Breaking the Glass Ceiling

by TheMoose63

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Reluctant, Blackmail, Lesbian, Heterosexual, Slut Wife, Group Sex, Oral Sex, Cream Pie, .

Desc: Erotica Sex Story: Helen, at 49 brakes the glass ceiling at a downtown law firm and becomes a senior director. With that promotion comes access to the 'Director's Spa' and Helen uses it to dire consequences. Helen has a great job but a lousy marriage and is looking for someone to satisfy her need for sex. She finds that she can get a massage and much more and she takes advantage not realizing that she is being filmed. By whom and for what?

Helen Woodward took off her glasses, rubbed the bridge of her nose then sat back in her leather chair in her brand new office and surveyed her domain. Helen, at the tender age of 49, was the first woman in the history of Bass, Newman and Willis to break the glass ceiling and actually be appointed as a director of the firm and as senior director at that! She had moved from the 49th floor up to the 59th floor, the highest in the building, and was awarded, for her hard work and expertise, a corner office with windows overlooking the city from two sides. As she leaned back in her chair and looked at the museum quality art work on her walls and the scenic view of the city far below she reflected on how lucky she was, not on how good she was or on how hard she had worked or how much she deserved the promotion, just on how lucky she was ... at least at work!

Helen's married life was something else again. Her husband Myron is a prestigious cardiac surgeon as well as the Chief of Staff at Fennimore Regional Medical Center in the suburbs and spent even more time at the hospital than she did at the law offices. He was out of the house by six each morning while she normally left by six-thirty. Even if she got home by nine or ten at night he was seldom in the house before midnight. They hadn't made 'love' in the truest sense in years ... although to be fair about it they did have sexual intercourse or what she thought of as a mercy fuck, now and again. It was her husbands attempt to placate her a couple of times a month and usually on a weekend. He would indicate to her that he was interested and she would go into the bedroom, strip out of her clothes and wait for him. He would follow her into the bedroom, take off his clothes and get between her legs. He would slip himself inside, grunt a few times and cum and that was it. No foreplay, no kissing, no nothing, especially no orgasm for her ... no she had to finish herself off in the bathroom! Well she was tired of being virtually raped so she tended to avoid him whenever he seemed in that mood.

Tonight she was at her office window looking down and watching the minions of workers in the building leaving for their homes and families and she wished that she had taken the time to have a family but she hadn't and that, as they say, is that. Back at her desk she was reviewing yet another contract, making marginal notes to be corrected the next day by the 45th floor attorneys when she looked up at her clock and realized that is was almost nine o'clock. God, where had the day gone? She rubbed her back and thought that a workout might be nice and then remembered that now that she was a director it gave her access to the 'Director's Spa" on the fifth floor. She looked at her phone listing, found the spa's extension and dialed 699.

"Director's Spa, Richard speaking, how may I help you sir?"

The 'sir' remark stung a bit but she decided to just ignore it. "Richard, this is Helen Woodward and I would like an appointment for tonight, do you have any times available?" There was some hesitation before he spoke.

"Uh ... Miss Woodward ... this is the Director Spa!"

Now she was upset. "Yes, I know that Richard, why else would I call ... now do you have an opening or not?"

He quickly looked through the directors list and found her name. Well I'll be damned he thought. "Well Miss Woodward, I have one client right now and he'll be gone in about five minutes so I'm available whenever you are, say around nine fifteen ... is that alright? Oh, and I'm sorry about the 'sir' remark."

"No problem, you're forgiven and it's Mrs. Woodward Richard and yes, nine-fifteen will be just fine ... do I need to bring anything with me?"

"No ma'am, we have everything right here."

"Good, then I'll see you in ... about ten minutes."

"Yes ma'am, ten minutes." Richard hung up the phone and thought about having a woman in the spa ... Christ what was the world coming to? He put the phone back in its cradle and looked at himself in the mirror. 23, 6'2" and a 194 pounds with rock hard abs and a body to die for, yet he just wasn't ready to accept some old bag in his spa. The phone rang and Richard answered it, recognized the voice on the other end, listened and heard what the man wanted. Richard nodded his head several times then said, "Yes sir, I'll let you know. Yes sir I can do that too." He hung up the phone and just stared at it for a minute then he began getting ready for Mrs. Woodward's visit.

