The weirdest gift from the past

“I know this will is kinda awkward and weird” my mom said as she handed me a picture of my late grandma. “What is this?” I asked. I had never seen my grandma in such a young and fit shape, and worse of all, dressed like some kind of burlesque dancer. “Wow, nana was hot” I said mockingly. “Yeah, I know. You can say her looks are out of this world” my mom said. “Mom, that is weird coming from you” I responded.

Anyways, she handed me the picture. “Nana said this is yours to keep” she said. “Ok” I said and rolled my eyes. “That’s not all, she said that you must keep it under your pillow for one night” my mom instructed. “And if I don’t?” I asked. “No big deal” she responded.

Anyways, I was not going to put the picture anywhere near my bed. So as soon as I got into my room, I placed the picture inside a notebook and hid it in my closet. “Grandma was weird” I said as I jumped into my bed.

As I was about to fall asleep, I swear I heard her voice “put the picture on your bed”. I felt compelled to do so.

I picked the pic back out, and placed it right under my pillow. That night I had the weirdest dream. I dreamt I was with my nana, but as time passed by, I was acting more and more like a young version of my nana. Suddenly, I realized I was looking at myself in a mirror. I was her, I was nana, and apart from my brunette hair, I looked just like her.

Suddenly I woke up. I was hyperventilating. I took off my covers, expecting to see my flat chest, but instead, I had breasts. “It’s gone!” I said as I realized my equipment was gone too. “Ahhhhh!” I screamed. My mom and dad came into my room. “What’s going on?” I asked them. “I see you placed the picture below your pillow” my mom said. “Sweetheart, you scared me” my dad said. I realized my dad was unaware of any change, while my mom knew everything about it. “Dad, I need some time with mom” I asked my dad to leave.

“Why?” I asked my mom. “Nana’s last will” she responded. “To turn me into a woman?” I asked. “Yes” she answered and smiled. “What? Once again, why?” I asked. “Well, you are not the only one, I used to be… a guy too” she whispered. “Wait what?” I asked. “A straight guy, but once she transformed me… everything changed” my mom said.

She handed me a dress. “Let’s go out, together” she said. Surprisingly I put in the dress without an issue. I spent the day with mom. We went to the spa, shopping, brunch. I was acting girly. And while I hate to say it, I was checking out guys. “How about that one?” My mom asked. “He seems hot” I responded. “Shit! No! Please, I want back” I said.

This was our first day out as girls. But by the end of the day, I was walking on heels like a pro. And the flower dress my mom had handed me in the morning me felt good on my skin.

Anyways, the next day she took me out for some coffee. Trying to hide my assets, I wore a pink sweater. My mom kept asking me about who of my friends was hotter. “Mom! I want back, please stop this” I said and refrained from talking for a while.

She the  took me to a small antique shop. She wanted to buy an old oil lamp for a friend of hers. “How about this one?” I asked her, but was immediately interrupted by the store clerk. He was a handsome guy. Since my mom was nowhere nearby, I started flirting with him.

I even took my pink sweater off. I wanted him to see my perfect figure. I realized it was too late for me. I would probably remain a woman for the rest of my life.

We exchanged numbers. I had an awkward smile. My mom was looking at us from afar. When we left she couldn’t help but giggle. “Shut up” I said. “Don’t worry, just losen up — wait until you get to have sex from this perspective” she said. It was quite a mental picture, “Mooooom” I complained. “That reminds me” she said as she pulled me into a pharmacy. She bought a few condoms and the pill. “You don’t want your first experience to be that of a pregnant woman” she said.

The following day, Josh, the guy I met at the antique store called me. I felt butterflies in my stomach. I sneaked out of my place to go have coffee with him. I didn’t want my mom to find out, after all I was still telling her I wanted her to turn me back.

He was fun, handsome, and quite a talker. We connected right away. We ended up making out in his car. His hand running ip my leg, my hands grabbing his face, as I french kissed him.

I told him sex was out of the question. “Not until our third date handsome” I told him.

As I arrived home, my mom greeted me, “so? How did it go?”. I just smiled and giggled. “Do you want me to turn you back?” She asked. I was about to say yes, but changed my mind almost immediately, “actually, let’s wait until Friday” I answered and went up to my room.

The following day, Josh took me out for some coffee. I wore a pink flower dress. I still felt butterflies in my stomach. I wanted him inside of me. But I did say three dates, so I refrained from it. But I allowed him to get to 3rd base.

The following day, my mom and dad went out to a party. So, I took the chance to invite Josh to my place. I wore nylons for the first time. I felt sexy, I applied my own makeup. I was ready, I knew this was the point of no return. After about 20 minutes of watching a chick flick, I moved my hand over his crotch area.

He looked at me, I smiled. I pulled down my breasts, revealing my perfect breasts. He kissed and sucked those babies, until they sore. I was over him, his thing inside of me, myself thrusting up and down, while he held me from my waist, and sucked on my nipples.

I was moaning, sweating, and enjoying the hell out of it. Mom was right, sex from this pov was amazing. Anyways, after sex we cuddled for a while. I learned something that night: Cum drips. As a guy, I used to be a virgin, how was I supposed to know. Anyways, after he left, I had to clean my sheets. I didn’t want my parents to know what had happened.

When my mom came back home, I had already cleaned everything, nothing left that would give up what had transpired. But as soon as my mom saw me she said “you had sex”. I blushed. “How was it?, well,  sorry, I don’t want to be awkward, let me just ask you one question, turning back is out of the question . Right?” She asked, I nodded. As she was going upstair, I stopped her, “mom, what gave it away?” I asked. “The smile on your face sweetheart.

Josh and I continued dating. We enjoyed our time together tremendously. I really enjoyed swimming at his parents house. The water touching my perfect body made me feel self aware of my new form. The lack of equipment, the two mounds on my chest, the softness of my skin. It was just wonderful.

We loved to joke and talk shit. But something surprised me, when it came to talking about my past, I remembered being a girl so vividly, and being a guy felt like an old distant dream. 

My mom told me that was normal, the same happened to her. Weeks passed, when finally, I realized that I had found in Josh the man I wanted tocspend the rest of mylife with.

Imagine my surprise when he popped the question. I immediately said yes. We went partying that night. And oh god, that night was the best sex I’ve ever had. He went down on me. His tongue worked wonders. I felt my clit get erect. Then we ended up doing a 69, I thought it would be weird. But it felt amazing. Eventually, he shoved his big equipment inside of me. We both came in synch.

After 11 months, we got married. And it was the best day of my life.

My mom, right before the ceremony told me how everything worked in our family. “Our first born child is always a boy. When he reaches a certain age, you will hand him this picture” my mom said as she handed me a picture of herself. “And you will tell him to put it under his pillow… you know the rest” she explained. “Oh, and don’t forget when your son… daughter, gets married you have to hand her…” she was saying as I interrupted her, “a picture of myself, and tell her the same instructions” I whispered and smiled.

Anyways, that was 7 months ago. Now, here I am, pregnant, expecting my first child. And I couldn’t be happier. I thanked my grandma, as I rubbed my belly.