"Squadron Leader" by Lucy Roberts.
This story was written after a request from a friend. If you like this story please let me know
It was Tuesday evening and Gary had just got home from school.
He opened the front door and shouted. There was no one in. Mum was clearly out somewhere and his older sister obviously hadn't got back from school yet.
Gary went upstairs to change.
As a 13 year old boy he couldn't wait to get out of his school uniform.
Taking off his shirt he went to the bathroom to drop it in the washing basket as he did so he noticed something that caught his attention. It was a pair of his sister Kate's panties. The familiar temptations came over him and he picked them out of the basket and took them with him to his room.
Once in his room he studied the panties. They were white with a trim of light pink lace and a little pink bow at the front.
Gary quickly stripped off all his clothes and put the panties on. Ohh so lovely. The familiar feel of girl's panties over his bottom felt so good. He knew what he had to do next. He opened his bedroom door and, checking there was still no one else in the house he returned to the bathroom and yes, there at the bottom of the washing basket was what he wanted, a pair of tights.
With his new treasure he returned to the bedroom and soon had them up his legs and round his bottom.
The next half hour was bliss as he wandered round his room or lay on his bed rubbing his hands over his legs and bottom.
Finally, hearing a sound downstairs, he put on his jeans, a tee shirt and some socks and went down to see his mother.
After tea Gary was back up in his room with his jeans off enjoying his tights again when his Mum shouted up, "Gary hurry up it's time to take you to cadets."
Gary jumped to it. He pulled off his tee shirt and the tights. He was about to take the panties off when he thought, "no I'll wear them tonight no one will know."
It was not the best thought Gary would have that day!
He quickly put on his uniform, white shirt dark tie and airforce blue trousers, rushed down stairs and jumped into the car with his Mum.
When they got to the meeting hut there were already quite a few people there and parade was just about to start.
Gary stood there in line looking at the others. He was the youngest and newest of the company. Alongside him were some much bigger boys all in the same uniform and a number of girls in similar uniform but with skirts and navy blue opaque tights.
Gary envied them. How he would love to be on parade in a skirt and tights.
The evening proceeded with various teaching points and drills. Then there was a period of group activity.
It was during this that things went badly wrong for Gary. He made a vital mistake which caused his group to lose the competition.
During their breaktime Gary was faced by two large angry boys.
"You little creep," bellowed Tom, "you just lost that and the points for the squadron cup that went with it. I ought to stuff your head down the toilet."
"You can't do that," whined Gary.
"No we can't," said Nick, "cos the Leader would find out but I think we'll just debag you instead and push you out where the girls can see you."
With that the two boys grabbed Gary and in a trice has his trousers off revealing the small boy in his panties.
"Oh my," spluttered Nick, "what have we got here?"
"We've got ourselves a little girly," laughed Tom. "I think we ought take him to the other girls where he belongs."
The two boys ushered Gary to where the girls were.
"I think this little girl got into the wrong group," said Tom.
There were peals of laughter from the girls.
"She can't go around like that," said Jenny. "Leave her here and we'll get her dressed properly."
"O.K.," said Tom. "But then bring her back here for us to see."
So Gary was left trouserless in the hands of half a dozen older girls.
There was no way out for him. He simply had to do what he was told.
So in no time at all he was standing before them in just his panties. But not for long. One of the girls raided the spare clothes store and soon Gary was wearing a nice white bra, which the girls filled out with tissues. Then they helped him into some regulation navy blue opaque tights.
The effect of the tights on Gary was electric. Immediately he felt a tingle in his prick and he couldn't help rubbing his hands over his bottom to feel how good they felt on him. The girls noticed this.
"Look the little cissy likes his tights," Jenny shouted.
The laughter rang round the room as Gary held his head down and blushed. But it was true he did like wearing the tights and while he was scared he was enjoying being dressed up.
Then they gave him a blouse and tie and then a uniform skirt. He willingly put them on.
"Seeing as how he is enjoying it," said Jenny, "let's do the job properly and put some make up on him."
The girls set to, combing out his hair and tying it with a ribbon then some mascara, eye shadow and lipstick.
Once they were satisfied they took him back to Tom and Nick.
"Well look at this," crowed Tom, "we have our own little cissy girl."
The two boys gave Gary the once over.
"She makes a pretty girl doesn't she Nick?"
"Actually she does make a surprisingly pretty girl," Nick added and again Gary could feel the colour rising to his face.
He couldn't understand why he felt so good in such a bad situation.
Tom walked round behind Gary and lifted his skirt and put his hands on Gary's bottom.
"Hmm, feels good as well."
That was all the encouragement Nick needed and soon both boys were rubbing their hands all over Gary's legs and bottom.
Nick noticed that there was a bulge in Gary's panties.
"Oh he is a little cissy look how he's enjoying it."
"Perhaps he wants to be a girly," added Tom. "Well let's see."
With that Tom pushed Gary down onto his knees.
"Go on cissy unzip me and take my prick out."
Gary had no option but to do what he was told.
He reached out and pulled Tom's zip down and then with trembling fingers reached inside his pants and freed the prick. It stood out straight just a few inches from his face.
"Go on cissy," urged Tom, "you know what to do now."
Gary didn't know what to do but he knew what Tom wanted him to do.
Gary held the prick for a few moments before sticking out his tongue and licking the end. It didn't taste too bad perhaps he could do it. But did he want to? In a sense he had no option but did he actually want to? In those few moments as he held the firm flesh in his hands with his mouth poised Gary realised that actually he did want to suck Tom's prick. He could feel his own prick straining against the panties he was wearing telling him very clearly that, difficult as the situation was, he was excited by it.