Up on the 59th floor Helen walked over to her private bathroom, opened the door and stepped inside and looked at herself in the mirror. She was 49, 5'7" and a 123 pounds and not half bad looking ... for 49. She turned sideways and looked at her bust line and nodded her head with the knowledge that in a $2000 business suit, $250 blouse and her imported French silk bra and matching panties she looked terrific ... still she also realized that if she took off everything her breasts would sag and so would her butt and some of the cellulite on her thighs would become apparent. Given those drawbacks she still looked nice enough, clothed at least, that there were several of the attorneys in the building that would be happy for a chance to get into her panties! Helen thought back to the last time she successfully lured a man into her proverbial marital bed and realized that it had been sixteen months, at the hospitals Christmas party ... she had snuck away with that handsome ... anyway, she thought, that was way too long to go without sex. Helen sighed and turned out the lights then stepped out of the bathroom and headed out to the elevator banks and down to the spa.

Richard was just coming out of the office when Helen walked into the spa. "Good evening Mrs. Woodward, how may I help you tonight?"

Helen looked at the 23 year old and his body was and remembered back to her youth and her first real love, Jack McKeon. Jack had been the co-captain of her college's football team and the first true love of her life until ... well who knew where the bastard was at now. "I assume that you're Richard?"

"Yes ma'am."

"Well I'll need some workout gear then I want to do maybe a half an hour on the treadmill or a couple of machines, take a short sauna and have a massage ... I read the company's brochure and it said that you gave massages, are you any good Richard?"

"Oh yes ma'am, I've had massage therapy training." He looked at her body for a second then said, "Now for your clothes I'd suggest that you use Room One just inside the doors on the left, over there," he pointed to the doors, "and use the men's small shorts and a medium tee-shirt. I apologize for the men's clothing but until tonight this has been a men's only spa ... sorry."

"That's perfectly alright Richard and please feel free to call me Helen. Now I'm going to go and change clothes then I'll meet you by the machines, I assume they are right inside there too?"

"Yes ma ... Helen."

When she walked through the doors Richard walked back into the office and turned off the lights. He picked up the phone and dialed a three digit extension and listened as it rang, and then was picked up. "She's here, going to use the treadmill then the sauna and wants a massage, I'd say she'll be here maybe an hour and a half, maybe two." He listened and nodded his head then watching through the two-way mirror saw Helen walk into the changing room. "Yes sir all the cameras are set and working and yes I'll do my best. Yes sir and thank you sir."

Helen walked into the changing room, closed the door and locked it. She looked around and saw two ceiling to floor lockers, a shelf containing various sizes of workout clothes as well as clean towels. In the center of the room was a leather high back chair and next to that was a large leather massage table covered with a sheet. She fingered the leather table and thought that it would be nice and comfortable when it came time for her massage. She was looking forward to a massage as she hadn't had the time to visit to her regular spa in months. Helen walked over and looked into the huge mirror on the wall and ran her fingers through her short hair and then went over to the lockers, opened the first one and began to take off her clothes.

Richard watched her checking out the room and almost fainted when she looked into the mirror. Her face was so close to him that he could have reached out and touched her. He briefly wondered if she knew it was a two-way mirror, then when she didn't do the 'fingernail' test ... putting a fingernail up to check the image, he knew she didn't have a clue. When she walked over to the lockers he started breathing easier and he watched her as she started to get undressed. He flipped a switch and the cameras began to whir.

Helen took off her coat and hung it up in the locker then began unbuttoning her blouse. Finished, she pulled her blouse out from her skirt, took it off and hung it on a hanger. She unzipped her skirt and stepped out of it and hung it up with her coat. Standing there in her pantyhose and bra she walked over and dug through the workout clothes until she found a pair of small pants and a medium tee shirt.

