OMG My Daddy’s a Sissy (Prequel)

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All characters are purely fictional and of legal age (over 18).


I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn’t take us long to realize that we weren’t like the others at this school. As it was located in the Southern part of the country, our college was popular with country boys and girls from all over. Lots of jocks,cowboys and prom queen types. I have nothing against these folks, but I just don’t fit in with them.

I’m a bit of a bookworm and somewhat introverted. We began hanging out platonically on Friday and Saturday nights. Deidre was 5′ 5′ about 105 lbs., with small perky tits and a tight ass. She had alabaster skin, black lipstick, and a nose ring. I once asked her why she thought we were friends and she said that liked that I wasn’t a jock or part of the bourgeoisie. We’d read many of the same books, most of which were philosophical in nature and way over the heads of those who lived in our building.

Near the end of the first semester, my brother spent the night while traveling home from his school to my parents house. My brother Alex is a man’s man. Tall, muscular, and very good looking and he liked to drink beer. The plan was to drink some beer and maybe watch a movie. Early on, I caught Deidre looking at his crotch and called her out while Alex was in the restroom.

“You were so, just looking at his dick!”

“So what if I was? I bet he has a nice one! From that bulge, I know it’s big for sure.” She said with a mischievous grin.

Like he did on most Friday nights, my brother ended up getting wasted and passing out. Deidre and I watched movies until we both fell asleep. The next morning Deidre and I walked Alex to his car and said goodbye. When we got back to Elliot hall, we went back to my room.

Out of nowhere Deidre shoved her tongue in my mouth like a whore. It was a hard kiss, an aggressive kiss. It was nothing like the girls I kissed in high school.

“So is your cock as big as his?”

“Deidre, what the fuck are you doing here?”

“Well is it? I saw it you know? Alex got up in the middle of the night to pee and I saw it. It was huge! I was tempted to jump him right there, but I don’t fuck guys who’ve never read Dostoyevsky.”

“I’ve read Dostoyevsky.” I said with a sly smile.

“I know! And now I know if your cock is like your brother’s I’ve hit the mother load!”

“Lemme see it!”

And with that she threw me onto the bed, and in no time she pulled my shorts down and was staring at my completely pathetic little cock.

“Wait? What? I mean, it gets bigger right? Oh my goodness! It’s so cute! “

I was humiliated. I felt myself tearing up. I didn’t want her to see it so I looked away. Then I felt her lips around my cock. In a few seconds I was completely hard. She popped it out of her mouth looked at it and said “Well, I’m too horny to turn back so, I guess this will have to do.”

Ten seconds later she was riding my cock like there was no tomorrow. She looked so beautiful and pale. Soon I started to moan. Deidre’s face changed from ecstasy to anger. She stopped riding me, and reached back and squeezed my balls hard.

“Don’t you dare fucking cum. I’m letting you fuck me so I can cum got that? If you’re a good boy maybe I’ll let you cum too, but I’m first.”

She let go tuzla escort of my balls and continued rocking back and forth. She was an Angel and I was smitten. She bit her lip and began digging her fingernails into my chest. A few seconds later I watched a girl have an orgasm in person. I’d love to tell you that I gave it to here but that isn’t true. She didn’t let me do anything. I basically laid there motionless as she rode my dick. Watching her cum, I knew now that any orgasms I thought I had given my girlfriend in high school were fake. She smiled at me like a Cheshire cat, and dismounted my cock.

I began rolling over on top of her, but she stopped me with a hand on my chest.

“Sorry Romeo, but this pussy is closed. Go to the bathroom and jerk off if you want to cum.”

Then she kissed me on the cheek, jumped in my bed and under the covers. I could still smell her pussy on my cock. I was so crushed, I didn’t want to masturbate, I wanted to fuck! I crawled into bed with her and fell asleep.

The next morning I woke up with Deidre’s head on my chest she was sleeping peacefully. She was topless, wearing only a pair of blue silk bikini panties. I laid there smelling her hair for a good 10 minutes before she woke up. She looked up and smiled.

