Our First Dance

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He insults the frat leaders girl, now he has to pay.
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PenanceS
PenanceS
60 Followers

Steve sighed slightly as he looked into those eyes, in them he was able to see his own reflection, and he was surprised at just how things had turned out. If anyone had told him that he would be sitting there, in the Alpha Tao Omega house, dancing, in a blonde wig, and a low cut evening gown, he would have said that they were crazy.

It had started out innocently enough all right, there was the Friday night pool game with the guys, tossing back a few brew ski’s, and then letting the alcohol affect his judgment ever so much that he managed to convince them that he would look better in a dress than Samantha Hathaway did.

Sam, just happened to be the captain of the Cheerleading squad, and the girlfriend of the head of Omega.

Though the leader was a good sport about it, he easily convinced Steve that she should either apologize to his girl, or be prepared to take the consequences.

Steve being a hot-headed one didn’t want to do anything of the sort, but was convinced that he should at least make-up for it in some manor.

Steve – after being placed in a headlock, reluctantly agreed.

‘Whatever shall we have dear, old Steve do boys?” The leader asked them, the other chums of the Omega house were already soused from so many beers as it was, and St3eve didn’t think that he would be able to take all of them on.

“Got it!” Tony Lombardo belched slightly as he staggered around. “I think that we should have Steve go as a girl to the Mardi-gras ball on Friday night. What’dya think about that, Leader one?”

The leader, who happened to be named Tom, seemed to think that it was a very good idea. “Then it’s all settled, Steven. At approximately seven PM, you will get dressed in a dress of some sort, and all of the other accoutrements, and head out on the town with the rest of the college. Doesn’t that sound fun?”

Steve started to nod “no” but as Tom approached him with a sense of malice in his eyes, Steve thought it best not to argue. “S-sounds great.” He smiled weakly at the rest of the group, and wished silently that he were back in his own dorm room, with the door securely locked.

“I’m sure that we can have one of the girls spot you a dress of some sort for the big shindig, don’t you think?”

“Sure no problem.”

“That’s a good lad.” Tom clapped him heartily upon the back; it’s getting late, Steven. You probably need to be heading back to your own room don’t you?”

“Sir, yes sir!” Steven barked.

“Good boy. Have a good night, and try not to worry, everything will be just fine, count on it!”

Steven nodded weakly and headed back to his own room, crashing heavily upon the board like mattress and falling into a deep sleep.

His head buzzed slightly, in the morning, and for a second, as he looked out his 1x1 window, Steve thought that the whole thing had just been an intoxication dream.

Yet as he stumbled out of his bed, and headed into the bathroom to take a leak, the slight of a silver strapless evening gown, bra, panties and high heels hanging from the door jamb of his room, brought it all fresh to light.

There was a note clipped onto the dress. “Steve, be ready at nine tonight, the partyt starts at 9:30, and you wouldn’t want to be late would you?”

Steve took a deep gulp, grabbed the garments and placed them upon his bed. “If I’m going to do this, than I’ll do it in style.” He thought to himself.

He closed the door and headed onto his morning classes.

The day zoomed by, until at last, the clock read five PM, and it was dinnertime. As he was rushing out of the doorway, he bumped into none other than Tom.

“Hey Steve, aren’t you forgetting something?”

“Nope, just going to put it on now, the party doesn’t start till 9:00 anyway, remember?”

“Yup, come on. “

“Wh-where are we going?”

“Back to your place, we’re going to get you all set.” The two men stopped on their way to the girl’s dormitory, and Tom knocked on a particular window. A few moments later, and Sam stuck her head out.

“Baby!” She sounded excited, until she realized just who was with her beau. “Oh, its him.” She added dryly.

“Just relax baby, we got it covered, don’t we Steve?”

“Yep.” Steve laughed nervously as the three of them headed back to his room.

Steve opened up his door, and graciously asked his ‘guests ‘ to come in.

Once inside, Sam locked the door.

“Alright, Steve, get on with it.”

For a minute, Steve wondered just what Tom was talking about, but then icily realized that he was supposed to strip, and re-dress in the dress… with Sam in the room! With a shrug, Steve kicked off his shoes and pulled off his shirt, letting it fall onto a pile on the floor. His muscled abdomen and pecks stood out firmly, and Sam gave a low whistle.

