Being A Sissy, John tells his first time.

What would you do if you could be a woman for one day?

So I want to get started by this isnt about me 🙂 Jon the nudist but more of a helpful chat to get you thinking if you would you like to play the role of a submissive housewife, keeping the house up to par and making sure all the household chores are done with the utmost care? Maybe you would undertake all these duties while wearing some sexy maids gear. How about obeying your partner’s every demand and order, striving to be the best little subservient housewife you could be. Is being a sissy for a day one of your fantasies? Would you rather be sexy and dolled up than look masculine and rugged? Do you enjoy role playing and secretly have a closet full of sexy dresses, lingerie and costumes?

Are you a sissy?

If you are finding it hard to come out to yourself have a check of this by redditor Johnphillips26 yes it might seem a bit far fetched but who saying your first time can’t be a dream!

I’m straight and been with with only girls all my life but every time I get horny I can’t help but want to submit myself to pleasing a man. Finally it happened, I was especially horny one night and instead of just reading the posts on Craigslist I made one.

It said inexperienced bi-guy looking to suck and bottom for the first time. Minutes later my inbox lit up with emails and more hard cocks than my imagination could begin to play with. I was too nervous to meet at someone’s house or to have someone over, so one email stood out to me. He had a beautiful hard cock and told me he was in his office and wanted me to stop by.

Being A Sissy, John tells his first time.Before I could talk myself out of it I told him I would be there and to send me the address. I hopped in the shower and cleaned myself inside and out, shaved my ass smooth, got dressed and hopped in my car. I drove toward the address he sent me, every minute convincing myself I needed to finally try it.

When I got there it wasn’t a private office like I had in mind but a huge office building. It being 6pm there were still plenty of people and I nearly started the car back up. I couldn’t fathom the idea of moaning and taking my first cock in a building teaming with people. But I decided I had made it this far and I shouldn’t go back now.

I walked up the stairs and sat in the lobby where he instructed me to. I emailed him back with four letters, “Here“. I watched every man that passed by in anticipation of whether it would be his cock I would be sucking in the next few minutes. Finally one of the men came through the lobby a second time and with his finger motioned me to follow.

This was it, go time. No turning back. I gave him a sheepish grin and followed him to what I assumed would be his office but instead he went into the men’s restroom. No way I thought, this was not where he intended was it? I peaked in to the large bathroom with 3 stalls and 6 urinals, empty of everyone, except my man.

I followed him into the first stall, to my delight I saw it was large and the door went to the floor. No one could see there were two of us in here. I found myself in an all new, scary, but exciting situation. Alone in a stall with another man that I know has every intent to use me until he’s satisfied.

I fall to my knees and looked up into his eyes. He took my hands to his belt and I began unfastening it slowly, then unbuttoned his pants, and, for finally for the big real… unzipped his pants. There a found a bulge ballooning from his boxer briefs. I laid my hands on my first cock, rubbing it through his boxers, feeling it semi-hard. With both hands I slid his underwear down to his ankles and with one motion of my neck, slipped his warm fleshy dick into my mouth.

I began slowly, sliding my lips to the bottom of his shaft and back up to the head. I tried to do just as I’ve seen countless beautiful women do online. “Look him in the eyes“, “make sure not to use your teeth“, “go all the way down“, all swirled through my head.

Then it happened, the door opened to the bathroom and feet away I heard footsteps walk by. He didn’t even hesitate, with both his hands he softly grabbed the back of my head and began fucking my face. I now had a hard as rock throbbing cock in my mouth and I could taste the slight but distinct taste of pre-cum. I took both my hands and grabbed his bare ass, pulling his cock into my throat over and over again. I drowned out the sounds of men coming in and out and focused on the wet sound of my throat being fucked.

Being A Sissy, John tells his first time.A few minutes passed and I couldn’t help it anymore, I took his cock out of my mouth and whispered to him, “do you want to fuck my ass?“. He nodded and I took one of my condoms out of my pocket and handed it to him along with a bottle of lube (both purchased a while ago for the intent of me using them on a girl). I got on my hands and knees on the bathroom floor, toilet inches away from my head. I thought, “this is it, I’m officially a cock whore“, and slid my pants and boxers off.

He took my hips and pulled them toward him, spreading my cheeks apart. I looked back to see his hard cock wearing the condom I provided and him rubbing the lube up and down his shaft. I looked straight ahead, fearful of the notorious pain of the start. He began running lube on my asshole, and the amazing feeling of his hard cock running up and down my crack. Then he pushed.

I could feel the pressure of the head of his cock my exposed ass, gently pushing to make its way inside of me. Then it penetrated, and inch by inch his throbbing cock filled my virgin ass. I knew then I was his and I liked it. I started to push back on him feeling what all those women must have felt like with me. The pain never happened, my tight ass began to relax as I handed myself over to him.

For the next 20 minutes or so I fucked him right there on the men’s bathroom floor. Biting my arm to keep my moans silent to the men feet away, oblivious to my submission. I looked back to watch him as he fucked me and could tell on his face he was close. Several deep thrusts later he came deep in my ass, filling the condom. He pulled his cock out exposing my gaping hole. As he removed the condom I noticed his dick, slimy with cum, and as my way to thank him sat up and took him back in my mouth one last time.

After sucking and licking him clean I pulled my pants up and slipped out of the stall. Walking toward my car I could not believe that just happened. When I got home I checked my email, he said he can’t believe that was my first time and wanted to setup another date.

Do any of these indecorous behaviors pique your interest? If so,I may have described your fantasy and/or lifestyle.

Jon the nudist

Jon the nudist

Well, my name is Jon the Owner of You Only Wetter a 37-year-old, Poly practicing, Dom with two great kids. I am a happy busy internet geek with a love of all things Google and I love spending time sitting on the sofa watching the latest Dr. Who, Mythbusters or a movie. I am a nudist mostly at home but do like to go down to the beach and bare all or go for a little walk around some hidden woodland really would like to do the whole nudist holiday :)

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Being A Sissy, John tells his first time.

by Jon the nudist time to read: 9 min
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