Blackmailed to be Me

The night was warm with an occasional breeze tickling our skin. Max's arms held me tight and made me feel safe, safe and loved. I leaned my head back against his shoulder and closed my eyes. Max's breath skirted along my neck like flame. With every breath I wanted him closer but there was no way for him to get closer to me, except there was. Gently I pulled the back of my dress up. Now all that was between he and I was my panties. And then I pulled them down. His slacks were rough against my bare ass. I forced my hands between us and un did his pants. Max's teeth teased the skin at my neck. Pulling his cock free of his boxers it felt like a steel rod between us.

"I want you inside me." I whispered as he nibbled on my ear. I need to feel you inside of me."

Max reached into his pocket and pulled something out as begged for him some more. "Hold on I am just getting ready for you. I heard a cap pop right before I felt Max snake his hand between us and rub something cold on the outside my asshole. Before I could speak again, he pushed inside of me. My heart exploded, it was nothing like when Tommy fucked me. Every inch of Max's cock felt amazing as it slid up in me. He was never fast, never pounding away at me. He was always gentle and smooth up and down, up... down. He continued on like that as I came again and again for almost an hour.

"Are you read for me to come." Max asked as he pushed his cock deeper then I had felt him go before. "I can keep going if you want more."

"Please fill me up with your cum." I said breathlessly.

With his hands on my hips Max started to pound into me faster then before and I came again flooding my cum soaked panties with another load as I felt his cock burst inside of me. His cum felt amazing inside me. Max pumped into me three more times before pulling out.

His softening cock hung between us, resting against my inner thigh.

"I don't deserve you." I said as turned my head and kissed Max full on the lips. Our tongues played together in his mouth. I turned around as we kissed and reached down to hold his cock in my hands. He twitched and started to stiffen. I knew exactly what I wanted to do next.

Dropping to my knees I lifted his cock till it was sticking straight out from his body and swallowed it hole. He tasted of strawberry's and cum, I would never be able to eat strawberry again without flashing back to that night. Reaching into my panties I scooped some cum onto my fingers getting them nice and wet. Then I reached between Max's legs and slipped first one and then two fingers inside him. Him let out a quite moan as his cock spasmed in my mouth. I wanted to draw this blow job out so I slowed down. I moved my fingers and mouth in unison - Cock in, fingers out. Cock out, Fingers In. I sucked on him and played with his ass until my jaw was sore. For the first time in an hour I pulled Max's cock completely out of my mouth, "Can you cum again."

With a big smile Max took his cock from me and started to stroke himself. I closed my eyes and opened my mouth wide. It only took a second for the first rope to splash across my face. Max let out a deep sigh as he layered stripes of warm cum across my face. A moment after the last rope draped across me, Max reached down and cupping my face pulled my to my feet.

Taking his time, Max repeated our lunch time encounter. He was less frenzied as he sucked and licked the cum from my face now though. I kept my eyes closed until he was done, savoring the feeling of his tongue on my face. When he was done he pulled me in close and kissed my neck.

"My turn now." He whispered in my ear as he spun us around and dropped to his knees. I was still in a glow from the last few hours and didn't realize what he meant until he lifted the hem of my dress up. His fingers had wrapped themselves around the waistband of my panties before I found my voice.

"Wait, no you cant." I said the words tumbling out of my mouth faster then my lips could move. Causing some of them to almost run together. "I mean it isn't."

"I know you have a dick." Max said his voice cold with confusion.

"Ok, I am super stupid." Max leaned back looking up at me as I spoke, "I sort of locked my clitty up and mailed myself the key."

"Clitty." Max said as he started to fish into his pocket once again. "You know those things aren't exactly made by master locksmiths."

Pulling a set of keys from his pocket Max flashed me a broad smile. "The little locks that come with them, they usually have a universal key."

I stammered over a few words as Max pulled down the front of my panties and unlocked the cage. The cage fell to the ground and Max took me into his mouth. I am a bottom and I have always been on the bottom. No one has ever taken me into them like he did and I just started crying he started to pull up but I held his head in place, "Don't stop."

