I'll try to keep this brief but I'm so very excited it may get out of control. A few days ago after a long "avoidance" of sissy stuff I went completely overboard and dug out a suitcase I hid my old toys in. I posted photos here, another site, and a ad on Craigslist. Which I later deleted. A cycle I have repeated 100 times probably but never acted on. I kept talking to 1 guy from Craigslists though. I never really intended to go through with the filthy ad I posted and he called me out immediately. Told me to just send him some pictures he could jerk off too...and I did. Including my first face pic. For brevity sake I'll just say he pushed all the right buttons until today when I drove nearly two hours to fulfill my fantasy.
When I knock on his door he is wearing a wife beater and white boxer briefs, he is older,in his 40s. White, shaved bald head but chest hair protruding from his wife beater. Before he let's me in he tells me to spin around, he checks me out and says I'm cuter than he expected. I see his briefs grow tighter and a slight bulge holds my gaze. I'm grinning "he thinks I'm cute and I'm making him hard" I think. He pulls me in by my scarf and we sit on his couch. He fires up a joint and we smoke. He tells me to get on my knees in front of him which I do. He slides down his briefs revealing the slightly erect cock it was hiding. He tells me to start with my tongue and get him ready. I hesitate he tightens my scarf around my neck until I slowly start to lick the underside of the shaft. The taste briefly nauseated the (9-5) me but excited sissy me to the point that my tongue kept seeking the taste. He asked if I liked country music (I loathe) country music. I nodded my head yes. He clicked on country music and lit himself another joint. I continued licking his now soaked and magnificently hard cock. I felt so close to cumming from sucking his cock I whimpered, he mocked me repeating lines from our chats about worshipping his cock. He told me he was going to see how much of my chat was true. Then began forcing my head as deep as he possibly could. I gaged he confirmed that part was true and thrustedd deeply several times fucking my mouth like a pussy reminding me I begged him to do it. I pulled back to catch my breath he began stroking as I was coughing surprising me with a load directly to the side of the face. He smeared it across my face and 3 fingers full in my mouth. My cock oozed, wetting my panties as if it was a real pussy. He said he had to piss and directed me to the bedroom. "Face down ass up" I was instructed. I obeyed. He returned pushed aside my panties. He sat on the corner of the bed and smeared ice cold lube on my asshole. I flinched, sincerely fearful that he would act on my requests. He asked nicely before inserting a small, but gigantic feeling dido. Slowly it entered, lightly, vibrating which elicited perhaps the most genuine moan of pleasure I've ever experienced. That quickly gave way to the abuse of my asshole I begged for. I lasted maybe a minute before begging him to stop. He reminded me I told him to ignore if I begged. After a few more painful thrusts however he stopped and told me to change into another outfit and he was ready for more head. I returned from changing and he returned to his joint smoking couch position. He just pointed and told me to take it slow. I truly felt such passion for his cock this time. Made love to it with my mouth, adorded it, feared it, craved it, humbled by it. He allowed me to truly appreciate every inch. He complimented my 2nd blow job ever. He pushed my head deeper down the shaft and I could feel the thing I truly craved swelling. The last confirmation I needed to confirm my desires. The precum ignited all my senses, my taste buds desired more. More quickly followed directly into the back off my throat, I involuntary spit some up covering my lower lip and allowing a good deal to drop to the floor. I licked my lips clean. And he reminded me I promised not to let a drop go to waste. I dropped to my belly and sucked what I could from the floor. ....We smoked another joint together and discussed a next meeting. ...shit sorry this went way too long