Niki's Story (Black Ring Series)

Niki’s Story
(Spinoff from Black Ring I-III)

It all started when Jack, at the time, became my roommate. I was a mechanic engineering student and a total nerd. I kept to myself, played World of Warcraft with my overseas contacts, and tried to make the family proud back home. I was eighteen and felt an array of feelings that I had successfully repressed during high school. I found a way out of gym, never did any sports, and had very few friends. Those who were friendly tended to be girls who would never have dated me under any circumstances.

Jack arrived a week prior to classes start. He was White, slender, and upbeat. It was immediately obvious that he would be the dominate personality between us. I immediately felt torn as he appeared generally good looking. He got haircuts regularly, kept his skin free of acne, shaved consistently, and dressed nicely. I quickly found myself wanting to emulate his grooming habits. I couldn’t bear the idea of being criticized on appearance.

Throughout high school, I had struggled to determine my sexuality. I felt attracted to men, but I knew how much of a disappointment it would be to the family. I was the second boy in the family, and everything my older brother did was exceptional. My parents demanded that I be at the same level as him. Right away, I realized I would have to suppress any feelings of attraction for Jack.

“Good first day,” Jack commented on his first day of classes. “Oh, if you knock on my door, and I don’t answer immediately, it’s because I’m a heavy sleeper,” he said.

“Alright, good to know,” I said not realizing at the time that it was a lie.

Jack was a psychological anomaly. He harbored a male and female personality that would switch control roughly twice a day. I noticed an oddity with him when I saw that he never seemed to sleep. His light in his room would always be on, he would come to the kitchen to eat a snack at all times of the day, and he frequently watched television at odd hours. At first, I figured he would stay awake to cram for papers or midterms, but it became an everyday occurrence. I also considered the idea that he was one of those Thomas Edison geniuses that only got three or four hours a sleep a day.

At night, Jack would act a little differently. He would watch dramas on lifetime, cooking shows, fashion design shows, and chick flicks. He would also cook meals only to later put them in the refrigerator to eat several hours later. Occasionally, he would take walks at midnight around the neighborhood, and I noticed a quirk about him where he would mouth words as if he were talking to someone.


One day, he came into the kitchen during the day time which was odd of him. “Hi, how’s it going?” I asked awkwardly.
“Good, what you cooking there?” he asked.

“Just a dish that reminded me of my family’s cooking,” I said.

“Can I help?” he asked.

“Sure,” I said wondering what was up with him. He had never offered to cook with me before. While, I couldn’t detect it back then, there was a subtle voice difference in his voice. At the time, I had no idea I was talking to Jill.

We worked on the meal together, and I was surprised at how well Jack could cook. It was as if he had practiced this cuisine before. After the meal, we cleaned the dishes together. My mind wandered on the possibility that the two of us could do this more often. It was as if we were already a couple. I felt butterflies in my stomach at even the possibility.

“That was great. We should do this more often,” Jack said as we finished.

“Yeah, sure,” I agreed. I wanted to shout “yes” but I kept my cool. It was also very possible that I was overreacting to a very small thing.

He then did something I would never forget. He came close to me and kissed me on the lips. It was the first time anyone had kissed me before. I knew I should have resisted him, but I didn’t want to. I didn’t want this to be fake. Never did I think a random roommate would also be gay. He not only kissed me, but he went down and grabbed my dick. He massaged my dick getting it instantly hard and then let go. He patted me on the shoulder.

“Until next time,” he said and then went upstairs to his room.

I stood there in stunned silence for several moments. Should I go after him to his room? Should I yell at him? If I didn’t immediately correct him, he would really think I was gay. But maybe that is what I wanted. Was it real? Was it him just fucking with me? How did he know I wouldn’t immediately shove him away?

To my regret, I didn’t follow up on it. I went to my room, took my clothes off, and massaged my dick thinking of Jack as I did. After I came in my hand, I realized then there was no going back. I truly was gay, and I would have to deal with the consequences. I wasn’t ready to come out, but I could no longer deny it. I wanted Jack, and I fantasized being his lover for the remainder of the year.


The next morning, Jack came down while I was watching TV. “That was a great diner last night. Want to do it again, tonight?” I asked hopefully.

Jack gave me a look like he didn’t know what I was talking about. His face was hardened as if there was a wall between us. He didn’t have the soft expression that he had the night before. “Maybe, we’ll see,” he said.

His voice was cold and indifferent, but I couldn’t let this moment go. I couldn’t let him leave like last time. I had to show him that he wasn’t alone. We were two of a kind, and he didn’t need to fear any backlash from me. I came over to him and kissed him on the cheek.

He gave me an odd look as if he didn’t expect it. Without a word, he left leaving me confused, empty, and crushed. Was I being played? Was last night a test to confirm my homosexuality? How could I like such a horrible manipulator? My roommate was an obvious sociopath. There was no way else to explain it. And then I felt a chill, as I began to realize there were signs of mental illness. He acted differently as if he were two different people.


That evening, I was in the living room watching TV when a young woman quickly went down the stairs and exited the door without saying a word. At first, I wondered if I had just imagined it. I quickly went to the door and looked out. The girl had left in Jack’s car.

My first alarmist thought was that this girl had broken into Jack’s room, stole his keys, and darted out. I proceeded upstairs and found his room locked. The door could be locked from the inside without a key, so I knocked a few times to see if Jack would answer. He didn’t, so I called his phone number, but he didn’t answer.

I considered getting the police involved but another more plausible explanation came to me. The girl was obviously Jack’s girlfriend. He was straight, and I had been played. For a long time, I just sat there staring off into space. My fantasy of being with Jack was gone. Not only did he not kiss me back this morning, but he had a girl in his room sometime this evening. I had been manipulated and violated, and at the moment I truly hated him.


Jack arrived early morning and found me in deep contemplation in the living room. He looked surprised to see me as if he wanted to sneak inside. “Who was the girl?” I asked hurt.

“My sister,” he said immediately.

“Oh, I see,” I said still feeling confused. I hadn’t asked about Jack’s family and neither had he about mine. I had always assumed he was an only child. It would make sense that his sister would have access to his room key and car key. Who else would he trust with that?

“You have something you wish to say?” he said rudely. His voice was cold and unfriendly. He was being a bully, and I had to stand up to him.

“It’s just that you have been given me some mixed signals,” I said and immediately felt pathetic and weak. I should have shouted and screamed at him. I should have demanded answers. Why was I so weak; so easy to abuse and bully by others?

“Oh, really?” he said sarcastically. “Nick, I’m pretty chill on the surface but deep down, I’m an asshole. Remember that,” he said. His face was menacing as if he really wanted to convince me. Maybe deep down, he was hiding the same feelings I did. In any case, I felt only anger and bitterness. I was angry at him for tricking me and angry at myself for allowing it to happen.

I went upstairs to follow him. I would demand that he give an explanation for why he had kissed me first and for his rudeness. As I approached, I heard ranting through the door. I couldn’t make out what was being said but Jack was shouting at someone. In my weakness, I decided not to disturb him.


The next morning, there were knocks on my door. I got up groggily and answered the door. I felt a chill go through me as it was Jack. He was going to tear me down once more. Instead of his hard cold expression, he was nearly in tears.
“I’m so sorry,” he said and then kissed me before I could stop him.

I wanted to push him away. He wasn’t going to manipulate me again. Jack kissed me with more enthusiasm putting his tongue in my mouth. I forgot who he was and just went with it. He then went low and pulled down my shorts. He stroked me a few times to get me hard and then started to suck me. I had never been sucked on before by man or woman. It felt so good that I couldn’t muster the will to protest. This was heaven. If only he wasn’t such an asshole. I began to think that he was just as conflicted as I was, lashing out.

