A Sissy Slut's Diary Ch. 04

For the last two months university had been all I'd been able to think about - exam season was in full swing and that meant my wig, my girly clothes, and my toys had all languished in the back of my closet, and for every day I spent studying and taking tests was a night I spent lying in bed longing for the feeling of stockings on my legs, a man's hands around my waist, and a cock in my ass.

Still, I had my priorities in order, and a whole summer break ahead of me. I had nothing planned yet, but hidden in a folder on my phone, notifications turned off, were Grindr and Kik and the dozens of men I talked to on them who were just waiting for me to say I was free to be their slut for a night. That was what had kept me going, knowing that once my final exam was over I'd have three whole months with no work, no responsibilities, nothing to keep me from giving in fully to my urges.

I hadn't been crossing days off of a literal calender, but I had kept them ticking by in my head and as the final few arrived I was struggling to keep my mind focused on my studies. In a lecture hall, sat up at the back row, my eyes drifted from my notebook to the guys around me. I still noticed the girls on my course, and every now and again I would picture myself sleeping with one of them, but more than anything I was jealous of them now - focused on the outfits they wore and the guys that talked to, wishing I could sit there like they did in their short skirts, in tight jeans and leggings, catching the eyes of the guys who would love to fuck them. How they restrained themselves I never understood - they must have known that if they wanted after every lecture they could grab a guy, lead him to somewhere private, and have him racing to get his cock out for them to suck. In their position I doubted I'd ever have gotten any work done, I'd have been skipping lectures for the chance to be fucked by every one on my course.

Instead though, the most I did was put on a pair of stockings underneath my jeans, and of course a lacy little thong, smiling to myself as I imagined what it might be like for someone to notice, for someone to catch a glimpse of it - like Anthony maybe, the six foot five wall of muscle I struggled to take my eyes off of while supposed to be making notes. It was impossible not to picture him grabbing me in the toilets, forcing me into a stall, pulling off my clothes to reveal the lingerie beneath, making me gag on his huge cock, his hand over my mouth to keep my quiet as he pushed me up against the stall door and fucked my ass, left my dripping cum from it onto the men's room floor, feeling less like a man than I had ever done.

By the day of my final exam I came with a backpack filled with all the essentials: my notes for last minute revision, plenty of spare pens, a water bottle - and, beneath all that, a blonde wig, a lace teddy, pink lipstick, and a bottle of lube. The lace topped stockings I was of course already wearing, and as I left my backpack at the back of the gym and took my seat at the exam table, my heart raced. At least it made sure I wasn't nervous about the exam, my mind far more occupied with what I might get up to afterwards.

With the final question answered I had sat anxiously twirling my pen, stockinged foot tapping in my shoe, just waiting for everyone else to finish and the university year to finally be over. As the clock finally ticked around and we were dismissed I picked up my bag with a smile on my face, quickly greeted by some friendly faces - Curtis, a talkative boy who I had sat with in most lectures, Becca, a short haired and short statured girl he was friends with, and her girlfriend Kim, a freckled girl with eyes huge behind round-framed glasses.

"Hey man," Curtis said with a wave, "you fancy getting a drink?"

"Yeah," Becca chimed in, "we're heading to the pub, end of the year celebration, you're welcome to come."

I had no concrete plans of course, so I found myself smiling and accepting the offer. A couple of drinks would only make me more eager for some fun, and I definitely felt like celebrating the freedom of the summer ahead. That was how I found myself sat with the three of them at a pub only a mile down the road from our campus, as we swapped stories about the year.

"You know," Curtis said, pint in hand, "The whole long distance thing has actually been harder these last few weeks than it's ever been."

Becca nodded. "Well yeah, it's like you know once you're getting close to seeing her again it's harder to wait. Like you're just aching for these last few days of waiting to be over, it's agonizingly close."

Curtis took a sip of his drink and nodded along, and I did too - not through some longing for my own far away girlfriend, of course, but with a good understanding of that sort of feeling nonetheless.

"Yeah, it's been a real challenge this yeah," Curtis said, and then slapped a hand on my shoulder. "Of course, the challenge now is finding you a girl." I smiled, and might have blushed a little - I had a tendency to do that, and was never very comfortable with people talking about my love life. But still, I was a few drinks down by now and that awkwardness was fading.

