Finley and his Land-Lady


As a child, I was rather sickly. My mother knew there was something wrong with me and after dozens of appointments with doctors and countless tests, it was determined that I had a pituitary issue. My mother took me to an Endocrinologist who prescribed several different pills to correct for my damaged pituitary gland. He also put me on growth hormone and taught my mother how to perform injections. I was far smaller than other children my age and the doctor warned my mother that I would probably never grow to a normal height. And with my low functioning adrenal glands, I’d never have the energy of a normal person.

Very early in my education, mother decided home-schooling would shield me from the other children and their teasing. She had always been overprotective. But once I began staying home with her every day, her idea of looking out for my safety went to new levels. She never let me do anything strenuous, the only time I was allowed outside was when she was with me and she banned me from playing with other children. My entire childhood was spent at my mother’s side.

Two things happened on my nineteenth birthday. My doctor took me off of growth hormone and announced I was as tall as I was going to get. At 5 feet even, I was still small, but thrilled I wasn’t 4 feet tall! The second important thing that occurred was my doctor determined I would not begin puberty without assistance. I should have begun going through puberty years before, but everyone hoped my body would do it on its own. It didn’t happen. So I began getting weekly hormone injections.

My body began to slowly change after 3 months. By the time I turned 20, we learned my body had begun producing its own low levels of testosterone. After being taken off the injections, my body completed its transition on its own. I’d always been fair skinned with wispy, light blonde hair. And even after going through “the change”, I had to search really hard for pubic hair!

At 20 years old, I was 100% a virgin and completely naïve about sex. For the first time in my life, I was experiencing erections and struggling to find private time so I could play with it. Mother seemed to always know when I tried to masturbate. She would knock on the door or barge into the room. She caught me with my skinny, little, three-inch erection between my fingers on dozens of occasions. She would tell me it was a natural thing and I shouldn’t be embarrassed. But every single time I tried to masturbate, she would interrupt. It was so frustrating!

For the next two years, I lived under her roof but knew I’d have to leave someday. I couldn’t live with my mother forever. But I had no clue what living on my own entailed. I still got ill very frequently, and when I was sick, I got really sick. So sick I could never hope to care for myself. My energy level was still far below a normal person. I’d never had a job, nor would I be able to work a normal 40-hour work week. I would be dependent on others my entire life.

So when I told mother I thought it was time I moved away from home, I was shocked when she agreed. She didn’t agree right away. She had to think about it for several days. But she did eventually agree I should try moving away from home. Of course, she insisted on helping me find a place to live. She wanted me to move in with one of her lady friends a few blocks away, but I wanted to move further away than that. I whined and pouted until she finally gave in.

She and I packed up two suitcases with my belongings and made the 2-hour drive to the next town. Before we left, she and I had searched the internet for rooms available for rent and made appointments with three people. The first two ladies were very nice, but for some reason, mother didn’t approve. The third lady we met with, Bessie Ackerman, was exactly the woman mother hoped to find.

Bessie was in her mid-fifties and was a substantial woman. She stood at least 5’10” and had to weigh more than my mother’s 250lbs. She had giant boobs, thick thighs and wide hips I briefly imaged her carrying me around on. Bessie was a widow, her husband had been a doctor while she was his nurse. She had retired a few years earlier. She had a daughter who ran away from home when she was 17 because Bessie was so controlling and overprotective.

Bessie hadn’t seen her daughter in more than 15 years. She told my mother and I she’d always hoped her daughter would return home. And only recently had she finally accepted that she would not. It had taken a long time, but she was ready to close that chapter in her life.

After Bessie had told us about her situation, I sat silently beside mother while she went into great detail about my life and special condition. Bessie interrupted mother shortly after she’d started to get a pen and tablet so she could take notes. After reviewing my medical history and going over each of my medications, mother told her about my lack of education and general upbringing. The last piece of information she shared was that I absolutely no experience with girls and she preferred it to remain that way. She told Bessie that burdur escort I wasn’t mature enough to deal with a typical boy-girl relationship.