I came in his mouth and gasped in pleasure. He quickly swallowed and got off his knees. “Let me give you one,” I said gratefully. I wanted the fantasy to continue. I wanted us to be real lovers giving each other pleasure whenever we needed it.

“It’s okay, Nick. We’ll keep this our little secret,” he said and then left my room.

I wanted to go after him but stopped myself. He was working this out his way. I just needed to be patient with him.


Throughout the day, Jack went up and down the stairs moving boxes into the dumpster near the apartment complex. When he was done, he came down wearing a black leather jacket. “I saw you move a lot of stuff out this afternoon. Anything wrong?” I asked curiously.

He gave me a cold look of disgust. “After winter break, I’m moving out. My parents will compensate you for the rent. In fact, you will have the place all to yourself,” he said with a snide smile.

I simply stared at him speechless. It didn’t make any sense. “I’ll be at my girlfriend’s place,” he said with a special emphasis on “girlfriend.”

So, the girl from before wasn’t his sister after all. It was his girlfriend that he had this entire time. My dreams were dashed. I wanted to lash out. I wanted to tell his girlfriend, whoever she was, that he was not true to her. He wanted it both ways. He was the epitome of every negative bisexual stereotype. I wanted to scream and shout but said nothing as he left.

As I contemplated Jack’s behavior towards me, alien thoughts entered my mind. “If I were a girl, he would love me,” I said to myself.

What followed were a series of triggerable moments. I casually surfed the web for examples of gay men who cross-dressed. They appeared straight to everyone in public but made love to each other as men in the bedroom. With finals over, I started researching more-and-more into drag queens and male-to-female transsexuals. I watched videos showing how shemales made love to attractive men. I saw dating websites specifically for shemales. I wondered how they could be successful in getting a man while I couldn’t.

With the apartment all to myself, I was free to experiment without anyone noticing. I discreetly started buying woman’s underwear and bras off the Internet. Once they arrived, I tore open the package and immediately put them on. Somehow, it felt right, and I became aroused simply by wearing them. I even wore woman’s underwear underneath my clothes and felt the excitement of no one knowing but me.

In my enthusiasm, I looked to see how much it would cost to buy female hormones. I never intended to transition at this point. I had heard that it could clear up my skin and make me less restless. I was a gay man that wasn’t getting any. Every time, I stroked my cock I felt ashamed. I would just try it and see how it felt.


A few weeks later, I saw a news article on Facebook of a brutal crash. A girl named Maria had been killed by a drunk driver, and a second occupant had been hospitalized. As I read on, I read that the survivor had been Jack. A school picture of Maria was on the site. She wasn’t the one that had been in Jack’s room. None of it had made any sense. Secretly, I wished Jack had died instead of that sweet girl.

Soon thereafter, Jack came to the door with the key he hadn’t surrendered yet. He quickly went upstairs without saying a word to me. It was like seeing a ghost. I hadn’t expected him to ever come back. He then went back downstairs and stared at me.

“Hey Nick, I’m sorry about how I have been acting recently. I’m not moving out after all,” he said sincerely.

“You were in the crash, weren’t you?” I asked delicately.

“Yeah,” he said flatly.

“Do you want to talk about it?” I offered.

“No, I’m good,” he said sadly and went back upstairs.

I couldn’t understand the man but this wasn’t the time to argue with him. He had just suffered a huge loss. I thought it best to just leave him alone. Even so, I felt a chilling fear. Now that I wasn’t alone in the apartment, I had to conceal my activities to the confines of my room. I would have to be careful not to reveal my secret.


By late February, there were some noticeable differences to my face. If I didn’t stop self-medicating, my face could become permanently altered. I knew I had to stop, but I didn’t want to at the same time. Finally, the choice was made for me when I spotted a woman going downstairs and quickly leaving the apartment. I couldn’t believe that Jack had taken up a new girlfriend so quickly after such a loss. I ran out to see who it was and then saw the girl move towards Jack’s car.

“Who are you?” I demanded of her.

“Why should I tell you?” she asked sneering at me.

“You just exited my apartment,” I said obviously.

“I’m Jack’s sister. Now, bug off,” she said aggressively.

“This is Jack’s car,” I said stalling. I couldn’t tell if she was lying but there were some definite resemblances between them.

“We share it,” she said simply.

I looked for a clue that would give her away. Was she really Jack’s sister? Was she his girlfriend instead but why would she lie? Was she actually a burglar stealing Jack’s car. I then saw a scar on her wrist. It was the same scar on Jack’s wrist. It couldn’t be true. There was no way, but I had to make sure. It couldn’t be a coincidence.

“That scar…it looks like Jack’s,” I said continuing to stall.

I then looked at her carefully. It was more than just a resemblance. It was him. I had watched so many drag queen videos of before-and-after transformations. This was the best I had ever seen. His face looked perfectly feminine and so was his voice. He was perfect.

“It is you,” I realized.

“Fuck yourself,” she spat.

It was all the confirmation I needed. I had to get to the bottom of this. “"You seem very confused with yourself. You act indifferent to me, then you suck my cock, then you disrespect me, and now you're back to being indifferent. What are you?"

The woman eyed me angrily and retaliated. “You think you’re so different? You’ve been taking hormones, and you have woman’s underwear in your room.”

“How did you know?” I asked stunned. I could have denied it or kept questioning her. In my fear, I needed to know how I was so easily exposed. What had I done to make it so obvious?

“I broke into your room,” she said nonchalantly.

“You can’t tell anyone. If my parents find out,” I stammered trying to do damage control. This man, woman, person, whatever it was could destroy me if this leaked out.

“As it so happens, I have their number too. So, don’t fuck with me,” she said and then entered the car. She locked the car door and then drove off leaving me speechless.

Despite the odd situation, the power dynamic had shifted greatly. I didn’t have Jack’s parents’ number, and I didn’t know if they even cared. I couldn’t win in a game of mutually assured destruction. I had been caught by a roommate that had no qualms breaking into my room and leaving without a trace. This person was a monster toying with me with reward and punishment while all the way even more fucked up than myself.

I went back inside the apartment and contemplated self-destruction. I couldn’t live this way with a roommate that could destroy me at any moment. As I thought of the way to do it, the girl came back into the apartment startling me.

"I'm mentally ill," she began. "I have multi-personality disorder. That is why I have been inconsistent with you. I have a male personality and a female personality. Do you understand?" she asked me.

I simply nodded. "Right now, my female personality has taken over...ever since the car accident. There is no Jack. There is only Jill," she said.

"Are you Jill all the time now?" I asked.

"For the time being until Jack returns," she replied.

"I have seen you talk to yourself. There is another personality isn't there?" I asked.

"Yes, but he's not in control," she clarified.

I stared at her wondering whether to believe her. I knew this to be exceptionally rare but what she was saying fit the criteria. She had been acting like two different people. "If you have multiple personalities, how can I trust you? One personality could say one thing and the other could do another," I said.

"For the moment, there is only one personality in control. I haven't done anything against you," she said.

"Other than breaking into my room," I said annoyed.

"You are self-medicating. What do you think would happen to me if you overdosed?" she asked. Her voice was cold as if my self-destruction would be a slight inconvenience for her. She might have been the friendlier of the two personalities but not by much.

"I think we can help each other," I said finally. If what she was true, she was clearly mentally unstable. If I made her an enemy, we would destroy each other. I had to make her an ally.

