My Landlord pt. 1
When I first moved out on my own, I was excited to finally have all the freedom and independence of a full grown man. I had a decent paying data entry job which I could do from home, and I found a very affordable living situation: renting a room in a house with a middle-aged guy named Bob. I would be in a new town where I didn't know anyone, but the ad said there would be 2 other tenants living in the house, so at least I'd have some roommates.
I moved into my new place in late October. The Landlord Bob was in his late 40s, 6'4", with a stocky build around 225 lbs. I on the other hand was 23, 5'6', and a very slender 125 lbs. Needless to say he towered over me, but he seemed very nice and likable. I felt comfortable around him, and as I got to know him, I quickly began to trust and respect him. He had the friendly demeanor of a good pediatrician with the charisma and leadership of a football coach. A very manly man, but not in a violent or threatening way. He and his wife had divorced several years ago, and his daughter had just gone off to college that fall. Naturally, he decided to rent out the unoccupied rooms in his house for some extra income and to keep from becoming isolated.
A couple days after arriving, I noticed I hadn't seen any trace of other roommates. I asked Bob about it, and he informed me the two tenants he was expecting had changed their plans last minute. So until he found new tenants to move in, it would be just he and I. Because I didn't know anyone in town, Bob and I ended up hanging out a lot. We would mostly just sit around and watch TV. We took turns cooking dinner. A couple times we even went out to the movies together. We must have looked like an odd pair when we went out in public - a large imposing man and his meek little sidekick. We joked that he could hide me in his backpack so we'd only have to pay for one movie ticket. I was just a little fairy of a boy compared to him, but I felt safe with him towering over me. I began to really trust and look up to him. I would confide in him about my inner thoughts - my insecurities, fear of failure and inadequacy, my difficulties attracting women. He always had something kind and reassuring to say. He was so calm and confident, and I had pretty low self-esteem. I found myself really depending on his validation. I'd find myself just following him around the house sometimes. He didn't seem to mind the attention.
One evening I noticed him moving some boxes from one of the spare rooms into the basement. I asked him what they were and he explained that his daughter had left a bunch of old clothes behind, and he was just moving them into storage. He made a joke that she was about my size, so her clothes would probably fit me. I laughed uncomfortably as I peaked into the open box he was holding. It appeared to be mostly filled with bras and panties of varying styles and colors. I could see a matching set that were satiny pink with white lacy trim. I felt a quiet surge of excitement at the sight. He interrupted my gaze and asked me point blank if I'd ever worn girls' clothes. "No of course not!" I said with a defensive look. He smiled and told me it wouldn't be weird if I did. He said a lot of guys cross-dress, especially ones with my 'body type'. Something about tiny guys being able to naturally fit in women's' clothes. I hung my head and stared at the floor. I felt really self-conscious and embarrassed of my size. He looked down at me sympathetically and felt a need to make a kind gesture.
"You know, my daughter doesn't want these clothes anymore. They're just going to be sitting in storage collecting dust. Seems like a waste of some nice stuff. Why don't you go through them and see if there's anything you'd like to keep?"
I looked up at him waiting for him to chuckle or hint that he was just messing with me, but his face was totally sincere. He was really offering me boxes of hand-me-down girls' clothes as if he believed this was something I needed in my life. I was stunned. My heart was pounding and I honestly couldn't tell if I was mortified or overjoyed.
"But I don't wear girl's clothes" I declared sheepishly.
He replied "How do you know if you've never tried?". He seemed really confident I was missing out on something important. As if this was some type of rite-of-passage for boys.
I chuckled awkwardly and said "maybe later?" hoping to end the conversation for now.
"Why wait?" he said cheerfully. "We don't have any plans tonight anyway and the curiosity is killing me now haha. Come on upstairs. Tonight you're playing dress-up"
He didn't leave me any chance to say no, with box of underwear under one arm, he took me by the hand and pulled me upstairs into the spare room where the rest of the boxes were. He set the box of bras and panties down in front of me and told me to go ahead and pick out a set to try on while he dug out some outfits from the other boxes for me. Wanting to be a good sport for my landlord, I knelt down and started fishing through the girly undergarments for something resembling my normal underwear. To my relief I found a plain black pair of boy-shorts. I pulled them out and presented them to Bob. He held them out in front of my hips, revealing that they were far too big for my frame.
