Dylan's Training F/M
Posted: Tue Feb 25, 2025 8:44 pm
My name is Dylan, I'm 25, blonde, athletic. This is about something that happened with me two years ago, something I'll never forget.
I'd come home from college for summer to find that we had a new neighbor. My parents were talking about her over breakfast one day. She was about 40 they said, divorced and didn't have kids. Our neighborhood was a nice one with mostly old Victorian houses, not rich but definitely not the worst place to live. The one thing that made this woman stand out was the fact that she didn't have to work, unlike my parents and most of our neighbors. They weren't sure where she'd gotten her money, she wasn't from around here so the local gossip on her was still limited. Anyway I felt my parents were a little jealous. My mom had only spoken to her once, Susan was her name...the last name she couldn't remember.
The first time I got a glimpse of Susan, I was out mowing the lawn. It was hot and I had my shirt off, and I was wearing just a pair of shorts and my sneakers. She was sitting out on her veranda sipping iced tea. Even for a woman her age she was absolutely beautiful. Long brown hair pulled black, pink full lips, slim waist and flat stomach, dressed in a tiny white halter top and short shorts.
I tried not to stare and turned my gaze away. The next time I looked in her direction she was staring straight at me. She smiled..I blushed and waved. That was it. The next day Susan called my mom and asked if I wouldn't mind helping her move some boxes upstairs that she had yet to unpack, she'd pay of course. I was needless to say more than willing.
When I went to her house Susan answered the door wearing a flowered sun dress, very short. She was barefoot and her hair still wet from the shower. She smiled and invited me in.
"I'm sorry I'm such a mess! It's Dylan right?"
"Yes Ma'am, Dylan."
"Oh please don't call me that!" She looked a bit scornful. "Susan is fine, but please don't call me Susie, I never liked it."
"Ok, Susan, no problem."
"Such a good boy. So here are all the boxes, you can start carrying them up the stairs and put them in the first room to the left. I'll unpack them later."
I got to work while Susan went to the kitchen to make some iced tea. The house was hot with only window air conditioners in a couple rooms. I began to sweat as I carried the boxes.
Later Susan came upstairs with two glasses of iced tea and offered me one which I gladly took and began to chug. She leaned against the doorway, sipping her tea and watching me. A few drops dribbled down my chin and fell onto my T-shirt.
"Really Dylan, you're such a messy boy... you should be spanked!" She giggled and continued to sip.
I paused for a moment, a bit taken back by the comment, but very much aroused. She noticed it.
"You know I think you've done quite enough for today, why don't you go take a shower and then I'll make you something to eat."
"A shower?" I stammered.
"Yes of course, you don't think I'm going to send you home all sweaty and smelly do you? Now do as you're told and don't try to argue."
I liked this. It was something new for me, but being told what to do by an attractive woman was so erotic. I went to the bathroom and closed the door, undressed, and started to take a shower. While I was in there I heard the door open. The shower curtain was opaque but I could see from the light entering the room that the door remained open. I finished quickly and turned off the water.
"Susan?"
"It's alright Dylan, it's me. Now I want you to come out."
Cautiously I pulled back the shower curtain till I could see out. Susan was standing there looking completely different than before. Her hair was down, she had on red lipstick, and she was wearing nothing but a pair of nylons and garters, and stiletto heels. Her breasts were small but very beautiful in form, and I could just barely see her labia protruding from her pussy as she stood there with her legs spread. Her public hair was trimmed to a thin fine strip. Instantly I began to get hard.
"Pull back that curtain all the way."...I complied.
Glancing at my hardening cock she smiled and looked up at me. "You want this don't you Dylan?"
"Yeah, I ahh ..."
"Yes mistress."
"What?" I asked confused.
"If we're going to have this kind of relationship, then in private you will call me mistress. Is that understood Dylan?"
"Yeah ahh, yes mistress."
"Good boy, now come out of there."
Still embarrassed, I obeyed, my hard cock stuck out before me. When I approached her she ran her finger along the underside of it and smiled. "If you want it you're going to have to work for it... Now down on all fours, I want you to crawl for me."
I immediately dropped down and began to crawl behind her as she walked down the hallway. Looking up I admired her firm ass as she walked. She stopped in the hall and took a leash and collar from a table and bending down, fastened it around my neck. The leather was cold and unfamiliar against my skin.Taking the leash in her hand she led me into her bedroom and to a corner of her antique iron bed.
