Editor's note: this story contains scenes of incest or incest content.


This is not a quick story for everyone to get off to. It takes a while to develop, but I hope you'll enjoy the trip. As with my last story, all those years ago, this has an element of truth to it, although this is not my son. A TG male that has... "adopted" my wife and I told me of his first and only time, and that he wished it was more than what it was. This story is for him

"Hey, Mikey, I got that new binder for you! Cone out here and grab it! And, while you're at it, help me get the groceries out of the car, and put them away!"

Not that I didn't expect it. They knew I was going grocery shopping, and they all had given me a list of things they wanted. And, they weren't home.

"But, they'll be the first in line when the bread is baked, now, won't they?" I asked myself, referencing my favorite fairy tale. 

Things had been strange for us the last few months. Their mother had gone to rehab for a pill addiction no one knew she had, and then had simply disappeared. I got an email stating that she was safe, and that she wouldn't be home because it was too stressful, and that I was to not come looking for her. She was starting her life over.

I called the kids into my office and showed them the email. They were, to say the least, confused. "What stress?" they asked. "If she loved us, why would they abandon us?" I told them I didn't know what she meant, or why she left, but I did.

"Stress" was our 22 year old son, Michael, who was born our daughter Michelle. "Stress" was our barely 18 year old daughter (Laura) who had been molested by a "friend" of her mother's from the neighborhood repeatedly over the course five years or so years (we found out at the Fourth of July bash we held a couple of years ago when I had gone to my bedroom to change into my trunks and heard her trying to fight him off), and was now in therapy with a forensic psychiatrist. "Stress" was me having to deal with the legal system after putting him in the hospital (the DA refused to press felony assault and attempted murder and offered me a handshake deal that the file would stay "lost" in his desk drawer as long as I kept my nose clean for, well, until the Fourth of July party this Summer). "Stress" was a 19 year old daughter (Katie) who caught her ass-fucking that very same neighbor and refused to have anything to do with her, and who was home schooling after being sent home for sending a kid who teased Laura about being molested to the emergency room. "Stress" was... her bullshit way of bailing on her family.

Anyhow, now it was just us, the single Dad, a trans-gendered son, a pissed off teen girl, and a daughter who was too scared of her shadow. We are an American family (random "You've Got Mail" reference). Luckily, when the kids were younger, I had inherited the two-bedroom house next door, after old man Lindgren died without a family, and moved "Doc Lollipop's office" there (see the doc, get a lollipop, right?). If my daughter needed me, I was just steps away. I was- thanks to being "Doc Lollipop"- also able to afford to support my family, and pay for Mike's college, and Laura's therapy.

About the time dinner was working, the kids came strolling through the door, laughing and carrying on as if they had not a care in the world. Normally, my kids having a happy, and carefree time is my favorite sound in the world. Tonight, the sound was irritating me to no end. I was going flat out trying to keep this family together through everything, I was still stressing hard over my wife of twenty-six years, and I was doing everything I could not to show it was bothering me... and, they couldn't be bothered to be home when they were supposed to be.

"Hi, guys, sounds like you had a good day." I got hugs and kisses. "Suppose you tell me about it."

The next few minutes were a cacophony of kids telling me where they were, what they had done, who they had seen, and how much of my money they had spent as I prepared our one meal of the day together. 

Anyhow, I seem to have gotten off the point of the story...

Later that night, the girls were watching whatever the latest teen-aged binge that was on Netflix, Mike was studying, and I was in my office preparing for the patients the next day when Mikey knocked on my door. I didn't think anything of it, because he was studying pre-med with an eye towards getting his doctorate of psychiatry and helping people like him. He often came in to ask a question about one thing or another. This time, he came in without his books.

"Hey, Dad, I know you're busy. Can I talk to you about something?"

"Mikey, you know I am very rarely too busy for my kids. What's on your mind?"

He came over and sat in the chair beside my desk. He glanced over at the computer screen.

"Larry Chester. hm. How's his leukemia coming along?"

I turned off the monitor. "He's doing fine, you know better than to ask. What's up? Was the binder the wrong size?"