Tears streaming down my face I twisted my fingers into Max's hear and squeezed as he bobbed up and down on me. His hair felt like silk ropes entwined in my fingers; as he sped up I felt like I was holding onto a thoroughbred as he pounded away against me. I tried to hold back, I begged my body to wait to let him keep giving me this pleasure. My body betrayed me, and I exploded in his mouth. As the orgasm, the first of its kind for me racked my body I let go of his hair and fell back onto the hood of his car. Laying there I couldn't catch my breath my clitty trembled remembering the heaven it had just been expelled from.

Standing up Max smiled at me, a dribble of my cum running down his chin. Pulling myself up I returned this afternoons favor and licked my cum from his face. We kissed and he pulled me close, his cock rubbing against my clitty. Both our members were excited by this and started to stir. Pulling from his embrace I turned around and bent over the hood of his car, "Fuck me again."

Max smiled as he slipped a finger inside me. "I could go again." Popping his finger out of my ass Max continued. "I have a better idea."

Max walked off towards the back of his car leaving me bent over with my panties around my knees and my skirt flipped up. I couldn't possible think of a better idea then feeling his cock inside me again and I told him so. Just the same Max continued rooting around in the trunk. Finally calling out an excited yes.

Returning Max laid out a flannel blank that when laid out made a rather large bed. Max then smiled and started to strip his clothes off. I followed suit and within a few seconds we were completely naked in the woods. I walked over to where Max was standing and he pulled me close his mouth touching mine as his tongue slipped past my lips and caressed mine.

I knelt down and took a hold of Max's cock, he was rock hard again. I licked the tip as I rolled his balls around in my palm. His eyes rolled back as he asked, "Do you want to be on top this time?"

His cock made a very audible POP, when I pulled it from my mouth. "No."

Laying on my stomach I spread my legs wide and looked over my shoulder at Max. "I want you to make me your bitch."

"My bitch." Max said as he knelt down behind me and applying more lube to my back said. After he fingered my opening till I was almost ready to cum again, Mad got down on his knees and gently slid his cock inside me. "You will never be my bitch. But you will absolutely be my queen."

I came right then and there so hard I thought my clitty would never stop shooting. Max took his time slowly and methodically pumping in and out of my ass. When he finally came he collapsed on top of me. Max laid there until his cock softened completely to roll off of me. I cuddled up to Max laying there basking in the afterglow surrounded by the sounds of the jungle.

The sun breaking the horizon woke me up, Max was still holding me tight though in the night he had pulled the flannel blanket on top of us. Just as I moved Max started to stir, he kissed me again and I was reminded of last night. As he broke the kiss I was reminded that it was morning. "Oh god, I have to get home. I have to work in like. Soon."

Max chuckled as he started to get unwrap the blanket from around us. "Yeah I need to get going to, my flight leaves at noon."

Flight, what did he mean flight. Was I just a one-night stand for him; I mean it was a good night. An amazing night really, and I didn't deserve more than that, but I wasn't ready for him to be some pump and dump not anymore. I stood there naked as Max pulled his pants on tossing his boxers onto the blanket and rolling it up.

I leaned against the hood of his car, my legs spread just slightly, and bit my lip as I asked him, "So your flight leaves at noon."

Max only tossed me a glance and a smile as he walked the bundled-up blanket to the trunk. "Yeah, my boss wants me in Des Moines Saturday. We are trying to close a deal on some property and the owner is a big Bulldogs fan. So, I am flying into take him and his wife to a game."

"So, you're coming back?" I asked in a demure voice. That caught Max's attention.

"Yeah, I am coming back." I live here. Max grabbed his shirt off the ground and wrapped it around himself in one smooth motion as he approached me. "And I could pick you up straight back from the airport and we could spend the afternoon, well."

"We could fuck like bunnies." I said as slipping my hand in his pants and wrapping around his cock.

"I was thinking of lunch and a movie." Max leaned in for a kiss while squeezing my ass and slipping a finger inside me. "But after that we can definitely have a good time."

Max tried to pull away, but I kept a firm grip on his manhood while running my thumb along the length of it. "How about you fuck me right now."

"I thought you had work." Mad said as he slipped a second finger inside of me. I unbuttoned his pants and let them slide down as I turned around, bending over the hood of his car again. Max placed the tip of his cock gentle against my rosebud and asked. "Are you sure we have time for this."

