I Dressed Charlie Like A Girl And She Never Went Back free porn video

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Today is our long awaited graduation exercises. I am just waking up from last night's party, Charlene is already up and in the shower. Not surprising, because she always loves to look her best in the morning. This morning was going to be very special in honor of graduation and celebration of our almost four-year love affair. Well, at least that's what she promised.

I kicked off the sheets and admired my morning wood. I could hear Charlene humming so I knew she was done showering and was now during her make-up. Just thinking about her making her grand entrance into our room was turning my morning wood into a full hard-on. I made just enough noise to let her know I was awake. I knew she got my message because I could hear an occasional giggle. The bathroom door opened and there she was, so beautiful in every way.

Her hair was wrapped in a towel and she was wearing sheer panties that hid nothing. Off came the towel and her curly red hair fell to just above her ass, the towel thrown on our bed. What a picture, her make up was knock out slutty, ruby red lipstick, matching rouge, light blue eyeshadow that highlighted beautiful blue eyes, and just enough mascara to highlight her already very long eyelashes. She gave me a smile as played with her unbelievable tits. Every inch of her skin was pure porcelain in unblemished perfection and soft beyond description.

Her breasts were perfect C's, with huge pink areolas, and dark, full nipples. I took a certain amount of pride in my responsibility to mold those nipples with my constant attention and sucking. She gave me another sexy smile before twirling her body to brush her hair. I love watching her do that, and she knew it. She made sure to show off her body with every brush stroke. Blinded by her tiny waist and perfect round bubble butt my hard-on was almost painful by that point.

Finished with her hair, she wiggled sensually over to our bed, grabbed my cock, smiled, then sat down close to me, and started to slowly jerk me off.  Her knees were planted between my legs and spreading them. I was in another world then she started with my cock, licking the cum off the tip then slowly licking down my cock to the balls which took in her mouth while licking them driving me near to explosion.

After pulling her panties off and flashing her hairless teeny cock, the serious blow job was to begin. She switched position so her mouth was on my cock and her ass was wiggling in my face. I knew instantly what Charlene wanted. Grabbed some lube from the bedside, because Charlene loved to be finger-fucked while sucking my dick. I love that too, she would begin to transform into womanhood, slurping my cock wildly with her wet mouth and tongue, letting moans and squeals release from the deepest parts of her body.

I  started to cum but after swallowing one rope she clamped down hard on my cock with her teeth, which was a trick of hers to stretch out the fun. After she was sure I was not going to immediately cum some more, she relaxed her teeth death hold and started to slowly deep throat me, then stopped. Slipping on top of me to start grinding her little dick on mine.

Moaning as she climbed up some more, she started dry-humping my cock between her ass cheeks. She reached behind herself to grab my cock and direct it to her pussy. As her ass started to swallow all of my cock, her facial expressions turned lustful and her pace became maniacal. She rode my cock a long time until I couldn't hold back any longer, I exploded inside her and seconds later, she came herself all over my stomach and chest.

Charlene cleaned me and herself with the towel, fell back onto me, her face inches from mine and fell asleep. I struck by her beauty just stared and began to think of the first day Charlie became my Charlene forever.

Charlie and I were dorm mates from our freshman year. I would always look out for him because he was so petite and could not handle his alcohol. Charlie liked girls all right, but he attracted more men with his shockingly feminine features, girlie voice, long red hair, and beautiful face.

Either by mistaken identity, general curiosity, or out and out perversion, it seemed like, at almost every party, I had to stop some guy from fucking him. Really sometimes, it was just crazy, because no matter how dangerous the situation I had to save him from, he just had no recollection of it the next day.

The final party before the break was supposed to be the wildest party of the semester. We arrived together, but as soon as he started acting crazy, I left him to his own desires while hanging out with other friends. I would see him in the distance, in different states of undress, but kept promising myself to ignore him for once.

But as the party was starting to end, I got busy trying to find him and bring him back to our dorm. He was nowhere to be seen. I started to worry and was asking everyone if they had seen him.

Finally, one very drunk guy said while laughing, "two guys nearly had to carry him up to the master suite."

So I run up the stairs and try the door, but it was locked. Then I heard two guys laughing and telling Charlie knows what to do next, so I kicked the door open. Charlie was on his knees wearing full make-up, pretty pink panties, and holding both guys' cocks.