Bessie finished scratching down notes and when finished, looked at mother and smiled warmly. She asked if I had any food allergies and wrote down each item as mother listed them off. Bessie then asked about activities I was not allowed to perform. Mother began with all outdoor activities and sports. She said I could assist with some household chores, but I would get tired easily and mother was willing to pay an increased amount of rent to make up for that. Bessie told her that wouldn’t be necessary.

She told Bessie I could watch movies and television shows as long as they weren’t violent, had sexual references, or foul language. She didn’t approve of the horrible things that could be found on the internet and had never allowed me access. Mother told Bessie I didn’t have a cell phone for that very reason.

Bessie smiled again while still writing down notes and told mother that she had a corded land-line that I could use to call home. Bessie went on to promise that she’d have me call home every single day. She also promised to call my mother directly if she had any questions or concerns about my health or behavior.

Bessie and mother exchanged phone numbers, email, and home addresses. The two of them discussed the rent amount and due date. They were talking like they’d known each other for years. All the while, I sat right beside mother, not saying a word. But I was terribly excited to finally move out on my own. Sort of. I was also afraid of not living with my mother. I’d spent my entire life with her. The entire experience was bitter-sweet.

After a pause in their conversation, mother said, “Bessie, I believe you are the perfect woman to look over my special boy. With your nursing background and maternal nature, I can’t think of anyone more qualified. I know it is a lot to ask, but are you interested in having Finley as your tenant?”

Bessie looked right at me and smiled warmly. She spoke to mother, not me when she answered, “Yes, I’d be happy to look after this precious angel.”

There was no lease to sign, it was a verbal agreement. Mother wrote out a check for the first month’s rent and all three of us then walked out the driveway to retrieve my suitcases. After closing the trunk, Bessie told mother she had a long drive home. She didn’t need to stay any longer.

Right there in the driveway, mother and I said goodbye to each other. We hadn’t been apart since I was a small child. When we embraced, tears welled up in my eyes and began running down my cheeks. I began sobbing uncontrollably. Mother bent down, kissed me on the lips and whispered goodbye. She turned quickly, got in her car and drove away.

Bessie wrapped her arm around my shoulders and held me close against her. When mother’s car turned the corner and disappeared from sight, I completely lost it and began bawling. Just when I was about to run after her car, Bessie picked up my two suitcases and guided me into my new home. She set my bags down just inside the door and led me to the couch I’d been sitting on moments before. Bessie sat down and pulled me onto her lap. She wrapped her arms around my body and gently rubbed my back.

She whispered softly while holding me on her broad lap. “It’s hard to say goodbye, isn’t it, Finley. In just a few hours we’ll call her up and you can talk to her on the phone. It’ll be okay. I’m going to take good care of you. Just like your mother, I’ll never let anything bad happen to you.”

I eventually calmed down and Bessie took me to the bathroom and washed my face with a warm cloth. Whenever I got overly emotional, mother used to wash my face too. Having Bessie perform that simple act made me feel warm inside. She informed me that the bathroom we were in was all mine. She used the master bath which was adjacent to her bedroom. In my bathroom, the towels, washcloths, rugs, shower curtain, toothbrush holder and cup were all a soft, pastel yellow. Everything else in the room was perfectly white, except for the glistening chrome faucets and handles. It was a very bright and cheery room and I loved it.

From there, Bessie guided me across the hall to what would be my bedroom. As I stepped into the room, I gasped and felt a chill shoot up my spine. It was by far the most feminine room I’d ever seen. It looked like it belonged to a princess. The walls were painted a soft, pastel pink. The bed, night tables, dresser, rocking chair, and vanity were all painted perfectly white. Until then, I’d always slept in a single bed. My new room had a giant, queen-sized canopy bed! It was way bigger than what I was used to. The comforter and pillows were frilly and lacey. There were some teddy bears stacked up in the corner and a shelf with a row of books trapped between ballerina bookends.

Bessie stood beside me, holding my hand letting me take it all in. When I looked up into her eyes, she spoke in a soft, caring tone. “Finley Sweetie, I know the room isn’t really bursa escort decorated for a boy. I suppose we can change it however you’d like.”

I didn’t respond at all. I knew she had more to say and wanted to give her a chance to finish.

