Personal Assistance


Helena was satisfied that she was making a fairly strong impact on David and that this could only be having a good affect on the potential financial situation of the company. Her opinions were confirmed when after dinner David, slightly unsure of himself, asked Helena if she would like to come back to his hotel with him. In the cab to the hotel, Helena decided to put David's mind at ease as to what was going to happen so he wouldn't be so nervous to ask for it. She bent over and began to kiss all over his face and neck, rubbing her hand over the crotch of his pants where she could already feel a straining bulge. Getting to the door of David's hotel room, he eagerly fumbled for the keys, obviously desperate to get inside the room and allow Helena to do her thing. Getting inside the room, Helena instantly freed herself from the black velvet evening dress and let it fall to the floor, stepping out of it to reveal her sexy, smooth body in its sensual lingerie, a black lace basque that barely contained her huge breasts and the black silk stockings, supported by a black lace suspender belt. David let out a groan at the sight of Helena in her lingerie and Helena thought it possible that he might cream in his pants right there and then. But, seeming to control himself, instead he quickly stripped from his suit until he stood, naked, before her with his cock jutting out, erect and alert, from his body, awaiting Helena's attentions.

Helena got to her knees before him as she had so many men before and flicked out her tongue, licking the quivering head of his cock in a way that made his body tremble and his mouth groan. Her own cock was feeling quite excited by the situation and she knew that it wouldn't take much of her talented and experienced attentions to produce a climax in David. She swallowed the whole length of his cock into her throat and caressed it with her eager tongue. Knowing David was now not far off reaching his orgasm, Helena, whose hands were currently all over his ass, stuck one of her fingers up inside David's ass. That was enough to send him over the edge, with a loud cry of pleasure David emptied his cock down her throat, giving her bucket loads of cum, much to Helena's pleasure as she eagerly swallowed it all.

"Wow," David grinned, "That was amazing."

"That's not all," Helena winked seductively at him.

She stood back up and put her lips against his, kissing him passionately and using her tongue to push his cum back down his throat, David offered no resistance to this and, indeed, seemed to enjoy it as much as Helena did herself. Walking over to the bed, she lay face down on it and spread her legs wide and invitingly. Looking back over her shoulder she smiled at him and winked seductively again, beckoning with her finger.

"How would you like to fuck my ass, David?" she purred.

David obviously didn't need to think very much about it and the hot, salty, cummy kiss had already made his cock become hard again. Positioning himself behind her, he pulled her underwear aside to give access to her ass and began to shove his cock up deep inside her ass. At first he slowly and gently thrust himself in and out of her until Helena encouraged him to do it more and more forcefully. Sure enough, soon David was thrusting athletically and violently deep inside Helena in a way that was making her moan and beg for more. Caught up as she was in the joy of the moment, Helena carelessly failed to notice David reaching round underneath her, hoping to find her pussy and instead being greeted by Helena's surprise package. David stopped fucking her ass for a moment while his hand remained clasped on her firm, hard cock, seemingly not knowing what to do. Helena was about to say something, make some excuse or encouragement when David ploughed back into her ass, deeper, harder and more eagerly than before in a way that made whatever Helena was about to say turn into a loud and grateful moan of pleasure. As he ploughed in and out of her, stimulating her like she hadn't been for some time, his hand that was clasped around her cock began to jerk her off equally eagerly. It didn't take long for Helena's ass to tighten around David's cock and for her to feel her orgasm spreading electrically out from her prostate through her body until her cock exploded in his hand and came all over her sexy lingerie and the sheets of the hotel bed. With that, and one more powerful thrust deep into her ass, David too reached his climax, for the second time that evening and filled her ass to overflowing with warm, sticky cum.

Lying on the bed, in a warm sticky embrace, cocks touching, David smiled at Helena:

"Well, it looks like I'm going to be investing heavily in your company, and it looks like I'm going to need to be making plenty more trips to San Diego to check on my investment," he winked at her to suggest what else he might be checking up on and Helena smiled back, with her transformation from Henry to Helena complete she was finally realising the possibilities and opportunities open to her.


Look out for Part 3, "Sexretary"

Report Story

bysexy_jessie© 12 comments/ 99115 views/ 30 favorites

Share the love

Similar stories

Report a Bug

2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartbralover1977, lockee and 28 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous05/17/18

Good story, but....

I find it difficult to see exactly how Jemma found out about Helena. Yes, it was mentioned that Naomi said something to her, but if Henry kept it a secret, how did Naomi find out? And how did Jemma managemore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 12 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: