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The Question
That had to be so discouraging and depressing, being in diapers like that, especially when you had the trauma of moving, changing schools and having to decide whether to live as a girl.
This is a wonderfull story and beautifully told. How I wish when my mother caught me in her clothes and make up she had encouraged me to learn to be a girl and not threatened to tell my divorced father which in those days would have meant being sent to have aversion treatment. 
I've had some stuff come up where I haven't been able to write that much lately, but here is the next part.

I certainly wasn’t happy about being back in diapers, while my mother seemed not to be too bothered by it. She seemed more interested in keeping me dressing as a girl. There were plenty of times I was asked to dress up for dinners or other events, not to mention that she kept me on a cycle to match her period. I still kept getting new clothes for dressing up in, though she also bought me boy’s clothing as needed for school.

My nightly diapering was something I tried to take over as quickly as I could. Even with my mother’s admonishment about how much she had seen me naked through my life, it just didn’t feel right to have her seeing me naked so much at my age. Even with immediately trying to be the one to put my own diaper on at night, my mother insisted on checking to make sure I had it on tight enough to avoid leaks.

“Be grateful,” she told me one night, “at least the diapers they have out now are better than the ones I used for you when you were little.”

“How so?” I asked.

“Back then, diapers weren’t much more than a basic absorbent sheet that got bunched up between the legs,” she explained. “They didn’t conform to the body very well, so you had to have plastic panties over them or you’d get leaks everywhere. The diapers that are available now actually fit your body, so leaks are less likely to happen with one that’s taped on right.

“I know, they’ve had these diapers out for babies now for probably five or six years that I’ve been seeing them,” she went on, “I guess the ones for adults took a few more years to get out, but at least we don’t have to get plastic panties to go over these.”

Whether or not I needed the plastic panties didn’t really matter to me. Just the fact I was wearing diapers at my age was humiliating enough. My mom made sure she kept a supply of them on hand for me at all times, and I wasn’t happy about her leaving everything out, so I eventually found a place I could put things where they weren’t out in the open.

The wetting continued nightly for at least six months before starting to taper down a bit. I definitely had a better understanding of how a thick menstrual pad could remind one of a diaper after that time. It took a few weeks, but my mother finally stopped wanting to check the fit of my diaper every night, and just resorted to a quick pat on my bottom to make sure I had one on before bed.

It was the following summer, and I got a phone call from the town where we had lived before. It was Ryan, he was going to be down in our city scouting a college he was going to try and get into and was going to stop by. I talked to my mother and stepfather about it, it turned out that he was going to be in town when they were off on vacation.

“Ryan is scouting one of the local colleges,” I informed them, “he was wanting to stop by and say ‘Hi’, but it’s the week you guys are going to be gone.”

My mother and stepfather looked at each other for a minute, then answered. “That would be fine, it’s not like you two ever caused trouble, so I don’t think it would be a concern. Was he wanting to stay here while visiting?”

“I don’t know,” I told them, “I think he might want to stay one night, but he wants to see some of the stuff around the city, not just the college.”

“That’s fine with us,” came their answer. “As long as you two don’t cause any trouble.”

“We won’t,” I assured them.

When Ryan arrived, it was late in the afternoon after he had spent most of the day touring one of the local college campuses. We quickly ran down to one of the local fast food joints in the area to get dinner, and came back to the house.

We ate downstairs in the family room, which was nice in that it had a pool table to while away the time, but it also had my parent’s well-stocked bar. I figured it wouldn’t hurt for us to have a couple of ‘small drinks’ where they wouldn’t notice the amount missing from the bottle. I knew which bottles were the ‘good stuff’ that they cared about and which ones were not as valued, as they had taught me to be bartender at a couple parties for them before.

We didn’t drink much, only a couple drinks apiece, and we shot a couple games of pool, just relaxing as the night wore on. After making one shot, Ryan asked me, “So, do you still dress like a girl?”

“Sometimes,” I admitted, “my mom likes having me dress up, and it’s nice to feel pretty like that sometimes.”

“Do you still look like just like a girl like that one time I saw you?” he asked.

“I think so,” I said, “I don’t hear people say I don’t.” I took a shot and just missed sinking the three ball. “Why? Did you and your mom think I didn’t look like a girl?”