"It's fine. I need to talk to you, and I need you to promise you won't get upset."

"I won't promise that, but you know I always try and keep an open mind when I'm talking to you kids." "We talked about something shortly after I came out as trans-"

"You're going to have to do better than that." He seemed more nervous than I had seen him in a long while, so I got up and walked towards the college refrigerator in the corner to grab myself a beer. "Do you want one?"

"Thanks. Anyhow, when you found out I was trans, and had a girlfriend I was getting physical with-"

I handed him a bottle and sat down. He took a drink.

"Thanks. Anyhow, you discovered my prosthetic penis and asked if I was becoming sexually active."

"OK, yeah."

"We were sitting right here at your desk, and you asked if I had been sexually active as Michelle. I told you 'no', and towards the end of our discussion, you told me two things. Just because I was choosing this lifestyle, I should never close myself off to love simply because the other person was a guy."

"Yeah., that sounds like something I would say." I took a drink. This was where he told me he fell in love with the starting quarterback for Notre Dame and I had to go back to calling him "Michelle".

"The second thing you told me was to find someone, one of my friends that I trusted implicitly, who didn't have a big mouth, and who would treat me properly and with love and respect, and lose my virginity as a woman so that I would know what I was giving up and so that I would be able learn what it felt like so I could be a better lover to my girlfriends."

"OK. I don't remember saying that, but if you say so."

"Well, I pretty well blew you off because, I was uncomfortable with anyone seeing me naked as a female or touching me, and I damned sure don't want anything inserted in there."

"OK" I was always available to my kids, but I was hoping he was going to get to the point of this sooner, rather than later.

"Well, my girlfriend and I were talking about it a couple of weeks ago, and she said that our sex life was OK. It feels good, but I had never given her an orgasm and she wished I could feel what it was like to have sex as a girl so I could please her."

"OK". I damned sure stopped being interested in this conversation, but he was my son, and I was going to see it through. Mike took a long pull on his beer and set it on my desk. 

"When she told me that, I remembered what you said. After thinking about it, I decided that you were right, and I needed to have sex as a woman. I still don't know about anyone inserting anything, I don't know if I would be comfortable with that. But, I want to experience everything else."

I kept my face straight, but inside I was eye-rolling myself into another dimension.

"Well, it seems that you need to find someone who is willing to, I can't believe I'm having this discussion with you, willing to engage in manual and oral stimulation with you, and who is willing to stop immediately if you say so, and who would be fine with you not reciprocating, if you didn't want to. Do you have a friend like that? Who is willing to go against his very nature and go home alone and unsatisfied?"

"I think so. Not a friend, exactly, but someone who loves me, cares about me and my feelings, and who has always wanted the best for me. Someone who remembers me as Michelle and accepted my change without hesitation."

"Well, you know I can't give you a prescription for birth control pills, if that's what you're asking. The AMA would hang me by my body parts if I did."

"No, Doctor Davidson has that taken care of. I've been on birth control for a few years to regulate my periods."

"Then, what do you need my help with? Do you need me to meet him to give you my impressions and make sure he knows the rules? Or, are you just wanting me to weigh in to give you my opinion?"

"Actually, I am not sure how to ask him. I want to tell him that I need this from him, but I don't know how."

Finally, something I could understand. "Well, I've always found that the best course of action is to simply come right out and say what's on your mind. It might be tough, but that way, everyone involved knows exactly what the others think, and what is being said."

"Yeah, but this is a particularly tough discussion."

"Who is it? Anyone I know?" I took a drink from my beer.

"It's you."

After I finished choking on my beer, and had my son beating on my back, I sat back and looked at him in silence.

"Dad, say something."

I didn't want to say the first thing that came to mind. I certainly wasn't interested in shoving my dick into my son's pussy (that just sounded weird), but I needed to find a way to regroup and figure out how to turn him down by some means other than, "are you out of your mother fucking mind, you perverted shit?"

"Dad?" He was looking at me with pleading eyes.

"What- why me? What made you decide I was the person to give you this education?"

