In chapter 1, I described how a trip to donate boxes of clothes a neighbor had left in our care led to me keeping several bra and panty sets, which ultimately introduced me to crossdresing and oral play with a dildo. This chapter uncovers much more.
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I bit my lower lip as I settled back further, finally feeling Max’s warm balls snuggle against my ass cheeks. I let out a long breath, and remained perfectly still, adjusting to his size, My eyes closed, and a grin spread across my face.
The fullness remained, just not as bad as before, I held my straddling position and softly caressed my thighs, slipping a finger below the metal clasps of the black lacy garter belt that held the stockings in place on my smooth, pale white thighs.
I brushed my long blonde hair away from my face and glanced over my shoulder to the mirror propped by the bureau. The reflection that greeted me was a different person. The woman that gazed back took a slow deep breath and leaned forward lifting her ass and for the first time, witnessing the thick cock emerging inch, by glistening inch from her badly stretched pussy.
Well, mostly.
Max, ‘my Lover’ was actually a dildo I had purchased a couple of months before. Initially, I wanted it for oral play, but the truth is, I just couldn’t ever enjoy trying to suck it as I had hoped, my jaw would begin to ache and this part of my ‘girl time’ just didn’t turn out as I had dreamt. I decided that I may as well see if I could get the eight-inch plastic cock into my ‘pussy’, but that hardly seemed possible. If I couldn’t suck the cock, there was no way it was going to fit inside me.
Wrong.
My first attempts were slow, I made sure to use copious amounts of lube, I’d typically lay on my back, with a towel draped over a pillow beneath me. I’d also slip into one of my bras, and simply not bother with any of my panties. The first night of trying to get Max inside me, turned out, accidentally, to be the only reason I continued trying. I remember placing the head of the dildo at the opening of my ass, or my ‘pussy’ as I referred to it while dressed in women’s lingerie, and then slowly began pushing it forward, attempting to relax my ass as the pressure increased.
This was working, and I actually could feel like I was progressing, I could begin to feel my pussy opening, and then the feeling as more and more of the head of the cock began first pressing into, and then out of me. In truth, I’m sure it was just a very small amount, but I was progressing, and I had no expectation this would ever actually end up balls-deep inside of me. I just wanted to see if I could get some of it into me.
As I would alternate between pushing out then relaxing, and the cock was slowly attempting to gain entry, I couldn’t help notice my own cock, as stiff as it had ever been with a large drop of pre-cum beginning to drip towards my stomach. This is where things shifted a bit. You see, I had initially wanted the dildo, to cum on, and then suck my cum off of it, but as I said, that was really not turning out as erotic as I had hoped. What about pushing my own cum up into my ‘pussy’ with this dildo?
So this gave me the motivation to truly make an effort, although the chances seemed unlikely of my ass ever being able to accommodate the thick cock. So for a couple of weeks, each night, I’d lock the door to my room, I wouldn’t bother with any makeup, just slip into one of my bras, and keep trying to see if I could make this work.
The one time I tried to go too far nearly ended it for me, and that searing pain scared me badly enough to re-think things. I decided to take a break. A few days later, I tried again but was nervous about the pain, and so I stopped early that night and did some serious thinking the next day.
I would ‘reward’ myself with any milestone progress. If I could get the head of the cock into my pussy, I’d buy a garter belt. I have always felt that a black lacey garter belt and black seamed stocking are the sexiest lingerie a woman could wear. I can’t explain it, but that does it for me. If I could get just the head inside, I’d order a set.
I felt like, if I could get that far, I’d worry about more later, and so for the next week, every night I’d keep practicing, and each night I was able to feed just a little more of that big cock into my hungry pussy. Finally, it felt like I couldn’t go any further, if you’ve ever been there, you know exactly what I’m talking about, ‘this is the limit!’ and there’s no further you can stretch, but I was so close. I could feel the ridge of the dildos head, I knew I was almost there, if I could manage to get the head inside, the worst would be over.
Again, completely by accident, I did the right thing I didn’t press further. I stayed at that limit, I kept the head tightly pressed in as far as my sphincter would allow and just held still. I kept the pressure steady, not trying to go in further, but not willing to slip out any. I stayed like that for a while, and then pressed just a bit more to see if I could make any more progress before calling it quits.
