How i Learnt The Pleasure of Anal

How I learned the pleasures of anal
This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end…

I was born and grew up in what many would probably call an average small suburb. In my early years, while starting puberty I began to explore sex the way I assume many boys across the world did to start. A few times during this period I became curious about girls and what made them so different from boys. One of the obvious differences were in clothes. Bras, thongs, dresses, skirts, and bikini’s vs suits, ties, boxers etc. Girls always seem to have much more variation in styles and I was always curious why. During this exploration, I decided to try on girls clothes a few times and see what some of them were all about. When I did it, it wasn’t done as anything “sexual” but I do recall that it did make me feel different in a good way. This is where my appreciation for femininity started, and what ultimately, many years later, lead to my transition.

I was constantly exploring and once I hit puberty, growing to be a hormonal teenager, none of those curiosities died out, rather, they only increased in voracity. Sometime during that time I discovered the pleasures of masturbating and sometime during that time (while also having access to the limited internet at the time) I was able to explore pleasure outside of masturbation and I found anal stimulation to be very exciting. While exploring myself anally I never did think to call into question how that could have possibly related my gender identity nor did I think of what it meant about my sexuality in any way. I was biologically a boy, enjoyed masturbating, very thoroughly enjoyed anal stimulation, and enjoyed dressing like a girl. It wasn’t till the mid-teen years of course that I bothered to start to call into question if my appreciation for those things related in some way to my sexual preferences or sexual identity. I certainly didn’t reach any conclusions at the time but didn’t let the internal exploration of it worry me too much either. I was who I was.

I knew I was attracted to girls and never really was attracted to boys in the same way I was to girls. I did, however, have curiosity about how they could potentially (or not) fit into a situation that I would find sexually pleasing considering my fondness for anal. This curiosity persisted but it wasn’t till I was 17 that it ultimately lead me to trying to find someone (using the internet) that I could explore my anal sexuality with. I knew I was very intrigued by trans-girls, but with the somewhat-small town I lived in, I knew there wasn’t going to be any chance of me finding one to get to know and learn from, so I figured a guy to experiment with sexual was just as good, at least for those earliest experiences. I started chatting in adult forums and found a few adult oriented sex sites and ultimately stumbled upon a gay site with guys who were local to try and seek a guy who would explore the phallic sexual experiences with me of which I was so curious.

I found a guy who lived about 10 minutes from me and we chatted for days and days and after a few weeks, I finally decided that I wanted to try it out genuinely, my curiosity and sexual drive outweighed the potential stigma or concern I had about what it actually meant for me to do it…essentially I was too horny to resist. I had been playing with anal insertion a good bit, trying to find phallic shaped “anythings” I could get my hands on to pleasure myself… a few vegetables and bananas suffered a horrific fate as some of those random objects. I arranged to meet a guy, in his late 30s, at his house. His wife was away on vacation while he worked so he invited me over. I borrowed a few pieces of clothes from my mom and s****r which I wore under some of my regular clothes when I went over to his place.

When I got there I freaked out and was of course nervous about what it meant. I ended up just getting too panicked and went back home and apologized the next day for flaking out. That happened once more that same week and before I finally pulled up to his place 5 days after that original set meet, I decided to actually go through with it. When I arrived at his door, I knocked and within a minute he opened the door (felt like a long 5 minutes, but was probably closer to 30 seconds). He was an average looking guy who was about my height, he invited me in. I was so nervous I am not sure I said anything intelligible but just followed him into the house. He asked about 3 times if I was sure I wanted to do this and every time I nodded yes, so we slowly made our way to his bedroom.

It was a very, very nice house and everything reflected that. When we got to his bedroom he had some slow music playing in the back ground and the room was dimly lit. I noticed he had a few things laid out on the bed and so he noticed me checking them out. He gestured towards them and said something to the effect of, “I have a few things here… if anything interests you let me know…”. First thing I recall noticing was a set of lingerie, a silky/lace nightie with matching bra and thong. He said something like “I know you said you like wearing girls clothes so you can wear these if you want…I bought them for my wife, but never gave them to her…”

I had actually already had on the stuff I borrowed from my house so I said, thanks, and that I really liked them but I had already been wearing some. I then began undressing the boy clothes I wore to show him what I had on underneath. I was not sexually attracted to him, but was so sexually excited by the idea of what could happen, I knew I wasn’t going to leave until I tried it. As I undressed and stood there in my thong (it was pink and a little too small for me as it was my s****r’s) and bra (which was black and a few cup/bust sizes too big for me), my heart pounded and there was an obvious excitement growing down below. I had just started shaving my face at the time, although I didn’t really need to do it much, but I had also shaved off all of the hair from my body with the exception of my arms and legs (again, not all that hairy, but not as feminine as I would have preferred…) because I was uneasy about the social stigma surrounding boys who have shaved bodies and didn’t really want to have to deal with that when someone noticed.

