When I was in my second year of college, I had a girlfriend who was so into anal it was like an obsession.
I’d had plenty of pussy up to that point, but Sandra introduced me to the wonders of fucking a woman in the ass.
First of all, she initiated me slowly. She taught me to appreciate the sweet vulnerability of this particular sex act. Even as a novice, I immediately understood the delicacy it required. I fed my shaft into her gradually, mindful of her responses. The strange grasp of her butt hole thrilled me. It all felt so wonderfully strange.
Sandra was an aficionado of anal fun. I would fuck her doggy-style, fuck her ass while she stood facing a wall, and even drill her butt while she was on her back with her knees up to her chin. Her beautiful face would be twisted with pleasure as I bypassed her pussy for the ripe pearl of her asshole, plowing her deep with my cock and reaping intense sexual pleasure.
I didn’t know it at the time, but I realized later how exceptional she was. The women I subsequently dated had what seemed to be a common aversion to anal sex. Either they’d never even considered it, or they thought it was nasty, or they’d tried it with somebody clumsy and been put off the idea forever.
Memories of Sandra’s grasping asshole still haunted me years later. I belatedly realized just how emotionally intimate the act was, how much trust was involved. I had felt so connected to Sandra with my cock sliding in and out of her ass — especially when she’d wriggled with pleasure and squeal as she came.
Lucia’s my current girlfriend. She’s a smart, compassionate, gorgeous woman. The sex we’ve had has been great. I was lucky when I found her, but Lucia’s ass had been off-limits.
I’d gotten the message in the first weeks of our relationship. We were in bed, getting things going. I was fingering her pussy, and she moaned against me as I delved into her soft, shaven groove. My cock throbbed with need, but I was happy to take the time to bring Lucia to a state of full-on excitement.
I stroked my fingertips up and down her pussy, teasingly parting her lips and probing delicately inside. Her hips started to buck violently as her ecstasy soared. Then my fingers slipped, and I inadvertently grazed the pucker of her butt hole.
The touch sent a shock of joy through me. I recalled all the times I’d fingered Sandra’s asshole prior to sliding my cock inside its snug, welcoming grasp. But Lucia did not react with Sandra’s usual joy. She responded with a sharp yelp, backing away in horror. I muttered a vague, “I’m sorry,” and the incident seemed forgotten after that. Forgotten by her at least.
For me, that single incidental touch had wholly reawakened my memories of anal frolics with Sandra. I decided I would test the waters again with Lucia, gently so as not to pressure her. In the midst of a really wild fuck with her, with the two of us getting into all sorts of fun positions, I put my finger very deliberately against her butt hole, wiggling it a little to let her know I knew I was doing it.
Lucia froze. She looked me in the eyes and shook her head. So that was that, I’d figured. I certainly wasn’t going to make an issue out of it. What kind of schmuck would do that? I still really liked her and enjoyed sex with her.
I especially liked eating her pussy. She was so responsive it made me feel my tongue was magic. I could lick and lap and suck and nibble her cunt for an hour at a time. I loved her taste and the feel of her hot love-oil gushing down my throat. She would thrash about when she came, lifting her taut ass off the bed and crying out rapturously
One time when she did this, there was another slippage incident. I swear I didn’t do it on purpose. It was as innocent as the first time I’d unintentionally touched her asshole.
But after 20 minutes of going down on her, Lucia gave a climactic howl. My face was wet with her juice, and my tongue was still slithering like a crazed eel. Lucia’s hips jerked upward, and my tongue slipped from her flowing cleft and went sliding right through the valley of her ass to the forbidden ring of her butt hole. My stiffened tongue dipped inside her.
Once again everything froze.