Endearment
- 2 years ago
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A Condition Of Endearment free porn video
I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way.
Because of my exotic and sexy appearance, things could get interesting at times. When you are dressed as an alluring, sensual woman in high heels, and tight, little dresses, there are many assumptions that are made. Especially when one is a bit short, wispy and blonde, and has created a look even a cheerleader would adore.
I’d learned of the dangers and the risks of being a gender mixed gal. As a result, I always took great care not to deceive men or to find myself in a place where I might not be accepted. Now twenty, I’ve graduated from college and now have a very good paying job.
My weekends, spent dressing as a girl, are still considered sacred to me. As soon as Friday afternoon comes around, I return home and I shave my entire body smooth. I then use my skills to get all dolled up as Cari. She has become very good looking, and is a quite pretty and sexy looking girl!
My new job takes me many places. I find the travel to be exciting, and my work pays well. My connections through my Ivy league college experience helped land me my position. I live very comfortably as a result. I am very lucky because in some of my travels, I have been able to turn the end of my work weeks away, into short, extended vacations.
Recently as a result, I’ve been able to explore several American and Canadian cities. I usually am able to do so as my girl side, who very much enjoys going out on the town. I always do my on line research to find the right places to visit as a femme gal.
I am also lucky to be blessed with a short and slim body, a cute fine featured face, and a great eye for my own make up and appearance. Usually very few people can read me as a guy all dressed up. There is an assumption in my brain, that when I am dressed, I’m all girl.
I have worked hard at my appearance, and it has paid off in how truly convincing I feel I can be. Confidence is a girl’s best friend, and I have developed mine to a point of great comfort. I feel especially feline, when walking sensually in five inch high heels!
I had flown from Boston to Toronto on Monday for work, and had been staying at a Marriott Hotel in the downtown area. This past week was hectic. I had worked a good fifty-five hours by Thursday.
Fortunately I had Friday and the weekend off. As I’m allowed to book my own hotels, I had chosen this particular one due to its proximity to a couple of clubs I had researched previously on line. There is a method to my madness!
During the week, I had checked out one of those clubs late at night, as my guy self. It was called Crews and Tangos, and it was only about three blocks away from my hotel on Church Street. It had dancing, a large bar, and the crowd was a mix of straight folks, transgendered and gay. It was quieter during the week, but I was told that it was quite crowded on weekends.
It was the kind of club I felt most comfortable visiting as my girl self. They have nightly drag shows and in a club like this one, people expect that regardless of how pretty the girl must really be – she is really male! I’ve gone out with friends to straight clubs and have often passed “dangerously” as they say. I never wanted to fool anyone as to my true identity! It was the right kind of place.
I was pleasantly surprised to find people dressed fairly well here. The crowd was younger and mostly gay, but all kinds seemed to land at the bar here, including admirer types. I would come here as Cari.
I had virtually all day Friday to shop and get dressed. I could be my sensual girl self at last. Walking and shopping on Yonge Street, one of Toronto’s major streets, was fun. I found a dress in a dress shop that made my heart race. I bought it right then and there.
So excited by my dress purchase, I returned to my hotel. The dress fit perfectly, and I was very excited about wearing it this evening. I took my time getting ready in my room. I started with a bubble bath that was aromatic and lilac scented, and it was also skin softening perfection.
The joy of shaving and smoothing my body into a hairless delight is almost a spiritual experience for me. A little French perfume and in just my panties, I’m ready for the time in front of the mirror. I am always very detailed in my make-up.
I add long eye lashes, line my lips carefully and utilize every skilled detail I know - to highlight what the best features of my face. I lengthened my naturally shoulder length blonde hair with matching hair extensions, and then brushed it out. It was long, flowing and sensual looking. My hair always looks good with extensions, as it looks like it is one hundred percent all mine.
I finish my artistry with stunning bright red glue on nails, and paint my toes to match.
Now I was ready to get dressed. I always have a full bag of my favorite girl clothes. I love to try them all on if I have time. I got out my stockings and heels. I was ready to choose just what would be perfect and sensual, without being overtly sleazy or being too sexy.
