FINAL Chapter

Dressing as a woman in secret, how far would he go?


Once my manpussy stopped throbbing I decided to freshen up and have some more wine and enjoy the porn movies that were on the television I had ordered. The girls in the video were shoving this big double headed dildo into each other. They were eating each other out and were cuming over and over. They were making me horny again and the wine was going down so smooth.

I started felling brave again and getting a little tipsy and wanted to test my courage. I decided that I was going to take the chance and drive to the nearest liquor store and buy another bottle of wine dressed as CandyCane. I was hoping to be seen by someone, anyone and hopefully not laughed at.

I freshened up my makeup and put my red miniskirt back on and wiped the excess Vaseline off my manpussy that was making my butt cheeks slide too much. I even got a feminine pad and stuck it to my skirt just in case I leaked a little from my big dildo that had just fucked and gapped my ass so good. I was getting so nervous as I gathered my keys and wallet.

I stood at the door and took a deep breath and opened the door to the hallway and hurried to the nearest staircase which leads to the parking lot. As I started down the second set of stairs from the third floor, someone was coming up! I didn’t know where to turn or to stop so I just kept walking at a steady pace holding my breath.

As I approached the couple, a man and a woman, I hid my face under my wig hair but peaked out of my bangs as we started to pass. The man was a tall handsome European looking man in his mid 40′s and was talking sternly to the woman who he had by the arm. As we passed I noticed he looked directly at my face and actually turned a little to see more of me as we passed.

I was so afraid he was going to laugh but didn’t hear anything except his voice directed at the woman. After they were almost out of sight I looked back and caught him still looking at me. Oh my god, did he know I was a man? Did he think I was ugly? Did he think I was a hooker?

I must have looked very different than anyone else in the hotel and all I could think about was if he found me attractive or not and how big his dick was. I finally reached the door to exit the building and as I searched the parking lot for anyone else I realized I still was holding my breath and let out a huge sigh.

The coast was clear. I hurried to my car but felt a complete feeling of freedom walking in plain sight dressed as CandyCane, as a hooker, a little slut! The cool air rushing up my skirt and was so cool and soothing. So this is how a woman fells when she is outside in a skirt?

Mmmm, the breeze was cool on my face, my makeup, and it cooled the back of my neck. I could feel it going through my thin white blouse and was cooling me off all over my chest and shoulders.

Once I arrived at my truck and got in, I looked in the rear view mirror and started to check my makeup like my wife always does when she gets into the car. How funny I thought to myself. After I adjusted my skirt and got situated, I started the truck and headed to the liquor store I had been to earlier in the day. Would it be a guy or a girl at the window this time?

Please let him or her be nice and not make any comments that will embarrass me I thought. Once I arrived at the drive up, there was a car in front of me. I decided to remove cash and my ID from my wallet so the guy which I could see didn’t suspect I was a man if he saw my man wallet.

“Hello,” I said in as low a voice as I could, “could I have a bottle of Sangria in the green bottle, please?” The guy looked into my eyes, then the car, leaning out of the drive up window a little more than usual I imagined and said, “sure young lady, you partying alone? Can I see your ID?” Just then I hesitated with my ID card, it was a man on the picture, me!

Oh my god, what an idiot I thought to myself that instant and slowly handed it to him. He looked at the ID, looked at me and smiled from ear to ear and handed it back to me and said “$12.75 please” as he went to the wine cooler. Whew, he wasn’t going to make a big deal out of my ID not matching my face.

I handed him a $20.00 as he handed me the wine and I nervously waited for my change. He reached out and handed me my change and again he looked into the car and down at my shaved legs in my thigh high stilettos. I looked up at him right into his eyes to see his reaction and he gave me a little wink as I drove away. I did it! I did it! Someone finally saw me as CandyCane and I even got a wink from a man I thought to myself, WOW!

Now, after being seen I was getting even braver and decided before I go back to the hotel I wanted to drive around a bit and feel the freedom of just being a girl in a car driving down Main Street. It was exhilarating and it felt so good to have my bare butt cheeks on my heated seats and it was making me tingle all over again.