"Oops. Those must have been from her old boyfriend or something. Sorry about that." He reached down and picked up the matching pink and white lacy set that had been on top of the pile. "Here, lets try these" he said as he handed them to me. I accepted, simply hoping to move on from this embarrassing interaction. He reached into another box and pulled out a short pink miniskirt and some white thigh socks. From another box he produced a small black T shirt. "Okay I'll let you get changed and we'll see how everything fits you."
I opened my mouth to ask "do I have to?" but he had already left the room and shut the door behind him - leaving me in the room with all the girly clothes. I took a deep breath and removed my normal clothes, tossing them in the corner. My naked skin felt very exposed, and I was eager to be clothed again. I gingerly unfurled the underwear he had chosen for me. It felt smooth on my fingers and some part of me was excited at the thought of putting it on. I realized this particular pair of panties was a thong! I'd never worn a thong before - it seemed so humiliating to wear underwear that is constantly giving you a wedgie. I looked at the box of underwear on the floor and thought about switching this pair for another. But then I'd have to explain to bob why I chose a different pair over the one he picked out for me. I didn't want to seem disrespectful to him in any way, so I bent down and stepped into the smooth, lace-trimmed panties. I shivered as I pulled them up my legs and up over my hips. The thong slid into my butt crack, making me feel violated, but a bit sexy. To my surprise, my smooth little cock and balls were actually contained quite nicely in the stretchy fabric, though there was a visible bulge. The tight delicate hug of the girly underwear on my private zones felt highly erotic and I could feel my heart start to race. I ran my fingers over my pink shiny bulge, and the touch felt electric, blissful even. Wearing panties was giving me sexual pleasure.
Before I got too carried away, I remembered Bob was outside the door and could barge in any second and catch me touching myself in girls' underwear. I hurried to get dressed. I fumbled a bit with putting the bra on but after a couple minutes I got it. I threw the little black T shirt on and pulled the miniskirt up my legs and over my hips. It didn't cover me as much as I would have liked, but once I put on the long white socks my legs were mostly covered at least. There was still a thin exposed section of my upper thighs between where the socks ended and the skirt started, as well as a patch of my belly that the shirt didn't cover. I wasn't used to being so scantily clad, but I'd seen girls dress a similar way in public so I decided this was acceptable behind closed doors. I was as dressed as I was going to get - unless I wanted to go through all the boxes and find more things to wear, which I did not (although I can't honestly say that I wasn't a little curious to eventually see what other outfits I had access to).
I opened the door to find bob waiting patiently in the hallway.
"Let me guess" he said "Getting the bra on was a bit tricky for you haha"
"hehe yeah" I confirmed.
"Everything else go smoothly? Do those panties fit you?"
"Yeah I think so... I guess its hard to tell because I've never worn anything like these before..."
"Oh well come here and let me see." He beckoned me as he crouched down to have a better view of my hip-line. I compliantly stepped closer to him. Normally I would be mortified for some guy to see me wearing a skirt, but for some reason with Bob I couldn't help but want to know what he thought of my appearance. I wanted his validation. I stood right in front of him with my hands folded modestly in front of my skirt. He took my little hands with his big strong ones and moved them out of the way, placing them on my hips instead. "Keep these up here" he instructed in his naturally deep voice. I froze in place, posed like a coy little doll. I enjoyed this... I enjoyed following his instructions. He slid his hands down to the bottom edge of my skirt. "Let's take a look" he muttered under his breath before lifting the whole front of my skirt, revealing my little pink lacy bulge. My heart raced. I was so vulnerable right now, but somehow I knew I was safe with this man. I submitted myself to his gaze, hoping that he would approve. "That looks great" he said, bringing me relief and pride. "Now let's see the back" he said as he took me by the hips and physically turned me around. His big hands manipulated my body so efficiently and naturally, I didn't even move my hands from where he had placed them. I was now standing with my back to him, hands on my hips, posed like a doll, staring blankly at the wall, obediently awaiting his next move. I felt his hands slide along the sides of my butt down to the bottom of the skirt. It hit me suddenly that he was about to lift the skirt and see my mostly-exposed ass in a thong. The feeling of nervousness hit me immediately as I felt the skirt brush my cheeks on its way up, followed by the cool air on my skin. I froze in place and swallowed hard. I knew that bob was getting an up close look at most of my ass. Did he know he gave me a thong to put on? Would he be surprised? Would he scold me for being indecent? I closed my eyes and braced for humiliation.
