Yes (Strap-on Anal)

"Damn," I said surprised. "I didn't know I was supposed to save room for dessert, but if you really want to go again..." I trailed off with seductive look followed by a playful wink.

"That wink... just gave me an idea," Amanda said with a look so kinky it would have made a pornstar blush.

"Tell me more," I responded, needing to know what that look could possibly entail.

"Well if you liked my cock in your pussy sooo much...," she beat around the bush before finishing, "how about you try and see what it would feel like in your back door". She said those last two words so even a sexual novice like me could understand what she was talking about. Still, I couldn't believe what she had just put on the table.

"My ass," I asked incredulously, staring into her big excited eyes. I'd heard about anal sex before but put it out of my mind as something crazy people would do. If I didn't like putting things in my vagina, why on Earth would I want to put something in my ass?

"I totally get if you say no, but... PLEASE?" Amanda put on her best begging face. "I promise I'll be super extra gentle back there. It's totally the best time, I love it so much," she finished trying to persuade me to let her take my anal virginity. I did just swear to myself that I would try anything with her once if she really thought it would be pleasurable. And if she loves it that much how could it possibly be bad. I took a deep breath and cleared my head before opening my eyes and finding them locked with Amanda's eager orbs staring back into mine. Summoning my courage one more time, I agreed to let her put her dildo in my asshole. She screamed in delight and hugged me tight and I could feel her wet strap-on pressed up against my tummy.

"But I get lube this time!" I interjected as she broke the hug.

"Of course, of course!" she agreed and went to fetch the bottle from inside her toy chest under the bed. She returned moments later with a bottle of lube and a roll of baby wipes.

"Wipes?" I inquired.

"Buttholes are dirty business, ya know." she said nonchalantly. "Gotta make sure you're cleaned up back there before the fun can begin. Now turn over, onto your hands and knees," Amanda commanded.

I trust her completely, I reminded myself and did what she asked. Sparing all of the dirty details, suffice it to say Amanda got my ass plenty clean for our upcoming anal adventure. After she was done, she tossed the baby wipes off the side of the bed and gave my ass a playful swat. I let out a little yelp of surprise as her hand met my fleshy ass and peeked back at her.

"Oh you liked that didn't you?" Amanda laughed, noticing my lusty gaze. I could only nod in response. "I'll keep that in mind. But for now, look at this wonderful little ass," she commented as she groped at it. "In fact, it looks good enough to eat," she said spreading my cheeks apart and stuck out her tongue. I yelped again at the sudden sensation at my back door. It was weird but it wasn't bad at all.

"Do you want to stop?" Amanda dutifully asked me again as she took her lips and tongue off my asshole. I shook my head vehemently against the idea.

"Please don't stop," I called back. "I'll tell you if you should stop. Everything has been so wonderful, please keep going," I said, letting the words spill out of my mouth.

"I always want to keep the option in the back of your mind, just in case," Amanda reassured me, before going back to working over my now spotless asshole with her tongue. We laid there for a minute or two, on our hands and knees with Amanda attaching herself to my ass both with kisses and licks up and down my bottom.

When she thought I was sufficiently licked back there, she got up on her knees and started applying a generous amount of lube onto her strap-on and then directly on my asshole.

"You've never had anything back here before right?" she inquired.

"Never" I answered. For as much as I love to look at and grope my own ass, I've never put anything inside of it, not even a finger.

"It will hurt in the beginning, but it will turn all to pleasure soon," Amanda assured me while soothingly running her hands across my ass. "Do you think you're ready?"

"Yes." I answered quickly and solidly, not waiting for my resolve to falter. I wanted to at least try anal once, and I can't think of a better partner than the person lining up her rainbow strap-on up to my virgin asshole.

"Then, here we go. Please keep in mind what I said about stopping," she reminded me again. I nodded before burying my face into the bed and preparing myself for the initial pain that Amanda had warned me about. After a moment, I felt the head of her cock poke against my asshole ever so gently.

