The Education of Tami

This is one of my oldest stories. Recently found it again. I have some new stories on the way.

The Education of Tami By Tami

Chapter One - The emergence

He never thought anything like this could or would happen. Tim was always a rather reserved, quiet person, and was, in fact, a complete professional in his normal, everyday life. He has a successful career, and was constantly receiving praise for his performance from supervisors and co-workers alike. He enjoyed the things that most men did, drinking, sports, flirting with women. He was very much a normal everyday "guy" for the most part. He did, however, have some special interests outside of his everyday life that very people were privy to.

Most people would never have guessed that he had been dressing in female attire since he was 18. During his latter days in school, he started out wearing his sister's clothes, which aroused him very much. He often would dress to the nines in his sister's clothing and go out to the city for a drive. On some occasions, he even got up the nerve to get out of the car and walk the streets. He was always too scared to have anyone notice him, though. During his college days and early professional career, he attempted to dissuade himself of his secret habit and ventured into the vanilla lifestyle of the normal boyfriend/girlfriend relationship.

After a number of failed attempts, during which he attempted to "out" himself unsuccessfully, he decided to indulge his desires more, and began accumulating a rather extensive wardrobe of attire, mainly of leather and latex garments. He also began to "play" more often and accumulated toys for his "fantasy", including ball gags, collars, dildos, and butt plugs. He still saw himself as a 'normal' guy, but likened his interests as simply a hobby. He never really got up the nerve to venture out as his feminine self, save for the occasional Halloween costume when he would dress completely slutty, but this was always overlooked as simply a Halloween adventure.

No one really knew how 'kinky' Tami really was. After years of dressing up at home, applying self make-up and fantasizing about forced femme scenarios and meeting with a Dominant, Tami decided that she was going to finally meet a Dominant Female to help her explore her submissive tendencies and desires. Tami had occasionally fantasized about having sexual relations with another transvestite, but never about men. She somehow equated transvestites as women, which somehow did not equate him with being homosexual.

Tami had been online for a number of years and had chatted with tons of people claiming to be Dominants who would provide her with what she sought. Somehow, she had always found an excuse to chicken out. Not this time. She had set her mind to the fact that she would find a Mistress and meet her somewhere so that she could experience what, to this point, she had only dreamt about.

She was online in a Dominant Female chat room and had been chatting with a particular Mistress for a few weeks when Tami realized Mistress Jazmon would be the one she would attempt to meet with. Mistress Jazmon enjoyed many of the same 'kinks' that she did and was buxom and beautiful like Tami had imagined. Mistress Jazmon was very strict and was very much into humiliation and degradation of slaves, which Tami found irresistible. Mistress Jazmon lived in Detroit and as luck would have it, Tami's business was taking her to Detroit anyway. Mistress Jazmon suggested that they set up a meeting at a local hotel room.

Tami's heart was racing. She couldn't believe she was finally going to throw caution to the wind and submit to her desires as well as this beautiful woman. Mistress Jazmon's instructions were rather specific. Show up on Thursday night 9pm, at the Dew Drop Inn Motel, Room 215 in downtown Detroit, wearing your sexiest outfit and with all of your toys. You may wear an overcoat, but you must be wearing your outfit or I will cancel the whole encounter.

Tami couldn't wait. She was so excited. Thursday had come, and she got ready as per Mistress Jazmon's orders. She took the whole day off, carefully shaving her entire body so that it was nice and smooth. She carefully applied her makeup in her usual heavy fashion, from her lipstick to her deep rouge and pink eyeliner (she preferred the pink colors, much more sissy, which she likened herself to). She decided to skip the pink French maid's outfit she had purchased a week ago, and decided to wear her black patent leather dress with a choker collar attached. It ran to just below her upper thigh and was low cut in the front. The back was cut in a "V" shape.

One more decision: Heels or boots? She could wear the heels with her "SLUT" thigh high stockings, or wear her thigh high patent leather boots with a 5" heel. She chose for the boots, thinking Mistress would be much more impressed, even though they were tough to walk in. She couldn't resists temptation though, and put the stockings on underneath the boots.

Tami completed her ensemble with her gold hoop earrings, and she took a look at herself in the mirror. WOW! Did she look good.

Tami thought to herself, "This is the best I have ever looked."