I looked over my shoulder at him with as stern a look as I could muster, "If I don't feel your cum dripping from my ass for the rest of the day. I am going to cry."

Max arched one eyebrow at me as I continued, "Do you want me to cry."

Without answering Max slide his cock completely inside of me. I moaned and he started pumping his cock in and out of me like an express train. I grabbed his hand and guided it to my head, my blond wig gone, and begging him to pull my hair. As he did, I moaned loader and he pumped faster. As he drew closer to climaxing. I felt his cock twitching as he held back. I moaned loudly and called him daddy and that did it. He pumped his warm cum inside me for a solid minute. Blast after blast filled me completely.

Pulling out Max knelt behind me and licked my hole cleaning up the small amount the dribbled out when he freed himself from me. I laid there savoring the moment. I knew it would be over soon and like Cinderella I would have to go back to my real life soon. My boring boy life.

Setting my dress on the hood next to me, Max gave me light pat on the ass to get me moving. I pulled the dress over my head and climbed into the car as we backed away from the clearing and started home. I was half way home before I realized I had left my cage, panties, bralette and wig back at the clearing. I didn't say anything the whole way home and neither did Max. Pulling into my apartment Max put his hand on my knee and squeezed.

Stopping in front of my building Max turned and gave me a sad smile. "I am never going to see you again am I."

"What."

"It is ok, I know a closeted." Max stopped and returned his gaze to the parking lot in front of us.

"I'm not, I mean I am or was. I never really talk about my life with the people I work with." I said Max looked to me and I couldn't meet his gaze.

"Like I said."

"No, you don't understand. I want." I paused to take a deep breath, "I signed up to this website it is supposed to help you become a new you. I didn't know what they would do it turned out to be Blackmail."

"What the hell." Max said as he tried to pull my gaze to him, but I resisted.

"So, I submitted all of these pictures and waited. The website said it help me be a better me." I looked up finally meeting Max's gaze. "That was a year ago, and I had changed my mind but then I got a letter and...

My voice trailed off as I looked away. Taking another deep breath, I started again, "It started Monday and these last four days have been the greatest of my life. I want to date you I just don't know yet who I am."

"So, Sunday is off?" Max asked as he let his hand rest once again on my knee.

Taking Max's hand, I slid it up my skirt "Wild horse couldn't drag me away from you on Sunday. But a jet liner can today."

Max brushed his knuckles against my sticky clitty and gave me a deep kiss. We didn't say another word as we parted. I was running late so I hurried inside and pulled off my dress and jumped in a hot shower. I didn't want the smell of last night to wash off, but the hot shower helped wake me up. I didn't quite realize how tired I was. When I finally turned the water off, I was ready to get through my day.

After I dried off, I tossed my towel over the shower curtain and started to leave the bathroom when I saw something out of the corner of my eye. Standing in the mirror was a girl. I was a girl. I wasn't wearing makeup or panties I was naked. Clean from a shower and I was a girl. I was always a girl and would always be a girl. Standing there looking at myself I realized I need to stop wearing the boy costumes. I was done with that.

Looking through my panty drawer I needed something amazing for today. I grabbed a green lace thong and slipped them on before moving on to my bra drawer. The only green bra I had was a full coverage granny bra, I debated going braless but decided screw it all. I will be me. I wrapped the bra around my chest and stuffed a silicone titty into each cup. I decided right then I was getting implants sooner rather then later.

Remembering the Tartan school girl skirt from the night before, I moved on to finding a blouse. Most of the ones I grabbed while not sheer did show a bit more of my green bra then I wanted to. After fifteen minutes of looking I broke down and changed to a white bra. I left the green thong, I just wasn't going to match. I looked like a proper school girl, which honestly, I acknowledge was maybe not the best look for work. But I simply didn't care.

Without a wig I got a few more stares on the bus ride to work. I smiled back and even waved a few times. Once I got downtown and to the office the elevator ride was the quietist I have ever seen it. Four floors up Jack Dorset grabbed my ass and said I had nice tits. All the guys on the elevator laughed right up till I asked Jack if his wife still worked in the building. A hush fell over everyone as a big smile spread across my lips.

