Letting Debbie Out

Ok, this story has some explicit sex stuff, so if you shouldnt or dont want to read naughty material then please go away.

Also, I write because I want and like to. I am not a writer. Typically I write in one sitting and just do a stream of thought. I rarely edit.
But please let me know what you think. I will hopefully improve over time. And if i get enought replies that i need to edit or do something differently maybe I will.

Luv Submissive/Slutty/Sissy Sally

"I'm not sure what to do" Don said to Sam, "It sounds fun and all, but I really dont typically hang out with my employees"
"Awww, come on now Don, you used to hang out with me plenty going out for beers. This will be good, come over to Marks house, we can play some poker and just hang out for a bit. It will be like old times."
Don hadn't gone out with Sam in ages, infact its been sort of a sore spot with him and his relationship with Mark. For years Don and Sam used to go drinking, then about a year ago, shortly after hiring Mark it all seemed to change. Sa, had referred Mark to work at the company, Mark and Sam knew each other since Mark had been dating Sam's s****r for maybe a month before I hired Mark. He and Cindy still were dating, and infact she recently moved in with him.
"Ok, I'll show go" Don agreed "Will you s****r be there? I've been dying to meet her. I've only seen pictures of her on Marks desk."
She was a very pretty meek girl. Dressed styish and aside from being a year younger and bit taller and thiner than Sam could have been his twin.
"Great, this will be terrific!" Sam said excitedly. "Now we can really have a good poker party. Mark and I have been talking about pulling this together for months. He's going to be stoked. Cindy will be out most of the night, but if things go well I expect to see her show up eventually."
Don was a bit startled by the zealous reaction from Sam, but Sam was always a bit excitable, so he let it go and thought nothing more of it. Friday night was only a couple of days away and it would be nice to spend a night with the guys for a change...
Friday night rolls around and Don finds himself in Marks house. Mark opens the door after the first knock, as if he had been standing right behind the door. "Hi Don, Great that you could make it!" and with that Mark grabs Don's hand in a firm shake and pumps it with a firm handshake. Mark had been working for Don for nearly a year, and Don had always felt a little intimidated by him. Mark could pass for a construction worker in a romance movie set. He is build like a brick house and stands at least 6'2" which towers over the out of shape if not a bit chubby 5'8" of Don. With out letting go of his hand Mark firmly guides Don inside house, only releasing his hand when the door closes behind them. WIth a grin on his face Mark slaps Don on his back and says "Great! This is gonna be Great! Hey, how about some beer and some cards. Sam is already here, Cindy should be back in a bit with grub." and ushers him into the living room where Sam is sitting patiently, with cards on the table. "Hey Sammy, how about grabbing us some beer." Mark asks, or was it more of a statement than a question, for Don thought the tone was off, but Sam didnt seem to mind and bounced out of the chair and rushed off to the next room. "sure M" Sam replies as he hustles off. M? Don wonders when did Sam start calling Mark "M"?