I pulled out my phone to take a pic while telling the two dudes, "this will be proof of assault!"

To my surprise, both guys pulled up their pants and ran out of the room.

Charlie just looked in my direction then flopped to the floor, right beside a pink pocketbook. As I started to collect his pants and shirt, the anger hit me and revenge took over my thinking. I folded his boy clothes, stuffed them into the pocketbook and looped it around his neck. I got him to his feet and told him to wiggle his way home. Still very drunk and probably doped up on something else, he smiled, reached out for my hand and wiggled all the way back to the dorm in nothing other than his pretty pink panties.

Once in the room, he just plopped face first into his bed. For the first time, as he lay there, I couldn't help noticing his very feminine ass in that pretty pink panty, so round and full. His make up was perfectly applied and whorish. Then I turned him over to free the pocketbook from his neck. He gave me a cute smile and I immediately noticed how tiny his cock was, and him proudly spreading his legs to show off.

I started to rifle through the pocketbook, hoping to find evidence of its actual owner when the only thing that became clear was this was Charlie's pocketbook! All the make-up he had on matched everything in his purse and when I spotted bright red nail polish, I decided to paint her toes and nails. Then shaking her to a more alert state I had her blow on them till they dried.

After a little more digging her pocket, I spotted her matching jewelry set, pearl earrings, necklace, bracelets, and ankle bracelets. I put them all on her. Then, still confused but obeying, I had her wiggle over to the mirror to fix her lips. That's when she seemed to fully wake up, but in a panic.

"What did you do to me!" she screamed.

Walking up to her from behind I said, "Nothing Charlene, you did this to yourself."

I held out my phone so she could see herself kneeling before two guys holding their cocks.

"I guess I'm going have to send this pic to your parents and friends as a Christmas gift. Right, Charlene, after all, you look so pretty in this pic."

Immediately she started begging, "Please, Rick. I'll do anything. don't let my secret out."

"Is your secret that you are a sissy and love sucking cock?"

"I've never sucked cock in my whole life, but do I love dressing."

"You love being a girl don't you, Charlene, and you want a man to fuck you as a girl, don't you, Charlene?"

She tried to deny it at first, frantically shaking her head no, but then, after I pulled her hand to my cock, she kept it there when I let go, rubbing it and feeling for its size. Already, she was becoming the whore I wanted.

"I'm going to make you my secret Charlene and teach you how to be my sissy slut. I know now, you always wanted to be my secret sissy slut. Now take off my shoes, socks, and pants, to get a good look at the cock that's going to fuck you."

She started to cry but followed my instructions. Now on her knees, her mouth inches from the tip of my cock, and still crying, she started to jerk me off without me asking. I started to leak lots of cum.

"Now lick that up, Charlene."

She did with a smile and slurping tongue.

"I can tell you like that, whether you cry or not. I'm going to have you swallowing lots of my cum from now on, bitch! Now take more of my cock into your mouth. Now as you suck back up towards the head keep it in your mouth, but lick the head with your tongue. Now repeat and repeat each time going deeper down my cock then more passionately licking the head."

I don't remember exactly when she stopped crying, but she did, and started to give me the best blow job of my life. I didn't have to force her or give her any more instructions and before I knew it, she had my cock all the way in and her cute little chin was hitting my balls on every down stroke. She began to suck feverishly, hell-bent on pleasing me with her mouth.

I started to take more pics of her sucking my cock and having her smile as best she could for the camera. When I knew I was just about to cum, I had her look me in my eyes, so I could tell her not to spill a drop, and she didn't. I exploded at least three ropes of cum down her throat. She swallowed it like candy then sucked my cock until every trace of cum was gone.

"That was wonderful, Charlene. Now fix your make-up. I need to lay down, but when you are finished come lay in bed with me."

She seemed so happy that I liked her blow job, she giggled, grabbed her pocketbook and wiggled her ass to the mirror.

I lay there, watching her apply her make up so expertly I started getting hard again, and I could see how that pleased her as she regularly looked back at me to watch my cock grow.

"Pretty enough for you, Rick"? Turning to show her pretty face, then spinning for me to show off her gorgeous body.

"Pretty enough to fuck, holding my bulging cock. Now get your sissy ass over here."

Just before she reached the bed, I sat up grabbed her tiny waist and said, "I want a real close look at my new girlfriend."

