Tom and Sophie

At 10:00am we had the board room set and the executive staff filed in together. There was one new face that the vice-president Matt Heffernan introduced as the owner of the company Barry O'Neil. I was a little surprised that he had travelled all this way. There was a corporate retreat scheduled for Friday so I assumed he came for the week. As it turns out, they had planned mass layoffs for this Friday to coincide with the retreat, to soften the blow for the employees that were to remain.

Matt had been the biggest critic of my changes. He had worked up from sales, to managing the sales team to recently taking over the VP position when the company started struggling due to the problems with the economy. But managing a sales team is very different from managing a division. His first thought was to cut away the 'dead wood' as he called it. Before the company I had spent the better part of my life building had gone bankrupt, I was inclined to agree with him. Seeing so many people lose their jobs, including myself, I was determined not to let that happen here.

My gamble paid off. Many of the initiatives I had put into place meant that the layoffs were not necessary, in fact, my entire presentation was not necessary since the unexpected increase in revenue in this branch had already been a topic of conversation for the last several weeks. Needless to say the meeting went very well. We were asked to provide our research and the data we collected over to corporate for review. Barry asked us to provide some recommendations for the other offices for Monday. I told him we could, even though it was going to be a tremendous amount of work for two people.
Everything wrapped up by 11:30 at which time we were told that Barry had a lunch meeting with a client so they had to go. Gwen and I were left to get to work. Gwen offered to buy me lunch. Gwen dropped off her grey suit jacket at her desk and grabbed her purse. She was wearing and navy blue patterned dress, which I would have considered inappropriate for work, without the jacket. The moment we stepped outside a wave of heat and humidity hit us. I hadn't been out at noon in weeks I realized. We walked a couple of blocks and turned down an alleyway. The streets weren't crowded, lots of people were staying inside.

"I hope where we are going is close, I need to get back into the air conditioning."

"It's that wool suit of yours, even sheep shed their wool in the summer. Look at me." She lifted the straps of her dress and pulled them up over her shoulder and down well below her waist. She was completely naked underneath. I got a closer look of the tattoos and the piercings. There were hoop rings on her nipples, navel and labia. "See, nice and cool for the heat, no undergarments to trap in the heat and the fabric is sheer so it is like wearing nothing at all."

"Cover yourself up before someone sees you" I said sternly.

She looked at me amused. "I will if you answer me a couple of questions."

"Sure, whatever, quickly." I said looking around.

"Did you enjoy the show last night, you were gone when we were done."

"Yes." I answered nervously.

"Did you masturbate?"

"What? No, of course not."

She laughed and slowly lifted her dress back into place. "You know what I like best about you Tommy? You are not a very good liar."

"I don't know what you are talking about." I didn't like the way this conversation was going.

"You don't? OK, let me illustrate. Did I turn you on when I took off my dress? Did you like my piercings, what about my tattoos, did that get the blood flowing? Were you thinking about me and Clive last night?"

"Stop this, no. I am just concerned for you if anyone saw you, you could get into a lot of trouble."

She got in cluster to me and cupped my cock and balls. She felt that I was hard. "See Tommy, you say one thing, but your body language tells a different story. I know a better place for lunch follow me."

We backtracked a little and walked through a few more side streets to an older area. We got to a place and Gwen opened the door. I stopped her.

"This is a strip club."

"Yeah, but they make a great Reuben."

We got inside and there were a few patrons, but clearly this place couldn't survive on the day crowd. I suspected it filled up after five. A tall brunette came up to us, she was topless wearing metallic silver panties. She was thin but her breasts were huge, obviously fake. "Hi Gwen, who's your friend?"

"This is Tommy, we work together. We came in for lunch."

"Cool, there is a booth over in the corner." She walked us over and we sat down. "Do you know what you want?"

"Two double bourbons and two Reubens."

"I don't drink bourbon, and certainly not during the day."

"Relax Tommy. Order your drink then."

"Ok, a scotch and ice I guess."

As the waitress walked away Gwen called out "Make his a double." She nodded.

"Listen Gwen, I don't think that..."

"Stop Tommy, we did good today, the meeting went well, jobs were saved, you make the company money, it is time to celebrate. Don't worry, this is not a seduction thing. I am not going to force you in an uncompromising position. I think you need to relax and blow off some steam once in a while."

