The Black Ring III

The Black Ring III
(Sequel to Black Ring II)
Black Ring II
Black Ring I

“I need to call an old friend,” I said dialing the number on my cell phone. Niki picked up and greeted me with a feminine voice. Not as good as my own but a considerable improvement from the last time we met.

“Hi, I need to talk to you about those pills you are taking,” I said bluntly.

“Why? You want them now?” she asked.

“Yeah, just tell me how much you want for them,” I said becoming impatient.

“I don’t know…I might have to see a doctor’s note,” she said reluctantly.

“I don’t have time for this shit. Just tell me your terms,” I said irritably.

“Alright, we can meet at my place, so I can educate you on how it all works,” she said condescendingly.

“Much appreciated,” I said with fake sincerity.

Niki then sent me a text message on the time, date, and place. I turned to Jake to hear his thoughts on the matter. “We’re going to need money,” he said.

“We’ll use my credit cards while we wait on the student loans,” I said.


I showed up at the student loan office as Jack. I submitted all my financial documents, job history, and filled out their forms. I felt giddy as I started signing documents. For the first time in my life, I felt I was in control of my own destiny.
I finally came over to Niki’s apparent. She greatly improved on her appearance since we had last met. If I hadn’t none better, I would have assumed she was born female.

“Well, hello Jill,” she said.

I smiled politely, her voice still gave her away. I was dressed as a woman and despite not having any hormone therapy was still the more feminine of the two. Was I competing against Niki? Of course, I was.

“Alright, does cash work for you?” I asked wearing a purse.

“Come inside and we can talk about it,” she said.

I went inside the apartment and hung out in the kitchen area. “Want a glass of water?” she asked.

“Sure,” I allowed. Using my female voice did put a little bit of a strain on my vocal cords.

“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,” she said mockingly.

“If only my parents were so understanding,” I replied.

“Yeah, so, they’re paying for the hormone treatment and the eventual surgery,” she said.

“So, you’re going through with the whole thing?” I asked.

“Of course,” she 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,” she said.

“Got it,” I said annoyed. I knew how hormones worked. I didn’t need a lecture from my own drug dealer.

“You do it wrong and you’ll end up with a heart attack or stroke,” she continued.

“Let’s discuss money,” I said changing the subject.

“As I said, my parents are paying for everything. I don’t need your money,” she said.

“So, what do you want?” I asked confused.

She got close to me across the table. “I want your dick,” she said seriously.

Jake burst out laughing, and I had to keep from smiling. “What?” I asked.

“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,” she explained.

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

“He cheated on me with another man. Who would have thought he was gay?” she said disappointed.

“Yeah…who would have thought,” I muttered.

“How many women have you slept with as your male self?” she asked.

“One, but it was an accident,” I said.

“An accident? Like your dick just fell in her?” Niki mocked.

“It’s complicated,” I replied.

“Well, that’s one more than I have. So, you know how it works,” she said.

“Yeah, I got the mechanics down. We’ve done this before,” I reminded her.

“That was different. I want you to treat me like a real woman,” she said.

“How am I supposed to do that?” I asked.

“Practice,” she said obviously.

I looked at Jake for help. He merely shrugged. As a male-to-female transsexual, the prospect of prostitution with men was a well-known fear. But never had I ever dreamed I would end up a male gigolo. “Are you insane? The idea is for me to transition into a woman. How does fucking you as a man accomplish this?” I asked.

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

She giggled at that and then became serious. “You wanted my terms. That’s what I want,” she said.

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

“So, don’t tell him,” Niki said obviously.

I simply stared at her wondering if she was totally serious. “Allow me to consult my other personality,” I asked.
She nodded knowing well enough I was nuts. I walked over to the dining room to discuss the issue with Jake in private.

“What do you think?” I asked.

“We do need to watch our money supply, and we can’t get this stuff through legitimate channels,” Jake said.

“But it’s cheating on Chris,” I said stubbornly.

“Chris isn’t going to want us as we are forever. We need to make a play,” Jake said.

“Damn it. I wish you could take control once in a while,” I sighed.

“Same here,” he smirked.

I walked over to Niki. “It’s a deal,” I told her.


I reluctantly followed Niki to her girly bedroom. She had really over-compensated from before we lived together as men. She unzipped her dress dropping it before me. I noticed she wasn’t using padding inside her bra this time. With implants, her breasts were full inside her bra. She undid her bra revealing C-cup size breasts.
“They look good,” I complimented, a little jealous of her.

“Could you tell the difference?” she asked.

“A man wouldn’t,” I allowed.

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

“Very well,” I said annoyed.

I got out of my clothes until I was naked in front of her. “I think we need a condom or something,” I said awkwardly.
“Not this time. This is freebie,” she said going to her knees.

She pulled my underwear down and then touched my flaccid penis. “Act like you enjoy this,” she said and put her mouth on me.


Moments later, I was in my car totally shell-shocked. “That was disturbing,” I said out loud.

“At least you got your pills,” Jake said brightly.

“These better not be placebos. I’ll kill him…her….it…whatever,” I said annoyed.

I went home and started taking the medication as instructed. It didn’t magically turn me into a woman like some fairy tale. For the first few weeks, nothing seemed to change. Knowing the hormones could have an adverse effect on my sperm count, I went to the clinic. I had my sperm saved in case I wanted my own children in the future.

“You think this is really a good idea?” Jake asked me.

“Why the hell not?” I asked offended.

“Well, we are a bit fucked up,” he said putting it lightly.

“It’s probably a really really recessive gene. Our kid isn’t going to have what we have,” I said dismissively.

“What if the kid does?” Jake asked darkly.

“Then my future husband and I will treat that kid with respect unlike our parents,” I said.

“Still, we have a rather benign form of it. Some people with this disorder have unfriendly personalities,” Jake said.

I knew exactly what he meant. Jane had tried to kill me. “Look, it’s just in case. I rather have it be available than not. After I am chemically castrated, I won’t have any chance at all,” I said.

“Since we are going to marry a man, who will be the surrogate mother?” Jake wondered.

“That’s a good question,” I replied.


At my next session, I spilled the beans to Dr. Stein. “As you know, everything you say in this room is confidential,” he said in a boring monotone voice.

“I’m on hormones, now,” I said bluntly.

He simply stared at me with his spectacles. “What kind?” he asked.

“The female kind, duh,” I said impatiently.

“Where did you get them?” he asked curiously.

“That’s my business,” I said. I wasn’t going to tell him the truth just yet.

“Very well. You are aware of the risks involved. Once you start forming breast tissue, you will require surgery to remove it,” he said.

“I have no intention of removing it,” I said.

“And what if Jack returns? Won’t he be a bit surprised by this?” he asked.

“Jack is dead,” I said firmly.

“I see. So, you have come to accept it?” Dr. Stein asked.

“Yes,” I said flatly.

“Will you tell your parents at some point?” he asked.

“Not just yet. Once I am completely financially independent, I can tell them to fuck off,” I said.

“I think it would be a good idea to have a diary. Write down any physical, mental, and emotional changes you may have during this transition,” he advised.

“Yeah, sure,” I agreed.


Chris and I continued to date and that included our runs. One day, I was panting and out of breath as we reached the finish line. Chris seemed fine as if it were nothing. “Hey, what’s wrong? You’re usually faster than this,” he said concerned.