So standing there he walked up to me and started touching me and telling me how cute and sexy I looked. This delighted me and pushed my desire for this to happen even more. He then took off his shirt and pulled down his shorts. He proceeded to place his hands on my shoulders and pushed me down to my knees. I was inches away from the object of my curiosity and desire and I can recall feeling (what I could describe at the time) of being a little dizzy/lightheaded. He grabbed it and held it with his hand and told me to touch it. I reached up my hand and put it around it, like I had my own so many times. He then told me to suck it. It wasn’t large, 6” or so, but it was a decent shape and size. It fit what I wanted at the time.

I had known from playing with myself, that my capacity for anything “large” wasn’t really there so I wanted to make sure it would be one that I could fit without feeling the pain that I would when I tried to use something too big. My body was so tense and rigid that I barely moved when grabbed my head and pulled me closer to it. Finally I opened my mouth and slowly started taking a little by little bit of it in my mouth. I had of course watched plenty of porn by that time and knew what I was “supposed” to do, but being so nervous and anxious about it, I could barely move. Finally it was all in my mouth and he slowly moved his hips back.

I had finally come down from being dizzy/lightheaded as I was before and started doing what I knew I was supposed to be doing. I had so much and yet so little running through my head at that time that I wasn’t so much focusing on what I was doing, but more on what it meant to be doing what I was. I did find it sexually gratifying and enjoyed pleasing him orally, but I couldn’t help my touch myself in the one place I really wanted to be touched…my ass. After a few minutes of having him in my mouth; feeling and tasting it moved across my tongue. I pulled my head away and said something to the effect of, “Can you please fuck me now”… this obviously excited him as he grabbed me by my shoulders lifted me up and then pushed me towards his bed. He bent me over and immediately started rubbing it between my ass, placing it gently but just rubbing over the entrance to me.

I know my body was so tense that there was no way he was going to get it inside of me, but that didn’t mean I didn’t want it. He said, “Don’t worry… I have some lube ready which should help out” and I saw him grab a bottle off the bed from the area where the lingerie was still laid out. I remember feeling the cool touch of the liquid as he rubbed his finger on my entrance. I was so nervous and my body was locked so tight just couldn’t move past the torrent of thoughts swarming through my head. I wanted it so bad, but yet my body was betraying me by not allowing anything inside of me. I was so flushed and remember my face feeling hot as I was there bent over the bed with this guy standing behind me trying to get inside of me. I looked over at the mirror and saw myself at that moment.

While I had short hair, I did have a nice and slender body, but it was also athletic and not particularly feminine. When I say myself with the thong on and the bra on, I actually saw what could be a cute girl. Excited and distracted by that thought my body released and the finger with which he was rubbing my ass, finally slipped just a little inside. I was momentarily surprised and tensed up again, but he didn’t waste any time placing his tip at my entrance and slowly starting to push in. Still quite nervous, but now a little more relaxed he slowly started to enter me. I felt the pressure I had before whenever I had played with myself, but this was different because it wasn’t me directly causing it, my hands were on the bed, holding up my body as I was bent over. He kept pressing and after about a minute of just pressing on the outside, he finally pushed one last and final time. Excruciating pains shot through my body and I can recall screaming out from that short surge of distress. He was now inside of me and while, only a moment ago, I knew 100% that I wanted it inside of me, after those sharp pains I couldn’t help but pull away. The throbbing pain persisted and he apologized for hurting me but said I was just too tight to take him in. I was still aroused, but knew that I couldn’t do that again…not tonight at least… so he ended up taking care of himself while he touched and played with my body.

We hadn’t contacted after that for a few days and it wasn’t till about week later, that I contacted him again. All of the negatives from the experience had faded from the intense desire to be pleased anally. We set something up again a few days later but this time, I decided to go over to his place not wearing my own stuff and wear what he had laid out for me that last time. I remember loving it because it was so much closer to my size and looked so much nicer than anything I was getting my hands on at the time. So once again, after we went to his bedroom, I got dressed while stepped out for a moment, I was there again standing in the middle of his bedroom wearing the black nightie with black and red lace trim bra and thong. He clearly liked what he saw when he came in. I felt and looked so incredibly sexy with what I was wearing I was extremely turned on just from looking at myself.