“Honestly, we didn’t realize it was you at first,” he said. “After, my mom actually asked me if I had ever thought about dressing up as a girl and if I wanted to try it.”

“Did you?” I asked.

“No way,” he stated, “besides, I doubt I could pull it off as well as you did back then. Probably a bit harder for you to pull it off now, huh?”

“What, you want to see me dressed up again?”

“If you want to do it, that’s cool,” he said.

“Once we finish this game, maybe,” I answered.

It wasn’t too long and the eight ball was sunk. I took a deep breath and went upstairs to my room. I shucked off my clothes, pulling out a bra and panties to wear, and then a light dress for the warm summer evening. I slipped them on, then took a few minutes in the bathroom to just put on a light amount of makeup and try to do something with my hair.

As I stepped off the stairs back into the living room, Ryan turned to look at me. “Wow,” he admired, “you still look like a girl.”

“You think so?” I was unsure about whether he was being honest or not.

“Seriously, yeah,” he said, “I’d date you.” He walked over and stood in front of me.

I looked at him, not sure what to think. Before I knew it, he leaned in and kissed me gently on the mouth. I was startled by this, but then realized I enjoyed it. He looked at me closely, and when he leaned in to kiss me again, this time, I kissed him back.

It wasn’t long before our mouths were open during the kissing, exploring each other. Our hands soon began to feel each other’s bodies, and I felt his hands soon on my bottom, squeezing gently. We probably spent a solif twenty minutes just kissing and petting each other.

I soon realized that his hands were slowly lifting my dress up higher and higher. I had a feeling as to what he wanted. I pushed his hands from my dress and dropped it down. I didn’t think I was ready to actually engage in sex as a girl, but I felt that I did want to satisfy him.

“I’ll make sure you’re satisfied,” I said, “but I don’t know that I’m ready to go all the way yet.”

He smiled at me, and we engaged in another solid five minutes of kissing and petting. I knew now that I needed to start with satisfying him or else I might lose my nerve. I slipped my hands down to the front of his pants, feeling the bulge hidden underneath. I had my own bulge under my dress, but it was nowhere near the size of his.

I broke off the kiss, and slipped down onto my knees in front of him. I wanted to see what was hidden away, to know what he had in store for me. I released the button on the front of his jeans, and unzipped them, then pulling them down just slightly to have access to his underwear. The bugle was much more prominent, and when I pulled the waistband of his underwear down, I was surprised to see just how big he was.

He was probably two inches thick, and ten inches long. It had been quite a while since I had seen another boy naked, especially with an erection like this. My last memory was of my neighbor from before we had moved and how he got hard when wearing a bra and panties. Ryan was easily this big, and it took me a minute to get over the surprise at how big he was.

Once I was past the shock, I leaned forward and kissed the head of his penis. It was warm on my lips. I opened my mouth and took the head in my mouth, tasting him with my tongue. I felt Ryan’s hands caressing my hair and I eagerly began to bring him deeper into my mouth.

I went back and forth, trying as much as I could to bring him deeper and deeper into my mouth. I could taste the salty pre-cum in my mouth, and I realized he would probably be exploding into my mouth before too long. It dawned on me that I wanted this, I wanted to feel what it was like to have him release into my mouth. I knew that the ring at the base of his head was going to help bring him to orgasm faster (from my own masturbation) and concentrated my tongue and lips on that.

It wasn’t long before I felt him tensing his body, his hands pushing slightly harder on my head. I knew he was right on the edge, and sucked harder to get him off. He moaned loudly, and the first of his ejaculate shot into my mouth. It was salty and warm, and I felt a few more blasts enter my mouth. I let him pull out slightly as he did, so I would have room to accept the rest of it.  I licked the last drops from the tip of his penis, and swallowed hard.

Ryan smiled down at me, and I smiled back, licking my lips. He pulled his underwear and pants back up, and buttoned his jeans. We went over to the couch and sat down next to each other. “So, are you satisfied like I said?” I asked him.

“Oh, yeah,” he answered, “I’ve never had a blow job that good.”

