Cheap Trip

"Please be gentle." I mumbled into the pillow I had ground my face into.

"I wouldn't have it any other way cutie."

I could soon feel something else push itself against me. I did what she had told me before and relaxed as best I could. After only a few attempts I felt her head slip past my opening. I gasped in shock as I got used to the feeling.

"Please..." I whimpered.

"Please, what?"

"Please. Be gentle..."

"I know."

It was only a few moments before she started to push again. Her length sliding with ease into my lubed up and no longer virgin hole. It seemed like ages before I could feel her hips pressing against my own. I realized then that she had bottomed out and I had taken my first cock inside me. She moved her body weight so that she rested on my back, her lips beside my ear.

"You are such a good boy." She cooed to me. I moaned in please at the words.

I am a good boy, aren't I?

She slowly started to shift her hip afterwards. All the way out, until most of her length was retracted, then all the way in, until her hip met mine again. In slow full strokes she did this. In, and out. Back, and forth. Until she felt I could handle the feeling. Then she sped up her thrusting, and before knew it, the sound of our hips slapping together, mixed with our mutual moaning and groaning of pleasure filled the room. I could feel her cock rubbing every part of my insides as my erection hung forgotten in the heat of passion. She would grip my hair and lean in for a kiss, or grab my hips as she trusted inside me. Other times she would push me down into the bed, or bring me up to meet her as she reached around and stroked me, but never to the point of orgasm.

We continued like this for what felt like hours until she slowed down. I didn't feel her cum so I knew she wasn't done. She withdrew fully from me with a pop and told me to roll over. While I did so she applied more lube to her wrapped cock. It wasn't long before her legs were spread under mine and she was thrusting again into me. I could feel her pounding away at my prostate now. Her relentless onslaught making my ooze out. She rubbed her hand on my precum and used it as lube to stoke me with it. We were both very drunk at this point, both off the wine and form the sex.

"Cum for me." She pleaded. She needed it as much as I wanted it. "Be a good boy and cum for me!" I wanted to be her good boy. I need to be. With those two words leaving her lips I felt myself loosing all control and spurted rope after rope of sticky seed across myself and hitting just below my chin. I don't think I had ever cum so much before in my life. The contraction must have been too much for her, of maybe it was the scene in front of her, but she soon plunged as deep inside me as she could go and I felt her pulsing as her own jizz filled her condom. We stayed like that for a while regaining our breath and basking in the afterglow. Her cock slowly softening in my ass before it slid out.

I was almost ready to fall asleep when she started to move again. She crawled over me and gave me another extremely passionate kiss before dropping and laying beside me, both of us still breathing heavily. A few minutes later she spoke up. "So," she looked at me "how was your first cock."

Without thinking, or having a need to think, I said the only words on my mind. "That was phenomenal. You were incredible." She looked so pleased with herself, and I was as well. It was absolutely a night I would never forget. We continued for a few more rounds that night. Me inside her, mutual oral, lots of condoms used. By the time we were well and truly tired the sun was starting to peek in through the blinds.

When we both got cleaned up in the morning and she was about to leave for some quality R&R she did something I did not expect, she took a pen out of her purse and wrote a number down on my hand. "Before you leave, give me another call. I have a few friends that would love you." She backed up out the door as she spoke. "And if your lucky, I might be able to convince them to do a 'group discount.'" She winked at me before she practically skipped away towards the elevator.

It was going to be a very fun week in Thailand.