After about two hours and a few hands of cards and a few more bottles of beer things are going really well. Don is feeling great, better than great. Don is feeling down right fantastic. The alcohol, the cards, good friends... Mark, instead of Sam who has gotten every round until now gets up to get the next round of drinks. "Damn" says Don as he returns to the room "We've run out of beer. Hope you don't mind wine." Don looks up and sees two wine glasses with white wine and a can of beer. "Well, there was still one beer, but you and Sammy will drink wine, right?" For a moment Don thinks about passing on the wine, but hey, its booze and Mark had already put it infront of him. Plus did Mark give him in option.... Don couldnt decide so figured the easist thing would be to not make a fuss and enjoy the wine and company. "Wait, there is lipstick on my glass, can i get a new one?" Don said as he noticed a very heavy smear of thick lipstick running nearly all along the edge of the glass. "Sorry Don" was Marks reply "But it was the last clean glass, hear I'll wipe it for you." Mark grabs the glass and wipes the edge and give it back, but Marks effort seemed to have no impact at all on the lipstick. "go ahead Don, a little lipstick won't kill you, are you a sissy. Cindy always says her lipstick makes the wine taste better, let me know what you think. Go ahead! Now I'm interested, let me know." Don's head was kinda spinning a little from all the booze he had already d***k and wasnt used to being talked to this way. Was Mark ordering him to drink and report on the taste of wine and lipstick? How absurd. But it sounded like it.... and now Mark and Sam were just staring at him. Don felt very very uncomfortable. "heh, ya ok" Don said, thinking that perhaps just drinking some would resolve the situation. Don puts the glass to his mouth and takes a long swig. "MMMmmm, ya actually its is pretty good. Kinda wierd though, and I'm not sure I like the feeling of the way the lipstick feels on the glass." Mark laughts heartedly at this, and declaries "he's not sure! He actually may like it, he's just not sure. Oh Don you are too funny." and with that he reaches across the table and punches Don on the sholder. "Fuck!! That hurt" Don shouts, caught off guard and it actually did hurt pretty bad. "awwww come on, Mark laughs its only a love tap, shake it off baby." Don thinks to himself, "what the fuck, I didnt come to get beaten on. But both Sam and Mark are laughing like its just all a good game. Then Sam stands up and says "gotta go tinkles folk, be backin a few!" and leaves the room. Don sits in his chair rubbing his sholder letting the alcholol haze deaden the pain. Mark asks "really does it hurt that bad?" "yes it does" Don replies "fine, here let me massage the muscle for you" and before Don can reply Mark is behind his chair rubbing and massagign Dons shoulder and back. "oooooh thats nice, uuuuuuhhh" Don moans under Marks applied pressure, the booze and ministrations taking thier toll. "Ya, Cindy says I got magic hands" Don claims as he continues his manimpulation of Dons body. Mark has Don move to a standing position and then with out asking pulls Don's shirt up over his head. Don being a more than just a little bit d***k isnt fast enough to know whats happening before the shirt is off and sailing across to the other side of the room. "There, now I can really relax that muscle and make up for causing you so much pain." and Mark starts working more and more agressivly on Don's back. Don wants to argue or fight back, it just dosnt seem right. No man has ever touched him like this, but Mark is acting so matter of fact that Don really dosnt feel as if he has a choice. Don starts to say "wait, I don't think we really should be doing this" and gets as far as "wait, I don't.." and Mark has reached with both hands and grasped Dons nipples and gave them gentle twists while pulling them upwards. Don shudders with the new sensation, as his nipples are pulled upwards he needs to raise to his tippy toes and as they are twisted the sensation sends thrills down his spine and takes the words out of his mouth as his mind spins. "Uuuuuuuhhhh, buuuuutt..." Don struggles to form a thought and a sentance. He needs to stop this before it goes further. Never has a man or woman made him feel like this, but its wrong.. it has to be wrong... but damn it feels so good. Mark continues to play with Dons nipples, neck and airlobes and Don slowly falls deeper and deeper into a passibe lustful state. Mark deftly unbuckles Don's belt and pants with one hand and in seconds Dons pants are on the floor, followed by his boxers. Dazed, Don can't believe this is happening so fast. Mark whishpers into Don's ear "Oh, Donny your muscles are so tight and you are so stressed you just need to let all this go. Here, put these silk shorts on. They are cool and comfortable and will relax you more than your pants and boxers would allow." And with that Don felt a pair of silk panties sweep up his legs and snuggle against his cockand ass. "Now raise your arms up." With out knowing why, other than because Mark has asked him to Don complies, doing what he is told, Don muses, is sooooo much easier than thinking or worse arguing. Silky fabrics come cascading down his arms and glow across his body. A dress? Don is startled and wants to run screaming from the house and reclaim his manhood... this has gone too far! But in the back of his mind a little voice says "of course a dress, its exactly what you want"