I just smiled at him, happy I was able to do as well as I had, especially with never having done this before. I could still taste the salty nature of his ejaculate in my mouth, but otherwise not feeling any ill effects. I laid my head over on his shoulder, and relaxing with a happy feeling, knowing I had given him pleasure.

It only took a few minutes for us to be back into the heavy kissing and petting again. I climbed into his lap, sitting astride his legs as I probed his mouth again with my tongue. This time, as I felt his hands on my legs, I helped him lift my dress up. He was a little surprised and asked, “I thought you weren’t ready for that?”

“I wasn’t before, but I am now,” I responded. I climbed off his legs and stood up, taking his hand to follow me upstairs to my room. Once there, we continued with our kissing and petting, and I helped him take his pants and shirt off. He lifted my dress over my head, and I stood there only in the bra and panties. Ryan stepped forward and kissed me again, and I could feel his erection pressing against me.

I pulled his underwear down and off, releasing his erection again. I turned around in front of him, and he reached around me and cupped the front of my chest where my breasts would be if I had gone on hormones. He kissed my neck, and pulled my panties down my legs. I climbed up onto the bed on my hands and knees, guiding him into position behind me.

“Take it slow to start,” I told him. He lubed himself with spit, and slowly began pushing against my anus. I pushed out, like I did when inserting a tampon, trying to relax as I let him enter me. He was much bigger than any tampon I had used before, and it was slightly painful as he slid back and forth, slowly entering me all the way.

He slowly began thrusting back and forth against me. I could feel his testicles smack into me as he bottomed out all the way inside me. The pain subsided, and pleasure soon took its place as he picked up the pace. I could feel Ryan’s hands on my hip as I bucked back and forth against him. I couldn’t believe it felt so good to have him doing this.

It wasn’t too much longer before I felt waves of orgasms washing over me. I had masturbated before, and knew the one big orgasm that I could achieve that way, but this was a larger number of orgasms that were not quite as strong. It was still slightly rough as he plunged in and out of me, and he picked up his pace one last time before I could feel him slipping in and out of me much easier. I knew he had just shot his load inside of me.

I collapsed on the bed as he pulled out, and he laid down behind me. He put his arm around me and hugged me tight. I rolled over to face him and said, “That felt good.”

“It sure did,” he said, leaning forward to kiss me again. Suddenly, I realized that I needed to empty my bowels—I kissed him and said, “I’ve got to use the bathroom, I’ll be back.”

I picked up my panties and went into the bathroom to sit on the toilet to release everything. I wiped myself gently, and slid my panties up my legs. Heading back into my bedroom, I found Ryan had already put his underwear back on and was laying on the bed, eyes closed, and his breathing slowing and getting deeper as he fell asleep.

I grabbed a nightgown, and slipped by bra off. I dropped the nightgown over my head, and then looked towards my closet where I now kept my diapers. I stepped out of my panties, then reached into the closet to pull a diaper out for the night. I lifted my nightgown, hoping Ryan would understand if he found out my need for them. Rather than using the bed to put it on, I decided to do it on the floor, not wanting to wake Ryan. I was too worn to bother with powder or rash cream, and just slid into bed next to Ryan.

I fell asleep with a smile on my face.
That's a lovely story. The first time having sex while dressed as a girl is so special.
This was wonderful to read.  You wrote so tenderly about your first time and how much you enjoyed everything.  All I could do was smile. 

Your writing is excellent- you are a compelling story teller.
For those of you following, I wanted to let you know this is the last chapter before an 'Epilogue'. As always, if there are things you want to know more about, or feel I could have gone more in depth about, feel free to comment here or via PM.

The next morning, I was glad when I realized I was the first of us two to wake. It gave me a chance to grab my underwear and head into the bathroom to remove my wet diaper without Ryan finding out about it. I went in, lifted my nightgown, and undid the tapes on the diaper, letting it fall to the floor. I grabbed a couple wipes and went over my crotch and backside as best I could, trying to get rid of the wet diaper smell that seemed to linger every morning. I did notice that I had leaked slightly through the night out my backside, apparently I had not managed to clean everything out of my bowels the night before.

I dropped the wipes into the diaper, rolled it up, and dropped it into the trash can. I was grateful that my mother had insisted on a can with a lid (as a way to control odor from the wet diapers), thinking that Ryan would likely have no need to look inside and see the diapers. I sat on the toilet to pee as best I could, flushed, and slid my panties on before heading back into my bedroom.