I noticed his hand was shaking. He looked at me for a second, very obviously choosing his words before speaking. 

"You are the only obvious choice, for several reasons."


"I lost most of my friends from high school when I came out. They could handle gay, but trans was beyond them. The girls, some of them, feel I am a sex-traitor, and the guys are weirded out and don't know how to handle it."

"What about-"

"There is no one in college that I am that close with. I tried to get Jeanine to use my prosthetic on me, but she says she's not a lesbian and would not be comfortable using it in that manner."

"Yeah, but-"

"Look, Dad. Mom, back when I was first starting to date boys, took me aside and had "the talk" with me, even though I had learned all of that in school. She told me that losing my virginity was a personal choice that only I could make. I had to choose who and when, and I had to make sure both were the correct decision. She told me that I had to find someone like my father. She explained to me you were her first and told me the whole story about that night. She said you were romantic and caring and gentle. She told me all about how she got spooked halfway through, and you were willing to stop before any there was any real sexual contact and before you came, and how you held her until it was time to take her home."

"Yeah, well... I didn't want to be one of the guys who were pseudo-rapists who used the hard sell and dumped the girls the next day."

"I know. She also said that you made sure her first time, when you finally got to have sex with her, you made sure it was perfect for her."

"Yeah, well..."

Mike put his hand on my knee, and I don't know why, just natural reaction, I guess, I started getting a familiar tingle.

"Look, I know this is absolutely the strangest thing you have ever been asked to be a part of. Having your daughter ask you this would be strange. Having your son ask you is worse. Having someone who is both is some truly weird shit. Don't you think I know this? I didn't just figure, 'well, hell, I'll just ask the old man to fuck me.' I have thought about nothing but for a while."

"Yeah, well..."

"I love you. I know you love me to the ends of the earth and would never do anything that would hurt me. I want this to happen, and I need you to do it. I know you will make it right and make it perfect, and you would be willing to stop at any point if I felt uncomfortable, and didn't want to go any further. You are my Daddy, and you are the only one I trust to love me. Please?"

I was completely flabbergasted and was at a total loss of words. This was obviously something he had given a great deal of thought to, and had made up his mind. I wasn't sure if I was the one to... I didn't know if I could be... I...

"I have to think about this before I can make a decision like this."

He stood up. "I understand. At least you didn't yell and kick me out of the house."

I stood up. "Come here." I gave him a hug, "You are my son, and I love you to no end. I just don't know if I can break this barrier."

"I understand. I will love you either way."

With that, he left my office.

He made himself scarce the next few days, I'm guessing to give me time to sort through everything. The biggest question I had was why didn't I say "no" from the beginning, and not give him a chance to explain? Why didn't I remind him about the legalities of it, and what would happen if anyone found out? Why did I even listen?

A few nights later, I was just about asleep when I heard the door open and felt someone crawl into bed with me. I rolled over to see my son. He lay his head on my chest, so I put my arm around him and held him, We laid there for a couple of minutes.

"Dad? Have you made up your mind?"

The truth is, I hadn't until just that minute.

"Is it really, truly that important to you? This isn't just something you can take back if you change your mind."

"I'm not going to change my mind. This is something I want more than anything in the world. Something I want from you. I want to share this with you."

We lay in silence a few more minutes.

"Fine, then. Unless you change your mind, we're done talking about it. Tomorrow, you will receive instructions, and I expect that you will follow them to the letter."

"OK, I promise."

With that, Mike rolled over, and I rolled over, also, and put my arm around him and we fell asleep, cuddling.

When I awoke the next morning, my arm was still wrapped around Mike, protectively. I got out of bed and got ready for my day. My last stop was to head to my office and print out a note for my son.

"My Dearest Son,

While I have misgivings, I made you a promise, and we are going to spend our evening together fulfilling your wishes. I will be home from the office about 7:30 tonight. You need to have dinner for the girls done, and the dishes all cleaned. You need to shower and be dressed. Here is the catch: you are not to wear your binder. You do not have to wear a dress, or anything other than nice outfit that you would normally wear; however, you will keep your breasts free and available. You will also wear panties and a bra. I would prefer a sexy, matching set, but that is up to you. If you need to go shopping, my credit card is in the top drawer of my desk. Do not eat. Remember, you may change your mind at any time throughout this evening, and unless you are doing so, this is the last we will speak of it. We are going on a romantic date, and that's all you need to worry about. I will see you tonight. I love you.