There is that point, that second or two that you feel yourself open that fraction more, which is just enough to let the head slip inside you, and then it feels like you close back up around it. It really is a defining moment. The most difficult part was now past, although I didn’t know it at the time. I just lay there, amazed, I had actually done it. To be fair, I felt like I was going to be ripped in half and so I didn’t dare move, even a bit, but at that moment, lying there with that thick cock head having just slipped past my incredibly stretched virginal sphincter. I felt like something very very naughty had woke within me.
The next day, my ass was sore, I worried a bit but I also realized that I was not stopping now, my ass would just get used to it, or the rest of me would just get used to it, I searched online and found a garter belt and several sets of stockings that could be delivered that week.
The same evening I began shaving my armpits, my legs, and all but a little patch of shortly trimmed hair directly above my own cock. I’ve never been ‘hairy’ but, but I wasn’t going to be one of those gurls with the hairy legs and crotch in stockings. Listen, it’s not like I was getting laid at the moment, I didn’t have to wear shorts and I didn’t need to lift my arms and show the world my hairless pits, so this wasn’t a big deal for me.
I was feeling more sexual than any other time in my life, I had a lot of questions, I had always considered myself straight, and to be fair, it still felt like a big part of me dressing, was portraying the kind of woman I wanted to have sex with. Almost like I was temporarily living outside of my body, and watching a sexy woman dressed just how I would want a female Lover to dress, and act for me.
I took that night off because I was honestly concerned with the pain, but the following night, I was right back to it, and now had the confidence to actually know ‘Max’ could fit inside me. It took less time to feel him slip inside, and after I adjusted to the feeling of being utterly stretched, I started working on the feeling of being utterly stuffed. in less than a week I was managing to get the majority of Max inside me, I also found that this could all be a bit messy, so the following day, while picking out which wig I would be ordering to reward myself for my progress with Max, I ordered an enema kit as well.
The wig was a long blonde style, that hung straight and to the middle of my back. coupled with the black bra and panties, and my new garter belt and stockings made me swoon. Now that I had feminine hair, I really started looking more like a female. When I had first started down this path and had practiced applying makeup, and watching online tutorials, it had taken a lot longer than I had ever imagined, but now, with my face framed with my long blonde hair, I really did look female, and it did feel naughty knowing that I’d planned to take him balls deep on our date tonight.
So to continue..
As I looked away from the mirror in my bedroom. I set my hands on the mattress in from of me and lifted my ass up along the length of the dildo, till only the head remained inside. I then wiggled my butt and began settling back down on it till the balls pressed against my ass cheeks once again. I felt like such a Slut, my mouth couldn’t give Max the release he deserved, but I knew that my pussy could, and as a low moan escaped my painted lips I began raising up off him again, the going was becoming easier now, my pussy wasn’t burning as much as it had been a few minutes earlier, and if I pushed my ass out just right, I could feel something that felt really nice inside me as I slowly fucked Max.
I looked down as my own cock stood out stiffly from below my garter belt, a long string of pre-cum had stretched to the mattress below, and I began slowly stroking myself, the way I would imagine the way a woman would stroke herself if she had a cock. The feeling was indescribable. My pussy was filled with Max’s cock, I could now easily move up and down his length, taking him completely inside me, any pain now had gone, Max had re-shaped my pussy so that he fit perfectly inside me, he had made me his.
I rolled onto my back, positioned with the pillow under my ass as Max continued to work his full length in and out of me, once fully withdrawing, and my pussy emitting an obscene sound in the process. He quickly found my opening once again and easily pushed inside, staying fully buried for a few moments, as if to re-establish he now controlled and owned my pussy. All of these wicked thoughts pushed me over the edge and I felt the telltale pressure rapidly building inside, I knew my own climax would grip me in moments, and I had to prepare so as not to ruin the moment. Max pulled out one last time, I took him in my hand as my own orgasm ripped through me, liberally spraying cum along his length, and then just as quickly I felt him slip easily back inside me, my walls liberally coated with the hot cum that had only seconds before erupted from my balls.
My body twitched and my hips shook as my orgasm subsided. I had my eyes clenched tightly shut as my breath came in gasps and I tried not to move as every nerve ending in my being was overloaded and needed a moment to reset. That had been the best sex I had experienced in my life. I smiled contentedly and lazily opened my eyes to see Max’s cock poised directly in front of my face. I understood what was being asked and so I parted my lips and as the head of his cock entered my mouth, I recalled the taste of his cum as I closed my eyes once again and went about my cleaning duties.