Mom, This is So Wrong

'William, what is going on with your Mother?'

'What do you mean Kate?'

'Yesterday after work, Leslie and I had drinks at the bar in the Presidio. You know the place, the 5 star hotel down the street from Mom's law firm, across from my ad agency.

Very familiar with that hotel - the bar, the suites, the beds, the great room service, the women.

'Yes, been there, very classy. So what was wrong with that? Probably meeting a client to close a deal. That would be my guess.'

'Didn't you tell me she doesn't drink much?'

'Yes.'

'She was at the bar, drinking martini's, lot's of martinis. A man walked in and sat next to her. He sported one of those $3,000 suits you have your eyes on.'

'Ok, that sounds like a client.'

'Ready for this? She left with him! From where we were sitting, I could see the lobby. They went straight to the elevators! Oh my god, they were going to his room I bet!'

'Kate, so you are saying that's a problem or just out of character for her?'

'The latter. It's been what... 6 months from the divorce. I guess she can fuck whoever she wants to now. So, it's fine. I would probably do the same thing when we are divorced.'

'Kate, I don't know... what did you say?'

'Just joking William! Lighten up! Glad your Mom is getting laid.'

I wonder if she knows about me and my $3,000 suits.

***

That was worth every one of the $5,000! Hotel suite with a separate bedroom. Oversized king bed with plenty of room for a threesome. Maybe next time.

Since the divorce finalized, I can't get over how often I think about sex. My sexual frustration grew everyday.

Even before the divorce, my time in bed with Julian was a rarity. I suspected he was having an affair. It took a clever private detective to catch him with someone half my age.

It was difficult to look at the pictures. So many of them. Running the gamut of simply holding hands in public to rapid fire photos of her naked body riding up and down on Julian's big cock.

I will miss his abnormally large penis. Hard to replace something like he had. It was the only one I knew.

Eventually I started fantasizing about sex at work.

I looked at my male employees in a different way, wondering how big they are and their skill level in the bedroom versus the court room.

No way will I ever approach them. As the Managing Partner of 200 attorneys, my job would be at risk. I would be dead meat if I crossed the sexual harassment line even with a willing subject. Someone might blow the whistle and my time with the firm would be ended. Margaret was waiting in the wings to pounce on something like that. She wanted my job.

And what would William think about his mother canned from the very law firm he just started working at as an associate?

I had to find someone outside the firm to release my burning, desperate need for sex. I did. A service, a discreet service where false identities were accepted and money exchanged with no traces.

I replayed the whole night.

Sumptuous candlelight dinner served by a waiter in the dining area of the suite. Fine wines, after dinner drinks, such a romantic build up to a night of sex. Waiter leaves, the guy returns in a short silk robe, the cock head visible at the bottom. Off to the bedroom.

He was simply awesome in bed.

His talented tongue and lips working my pussy like no other man, well like only one man.

His cock! I loved every inch of it. Sucking his cock until he exploded in my mouth, it has been so long.

His girth splitting open my labia, a feeling I will never forget. His cum filling up my pussy. Ahh what fun!

I am going to sleep so good tonight. So satisfied, but I know it won't last long.

Will I pay another $5,000 for another one nighter? Maybe. For this mature guy yes but maybe I should try another. He was only the second man I had sex with. A third would be exciting, especially with someone younger. Time to explore. Threesomes down the road a bit.

Next week, yeah next week, I will do it with a young stud. This is going to be fun! With no risks of anyone finding out.

***

I answered, it was my handler.

'William, a Mom and daughter booked the luxury package at the Presidio. It's her daughter's 19th birthday. My guess is she is a virgin, so be gentle with her if that is the case.'

'Is the Mom going to join in or is she just going to watch?'

'Don't know, I guess you will have to react to that.'

'Ok, how do I engage?'

'The usual, meet at the bar. Mom will wear black, daughter red.'

'The suite with the big bed?'

'Yep, use your app to open the door.'

I really wanted to ask if Mom has used the service, but I couldn't, she probably used a pseudo name like most people do. But, what Kate saw fit the description. Enough for me, plus more money for our Gigolo company.

'Got it, have to get back to work, taking a deposition this afternoon. Working with one of the senior partners Margaret Williams.'

'Have fun!'

I hate not knowing how I should handle the two of them. I've done threesomes before, one time a foursome. They wear me out.

