Chapter 6
(FINAL CHAPTER)
Was He Becoming A Cross Dresser
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 the big double headed dildo into each other and 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 and be seen by someone, anyone and hopefully not laughed at.
I freshened up my makeup and put my red miniskirt back on and whipped 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 underwear just in case I leaked a little from my big dildo that had just fucked 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 staircases which lead to the parking lot. As I started down the second set of stairs…….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?
OMG, did he know I was a MAN? Did he think I was ugly? Did he think I was a hooker? I must have looked different than anyone else in the hotel and all I could think about was if he found me attractive or not and how big was his dick? 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 SLUT! The cool air rushing up my skirt was so warm and soothing. So this is how a woman fells when she is outside in a skirt? Mmmm, the breeze was warm on my face, my makeup, it cooled the back of my neck and 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, 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 car 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? 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 and 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 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? OMG, 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 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. 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, being seen I was getting even braver and decided before I go back to the hotel I would 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, 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 was? 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 am very surprised that all the practice I had in walking in heels at home, I can actually walk pretty unnoticeable in my stiletto thigh high boots, and 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 get the wine unwrapped and poured, I sit with my legs crossed over my shaved sack and can feel the warmth creeping up my thighs again and my cock stating to twitch. I wonder if that guy at the drive up would fuck me as I sipped my wine. I wonder if he was gay and how big was his cock? I guess I’ll never feel that REAL feeling of a cock in my man pussy.
After having a few 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 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 and 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 finish relieving myself, I wrapped a few wraps of toilet paper on my hand and reach between my legs and wiped the tip of my cock and manpussy off, just like a girl would do. I was feeling so feminine and girly and it was wonderful. I then freshened up and 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, I’d hoped. I just want to be told I’m beautiful, just once.
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 belly and wide shoulders, the thigh high boots hid my very muscular manly legs, the fingernail polish 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 a few 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; two tables away form the man at another table 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, and 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 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 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 stated 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. He was persistent and continued to get closer to me which was making me real nervous.
Just then the gentleman who was seated two 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” and he looked at the man who was still standing there and he walked back to his friends who laughed at him once he was back. 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 and squeaked out a “yes?” and asked “if he was 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. 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 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 in his hand through my blouse as the door opened he eased me forward into the elevator. Once we stepped inside he pressed the “3” button knowing I was on the 3 rd 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 is cologne, I could feel his unshaven face pierce though my makeup and I could feel something on my thigh…..was he getting hard? Was that is 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, 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 hand and 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 and 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. 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 hands 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 and would lean 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 touched my face 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 squeezed my cock and said “I was hoping I had a cock I could suck” and 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 skirts 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 crouch 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 shaking near collapse form the fear I had thinking I was going to lose him or anger him once he found out I was a man. I slide back onto the couch, and started to cry 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 lifted him up to his feet as I kissed him.
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 grown of pleasure and I reached between his legs to find a MONSTER COCK! He must have been 10-12 inches long and at least 6” 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 undo his belt and then his pants. His pants once unbuttoned slide down his muscular legs and I immediately dropped to my knees to see this gorgeous cock. The head was huge and barely fit in my mouth much less the 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 on fire and 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 wanted to go further and grabbed his ass as he pushed forward. I pulled as he pushed into my mouth, intermittently stopping him for air as he lunged forward. I know girls take a cock and swallow it so I thought so can I. I continued to pull him in further until I felt my throat give at the deepest point and he went down my throat to my Adams apple! I could feel him in my throat. He knew he was in deep and he even reached down with one hand to feel his cock in my throat and immediately started to moan and groan holding back his cum. I could feel it boiling up in his shaft as I held it with my hand.
I wanted every drop of his manhood in my throat so I pulled him out for a few seconds of air, took a deep breath and shoved him in as far as I could get him. His balls were against my chin and I could feel my mouth stretched open farther than it had ever been opened and he reached behind my head and started to pump his monster into my mouth 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 into my cloth as I sucked him dry. He pumped and pumped cum into my belly till I felt like I was getting full, then pulled away gasping for air. I immediately sank his cock back into my throat remembering a video of deep throating. If I stuck my tongue out under his cock I could breathe air through my nose and could last longer with him holding my neck so he could feel his cock pulse his lave down my throat and I could feel his meat in my throat. Once we pulled away we both collapsed into each other’s arms on the couch and both breathing hard from the experience we had just enjoyed.
