Quickie: Ride of a Lifetime

I smiled down at her and asked, "Did you like that?"

"Mmm, yes... you're a quick learner but you did forget one thing. One thing I figured you'd know was important to me," she said.

My mind raced. What the heck was she talking about? I've known her for less than a day. What did I forget that I should have known? I gave her a shrug and the look of confusion.

"Really, Jase... what else is available down there?" she asked, motioning to her sex.

I still didn't know what she was talking about. I licked every inch of her pussy, stuck my tongue in her tangy hole, fucked it with my tongue, licked and teased her clit and lips... what... oh shit! The look of realization must have showed on my face.

"Exactly. You never even touched or tongued my anus, Jase. It's very sensitive and after I fingered it earlier, I would have expected you to know I like to be touched and played with there," she said.

"I'm sorry... I was just so focused on everything else..." I started to apologize.

She started laughing. "I'm just messing with you... you did great, but I wouldn't mind next time," she said.

I kind of missed out on a golden opportunity I thought, but that quickly went away when she reached forward and grabbed my hard cock, pulling me on top of her. I snuggled between her legs, still not inside her, but placed my hands on her breasts, my favorite thing, and fondled them for a few seconds before inching forward until I felt my cock entered her extremely hot and wet tunnel.

"Mmm, yes... nice and hard... just like I like it," she said as my length ended quickly inside of her.

I slowly thrust my cock into her, doing the best and going as deep as I could while fondling her breasts. Moving my face over the left one, I sucked on her nipple and thrust my cock over and over into her body, loving every sensation from my cock to my hands and mouth... there was nowhere I'd rather be. We were pretty much the same height and our bodies fit together so well. She caressed my back and ass as I sucked and fondled her breasts and thrust my cock in, over and over and over.

As I continued, I noticed the room getting darker as the minutes passed. I had no idea what time it was but I started thinking it was getting to be evening and the sun was about to set. I had spent a lot of time with her, but I wasn't complaining. My cock was just humming with pleasure, staying hard, and I basked in the woman under me. I think she realized how late it was getting as well because about then, she told me to raise up on my knees and fuck her harder.

I kneeled below her, raising her legs up and bent at the knees. She held them for me so I could play with her clit and thrust into her at the same time. Friction was much better this way and my cock got harder as my pleasure increased.

"Yes... oh... yes... it's perfect... your head hits the perfect spot every time you push in!" she voiced.

I rotated between her tits and her clit with my hands as I rocked in and out of her fast, building up a constant rhythm as sweat began to appear on my body. I knew I would have to work for this one, after cumming so hard the previous two times. She reached up and caressed my chest as I fucked her hard and fast, breathing heavily from the effort. Pleasure grew and grew, the delay time only made it better. I wanted her to cum one final time before I did.

Pinching her clit and driving my cock hard, got her going. Her nipples hardened on their own as I kept working on her clit and driving as deep as I could each time with as long of a thrust as my cock could manage. Fuck it felt so good, she looked so sexy and perfect below me on the lounge. Nothing could rival this experience or this day for me... probably for my entire lifetime.

"That's it... Jase... I'm... I'm... so close... don't stop... I'mmmm... going to... cummmmmm!" she screamed.

Her body tightened beneath me, her legs shook in her own hands and I saw the waves flood her face and body. Nipples hard as ever and her eyes closed as she came for me one final time, making my thrusts more meaningful. Her pussy flooded as it clenched over and over on my cock, taking me closer to cumming but I still had work to do. I fucked her as hard as I could, through her orgasm, trying to cum with her, pounding away at her as she spasmed and panted for air.

I was working so hard, sweat was dripping down onto her and the lounge chair. I was pounding away at her pussy but I just couldn't get myself to reach the point of no return. I was so close but my energy level was waning, making me slow down to catch my breath as she finished her orgasm.

"You... didn't... cum," she stated, as I slowly thrust in and out as I caught my breath.

"Nope... not quite," I breathed heavily.

"You worked so hard... made me cum big time... such a stallion," she said, grinning up at me as my cock slowly entered her and withdrew.

She was so wet and open that the friction was almost nonexistent. Possible con of having a smaller dick. I didn't really know what to say to her. I was wishing that I had cum but for some reason hadn't. I just shrugged my shoulders.

"I know what will make you cum. My gift to you, before you go?" she said.

"Gift?" I asked.

"Yes, Jase. I want to give to you something even my husband has never had," she said.

"What do you mean?"

"I want you to put your hard cock in my ass," she said, taking my breath away.

My heart skipped a beat. She had just offered me her ass, her virgin ass. I had never done anal but I was surely not against it, finding a woman that is willing isn't an everyday occurrence.

