A Sissy's Fun Campus Meetup

It was Friday and I was coming back from an early afternoon class, the only one I had today. I walked in to my dorm building and headed up the stairs to my room, my roommate was already gone for the day, likely with some friends and I wouldn't see him until tomorrow morning. So as I kicked off my shoes I felt comfortable slipping off my socks, wiggling my toes in the refreshing air and admiring my nails painted a cute shade of periwinkle. I stepped into some flip-flops dropping off some things and organizing my space before falling into bed.

I softly sighed as I stretched and relaxed, it had been a busy week with a couple of exams but at least I wouldn't have any homework to do over the weekend. I texted a few friends seeing how they were doing and setting something up for the weekend, they were busy today so it was setup for Saturday night. I'd basically have the evening to myself, I smiled as I thought of my secret stash hidden in the bottom drawer of my dresser.

I turned in bed and opened up my grindr app, swiping through a few new profiles I spotted and messaging some people I regularly chatted with. A few minutes later my phone buzzed with a message, it was from a guy I'd been chatting with for a few weeks but hadn't gotten the chance to meet besides a quick evening chat. His name was, Matt. A guy in his early 30s he was relatively tall at 6'0" with a toned body since he liked biking and running so much, I thought he was attractive with his short black hair, brown eyes, and charismatic smile. "Hey girl. Happy weekend :)" he texted.

In real life you wouldn't suspect there was anything unusual about me, just a slim and kinda short guy at 5'6". Though online I was, Katey. A 20 year old college girl, with long and slim legs, a thin upper body with a flat chest, neck length wavy dark brown hair, and wide brown eyes behind my glasses. All of my pictures were in cute outfits like short dresses, skirts and snug tops, leggings and cute sweaters, all in the fashion of an average college girl. "Heya, Matt. How's it going?" I texted while admiring a shirtless pic of him at the beach, loving the look of his fair skin and imagining myself in his embrace.

"Not much. Just getting home from work, not much planned for the weekend," he replied.

"Oh that's too bad, some friends want to meetup tomorrow but I've got nothing for tonight :/" I replied hoping he got the hint.

"Well that sounds like no fun, a pretty girl like you shouldn't be all cooped up!"

"Haha, yeah it would be nice to have something to do ;)" I sent back, smiling to myself.

"Well since we've both got nothing going on maybe we can plan something for later?"

My heart beat a little faster reading that, feeling a flutter in my stomach. I wasn't new to meeting guys dressed up like a girl, but it was always very exciting when the opportunity presented itself. I bit my lip as I fantasized about being with him, he seemed like a nice guy through texts and that one conversation we'd had in person, always happy to chat and get to know each other. He also knew just the right way to get me going and feeling like a horny girl, calling my legs and butt sexy, writing about all the things we could do if we ever got together. He lived in a nearby neighborhood close to the suburban campus I lived and studied on, though we would always get incredibly excited about doing something a little more public.

"Sounds like it could be lots of fun. How about 8pm?" I sent eagerly staring at my phone waiting for the reply.

"Sure! Sounds great to me, where?" was his message.

"I'll let you know later, first I want to get ready!" I sent, waiting for his confirmation before setting down my phone.

I had a couple hours before we'd have to meet so I relaxed for a little bit longer, eventually heading down to the dining hall for an early dinner. When I came back upstairs I got ready for a shower grabbing my towels, a razor, and some floral scented shampoo and soap that I'd gotten out of my girly stash. I walked into the communal bathrooms and picked an empty shower stall, stripping down to just my flip-flops and getting the water running. I took my time, letting the warm water wash away the stress of the week, my wet hair sticking to my face and neck. I carefully washed myself, making sure all the sweat and dirt went down the drain, replaced by the sweet smell of wildflowers. With that done I gave myself a quick pass with my razor, much of my body was hairless and I usually shaved the rest. So it was easy to knock off the stubble on my slim tan legs, my flaccid cock, and under my arms. I rinsed off with some cool water, watching how my average cock shriveled up. Drying off I wrapped myself with a towel and tied up my hair in another, quickly walking to my room and locking the door.

I applied some nice smelling lotion and hung my towels to dry, stepping in front of a full length mirror. Admiring my slim and smooth form, my flat chest, my toned stomach, my flaccid cock and balls swaying with every movement. I turn to see my perky butt and long legs as I posed on my tip toes, loving the look of the polish on my toes.

