Transgender Takes Control Pt. 01

Author's Note: The following story contains scenes of transgender sex. All persons are over the age of 18.

****

My name is Matthew Harris.

I am 20 years old and attend Madison University.

I stand 5'10" tall and have short blonde hair and blue eyes. I weigh around 145 and have a slender body. All the hair on my body is very fine except for the hair on my head.

I got teased a lot in high school for acting very effeminate and didn't make many friends. My higher pitched voice and lack of an adam's apple made guys leery of me.

My parents died in a car accident a month after I graduated and it propelled me on my journey of rediscovery now that I was finally on my own. I have no other siblings and before I started college the next year, I changed my name to Maddy.

****

I was working as a nutritionist for GNC. I had plenty of down time and did a lot of browsing on the web about different herbs.

One day I picked up this Transgendered magazine at an adult store that I frequented now that I was dressing the part and becoming more like a woman every day. I read an article about how to grow breasts naturally without the use of estrogen. It intrigued me because I still enjoyed whacking off and didn't want to lose the only thing that made me feel good about myself.

The article talked about combining Elderberry Extract, Fever Few, Dandelion, Devil's Claw, Hawthorn Root and two other known but obscure and hard to find ingredients along with coconut oil and Ceramides in a unique combination to make a paste that you apply directly to your chest every morning for a month to grow breasts. I know, I know, I was skeptical too since I was familiar with all of these products and didn't know how they could help me to grow some tits. But I figured it was worth a try, so I did it.

I loved tits. I loved to look at women's tits. I had yet to play with any, but I always wondered about them. How they felt, how heavy they were, how stimulating it would be to have nipples that worked unlike my own small nipples that had no feeling whatsoever.

And guess what? It worked.

Little by little, I grew tits. Who knew? I sure didn't.

My new tits were a perfect 36c and my nipples grew longer as well. The best part was that the effects were permanent and once my tits reached the desired size I wanted, I stopped applying the paste.

A pleasant side effect was that when I played with my nipples, it made my dick grow erect.

I went and bought some bras, perfume and some makeup and painted my fingernails and come Fall, I looked like one of the girls only I still had a dick which I concealed by always wearing pleated skirts.

****

I started the Fall semester.

I got hit on all the time by guys and it was a real confidence booster. I even got asked out 11 times by guys, but that wasn't my focus. I wasn't gay, not yet anyway. That would come later.

Various women would look at me from time to time, especially when I would enter the women's bathrooms and sit to take a pee. I loved being in a stall next to a hot girl as she urinated and wondered if I had a fetish for being peed on as well.

I had a full schedule and one of my classes was Physics. The classroom was arranged with tables and this really cute Asian girl sat next to me. Her name was Alice and she was really petite at only 5'2" tall.

We got to know one another pretty well and worked on assignments together and became really good friends. We even moved in together in the Spring and shared a small apartment.

Alice was really open about her life to me. She was really promiscuous and slept around a lot.

"You know what I hate most about guys?" She said one day in the apartment.

"No what?" I asked in my soft feminine sounding voice.

"I hate how guys lie about their dick size. Every guy I have had sex with has had a smaller dick than what he claimed to have." She blurted.

"Really?" I asked.

"Yeah! I mean come on guys. I'm gonna find out eventually so why lie about it?

This one guy, Steve. He was so handsome and I asked him about his dick and he said that he's packing and I'm getting really wet right?

He tells me that he is hung and I'm practically salivating. Finally a guy with a big dick and when we finally do it and he pulls it out it is barely 6 inches long." She threw up her hands.

"That's nuts!" I reply.

"I know, but I was already so worked up about it that I fucked him anyway even thought I needed another 5 inches inside my greedy little cunt to really get off." She laughed.

I laughed too.

Alice loved to talk about sex and was always telling me about different guys that she fucked or sucked off. But never once did she ask me about any of my sexual exploits. I was thankful for that because I didn't have any. But it definitely got me thinking about it while I jerked off at night.

****

This one weekend, Alice went home and I had the place to myself.

I got myself all pretty and then I made a jerkoff video and uploaded it to Pornhub. It was so thrilling to see how many likes I got and the comments were especially encouraging. Dozens of guys and a few girls wanted to meet me and do all kinds of nasty things to my dick. Talk about a confidence boost!