"First we need to teach you exactly your place. Hands on the bedpost!" As I gripped the post she took a pair of handcuffs from the dresser and cuffed my wrists, securing them to the bedpost. Then from the drawer she took an object which I knew of but had never seen in real life..a ball gag.
"Open up." As she held it in front of my mouth I hesitatingly opened my lips and the firm rubber ball was pressed between them and strapped into place. I felt oddly aroused and humiliated at the same time.
Then, taking a riding crop from the drawer, she began to spank me with it. First slapping one cheek, then the other, slowly at first, then quickly. Then she stopped slapping, and slowly caressed my ass with the crop, slowly down between my ass cheeks and over my scrotum, up and down. I arched my back, moving my butt closer to her touch. "Smack!" The crop again hit my ass.
"Did I tell you to move boy?"
"No mistress," I mumbled through the gag.
My punishment continued for some time, alternating between spanking and the light caress of the crop over my anus and genitals. My mistress reached underneath and stroked the crop along the length of my throbbing cock...I was in ecstasy... Suddenly I could hold it no longer, I tried to stop myself, but I came, my semen leaking from the end of my cock onto the carpet.
"Oh, look at the mess you've made you naughty boy!"..."Smack!" Again three times across my ass.
She then removed the gag and uncuffed me.
"Now, go to the bathroom, get a wet cloth, and clean up this mess and yourself... bring your clothes also but don't dress yet."
"Yes mistress." I replied.
Going to the bathroom I got a wet washcloth, cleaned the end of my cock, grabbed my clothes from the floor, and then returned to the bedroom. I knelt down naked and cleaned up the mess as best as I could. She stood there, still nearly nude in her stockings and heels, watching me.
When I was nearly done she came close to me, putting her pussy nearly against my face. "You want this don't you?"
"Yes mistress." I moaned and tried to rub my face between her legs. She stepped back.
"Let's make a deal... your mother told me that her and your father are planning a trip to the lake next weekend and that since you will be home all alone you will have plenty of time to help me, is that right?"
"Yes mistress, I'll be glad to do whatever you need."
"I'm sure you will pet. What I really need more than anything, is a servant boy to be completely at my bidding for the whole weekend. Do you consent to that?"
"Absolutely mistress!"
"Good."
Going to a drawer she pulled out a pair of black lace panties and threw them at me. I looked at her confusedly.
"Put them on boy, this is just one part of what you must get used to as my servant. The rest you'll find out next weekend. I stood up, and, picking the panties from the floor slipped them on. The silky material felt pleasant and unfamiliar against my skin.
"Now you may dress and wait for me in the kitchen. I'll be down shortly to fix you something to eat like I promised before."
I quickly threw on my shorts and T-shirt, and grabbed my sneakers from the bathroom floor as I went down to the kitchen. I sat at the table and waited until Susan came downstairs. And now she really was Susan again and not mistress. She was dressed in the same cute little sundress as before. I sat as she made me a sandwich and poured me another glass of iced tea. While I ate she sat and chatted with me about my studies as if nothing had happened, but the whole time I was thinking about everything and could feel her silky panties pressed tight against my cock and balls. It was so erotic!
I tried my best to shift my mind to other things so I wouldn't have a hard on when I got up. Finally I finished and it was time to leave. Susan walked me to the door, pressing her body against mine as I went to leave. She reached out and ran her fingers across the back of my neck as I passed.
"See you this weekend Dylan," she whispered in my ear as I passed. I got the tingles and my toes curled in my shoes, just thinking of what my mistress would do with me for two whole days.
.....Dylan went home and thought about everything that had occurred at Susan's. It was something he'd always dreamed about, and incredibly new and erotic. However, now that it had finally happened, he felt a bit disappointed. "Why am I feeling this way?" He thought. Then he realized something deep inside of himself. Though he'd always dreamt of being submissive to a woman in this way, in his mind there was always an undeniable spiritual and emotional connection between him and the other person. With Susan it wasn't so. She merely looked on him as an object to be played with for the time being, and to be thrown away when she was tired of him. He was not a human being with a soul to her, but merely an attractive body. Though it had been an interesting experience, something very erotic that he would never forget, he realized he wanted more from a relationship. Alone in his room, he took off his shorts, removed the panties and threw them in the trash. He put on a pair of boxers and climbed into bed.
