The Chance Fantastic Pt. 02 - The Roots

I made my way to the back of the shop again, holding panties and other clothes in my left hand. I knew I should feel ridiculous, but I didn't. I just felt hot and horny, which made grabbing my next two items easier. The dildo I had found, along with a small bottle of lube. I had never bought lube before. I had always just used spit when masturbating. But I had vague ambitions of finding out what pegging actually felt like, and I knew I was going to need some help. The girls in the videos made it seem so hot, and I knew guys had their g-spots up there. I was eager to find out.

I quickly checked out. Unlike how porn stories had made me picture them, the sex shop clerk was quiet and discrete as she scanned my items. I had a whole story prepared, about how these were all gifts for my girlfriend. It even sounded flimsy in my head, but it helped me feel better about engaging with another human in this rather intimate transaction. But she didn't ask. The only thing she asked was for my ID, to confirm I was over 21. With that over, I exited the store, quickly walked to the car before anybody saw my bag, and jumped in. I don't know why I thought the bag was so conspicuous. It was a plain black paper bag with no logo on it. I was just feeling all twisted up inside, with excitement, lust, and shame all mixing together for a confusing feeling.

I used the car ride home to try to calm myself a bit. Luckily, I had a backpack in my car in which I could stuff the bag from the store so that no one would ask me what it was as I made my way back up the stairs. Once inside, I was glad to see that no one else appeared to be home. Almost running to my room, I quickly closed the door, locked it (not even bothering to hide the click), and started stripping. It was time to try on the panties.

I had looked up my size before buying them. I had measured my waist and hips before leaving for the store, and determined that I was roughly a medium. My waist was a little larger than the average medium, and my hips a little smaller, likely on account of having a man's proportions. I started with the most conservative. Slipping them up my legs, I soon discovered the most immediate problem all guys must have when trying on their girlfriend's, sister's, crush's, mother's panties: my boner would not stay down. I couldn't tuck it - I was far too hard for that. I had two options. Either I could just slip it out the front, and have my panties on a little off-kilter, or I could try to point my dick straight up, with the danger of having it push the panties back down. I opted for the former, reasoning that what I really wanted was to check out how my ass looked, and my dick shouldn't affect the view back there.

To my disappointment, boyshorts, which I found so hot on girls, didn't look that great on me. I was flat back there, and the cut of the panties seemed to emphasize that. Besides, with a dick poking out the front, it looked like I was just in a pair of briefs. I took them off and decided to try the other end of the spectrum. There too, I found nothing but disappointment. My raging boner completely ruined the front of the thong. With the clear panel, there was no hiding my hairy dick. While the string did disappear satisfyingly into my ass crack, it also showed how hairy I was back there. Less skin would be better, I thought.

The frilly panties were my last hope. As I pulled them up, I first noted that these seemed to fit the best. While the boyshorts lost the battle against caging my dick, and the thong didn't have enough fabric to put up any sort of fight, the bikini bottoms trapped it upright against my torso, giving me a more feminine fit. They hugged the slight curves of my ass. For the first time, when I looked in the mirror, I could see the vague outline of a girl shaking her ass. I had found my winner.

Elated, I couldn't wait to tear open the stockings next. But I ran into a common problem - fishnets just didn't look as good on hairy legs. For the first time, I started to consider shaving my legs and dick.

However, for the time, I kept them on. While they weren't as hot with my hairy legs, they didn't detract from the image in the mirror either. Next came the pink tartan schoolgirl miniskirt. Pulling it above my panties, the image in the mirror was starting to come together. I gave it a little twirl, and then bent at the waist to admire the view. I was starting to get really turned on. I almost skipped the next few steps to just rub one out, but I exercised what little self-control I had left to take out the white crop top.

Looking at myself, I couldn't help but frown. My top half had a lot more work to do than even my bottom half. Without breasts, I just looked silly. Besides, I could see a faint outline of a mustache, and my face was undoubtedly boyish. My short brown hair lent nothing to the image. Sighing, I quickly put on the small pink tartan tie, and bent over (at the waist, almost without thinking) to open the dildo.

I pulled it out of its package and just spent some time admiring it up close. It wasn't the most realistic thing, but the manufacturers had put forth some effort. The balls were rough, just like a real scrotum, and the shaft had a few veins running down it. I couldn't tell if that turned me on or off. I didn't bother to pursue that train of thought further. Hesitatingly, I did what I thought I should do next. I poked out my tongue, and gave the tip of the fake cock a little lick. It didn't taste much like anything, which I categorized as a pleasant surprise. With a little more boldness, I decided to try to recreate what I had seen some of my favorite pornstars do. Clumsily, I gave the tip of the cock a little kiss, and then I kissed down the shaft and back up again. I then stuck the tip in my mouth and just sucked that for a little bit.