"How's that?" she asked skeptically.

"You haven't taken any hormones or had any surgeries, correct?" I asked wanting to clarify a few things first.

"Right," she agreed.

"And yet, your voice and appearance are perfect," I said admiringly.

"I have years of practice," she revealed.

"You could teach me how to pass," I said hopefully.

"Whoa, I can't promise that," she protested backing away.

"If it were possible, if it could be done, you could help me do it," I said hoping I didn’t sound pathetic.

"Possible," she allowed. "What's in it for me?" she asked.

"I can get you the drugs you need for your own transition," I offered.

"I don't self-medicate. That's a bad idea," she rejected.

"If what you say is true, you will never be approved by the psychiatrists. You will never be able to transition through the normal way. As the years go by, it will be more difficult to transition," I pointed out.

"I have no intention of transitioning. Jack will return," she replied.

"What if he doesn't return?" I asked almost hopefully. He was a total ass.

"He will," she said stubbornly.

I simply shrugged. "Very well.”

"I'm not taking any of your pills, but I'm curious what I can do for you," she offered.

I brightened up not expecting this reaction. "When do we start?"

"Now," she answered.


I sat in a chair as this unknown woman began to work on my hair. I still had trouble believing this was the same person as Jack, a homophobic man that was a complete asshole to me. Yet, I couldn’t doubt it. She had admitted to it, she had the same scars, and I could see the resemblance in her face. She still remained in drag and spoke in a female voice as she worked on me. After she was done with my hair, she worked on my face expertly applying make-up. Once she was done, I stared at myself in the mirror. I could barely recognize myself. I looked absolutely feminine. No one could have known otherwise unless I told them.

She wasn’t finished yet placing fake breasts on my chest. They were pale in complexion contrasting greatly with my own tan skin. I just had to trust her that she knew what she was doing. She used an adhesive to keep the breasts in place. She then came back with a collection of clothes. I tried on a dress and looked at myself in amazement. The black bra completely covered my off-color breasts. I felt my chest wanting my breasts to be real.
It felt so exciting and right. Up until this moment, everything had been boring and wrong. This is what I should be allowed to wear. This was what I wanted to wear. If only I could outside this room. I tried on a number skirts, feminine pants, shoes, and even swim wear.

“Wow, I had no idea,” I said amazed.

“Now, we have to work on your voice,” she said.

We worked on my voice for two hours with some progress. She was patient with me as my voice cracked. By the time we were done, my voice was shot.

“Thank you for helping me,” I said gratefully.

“Sure, no problem,” she said amused. I was her eager experiment. I looked at her beautiful face, but I couldn’t help but see a little Jack in her. I then realized a new opportunity. Jack could come back, physically anyway, without the asshole personality. He was good-looking when he wasn’t scowling or sneering at me.

“We could be more than just roommates,” I suggested hoping she wouldn’t become offended.

“What do you mean?” she asked coyly.

“We’re both attracted to men, right?” I asked hopefully. In truth, I had no idea and just assumed.

“Right,” she answered.

“We can dress as women must of the time except for special occasions,” I said not daring to say the obvious.

“Alright, let’s make now a special occasion,” she smirked.

“Okay,” I said nervously and went to wash my face. I had never had sex with a man, not all the way. Could I really do it? What if this was all a ruse? What if his male personality came out and called me names or became violent with me?
After we were both undressed, we were two males looking at each other. I looked at him fearfully half-expecting Jack to return and tell me this had all been an elaborate prank to destroy me. Instead, the very male-looking Jack came over to me and kissed me. We kissed for a few moments and started touching each other’s bodies. Our cocks were both flaccid even as I felt aroused and excited to be with a naked man for the first time.

Jack went down to his knees and began sucking on my cock. He eventually got me hard and it felt as good as the last time he did it. I came into his mouth and felt a bonding with another person I had never felt before.

“That felt good, thank you,” I said lamely. I couldn’t bring myself to say I loved him. I just couldn’t wrap my head around his unique condition. I couldn’t allow myself to be that open and surrender to him.

“Your turn,” he said in a business-like tone. His voice was still female as if to assure me his personality had not changed.

I eagerly obliged sucking him until he came. Could I dare to hope that this could happen again, even become routine?


Over the semester, Jack became more comfortable dressing and acting like a woman full-time. She called herself Jill and from that time on that was what I called her. I didn’t have the courage to go out in drag for my classes. My mechanical engineering classes were small, and we all knew each other. Jill went to large lecture classes where she could enter and leave without being bothered by anyone. Other than class, I tried to dress as a woman as much as possible. If this was really what I wanted, I needed to act the part. At this time, I still held out the possibility of just being a gay man.

Jill went out in public completely confident. Her dress, make-up, hair, and voice were all perfect. Even if she was caught, she didn’t give a fuck what other people thought. I was always a nervous wreck, and I never spoke for fear of my voice giving me away. Jill was patient with me not pushing me to do something I wasn’t comfortable with.

On an almost daily basis, we would come to each other’s rooms and make out while as men. One day I requested that he penetrate me, but he denied me. It was understandable. He felt like a woman and wasn’t interested. I considered the idea of getting a dildo and do it on myself but then felt the need to ask him a few more times.

He eventually relented, put a condom on, placed a generous amount of lube on his cock, and then penetrated me deep. He was rough as if punishing me for even asking. This only made me feel more into it. It was painful and yet pleasurable at the same time. More than that, I felt closeness between us that made me want to bond with him. I put aside that his personality was female and wished that somehow Jack the man could love me. He fucked me missionary at first, then put me on my back, and then got me on all fours. He eventually came inside the condom leaving me exhausted.

He gave me a look as if daring me to ask for it again. He believed he had gotten out of my system and that I would never ask again. On the contrary, I wanted more. I could never be a straight man after this nor did I have any interest in being on top.

“You actually enjoyed it?” he asked skeptically as I must have had a euphoric expression.

“You should try it,” I said.

“I’ll pass,” he said disinterested.

A part of me was glad. I never wanted to be on top after this, but I had to explain to him my feelings. “It’s not just about the pleasure. It’s about being submissive during sex, being treated like a female. I imagine myself being a woman making love to a man,” I said.

He wasn’t convinced but a few weeks later, he asked it of me. When it happened, I tried to get hard with difficulty. The pills were making it increasingly difficult to get hard. I finally penetrated him and had difficulty staying hard. He didn’t moan or grunt. He just went with it until I came. Afterwards, it became apparent that I couldn’t be on top anymore. The hormones and my mind weren’t in it anymore. I would have to always be a bottom gay man or continue until I transitioned to womanhood.


Near Spring break, Jill brought home a real man to the apartment. I was in drag at the time and stared at him. He was impressively built and handsome. I was immediately attracted to him more so than Jack’s male body. “This is my roommate, Niki,” Jill introduced me.

“Nice to meet you,” Chris smiled.

I merely nodded too scared to open my mouth. I didn’t want to expose myself in front of such a powerful man nor ruin Jill’s date with him. “She’s a little shy,” Jill excused me.

Even after so many voice lessons, I couldn’t dare to speak. Chris and Jill chatted while I made my exit. I saw them kiss outside and then he drove off. I felt jealous but happy for her all at the same time.

“Thank God, you were in drag,” she said to me once she came in.

“Are you with that guy?” I asked softly. I didn’t know how to feel about this.

“We’ve dated a few times,” she said.

“So, what are we?” I asked.

“We’re girlfriends. We’re both women stuck in male bodies,” she said simply.

