Sissy Self Actualization

Hi. My name is David. At least it was, as this story starts.

I grew up in a very strict, religious family in the Midwest. My family members are the types who will say things like, "Men (meaning Trans Women) shouldn't be allowed to use the ladies' room." And, every time they would say something like this, I would cringe inside. You see, I am a sissy. I have been a sissy for as long as I can remember and will probably always be a sissy. It wasn't some choice I made, it's just who I am. Even as far back as preschool, I have had more girl friends than boy friends. I just like their more gentle ways, and their pretty clothes! I always felt so jealous about the pretty dresses that the girls got to wear.

Of course, I had to hide my sissy personality from my family, which I did, more or less. There were some physical traits that I couldn't do anything about. I was short, with a slight frame and soft features. I was neither brave, nor good at sports. But playing sports was expected in our family, so I did my best, enduring the taunts of the more talented boys on the various teams I played on. "You suck" was one I heard a lot.

I think all this was OK with my father. He could tell that I was no good at being a boy, but at least, to him, it seemed like I wanted to be good at being a boy and that was enough for him. It was at least until one day when he took me hunting and I burst out in tears after he shot a deer. We don't talk about that day.

My mother was a different story. I got the sense that she knew what I was and that she didn't really hold it against me. She would have loved me regardless of my sissiness but she was concerned about the family's reputation in town. So mom was very comfortable never mentioning my obvious discomfort in trying to conform to the male ideal. To her, it was a pandora's box. What if word got out that she and her husband had raised a sissy! Oh my! They would never live that down! They might not even get invited to some parties and that would never do.

My sister, I think, knew. She was, unfortunately, very meticulous and careful with her things and, of course, I adored borrowing her pretty outfits. Even though I would be as careful as I could to put things back the way I found them.

A couple of times she asked me, "Do you know if someone went through my drawers?"

There was a certain look in her eye that made me think she knew...or at least suspected that that someone was me.

My parents were very strict about computer usage, and it made my searches into gender fluidity difficult, but one day I discovered a site called literotica and from there, I quickly found there was a chat room for transgender people.

For the first few weeks, I didn't post anything or chat with anyone. I just wanted to absorb what was being said like a sponge. It was comforting to find a group of people like me. After a few weeks, I began to chat with others like me - girls who often defined themselves as some sort of sissies. It felt so nice to engage with 'girl talk' with others like me! We would chat about fashion and makeup, and sometimes pretend we were sissies being intimate with each other and sometimes we would even chat about men!

I had always been a good student, and at this point I knew what University I was going to attend. It was a well-regarded institution on the East Coast and because my grades in High School were so good, my parents, who had very little money, wouldn't have to pay any tuition.

Usually, when men pm'd me, I wouldn't respond but one day a man, MasculineDaddy4Sissy pm'd me, introducing himself. Curious, I looked over his profile and, as he sounded interesting and safe, began to engage in chat with him. Immediately, I took a liking to him. He was quite a bit older than I was (which was ok because I have a thing for mature men) and, as I learned, he was Ex Military! Somehow, that really appealed to me! He was also tall and fit and just perfectly fit into the kind of man that I had fantasized about for years! Tall, strong, and commanding - everything I wasn't.

We began to chat on a regular basis, and every time we did he would leave me wanting Him even more!

The days and weeks until I left for college were ticking down and I couldn't wait! The strain of hiding my true nature from my family was taking a psychological toll and I couldn't wait to get out of my hometown. I was working two jobs and saving up as much money as I could. I knew it would be difficult to afford college because, even though my tuition was covered, I still needed to pay for room and board, as well as textbooks and other incidentals.

Meanwhile, I was spending what little spare time I had reading stories about trans girls and chatting with my favorite Daddy. More and more, I was realizing that I not only had a sexual attraction to masculine guys, but a romantic one, as well. Sure, I could imagine myself cuddling with a woman or another sissy, and maybe even lovingly touching them in an intimate way but I was sexually drawn to Real Men. I began to wonder if I could actually meet a man while I was at University. Was I ready to take that step?

Finally, it was move-in day! I hugged my family goodbye and moved my few belongings into the small room I had rented in a house about three miles from campus. I wanted to live off campus rather than in a residence hall in order to afford myself a little privacy. I hope that if I could earn enough money, that I would be able to finally build a feminine wardrobe for myself.