I already knew that I’d be wearing my new dress tonight. It was black and lacy and made of a stretchy silk feeling material. The dress had straight half inch shoulder straps and a plunging v-shaped neckline. It was also low v-cut in the back – so a bra was out of the question.
The waist was quite tapered. With my constant evening corset training, my waist is down to 28 inches. My waist looked almost wasp like in the stunning dress, making my sometimes torturous nights sleeping in a corset - quite worth the trouble!
From the waist the pretty feminine dress flowed around my hips and then ended with delicate sheer lace at mid-thigh. It fit like a dancers dress, yet the soft fluffy lace layers made it fuller and frillier. It was tasteful, yet at the same time, it was incredibly feminine and sexy.
This dress would look great at any wedding, prom or formal occasion. My plan was that I would wear it from my hotel room to the night club, but with a shoulder cover up to subdue its overt sexiness. I chose a G-string for my waist and attached beautiful, black, silk, back seamed stockings. I strapped on my favorite pair of black leather, five inch sandaled high heels.
I finished my outfit with a short black fitted coat that still exposed my narrow waist.
Putting this all together was such joy. The total result gave me as spectacular an appearance as I have ever had. I was smitten with my reflection. I felt every bit as good as I looked!
I sure didn’t look a bit like a boy in a dress! I looked like an elegant, fashionable young woman, who in my mind could be on a magazine cover. I even had unteased my blonde hair slightly, to look as realistically female and as classy as a sexy young lady could. I was coming out of a four and a half star hotel, and I wanted to look the part.
Toronto was a new city for me, but I felt safe in the hotel's neighborhood. I wanted to enjoy the simplicity and delight of walking in my high heels in my fashionable, graceful outfit. I was in my mind - a pretty woman headed out for the evening. I had purposefully taken care so as to not go over the top. In the mirror, I felt self-assured, buoyant and delighted with my stunningly vogueish good looks.
I filled a small leather shoulder bag with make-up and my necessary things. I was ready for the elevator ride down to the lobby. I took a deep breath and felt some nerves, but also excitement. I simply needed to stay cool, walk as I’d learned for the past two years, and enjoy my walk for my fun night out!
The Marriott lobby is large and very well lit. I realized immediately that I fit in – but did get a couple of glances from men who noticed my sexy sway, and one who could see my exposed cleavage. The door man smiled and greeted me – nodding with a “ma’am” as I walked through the automated doors. His formality and smile helped convince me that I was indeed looking great.
The three block walk was marvelous and so thrilling. Being fancy free in heels and a dress with my seven inches tucked into a gaff is so erotic and sensual. My bum had perhaps more wiggle than it should have had. I was in an enchanted state of girlish delight, and I was working it as they say.
I was just happy, pleased with myself, and feeling fancy free. When I got to the club, a door man got the door for me and I entered a world of music, darkness, light, noise and confusion.
The club was three times as busy as it was during the week. The lighting from the dance floor strobed even into the bar area, yet it was still only nine P.M. I walked to the bar and found a single stool that was unoccupied. Before I could even remove my sweater, I was being bought a drink by a good looking man about six feet tall.
He greeted me, asking how I was and I thanked him for the drink. I sipped it and he asked me if I felt like dancing. I was in the mood for most anything so I said yes. We went to the dance floor after I left my sweater on the barstool, keeping my small pocketbook over my shoulder.
The first song was frenetic and fast. We both got into it among the growing crowd. Dancing and swaying sensually in high heels was just another delight for me. My new friend was smiling and winking at me.
While dancing, he asked me my name and we exchanged pleasantries. With the loud music interfering, I did hear him tell me something about his working at a car repair garage – but I clearly heard him tell me I was beautiful. He made me blush in embarrassment!
There was a pause in the music, and a surprisingly slower dance began. He wasted no time in holding me close. I felt his strength as his hands held me just above my derriere. I was getting flashes. I was already smitten, and feeling the submissive urges of feminine surrender!
In moments we returned to get my sweater. We had already agreed to go to my hotel! In but fifteen minutes, I was being walked back as he held my hand. We just knew and felt the raw sexuality and attraction to each other. He wanted me and I wanted him! He wore slacks and a dressy rolled up shirt. His hand felt coarse and strong. He stopped for a moment on the sidewalk and looked me in the eye.
