I was in my later college years and the urge to explore was as strong in me as ever. I was fresh off my escapades at the gay sauna while visiting home. Now I was itching for more. I began experimenting with my ass shortly after the trip. Trying fingers and eventually getting a plug and a dildo. I also had a once in a million chance when I was tasked to retrieve something from a girls car and under the seat was A THONG.
This had me feeling bolder than before and I took to the Craigslist posting. I eventually found a guy in his 30’s, 5’10 and average build with a nice looking cock. I asked if it was chill to wear the thong while he fucked me and he happily agreed. When I showed up we wasted no time and made straight for his bedroom. I was out of my clothes in a nano second, down to my thong. He was slower with taking his clothes off, first his shirt, then the belt and then he told me to undo his jeans. I was still new at this and went slow, with a shaky hand. I undo the button, unzip the fly and out pops his 7.5” thick, smooth and hard cock. I was not anticipating him not wearing underwear at all and was wide eyed and excited.
I started jerking him and then tentatively started running my tongue along his length. He had a slight musk to him that felt like he had showered but that he jerked it anticipation to my arrival. I got back to the tip and gave it a few licks before finally going for it. I gagged immediately but found my sweet spot and started bobbing my head. He ran his fingers through my hair letting me know I was doing great and soon after he asked if I was ready. I had prepped at home and was already prepared with my plugged and lubed ass. I leaned over his bed affirmatively and said he should come find out. He put on his magnum condom, squirted some lube on his dick and pulled my plug out gently.
He pulled my thong to the side and circled his dick around my hairless virgin hole. I tried to relax but I was so nervous. I was really giving in to being a panty boy slut. I took a deep breathe and he reassured me he’d go slow. He started to work his 7.5” in and out of me with small, slow strokes. My moans told him when he could push more. The strokes started to get bigger and faster until soon he was pumping his full cock in and out of me. I loved it. My moans were dainty and feminine showing me I’d always be a femboy inside. He started to pump harder and I could feel my own cock straining against the bed. Each pump led to another effeminate cry, a twitch from my cock rubbing the bed and waves of bliss from the cock slamming my prostate. Soon he said he was going to cum and I was right there with him. My legs started shaking as his breathing quickened. Soon my cock was exploding as my ass was spasming out of control on his dick. He let out a groin and his cock began to twitch and pump deep in me, I could feel the condom filling and we both rode a wave of bliss for what seemed like forever.
Sadly, we came to eventually, he was still hard in me, I massage him with my ass a bit until he slowly pulled out of me. I flipped over on the bed with my cum smeared across my stomach. He pulled his condom off and it was unbelievably full. I told him I couldn’t waste that. I took it from him and poured it on my tongue, chin and down my chest. I then started taking my finger to wipe it up and lick it. He began to help me until I was all clean. We then went to get a shower and things would get steamy again but that is for another story.
Source: reddit.com/r/Erotica/comments/xdc9h4/my_first_time_with_a_man_was_in_a_thong_m22