Margaret popped in my doorway. She was wearing a sexy black dress, not her typical outfit for a deposition.

'Are you coming William?'

'Yes boss.'

I picked up my legal pads and files and hurried after her admiring the curves of her body in that tight fitting skirt.

Nice distraction as this deposition is a little nerve wracking. And she told me I was leading the questioning. I need to nail this..

***

That evening...

Man that was tough, I was ready for a drink and sex after all that. Margaret told me I did good which means a lot. I always liked her. She wasn't the typical kick ass senior partner, she took a kinder, gentler approach with the associates, kind of like Mom. Bad ass with the opponent attorneys.

Plus she was a fox - pretty, professional but hot. I knew she was divorced with a grown kid. I had a thing for her that I would never act out. But I could think about it.

My favorite fantasy about Margaret, taking her into a supply closet at work, lift her skirt up, pull down her panties and fuck her up against the door. I am pretty sure I would please her, I am good at making women feel good. Big, thick cock and I know how to use it. Years of refining my skills. I have come a long way since I turned 18.

Back to thinking about work.

Sitting in the back of the bar, I was strategically placed so I could see who enters. They were late but I didn't care, on my third drink I enjoyed my accomplishment today.

Margaret walked in with a woman, a young woman dressed in red! Holy cow! Is it them? Are they my threesome?

They sat at the bar. The lady in red looked nervous. A girl about to lose her virginity? I can't engage, I need to let my handler know that I know the Mom, that I work with the Mom, I work for the Mom.

I was about to call when Margaret walked over to my table. She had unbuttoned her blouse down low, her breasts cleavage visible and oh so close. Supply closet, supply closet, fuck her standing up...

'William, fancy meeting you here. Looks like you have been celebrating. Good for you!'

'Are you alone or is someone joining you?' she asked.

'Someone is joining me, but they are late.'

'Me too. Come sit with us at the bar.'

I had the urge to run out of the bar. I can't be rude.

'William, this is my daughter Meghan. Meghan, I work with William.'

Meghan was striking. She got her Mom's beauty DNA.

I turned on the gigolo charm.

'Well I see you inherited your Mother's good looks! Oh and Happy Birthday!'

Margaret gave me a strange look.

I screwed up! She didn't tell me it was Meghan's birthday, my handler did!

Margaret whispered something in Meghan's ear. She nodded and excused herself.

'How did you know it is her birthday William?'

Think fast! I am about to be interrogated by one of the toughest litigators on the planet.

'I... uh... I,' I stuttered.

'Thought so. You are the person we are waiting for. Really? You work for the gigolo service? Married man? Fucking women for money? Does your wife know? Does your Mom know?'

'My Dad knows, that's all.'

'Your Dad?' she said indignantly.

She said, 'The guy caught cheating with someone half his age. You confide in him?'

'Actually, he started me in the business in my high school senior year. I handled all the Mom's wanting a young stud. He eventually sold the business - Stallions LLC. The asshole stiffed me out of any money. Now I work for the new owners.'

'Why? You make good money and are on track to be a partner.'

'What? I didn't know that.'

I paused. Confession time. Partner? I probably screwed that up.

'I lied to Kate about what I make. I get away with the lie as I manage our money. I do this to make up the difference. I only take jobs, sorry, clients to close the gap.'

Margaret was thinking.

'I paid in advance. Can I cancel and get my money back?'

'Did you read and sign the agreement? It clearly states no refunds.'

'Yes, but I couldn't think of a reason why I would cancel.'

We stared at each other. She subconsciously bit her lip.

She asked, 'Are you any good?'

Well, well. She is thinking about going forward. Interesting.

'All I can say is that I have many return clients.'

'I am really doing this for Meghan. I signed us both up as a protection of her. I plan to be there, but not participate. Are you clear on that?'

'Yes. But I have to ask. Will you tell anyone about me?'

'I have the same question for you.'

'You saw the confidentiality agreement. I strictly abide to it. You would be surprised who some of my regulars are. I will never kiss and tell.'

She called Meghan telling her to meet at the elevators.

'You better treat my daughter well. She is a virgin. You need to be gentle and almost loving. Can you do that?'

'I do that all the time unless a client asks me to be rough.'

'Rough, really? That's intriguing. I like rough sex. I shouldn't have said that.'

'You would be surprised. Happily married women looking for excitement outside the marriage, divorcees starved for sex, single women needing sex. Rough, loving, mechanical - whatever appeals to them.'