I use a fresh towel on my head while I booted up my laptop and got my bluetooth headphones in. Quickly navigating to a porn site and getting some of my favorite videos going, cute sissies or crossdressers with a big masculine man with a nice cock. Just the thing to get me in the mood as I pulled out my small girly wardrobe from my dresser drawer. There were a couple of outfits worth of clothes from dresses and skirts, tops and sweaters, socks and hosiery, bras and panties, even a pair of flats and strappy high heels. Hidden best of all was a little plastic box holding a dildo, a set of butt plugs, a chastity cage, and a big bottle of lube.

I laid a towel out on my bed, making sure I had a few videos queued up on my laptop before crawling onto the towel. Sitting against some pillows set against the wall I could comfortably lay back while I watched my sissy porn and toyed with my tight hole. Using just a little lube, the cool gel resting on my finger before I applied it to my smooth and tight hole. I shudder with delight at the cold sensation and bite my lip as little tingles radiate through out me. I keep this up, applying more lube to myself and teasing my entrance with the pad of my finger, my body quickly becoming hot from the teasing pleasure.

Eventually my eager hole can't take it anymore and with the lightest of pressure the tip of my finger slides in, it isn't the biggest of stretches but it's enough to make me softly moan at the sudden penetration. I keep going, sliding it deeper wiggling it around applying pressure until I find my prostate. Now moaning a little louder, "Fuck..." I murmur as a drop of precum leaks out of my hard six inch cock. I keep this up, switching between gently fingering myself and rubbing my prostate until my relaxed hole can easily take two fingers. Staring at the porn as some sissy rode that big cock like a champ, her little cock limply slapping around leaking all over the place. I softly groan and manage to fit in a third finger, nicely stretching myself. A very exciting and filling feeling after having gone without anything in my butt for a few weeks.

My hand eventually begins to get tired and the three fingers slide out, a slight empty feeling left in my hole. My other hand swiping at a strand of precum hanging from the tip of my head, softly sucking my finger clean enjoying the salty taste. I reach over and grab my small plug, a little thing made of soft and smooth black silicone. I lube it up and pop it into my hole with little effort, shuddering in delight as my entrance snuggly gripped it and was kept constantly stretched. I even thrust it in and out at the widest point to make sure it comfortably rested between my perky cheeks. I slip into a robe and quickly head out to wash my hands.

Coming back in I grab my phone and text Matt again. "Hey, gonna start getting ready soon! I was thinking of a place we could meetup," I send, looking over the variety of clothes I could pick from.

"Cool! I'll start getting ready too then, where did you have in mind?" he asks.

"Umm, there's this pretty private place I know on campus, though I'd have to walk through the building to get to it, which is fun ;3," sending him the details.

"Oh you naughty girl, I'll be there! ;3" loving the idea and saying he'd be a little early and telling me of a special knock to use, sending an audio of it.

With that settled I set my phone down and focused on my porn again, sitting back on the pillows and towels. Toying with my little plug, stretching my hole until it would pop out with the slightest of efforts. I move up to the medium one and repeat the process, warming up and stretching my hole to be able to comfortably take the plug. Eventually moving up to my larger and final plug, feeling I could take my dildo with no issue since the head was actually a little smaller. Though I decide to wait and felt the real thing would be better anyways, sitting on the edge of my bed feeling the pressure and amount of stretching my hole was under. It was simply amazing as I played with my nipples, squeezing around the plug and making myself leak.

Wiping my hands clean I take a few deep breaths at the open window, the cool early autumn air helping me relax. I eventually feel my cock soften, the plug applying gentle pressure everywhere and making me leak a little.

Grabbing my phone I read another text, "Oh! Make sure you're wearing your cage, sissies don't need their little clits! ;)" I bite my lip as I read that and struggle not to get hard, having to take another few deep breaths and pace around my room.

Having finally relaxed I stop before my bed, grabbing a little lube and the metal ring of my chastity cage. Getting it slippery and sliding it on until it was snuggly against me, quickly squishing my soft cock into the small nub sized metal cage, locking it and tossing the key onto my bed.

