About 4 years ago, I was to attend a friend's wedding in the city I grew up in. I was in my mid-20's and still in school and had no wish to spend all of my money on a hotel, so I started asking around to see if I could stay with a friend. I finally settled on Ron. Ron was a former employer and recently divorced, in his late 40's and could have used to company. I packed up and made the 4 hour drive about a week before the wedding. Ron was very nice and let me stay in a guest bedroom.
He departed everyday for work at 8 in the morning and I had free run of the house. Eventually I decided to access his computer to check email and found that he never turned his computer off. He had a few instant messages on his screen and never bothered to clear out his history file. Curiosuity got the better of me and now I'm glad it did. Ron was really into TV/TS/CD porn. That's all he looked up and had several pictures and mpegs saved to his harddrive. I closed out his internet page and found a most interesting message window waiting for me. It was from someone in his friend list and asked "so did your friend make it in?" to which Ron had replied "yes, last night". "Crossdresser material? lol" to which Ron had replied "I wish!". Now, being that I was the only person staying in the house at the time, I assumed that this had to be about me.
I had more than a few fantasies about this over the years and quite nervously, decided to go with this. The wedding was in late October, so I had an excuse to dress up, and an out if I decided not to go through with this. All I had to say was "I'm dressed this way for a Halloween party". I hit the local malls and found everything I needed. I got back to Ron's and drew a hot bath. I very carefully shaved every last inch of my body, save for my head and eyebrows, of course! I went to my room and put on my brand new shiney black satin bra with a lace trim, matching bikini cut panties and a black garter belt. After painting my toenails crimson and letting them dry, I slid on a pair of black silk stockings, which had a seam running down the back and a little satin bow at the top. I applied a bit of makeup, a light blue eyeshadow with some black liner and mascara and crimson red lipstick. A bit of blush and pearl ear rings completed the look. I slid into a black satin french maid uniform with a black satin choker and a spiral curled wig which I swept up in the back and pinned it down tight.
A pair of 5 inch heels with straps for my ankles and crimson red press on finger nails later, I was ready for a new experience. I checked myself out in the mirror for an hour or so, fixing this and adjusting that and I heard Ron's garage door slide open. My heart was in my throat! But I had an out if I decided to not go through with it. Ron cam in and dropped his keys on the counter and was reading a paper and I situated myself on the living room couch, watching t.v. . I'm not sure how long he was standing there but when I looked up he was wide eyed and frozen. "Hi Ron". "uhm.. uh.." he replied. "Oh, I have a Halloween party tonight", I told him.
This seemed to relax his a little, but not much. "Oh, you look.. amazing!" he remarked. I just smiled. Ron was so visibly nervous for the next hour or so and my bending over on occasion to show off my black satin panty covered ass didn't help matters much. Ron eventually said, "well I hope you have fun tonight!". "Thanks! Me too, I'm hoping to have a good time, maybe even get lucky!" I stated as we nearly passed each other in the hallway. Ron smiled, "anybody in mind?" I just looked at him. "... yeah, you." He turned white. He started to stutter something but something overtook me and I pulled in close and kissed him. Ron pulled me closer and I could feel his heart beat through his chest! I stopped and coyly stated in a french accent (french maid and all) "may I be going out tonight, sir? I fininshed all of my housework!". Ron played along. "All of your work?" I nodded. "You washed the windows?" "Oui". "You mopped the kitchen?" "Oui!" "You dusted too?" Oui, sir". "Wiped down the doors?" I nodded again. "You.. polished all the knobs?" Oui, I did". "All of them?" "I.. think so. Did I miss one?" "You did, follow me." Ron let me to his room and dimmed his lights. "No, sir, I polished the one in here too." "Even the one in my bathroom?" I went to look in the bathroom, playing along, "oui, I did". "Oh, silly me, it's out here.. um.. um.." "Chelsea" I replied. "It's out here, Chelsea." I walked back into the bedroom and there Ron stood.
Pants at his ankles, his stiff cock pointed right at me. "Come here" he said. "Sir, this was not in my contract. I .." Come here now, I said". His stern voiced washed over me and I floated closer to him. Still at about 2 feet from him, he looked at me and said "now, bitch!". I melted. Ron pulled me in, kissing me. He took my hand and wrapped my fingers around his cock.. I could feel it throb in my hand. I gently massaged it as Ron kissed my neck, inhaling my perfume. He pushed a hand into my uniform and began to stroke my chest through my satin bra, flicking at my nipples through the soft material, sending waves down my spine. A light pinch here, a stroke and a flick there and I was jelly. Ron pulled the top of my maid uniform from my shoulders and I pulled my arms back out, exposing my bra.. He went to work on both nipples in the same fashion. I whimpered.
After about 10 minutes of this, Ron said "alright bitch, kneel". I playfully started to refuse but he scolded "get on your knees slut!". I gazed softly at his eyes as I sank, slowly to my knees. Ron carefully placed me, as he later explained it, so that he could see my heels sticking out from the lace trim of my maid costume. He tilted my head back with his finger under my chin and began to rub the head of his swollen cock all over my face. "You want this don't you" he whispered. "You want my hard prick in your mouth. Well come on bitch, suck it". I began to lick and kiss all over his dick, all the while looking up at him, giving him innocent eyes. I took my time, making sure he could feel my warm, wet lips and tongue on his skin. I began sliding his wet cock into my mouth, a little deeper with every pass. Ron responded by pushing harder into my mouth and placing his hands on the back of my head. "Oh yeah.. that's it, take my fucking cock in your mouth you whore" Ron moaned. His words turned me on even more. I loved being spoken to like that.
I pulled his cock out of my mouth and slapped it against my tongue, which caused him to moan louder. I spit on the head of his dick and let him watch my spit beads roll down his cock. I touched my tongue to them and pulled back, showing off the strands of saliva that connected my tongue to his prick. Ron let out a deep moan and pushed himself back into my mouth. This time he pushed deep, slow and hard causing me to gag a little.
This seemed to excite him as he repeated any action that resulted in either a gag or a slurp sound. Suddenly, and without warning I felt my mouth begin to flood. I tasted something warm and salty and knew what had just happened, Ron pulled out and told me to hold my mouth open. He jacked his cock off and came what must have been a gallon into my mouth, on my face, and finally stuck his cock into my bra and shot one more load between my satin bra and my chest. He told me to suck him until he told me to stop. I sucked until he was pretty sure I got out the last drop and then used his dick to push the cum from my face into my mouth.
He told me to look up and open my mouth and show it to him. Ron seemed very pleased with what he saw as he stood and looked for a couple of minutes before telling me to swallow. The rest of my stay at Ron's was very similar to this as I was sent shopping with his credit cards for more outfits and when he returned from work everyday we played for most of the evening. I frequently woke him in the mornings before his alarm went off wearing a slip and a pair of heels by sucking his cock. I have a few more Ron and I stories, but this was the first. I visit my home town as often as I can now.
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