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SANDY - Lessons from a Trans Woman Part 2 - Bob's Ass Author: Mystic1999 Date: 25 September 2026 Non-consensual sex, Humiliation, Transsexual, Rape
![]() The lesson continues with Bob's ass. She leaned over and took something out of her bag. It was black and looked like a cock or dildo. It was attached to belt. “I’ll bet you never seen a dildo gag. Some face outward and are used for on pussies, but yours has the rubber cock facing inward and goes in your mouth.” She explained. She stepped behind Bob and he saw the dildo appear in front of his face. “Open your mouth!” she ordered. As he did, she guided the dildo into his mouth. It was about four inches long with a cock head at the end. She stuffed it into his mouth and pulled the strap around his head and secured it. Now he was on my knees with his mouth filled with a rubber cock. His hands still tied behind his back. “Stand up and walk to the side of the couch.” She said. “I love couches with rolled and padded arms, it make anal sex much easier. At least for me.” She laughed. She bent him over the arm until his head was down on the seat of the with his ass on the top of the padded arm. “Time for the main event.” She said as she began to push and pull the butt plug in my ass. “It takes a few ass fuckings to really stretch out a cherry ass, but we don’t have time for that.” She said She was roughly working the plug in and out of his ass. He was trying to ignore the pain and began grunting into the dildo in his mouth. “Yes, yes, please let me know what this all feels. A dildo in your mouth and a butt plug in your ass. Get ready for the real thing.” She chuckled. He felt her abruptly pulled the plug out of his ass. He screamed as this was done, but it was just a moan around the gag. She walked around where he could see her. In her hand was the anal lube bottle and she was squeezing some of the clear liquid on her cock while stroking it. It looked evil, bright red and gleaming in the lamp sight. She moved out of his sight and he felt her pouring lube into his ass crack and ass hole. She shoved three fingers into Bob’s ass while doing it. He yelled again. “Please keep that up. It gets harder every time I hear one.” She said. He could feel her straddling his legs behind him. Then he felt her running her cock up and down his ass crack. She did this two or three times.” “Say goodbye to your cherry ass.” She taunted. He felt pressure as she placed the head of her cock against his ass. He could feel it trying to enter his asshole. It slipped a time or two and then she adjusted her stance to be on top. With this new angle she managed to shove the head into Bob’s ass. He thrashed around and let out a yell as he felt her cock enter his ass. “Very good! This will take a few minutes, but I promised you I could get all of it into your ass and I will!” she said softly. With that she put her weight behind her cock and began showing more into his resisting anus. She would pull back a little then lunger forward. Back and forth she went each time getting more on her cock into his ass. He moaned and groaned and tried to pull away from the tormenting cock, but to no avail. He realized he was biting down on the rubber cock in his mouth. He bit so hard he expected to bite it off. “There’s nothing more pleasurable that watching my cock disappear into the ass of a helpless victim like you. I have done this many times and it’s still the greatest thrill.” She taunted. With a final shove he felt her balls pressing against his ass crack. “Feel my balls on your ass? That means all nine inches of my cock are buried in your bowels my ass fucked sissy. I’ve always liked the old fashioned name for this. ‘Sodomizing’. ‘Sodomy’. Now there’s a polite word for fucking someone in the ass, isn’t it?’ she laughed. She then began to pull her cock back out of his ass. He thought it might hurt less, but it didn’t. His ass was on fire. The pain radiated from his ass through his entire body. It ached and felt hot. The stretching of his anus was worse than he had thought. When she had only the head in him she lunged forward and burying all of her cock in Bob’s backside. This was how they spent the next ten minutes. Her pulling and shoving her cock into His ass. He lost interest and explored the taste and texture of the rubber cock in his mouth. It had no taste, but it did have veins covering it like a real cock. He licked them for distraction. Then he heard her say: “I’ve had my fun. Now it’s time to fill your ass. I’ve been told you can feel me shooting my cum into your bowels. We’ll see.” She said. She picked up her pace with her balls slapping against his ass when all of her cock was deep in him. Within a few minutes, he heard her groan which meant she was cumming. He knew she was shooting her loads into his ass, but he didn’t feel anything except the pressure of her cock in his ass. After a few more lunges she stood up and he felt her cock sliding out of his ass. It didn’t feel better, his ass still hurt. “I got some good pics of my cock in your ass. Now I want some of your ass stretched and leaking cum. That’s the second best part of “Sodomizing’ someone like you.” She laughed. “We’re not quite through, Sweetie. Lick my cock and balls very clean. I always enjoy watching my pupils tidy up after a cock sucking and ass fucking lesson.” She giggled. She pulled his head toward her cock, which was not quite so hard now but still big. He began to lick her cock shaft. He then sucked on her balls. They were both covered with her cum. “Yes, that a good boy. You take directions very well. Like the taste of your own ass? Now I want you to lick my ass and I want to feel your tongue in my asshole.” She said. She stood up, knelt facing the back of the sofa and spread her full ass cheeks. This let him see her red puckered asshole. Bob knew he had no choice so he began lick her ass crack with my tongue. “Now stick it in my ass, Sweetie.” She said. He did as he was told and he managed to get the tip of my tongue into her sphincter. She wiggled her ass and moaned as he did this. “Very good, my little ass licker, not everyone has the talent you have. How do like the taste of my ass compared to your own? He said nothing. “I told you that your ass would be sore for a few days. I’m going to undo your hands and I want you to lie on the down on the couch.” Bob did as he was told. “Well, tonight’s lesson is just about complete. You’ve learned to suck cock, swallow cum and have your ass fucked and filled. A busy night, huh? She said. “Now it’s time for me to go. I suggest you think about how you’ve lived your life and how you can improve it. I have some very nice videos. In case you think about calling the police. I know your performances would be popular on the Internet. You keep out secret and I’ll keep our secret. I come to Las Vegas a couple of times a year. Maybe I’ll contact you and arrange for another session. I enjoyed this one very much.” Sandy reached into her bag one more time and brought our a small spray bottle. She walked over to Bob. “I’m going to spray this into you nose. It will help you sleep.” She said. She inserted the bottle into one of Bob’s nostrils and squeezed a burst into his nose. Bpn coughed as this was done. “In a few minutes you’ll be asleep. I’ll leave you hear on the couch for the maid to find you. I’ll take the cage and butt plug with me, so those secrets are safe. Have a nice sleep.” She laughed. Bob dozed off looking at her standing over him. Sandy went to the bathroom, showered, repaired her make up, dressed and then left. She was thinking about the next encounter she would have and looking forward to it. THE END 1948 9 7748 1 Leave your commentSign Up and leave comment
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