I couldn’t lie to him. I had to tell him the truth of the matter. “I am taking hormones,” I told him.

“Wow, so, you’re finally doing it?” he asked surprised.

I didn’t sense he was over joyed by this or enthusiastic. He looked concerned more than anything. “Yeah, the sooner the better,” I said.

He nodded. “Well, good for you,” he said giving me a hand shake. I shook his hand. We were both dressed as men after all.


Niki got more demanding with my next visit. I put on a condom and a generous amount of lube as I stuck it inside her. She was on all fours with me on my knees. I grabbed her hips and started fucking her hard. Every so often, she would instruct me to touch her breasts or kiss her a certain way. It was an absolute negative to ever touch her penis. She acted as if I wasn’t there as she cried out and became vocal. I was her ultimate fantasy, a straight man making love to her. Eventually, she collapsed on the bed and I got on her back. I continued to penetrate her until I came in the condom. I grunted a few times as I did to further her fantasy.

After sex, we showered up, and she gave me more pills. As time went on, she became more imaginative. We had sex in the shower, on the couch, on the kitchen counter, and even on the floor. Not everything was work between us. We would both dress up as girls and go to the club. I invited Chris to come. He was completely oblivious that Niki and I had a “business relationship.”

The hormones were making some progress. I felt a little swollen under my nipples, and I felt scared for the first time. “I’m really doing this,” I said to myself.

“Isn’t it what you want?” Jake asked.

“Yes, but what if things don’t work right. What if one boob is bigger than the other. What I they don’t look right?” I asked.

“Just get a boob job,” he said simply.

“I don’t have that kind of money,” I said.

“Not now but later you will,” he assured me.


At the bookstore, I still dressed as a man. No one could tell I was on hormones. I did my job well and got paid a measly amount. I continued to excel in my subjects and was meeting my goal of graduating early. One fateful day, I went jogging with Chris. Nothing seemed out of the ordinary until I felt my vision get blurry.

“Hey, Chris, I have to stop,” I said but my words came out slurred.

“Are you alright?” Chris wondered concerned.

“Just a really bad headache,” I said and then blacked out.


I woke up in the hospital and saw my parents talking with the doctor. A sudden dread came over me. I would later find out that the doctor had told my parents I had a brain aneurysm which was caused primarily by the car accident two years prior. The doctor also informed my parents that they detected an unusual amount of estrogen in my blood indicating hormone therapy. To fix my aneurysm, surgery was required which resulted in my head being shaved.
At first, I wasn’t aware of my condition. My initial thought was that my illegal hormone therapy had given me a stroke. I flexed both my fingers and then noticed Jake in the room. A nurse came over to the doctor to inform him I was awake.

“How are you feeling?” the doctor asked me.

“Groggy,” I replied.

“The anesthesia will wear off in several hours,” the doctor assured my parents.

“Jack, you suffered a blood aneurysm in the brain. It should have been caught after your car accident. We did a surgical procedure to correct the problem,” the doctor informed me.

I felt a little relieved that it hadn’t been my fault that it had happened. The car accident had killed Maria, Jack, and was now threatening me. The doctor didn’t feel to need to discuss the “other” details about me and went back to my parents.
I exited the hospital in a wheel chair and was taken to my parents’ SUV. Thankfully, I had collapsed in male clothes. My parents took me back to their place and then let me sleep for the rest of the day. If there was small talk between us, I
didn’t remember it.


As soon as I awoke, it was early morning. I put on some gender-neutral clothes and strolled into the bathroom. Fortunately, the surgery didn’t affect my motor functions. I could walk and grasp objects as before. Looking at my reflection, I saw a sickly-looking person stare back. My head was shaved and there was a bandage on my skull. I looked neither male or female; more like Ripley in Alien 3.

As I entered the living room, the dachshund instantly betrayed me by barking at me. The dog never barked at Jack, just me. My parents exited their bedroom upon hearing the dog barking.

“I hate you,” I said to the dog.

“You finally woke up,” my mother said condescendingly.

I wasn’t sure what to say, so I kept my mouth shut. At this point, I wasn’t aware how much they knew about me. My father also entered the room and took a seat near the fire place to the right of me. My mother was on a couch to the left of me. The parents had planned this intervention. I was being ambushed.

“Want something to drink?” my father asked.

“No,” I said softly.

My father took hold of the excited dachshund. “I assume you are Jill right now?” my father asked.

“Yes,” I replied honestly.

“The doctor told us that you have estrogen in your blood. He told us the only explanation is that you’re undergoing hormone therapy,” my father said without emotion.

A felt a chill go through me. My car keys, my wallet, and my phone were in the hands of my parents. I had nothing if they kicked me out of the house. “Is there a question?” I asked defiantly.

My father paused creating awkward tension between us. “Are you taking female hormones?” he asked finally.

“Yes,” I answered shakily. I had never felt so much fear in my life. In almost all cases, Jack had been in control of the direction of my life. He was the one that got the lectures, the punishments, and humiliation. I was simply there for the ride. My parents never punished me; they simply ignored me.

“Where did you get them?” my father continued the interrogation.

“From a friend,” I said vaguely.

“A licensed doctor?” my father asked already knowing the answer.

“No,” I said simply.

“Where did this friend get these drugs?” my father asked.

“I don’t know,” I said truthfully.

My parents looked at each other as if condemning my drug source. “How can you be sure these drugs are safe?” my father asked.

“I don’t. I simply trust this friend,” I replied.

“How are you paying for these drugs?” my father continued.

“My friend doesn’t have a car. I take this friend places,” I lied. I had to think quickly to explain how I spent my money. My father knew how much I spent in gas but couldn’t know where I was going with it. I also made sure to mask the gender of my so-called friend.

My father was smart enough to detect the deception but decided to drop this line of questioning. “Is it your intention to transition from male to female?” he asked.

“Yeah,” I said flatly.

My parents didn’t make any sudden emotional outburst. It was as if the entire scene had been prepared in advance. My parents were simply confirming what they already knew. “You are attempting to transition without psychiatrist counseling, legal prescriptions, or consulting with us?” my father accused.

“I knew I would never be approved, not with my condition,” I replied. “I knew you wouldn’t approve either.”

“Did you think you would be able to get the surgery necessary to transition from your own pocket?” my father asked.

“I figured I would save up for it,” I replied stubbornly.

“More likely you thought you would get a number of student loans to pay for it,” my father said knowingly.

I said nothing revealing nothing. My father sighed as he considered what he wanted to do. “The honest truth is that you appear to me as my son Jack, but I don’t know the person inside. I am not sure who you are, but you are not my son.”

What my father said was true but somehow it felt very hurtful. My father was grieved that his son was gone as I was too. “I miss Jack too. He was in my head every single day and now he is gone. No one feels his loss more than I,” I said daringly.

My parents studied me perhaps to see if I was sincere. I had the distinct impression they saw me as an alien in their son’s body. “We haven’t treated you as a member of this family. We saw you as part of the disease we were trying to cure. We didn’t understand what we were dealing with, no one did,” my father began.

“It has become obvious to us now that you are our child just as Jack was. We should have treated you both as siblings. Jack has died…but you are still our child,” my father said controlling the grief in his voice.

“We don’t want to lose you too. So, I am going to offer you a deal, a new beginning,” my father offered.