"Yeah, maybe," I said with a shrug, and swigged back the last of my own drink. Even feeling a little tipsy my awkwardness must not have been washed away entirely, as Curtis laughed.

"No need to look so sheepish dude, just tell us the kind of girl you're looking for and we'll wingman you. Everyone loves pussy here, no need to be shy, we'll get you a girl."

I chuckled as I put down my glass, and maybe it was the alcohol, or just the company at the time, but as I did I replied "How about a guy?" As the words left my lips my heart skipped, my face suddenly freezing as I realized I'd not actually talked about this to anyone - I'd put on a wig and let strangers fuck my asshole, but I'd yet to sit here as myself and tell anyone I knew that I was even attracted to men.

Without missing a beat Curtis slapped my shoulder again and said "Even better, you've got three people here who don't like dudes so you don't have to worry about competition, the perfect wingmen." I smiled.

As the three of them tried to prod me for details of the kind of guy I liked, I struggled to avoid answering their questions. What was I supposed to say? I wanted someone dominant? Someone wwell hung? Someone who looked like they could snap me in half? Someone who liked fucking a guy in a schoolgirl uniform?

"I don't know," I ended up saying, "Confident maybe. I like someone confident, who's laid back, sure of themself?"

The conversation thankfully didn't lead to them trying to find a guy in the pub to wingman me with, but instead lead to Becca flicking through her phone.

"There's no pressure right, don't feel like because I'm recommending a friend you have to say you like him or anything, but you guys would be a great couple. He's really cute, he's actually just got out of a relationship with a girl but he's bisexual for sure - here, this is him." The phone waved towards my face had a guy's Instagram account open, and I had to admit - he was cute. More boyish than my usual type, slim, but clearly toned, a shaved head and dark skin, and gorgeous eyes. I'd long since moved past the phase that almost every sissy has, of pretending they're not really attracted to guys, that they want dick but don't find men attractive in the same way they do girls. No, I could fully admit he was hot and I could absolutely see myself letting him bend me over a bed and spank my ass. Of course I wasn't going to say that right now.

"Yeah," I said instead, "He's cute." An attempt to act nonchalant failed as I felt myself blush again, and as everyone laughed Becca waved her hand for my phone.

"I'll put his number in for you," she said, "give him a text if you want."

***

After a drink or two more Curtis had to leave, eager to be back home ready to meet his girlfriend the next day, Becca and Kim were off home, and I stepped out of the bar and into the street with my fingers twitching over my phone, the new contact added - Matthew. It would be a bad idea, I thought, to text him. I wasn't looking for a date, I wasn't looking to find a boyfriend, however cute he might be. I was looking to be fucked, and not even just that - to be fucked like a girl. It was one thing to let strangers know that, men who walked into a hotel room and found me already dressed up and ready for them, who never saw me as anything other than a sissy girl. It would be another thing entirely to get involved with this guy, to tell him what I liked, especially if he was friends with Becca. University wasn't over yet, just this one year, and I didn't know how I'd look anyone in the face again if he balked at me, told her that her friend was a freak who liked dressing up as a girl.

But still, I was drunk on both alcohol and the promise of the summer, and before I knew what I was doing I had texted him. "Hey, so Becca gave me your number and said maybe I should text you, playing matchmaker I guess." Then another: "I'm a friend of hers from university." The one more: "I'm a guy by the way, just thought I'd clarify."

After a minute a buzz of a reply. "Yo, yeah she said you might drop me a message." Another: "She sent a pic, you're cute - wanna come round mine?" One more: "4 a drink, chat, hang out?"

Before long I was on a bus to the other side of the city, then knocking on the door of a block of student housing. The face that greeted me as it swung open wasn't Matthew, but a long haired guy who told me was his housemate. He led me through a kitchen, past another couple of guys I nodded at with an awkward smile, and to a door numbered 6 that creaked opened just before we stepped up to it.

"Hey, I was just coming to let you in," Matthew said, a slightly dazzling grin, standing around the same height as me in a loose fitting t-shirt showing of skinny muscled arms and gorgeous black skin. His housemate walked off and I let him usher me in, smiling and my heart racing a little as he shut the door behind me. "Just for some privacy," he said, "people like to have an eavesdrop around here." He stepped over to a mini fridge tucked under a desk and pulled two beers from inside, cracking them open and offering one to me. I took it with a nod of thanks, standing glancing around the room as he took a seat stretched out on the bed and took a sip of his drink.