My stomach was feeling jittery again as I thought to myself, I just want a warm throbbing cock in my ass but how would I do that without exposing myself? As I drove around keeping my face semi-hidden, I could hear people talking at each intersection in their cars or radios playing music as we passed on the street with their windows down.

No one was making a big deal out of me dressed as a girl but, who knew I wasn’t? No one but me.

Once I arrived at the hotel I hurried across the parking lot and up to my room without anyone seeing me. I was very surprised that all the practice I had walking in heels at home I can actually walk pretty unnoticeable in my stiletto thigh high boots. They make me feel so sexy with the leather on my thighs.

Once in the building, I start up the stairs and notice something. Oh great, look up there on the ceiling, hall cameras. Great, now I’m being videoed entering a room that was rented to a man. I wonder if they will report this or not even notice? Oh well, I’m here and I’m ready for a glass of wine.

Once I got the wine unwrapped and poured, I sat with my legs crossed over my shaved sack and could feel the warmth from my balls creeping up my thighs again and my cock stating to twitch. I wondered if that guy at the drive up would fuck me as I sipped my wine. I wondered if he was gay and how big his cock was? I guess I’ll never feel that REAL feeling of a cock in my manpussy.

After having a few more glasses of wine I was feeling no pain and the porn movies were getting to be boring. I said to myself,”You know what Candy, let’s go to the lounge.” I bet its empty and I can just sit at a little table in the back and just relax listening to some music.

Did I have the courage? I was drunk enough.

I grabbed the glass of wine and tipped it up and drank it to the bottom. Then lifted the glass of my imaginary friend and said out loud “fine, then I’m leaving” and giggled as I went to relieve myself before going downstairs. As I sat on the toilet with my cock between my legs I started to realize what I was about to do.

I was going to have to show my ID card again if asked and possible be exposed. You know what, the worst that can happen is I don’t get served and I come back to my room and fuck myself again with my dildo.

Once I finished relieving myself, I wrapped a few wraps of toilet paper on my hand and reach between my legs and wiped my manpussy off and the tip of my cock, feeling just like a girl. I was feeling so feminine and girly and it was wonderful. I then touched up my lipstick and powdered my face and rechecked my eyeliner. I couldn’t resist the full length mirror again and stood there admiring myself one more time before the revel.

Was I nuts or plain desperate?

I think it was a combination of the wine and my desire to be seen and admired, or maybe the craving to have a hot real COCK in my ass. I just want to be told I’m beautiful, just once dressed as CandyCane.

Once I finished in the bathroom, I practiced walking back and forth in the room from one end to the other so I could see if I needed to work on my walk or if I looked to manly. I was amazed that I looked the part, walked the part, and actually didn’t look to manly in the outfit I was wearing. The blouse hung perfectly to hide my small belly and wide shoulders.

The thigh high boots hid my very muscular manly legs and the fingernail polish and fake nails feminized my hands and my makeup was perfect. I had finally mastered the art of makeup and even toned down the small wrinkles and small bags under my eyes to the point they weren’t even visible. Using different tones of makeup to lighten the deep areas and darken the areas I wanted highlighted, I was ready.

I grabbed my key card to the room, my ID card and some cash which I stuck in my bra and headed to the elevators. Once I arrived at the first floor, I could hear the music through the doors and took a deep breath and walked out of the elevator. I scanned the room quickly and saw the room was fairly empty except for three guys playing pool and a man in the back where I wanted to sit.

The bartender saw me as I walked to a dark table in the back; a few tables away from the man in the back that looked like he was having a mixed drink. Once I walked to the table I could feel the guys at the pool table looking at me as my heels made their clicking sound on the wooden floor. As I sat I crossed my legs and faced them.

A few of them were gesturing obscenely as most men do when a lady walks into a room.

I was feeling no pain. I was numb but getting wet and excited seeing all these cocks in one place. Was this going to be the night CandyCane was going to be fucked by a real man with a big fat cock?

The bartender walked over and asked what I was having and I said “a glass of sangria wine if you have it?” For a second he looked at me like he knew something and asked for my ID card. I got nervous and said I had forgotten it in my room and he said “oh you’re a guest, what room?” I said I was in “room 308″ and he said “no problem” and went for the wine, whew!