I was chatting with Daddy about a week after I moved in and excitedly telling him about my move when He asked me what university I was attending.

"I'm attending Brown in Rhode Island.", I answered.

There was a long silence before Daddy responded. To be honest, this made me nervous - had I accidentally offended Daddy?

Then Daddy typed His reply, "Brown University is only seven miles from my house."

My heart skipped a beat! My God! Daddy was right here!

I had been at Brown for a couple of months now and I was getting into a routine. Classes in the morning and afternoon, bussing tables at a local restaurant in the evenings and maybe a bit of time for jogging, yoga, friends, or, my favorite, chatting with Daddy on lit!

One evening when I was chatting with Daddy after homework, he said, "I see you have a birthday coming up."

"Yes, Daddy!" I replied. "How thoughtful of You to mention it!"

"Well little girl, Daddy has been thinking about what to get you and I think I know just the thing! I have decided to buy you makeup lessons!"

"Really Daddy? That sounds expensive - You don't have to."

"No baby. I want you to learn to be the girl you really want to be! The only thing I ask in return is some photos of the finished product, OK?"

"OMG, Daddy! I am so excited - I can't believe it! You are the sweetest Daddy in the whole wide world!!!"

The rest of the evening was spent chatting with my Daddy about specifics. Where the makeup artist was located, how many lessons Daddy would pay for and things like that. I was so excited that my heart kept fluttering! I was so hoping that Elizabeth, the makeup artist, could make me look pretty and, more importantly, teach me how to make myself look pretty. I also worried....what would I do if Daddy didn't like how I looked?

Soon, the big day was upon me! I took a train to NYC where I was to get my makeup lessons. Much to my relief, the studio was in a nice part of the city and Elizabeth was wonderful and immediately calmed my nerves...She asked me what kind of look I wanted to achieve (very feminine, slightly innocent) and then slowly walked me through the makeup routine explaining the roles of foundation, concealer, eye shadow, mascara, makeup and how to apply all of it. She showed me how to lighten the corner of my eyes to make them look bigger and more innocent. After a couple of hours, she surprised me by fitting me with a long blonde wig. I looked at myself in the mirror and I could hardly believe what I saw. There, standing before me, was a young, pretty GIRL!

I asked nervously, "Do I look as good as I think I do? I mean, I think I could pass anywhere!"

"Yes, honey." She replied. "Fortunately, we had a lot to work with. You are quite slim for a guy, and your face has soft features, your skin is soft. I think you make a much cuter girl than a guy, if I do say so myself! Now, let's take some pictures for your Daddy!"

I felt my face turn red...this whole time she knew just why I wanted to learn to do makeup!

Elizabeth did a full photo shoot, carefully posing me to look extra cute! In the photos, I appeared to be a pretty young woman, with shining eyes and perfect makeup. I looked slightly innocent, soft, and vulnerable. Exactly as I wanted.

Elizabeth informed me that she wanted to touch up the photos a little bit before she sent them to me and three days later, they arrived at my inbox. I was so nervous and excited when I got them. Shaking, I opened them up and looked at them one by one...OMG! I looked even better than I had remembered. Excitedly, I composed an email to Daddy and sent Him the photos...i was hoping He would like them! Within minutes, Daddy responded telling me how pretty and feminine I looked!

I had been at Brown for six months now. One day, I was chatting with Daddy and confided in him how overwhelmed I felt between my classes and work and struggling to pay for necessities like food and rent when Daddy, totally out of the blue, suggested that He had an extra room and that I could move in with Him to save money!

"But, but Daddy, I don't know if I am ready for that!"

"Don't worry, baby." Daddy replied. "I don't expect anything from you other than you live as Kimberly for as long as you stay with me. I am simply asking you to live as your authentic self as you have described yourself to me. That means wearing pretty clothes and always behaving in a feminine manner."

Oh My God! This was a HUGE step! But the truth was that I had been dreaming of a day like this since I was a little girl and I had developed quite a crush on Daddy in the time we had been chatting! Daddy was tall and confident and everything I could never be! I imagined how safe and protected I would feel living with Him!

Still, I was quite nervous, and asked Daddy if I could think about it for a few days. "Of course, baby. You take as long as you need."