“What kind of deal?” I asked curiously.

“We will put forth the money for your hormone treatments and surgeries to aid in your transition. No daughter of mine is going to look like a half boy-half girl freak. You will look perfectly feminine after these treatments and surgeries are done. You will stop going to your ‘drug dealer’ and instead go to a licensed physician we will find for you. You will dress, behave, and speak as a woman at all times. You will end any student loans, credit cards, or alternative money supply you may have,” my father began.

I was too much in shock to note my father being an asshole about gender roles. My father was offering everything I wanted and more. There had to be a catch. “I assume you are attracted to men?” my father asked.

“Yeah,” I said lamely.

“And do you have a boyfriend?” he asked.

“Yes,” I said truthfully.

My father nodded as if he suspected all along. “I expect you to be monogamous and keep a decent reputation.”
“Sure,” I replied awkwardly.

“In return, you will keep your grades up and graduate early as you have been. When you graduate, I will find you a job that won’t ask questions about your past. You will also preserve a sample of your sperm that can be used later,” my father demanded.

“As you say,” I allowed.

“Do you need time to think it over?” my father asked.

“It’s a lot to take in. Can I just think for a moment?” I asked.

“Take a walk around the neighborhood if you need to,” my father permitted.

I simply stared at him. The asshole wasn’t going to give me back my keys unless I agreed to his deal. “Sure,” I said and then walked out of the house.


As I walked down the street, Jake appeared next to me. “What do you think?” I asked him.

“He’s a clever man. If you don’t do as he says, he will claim you’re not serious about this transition. He’s trying to see how committed you are,” Jake smirked.

“So, I have to go at his pace or else he will accuse me of not wanting to be a woman? I have to speak, dress, and act how he wants me to or else he will cut me off. I should just use the student loans and tell him to fuck off,” I said bitterly.
“Isn’t this what you wanted?” Jake asked me.

“I wanted it at my own pace. If I decide to dress or act a certain way that’s my business. I won’t be told when and if I can get surgeries. The truth is that I am scared of these changes. I have never been in charge of my life like this before. What if my parents are right? What if I am not really a girl but just a fucked-up part of Jack’s psyche? What if I was never meant to be a girl?” I asked.

“You’re happy when you dress as a girl. It’s obvious. Just ask Chris,” Jake said.

“I don’t know. I don’t know if I can pull it off. Can I really be a woman for the rest of my life, be a wife, and be a mother? What if Jack comes back?” I stammered.

“Forget about Jack. This is your opportunity to get what you want and make amends with our parents. If after the transition, our parents still don’t respect us, we can make our own way,” Jake argued.

“I don’t know,” I said indecisively.

Jake took out a coin. “Let’s say we flip for it.”

“That’s not a real coin,” I said irritably.

“Whatever side it lands on is our true intention,” he smiled.

“Fine, heads, we take the deal,” I said entertaining it.

Jake flipped the coin and let the coin fall on the ground. The coin spun on the sidewalk for a few moments. “Really?” I asked Jake annoyed.

“Wait for it,” he insisted.

The coin finally turned head up. “Alright,” I agreed.

Jake picked up the coin and placed it in his pocket. I l later learned that it was a two-headed coin.


I came back into the house with my parents still sitting. Jake took a seat next to my father as if he was my father’s long-lost son. I took a seat across from my father. “Let’s do it,” I said.

“You can start by dressing in proper attire,” my father said gruffly.

“I didn’t bring any of my clothes with me,” I objected.

“While you were in the hospital, your apartment was searched. You will find your clothes in your bedroom,” my father said simply.

I wanted to lash out in anger. He used my hospitalization to take my apartment keys and search the apartment. He knew about my clothes and the drugs before our little chat had even started.

“Chill out, Jill. Just go with it,” Jake said calming down.

“Thank you…for your thoughtfulness,” I said and then went to my room.

I went into my old room and sure enough female clothes from my apartment were in the closet. I also found my fake breasts on the top shelf of my closet. “This is so embarrassing,” I said displeased.

I put my fake breasts on my chest, put on a bra, and then used my specialized panties that hid my male parts. I then wore the black dress and finally the black high heels. Without doing my make-up, I still looked like a boy in a dress.
I exited my room awkward and embarrassed in front of my parents. “Did you also take my make-up as well?” I asked angrily in my female voice.

My parents were initially surprised by my female voice. “You can use mine,” my mother said.

My mother led me to my parent’s bathroom where her make-up was kept. “Do you need any help?” my mother asked condescendingly.

“No, I’m fine,” I said irritably.

My mother watched as I went to work on my hair and face. When I was finished, my mother looked at me impressed. I got the impression that my parents didn’t take my cross dressing seriously. They had never seen their son in drag before.

Once, I was done I came out to my father. He also was impressed by my look. “Well, you look presentable after all,” my father said condescendingly. “Enjoy the mall with your mother.”

I stared at my father. He was testing me to see how I would act in public. “I will,” I replied in my female voice.


My mother took me to a number of expensive women stores. “Have you thought to getting earrings?” my mother asked me.

“She noticed the indents on your ears,” Jake said helpfully.

“I have worn earrings before,” I replied.

My mother approached a jewelry desk. “Pick out something you would like.”

I couldn’t tell if my mother was being generous or testing me. If I picked earrings that weren’t feminine enough, it would betray me. I cast my index finger over the glass as I considered them all. Jake also placed his finger on the glass. We met in the middle picking one out. My mother made no comment as she bought them for me.

My mother then questioned me on my opinion of shoes and dresses. I gave my honest opinion with Jake helping me out. I could not be tricked. I had two minds in my head. We came over to the bra section.

“Ideally, what size would you like to have?” my mother asked me.

She was testing me to see if I would say something outrageous like Double D’s. “A, B or C cup would be fine,” I replied.
My mother picked out a few dresses and had me try them on. I awkwardly went to the female changing room and tried them on. “These fit and these do not,” I said handing my mother the dresses.

“You’ll probably lose weight, so I’ll get you these,” my mother said referring to the ones that didn’t fit.

I interpreted my mother’s meaning to mean that I would lose weight. I was under weight as a male and typical size for a female. I guess my mother wanted to make me a skinny female or have me fail trying.

After the mall trip, my mother took me to the salon. My hair was treated but not cut. My mother got me hair extensions that I knew I would be forced to wear. Looking into the mirror, I looked a lot more feminine with longer brown hair.


When I arrived back home, my father looked at me approvingly. “You look beautiful,” he said awkwardly.

My father complimenting me as his daughter was the oddest thing to me. “Thanks,” I said lamely.

“All your things are in here,” my father said giving me an expensive black purse. I knew then I wouldn’t be getting my back my male clothes.

I checked the purse to see that my wallet and keys were inside. “I’ll drive you back,” my father said.

I followed my father to his car. I would be his hostage until I arrived safely back at my apartment. I took the passenger seat while Jake sat in the back. Most of the drive was filled with awkward silence.

“This boy you’re seeing, what is he like?” my father asked.

I couldn’t refuse his questioning. I was stuck. “He gets good grades and is athletic,” I said vaguely.

“How well do you know his family?” my father asked.

“Well, I dated his sister as a guy while I was on break dating him, its complicated,” I felt like saying. “I’ve met his sister is all,” I said finally.

