This was almost 2 years ago, I was 27 One of those things that I had been trying for years, i wanted to be pegged, ruthlessly, by someone I barley knew. CL personals were still a thing back then, but I live in a small town smack dab in the middle of the US. I began trying posting ads in Wichita cl looking for someone to peg my ass raw. Not many replies most of which were spam. A few people got my hopes up but ghosted me after some very erotic conversations. I’d given up but hadn’t deleted my ad.
I had been having a rough week at work and had gotten a message through the messaging relay from a lady in a town about an hour and a half away from me. She was very interested in pegging a guy as she had done strapon play with woman. She only sent a couple messages back and fourth, gave me her phone number and wanted me to call her. I was super nervous and axious but called her on a Thursday evening. We talked for about 45 minutes, it was great, like talking to an old friend, I hadn’t seen any pictures but connected decently in a mental standpoint. We started talking about the kinky things and I was so excited.
She asked when we should meet up and I said no idea. We talked about what supplies and equipment we both had, then she started texting me pictures of her holding dildos asking “is this too much girth,” or “longer?”  Jaz as we will call her, gave me a ring after she left the sex shop and asked if was ready for Friday night. I stumbled and told her i didn’t know. 
She had been texting me all Friday morning,  teasing, convincing me to bring things such as my chastity cage. By noon i had called and reserved a hotel room. Went home during lunch and got a bag of things ready, I was a mess the rest of the day at work. Left immediately after I clocked out, it was a white knuckle drive, the longest 1.5 hours of my life. I checked into my room. She didnt get off till 9 or so that night, so i took a shower, gave myself and enema and locked myself in my cage to wait. She called, said she was on her way. My small penis strained inside my cage, i was ready to explode. I threw some clothes on and waited in the parking lot.
She pulled in, and got out, she was a fairly tall, bbw ebony woman. She giggled and gave me a hug and a kiss. I was going crazy, had only been sexually active with a couple ladies in my life. So I was really going out on a limb. She said ” well here I am lets get going.” 
We went to the room, kissed a little, she told me to get naked, so i did. I felt so venerable. She pulled off her pants to reveal some tight boyshorts and asked me to put the harness on her. I got on my knees and put it on her. Jaz softly asked, “yours or mine first?” I didn’t say a word, but picked up mine as it was smaller, still 8+ long but not as thick as hers. She made me put it on the harness so i did, I stayed still for a minute and she said, “well suck it.” I had never done such a thing and I tried to deep throat it and kept disappointing her.
After 15 mins of me being throat fucked she said it was time for my ass.  I got in position and she got behind me. I had done butt play before, but nothing quite this big, and never with a stranger, she put some gloves on and began to lube up my ass. Without warning, she thrust deep into me. I yelped and she told me I was a good little whore. It felt amazing and she proceeded for probably 20 mins or so. I rolled onto my back and she fucked me missionary style. I loved looking into her dark deep eyes while she fucked me deep and hard.  I laied on my side and she told me it wasn’t time for rest yet. “Get into doggy” so I did. About 3 minutes later she began working her dildo into me, its girth was almost twice as big as mine and 3 inches longer. I about passed out as she relentlessly pounded me. I collapsed onto the bed and she said.”Your a good boy, thanks.”
She pulled the dildo from her harness and slipped her pants up over the harness, said ” thanks for the good time sweetie, call me later!” Then she left.
I tried calling her, but must have been blocked, I’d love to make contact again with her again, but she is long gone…