Real Man Takes MJ’s Virginity

Around October every year, my fem side begins to overtake my body and mind. In recent years, i also started to self participate in Loctober wearing a chastity cage while I was home. I kept myself smooth as possible, watched sissy hypno every night, slept in nighties and use beefy BBC dildos every time I showered.

Because of the buildup, my desire for real men was at an all time high. Normally, my profile showed I was only interested in women, trans or couples, but I added men and any time I did that, I would get flooded with messages, likes, friend requests and flirts. I don't consider myself passable, but it was a real confidence booster to feel so desired.

Of all the guys that sent me messages, this guy from Windsor caught my interest, he was a Bills fan and we chatted for while before I had to take a break so I could workout. While I was working out, I couldn't stop fantasizing about him and his impressive cock. I decided after I was done working out, I would get dolled up and send him a pic.

When it comes to sex with anyone, I have really bad anxiety and found gummies to be very helpful. After eating a gummy, I turned on some girly music and started to get ready. I spent hours getting ready, making sure I was smooth, primping my wig, spending time on my makeup which I suck at and for the first time, I watched videos on how to douche. After I was confident I was nice and clean, I inserted my buttplug and finished getting dressed.

I picked out the sluttiest, sexiest outfit I had and my tallest, sexiest heels. The outfit included a corset, a black lacy long sleeve body suit, black crotch less pantyhose, black thong with a pink plaid pleated mini skirt. When I finally got done, it was late and I was horny and with the gummy, I was willing without hesitation. I took a pic and sent it to him. His response was quick and priceless, he actually stuttered in his messages. It was so cute. He gave me his phone number, then we texted a little and he told me he had to work early the next day. He wanted to wait until later the next day to meet, but I was dolled up, I douched and I was horny as hell for his gorgeous cock. I practically begged him to let me cover over and I promised I would make it quick. He agreed and asked me to hurry over.

I grabbed a tote, packed wig, a lacy eye mask, skirt and heels. I put on jeans and a hockey Jersey over everything else and near midnight, I made my way to his place. He left the door open and I got changed in his living room while he waited for me in his bedroom. I took a quick awful pic before I strutted down the hall and announced I was coming in my softest voice. When I entered his bedroom, he was standing by his bed and his room had a red glow, so it was dark, but we could still see each other. With my heels on, I was way taller than him. We hugged briefly and I reached down to feel him thru his boxers. I assumed he would already be hard, but was soft. I commented that I could help with that and asked to get comfortable on the bed while I removed my heels.

He was naked lying on the bed and after I joined him, I could see his cock in the dimly lit room just laying there curled up resting on his balls. He was also fairly smooth down there which I found hot. I took his cock softly in my hands and gave the a soft kiss then began to stroke him. I wasn't feeling any reaction and was getting worried he may be too nervous and wouldn't get hard. I started to lick his shaft from head to his balls, then sucked each nut before I licked back up his cock to his head and I could feel him growing a little. That excited me and I squeezed onto my plug in anticipation I would be fucked soon. Then I took him into my mouth and began giving him my first ever blow job. Like many gurls like me, I fantasized about this so many times, watch so many videos, it just felt natural like I have done it a thousand times. He started to moan and placed his hand on the back of my head. I continued to blow his cock and bob up and down, then swirl my tongue around his head which causes him to moan and after several minutes he was at full mast.

I don't remember actually how we changed position, but he was now kneeling on the bed and I just finished removing my buttplug and thong. I brought a bottle of lube on the bed, gave his cock a kiss, then dripped lube on his cock and stroked his shaft a couple of times to make sure he would be nice and slick. Then i turned around so he could fuck me doggy style. I undid the snaps to my bodysuit and wiggled my ass which made my caged clit giggle under me. He pushed my skirt over my back and i asked him to please fuck my sissy ass. He lined himself up and got the head in me easily. I was worried it might hurt, but my shower BBC didlo was bigger than him and he slid in easily. Soon he was balls deep and I moaned at thought of a real man was about to make me his sissy bitch. He grabbed my hips and began to fuck me, I fell to my elbows and enjoyed the feeling of being fucked. I think I called him daddy a few times and I know I begged him to give it to me harder.

It didn't take as long as I hoped, but in a few minutes, I heard him say, "You're going to make me cum." I replied with, "go for it big guy." He picked up the pace and soon he made a familiar moaned/grunted that he was having an orgasms, slammed into me a couple times really hard and inseminated me. I didn't feel it throb or feel him jet in me like I hoped, but it didn't matter, I just helped a real man cum. I wiggled my ass and squeezed down onto his cock letting him know I was most pleased with his efforts.

I thanked him for fucking my sissy ass and then he pulled out which felt slightly disappointing. Then I became a little frantic because I know he had to get up early. So I got off the bed, reinserted my butt plug, pulled my panties back up, grabbed my heels, thanked him and left his bedroom.

While in the living room, changed and packed quickly, said 'sweet dreams' down the hall and left. I practically skipped to my car I was so ecstatic. On the way home I thought, crap, I didn't offer to clean him up, I just left him kneeling on his bed with his cock covered in lube and probably dripping cum onto his comforter.

It was quick, it was hot and he doesn't know he was my first. When I got home I stripped to my outfit minus the skirt and heels, removed the plug and was able to confirmed he did cum in me. Then with water off, I fucked my self in the shower with my BBC dildo stuck to the wall until I came. I caught the cum ozzing from my caged clit it and eat licked up every bit of it.