But, honestly I didn't need time. I knew that I either had to face myself as I really was or never fully realize my potential as a truly feminine being. The next day I told Daddy that if His generous offer was still on the table, I would be honored to move into His home!

Two days later, I was living with Daddy! As per Daddy's instructions, I wore lingerie under my boy clothes and my first order of business was to transform myself into Kimberly. That meant removing what little body hair I had, doing my makeup, and slipping into a pretty dress with heels and hosiery. After two full hours of primping, I swallowed hard and stepped out of my room.

"Baby, you look beautiful!" exclaimed Daddy, grinning.

I felt so happy in that moment! My heart was overflowing! I went to Daddy and threw my slender arms around Him.

"Thank you, Daddy!" I gushed.

"You know what?" Daddy said, "We should celebrate! Let me take you out to dinner!"

"But Daddy, I have never been out in public as Kimberly before!" I protested.

"Nonsense!" Daddy insisted. "You look just like any other pretty young woman! This is a special day for you. Now let me take you out!"

Reluctantly, I agreed.

For our date, I wore a pretty black dress, sheer black hose and a black handbag and pumps. You can never go wrong with black! Daddy wore a nice pair of slacks and a sportcoat. Then, I took Daddy's arm and He escorted me to His car, even opening the door for me! What a gentleman!!!! I carefully entered the car, careful to keep my legs together like a proper lady.

I was so nervous, I could hardly eat! Plus, I didn't want Daddy to see me eat too much as that would be unladylike! Somehow, I got through dinner without having a nervous breakdown! Daddy paid for the dinner and left a generous tip and then I took Daddy's arm as He escorted me back to His car.

"That wasn't too bad, was it?" Daddy asked.

"Oh Daddy! I had the most wonderful time, thank you!"

And then, without even thinking, I got up on my tiptoes and gave Daddy a kiss on His cheek! He pulled me to him and brushed a little of my hair from my face and said,

"Kimberly, I am so happy to see you developing into the girl I knew you were from the first time we chatted."

Then He gave me a kiss right on my lips! I thought I had died and gone to heaven!

Daddy drove us home and I hung on His arm as He walked to the door.

I wanted more, but Daddy, being wiser, said, "I think that is enough for you for one day, young lady. I'm sure you have homework to do and I wouldn't want you getting bad grades because of me. Now get along and go to your bedroom."

I felt both disappointed and simultaneously thrilled. One thing for sure-i was falling in love with my Daddy!

The next morning, Daddy woke up to the smell of toast, fried eggs, bacon and coffee.

"I made breakfast for you, Daddy!" I said gleefully. I hope you like it!

"I love it, baby!" Daddy said and gave me a kiss!

Later, as Daddy was about to leave for work I called out, "Daddy wait! I want to give You a kiss before You leave!"

Then, Daddy picked me up in His strong arms and lifted me so that our faces were at the same level and gave me a kiss right on the lips!

"I'll be thinking about Kimberly all day now!" said Daddy in His masculine voice.

Alone, I cleaned up the dishes and prepared myself for class, getting back into my boy clothes. I would be thinking about Daddy, too!

A few days had passed and my life settled into a happy routine. I would wake up early and shower and do my makeup and dress for Daddy. I would then make Daddy's breakfast and kiss him goodbye as he left for work. Then I would remove my makeup, get into my hated boy clothes and attend university until I got home, when I would once again become Kimberly. I would start dinner, and anxiously anticipate Daddy's return. Before He arrived, I would ensure my makeup was fresh and that I would be in a pretty dress for Him. As he pulled in, I would be sure to greet Him with His favorite drink and a kiss.

And, although I felt like I was ready for more, it felt like Daddy was slowly nurturing my femininity until I was ready for more intimacy. One evening, Daddy and I were cuddling on the couch watching a movie together and I felt so safe and happy and feminine with His strong arms around me! I am quite petite, only 5'5" and only 128 lbs (I was trying to slim down for Daddy) and I always feel so small and cute when I am with Daddy, who is quite tall and muscular. From time to time, Daddy would pull me to Him and kiss me tenderly and I would just melt every time He did this. I felt so much His!

I really don't know what came over me that night, but, after one of our kisses, I slid down off the sofa and positioned myself between Daddy's legs and then, looking up at Him, whispered, "Daddy, please?"