I pulled her tighter to me and started sucking on her nipples. That's when the deep feminine moans started floating out of her mouth and a sexy girl smile came over her face. I kept sucking on them and as pulled my lips from one hard nipple she would quickly shove the other nipple into my mouth, giggling and panting at the same time.

"Charlene, your panties are soaked, is that just from sucking my cock?"

"Yes, and swallowing your cum."

"Oh, sweetie," I said, as I moved my hands to her ass, spreading her cheeks, and lightly rubbing my finger all around her hole. "Having my cock up your pussy will make you my bitch forever."

"Yes."

"Now go bring me your pocketbook. I saw some lube in there. We'll use that to finger fuck your pussy until you beg to have your pussy cock fucked."

And she wiggled and giggled to her pocketbook then back to me, she gave me the lube and a sexy smile.

I had her lie across my legs, stick her ass in the air, while spreading her cheeks, the little whore. After applying the lotion, I started slowly finger fucking her, one finger then two, then faster as her girly moans got louder, and I could feel her pussy clamping down on my fingers with each stroke. Without me saying another word, her hands were all over my cock, then her mouth, till she started pleading, "Please, Rick, fuck my pussy. Please make me your bitch. Please put your big cock in Charlene's pussy."

So I did.

I had Charlene pull her panties off, lie on her back, I spread her legs and started to dry hump her ass, stopping near her pussy with each stroke until she started screaming, "Please, please please fuck me."

Thinking she had as much teasing as she could stand, I pushed the head of my cock into her ass hard, and fast, then stopped.

Her face shocked and scared, I moved to short slow thrusts and her face fell into lust and the girly moans which became shrieks of joy. Then I shoved it all the way in and hard. Again, that look of panic. Then as I slow fucked her, taking full strokes inside her, the moans and shrieks flowed out of her mouth like songs, and jets of her cum started shooting from her tiny clit. Laughing, I scooped most of it up in my fingers and had her lick them clean while continuing to fuck her, which made her shoot more tinkles of sperm that she happily sucked up.

"Well, Charlene, a good girl would already be cleaning my cock with her tongue and mouth after such a great fuck!"

Almost jumping to my cock but before literally sucking it, she gave me a sultry smile and asked, "What else would you like your sissy slut to do?"

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They found the door unlocked when they got back to Karen's. Gilly was sitting in the lounge with one of Karen's videos playing. She obviously had something on her mind as she was hardly taking any notice of what was happening on the screen. "I guess things didn't go too well at home," Karen said, sitting beside Gilly and hugging her. "Come on, tell us what happened." "Mum had talked to him but it made no difference. We tried to make him see reason and relax his rules but he...

3 years ago
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Charlie and KarenChapter 2

Karen was ready and waiting when Charlie arrived a few minutes before eight. She was dressed in an almost transparent white blouse through which a bra would have been visible if she had been wearing one. It barely covered her nipples which were standing out invitingly through the thin fabric. Her black skirt was the shortest she had and didn't quite cover the lace trimmed tops of her hold-up stockings. She had never gone out in it a few times but never with stockings and always with shorts....

2 years ago
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Charlie Ch 0912

Chapter 9 The bouncer moved the rope out of her way, and Charlie entered the club. Music assaulted her ears. The smell of smoke, alcohol, and bodies filled her nostrils. It was just the distraction she was looking for. She pressed her body between different people to get to the tables in the back corner. Melanie always had a table for entertaining. Periodically, Charlie would have to rub against the back of some random male. One guy actually turned to say something about being rubbed with a...

3 years ago
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Crossdressing Charlie Episode 6 The Tennis Uniform

CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...

2 years ago
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I think Charlie is cheating on me again

I think Charlie is cheating on me again. The first time occurred just six months after we were married. He had a torrid affair with my mom’s sister, Bessie. Aunt Bessie was a notorious whore who would fuck anything on two legs.Aunt Bessie was a voluptuous teen when he was seduced by a male teacher in high school. The teacher taught her the fine arts of pleasing a man. She became an accomplished cocksucker with the ability to deep throat. Bessie was a willing and eager student who became...