Once in my bedroom, I picked up my bra off the floor and began to think about how I wanted to dress for the day. Did I want to go out as a boy or as a girl? I thought about going as a girl when I heard Ryan say, “Good morning.”

“Good morning yourself,” I replied.

“I’ll be back in a minute,” he said, heading into the bathroom to relieve himself. Meanwhile, I slid off my nightgown and picked up my bra off the floor. I was hooking it in the back when he walked back into the room.

I turned around to face him. “Hey,” I answered, “I was trying to figure out what to wear when we go out and around the city today. What do you think, go out as normal, or would you rather I wear a dress and go as a girl?”

“I wouldn’t mind you in the dress, you look really nice as a girl,” he told me.

“A dress it is then. By the way,” I said, hesitating slightly, “I wanted to talk to you about last night…”

“We had a bit to drink, we can forget it ever happened,” he replied.

“Well, that’s not really it,” I said. “I actually liked it a lot, and was wondering, if you, uh, you maybe wanted to go again?”

“We can do that he said,” sitting up on the edge of the bed. I walked over in front of him, and he reached up to pull me down to kiss him.  We kissed heavily for a minute or two, with his arms reaching up to my sides while I draped mine over his shoulders. I broke off the kiss and climbed into bed next to him to cuddle for a bit before we got too heavy into it.

As we snuggled and kissed gently, Ryan asked me, “I forgot what your mom called you the first time I saw you dressed up, what was it, Tonya, or ...?”

“It’s Tina,” I answered.

“Tina,” he said in response, “well, I’m glad we’re together right now, Tina.” He smiled and kissed me. We began kissing more deeply, and I slid my hand down to his crotch to see if he was hard yet. My hands found he was more than ready, and I slipped out of his embrace to position myself between his legs.

“Well,” I smiled, “it looks like somebody is definitely ready for something more.” I fondled him through his underpants, stroking him gently. I slipped my fingers in the waistband, and he lifted himself up as I pulled them off and dropped them on the floor. I gently caressed his testicles, feeling their weight in my hand while I also stroked him gently. He was certainly much bigger than I was, not only with a larger penis, but bigger testicles as well.

I knelt down and, once again, took the head of his penis into my mouth, slowly working my way further and further down the shaft. I sucked gently, bobbing back and forth on his erect member. I knew the concept of ‘deep throating’ (I was in high school after all, kids talk about this stuff!) and wondered how much of him I could actually get in my mouth. I relaxed and slowly tried working more and more of him into my mouth.

I soon was able to feel him pushing into my throat slightly. While I wasn’t gaging on him, it wasn’t the most comfortable thing to do either, swallowing as much of him as I could like that. I backed off and focused my efforts on his glans and the sensitive edge around it. I could taste the pre-cum that was beginning to leak from him, salty and thick. It was only a couple minutes before I felt him begin to tense up in my hands and mouth, and I took him deeper into my mouth to let him shoot his load where I could catch it all.

He finished shortly, and I swallowed everything he had put into my mouth, enjoying the feeling as it slid down into my belly. I licked him gently with light sucking, wanting to make sure I got him fully clean after. I clambered up next to him on the bed, licking my lips to make sure they were clean. “Oh god,” he moaned, “you give such great blow jobs.”

“Believe it or not, I never did it before last night,” I confessed.

“You’re okay with swallowing, too?” he asked.

“Surprisingly, I like the taste,” I admitted. “Besides, if you’re going to give it to me, who am I to refuse? Have you ever tasted it?” I smiled and leaned over to kiss him gently on the lips.

“A girl I was with one time tried French kissing me right after a BJ,” he said, “I could taste it in her mouth. Not something I liked.”

That certainly explained his hesitation at returning my kiss. We lay there quietly snuggling for a few minutes before we began to kiss again, this time more passionately. I reached down and realized he was already hard again after just a few minutes. Youth was definitely helping him out as he was more than ready to go after less than ten minutes.

This time, I helped Ryan up off the bed and had him stand in front of me, naked with his penis standing at attention. I stood up, turned around in front of him, and hooked my fingers into the waistband of my panties to slide them down my legs. They dropped to the floor and I stepped out of them, climbing onto the bed to get on my hands and knees. He climbed on the bed and positioned himself behind me.

