing on things that turned us on best, so this thing was almost bound to happen. And I know what you're thinking. It sure would be spicy to think he was showing himself on purpose, but I can honestly say he wasn't. If I said we were kinda low key over all, you could add in a dash of shyness in there for him, and that's probably why we got along so well. The truth is, he was just in the moment. Don't believe me? Try watching porn without touching yourself and see how well you do.
So, the time came that he absentmindedly caressed his cock a little where it lay just at the leg of his boxers. More through the fabric of his shorts, than actually right against it. Probably from his own sense of trepidation, he stopped just as quickly, though, and tucked it away. This probably would have gone on forever because he wasn't bold enough to do more.
That fell to me.
I did feel that perhaps he just trusted the situation enough to be comfortable with it, so there came a night on the other end of the big L that...I did the same thing. For those of you who don't wear boxers, just know that the people who do, understand how loose they are. Your junk will obey gravity, while your boxers will pretty much go where they please. Boxers are like a basketball net, if you take my meaning. The balls just fall right through. Worse when it comes to moving around a lot on a sofa. Depends on the size and brand really, but their nothing compared to an actual pair of panties! (haha)
I'm getting ahead of myself.
Anyway, when we both were aware of what was shaping up by the low light of the TV, the thing I remember most is that when it continued...neither of us...said...a...word. We both knew what the other was doing, and so, without any real fanfare, we masturbated in the same room. It wasn't outrageous and it wasn't rife with tension. It just happened. The movie made noises and we made noises, but we never said a word and stayed where we were on opposite ends of the couch. There was something nicely natural about all of it. Private, if you'll believe me.
The next morning, though, we didn't mention it, and that was a shift, because we usually talked things out the next day, as was our way when discussing porn or anything else. I guess we both wanted to pretend it didn't happen? But then we did it again a few nights later. After that, we did talk about it, and I guess we just eased into it, in the times that followed.
For another long length of time, we were content to just let the dicks show, or let them lie. Sometimes we did, sometimes we didn't. Sometimes we took care of business, sometimes not. Of course we started making comments to each other, with no real coordinated effort, yet all the same feeling compelled to point something out up on the TV screen.
Oh, wow, look at that. She's hot and the like. Then we could stroke to it. It was almost like we were explaining it, and so giving ourselves license to masturbate more openly in front of each other. It was an easy thing, still without any real sexual tension, that went on quite content to just be what it was. You could read this and say Yeah, right! and you'd be right.
But those things didn't happen immediately either.
Apparently, we both seemed to feel the same way about this risky little business we had going on. Neither of us wanted to ruin it by being too obvious, but being comfortable with each other and having a quiet chemistry goes a long way. Masturbation became the point of what were doing. We still watched porn, but it was no secret what was on the menu if we did. Pardon the pun, but it became a firm go-to that we made time for, jerking off together, and so we started watching more porn. You don't link up sexual interests in this manner over the course of a year and not have things happen, but there's quite a distance to be covered when you always camp out on opposite sides of the couch.
You just don't stand up one night and go Hey, wanna sit together?
To summarize again, one night much further along on the calender, we charcoaled a frozen pizza both of us had forgot about in this little roaster oven we had. When we came back from the kitchen after everything that entails (beepbeepbeep! cough cough!) and we ended up sitting back down closer together so we could view the TV straight on. And that was it. Was it a subconscious thing? Did we want to sit closer together? I don't know. The ice wasn't broken so much as there was less shame and embarrassment in the doing, if that makes sense. I supposed we figured, why not? Moving back apart is what would have made things awkward, so we did our viewing side by side that night. And our masturbating. After that? Well, things went down like ducks in a row.
Sitting together all the time. Doing it together. Doing it in front of each other. Showing each other. Checking each other out. Comparing. Talking about it. Watching each other. Encouraging each other. Calling out things you knew the other guy liked. Egging him on as he did it. Stroking together. Watching each other cum. Cumming together. Teasing. Touching. Feeling. Rubbing. Stroking each other. And finally (drumroll) stroking each other off. Yep. You can go right down the list and graduate at the end.
I said I would summarize.
However, those things took a long, long time to occur. One by one. And neither one of us were under any delusions about what we were doing. We knew what we were doing. We liked it. We made time for it and we took our time with it.
As it was, I suppose we didn't rate too high on the social scale outside the home. He was a good enough looking guy, but like I said, quiet and a little nondescript, and he kept to himself. I could be quiet, yet tended to be a bit more bold. Bold doesn't have to mean loud, and it's not the same as daring. Just...bold. Dating girls wasn't big on my pay scale at the time. A lot of my jobs just came to an end. I won't bore you about that, but the situation was at best considered unreliable, so I didn't go out much. I wasn't very masculine anyway, and was always a little off putting to girls. Anyway, there didn't seem to be any hurry about having a girlfriend, much less getting married, so that was that. We kept right on doing what we did, and were rather content with it, too.
