Ugly Duckling to Sissy Princess Ch. 06

I was terrified, yet part of me was aroused to have such beautiful girl and gurl touching my body. It felt as if they were preparing my body for a sacrifice.

Vanessa and Bernice seemed to want to sync their attacks. I could feel the tip of Vanessa's cock at my back door and the tip of Bernice's strap-on cock on my lips.

I looked straight into Bernice's eyes, imploring her with my facial gestures to stop this. I was not ready for it.

But, my expression of supplication seemed to only embolden her to abuse me. She gripped my face and slid her silicon cock into my mouth and deep down my throat, as if this was the most normal thing in the world.

I had to swallow it fast and apply all the lessons I had recently learned with Simon. I could choke on it, even die, if I panicked.

I couldn't try to resist it, that would only cause me to gag violently. I had to swallow it down my throat and remember to breath the whole time through my nose.

Bernice's attack on my mouth must have been Vanessa's cue, because, I felt the pressure of her cock trying to penetrate my tight virgin hole. Vanessa met with resistance, I was too tight.

My hole did not stretch wide enough for Vanessa's fat cock. But, she was not discouraged. She seemed determined to stuff it inside me, whether or not it fit! She grabbed my hips hard and pushed as hard as she could.

I screamed, "What the fuck! Can't you see it don't fit! Stop it!"

But, my protests only made her redouble her efforts.

"Use more lubrication, Vanessa." Bernice advised her. Then she threw out another idea, "Maybe we should give Vicky some alcohol to get her to relax her muscles."

But Vanessa ignored her pushed harder and harder.

I felt my hole stretching very wide, beyond what it was designed to stretch. I screamed in terrific pain!

I was sure my asshole could not stretch any more. I cursed at Vanessa, "Damn it! You are hurting me! Stop trying, it don't fit!"

But, Vanessa seemed to not give a fuck. She was going to tear my asshole!

"If don't fit, damn it!" I yelled!

Then suddenly, the head of her cock popped inside me, shocking me with excruciating pain. My body jumped like I had just been branded with a hot iron.

When the tip of Vanessa's cock popped inside me, it didn't just stop there. She had pushed forward with so much force that it rammed full speed deep inside me, stopping only when her sack hit my ass.

Her fat cock head ended up somewhere deep in my body that I did not know existed. It felt like a baseball bat had been rammed inside me! The pain was intolerable!

Her cock must have slammed into a bone inside me, because, I felt something like a bone inside me pulsating with shocking pain! I was so shocked that I could not scream for a few seconds. I stood frozen, my head exploding from the pain.

Then, I started to scream and tremble. "Ahhhh! Oh fuck, fuck, fuck! That hurts! Take it out!" I yelled at her.

Vanessa started to slowly withdraw her cock and the pain of her pulling it out was almost as excruciating as the pain when she shoved it inside me. "Stop! Don't move!" I yelled at her.

But, of course, she couldn't leave in there forever. She pulled it out with me screaming my head off.

"You fucking bitches! Get these fucking ropes off me? I'm out of here!" I said, angry as hell, but, surprisingly, I was still using my feminine voice.

"Sorry Vicky, I didn't mean to push it in all the way like that. I should have used more lubrication, like Bernice said." Vanessa said admitting her mistake. They stopped attacking me for a minute. Maybe they were feeling sorry for me, but, neither Vanessa nor Bernice was cutting me lose.

"Let me go home! I'm done for the night! I'm hurt! I want to go!" I yelled and cursed at them. But, the ropes on my body had a tight grip on me. Vanessa seemed to look at Bernice waiting for some direction from her. Bernice looked down at me, held my head and pushed her strap-on cock back in my mouth.

Vanessa quickly greased her cock with more lubrication popped the fat head of her cock inside me again. I yelled at her, "Are you fucking crazy! I told you it hurts too much! Don't do that!" But, she did! She was much gentler this time, but, she started to slowly fuck me, ignoring all my protests!

I tried my hardest to shake free of the rope. The whole bed shook, but, it was no use.

"It always hurts like a bitch the first time." Vanessa said. "Just stop being a pussy about it. You'll thank me later when you turn into a cockloving slut!" She said.

"I will never become a cockloving slut! I hate this! I'm a crossdresser, not a queer!" I yelled.

Then, Bernice said, "Are you forgetting about Ted, your new boyfriend? He won't have any use for you if you cannot take his cock up your ass! And, his cock is twice as big as Vanessa's!"