“You are stunning, beautiful one! The only reason I know you are a Trans girl - is because no straight women ever come in there alone. I so want you!” With that said, we kissed – right in the middle of the sidewalk. His raw passion had me breathlessly reeling in anticipation.
His hold on me made me feel so small, so vulnerable and so feline. I was simply a young girl with a handsome, youngish guy. The rest of the walk had me feeling as beautiful and as happy as I ever could recall. Holding hands made me feel like I was a carefree girl.
He was impressed with my small suite. The bedroom was separate and had a bath adjoining. He laid down on his back on the bed as I grabbed a nighty, going into the bathroom to change.
I looked at myself in the mirror - all changed now into a sheer, black baby doll and smiled at my reflection. With a smile, I devilishly told the girl in the mirror she was about to get fucked! I giggled to myself. I sure knew what I wanted!
I came out and posed for him. He was lying on the bed completely nude. He was hard, huge and more than ready for his new found girl. His body and cock had me flush with excitement. He smiled, arms comfortably behind his head on the pillow.
“Wow! Come on over, you sexy thing!” He said with a sly grin. I was thrilled, yet played the game and femininely went to the end of the bed - posing with my arm on my hip and smiling in an absolutely genuine way. Almost staring at his stunning male member, I told him that “Someone is happy to see me!” I said it with sly and sexy grin.
I was so smitten with his stunning, large, wondrously erect cock that I couldn’t help myself. I got onto the bed and gave his muscled thigh a teasing kiss. Then another and another. Soon I went straight to his cock and gave it a long, tantalizing lick.
I was trying my best to act like a seductress. His flat abs and his strong, smooth, muscle rippled chest had me swooning. I never felt like a luckier girl! This guy was a hunk, and his cock was as well. I just instinctively had to take it into my mouth. I looked up at him, smiling broadly just before I did.
His cockhead, shaped like a missile tip, was beautiful and so was his shaft. He was long and thick and just perfect for me. I was so excited that I slid off my panties as I went to work on him. I was trying to stay cool, but this guy really moved me. He was perhaps in his late twenties, and far younger than my usual type. He was truly a young hunk of real man!
I began sucking and slurping and enveloping his shaft. He was delicious! I looked up at him and he smiled at me. He was watching my every move. I’m sure he could see the smile – well at least in my eyes! I was loving every second of his taste, and my own cock was throbbing as I savored his cock. Sucking cock was so great, but even better for a hot stud guy like him.
“Mmm yeah baby!” He began moaning. “Ooh that’s so good!” He said a few seconds later. I was really getting in to my work, as his pretty barfly pick-up. I had already turned into a needy and wanton slut. I felt insatiable and even ravenous in my desire to suck on it all!
I felt feminine beyond belief during this act - yet when I look down at my nighty, my rigid throbbing cock is dripping wet and standing upright. Tranny’s I know say this is typical of us girls. It just shows how much we are so good at pleasing, because we just love doing it so much! It really turns us on!
His prick was so beautiful and so hard. It was perfect and so big, and I loved the taste of his pre-cum and the smell of a man who was clearly blue collar and strong. His hands rubbed my back. They were rough and calloused. I even noticed his fingernails were quite dirty. That just turned me on more!
I am really good at sucking cock, especially when I really like the guy. I would go down as far as I could and then come back up almost all the way. I’d lick, then tease, and then make it disappear so that my lips completely enveloped each of his full eight inches.
My deep throating was clearly enthralling my young stud. My strong mechanic was beginning to groan almost too loudly. I knew I had to temper my efforts, but I was enjoying the act of sucking his cock as much as he was enjoying my talents!
I knew he was close, but I selfishly wanted more. I intentionally slowed down. This marvelous, stunning, godlike cock was not going to be wasted! I needed it so badly. I selfishly stopped. I practically jumped off the bed and took a condom from the bed stand drawer. He looked at me at first, wondering why in the world I would stop, but he knew what his new girlfriend wanted!
I was hasty and almost trembling while rolling the condom over his magnificent tool. His cockhead was so big and missile shaped. I was quivering in nervous excitement and anticipation. I knew from how he handled himself that this mechanic would be skilled with his tool! Finally I got the condom fully rolled on. I paused briefly while adding a little gob of lubricant to my bum.