“After all these years, I’ve accepted the fact that I am responsible for my daughter running away. I was extremely controlling. I chose the clothes she wore. I never let her decorate her room so it matured while she did. I insisted on knowing where she was every minute of the day. I treated her like a prisoner. I’d give anything to have another chance at being her mother.”

Looking up into her eyes, I spoke in a soft voice, “My Mother treated me the exact same way and I think she was a very good Mother. She chose the clothes I wore, the TV shows I could watch, she knew where I was and what I was doing every minute of every day. You don’t need another chance at being a mother. I’m sure you did a perfect job the first time.”

After she’d just consoled me while I cried, I found it was my turn. I tried to wrap my arms around her, but they didn’t reach. She sobbed quietly and wrapped her arms around me. She pulled me against her warm, soft body and I felt loved. Loved just as much as I did when with my mother.

Bessie guided me to the rocking chair in the far corner of the room and sat down, pulling me onto her lap, we snuggled together and she told me about her daughter Chloe. She told me Chloe was basically a good girl. She only started getting into trouble as she grew older. She rebelled against the clothes Bessie insisted she wear. She began sneaking out at night. And her grades began to fall. Bessie tried grounding her, taking away her privileges and eventually resorted to spanking her. The first spankings were with her hand, but she learned that wasn’t enough and began to use a belt.

While stroking my back, Bessie asked if I’d ever been spanked. I squirmed on her lap and told her I hadn’t. She chuckled and told me she didn’t think I had. She knew I was very well-behaved from the moment she met me. But she warned me that if I ever behaved poorly, she’d not only give me a firm spanking, she’d call my mother and tell her all about it. A shiver ran through my body and my butt cheeks clenched together at the thought of receiving a spanking. I know Bessie could feel me squirm on her lap, but she completely ignored my reaction to her promise of a spanking.

Bessie rocked us back and forth while reminisced about Chloe for a little while longer. She stopped when I heard her voice crack and knew the emotions were rising up again. She hugged me and said she was very happy that I’d be living with her. She told me how much she missed having someone to take care of.

She held me in her arms and snuggled me against her large, soft body. Neither of us spoke for a time. We were lost in our thoughts. I had something I wanted to say, but I struggled to work up the courage to do it. When I was ready I whispered, “Bessie, do we have to change my room? Can we leave it just the way it is?”

She had me sit up on her lap and look into her eyes. “Sweetheart, the room is pink. Are you sure you want to leave it as it is?”

I snuggled back against her and said, “I have never been in a girl’s room and I like it the way it is. Plus, this was Chloe’s room. Can’t we just leave it the way it is for now?”

She pulled me back against her body, kissed my cheek and told me I was a precious gift she’d needed for a very long time. After rocking back and forth for several more minutes. Bessie decided we should get me unpacked. We brought my suitcases into my room and opened them on my bed. While I took my toothbrush, comb, and other personal items into my bathroom, Bessie began unpacking my clothes. When I returned, Bessie handed me the pile of my underpants. She told me to put them in the top drawer of the dresser. When I opened that drawer, I found it was filled with neat stacks of panties, bras and other lacey things.

I whimpered softly, “Um, Bessie? Chloe’s things are still in this drawer.”

Bessie stopped what she was doing and walked beside me. “I never thought to pack up her clothes. They’ve been here this whole time.” She closed the drawer and opened the next one. It was filled with neatly folded camisoles, tops, and a few sweaters. The next drawer contained shorts, tights, and two swimsuits. And the bottom drawer had nightgowns and pajamas.

I stood there watching one drawer open after another. All those pretty, feminine clothes had a strange effect on my penis, it became very stiff in my underpants. And I felt my face get warm while I blushed. No matter how hard I tried, I couldn’t stop my hips from wiggling around.

Bessie took my hand in hers and led me to the closet. She opened the door slowly and what I saw took my breath away. It was a walk-in closet. There were dresses, blouses, skirts, and jumpers in every possible shade of pink, yellow and lavender. There were dozens of pairs of shoes neatly arranged on the floor along the walls.

I’d never really çanakkale escort thought too much about girl’s clothes before that moment. But as I stood there looking at all the feminine outfits in the variety of fabrics, I wondered what it would feel like to wear them. I’m not sure if I took that first step into the closet on my own, or if Bessie gave me a gentle push. But I found myself standing in the middle of a closet filled with the girliest clothes I could imagine.