Though he sometimes saw her in passing, Dylan never went to Susan's again.
I'd come home from college for summer to find that we had a new neighbor. My parents were talking about her over breakfast one day. She was about 40 they said, divorced and didn't have kids. Our neighborhood was a nice one with mostly old Victorian houses, not rich but definitely not the worst place to live. The one thing that made this woman stand out was the fact that she didn't have to work, unlike my parents and most of our neighbors. They weren't sure where she'd gotten her money, she wasn't from around here so the local gossip on her was still limited. Anyway I felt my parents were a little jealous. My mom had only spoken to her once, Susan was her name...the last name she couldn't remember.
The first time I got a glimpse of Susan, I was out mowing the lawn. It was hot and I had my shirt off, and I was wearing just a pair of shorts and my sneakers. She was sitting out on her veranda sipping iced tea. Even for a woman her age she was absolutely beautiful. Long brown hair pulled black, pink full lips, slim waist and flat stomach, dressed in a tiny white halter top and short shorts.
I tried not to stare and turned my gaze away. The next time I looked in her direction she was staring straight at me. She smiled..I blushed and waved. That was it. The next day Susan called my mom and asked if I wouldn't mind helping her move some boxes upstairs that she had yet to unpack, she'd pay of course. I was needless to say more than willing.
When I went to her house Susan answered the door wearing a flowered sun dress, very short. She was barefoot and her hair still wet from the shower. She smiled and invited me in.
"I'm sorry I'm such a mess! It's Dylan right?"
"Yes Ma'am, Dylan."
"Oh please don't call me that!" She looked a bit scornful. "Susan is fine, but please don't call me Susie, I never liked it."
"Ok, Susan, no problem."
"Such a good boy. So here are all the boxes, you can start carrying them up the stairs and put them in the first room to the left. I'll unpack them later."
I got to work while Susan went to the kitchen to make some iced tea. The house was hot with only window air conditioners in a couple rooms. I began to sweat as I carried the boxes.
Later Susan came upstairs with two glasses of iced tea and offered me one which I gladly took and began to chug. She leaned against the doorway, sipping her tea and watching me. A few drops dribbled down my chin and fell onto my T-shirt.
"Really Dylan, you're such a messy boy... you should be spanked!" She giggled and continued to sip.
I paused for a moment, a bit taken back by the comment, but very much aroused. She noticed it.
"You know I think you've done quite enough for today, why don't you go take a shower and then I'll make you something to eat."
"A shower?" I stammered.
"Yes of course, you don't think I'm going to send you home all sweaty and smelly do you? Now do as you're told and don't try to argue."
I liked this. It was something new for me, but being told what to do by an attractive woman was so erotic. I went to the bathroom and closed the door, undressed, and started to take a shower. While I was in there I heard the door open. The shower curtain was opaque but I could see from the light entering the room that the door remained open. I finished quickly and turned off the water.
"Susan?"
"It's alright Dylan, it's me. Now I want you to come out."
Cautiously I pulled back the shower curtain till I could see out. Susan was standing there looking completely different than before. Her hair was down, she had on red lipstick, and she was wearing nothing but a pair of nylons and garters, and stiletto heels. Her breasts were small but very beautiful in form, and I could just barely see her labia protruding from her pussy as she stood there with her legs spread. Her public hair was trimmed to a thin fine strip. Instantly I began to get hard.
"Pull back that curtain all the way."...I complied.
Glancing at my hardening cock she smiled and looked up at me. "You want this don't you Dylan?"
"Yeah, I ahh ..."
"Yes mistress."
"What?" I asked confused.
"If we're going to have this kind of relationship, then in private you will call me mistress. Is that understood Dylan?"
"Yeah ahh, yes mistress."
"Good boy, now come out of there."
Still embarrassed, I obeyed, my hard cock stuck out before me. When I approached her she ran her finger along the underside of it and smiled. "If you want it you're going to have to work for it... Now down on all fours, I want you to crawl for me."
I immediately dropped down and began to crawl behind her as she walked down the hallway. Looking up I admired her firm ass as she walked. She stopped in the hall and took a leash and collar from a table and bending down, fastened it around my neck. The leather was cold and unfamiliar against my skin.Taking the leash in her hand she led me into her bedroom and to a corner of her antique iron bed.
