Rewind to back when I was eighteen, recently graduated and was in the midst of couch surfing after my mom gave me the ultimatum about living with her, which I immediately opted out of. After doing so, I spent a significant amount of time at my former gym teacher's house. I'll refer to her as Jenna; she was thirty at the time. She was a family friend, and when I asked if I could stay with her till I figured my shit out, she happily accepted. At the time, she was recently divorced after two years of marriage, so she had room to accommodate me. It felt weird at first to stay with her since I always saw her as my teacher, and interacting with her daily and building a friendship with her was very surreal. She also knew about my mother and was actually one of the few people who didn't end up judging the actions she took to raise my sisters and I.
Anyway, I had stayed with her for close to a month before this takes place, and we had been building a decent amount of trust with each other. She even gave me a key to the house. Around the same time, school had started back up, so I was left alone most of the day, which was fine. Not gonna lie; I'm pretty sure I had an orgasm on almost every surface in her house. However, during one of my raging horniness spells, my sexual curiosity got the better of me, and this wasn't by any means the first or last time. What sparked this, however, was during the night, our rooms were on different floors, but I could swear that I'd hear faint moaning echo through the floorboards. I never brought it up, but it did make my mind race which is how I ended up in her room, looking through her drawers, trying not to move anything out of place. I checked the bedside table prior, but there was nothing there. While going through her dresser drawers, it was pretty mild at first. She had simple bras, thongs, and boyshorts but nothing crazy. However, it wasn't until I got to the drawer closer to the floor that I realized what a kinky freak she was.
Inside was a lot of BDSM "equipment," from ball gags, handcuffs, and blindfolds, to things that actually needed to be assembled. There were also some floggers, and she had very good taste in lingerie, speaking from a VS sales associate perspective. However, the BDSM stuff was mainly in the back of the drawer, while in the front was a plastic bag with multiple vibrators in it. My heart started racing when I made this discovery, and I had never used a toy, but there was one in the bag that felt like it was calling my name. It was blue, almost sparkly, moulded like a penis, and quite thick. Losing all means of self-control, I took it out and was practically drooling at the sight of it. Feeling it, it was a firm silicone toy with a nice girth. I started jerking it off to get an idea of how much it could stretch me. Then delving too deep into my deviancy, I started licking the tip and then put it in my mouth before turning the knob on the base of it by accident. To my surprise, it immediately started vibrating. Now you may be thinking it's a vibrator; of course, it vibrates, but the thing is, in the plastic bag was a bunch of batteries, so I assumed this one was also empty. The fact it wasn't made me start to think that this was her go-to toy and the one that likely made her moan in the midnight hours.
Coming to this revelation made me want to try the toy even more, but having lost track of time, she was close to being home, and it was about to be the weekend, so I wouldn't get a chance till the coming Monday. After giving the toy a goodbye kiss on the tip, I put it back in the bag with the others and then tried to put everything away the way I found it and went about my business. That night though, I couldn't stop thinking about that toy. The fingers I had inside myself simply weren't cutting it, and I even attempted to fill myself with three, but I wanted to feel those vibrations. Having given up for the night, I laid there and just stared at the ceiling when I started to hear Jenna's moans again. They were faint, but she was definitely enjoying herself. Then I wondered if she was using the toy I had just given a blowjob to earlier, which made me drip. It didn't take me long to finish after that to finally cum, yet the curiosity remained.
Like a secret agent infiltrating a high-security base, I made my way to the upper floor. Her room was on the same floor as the kitchen, so it wasn't unusual for me to come up at night and get a snack, but being near her room down the hall was. I don't remember how I did it exactly to avoid the creaky floor from giving me away, but I do remember crouching down and almost tiger crawling quite a bit until I got there. The door to Jenna's room was ajar, and I did my best to peek around it, but I didn't have a clear line of sight. However, she was definitely moaning that not touching myself was a definite challenge I wasn't willing to attempt as I listened for a minute with my hand in my thong, drawing circles on my clit. Still, I was craving the visual, and with one hand occupied, I only had the other to slowly open the door a little while praying she didn't notice. It swung open enough that I could see her; she was face down, ass up and sure enough, using that blue vibrator on herself. Things started to make more sense once I saw this. She was using the pillow to muffle her moans. However, unlike her, I didn't have that luxury. My orgasm hit me spontaneously and made me lose control of my basic motor functions.
