Crossdressing Into Motherhood

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“Oh my fucking god…”. I gasped, I couldn’t believe what my womanly eyes were seeing. I just woke up, being received with a new perspective that I doubted was real to begin with, but after many attempts of trying to ‘wake up’ from this nightmare, I would come to the realization that this was the real world, the same one where I was a young man a couple of hours ago.

You heard that right, I was a man, not the most masculine one out there, but I was one nonetheless. You see, I was a crossdresser, I love wearing feminine clothing and preferred them over any piece that was made specifically made for men. Probably just a me thing, but these clothes are just so much more comfortable and cuter, not to mention that they make me feel like my true self, something very fun and liberating.

I did this whole thing in secret though, as like many other families, crossdressing was a taboo topic to talk about, let alone have someone close experiment with it. I didn’t mind, I was quite the sneaky guy and managed to try on some of my mom’s clothes, they didn’t fit me well, but it brought me a lot of joy and she had a sense of fashion that I resonated with, finding a lot of her wardrobe desirable.

Yesterday was such a perfect opportunity as my parents were going to go to a friend’s wedding and because it was quite far, they’d spent a night in a hotel before going back home today. “Perfect!” I thought to myself as I had plenty of time to wear some of my mother’s adorable clothes.

Once the coast was clear, I stormed into my parent’s bedroom and excitedly picked out some clothes I wanted to try. It was a very fun experience, just like all the others, trying out some casual stuff alongside some lingerie that I couldn’t resist trying. The final piece of clothing I would wear was quite different from the rest though.

It was a patterned dress, one I never saw my mom wear before. It caught my attention and I decided to wear it, after which I realized that it wasn’t a regular dress, but rather a maternity one. It was quite tight around my shoulders and waist but very loose around my hips and the area around my belly was very baggy, likely made to be filled with a pregnant woman’s baby bump and her curves rather than a 5’11” 19-year-old male like me.

Despite not being the most comfortable fit, I still thought the dress was cute and wearing something that my own mother had likely worn while I was inside her womb was kinda fascinating to me. I liked it enough that I decided to wear it throughout the rest of the night, thinking that I should remove it before going to sleep to avoid getting caught in case my parents came back early in the morning. I would fall asleep late at night after scrolling through social media for a while, being too sleepy to remember what I said earlier.

The next morning, my parents weren’t home yet, what a relief!... is what I would’ve said if I hadn’t woken up in the body of a woman in her mid-30’s who’s ready to pop with a baby or two. All I did for a solid ten minutes was breathe heavily, letting out feminine squeals and soft screams as the feeling of life forming inside the womb I never had before felt like something out of a fever dream.

The next few minutes after the initial shock was spent denying that this was my new body. I was a young man the day before and now I’m a milf with big tits and a pair of babies stretching my belly? This didn’t make sense at all. The only reasonable thing I could come up with was the fact that sleeping with this maternity dress had transformed me into the state my mom was in at the time of wearing this dress. As to how or why? I have no clue, and I honestly don’t really care as what I do care about is turning back into my male self.

I sat there thinking for a whole hour trying to solve this insane conundrum I found myself in, during which I would experience many uncomfortable and crazy sensations. To start with, I was super heavy, despite losing half a foot in height and losing plenty of muscle in a lot places, the weight of my babies… oh god, that feels so fucked up to say out loud… uhh… anyways, the weight of my babies really took a toll on my mobility, and I doubt my huge F-cup tits helped in anything.

Oh, speaking of titties, I had always wondered what it felt like to have them, and now that I have the real deal… I’m not sure what to make of them. I won’t lie, they feel super good to squeeze, making me let out some embarrassing moans from the pleasure they brought. I had heard that they can be very sensitive, but I didn’t know they were that sensitive! That could be due to the pregnancy though.

Pleasure and fun aside, something not as fun and not as pleasurable was the fact that they were very heavy, easily lactated and felt very full of milk. Perhaps I would appreciate these boobs a lot more if they weren’t ready to feed hungry babies.

Oh yeah! Speaking of them… oh boy… They moved quite a lot inside of me, feeling it while also occasionally seeing a little fist or foot on the heavily stretched skin of my belly. In a way, it was kind of cute, but the whole thing still felt strange and very much like something I shouldn’t even be experiencing in the first place. Absolutely no hate towards these little ones, I just so happen to be completely inexperienced with being a woman, even more so as a mother, you know?

At least my hips were wide, and my thighs were nice and thick, they helped a little bit in carrying all of this motherly weight. Despite the curves threatening my panties, I wished they were even more pronounced so they could make carrying twins and two milky tits much easier.

Finding clothes that fit me, the fact that I might be giving birth and my parents finding a full-term pregnant milf instead of their son are all topics I don’t even want to get into. Hopefully, I’ll find a solution soon, so I don’t even have to cross those bridges!... Is that… knocking on the door I’m hearing… Fuck…