A sly smile crept across her face, maybe she will do more than watch. I could do a lot to fill her fantasies and... mine.

***

Damn, what luck, a bluebird in our lap. Huge corporate merger. Lot's of work, lots of billing. I gathered the core team together.

'We have a month to get this done. Buckle up. Expect 16 - 20 hour work days, half days on Sunday - 12 hours. Let's get this done. I will be right there with you.'

This will take my mind off sex. No time to engage with a young stud. It will have to wait.

***

It was a great dinner in the suite. The waiter knows me well, we use this suite a lot, he really took care of us, especially Meghan, making her comfortable. He knows what is ahead for her. Hotel staff talks.

The waiter was told about her birthday. Before the after dinner drinks, a parade of hotel staff entered the suite, carrying bouquets of flowers and presents provided by my company for Meghan. She and Margaret were blown away. We are a first class gigolo service.

So we lose a little profit. It will pay off down the road.

Margaret allowed Meghan to drink. After the wine and dinner drinks she looked a little bit dreamy.

Meghan's conversation abilities were awesome. I really took a liking to her. We hit it off. This will be fun for me, taking her virginity.

It will be weird to have an observer. I hope Margaret stays in the living area while I take care of Meghan in the bedroom.

It was time. I excused myself and changed into the short silk robe that the handler provides.

Returning, I sat next to Meghan at the dinner table. I took her hand and gently caressed it.

I leaned in and kissed her on the cheek. She smiled.

Placing both hands on the side of her face, holding it still so I could kiss her on the lips. Once, then again. She kissed me back.

'Meghan, let's go to the bedroom and make love. May I take you there?'

She enthusiastically nodded yes.

I helped her out of the chair. I kissed her again when she stood. I took her hand and led her to the bedroom. My peripheral vision sighting Margaret as she stood up and followed us.

Looks like I will have a judge and jury watching me having sex with her daughter.

I'm ready.

I motioned to the edge of the bed.

'Meghan, sit it there.'

She complied. Margaret sat off to the side in an arm chair up against the wall next to the bed. She brought a bottle of wine and a glass for herself.

It's showtime!

My body gets most women going. Standing in front of Meghan, I undid the tie and let the robe slowly slide off me, a full frontal view for Meghan. My limp penis inches from her face.

I am quite proud of my body after years of weight lifting, cardio and flexibility training to sculpt my body.. My biceps, triceps, pecs and six pack stomach, all rock hard. All complimented by my long and thick penis.

She gasped. I looked at Margaret, her fingers to her mouth suppressing her opinion.

Meghan was staring at my cock.

'Meghan, can you touch me?'

She said, 'Uh-huh'.

She took my penis in hand. I closed my eyes and pictured her sucking it. An erection slowly building.

'Go ahead and stroke it a little.'

At first she hesitated, but quickly got over that and began stroking me. It worked. It grew in her hand. She let go of it like, probably surprised at what she did.

My semi-erect cock pointing up to her chin.

'Oh my!'

It was Margaret who said it. Clearly she appreciates a big cock.

I sat next to Meghan and said. 'Your turn.'

Meghan stood up and with lightning speed took off her clothes. No teasing, she needs to learn how to do that.

What a body! Nicely formed breasts with small areolas, and little pillar nipples. Her slim waist angling down to her virgin pussy, a small patch of pubic hair right above it.

She sat next to me. I was turned on by her body. My erection now standing straight up.

I didn't have to ask her, she took my hard cock in one hand, stroking it while kissing me. A definite turn on for me, I am going to enjoy taking away her virginity.

Plenty hard, I whispered in her ear.

'It's my turn.'

I eased her back on the bed, motioning for her to move up to the pillows. I fluffed them up for her, leaning her gently back. I crawled on top her, resting my pulsing erection right on her virgin pussy. I kissed her on the lips, then the neck. The nipples next, kissing then sucking on them.

Downstairs, I pressed my hard on in between her labia.

'Oh my gosh. It is time?' I am ready William.'

I didn't respond verbally. I scooted down to kiss her stomach, then the area right above her clit.

I knelt in front of her.

She spread her legs wide open beckoning my mouth, tongue, and fingers to deliver satisfaction. Her pussy was inviting. She was ready. I moved in and placed my hands on her inner thighs. I moved in close to her. I looked up to her for eye contact. She smiled.

