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Caught In My Best Friend's Wife's Underwear

"I shared a flat with my best friend and his wife; and he caught me in her underwear"

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Last summer I lost my job and couldn't afford to pay the rent on my flat. Fortunately, my best friend Jim said I could stay at his house with him and his wife until I found another job.

I had been best friends with Jim since high school and had always fancied his wife Sally. She was drop-dead gorgeous with a figure to die for. She had long slender legs, was slim, and had a wonderful set of breasts. It helped that she was a wonderfully sexy dresser as well.

Now, I am a bisexual guy who likes to cross-dress and I always fantasised about both fucking Sally and being dressed up like Sally. One winter night I got the opportunity to try out dressing up like her. She was away on business and Jim was out working late. I had recently met a guy on a chat website who liked me to dress up for him. I decided that it was a great opportunity to dress up in Sally's sexy clothes and take some pictures of myself to send to my new guy in the hope that they would rev him up for our next meet.

I snuck into Jim and Sally's room and slipped on her sexy basque stockings and suspenders set. I then topped this with a tight white blouse and a short black pencil skirt. I even managed to find some fuck me shoes that fitted. I set my camera up on a tripod and set it to take a photo every twenty seconds. I then started to pose for the camera. I started tame and flashed a basque strap or suspenders top. But soon I began to feel sexy and my cock started to stiffen. I got on the bed on all fours and hitched up the skirt so that the basque knickers would be visible in the next picture.

Then, to my surprise, the door opened and Jim exclaimed, “Sally, what are you doing back?” He quickly realised his mistake and inquired, “What the fuck was going on?”

I shuffled forward to turn the camera off and Jim caught me by the arm. “So you like dressing like my wife do you, you fucking sissy?”

I just whispered, “Yes,” back.

He noticed the camera and asked who the pictures were for. I told him about my online friend. He replied that looking like that if I wanted fucking all I had to do was ask. I had been friends with Jim for years but neither knew he would be with a guy.

He turned me around and pulled me close. I could feel his stiff cock pressing against me and he lent in and started to kiss me. His tongue was deep down my throat and his hands felt me through the skirt.

My cock stiffened even more and I groaned.

He laughed and told me he knew what little sissy’s like me needed. He forced me to kneel down and dropped his trousers and boxers. I had never seen his cock before and was surprised at just how large it was. It must have been ten or eleven inches of throbbing hardness. I couldn’t control myself and got to work. Initially, I pumped his cock with my hand, then I began to gently run my tongue up its length.

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Finally, I took it into my mouth and enthusiastically sucked. He loved it and told me I was a good girl, which turned me in more so I sucked harder and harder. His pre-cum oozed into my mouth.

I stopped to catch my breath and he begged me not to stop. I told him I didn’t want him to cum yet as I needed him inside me.

“Fuck yes,” he screamed.

We climbed into the bed and he gently took the blouse and skirt off. He told me I was wearing his favourite underwear and that Sally never wore it for him.

I replied, “Little sissy sluts like myself need Daddies like you to fuck them.”

“Oh yer,” he replied and he pulled the panties to one side and roughly entered me. He quickly got into a rhythm and I keep moaning and gasping with pleasure. He leaned forward and kissed me as he fucked me. His hands held mine as his tongue probed my mouth, and his cock my arse. My hands firmly grasped his bum cheeks as he pumped me. Their firmness turned me on so much.

My cock was still straining and I needed to cum. I told him this and he told me to get on all fours. I quickly move into position and he re-entered me from behind, his hands holding my hips steady as he fucked me hard. After a few thrusts, his hand slipped down and started to play with my cock. I instantly groaned and begged him to make me cum. He leaned forward and started kissing my neck and ears before he started to wank me very hard. His cock still thrusting deep inside me.

I couldn’t hold it and exclaimed, “Daddy, I’m cumming.”

I shot my load onto his hand and he seemed to like this as he thrust harder and a few seconds later he exclaimed he was cumming too. I felt his hot load shoot inside me.

We collapsed into a hot sweaty mess and gently kissed and touched each other for another ten minutes or so. He eventually got up and told me I was now his bitch and we were going to have to find a way to get Sally to go away more often. He then went over to a cupboard and picked out some different lingerie. He told me he going out but I should be in bed wearing that lingerie for when he got back.

And so started a summer of endless fucking.

Published 
Written by dave99
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