This naughty, needy girl was soon centering herself atop him. In seconds, he began to slide inside me - as I gasped, not so much in pain, but in the joy of feeling him inside me! His rough, powerful hands held my waist as I was now getting help sinking down onto each inch - of his astoundingly, impressive, thick cock!
When my bottom met his balls, I let out a high pitched wail! “Oh yes baby!” I cooed. Nothing ever felt better. He reached up under my little black sheer baby doll and cupped my soft, perky breasts. I rode him with a craving want, need and desire. I was crazed in joy and relished each and every down stroke!
I never felt more natural in any place or form. Riding him was pure lustful instinct! My unconscious reflexive fuck strokes were inbred in me. As I humped his magnificent cock, I was practically crying in a state of joyous rapture and ecstasy. Ingrained in my female persona was this needy, wanton, woman who so loved the reality of procreating with a man even though he was wearing a condom.
To feel his hard member filling me in animal like thrusts is the ultimate mating and breeding dance for a girl like me. Nothing moves me more intensely than this ultimate celebration of affection. Getting fucked by a man so magnificently hung and skilled makes me frantic in joy and in passion.
My grinding down thrusts were breathlessly frenzied. I was filled with cock and the purest of lust. I never felt more happy and free. My own hard springing cock and balls were a blur, as the wet spanking sounds of our voyage to consummation thundered onward. Never had I felt more alive and happier with my being.
The bedroom was on a corner, and was windowed all across. I glanced at the wide skyline that was spectacularly visible in the well-lit lights. I was already in love with Toronto. It had given me a real man, and so talented as well. Suddenly hotel sex seemed perfect. I was riding upon the man of my dreams, and I didn’t even care that I didn’t know his name!
I’ve never been better in pleasuring a man because I was so pleasuring myself. This position enables me to grind on his entire boner while doing my best to grip him with my wildly ravaged sphincter. I was getting close to madness when my bouncing over stimulated cock became fully overwhelmed. It suddenly exploded, shooting stream after stream of cum onto my lovers stomach and chest.
I let out high pitched yelps that shook the bedroom. The full blown anal orgasm had such intensity that it caused my whole body to tremble. Now my spasm ridden and helpless sphincter was too much for him as well.
Now his grunts and huge groans filled the room as he tensed and released. He sent shot after shot into the condom, so deep into my depths. To say our mutually timed orgasm was amazing - would be but a fractional explanation of the euphoria and bliss that we felt.
I feel so blessed to be physically and emotionally wired with the ability to realize the wonder of true anal orgasm. I find that my anal orgasms multiply the intensity of my orgasmic experience almost ten-fold. The quivering delight that my entire body experiences as a man’s submissive lover is mind blowing and unforgettable. The appreciation and rapture during and after is truly an emotional and spiritual experience for me.
When we found our breath, I bent down and kissed his lips. His tongue swirled forward meeting mine as we were content as lovers, having just becoming one. We lay together, totally spent. I had been such a naughty slut, yet I felt wondrous and well rewarded!
He explored the curves of my smooth, lithe body with his calloused hands. It made me feel even more like the girl I so loved to be. We would sometimes kiss and caress each other. He would kiss my neck and chest. It had felt incredible and mind-blowing to be so ably loved by him.
I never even asked him his name. Contented, the two of us fell asleep while he was holding me and spooning me. This was the bliss and joy I so often found myself wanting and needing.
An hour later, I felt him stir. He slipped out of the bed quietly, trying not to wake me. He got up and quietly got into his clothes.
I let him slip out unobtrusively as I pretended to sleep. I could have used a last kiss, but I was more than content. That stud was one of the best men I could ever imagine meeting. His good looks, hot body and skills made my day, my week and my month.
I was gratified and so satisfied. I had just had the kind of sexual experience that I would have never dared to in the past, and with a guy that was so much younger than my usual type.
I’d always look forward to trips to Toronto, though I never found out his name - or how to get my car repaired by him! That man gave me a tune up and oil change that for me was one for the ages! I’ll never forget my mechanic and the special tool that he used on me that made me run like a charm!
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