“But you haven’t transitioned at all. You just dress as a girl sometimes,” I pointed out. A part of me wanted her to stay male, to fuck me, and remain my boyfriend fantasy. If she fully transitioned or got herself a boyfriend, the fantasy would end.

"Niki, I can't be your boyfriend," she said bluntly. "When we were both boys, we saw each other as attractive. Now, you have small breasts and your dick doesn't work," she added.

I didn’t know how to take that. If I were a gay man, I would be irate at losing a male partner. However, if I was truly a woman, I wouldn’t want to be with a cross dresser that had a female personality. I would want a real man that dressed as a man and loved being a man. I was at a point where I had to decide what I really was.

"It's just that physically you still look like a man. It's a little unfair that I find you attractive but you don't with me," I said stalling.

"I can't transition," she said to me.

"Why not?" I asked. The emotional torture was becoming too much. I had an attractive man in the house that I had sex with that was now rejecting me. I wanted him as a man with me or completely female and end this struggle.

"Jack may return," she said flatly.

"Jack was an asshole," I said bluntly and then regretted it. Even if a sibling was an asshole, I would never wish them to be gone. Not my own brother, not for anyone.

"He's part of me, like my brother," she said.

"How long are you going to wait for him?" I asked softly.

"I don't know," she said honestly.

"You called me Nicki. I like that name," I smiled and then went back to my room to think.

It didn’t take long for Jill to barge into my room. "Take off your clothes but leave the breasts on," she ordered.

I obeyed her immediately. Once I was naked except for the fake now-tan breasts, she got on top of me and started kissing me. She massaged my fake breasts turning me and then went down on my penis. I imagined my penis being a clit as she sucked on me. I bucked my hips and arched my back as my penis became more sensitive than ever before. She then took my legs above her shoulders. Our yoga classes had paid off.

“You ready?” she asked me.

I nodded even though I hadn’t been lubed up. She penetrated me forcefully without a condom as I stroked my cock. Within a few minutes, I came on my stomach. She kissed me for a few moments and gave me reassuring words.

“I’ll stay with you until you find a real boyfriend,” she whispered in my ear.

I lay there stunned as Jill went off to take a shower. Even though she had a boyfriend of her own, she was still taking care of my needs. I tried to think of what I could give her in return. Once she came out of the shower, I entered. My nipples had expanded slightly and my breasts were swollen. I would require surgery to get rid of them but for the moment I could hide them from my parents if I always wore a shirt around them.

I had not yet finished my freshman year and would be dependent on my parents for another few years more. I was expected to come back home for the summer unless I convinced them that I could do summer school. In any case, I would be so dead if my parents ever found out.


Jill dressed as a man and went back home for spring break. I envied her ability to switch genders at will. It was becoming increasingly difficult to look normal. I was neither male nor female, somewhere in between. With Jill gone, I considered what she had told me. She would still have sex with me until I found a real man. I was a charity case. I was pathetic.

I decided to send messages online to gay men, anything to keep the fantasy alive. It was reckless and stupid. If they discovered I was transitioning, I could have been beaten or worse. Thankfully, I met a man that was understanding. I created a gay man profile and a separate profile that was completely honest about my transition. As it happened, the transsexual profile got the first hit.

James was a straight man, Asian, and very masculine. He was also a student, he liked to lift weights, play video games, and have sex. He treated me like a woman never allowing me to wear male dress in his presence privately or publicly. Every night of spring break, he came over to the apartment and fucked me raw. Unlike Jill, he really wanted to fuck me. He had me wear tan underwear with a hole in the backside when we had sex to cover up my male parts. He sucked on my nipples as if they were female. He would tell me that they were no different than a flat-chested girl.

We would have sex on the bed but also the floor, the kitchen table, the stairway, and even the couch. I instantly fell in love with him and always made myself available for him. After a wonderful week, Jill came back in drag and found us both fucking on the couch. He had his cock in my ass as he pulled my hair if I recall correctly.

“What the fuck?” she said as quickly closed the door.

“I’m so sorry,” James said getting up.

“How much does he know?” Jill asked me.

“Everything,” I said honestly.

“We’ll talk later,” Jill said and went upstairs.

“Should I go?” James asked awkwardly.

“Not until you finish,” I said to him.

He smiled at me, kissed me passionately, and then fucked me until he came inside me.


As the semester ended, I convinced my parents that I should take summer classes. I continued with my hormone treatments and felt emotional roller coasters I had never felt before. With James, I was the happiest I had been in a long time. He always treated me as a female and even showed me off to some of his friends. I became confident enough to talk to people in public in my new voice.

Jill, on the other hand, was lonely the entire summer. Her boyfriend Chris was gone. She took summer classes and stayed mainly in her room. In August, she came back to the apartment crying and went to her room. I figured she must have broken up with Chris. This wasn’t an act. She really was a woman crying over a break up. She didn’t want to be consoled, and she didn’t tell me about it.

However, not too long afterwards, she started dressing as a man, and I feared Jack had returned. Jill assured me that wasn’t the case but gave me nothing else. She dressed and looked like a man and even had dates with a woman. She never brought this woman to the apartment for fear of creating jealousy between them. I found it amusing that I had reached the point where I could pass so easily.

It didn’t take long before Jill broke up with this woman and started dressing as a woman again. “What gives?” I asked her.

“I couldn’t tell Chris the truth. So, I tried to be normal for a change and date girls like I am supposed to. I tried to fit in with society’s expectations,” she said bitterly.

“What went wrong?” I asked.

“She’s into girls. Go figure,” she said.

“I’m so sorry,” I said half-heartedly. In truth, I wanted her to embrace her femininity as I had and get back with her old boyfriend.

“I’m not unhappy we broke up. It’s just that I trapped. I can’t date men without being found out, and I am not into women,” she said.

“Why not transition now?” I asked her.

“I can’t. Jack could come back,” she said.

Jill always used that as an excuse for non-action. She eventually did get back with Chris, told him everything, and they stayed together as a couple during the fall semester. James continued to be good to me but something changed over the months. He insisted on sucking my cock even though I told him it wasn’t necessary. We got into kinkier sex when I put a strap on, and fucked him hard with it. He liked it so much that we did it more often.

In January, Jill had a serious reaction to medication and got herself arrested and then brought to the hospital. I checked up on her every so often and usually found Chris there. It was then that I began to wonder about my relationship. We were so sexual that we rarely spent time doing the normal things. Chris and Jill had yet to have penetrative sex, and yet seemed so happy together. I had been so happy at being accepted sexually that I had neglected some important things.
James and I continued dating and having sex. All the while, I continued hormone treatments that feminized my face and increased my breast size. I also made a point of losing weight and remaining perfectly hairless. I kept my hair short but feminine. My barber couldn’t even tell I was a man. The only obstacle to complete transition was my parents.


At the close of our sophomore year, Jill moved out and James moved in. She was working at a bookstore, as a man, and wanted to find a cheaper place. She was being punished by her parents financially for having the audacity to get a job instead of summer classes. I helped her move out and gave her a tearful goodbye. She would still be in town, but it wouldn’t be the same. She had given me hope and inspiration to go through with my transition.

However, as soon as James moved in things went downhill. He started asking me to not wear female dress and started making fun of my feminine mannerisms. He would allow his friends to joke about me and not defend me. In the bedroom, he would favor fucking me from behind and playing with my penis. He became anger with me when I refused to penetrate him with a strap on anymore.