I watched as he spit into his hand and used that to lubricate himself. I relaxed as well as I could, pushing like I was going to the bathroom while he slowly pushed into me. He got part of the way in, pulled back slightly, and slowly pushed further inside me. Slowly, he worked himself in and out until I felt his body up against my backside.

He took it slow at first, letting me adjust to him. It only took a couple minutes before the pain and discomfort gave way to pleasure for me, and I began to urge him to go faster and harder. His hands were on my hips, helping me thrust back and forth against him. The night before, it seemed like things only lasted a few minutes. This time, he certainly seemed to last much longer.

After several minutes, I could feel myself building towards orgasm, soon feeling the multiple orgasms building as he kept pounding me. I could feel his large testicles slapping against my legs every time he bottomed out inside me. I begged him to keep going, to come inside me, and wondered how much longer he would last.

It was probably almost ten minutes of hard sex before I felt him pick up the pace as he neared orgasm. “Don’t pull out,” I begged, “come inside me. I can’t get pregnant, so please, just come inside me.”

Thirty seconds later, he obliged me. I felt him slipping in and out easier as his ejaculate helped lubricate things while he slowed to a stop. A few seconds later, he slid himself out of me and we both collapsed on the bed, smiling and happy.

He leaned over and we kissed deeply. “That felt good,” I told him, “thank you.”

“Thank you,” he said, “not a lot of girls are as good in bed as you.”

“Can you believe I lost my virginity with you last night?” I chuckled. He just smiled at me and caressed my cheeks before leaning in for a few more kisses. I didn’t want to get up from our post-coital bliss just yet, so I focused on trying to keep my bottom clenched tight to avoid leaking. At least I didn’t feel like I needed to empty my bowels like the night before.

We snuggled and kissed gently for the next ten to fifteen minutes. I snickered slightly as he put a finger into the cup of my bra, and I caressed his stomach and reached down to fondle his penis once more. “Want to try once more?” I asked, gently rubbing him. He just smiled at me, and it was only another moment before he was again hard and ready for action.

This time, I climbed on top of him, facing towards his feet. Somehow, it didn’t feel right to be bouncing up and down on top of him with my penis where he could see it. I lowered myself down onto his erect member, gently guiding him inside me. This time, it didn’t really need to be lubricated as I still was full from our previous romp. I had much better control over where he hit me inside, and was soon riding and grinding myself down on him as he rested his hands on my hips.

This time it seemed to take even longer to get him to come. By the time he did, he was moaning, “Tina, god yes, just…”

He shot another load inside me, and I gently pulled off, both of us spent, my legs aching from our lovemaking. “Good for you?” I asked him.

“Oh yeah,” he smiled back at me. We snuggled and kissed for several more minutes, and finally decided we should get up to get ready to go about the city for the day like we had originally planned to.  I pulled a pair of panties and a bra from my dresser together with a light sundress, draping them over my arm while he grabbed a clean pair of underwear, his pants and shirt. We headed into the bathroom together to get ready.

Ryan turned on the shower to let the water warm up. While he did that, I reached under the sink and grabbed a tampon out of the box, unwrapping it. Ryan looked over at me while I did, and I explained, “I leaked after last night, I don’t want to be leaking all day and ruin my panties.” He turned around and tested the water while I slid it inside me. We stepped into the shower and rinsed off. I was grateful to get the water down between my cheeks and clean up what hadn’t all been shot inside.

We soaped each other up playfully, Ryan seemed to want to concentrate on my chest and bottom. I had no problem cleaning my own crotch, and then grabbed his penis and rubbed him up and down with my soapy hands. Not surprisingly, he grew hard right away. “Hmm,” I surmised, “it looks like someone is ready for one last go.”

I rinsed him off while continuing to stroke him, then dropped on my knees in front of him, taking him in my mouth again. I could feel his hands on either side of my head with the warm water cascading down around both of us as I worked to get him off as quickly as I could. Once more, he filled my mouth and I swallowed every drop I got.