No ID needed and no embarrassment in front of all these guys. I was starting to feel good about the situation.

Once I got my wine I noticed that the guys at the pool table were drunk and one of them started to approach me. I turned away from him as he stepped closer and asked if I wanted to join him and his friends. I slowly raised my eyes to him and said “I’d rather be alone if you don’t mind” and sipped my wine again. He was persistent and continued to get closer to me which was making me real nervous.

Just then the gentleman who was seated a few tables away got up from his table and said “the lady’s with me” and sat at my table!

I was in utter shock. It was the man from the hallway. He was gorgeous and had the most piercing blue eyes and perfect kissable lips. I looked up at him and said “Thank You.” He looked up at the man who was still standing there and he took the hint and walked back to his friends who laughed at him once he was back at the tables.

I sat staring at this hunk of a man and slowly his gaze reached mine and we were staring at each other. I finally blinked and he said “are you really alone?” I cleared my throat, took a tiny sip of wine I thought, and squeaked out a “yes” and asked “if he was alone as well?” He said he was for the night and put his hand on top of mine.

I almost screamed with fright, joy, delight. His hand was heavy and warm as he caressed my hand with his thumb and said if I remembered him from the hallway.

I looked up and said “yes” in a shaky voice and he said “then you know I’m with a woman in this hotel.” I again said “yes” and sipped my near empty glass of wine. I hadn’t realized I wasn’t sipping anymore, I was gulping it down nervously. He then said if I was offended by him coming on to me with another woman upstairs and I said “no.”

As I stared at his handsome face I felt a connection with him and felt like he knew my secret, or did he? He ordered both of us a drink as we watched the guys at the pool table leave. We were alone except for the bartender. He looked at me as we drank our drinks and asked “if I would be more comfortable in my room?”

I actually started to feel my cock get hard and my manpussy get hot and wet as I said “I would” and started to stand up as a gesture for us to leave. He threw a $10.00 bill on the table and asked the waiter to send up a bottle of Sangria to room…hesitating as he looked at me and I said “308.”

He placed his hand on my shoulder and walked me to the elevator and pressed the up button. My legs started to shake and my manpussy was getting real hot and wet. I could feel the warmth of his hand through my blouse as the doors opened he eased me forward into the elevator. Once we stepped inside he pressed the “3″ button knowing I was on the 3rd floor.

The doors closed and he turned himself towards me, looked into my eyes and pressed his swollen lips into mine! I instinctively opened my mouth as he snaked his flaming hot tongue into my mouth. I could smell his cologne…mmm. I could feel his unshaven face stubble pierce though my makeup and I could feel something on my thigh. Was he getting hard already? Was that his cock or his keys?

I could only imagine what his motives were, his thoughts, did he know?

I didn’t care at that moment when the elevator started to move up to my room. I just continued to suck his tongue like my wife would do mine and tried to remember to be gentle with my hands. I even raised one of my thigh high boots and rubbed his leg with my thigh as we entwined for the brief ride.

As the elevator started to jerk in the usual stopping motion, we slowly separated and for an instant looked into each others eyes knowing this was going to get hotter and hotter by the second.

He reached down and grabbed my hand as the doors to the elevator opened and he lead me to room 308. We stood there for a second and again he kissed me as I reached for my room card in my bra. He took the key, inserted it into the slot. As the green light flashed I knew I was going to be in for a treat and hopefully a good fucking.

As we entered the room, he stopped and looked around and said, “I thought you were alone” as he pointed to the two glasses on the table. I looked up at him and said “they were both mine” blushing I’m sure. I know I must have had an embarrassed look on my face so he took me into his arms and kissed my swollen lips and stuck his tongue down my throat.

I could feel his muscular hand on my neck as he continued to tongue fuck my mouth and squeezed my ass through my miniskirt. I was starting to get hard as a rock but leaned my pelvis away from him so he wouldn’t feel my cock on his body.

Should I tell him now? He has to know or he might get angry once he reaches down to touch my pussy and all he grabs is cock. I stopped him for a second and put both hands on his chest and looked up to his eyes and said, “I need to tell you something.”

He reached up with his hand and gently touched my lips and said “I need this” and proceeded to shove his tongue in my mouth.

