First time being a sub to a woman [MF]

Meeting Heather was just like meeting anyone else at a Meet Up type group. Except for this was a Munch and she was a little over 20 years my senior. Being 23 and talking to a 45 year old knock out about kink, fetishes, and sex was a new experience for me. I wasn’t used to talking to adults like adults, and having them treat me the same. It was a little odd with the age difference, but that was what also made it exciting.

Life was going well for me. I was going to community college, working a day job, and my social life was in transition and changing. So like any other horny as fuck 23 year old man I fell down a rabbit hole and decided to seek out others to find out if I’d be into kink. Now I’d done some experimenting a couple of years before with an older male friend, but no one in the area or outside of that room knew. So, when Heather pulled me aside after chatting in groups the last few Munches I figured it was good sign.

Now Heather was a knockout. 45 and didn’t look a day over 32, pale skin, wavy chestnut hair down to the middle of her back, 38 F breasts, a nice ass, all in a 5’4″ frame. She had a couple of kids who were grown and moved away already, was divorced, and ran her own business. This threw me a bit for a loop as I didn’t seem to be her type. I had pale skin, blond hair, blue eyes, shaved face, all in a 5’10” scrawny frame.

Yet Heather wanting to talk to me exclusively was a very good sign, but not in the way I thought. See I was looking to Top or Dom women. It was what I was there to figure out how to do without being a dick. However, Heather was experienced and smart enough to know what I was into just from a handful of conversations. So, when she asked if I’d be interested in a scene with her at her place I got really excited. Then I was confused excited when she wanted to talk about a D/s scene with me where I’d submit to her. Needless to say this was the opposite of what I was looking for. Yet for some reason I wasn’t ready to admit to myself yet I was interested.

For the next couple of hours we chatting about a lot of things. Mostly what we’d want to do with one another with me as her sub. I wasn’t experienced enough to know she was feeling me out, in a BDSM D/s kind of way. As the night was winding down and we were going to have to part ways (the venue was closing) she asked me to walk me to her car. So, excited and a little confused I did. At her car she reiterated all the things we discussed, what limits there were, and what things we both wanted to try doing the most with each other. It was a verbal contract of scene agreement. Before she hopped into her car she asked me if I agreed. Seeing as how it wasn’t too out there I did, and the possibility of having sex with her was on the table, I agreed. The smile on her face was glowing. We exchanged phone numbers, I waved her goodbye, walked to my car, and drove home.

That was Tuesday. I looked at my phone a lot more than I thought I would wondering if Heather would call or text me. By Wednesday night I was playing computer games with my phone behind me just trying to not constantly look at and go crazy. On Thursday I woke up late morning and looked at my phone. No notifications. So, I got ready for the day and dropped the idea of Heather and I having a scene. A few hours after that Heather texted me.

*Hey [NAME]! Hope you’re doing well. Took me awhile to get some time this weekend cleared. Saturday from 10am to Sunday 10am. If you still want to have the scene about some (or all) of the things we discussed please let me know no later than Friday EOD.*

Blood flowed straight to my crotch and it took more willpower than I’m comfortable admitting to put the phone down and walk away. I calmed down but was excited! I was able to wait a couple of hours before replying to her and agreeing. Heather texted back soon after with her address with some instructions.

*Wonderful! Here is my address [INSERT ADDRESS]. Be here at 10am sharp. No earlier or later.*

*Also, arrive with your face, cock, and balls fully shaven. I’ll be inspecting.*

My body shivered a bit at the control she already had over me. Yet now I had a new problem. What the fuck was I going to do to fill the time until I was to meet Heather at her place?! I filled it with work, video games, and shaving like she asked on Friday night. With a touch up right before I head out to meet her.

As I drove to Heather’s house my mind couldn’t focus on one thing. Arriving at her place I double and triple checked the address and the time. I was 5 minutes early and fiddled on my phone in my car parked outside her house for a few minutes until I walked to her front door. At exactly 10am I rang the doorbell. My mind blank, my heart pounding, and my emotions all over the place making me feel a little queasy. Most of that went away when Heather opened the door. Her chestnut hair was up in a bun, she was wearing a button up white blouse which barely contained her, a black pencil skirt, black stockings, black flats, and a black bra. Her smile was wide and excited as she greeted me. “Hi [NAME]! Glad you could make it. Ready to do as I say the moment you come inside until the moment you leave?” The question hung in the air for probably a few seconds, but it felt like a minute to me, “Yes, I am.” The smile I flashed her was half excitement, half uncertainty.