“Hey Romeo! How’d you sleep?”

“Fine I guess. Wanna talk about last night?”

“Only to say I’m sorry. You’re a good guy and it’s not your fault you have a little weenie. I’m going to make it up to you right now!”

And with that she dove under the covers, and took off my boxers and put my dick in her mouth. I lifted the covers to watch the show. Boy did it feel amazing. Deidre really knew how to suck cock. She stopped for second to catch her breath and looked up at me.

“It’s just so cute! I knew this girl in high school who had a huge clit! I mean really huge. Everyone in our gym class called her the “cock girl”. Yours is a little bit bigger than hers! So cute!”

She put me back in her mouth and finished the job. She even swallowed my load.

We laid in bed for a few minutes talking. I told her that as much as I was enjoying things, I had a speech and debate class I need to leave for soon, and that I was dreading it.

“Why?” She asked.

“I’m just nervous. Public speaking really isn’t my thing. I mean, I know the material, but I’m just afraid everyone will see right through me. I’ve heard you’re supposed to imagine everyone in their underwear. Seems like bullshit.”

Deidre caressed my cock with two fingers and asked, “So you need a secret no one can guess. Then you’ll know that they can’t see right through you. Make sense?”

“Yeah, I suppose, but I can’t think of a single thing.”

Deidre sat up, I watched her pale frame with little titties and pink nipples. She reached her thumbs under the elastic of her panties and slid them off her beautiful pale legs.

“Put these on.”

“Deidre, I am not gay. I am not putting on your panties.”

“Listen Romeo, wearing panties doesn’t make you gay and if you ever want to put your little win weenie in my pussy again, you will put these on.”

I knew I wasn’t going to win so I slid my feet into the panties.

“Lift your hips, come on you can do it.”

She then slid the panties up and onto my butt. I couldn’t believe it. I was actually wearing girl’s panties. The blue satin fabric felt amazing ümraniye escort against the underside of my cock. Deidre sat back with a smile on her face and her hands on her hips like a proud parent.

“Look at you! They look so good on you! I can barely see your little weenie. You look just like a girl!”

What she was saying wasn’t nice, but somehow it was turning me on. She was kind in her tone, but cruel in her content. Somehow this gave balance to the things she was saying and made me rock hard.

“Ok now Ricky.”

No one ever called me that.

“I want you to put your jeans on, and a nice button up shirt. Wear your loafers with argyle socks, and go give that speech knowing that you have a secret no one can guess. You are wearing pretty blue panties.”

A couple hours later I knocked on Deidre’s door. When she opened it I was beaming. I grabbed her and hugged her as tight as I could.

“They worked! The panties worked! I nailed that speech and it’s all because you made me wear panties! I can’t thank you enough.”

Deidre was so happy. Like a mom who just heard her son was accepted to college.

“Oh come hear, honey that’s wonderful! I knew you could do it! Now tell the truth, did you like wearing the panties? Did they feel sexy?”

I had to admit they did. There was a sexual charge in the air. I seconds she was topless, in a new pair of silk panties this time they were red with little hearts on them. I unzipped my jeans and started to get naked.

“Uh jeans yes. Panties no. Keep them on sissy boy.”

“Sissy? I’m not a fucking sissy?”

“Not gay stupid…sissy. Gay guys want to fuck other gay guys. We know that’s not you. Sissy’s like to act gay but with a girl. Get it?”

She slapped me on the ass for emphasis.

So I crawled into bed with Deidre. We were both topless and both wearing panties. We kissed for a while. During that time our panty clad bodies were rubbing together. My cock was hard and the tip poked just past the elastic. The feeling was amazing. Deidre pushed me down towards her crotch and I knew she wanted me to lick her. Being the bookworm that I am I’d read up on this and was eager to put my skills to the test.

She had 3 orgasms in a row! Finally she pulled me back up to her and we kissed some more.

“Boy what you lack in cock you make up for in pussy licking! It’s almost like you’re a lesbian! No cock, but good at eating pussy! Good job sissy! Now it’s your turn.”

