En and Sara Get a Room

With our relationship now resembling an episode of Star Trek (boldly fucking where no one has fucked before), it was soon time for us to make the next logical leap - to get a hotel room for one of our rendezvous.

The idea came about when I was telling Sara about my family's plan for a vacation. Since my wife and kids had a little extra time off for the big family visit back home, and work needed me back sooner than I could accommodate by traveling with the family, I had a one-week window where I was going to be home by myself after returning from the trip. I half-jokingly threw out the idea of us getting a hotel room for the day when I flew back, when Sara's eyes lit up.

"You know," she said, "I could just drive to the airport, pick you up, save you the cab fare and we could put that toward a hotel room where we could have some real fun."

At first, I was put aback. I didn't want to be 'that guy', running to a hotel with my mistress. Then - duh - I had to remind myself that I was already 'that guy', fucking her in our cars and at work - which was probably a whole lot more risky to begin with.

So, Sara made the arrangements, and as my family vacation started coming to an end, almost time for me to travel back home, Sara's e-mails came more frequently. She started to come up with ideas of what we could do with our leisurely hours of alone time.

Top of her list: She wanted me to pop her anal cherry.

Oh. My. God. When I read those words, I couldn't believe what I was seeing. This was the ultimate taboo that I was told would never happen by the women I had been with, and here was Sara, this gorgeous woman who wanted me, begging for it.

What I shouldn't have done was read about having anal sex online. All the advice on the women's websites was to go slowly and gently for the first time. There were horror stories written by women about how painful and disastrous the experience was, and admonitions from self-proclaimed sex experts warning to proceed slowly and with great caution. I was just about paranoid when the 'big moment' came.

The whole time on the flight, I played the scenario through my mind. What would happen when that 'big moment' came? Would I be able to overcome my anxiety and perform?

When I landed at the airport on a rainy, dreary day, I quickly grabbed my bags and hustled to the main terminal. There was Sara, perfectly made up and looking fine. We kissed each other quickly, wondering if anyone we knew who could recognize us would be at the airport. We held held hands nervously, giggling like middle school kids on our way to our first dance as we walked to the car and headed off to our hotel room.

Once we got inside, we couldn't control ourselves. With a few hours to play with, the clothes came off quickly. We got busy fucking and sucking. I came once, deep in her pussy with her legs wrapped tightly around my waist, and she came a handful of times, each time talking about how shaky her legs were.

As we lay in bed recovering from our exertions, I could tell that Sara was starting to get ready for another go. I love when Sara starts to talk dirty, focusing her attention on my flaccid cock. Touching it. Stroking it. Kissing me while she pressed her tits into my chest. I was starting to come around, ready to go again.

She reached into the nightstand and pulled out a couple of items; a tube of lube, a condom and a small vibrating butt plug. "That," she said, "is to get you in the mood." I hadn't realized that she planned on both of us to share the experience that afternoon. I wanted to decline at first, but so far, everything she had done with me ended in an earth-shaking orgasm, so I'm glad I kept my damned mouth shut. With that, my cock sprung to attention thinking about what new tricks she had up her sleeve.

She knelt down beside me on the bed and lubed up her little toy, then took my cock into her mouth, sliding up and down the shaft. With her right hand, she rubbed a dollop of lube on my asshole and slid a finger into me. I had never done anything like this before, but as she worked her finger inside me, she was rubbing against my prostate. What started out feeling a little strange soon became exciting, and that was soon magnified as she slid the vibrating butt plug where her finger was just exploring. My heart was racing, and all I could hear was the blood pounding in my ears as I arched my back, enjoying every second of this special treatment.

By this time, the head of my cock was a deep crimson, swollen large by the excitement Sara was developing in me. She distracted me from my reverie and handed me the lube, asking me to grease my finger before I put it up her backside. I quickly obliged, pushing past the initial resistance of her hole. While I was doing this, she broke out the condom and rolled it over my hard cock head, down my veiny, throbbing shaft. She smeared a healthy dose of lube over me and removed the butt plug from me. "I want you inside me now!"

We both stood up, and Sara bent over the bed, piling up pillows for her to lean on. Her supple breasts pressed into the mound of pillows as she braced herself against the bed. I gently parted her ass cheeks and rubbed the tip of my cock against her asshole. She moaned and begged me to go inside her.

I was surprised by just how tight her ass was. Slowly, I pushed in until every inch of me was buried deep within her. The feeling was totally different than her beautiful pussy - a whole lot tighter - and I became concerned that I was hurting her. My thrusts were slow and careful, and with each one, her legs shook. I reached around Sara to cup her tits and play with her hard nipples as we coupled. I pressed the side of my face onto her back, and I could hear her heart racing with excitement.

After a while, she asked, "Why are you going so slow?" I told her about the stuff I had read, and she laughed. "This feels way too good! You pound as hard as you want to!" With her encouragement, I began to speed my thrusts. Sara worked a hand down to her pussy and began rubbing her clit. Her excitement built with every thrust, and eventually, I could feel her asshole pulse as the waves of her orgasm broke over her.

For me, though, I was just too psyched out to cum in her that way. Sara realized that, and after her orgasm, she asked me to back out of her. She rolled off the condom and began sucking me with abandon, taking her mouth off me while stroking my cock to tell me how awesome it felt to have me inside her like that, and how having my cock up her ass intensified her orgasm. With the thoughts of the curves of her gorgeous ass in my mind, I closed my eyes and thrust into her mouth, shooting my hot cum.

With a shower waiting nearby, Sara didn't have to be so careful to catch every last drop. She let some of my hot semen slide out of her mouth, down her chin onto her large tits. Looking up with her piercing blue eyes, she said, "Wow, now that was fun!"

While we haven't tried anal again since, I can't tell you how many times since then I have masturbated with the though of sliding into her hot willing ass being the trigger that takes me to completion.