Daddy just looked down on me and smiled. I smiled back and then lovingly kissed him right over the fly of His pants. I looked up again, looking for Daddy's reaction. Daddy just smiled at me and nodded. I then unbuckled Daddy's belt (hopefully seductively) and then pulled up His shirt a little and kissed his belly. My hands shaking a bit, I undid the snap on His pants and then slowly lowered His zipper. Nervously, I exposed the top part of Daddy's boxers and planted a soft kiss right over His penis, which was already beginning to swell! I looked up again, eager for Daddy's approval. Daddy gently cupped my face and guided me up and kissed me passionately with lots of tongue! OMG! I think Daddy liked what I was doing!

Daddy guided me back between His legs and I kissed his cock over His boxers again and this time His cock felt even bigger and harder! I hooked my manicured fingers around the waistband of His pants and gently guided them down over His hips and strong butt and thighs. I kissed his thighs lovingly and then removed His pants entirely! My small hand moved up over His cock and my fingers gently outlined the contour of His manhood. Daddy groaned with pleasure as I lovingly caressed His now rock hard cock. Looking up once again for His approval, I then began to work His boxers down over His muscular butt and thighs, his cock springing forward as the boxers freed it! It was huge! Probably 8", and thick and veiny. Nothing at all like my little sissy clit and it showed me, once again, that Daddy and I really are different genders.

Taking my gaze away from Daddy's cock to his eyes I plead, in my best little girl voice, "Daddy, may I kiss it?"

"Of course, baby."

Then, without breaking eye contact, I began to kiss Daddy's delicious cock and it felt so perfect and so right and so natural. It just felt right.

Daddy let out a deep contented masculine groan as I ministered to His cock, planting little kisses all along the length of it and then planting a kiss right on the head before taking the head into my wet mouth and running my tongue all around the circumference of it.

"Kimberly, I think you are ready for the bedroom." Daddy said before helping me up and leading me by the hand to His bedroom.

Once there, Daddy had me turn around and then He carefully unzipped the back of my dress and bared my shoulders, kissing them delightfully and causing me to break out in excited goosebumps. He guided the dress the rest of the way over my shoulders and it fell into a crumpled heap around my ankles. Daddy steadied me as I gracefully stepped out of my pretty dress leaving me in just my panties, bra, stockings, garter belt and heels. I turned around and, after Daddy kissed me on the lips again, started to undo the buttons of His shirt. I gently kissed each newly exposed bit of flesh as I undid each button. Daddy then held me tightly and kissed me deeply. Then, he gently scooped me up and deposited me on His bed.

Climbing into bed next to me, Daddy started to kiss me passionately and deeply. He then announced, "I think it is time for Kimberly's panties to come off!"

I was on my back and Daddy grabbed the waistband of my panties as I arched my back so that He could pull them down over my cute butt. He then expertly guided them over my smooth thighs and calves and then over my heels. I was so excited, but my little clitty somehow managed to stay limp and not embarrass me!

Daddy then slid on top of me and began to kiss me and caress my nipples, making them go erect. Then, He reached down and began to gently touch my crack, gently spreading my legs so that he could reach my most sensitive regions. I was shaking with nervousness and excitement! Daddy reached into his nightstand and removed a bottle of lubricant and, after warming it up in his big hands, began to slowly caress my hole with the warmed slippery substance...i was panting by this point!

Daddy then kissed me deeply and inserted a well-lubricated finger into my 'pussy'...at first just a little way and then deeper.

"Just relax, baby. Daddy won't let anything bad happen to you."

Kissing me again, Daddy started to move his big finger in and out of my hole.

"Oh Daddy!" I squeeked, "Don't stop!" as I reached down and began to stroke his rock-hard cock.

Daddy then positioned himself over me and looking straight into my eyes asked, "Is Kimberly ready to feel Daddy inside of her?"

"Yes" I answered and I felt Daddy's big mushroom head against my sissy pussy. "No...i mean....Daddy....i'm not sure i'm ready."

"That's ok, baby." Daddy said. "I won't penetrate you until you are ready."

Not wanting to disappoint Daddy, I kissed him and continued to stroke his cock. After a bit, I got really turned on and asked Him if I could again have Him in my mouth.