With my clitty and sissy ass all ready to go, I felt like I could start getting dressed. Picking things and putting things away as I decided on tonight's outfit. It's all eventually narrowed down to a pair of crotchless fishnet stockings, a pair of black cotton and lace panties, and a matching black lace bralette. Loving how it hugged my flat chest and teased my sensitive and stiff nipples, the panties snug against me giving an inviting look to my ass while it closely pressed my little cage to my body creating a small bulge. The fishnets were delicately rolled up my tone and long legs, tightly pressed against me with easy access to me once my panties would be pulled out of the way. It's all quite an arousing and slutty set of undergarments.

I snap a few pictures and send them to Matt. Replying with a mouth watering picture of his hard cock and a message that he'd be heading over soon.

Over this I slip into a pretty maroon skater skirt, pulling it up until it rested at my waist and extended down to my mid thigh. Absolutely loving the look of this skirt with the fishnets. For my top I go with a tight black top with snug sheer long sleeves, showing an exciting view of my slim arms, shoulders, and slim chest. Not quite a crop top it still showed a bit of my tone midriff.

Standing in front of my mirror I smile to myself, looking just like a college girl getting ready for a party. Here I spend some time brushing and styling my now dry wavy neck length hair, finishing the look with a few hair clips and a quick blowdry. I felt I looked feminine enough so for makeup I just do a bit of smoky eyeshadow and red lipstick that really makes my soft lips pop and look very inviting. With only one pair of heels I grab my three inch strappy heels, setting them aside while I got a few more things ready.

My phone buzzes again with a message from Matt. "Hey, just got to the parking lot. I'll be inside, take your time!" I smile as he sent a picture of the building, sure he'd be there.

I didn't have a purse so I went with the next best thing, my bookbag I'd emptied out earlier. It certainly clashed with my outfit but it would have to do, tossing in my big bottle of lube, some condoms, the keys to my chastity cage, and my high heels.

I didn't feel like dealing with the embarrassment of running into a friend on the way out of the building so I decided on putting them on outside. Throwing on a loose sweater and sweatpants, and slipping into my sneakers. I made sure everything was put away before heading out and locking the door. "Hey! On my way, I'll be there in 10!" I quickly send off, heading downstairs and out through the side door.

It was early autumn so it was already dark, with a cool breeze blowing though still comfortable without a sweater. I walk towards a nearby lake, finding a bench away from a lamppost and hidden by some overgrown bushes. Here I take out my heels, pulling off my cover and taking off my sneakers, stuffing it all into my backpack. I slip into my heels and tie the cute straps around my ankles.

Fully dressed I grab my bag and head off, becoming just another sexy girl out for a night of fun. Though I was the only one walking towards the buildings of campus instead of the surrounding neighborhoods where all the parties were. I walked quietly loving the gentle breeze in my hair, how it tickled my smooth fishnet wrapped legs, enjoying the rhythmic sound of my clicking heels on the pavement. I avoided large crowds, or really anyone since I was still nervous about being caught though this was very exciting. My cock straining in my cage and my hole squeezing around my plug with every step. I kept to dimly lit paths and make my way to the tall building I knew would be perfect for all of this.

The sound of heels clicking on concrete quickly turns to echoing clicks on tile as I swung the door open and entered the empty building. The university was mostly for commuters and the small amount of people who lived in the dorms would be off partying, so most of campus was a ghost town with entire buildings left vacant over the weekend.

I rode up on the elevator, my heart beating faster with each ding I heard, climbing up to one of the highest floors. With a sudden jolt the doors slide open and I step out, walking down a hallway with my heels echoing across the entire floor. I eventually reach where I was heading, nervously standing before the door. I take a quick deep breath before knocking the pattern I'd been told.

The moments feel like an eternity until the door unlocked and swung open. Relieved to find Matt standing there with a big grin, looking up to meet his eyes and smile too. He quickly lets me inside and locks the door behind us.

The place I'd chosen wasn't a classroom, they had too many windows and didn't lock properly. I'd gone with a private bathroom meant to be used by one person at a time. It was clean and spacious, it must have also been meant for breastfeeding mothers because it had a table and a large comfortable chair, it's why I had picked it. A private room to have all sorts of fun in where nobody could disturb us.

I set my bag on the table as Matt approached me. In this light I could see how tall he was even with me in heels, the definition in his body through his snug shirt, it was all so attractive as he held me by my waist. "My, you're even prettier in person, Katey," he said in his warm tone.