While he was gone, I cracked the password onto his computer and saw large libraries of gay male porn. “No way,” I said to myself and then checked the whole hard drive for any other kind of porn. “He could be bisexual,” I said hopefully.
I checked his browser history and there was significant gay porn. I was beside myself. He had said he was straight but his recent actions were the opposite. Everything was starting to make sense to me. I scanned the profiles of his friends on Facebook and sure enough evidence came back that they were all gay men. His photo gallery had no pictures of any ex-girlfriends.

Could I even blame him? I was by all accounts still a gay man until I fully transitioned. I hadn’t even received an operation yet. When we had sex, a person could easily mistake us for a gay couple. How could I not see it after so many months? I felt like I had no right to question him about it but a part of my mind told me the obvious: he had lied.
It didn’t make him wrong. It just meant we couldn’t be together anymore. I wanted to be a straight woman with a straight man. It was simply a matter of compatibility. Still, I didn’t think I had sufficient proof.
“Can you stop wearing dresses and bras in the apartment? No one can see you,” he said annoyed.

“I’m transitioning to become a woman. I have to act the part,” I refused.

“You don’t have boobs, you don’t have a vagina, and you sure as hell don’t have an ass,” he said insultingly.

“I’m working on it,” I told him.

“I think you should give it up. It’s going to be expensive and painful,” he advised.

I decided I had enough. “James, are you gay?” I asked him.

“Fuck no, why would you say that?” he asked angrily.

“Why do you have a full terabyte of porn on your computer?” I demanded.

“You got into my stuff?” he asked outraged, and I saw fear in his eyes.

“You’ve been acting weird recently. All of your friends are gay,” I said.

“Fuck me,” he said shaking his head. “What the fuck does it matter? Don’t I fuck you enough?” he asked rudely.

“I am not a gay man. I am a woman and as a woman I am going to dress, speak, and act like a woman,” I said firmly.

“When are you going to knock this off?” he asked me. “Your parents will never allow it. You’ll never get the money to afford it. Even if you did, no man is going to go for a tranny. Save yourself the headache and start acting like a man again,” he said.

I was hurt and stupefied by what he was saying. I had always thought he had supported my transition and that he was straight. “You listed yourself as straight when we first met,” I said teary eyed.

“Things change,” he said simply.

“Not this. I knew I was gay when I was a teenager,” I said angrily.

“So, you think everyone is like you? People can change. I thought I was straight back then but now I realize it’s more complicated than that. Stop pigeon holing people,” he said.

He was trying to be more progressive than me, and I wasn’t having it. “You either love me as a woman or not at all,” I said finally.

“Alright, I am going to take a walk,” he said and left.

As he did, I felt empty inside. I thought I would never have anyone again and began second guessing myself. Maybe if I flung myself on him and told him I would dress as man but only when he was around things would be okay. In the end, I stuck to my guns, and he moved out shortly thereafter.


I took on a female roommate who was oblivious to my backstory. She never suspected the truth. With James gone, I felt free to dress as a female. The only time I ever dressed like a man was the occasional trip home where my strict parents applauded my grades. They actually had to use make-up to make myself look more masculine. One fateful day, they had a family meeting with me.

“Your brother is married with children now. He has twin sons,” my father said pleased.

“Good for him,” I said in my male voice.

“The family legacy is secure. I hear his wife is pregnant with a third child,” my father continued. “He is my heir.”

I felt uncomfortable with this. I didn’t care about my parents’ money but it sounded like they were throwing me away. “You are the second son. You do not have the same pressure as your brother to continue the family name. I only ask that you do not bring shame to the family,” my father said.

“I have worked hard at school,” I said feeling belittled.

“Ah, but there is more to one’s character than school. I have suspected for some time that you are a homosexual,” my father accused.

I felt a chill go through me. “Of course not,” I denied.

“Do not lie to me,” my father said disappointed. “We have proof from one of your boyfriends.”

James had thrown me under the bus. He must have discovered my parents address from a letter. I couldn’t imagine what he could have sent to my parents as proof. I was royally fucked!

“I can tell from your face that it is true,” my father nodded.

“I may have had discretions,” I allowed.

“More than that, I am afraid,” my father replied.

I got on my knees and bowed my head. “I will do whatever you want to regain your trust, father,” I said sincerely.

“Hmmph, you cannot change your nature. No more than I can make this cat behave as a dog,” he said while holding the family cat.

The evil cat glared at me. “You condemn me?” I asked fearing the answer.

“There is no place for a practicing homosexual in the family. I will give you three honorable choices. You can be a celibate monk the rest of your days. You can do your family duty, marry a woman, and have children with her…”

“Father, I…,” I protested.

“What? Do you believe your mother and I loved each other at first sight? Our marriage was arranged by our parents, and I have been faithful to her this entire time. Throughout history, men have married ugly, repulsive, and disagreeable women, because it was their duty to the family. Do you put your carnal desires over duty?” he asked.

“No,” I was forced to say.

“So, as I was saying, you can be a celibate monk, a married family man, or…

I couldn’t hear the rest. I was doomed to a miserable life. I was dependent on my family and would be cut off if I didn’t comply. Once my father knew about my illegal hormone treatments, he would cast me out or force me to undergo surgery. All because I refused James; why could I have just played along for a little longer until I had my degree?

“Or you become a married woman and godmother to your brother’s children,” my father finished.

It took a few moments for my brain to realize what he had just said. I looked up in confusion. “So, the third option intrigues you, doesn’t it?” my father asked condescendingly.

Had James revealed my transsexuality to my parents? Would he really go that far? Was my father joking hoping to catch me? Transsexuality was a dishonor and shame beyond anything else. It would be better if I killed someone and went to jail for life than that.

“Merely curious,” I said flatly.

“I knew a family that had a girl who married an infertile man. They remained childless but supported the family as expected. This girl was loyal to her husband all her days, dressed respectfully, walked properly, cooked exquisite dishes, and watched over the young children of her husband’s siblings. We all knew who she really was, but she acted with such feminine grace that we did not put them to shame,” my father said.

“An interesting story, father,” I said lamely.

“As it happens, there is a respected family who has a son without…testicles. It was due to a motorcycle accident, I understand. It happened to him fairly recently, so have no doubts that he grew up strong and masculine. His testicles were replaced with synthetic balls,” my father detailed.

“How unfortunate,” I muttered.

“But fortunate for us!” my father said wide-eyed. “I could ‘arrange’ a meeting between you two to discuss shared interests.”

I stared at my father. What the fuck was I supposed to do? It was clear what my choices were. I had to go along or I was finished. “I…would be happy to meet this young man,” I said finally.

My father nodded. “You are not yet presentable,” he said and left the room.


My mother was terse and annoyed with me as she took me to the mall to pick out clothes. She chose a number of slim dresses, and C-cup bras. “I don’t think these will fit,” I said dryly.

“You will lose twenty pounds by end of this year,” she said scornfully.

I sighed embarrassed by this whole affair. What made matters worse is we were shopping for me while I was still in male dress. My mother bought me high heels that would presumably fit me. “I’m not really a fan,” I said awkwardly.

“Nonsense, your legs will look slimmer this way,” she said.

We went to the hair section where my mom found extensions. “I kind of like it short,” I said.

“Your hair makes you look like a boy,” she said annoyed.

Ultimately, I stopped arguing with her and followed her home. Once I was home, a family doctor was already present. “Strip,” my father ordered me.

I complied as my parents left the room. The doctor examined me thoroughly, didn’t speak to me, and simply wrote notes. I kept my mouth shut as he touched my swollen chest. Shortly thereafter, I was given pills from this doctor.

“You will show progress,” my father demanded of me.

“Yeah, sure,” I agreed.

