Sam and I met back up in our second city. While there was no shortage of kink and sex in this city, we didn’t find a club to enjoy, we were lucky enough to have gotten an AirBnB of some artists who were out of town. The design was minimal, but far from boring. There was a nice balcony to enjoy the fall weather, a decent sized living room, and a comfortable bed. What more could we ask for? We put out feelers to meet with women or couples, but didn’t have much success. The male half of a couple from a very conservative country reached out hoping to explore while they were in a more sexually liberated region of the world. The idea was hot, but the vibe was wrong. Everything was being driven by the man, they very obviously hadn’t had NEARLY enough discussions about it, and I was going to be the only person with group experience. I didn’t nearly have the bandwidth to facilitate, given the lack of communication, so we passed. I digress. Sam and I were having a great time exploring the city, eating and drinking our way through. To try and tell anything in some sort of coherent connected story would be an exercise in fiction, so I will stick with some memorable Anecdotes.
For those who read my first stories with Sam, I had introduced her to anal play, and she was starting to get excited about it, so I had purchased a nice bejeweled stainless steel butt plug as a souvenir for her. On one of the first nights, I asked Sam to go take a shower, clean up, and prepare herself for the butt plug. She walked out in a towel, which was quickly lost as we furiously started making out. I laid her down on the bed and began kissing down her neck, trailing kisses, and drawing my tongue down to her nipple where she gasped as I took it between my teeth. My fingers found her nipples as my kisses continued down her stomach, and teasing and exploring the space between her naval and her clit. As I sucked her clit in between my lips, she moaned and arched her back. I continued licking and sucking as I worked a finger into her pussy.
As I felt her ramp up and get excited, I pulled back and told her to get on all fours. I teasingly stroked her pussy while I grabbed for the butt plug and anal lube. I warmed the plug up in my hand while I continued to stroke her pussy. Once I had lubed the plug up, I began to slowly inset the plug into her ass. A long drawn out inhale emerged from her chest as she collapsed into the bed and pushed her ass towards me. I kept my slow progress moving further until I passed the widest part of the plug, and her ass sucked in the rest until it hit the flared base. This caused her to moan as she pushed her chest off the mattress, and looked back at me, biting her lip, pure hunger in her eyes. I walked to the side of the bed and without any instruction necessary she pulled my boxers down and started sucking my cock. I enjoyed the feeling of my cock head hitting her throat while I unwrapped a condom.
I rolled the condom on, lubed up, and slowly entered her from the back. I felt the bulbous contour of the plug run down the length of my shaft as I slowly entered Sam’s pussy. This new level of tightness was heaven, while the feeling of the plug was sending shivers down my spine as it stroked the top of my cock. Sam was moaning as I slowly stroked, enjoying the sensations running through my body. I placed my hands on her hips while she dropped her chest into the mattress and let out breathless expletives. I continued to pump as I could feel Sam’s pussy clenching down. After a long guttural moan and her shudder, I pulled out, rolled her onto her back, and thrust back into her pussy. She was a sweaty mess at this point, her face was jumping between a smile of elation, and a fully clenched face, as she moaned out. I was getting close but don’t usually come from intercourse, so I pulled the condom off and started stroking myself as Sam started playing with her clit. I towered over her while she tilt her head back in ecstasy. Around the same time Sam was coming again, I felt myself building, and squirted ropes of cum onto her stomach. She laughed and sighed as I dropped to my left arm, right hand slowly stroking my cock, panting as I came down. I grabbed a warm wash cloth to help her clean up and we cuddled as she came down.
Source: reddit.com/r/gonewildstories/comments/10k3vl0/mf_samss_shorts_pt_1_anal