Vanessa talked while she slowly fucked me, "Your boyfriend Ted used to be in porn, you know. Ted has the fifth largest known cock in the planet! And, he is the most brutal son-of-bitch, too. I've stayed the fuck away from him, but, I've heard the stories. He tried to make it big in porn, but he sent quite a few gurls to the ER with serious injuries! Even with all the training in the world, he's going to split you open like a Turkey on Thanksgiving! You should stay away from him!"

Bernice also talked while she slowly fucked my face. She said, "I swore to him that I wouldn't say anything to scare you off. But, I'm glad Vanessa warned you. Ted is a nice guy, but, his cock is better suited for cattle than for humans. If you change your mind about Ted, I'll help you avoid the situation with him."

I decided at that moment that I am giving up this sissy shit and going back to being a straight guy! I don't care how beautiful I am as a gurl anymore. This pain is not worth it! And, there was no way I would ever have sex with Ted!

I felt excruciating pain and I felt violated and humiliated.

But then, Vanessa did something that made my ordeal just a little more tolerable. She reached down with her right hand to play with my dick. Despite the horrible experience I was going through, my dick responded to her touch immediately. It twitched and it got hard in its cage.

Vanessa disparaged my cock, "Wow! It is so small! It looks like a clitty! Are you sure you were born a dude?" She was a total bitch and I felt hatred towards her at that minute. Yet, her hand felt so good teasing my dick.

Bernice had not locked my cock cage. Vanessa opened it and pulled out my dick. The girls continued to violate me on both ends, but, Vanessa's fingers teased and stroked my dick. My 'clitty' started to feel real good. I started to moan from Vanessa's teasing my clitty.

On hearing my moan, Vanessa became more aggressive.

I became very confused, because Vanessa's hand on my dick felt wonderful, but, my ass was throbbing with pain. I tried to protest about Vanessa getting rougher with me, but, Bernice was holding firmly to my head and she was also getting more aggressive with her cock in my mouth and throat. I had to suck her strap-on cock like I had sucked Simon's cock, because I did not want to piss her off. Bernice loved to see me worship her cock and kissing, sucking, licking; rolling and twirling my tongue all over it.

Vanessa knew very well how to pet a clitty. I purred like a happy cat. I moaned and leaked pre-cum, at the same time that I felt tears rolling down my eyes from the abuse at both ends of my body.

"Are you my bitch, Vicky? Nod your head to say yes, Vicky." Bernice yelled at me while fucking my face. I nodded and moaned, because Vanessa's fingers on my clitty was pushing me so close to orgasm.

"Are you my bitch, too?" Vanessa yelled, and, she pumped her cock inside me harder, faster and deeper. I nodded and let out a long moan, not sure myself if I was crying with pain or moaning with pleasure.

Vanessa's pounding progressed to jackhammering. She had incredible strength and stamina. She was seriously fucking me. Her eight-inch cock was jackhammering me like it was on a mission to break through to the other side. My back was completely arched, my legs spread wide open, my head lowered and my ass raised high. I suddenly realized that the reason Vanessa was fucking me to oblivion - so hard and deep - was because I was helping her to do it!

I was subconsciously slamming back into Vanessa's body at the same time she thrust forward into me. This caused us to violently collide and penetration was brutal. What the fuck was I doing? Had I snapped and gone fucking crazy? I was complicit in the brutality inflicted on me. My body seemed to be acting on its own, wanting to be punished!

Vanessa was right! I was turning into a cockloving slut! My body wanted to impale itself on Vanessa's cock! My ass was being destroyed!

We were moaning, sweating, and trembling. I might have cried a little. Bernice had to pull her cock out of my mouth, because I was having trouble breathing at this point.

"It hurts! It hurts so much! And, I'm going to cum!" I yelled.

Vanessa gave one last final brutal thrust inside me. It was so tough, hard and deep, it almost made my head pop off! The three of us yelled and spasmed simultaneously. I felt an orgasm that was strong enough to knock out a horse! I must have lost consciousness. It was like a tidal wave hat hit me and I could not swim up to the surface! I couldn't breath!

I was trembling uncontrollably and trying desperately to catch my breath.

I felt Vanessa's cock throbbing, pulsating and exploding inside me. She shot and squirted about a gallon of her cum inside me. Her warm milk felt fucking amazing inside me! I felt my ass muscles contracting, squeezing every last drop out of her cock. I had no idea ass muscles could do that, like a pussy!

Bernice was cuming too. The strap-on cock must have something on the other end that rubbed her clit to make her cum. She orgasmed and squirted her juice all over her beautiful black satin sheets.

The experience was so surreal, and, it seemed to last forever.

When the insane orgasms finally ebbed, we were completely spent. We collapsed on the bed drained of all energy. The sheets were soaking wet from sweat and love juices, even though I had captured most of Vanessa's milk inside me.