Strangely, it was the porn that finally broke the pattern. Porn was becoming a little predictable and stale, and when you've graduated to more direct stimulation with your now pleasure pal, in a strange reversal of fortunes, full on porn can quickly loose it's flavor. Porn is the chewing gum of sex, and it stopped working for the two of us and the somewhat moderate pacing of how we slowly got around to stimulating each other. Regular movies and beautiful actresses became a thing. Able to be viewed longer and savored more, discussing those ultimate women of fantasy and why we liked them was just the ticket. We could stay hard for hours. Plus, we got to watch a real movie.
By now, we were more than open about things. It was quite common, and little thought of, to be erect and exposed nearly the entire time we decided to have a session at home. One of us would get up and leave the room, come back, carry on and the like, all while erect, or at least, exposed in front of each other. We both knew it added to the atmosphere, even though we were always a bit slow to reach the point we touched each other. There was still this little barrier of uncertainty about it, I guess, but showing your cock was no big deal.
I have to say, to make things clear, we didn't go around bottomless. We weren't flamboyant about anything, but boxers usually have a handy little fly in the front. Handy for how they could show your dick, or act like a curtain, depending how and when your cock wanted to take center stage. We used this to our advantage, see? We knew what we were doing, but we were definitely in our own little world letting that happen.
There was a mild little intimacy here, which might have been the reason for our uncertainty, I don't know, but we became free and easy with each other the longer we did it. Real easy. I knew his cock by sight as well as I knew my own. We both were circumcised and he was bigger than me by a solid inch, and he looked larger because I had smaller hands.
(That so made me laugh just now. Reading this back to myself, it's like I'm trying to defend the difference in our dicks. Lies, I tell you! Lies! It was all camera angles!)
The truth is I didn't care. We both did just fine in our size. Sometimes I teased him about it, though, being bigger than me, to try and get him to loosen up a little. By then, we were doing what we did on a regular basis, though I had a sense I was a bit more comfortable with it than he was.
Yes, you know where this is going, and I must confess, it was me who took the leap.
There was, as I remember, less time between stroking each other off and the first time I put my mouth on him, than at any other point we had reached. The ice pretty much was broken at that point and things came easier. No pun intended. By then, we had been roommates for well over two years.
The only thing that distracts me, is that I can't remember the movie we were watching when it happened. When I did it. I can't remember who the actress was. I really can't. I don't even remember the date or time of night. I just know that I enjoyed this thing we had going, and it was probably a typical evening for us. In fact, I was starting to enjoy the thrill of him. And how we would actually plan out these sessions and be excited about them together, getting ready and basically freeing ourselves up as part of the show, but that night I was so nervous. I remember that much at least.
So why did I do it?
Without realizing it, and behaving like we were to back it up, something was stirring inside me. An enjoyment I felt at being this way around him and with him. About a particular cock that I knew I would get to see. His. Imagine my surprise on the day I decided I had different ideas about that. At how I felt when I realized what I had made up my mind to try? When did that happen? When does that happen? I had never thought much on it before, but perhaps hitting so close to home like this made the situation more agreeable? Like I said, this exchange of thrills between us had drawn out for such a length of time, I guess I felt comfortable with it? Trusted him? Trusted the situation?
I felt the limits of such trust, and this platonic little intimacy we had going on, could handle it and maybe even make it something exciting. But more than that, I guess you could say I wanted to surprise him. I liked that idea a lot.
I do remember we were watching a favorite actress of his, and I was so nervous about what I intended to try, I couldn't focus on any thing else.
I really don't remember the movie, but I remember wanting to do this thing while we watched it. For him. I wanted to make him react. I wanted to see him in pleasure, like the times I made him climax with my hand. You could say this was the moment I took my first step as a sissy, but at the time it was more pleasure giver. And I was always a bit more fluid when it came to sexuality, so there was no great barrier of ego and fear to stop me from thinking about sucking a dick.
You mean to tell me, two roommates up and decide to masturbate together and then one night you decide to suck his dick!? I thought you guys said you were hetero!? LOL!
My answer to that, is this. What took place between us is only improbable for you when you apply it to your own belief system. You weren't there. You weren't him, and you weren't me. Stating we were basically hetero is a starting point, not an iron clad contract made out solely to you declaring I won't color outside the lines. Things happen. Sure there were reservations, worries, and doubts, but I wouldn't be writing this little memoir down if I hadn't been capable of accepting where things went. When they did, I wanted them to. So did he. And I can't deny how much I absolutely overdosed on where it took us.
But I'll get to that.
So anyway there I was. I do remember how my mouth was as dry as a bone when the movie began. We were again sitting side by side just like before, and I started with my hand a little sooner than usual. In fact, I didn't often touch him so directly like this. A detail to note is, if it wasn't clear, we usually only did each other when we were extremely worked up and getting close to cumming. Now though, almost right away, I sat up a bit and reached into his lap, getting his soft dick out of the fly of his boxers and working him up.
This was rather unexpected...for us both. Well, I was nervous. Was I rushing the issue? He was more or less used to me touching him, for we had some casual petting going on in between scenes and such before. He reacted more than favorably, though, jumping a bit and looking down, then getting this little smile on his face and looking over at me, as I went to work with my fingers.r"
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Pub: 22 Jul 2021 11:45 UTC
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