Cheating
4 years ago
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Uncle Charlie and my Summer Family Ch 4

Chapter 4. Thunderstorms (4600 words) As Tess entered her third week in Arkansas the weather turned nasty. The days became exceptionally hot with heat indexes in the high 100s between 10AM and 2PM. Between that and the bugs the outdoors were nearly unbearable. Then the afternoon thunderstorms would roll in and cast severe downpours that would soak you to the bone in moments. This led to them hanging out indoors much more than they’d like. For a family that chose an outdoor lifestyle it...

2 years ago
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Charlie I

Personally I found her gorgeous. Her hair was a hybrid of blonde and brunette and she had incredibly thin legs which were accompanied by knee socks or the standard type of tights and a miniskirt which generally left very little to the, or in this case my imagination. Her breasts were just the right size, not too big and not too small either. I had talked with her on several occasions and it seemed to me that she, in personality terms was just as nice as her body. Her personality...

2 years ago
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Charlie Ch 3337

Chapter 33 Nathan sat on Charlie’s bed with his head in his hands. How could this girl not understand what just happened? Did she not feel anything about the way he touched her? What the fuck? He let go of his head and looked towards the bathroom door. For a brief moment, he smiled when the sound of the door lock engaged. With a small huff, he moved to the bathroom door and put his hand in the middle of it. Though the door stood between them, he could feel a larger chasm building. It was time....

4 years ago
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Charlie

Charlie was struggling to get free from a swarm of opponents when he heard the referee’s whistle and the siren indicating the game was over. His team had been defending hard for the last few minutes protecting a three point lead in their first Northern district Rugby League final. Now as reality set in they knew that they had achieved what was deemed impossible by the critics. Against all odds their small country town had broken the games longest running drought by defeating the highly...

1 year ago
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The Ladys House Part 1 of 3 Three Dresses for Charlie

The Lady's House Part 1 of 3: Three Dresses for Charlie By Gail Blue The tires made a dull thunk-thunk noise as they ran across the cobble stone street. The bus looked out of place next to 1800s style shops and houses. Just a few blocks away, the town was more modern, though still well- mannered and quaint. But in the town center, there were no cars, and no modern electronics were visible from the street. Charles got off the bus behind a load of Japanese tourists. He tried...

2 years ago
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Bruce Charlie Daniel and My self

It was Nonmember twelve, the shool was having a Pep Rally for our home coming game that evening. The gym was full of students our football team was on the floor the cheer leaders were cheering. My friend and I has sneaked beneath the bleachers and was getting peeks up the girls dress and skirts. As we worked our way out the end we made sure to move so it would not attract attention so we left one at a time. There was two huge portable chalk boards at the open end of the bleachers and my friend...

4 years ago
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Looking After Charlie

It was the phone call that every parent dreads, the one from casualty."Hello, Ms Williams, this is Nurse Ratched from the Royal Infirmary. We have your son Charles with us at the moment." At this point I died a little. "It's not too serious, he's got a broken arm and some cuts and bruises but he's basically fine. Would you like to come and collect him?""Five minutes, give me five minutes," I said as my heart pounded."As I said, Ms Williams, he's basically fine. There's no great rush."There's no...

3 years ago
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Charlie Ch 2932

Chapter 29 Nathan stood in a bit of shock. Those weren’t the words he was expecting to hear from Charlie. Yes, they were what he wanted to hear, but definitely not expecting them. Her hands on his back were making it difficult for him to think. The only thing that kept crossing in his mind was how close she was standing to his erection. The soft feeling of her lips brushing against his was not helping either. A voice in his head kept telling him to grab her and rush her up the stairs to his...

3 years ago
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Charlie Ch 2124

Chapter 21 It was about five o’clock that same afternoon, when Charlie’s phone beeped. She was laying on her bed, half dozing and half reading a book. Nathan: Need movie night Charlie: I’m okay. Nathan: I need one! Charlie: Okie dokie She rolled onto her back, wondering what weird movie Nathan would play this evening. It even made her smile that he would need a movie night, and that it wasn’t just about her lack of sleep. Sometimes, everyone needs a ‘Chinese comfy movie’ night. It was a...

4 years ago
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Charlie Ch 0104

Chapter 1 Charlie stood on the balcony, watching the rain fall from the darkened sky. It made a soft cascading noise that felt vaguely comforting. She inhaled another puff from her cigarette and exhaled it just as easily. Charlie took a moment to think back on some of her past experiences. Sure, there were men that had stirred some feelings within her. There were others that satisfied a few primal needs and urges. However, none in particular stood out in her mind, there just hadn’t been the...

