You Can Be Anything You Want Pt. 01

Soon she wanted more, we started copying even more stuff from porn. Facials and deepthroating were added to her list, eating her out to mine. The next defining part of my story came next.

We were watching a scene where a woman was blowing a guy who was slouched on the couch. We were in bed and Sam was playing with me. What happened next in that scene shocked me -- the woman licked her index and middle finger and started fingering the man's asshole. He came almost immediately. Sam, of course, wanted to try it. We had a brief argument about whether it was gay or not, but she had a valid argument up her sleeve. She enjoyed anal so much and the biology between a man and a woman is not so different down there. If anything, we had a prostate and according to an article she had read, stimulating it could lead to tremendous orgasms.

The porn and conversation felt like a trap, but her arguments were sound. We agreed to try it and I sat on the chair while she knelt in front of me. In the beginning, it felt weird, but in a good way. There was a bit of pain, but nothing I couldn't handle. Then I started to enjoy it more and more. My mind was blank, I could only hear static, and my entire body was filled with pleasure. I came so hard I flooded her mouth with my cum I still remember the audible 'gulp' sound as she swallowed.

We repeated it at least two more times while we were together.

At the end of the summer, we split up, each of us going to a different college. We both felt like our relationship would never turn into anything more. We were great friends, and the sex was amazing, but that was all. Mike had decided to stay in town and started working for my father. He loved the job, and my dad was happy that someone had the same enthusiasm as him. I left for college a week later. In the two years I was there, I studied hard, and wrote my first two books. They were published under a different name and got great reviews. I made a lot of money from them and found my calling.

The third turning point in my life was Mike's wedding. He had proposed to Linda, a girl he dated since school, and had invited a small group of friends to a resort to celebrate. That was the weekend I lost my parents. This is still a sore subject for me, and I would like to leave it at that. When I got back, I sold my parents' house to Mike and made an arrangement with him. He would continue to run my father's business and I would continue to own half of it. I bought a small condo in the city and moved there.

I was a wreck. Sam had also moved to the city and stayed with me for a month. She was very supportive and probably the reason I got through the grief as quickly as I did.

The fourth turning point was one night while Sam and I were watching a film. She blurted out of nowhere she hadn't called her boyfriend in two days and grabbed her phone. I was shocked. I thought that during the time she was staying with me she was single, but the truth was the opposite.

When she got back, I confronted her. She explained that their relationship is different and it wasn't a problem for either of them. If anything, it made it even better. I did not believe her until she snapped at me to shut up and listen. I sat there in a quiet rage while she explained the situation.

Apparently, he was a cuckold. He got off watching her have sex with other men in front of him. She on the other hand, still liked to experiment and the relationship worked for both of them. They, of course, loved each other but managed somehow to separate their sex lives and love lives. The more I listened to her, the more my rage started to die down and I got interested in their agreement.

Sam showed me a key around her neck. She explained that it was for a cock cage she had fitted him, so he could not have sex unless she unlocked it. Not just sex, he couldn't even get hard without some serious discomfort. They both loved it. I, on the other hand, was intrigued and kept asking for details.

Sam explained everything in as much detail as possible. How she 'milked' him with prostate toys instead of having sex with him, how she would sometimes dress him in her lingerie and have him service and prepare her 'boyfriends' before she had sex with them. She even made him clean up their cum from her pussy and ass.

Her greatest turn-on was taunting him with anal. She would deny him her ass, but readily give it to her other lovers while explaining in great detail how good it made her feel. He got off on the humiliation, she on the assfucking.

By the time my questions were exhausted, I was hard as a rock and she was flushed. We were both so turned on, we ripped our clothes and did it right on the couch.

She was even more experienced than the last time we had sex. The blowjob was amazing. She commanded me to 'face-fuck' her, swallowed my entire cock in one go, put my hands on her head, and looked up at me expectantly. I skipped the slow buildup and immediately started to jam my cock in her mouth and down her throat. It felt amazing. She had tears running down her cheeks, and drool on her chin and her breasts.

The sounds in the room were intoxicating. There was so much gagging and slurping, I barely lasted three minutes before I grabbed her firmly and pressed my cock as deep as possible. I came buckets down her throat and just held her there gagging. As soon as I released her, she grabbed my cock, slurped all the drool and cum from it, and smiled wickedly because it was my turn to please her.

