She’s got an Experienced Eye by Funmark1997

My girlfriend and I just recently celebrated one year together, and things have been going very well between us. Despite only just turning 18 and approaching the end of high school together, we really felt like we were figuring out love and sex beyond our years. I agreed every time during these conversations, but a part of me knew something within me was changing. I didn’t want to break up, not at all- this change was much more subtle. Recently, I have been spending almost every single night that I am away from my girlfriend dressing up in her clothes and fucking myself with a dildo I bought without her knowing, all on camera for older men I met online. It started as an innocent and casual interest in submissiveness, as well as finding myself watching porn and imagining being the girl rather than the guy. Eventually that spiraled into me falling asleep to sissy hypno tracks with increasingly larger butt plugs in my slowly loosening ass. As I dove deeper into my fetishes, my sex life with my girlfriend also started to slow. This didn’t cause much of a problem however, as she didn’t have the highest sex drive in the first place.

On one fateful day, my girlfriend and I went on a small shopping trip to our local shopping center, eventually entering an expansive and largely empty bed, bath & beyond. We took our time wandering through aisles, individually exploring and reconvening every so often. As I wandered through a small aisle featuring an assortment of household vacuums, I came across another wandering customer. “It’s been a while since I’ve seen someone else… lucky me though, she’s quite nice to look at,” I thought to myself. The busty Latina woman paused briefly and looked me over, before continuing to look through the array of vacuums. She was quite tall, about 5’9” or so, making my 5’6” scrawny Caucasian frame look small in comparison. I quickly caught myself staring at her perfectly shaped butt in tight high-waisted skinny jeans and her large breasts practically bursting from her low cut, skintight shirt. “I always wondered how these worked,” she said in a feminine yet deep voice, motioning towards a fancy airflow hair dryer nearby. “Maybe I should get one?” I glanced around awkwardly to see if she could possibly be talking to someone else, but we were the only people nearby. “Uhh, yeah you should! I’m not too sure how they work either,” I said with a nervous laugh. We walked our separate ways, but I couldn’t help but notice we met each other’s gaze in glances many times as we did so.

I once again met up with my girlfriend, where she mentioned a few things that might be neat to buy. We wandered together a bit longer, before I once again crossed paths with the woman, again making eye contact multiple times. After a minute, I made just a slight distance from my girlfriend when the woman crossed me in an aisle. “Would you like to maybe… come with me for a bit?” She whispered with a smile. “I.. I can’t!” I said softly, “I’m with my girlfriend!” With a disappointed look, we went our separate ways through the aisle once more, this time clearly stealing glances back and forth. After this interaction, my young mind was racing, my heart was beating, and I was struggling to conceal my hard cock in my thin athletic pants. Yet, I was still unsure of why I was feeling this way.

For a little longer I walked and talked with my girlfriend, constantly keeping one eye out for the woman and occasionally catching her alluring gaze. “Hey babe, I actually gotta go to the bathroom, why don’t you go on without me for a bit okay?” I told my girlfriend, to which she jokingly told me to not take too long. Without thinking, I walked towards the last place I saw the woman, the exact opposite of the bathroom. I soon found her, and from a distance we met our eyes, and I simply nodded at her and turned around to head to the bathroom. On my way, I took several looks behind me as I made my way slowly to the bathrooms, and watched as the woman followed while keeping some distance. The mens and women’s bathrooms were located around the corner after a small hallway with water fountains separating them from the shopping area. I stopped at the fountains and took an elongated drink, quickly adjusting my throbbing cock against my waistband. Soon, the woman joined me to take a sip of water at the fountain. Without a word, we both walked over to where the hallway opens to the men’s bathroom door, and the women’s bathroom door. Between them, there were tall, empty racks for holding merchandise.

“I wonder were you can get racks like that, I can use one I bet,” she said as we stood side by side looking toward the racks. “Y-yeah, that’s a good question…” I started, but was cut short and trailed my words into an embarrassing moan as I realized she had moved her hand directly onto my hard cock, hardly concealed in my waistband. “Come here,” she said sternly, grabbing my hand and placing me against a wall by the men’s bathroom door. Before I could even think, she had pulled down my pants and underwear, and my throbbing 6” cock springs forward before it is quickly engulfed by her clearly experienced mouth. Practically all I could remember is thinking how warm and silky her mouth and tongue feel, before she skillfully teases a sensitive area. “I-I think I’m gonna.. gonna cum!” I said. Hearing this, she quickly takes her mouth off of my cock and strokes it with one hand, while the other is cupped in front of me. I can’t help but blow my load, with most of the milky cum being caught in her hand, while some goes over and onto the floor. “Hmm that was too quick boy,” she said, with a mix of disappointment and happiness. “I’m sorry hehe, it just felt really good…” I responded. “Come here,” she said again, this time making her way into the women’s bathroom door. I nervously followed, thinking she would wash her hand holding my cum. Instead, she makes her way into a stall, all the way in the back of the empty bathroom, and motions for me to come in. Once I entered the stall, I realized my cock was hard once again, anticipating the next feeling to be the woman’s wet pussy siding over it.