“Obviously, I am not worried about you getting pregnant or getting anyone else pregnant,” my father said
condescendingly. “I am worried about diseases, the incurable kind.”

“There is nothing to worry about,” I said feeling uncomfortable.

“I would like to meet him sometime,” my father expressed.

“Sure,” I said. How could I refuse him at this point?

It was night as my father dropped me off to where my car was. My father looked around and noticed there was a running/bike trail nearby. “You might want to take it easy,” my father advised me referring to my runs.

I simply nodded. Typically, a father would give his daughter a hug. My father wasn’t ready for that. He simply offered his hand. I painfully shook his hand and went to my car. Had I won or lost?


Despite my parents’ insistence that I always dress in female clothes, I felt liberated once I got to my apartment. I could dress as I pleased and present myself as either gender if I wanted to. After all, dressing as a female was still a lot of work. I went to class as either sex and thought nothing of it. Still, I felt like I was being watched.

While I was eating lunch on campus, an older man in black clothes came by to sit across from me. “Can I help you?” I asked in my male voice. I was wearing male clothes at the time.

“I work for your dad,” he said.

“Good for you,” I said sarcastically.

“My job is to take pictures and take notes. I just felt I should give you the heads up,” he said.

I simply stared at him. “I’ll find a way to get you arrested,” I promised.

“Been there, done that. What I do is perfectly legal,” he said dismissively.

“How much is my father paying you?” I asked angrily.

“I can’t say but its more than you can afford,” he smiled.

“You stay away from me,” I told him.

“This will be the last time you will see me,” he promised. “You look prettier in a dress, really,” he smiled and then walked away.

“Fuck me,” I said frustrated.


I met up with Chris at a restaurant. I was dressed in female attire. He asked me how I was since my hospitalization. After I assured him I was alright, we discussed my parents’ deal.

“Wow, your parents paid a private eye to spy on you. That’s mental,” Chris said.

“I have to be a woman 24/7 in public or that fucker is going to report me. Then, the deal is off, and I lose everything,” I said angrily.

“It’s just one guy. He can’t see everything,” Chris said.

“I don’t know if it’s just one guy, and he just has to bust me once,” I said frustrated. He could be in this restaurant for all I know.

“Or in the parking lot,” Chris said helpfully.

“If he’s spying on me, he’s spying on you too,” I said.

“It doesn’t matter. So what if your parents know who I am,” Chris said dismissively.

“Thanks, Chris,” I said appreciatively.

After dinner, I gave Chris a loving kiss in the parking lot. I hoped the private eye caught it.


I called up Nicki and told her everything including my parent’s deal. “Don’t worry about it. I already got a man now,” she said. “Good luck.”

I stayed in touch with Niki as she went through her therapies and operations. She was always one step ahead of me giving something to look forward to.

Due to personal preference and fear of the private eye, I dressed as a female whenever I exited the apartment. I even started doing it when I was alone in the apartment. I was now taking prescribed hormone pills and discussing my issues with Dr. Stein. The hormones did change my emotional balance but not to any serious extent. I always had Jake to balance me out if I was about to do something stupid.

As a way to test my resolve, my parents ordered electrolysis appointments. Each appointment would be time consuming and painful. It would permanently end the growth of facial hair. I discussed the issue with Dr. Stein.
“You think your parent’s new-found enthusiasm for your transition is a test?” he repeated in his boring monotone voice.

“Yeah, they’re testing my resolve. They want to see if I am serious about this,” I said annoyed. “If I go at my own pace, they’ll cut me off,” I added.

He nodded as if he had heard such things before. “What of your own financial independence?” he asked.

“Somehow, someway, my parents managed to block my student loans. I had to quit my job at the bookstore as well,” I said frustrated.

“Why?” he asked curiously.

“There’s a private investigator following me wherever I go. If I dress as a man for my job, I’ll get busted. My parents don’t even want me to get a job. They want me to do nothing but study, and they can handle all the expenses,” I said bitterly.

“Well, it would appear your parents have won,” Dr. Stein said.

“Thanks,” I replied sarcastically.

“Even in defeat, there are things you can learn about yourself. Do you want to transition or not?” Dr. Stein asked.


I decided to have a chat with Chris on what was happening to me with my parents. “Wow, that’s kind of fucked up,” he commented once he heard everything.

“The first step is electrolysis sessions. It’s going to hurt like a bitch,” I said irritably.

“It’s all part of the process,” Chris allowed.

“Look, where are we going with all this? In a year, we will graduate and go our separate ways,” I said.

“I don’t know,” he admitted. “I like the idea of staying together even after graduating.”

“What would be the point?” I asked.

“Look, you’re looking at this all wrong. You’re coming from a position where you’re a guy pretending to be a girl. You need to see yourself as a woman that just has a small birth defect,” he said.

“Even if I go through with the transition, I couldn’t give you kids,” I said obviously.

“That isn’t the only point to having a relationship. Besides, we could always adopt,” Chris said.

“If I don’t transition, we will eventually break up. That is the truth,” I pressed.

He hesitated to reply confirming what I already knew. “You have to transition for yourself, not because of me,” he said flatly.

I had my answer. If I didn’t transition, I would lose Chris. My parents would never take me seriously again if I backed out. There was only one choice, one option. Despite all the pain I would have to go through to achieve the goal, it was unavoidable.

“For next several months and years, I am going to be struggling. I am going to need your help,” I said finally.

“Absolutely,” he replied.


My electrolysis was scheduled by my parents. It would be one of many sessions to permanently end hair growth on my body. At the last minute, my parents canceled the session and rescheduled. My parents gave some BS excuse for doing it. They were testing my resolve. They postponed a few times until I finally went in to have it done. I suppose my parents rationalized that it would be acceptable to have a son that couldn’t grow a beard. They were still in denial that I would go through with the whole thing.

Eventually it did happen finally giving me relief from shaving every other day. I did two treatments a week blending heat with chemicals that worked to kill facial hair. The commitment would be long with several months to a few years to make facial hair permanently go away. Thankfully, Jake had trouble growing any significant facial hair.

My hair grew longer to the point where extensions were unnecessary. After a few months, my breasts were noticeable enough that I couldn’t go outside shirtless without causing controversy. I began using a sports bra when I walked in the park. As I became more feminine, I started to wear skintight gym wear. I took my father’s advice to take it easy, so I walked instead of jogging. Chris would lap me a few times and then walk with me the rest of the time. He would glance in my direction occasionally eliciting a smile from me. I was finally enjoying the attention of the male gaze.

Occasionally, I would come over to Chris’ apartment after our walks. I would use his shower and change into gender-neutral shorts and t-shirt. I felt perfectly safe at his place away from shady private eyes. The existence of them made me paranoid although my parents never spoke to me about their findings.

One time, Chris began to play an old action movie. “Let’s watch something else,” I said slightly freaked.

Jake gave me an odd look. It was one of Jack’s favorite movies and could potentially trigger his return. “Sure,” Chris said and chose some sappy romantic comedy that we both ended up hating. It didn’t help that Jake talked to me during the movie.

“I thought our goal was to bring back Jack,” Jake said.

I gave him a dirty look. Bringing back Jack would be complicated now. I was in between male and female and dating a man. Jack’s return could seriously undermine my progress. I decided to reply to Jake in the bathroom away from Chris.
“This isn’t a good time,” I said to myself and Jake in the mirror.