She turned around, peeled her soaked panties from her pussy, and climbed up on the couch on all fours. She was dripping her juices all over the cushions and begging me to eat her out. I did so, as best as I could, until I was hard again, stood up, and slammed my cock in her dripping pussy in one go. She just gasped and moaned, begging me to fuck her as hard as possible. I kept going harder and harder, but it felt like there was no pleasing her. The harder and faster I slammed against her firm buttcheeks, the louder she got, but never fully lost control.

Then I remembered her weakness -- anal. I withdrew from her pussy and lined up my cock again her tiny pink asshole. 'You finally remembered' was the last coherent thing she said before I pushed in. She was tight but not as tight as I remembered. That little ass had seen some serious fucking. This was to my benefit as well. I could just go all out, without the need to be as careful as the last time we did it, but as soon as I started going faster, I knew I wouldn't hold back for more than a few thrusts. I still gave it my best, but I exploded deep inside her in less than a minute.

I couldn't remember the last time I came this much. She loved it and kept saying dirty things to encourage me to fill her up. 'Fill my slutty little asshole with your cum' was my favorite.

The next day while she was at work was interesting, to say the least. I was horny. Hornier than I have ever felt before in my life. My thoughts, however, were full of scenes from her stories with her boyfriend and 'boyfriends'. I kept imagining her being run through by a huge man with a big cock cock while her boyfriend was on his knees on her bed encouraging them both.

The scenes slowly moved more towards him being milked and sucking her lovers' cocks. I remembered the few times she had her fingers in my ass and wanted to try it again.

That night when she got home was difficult. She kept talking about her day at work and all I could think about was asking her to stick her fingers in my ass. She eventually asked me why I was so distracted and I had to confess.

"Why didn't you just say so?" she asked, "I was starting to think there was something wrong with you."

"I don't know. I was embarrassed.", I replied.

"Why? It's not like we haven't done it before..." she said as she started to undress.

There was no arguing with that woman.

Minutes later I was on the couch and her fingers were in my ass. I felt just as good as before. Even better. We repeated it the next night, and the night after that as well.

Unfortunately, her stay had to end someday. And it did - the next weekend. She had to go back to her boyfriend and I had no right to ask more of her. He came to pick her up on Saturday.

On Sunday, I kept thinking about sex. I couldn't get any writing done, but fortunately, there were no deadlines to keep. I sat on my computer the whole day watching porn. That was my routine for the next week. Wake up, have coffee, and watch porn.

I started to look for more and more specific things. 'Cuckolding' and 'milking' were almost always present in my search history. Eventually, that lead to a desire to try anal by myself. My cock was no longer enough to satisfy me, or so I thought, and I ordered a buttplug and a p-spot massager online. My masturbation sessions slowly changed and so did the porn I watched.

The culmination was a session one evening a few days later. I had left the porn on auto-play and played with my ass with the massager. I was so lost in the pleasure from my prostate that I barely looked at the screen. My eyes were closed and the only thing I could think of was - pleasure. My cock was soft and just rested on my thigh as I moved the toy inside my ass, but I was getting nowhere. Then, in a moment of frustration, I looked at the screen. Every detail of that scene is still in front of my eyes.

A woman was lying on her back with her legs near her head. I remember them being completely straight. She had amazing flexibility. She had messy short dark hair and her body was covered in sweat. Her boobs were not that big, but they were amazing - small nipples and areolas, and a dark pink color contrasting her fair complexion. She had her eyes open, looking up at the man fucking her. Her sight was hazy, as if she was so lost in the moment, that the only thing important to her was just pleasure.

Then the camera panned and I was shocked. She had a dick. A small penis that was resting on her lower stomach. Her balls were tiny. The contrast between the camera angles was what got to me. She clearly looked like a young, and very attractive woman, but there was no denying it -- she had cock and balls. Then I started to look more closely. Her cock did not look like it belonged to a man, but it looked feminine. It looked soft and pink. I could imagine a sweet smell from it, not the raw primal one that men carry. I started to move my toy again, in love with the image on the screen.