I stopped him again and said as I grabbed his hand and pressed it to my cock “does this change anything?” He gently squeezed my cock and shaved sack and said “I was hoping you had a cock I could suck.” Than he slowly knelt to the ground kissing my chest and then down to my waist as he reached into the waist band to pull down my skirt.

I shuddered as the cool air from the air conditioner and his hot breath hit my upper thighs as my skirt slid down my thigh high boots. He licked all the way around each boot at the thigh and with his other hand slide a finger into my manpussy. I let out a small moan of pleasure…”mmm” as his hot mouth continued to search for my now engorged cock.

I could feel him nibble at my silk thong underwear at the crotch and finally letting my cock out of the mesh. He slowly kissed the tip then slurped my cock down his throat. I stood there looking at myself in the mirror with a man sucking my cock and trembling near collapse from the fear I had thinking I was going to lose him or anger him once he found out I was a man.

I stepped back and slid onto the couch and started to sob and he quickly came to me on his knees and said “why are you crying, YOU’RE BEAUTIFUL!” I stopped crying, looked into his eyes and said “I’ve waited so long to hear those words and I thought you were going to be mad and leave once you knew I was a man!”

He wiped my tears and kissed me passionately with his sexy lips, sliding his hot tongue passed my enflamed lips and down my throat.

I stepped out of my miniskirt and started to unbutton his shirt and looked into his eyes and said “I want this to last all night” as I sucked his nipple into my mouth. He let out a moan of pleasure and I reached between his legs to find he had a monster cock. He must have been 10-12 inches long and at least 5″ in diameter!

I wanted that cock in my mouth, in my ass and wanted it now. I continued to suck his nipples and with the other hand undid his belt and then his pants. His pants once unbuttoned slide down his muscular legs from the weight of his belt and I immediately dropped to my knees to see his gorgeous cock and to my suprise, no underwear.

The head of his cock was huge and purple and barely fit in my mouth much less his length. I opened my mouth as wide as I could and put that throbbing head into my mouth and slide all I could into my mouth. His cock was huge and on fire. I could feel every vain engulfed in blood with my tongue as he pumped it deeper and deeper into my throat. I could fell his cock head at my deepest point but I wanted him in further and grabbed his ass as he pushed forward.

I pulled as he pushed into my mouth stopping him every few seconds for air as he lunged forward. I know girls take a cock and swallow it so I thought so can I if I’m persistent. I continued to pull him in further until I felt my throat give at the deepest point like something broke or give in as he pushed down my throat to my adams apple!

I could feel him deep, deep in my throat.

Could my throat ring I had read about finally be broken? He knew he was in deep and he even reached down with one hand to feel his cock in my throat. Once he felt my neck and his cock inside my throat he immediately started to moan and groan holding back his cum. I could feel it boiling up in his shaft on my tongue as I held his cock deep in my throat as I inserted a finger in his ass.

He let out a moan of joy “uuuhhh,” as I finger fucked his ass.

I wanted every drop of his manhood in my throat so I pulled him out for a few seconds to get some air. I took a few deep breath and shoved him in as far as I could get him in with hot wet saliva dangling from my chin. His balls were against my chin and nose and I could feel my mouth stretched open farther than it had ever been opened.

He reached behind my head and started to pump his monster into my mouth and throat like he was fucking a pussy.

Inch by inch he pushed and inch by inch I swallowed until I could feel his legs tense up and then the lava rising up his shaft gushing down my throat. It felt so good that my own cock began to twitch and squirt cum onto my cloth and thighs as I sucked him dry. I could feel every pulse of his cock on my tongue as he came.

He pumped and pumped cum into my belly till I felt like I was going to bust. Then I pulled away gasping for air with sticky saliva running down my chin and clinging from his cock and my lips. I gasped for air and looked up at him with my tear filled and mascara smeared eyes and immediately sank his cock back into my throat remembering a video of deep throating and how men loved it.

I remembered from the video if I stuck my tongue out under his cock I could breathe small amounts of air and could last longer with him in my throat. I could feel his hand holding the front of my neck again so he could feel his cock pulse his hot lava down my throat. I could feel his man meat deep, deep in my throat.

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June 2018
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