When she first met him online, she said to herself, “Oh shit, not another guy who loves to wear woman’s clothing. He is probably an old ugly fart who can no longer get his dick up, or a fucking fag.”
Amanda had never done anything like this before. She loathed the humiliation and pain people used just for sexual pleasure. Or at least she did until she learned there were many phases of it. She had no idea she would soon become a Mistress to a submissive male online.
After chatting with Skip a few times, she found it exhilarating. It thrilled her whole body and made her cum harder than she had for a long time. Skip, who she calls, my-male-cunt-slut, is a normal hot blooded sexy man who just happens to get off wearing woman‘s lingerie.
Skip, at first, must have thought Amanda would blow him off and type, sorry-not interested, like many women he chatted with did. Somehow she was different. She accepted him as a hot sexy person, who was kinky…just like her.
He told her, “Amanda, we can role play as a Mistress-sub and if you don’t like it, I will understand.”
To his surprise, she accepted, saying she was curious and want to try it. “Oh, fuck, she was one hot BBW. Just the kind of woman he liked. When she talked dirty, he nearly came right then in his pants.
Amanda said to him, “Cunt, go change into the black bra and panty set you were telling me about. Do It Now, or you will not be able to chat with me!”
He typed, “Yes Mistress! “ He could hardly run fast enough or dress with out blowing his load.
Then he typed, “I‘m back Mistress,” not daring to say anything else. His dick was throbbing and dripping precum like crazy. Fuck he loved it.
She then told him, “Turn on your cam cunt, I want to see if you did exactly what I told you to do. Don’t ask me to turn mine on slut, because you have to earn that privilege. Now, stroke that hard cock thru the silky fabric… do it! That’s it my fucking slut, rub it, now pinch your nipples hard, I want to see the hot perky nipples, or I will leave this chat and you will not hear from me again! Play for me, BITCH! And don‘t say a thing till I tell you it’s Ok to speak!!”
Skip did as ordered, ran his fingers over his cock, felt it throb, and thought, “I hope this pleases my Mistress.”
He dared not talk. She’d leave and his life would be crushed. He needed her as much as she needed him.
Amanda yelled, “Oh that’s good, my little cock-sucker, make your Mistress’s clit throb. Hell, if you think I am showing you my cunt…I’m not! “She loved it. Never would she dream this type of sex would make her clit swell so big and throb so hard…..GOD she wanted him to be their servicing her.
Skip continued to stroke his hard cock, and pinch his nipples hard. They were protruding like little bullets under the sheer black bra. “Oh god.” He thought. Please, Mistress, let me cum for you and eat it.
Amanda typed, “You have done well my male cunt. As your reward, I will let you remove your silk panties and jack off for me, but you must eat it for me.”
She watched the male cunt do as instructed, and since he could not hear or see her, she typed and screamed, “You fucking bitch, I am cumming!”
She then typed, “Maybe next time, you might see me, on cam! First, you must do this, and write me ALL the details. Wear your pantyhose to work every day this week and nothing else under them. If you fail to write me by Saturday, we will not chat again…you fucking son of a bitch!!!
Amanda left the chat still turned on. She thought, “I wonder if I did what a mistress was supposed to do. I must have, that male slut came so fucking hard.
Since she was alone, she lay down on her bed and slid her 8-inch vibrator deep in her cunt hard. She fucked her cunt slowly until the vibrator it was coated with her juices. Then put it against her anus and pushed the toy slowly in her tight asshole. She rubbed her clit vigorously and shouted, “OH, FUCK, I love it, I‘m cumming!
When she finished, she laid back and thought of all the ways she could humiliate her male slut. Then said, “I will just have to go online and study Mistress-Sub relationships. That fucker belongs to me now!”
Amanda and Skip had an exhilarating online relationship and the more she learned about Mistress-Submissive relationships, the more it turned her on. She wondered how it would feel to experience a real Mistress-Submissive relationship.
Skip lived within traveling distance of Amanda. They often chatted about the hot times they have during role-play. He said, “Oh Mistress, I wish you were really here doing all those things to me. You make my cock so fucking hard.”
One evening they were chatting and Skip asked, “Amanda, you’ve turned into a sexy Mistress, and in my words, a great one. You seem to know exactly what to say to make me obey. However, unless you actually have a real life experience, you are missing out of the best part. I will do anything you ask, if we met and I mean anything! Mistress, how would you like to meet me?”
Amanda replied, “I am not sure I’m ready for a real Mistress-Sub relationship yet. Do not get me wrong I would love to meet you for real. Is there a possibility for us to meet for dinner casually?”
Skip replied, “Sure we can, I think that’s a great idea. Maybe we can meet at a half way point between your place and mine.”
