His Sister's Panties

Peter sat on the edge of his bed looking somewhat blankly at the table in the corner, upon which rested various bottles and tubes of makeup. Tonight would be the first time that he would actually go out wearing it. His clothes were laid carefully on his bed and the black pumps neatly placed on the floor. The anticipation was almost overwhelming for him. He had shopped online and found a shop that catered to transsexual clothing and purchased them to make his hips more like a woman's and a special silky bra and matching thong to give him a more feminine feel. The little black dress, also purchased from the store was both sensual and strategic in covering the Adam's apple. He looked upon tonight's date as a sort of coming out and a test of how "she" would look to others. As he sat staring at the table, his mind wandered back ten years when, as a seventeen year old, he snuck into his step sister's bedroom and opened her clothes hamper. She was a year older and would soon be on her way to university and he decided now was the time to act. Initially he convinced himself that it was his male hormones that had driven him to check out her bra and panties. He sniffed the crotch of her bikini and the aroma of her fresh pussy filled his senses. What was more noticeable to him, however, was that when his fingers stroked the silky material of her panties and bra his cock raged with desire.

Peter would sneak into her room whenever he was home alone and before long, the slender youth was tiptoeing into her room naked and he was slipping her silk panties up his legs encasing his cock in a mist of softness. As soon as the sensation of silk on his cock made its way to his brain, his cock would harden and Peter rubbed his hard meat through the thin fabric. On one such occasion, his step sister surprised him by entering the room. At first, she was shocked but quickly became aroused at the sight of Peter dressed only in her panties. Her makeup instructions and tips were meant initially to be funny but soon she realized that Peter was a very attentive pupil and although they tried having sex once with miserable results, they became the best of friends which baffled their parents and youngest brother. She had taught him well!

In his last year of university, Peter had met Phil and one night, over a beer at a quiet pub, learned that Phil was gay but played the part of a school jock to hide the fact. There was something about Peter that Phil felt comfortable talking about such things and they became inseparable throughout the balance of the year although they did not draw any attention to their private lives making it more a matter that Peter, a mathematical wizard, was tutoring Phil. In fact, throughout that year, they did not explore their sexuality and indeed, Peter had never had a sexual relationship with a man and did not consider himself to be gay. After graduation, the two went their separate ways until Phil found himself transferred to 6 years later to New York where Peter had become a highly successful investment banker. He decided to call his old friend and Peter agreed to see meet Phil who had now taken a job with a professional sports team and keeping up appearances was critical.

They would get together occasionally and when they were at Peter's place they began to get intimate. It started off with jacking off together and soon, each was sucking on the other's shaft and getting a mouth full of cum. Peter refused to have sex though and, although he was attracted to the six-foot jock, the barely five and a half foot Peter just didn't feel right. That was until one night, he decided to put on his sexy thong and bra and dress up before Phil arrived. Phil was surprised at his friend's appearance but thought it was cool that Peter was a cross dresser. That night, Phil sat at Peter's side and before long the two were feverishly petting each other. Phil undressed Peter down to his bra and panties and after sucking Peter through his silky thong, Peter bent over and invited his boyfriend to fuck his ass. Before Phil left later that night, they had both experienced anal sex with a fire not previously known and, standing before a full length mirror in the bedroom, Phil remarked that they made a great looking couple igniting the imagination of both. The plan, they hoped, would solve both of their problems.

A week later, Phil called Peter and told him there was a team function at the theater and asked f they could pull off being a straight couple. "Let's give it a try," Peter replied with enthusiasm. "I think I can do it but if you see me and don't think we can, then you will have to go by yourself.

Peter had taken all day to get ready. It was now an hour before Phil was to pick him up and he shaved for the third and final time then applied his makeup as meticulously as his sister had taught him. He studied his face carefully in the magnifying mirror and could find no flaws then carefully placed the sandy brown wig over his short, similarly colored hair and looked admiringly upon the result. He slipped on his silk bra with the breast enhancers and then his matching thong followed by the pantyhose with the hip forms to give his slender hips a well-contoured appearance and stepped into his dress. He had made a few test runs of being a woman before but this was the first time he had completely done himself to the nines and he turned tentatively and approached the full-length mirror. He looked for what seemed an eternity at the reflection trying to find Peter in the image. What he saw, however, was a woman. It was the woman that he wanted to be and if he did say so himself, she was stunning. His concentration was broken by the knock on the door and, sucking in his breath he answered.

"Holy shit," Phil gasped, "you look incredible." Then without waiting for a response continued, "We can do this!"

They looked at their reflection in the mirror and both agreed and, sliding his arm into that of Phil, the lovely looking couple went to the ball. Phil introduced Peter as Sandy because of the color of her hair and neither could see any glances that would make them think that Sandy was suspected of being a man. Halfway through the evening, when Sandy had gone to the ladies room, a player on the team came over to Phil saying, "You really have a hot babe. Are you two dating or can I maybe get in on her." Phil had to laugh and said they were a couple and Sandy tended to be a one man woman. As Sandy returned to the room, another member of the team tried to pick her up but she graciously refused before joining her date. The two found themselves becoming very aroused at being able to pull this ruse off and it was good that Peter had bound his cock and balls tightly or his hard on would have been very noticeable in the dress. The would sneak kisses and Phil would caress her bum as they stood close together and it soon became apparent to both they were going to have to get some relief to their horny cocks as soon as possible. As soon as the official part of the evening was over and after they had enjoyed a couple of slow dances, Phil told his boss that his girlfriend was not feeling well and the two were going to leave.

Throughout the trip home, Sandy could not keep her hands off the throbbing bulge in Phil's pants making it difficult for him to concentrate on driving. He parked the car quickly in front of Sandy's house and the couple entered quickly. Phil, spun Sandy around to face him and kissed her deeply while pulling her ass tight to him so she could feel his hard cock pressing against her belly ...

-Continued-

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