Finally, she packed a bag with all of her good toys and outfits. Among her clothes were her two maid uniform, black leather dress, and even her tailor made clear plastic skirt, which she adored, but couldn't imagine herself wearing in front of another person. You could see everything! She also made sure she had all of her toys. Large and small dildos, Large and small butt plugs, ankle and wrist restraints, ball and ring gag, and even a nice crop. She was rather proud of the collection she had accumulated.

The time was 8pm. She should leave now to arrive nice and prepared at about 8:45pm. She took one last deep breath and left her company hotel room with her black trench coat and bag in tow. She had hoped no one would take much notice, since she was wearing her wig and the heels were rather loud. No one on her floor. Whew! Just a quick elevator ride and down through the lobby and she was clear.

Whew! No one in the elevator. The doors of the elevator opened as she hit the lobby. Uh oh. Looks like a convention of some sort checking in. A quick glance of the placard read "Welcome Teamsters!" Gulp! Just what she needed.

She decided to just put her head down and walk straight through the lobby. Click, click, click, she was unable to silence the heels. The men started to turn their heads and a low murmur began. Tami tried to stride as quickly as possible, but the height of the heels limited her speed. One rather large man approached and stood directly in her path.

"Hi honey, where are you off to tonight? Your next trick?"

A laugh came from the crowd Tami gulped and tried to answer as politely as possible, "Excuse me sir, I am just on my way out, pardon me."

She felt someone's hand on her rear. She was not attracted to men, so the grab through a coarse sensation through her body.

Someone from the crowd yelled, "Hey, Bruno, I think she likes you!"

Again, another laugh from the crowd. Apparently, Bruno was the hefty man obstructing her departure.

"Excuse me, sir, may I please get by?" She did not want to be too assertive for fear the men would find out she was a transvestite.

"Actually, I think you should come up to my room with me, bitch."

Bruno grabbed her necked and tried to forcibly kiss her. He smudged her lipstick with his coarse, unshaven chin. Tami welled up with a combination of embarrassment, disbelief, and fright. She quickly kicked Bruno in his groin area and broke his grip. She ran as quickly as possible out of the hotel. The kick must have been a good one, because it took Bruno a moment to recover,

"YOU BITCH!"

During her escape, Bruno's clutch ripped her coat, which gave way to her dress, sending roars through the mass of men. With Bruno close behind Tami jumped in her car and was able to drive away safely, although Bruno stood in anger, cursing her the entire time.

Tami was amassed with anger, fright, and fear. She pulled to the side of the road to fix her smeared face. She couldn't believe what had happened, something she was not expecting. She couldn't believe a man had kissed her. Yuck!

Okay, she recomposed herself and began driving again. She glanced at the clock. Oh no, it's 8:40. I only have twenty minutes to get there.

She pulled up to the Dew Drop Inn Motel at about 8:58. She had only two minutes to get to the room. Fortunately, at least she thought, this motel was the seedy type with no lobby, and the entrance to each room on the outside, although the room she needed was on the second floor. She quickly fumbled through her makeshift purse looking for the note she had written with the room number. During the scuffle, a perfume bottle had leaked. She found the note somewhat smudged: Dew Drop Inn, Room 213.

She clacked her way up the stairs to the motel. Fortunately, it seemed rather quiet. She could notice no one in the area as she approached the door. Here it was, Showtime. The moment she couldn't wait for. Finally, she was going to delve right in.

She gathered all of the courage she could and rapped quietly on the door. She heard voices inside, which confused her. Tami wondered if Mistress Jazmon had brought a friend. Standing at the door, jacket partially ripped, her bag containing her entire transvestite life in her hands, standing tall in her heels, slowly the door opened. What Tami saw dropped her chin. There were 3 men inside the door, having what looked like a meeting. The man at the door had a gun in his right hand, and slowly a sly grin overcame his face.

"Come on in, baby", offered the man.

Tami was flabbergasted. She could hardly speak. She realized the room she was looking for was 215! On the other side of the building.

She softly replied, "I am sorry, Sir, I must have the wrong room."

She slowly tried to leave her spot of standing, but the man's response wasn't to her liking. "Well, Bitch, that's too bad for you, but good for us. I would suggest you come in here with me or I may have to damage that pretty little face of yours. I assume you see what I am holding."