“In six months, you will meet this young man,” my father said. So, in six months I needed to be presentable or lose everything. My father was rarely direct with his words, but he was with his actions. I went home humiliated yet somewhat satisfied. I hadn’t been cast out or beaten into submission. It wasn’t exactly what I wanted in life but there were worst things. Soon thereafter, I was made to get an appointment for breast implants.


It was then that I got an unusual phone call. Jill visited my apartment wearing full female dress. Despite my progress with the hormones, she still looked better than me and it pissed me off. “Well, hello, Jill,” I said pleasantly hoping she would complement my voice.

“Alight, does cash work for you?” she asked bluntly.

“Come inside and we can talk about it,” I said. “Want a glass of water?” I asked her.

“Sure,” she said taking the glass.

"So, guess what? My parents thought it would be an even greater shame on the family if I lived as a gay man. They said that if I behaved as a straight female, they could pass me off as their daughter and bring 'respectability' back to the family," I said bitterly.

"If only my parents were so understanding," she replied.

"Yeah, so, they're paying for the hormone treatment and the eventual surgery," I said.

"So, you're going through with the whole thing?" she asked.

"Of course," I said. She then placed a number of pill bottles on the counter. "You take too many, and it won't do you any good. You can't speed up the process by taking more than prescribed," I instructed.

"Got it," she said.

"You do it wrong and you'll end up with a heart attack or stroke," I continued with genuine sincerity. I also didn’t want to be part of an overdose investigation.

"Let's discuss money," she said changing the subject.

"As I said, my parents are paying for everything. I don't need your money," I said.

"So, what do you want?" she asked confused.

I smiled amused as I played the same kind of mind games my father would play on me. I got close to her across the table. "I want your dick," I said seriously.

"What?" she asked as if she hadn’t heard me.

"You heard me. You haven't been taking hormones, so your dick is good and strong. I want to know what it feels like to be in a straight relationship with a man," I explained.

"First of all, I may look like a man but mentally I am all woman," she objected. "Second of all, what you're suggesting is basically prostitution. I mean, what happened to your old boyfriend?" she asked.

"He cheated on me with another man. Who would have thought he was gay?" I said disappointed.

"Yeah...who would have thought," she muttered as if she knew.

"How many women have you slept with as your male self?" I asked.

"One, but it was an accident," she said awkwardly.

"An accident? Like your dick just fell in her?" I mocked.

"It's complicated," she replied not wanting to discuss it further.

"Well, that's one more than I have. So, you know how it works," I said obviously.

"Yeah, I got the mechanics down. We've done this before," she reminded her.

"That was different. I want you to treat me like a real woman," I insisted.

"How am I supposed to do that?" she asked.

"Practice," I said obviously.

"Are you insane? The idea is for me to transition into a woman. How does fucking you as a man accomplish this?" she asked.

"Even while on hormones, your dick will still work. Once your transition is complete, we stop having sex and become girlfriends," I said excitedly.

"Yes, because that's how it works. When we go shopping for bras, I am just going to have to forget I once had my cock in your ass," she said crudely.

I giggled at that and then became serious. "You wanted my terms. That's what I want," I said.

"Look, I have a boyfriend of my own now. This is technically cheating," she said.

"So, don't tell him," I said obviously. I didn’t want to put her in this position, but I was dying to get some dick before I was sentenced to marry a man without testicles.

She simply stared at me wondering if I was totally serious. "Allow me to consult my other personality," she asked.

I nodded knowing well enough she was nuts. She walked over to the dining room to discuss the issue with her other personality in private. She came back a minute later.

"It's a deal," she said.

Jill reluctantly followed me to my bedroom. She looked over my room noticing what a difference a year could do. I unzipped my dress dropping it in front of her. I puffed out my chest showing her C-cup breasts and then cupped them in my hands.

“They look good,” she complimented.

“Could you tell the difference?” I asked.

“A man wouldn’t,” she replied.

I smirked at that and leaned against the bed. She sighed and started taking her clothes off. "When you come back to me, I want you dressed as a man,” I ordered.

"Very well," she said annoyed.

She got out of her clothes until I was naked in front of her. "I think we need a condom or something," she said awkwardly.

"Not this time. This is freebie," I said going to my knees.

I pulled my underwear down and then touched my flaccid penis. "Act like you enjoy this," I ordered and put my mouth on her.


Jill came over two weeks later, and I was ready with my demands. She was dressed as a boy and I immediately mentally prepped myself. I was going to get fucked by a real straight man. His name was Jack, he loved coming over, and taking me to bed. As required, Jill put a condom on and a generous amount of lube. I got on all fours and waited patiently as he penetrated me. He grabbed my hips and started fucking me hard. He wanted it to be over quickly but that wouldn’t do. I would distract him by having him touch my breasts or kiss me; anything to stop him from cuming too quickly. He was never to touch my penis. I didn’t even want to know it existed. He was a man and I was a woman, period.

I cried out not caring if he gave me dirty looks. I didn’t even need to see his face as he hammered me from behind. Eventually it became too much, and I fell on my stomach on the bed. He continued to fuck me while I was on my belly until he finally came. He grunted like a satisfied straight man.

Exhilarated, I looked behind as a very male-looking Jill took care of her condom. “We’re not done yet,” I said ambushing him in the shower. I kissed him all over as we got clean. “I know a better conditioner,” he began.

“Stop,” I shushed him. “Stare at my breasts,” I ordered.

He complied but disinterested. “Rub them,” I ordered.

He did an amazing job working on my breasts as I worked on my longer hair. Once we were done, I noticed she had brought her bag. “Hurry up and get dressed, so we can go clubbing,” I told him.


What followed were several weeks of Jill coming over as a man, giving me a great fuck, and then us hanging out as girls at the club. Chris would occasionally show up completely oblivious to our business relationship. All of our fun came to an end when Jill collapsed during a jog with Chris. She had a brain aneurysm that nearly killed her. Jill’s parents found out about her self-medicating and our business relationship was over.

“My parents are giving me the drugs I need to transition. I made a deal with them,” she said.

“You too,” I realized.

“They have private eyes spying on me to make sure I dress as a woman at all times,” she said bitterly.

“That’s mental,” I said although I was paranoid my parents were doing the same.

“I am going through with everything. The whole operation,” she told me.

“Same. My parents want to marry me off to a friend of the family who has no balls,” I said.

She smirked at that. “Maybe he’s the one that should be the wife,” she joked.

“Yeah, well, the pictures give me the impression he’s manly. I would give him my balls if I could,” I said honestly.

“He still has a dick, right?” Jill asked concerned.

“Yeah, he’s got synthetic balls, so you can’t even tell,” I said.

“It does take the fun out of squeezing them though,” Jill remarked.

“Or kicking them,” I smiled.

“Ouch, I could never kick a man in the balls after what I have been through,” Jill said.

“You’re going to marry Chris, aren’t you?” I asked her seriously.

“I hope so,” she said.

“Well, I’m likely to get married before you do,” I said sadly. “I’ll get you an invite. You’ll be the only white person there,” I said awkwardly.

Jill looked at me sympathetically. “It’s not like the old days. If things go south, you can escape.”

“Thanks,” I said.


Under obligation, I met Tom at a botanical garden. I had my hair long and made perfectly straight and shiny and was wearing a summer dress. He greeted my parents while wearing a suit and tie. After some small talk with my parents, they left me alone with him.

“Pleasure to meet you,” Tom said politely.

“Same,” I said awkwardly.

He gave me the male gaze for a brief moment and then the two of us walked through the garden avoiding eye contact with each other. He discussed his job and what he had done at the university. I was barely listening. With his suit on, I had to use my imagination on what he might really look like underneath.