That eased my mind, but I also felt a little disappointed. Then a little embarrassed by my foolishness. Obviously a young, beautiful, carefree spirit like Gwen wouldn't be interested in a guy like me. "Sure."

The drinks arrived and I swallowed down half of it in a single gulp. By the time the sandwiches arrived I was feeling a little better. I had been years since I had been to a place like this. I was enjoying seeing real live women. There was one dark skinned woman, possibly of mixed race, and very shapely that caught my eye. Gwen asked me about my life, friends, and so on. She ordered another round of drinks.

"I moved here with Sophie. She grew up here. We met in college and when school was over she wanted to move back so I got a job here and asked her to marry me. I lost track of most of my high school and college friends, worked hard and moved up quickly in the company, which was hard with two kids. Sophie pretty much raised them. Next thing you know it is twenty years later and the company goes bankrupt. It is weird, you spend all those years working with people and suddenly they are gone and you realize that you didn't really know them all that well. You know what I mean?"

Gwen just shrugged. I don't know if it was the booze, the fact that I was completely out of my element or that I simply hadn't had anyone to talk to for such a long time, I just laid it all out to Gwen. I told her how when I lost my job I felt worthless. I told her that I blamed myself for the company going under, I should have known what was coming and prepared better. So many people's lives were hurt by that. I told her how the eight months I was off work was the worst time in my life. I knew that Sophie was cheating on me, had been for years, and now that I couldn't provide for her like I did she would probably be leaving me. I didn't blame her since I never spent any time with the family. I told her I was grateful for this job, not for the pay but because I was in a position to help other people save their jobs, and in a small way redeem myself. Letting all that pour out of me was a huge release, I actually felt lighter.

I paused and Gwen looked at me and smiled. "You know Tommy, you put too much pressure on yourself, and too much importance to your work. It isn't your fault the economy tanked, and it isn't your fault that those people lost their jobs. I think that because you have put everything else aside in your life, family, friends, everything, you don't have anything else to look to for guidance. Without work Tommy, you don't feel like you exist. You really have to fix that."

I couldn't argue, she was right. I was worse off than before because now I was working from home I could go an entire week without leaving the house. The only people I saw were Sophie and Jake, and I barely had any interaction with them. Gwen was the only other person I every spoke with.

"I am really sorry to hear about you and your wife. I realize that is tough, but there are two options, one you could possibly fix the relationship, or two, you could move on. Either of those are going to be difficult for you. You have to stop living like a hermit, and start living. When was the last time you and Sophie had sex?"

"Several months."

"Are you getting anything on the side?"

"Of course not."

"So you haven't gotten a good orgasm in months?"

The last few times Sophie and I had sex were an unmitigated disaster. She could read my humiliation on my face.

"For fuck sakes Tommy, you can't spend your whole life whacking off by yourself."

"I don't..."

"Save it. I have an idea." She got up and spoke to a waitress and pointed to the dark skinned woman I had been eyeing. Gwen came back and the waitress walked over to the other stripper.

"What did you do?" I asked. Gwen didn't answer.

Both ladies showed up at the table with some portable dividers which hid the booth from view. The dark skinned stripper came in and pulled the table back. She took my hand had me stand up.

"Your wife tells me that it is your birthday and she got me for your present."

Before I could answer a new song started and she began dancing seductively around me, clawing at my clothes. She slipped off my jacket and removed my tie. She then pulled my shirt loose from my pants and unbuttoned it then slid it off. I stood there bare chested as she ran her tits over my chest, belly and back. She undid my belt, I tried to stop her but Gwen shook her head, and stood up. Gwen pulled her dress over her shoulder again and let it drop to the floor. The stripper smiled, unfastened my pants and let them drop, then she pulled my boxers down to my ankles. I stood there in nothing but socks and shoes. She had me sit down again. When the next song started Gwen pulled a condom from her purse and handed it to the stripper. She opened the package and started to roll the condom onto me.

"I can't, I am married." I said.

"I know sweetie, you wife is right there." She laughed.

"The condom is so your cum doesn't go everywhere when you jack off, darling. We want to see you pleasure yourself."