I giggled, "Thanks, you look great too," I smiled taking in his scent, a lovely cologne.

He holds me a little tighter, pulling me towards him. Leaning his head down to whisper in my ear, "Thanks for coming, we're going to have lots of fun and you're going to be a good girl, okay?" I bite my lip and nod, blushing as he kisses my cheek.

He lets me go and steps towards my bag, "So did ya bring your keys?" he asks, gesturing towards my bag. In my softest girliest voice, "Yeah... They're in there, you can check." With that he unzips it and pulls out my regular clothes, setting those aside without a word. Next he pulls out the lube and condoms with a smirk, "Someone came prepared," he teases. Finally grabbing my chastity keys, spinning them around their key ring playing with them before pocketing them, "You'll get these later," he smiles walking back towards me as I nod, excited to give up the keys if only for a little while.

He returns in front of me, grabbing me by my hips and gently squeezing. I turn my head up to see him, "Mmm such a good girl. Knows that she doesn't need her clitty," he purrs as he softly presses his lips to mine. I feel myself melt in his grip as we begin to make out, his lips were soft and warm, when mine part and his tongue teased out to dance with mine he tasted like mint toothpaste. I breathe in deep, taking in his masculine scent, enjoying how he felt me up, rubbing my back, caressing and squeezing my ass. With me softly moaning with each teasing squeeze and gentle spank.

"Such a nice and perky ass," he purrs, absolutely straining in my tiny metal cage and already leaking into my panties. While he kept feeling me up, I caressed his strong arms, feeling the definition in his shoulders, and the muscle in his chest. I felt safe in his grip, feminine, and submissive.

One hand leaves my ass and gently grips my wrist, guiding it and placing it on his hard bulge in his jeans. Making me rub and caress it while his hand slides under my skirt and between my legs. He finds the small bulge in my panties and gently cups it, feeling my precum soaking through in his palm. He whispers into my ear as I gently rubbed his manhood, "Feel the difference, sissy? That's a real mans cock, good sissies stay locked," he says as he gently squeezed my balls. I cry out in a whimpering gasp, chuckling at my girly moans. His hand slides further back until he can feel the firm base of my silicone plug, "Good girl, Katey. That's the only way sissies are supposed to be pleasured," pulling away his hand to keep touching my slim body while he kissed me and I rubbed him through his jeans.

We eventually pull away, a little breathless and eager to do more. He steps backwards, guiding me towards him. Falling back comfortably in the large chair, reaching out to grab my shoulders with him pointing down with his eyes, "Kneel," he says sternly.

It's enough to send a shiver shooting through me and with a gentle pressure I'm slowly brought to my knees. Resting my hands on his legs while I looked up at him with an excited smile. He spreads out and gets comfortable on the chair, making enough room for me between his legs. He's slowly rubbing his bulge while he hungrily gazes at me, "Be a good girl and show daddy your skills with those pretty red lips," he says moving his hands away.

I'm blushing bright, "Yes, daddy," I say softly. Wiggling a little closer, leaning forward and resting my small hands at his waistband. With excited and shaking hands I manage to undo his belt, unbuttoning his jeans, and pulling down his zipper. Sliding them down his thighs, without that his erection is more noticable as it pushes against boxers already a spot of precum on them. Grabbing his waistband I slowly pull down, eager for the big reveal to pop out.

It's everything I could have hoped for and more. His erection standing proudly at attention, twitching and throbbing with several veins visible. As I gently held his white shaft with both hands I reasoned it must have been eight inches long and thick, topped by his big round pink head leaking another drop of precum. It felt so firm and hot as I gently squeezed it and watched the precum rundown to my hand. "Good girl, it's all for you, enjoy," he smiles allowing me to take my time.

I excitedly lick my lips, gently stroking his length rubbing in his leaking precum. My breath is warm and teasing against his cock, gingerly teasing out my tongue and tasting him. His precum was warm and salty, gently lapping my tongue against his head to tease out another drop. "Good girl, just like a lollipop," he murmurs, driving me to fully stick my tongue out and swirl around his large cock head. Coating it in my warm saliva while my hands continued to stroke his shaft, rubbing in my saliva that dripped off my tongue.