They chatted and agreed to meet him in a neutral location for dinner. She told him to make the arrangements and then email her the time and place since she was new to the area.
Three days later, she received an email from skip, “Meet me at, The Tropical Island, a favorite elegant dinner, at 7 pm next Saturday night. He gave her the direction and added, bring an overnight bag if you want, just in case you’re feeling like becoming a real Mistress.”
She replied to his email typing, “Your Mistress will be their, my male cunt-slut. You already know what I look like. Be there promptly at 7 pm, and do not disappoint me or be late, or you will not meet me at all slut!” Amanda told him she would make reservations at local hotel their too. That way they could take there time getting to know each other and she could return home the following day. Then typed see you soon, good-bye, Mistress Amanda.
Friday she went shopping at Fredrick’s of Hollywood. Amanda told the salesperson she was going to a party as a Mistress and wondered if she could help her get the things she needed.
She helped her pick out some stunning hot pink lingerie. It consisted of a lacy see through bra, matching silk panties and garter belt. She found the perfect shiny pink hose and fuck me heels to accentuate the outfit. She went into the dressing room and put the items on.
When she walked out to look at herself in the mirror, the sales-person came over to she if she needed more assistance. The woman grinned and said, “You’re a knock out lady, but you’re missing something.” She walked over to a table with leather cuffs, chains, handcuffs and whips on it, and pinked up a white ridding crop. She walked over to Amanda and handed her the whip.
Amanda turned around and looked at the sexy reflection in the mirror. She excitedly said, “Oh my god is that really me?” What do you think; do I look like a real Mistress?”
The woman said, “Yes, and with that outfit, you’ll have any man you want bowing and asking how they can serve you. Can I get you anything else? “
Amanda smirked and replied, “Oh yes, can I get this same outfit with, “A,” size bra. I am not sure of the man’s exact size but he is about six ft and weights 200 lbs and wears a size ten shoe.”
The salesperson said, “Why yes, we have them ranging from extra small to four x with bra sizes up to EE and shoes up to size 11. Shall I have that gift wrapped?”
Amanda said, “Yes, make it a white box with a golden ribbon, so I will be able to tell which one is mine.” She could not believe she had actually bought the items.
She thought to herself, “I can’t wait to see the look on Skip’s face, maybe I should buy a disposable digital camera too.”
On Tuesday, she went to a famous fashion store and bought an L’Amour gown. It was floor length and pink colored, sleeveless, cut low in the front, and slit to the hip on one side. She like the way she looked in the mirror, the dress fit her full figure like a glove. She could not wait to wear it. On her way home, she stopped and bought a digital camera. She was not certain Skip would like it, but he would not have a choice in the matter.
The rest of the week went by as usual. When Friday rolled around several coworkers noticed her behavior and asked if she was all right. She just nodded her head yes, but inside she was a bundle of nerves. Amanda wondered, “Could she actually go through with the scenario?” She has never thought of herself as being that assertive and was having second thoughts.
Skip met her online that night and typed, “Is everything a go for Saturday, Mistress.”
Amanda replied, “Oh, Skip, I am so nervous, this is all so new to me. I don’t know if I will be able to be your Mistress. “
Skip said, “Oh don’t worry about it, we will go slow. Just think about having a good time, OK. Then if you feel your not doing the right thing, we will stop. Then I will just hold you….and fuck you silly all night.”
Saturday Amanda made sure she had everything needed packed. Then drove to the hotel early and checked her in. She went to her room and unpacked a few things. Then sat on the bed wringing her hands nervously, she hoped she was doing the right thing and she would live up to the role of Mistress.
She looked at her watch and noted it was it was 5 p.m. She decided take a relaxing bath then start getting ready. When she got out of the tub, she felt better and eager to meet Skip.
She stated getting dressed for dinner, taking her time. She wanted to be dazzling tonight. She slipped on her heels then turned around to look at herself in the mirror over the dresser. Then whistled and said, “You look ravishing, Mistress Amanda.”
Amanda glanced at her watch, and saw it was time to go. She grabbed her purse and walked to her car. Then drove to the restaurant, parked her car and walked inside.
Amanda introduced herself to the host, giving her the name of the person she was waiting for. The host informed her that he was already there then asked if she wanted to go to his table. Amanda nodded her head yes and followed the host across the room to Skip’s table.
As she walked, every man in the room was ogling her. She made sure they would notice the contours of her full breasts and see a glimpse of her long sexy legs.
When she came close to the table, she blinked and uttered,”Oh wow, he is so handsome!” She really loved the way he has opened a whole new world for her.”
Skip watched Amanda coming across the room toward him. He took a drink of water, then swallowed hard and said to himself, “Oh God, she’s more beautiful than I imagined. I hope I please my Mistress.”