"Yeah that looks great on you. How do you feel?"
I practically gasped a sigh of relief.
I wasn't fully sure how I felt. There was some fear and shame, counteracted by the deep trust I had for Bob. There also excitement at the novelty, mixed with a lingering hint of arousal. I was a cocktail of nervousness, anxiety, and utter glee. The only thing keeping me grounded was Bob's calm and authoritative demeanor. Being around him made me feel safe to try new things that would otherwise be unthinkable. But I didn't want to say all that out loud, so I settled on:
"Ummmmmm a bit weird I guess?"
"Weird how?" He inquired, as he let my skirt fall back down and began lightly stroking my hips and thighs. The gentle massaging made me feel comforted. This was really happening, and I was totally safe. I let my guard down and elaborated on my answer.
"Well on one hand it feels kind of good... like fun and exciting you know? Almost like an adventure.."
"And on the other hand?" he coaxed me to continue, still running his hands along my body.
"I guess on the other hand I feel ashamed or humiliated or something... Boys aren't supposed to wear this stuff, know what I mean?"
"Yes I do know what you mean. Society has taught you from a young age that you are supposed to dress a certain way, act a certain way. And that doing anything different makes you some sort of failure right?"
"Right!" I concurred. He hit the nail on the head.
"Tell me, do you feel like you've always had a hard time meeting societies standards for manhood?"
I nodded silently, now feeling emotionally vulnerable to him as well as physically. It felt good to finally get it off my chest. He must have sensed my need for comfort because he wrapped his arms around me and held me in a gentle bear hug from behind. Kneeling down, he was about the same height as me standing. I was amazed how much his embrace calmed me down.
"Do you sometimes wish there was some way to escape all the pressure? Wish someone would come along and free you from the restrictive role of masculinity?"
"That sounds nice" I whispered.
"Good" he said. His left arm still holding me, his right hand began to migrate all over my body, caressing my belly, my chest, my hips. His touch was soothing, but also a tiny bit 'charged'. I felt myself letting go of my autonomy, drifting into the peace of his control. I gave up my personal sense of balance and leaned back into him, allowing him to hold me up. It felt like a great burden was being lift from my feeble shoulders.
"Listen to me. I can relieve you from all that shame and disappointment. This house can be a haven to be your true self. But you'll have to trust me and do everything I say. Do you want that?" I felt his hand slide down my belly and over the front of my skirt before slipping under and climbing back up to the bulge of my panties. I didn't try to move away or stop him. I was totally passive and compliant. Its like I was hypnotized.
"yessss" I whispered as my eyes gently closed. He caressed the bugle of my panties while slightly tightening his grip around my torso and arms. I squirmed against him - not to escape - but to feel his control even more. I felt helpless but safe, and that was a very exciting feeling.
"Good. I'm going to help you break free from your old insecure self. I'm going to teach you how to stop trying to be masculine. You won't have to worry about making any decisions about how to dress or act. I'll to decide everything for you. You won't have any control at all. You won't have to feel responsible for anything you do, because it's not up to you. I will be in charge of you, and we won't stop until we both know what kind of person you really are. Does that sound fun?" His fingers now crept down passed my bulge and between my thighs, finding their way into my butt-crack. With his palm still massaging my crotch, the tip of his middle finger followed the thong to my anus, which began gently massaging. The more I squirmed, the tighter he held me. I knew I had no control at all. He had absolute power and there was nothing I could do. In that moment, I felt the sweet freedom of submission. There was nothing I could do, and so nothing could possibly be my fault. I didn't have to 'try'. All I had to do was give in and let him do the rest.