Richard was amazed by the older woman's body, even though she hadn't finished undressing. When Helen pushed her pantyhose over her hips and then sat down and pulled them off Richard couldn't wait to see her nude. She stood, reached behind her back and unsnapped her bra and pulled it off. Amazing, he thought, hardly any sag at all and she's 49! Soon her panties disappeared and Helen was standing there in all her glory and Richard was thinking that he was going to be proud to be able to fuck this woman, God what an amazing body!

Naked, Helen walked across the room and looked at her body in the mirror. She saw the slight sag to her butt and breasts but rationalized that any sane, mature man would want her. She lifted first one breast and then the other and watched as they bounced when she let them go. She pinched her nipples and felt herself getting wet then she slipped her finger in between her labia, pulled it out and tasted herself. Yep you still got it girl she thought as she slipped into the shorts and tee-shirt. She thought about putting on her bra and panties but decided that Richard probably wouldn't notice that she wasn't wearing any.

Richard almost creamed in his shorts when Helen began playing with herself right in front of the mirror. When she put a finger into her pussy and tested herself for wetness and then sucked off her own juices he knew that she was going to be one hot fuck!

45 minutes later and after spending 15 minutes on the StairMaster, 15 minutes on a treadmill and running twenty laps Helen walked back to the front of the spa and rang the bell. In just seconds Richard appeared.

"Yes ma'am?"

"Well Richard I think I'm ready for a massage. Do you want me to take a shower or can you do it like this? Oh, can we use the massage table in my changing room?"

"The shower is up to you but most prefer to shower after the massage. Uh, the table in your room will be perfect. Here is a remote buzzer, when you're changed and ready for me just press the buzzer and I'll come in."

"I see, and how would you like me dressed?"

"Well it's really up to you ma'am, without clothing is the best for a massage but you can pretty much wear what you like and I'll work around what you have on ... now if you'll excuse me." Richard closed the door behind him then went into the office to see what she decided. He was guessing that on her first visit she would wear at least her bra and panties but you never knew. He saw her looking at the massage table, running her fingers over the lightweight sheet then she turned and pulled her tee-shirt up and over her head and stepped out of the her shorts and nude, grabbed a large towel and hopped up onto the table, lay face down and spread the towel over her lower back, butt and thighs. Then she pressed the buzzer and waited. He smiled to himself.

The door opened and she turned her head sideways and looked at Richard. "I'm ready, how long will this take ... not that I'm in any hurry."

"Well I prefer to do at least an hour, an hour and a half is better if you have the time but it's really up to you."

"Okay Richard, let's go with the hour and a half."

Richard turned down the lights, walked over to a shelf and turned on some relaxing music and lit several scented candles then took a bottle of scented massage oil off the shelf. Most people thought the lights and candles were used to improve the mood of the room and that was generally true but in this case he was using them to provide a background for the cameras so they got a better picture.

He started with her hands, spending almost three minutes massaging each hand then working on her forearms and finally working up to her shoulders where he stopped. He put some more oil on his hands, rubbed them together then worked on her neck. She was a little stiff but he could feel her relaxing the longer he worked on her. He walked around the table and noticed her breasts were mashed down on the sheet and he was tempted to touch her then and there but he managed to restrain himself.

He walked down to the foot of the table and lifted one leg up onto his chest then began massaging her foot and then her calf. He stretched her leg out and then worked on her calf with expert fingers. He lowered his head as he squeezed her muscles and looked up under the towel at her pussy and saw that her lips were already puffy, almost a sure sign that she was just a little bit turned on.

Helen was as relaxed as she had been in months! Richards' fingers were indeed 'a miracle' and she loved the light, almost sexual way he was touching her body. When he lifted her right leg and put it on his chest she knew that he could probably see her pussy but instead of being offended she was excited. As his fingers moved up on her thigh she wondered if he would be bold enough to actually touch her pussy ... she hoped so, it had been a long time since a man had caressed her there.