We finished showering shortly after that, and dried off before starting to get dressed. I added a panty liner inside my panties, not sure if the tampon would keep me from leaking entirely or not. It didn’t take Ryan long to get dressed, but I spent a fair amount of time getting my hair and makeup ready.

“What is it with girls taking so long with all this?” he asked.

“Well, if you want me to go out with you as a girl, I don’t think you want anyone to know the truth,” I said. “Besides, we like making other boys jealous of you.” I kissed him quickly on the lips and he smiled at me.

Once ready, I grabbed a pair of wedges and we set out to visit some of the sights around the city, spending a lot of the time holding hands and sneaking quick kisses. After we finished sightseeing, Ryan bid me farewell with a last long kiss; he still had plenty of stuff to see and deal with at the local college.

It was two days later when my mother and stepfather returned home from their vacation. I spent the whole time after Ryan left dressed as a girl, trying to collect my thoughts about what we had done. My mother asked how the visit with Ryan had gone, and I simply told her it was, “Fine.”

She noticed my outfit and looked me over a bit more intently. “Is this what you wore when he was here?” she asked.

I knew she would figure out the truth even if I tried lying. “Yeah,” I replied, “he remembered meeting me as Tina that time and asked me if I still dressed, and then wanted to see me dressed again.”

“So what did he think of how you looked?” she probed.

“He thought I was pretty,” I admitted.

“Did you just dress for him, or did something more go on?” My mother certainly had an idea of what might have transpired.

“Yeah,” I confirmed, “we did something more.”

“So you two had sex then?” she asked.

“Yes,” was the only thing I could say.

“So was it good? Did you enjoy it? Or was he not that good in bed?” she continued to dig.

“It was good, I did enjoy it,” I confirmed.

She smiled at me knowingly. “If you think anal sex feels good, wait until you have a vagina. Having a man inside your vagina feels wonderful.”

I was left wondering if my decision to not transition was the right one or not, and I would remain confused about it for quite a while.
This is such a wonderful story and extremely well written.  Thank you.

I will be very interested to read your Epilogue and your thoughts (confusion?) over whether to remain a boy, or go girl, especially after you enjoyed intimacy as a young woman so much.

I also want to compliment you on how you wrote about your sexual experience with Ryan. It came across so well as the first erotic experience of a pretty girl, who just happened to be born male. This really made me smile.

So this is where I’m going to end the story at. I'm still not 100% certain what was my mother's motivation behind all of this, even to this day. I know from comments that she made to me that there may have been her own reasons for it, but any time I asked her about it, her response was simply that it was because I had asked for it, that she was helping me experiment and find out what I wanted in life. Yet I know from what she told me that she had wanted two daughters, that she had not wanted a son at all. I know that the divorce she had from my father was extremely bitter, and that I both looked almost exactly like him and had a personality just like his. I'm not sure whether there was something about getting back at my father through me as well. Add in to that the fact she had me in my sister’s hand-me-downs when I was much younger when I was still in diapers as well. So there's a lot of questions behind why, and I doubt I will ever know the full answer.

The biggest thing I have figured out with my mother is that she is an extremely controlling person. I think a lot of this is why her and my father ended up getting divorced, he was tired of her trying to control everything in his life and she was upset over not getting her way. I know most of the fights my sister and I listened to between my father and her were with my father being calm and reasoned, while she was just blubbering in tears. A lot of this was probably about getting her way. I know that when she dropped into the tears with my stepfather he was willing to do anything to make her happy again, probably the reason why they are still together after all these years.

When I turned 18, I went immediately into a military college at the urging of my mother and stepfather (probably trying to get me to ‘man up’ after deciding to not be feminine). I left after six months because I hated it, and my mother and stepfather were upset by me leaving, telling me that I would never get a dime of support to pay for school if I did (a lot of their reasoning was that I got a scholarship, though it was contingent on me serving several years in the military after graduation). I didn't care, I left, and worked full time to pay for my own school even though my sister and stepsisters had most of theirs paid for by my mother and stepfather. My mother originally kept in touch with me a lot, reminding me when it was 'that time of month', and getting me the occasional feminine things to wear (when I went to visit once and she thought I needed new clothes, she pushed for me to shop in the women's sections).

