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.