FreeFirst-time experiment for a man to dress. Sex Pics

Alyssa is pleasured, Scott connects the dots.

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.