I wasn’t prepared for sex that night. I was having a period and we had agreed before the date that it would simply be time spent hanging out, enjoying the easy conversation that had marked all of our dates thus far. I was disappointed of course, having formed some seriously erotic intentions since the last time we were together. But I had resigned myself to an evening of companionship with clothing on.
The last time he came to my place, he brought a black duffel bag that piqued my curiosity to no end. When I finally worked up the nerve to ask about it, he gave a coy smile and uttered one word that left me dripping into my black thong: “Toys.”
He came prepared. He is a former Boy Scout, after all.
Our first encounter had left me teetering on an unfamiliar edge: satisfied for the moment yet still craving more. My nipples, tingling and sore for three days afterwards, were a constant reminder of his firm touch, his surprisingly devilish ways. I was as eager for my next taste as a fat kid allowed to lick the frosting knife.
We enjoyed a leisurely day together, retiring to my place for an impromptu meal. As we sat on the couch talking, his eyes wandered over my body while I pretended not to notice. They lingered on my breast and I could tell from the gleam in his eye he was remembering the feel of my tiny, hardened nipple in his mouth. We continued our conversation, both of us acting normally in spite of the heated tension building between us.
Finally the tension was more than he could bear and as he made a casual comment about god-only-knows-what, his hand reached out and began pinching and rolling my nipple through my shirt. My thoughts, incoherent and disjointed as they were, evaporated in a steamy cloud of lust.
He was not going to make it out of my house without giving me an orgasm.
My eyelids fluttered involuntarily and I sighed as the pleasure zinged between my nipples and my clit. “You are going to cause trouble.” I told him.
He smiled, revealing his intentions with the hungry look in his eye. “What are you going to do about that?” He asked me as his fingers tightened around my nipple.
Oh yeah. Game on.
I reached over, tracing his crotch until he sucked in a breath and stifled a groan. “You have no idea how bad I want you in my mouth.” I told him. His cock swelled in response as he flashed back to our last encounter: his hands holding my head as he fucked my mouth with vigor.
“Duffel bag is in the car!” He declared buoyantly and jumped up to retrieve it. I raised a brow and asked the obvious question, “But what about my -”
He cut me off with a finger over my lips and a boyish grin that stood in stark contrast to his words: “I think I’ll fuck your ass tonight.”
Game most definitely on.
He took me to the bedroom and undressed me. Then he took out an enema kit from his bag. Umm… a what?
Yes folks. He came prepared. He is a former Boy Scout, after all.
He explained, almost clinically, what he would do. I nodded and decided to just go with it. After all, he seemed to know what he was doing and you don’t wait until the first drop on a roller coaster ride to decide you’d rather be on the ground.
We went to the bathroom and I followed his instructions, fighting back the incredible shyness that was overtaking me. I waited until I needed to use the toilet and announced I was ready. A brief pause and I firmly instructed him to wait outside while I took care of this most intimate business. I mean jeez, there are a few things even I won’t do on a date!
I reminded myself that an ounce of prevention was worth a pound of cure and waited for what seemed an eternity. I silently prayed the sound would not carry and my cheeks flamed red at the thought. At one point, I thought I was finished only to discover that no, standing up shifted things around. I sat back down and that scene from Austin Powers ran through my head, complete with computer voice: “Evacuation compl-“… “Evacuation com-“… “Evac-“…you get the picture.
Pretty soon, I could not stifle the laughter any longer. A serious bout of hysterics ensued. Giggling and making farting noises on the toilet is not exactly what I would consider erotic foreplay, but when I considered the fact I let my date give me an enema, I figured he brought it on himself.
Finally, I emerged. Refreshed, carefully cleaned, wiping tears of laughter from my face and trying not to think about what was going through his mind.
“All ready?” He asked with an amused grin as I walked into the bedroom. I nodded.
My laughter and embarrassment faded when his hands touched my skin. His cock was already rock hard, straining toward me as he led me to the bed and put me on all fours. He was, of course, prepared. His hands began stroking me, spreading the copious moisture that even with a tampon in, was seeping out of my pussy. He stroked the outside of my ass, tracing lazy, sensual circles that mirrored those his other hand was tracing over my clit. How he managed to erase the previous 15 minutes of cringe-worthy moments from my mind with two small circles is beyond me. But he did.
He applied the lubricant and slid his finger inside me in slow motion. Easing into me, breaking the seal of my virgin ass and beginning to finger me with long, smooth strokes. It didn’t take a genius to figure out this guy knows a thing or two about ass play. He inserted a plug, again easing it in gently and slowly, letting my body adapt to the intrusion as his fingers coaxed yet more longing out of my swollen clit. He clicked on the plug and the vibrations made me groan. He instructed me to remove my tampon and I grabbed a kleenex and obliged. I didn’t think he was going to go there but he slid his fingers inside my drenched pussy and my last thought before my brain stopped functioning was gratitude that my flow was very light.
He fingered my pussy, stroking my g spot and I took over massaging my clit while he worked the plug in and out of my eager ass. I felt the orgasm building and knew it would be epic. He teased me to the edge, pulling back, stopping his sensual onslaught and leaving me moaning, begging for more and pushing my ass back against him like an eager slut. He laughed softly and decisively filled my holes again, this time stroking faster and harder. I came so hard I saw blinding, white stars behind my eyes, my entire body shaking as the sensations overwhelmed me.
He removed the toy from my ass, kissing and stroking my hot skin as I shivered and twitched in the aftermath. He pulled me to the edge of the bed, one hand pushing gently down on my low back to position me to receive him. As my body continued to twitch from the first orgasm, he filled my ass with his cock and began to fuck me just as he had promised.
I loved it. I loved the fullness of him inside me. I loved the way his cock sliding in and out of my ass made me feel like the dirtiest little whore. I loved the fact that when he came, he thrust balls-deep inside me and I took every inch of him. I loved the fact that I barely touched my own clit and went off again, cumming like crazy for the second time, squirting my pleasure across his pelvis and down my thighs.
As I lay in his arms, feeling his hands stroking my soft skin as we talked, I realized there were very few lovers with whom I could have had this experience so comfortably. That thought led me to wonder what other aces this Boy Scout has up his sleeve. I stifled a giggle against his chest, impishly flicking my tongue across his nipple as two words ran through my brain: Game on!