Steve felt himself blush, and almost refused to go any further.

“Come on boy, you promised Sam that you would.” Tom started to bully Steve into undressing, but Sam placed a finger to her beau’s lips.

“Here let me take care of that.” She walked up to Steve, and gently unzipped his pants; she grasped his pants and underwear and pulled them down in one swift movement.

Steve reddened as he felt himself harden, and a sweat broke out upon his skin as he realized Tom was right there.

“Lift a leg;” commanded Sam, and Steve obliged. Sam gently pressed the pants down further and helped steady Steve so that he could step out of the garments.

Sam then turned to Tom and took a line of duct tape from him.

“What are you going to do with that?” Asked Steve, nervously.

“Just watch.” Sam gently stroked Steve, and despite himself, he could feel himself get hard. Once Sam thought that he was at the sufficient length, she deftly taped Steve’s engorged prick next to his leg, slightly back towards his buttocks.

If anyone were to look at Steve now, he would look like an extremely flat-chested woman.

Sam reached out for something witch Tom handed her. “Lift your leg again sweetie.” Steve obliged, and realized that he was slipping on a pair of cotton Haynes Her Way panties; he grimaced as he felt the elastic snap tightly around his waist.

A bra, complete with gel inserts was snapped tightly around his chest, shoulders and back. Steve could already tell that the weight of the implants and the tightness of the elastic straps were going to leave marks on his otherwise pristine shoulders, but there wasn’t really anything that he could do about that.

It sounded like gunshots as the clasps of the bra were slung together. He got a quick glimpse of himself in the mirror, and for all intents and purposes, he did look like a woman. A rather LARGE woman, but a woman nonetheless; Sam pressed him back in a seat and added a pair of purple nylon stockings to the ensemble, gently drawing them over Steve’s legs.

Steve began to sweat, as it was a pet peeve for him to have anything over his legs that was that tight and constraining.

The last thing that was left was a purple dress, and a big, floppy, green hat to complete everything.

“There now, don’t you look cute?” Sam smiled coyly at him, letting Steve turn around and ace the mirror. “You look absolutely beautiful, doesn’t he tom?”

”Just perfect,” Tom sneered, as he looked Steve over. He slid a hand under the dress and caressed Steve’s bare skin. “You look good enough to eat boy.”

“Can we go now?” Steve asked, miserable, and wondering when the torment would be over.

“Almost.” Sam reached into a bag and handed Steve a harlequin mask. “Here put this on. We want you to look good for the ball.”

Steve said nothing but did as he was told. Then the three of them headed out the door, Sam stopped in the ladies room and changed into a Lumberjack ensemble, while Tome decided that he could stay in his normal clothes.

The gym was heavily packed and noisy as the DJ was going at it full blast. Steve gulped, there had to be at least 500 people in that room.

Sam came up next to him and grabbed his arm. “Are you ready, my dear?”

Steve didn’t know what to say and allowed himself to be pulled into the room. There were so many people there, the skirt felt tight, yet at the same time, he felt daring.

The DJ put on a soft song and Sam put her arms around Steve in the traditional male role, clasping him close to her, her palm upon her butt. “Care to dance, Miss?” Sam laughed heartily.

Steve nodded, unsure what to say. He gently laid his head down upon Sam’s shoulder, and was surprised to feel Sam’s warm hand sneaking up the dress to clasp at his inner thigh, and penis!

“Sam, Sam, what are you doing? Tom’ll kill me if he finds out.”

“Just relax, Tom isn’t here right now, enjoy these feelings, and besides…” Sam gently started to stroke him a little more, feeling him become hard underneath the dress. “The dress will hide anything that…”

Suddenly Steve stiffened, and felt his cock spit up copious loads of cum into the panties he was wearing.

“...Should happen.” Sam smiled and with her other, clean hand, gently laid Steve’s head upon her shoulder. “Dance with me, miss…”

In the throb of the music, Steve forgot all about his troubles with Tom, the misplaced insult that he had placed upon Sam, and the fact that he had just cum while wearing a dress. He laid his head down upon Sam’s shoulder, and felt just like a good little girl.

“I don’t ever want this night to end…” Steve whispered to Sam.

“Don’t worry baby, it won’t… it won’t.”

PenanceS
PenanceS
60 Followers
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