This story is fictional, and contains sex scenes between adults.(MM)
My Lucky Night
All night this lovely young girl has been looking across at me from her table but I'm shy and not game to approach her. Finally, at closing time I collect my coat and on my way out she is waiting at the door. "Hi I'm Annie, I've been watching you all night." "Well, um, I'm Ryan, I've been watching you too, and you really are very pretty." She smiles and holds my arm, "I live just across the street would you like to come over for a drink?" I looked at her and she must have seen the excitement in my eyes, "Yeah, I'd love to" We walk across the street, down an alleyway and into a small door, up some stairs and she unlocks her door. She offers me a drink and I sit on her couch feeling quite nervous. She is about 5'6, shoulder length light brown hair, slim, and only a small chest from what I could tell. She sits beside me and runs her finger along my leg then snuggles in closer. I pull her hair back and she leans forward and kisses me. I pull back straight after the kiss. "I'm not very good at this, sorry, I really haven't done much before." She smiles and kisses me again this time more passionately and I feel her hands on my shoulders. I run my hands down her slender back and feel for the bra strap, but there are no straps. She sits back and undoes my shirt and pulls it off me, then kisses my chest. I lean back on the couch and she undoes my belt and then my fly. As she pulls at my pants I lift my hips and allow them to come off. Annie is in complete control as she kisses down to my boxers and rubs my growing cock. "Annie, I don't know what I should be doing?" I gasp as I feel her fingers squeezing my cock. "Just lie back and relax, just let me do it", her voice is husky. She pulls down my boxers and kisses the tip of my erect 6" cock. I moan and lean back closing my eyes and taking in the feel of someone else's hand on my cock for the first time. And then her tongue and lips circle the end of my throbbing cock. I'm now lying naked on her couch and she sits between my legs sucking on my cock and her hands are rubbing round my balls and the crease of my arse. Her fingers press and probe my small arse hole as she keeps sucking on my cock. She stops and looks at me with a sly grin. Then she pulls her woven shirt off over her head exposing her small boobs, mainly swollen nipples. They looked like my little sister's when she was just starting puberty. She reaches down and undoes her skirt at the side and pulls it off. Leaning forward, Annie kisses my chest then up to my mouth and we kiss hard for several minutes as my hands move over her bare smooth back and gently squeeze her tight arse. I can feel her pubic bone rubbing on my cock giving me goose bumps. I decide to take the initiative and I move over kissing down her neck and over her chest to her puffy nipples. I take each in my mouth flicking my tongue over them. I'm so excited I feel all shaky and desperate to get relief. Kissing down further over her belly button and down to the waistband of her panties. I feel her pulling me so I turn round and get in a 69 position with her. She takes my cock in her mouth and her finger presses into my arse and it feels so good. She then presses a second finger in, and although it hurts a bit the pleasure shoots into me. "Annie, that's so good, I love your finger in my arse, oh yes, fuck my arse baby", I surprised myself with the intensity of my desire for her. She squirmed round and I felt her tongue licking under my balls then into my arse crease. I had forgotten about pleasuring her and my head was spinning. She opened my legs wider pressing her face between my arse cheeks and her tongue flicks my tiny hole. A shiver rips through me and I groan and try to open my legs wider. I roll onto the floor and Annie is on top of my back still licking my arse. I just laid there taking in all the pleasure she could give me. I felt her again press her fingers into me wiggling them round and she seemed to have opened my arse hole a bit. The feeling was still so good. I got up onto my hands and knees and buried my head in the seat of the couch as she licked deep into my arse and gently pulled my foreskin back and forth over my cock head. I was losing all control and I was her slut to be treated, as she wanted. I felt something bigger than her fingers pressing into my arse and it felt nice so I pushed my arse back and is started to slide into me. It felt unreal as she kept gently rolling her fingers round my cock. I could feel this thing filling my arse, stretching me. The pain was offset by the sheer pleasure. Then it seemed as though I was being fucked by this thing, oh yes that's what is it. As I reached back she moved my hands to the front again. Annie kissed my shoulder and moaned holding my cock tight then she grunted and I felt this thing jerk hard into me. Ooh yes its alive I can feel it throbbing and jerking. Everything stopped and Annie held me tight and I leant forward on the couch. My cock was ready to blow, as I needed more action. The thing inside me seemed to be getting smaller. Annie moved and I felt it slide out of my arse. She moved back and I turned and shuddered. Annie had a small cock hanging between her legs. I stared not knowing what to do. I looked at her slender body with her small budding nipples. There was no hair round her cock or on her balls. She actually looked very sensuous. My cock stayed hard. Annie turned round and put her head on the seat of the couch with her cute arse pushed out and open. I stared at her cute body for a moment then I moved closer and ran my hand over her bare smooth skin, between her legs and through to her cock which was still semi erect and about 4" long. I kissed her cheeks and my tongue ventured towards her tight hole. She moaned as my tongue touched her small button. The taste was not bad, just different. She wiped a blob of cum off the tip of her cock reached between her legs and rubbed it into her arse. I reached behind to my arse and wiped some of her cum that had started to ooze out onto my finger and rubbed that into her arse. Holding my cock I rubbed the head into her hole and started to press gently at first then harder. "Yes Ryan, push harder but be careful." I pushed keeping the pressure up and slowly my cock head disappeared into her arse. I watched as her arse swallowed my whole shaft. I reached round feeling her cock and it was erect again. I had never even thought of playing with a cock before but here I was gently jerking one off as I fucked her arse. I slowly fucked her arse getting faster and more aggressive until I could feel my cum about to blow from my balls. I squeezed her cock head and pushed in hard one last time. I felt her cock throb as a rope of cum covered my hand, and her arse contracted round my cock. I almost screamed as I had the biggest orgasm I'd ever had. Spurt after spurt filled her hole and I kept rubbing her cum over her cock and balls. As I sat on the floor with my shrinking cock I looked up at Annie who had a very satisfied look on her face. She told me that tonight was her first night out and that I was her first one. She had only started taking the hormone treatment 2 months before and that was why her chest looked like my 12 year old sisters. She told me she was 17 and hoped to be an erotic or lap dancer. That was the start of an amazing 6 months for me and there are many more stories to be told.