I was on cloud nine the whole weekend and every time I checked the website, I had a few more comments and a hundred more likes. By the time that Alice came back I had 2200 likes and 37 comments.

****

Alice walked in with her arms full of groceries and I noticed a large cucumber sticking out of one of the bags and grabbed it and stroked it in front of her and then placed in front of my crotch and wagged it.

She laughed and got down on her knees before me and began to plead, "No, Oh my god sir, please don't put that thing inside my greedy snatch. It's far too big!"

And we both broke out in laughter.

I did notice that her nipples had grown erect.

But then she rose up and attempted to put the thing in her mouth. And succeeded. It was so hot to watch my petite roommate felate this massive cucumber.

"Wlech!" She choked herself on the massive vegetable before removing it from her mouth.

"If you met a trans who had a dick this big, would you fuck him?" I teased.

"Fuck yes I would! I would probably marry him. Why, do you know anyone who has a whopper like that?" She teased.

"Noooo!" I laughed but it did make me smile.

****

This one time we went out drinking and came back to the apartment and she got up from her chair and stumbled and reached out and her hands grabbed my tits.

"Sorry about that Maddy." She laughed.

"Hey, no worries." I told her.

"You have great looking tits, by the way." She smiled at me.

"Thanks. You have a nice looking set yourself." I smiled back.

"Have you ever done any girl girl stuff before?" She asked.

"No I haven't, have you?" I asked.

"No, but I want to." She winked at me.

"I want to too, but only with another virgin like myself." I told her.

"You're a virgin? Oh my god! I thought that might be the case since you never talked about any guys that you've fucked or sucked." She blurted.

"It is what it is." I told her sadly.

"Hey, I'm sorry if it's a sore spot for you." She said kindly and touched my arm with her hand.

"Thanks, it's just that I really want to, but I'm scared too. You know?" I told her.

"I do know. My first time hurt like hell. I didn't think that I would recover, but when I did I became ravenous for dick. I bought all kinds of toys and masturbated for hours and hours but it wasn't like the real thing." She told me excitedly.

"It wasn't?" I asked curiously.

"No it wasn't. For starters a flesh and blood penis is softer and I loved the feeling as it ejaculated inside of me. That was the best! I lived for that. I even liked the way the fresh sperm dripped out of me." She laughed giddily.

"I'd like to see that." I told her.

She took my hand and led me into her bedroom.

Right away I picked up the smell of something unusual and it made me horny and I had to will my dick to not get hard.

I then saw several small wet spots on her bed sheet and even saw a long thin vibrator laying on her bedside table.

Alice went over to her computer and got on the internet and went to Pornhub and pulled it up. I grew a little nervous and wondered if she had discovered my secret.

She then typed in the word creampie and several videos popped up and she selected one that had a star next to it.

"Here is one of my favorites!" She said.

The video played out and after the guy came in the woman, she got to her feet and we watched at the man's sperm began to drip out and go down her inner thighs.

"God I just love that!" She said and her breathing grew heavier.

I partly watched the video and partly watched Alice as her nipples grew hard and pressed out of her t-shirt. I so wanted to reach out and touch them. I wondered if she felt the same about me.

"Would you ever consider having sex with me?" She asked curiously.

"I would, but you would have to be totally celibate for at least a year for me to even consider it." I told her.

"A year? Shit. You sure I can't tempt you to reconsider?" She asked and began to circle her erect nipple through her t-shirt.

I gulped and Alice smiled.

She took my hand and placed it on her right breast.

"Go on and feel it Maddy." She told me and grabbed my other hand and placed it on her left breast.

"You do have nice breasts Alice." I told her as my cheeks grew flush.

"You should feel them without my shirt." She said and pulled off her shirt and cupped her small breasts with her hands.

I placed my hands on her medium sized breasts and felt their weight.

"Go ahead and work your thumbs over my nipples. That's it. Pluck them with your thumbs and index fingers. Yeah just like that." She encouraged me.

"I really like this." I told her.

"I can tell because your nipples are showing through your shirt too." She said with lust.

Her eyes grew glassy as I began to tweak her nipples a little harder.

"You're making me wet Maddy. The harder you play with my nipples the wetter I will get. Most guys barely even touch my tits or nipples before going down and fingering me. Another thing I hate about guys. Yessss. Mmmm. Ohhhhhhh." She closed her eyes and moaned.

