SEXretary

David's hotel room was every bit as elegant and luxurious as the rest of the hotel. It was a huge room, dominated by a king size bed and with doors leading off towards the en suite bathroom and the balcony. As soon as the door was closed behind them, David took Samantha in his arms and leant towards her, placing a kiss on her soft, supple lips. Apart from the little peck she had planted on the cheek of Brock the sales assistant in the shoe store, Samantha had never kissed a guy before and what she would do next was important in influencing anything that could happen in her future life as Samantha. David broke from the kiss.

"Sorry," he said, "I couldn't help myself, we don't have to do anything if you don't want."

In reply, Samantha threw her arms around David and locked lips with him in a passionate kiss that lasted some time as she, almost instinctively, opened her lips to let his tongue in to explore her mouth. Samantha let out a little moan of pleasure as David's tongue violated her mouth When they finally broke from the kiss, David's mouth was smeared with pink glittery lipgloss. Eagerly, David tore off his jacket and shirt as Samantha began to kiss all over his neck and chest. She wanted him now, she wanted him badly and she remembered what Jemma had told her about making a good impression on David. Still, she remembered the secret that she carried between her legs and was careful not to let it out and ruin any good impression she might make on David. David was now standing before her totally naked while Samantha herself remained fully clothed. As David and Samantha locked lips in another passionate kiss, David began to undress her, untying the fastening of her dress round the back of her neck and allowing her breasts to fall free from it. Much as Samantha yearned to have him undress her she knew that she couldn't, she was having enough trouble as it was concealing her growing arousal and pleasure from him. All she could think to do was to drop to her knees in front of his naked body with her lips just inches away from David's hard, erect cock.

She thought back to the one expert blowjob her own cock had ever received, the one given to her a month earlier by Lucille, the very helpful girl from the lingerie store, and tried to remember how Lucille had done it. Samantha had never felt a desire for a guy's cock before but that all changed now with David's hanging erect and enticing just before her lips. Samantha inhaled the musky scent of it and knew that she wanted it inside her, some way, anyway, even inside her mouth. She opened her lips and flicked her tongue out over the swollen purple head of David's eagerly awaiting member. This seeming to go down well with David, Samantha opened up her mouth and began to take David's cock between her lips. At first, Samantha could only get a couple of inches of David's cock into her mouth and so she began to bob up and down on this as she used her hand to jerk off the rest of his shaft, gradually managing to take more and more of his cock into her mouth. It probably wasn't the most skilful or expert blowjob that a woman had ever given a man, but it was done with an eager hunger and passion. As Samantha began to be able to take his whole shaft into her mouth she could feel his groans of pleasure becoming more and more urgent and began to taste the salty sense of pre-cum on the end of his cock. The taste further reminded her of the blowjob Lucille had given her and of the pleasure Samantha had gained from the salty, cummy kiss that they had exchanged afterwards. The memory of her enjoyment of this taste drove Samantha on and soon she heard David begin to groan louder and louder and then she felt his warm, salty juices hit the back of her throat with some force. Eagerly she began to swallow all the cum that David could shoot down her throat but she wasn't quick or experienced enough and she had to let his cock slip from between her lips as he continued to ejaculate all across her face and breasts.

The whole experience had left Samantha really aroused and excited. It was her first sexual experience with a man and, though she had thought she could abate her lust by taking David in her mouth, the pleasure of it only made her want him so much more. Underneath the skirt of her aquamarine designer dress, Samantha's cock was straining against the elastic she had used to strap it down. One part of her hoped that David would send her away now, having done her bit for the company she could relieve her arousal herself in peace, but another part of her still longed for more, closer contact with David, still longed to have him truly inside her, still longed to be fucked truly as a woman should be.

"Thank you Samantha," David sighed, 'That was great. Now let me do something for you in return."

Samantha had stood up again now and David had taken her back in his arms, passionately kissing her all over her face and breasts, seemingly not deterred at all by the fact that they were still sticky with his own salty cum. David pushed Samantha back onto the bed and continued to kiss her. Almost against her own will, Samantha found herself spreading her stocking clad legs to let him between them as David's hand ran up her thigh, beneath her skirt, as it had in the office earlier that week. Suddenly he stood back up. Samantha experienced a rush of mixed feelings, relief that he hadn't gone further and discovered her secret, but regret at the loss of the closeness of his body. David smiled at him.