Heather stepped to the side and told me to come in. I stepped through the threshold, stopped, and she closed the door behind me. Walking in front of me she told me to follow. I did and just as I was about to get to the carpet from the tile Heather tells me to stop. “From this point forward you will call me Mistress, and you will do what I tell you to. As we agreed the Red, Yellow, Green system is what we will use. Red means stop, Yellow means pause and talk, and Green means keep going. Agreed?” I eagerly nodded my head yes and said ‘Agreed’. Her green eyes became devilish as she gave me my first command. “Good, now strip naked. I want to see if you followed my instructions.”

My heart started pounding again, my mouth went dry, but before I got too queasy I started to strip. Within a moment or two my clothes were in a neat pile over my shoes against the wall by the end table (the kind you put your keys and purse on when you walk through the door) against the wall. Heather looked at me like prey. “I’m going to touch you now. Follow my commands when given. I’ll go slow to start okay?” I nodded and said, “Yes, Heather… I mean Mistress!”. She giggled to this and told me to spread my feet to be equal with my shoulders. Heather started by touching my face. “Good, nice and smooth.” Her eyes kept looking me over and I did my best to not lose my composure. Heather walked behind me and groped my ass. “Hmm, nice and firm!” Then I felt two of her fingers feel my hole. “And tight too!” The way she said this was praising and mocking at the same time. I tried to not like it as much as I did. Walking fully around me she looks me in the eyes and grabs my junk. Fondling me in her hands she smile. “It seems you can follow a direction. Very smooth.” The grunting giggle was unexpected but hot. “You’ve got a nice cock, and full balls! You didn’t jerk off did you?” She held my balls firmly in her hand gently squeezing. Trying to not wince I answered, “Yes, Mistress. I couldn’t finish for some reason.” Which was true. I tried to jerk off to get some release but this just turned into edging which I stopped the day prior. “Good to know.” she pursed her lips as she let go of me and looked me over. I stood there naked and inspected like meat for her next instruction.”

“Get on your knees, spread your legs open, and put your hands on your thighs.” I paused for a moment as the realization this was happening slowly started to hit me. On the cold hard tile I got on my knees as she told me to. I looked up at her as she smiled. Then she walked away from me. I was confused as I watched her. Heather went to the table in the corner between the two couches in her living room and pulled out from the drawer a black leather collar with a silver ring. Walking back to me she commanded me to lower my head and expose my neck to her. It wasn’t long before the cool black leather wrapped around my neck. The buckle going tight with enough room to be comfortable, and the excess of the strap secured in the loop. I had a slight shiver run through me as I accepted I would be the submissive for her today. Then I heard it, a small padlock click closed. “There, now you’ll get it off when I think you’ve earned it, we run out of time, or you Red Light and want to be done.” The shiver then included a bit of dread. Heather stood in front of me, cocked her head as I looked up at her, and then walked across the living room to sit on her couch. Silence was in the room for a few moments.

“Come over here and rub my feet.” I begin to stand but don’t even get off my knees before being corrected. “No no. On your hands and knees. Like a good sub boy.” The smile was inviting and chastising at the same time. I got on my hands and knees and crawled over to her. Once in front of her at her feet I returned to my knees. She put one of her feet in front of me and wiggled it. “This one first.” I looked down and saw her flats were still on. It took me a few seconds to think before I realized what she wanted me to do. I gingerly removed her flat, placed it gently to the side, and slowly started to rub her feet. They were warm, but not sweaty thankfully. As I rubbed Heather told me to either go harder, softer, move to another part of her foot, and so on. As I looked up at her to see if I was doing a good job I’d see her head back, and small moans and grunts of pleasure and relaxation come from her. Once the first foot was done she told me to put her flat back on and do the other. I was probably rubbing her feet for an hour or so before she was done.

As I put her flat back on her foot I could tell I was in a sub space of sorts. It was fragile, but I could easily slip deeper. The next thing Heather commanded pushed me deeper. “That was lovely pet. I’ll have to tell all our friends at the Munch how good you are at rubbing feet.” The tease of the threat of discretion being broken was hot and scary at the same time. I trusted her not to, but in my current state could not focus on that. “Now, I have a surprise for you. Turn around and get on your hands and knees. I don’t want you to see it just yet.” Doing as I was told I got on my hands and knees and crawled away from her just enough to be where I was just backwards. I heard Heather go into her table and pull out some items. “I think you’ll enjoy this. Besides I know you’re into anal stuff.” Heather giggled like only a woman in charge could. Before I had the moment to realize what she might have had planned the giggle stopped and another command was given. “Face down, ass up.” Reluctantly I agreed wondering if I wanted to say Yellow or Red. As I chewed on that though I felt lube on my ass and something squishy but hard pressing against my hole. I was too far down into sub space to keep the noises I made in check. Part of me thinks Heather teased me with the plug a bit because of that. Yet in what seemed like no time at all my ass was filled with a black spade silicone butt plug. I felt my ass close around it until the circle base kept it in place.