His face was clean shaven without imperfections. His face looked almost beautiful. His hands were delicate as if he had never worked with his hands before. His voice was normal, but I could tell he was putting some effort into his speech as if being very careful not to offend me or more importantly my family.

After walking through the garden, he asked me out to dinner which had already been planned in advance. We made small talk about our studies at the university without going into personal details. By the time dinner was over, I didn’t feel I really knew him at all. All throughout, he was polite but seemed bored.

Afterwards, I assumed Tom would call the whole thing off. So, when another date was scheduled I was actually shocked. It soon became obvious that he was dealing with some family pressure to date me, because he quickly changed his tone with me by being a total ass.

He looked me over with a cold stare. “You have split ends. I know a place that can help with that,” he said.

“Thanks,” I said a little surprised by the criticism.

He also took the opportunity to critique my dress and shoes. While still polite on the surface, I could tell he was trying to push me away. He was looking for me to call the whole thing off. Unfortunately, I was under pressure to keep giving Tom a chance.

During one of our dates, I wore a white t-shirt and pants. He commented that he could see my nipples bulge from my t-shirt and that my bra was the wrong size. I shot back that I didn’t know too many men that would complain. I figured threatening his sexuality would piss him off, but he simply shrugged it off.


During this dreadful month, I met Jill for lunch. She had gotten a boob job since we had last met. I was actually curious to see them uncovered but felt it would be too weird to bring it up. She was quickly catching up to me, and I felt an irrational fear that maybe she would end up finished before me.

“It’s like he’s trying to sabotage us before we even start,” I said irritably.

“Maybe he is,” Jill said.

“It’s a real shame. He is good looking,” I admitted.

Jill saw a picture of Tom on my phone. She shrugged and gave it back to me. “Not really my type,” she said.

“Because he’s Asian?” I asked trying to provoke her.

“Not really. He’s too effeminate. You sure he isn’t gay?” Jill remarked.

“What gives you that idea?” I asked not detecting any such thing.

“It’s the face. Something about it isn’t right,” Jill said vaguely.

“Well, he is missing his testicles,” I reminded her.

“That could be it,” Jill allowed.


After a brutal month of having every aspect of my appearance criticized, I went on the offensive. There was very little to work with though. His choice of suits and shoes was perfect. He never wore outrageous ties, and they were always straight.

“You slouch too much. It’s bad for your back,” he told me while we were at lunch.

I straightened up and gave him a defiant look. “You still ride?” I asked hoping to piss him off.

“A motorcycle? I don’t ride,” he replied.

I gave him a flustered look. “I just had the impression you did.”

“How odd,” he remarked.

From that point on, I began to wonder about the story my parents had told me about Tom. I invited him to the beach, and he hesitantly agreed. At last, I would be able to see him underneath the suit he always wore. It was also an opportunity to show off my curves in my new black bikini. It took a while to “tuck” myself but it was worth it. Looking in the mirror, no one would know the difference.

He met me on the beach as planned wearing swim shorts and a t-shirt. “Nice day, isn’t it?” he asked awkwardly.
“Yeah, nice and sunny,” I replied.

I wore sandals as we walked, but he was in his tennis shoes and never took them off. For some odd reason, I wanted to see his feet. “You know, the feel of the sand on your feet is great,” I encouraged him.
He simply nodded and glanced at my feminine looking feet. I had taken pains to make them presentable. “Want to swim?” I asked him.

“Not a good idea: rip tides,” he replied.

I had never known this beach to have rip tides and wondered what he was talking about. “Well, I want to cool off. Care to join me?” I asked him.

He followed after me as I went waist-high in the water. I just loved it as the water would crash against my ass and flow around my breasts. Tom reluctantly took off his shoes and reluctantly entered the water while still wearing his t-shirt.
“You going to get your shirt wet,” I teased as the ocean water had already soaked it.

“It’s fine,” he replied back.

I gave him an odd look. I had thought most men would enjoy taking their shirts off at the beach and displaying a nice muscular chest. I was almost tempted to take my bra off to encourage him but thought better of it as I noticed other people were watching me.

He never did take his shirt off the entire time we were on the beach.


Jill smiled in amusement as I detailed the event. “Maybe, he has a horrible chest scar from the motorcycle accident,” she suggested.

“When I mentioned a motorcycle, he acted like he never rode one before,” I objected.

“Careful, he could be suppressing a bad memory,” Jill advised. She would know after the car accident that nearly killed her.

“I want to know what’s underneath that shirt,” I said curiously.

“There is another explanation…no way, it couldn’t be,” she chuckled.

“What?” I asked impatiently.

“He could be like us,” she replied amused.

“You mean he’s growing breasts?” I wondered.

“No, the opposite. He did have breasts,” she said holding her own for emphasis. “But now they’re gone,” she smiled.

It took me a few seconds to register. “That’s crazy,” I rejected.

“Even crazier than the story your parents told you about him?” Jill questioned.

“Yes, that’s a lot more plausible than this,” I said stupefied. The very idea was absurd. There was no way my parents would have tried to pair me off with…

“Oh my God,” I realized the truth.

“Yep,” Jill confirmed.

“What do I do?” I asked unsure of myself. I had never confronted such a possibility.

“You have to confront him about it,” Jill said.


Before I would question Tom about this, I decided to search the records of his university. I found his graduating class but Tom’s name was nowhere to be found. I found a number of students with the same last name and zeroed in on a particular name: Tam. Searching for Tam, I finally found her picture in the yearbook. The resemblance was striking: this was him. The picture of a stone-faced young woman was the same person as Tom.

I felt a chill as I concluded my investigation. Tom had been born a woman, a female-to-male transsexual. The story about the motorcycle accident was all a ruse. He had no balls, because he had never had balls. He didn’t feel comfortable taking off his shirt because of the scars. It was the reason why he was so critical of my appearance. He knew everything I had done incorrectly, because he had lived years of his life as a woman.

I took a moment to process this. I had no doubt in my mind that I was attracted to men but could I love a man with no dick? Was he really a man at all? And who was I to judge? No, I didn’t have to settle for less than what I wanted. I wanted a man with a penis, end of story. I didn’t have to lower my standards just because I was a transsexual. That’s not how it was going to be. I was going to confront him and call the whole thing off.

Tom and I met to play a friendly game of racquet ball at the club. I felt a little uncomfortable bringing up the subject while being alone with him in such a confined space. As it was, he was kicking my ass easily. I had never been the athletic type but damn.

“Tom, we need to talk,” I said after I had regained my breath.

“What is it?” he asked almost bored of me.

“Were you born female?” I asked bluntly.

He gave me a look of shock and then defensive anger. If he had been a real man, he would have just laughed it off. What I saw from Tom was genuine fear. “What are you talking about?” he demanded.

“I was told you lost your balls in a motorcycle accident and now you tell me you’ve never rode one. You never take off your shirt,” I began.

“You want me to take off my shirt?” he asked rhetorically.

“I do,” I replied forcefully.

“Fine,” he said and then proceeded to take off his shirt.

I expected long scars indicating breast removal and nipple reduction. Instead, I saw nothing out of the ordinary. It was a normal male chest with even some chest hair to boot. My confidence in my theory started to erode.

“Satisfied?” he asked.

“I want to see your dick,” I said softly.

“We’re not at that level, yet,” he replied.

“When then?” I asked incredulous.

“After the wedding, if it happens at all,” he said annoyed.

“That’s not good enough. I want to know what you got now,” I demanded.

“You’re one to talk. I know everything about you,” he said insultingly.

