Gay Sex One Shot 🔞

My introduction to sex and sissyhood

I was a horny teen growing up. I discovered the joys of Internet porn and pleasuring myself as a pretty young age, all I thought about was sex but unfortunately I hadn't been gifted with the greatest genetics. At 14 I stood at an impressive 5 foot tall exactly and only weight around 100lbs, blue eyes, dirty blonde hair and a very avarage cock I wasn't going to be impressing any girls in my class anytime soon.

I was starved for sexual attention, all those hormones swelling up in me, it got to the point where I would spend hours locked away in my room watching 100's of hours of porn desperately wishing I could take the place of any of these actors I didn't care who I just needed a release!

After a while porn wasn't enough, I began frequenting chat rooms looking for girls to talk to but as I soon found out on the Internet Men are Men and so are most Women and the Women who were actually Women didn't usually respond to any messages. I did however have guys messaging me first, at the time I had no interest, I only wanted women but with a mixture of loneliness and curiosity I started to casually send a few messages back.

This became a very slippery slope, it would start with a few messages but when the conversation turned sexual I'd have this swell of anxiety and ghost them, I kept telling myself I'm not gay, I have no interest in guy but I kept going back. This time maybe I'd reciprocate, tell them how much I'd like to try sucking their cock, how I would love to be treated like a bitch by them. A few weeks later I find myself exclusively in the gay chat rooms but it wasn't long before I craved more. I needed an actual touch, I'd already figured out guys are an easier bet and I've spent the last 2 months telling guys how much I crave the feeling of a hard pulsating cock in my mouth maybe it's time to except I like guys and I want to experiment.

I found a decent free gay hook up site and created a profile, it was great, immediately I start getting messages, now most guys were put off my age all except one and it just so happens he lived on my street his user name was DizzyDevil, 54, tall slightly overweight guy with short grey hair. At this point I didn't care what he looked like but for some reason the age gap was getting me even more horny.

We spoke online for a while and eventually swapped numbers, we chatted at length about what I wanted to do, he was very unstanding and patient with me, asked for my boundaries which at this point was only I wanted to give head.

I asked him what he wanted and he told me his ultimate fantasy was a school girl, this got my mind racing, I wanted nothing more than to please.

We eventually set a date, it was late on a Thursday night, my entire household was asleep, I grabbed my sisters school uniform out of the clothes hamper and got dressed

I took a look at myself in the mirror, a short, navy blue and green skirt, white blouse, pantyhose, a school tie and pair of pink panties. My heart is racing now, if I get caught sneaking out I am dead also I couldn't believe I was doing this. I managed to queitly get out of the house, making the short 2 minute walk with nothing but a coat and the darkness to obscure my girly attire, I got to his house and I froze, this was it was I actually going to do it? I could feel my heart pounding and as if I was autopilot I unconsciously approach the door.

I knocked on the door and it felt like forever until he answered, looking exactly like his profile picture Dizzy answered and invited me in. He led me into the living room and asked "so are the nylons for me?" too nervous to answer I nodded and took my coat off to reveal my full girly outfit and his lit up. He looked me up and down and told me how amazing I looked. We sat on the sofa together, he had some very explicit gay porn on the TV a little twinky guy getting fucked by an old man.

He asked if I was OK and I told him yes I'm fine, I could see his cock bulging in his sweatpants, I reached over and started to stroke him through the material. Dizzy asked me if I wanted to see it and all I could get out was a sheepish "OK"

He pulled his sweatpants and released his hard throbbing cock, it wasn't like pornstar huge but it was far bigger than mine, I wrapped my hand around it, fingers barely being able to touch my palms and slowly started to jerk him off, I loved watching his foreskin slide over his head, the warm feeling of his hard cock my hand, I was mesmerised. I was snapped out of my day dream when I felt his hand on the back of my head, he gently started to guide my head downwards towards his rock hard cock, instinctively I open my mouth as wide as I can to accommodate his thick throbbing head, I hold him in my mouth for just a minute, I use my tongue to explore as much as I can, swirling it around his tip, flicked it across the underside of his head, I can hear him sighing in pleasure, sometimes I'll hit a sensitive spot and he'll thrust up into my mouth before remembering its my first time and then letting me explore.

I start sliding my mouth down, slowly taking as much of his length as I can, I loved this feeling of holding this warm, hard cock in my mouth, I loved the way he had one hand on my head and the other running his hands over my nylon clad legs, grabbing my tight virgin ass.

I picked up my pace a bit and started to bob up and down listening to his sounds of pleasure, I would take breaks to rest my jaw wear I would worship his cock with kisses, or lick his balls.

I was fully into this now, loved this feeling but I wanted more, I wanted to feel dirty. I looked at him and nervously asked him to "use my mouth" and his eyes lit up, he stood up and made me kneel, placed both hands on my head and started to fuck my mouth, he was slow, every thrust I'd take him a little bit deeper until he asked if I was ready for the whole thing, I gave him a muffled yes and he pushed his cock all the way down throat and held it for a few seconds, my eyes went wide and started watering, he pulled out and coughed, spot everywhere, I didn't have long to recover before he was down throat my throat again, I had to tap out this time, I was gagging and choking but he seemed to be enjoying this.

After a few more slow thrusts into my introdution to deep throating he started to get a bit quicker, it wasn't long before he was full on fucking my mouth, all I could do is kneel there and taking, using bit of me not to gag too much.

His panting sped up as well, it was long before he was moaning, he pulled out and told me to open my mouth, I did as I was told, I knealt there while he gave his cock a few big strokes and with one last groan he shoot 5 thick ropes of cum into my mouth and onto my face. I swallowed my reward and felt an almost sense of pride, I took a look myself again in a mirror, dressed like a little school girl, my face plastered in an old man's cum, my jaw aching and my throat sore and loved it. I knew this was what I wanted.

After we got cleaned up he did suggest he has lube upstairs if I wanted to fuck but I wasn't ready for that yet, my head was still swimming from the throat fucking I had just received and declined this time.

I snuck home, checked the uniform for any unwanted fluids before putting it back in the hamper and then spent the night stroking my cock and reminiscing.