Again, sorry for the delay in trying to get posts written. I wanted to pick up on my Nashville stories. To review, I had been completely humiliated by a professional domme from an escort service in front of my new friend Anna. This had been Anna's first exposure to humiliating men, but she really enjoyed it. The next night at a group dinner, she openly told everyone about my scene of dressing up, being spanked, licking up cum, etc. Read the posts below for more details.
I had been doing some humiliating sissy shopping the next day and was just coming back to my hotel when a car pulls up and parks next to me. Out come Anna and a man. I started to get panicky. It turns out he was her boyfriend, and she brought him along to have some fun. I had this sinking feeling because I was afraid that she had brought him over to have me suck his cock. Besides, I've never really gotten into these scenes with other guys, and I was already embarrassed that she had told me about what I like to do. Dan shook my hand and was pretty normal.
We went into my room, and after a short while, Anna told me they wanted to see me put on my sissy things. I sheepishly got out my bag and started selecting some things to wear. Anna and her friend sat on the other king-size bed and watched as I started to strip and put on my underthings. Anna told me that Dan had a particularly interesting talent: he could cum repeatedly. I was a bit curious about it, and she started playing with him and sucking his cock in front of me. His cock was about average size.
After getting him all worked up, she had him stroke himself to orgasm. After cumming, he kept stroking, and about a minute or so later, he came again! Again he kept stroking, and he came a third time and a fourth. I was utterly amazed any man could do this. By this time, I had my girlie things on, and Anna told me to get out my toys and start playing. It was difficult to act out my sissy side in front of Dan, but I was starting to get prissy as I slid in the butt plug. Anna laughed and said, "See, he's a sissy pantyboy! He likes that plug in his cunt." Then she told me to start sucking my 10" dildo. Anna told Dan, "He cums on it and eats it!" Embarrassed, I closed my eyes and started sucking it while she laughed. Dan didn't make too many comments, but I truly felt degraded and like I was on display.
Anna had stripped and got on all fours on the bed across from me. In no time, Dan was in her from behind and was fucking her. I was a bit stunned, and I asked "Oh my... is he fucking you?" Anna smiled big and said, "He sure is! It feels so good to get fucked by a real man!" She closed her eyes and moaned while I, the sissy cuckold, knelt on my bed straddling a pillow with a plug in my pussy bottom. I rode it up and down while I sucked on my pretend cock. All the while Anna and Dan were fucking each other silly.
I eventually started to cum. I whimpered like a sissy and dribbled on the dildo. It's difficult for me to stay in the moment and actually eat the cum unless I'm being dominated. I was overwrought with the shame of being in front of them, and I just laid over on the bed. When she realized I wasn't planning to lick up my mess, Anna snapped, "You lick that dildo clean! Lick it up! Now!" I sighed and slowly put the dick in my mouth. The humiliation was very deep. Here there was a couple watching as I sucked my cum off a dildo.
Anna cooed in her southern voice, "Does that taste good, Honey?" I quietly nodded. She laughed and said to Dan, "See, he's a sissy wannabe cocksucker." By this time, I was terrified she was going to have me do something really disgusting like lick Dan's cum out of her pussy or suck his cock clean. It was enough cuckolding to have them fuck in front of me knowing that I wasn't going to participate.
Thankfully our encounter didn't last too much longer. I cleaned up and put regular clothes back on and they headed out. Anna would return later. Dan was married, and they had been having this ongoing affair for some time. I was their entertainment for the evening, and I certainly felt like an object.
What a pathetic sissy. Watching a couple fuck while they watched me fuck my pussy bottom and my mouth with sex toys. I could imagine their drive back together: him asking her, "Where did you meet this queer?"
There's more to come on the Nashville story. Stay tuned!