3 years ago
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Finding Charlie

After sixteen hours on the bus, I arrived in Tulsa, Oklahoma just before noon on a hot July day determined to find Charlie, actually Charlotte, but that’s not what I called her. I flew into Chicago and then took the long bus ride to Tulsa, wanting to experience Route 66. After almost two years of meeting Charlie, my cyber lover, I wanted to surprise her, just show up, a daring act in itself as fear of what a disaster this might be swept over me. What would she think when she realized who I...

3 years ago
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Finding Charlie

After sixteen hours on the bus, I arrived in Tulsa, Oklahoma just before noon on a hot July day determined to find Charlie, actually Charlotte, but that’s not what I called her. I flew into Chicago and then took the long bus ride to Tulsa, wanting to experience Route 66. After almost two years of meeting Charlie, my cyber lover, I wanted to surprise her, just show up, a daring act in itself as fear of what a disaster this might be swept over me. What would she think when she realized who I...

Straight Sex
3 years ago
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Charlie Zeros Lastditch AttemptChapter 3

He woke up the next afternoon not remembering what had happened the night before. He stumbled to the telephone and quickly dialed his boss in a heated rush as he wouldn’t be showing up for work that day, and judging by the crumpled crème-colored card that he found in the palm of his hand, he also had an appointment with Artie Tedesco that he hoped to avoid, considering how nauseous he felt. He swore that he would never go to the bar to drink again, regardless if this Artie Tedesco brokered...

3 years ago
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Charlie and KarenChapter 16

After getting the new staff settled in on Monday Karen arranged another visit to Luke's SM studio. Charlie wanted to go to see if he could learn Luke's technique and Helen wanted to be punished by him again. She fixed it for Wednesday night but asked if he could get more guests there. "Especially men, there'll be two of us to be used this time." Karen wanted to set off early so they could have some fun with Helen on the way but Charlie said no. "It's not fair to leave Gilly to do all...

2 years ago
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Charlie Avoids Being Fired bimale MMF DP

My name is Sam and I manage a small company offering leisure services. There is a small team of staff and the nature of the business means that some weeks we just see each other at team meetings and work independently the rest of the time.Four weeks ago I was working on my own at a computer in the office. I needed to research something on the internet and opened the browser to look for the information that I needed. When I started typing something into the address bar the autofill came up with...

2 years ago
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Charlie Miley Ch 05

‘I was afraid to admit that I even had a problem. After my first week here I almost snuck out in the middle of the night. I had a bag packed and everything, but then my boyfriend called. Well, my ex-boyfriend, I guess. He told me how proud of me he was and that he loved me. It reminded me that I still had hopes for our future, you know? I want us to be together, but I realized it would never work if all I did was drink every night at a frat house until I blacked out in some strange guy’s bed.’...

4 years ago
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Charlie Ch 0508

Chapter 5 Charlie’s eyes felt like they had been glued shut. It took a herculean effort to open them. There was a steady stream of fuzz on the television screen. Nathan’s legs were propped up on the coffee table. The pillow and her head were now completely in his lap. As the rest of her body gained a bit of consciousness, she realized that one of his hands was wrapped in her hair. The other one rested on the side of her body. She shifted her head slightly to look up at him. His head had lolled...

2 years ago
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My Charlie

His name was Charlie and I’d known him forever, or so it seemed. We were kids when we first laid eyes on each other; only just entering adolescence and for about ten years or so, we remained very much in love. I can’t begin to describe the closeness and affection that grew alongside us all those years ago, and I can only put to words the affirmation of this and hope dearly that you’ll understand what it means to truly love someone, as I did Charlie. We were in love, yes, I’ll say it again and...

Gay Male
1 year ago
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Charlie Zeros Lastditch AttemptChapter 10

As soon as Charlie stepped into the cool interior of the castle, he knew that when Artie Tedesco tells someone to do something that he just better well do it. Artie had his gym shorts on and a muscle tee- shirt that exposed a pair of meaty arms that could have been pistons in a V-8 engine. His body was bronzed from sitting out by the pool for most of the morning. Charlie spotted his open laptop and a pile of his legal papers spread out on a patio table that touched the edge of the pool. He...

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