“Sit.” She said, with a dominating voice. I quickly sat on the closed toilet, excited for what may come. “You’re quite the horny boy aren’t you?” She asks. “I am a horny boy…” I respond. “Horny boys need to be taught not to cum so soon, I wasn’t done with you yet.” She said with a demeaning tone. “I-I’m sorry…” as I apologized, the woman used her free hand to quickly grab my jaw, and opened my mouth. Before I even realized what was happening, her other hand shot to my mouth, covering it and sending the thick cum into my mouth. I was shocked, and tried to garble out a “What the fuck,” but was completely unintelligible through the salty cum in my mouth and her hand. “Shut up and sit there, and maybe I’ll still fuck you… how about that boy?” She said. I quickly nodded in agreement. The woman removed her hand, but before I could spit the cum out she glared at me and sternly said “Swallow it. Now.” It took me a second but I buckled up and gulped the cum down, leaving a salty taste in my mouth. “Good boy,” she said, as she pulled her breasts out from her shirt. She leaned over, pressing her tits on and over my face, obstructing my vision as I hear her removing her jeans. As I kiss and fondle the handfuls of tits in front of me, she says a phrase that confused me. “Now, it’s your turn boy,” she says as she leans back again, and I quickly realize the gravity of what she said about ‘fucking me’ earlier. As I bring my gaze down her now nude body, I see a cock the size I’ve only seen in porn. It was easily 8” long, and thick, making me instantly insecure about my own size. Before I could process what I was looking at, she grabs the back of my head and the base of her cock, draping the still-hardening meat over my forehead and her clean-shaven balls on my chin. With one hand holding a fistful of my hair, she quickly takes her phone with the other hand and manages to take a picture of my surprised face half covered by her thick cock. “Be a good boy and do your job or I’m showing this to that girlfriend outside.” She said. “O-okay… I will…” I respond, defeated. With that, she slides her cock off my face, and instead points the tip at my mouth. “Suck.” She demands. I open my mouth, and it is quickly filled by the massive head of her thick rod. I soon found that, despite her thrusting, that I could hardly stretch my mouth around the girth, and could barely make it further than the head. “Watch your teeth, slut.” She scowls, following with two quick slaps to my cheek. I adjust in order to minimize the contact from my teeth, but the only practice I’ve had with sucking cock was on my dildo, which was significantly smaller and thinner.

“You’re lucky I have this with me,” she said, pulling out a small bottle of lube from her purse. “You’re going to need it.” She pulled her cock from my mouth, and I let out a gasp as I flex my sore jaw. “Stand up, slut. Take those pants off and turn around.” She demanded, as she squeezed lube onto her now fully erect, engorged cock. “Wait, I can’t do that! It’s too big!” I squeaked, but I quickly followed her directions and was soon displaying my smooth hole for her. “Mmm, I know a sissy boy when I see one… you’ve played with this boipussy before haven’t you?” She chuckled, spreading my cheeks apart, slightly stretching my hole open. She squeezed a small drop of lube onto her finger, and massaged it gently around my open and eager hole. I realized then that my own cock, which had gone somewhat soft while I was attempting to fit her massive rod into my mouth, had sprung to attention, once again throbbing almost painfully with arousal. Suddenly, the finger that was gently circling my hole was quickly slid into my ass, down to the knuckle. As she did this, she spun her hand and pressed with her finger directly onto my prostate, almost making me cum right then and there. “Ohhhh fucckkkkkk….” I moaned, trailing off. “Nice and sensitive I see, that’s a good boy.” She said, as she inserts a second finger into my hole, and gently fucking it as she gently holds my balls with her free hand. “Don’t you dare cum until I say you can.” She commands, as she inserts a third finger into my rapidly loosening ass. “Do you hear me slut?” “Yes! I hear you! Oh.. mmmm..” I said, as the familiar feeling of anal pleasure was beginning to make my mind go blank.