During this time I spent a lot of time questioning what I really wanted in life. While I never slept with another man, I debated whether or not that was the direction I wanted to go. While I had certainly enjoyed my one sexual encounter that way, I was wondering if I also wanted to have sex with women as well. Not having done it before, I was unsure if it was what I wanted or not. I certainly enjoyed looking at women, and had seen plenty of porn magazines, so I wasn’t wanting to restrict myself completely. Still, I had my mother gently pushing me that direction, and I kept wondering if it was the direction I should have taken. That was when something happened that made me realize I wanted to live life as a male.

I met a woman I fell in love with, and we did what most young people do: have kids, get married, etc. My mother couldn't stand this, my new wife was from the 'wrong side of the tracks' and 'low class', and ‘just trying to trap me with getting pregnant’. I spent a lot of years trying to smooth things between them, and when I finally stood up for my wife to my mother, things got really nasty. She berated me for not being able to ‘forgive and forget’ with one breath, and in the next blasted my wife for being ‘low class’ and ‘trapping me by getting pregnant’. What she beat on me about was the same behavior she wanted to engage in herself.

The end of my relationship with my mother came not too much later. She wanted my son and daughter to spend the weekend of my son’s birthday with her. My wife and I discussed it and decided we always spent our children’s birthdays with them as we considered those dates special and important. My mother had my sister call me to find out if we were going to send the kids to her for the weekend, and I said we weren’t.

That afternoon, as I drove home from work, I got a voice mail on my cell phone. It was my mother. She was threatening to get a lawyer and ‘sue me for every penny I’ve got’ for not letting her see her grandchildren. I was livid, to a point that my wife has never before or ever since seen me upset to that level. I was shaking so hard, and I could barely see straight I was in such a state.

It took weeks for me to get to a point where I could call my mother back to try and discuss things with her, as every time I thought about it I just got pissed off again. When I finally did calm enough that I felt I could talk to her, she immediately launched into attacks on my wife and I, arguing that we were using our kids as pawns to get at her. I tried to point out that she should know me well enough, as she had been the one to raise me. Her response was what finally killed our relationship.

“I’m sorry I ever gave birth to you.”

I cut my mother out of my life for good at that point. My marriage has only gotten stronger since, and my wife and I are happy.

My wife isn’t a fan of my dressing up, but recognizes what it did in teaching me to see life from someone else’s eyes. I’m successful, working a job that allows her to remain a stay-at-home mother. She doesn’t have a problem taking a dominant role in the bedroom, appreciating my oral stimulation skills and enjoying pegging me from time to time. She even has me using tampons after pegging so that I don’t leak lube through the night after.

My wife certainly didn’t mind when I faced the loss of my testicles due to medical issues (not cancer at least). Her view was that they didn’t define me as a man, but I certainly didn’t need them anymore, and now she wasn’t the only one having to think about birth control.

I’m also in diapers constantly now, a result of the worsening of the bladder control issues that have plagued me my entire life. My wife doesn’t mind them, and warns me when ‘things are showing’ if my pants slip down slightly. My wife actually has much more masculine sides to her personality, never liking dresses or skirts, never carrying a purse, and not one for being emotional.

In the end, I am happy where I am today. While I live my life as a male, I have feminine traits that complement my wife’s masculine side well, and we celebrate 25 years of marriage this year. While I may question my mother’s motivations and reasoning, I don’t regret the time I spent living as a girl and wearing a dress or skirt.

It did take me a lot of years and some time with a counselor to get to this point. The first few years after I moved out were a mix for me—I harbored a lot of resentment towards my mother for what I perceived as her pushing me towards living life as a girl or woman. There were definitely points I thought it was her desire completely that drove it all, and her emotional manipulation of me that left me enjoying it so much.

It seemed like I got little attention in the family as the only boy, but that changed dramatically when I was in a skirt or dress. I often felt my mother was fairly cold towards me, but suddenly became much more affectionate when I was seen as a girl. Last, it seemed like my sister and stepsisters could do no wrong in my mother’s and stepfather’s eyes, but I was always criticized for not meeting the high standards they wanted for me. As a girl, instead they accepted me as I was, making me feel like I was finally worth caring about in their eyes.