“I love when my subs are plugged and filled.” The giggle that accompanied this statement was humiliating in all the best ways. Heather then told me to stand up, walk around a bit, squat, and sit down. All the while asking if the plug felt comfortable. It did, but is also was pressing my prostate lightly which kept me *just* on edge. Heather then told me to lie on the ground, hands behind my head, and legs spread. I stayed there for a moment, getting comfortable, and trying to control myself. The best I could figure Heather realized this. “I’ll be right back. I have a toy I want to use on you!” With that she got up and went down the hall, probably to her bedroom. What felt like five minutes later Heather walked back into the room, past me, into the kitchen, to the freezer, and returned with the toy and a ziplock bag filled with crushed ice. Looking up and down at her she grinned more than she had that day.

My eyes caught the toy and the ice and I looked at Heather confused. Before I could speak she told me what she was going to do. “I think you’ll really enjoy this. You’ve been so good at following directions and doing what you’re told… I just want your focus to be on *my* pleasure.” With that she tapped my thighs to tell me to open them. I did and she got on her knees in between my legs. Ice pack to my left, and toy in her hands. “Ready to be locked up?” I nodded yes. Inside I was conflicted. Heather *really* liked control. I *really* liked to give up control. Yet I had no idea what chastity would be like. Never gave it a thought until she mentioned it. Those thoughts left me as I felt the steel ring go around my cock and balls and nestle itself in place. Then I felt Heather put the cool steel cage around my cock. Not able to get it closed she took it off and grabbed the ice and wrapped it around my cock and balls. “You’re being difficult [NAME]. I’ll have to think of a punishment for you after this. Maybe more.” It was FREEZING (obviously), and it took all my self control to not move my hands from behind my head or close my legs. After a handful of tries my cock was in the cage, and the lock clicked close with an audible *click*.

“There, now you’re all locked up.” Heather giggled as she wiggled my cock and balls that were now caged. “You should see what you look like!” With that she stood up, offered me a hand, and lead me into her hallway to a full length mirror. I turned red when I saw myself. “Like what you see? I know I do.” Heather stood next to me as I took it all in. The collar with the ring, the cock cage, the butt plug, and how she was still fully clothed and I was naked except for the items she gave me. It was here she got excited and laid down the law. “Now if you want out of that cage you’ll do what I tell you to for the rest of the night.” She tilted her head down as she put the keys around her neck so it hung perfectly over her cleavage. “See I own your cock now, so I might as well own you.” She jiggled the cock cage again with a beaming smile. “But don’t worry I’ll let you out, and I’ll even let you cum!” She let that hang in the air for a moment. “You just need to do as you’re told.” The realization of how much power I had given to her hadn’t fully set in yet before she grabbed the ring on my collar. “Are you hungry? I’m hungry. Lunch time!”

Pulling me into the kitchen by my collar she dragged me to the dinning table, pulled out a chair, and told me to sit down. I tried to get comfortable, but the table looked right into her backyard. It was private, but with the drapes open if anyone went back there, they’d get a show. I could also feel my cock getting slightly hard because the plug was pushing against my prostate. It was enough to have me straining against the cage, but not enough to make it more than uncomfortable. Heather brought over some sandwiches and for the next couple of hours we talked. Making sure the whole time the shiny silver keys were promptly on display. Heather made sure I felt okay, reminded me about the Red, Yellow, Green system, asked how the plug felt, how the cage felt, what emotions I had going through me. It was right before I was commanded to clean the table when Heather asked a bombshell of a question for me.

“So, [NAME] I have a feeling about you and I want you to answer me honestly. Have you ever sucked another man’s cock?” I wanted *badly* to answer, yet I fumbled. I also didn’t want everyone to know. Heather realized this and added, “You know all that happens today, and has happened, is between us right? I won’t tell another soul.” She grabbed my thigh and squeezed reassuringly. I took a breath and relaxed. I felt safe with her, and trusted her more in that moment. “Yes, I have.” Heather looked like a young girl in a candy shop when I answered. “Now tell me all you’ve done with a man.” The authority creeping back, and her soft foot in stockings stroking my cock through the cage. I told her I had also had my ass fucked, and where he had cum. My cock straining against the cage as I answered. “You’re quite the cockwhore and cumslut aren’t you [NAME]?” At this point I was certain I couldn’t get more red than I was. “This gives me an idea, but for now clear the table.” Her foot left my caged cock, it was bittersweet, and I got up and cleared the table and cleaned like I was commanded.