"Samantha," he said, "Have you ever had your ass fucked," when Samantha didn't say anything in reply for a moment he continued, "You don't have to if you don't want but you do have such a great ass and it would be an honour for me if I could be the first man inside it."

A moment's thought and Samantha realised that not only did she want that very much, she wanted his cock inside her so much it was painful for her own cock, but that this could be a way of doing it and not having him discover who or what she really was. Samantha got back onto hands and knees on the floor and pulled up the skirt of her aquamarine dress to around her waist so that her ass stuck enticingly into the air with just the thin blue silk panties between it and David.

"I would like very much for you to be the man to take my cherry David," she smiled at him as David went over to one of the drawers of the bedside table and took out some lubricant, that might have surprised Samantha had she been thinking about anything more than how badly she wanted him.

David moved around to behind her and pulled her panties down to around her knees, Samantha had made sure that her cock was pulled forward beneath her so he didn't notice it. After a moment spent lubricating his cock, David placed the head of it at Samantha's awaiting anus and paused for a moment. The wait and anticipation was killing Samantha, she so desperately wanted to feel his manhood inside her that she felt her ass moving up to meet it.

"This may hurt a little at first," David warned her, "But it's worth it."

Having said that, he grabbed her by the hips and slowly began to thrust his lubricated cock up into her ass. He was right about the pain of it, Samantha tried to relax the muscles in her ass to allow him to thrust up into it but the pain of it brought a tear to her eye. However when David offered to withdraw she didn't let him, she really badly wanted this and wasn't going to let a bit of pain put her off it. As David pulled his cock back out of her ass, she felt an emptiness that was only filled when he thrust it back in again. It didn't take long of David's gentle fucking of her ass for Samantha to accustom her self to the pain of it and to appreciate and to lose herself in the heightened sensitivity and stimulation as David thrust up towards her prostate.

"That's it David, fuck my ass," she moaned, utterly turned on by the whole situation and by David's control over her, "Oh YES! Harder, David, fuck me HARDER! Use me David, use me like a little slut." This talk seemed to drive David on as he began to quicker the pace and force to his thrust, much to Samantha's ever increasing heady pleasure. Her own cock was dying for a release now as she became ever more totally stimulated. Her total losing herself in the ecstasy of that moment meant that Samantha didn't notice how David's hands, which had been caressing and kneading her false breasts, had moved down her body and between her legs until he was holding her cock, strapped down as it was, in one hand.

"Samantha," he reproached in a slightly playful way, he didn't seem particularly surprised by her secret package, "You've been keeping that little secret well hidden from me."

With barely any break to the rhythm of his ever harder thrust deep into Samantha's tight virgin ass, David freed her cock from its restraints and it sprung free, hard as a rock and fully erect. Samantha let out a very loud and appreciative moan when David unexpectedly began to stroke the shaft of her cock as his own continued to plough into her virgin ass. With this last hold on her inhibitions destroyed, Samantha began to moan and scream ever louder with the total stimulation of the experience.

"Fuck me, David!" she yelled ecstatically, getting louder with every thrust, "Fuck me like a woman! Fuck me like a slut! Fuck me like your little whore! FUCK MEEE!"

As she gave off this last scream, Samantha looked up and was stunned to see the door to the en suite bathroom open and standing there before her Jemma and her sexy room-mate Helena. David stopped his thrusting into her virgin ass, which, even in the strangeness of this situation, disappointed Samantha. She didn't know how Jemma would react to this but she looked pleased.

"Well done Samantha," she said, "You certainly seem to know how to show a man a good time."

"But David," Helena purred in her throaty, sensual way that Samantha's fluttery, giggly voice could never quite manage to imitate, "It's very selfish of you to keep Samantha all to yourself, we'd like to join in the fun too."

With that Helena walked over and unzipped her tiny black leather mini-skirt which she let fall to the ground along with the tiny red panties beneath it. Despite all that she had seen and done today, Samantha's jaw dropped with surprise as she saw a six inch cock sticking out from between Helena's smooth, sexy thighs.