The elevator dinged and I stepped out into the bull pen. I don't know what I was expecting but no one gasped, or fainted, not a single person dropped their coffee mug. I took my seat clocked in and got to work. It was almost lunch time before anyone said anything, and then it was Mr. Hughes secretary. She was a couple of years younger then me and looked completely terrified standing just outside my cubicle.

"Yes, Beverly." I said never looking up from my monitor.

She cleared her throat but didn't start talking right away. That was when I started to faulter. I was playing the bad ass, but I couldn't look at her while I was doing it. When I didn't look up after almost a minute she finally spoke up, "Mr. Hughes, would like to see you in his office immediately."

As soon as she finished speaking, Beverly hurried away. I stopped typing and took a deep breath. I rolled back from my desk and stood up smoothing out the back of my skirt I started towards Mr. Hughes office. You would have thought I was walking to an execution the way everyone's eyes followed me. Debbie Perkins is the only person who met my gaze when I looked at her, she looked mildly disgusted with me. She held my gaze as if she was daring me to stop when I passed her desk, so I did. I was ready for any insult she could through at me, and then she talked. "No makeup, no stockings, your nails aren't done. You are coming to work not the corner store, show some self-respect."

That was not expected. Debbie turned around in her chair and went back to work. She sucked all the confidence I had right out of me. I put my head down and hurried into Mr. Hughes office. He was on the phone and kept me sitting there while he talked.

"I understand what your saying, but you saw him at the meeting Wednesday he was zoned out the whole time." Mr. Hughes said tossing me a sideways glance.

"I think he is on drugs, he showed up to work this morning in drag. Complaints are the issue here, I understand your feelings on this, but this is my..." He was talking about me.

"I see well then. We may have to part ways." Mr. Hughes hung up the phone and looked at me. He was angry at first but then once he looked me up and down from head to toe. His disgust flashed briefly to lust. "Look here waters I don't know what you are playing at here showing up in Drag like this."

"I am not in drag." I answered back, though my words carried almost no conviction.

"I run a business here. Not a playground." Mr. Hughes said as he stood and crossed the room to a small office liquor cabinet. "I don't know what you are on right now. But get your head right or I will fire you faster than you can twirl that little skirt of yours."

"I don't think you can fire me." I answered. My hands would have been shaking if I hadn't been holding them so tight together.

Mr. Hughes took a swig of cheap whiskey and set the glass down before crossing the room to stand next to me. "I own this company and I can fire whomever I like."

Before I could respond Hughes bent over and slid a hand up my skirt. His hand resting barely an inch from my panties. All the fear I had pumping through my body the second before was gone. I was going to be perfectly fine. I looked up to Mr. Hughes my eyes meeting his and slapped her hard across the face. Hughes stumbled back his mouth hanging open like a fool.

"So, what one second I disgust you and the next you want to fuck me." I announced as I stood up. "Well you can fuck right off, I quit."

I turned and started towards the door when Hughes called out to me. "Wait stop. You can't quit." I just laughed and kept walking towards the door. "I'll raise your salary."

That made me stop. I waited a moment and then said, "You have a minute."

"I can't lose this account." Hughes walked back to the liquor cabinet and poured himself another drink. "They want you, so they get you. I lose this client and we go under six months a year tops."

I took ahold of the door ready to leave but I thought off all the people in the office. All of them out of work, sure most of them sucked but they didn't deserve to be unemployed. "First, you ever put your hand up mine or any other woman's skirt I will be gone. Second, you have to be less of an asshole around here."

"Fine." Hughes muttered as he took a long draw straight from the bottle.

"Third."

"Fuck off." Hughes muttered under his breath. I didn't leave or even respond I just waited. "Fine, third."

"This is who I am. I am don't hiding that from the world." I opened the door to leave and stopped looking add one more thing. "My new title is Senior Account Manager."

The door closed before I heard Mr. Hughes response, but an email was sent out later announcing my promotion. Walking back to my desk I stopped at Debbie Perkins and gave a sharp knock too announce myself. She never looked up from her monitor while answering, "Yes."

"I was wondering if you wanted to grab lunch later. We have never really talked much." I said as I gave her cubicle a once over. She had a few pictures and in all of them she was dressed to the nines.