"yes" I whispered again through shallow ecstatic breaths.
I moved into my new place in late October. The Landlord Bob was in his late 40s, 6'4", with a stocky build around 225 lbs. I on the other hand was 23, 5'6', and a very slender 125 lbs. Needless to say he towered over me, but he seemed very nice and likable. I felt comfortable around him, and as I got to know him, I quickly began to trust and respect him. He had the friendly demeanor of a good pediatrician with the charisma and leadership of a football coach. A very manly man, but not in a violent or threatening way. He and his wife had divorced several years ago, and his daughter had just gone off to college that fall. Naturally, he decided to rent out the unoccupied rooms in his house for some extra income and to keep from becoming isolated.
A couple days after arriving, I noticed I hadn't seen any trace of other roommates. I asked Bob about it, and he informed me the two tenants he was expecting had changed their plans last minute. So until he found new tenants to move in, it would be just he and I. Because I didn't know anyone in town, Bob and I ended up hanging out a lot. We would mostly just sit around and watch TV. We took turns cooking dinner. A couple times we even went out to the movies together. We must have looked like an odd pair when we went out in public - a large imposing man and his meek little sidekick. We joked that he could hide me in his backpack so we'd only have to pay for one movie ticket. I was just a little fairy of a boy compared to him, but I felt safe with him towering over me. I began to really trust and look up to him. I would confide in him about my inner thoughts - my insecurities, fear of failure and inadequacy, my difficulties attracting women. He always had something kind and reassuring to say. He was so calm and confident, and I had pretty low self-esteem. I found myself really depending on his validation. I'd find myself just following him around the house sometimes. He didn't seem to mind the attention.
One evening I noticed him moving some boxes from one of the spare rooms into the basement. I asked him what they were and he explained that his daughter had left a bunch of old clothes behind, and he was just moving them into storage. He made a joke that she was about my size, so her clothes would probably fit me. I laughed uncomfortably as I peaked into the open box he was holding. It appeared to be mostly filled with bras and panties of varying styles and colors. I could see a matching set that were satiny pink with white lacy trim. I felt a quiet surge of excitement at the sight. He interrupted my gaze and asked me point blank if I'd ever worn girls' clothes. "No of course not!" I said with a defensive look. He smiled and told me it wouldn't be weird if I did. He said a lot of guys cross-dress, especially ones with my 'body type'. Something about tiny guys being able to naturally fit in women's' clothes. I hung my head and stared at the floor. I felt really self-conscious and embarrassed of my size. He looked down at me sympathetically and felt a need to make a kind gesture.
"You know, my daughter doesn't want these clothes anymore. They're just going to be sitting in storage collecting dust. Seems like a waste of some nice stuff. Why don't you go through them and see if there's anything you'd like to keep?"
I looked up at him waiting for him to chuckle or hint that he was just messing with me, but his face was totally sincere. He was really offering me boxes of hand-me-down girls' clothes as if he believed this was something I needed in my life. I was stunned. My heart was pounding and I honestly couldn't tell if I was mortified or overjoyed.
"But I don't wear girl's clothes" I declared sheepishly.
He replied "How do you know if you've never tried?". He seemed really confident I was missing out on something important. As if this was some type of rite-of-passage for boys.
I chuckled awkwardly and said "maybe later?" hoping to end the conversation for now.
"Why wait?" he said cheerfully. "We don't have any plans tonight anyway and the curiosity is killing me now haha. Come on upstairs. Tonight you're playing dress-up"
He didn't leave me any chance to say no, with box of underwear under one arm, he took me by the hand and pulled me upstairs into the spare room where the rest of the boxes were. He set the box of bras and panties down in front of me and told me to go ahead and pick out a set to try on while he dug out some outfits from the other boxes for me. Wanting to be a good sport for my landlord, I knelt down and started fishing through the girly undergarments for something resembling my normal underwear. To my relief I found a plain black pair of boy-shorts. I pulled them out and presented them to Bob. He held them out in front of my hips, revealing that they were far too big for my frame.
