Popping my anal cherry.. - Sex Stories

Popping my anal cherry..

He is older and more experienced than I am. I was nineteen and only had experience with mediocre vanilla sex and was eager to experience more. I wanted to help endear myself to him. I decided that I was going to give him my ass, I was going to give him my anal cherry. We began to make-out on the couch, I was flush with excitement and anticipation. His hands darting over my body. One up and down my thigh, flirting with the hem of my shorts. The other skillfully unhooks my bra and reaches around to cup my breast. I’m in love. I hold the back of his head as our tongues whirl around. I can feel his hard cock through his shorts. I hope I can take it. I reach under my own shirt and tug at my bra, the underwire held in place by the weight of my tits; and toss it to the floor. I stand up and lead him to the bedroom, pulling my little t-shirt up and over my head as I go. I turn to look to him and he’s way ahead of me, he’s standing there naked, cock hard as steel with a glistening of pre-cum at the tip. A hungry look in his eyes. His cock looks amazing, I’ve never been with a guy who is totally shaved before. He’s already made me his cum slut and I need more. I unbutton my shorts as he reaches out to me and with a single quick motion both the shorts and my damp panties are past my knees. I kick them off and crawl onto the bed giving my ass a little wiggle as I do so. I lay myself out on the bed like the wanton slut I feel like as he follows me onto the bed. My nipples are hard and ...

... sensitive as his mouth first the right one and then the left. I arch my back in ecstasy. I reach down instinctively to fondle my throbbing clit to find that he has beaten me to it. I squirm as he nibbles on my nipples and fingers me with two fingers while his thumb rocks back and forth over my clit. I whisper into his ear that I need him to ‘fuck me’, he looks at me and smiles. I whisper that I want him to ‘fuck my ass’ and his eyes flicker with a mix of surprise and excitement. I shimmy up the bed and spread myself open. He reaches over to the nightstand and pulls out the bottle of lube. He runs his tongue along the full length of my slit before popping the lube open. He squirts a small dollop onto his fingers and slowly massages my tight little asshole. Small circles round and around, teasing a fingertip inside. It feels good. It feels strange. I’m excited and scared. I hope I can do this. He continues to play with my ass, licking my pussy as he does. There is so much going on down there. I tell him that I think I’m ready. He lubes his cock and moves between my legs. He teases my pussy with his cock before placing his cockhead against my asshole. My legs wrap loosely around him. I hope that this doesn’t hurt. He slowly and gently begins to push into me. I clinch my ass as a natural reflex. He knows what I’m doing and asks me to try and relax. I will myself to relax a bit and his cockhead pops in. My eyes shot open and I let out a long gasp. He holds his position to let me ...