I licked her inner thighs, one side, then the other. I continued licking and then kissing my way up. I stopped short of contacting her pussy.

Surprisingly she placed her hands on the back of my head forcing me in closer.

I licked and sucked on her swelling outer lips. I pinched them together, kissed them, then ran my tongue back and forth across them. Placing my mouth around her labia, sucking on them. I paused to look at her. Her head was back, her eyes closed. She was enjoying the ride.

With my fingers, I spread her lips wide open, I inserted my tongue into her pussy playing around inside while resting my upper lip on the very bottom of her clitoris. I pulled back then inserted several times in a fucking motion always giving her clit a quick lick. She trembled.

Moving up, I ran my tongue back and forth across her clit while inserting a finger into her. The clit was engorged. I sucked on it once. She almost levitated off the bed. I sucked again. I backed off to just swipe it with my tongue.

'Oh William! Give me more. I want it.' she screamed.

Margaret moved onto the bed, she cradled Meghan's head. She surprised me when she caressed her daughters breasts, squeezing the nipples, pulling them up, then sucking on one then the other.

I gave her a look like 'what the fuck are you doing to you daughter'.

She said, 'Just trying to help.'

I sucked on Meghan's clit. Once, then twice, then three times releasing and pausing each time to tease her, letting the anticipation build. My finger fucking her in the same rhythm. One more suck.

'Oh my god I am cumming! Oh my god, oh my god, oh god.' she shouted rolling her head back and forth. She grabbed the back of my head pulling it hard onto her while I kept her clit between my lips flicking it with my tongue.

Her body rippled from top to bottom, bucking up and down. Her pussy soaking with her juices. I didn't stop, I kept the ride going.

She whimpered, 'Oh my...oh my... oh my William.'

Her voice dropping down to a whisper. Eventually she went quiet.

Meghan said, 'Mom, he is as good as you.'

I said out loud, 'What did you say?'

She replied, 'Mom, he is...'

Cut short by Margaret, 'Remember William, confidentiality. I can't do one thing you can do for her. Go ahead and fuck her now.'

'Okaaay.'

I changed my position moving right on top of Meghan. I laid my cock lengthwise on her pussy lips, spreading them open from top to bottom. The head laying on her swollen clit.

My face and lips inches from her. I kissed her easily, then harder. The dying embers of her orgasm rekindled. She kissed me back hard, slipping her tongue against mine. she wrapped her arms around my muscled back.

'Mom, finally I am going to get fucked!'

I pulled back and whispered, 'Tell me you want it, Meghan.'

'I want it,' she said.

'Tell me what you want?'

'I want your big cock inside me.'

'Are you sure I can take your virginity?'

'Fuck yes, do it fuck me.'

Margaret chimed in, 'Stop the teasing William, fuck my daughter if you need your job.'

I got the message.

'Guide me in Meghan.'

She went all in. She took hold of my big, thick erection and placed the head barely inside her. She pulled it in further parting the lips. I took it from there. I felt the head slide further into to her as I pushed my entire erection in. I felt the resistance of her hymen. A harder thrust and I pushed past it. It felt so good, so good. Such a tight, wet virgin pussy.

I pulled out to just the head touching her swollen lips. I moved back and forth against the lips and plunged in hard and deep. Gosh, I was loving this too much.

'Meghan do you like it?'

'William you feel so good inside of me. Don't take it out. Keep fucking me. Please fuck me, fuck me till I cum on your huge erection. Cum inside me. Let me lick your cum when you are done.'

What kind of talk from a virgin, sheesh!

All during the dirty talk I was working hard fucking her, sweat pouring off my chest on to her rock hard nipples. She offered one breast to me, I squeezed the nipple and gently pinched it.

'Oh yeah,' Meghan said.

I could tell she was once again close to an orgasm.

'William, I think I am close, fuck me harder, cum inside me.'

I pounded her so hard, I grunted and groaned every time I landed on her pelvis. The feeling I love so much was taking over. My world narrowed to what was happening between her legs, the only thing in my world right now. I needed to orgasm when she did.

'William cum inside me, please cum, I need your cum inside me. I need to feel it. Hurry William, hurry.'

I went crazy on the speed, I began to shake, I was ready to cum.

'Meghan, I am cumming.'

I closed my eyes, ready to unleash a load of cum in her tight pussy.

Margaret shouted, 'Pull out, pull out, she is not protected, pull out!'