“Who did you fuck over to get arranged to someone like me?” I asked. “What crime could you have committed for your parents to force you to marry a tranny like me?”

Tom had nothing to say to that. “Just call off the engagement,” he said simply.

“No, not until I know the truth,” I replied.

“What does it matter?” he asked becoming slightly upset.

“I have already made peace with it, if you tell me everything,” I said.

“What do you want to know? If I have a dick or a vagina?” he asked rhetorically.

“To start with,” I said obviously. “Can you still have children?” I asked.

“Wait…you’re suggesting…no, never,” he rejected.

“It’s a hell of a lot easier than a surrogate,” I said amused.

“You’re out of your fucking mind if you think I would let you impregnate me after everything I have been through,” he said confirming what I had discovered.

“So, it is true,” I whispered not wanting to believe it. Our parents had set us up together to correct two problems at once. My parents had sought out family that had a female-to-male transsexual just for me.

“I don’t even know if it would work,” I said honestly.

He was visibly distressed at this point. “I can’t be with you knowing that you know about my past,” he said finally.

I got close to him to reassure him. “If we are together, you will always be the man. Whether, you have a real dick or a fake dick, I just want to be fucked hard,” I said.

“God damn,” he replied softly. “You really mean it?” he questioned.

“Before the wedding, I want your best,” I told him. Although my voice was confident, my mind was in turmoil. Could I really do this? Only a few years ago, he was a woman. But Jill had fucked me as a man and was now a woman now. She was great as a man. Real men had just been disappointments.

“Alright, tonight then,” he said regaining back his confidence.

He had been a woman and could teach me to act and behave as a woman should. I had been a man and could teach him how to be a man. In a twisted way, it was a perfect match. I followed him out of the gym and then drove with him back to his house.


I had never been to the house his family had given him. There was nothing feminine about it. Instead, there was a male-looking study, pool table, game consoles, a library of only male authors, a liquor collection, and sports memorabilia. Tom had over-compensated to the extreme.

“We should shower first,” he said now confidently.

It made sense. We were both sweaty from racquetball. “Okay,” I said a little nervously wondering what I would end up seeing.

He led me to a large bathroom with a shower that could easily fit two people. He casually took off his shirt and shorts. I noticed that his body was strong and lean. He hesitated briefly, turned his back to me, and took off his underwear. I didn’t get to see his front as he entered the shower. I felt a little uncomfortable exposing myself to him. I was also ashamed of mis-gendered parts. I took my time taking off my clothes and then entered the shower with him.
“It’s okay,” I assured him.

He turned around giving me a normal male torso with defined abs. I lowered my eyes and saw what I had figured out weeks ago. Where there should have been a penis and testicles was nothing. I had never seen female parts before in real life before. I titled my head indicating to him that it wasn’t a big deal. He then touched my breasts feeling the implants in his hands. He nodded as if to confirm what he already knew.

“We’re both kind of fucked up,” I remarked.

“Maybe we are,” he smirked.

“Get your cock and take me,” I told him turning my back.

He exited the shower and came back a few moments later. I kept my eyes away from him not wanting to see it or how he was putting on. I just wanted to imagine there was a man in the shower with me. He put his hands on my hips, and I took a deep breath knowing the pain would soon follow. I had no idea whether he knew what he was doing. Had he fucked real women with this cock before?

He then moved closer to me and then I felt it. It was soft yet sturdy. It felt like real flesh. I didn’t dare turn around and risk the fantasy I had created for myself. It was a real flesh-and-blood penis. That’s all I needed to know. He gently and cautiously pushed farther in. I sighed as he penetrated me for the first time.

“You alright?” he asked me.

“Yeah, keep going,” I encouraged him.

He pushed all the way to the hilt and slowly moved back-and-forth rubbing me the right way. I placed my hands on the wall of the shower and pushed into him. “Faster,” I whispered.

He complied picking up speed. He placed his hands on my breasts keeping me steady. My legs were starting to become weak as I was getting close. Finally, I couldn’t wait any longer and started stroking my dick. It immediately shot out, and I gave a feminine moan.

“That was easy,” he said pleased with himself.

In my sexual euphoria, I wondered just how many girls he had fucked before me. “Aside from me, have you ever fucked a man?” I wondered.

“Never and that includes you,” he replied.

I turned around and stared at his masculine face. I looked down and saw a very realistic fake cock. “Take it off. I’ll lick you until you cum,” I offered.

“Don’t worry about it. It rubs me the right way whenever I thrust,” he said.

“Oh, okay,” I said. Still, I didn’t think it was enough. I got close to him and started kissing him. He held me and returned my kisses. Yes, this could work. One day I would get him pregnant and have our first child but until that day, he would be my husband.


Soon thereafter, I told my parents I would marry Tom despite his “condition.” My parents never confirmed Tom’s true nature, and I never told them. Tom’s parents also kept up the ruse acting as if he had always been a man. The only ones that would know would be the immediate family. So, at the wedding, hundreds of relatives and friends showed up none-the-wiser. I wore a beautiful thin wedding dress and spent hours in the make-up chair. My make-up artist and hair dresser had no idea I had once been a man.

After the ceremony was over, I bumped into Chris and Jill. “Glad you could come,” I said to Jill. She gave me a hug. She had recently gotten her sex-change operation out-pacing me. It didn’t matter though. I had come to terms with my male parts. There was no need for any operation until I had a child or two.

“Wouldn’t miss it,” Jill smiled.

Later, I would go to Jill’s wedding but something was off about her. During half the day, she acted like she didn’t recognize me, and her mannerisms were different.

On my wedding night, I took a pill to get my dick hard and ready. I lubed it up good and then saw my naked husband on the bed waiting. “Hopefully, we only have to do this once,” I smiled.

“Whatever it takes,” he allowed.

Someday, he would get himself a flesh-and-blood penis, and I would invert my own into a neo-vagina. It was only a matter of time but tonight we would have use the tools we were born with. I kissed Tom to reassure him and then slowly pushed inside of him. I had never penetrated a female vagina before. It was warm and moist. I cautiously moved around a little and then worked to cum as quickly as possible. I knew Tom was feeling pulses of pleasure, but he kept his mouth shut giving nothing away. In spite of myself, it did feel kind of good.

I finally spilled my seed into his womb and was immediately tired from the effort. After a brief recovery, he went to fetch his fake cock. “Now, the rest of the evening is mine,” he smiled.


A few months later, after an exhilarating game of racquet ball, I hit the showers. Despite my best efforts, Tom easily defeated me. I almost enjoyed being defeated. If I were to win every time, Tom might feel his masculinity was threatened. I took a shower stall, stripped in private, and then enjoyed the warm water. I never stripped down on the common floor for fear of someone freaking out and reporting me. When I got out, I was in a new set of clothes with a towel around my long hair.

Jill entered the locker room in a tennis outfit. She looked a little more masculine since the wedding but of course she wasn’t wearing any make-up this time. Jill stripped down and put her clothes in a locker. She had a slight difficulty getting her bra off but was soon naked in front of me. Her body was perfectly shaped making it impossible for anyone to know anything was amiss.

I was about to greet her but something was odd about her. There was something in her walk and movement that raised alarms. I couldn’t pinpoint what exactly at the time, but this version of Jill was different from before. She gave me a strange look giving me elevator eyes as she looked over my body.

I waited for her to recognize me or acknowledge I was real. Instead, she smirked at me and then went past me to the showers.

I looked back as she disappeared inside the shower stall. I felt a sudden chill as I realized what was going on.

Jack was back.

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