I put the letter on my pillow beside him, gave his sleeping form a kiss on the head, and went to work.

When I returned home that evening, there was none of the typical noise. The house was silent, Mike watching some show or another in the living room.

"Where's the girls?"

Mike got up and came over to give me a hug and kiss hello. He was dressed in a new pair of grey suit trousers, a matching blue shirt, new tie, and new shoes. I would guess he had new socks, but, whatever.

"They went to a sleep over at one of their friends."

"I'm going to take a shower and change, and then we can go."

I began to walk down the hall to my bedroom.

"Where are we going?"

I kept walking. "All will be revealed in time." I shut my door behind me, showered and dressed in a suit.

It was just before 8:30 when we arrived at Jason's, the fanciest, most expensive restaurant in the area. It was the romantic place that guys took their ladies to get engaged, and where couples went for a special night out, or for special celebrations. I had set the reservations for Mike's mother and I several months ago, and had requested a private room, one of four they have. Instead, tonight, it was for Mike and I to have a quiet romantic dinner. Things were still a bit tense when we first started, but as the dinner went on, things got to be more natural, and more relaxed, and we could have been just any other couple on a romantic date.

After dinner, we drove down to the lake and parked. We walked along the banks, not really talking about anything important, just having conversation and being together, The moon was nearly full, and hanging low in the sky, and there was no one else around. We got to a clearing and sat together. Mike sat down, then I sat behind him and wrapped my arms around him in a loving embrace. At first, he seemed a bit unsure if it was what he wanted, or if it was uncomfortable for him, but he eventually relaxed, and leaned back into my chest. It would have been easier had I been out with my daughter, but he was making himself just feminine and submissive enough to make me more comfortable, but not make him feel overly weird. As we sat there talking, I would, every so often, give him a small kiss on the side of the head. Nothing big, just a small peck. After about half an hour, we got up and walked back to the car.

We got back to the house about 11:00. We walked into the house, and after I shut the door, I walked up behind Mike and wrapped my arms around him, again. He took his hands and lightly grabbed my arms. I began to kiss his neck. His breathing started to get a bit quicker, and when I gave him slight nibbles at the base of his jaw, he drew in a surprised breath. As I kissed him, there, I slowly took off his tie and unbuttoned his top button, giving me better access. I turned him around, undid the first two buttons, and began kissing and biting at the base of his neck. When I got the first small moan, I led him back to my room.

As we entered,. Mike saw what I had set up. There were electric candles around the room giving it a dim light. I had placed a couple of drops of lavender oil on a couple, giving the room a slight scent, but nothing too overpowering. There was soft, romantic music playing, as well. Under different circumstances, this could have been lovers having an intimate night in... well, I guess it actually was. I took my jacket and tie off and threw them on the chair by the door.

"Oh, Daddy, this is perfect. Mom was absolutely so right. Thank you."

He hugged me, and I took his face in my hands and kissed him ever so slightly on the lips, and moved to his cheeks, and back down to his neck and shoulders. His breathing increased and he began with the small, involuntary moans. I had planned on making this night special, and it seemed like it was working.

While kissing him, I slowly unbuttoned his shirt and started to remove it. At first, he hesitated, and started to keep it on.

"Shhh," I said, "Just go with it. I promise you'll enjoy this."

I continued kissing his neck and shoulders as I gently lowered his shirt. He stiffened slightly, but he did not resist. He started to kiss the side of my face as I kissed and nibbled on his shoulders. 

"Remove my shirt."

He did so, slowly, kissing my chest with each new button opened. Once my shirt was opened fully, he started on my belt, and my trousers and pulled them down. I kicked off my shoes and stepped out of them. My cock was hard and poking through my boxer shorts.