Richard finished with her right leg without going any higher than her thigh then he moved over to her left side and repeated his massage again carefully avoiding anything above her thigh. He knew that the more he teased her, the more willing she would be when he finally touched her breasts or ass or more importantly, her pussy. The only question was ... would she initiated the touching or just allow him to do it. "How are you doing Mrs. Woodward?"

"Oh God Richard, I'm fine, but please ... it's Helen! I have to tell you that so far this has been a wonderful massage."

"Thank you ma'am, but I have to tell you that I'm uncomfortable with calling you Helen ... you know, house rules and everything. Now I'm ready to do your shoulders and back and if you get at all uncomfortable with my technique or touching, please just say so and I'll stop." He loved using that line because so far no one had ever told him to stop and on film it made it look consensual.

"Alright." She purred.

His fingers dug deep into the tissue around her shoulders and she moaned, not with sexual pleasure but with the pleasure one got from a good deep massage. His hands worked farther and farther down her back until they were massaging the small of her back then he gently removed the towel. She stiffened and sucked in her breath. "Are you alright Mrs. Woodward?"

"Yes, I'm ... fine Richard, please go on." She felt his fingers slide down onto her butt and begin squeezing her cheeks. For sure he could see the folds of her labia now and if he looked she knew he could see her wetness ... but would he look? Would he touch her, would he caress her?

His fingers stopped just short of her pussy. "Uh, Mrs. Woodward, I would like to finish off with your front, is that alright or would you prefer that just I stop now?"

She answered him by rolling over on the table and lacing her fingers together then putting them underneath her head. She smiled up at him as he looked at her breasts. "No Richard, please continue."

The move surprised Richard but he didn't let on. "Alright then let's get started." He looked at her breasts as they lay spread flat on her chest. She had light pink areolas that were maybe three inches across and small dark brown nipple almost perfectly centered and they were hard! He poured some more lotion into his hands, rubbed them together and started on her right breast. He cupped the breast and lifted it off her chest then massaged it from the sides out to the center all the while rubbing small circles on her nipples. He looked up and saw hat she had closed her eyes and was breathing deeply in rhythm to his manipulations. "Does that feel good Mrs. Woodward?" He asked.

Helen opened her eyes and smiled up at Richard. She saw him smile back then she noticed that he had a hard-on. She took one hand from under her head and reached down and lightly touched his cock rubbing her fingers up and down on his shorts. "God yes Richard that feels wonderful. Look, I'm laying here all naked ... and it only seem fair that you should join me, any chance of that happening?"

"If you like ma'am, this is, after all, the Directors Spa and I've been instructed to do what I'm told." He pulled his white polo shirt up and over his head and dropped it on the floor then pushed down his shorts and underwear revealing his hard cock.

She turned onto her side and just stared at him. His cock had to be eight inches and almost as thick as her wrist, God she had never seen anyone so well endowed. She touched him and felt the soft, pliable and warm skin and she wanted him inside her. "God Richard that is the nicest looking cock I've ever seen!"

"Yes ma'am, I've been told that before ... now is there anything ... uh ... special that you might like me to do for you?" He said it with a straight face but inside he was beaming. When he had been approached about seducing Helen Woodward for them he wasn't sure he wanted to be involved but, as they pointed out, his job was on the line so he agreed. When he first me Helen he was expecting someone stuck-up but she was just a real person and when he first saw her undressing he was amazed by her sexuality and now he wanted her, oh how he fucking wanted her.

"Yes ... yes there is..." Helen reached out and pulled Richard close to her head and as she stroked his cock he reached down and began running his fingers through her hair and lightly stroking her face.

"I can see what you want Helen, I can tell that you want to taste me, want to lick some of the cum off my cock, you do, don't you?"

"Yes ... yes I want to taste you." She nodded and as he moved closer he leaned down and kissed her cheek and when she opened her mouth he slid his cock inside.

Oh my God Helen thought, I can't possibly take all of him!