I watched as she began to grind her hips into the chair.

I trailed my left hand down her body to her crotch and tried to work my fingers under the waistband when she opened her eyes.

She smiled at me. But then she took my hand and placed it back on her breast.

"It's getting to you isn't it? I want you to touch me Maddy, but I also want to touch you too. May I?" She asked quietly.

"Yes, but be gentle. My nipples are really sensitive" I told her.

She reached a hand out and roved her fingers over my erect nipples.

"God Maddy, your tits are perfect." She blushed.

I pulled off my shirt and and unclasped my bra and she cupped my breasts in her hands.

"They are heavy. I love the way your nipples are erect." She cooed.

I placed her fingers on my nipples.

She then pinched them hard and I slapped her in the face.

"This isn't working for me Alice!" I said heatedly.

"I'm sorry Maddy. I got carried away. Please don't go!" She said in a quiet voice and grabbed my hand.

I just smacked her face and she apologized to me? Something wasn't right here.

I grabbed her throat in my hand and said, "Open your mouth!"

She did and I leaned over her and opened my mouth and spit into her mouth.

She closed her mouth and swallowed.

"Take off your shorts but leave on your panties. Now!" I commanded her.

Alice got to her feet and removed her shorts.

"You need to show me respect Alice. At all times. I won't tolerate anything else from you." I said sternly.

She nodded her head.

"You need to be taught a lesson." I told her and sat on her bed.

She looked at me and held her fingers in front of her crotch.

"Lay down across my lap." I told her.

Alice laid down across my lap.

"You have a really nice ass Alice. I love the way your panties are wedged between your ass cheeks." I rubbed my hands over her cheeks and slid my fingers between them.

I moved my fingers down to her pussy and felt along her slit and noticed that her crotch was damp which made my dick lurch between my legs.

I brought my hand up and smelled my fingers and noted the dew on them.

"You're wet slut. That is my pet name for you Alice. For all the men you have fucked and sucked, you are a slut. What was it you said? 205?" I asked her.

"255." She replied.

"Mistress. Call me Mistress for now." I told her.

"Yes Mistre..." She trailed off as my hand came crashing down on her ass cheeks.

"Smack!" It resounded.

"Little sluts like you need to be punished regularly!" I blurted.

"Smack!"

"Such a gorgeous ass!" I commented.

"Smack!"

"A perfect set of tits." I added.

"Smack!"

"Responsive nipples." I groaned.

"Smack!"

"But an insolent little tart!" I shouted.

"Smack!...Smack!...Smack!...Smack!"

I slid my hand between her legs and her panties were soaked.

I removed her from my lap.

"On your bed, on your back." I told her and walked back in my room.

I returned with 3 ties.

I secured her hands to either side of her queen sized bed and then tied one around her eyes as a blindfold.

I then removed her panties and draped the crotch over her mouth.

I started at her right breast and began to kiss and lick her nipple. I lightly chewed on it before going to her left nipple and doing the same while I drove my knee into her wet crotch.

I kissed my way down her stomach and got between her legs. I pushed her knees up and splayed them open and just gazed at her pussy.

"Such a sweet looking pussy. A nice large clit and thick purplish pussy lips." I told her and opened her meaty flaps with my fingers.

"Ohhh Mistress!" Alice moaned.

Juices leaked from her opening and I pressed my right nipple into her pussy. I got my nipple good and wet with her juices and then brought it up to her mouth.

"Lick your slimy juices from my nipple slut. That's it. Mmmm, yes. Lightly chew it. Harder. Harder. HARDER!" I demanded.

I then smacked her cheek with my hand.

"Such an insolent little tart. Maybe I should just leave you here to wallow in your horniness and not give you any pleasure." I teased.

"Please don't Mistress. I'm so horny. Please make me cum!" She begged.

"Oh I'll make you cum alright. You'll need to be wet enough to handle the massive strap on I have for you. A new toy I picked up with you in mind after watching you suck that large cucumber the other day." I sneered.

"Ohhhhh, mmmm." She moaned as my fingers entered her slick honey pot.

"Or perhaps I'll just whore you out and watch as multiple men fuck you repeatedly and then give you multiple creampies. Is that what you want slut?" I taunted her.

"No Mistress." She whined so I grabbed her nipples roughly and twisted them hard.

"I mean yes Mistress! Anything you want!" She quickly changed her mind.

