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?”