Amanda took his hand and said, “Hello Skip.” She felt a spark of electricity pass from his hand to hers right to the center of her pussy. For now, she would act casually; they could have their fun later in her hotel room.
When Amanda touched him, he felt a tingle clear to the center of his balls churning his already growing desires. He pulled out her chair then sat down beside her. They ordered diner, and enjoyed a laid-back conversation.
Skip said, “Do you want some desert Amanda?”
She smiled and whispered, “All I want for desert honey is you! I have a room for us at the hotel near here. I wanted to feel your hot lips caressing every inch of me, like a good slave services his Mistress. Skip I cannot wait to learn more about a mistress and submissive relationship.”
Skip could not believe his ears, she said, “His Mistress.” Oh god, he could not wait to obey her. He quickly paid the check and escorted her to her car. She told him to follow her with his car as they drove to the hotel.
He parked his car, got out, and immediately went to Amanda’s car. He then escorted her into the hotel and up to her room.
Once they were inside the room, Amanda looked into his eye and said, “Skip, you can talk, I am not playing your Mistress yet.
Skip walked over to Amanda, pulled her close, and kissed her passionately. Then said, “Oh baby, my cock has been hard ever since I seen you in that gorgeous dress!”
Amanda kissed him then stood back and asked, “Ooooh I could not wait to meet you. I love calling you, my male cunt, and I have a surprise for you.” She pulled out a medium sized box tied with a golden bow and handed it to him.
Skip said, “Amanda, you didn’t have to buy me anything. I am so happy you decided to meet me.” His fingers were shaking so hard, he could hardly open the gift. When he did, his eyes widened with excitement, there laid hot pink lingerie with, panty, bra, garter belt, matching nylons and heels.
Amanda said, “Lay the box down for a minute, and unzip my gown, will you.”
Skip did as instructed and helped Amanda out of her dress. She stepped out of the gown and laid it on the chair next to her. Their Amanda stood, in from of him wearing the same sexy lingerie, he gasp then licked his lips and uttered, “Oh my god, darling!”
Amanda moved over and sat on the bed then ran here index finger down her leg seductively. Then said, “Skip, do you like what you see? Now, put your outfit on, I want to see how sexy you look. I have fantasized about you all week and now here we are.
Skip shouted, “Oh Amanda, you look ravishing. Thank you for the lovely outfit, I shall wear it every time we chat.”
He hurriedly stripped off his clothes; his fingers shaking so bad with excitement he nearly dropped everything. He put the items on then sat down on the edge of the bed and slowly pulled up the nylons. Oh fuck, he loved the silky feeling of nylon against his legs! He stepped into the heels, then stood and almost lost his balance.
He then moved so he could see his reflection in the mirror. Then said to himself, “Damn, you really do make a good-looking woman.”
Amanda squealed, “Ooooooh, you make a beautiful woman. I am now your Mistress, and you are my slave now! You will go by the name, my male cunt slut. Come here bitch, I want to inspect my male cunt, very closely! ”
Skip walked over to her, then slowly turned around feeling her finger prod every inch of his body and hoped she would not whip him for having a hard on. Mistress Amanda said, “I can’t believe how good it fit’s you cunt and pink is definitely your color. Now back up and stand next to the table, I want a picture of you. I am going to label this one, “My male cunt slut, with a hard on.” She then instructed him to stand facing her, then said, “Oh god, your cock looks so delicious covered with silk panties.” She licked her lips and slid her hot tongue the entire length of his hard on through the fabric.
Ship shivered and said, “Oh fuck, please Mistress, use me! I am your male cunt, suck my cock, finger, and fuck my male cunt! Have your way with me, I am your slave, and I will do anything you ask!”
She replied, “Good bitch, walk me out on to the patio. There is some chilled wine on the table, pour me a glass. I want everyone to see my male cunt in his sexy outfit. Ooooh, I can’t wait to fuck you damn ass!” She then grabbed a small bag near her, took his arm, and walked out on the balcony.
When his Mistress sat down Skip noticed the city lights made her lingerie glitter as if sprinkled with silver glitter. He could not keep his eyes off her and said to himself, “Oh fuck, I could cum right now; she is so sexy!” However, he ignored his desire; if he came without her permission, he would feel her whip on his cock and balls.
Skip walked over to the table and poured her a glass of wine. Then walked over to her, gave it to her, then stood erect at her side awaiting orders.
Amanda sipped the wine then uttered, “Male cunt, its time for me to have some pleasures with you. Slave, take off your panties completely, and leave everything else on, I want the whole world to see how much of a slut you really are! DO–IT–NOW, or I will punish you right here, maybe I will anyways!”