“So, we have decided to only trigger Jack’s return when it is convenient now,” he accused.

“What do you care? You hated him as much as I did,” I pointed out.

“I am beginning to doubt your commitment to bringing him back. Now, you’re actively avoiding things that could bring him back,” Jake said.

“What the fuck do you think is going to happen if he does come back,” I hissed.

“You good in there?” Chris asked.

I shut my mouth not wanting to reveal my insanity to him. “All good,” I said cheerfully and exited.

That night, we made dinner together. I could definitely see myself moving in with him. That would be a considerable step that neither of us seemed prepared for. As we watched TV, I got close to him and we began to kiss. Before, we would give each other pecks and goodbye kisses. This time I kissed him for a good moment and dared to even use my tongue. He reciprocated with his own kissing skills. I felt so aroused by him and yet felt nothing coming from my penis. It was something deeper inside my gut.

“I want to do something for you,” I said breathlessly.

I reached for his shorts and held his erect cock in my hands. He didn’t pull away or tell me to stop. “Are you sure?” he asked me.

“Absolutely,” I said and then lowered my mouth onto him.

It became such a thrill to know I could provoke all sorts of reactions from him. He moved his hips slightly while his cock was in my mouth. I could hear his soft moans and sighs. Niki had taught me well when she had sucked my own cock months before. This would be the first time I had truly pleasured a man, a real man.

“I am about to…,” Chris warned.

I didn’t care. I wanted to get him to the finish line. I kept going until he inevitably came in my mouth. I withdrew from him and quickly swallowed. I gave him a sheepish smile.

“That was great,” he complimented.

“I can’t believe I did it. I got you to cum,” I said enthusiastically.

“Well, it’s only fair I return the favor,” Chris said.

I froze at that. As much as it would be pleasurable for him to try, it would be border-line gay. I didn’t want my straight boyfriend to suck on my cock. That just wouldn’t do.

“Let’s do it,” Jake encouraged.

“That’s alright, Chris. I didn’t mean to go this far,” I rejected.

“I’m happy you did,” Chris assured me.

“Look, I would rather you not play with my male parts,” I said delicately.

“Fair enough,” Chris agreed. “Do your breasts count as male parts?” he asked rhetorically.

I stared at him and then took off my shirt revealing A-cup breasts. “They’ll grow,” I promised him.

“They look fine,” Chris replied.

“They ache sometimes when they’re squeezed. If you could just focus on the nipple,” I said awkwardly.

He nodded and then gently kissed my right nipple. I sighed as they felt very sensitive. My anxiety that we were just two gay men evaporated as he passionately kissed and licked my nipples. This wasn’t something two men did. I was engaging in sexual foreplay as a woman for the first time. After a few minutes, it was too much for me.

“That was great. Thank you, Chris,” I said sincerely.

“It’s getting late. I should take you home,” Chris said as he straightened out his shorts.

“I want to sleep with you,” I blurted out. “I mean…with our clothes on,” I clarified.

“Sure,” Chris allowed.

Chris went to sleep, and I immediately went to the bathroom. Chris was getting me too aroused. My penis was usually limp but was now attentive. I pulled down my shorts and stroked my cock quickly.

“Need any help?” Jake mocked.

“Fuck off. I can’t sleep with Chris with this erection,” I said. I thought of Chris making love to me as I stroked myself. If only it were possible. I quickly came and felt relieved. All was calm again.

I exited the bathroom and went to sleep with Chris.


Despite my better judgement, I went through dozens of shemale porn vides on my laptop in the privacy of my own room. Jake was present with me to determine the “hotness” of each porn actress.

“No, no, no, maybe, no, no,” Jake said as I scrolled down.

“Well, aren’t you picky,” I said annoyed.

“Can’t you determine attractiveness for yourself?” he asked me.

“No, because I am a straight woman,” I shot back.

“Please,” Jake smirked. “That one looks good.”

“The man or the woman?” I asked sarcastically. “You see what I did just there? I implied you could be a homosexual.”
“And?” Jake shrugged.

I went back to my laptop and clicked the video. “So, I am definitely not going to penetrate Chris,” I said.

“Some straight men like to be pegged,” Jake reminded me.

“I know, but I don’t enjoy it. I can’t even get very hard anyway,” I said.

I watched the shemale women make love to men from various positions and tried to imagine what I would do. It was both strange and unsettling to know that I would soon join their ranks.

“Only temporarily,” Jake assured me.

“Right,” I said fearfully.


My lease was up before I was to graduate. There was no way to avoid getting a new lease on my apartment. I would have to go to my parents to review whether I was worthy of it. I met my father at his country club for breakfast.

He casually looked through the lease, the same lease he had signed a few times already. “Nothing’s changed,” I said.

“Actually, everything has changed. The last time I signed this lease, I thought I was talking to your brother,” he reminded me.

It felt odd thinking of Jack as my brother. “I have a proposal that would cut costs,” I said.

“Oh really?” he asked condescendingly.

“If I had a new roommate, it would cut the cost in half,” I said vaguely.

“Oh yes, your roommate Nick moved out,” my father recalled.

“Yes, Nick did move out,” I replied controlling the urge to tell him everything that had happened.

“Well, do you have someone in mind?” my father asked.

“Yeah. Instead of renewing this lease, I was thinking to move in with…Chris. His lease ends after I would graduate,” I said delicately.

“Doesn’t he have a roommate of his own?” my father asked.

“He went back home,” I said truthfully.

“So, your plan is to split the rent three ways then?” my father asked.

“Right. Even though Chris’ roommate isn’t present, he still has to pay half the rent. This would help all involved,” I said.
“Unless of course this roommate reappears,” my father said suspiciously.

“Unlikely, he’s totally moved out,” I replied.

“Cost isn’t really the issue…Jill,” he said.

“What is the issue…dad,” I said in the same tone.

“If you were boy and straight, which you are not, I wouldn’t have a second thought about it. However, I know that you are involved with this boy and moving in together with him will just be an unacceptable risk,” my father said.

“So, if Jack were gay you wouldn’t have agreed to this, right?” I asked pissed off.

“If Jack were gay I wouldn’t have him live with another gay man,” my dad clarified.

“It’s not like I can get pregnant,” I protested. I didn’t think this was such a big deal. “In fact, it would be even more risky if I had a female roommate,” I added.

“I am not concerned about you getting pregnant or getting someone else pregnant. You’re so far gone that your sperm must be useless by now,” my father said.

I wasn’t sure whether to be insulted by this remark. “So, what’s the deal?” I repeated myself.

“If you end up breaking up with this boy, there will be non-stop drama between you two. I would rather not have to get involved in this queer state of affairs,” my father said.

“That won’t happen,” I promised.

“You can’t promise me what he will do,” my father corrected.

“I’ll join the club. I’ll play golf,” I offered.

“We negotiating?” my father asked skeptically.

“Yes,” I replied subdued.

“Chris has to join too. I want to know his true intentions,” my father said.

“His intentions are noble,” I said vaguely.

“Has he proposed?” my father asked.

“Well, no, but I haven’t fully transitioned yet,” I excused. “You know what? This isn’t fair. Right before the accident, Jack wanted to move in with this girl. Would you have allowed that?” I asked accusingly.

“No,” he said flatly.