"You can sit down man, relax," he said, waving to the bed in front of him, and I shrugged my backpack onto the floor, perching on the edge of the bed. "So, you go to uni with Becca?"

The conversation began with that, moving from how we knew Becca, to what we were studying, to interests and hobbies, to music, and before I knew it I was three more beers down and letting Matthew, who had since told me to call him Matt, point me towards a small stack of records to pick something to play. I stood bent down, fingers flicking through the stack of musicians I'd never heard of before settling on one at random and placing it onto the record player, focused on what I was doing until I heard Matt speak from behind me.

"You know, you've got a great ass." I froze, fumbled a little with the needle as I got the record spinning, and turned around in full awareness that my face was hot and flushed red. I took a seat back on the bed and realized he's shuffled over closer to me, his hand reaching out and touching my thigh as I laughed and tried to pretend my heart wasn't racing at the feeling of his hand on me, trying not to let me eyes flicker to his crotch as I pictured the black cock hidden underneath his sweatpants. Whatever nerves I had he didn't share though as his hand quickly found my face, a finger pulling my chin to one side as his lips met mine, and I let him kiss me. One hand of his was on my cheek, pulling my face close to him as his lips moved against mine and I kissed him back, and I felt his other hand leave my thigh and find my waist, pulling me to lean into him as it slid beneath my shirt, caressing the skin of my back and making me shiver slightly from the gentle touch.

"You seem pretty nervous," he said with breath hot on my lips, "we only have to do what you feel comfortable with."

The idea of backing out now was nowhere on my mind and my response was to kiss him again, my own hand sliding along his thigh, moving up and searching for the bulge that I found beneath the fabric of his pants, a growing cock already bigger than mine that my fingers closed around, stroking him slightly through the material. My obvious anxiety had clearly had him holding back before as he now grabbed my waist, swiftly pulling me onto his lap, hands grabbing my ass and leaving me leaning down slightly to kiss him, stroking a stubbled cheek with one hand while the other moved under his t-shirt to his chest. Strong hands gripped my ass tight, squeezing as we kissed and he pulled me again to fall onto the bed beside him, legs wrapping together as we lay together, lips still locked.

His fingers quickly found the buttons of my shirt and I shrugged it off, moaning into his mouth a little as he stroked my chest and brushed against my nipples, all the direction he needed to take two fingers and gently pinch a nipple between them, stroking them and leaving my own little cock straining against my jeans.

I could feel his bulge against me now and I reached down, sliding beneath his waistband of both sweatpants and boxers, gripping a cock that was everything I'd been craving for so long now, so hard, so big, throbbing in my hand as I stroked him. He reached and yanked his pants down, shuffling them and his boxers off his legs, letting me look down for a second and catch a glimpse of the gorgeous black cock in my hand before he pulled me back in to kiss him and he grabbed my belt, unbuckled it and unfastened my jeans with ease and pulled them down.

I was so focused on the feel of his cock in my hand, of how badly I wanted to get my lips around it, and of how much I was enjoying for the first time properly making out with another man, that I had forgotten what I was wearing beneath my jeans until I felt his hand slide them down and then his fingers brush against the nylon of my stockings. I felt him move back slightly, glancing down at me, at my cock straining against a thong, the lacy top of my stockings on my thighs, sheer black nylon covering my legs that peeked out from my half removed jeans. My chest felt tight and I froze as he looked down at me, a dozen scenarios running through my head where he laughed at me, or looked up disgusted, or kicked me out, where I ran past his laughing housemates as he told them what a sissy I was. When his eyes came up to meet mine though he was smiling, but not at my expense.

"Fuckkk, you like to dress up, huh? That is so hot." My heart kept racing as he pulled me in to a kiss again, and as I kicked off my jeans and felt his legs brush against my stockings it took everything I had to stop myself from begging him to fuck me there and then. Instead, what I managed to say was:

"I'm only half dressed, I have more in my bag."

Matt's eyes were wide and eager, and he shoved me over to hastily unzip my backpack and pull out everything from within.

"Holy shit, you get dressed," he said, turning his head away from me. "Tell me when you're done, I want the full reveal."