I sat up looking for something to clean myself with, since my cloths were covered in my own cum. He handed me the tissue and we both laughed and he poured us both a glass of wine. As we sat in my little foyer, I asked him who the woman was with him. He said it was his wife and they had come to see a divorce lawyer. I said I was sorry and he said “don’t be, she has lost the drive to have sex and I can’t live without it.” He then said if I wanted to tell him my story and I said it was a long one but as he could see I was a man who had retired and was felling alone, lonely, ugly and wanted to be loved like it used to feel. He reached out to me and slid me close and said he would be happy to fulfill all my dreams as he raised my chin and kissed my lips ever so softly.
I leaned into him and put my head on his chest as the porn movie on the television changed to a new one with a girl getting hammered by a huge cock. I glanced at the television and looked at him and he began to kiss me ever so gently. I reached down to his flaccid cock and started to massage his sack and could feel his body warmth. I wanted to feel a real cock in my manpussy and he knew it. Once the move started, he suggested we move to the bed. I asked if I could freshen up and took off my cloths except my thigh high boots and my bra which concealed my breast less chest and redid my makeup and lip stick. I walked over to the bed and he reached out for me, said he loved my lip stick and I rolled into his arms thanking him. AS the movie started to progress so did we. My manpussy was getting hot and tingly and I could see his monster getting hard under the sheet. I leaned forward and slowly started to kiss his sack and lick his rod up and down leaving bright red lipstick on his cock. I looked up at him and said, “Will you fuck my manpussy?”
He smiled and reached down and raised me to my feet and slid me onto my belly on the silk sheets. I instinctively raised my butt off the bed and exposed my bright red love hole and he immediately leaned forward and kissed it. He then inserted his tongue into my butt and started to tongue fuck my anus and he was experienced. His tongue darted in and out of my home sending shock waves up my spine as my butt got higher and higher of the bed. Eventually he had me coming out of my skin and crawled up behind me on the bed. He nibbled on my shaved butt cheeks and stated to lick my back sending shivers up and down my spine. I was already rocking back and forth giving him the green light to bury that monster in my ass. He didn’t need much persuasion and was in position ready to stab my waiting manpussy. I looked back at him as he kissed my shoulders and I could feel the head of his cock aimed at my back door. I whispered “this is my first time, please be gentle” and he kissed my back and slide his tongue down my spine and once more penetrated my ass with that meaty tongue, lubing me good for his cock.
As his cock pressed into me, I tightened up and I could feel the pain surge through my body and I said “stop, stop” and he backed off just for a second and just eased forward till his knob penetrated my entry and continued to slide in and out very slowly. I could feel my own anal lubrication start to flow and he began to pump in deep e and deeper. I thought he was going to bust me in half as his enormous cock started to engorge with blood and it seemed he was in as far as my tummy and I could feel every ridge of his veins and cock head as he slide in and out. The pain eventually began to become pleasure and the warmth began to rise as his pumping began to increase in speed and strength. He grabbed my shoulder and whispered “if I was ready for the fucking I had wanted” and as I looked back I said in a whimper “fuck me good, please, please.”
All the times I had fucked myself with a dildo and imagined how it was going to feel with a real cock didn’t even compare to the real thing. It felt hotter and I felt fuller and the real cock felt WAY better than a rubber cock. It moved with my back pushes and bent as I moved and throbbed inside me and I could almost feel his heart beat through his monster cock sliding in and out of my love hole. He was huge and I couldn’t have asked for a better fucking then the one I was getting. He was grunting and groaning and was making deep growling sounds as he pumped forward. I wanted him to shoot all his juices in my ass and as he started to tense I was ramming backwards as he rammed into me. I no longer had the pain that I had experienced initially. I was cumming and as I closed my eyes I imagined how my wife would move when we did it doggy style and the sounds she made as her pussy contacted around my cock. I wanted my lover to feel my contractions; I wanted to be a woman getting fucked right at that moment.
As his cum started to fill my ass I started to squeeze with my anal muscles and I could feel him squirming with ecstasy. He was screaming, “yes, yes, oh god, yes” as I tightened and released my anal muscles and my own cock was throbbing and slapping my belly with every twitch and thrust. As he dumped a gallon of cum into my hole my cock began to squirt cum all over my stomach and bed. I could feel the heat of his cum inside my belly and it felt so good being filled up for REAL. My lover still had one more surprise up his sleeve and as he rose off of me he nudged me to get up in a doggy position. Before I could say anything he had his tongue darting in and out of my cum filled ass and he had me squirming with pleasure. He sucked my little hole and it felt like he was eating me alive. I rolled over on my back and he continued to clean my manpussy and cock spic and span. I looked back into the mirror and could not have imagined CandyCane was going to get the fucking she always wanted, but she finally did. The End
Candy XOXO
August 24, 2016- -
-
1 likes this
- -
-
Report
August 24, 2016- -
-
1 likes this
- -
-
Report
August 24, 2016- -
-
1 likes this
- -
-
Report
August 28, 2016- -
-
Report