I sighed stumped. “If he proposes to you, the two of you can move in together. Otherwise, I won’t agree,” he said finally.
“Is this about the sex? I can assure you that I can get sex from Chris whenever I want,” I said boldly.

“Perhaps you can, but I can’t make it easy for you. Adversity will strengthen your relationship or it will cause it to end, in which case it was never meant to be,” my father said.

“We’re both students. We can’t afford a ring right now,” I said.

“A proposal doesn’t require a diamond,” my father smiled.


I went home defeated. I couldn’t tell him about my father’s deal. If he proposed just to live with me, it wouldn’t be sincere. He would have to do it on his own accord. “What if we proposed to him?” Jake suggested.

“Women don’t propose to their men,” I rejected.

“That is old-fashioned thinking,” Jake reminded me.

“Yeah, well, I want an empowered confident husband,” I replied.

“Husband?” Jake questioned.

The word did seem odd coming off my lips. Before, all I could hope for was a boyfriend or partner. As I transitioned to womanhood, I was going to inevitably face the prospect of being called a wife and mother.

“Wow,” I said out loud.


That night, I went to Chris’ apartment to tell him the news. “My father said no,” I sighed declining to give further explanation.

“Not too surprising I guess,” Chris said disappointed.

“We can still do things at your place, and you can still come by my place,” I offered.

“What kinds of things? Board games?” Chris joked.

I got close to him. “I am going to have my boob job soon. When I get them, I want more from you,” I said.

“We can do it now if you want,” he said.

“No, I am not yet ready. I don’t look female enough,” I said.

“Shouldn’t that be up to me to judge?” Chris asked.

“You worry me sometimes, Chris. I can use make-up to give you a pretty face but my body shouldn’t be arousing to you unless…you’re gay,” I said nervously.

“Well, I’m not gay. I know that,” Chris said while drinking a beer.

“Then, how could you be interested in my body?” I asked.

“It’s not a matter of arousal, it’s a matter of love. I want you to feel pleasure and happiness,” he said.

“Okay, in that case, we can do it in the dark,” I said.

“Whatever feels most comfortable,” Chris agreed.

We went to Chris’ bedroom and took off our clothes. This would be the first time showing myself fully naked to him. I had made progress in my transition eliminating facial hair permanently, having my whole body shaved of body hair, developing breasts, and a more feminine face. Still, it didn’t seem enough.

I went over to the bed and bent over. With my right hand, I held my genitals, so they wouldn’t flop around. Chris put a generous amount of lube on his cock and got closer to me.

“If it hurts too much, you tell me to stop, alright,” he said concerned.

“It will be fine,” I assured him.

He was hard as he pressed inside. Should I be alarmed that he was hard? Was he truly straight? Would I go through this painful transition only to find out he was actually gay this whole time? My anxieties disappeared for the moment as he entered me.

“You okay?” he asked me.

“Yeah, no problem,” I said to him. I couldn’t tell him I had done this before with Nicki who was now a transsexual herself. Wait, if Chris ever knew about what I had done with Nicki, he would be right to question my sexuality. Even more so if he knew about Jack and Maria. I was being a total hypocrite.

Chris thrust inside me at a slow pace not wanting to hurt me. Unlike Nicki, he was a much larger man in all areas. In the dark, I tried to imagine what his cock looked like as it entered me. After a few moments, he managed to cum inside me.
“Let me do something for you now,” Chris offered as he finished.

“No, I am very satisfied,” I said turning to face him. I kissed him passionately. “You fulfill me, Chris.”


I occasionally went to Dr. Stein during my transition process. “So, you’re concerned that your boyfriend could be gay?” Dr. Stein repeated.

“Yeah, that would be a deal breaker. I really want to live as a straight woman with a straight boyfriend,” I said resolved.

“You are entitled to your sexual preference, Jill. Never feel you should change to accommodate someone else’s sexuality,” Dr. Stein agreed.

“What if he is gay though?” I wondered.

“Well, has he had any prior gay relationships?” Dr. Stein asked.

“None to my knowledge,” I answered.

“Has he stimulated your genitals in anyway?” Dr. Stein continued.

“No, I haven’t allowed him to. He said he would do it only if I wanted him to,” I said.

“And has he engaged in anal sex with you where he was on the receiving end?” Dr. Stein asked.

“No. I’m not interested in that,” I said embarrassed.

“I suggest you present yourself as a man, attempt to gain his affections, and gauge his reaction to you,” Dr. Stein suggested.

“My parents will think I have relapsed,” I said concerned.

“I will tell them otherwise,” Dr. Stein said.


So, I cut my hair short, wore loose male clothing, used make-up to make myself more masculine, and practiced a male walk. I even practiced my old male voice again. “Very boyish-looking,” Jake approved.

“If he kisses me now, he must be gay,” I said confidently.

I went to the university and waited for his class to end. He immediately recognized me somehow and came over. His male friends were close behind. Chris gave me a kiss in front of his friends despite my appearance.
“What’s with the haircut?” he asked.

I was too stunned to answer him. He had just kissed me while I looked like a man in front of his friends. “Chris, you never told me your girlfriend was so cute,” one of his friends said.

“Cute?” I wondered.

“Yeah, where did you find her?” another smiled.

“At the gym,” Chris said vaguely.

“You should invite her to my parties. We would love to see her there,” the third friend said.

All three straight males were able to see through my disguise. “Sure thing,” Chris said as the three took off.
“You okay? This is a strange look for you,” he said.

“Actually, I kind of regret it now. It took me a long time to grow it out and everything,” I said awkwardly.

“Short, long, it looks good,” Chris assured me. “Let’s get a bite to eat.”

“I’ll be right with you,” I said and then went to the woman’s bathroom. I stared at myself in the mirror. My disguise was as good as one could do. A woman washed her hands next to me, gave me a glance, and then walked out. She didn’t scream that a guy was in the bathroom. She didn’t even give me a second glance.

“I would think it obvious,” Jake said appearing in the mirror behind me.

“What’s obvious?” I asked.

“You can no longer pass for a man. Not even if you tried. You’re not merely passable now. You are a woman now,” Jake said.

I touched my face in stunned realization. There was no way Chris had confused me for a man. He saw me as a woman as everyone else in the world now does. As the shock wore off, I realized what I had done to my hair.

“Damn it,” I sighed.


Despite my ruined hair, Chris took me out to dinner for a group date. We had been asked to go by Chris’ sister, Sarah. I decided to stay casual with a sweatshirt and jeans. I placed my fake breasts on my still small breasts. I counted the days until my breast surgery.

“Glad you could make it,” Sarah smiled at her brother as we arrived.

“Sure. This is Jill,” Chis introduced.

We had met before when we had dated as man and woman. “You look really familiar,” Sarah said of me.
“My brother is Jack. He mentioned you before,” I said.

“Wow, I can definitely see the resemblance,” Sarah remarked. “What a coincidence this is. His sister is now dating my brother.”

Chris smiled and decided to break the tension. “And this must be Barbara.”

“Nice to meet you,” she said politely to him. Jake and I saw nothing to indicate Barbara was interested in Chris.

“She’s a Lesbian,” Jake pointed out the obvious. Barbara was also wearing masculine clothing, had short brown hair, and wasn’t wearing any make-up.

We all sat down across from each other in the seafood restaurant. Sarah attempted to pry into my past history, but I was well prepared for such questioning. Nothing could get past Jake and I.

