Pregnant and in Need

"I couldn't resist playing a little."

Based on my response earlier and eager sprint from the room, she assumed this was my first time having anal sex and figured she'd better give me a little instruction.

"Put some on my hole, a lot on your cock, and work your finger in me a little bit first. Just take your time working your way in because I haven't had a cock in my ass in a long time and ... well, you're pretty big, so I'll have to get adjusted to you."

Looking down, I realized that although my cock was only average length I had a lot of girth. I smiled at the compliment she gave me while I started working the lube onto my cock. Putting a generous glob on my index finger, I started towards her puckered asshole. The contrast between her asshole and pussy was rather drastic. Her pussy was dark, meaty, and sopping wet whereas her asshole was light colored, drawn up tightly like a disapproving mouth, and looked to be in need of lubrication. It also had a few wisps of hair surrounding it, but was nothing like the pubic hairs surrounding her pussy that were still soaking wet from our combined juices.

My finger reached out and touched her asshole. She gasped as I started to work my finger and the lube around and in her asshole. My finger started to press into her hole and her muscle contracted to block its advance.

"More lube." she mumbled.

I squeezed a giant glob directly on her asshole this time and started to work my finger in again. Her ass contracted but slowly opened up to allow my finger to freely penetrate her and work the lube into her. Her hips wiggled slowly as my knuckle reached her entry and pressed further until it was completely buried in her ass.

"Mmmm. Give me two." she cooed.

Placing another generous glob of lube on her asshole, I pulled out my finger and started working the second finger in alongside my first.

"Oh, easy."

I continued to work my fingers into her until they were moving freely in her ass. Her hips began swaying with each push and her breathing picked up.

I pulled my fingers out and aligned my cock. As I pressed forward holding my cock, I didn't think this was going to work because my head wasn't going in and my cock, although rock hard, was starting to bend from the pressure. She suddenly relaxed her asshole allowing my head to pop in but then quickly contracted again pulling on my head while denying the remainder of my shaft entry.

"Oh, god!" she groaned as she struggled to push herself up from the table.

Allowing her to adjust to the intrusion and me to the sensation, I slowly started to push again. Inch by inch, my cock slowly disappeared into her asshole while she grunted but held still until my pubic bone was flat against her ass.

I stood there for a moment enjoying the feeling of her asshole grasping my cock and the look of her perfectly toned ass cheeks spread out. I reached forward to gather her ass-length hair into a bundle and slowly withdrew my cock until my head was pulling against her asshole then I slid back in. She groaned with approval as I began a rhythm.

"Fuck my ass. Fuck it harder!" she quickly started grunting.

I pulled on her hair to pull her into me as I thrust forward. I could feel my balls slapping against her pussy lips while her pussy coated them with her juices with each thrust.

"Fuck me. Fuck my little asshole!"

Her ass was so tight and contracting around me so hard that I knew I couldn't hold off much longer. I pumped hard and fast pulling at her hair causing her head to arch back.

"Make me cum! Harder!"

"Fuck, I can't hold off!" I grunted as I felt my cock swelling. Stream after stream shot from my cock filling her asshole. I thought I was drained before, but the cum jetted out like I hadn't fucked in a year.

"Felt like big load." she sighed approvingly as I slumped over her back slowly releasing her hair.

"I can't believe how good your ass felt."

"Ya, that felt so good I came twice: once when you first entered me and again when I felt your cum in me."

We laid with my cock slowly going limp in her ass for a few moments while we both caught our breaths. I slowly pulled my cock out and watched as her asshole tried to close back but remained stretched allowing a view into her gaping hole filled with my cum. I was fascinated by the contractions of her asshole trying to close and push my cum from deep inside her. Grabbing some tissues, I wiped her asshole and my cock.

We gathered our clothing and left for the store. As I pulled up to the opposite entrance we used previously, she leaned over giving me a tongue filled kiss.

"I'm going to make him eat me out tonight for being such a jerk. He'll just think the taste is different because I'm pregnant, but it'll be because he's eating your cum." she said smiling wickedly. With that, she reached over, squeezed my cock that was growing from her dirty little mind, and she opened the door exiting my car. As I drove off, I couldn't help but smile thinking about him eating my cum and the mess of paperwork, cum, and sweat spread across my conference table.