Boyfriend Turned Girlfriend

Chapter 1:

My name Matt and this is the story of how my girlfriend turned me into a sissy.

In high school, I was always on the shyer side. If you saw my appearance, you would immediately know I wasn't a very popular boy. I was very short (about 5'5), flowy/long blonde hair, blue eyes hidden behind my glasses, and just about 0 muscle on me. In fact, the only large part of me was my butt. Along with my looks, I'm the typical nerd in all facets; studied hard, bad at sports, and minimal attention from girls. Well except for my girlfriend that was. She was in many ways, quite opposite of me. Her name was Ashley and she was captain of the softball team, loud in class, poor grades. The only thing we really had in common was that boys weren't interested in her the same way girls weren't interested in me. When I phrase it that way, it sounds like we both settled. However, that was not the case at all. We were attracted to each other... just not in the conventional boy meets girl kind of way.

As you may have already assumed, Ashley was the dominant one in our relationship. Not only was her personality louder and bolder than mine, she was also bigger than me. She was a lot taller than me (5'10), with big muscles and more body fat. She was in good shape, but definitely a more masculine and powerful build. In a weird way, I always found that attractive. When we would hangout, she would always decide what we do. I never minded because I'm naturally indecisive and loved to make her happy. Since neither of us were the most popular, we spent most of our time together. We did plenty of things together, but typically we would hangout at her house. She lived alone with her mom (who often worked). It was the perfect set up for a high school couple!

One night while we were hanging out in Ashley's room. Our usual routine was to smoke some weed, get some snacks, and lay on the couch together. Tonight was no different, we were flipping through the channels when she stopped at Rupaul's Drag Race. I didn't really want to watch this, but Ashley knew I wasn't going to complain so she left it on. We were talking and not really paying attention anyway so I didn't mind. After a little while, the "girls" were getting ready for their show. Ashley and I couldn't believe how pretty they became in what seemed like such a short time. While I wouldn't have admit it at the time, I was immediately envious of these stars. Ashley must have been thinking of something too as she was suddenly quiet.

"What's wrong, baby?" I said to her.

"Nothing. I just cant believe how good they look!" She said excitedly,

"Like they look so pretty I didn't even know boys could be so pretty.."

"Yeah, they do look pretty." I said admitting the obvious.

"I feel like you could totally be one of them." She said in both a matter-of-fact and teasing tone.

"Oh.. I don't know about that.." I said shyly while picturing myself as one of these divas on the tv.

"No, seriously! I'll prove it to you. If I can make you as pretty as a girl, you have to do something for me. If I can't, I'll have sex with you tonight." She offered.

Now this was a big deal. While we often made out, felt each other up, and both performed oral on each other, we were both still virgins. I've been dying at my chance to finally fuck her.

"Deal. Let's do this!" I said. Deep down, I knew I was going to lose the bet. But this may have been my only chance for a while. I had to go for it.

Ashley then led me to the bathroom and pulled out her makeup bag. She put my hair up in a small ponytail and immediately got to work. Neither of us spoke much while she began my makeover. She then put on hot girl music like they did in the show. We both started getting into it more and more. We were smiling and giggling. Ashley began by applying foundation, blush, mascara, eye shadow, and finally lipstick. She was repeatedly telling me how pretty I looked yet refused me from looking at the mirror. She was really going all out and I was nervous yet blissfully enjoying the experience. After my makeup was done, she began to straighten my hair. I was a little worried it would ruin my hairstyle but I figured a shower would sort things out. Before I knew it, my makeover was done.

"Before you look in the mirror, we have to dress you properly. Let's go pick out something cute to wear." Ashley said grabbing my hand and pulling me towards her closet.

"Wait here, I know exactly what to dress you in!" She yelped excitedly.

I waited on her bed, watching the show again. The stars were now doing a sexy strip tease for the judges. I secretly wanted to be them. Ashley came over to me and saw me staring at the show.

"Good idea. Go get dressed and you can dance for me!"

She handed me a pretty pink dress. I knew this must have been old because It seemed my size and I haven't seen her wear this color in years. Along with the dress, she passed me a pair of slutty pink panties and a pink bralette.

"Isnt this a bit much..." I started to whine when she cut me off -- "Excuse me, I have a bet I'm trying to win!"

I pouted back to the bathroom and put on the bralette and panties. They felt so good on my soft, nearly hairless torso. My cock was rock hard and leaking precum. I began to panic. She was going to see how horny this was making me and think I'm weird. I put the dress on next, hoping it would hide my erection. It was tight from top to bottom. I could see the outline of my nipples, cock, and my big booty was on full display. I didn't know exactly what I looked like, but I knew it was going to be clear that I was into it.