Richard continued to stroke her cheek as he slowly pumped in and out of her mouth. He didn't want to scare her off by choking her and he wanted it to be a pleasant sensation because his real goal was her pussy, although he knew it wouldn't be that night. As she sucked on his cock like a lollypop Richard reached down and played with her nipples and when she moaned she reached farther down and let his fingers trail up and down between her labia then as he rubbed her, one of his fingers on either side of her pussy he let his thumb slide across her clit. He could see the wetness on her pussy and when she began lifting her hips up to meet his fingers he knew she was close. Seconds later her whole body tensed up then she let out a cry of pleasure as her body shook as her orgasm overtook her.

His cock slipped from her mouth, "God Richard ... God I'm ccuumminnnggggggg!!!!!

"Good! Come on Helen, cum for me ... please cum for me and I promise I'll eat it all out of your pussy."

She spread her legs and felt his tongue slip inside her then the electricity of yet another cum started between her legs and she pushed her pussy into his face. "That's it Richard, eat my pussy, suck my clit and make me cum again. Oh yes, ohhh fuck yessssssssss. OHGODIMCUMING sshhitttttt!!"

Richard heard her beg him to stop and he smiled to himself as he stood up, walked to the front of the table and kissed her. She wrapped her arms around his neck and pulled him down and kissed him again.

"What about you Richard, you haven't cum yet. You have been so good to me that I want to take care of you too ... please?"

"Awww Mrs. Woodward, that's alright ... honest but not tonight. I mean just helping you get off is pleasure enough for me ... besides I have another appointment in a couple of minutes but thanks anyway, maybe next time." He kissed her again and left the room.

Helen watched him leave and was confused. Okay so there was another director coming ... but why hadn't he just given her a quick fucking, God she was looking forward to feeling him deep inside her? She shrugged her shoulders then stood up and walked over to the private shower and cleaned-up.

Richard was sitting behind the mirror and watching her shower and was slowly jacking off. When she stepped out to dry off he came, shooting his cum all over his legs. While he used a towel to clean himself up he watched her get dressed then she left the room and he didn't bother to see if she left the Spa.

For the next two days Helen sat in her office, her mind constantly thinking about what had happened that night in the spa. She had been expecting that at any minute Mr. Bass or Mr. Newman would walk through her door and accuse her of some perverted sexual offense, some crime against the company's policies or something ... but nothing had happened, no one came and soon she forgot all about it.

On the third day Helen was working late and when she looked up she realized it was already dark outside and she looked at the wall clock and saw it was half past eight. She thought about the spa, picked up the phone and dialed 699.

"Director's Spa, Richard speaking, how may I help you?"

"Richard this is Helen Woodward, do you have a spot open for me?"

"Uh ... let me see Mrs. Woodward. Yes, I have 8:45 open ... is that good for you?"

"That would be fine Richard, thank you."

"Uh ... excuse me Mrs. Woodward, what will you be requiring tonight?"

She thought about that for a minute. "Well if you're up for it a nice slow, long massage would be great."

"I'll get the room ready ma'am." He hung up the phone then picked it up again and dialed the number. When the phone was answered he said, "Yes sir ... she coming back again sir, 8:45 sir. Yes sir ... a massage only this time. Yes sir, no problem ... the cameras are ready and I'll make sure that you get the shots you want. Thank you sir!" He hung up and walked out of the office and into Room One where he lit several candles and turned on the music.

She hung up the phone and looked at the clock ... twenty minutes to kill. Helen read through one more contract then left for the spa. She arrived five minutes early and saw Richard standing there with a towel in his hand.

"Good evening Mrs. Woodward."

She nodded her head. "Good evening Richard, I hope you're as good tonight as you were the last time ... maybe even better?"

"I'll try ma'am." He led her into Room One and held the door for her. "I'll just wait outside Mrs. Woodward."

She looked around the room and thought it was perfect. "First off Richard I would prefer that you call me Helen, rules aside but especially now that we have ... ah ... been kind of intimate and there is no need for you to leave, let's just get undressed and get started."

He took a deep breath. "Fine with me ma'am ... Helen."

