That was this summer. I had very long relationship and last year i got ridden of it. So I sex occasionally wit various girls till then. One night this September I was very very tired of everything. Job went finally better and some private investing also, but I had being working for 14 hours a day at time. It was About 1 am in the morning and was just went of from long shower and about to lay down on my bad.The voice from the other side of cell phone was very pleasant, some kind of baby talking voice. Voice said" Annnn' what what do want from me now?...LOL.. i said "who is this?&... Continue»
Let me start out by saying that I was very much in the closet about my dressing and the fun I have when I'm dressed when this happened. But more and more I kept fantasizing about one of my male friends. He's very good looking and keeps in shape by jogging every day. Several of the times we've gone out boating him and I ended up skinny dipping, so I've got to see his cock several times and have secretly wished I could get him to screw Kristy. He's been divorced for about 5 years and doesn't go out much, and several times he's told me he hasn't been with anyone for a couple years.
Well on one of my trips out to the local ABS I only got to walk around and suck one guy because the place was empty so I decided to drive around and enjoy myself being dressed. Before long I was about a mile from my friends house and thinking of him again. I guess it was the though and the excitement of the moment but I turned into his condo parking lot. It was about 10pm on a Sunday night and all was quiet.
When I got out of my car, I had only planned on taking a few pictures of me walking near his door just to help with my fantasy's but after I set the camera up for the 2nd picture the door opened and I was caught. Fully dressed in my heels, black fishnet thigh highs and garter, with a tiny tight white g-string, covered only by my black spandex mini. My makeup was very carefully applied and the red lipstick and blush looked better then even I though I could put on. My medium length brown wig was brushed out and laid softly on my shoulders. At first he didn't realize who it was or even that I wasn't a girl. But before I could leave he saw the camera and picked it up to give it to the girl standing only 6 feet away, trying not to look at him I put my hand out to take it but he jumped back and it hit him who I was.
I was embarrassed and unable to say a word, when he asked me what the fuck I was doing. I could only stammer and tried to make up a story about a dare to tease him. Laughing and staring at me I started going on about the only way he was going to get laid was if some girl came and knocked on his door. Then he asked if my wife knew I was dressed like this and of course I told him no! I wanted to leave but he kept asking about my clothes and who put on the makeup and where I got dressed.
After about 5 minutes, which seemed like 1000 I told him I was going to get home. He asked if I wanted to change back into my clothes and I guess without thinking he asked if I wanted a beer, I said yes. I needed one bad so I walked into his living room and in the better light he told me I didn't look bad and he even though he'd gotten lucky when he first saw me. Sitting on his bar stool sipping the beer my dress had ridden quite far up my thigh and as I pulled it down some he asked what I had on underneath. I was too embarrassed to show him because of the slight bulge starting to push at my g-string, he teased me about being a little tramp. I laughed with him and noticed him adjusting the growing tent in his shorts. I still didn't want to tell him what I really wanted but I was wondering if maybe I could get lucky.
My mind started running through all the ways I could subtly arouse him till maybe he would forget about who I was and just give in to the moment. I reached for a cigarette and dropped the lighter as I fumbled to get it out of my purse. As I bent over I made sure my dress rode high enough up my thigh to see the garter and tops of my thighhighs, but I guess enough of my bare ass was showing that he reached over and smacked it fairly hard. Again he asked me more about my clothes and during the next few minutes I told him that it actually felt good and sexy wearing them. Becoming a little more bold I stood up and asked him how he though I looked, pretending to model and pose suggestively. Even blowing him a kiss as I walked around the room.
Then I started to talk suggestively, pretending to be Kristy. Teasingly asking him if he wanted a hot date. I knew he was horny, he couldn't even stand up by now. Still walking around I suggested maybe he'd like a lap dance, and before he could say anything I was standing next to him with my ass pretending to rub it in his lap. Then acting as if I caught my heels on the carpet I sat on his lap, with his hard cock rubbing at my ass. Acting supprised I asked if he was happy to see me or was he just keeping a sausage in his pants.