I couldn’t wait. She got out of bed went into the closet and when she came out my jaw hit the floor. She was wearing a strap on cock like in the porn movies.

“Uh, uh not me no thanks.”

“Awe come on Ricky! You didn’t think you’d like the panties and you did! Now get on your hands and knees and pull down your panties so I can lube you up. Come on now be a good boy!”

Again I knew that Deidre was not going to be denied. I got on all fours. I was facing away but I could hear her squirting lube onto it. Then I felt the cold cock at the entrance to my ass.

“Since it’s your first time, I’m going to be gentle ok Ricky?”

She pressed forward and I felt it enter my butt. A few minutes later it was all the way in.

“Mmmm you like that don’t you sissy? You know what you are Ricky? You’re a panty wearing sissy who apparently likes getting fucked in the ass. True?”

I üsküdar escort nodded my head. I had to admit it felt fantastic. My little cock was limp but it was so sensitive.

“No no no that won’t do now will it? Tell Deidre. Tell Deidre what you are.”

Deidre reached around with a lubed up hand and held my cock. She began thrusting the strap on into my ass as deep as it could go. “Tell momma what you are now darling….”

“Um…I’m a sissy”

“No that’s not good enough. Be proud! Tell Momma Deidre what you are baby.”

I was getting close to cumming and there was no way she was going to let me if I didn’t say it.

“I’m a panty wearing sissy who likes getting fucked in the ass!”



“From now on you’ll call me Mommy. Now say it again and Momma will let you squirt.”

She picked up the pace of her hips and her hand. It was going to be any second now.

“I’m a pany wearing sissy who likes getting fucked in the ass Mommy!!!!!”

“Ok baby squirt for Momma now. Make your little weenie squirt for Momma!”

The words “little weenie squirt for Momma” hit my brain like an electric shock. I came harder than I’d ever come before. It was so fantastic I couldn’t control myself. I was wailing loudly with each stream of cum that left my cock. Deidre kept jacking my cock and pounding my asshole.

Suddenly, the door to Deidre’s dorm room opened. Her roommate and her boyfriend walked in just as I was coming.

“Well what do we have here Deed? You finally got someone pathetic enough to let you fuck them with that thing? Oh and with panties on too? Oh how cute!”

Deidre smiled in satisfaction. “Show them your weenie.”

“Deidre I…”

“Go ahead Ricky and show them your little weenie.”

I stood up panties on my ankles, with a gaping asshole, and let them see my cock.

“Oh my God! Deidre it’s so tiny and cute!”

“I know that’s what I said!”

“We’ll leave you two so you can finish up. You guys want to go to town with us for dinner? We can double date”

Deidre told them that we’d talk about it and decide in a while. Her roommate and her boyfriend left. I could hear them giggling in the hallway.

Deidre and I cuddled for a minute and then she got up and got dressed. I also got up and began putting my clothes on.

“Should we have pizza or chinese?” I said.

“Oh Ricky..Sorry but you can’t go.”

“Um why Deidre? I was invited just like you were.”

“No I can’t be with you in public, or in private for that matter. Look I’m glad you had a good time last night and today, and I’m thrilled that your speech went so well. I’m also pretty proud I was able to help. But I have to be honest with you, I can’t respect a man who gives in so easily when a woman tries to emasculate him. I can’t be with you or be seen with you any more. I wish you the best but we’re through.”

And with that she opened the door to her dorm room to show me out. I walked outside dejected. I had to finish dressing in the hallway. My cock was still sensitive and my asshole was still stretched out. Oh and lest we forget I was still wearing blue silky panties. I wandered back to my room where I cried my eyes out, then I masturbated, cried again, and jerked off again.

A month later it was mid-term time and I had to give another speech. I felt all the old feelings boiling up in my mind again. I wondered if the “panty trick” would work again. I decided to find out, and guess what? It did! After my midterm speech I was asked to join the intramural speech and debate team. The following year I was team captain. I’ve been wearing panties under my boy clothes ever since.

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