In a soft voice, Bessie whispered, “Chloe was a very petite girl. She was about your size when she ran away. I’m positive most of these pretty clothes would fit you perfectly.”

I turned to face her while at the same time moving both my hands to cover my erection. It was small enough that it didn’t make a noticeable bump, but I still worried about it. Looking up in her eyes, there was no malice, she wasn’t trying to embarrass me at all. She was simply stating a fact.

Bessie continued, “Well, I suppose we need to pack all these things away to make room for your…”

I interrupted her a little too eagerly. I cut her off before she could finish her thought. “Maybe we don’t have too. I mean, not right away. We don’t need to rush. Maybe we could, maybe just pack my clothes again?”

I know I was blushing and felt like I may faint.

Bessie smiled as she stepped into the closet and took me back in her arms. She held my face against her giant chest and whispered, “Finley honey, what are you saying? Do you want to try living in a girl’s room and wearing girl’s clothes? You can be honest with me. I want you to be happy. Do you want to pretend to be a girl?”

I smashed my face between her breasts and whimpered softly. I couldn’t look at her. I was so embarrassed. But I’d never wanted anything so badly. With my face still hidden, I told her I did. I wanted to live in a girl’s room and wear girl’s clothes and even be treated as if I were a real girl.

Bessie hugged me as the emotions of my confession began to surface. I bit my lip and struggled to keep from crying. With Bessie holding me and rubbing my back, I managed to control myself. But a few tears did dampen her blouse.

She took hold of my arms and stepped away so we could look at one another. Bessie suggested we get started. We walked back to the bed and quickly packed away the clothes I’d brought. Bessie also sent me back to the bathroom to get anything I’d brought that was remotely masculine. When I left the bathroom, the only thing I’d left behind was my yellow toothbrush which matched the room perfectly.

After Bessie had closed one suitcase and packed everything into the other, she paused and looked back at me. Her eyes drifted from my feet to my face. She smiled and said there were only a few more things that needed packed. I realized she was referring to the clothes I was wearing.

Bessie walked to the dresser and chose a pair of white cotton panties with lace trim. She then bent down and picked out a little white and pink, cotton nightie. She crossed the room and sat in the rocking chair. While beckoning me to her, she explained that it was early, but she knew I’d had a long day. She knew I’d be tired and need to go to bed early. And that was why she was putting me in a nightgown.

When I stood before her, she reached out and began undoing the buttons on my shirt. She slid the shirt off my body, folded it neatly and set it on her knee. She asked if I needed help removing my shoes and socks. I told her I could do it and sat on the floor to accomplish the task. Rising up on my bare feet, I knew what was next and just when I moved to undo my pants, Bessie reached out and took over.

I didn’t have time to get embarrassed. Bessie undid my pants quickly and then slid them and my underwear down at the same time. I stood there naked in front of Bessie and she joined the very exclusive group of people to ever see me without clothes. My skinny, little penis was very stiff and I kept it behind my hands.

It was embarrassing to stand before this mature woman completely naked. I’d only met her earlier that afternoon. But Bessie made me feel unusually comfortable. Maybe even more comfortable than I did around my mother. So I was blushing like never before, but I didn’t feel like she would laugh at me or make fun of my small size.

While she folded my pants and collected my shoes and socks from the floor, she told me I had a very cute body and she was going to keep me in the most adorable outfits. I stood in the room naked while she packed the last of my clothes in my suitcase. Only when it was closed and sitting by the door with my other suitcase did she return. She picked up the panties and nightie she’d chose and sat back in the rocking chair.

Laying the nightie over her knee, she bent forward providing me with a perfect view down her blouse to her cavernous cleavage. She held open the panties for me to step into. I braced myself against Bessie’s shoulders while I stepped into my first pair of panties. She slowly slid them up my legs and over my stiff penis. As those panties slid up my legs, I was glad I worked up the courage to ask for what I wanted. When the panties were in place, Bessie gently patted my little erection and whispered that it was right where it belonged. I whimpered softly and nearly squirted.

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