TG Captions Pages

Thursday, December 09, 2010

TG Story: Caught crossdressing where he shouldn't be

A crossdresser goes a high-heeled step too far
The girls check out the new girl
Tommy was keen to get into the fraternity so when he was set a make or break challenge of obtaining secret journals from the Pi Beta Phi sorority house he breathed an inner sigh of relief. Only girls were allowed into the sorority building, and that was the challenge but Tommy had a secret that was going to make things a lot easier.
Tommy had been crossdressing in secret for quite a few years and was quite adept at completely feminizing himself. No one knew of his hobby but now he had a plan of how to use his passion for dressing as a girl to a real advantage. There were many girls coming in and out of the sorority dorm house visiting their friends all the time. All he had to do was dress as a college girl and sneak into the building. There didn't seem to be any other way of obtaining the journals that held all the naughtiest confessed secrets of the sorority members. He chose his moment well for a time when most of the girls were likely to be out and then packed everything he need into his car and drove to a motel where he changed into black outfit with a short black skirt. As nervous as he was he was also looking forward to walking around campus like a real girl. He put gel in his hair to make it more feminine, applied his make up and looked in the mirror. To his delight a young college girl was smiling back at him. He went back to his car and drove to the sorority house parking far enough away that no one would see him. Then he began the walk to his target. It was evening and as he walked through the darkness he felt his panic rising. What if someone saw him? Then to his horror he saw two girls that he knew coming straight towards him. There was nowhere to go so he kept walking and although they looked straight at him they didn't recognize him. Feeling more confident he continued on his way and began to enjoy his escapade. Here he was was walking around campus, fully feminized, his heels clicking on the sidewalk, and everyone who saw him thought he was  just another girl. Finally he arrived at the sorority house. There was some sounds of activity from inside which concerned him but he had come this far so he kept going. He walked up the steps wondering if the door was locked but just as he reached for the handle the door opened and three girls came out. The looked him right in the face and smiled at him, then held the door open for him before leaving themselves. Inside the hallway Tommy's heart was pounding. Two girls wearing tight workout shorts and tank top were just going up the stairs but they didn't hear him come in. He could hear shouts and laughter from the upper floors where girls were going about their business. The journals would be in the meeting room on the ground floor. He headed for a large door at the end of the corridor and as he did he glanced up an saw a girl on the first floor meander along the landing wearing only a white bra and orange panties. She paid no attention to him. Tommy reached the door and opened it. His guess was right, it was the meeting room and to his relief he quickly found the journals on a bookshelf. He grabbed three of the most recent journals and headed back out clutching the books to his chest. 
Tommy wishes he hadn't put so much detail into dressing as a girl
He was nearly at the front door when it opened and the two girls he had passed earlier came in. Their names were Karyn and Debs and as they came in they stared him straight in the face. Tommy continued on his way not daring to breath and was about to reach for the door when Karyn spoke. "Hey don't I know you from somewhere," she asked and he thought he heard Debs giggle. Tommy considered his options. He could ignore then or stop and answer the question. But his voice would give him away. He reached for the door and then to his horror he felt someone grab his skirt and try to pull it up from behind. He instinctively spun around to face Karyn who was still trying to pull up his skirt. He pulled it down but now Debs was grabbing his skirt as well. "I thought so, it's Tommy all dolled up as girl," shrieked Karyn. "What on earth are you doing here?" As he tried to fight off the girls Tommy dropped the journals. He decided to just grab the journals and run. If world got out that he had dressed as a girl then he could still pass it off as a great way of getting into the girls' dorm. But he was desperate to not have the girls get a look up his skirt. He bent over to pick up the journals and the girls seized their chance grabbing the hem of his skirt and pulling it right up to reveal the white thong pantie he was wearing.
The girls discover his thong panty
"Oooh, cute panties Tommy-boy, I'm wearing something similar myself," Debs laughed.
He could explain away dressing as girl to sneak into the building but there was no way he could explain why he went to the trouble of putting on sexy thong panties too. That was the kind of extra touch only a true sissy would bother with.
Tommy grabbed the journals but before he could straighten up Karyn kicked him hard in the butt. It was too much for him to maintain his balance in his heels and he sprawled flat on the floor with his skirt up around his waist.
By now other girls were coming out of their rooms to find out what all the fuss was about.
"What's going on?" asked a voice he didn't recognize.
"It's Tommy dressed as a girl in panties and who knows what else and by the looks of things trying to steal our journals," shouted Debs.
As Tommy struggled to get to his feet he turned to face a crowd of bemused girls charing towards him.
"Let's get him girls!" shouted a blonde girl wearing a robe.
Tommy went down under again and was quickly immobilized.
Five minutes later he was chained to the lamppost outside the sorority building clad only in his bra and panties. As an amused crowd gather around him out on the street, inside the building the journals were safely back in the meeting room.


Anonymous said...

Tommy would be better off than me....I would of worn a pink thong

Anonymous said...

oh that is so nice to be in his/her shoes

Tayphad said...

Absolutely a stunning story! Loved the pictures associated with it.