As I stood I placed my hand on his thigh to balance myself, and he helped me get my balance pushing my hips. My legs were weak and shaking knowing how close we were. Then trying to tease him even more I dropped to my knees and pretended to blow him. At first I though he was going to get mad, but he shocked me when he started to tease back, grabbing his cock though his shorts and telling me to suck it like a whore. I shot back, and what would you do if I did. Then he totally shocked me when he said he'd probably cum in my mouth. I wasted no time reaching my hand up his shorts and found him totally erect. When he didn't pull away I felt like a dream had come true.
Pulling his hips toward me till he was just leaning on the barstool I slid his shorts down. His cock was only inches from me and leaning out towards my mouth. I looked up at him, his hands on my shoulders, still not believing he'd go through with it. Licking my lips one more time, I leaned over and sucked the head of his cock between my lips. His body tensed as my tongue circled around the tip. Not wanting to overwhelm him at once I slowly sucked him deeper into my mouth, my lips squeezing the shaft till I had gone most of the way down. I slid my hands around behind him pulling his hips off the stool towards me. His soft moaning and occasional encouragement was making me suck him like I'd never get to do another. My hands had found there way to his ass and I was gently squeezing his cheeks with my fingers sliding close to his hole, then down to his balls. My lips were working up and down his shaft waiting for the creamy reward.
Sucking and slurping his cock, feeling him push my head back down every time I came close to the top. He started to say my boy name and I softly told him to call me Kristy. Soon his hips were pushing back at my mouth as fast as I would slide my lips back up his shaft. His moaning, Missy Oh Yea, Suck it Baby, and Take it all Baby and the tightening of his ass told me he was getting close. I slid my lips back up again and then moved my mouth down to his balls; my hand kept stroking him slightly as I took each in between my lips. Sucking and licking around each then running my tongue around the base of his hard cock. He lowered his cock to my lips again and I sucked him back into my mouth. With one hand on the base of his cock and the other between his cheeks I pulled him back harder with each stroke. His hips were thrusting hard, pushing his cock down between my lips and back out.
Oh Kristy suck it Babe was the last thing he said before I began to taste his warm sticky juices in my mouth. He leaned on the stool cum filling my still working mouth, as I milked his cock of the last warm drops. Slowly his cock began to soften in my mouth as I swallowed most of his load, with only a slight dribble running down my chin as he pulled out.
It immediately I could tell he felt as awkward as I now did. I was kneeling in his living room, in a dress, after just seducing my best friend of 20 years. He still offered to let me change clothes, which I had to get from the car. Buy the time I got back he was in the shower and when I walked into the bathroom to cleanup I caught him slightly erect again and rubbing his cock. Not wanting to waste another chance I reached through the shower curtain and started stroking him. The first time must have been good because he stepped right out of the shower as I sat on the toilet and took him back into my mouth. This time I pulled my g-string down and with one hand and stroked myself as I suck him hard again. Feeling his cock grow in my mouth made me so horny I didn't even think when I pulled out my small six inch vibrator and began working my ass with it.
With me sucking him between my lips and sliding up and down his cock, I heard him ask what I was doing with that vibrator. I told him it felt good and he had me so hot I wanted something to stimulate me too. Slowly I worked the whole thing into my ass, rocking it in till I was flat on the seat. I secretly wished it was him instead. Then he asked me to stand, pulling my dress high enough to see my smooth legs and ass. When he stepped back far enough, he turned my hips till my ass was just inches from his cock. I relaxed my ass as I pulled the vibrator out and dropped it in the shower, backing up till I felt him rub my cheeks. With the baby lotion next to me I leaned over and rubbed it on my hole and the tip of his cock, keeping his cock pressing against me. With only a little help guiding and spreading he entered about 3 inches into me.
After a few seconds to get used to his cock I backed up till all eight inches were inside. I felt him sliding slowly at first deep inside till his hips were slapping my cheeks with each thrust. It seemed to fast but I guess I just wanted it to last. When he came he kept his cock deep up my ass till I could feel the cum running down my leg. Slowly as he started to soften I felt him slip from my ass. He got back in the shower and I changed and left. Its been almost 6 months since that night and we have partied several times together but neither of us has said a word about it. I'd love to do it again but I'm not sure how to start. I have to relieve myself every time I think about it which I'm doing now. Hope you liked my story!