My mother has always been good at manipulating people, and I am left with a final feeling like my dressing was just another manipulation of hers over the years. Why she did that will likely always remain a mystery, I doubt she’ll ever be honest about it and I no longer talk to her, so I’ll probably never know. I’m not the only one who has cut ties with her and my stepfather; my stepsisters did as well, and it seems that the only reason my sister hasn’t is because of legal troubles she’s had.

So, I spent a lot of time in my life living as a girl, and though it wasn’t the final path I took, it certainly changed me. Even so, it left me with a lot of questions and insecurities inside. To this day, I still cannot help but feel like the person I am inside isn’t acceptable to those around me. Am I being the person my loved ones want me to be? Even with my job, I am hyper-vigilant about performing to the peak, and still wonder if I’m good enough to still hold my position. This is even after 20+ years of employment, multiple awards and promotions.

There’s demons that hide in the back of your mind with all of this, nagging doubts about whether any one decision was the right one or not. Getting to the point that I accept my time as a girl was just one step. Was it the right thing for my mother to do for me? Was she truly just wanting to help me decide what I wanted? Or were there her own selfish reasons hidden away in the back of her head behind it all? I live my life as a man now, though part of me sometimes wants to go back to being female.

I’ve given up trying to decipher the right and wrong of it, it is just my past.

To those of you who have read through and enjoyed this, thank you. In a way, it's cathartic to get this all down somewhere that people can understand and appreciate it without looking at me like I'm a freak. Sometimes, we just need that friendly ear to listen to us and allow us to process our thoughts.

Thank you for sharing your amazing journey and first-hand experiences of a boy experiencing life as a teenage girl. You got to do something that many of us always dreamed about. At the same time, you made it clear that not everything about a teenage girl's life is all roses.

It's been a pleasure to follow your story for these past months and read your insights about life as a girl for a boy. I am glad you found writing this to be cathartic and a worthwhile endeavor. I have recommended this to some of my friends, who like so many of us, are married with families, and yet always wondered what it would have been like if we too had asked, "Mom, what's it like to be a girl?"

I was born as a boy, I’ve always looked very much like a boy, and I’ve never wanted to be a girl. Still, I don’t believe I’ve ever felt the same way about my sexuality as most boys seem to feel. I’ve never been a sports buff, and my eyes have always tended to water very easily whenever the movie-makers “get out their violins.”  

I’m now 61, and I only recently came to realize that I also have a starkly variant way of viewing women. I tend to seek an emotional relationship first, while most other men tend to seek the physical first. Why am I so different from them? Why are they so different from myself? Only now I’ve learned that this seeking after an emotional relationship first, tends to be far more aligned with the female psyche, than with the male.

I say, “To heck with it all. I really don’t care if other men are wired like me or not. I am who I am, and the rest of the world can take it or leave it as they please! We are each a child of God, in so far as I’m concerned, and I will damn well let my tears flow in sappy movies if I want to, and to care deeply about the one I am with if I want to, and I will not allow any piece of physical equipment that may or may not be attached between my legs, dictate to me otherwise, for Christ’s sake!”

What is the matter with our society? Why does it care whatever one or two consenting adults might do in the privacy of their own homes? What f'n business does it ever have invading the privacy of our homes? What f'n business does it have wanting to probe and invade the privacy of whatever human "equipment" we might have chosen to conceal beneath the privacy of our own chosen garments?

This is a beautiful story about your fearless discovery of self. Yes, your mother herself obviously never had half of the courage that you had, but twice the self loathing, which she constantly expressed in her belief, that her ability to manipulate others was somehow essential for her own sense of self worth. I hope you might please forgive my preachiness here, but we are each a child of God, and the more we know this to be true, the more courage we will have to discover this one most beautiful reality about our own true selves.

I believe that the reason she disowned both you and your dad, was probably simply because you each dared to be true to yourselves, which happened to threaten her own obviously very fragile sense of self. Perhaps after some many years, you and she may cross paths again. I hope that by then you might be able to feel more compassion towards her than blame, for both of your sakes. Yes in cases like your own, blame is a healthy first step of self discovery, but the greatest self discovery comes when that blame is permitted to mature over time into compassion. Your true story has inspired me, and for that I am greatful.
Wink Blind in one eye.  (Hope I got the right avatar here.)

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