"Come on Samantha," she purred, "You didn't think you were the only girl round here with a little something extra."

Samantha looked up into Helena's gorgeous, sensual, feminine face and thought that she should have realised something so perfectly sexy couldn't be entirely real. The other thing she noticed now for the first time was something familiar about the face. It dawned on her now why Henry Stewart, the owner of the company hadn't been seen in a while. "Helena", as the company's owner had now become, smiled down at him.

"You don't mind doing me as well, do you Samantha?" she purred, "It's just that hearing you from in the other room has made me really horny."

Samantha couldn't really object to this. She may have faced some confusions recently about her identity and her sexuality, but whatever or whoever Helena really was, Samantha still found her utterly gorgeous and this evening's ever increasing love of cock just made this new aspect of Helena even more attractive and alluring. As Samantha opened her mouth to let Helena's hard cock slip between her lips, David began once more with his regular and powerful thrusts to pop her cherry and make her more of a woman than ever before. Out of the corner of her eye, Samantha could see Jemma sat back on the bed with her legs splayed wide, her skirt hiked up and her panties around her ankles. Jemma was furiously frigging her cunt as she watched Samantha, her shemale secretary, being fucked at both ends. Samantha felt himself totally in David and Helena's control as they both thrust their hard cock's in and out of him. There was something so wonderful for Samantha in this feeling of being used, of submitting to the forceful thrusts of these well endowed people. As David stroked the shaft of her cock, Samantha knew that the combination of all the evening's excitements were coming to a head as she moaned with increasing urgency round Helena's cock as Helena fucked her face.

With an electric rush of pleasure running from where David's cock filled her virgin anus right out through all of her body, Samantha experienced an orgasm unlike any she had ever had before. Her body almost convulsed with pleasure as her already tight ass tightened its grip on David's cock and her own cock blew its incredible load of hot, sticky cum uncontrollably all over David's hand, Samantha's chest and her expensive designer dress, not to mention the carpet of the exclusive hotel room. David kept stroking the shaft of her cock and Samantha's juices just kept on spurting out from her cock. David's own orgasm came only a few seconds later, as Samantha's ass tightened on his cock he let out a cry of, "I'm cumming Samantha," and filled her ass with his own warm juices until they began to leak out and stream down his thighs and all over his black silk stockings.

"Get ready Samantha," Helena cried as her orgasm was next.

Inside her warm mouth, Samantha felt Helena's cock twitch and start to empty its load of cum deep down her throat. Helena held the back of Samantha's head by her expensive new blonde wig, becoming ever more dishevelled, and forced Samantha to swallow mouthful after mouthful of her cum until the salty cream leaked round the edges of Samantha's mouth and Helena withdrew to shoot more other load into Samantha's hair, around her face and over her chest and breasts. All three of them continued to cum all over the place for what seemed like ages until finally Samantha collapsed in a sticky mess onto the carpet, feeling a satisfaction and joy that had never entered her life before as Sam. At that moment she finally heard the screams of Jemma's orgasm as she was treated to the sight of her boss cumming all over her fingers.

For now, Samantha was content to just bask in the ecstatic pleasure of the occasion. However, the next Monday at work, Jemma explained to her how David's continued investment in the company related to how he got to fuck Helena's ass but that Helena was looking for something new to do and they needed to replace her. So Jemma had formed the plan of transforming the nervy Sam Nichols, who she had long been aware had a stash of transsexual pornography on his computer, into sexy Samantha who could act as Helena's replacement for David's pleasure. Jemma told Samantha how well she had succeeded all their expectations and that, as a result, David was actually investing even more into the company than before and Samantha could expect plenty more nights like that from him. In the meantime, Jemma gave Samantha a very generous $1000 bonus for the night's work. Maybe she could afford those knee-high PVC boots after all, and there was always the possibility of flirting with the sales assistant even if not.

THE END

*

I hope that you enjoyed this story, it is the third part, although I hope it stands alone ok. If you haven't read the other parts, they are called "Revenge is Sweet" and "Personal Assistance". I wrote these stories quite a while ago, when I first started out writing stories, so I'm sorry if there are any major things you don't like about them. I know the first story has been criticised for its grammar and paragraphing, I only hope my more recent stories have improved on that.