"Oops. Those must have been from her old boyfriend or something. Sorry about that." He reached down and picked up the matching pink and white lacy set that had been on top of the pile. "Here, lets try these" he said as he handed them to me. I accepted, simply hoping to move on from this embarrassing interaction. He reached into another box and pulled out a short pink miniskirt and some white thigh socks. From another box he produced a small black T shirt. "Okay I'll let you get changed and we'll see how everything fits you."
I opened my mouth to ask "do I have to?" but he had already left the room and shut the door behind him - leaving me in the room with all the girly clothes. I took a deep breath and removed my normal clothes, tossing them in the corner. My naked skin felt very exposed, and I was eager to be clothed again. I gingerly unfurled the underwear he had chosen for me. It felt smooth on my fingers and some part of me was excited at the thought of putting it on. I realized this particular pair of panties was a thong! I'd never worn a thong before - it seemed so humiliating to wear underwear that is constantly giving you a wedgie. I looked at the box of underwear on the floor and thought about switching this pair for another. But then I'd have to explain to bob why I chose a different pair over the one he picked out for me. I didn't want to seem disrespectful to him in any way, so I bent down and stepped into the smooth, lace-trimmed panties. I shivered as I pulled them up my legs and up over my hips. The thong slid into my butt crack, making me feel violated, but a bit sexy. To my surprise, my smooth little cock and balls were actually contained quite nicely in the stretchy fabric, though there was a visible bulge. The tight delicate hug of the girly underwear on my private zones felt highly erotic and I could feel my heart start to race. I ran my fingers over my pink shiny bulge, and the touch felt electric, blissful even. Wearing panties was giving me sexual pleasure.
Before I got too carried away, I remembered Bob was outside the door and could barge in any second and catch me touching myself in girls' underwear. I hurried to get dressed. I fumbled a bit with putting the bra on but after a couple minutes I got it. I threw the little black T shirt on and pulled the miniskirt up my legs and over my hips. It didn't cover me as much as I would have liked, but once I put on the long white socks my legs were mostly covered at least. There was still a thin exposed section of my upper thighs between where the socks ended and the skirt started, as well as a patch of my belly that the shirt didn't cover. I wasn't used to being so scantily clad, but I'd seen girls dress a similar way in public so I decided this was acceptable behind closed doors. I was as dressed as I was going to get - unless I wanted to go through all the boxes and find more things to wear, which I did not (although I can't honestly say that I wasn't a little curious to eventually see what other outfits I had access to).
I opened the door to find bob waiting patiently in the hallway.
"Let me guess" he said "Getting the bra on was a bit tricky for you haha"
"hehe yeah" I confirmed.
"Everything else go smoothly? Do those panties fit you?"
"Yeah I think so... I guess its hard to tell because I've never worn anything like these before..."
"Oh well come here and let me see." He beckoned me as he crouched down to have a better view of my hip-line. I compliantly stepped closer to him. Normally I would be mortified for some guy to see me wearing a skirt, but for some reason with Bob I couldn't help but want to know what he thought of my appearance. I wanted his validation. I stood right in front of him with my hands folded modestly in front of my skirt. He took my little hands with his big strong ones and moved them out of the way, placing them on my hips instead. "Keep these up here" he instructed in his naturally deep voice. I froze in place, posed like a coy little doll. I enjoyed this... I enjoyed following his instructions. He slid his hands down to the bottom edge of my skirt. "Let's take a look" he muttered under his breath before lifting the whole front of my skirt, revealing my little pink lacy bulge. My heart raced. I was so vulnerable right now, but somehow I knew I was safe with this man. I submitted myself to his gaze, hoping that he would approve. "That looks great" he said, bringing me relief and pride. "Now let's see the back" he said as he took me by the hips and physically turned me around. His big hands manipulated my body so efficiently and naturally, I didn't even move my hands from where he had placed them. I was now standing with my back to him, hands on my hips, posed like a doll, staring blankly at the wall, obediently awaiting his next move. I felt his hands slide along the sides of my butt down to the bottom of the skirt. It hit me suddenly that he was about to lift the skirt and see my mostly-exposed ass in a thong. The feeling of nervousness hit me immediately as I felt the skirt brush my cheeks on its way up, followed by the cool air on my skin. I froze in place and swallowed hard. I knew that bob was getting an up close look at most of my ass. Did he know he gave me a thong to put on? Would he be surprised? Would he scold me for being indecent? I closed my eyes and braced for humiliation.