Tami could see the pistol in his hand. There was no confusing the fact that she would in a situation she was completely unprepared for. What she had thought would be the most exciting experience she could imagine was quickly turning for the worse. She slowly entered the room, and the door was closed behind.

"Well, what do we have here?" said the second man. "Must be our lucky night."

There were three men in the room. The man at the door, whom she later learned was Manny, the second man on the bed, "Richard", and a third man on the far side of the room, Sam. A quick scan of the room told Tami she wandered into the wrong room. Not only was Manny brandishing a gun, but also she could see Richard sifting through a suitcase of plastic bags of white powder and Sam counting a suitcase of money. It was obvious that Tami had stumbled into a drug deal. She couldn't believe what was happening.

"Take your jacket off, sweetie." said Manny.

"No, thanks. Really, please. I am not in the right place. Please just let me leave."

Manny replied, "No way Bitch, you see the three of us here? We could use a little pleasing after a hard night of work, so let's start by you taking your fucking jacket off."

He reached over and tugged at her jacket, but all Tami could muster was, "Please, no..."

The removal of her jacket only made matters worse. Standing there in her choker black patent leather dress, 5" thigh high boots, and heavy makeup, every guy in the room stopped and stared.

Sam, the third male, finally spoke up, "Hmmm... mmm, looks like the bitch is prepared for us tonight."

Once again Tami could only respond, "No, please..."

At this point, Manny put the gun to Tami's forehead, "Look Bitch, I don't give a fuck who you were coming to see, or coming to do. Either you start being cooperative, like the good little slut you appear to be, or it'll get real ugly, real quick."

Tami could sense that her only option was to obey.

"Holy Shit, look at this guys!"

Tami turned and immediately welled up with a combination of fears and tears. Richard had opened her bag.

"This is one kinky bitch, look at this stuff!"

"Well, we can certainly help her with this stuff!"

Richard brought over the ring gag and forcefully placed it over Tami's mouth. She tried to fight, but to no avail.

"This'll shut the bitch up as well as keep her mouth open for our cocks."

'Our Cocks??' Tami couldn't believe it, she wasn't gay, and there was no way she wanted any of these guys' dirty cocks in her mouth.

"I can't wait to fuck her myself!" piped in Sam from the back.

Suddenly, Tami began to tremble, 'These guys think I am a female. What will they do what they find out I am not?'

Tami tried to speak, to reason with these guys, but to no avail. The ring gag in her mouth prevented her from saying anything understandable.

"Now," said Manny, "you are going to do exactly what you came for. You must be a whore or something dressed like that and carrying a bag full of this. Now get on your knees."

Tami tried to resist, but the other two men forced her to the ground. Manny pulled out his cock, and Tami could immediately smell the sweat from his crotch as he moved closer to her.

"If you do a good job," said Manny, "maybe I will let you swallow my whole load."

Tami shuddered at the thought and tried to resist as Manny slowly pushed his cock beyond the gag and into Tami's unwilling mouth. Tami attempted to resist, but the gag prevented her from stopping the intrusion.

"Go ahead bitch, resist, it's more fun that way."

Slowly Manny slid his cock in and out of Tami's mouth. She couldn't take much of the cock in her mouth, as she had never felt anything like this before.

"Take it all in, bitch."

Suddenly, Tami looked up and to her horrification could see Sam standing over her with a video camera.

"Just a souvenir of the occasion, whore."

Tami was mortified. Not only was she sucking another man's cock, but also someone was taping the entire scenario. The thrusts became faster and faster, as Manny began to moan.

"Good little whore, you are an even better cocksucker than I thought."

Suddenly, and without warning, Manny's cock began spewing a hot creamy liquid. Tami quickly realized he had cum in her mouth. She nearly gagged from the amount of cum, and her knees became weak with submission. She couldn't even keep the cum in her mouth due to the ring gag. Sam came over and got a close up.

"Look at her, what a pretty site this is."

"You think that is good, wait till she feels me, I haven't cum in ages." said Richard, as he pulled down his pants.

Tami could barely muster a fight as Richard started face fucking her. She just tried to put it out of her mind and do what she had just done.

'Okay,' she thought, 'if I just suck them off, maybe they'll let me go, and I can escape without being hurt.'