I was getting off on this Dominance and rose from the bed and freed the monster cock I had been hiding under my skirt.

Alice's bathroom door was open and I admired myself in the mirror. My perfect tits and great looking ass as I stroked my huge 11 inch cock with both hands. How I wanted to ram this thing in the petite nymph's oozing pussy and fuck her deeply until I flooded her cunt with my sperm. There would be plenty of time for that in the coming weeks. So I resisted.

I was going to eat her out first. I was so looking forward to this moment. From the first time that Alice told me about the men who fucked her, I wanted inside her pussy.

I edged myself for days and then when I couldn't take it any longer I would masturbate in the shower and fire huge long streams of cum all over the shower wall. 8 huge ejaculations my cock would shoot out as I imagined it was Alice's cunt I was filling up.

And now, here I was between her legs.

I kissed her inner thighs. My lips working closer and closer to her strong smelling pussy.

I kissed up to her pussy mound and Alice breathed out, "Yesss Finally!" Only to be let down as I avoided her swollen clit and worked her right inner thigh with my kisses.

I then attacked her clit with my lips and began to trace the alphabet over her sensitive organ. I worked two fingers into her wet pussy and began to twist them in and out rapidly.

"Oh Mistress, oh Mistress!" Alice moaned and humped her hips up to meet my lips.

I used my free hand to play roughly with her right erect nipple and twisted and pulled on it again and again.

"Oh my god this is so amazing! Better than anyone has ever licked me before!" She groaned.

I purposely kept her on the brink or orgasm for well over 10 minutes.

"Are you ready to cum for me slut?" I asked her.

"Yes Mistress! Please! Please make me cum!" She begged me.

I descended back to her pussy and licked and sucked on her fat clitoris. I pursed my lips around her clit and flicked the sensitive pearl underneath rapidly with my tongue tip.

"Here I fucking cum!" She shouted.

I tortured her nipple and clit simultaneously until she peaked in orgasm.

"FUCK YEAH!!!!" She shouted.

Her back arched and my fingers were expelled from her pussy. I rose up at that point just as a giant gush of her syrupy fluids came out of her cunt. Like a fire hose on full blast her juices sprayed out and went all over my huge hard cock and stomach.

I was so full of lust at that point that I gripped my cock with both hands and jacked it off while using her slimy pussy juices as lube.

My orgasm was so intense and my cock went off and fired huge streams of semen all over Alice's face, neck, tits, stomach and pussy.

I thought that the ruse was definitely up as my dick lay against her pussy and continued to dribble semen down her slit lips, but Alice had passed out from the fierceness of her orgasm.

I retrieved my phone and took several pictures of her before licking up the mess I made of her body.

I loved the taste of my spunk and slurped it into my mouth as quickly as I could before Alice awoke and tasted it on her lips.

I then got a towel and wiped her body down with it before tossing it in my hamper.

I fingered her pussy and smeared her juices on her lips and under her nose to hide the heady smell of my sperm in hopes that that would be enough to cover my tracks.

I untied her hands, removed the blindfold, covered her body with the bed sheet, turned out her light and closed the door to her bedroom.

****

I was making breakfast the following morning when Alice came walking out. She was completely nude.

"Hey sleepy head. Want some breakfast?" I asked her.

"Yeah, that'd be great." She said tiredly.

We ate in silence and then afterwards she looked at me funny.

"What?" I asked her.

"What did you do to me Maddy?" She asked.

Uh-oh. I braced for the worst.

"What do you mean?" I asked her.

"I, uh, I think I love you." She answered.

I breathed a sigh of relief.

"It was pretty special wasn't it?" I told her.

Her hand covered my own and she brought it up to her face and kissed it.

"Special? No I'd call it like super-fan-tabulous!!!" She smiled and then giggled.

I felt like a fucking king!

"Where did you learn to lick pussy like that? Oh my god!" She said excitedly.

"I didn't. You were my first." I smiled.

Her mouth was open in shock.

"Do you remember any of it?" I asked.

"I remember cumming really hard and then feeling something wet spraying on my body before passing out." She told me.

"You gushed when you climaxed Alice. Have you ever done that before?" I told her.

"No never. Did you gush too?" She asked.

"I did. When your juices landed on me I rose up and gushed all over you in return. It was one of the best orgasms ever." I told her.