"First we need to teach you exactly your place. Hands on the bedpost!" As I gripped the post she took a pair of handcuffs from the dresser and cuffed my wrists, securing them to the bedpost. Then from the drawer she took an object which I knew of but had never seen in real life..a ball gag.
"Open up." As she held it in front of my mouth I hesitatingly opened my lips and the firm rubber ball was pressed between them and strapped into place. I felt oddly aroused and humiliated at the same time.
Then, taking a riding crop from the drawer, she began to spank me with it. First slapping one cheek, then the other, slowly at first, then quickly. Then she stopped slapping, and slowly caressed my ass with the crop, slowly down between my ass cheeks and over my scrotum, up and down. I arched my back, moving my butt closer to her touch. "Smack!" The crop again hit my ass.
"Did I tell you to move boy?"
"No mistress," I mumbled through the gag.
My punishment continued for some time, alternating between spanking and the light caress of the crop over my anus and genitals. My mistress reached underneath and stroked the crop along the length of my throbbing cock...I was in ecstasy... Suddenly I could hold it no longer, I tried to stop myself, but I came, my semen leaking from the end of my cock onto the carpet.
"Oh, look at the mess you've made you naughty boy!"..."Smack!" Again three times across my ass.
She then removed the gag and uncuffed me.
"Now, go to the bathroom, get a wet cloth, and clean up this mess and yourself... bring your clothes also but don't dress yet."
"Yes mistress." I replied.
Going to the bathroom I got a wet washcloth, cleaned the end of my cock, grabbed my clothes from the floor, and then returned to the bedroom. I knelt down naked and cleaned up the mess as best as I could. She stood there, still nearly nude in her stockings and heels, watching me.
When I was nearly done she came close to me, putting her pussy nearly against my face. "You want this don't you?"
"Yes mistress." I moaned and tried to rub my face between her legs. She stepped back.
"Let's make a deal... your mother told me that her and your father are planning a trip to the lake next weekend and that since you will be home all alone you will have plenty of time to help me, is that right?"
"Yes mistress, I'll be glad to do whatever you need."
"I'm sure you will pet. What I really need more than anything, is a servant boy to be completely at my bidding for the whole weekend. Do you consent to that?"
"Absolutely mistress!"
"Good."
Going to a drawer she pulled out a pair of black lace panties and threw them at me. I looked at her confusedly.
"Put them on boy, this is just one part of what you must get used to as my servant. The rest you'll find out next weekend. I stood up, and, picking the panties from the floor slipped them on. The silky material felt pleasant and unfamiliar against my skin.
"Now you may dress and wait for me in the kitchen. I'll be down shortly to fix you something to eat like I promised before."
I quickly threw on my shorts and T-shirt, and grabbed my sneakers from the bathroom floor as I went down to the kitchen. I sat at the table and waited until Susan came downstairs. And now she really was Susan again and not mistress. She was dressed in the same cute little sundress as before. I sat as she made me a sandwich and poured me another glass of iced tea. While I ate she sat and chatted with me about my studies as if nothing had happened, but the whole time I was thinking about everything and could feel her silky panties pressed tight against my cock and balls. It was so erotic!
I tried my best to shift my mind to other things so I wouldn't have a hard on when I got up. Finally I finished and it was time to leave. Susan walked me to the door, pressing her body against mine as I went to leave. She reached out and ran her fingers across the back of my neck as I passed.
"See you this weekend Dylan," she whispered in my ear as I passed. I got the tingles and my toes curled in my shoes, just thinking of what my mistress would do with me for two whole days.
.....Dylan went home and thought about everything that had occurred at Susan's. It was something he'd always dreamed about, and incredibly new and erotic. However, now that it had finally happened, he felt a bit disappointed. "Why am I feeling this way?" He thought. Then he realized something deep inside of himself. Though he'd always dreamt of being submissive to a woman in this way, in his mind there was always an undeniable spiritual and emotional connection between him and the other person. With Susan it wasn't so. She merely looked on him as an object to be played with for the time being, and to be thrown away when she was tired of him. He was not a human being with a soul to her, but merely an attractive body. Though it had been an interesting experience, something very erotic that he would never forget, he realized he wanted more from a relationship. Alone in his room, he took off his shorts, removed the panties and threw them in the trash. He put on a pair of boxers and climbed into bed.
Though he sometimes saw her in passing, Dylan never went to Susan's again.
but it was a fun little story that I thought could’ve went further