"Are you sure?" I asked.

"Yes... do it now and cum for me one more time," she said, pushing me away so my cock flipped out of her pussy.

It was hard, wet, and throbbing; especially with the thought of anal sex. She pulled her legs even further up, giving me an incredible view of her open pussy and puckered ass below. Her and my juices had collected around her anus and I was covered as well. I figured we had enough lube to do this thing, after all she had taken two of her fingers in her ass earlier, so I was sure she could handle me.

"Just go slow at first... let me open up for you," she said as my heart raced and my body felt tingly all over despite the fact that I wasn't even in her yet.

I bent my hard cock down, placing my purple head against her tight anus, holding myself level. I pushed slowly forward and watched her tight ass slowly spread over my head. I had never felt anything or seen anything so incredible in my life. The heat and the pressure were phenomenal! My head slipped in and I paused, froze actually, looking down at my cock in her ass. My heart was pounding in my head and chest.

"Mmm... that's good... just stay there for a bit," she said. "Play with my clit," she added.

I quickly started rubbing her clit and pussy as my cock was just into her ass. I could feel my cock pulsing and throbbing as her tight ring of muscles clamped down on the head. I didn't want to ruin anything so I stayed frozen until she told me to move again.

"Okay... a little more now," Madison said.

My heart was going to leap from my chest it was pounding so hard. I could barely hear her from the beating in my ears but I moved forward, sending another inch into her tight ass. Holy fucking shit! I can't even describe to you how good it felt. She urged me on and soon I had all of my length inside of her as we both panted and basked in the experience of anal sex for the first time.

"Oh... my... yes... you seem so big... it's so tight and I'm so full... I really like it," she panted.

"It's unbelievable," I was able to voice.

"Good, then, fuck my ass and cum for me," she said. "I'm ready for you."

I pulled my cock out to my head and almost nutted from the sensation of her ring tight against my shaft as I pulled out. It was so tight she scraped me clean. I don't think I had blinked since putting the head in. Pushing in again I knew I wasn't going to make five minutes like this. It was just too exciting, too hot, and too tight, but I was going to enjoy every second I could.

I continued to rub her clit as I watched my cock go in and out of the sexiest woman's ass I had ever fucked. I couldn't believe I was doing this, this gift she had given me. It felt like nothing I'd ever felt before and I was on the verge of cumming within three or four full thrusts. The combination of anal and the newness of the experience blew me away. I have never felt like that before or since.

"I'm... I'm going to cum!" I gushed.

I held myself deep and let it go, releasing my muscles and exploding inside of Madison's tight ass. My cock pulsed and spasmed as I sensed jet after jet spray inside of her. It felt even better than the oiled handjob she gave me as the first part of this experience. I just grunted and came, shaking and moaning as I jettisoned my load inside of her, before falling over on top of her totally spent.

"That's it... that's my good boy... cum for me... fill my ass," she said as she held me and my cock continued to twitch and contract.

**

We laid there for a quite a while, the room got even darker, and I knew I was running out of daylight to get home on my bike. I wasn't planning on being this late so I didn't have my lights, and riding without them was very dangerous.

"I've got to get going," I finally said to her, my head on her breasts.

"I know. I'd offer for you to stay but my husband is supposed to be home later tonight," she said.

This got me a little worried and I sprang up off her chest and crawled backwards off of her.

"When?" I said worried.

"Don't worry, he's not going to arrive until well after dark, like eleven or so," she said.

I relaxed a little until a mechanical voice sounded in the house that said "Front Gate". Both of us looked at each other in a panic and I asked, "What the fuck was that!"

"He's home early... that was the security system telling me the front gate is opening... You've got to go now!

"Fuck!"

"Run to the gym, get dressed and meet me at the front doors. I'll have your water bottles and your bike ready. He will go to the garage since he's driving; we can do this!" she said, as we both darted out of her private room.

I ran down the stairs and back through the dining room into the kitchen, going the only way I knew to the gym to get my shorts, socks, jersey and gloves. I've never put my clothes on faster in my life and ran as I put my gloves on, back toward the main doors. I passed the garage on the way and saw the door open to the outside. Ryan's car was already in the garage as I sprinted past.

Madison was at the front doors holding my bike with the door open and my water bottles in place. She had taken the time to put a robe on before I got back to her.

"Hurry. I'll open the gate before you get there... it will shut on its own... thank you for today, Jase... I'll never forget it!" she said, kissing me on the cheek.

I clipped in to my pedals and headed toward the opening front gate only glancing back once to see her waving to me before shutting the door and disappearing from view.