Mistress Amanda, reached into her bag, pulled out a riding crop, and moved it making a slapping sound. Mistress then yelled, “Turn around and bend over slut and let me see your god-damn ass!” She brought the whip down hard on his left ass cheek making a red welt appear. She laughed wickedly and exclaimed, “Oooh, this is going to be so much fun, for me, but not you honey. I am so hot my panties are drenched. Now bend over more and grab your knees, its time for me to initiate you and fuck your male cunt. Now hold it right there for a moment, I am going to take more pictures, whether you like it or not!”
She took more pictures and then placed the camera around her neck, after all she had 16 more pictures left to take.
Skip turned his head and smiled sheepishly, as he watched her take a number of pictures. In the back of his mind he shivered, oh fuck, he hoped she did not show them to anyone. He continued to watch her; she put down the camera and picked up something from her bag. He blinked and looked again, then went weak in the knees, she was strapping on a big thick cock. His mouth went dry and he squealed, “Oh yes, mistress, fuck my male cunt!”
Mistress looked at him and screamed, “Hey, cock-sucker, who in the hell gave you permission to talk? Now, you need to be punished for not obeying me, you ungrateful slut!” She slapped his ass hard with the riding crop until both cheeks were flaming red. Then said, “Damn bitch, you better get it through you pee size brain that you can only speak when I say you can!”
She walker around to the front of him and grabbed his chin and said, “Now that I have your attention, convince me how much you want me to fuck your male cunt! If you do a good job at persuading me, maybe I will permit you to fuck me tonight! If you are a wimp and I will make you jack off right here in front of everybody and eat it?”
The hardness between his legs did not abate with her verbal onslaught; it only made his cock harder. Skip said, “Mistress Amanda, I am your slave, your possession, and your cum-slut and fuck toy. I am here to serve you; your pleasure is my goal. Please Mistress; it is my desire to feel that fake cock rammed deep and hard into my male cunt, show me no mercy!”
Amanda raised the cock up against his lips and said, “Suck my cock well, because I am going to fuck you with it and you are going to love it. Now get on all fours bitch!” She then moved to his ass, lubed up her fingers and shoved two in his ass.
Skip winced when her fingers entered his ass and felt his own cock twitching. He reached for his cock and began to rub it. He was gasping and breathing heavily and his cock was so hard.
Mistress yelled and slapped his ass saying, “I did not say you could touch yourself, did I?” Skip nodded his head no and took his hand away. She withdrew her hand and introduced the cock into his stretched ass. She thrust it slowly into him at first, then quicker, deeper and harder. When it was all the way in, she paused then rocked him backwards and forwards on to her cock repeatedly. She then picked up the camera and started taking more pictures, saying, “Damn, the girls in the office will never believe I did all this without pictures to prove it!”
His mind raced for a moment and he said to himself, “Oh god, she would not dare, but then again he knew everyone would see the pictures. He felt so humiliated, and loved it! God, his cock was so hard he thought it would break if it was touched.” When she pulled the cock out until just the tip was in his ass and shove it all back in, he almost passed out. The cock seemed bigger each time she thrust it in his asshole, stretching it to the limits. He grunted with satisfaction and pushed his ass against her cock repeatedly. Oooooooh fuck, it felt so good!
Mistress stopped fucking him for a moment, but left the cock buried in his ass. She then reached down and grabbed his cock, and felt a hugh amount of precum oozing all over her fingers. Mistress slapped his ass with her free hand and said, “Lick your damn precum off my fingers, my male cunt! I will reward you and let you cum for me now!”
Before she resumed fucking him, she paused to take more pictures. His big asshole stretched with the fake cock, his hard red cock with a deep purple head, dripping heavily with precum. She said to herself, “Oh god, she thought, this is so fucking hot, and I think I am going to love being his mistress.”
The ass fucking intensified making the head of his cock swelling even more. She stroked his cock harder and faster, holding her free hand near the head of his cock. Skip, felt the momentum of the earth-shattering climax surging fast through his balls. He pushed his ass hard again the toy-cock, and ejected his own cum into her hand.
Mistress Amanda took the cock out of his ass, then walked around to the front of him, and dribbled his cum into his mouth. She smiled and said, “You did well my male cunt slut. You may speak now. You may kiss me!”
Skip, looked up at his mistress with loving eyes and she bent down to kiss him. They kissed deeply, her tongue dancing with his. Skip stopped kissing and said, “I love you, Mistress Amanda! How did you like our little scenario?”
Amanda replied, “Oh darling, I loved it, and I love you! From now on, I am your Mistress and you belong to me. I need a shower now, come with me slave. “They walked hand in hand towards the shower, then hugged and kissed once more. She was everything to Skip and she knew it.
