Leah was determined to be second time lucky when it came to her anal cherry.
When I was 18 years old I asked my boyfriend, Jonah, if he wanted to take me anally. He jumped at the chance, but we were young and it was nothing like I expected it to be. It was painful and uncomfortable and I had to stop before it even began. I vowed that one day we’d try again, and it would make me whimper with the pleasure I’d always imagined.
We talked about how he’d pop my anal cherry: gently and slowly to begin with, then harder, making me feel like I’d fantasised it would. He said he wanted to show me how it should feel. So we went shopping for lubricant, and also some extra presents that I wasn’t allowed to see. We set a date, and the anticipation made me feel weak and dizzy. I wanted to feel him up there so badly.
When I arrived at his house on the day, he stripped me straight away and kissed me all over my body. Then Jonah laid me face-down on his bed. He tied my hands behind my back with ribbons and covered my eyes with a silky blindfold. I felt helpless, but excitement took over as he began to kiss me all over my neck and back, whispering how he was going to fuck me hard and make me come harder than I’d ever come before. I quivered as his hands brushed over my arse cheeks and pulled them softly apart. I heard a small click and felt cold lubricant cover my arsehole. He massaged it into my skin, and slowly slid a digit into me. He stroked the wall between my arse and my pussy and I couldn’t help but let out a moan.
He removed his finger and replaced it with something cold and solid; a small glass butt plug he’d bought. It was pushed into me as Jonah circled my clit with a lube-coated finger, making me tingle and throb. I couldn’t believe how good it felt, and because of the blindfold my senses were on overdrive. Everything was magnified and I could already feel the burning sensation of an orgasm building in my pussy. Then Jonah eased the butt plug out of my arsehole and covered me in more lubricant, and I felt his erect, latex-clad cock ease lightly against my entry point. The hole opened and let his cock enter as I let out a long, low moan of pleasure. Slowly, he started to move in and out of me, growing steadily harder and faster as I writhed about on his bed. It was more than I’d imagined; I could feel my pussy throbbing and my clit pulsing. My thighs were soaked with a mixture of lubricant and come. Jonah’s movements grew faster and faster and the walls of my hole gripped his cock tightly. We moaned together as he moved his hand between my legs and slipped two fingers into my pussy. His cock felt the hugest it had ever been and the finger almost pushed me over the edge as I imagined two cocks were forcing in and out of my holes.
We were in a frenzy; Jonah tugged on my nipples, making me feel dirtier and closer to orgasm. As he reached the heights of his speed and force I felt my pussy begin to pulse and I began to moan louder and louder as I experienced the strongest orgasm ever, my arsehole clenching his cock, which made him spurt his hot come into the condom in my arse.
Since that time, it’s been something my man’s treated me to on the first day of every month. I can’t wait till next month!
