Adventures in Wedgies

Night Session

Rita's POV:

It was around midnight when, as I leaned close to the door of my parents bedroom, I heared the distinctive snoring of my dad. I cautiously crept back upstairs and closed the door behind me. I sent Jeremy a text informing him that everyone was asleep. I then sat on my bed waiting in anticipation for him to arrive.

Several moments passed, the slightest sound made me jump but it was never Jeremy. Suddenly I heard a creaking noise and I saw the silhouette of Jeremy's figure being cast through the blinds. I went over to raise them and found my friend Jeremy struggling to loosen the window. With my help we managed to finally open it. Jeremy stepped in and took a moment to catch his breath.

"Dang...it's a lot of work to climb your roof." He said panting.

"I could've let you through the back stupid." I said sarcastically.

"That wouldn't have been any fun, I'd figured it would be more thrilling if I snuck in."

"Whatever...." I rolled my eyes.

I grew restless. Waiting for Jeremy to regain his form seemed to take an eternity. I sat back on the bed and stared at the ceiling.

"I thought being on the soccer team would have gotten you in better shape." I said.

"Keep sassing me...you're gonna regret it." He quickly replied.

"Then do it already." I laughed.

I nearly screamed when I felt Jeremy's body pounce on me. Luckily, Jeremy was quick to cover my mouth with his hand. Staring into his eyes I could see a look mischief. I felt his hand reach into my pajama shorts. His pulled the front of my panties up and began to tug on them in a slow rhythm.

Earlier when I had given myself a frontal wedgie it hurt instead of sending waves of pleasure. This time, with Jeremy, I was purring like a kitten. He removed his hand from my mouth and I let out a sigh. He then turned my over and began to pull the back of my panties again tugging in the same slow pattern. I felt like I was in heaven, my moans grew louder.

"Get up. On all fours." He commanded.

I was displeased that he had stopped but obeyed nonetheless. I got up on my hands and knees and slightly stuck my butt up in the air. I wiggled it a little in order to tease him. Jeremy grinned and gave my butt a firm smack. I jolted forward but returned to position wanting more. Bracing myself this time, Jeremy peppered slight smacks all over my behind mixed with a few hearty ones. I bit my lower lip and closed my eyes as his spanks intensified this feeling of ecstasy.

My eyes shot open when he yanked my shorts down exposing my butt that still had my panties wedged between my cheeks.

"Jeremy!" Shouted in a soft whisper.

"Bad girls need to be humiliated. You deserve it." He said and he rubbed his hand up and down my back. "It's about time I saw your cute tush." He teased as he gave my butt another smack.

That one stung a lot more than the pervious spanks and I gasped. Regaining control of myself, I looked at him with a worried look. Jeremy knew that it meant I was near my limit. He rubbed my butt some in order to soothe me.

"Want me to return to giving you wedgies?" He asked softly.

I nodded my head.

"Okay, time for the real fun." He said. "Get up and follow me."

I got up and pulled my shorts back in place. I rubbed my butt which still strung from the last smack. We went downstairs and then out the back. We stood in my backyard and I was very confused.

Jeremy's POV:

Once we were outside, I told Rita to walk over to the large oak tree in the their yard. She obeyed and stood next to it puzzled. I pulled out the handcuffs from earlier and told her to put her arms around the tree. When she did I locked her hands in the cuffs leaving her tied to the tree. I walked behind her and gave her panties a hard tug. Rita winced and groaned as I had her on her tippy-toes. With the lighting from the porch lights I could get a good look at her yellow panties that were decorated with blue polka dots.

"You ready for phase two?" I asked.

Rita shook her head.

I went over to a large black bag I had left when came over. I pulled out a rope and looped it through her panties. Rita's eyes widened, full aware of what was about to happen. She pleaded me not to but I I ignored her cries for mercy. I got the rope over a high and sturdy branch. I slowly hoisted her up and as her butt was lifted in the air, her upper body remained tied to the trunk. Her feet dangled as the were nearly a foot off the ground. I then pulled her shorts clean off and Rita let out a squeak. I now got a nearly unobstructed view of her cute behind as her panties had almost completely disappeared between her cheeks. Her butt was still slightly pink for her spanking.

"Let me down Jeremy...please..." She begged putting on her adorable pouty face.

"Not just yet..."

I pulled out a makeshift ball gag I had constructed from a large rubber ball and a bandana. I used it to gag Rita and left her there with her butt in the air for all to see. I pulled out a lawn chair, sat back and enjoyed the view as Rita struggled and moaned throughout the night.