Suddenly, Manny began rubbing her ass. "I am almost ready for this, BITCH, you know I do enjoy anal sluts."

No way, there was no way she could take a cock up her virgin ass. The only thing she had ever had up there were small butt plugs. Not only that, if they saw under her skirt, they would find out she was a guy and probably knock her around.

Just as the thought hit her, Sam spoke up, "Wait, I've got an idea to get her ass good and ready for us. Take a look in her bag, these restraints are perfect."

With that, the men grabbed her arms and pulled her to the bed. The secured her wrists to the top of the bed in spread fashion and began to take off her boots to secure her ankles.

"Damn! This is one kinky bitch! Look at the stockings."

Tami almost forgot that her stockings couldn't hide her fate; "SLUT" was written all over them.

"Trust me fellas. When we are done, she will be."

She was terrified; there was no way to resist. And they still had no idea she was a man! There she was, face down, strapped to the bed, legs spread wide, ass in the air. With that, Manny crept up to the bed. Tami began to sob. There was no way she could hide her true gender now. Manny began stroking legs.

"Mmmm, what a tasty little cunt."

He began to kiss her neck. Suddenly, he jumped up.

"What the fuck? This bitch has a cock! She ain't no bitch, she is a fag in a whore's dress!"

"Well you know what? If that is what this sick mother fucker wants, that is what he is gonna get. Three hard cocks right up his ass! What do you think of that, WHORE? You like that?"

Tami tried to shake her head "No", but they would here none of it.

"What else is in that bag?" Manny grabbed the leather paddle Tami had brought along. "I think we need to get her ass nice and ready first."

Manny didn't even break Tami in. He started paddling right away. Tami started to cry more and more with each painful blow.

"Shut up and take it slut. This is nothing compared to what our cocks will feel like!"

Unbeknownst to Tami, she was becoming aroused.

"Look, the little fag is getting excited, look at the little cock. Keep it up Manny."

Tami couldn't believe it, this was turning her on as much as it hurt. Manny stopped paddling and Tami could feel the coolness on her ass. It was a nice, tingly feeling and she could feel herself pushing back, waiting for the next blow.

Suddenly, Manny pushed his cock into her ass. How quickly her emotions changed from enjoyment to fear. She could not believe that this, person, this "drug dealer" was penetrating her. She tried to resist, but her restraints kept her motionless, except for the back and forth motion of her red-blazoned ass. With that, Richard came in front of her and began removing her gag.

"Now, bitch, to go for the double play. You are gonna suck my cock, and if you dare bite me, I'll beat your ass so bad, even a fisherman's wharf sailor won't want you."

The gag was removed and Tami took a deep breath.

"Before you suck it though, bitch, I want you to beg." Richard said this particularly loud, as Sam moved in with the video camera to tape her response up close.

She could hardly believe her plight; has ass was full of this dirty cock grinding in and out of her body and now this other dirty guy was telling her to beg to suck his cock.

"Please... I can't." she murmured.

Richard smacked her face, "What did I tell you bitch? You want me to hurt you?"

"No, sir, please don't!" she replied.

"Then do as you're told, WHORE! Get this in close, Sammy." She could hardly believe the words leaving her mouth, "Please sir, I want to taste your cock, please fuck my face."

"Tell me what a sissy whore you are, BITCH!"

"Please sir, I know I am a sissy whore, I need your cock."

With that, Richard plowed into her mouth. The sensations running through her were endless. To be ass and face fucked simultaneously, well, she just couldn't keep up. Her body lost all muscle movement and seemed only to be held up by the motion of the men's cocks.

They fucked her for what seemed like hours. She could here them talking but barely could make out what was said. All she heard finally was, "NOW!"

With that, both men ejaculated at the same time. She couldn't believe it. She somehow at least thought they wouldn't cum inside of her. Both men emptied their pent up sperm inside of her.

"Wow," said Manny, "she was a pretty good fuck for a sissy whore."

Tami could feel the sperm oozing out of both of her ends.

"What do you think now, BITCH?"

Tami couldn't reply. She too, was too spent.

"What's your name anyway, WHORE?"

Tami could barely muster the energy to reply.

"Ah, Tami. What a nice name for a slut. You know what, just because you were such a good kinky whore, I'm gonna give you a hundred dollar bill and a sniff of our stash, just to include you with the party."