"Oh my god! What's taking so long!" Ashley said opening the door.

Her jaw dropped when she saw me. I was so nervous, at first I thought she was appalled to see her boyfriend look so feminine and pretty. She walked over to me and kissed me passionately. Completely dominating me with her kiss. She grabbed my ass like a girls and even reached for my tits. I was melting into her kiss. My cock was throbbing harder than ever now and she could clearly tell.

"You must like this as much as I do." She said running her finger along my cock.

"Are you ready to see the new Maddie?"

Before I had time to complain about her making my name girly too, she pushed me in front of the mirror. I was stunning. My feminine features were popping. My cheek bones and plump lips looked like that of a very pretty womans. I spun around and saw how well the dress accentuated my round butt. I couldn't believe this pretty girl looking back at me in the mirror.

"So we're obviously not going to have to argue over who won our bet..." Ashley said.

"Nope.. you win..." I said making girly expressions with my body and face into the mirror.

I was so wrapped up in how hot I looked, I forgot why we were doing this.

"First, let's see you do that dance." She said walking over to her speaker to play Megan Thee Stallion off her phone.

We both took a hit of her weed pen and we felt very high. It was time for my dance. I was horny, high, and more confident then I had ever been as a man. I began to dance while slowly taking off the tight dress for her. She cheered me on while she slowly touched her pussy watching me. Before long, the dress was off and I was just in my bra and panties. I was rock hard yet my cock wasn't falling out of the panties. I knew the song was about to end so I finished my routine crawling up to her and sitting on her lap.

She stared deep into my eyes and began kissing me roughly again. She was manhandling me and I was loving it. It felt good not to pretend I was the masculine one here. It felt right to submit to this superior woman. As she kissed me, she touched my body like a womans. She caressed my tits, spanked my ass, and rather than touching my cock, she teased by gliding right over it to my hole. She began to rub it like it were a pussy and called me her pretty slut while she continued this touch. I was too aroused to even think about what was happening here. I just moaned desperately into her passionate kiss. She dropped to her knees and pulled my panties to the side. At first I was excited to have my dick sucked yet she had something else in mind. She lunged for my hole and began to lick it hungrily. My cock was leaking violently now. I went to touch it and she pushed my hand away.

"Mmm you like this don't you, Maddie." She said devilishly.

"it feels... sooooo.... Good...." I moaned as her tongue reentered my hole once again.

Reading the situation properly, she began to slip her fingers into my mouth. I instinctively knew what she wanted and began sucking on them like a good slut. She moaned into my hole, causing my cock to twitch again. She pulled her soaked fingers from my mouth and slipped them into my hole. I moaned as she began to finger me. She pulled them in and out while massaging my prostate. It felt too good. For a brief second I contemplated telling her to stop. It's not what I wanted, but I felt like I should put up a fight. I went to say something when she began to lick my balls while fingering me. That was more than enough to keep me from denying this pleasure. Before I knew it, she slipped a third finger in and was really pounding my hole now. This had to be the horniest I had ever been in my life.

"You like being my good girl? My pretty sissy slut?" She said, increasing her pace.

"Yes, it feels... so... ugh fuck.. yes!" I moaned, incoherently.

"I love my new girlfriend. You're so fucking pretty, Maddie."

All I could do was moan in bliss.

"Is my little sissy gonna cum from her pussy being pounded?" she purred into my lips while kissing me dominantly once more.

This was too much for me to handle. I exploded into her panties without even having my cock touched. It was the most intense orgasm I had ever had in my entire life. Ashley looked very proud of herself and teasingly said "aw you really did some damage to my panties." When she looked back at me, she noticed I was crying. Before I could say anything she started crying.

"I'm so sorry, Matt! I must have gotten carried away! I didn't mean to make you feel bad or push you into something you didn't want!" She said half crying into me. Before I could say anything she continued: "I think I took out some of my own feelings on you. Lately, well I guess always, I've been confused about myself.. like Ive always been attracted to girls and in denial. I shouldn't have forced you into my own confusion and I am so sorry!!!" she said, now sobbing into me.

I grabbed Ashley's face and kissed her gently. First I wiped her eyes and then my own.

"Ashley, stop. I'm not crying because I'm sad. I'm crying because I just learned so much about myself. I've had my suspicions I might not be so straight myself and this was a whole new world of feelings. I cried because I loved that so much. I have never felt so good in my life. Whatever you started with this, I don't think there's any going back now."

Let me know in the comments what you think! I would also love to know which series you want me to keep writing!