I had been in the collar for almost 5 hours by this point, plugged for at least 3, and caged for roughly the same. I finished clearing and cleaning when I saw Heather stand. She had a stern, but playful look on her face. I had no idea what to expect. “Now, [NAME] you made things difficult for me earlier. For that I have a couple of punishments for you.” I stood in a bit of fear wondering what I had done to deserve a punishment, but it didn’t matter. I was her’s for the day. She could do whatever she wanted unless I said ‘Red’. Which I desperately didn’t want to do. I wanted to push myself. “Now, bend over the table, stretch out your arms, and spread your legs to the feet of the table.” I did as I was told not knowing what was about to happen. I felt the cool wood of the table against my skin, the cold tile on the bottom of my feet, and how exposed my caged cock and plugged ass were for her.

Leaving me exposed she went to a closet and grabbed something. My mind was swimming with what it could be. I didn’t have to wait too long to find out. She came back and showed me her wooden paddle. “I think 20 spankings aught to do it for being so difficult to get you into your cage.” The smile she had on her face was intoxicating. I didn’t want to get spanked, but I didn’t want to displease Heather more. Resigning myself to my fate she walked to the side and behind me. “Now, count them out as they land. Or we will start over.” A few seconds later the paddle smacked my ass. Not too hard, but not softly either. I counted as commanded. Heather made it a game to see how well she could hit the plug still in my ass. Every time she did the force of the spank went into me, and the plug rubbed my prostate just right. In turn my cock strained against its cage.

Red ass, a bit of a leaking cock, and a bunch of humiliation later we were done. I had made it and counted 20 spanks. Heather praised me on how good of a boy I was, how well I could take a beating, and how much that pleased her. I was happy to have endured it, but wouldn’t willingly go through it again. Heather put the paddle leaning up against the couch and told me to get on my knees in the same spot I had earlier. She wanted to test me with something. With that she left for her bedroom.

Sore, throbbing, and plugged I made my way back to in front of the couch and returned to my knees. Only this time my ass stung. I watched Heather come back from her bedroom and my eyes widened. Heather had taken off her skirt, was wearing black panties, but had a 7″ black strap on cock in a harness around her waist. “You like it?” she mocked me as she sat down on the couch in front of me. Leaning back with her ass forward and legs spread. “I really enjoyed you telling me all those things over lunch. Those things you said got my mind racing! Do you know what I want you to do?” She looked down at me, keys shining in her cleavage, hard ‘cock’ in hand, at my dumbfound face not knowing how to respond. Giggling she told me, “I want to see you suck cock, pet.” The shiver and queasy feeling returned for a moment. The next thing she said sealed the deal. “If you want out of that cage, you’ll show me how you suck cock.” The wicked control Heather had over me was intoxicating. It didn’t take me long to realize what I needed to do.

For what felt like an hour, but was probably shorter, I licked, kissed, sucked, and gagged on Heather’s “cock”. The whole time she teased me for how good I looked doing it, how well I was doing what she told me, and how I was probably a better cocksucker than she was. It was the best kind of humiliation I had up until then from a woman I have had. Yet it would take the evening of processing this to realize it. Yet once she felt I was pushing myself too hard, and I was as my jaw was getting sore, Heather told me to stop. Heather slipped out of the harness and put it next to her on the couch, cock facing up, and crossed her legs. “Ready to get out of that cage?” That made me very eager! Heather commanded me to return to the lying down position I was in earlier, got between my legs, and took my cock out of its cage. “Almost 5 hours. Not bad for a first time! We’ll have to try for longer next time.” Heather teased as she put the cage and key on the table between the couches.

My cock got rock hard and stayed that way. It felt so good to be out of the cage! It was obvious to Heather so she took control. “Do you want to cum before we finish our session today [NAME]?” It was said in such a lustful, kind, motherly way I felt my cock throb. “Yes, Mistress!” I probably answered too quickly, but could you blame me? “Good. Now stay there and stroke your cock for me. Stop when I tell you. And you had better **not** cum until I tell you! Understand pet?” I looked up at her, sitting on the couch, looking down at me, and answered “Yes, Mistress.” With that she edged me. Heather was an expert at it! I was so ready to burst, yet every time she could tell and had me stop. Sometimes for very long minutes until I could stroke again.