Bernice cut me free of the rope with scissors. I was finally free, but, I did not move. My body felt like it had been through a gangbang of prison inmates. It hurt so much just to put my legs together.

It took a while for our heavy breathing and our over-heated bodies to return to normal.

Then, Bernice put her lips on mine and started kissing me. I kissed her back affectionately.

Vanessa came over to join us. I kissed her, too, even though she had abused me so bad, and I would be hurting for days because of her. We took turns kissing each other very passionately. I felt a state of euphoria.

Then, we started to giggle like silly teenagers.

Bernice said, "Bitch, we fucked the shit out of you!"

"Fuck you, bitch. I can't walk!" I yelled at her.

I moved my legs around and felt flashing pangs of pain all over my body.

Vanessa said, "I don't know what came over me! I guess I still had some last bit of male testosterone left to get out of my system."

Bernice joked, "Yeah, you had some, but don't worry, you shot all of it up Vicky's ass!"

I could feel Vanessa's cum inside me. It felt good, like a warm lotion on my sore parts. I hoped it would stay inside me for a while and not spill out.

I went into the shower first, because I had to leave. I still had to study for my exam in the morning. I noticed as I walked to the bathroom that I was walking funny and I was extremely sore inside. The warm water felt nice on my body, but, did not wash away the soreness.

After my shower, I dressed up as a guy, and I packed my pretty gurly things. "It's too bad you cannot stay here for the night." Bernice said.

Vanessa said, "I think I popped your legs out of their socket! You are walking so crooked, Vicky!" I held my middle finger up and smiled at them.

But, there was no hard feelings between Vanessa and I. We hugged and kissed good bye on the lips. She is gorgeous and I was very attracted to her, though, not as much as I am attracted to Bernice. They made me forget all about my girlfriend, Carol.

Bernice walked me out to my car.

"How do you feel about Vanessa?" she asked.

"Before tonight, I had the impression she did not like me at all." I answered.

"Well, you're right, she didn't. She fucking hated you! She is a beautiful stuck-up and conceited bitch that cannot stand anyone that competes with her looks!" Bernice explained.

She added, "That's why I asked her to join us. I let her pop your cherry so she would feel invested in you. She is a very important person in the world you are becoming a part of. She has a lot of power and connections. She would have been a dangerous enemy. But, after tonight, she likes you very much now! You did very well tonight!"

"Tell that to my sore and throbbing ass. You guys destroyed me tonight." I complained, feeling the throbbing soreness in my asshole and inside me.

But, Bernice only laughed and said, "Yeah, Vanessa was so brutal popping your cherry. I am a real mean bitch, but, I felt sorry for you. It did not stop me from fucking your face like my bitch, though, because, I am attracted to you. I get rough when I am full of passion."

I blushed and did not know how to respond to this.

Bernice smiled, noticing my sudden shyness. She looked straight at my eyes and said, "I told you before, if you ever decide to grow real tits, and replace that pathetic pinky with a real pussy, I'll make you my lesbian wife!"

It was a fucking sick thing to say, yet, I was very flattered.

But, I would never chop my dick off, not even for true love. Would I?

"Why can't I be a sissy gurl? Why do you want me to cut if off?" I asked her, confused.

"Because, that pathetic little thing between your legs is useless to me. But, if you replaced it with a beautiful pussy, I would spend most of my time awake eating you out." She answered.

I blushed again, smiled at her, and left.

That night, before going to sleep, I reflected on everything that happened. I had been fucked by three people in one night. I had sucked cock and been brutally fucked in the ass.

I was curious whether the next time I got fucked it would hurt so much. Maybe the pain was over and it would be all pleasurable from now on.

I thought about Carol and I understood her completely now. She likes big cocks and she likes it very rough. I know exactly what that feels like now. It's terrifying, excruciating and extremely intense. And, it gives you the most fucking incredible orgasm; an orgasm that blows your mind. Straight guys could never come close to imagining even half of what they are missing!

Then, my thoughts turned to Ted. The whole point of everything was for me to be with Ted. Yet, what I heard about him tonight raised red flags. It was really scary.

It is one thing to be fucked by Vanessa's eight-inch cock, but, if Ted's cock was twice as big, that is not a cock, it is a weapon of massive destruction!

I had fallen in love with Ted on our first date. He is tall, black, strong, muscular, handsome, smart and refined, and a phenomenal kisser. He made me realize that I could improve my life by being a sissy gurl and he had brought me into this alternative world. But, I definitely don't want to end up in the ER with a torn asshole and rearranged internal organs.

I had a lot to think about, but, I was exhausted. I fell asleep.