"Yeah that looks great on you. How do you feel?"
I practically gasped a sigh of relief.
I wasn't fully sure how I felt. There was some fear and shame, counteracted by the deep trust I had for Bob. There also excitement at the novelty, mixed with a lingering hint of arousal. I was a cocktail of nervousness, anxiety, and utter glee. The only thing keeping me grounded was Bob's calm and authoritative demeanor. Being around him made me feel safe to try new things that would otherwise be unthinkable. But I didn't want to say all that out loud, so I settled on:
"Ummmmmm a bit weird I guess?"
"Weird how?" He inquired, as he let my skirt fall back down and began lightly stroking my hips and thighs. The gentle massaging made me feel comforted. This was really happening, and I was totally safe. I let my guard down and elaborated on my answer.
"Well on one hand it feels kind of good... like fun and exciting you know? Almost like an adventure.."
"And on the other hand?" he coaxed me to continue, still running his hands along my body.
"I guess on the other hand I feel ashamed or humiliated or something... Boys aren't supposed to wear this stuff, know what I mean?"
"Yes I do know what you mean. Society has taught you from a young age that you are supposed to dress a certain way, act a certain way. And that doing anything different makes you some sort of failure right?"
"Right!" I concurred. He hit the nail on the head.
"Tell me, do you feel like you've always had a hard time meeting societies standards for manhood?"
I nodded silently, now feeling emotionally vulnerable to him as well as physically. It felt good to finally get it off my chest. He must have sensed my need for comfort because he wrapped his arms around me and held me in a gentle bear hug from behind. Kneeling down, he was about the same height as me standing. I was amazed how much his embrace calmed me down.
"Do you sometimes wish there was some way to escape all the pressure? Wish someone would come along and free you from the restrictive role of masculinity?"
"That sounds nice" I whispered.
"Good" he said. His left arm still holding me, his right hand began to migrate all over my body, caressing my belly, my chest, my hips. His touch was soothing, but also a tiny bit 'charged'. I felt myself letting go of my autonomy, drifting into the peace of his control. I gave up my personal sense of balance and leaned back into him, allowing him to hold me up. It felt like a great burden was being lift from my feeble shoulders.
"Listen to me. I can relieve you from all that shame and disappointment. This house can be a haven to be your true self. But you'll have to trust me and do everything I say. Do you want that?" I felt his hand slide down my belly and over the front of my skirt before slipping under and climbing back up to the bulge of my panties. I didn't try to move away or stop him. I was totally passive and compliant. Its like I was hypnotized.
"yessss" I whispered as my eyes gently closed. He caressed the bugle of my panties while slightly tightening his grip around my torso and arms. I squirmed against him - not to escape - but to feel his control even more. I felt helpless but safe, and that was a very exciting feeling.
"Good. I'm going to help you break free from your old insecure self. I'm going to teach you how to stop trying to be masculine. You won't have to worry about making any decisions about how to dress or act. I'll to decide everything for you. You won't have any control at all. You won't have to feel responsible for anything you do, because it's not up to you. I will be in charge of you, and we won't stop until we both know what kind of person you really are. Does that sound fun?" His fingers now crept down passed my bulge and between my thighs, finding their way into my butt-crack. With his palm still massaging my crotch, the tip of his middle finger followed the thong to my anus, which began gently massaging. The more I squirmed, the tighter he held me. I knew I had no control at all. He had absolute power and there was nothing I could do. In that moment, I felt the sweet freedom of submission. There was nothing I could do, and so nothing could possibly be my fault. I didn't have to 'try'. All I had to do was give in and let him do the rest.
"yes" I whispered again through shallow ecstatic breaths.
5年前