"Try to relax as much as possible, it'll hurt less if you don't fight it," Amanda advised. I said a silent thank you to the universe for giving me such an angel to spend the night with. I did as she said and relaxed every muscle in my body. Just like with my pussy, Amanda quickly stuffed herself up to the tip of her cock into my hole. I let out a startled gasp as the pain shot through me like a lightning bolt.

"That's it baby," Amanda cooed. "That's the hardest part. It'll stop soon," she reassured me, going back to gently rubbing my back and ass with her hands. It took a bit for the pain to subside, and even longer for me summon the courage to tell Amanda to continue. Without saying a word, she continued to push herself into my back passage. This time it didn't hurt as bad, but it felt so weird as something was going into my ass for the first time. Leaning down so that her chest was on my back, Amanda whispered sweet nothings into my ear to keep me calm. The longer she stayed in and the further she pushed, the better the experience was. After a time, there was no more pain at all and when I relayed that to Amanda, she told me that the hard part was over, and that all that was left was pleasure. She started pumping her hips in and out ever so slightly. It felt weird but I was definitely liking it now that the pain had subsided.

As time went on, Amanda picked up the pace and applied extra lube when necessary. It wasn't exactly better than having sex with my pussy, but it wasn't worse either. It was just different. Eventually as Amanda was starting to really get into the groove of fucking my ass, she put down another playful swat onto my backside. I yelped, interrupting my usual moans of pleasure. I looked back at her where she was raising and eye brow with her hand in the air, poised over my ass ready to strike again. With her eyes she asked me, "Again?"

"Please," my voice came out as more of a ragged whisper but it got the job done. Amanda's hand fell from on high and landed with the most amazing SMACK I'd ever heard. Between the fucking of my asshole with her big plastic cock and the spanking I was receiving, I was definitely happy I had let her fuck me.

"Spank me again," I pleaded with Amanda for another blissfully painful spank onto my fleshy ass.

"What's the magic word?" Amanda asked slyly. I was stunned for a second, not expecting to be given a question. I decided to answer as simply as I could.

"Please?" I said, unsure of my answer. I was rewarded with another spank on the ass.

Please," I said again hoping to continue my spanking session while her cock was running laps in my ass.

"If you want more, you have to say 'Please, may I have another spanking?'," the strap-on wielding girl atop me commanded. I obliged in an instant.

"Please, may I have another spanking?" SMACK

"Please, may I have another spanking?" SMACK

"Please, may I have another spanking?" SMACK

This kept going on for longer than I had bothered to count. With each skin rippling spank, I was treated to another wave of pleasure. The spankings were alternated to even out the punishment of my ass. Right, left, right, left, right, left.

Slowly, my orgasm mounted. The mixture of blissfully painful slaps on the ass combined with the long fake cock running in and out of my ass put me into a fit of moaning where eventually I couldn't even ask for another spanking, but thankfully they just kept coming anyway. In between the sharp slapping sounds of Amanda's hands and her hips against my ass, I could hear her labored breathing as well. I tried to bring her closer to the edge with me running my hips back into her cock as she rammed forward to meet me. My orgasm built even faster, and judging from her own quiet moans behind me, as was her's.

With a mighty thrust into my ass, I came hard and every muscle in my body tensed, squeezing the multi-colored rod inside me. The slaps stopped as Amanda tumbled over the edge with with me. We were like a pair of wild animals, fucking harder than we had any right to, and it felt amazing. As my orgasm subsided, I collapsed onto the bed with Amanda right behind me. I could still feel her cock in my ass as her arms wrapped around me. She brought me into a tight hug and buried her face into my hair and neck. After a minute, she came back up to say something into my ear.

"I'm so proud of you. And thank you," she whispered.

"You're the best roommate I could have asked for," I answered as sleep pulled heavily on my eye lids. Wrapped in her embrace, I had the best night sleep of my life.