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This happened some time ago and was the beginning of my journey to becoming the slut I am today.
When I moved to London, my parents insisted that I stay with my cousin, at least in the beginning. I've always been a bit feminine, with a wider arse than most guys around me, puffy nipples, and was prone to getting bullied, even while I was at uni. Plus, I had started my transition by this point and was gradually getting even girlier. My parents figured that bunking me with a member of the extended family would help keep me safe. It helped that he was a bulky lad and quite tall, at least compared to me. I was nervous as I moved in. I hadn't seen my cousin for a while. Growing up he was always the big brother looking out for us younger lads. Whether it was getting into trouble, raiding our parents' alcohol or chasing after girls, he was always there for us. Come to think of it, he helped me get my first girlfriend by feeding me the cheesiest lines. So coming to live with him felt like spending time with your crush, I know, interesting choice of words; I was impressed by everything he did and didn't want to disappoint. As it turned out, I was nervous for no reason; Jake was still the awesome person he was when we were growing up. However, I wasn't sure how he would react to my transition so I kept that from him and dressed normally while he was around, at least on the outside.
We quickly settled into our respective routines. I started out as a waiter in a burger chain, not McDonald's, and would spend most of the day, and evenings, working my tushy off and chasing tips. Jake was busy with his own job but did the normal 9 to 5. He'd get home a few hours before I did and would usually prep (or order) food for us, ready for when I got back. He was caring that way. I often thought about repaying him and taking care of him some way but he would think of everything and I never got the opportunity. We would eat, joke around, watch tv, and eventually hobble to our rooms to get some rest.
Remember when I mentioned that I was looking for an opportunity to pay him back for all he did for me? Well, his birthday was coming up. I figured I'd finish work early and surprise him. I had the perfect plan in mind, involving a chocolate cake, party music and then dinner at our local gastro pub. For some reason, I even made an extra effort with myself that day. I showered, conditioned my hair, shaved my legs and chose a sexy pair of underwear to put on for the day. I am not sure what I was thinking. I certainly wasn't expecting anything to happen. I think I just wanted the confidence of looking good.
On the fateful evening, I got off my shift early. On the way home, I picked up Jake's birthday cake and walked to his flat, humming all the way. I was excited and looking forward to the evening. Once I got home, I took my keys out and started unlocking the door. "Hmm, just one turn?", I thought. Maybe I forgot to lock up properly as I left for work. No worries, I went inside and straight to the living room, humming and not paying any attention to anything around me. As I put the cake down and looked up, I saw Jake, sitting on the sofa with a shocked expression on his face. In his hand was his sizeable penis. His other hand was holding his laptop in place, the sound of a woman moaning coming from it. I stared at this like a dear caught in headlights. A moment, must have passed but it felt like eternity. I stuttered a sorry and turned to leave but as I did so I caught the expression on his face change to embarrassment. I managed to get to the door and thought about cracking a joke to ease the tension. I still thought highly of him after all, and this was something any healthy male would do when they weren't expecting company. I turned back slightly and said, "would you like a HAND with that?". Silly, I know but it made perfect sense in my head! "Umm, are you sure?", Jake replied, "I.. I .. I think that could help". I don't know what came over me but I felt like I owed Jake for the embarrassment he was feeling, so I went back and kneeled in front of him, took my hand and placed it gently over his swollen and vein-y shaft. He let out a soft moan as I did. It felt big in my hand and I started moving my hand up and down along the length of it. "Like this?", I asked. "Mmmhmm", came the reply and that made me blush crimson. Here I was, kneeling in front of someone who was like a big brother to me all my life, and holding his massive cock, looking up at him and trying to make him happy. After stroking his cock for a few minutes I was feeling arousal myself and that was making me braver than normal. I leaned forward and kissed the tip softly. But before I could do anything else, I felt his big strong hands grab my head and force it down, pushing his member into my mouth aggressively. And as soon as it was in, I felt something warm shooting inside my mouth. It had nowhere to go so I gulped as much down as I could with the rest exploding from my mouth and dripping down my shirt.
Jake pulled himself out of my mouth and apologised, "I got carried away. But you looked so damned sexy when you kissed it that I couldn't help myself". I looked up at him, his strong arms still holding my head, bit of cum still wet on my lips and smiled, "It's okay, Jake. I hope that relieved you a little bit". He didn't say anything and I noticed his eyes on my chest. The dripping cum had made my shirt wet and a little bit see through, thank you cheap work uniform, and he noticed my bra under it. "I didn't realised that you wore a bra, little bro", he said, "It looks good. I want to see it properly. Can you, ummmm, take your uniform off for me, please?". I was super horny by this point and while embarrassing, I got up, turned my back to him and proceeded to take my shirt off, followed by my trousers. I stood like that with my arms across my chest with Jakes eyes running all over me. It felt strange but also good, to have someone look at me with lust. Jake asked me to turn around and I obeyed him. His eyes were on my tiny but perky breasts and then they moved lower, catching my own small member straining and leaking against matching panties. Come closer he commanded and I stepped forward, just enough for him to reach behind me, grab a hold of my arse and pull me forwards. "Ooooooh", I moaned. His hands on my ass were driving me wild. It was the first time a man had touched me like this and it was everything I imagined it would be like. At that moment I was willing to do anything to please him, and he knew it. He moved one of his hands and grabbed one of my boobs causing me to moan even more. "You look so sexy in your underwear", he said causing me to blush even more, "But I think you would look better without it". I nodded, reaching back and unhooking my bra, my nipples hard and erect caught his attention and he couldn't help but pinched one making my yelp and moan ad the same time. "Now your panties", he commanded greedily. I looked away and pulled my panties down, stepping out of them, my hand shielding my dignity. Jake reached across and moved my hand away looking at my tiny clitty, hard and leaking precum. "Hmm, I always imagined that you would be the same size as me", he commented making me blush from embarrassment. "I.. I... is it okay to say that I want to fuck that sexy arse of yours?", Jake said. I giggled and blushed, "Yes, I would like that, mmmmm. Just let me get some lube.".
I ran to my room, my mind spinning from what had happened and what was about to happen. I opened the wardrobe door and picked up the lube tube. I turned around and froze. Jake was standing in the door. He came in wordlessly, led me by my hand and laid me on my back and on my bed. He lifted my legs and put them against his broad shoulders. He then proceeded to cover his fingers in lube. I saw this and was shivering with anticipation. Then I felt his finger against my ass hole, slowly circling, gently probing and without warning pushing inside me. I arched my back, this feeling was more intense than when I try to finger myself. Starting with one, he eventually made it to three and then announced that it was time and he could not wait any longer. I gasped as he entered me, thicker, bigger than any dildo I had used before. As he went in, I came a little from this new sensation. Jake laughed when he saw cum spurting from my clitty and dripping on to my tummy, "Guess my cock is a hit!", he gloated. In and out he went, his hands holding my legs and each thrust making my brain explode from ecstasy. He reached forward and held my limp clitty in his hand while continuing to have his way with my ass. "I need to hold on to something and your little cock is perfect", he laughed. I was blushing red from embarrassment and couldn't look at him. My eyes closed, I felt every thrust and all time seemed to stop for me. Before long he announced that he wanted to cum. I wanted him to cum in me! I wanted him to get me pregnant somehow! But I said nothing and Jake pulled his cock out and proceeded to spurt his cum over my stomach and tits.
Before I could say anything, Jake got up and said "I'm sorry dude. I don't know what came over me. I need to figure things out!". And with that he rushed out of the room, leaving me covered in his cum, satisfied and confused.
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