Trying to get more into it, I started to pump it in my mouth, stopping well before I hit the back of my throat. I had hoped that, at this point, I would start to feel turned on, but I honestly just felt a little silly, with a fake flesh-colored piece of silicon sitting in my mouth. I tried to do the last step - a deepthroat. Pushing past the point of comfort, I tried to force the eight inches down my throat. I don't even think I got halfway before I started choking. I coughed, quickly withdrew the dildo, and felt my eyes water. It wasn't worth it, I decided. So maybe that was one of my sissy limits, if I was one. I didn't particularly enjoy oral. Dressing up seemed to have its perks, but sucking a fake cock just seemed ridiculous.

I rested for a bit after that, just watching some of my sissy hypno as I thought about what I wanted to do next. I knew I always had the option of just masturbating in my clothes. I toyed with my cock as I thought about this option. I didn't jerk it, I just rubbed it in slow circles with the palm of my hand. Looking down at myself, in my skirt, panties, and fishnets, I did feel that this was a more immersive, and ultimately enjoyable experience. I just had one more thing I needed to try.

Grabbing the bottle of lube, I squirted some out on the dildo. I pooled around the tip before starting to drip down one side. Quickly, I started rubbing it up and down the shaft, a small smile playing on my face as I realized I was unintentionally giving an invisible person a handjob. I then squirted some more onto my hand, bent over, awkwardly pulled my panties to one side, and started rubbing it on my asshole. It was cool to the touch. It didn't seem quite so heavy as vaseline or lotion, but a little heavier than water. Taking a deep breath, I tried plunging a finger inside myself. After a little initial resistance, I was surprised at how easily my ass swallowed my finger. It didn't hurt at all, not with the lube at least. I just sort of left it there for a second, unsure of what to do. I tried exploring a bit, but other than my finger feeling warmer, it didn't really cause any pleasure reaction.

I tried a second finger. This one too came in fairly easy, though there was a bit more resistance. I felt a bit of discomfort, and so I just sat there, two fingers in my ass, letting it adjust to the new sensation. I had been pretty sure before this experience that the fingers would not cause me much pleasure, and to my disappointment, I was right. However, I could live without the physical sensation if it aided the mental picture in my head. I started slowly pumping my fingers in and out of my hole, and I tried moaning, just like I had seen the girls doing in the videos I always watched. Quietly, of course - no need to alert a roommate if one had come home without me realizing.

With my other hand free, I started to slowly jerk on my cock, using, as I typically did, spit as a lubricant. It was awkward and clumsy, keeping both hands going, kind of like trying to pat your head and rub your stomach at the same time. But it still felt good. It didn't feel too different from masturbating as normal. I decided I had to up my game. I stopped pumping my panty--clad cock to reach for the dildo.

I didn't know the best approach for

how to get it inside me. It took about a minute of me bent over at the waist, trying different angles, before I finally pressed it against my asshole. Apparently, I still didn't have it quite right, because as I increased the pressure to try to get it inside me, it just bent to the side. Extracting it, I re-aligned it so it was more straight on (from what I could tell), and tried again.

I felt the tip start to poke inside me. It was so much different from my fingers. Whereas my fingers slipped inside easily, and didn't seem to require my body to strain in any way, the cock made my ass part. I could feel myself opening up. It wasn't quite painful; I would instead describe the feeling as "difficult," like my body wasn't meant to be doing what it was doing. I quickly had to stop. Taking a few deep breaths, and still determined, I made another go of it.

This time, I got the entire head in. I felt full already, and uncomfortable. I just held it there for a bit, unsure of whether I wanted to go farther. I told myself that of course it didn't feel that great right now, my prostate and g-spot were much deeper inside. I had to keep pushing. I started to push it farther in me. Although it was easier to get the shaft in now that the tip had already split me in two, the next few inches still pushed me from uncomfortable to "in pain."

I stopped again. I don't know why I was so determined. I suppose there was something to the old adage to not do something halfway. I wanted to get to the point where I could fuck myself. Even if I wasn't a sissy, I wanted to be in a position where if a hot girl ever did want to peg me, I could take it and enjoy it. Feeling a little more adjusted, though still more full than I had ever been, I started to take the shaft out a little bit, and then push it back in for my first few timid pumps to fuck my own ass.

As I started to get into a rhythm, I took a look at myself in the mirror. Objectively, I still looked ridiculous. I was clearly a boy dressed in girl's clothes. But my brain, more and more lust filled with every step I took, saw it as hot. Particularly the mini-skirt, the panties, and the position, bent over my bed. Now that I had the hang of the dildo, I started to stroke my own cock again. I felt girly. I felt slutty. Even though the dildo didn't feel good, stroking my cock did, and the image made it hot. I started moaning again, this time only partially to make the scene hotter. It felt like an appropriate thing to do.

I came in my hand, with a good portion of my sperm dribbling down the front of my panties and the inside of my skirt. I had to brace myself against my bed as my knees buckled a little. Taking deep breaths, I felt satisfied. I knew that in a few moments, the disgust with myself would set in, as it almost always does when I try something new with porn, but for this moment, I felt happy and satisfied. Maybe I would sleep in some panties tonight.