Then I saw that wicked smile return to her face. “Do you want to cum [NAME]?” Of course my answer was a panting and enthusiastic ‘Yes, Mistress!’. “Then hands off your cock.” Heather walked around me to stand over my head as I put my hands to my sides. My cock was ready to burst even without stimulation. I wasn’t sure how much longer I would last. “Legs up pet.” This threw me. “Wh…what Mistress?” I couldn’t see her face, but she said just as kindly, but more firmly, “Legs up pet.” I lifted my legs up in the air and she took them, bending me like a pretzel a bit, and making my cock dangle over my face. With one hand holding my legs in place, Heather’s other went and gently stroked my cock.

Heather’s hands felt amazing! But I only got a taste before she stopped. “Want me to keep going?” Nearly pleading I answered, “Yes, Mistress!!” She held my legs against her hips and reached for the plug. “Then you are going to do something for me.” I didn’t ask what. I didn’t have to. I moaned and gasped as the plug was tugged. “You are going to give yourself a facial for me.” My heart stopped. I was going to do what?! Not having time to think about it the plug was pulled slowly out of my ass. It felt wonderful to not be filled, but the feeling didn’t last long. I felt something similar but different fill my ass as it tried to close. Then I yelped as, what I found out later was, the prostate stimulator hit me just right. “How long did you say it had been since you came last?” Heather reached down and started to stroke my cock pointing it directly at my face. I was pinned and couldn’t escape. I wasn’t sure how much longer I was going to last. “Ab… about 4 days Mis…. Mistress…” I was trying to hold back but it was a losing battle. “Then let me see it. Let me see you pump that 4 day load all over your face.”

It didn’t take long after that. Her soft strokes, the pulsing of the toy against my prostate, and the drips falling around and on my face all told me what I was about to experience. A few moments later I felt my orgasm build, I couldn’t hold it off any longer, and came. Heather made sure that I was coating my face as much as possible. I tried to keep my mouth closed but failed so a bit of cum got into my mouth. Heather shook the last drop of cum out of my shrinking cock, took out the toy and turned it off, and gently put my legs back down on the floor. “You should see what you look like!” Heather laughed at my humiliation. “I’ll be right back, don’t move!” At this point Heather was very playful, and it seemed out of Mistress mode.

A moment later I heard a drawer open, a sink turn on and off, and Heather returned holding a wash cloth and a hand held mirror. “Open your eyes pet…” I did as best I could and saw myself. I was covered in my own cum. “If only I could show my friends! They’d never believe it!” The teasing and poking fun had begun. It was humiliating, but also extremely pleasurable for some reason. Heather then gently plopped the warm washcloth on my face. “Clean yourself up pet. We’re almost done for the day.” I cleaned my cum off my face, swallowed what little got in my mouth, and when I was finished told Heather I was done.

I was told to get back on my knees. I did so but with a speed that showed how tired I was. Heather walked behind me, unclasped the lock on the collar, and took it off. It felt weird to have it off. After all that to return to “normal” was a bit of a shock. “Okay time for after care! Come with me [NAME]. Let me give you a shower.”

Heather took me to her guest bathroom, started a shower for me, and had me hop in. “I’ll be right back.” I stood in the water, shower curtain closed, in that moment of privacy, reflecting on all that happened to me today. Heather came back a few moments later, announced herself, and then hopped into the shower with me. She wasn’t nude, but was wearing a very curve hugging blue with white polka dot bikini. For the next hour she bathed me, comforted me, asked me questions, listened to me, and ensured I was taken care of. It was some of the best aftercare I have had.

After we got out of the shower, she put on a robe, and I dried off with a towel. Clean and dry I walked down the hallway to my pile of clothes, got dressed, and realized with finality the scene was over. Heather and I hugged, she kissed my forehead, and we said our goodbyes for the night. I texted her like I was told I got home okay, and then I went to sleep earlier and long than I had in a long while.

The Munch the following Tuesday was the next time I saw her. Discretion was kept about *what* happened that day. But she did tell them I was a good sub, and if I wanted could be a great Dom. Everyone was nice about it, not judgmental, and a couple of the other older women expressed interest about having me have a scene with them too!

I met with Heather a handful of times over the next few of months. She pushed my boundaries and got me to do things I otherwise might not have enjoyed as much had she not been there.

Source: reddit.com/r/gonewildstories/comments/gq6akw/first_time_being_a_sub_to_a_woman_mf