The private detective I worked for gave me a new assignment. 'His name is Bob. You follow him and see if he is cheating on his wife. Get some video or pictures if you can.' I was given his address and other info and set out on my mission. I followed Bob from home to work and waited in my car for 3 or 4 hours until I saw him walk out of the building and get in his car. He peeled out from the curb and I followed. Man this guy was in a hurry. I could barely keep up, weaving through traffic until he pulled into a parking lot. He parked next to a van, got out of his car and quickly opened the back door of the van and I saw a woman in there as he climbed in and closed the door. I crept up to the van and peeked inside. I saw Bob sitting in a captains chair with his pants around his ankles and this woman giving him a fast blow job. She was really working his cock good and quick. I started the video camera and filmed the action. Bob stopped the woman from sucking and they switched places. She slipped her panties off from under her skirt and gave them to Bob. He put them to his face and inhaled deeply. Bob threw the panties over his shoulder and put his hands on her thighs and slowly slid her skirt up until it was bunched up around her waist and from my vantage point it looked like his head was going up and down. I moved to another window on the van and focused the camera in on the action and oh my god she had a cock. Bob was sucking this 'woman's' cock. I stood there filming Bob giving this beautiful transvestite a blow job and realised my own cock was hard and throbbing. His mouth moved up and down the shaft, swirling his tongue around the head while he stroked her and cupped her balls. She pushed his head away and got down on all fours as he pulled some lube from a compartment and put some on his cock. Bob bent down and began licking her butt-hole gently at first then like a madman who could not get enough. She was groaning as Bob licked her and then grunted with pleasure as he started to slide his cock head into her butt hole. Bob started thrusting in and out of her until he was slamming his hairy pelvis against her ass cheeks. I moved to the back window and zoomed in on Bobs cock pumping in and out of her butt hole while her balls jiggled around and I realised I was rubbing my own cock through my jeans. Bob continued fucking her for about thirty seconds and then I heard him grunting and knew he was cumming in her ass. He stopped thrusting and slowly pulled his cock out of her. Bob laid down on the floor and she straddled his face. She ground her cummy butt hole on his mouth and I could see his tongue licking and searching for his own warm sperm. She was stroking her cock as Bob sucked his cum from her hole. She was stroking faster and faster when she cried out and pointed her cock at Bobs face and a thick stream of warm sperm landed in his mouth. Bob got his lips around the head of her cock and I could only imagine the feeling of warm sperm flooding his mouth. She stroked her cock for a moment then pulled out and bent down to put her lips on Bobs mouth and share her cum in their kiss. When she raised her head up I could see the sperm glistening on her red lips and I wanted to open the door and kiss her right then. They both got up and began to put their clothes on so I quickly went back to my car. I watched Bob get out of the van and saw him lean back in and kiss her cock and sucked it a little then he closed the door, Bob got in his car and I followed him back to work. As I sat in my car watching Bobs encounter with the transvestite on the cameras display screen, I had to pull out my cock and stroke it. I told myself I wouldn't cum but as I watched Bob licking his own sperm from her beautiful butt hole I stroked faster and went past the point of no return. The first rope of cum hit landed on my lips and I sucked my warm sperm into my mouth. I put my hand over the head of my cock to catch the rest and licked my own spermy hand clean. I was sucking the last of it off my fingers when a thought occurred to me. I drove over to the detectives office and showed him the video. He watched in silence and said 'well I don't know if we have enough proof, you can't really tell if that's Bob with the transvestite'. He stood up and I noticed a bulge in his pants. I said 'I could go undercover and get some better video.' 'What do you mean undercover' he replied. I explained that I would put on a dress and wig and get made up like a woman and seduce him on camera. The detective considered this and said 'alright, but make sure you get it on camera.' We already had this guy nailed on camera. You could clearly see it was him. My detective was obviously turned on by what he saw and wanted more video. I planned on giving him more than that. I called a female friend and told her what I needed. An hour later I was looking at myself in her mirror and I could not believe what a great job she had done. I looked like a gorgeous young woman with long black hair, a short dress and stockings with garter belt and panties that felt so silky next to my cock. The make up was perfect right down to my ruby red lips. I thanked her and drove back to the detectives office. When I walked in I saw him watching the video of Bob and the transvestite and rubbing his cock through his pants. I said in a sexy female voice 'excuse me, are you a private detective?' He stood up and stammered 'yes I am what can I help you... Holy shit is that....'
'Not to shabby huh' I replied. I could see his erection through his pants and a little wet spot of pre cum. I walked over and knelt down in front of him and opened my mouth. He said 'uh I don't know if this is a good idea' I undid his pants and pulled them and his underwear down. A beautiful hard cock was staring at me. I took his cock into my mouth and began sucking and flicking my tongue over the tip. I could taste the fluid leaking out of his hard cock as I worked it deeper into my mouth and throat. I held his balls in my hand while he fucked my face jamming his cock in and out of my throat. I pulled my mouth off his cock and started licking his balls and stroking his cock when he said 'oh fuck, I'm cumming'. I wrapped my lips around the head of his cock and stroked him until I felt the first gush of warm sperm spray my tongue. It tasted so good as streams of warm cum flooded my mouth and him groaning and grunting. I swallowed his sperm and then swirled my tongue around the head. I sucked the last drops from the tip and then repeatedly jammed his cock down my throat until I could lick his balls while deep throating him. He pulled away and said 'Jesus Christ!! That was amazing. I cant believe this happened' He pulled himself together and seemed to suddenly notice he was standing in his office with his pants down and a raging hardon pointed at the ceiling. I stood up and gave him a cummy kiss as his boner poked me in the stomach. I asked him to unzip me and with trembling hands he helped me out of my dress. I stood in front of him in my bra and stockings and garter belt, with a rock hard cock in my panties. He got down on his knees and put his hands on my ass so he could pull my panty covered cock to his face. He pulled my panties down and started sucking my dick. He was using his hands on my ass to pull my cock in and out of his mouth. I looked over at the monitor on his desk and watched as Bob fucked the 'transvestites ass'. That really got me going and before I knew it I was spraying my detectives mouth with my warm sperm. He swallowed and continued sucking every drop from the tip. He stood up and spit in his hand. I knew what to do. I got on my hands and knees and he poked around at my butt hole with his slippery cock until I felt it start to slide in. The pressure and stretching of my butt hole felt fantastic. I grunted with pleasure as he slid his cock deeper and deeper into my ass with each thrust. I was grunting and groaning and he was grunting and groaning as he slammed his cock in and out of my butt hole, his balls bouncing off of my balls. His thrusts were getting more frantic and I heard him cry out 'oh fuck, oh fuck' and felt his warm sperm shooting deep into my belly. Warm spurts and streams were hitting the deepest parts of me. He kept thrusting a few more times after he came and then he collapsed onto my back. We stayed like that for a moment and then he put his face down to my ass and buried his tongue in my butt hole. He was licking and sucking his sperm from my ass while I stroked my cock. It didn't take long, I laid on my back and he put his lips on the tip of my cock as I came in his mouth. He sucked my cock as I sprayed streams of warm sperm onto his tongue. He kept sucking my cock even after it began to get soft in his mouth. He moved up to kiss me and we shared a deep cummy french kiss, swirling his cum from my ass and my cum from his mouth together between our tongues. We were laying there like that for a few moments when the door to the office opened and Bob and his transvestite walked in and he said 'why are you following me'.
To be continued.