Had a history for this boy but was in for quite an unexpected surprise.
When visiting a friend, we played games and in all honesty got kind of out of it. I don't want to say exactly how on here but let us just say the four of us were dazed.
Two of my gal friends called one bed which left me to share the other bed with an old fling. At first I was in no way okay with it, but then after a while I realized all we would be doing was sleeping.
The two girls passed out and then Cici and I decided it was time to pass out. We each laid down on the bed talking a bit and then slowly dozing off. I was facing the wall and he was facing the opposite wall. A few minutes later I heard a noise and felt him roll to face towards me pressing his arm against my back and ass.
He slowly began to caress my ass with his fingers all the while I pretended not to notice. As he continued to caress and squeeze my ass I began to grind back against him. Slowly he then turned so that he was spooning with me and I ground my ass against his now hardening dick. It felt so good rubbing right in between my cheeks and as I began to get into that rhythm he brought his arm ever so gently over my waist and onto my stomach. First slowly rubbing and caressing it then working his way up to my sports bra, grabbing and feeling my breasts as he cupped them in his hand. Tweaking first one and then the other nipple as I began to writhe and really build up my rhythm against his hard dick. He heard me begin to moan took my arm and replaced it at my nipple so that I continued to tweak and pull at them as he reached down to slowly caress his way down towards my pussy.
He rubbed and pressed almost as though he was massaging me until he got to my closed legs poking and prodding at my panties as I instinctively began to part my legs. As he rubbed with one arm, he now helped my leg to open even further as my leg crossed over one of his.
He continued to rub outside of my panties and I began to moan softly and humping up towards his hand. I asked for more through sort of a grunt and he found his way inside my panties rubbing my clit directly and as I really began to writhe up towards him he slipped in his middle finger as well. He knew just what to do to please me and took me completely by surprise.
He did his best to press my stomach down with his elbow as his hand continued to finger fuck me hard, sliding in yet another finger and occasionally dabbing at my clit when all of a sudden my hips bucked up towards him and he continued to fuck me fast as my pussy contracted around him and I squirted on our friends bed and his hand.
He then brought his hand to his mouth licking his fingers clean and then I pulled it towards my mouth licking them off again slightly tasting myself. I then turned back towards the wall and he went back to spooning with me his hand resting on my breast.
The next morning I awoke to a lovely massage of my boobs and we never spoke of the night before until a year later when we decided to repeat it but going even further this time.