Midway through the meal, Sarah touched her lips and realized her lipstick was off. “Jill, mind coming with me?” she asked.

So, this was happening. It was a rite of passage for girls to go to restroom together and gossip. I was both annoyed and flattered. “Sure,” I said getting up.

I followed Sarah into the restroom where she immediately fixed her face. “I guess I used too much. You would know all about that, right?” she asked.

“I suppose,” I said wondering where she was going with this.

She got close to me and squeezed my fake breast. “You are Jack, aren’t you?” she accused.

“Get off me, bitch, or I will end you,” I threatened.

“What’s with your fascination with my family? You couldn’t get me, so you went for my brother?” she demanded.

“I didn’t know you were his sister,” I said honestly.

“But after you did find out, you decided to dress up as a girl for him?” she asked.

“It’s more than just dress-up,” I said pushing her back. “He knows everything about me.”

“Including the fact that you tried to get in my pants?” she asked.

“That’s an exaggeration,” I said.

“Does he know we were together?” she asked.

“Yes, he does,” I replied. “If you don’t believe me, you can ask him,” I said.

“I questioned my sexuality, because I felt zero chemistry for you. Now, I find out you were a fucking girl this whole time,” she said outraged.

“I’m sorry the pace of my transition inconvenienced you,” I mocked. “I don’t feel attracted to every man I see.”

“I felt comfortable being a Lesbian, because I knew my brother was perfectly straight. I knew he would continue the family line. My family is kind of a big deal,” she said arrogantly. “Now, I find out he’s with someone that can never get pregnant.”

“I’m an only child. My parents had the same concern, but you know what, I don’t give a fuck about that. Use a sperm donor or fuck some random guy; I don’t care what you do to continue your family line,” I said.

She stared at me and then gave me a creepy smirk as some weird idea must have popped into her head. “No worries. You just keep being…you,” she said giving me a pat on the shoulder.

The two of us exited the restroom and came back to our table. Sarah was as bright as ever as if our friendly talk had never happened. I didn’t know it at the time but my little chat with Sarah would forever alter my destiny.


My parents and Chris were present as I exited surgery. I had inserted the breast implant through the armpit to avoid any chest scars. I was assured the stitches would dissolve on their own. While receiving breast implants was not necessarily a permanent change, it was a milestone. I could now walk around in a bikini and never have to use my fake breasts again. My entire body was definitely more female looking than male.

Once I got home, I couldn’t stop looking at my new breasts. After a few days, I no longer needed any pain pills and the incision mark disappeared. Only a keen eye could tell I had implants. I knew that Chris would lie to me even if my breasts looked fake. So, I printed out a dozen pictures and female breasts in front of him.

“What’s this about?” he asked.

“Tell me which ones are real and which ones are fake,” I instructed.

“Really, Jill?” he said uncomfortably.

“Just do it,” I ordered.

He reluctantly sorted them out. After he was done, I gave him an odd look. “Did you even try?” I asked.
“How am I supposed to know? I’m not a plastic surgeon,” he excused himself.

He got half of them right, but the important thing was that my breast pictures were in the natural pile.

That night, Chris played with my now full breasts. I felt so female as he caressed them and cupped them with his hands. “Too bad you won’t be able to go outside shirtless,” Chris smiled.

“Yeah, too bad,” I smiled.


My father invited Chris and I to the golf course at his club. Gone were any thoughts that I would revert to my male self again.

“I got a good lawyer to work on your documents,” my father said to me.

“Cool,” I said lamely. I didn’t know how to even begin the process to legally change my name and sex.

My father sighed as I swung the golf club. The ball was quite short from the hole. “I don’t get it, Jill. You used to be so good at this,” my father said referring to Jack.

“Just out of practice,” I said giving him a fake smile. Jack wasn’t really into golfing either but practiced anyway to please his father. I, on the other hand, didn’t give a shit.

Chris swung hitting the ball much closer. “Not bad,” my father complimented.

“I practiced a little in high school,” Chris revealed.

My father did his swing and got the closest to the hole. No doubt, I was going to get third place.

My father and Chris walked off to talk while I sulked. “Fuck this game,” I said out loud.

“Now, now, you can be as good as Jack if you focus,” Jake said.

“But why?” I asked. Hearing about Jack used to tighten my throat with grief. Now, the pain of losing him had dulled. Jake had done a good job of filling in for Jack.

I eventually slogged through the course and had lunch at the club house filled with elite old people. My father continued to compliment Chris as if he were the son he never had.

The club leader then approached our table. “How you doing?” the club leader asked of my father.

“Just finished a round of golf with these kids,” my father smiled.

“Is this your son?” the club leader asked of Chris.

“No, he’s my daughter’s boyfriend. Jack is still at college,” my father said smoothly.

“I didn’t know you had a daughter,” the club leader said looking in my direction. “What’s your name, young lady?” he asked.

“Jill,” I replied politely.

“You have one lovely daughter,” the club leader complimented my father.

“Thank you,” my father said as the club leader walked off.

Chris gave an uncomfortable look as it was obvious my father hadn’t revealed my true nature to any of his friends. Jack would never make another appearance in the club house ever again.


Whatever my father must have said to Chris on the golf course must have had an impression on him. He invited me to the beach but not to swim. I was in white dress while he wore dress shoes, black slacks, and a white collared shirt.

“So, where are we going?” I asked as I followed him.

“There’s a restaurant not too far from here,” he said.

We continued to walk until the sun was about to set. “I know I’m just a student, but I have big plans. I want to live with you and be with you always,” Chris said.

“Sure, Chris. We can make it happen after graduation and when we get ourselves jobs,” I agreed.
“I want to be with you now,” Chris said and then got on a knee. I simply stared at him. What was he doing? Could this be real? Was this how countless women felt? Fear and joy swept over me.

“Will you marry me?” he asked finally taking out an unusual looking ring.

I placed the ring in the palm of my hand. It was a simple black-colored ring, the kind of ring my father spoke off. “Yes, Chris. Of course, I will,” I said.

He stood up and kissed me as the sun set. I placed the black ring on my finger and followed him where we had the best meal of our lives. The black ring would later be replaced by an expensive diamond ring that I would always wear. Still, I kept the black ring as a keepsake and never knew how important to me it would become.


Graduation finally came after three hard years. Jack had only done a semester with my help. This degree was mine. I owned it. Chris happened to be graduating at the same time even though he was a year older than me. Due to our last names, we were far apart from each other in the line. He gave me a kiss before we took our places. The black gown bulged a little from my new breasts. I went through the ceremony and had my named called.
“Jill ___,” the lector called out.

I accepted the degree that had my name on it. This was my accomplishment and no one could take that away from me.
After the ceremony, I reunited with my parents. “So proud of you, Jill,” my mother gushed.

“Good job,” my father said shaking my hand. He then noticed the black ring on my left hand and gave me a wink.

Now that I had graduated, the real hard work would begin. I would have to find a job while trans. Shouldn’t be too hard.


Chris found a job easily enough as a physical therapist. I finally got a job interview in the city in an office building. I dressed conservatively as a business woman and finally spoke with the boss.

“Your grades are excellent and your major fits right in with us, but I have a diversity quota to fill. How are you, a white woman, going to help me with that?” the boss asked skeptically.

“I’m…trans?” I said helpfully.