Overwhelmed with pleasure, I let out a not-so-quiet yelp and then raced to cover my mouth. The orgasmic waves made my knees shake, and I slid down the wall. All of this combined was more than enough to get Jenna's attention. The next thing I knew, she called out my name, then came to the door before standing over me completely naked and her toy still in her grasp at her side, dripping with remnants of her pleasure. Initially, she seemed hostile, but I was crying since I wasn't sure if she was going to kick me out, which I think made her go easier on me but also presented her with an opportunity. She crouched down and looked me in the eyes before asking if I was spying on her. I shamefully admitted I was and that I was sorry. She then asked if it was a regular thing I did, and I immediately said that this was the first time. Knowing that brought her some relief since she told me to stand up and wait in the kitchen.
As I did that, she put a robe on, then came and sat across from me at the kitchen table. She told me she wanted to know everything leading up to this moment. I told her what I deemed relevant but avoided mentioning sneaking into her room earlier in the day. It mainly boiled down to me making up the excuse that I heard her moaning and was both envious & curious about how she gave herself such a sense of pleasure, which was how I ended up spying on her. Whether she believed me is still unknown to me, but she seemingly understood my dilemma and then asked me if I had any toys. I told her I didn't and just used my fingers while also questioning why I was telling her all of this. She then asked if id like to try a toy to see what I thought of them since they aren't for everyone, and I had to repeatedly ask if she was serious, to which she told me to follow her.
We went to her room, and she instructed me to take my thong off and lay on the bed. I did as I was told while she took off her robe and grabbed a toy from the plastic bag. Sadly, it wasn't the blue one, but it was one with a G-spot bend at the tip. She handed it to me, and then a very eighteen-plus sex ed class started right then and there as she grabbed her blue vibrator again and sat in front of me, putting her legs over mine. Then came the lube, and she asked if I needed any, but just from feeling myself, I knew it wouldn't make a difference since I was soaked internally. From there, she proceeded to show me what to do. Now by this point in my life, I was by no means a stranger to sex, but when I put this toy inside me, I quickly realized the limitations of an actual penis. Face to face with Jenna, we both started to give in to our toy's vibrations as things got wet n' wild in her bedroom. I couldn't stop staring at her while her orgasms built up, and she narrated what she was doing or feeling. Simultaneously, I got to a point where I couldn't stop cumming, and Jenna started controlling the vibrations of my toy while making constant eye contact with me, referring to it as payback for spying on her.
At some point, my cumdrunkenness overwhelmed me, and all I really remember is her taking the toy out of me and putting it on the bedside table. Then she pulled up the covers, spooned me from behind, and whispered that I was a good girl and could stay as long as I needed to before we fell asleep. The next morning we were both naked and lying back to back, and the first thing to greet my vision was the toy, and instantly I was horny again. Trying to be quiet, I grabbed it from the table and turned it on to the lowest vibration and held it between my thighs to try and muffle the noise while also biting into the sheet on top of me to hide my moans.
What I didn't realize was that Jenna was already awake and had rolled over, and was watching me. However, she was courteous enough to let me cum before making me aware that she was awake. Saying simply, "Looks like we'll have to get you your own toy. Don't worry, I'll buy it for you, but you have to pay for the batteries." How could I say no to that, but it's also what started my toy addiction/collection.
After all of that happened, Jenna and I ended up having a very serious talk about where we stood. She went deeper into details about her divorce and the things leading up to it. Explaining how she wanted to do more wild sexual things, but her ex-husband wasn't interested, and that she was also bicurious and wondered if I'd be interested in helping her explore her sexuality. Needless to say, I accepted, and for two months after, we didn't hold anything back.