Then the camera panned again to a very big and thick cock going in and out of her very stretched asshole. Each time he withdrew, her ass gripped it like a vice, desperately trying to hold on to it. The sounds coming from her were one of the most erotic things I'd heard at the time. She was clearly enjoying being taken in that manner. My hand started to move faster and faster as the scene reached its peak. She started to beg the man to keep fucking her. Her voice was soft, her eyes were closed, lost in some sort of indescribable bliss.

I was glued to the video, emulating the movements of the cock as closely as I could. She then cried out and came. Her cock started leaking, not shooting, cum on her belly. Her mouth was open, but no sound came out. The man sped up, and soon after, I saw his cock convulse and pump her ass full of cum.

The camera moved again on her face. She looked radiant. A stupid grin was on her face, her eyes could finally focus again. I looked down at my cock and saw a few drops of cum on my leg - I had almost come just from anal. It didn't feel like a full-on orgasm, but I was close to one and it had escaped me.

I closed the laptop and cleaned up. Every time I closed my eyes I could see that daft grin on her. She was so beautiful. I started to wonder what it would feel like to be her at that moment. My train of thoughts carried on uninterrupted. I started to imagine what it would be like to be her, to look like her. I wanted to be just as beautiful. I wanted that stupid grin on my face. At the time I didn't realize it, but I was getting addicted to the idea.

*******************

"I think, this would be enough for tonight." Nicole said as she stood up. "I need to gather up my thoughts for the next stage of my transition."

"Ok!" was the only answer Chloe could muster. She felt hot. No, she felt in heat.

"Anything you would like to ask me up to this point?" asked Nicole.

"Yeah, why me? I mean, I'm thankful for the opportunity, but why did you decide to confide in me?" shot Chloe.

"Two reasons. First, I saw your application at the company and handled it myself. I liked the way you write. Your colleagues praised you, your editorial work was great and according to your boss, you could pick up on subtle nuances in conversation with people. That intrigued me." answered Nicole, not trying to hide her praise. "Secondly, you are very pretty, but you do not use it to your advantage. I just wanted to tell you that the whole 'Judge me for my work, not looks' vibe is pointless. You should use everything you have available. Don't get me wrong, though. This is not a trap to force you into anything."

"Thanks." was all Chloe could muster as a response.

"Ok! That's it for today. I think I need to sleep on the next chapter. Shall we continue tomorrow?" asked Nicole, showing just a hint of anticipation.

"Yeah, that would be lovely!" Chloe answered picking her boss' mood up immediately. She made sure she saved the recording and closed the laptop. It would be very annoying to ask Nicole to start again from the beginning.

She got up from the sofa, stretched her arms and back, and headed upstairs. Her room was small and currently occupied by her enormous amount of luggage in the middle of it. She opened her bags to get a change of clothes and finally saw the vibrator and dildo she had packed.

"I'm an idiot!" she whispered under her nose. She grabbed a pair of new panties and her pyjamas and threw them on the bed. The rest of the luggage could wait until tomorrow. She was tired so a quick shower before bed was all she had strength for. Her movements were routine, her mind was elsewhere. It was stuck on replaying over and over the scene Nicole described. She started to feel more and more aroused as the water ran down her body.

"Oh what the hell!" she whispered in feigned frustration and stopped the water.

She wrapped a towel around her slim body and got out of the bathroom leaving wet footprints on the floor. On the way to the bed, she picked up her toys and set them on the bed, and dried herself. She threw the towel on a nearby chair and lay on the bed with her legs spread. Her pussy flooded her fingers as soon as she started to rub her clit. She needed more than just her fingers though.

She grabbed the bullet vibe hoping she remembered to charge it. Fortunately, the battery was full. She pressed it on her pussy and let out a soft moan. Her mind went back to the porn scene her boss described, but with one subtle but important difference -- the woman wasn't just a random actress, but Nicole. She opened her eyes and started to stare at the dildo next to her.

"Is anal that good?" she thought.

There was only one way to find out. She grabbed the lube and applied some to her virgin asshole and a lot on the six-inch silicone member and lined it up. Her right hand was reaching behind her back holding the slippery toy firmly in place, while the left one was holding the vibe on her pussy. She started to push the head of the fake cock inside. She needed to have it inside her and her ass finally gave in and let the intruder in. She felt a small amount of pain masked by a huge amount of undiscovered until now pleasure.

"Fuck, this really feels that good!" was the last coherent thought that ran through her brain as she started slowly to fuck her ass.