She began to undress and Richard watched, still fascinated with her body. He quickly slipped off his polo shirt and shorts and underwear and stood there naked, his hard cock jutting out from between his legs.

When Helen finished undressing she turned and saw Richard and again she admired his cock. She walked over to where he was standing and wrapped her fingers around him and let him over to the massage table. "I think we can skip the preliminaries and just get started with you massaging my pussy and tits only this time Richard I want you inside me, alright?"

Richard helped her up onto the table, turned her sideways and held on to her arm as she lay back on the table. He bent over and sucked a nipple into his mouth and his fingers immediately found her pussy easily slipping inside her sliding up until he touched her clit. She moaned.

"Oh God Richard that's wonderful, please keep doing that."

"God you're so wet Helen, have you been thinking about me?"

"Jesus what a stupid question, of course I've been thinking about you Richard ... all day and all I've imagined is your cock inside me."

He kept his fingers inside her as he moved to the end of the table then with one had he lifted first one leg and then the other until they were resting on his shoulders then he moved closer to the to her gaping pussy and easily slipped his cock inside her.

She felt him entering her, stretching her pussy and it felt damned good ... it had just been way too long since she had been properly fucked. "AAARRRGGGHHHH! Oh My God! Oh sweet Jesus Richard, fuck me, please honey fuck me."

Richard was more than happy to comply with her wishes, Christ he had wanted to fuck her the first time but they had told him no ... but now he had their approval and was going to take full advantage of it. He slowly slipped in and out, going from just inside her lips all the way to the bottom then back out to the top.

"Fuck! Richard don't fucking tease me, fuck me with that prick of yours ... fuck me long and fuck me hard!"

He grabbed her and pulled her butt farther over the end of the table then pounded her pussy as hard as he could ... in and out, in and out — faster and faster until he saw her lift her butt up into the air and he knew she was going to cum.

"OH ... OH GOD ... Oh baby I'm ... I'm ... cccuumminggggggggggg!" She pushed into his groin trying her hardest to get all of his cock into her as she muscles grasped his cock and she felt the familiar spasm of her pussy and she came.

He continued to fuck her even though she had two more orgasms and was trying for a third. "You like that don't you Helen, you like my cock deep in your hot little pussy, filling you up and making you cum?"

"Ye ... yes, yes I do." She panted and another orgasm approached. "You ... are you ... almost there?"

"Yea, yea I'm almost ready but I want to cum in your mouth ... come on baby turn around and suck my cock."

Helen reluctantly pulled herself away from his cock and turned on the table and opened her mouth. "Come on Richard, give me that cock."

He complied by shoving himself into her mouth. "Go on Helen, suck my cock. God I'm so fucking close, come on you can suck better than that!" He wrapped his fingers into her hair and guided her head back and forth until he felt his cum swirling inside his loins and he got up onto his toes as his cock exploded into her mouth. He rammed his cock deep into her throat until she started to choke then he eased off just a bit. "OOHGODOHFUCMEI'MCUMMINGGGGG!!!!!" As his cock shot hot cum into Helen's mouth he watched her try and swallow and unable to do that she tried to pull back and catch her breath but he wouldn't let her head loose either. "Suck it down you fucking slut, suck it all down and don't let any go or I'll wait until I'm hard again and fuck your ass."

She had another orgasm as he talked dirty to her, told her he would fuck her ass. Would he really? She had never been fucked in the ass and had always wondered what it would be like but with the size of his cock ... God that would have to hurt! She gulped and did as he asked and swallowed all of his cum. Afterward they took a shower together then Helen got dressed and returned to her office and finished off that days work.

It was Tuesday of the following week before Helen had a chance to even think about using the spa and she was about to find out that things had taken a twist. Helen waited until after eight in the evening before she called down to Richard.

"Director's Spa, Richard speaking, how may I help you?"

"Richard, its Helen ... do you have time for me tonight?" She was horny and looking forward to a good fucking and hoped he had some time available.

"Yes ma'am, give me fifteen minutes and I'll have everything ready."

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