I quickly grabbed my jeans off the bed, stuffed them and my shirt into by bag for now as I untangled the scraps of fabric that made up my lace teddy, stepped one stockinged foot into it and then another, tying it behind my neck, a plunging neckline leaving it only barely covering my chest, while I pulled off the panties and let my hard little cock be held back only by the lace of the lingerie. I grabbed the wig, tossing it over my head and smiling as it fell against my shoulders, staring at my reflection in a mirror over the desk. Brushing the fringe evenly above my brows and running my fingers through it to neaten it out, I pulled out the lipstick - the only makeup I had with me, and ran it over pursed lips, leaving my smiling in pink as I stared at my slender torso in the mirror - slim face already looking girly with a head of blonde hair. Glancing at Matt, still sat with his back to me, naked on the bed, I quickly grabbed the hem of my stockings and pulled them up my thighs from where they had slid down to, evening myself out and then pausing for a second, before coughing slightly to get his attention.

Matt turned around and his eyes swept up and down me, taking in the full sight of me dressed up before him before he stood up and stepped over to me, a glint in his eye as he grinned.

"So," he said, a hand slapping one ass cheek and pulling me towards him, "you're a really sissy slut then, huh?"

I felt myself blush red, so unused to revealing it like this, but his hands on me had that embarrassment quickly fading and replaced by sheer desire, and I nodded, kissing him again as his hands cupped my ass and held me close against him.

"So you gonna suck this cock then, like a proper girl?" I nodded again, more fervently this time, and suddenly his hands were on my shoulders pushing me to my knees, Matt leaning back to sit on the bed with his hard cock pointing up towards me as I brought my head in, one hand grasping it and stroking the length of it down to the base, as my open mouth moved towards the head of his cock and I finally took him between my lips. The initial hesitance was totally gone, I was back where I belonged, and all the time I'd spent waiting to be taking a man's cock again had me practically moaning just from the feeling of it entering my mouth. If ever I had a moment where I doubted that I was a sissy, it was always washed away the second I felt the warmth of that hard cock on my lips, felt it slide across my tongue, as I opened my mouth wider to push it in further, tasted those inevitable drips of pre-cum that teased the full load I might get to swallow later - every time really is heaven.

I could hear Matt moan slightly, a deep sigh of contentment as I gripped his cock tight and set my lips to work moving up and down the length of him, not taking him too deep yet but enjoying getting him worked up, spit lubricating him as one hand stroked the shaft while I sucked. He was content to sit back, let me work, to worship his cock, and to speak in a hushed and breathy voice of how much he loved it.

"Fuckkk, you're really a perfect little slut," he said, and I felt my chest swell with pride and satisfaction, a smile twitching on the corners of my mouth. Taking my lips from his cock I planted a kiss on the head of it, moving down and dropping small kisses along the length of it until I reached the base, finding his balls hanging below. With my hand now stroking the full length of his shaft I brought my mouth to his balls, kissing the skin until I found one of them and took it between my lips, loving the way it made him moan as I sucked it into my mouth, my hand still stroking fast against his saliva-lubed cock. When I brought my lips back to his shaft he was no longer content just to let me go at my own pace, and my head was taken between his hands and pulled onto him again, his cock forcing its way between my lips and deeper now, pushing back into my throat and making me gag a little but not pulling back for a second. Instead I gave in to him, let his hands guide me as he fucked my face, as he pushed his cock deeper still and I felt my eyes water. Only when he let go again and stroked my cheek did I go back to moving my lips myself, being sure to match how far he'd pushed me down, to make sure I took his cock as far as he'd wanted, the way it made me choke only adding to how much of a slut I felt kneeling in his room, knowing full well his housemates were right outside.

When he pulled me from his cock it was up onto the bed with him, laying on top of him at first and feeling his cock against my stomach as he kissed me before he rolled over, trapping me beneath him and making my heart flutter. His hands held mine, pinning my arms to the bed as he loomed over me, the taste of his cock still on my lips along with the feeling of his own mouth from only seconds ago, and staring up at him I felt like I'm sure any girl would have done - a thrill of being submissive, weak beneath him, not fearing what he might do but excited by it, and yet with a pulsing nervousness of knowing he could be inside me any time he wanted. As he let go of my hands I lay still while he kissed my lips, then my chin, then my neck, and I giggled slightly from the tingle of his gentle kisses along my chest and nipples before he worked his way past that, across my stomach, and to my hips. Then it was his hands grabbing me, flipping me over so his lips could find my ass, kissing each cheek and making me shiver in anticipation.