“Can you prove it?” the boss asked skeptically.

“Yeah, I have tons of documentation on it. I kept everything,” I replied.

“Good, you’re hired,” the boss smiled and shook my hand. I have worked there ever since and only my first boss ever knew of my past.


With my graduation and new job, my parents finally decided I was worthy of their generosity to get the final operation. We couldn’t go through the normal channels, because I had multi-personality disorder and some kind of schizophrenia. So, we went to the one place that would do it, no questions asked: Thailand.

I felt nervous on the long flight as if I was heading towards my own demise. Thankfully, Chris was with me. We dropped down in Bangkok and checked into our hotel. We made love with him taking me from behind. I wasn’t yet comfortable doing it face-to-face. Soon, my cock and balls would be gone and it would open up all sorts of positions.

Before the operation was to take place, Chris and I visited the Buddhist temples and markets. We wouldn’t be able to do this after the operation. I was in a constant state of anxiety as I worried about the pain of being permanently disfigured.

The night before the operation, I showered alone. Well, Jake was with me as usual. “This could be our last orgasm,” he said wearily.

“Yeah,” I agreed. “You going to still be you after the operation?” I asked.

“Why wouldn’t I?” he asked.

“It’s just this is the last step. I figured you might change into a woman after this,” I said.

“Not likely,” he smirked. “I am a mental projection. You will always have a fraction of your mind that is masculine.”

“Maybe, I will eventually purge it,” I said playfully.

“Or the other way around,” he challenged.

I took hold of my weak flaccid penis. “Well, let’s give it a proper send off,” I said to Jake.


The operation was a success, but I felt the worst pain of my life. The drugs made me numb and incoherent. The mental projection of Jake was not clear most of the time. I even wondered if this of all things would finally spark Jack to reappear. Perhaps, he would finally arise to protest what I had done to his body.

The removal of my genitals was of little consequence in so far as I had already sterilized myself with hormone treatments. I would have to rely on the sperm that I had stored long ago.

The doctor assured me that everything had gone according to plan. I would have to take his word for it. It was a discolored painful wound at the time. Still, regardless of functionality my male genitalia were gone forever. To everyone else, I looked completely female biologically.

Months went by as I painfully used plastic dildos to keep the neo-vaginal cavity from closing. I felt numb where my clit was supposed to be. I had little interest in sex and felt miserable a great deal of the time. Occasionally, I even second-guessed my decision.

“Maybe it was a mistake,” I said to myself.

“Yeah, you fucked up,” Jake agreed.

“I hate you. You don’t have to experience all this pain,” I said enviously.

“Not all pain is physical. I have to constantly hear you whine,” he said.

“What if I can’t do with him? He might leave me,” I said distressed.

“The plastic you have been using is about the same size. You have nothing to worry about,” Jake said.

“You really are gay,” I concluded.

“You’re healed enough. Go to him,” Jake advised.

“Alright,” I said.


I found Chris reading a book on the couch. “I’ve made you wait a long time. I’m sorry, Chris,” I said to him.
He put the book down and focused on me. “What do you mean?”

“You could have scored some real pussy with some girl years ago, but you waited all this time for me,” I said appreciatively.

“Of course, you’re my gym buddy,” he grinned.

“Wow, that’s fucked up,” I said recalling all the time we spent together as male friends.

“What’s on your mind?” he asked.

“I think I’m ready,” I said finally.

He nodded thoughtfully. “Well, unfortunately I’m not. You’re going to have to wait a few hours,” he said.

“Fuck you. Get in the bedroom,” I ordered.

He smiled and kissed me as we entered the bedroom. I quickly got out of my clothes and had no hesitation showing him my front side. We kissed, naked, face-to-face. I felt his erect cock up against my thigh.

“If it’s too painful, we can stop anytime,” he said.

“I know,” I said just as worried.

He put a generous amount of lube on his cock and then hovered over me. We had never had sex face-to-face like this. He placed his hand on my entrance and felt around. “Tell me if I get the right spot,” he said as he felt for my clit.

He eventually found it and then placed a finger at my entrance. Slowly and cautiously, he entered me. “You okay?” he asked.

“Yeah, let’s try for two,” I said.

He put two fingers inside me giving me confidence I could handle him. “Okay, let’s do this,” I said. Finally, we would have male-female sex. I had waited so many years for this moment. I had been resigned to Jack’s plans but now I had accomplished everything I had ever wanted.

Chris gently pushed inside and then slid all the way to the hilt. “Wow, I didn’t think I could take all of you,” I said surprised.

“You calling me short?” he teased.

“Chris, it doesn’t feel painful anymore. Do your thing,” I said as I wrapped my legs around his hips.

“You’re the boss,” he said and started moving inside me.

Years of sexual repression was suddenly released. I became a real freak. Gradually at first, I moaned and screamed. I had him pull my hair as he penetrated me from behind. I clawed at his back as he pressed inside me. I rode him like a bull when I was on top. There was no fear of ever being outed or being rejected. When he came inside me, I worked to get him back up.

It took time, but I experienced my first orgasm. After that, I became addicted to sex. I wanted Chris all the time, every night. I had several years to make up for. He never saw me anything but a normal female. He went down on my and licked my neo-clit as if it were the real thing.

After a long love making session, my hair was a mess, my body was sweaty, and my muscles burned with exhaustion. “Chris, I want to be your wife,” I told him.

“I would be honored to be your husband,” he said and then gave me a real diamond ring. Taking the black ring off my finger, he placed the real engagement ring on my finger.

“I will love you always, be faithful to you always, and care for you for the rest of my life. I’m so thankful to have met you,” I said as happy tears came down.

“The pleasure is mine, Jill,” he said and then kissed me lovingly.


On the fifth-year anniversary of the car accident, I came to the cemetery with roses. I dressed in black, as I came upon Maria’s tombstone. What could have been had the car accident not occurred? Jack would have married her by now, and they would have had kids. I was so far behind.

“You might find it a little odd seeing me here every year, Maria,” I said to the tombstone. “But as far as I am concerned, you both died together,” I added referring to Jack.

I placed the flowers at the grave mark along with the others. “Well, Jack, look at me now. I’m about to get married to a loving man and maybe start a family soon. I know you would be proud of me, even if you couldn’t admit it,” I said.
I wiped away a tear as I thought of him. Yes, he had been an ass at times. Right before he died, things between us had been bad. Still, it was Jack that saved me from my darkest days. When I was a teenager, my parents tried to get rid of me with counselors and drugs. They hated me and only wanted Jack as their child. I was so close to ending it all, but Jack pulled me from the brink.

Yes, it was self-preservation. My destruction would have been his destruction, but he was the only one that gave me any love or kindness. I owed my life to him. As I departed, my hand shook as if I had Parkinson’s. I raised my shaking right hand and gave it a peculiar look. Jake gave me an odd look. I focused on my hand and shook it correcting the malfunction.

Thinking nothing of it, I went back home to Chris.


The next morning, I felt something odd. My body was moving on its own accord. It felt like an out-of-body experience. My body awkwardly moved over to the bathroom and a sense of dread filled me. I hadn’t felt like this since…
My body stared at the mirror, and I felt a rush of foreign thoughts enter my mind. They were male thoughts. “Oh crap,” I realized as my body touched my feminine face.

“He woke up.”

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