Gary leant forward and took the prick in his mouth. It actually tasted quite good and the movement of it in and out was quite exciting. As he was sucking Tom's prick he felt his skirt being lifted up and a pair of hands begin rubbing his bottom and legs through the tights and panties. Then he felt a prick rubbing up and down the crease between his cheeks. Gary thought he would cum on the spot but managed to hold himself back, which was more than Tom did because all of a sudden Gary found his mouth full of cum as Tom shot load after load of the creamy white juice into Gary.
Gary didn't know what to do and so he took the only option, which was to swallow the load. As he did so Tom pulled his prick out of Gary's mouth. Gary found he was disappointed but not for long because Nick's prick which had been rubbing against Gary's bottom was now in front of Gary's face and Gary gladly took it into his mouth.
Gary couldn't believe how excited he felt and how much like a girl he felt. He had no thoughts for later and what might be said or happen. He was just so enjoying being dressed as a girl and acting like one.
It didn't take long before he was swallowing his second load of cum.
A few minutes later with Gary sitting quietly while the two boys made fun of him the girls came back.
"Oh Gracie," said Jenny, "what have you been doing your make up is all spoilt."
She and the others began laughing as Jenny took out her lipstick and repaired the damage. It was at that point that the Squadron leader entered the room.
"What's going on," he bellowed.
With that Gary burst into tears.
The leader took Gary off to his office with dire warnings for the others about what repercussions this might have.
The leader sat Gary on a settee and sat beside him and asked Gary about what had been happening and Gary told him everything even about sucking the two boys off.
"That is awful," said the Leader when Garry had finished. "Mind you, you do make a very nice girl."
With that the Leader put his arms around Gary. Gary thought it was just to comfort him but then found the Leaders lips on his. Gary opened his mouth to protest and found the Leader's tongue inside his mouth. Gary knew he should try and stop this but then he realized he didn't want to. The Leader's hand was now on Gary's knee and moving up under his skirt as Gary concentrated on kissing him back.
For the next few minutes they sat there kissing as the Leader ran his hands over Gary's body, up his legs, over his breasts, everywhere.
Then the Leader took Gary's hand and put it on his crotch. Gary could feel the stiff prick through the rough blue trousers.
"Would you like to help me with this?" the Leader asked.
"Yes sir," Gary mumbled in reply.
The Leader stood up and quickly took off all his clothes.
He stood there with is prick standing out stiff and ready for action.
Then he came over to Gary and took off Gary's blouse and skirt.
He stepped back and looked at Gary.
"Oh my don't you look delectable little girl. I've always dreamed about having a little girl like you."
The Leader sat on a chair and pulled Gary onto his lap. Gary could feel the hard prick pushing at him as the Leader kissed him and touched his body. Gary had to admit to himself that he loved the feel of the Leader's hands on his legs and bottom. He just wanted to please the Leader and make him happy.
The Leader pushed Gary off his lap and onto the floor where Gary knelt between the Leader's legs. He leaned forward and took the Leader's prick into his warm mouth. The Leader's prick was so much bigger than the boys he'd sucked earlier and Gary had trouble getting it into his mouth.
As he sucked the prick he could hear the groans coming and this excited him even more that he could give such pleasure to this man. Gary gave a little girly wiggle with his bottom.
After a few minutes the Leader pulled his prick out of Gary's mouth.
"Not so fast my little darling," he said as he helped Gary to his feet. "I have a better idea for a special girl like you."
Gary watched as the Leader went over to the first aid kit and pulled out a tube.
He came back and pulled Gary's tights and panties down to his knees. Then he bent Gary over the desk. Gary felt something cold being rubbed on his bottom and suddenly one of the Leader's fingers was inside him.
"Now my little girl," the Leader said, "you are going to become a real girl and I'm going to be the first one to fuck you."
Gary was not at all sure that he wanted this but stretched over the Leader's desk wearing just a bra and with his panties and tights round his knees he didn't see he had any choice.
He felt the Leader pull his cheeks aside and he could feel something pushing at his little rosebud opening and he was in no doubt as to what it was.
Suddenly the pain was searing as the Leader's prick forced its way in. Gary let out a little sob and the Leader paused for a moment and then slowly began to ease in and out. To start with it hurt but then Gary began to find the pain subsiding and he began to quite enjoy it.
In fact when the Leader began to rub his cheeks and then reach round and hold his breasts and pull Gary onto him more, Gary began to really enjoy it and started to move his bottom to fit the Leader's rhythm.
Now it wasn't just the Leader who was groaning but Gary too was giving out little girly whimpers of excitement and joy. His little prick was hard and rubbing against the desk but his thoughts were all on the wonderful prick that now was filling him and now drawing out. Gary was in heaven. He was a girl who was being loved by a man.
Suddenly the Leader gave a big jerk and Gary could feel the cum spurting into him. He was so happy. He felt so good.
The Leader lay across him for a few moments and then let his prick slide out.
Gary stood up and pulled up his panties and tights conscious of the sticky cum that was beginning to dribble out of him.
The Leader sat back on his chair and again pulled Gary down onto his lap.
" That was wonderful," the Leader said as he caressed Gary's legs. "I hope we can do this again some time. Would you like that? Would you like to be my special girl?"
Gary's answer was to kiss him and at the same time reach down and fondle the Leader's soft sticky prick.