This time when he approached me, he actually leaned in to kiss me. I was very taken aback by this because I wasn’t at all attracted to him in that way and the idea of kissing him didn’t appeal to me at all, I actually pulled away very quickly and panicked for a second. He seemed to get the message without saying anything and proceeded to slowly touch my body again. Stomach, ass, chest, neck…focusing on the areas where I always seemed to be the most turned on. He dropped his boxers off and walked toward me naked. This time however he didn’t push my shoulders down, I just knelt down to him myself excited by the prospect of actually being fucked. Once he was good, hard, and warmed up, he climbed on the bed and told me to straddle him and lower myself down on him slowly. Slow was indeed always what I did when I would play with myself in the past. I had been practicing since that last time we tried and was confident this time that it would work. So I climbed on top of him and place the head of it to my ass and slowly pushed back. It took what seemed like minutes before I relaxed and let him in a little. After a few more min, I was finally able to get him all of the way inside of me and we just sat there for a bit. He smiled and told me how incredibly sexy I was and that he felt so incredibly good. This seemed to help relax me a lot and I could feel myself relaxing around him while he was inside of me. It did still hurt a little, but it wasn’t too much this time and the little bit it did hurt actually felt good. Pain and pleasure have always seemed like a very fine like with anal, and a good mix of it can be incredible invigorating.

Finally I slowly started rocking back and forth. I felt him inside me. I felt as he was smoothly gliding in and out of me. It felt incredible but still hurt quite a bit. I hadn’t even been touching myself at all because I found when playing with myself that I could cum too quickly if I played with myself too fast and I wanted it to last. It felt incredible as my little dick was slowly rubbing between our bodies while he moved in and out of me. It wasn’t very long though till I felt myself being overcome with pain as it felt a little sore, but was still very pleasurable. He was moaning and talking dirty to me which helped turn me on even more. Within only a few minutes, I started to cum. It was incredible, I was never previously able to cum from just anal and not touching myself when I played, but this time I did. In fact I wasn’t even hard really, the orgasm actually felt like it erupted from an entirely different place and was indescribably more intense. My entire body shuttered and pulsated. This must have turned him on too because he started moaning louder and within seconds started screaming that he was cumming. I was a young and so doing stupid things k**s do, I didn’t make him wear a condom (thankfully later I found there were no consequences to my actions). I recall actually felt him spurting inside me as came. It was incredible, nothing like what I had ever felt before and I knew from that moment that I do very very much enjoy anal sex, but there gender wasn’t really a concern.

So I sat there with him still inside me for a few seconds as he caught his breath. I slowly pulled him out of me and, holy crap, it hurt a lot. I was sore and my ass felt like it was burning hot. I felt a little unsure and a bit of regret at the time, so I was trying to make a swift exit. I got what I wanted and so I was ready to leave. I started to take off the nightie, my thong was pulled off earlier before I climbed on him, and was going to take off the bra, when he told me that I didn’t have to take it off and could wear it home if I wanted so I could have it on already when we played the next time. I recall thinking, “next time? What next time? I got what I wanted and didn’t think I’d see him again.” I smiled anyway and just said sure (halfheartedly though).

As I bent over to put the thong on, I felt something warm slowly drip out of me, and when I looked down it was white, I realized it was his cum from inside me. It ran down my leg and I just wiped it with my hand and proceeded to put my boy clothes over the lingerie I was wearing. It made me feel kind of dirty at the time and so I felt a bit of regret as my face turned red thinking about what had just happened. He noticed my panic and so just remained on the bed and told me to show myself out.

I made it home a few min later and went directly to my bedroom. I immediately pulled off the girl clothes and hid them under my mattress still feeling a little ashamed. Not more than 30 minutes later though, I started to get sexual aroused again and I know it was because what I had just done was still swarming in my head. The thinking about moved from regret of what it meant and why I did it till rationalizing that it didn’t really matter, only what I thought mattered and so I eventually stopped feeling bad and it started making me recall how intensely erotic it was and how much I enjoyed it.

A little bit of his cum was still in me and I could feel it slowly dripping out, and as that last little drop slid out, I decided I needed to take care of myself again. I was so turned on now thinking about how much it excited me that I jumped up and proceeded to lock my door. I decided to put the bra and thong back on as I pleased myself. I tried to do what I could to recreate the experience I had just had but when I finished touching and pleasuring myself it was just so far from the same experience that it was a bit of a let-down overall. I realized at that moment that I need to not regret anything and the only way I was going to enjoy it again, was to accept that if I wanted to feel that pleasure again I would need someone else to help me reach it. I met up with him again a few times every few weeks over a few years before I just stopped going home as when I got to college.

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