"Oh Debbie, you are so cute, and your are mine aren't you Debbie?" Don wonders who Mark is calling Debbie and where she is. "I love your tits Debbie" and Mark starts rubbing Dons chest and pulling Don's nipples. "and I love your sexy little ass Debbie" and Mark pushes Don's backwith one hand forcing Don to lean over the table while Marks other hand gropes and plays with Don's ass, tracing his ass crack and pausing at his balls and anus putting slight pressure at each point. "wait, Mark! I'm not De..." Don starts to protest. "and I sooooo love your lips and mouth" and Mark placed a finger into Don's mouth, stopping his protest. With a finger resting in Don's mouth Mark lay across Dons body spooning him on the table. Mark gently but firmly pushed his cock against Don dress and panty covered ass crack, slowly dry humping his pinned friend allowing Marks cock to swell against the silk covered virgin ass. Mark was not suprised when Don started absent mindly sucking on Marks finger that was still in his mouth, Don really didnt even notice he was doing it, he mind was awash with the feeling of being fucked, but not being fucked. After being dry humped through the silk for 10 minutes Don was nearly in tears, moaning and groaning for more. "MMMMMM Debbie, you are such a little slut arent you?" "Oh, yes Mark, I'm a slut" "Of course you are Debbie, I knew you were from the moment I saw you. I just needed to finish my first project before I took you on. If I knew you would be so easy I probaby would have started with you first" "Uuuuuuh, more Mark.. please more.... ahhh whaaaa project?" "Cindy, can you come out and help me break-in Debbie." Don hadn't heard Cindy come in, and relized that he hadn't heard from Sam for a while. As Cindy came in, wearing a black leather catsuit and lifelike strap-on dildo Don was caught off guard by the beauty of the view. Cindy walked slowly straight towards Don's head, all the while the dildo bouncing infront of her getting closer and closer. Then all of the sudden Don notices, its not a Dildo at all, the flesh colored plastic is actual flesh. As the cock slides into Don's mouth he loses his last oppurtunity to call out his friends Sams name before his best friends start to slowly face fuck him. All he can do is look pleadingly up into the eyes of his long time friend as the cock slides in and out of his mouth. The expression in the eyes of Cindy/Sam is one that Debbie/Don understands all too well now, All four of them are just toys for Mark, his plaything, and they all better get used to it. Debbie can feel her dress being pulled up to expose her ass, but its only a distraction she is focused on the cock in her mouth. Debbie can feel her panties being pulled down and the cool air caressing her ass, but its hard to focus as the thrusts from the cock sliding in and out of her mouth are causing her cock to slide in the silk fabric pinned between her and the table, and she thinks that she is very likely to cum any moment. Debbie feels the slow but continous pressure as Mark slides his throbbing cock into her gurl pussy, and for the first time in her life she is fully content. And Don, well Don is enjoying letting Debbie have her fun and wondering why the hell it took Mark so fucking long...
81% (8/2)
Posted by GreyMan44
2 years ago    Views: 756
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1 year ago
I haven't checked here in ages. I love people have enjoyed the story. Lol. Thanks for the comments.
1 year ago
love it!
2 years ago
oh hun...dont be afraid...youll find a lot of people who will love your stories on here
2 years ago
Wow you got me all excitted and made me cum all over myself
2 years ago
love this srorie
2 years ago
Thank you for your kind critism and comments. If I can figure out how to edit it, I'll paragraph it and perhaps try to make what's going on a little clearer. It's sort of like writing in a dream state for me. It makes total sense when I'm writing it, and then I hit send for fear of "chickening out" and deleting it all. Something that I've done already to 3 other stories in the last few weeks.
2 years ago
That is a really strange story... Sorta mind bending and not sure who is who or what is what. I guess a really bis sexual mind trip..
2 years ago
great story...would help make it a little easier to read if you broke it into paragraphs though