The stripper continued to roll the condom on then stood up and pulled off her panties. The two of them began to caress each other, kissing lightly, and slowly began to paw at each other more intimately. Gwen whispered something to her and the stripper began to suck Gwen's nipples. Both women began fingering themselves, spreading their legs wide to give me a good view. I felt my cock twitch at the sight, that was when I realized I was playing with myself. At the start of the third song both women moved towards me. Gwen sat at my feet with her legs spread wide as she fingered her clit. The stripper stood on the bench seat with one leg on either side of me, her pussy inches from my face and two fingers were deep inside her cunt. I could smell her, it was intoxicating. I started stroking faster she turned around and bent down low and held her balance by putting her hands on my knees. Then she pushed her pussy into my face. I wanted to lick her, but I didn't know what she would have done. I was getting very close.

She pulled away from me. She straddled one of my legs while Gwen straddled the other, their wet pussies rubbing against my thighs. They both pressed their breasts against me, kissing me, begging me to cum.

"Oh Tommy, please cum. I just need to see you cum Tommy."

"Oh yeah shoot your load I want to see your cock pumping your cream."

I couldn't hold it any more I came. I shot a huge load of cum into that condom. I felt instantly drained. I sat their panting as the girls got up. Gwen reached into her purse and handed her some cash.

"Thank you" she said "take your time cleaning up." She pushed the divider aside and left. We quickly dressed, I didn't know what to say to Gwen.

"You are pretty quiet."

"Sorry, I am just feeling a little guilty, I think I have just cheated on my wife."

"You told me she was having an affair, but you have never fooled around on her?"

"No, this is the first."

"Well, I don't think that jerking off in a strip club counts as cheating, but I will have to check my rule book when I get home."

We got back to the office and went into the boardroom we used for the presentation, it wasn't booked for the rest of the day. We started gathering information on the other offices to sort through. It would certainly be faster to download them here than to do it from home. We spent most of the afternoon working, barely talking. I noticed it was after five and I mentioned that I should get home. I told Gwen I would be online again after supper, likely around seven.

"You know, you work too hard. I have something for you, hang on." She went to her cubicle, the office was deserted. She took picked up a clock from her desk. "I want you to have this." It was a digital clock made to look like an antique that had LCD numbers as hands. There were several buttons that where hidden as icons as part of the design. When you pushed the middle one it showed the weather. It also had a buttons that could be used as a timer: start, stop and reset. Gwen said that I could use it to track how long I worked every day.

"No I couldn't"

"I insist, do you have a clock in your office?"

"Actually, no."

"Well you need one. Let me set it up for you, it connects to the Internet to get the weather, what is your wifi address?"

I have her the password and she entered it.

"There, all you have to do is plug it in and it is ready to go. Hit this button to start your timer when you sit down at your desk, hit the other one to stop it. I thanked her and left. On the way home I remembered I promised to pick up some condoms for Jake, I thought about going to the drug store, but I thought I would drop in the sex shop instead. I always got a strange thrill wandering through the sex shop, seeing the seemingly normal people browsing through strange sex toys. If I see someone looking over at me, I like to do something to catch their attention like look the bondage equipment. I imagine them thinking he is a normal looking guy, but he likes to get tied up and spanked. I went over to the condom aisle and picked up a variety pack for Jake. I found a hundred pack on sale, it contained lubricated, ribbed, scented, colored, flavored, and even glow in the dark. I find it hard to pass up a bargain. I remembered my conversation with Jake earlier about lube, I thought it would be awkward to buy it for him but I might check some out for myself. I found there were a few in tubes and jars. I found one that was specifically designed for jacking off, I made sure it was unscented, I didn't want my office to be smelling of some exotic massage oil. I was wandering over to the DVDs when I saw a woman shopping for strap-ons. I wanted to get a closer look, was she a lesbian, or does she want to fuck her husband or boyfriend up the ass? She was comparing several models and I snuck up behind her pretending to look at the masturbators. From behind she was attractive, late thirties, early forties maybe, petite frame, short. She seemed familiar.

"Oh shit." I thought to myself and I put the sex toy back on the shelf and fumbled it. She turned around, it was Sophie's friend Peggy. We both turned beet red.

"Hi Peggy."

"Hi Tom."

I hung the masturbator on the hook and she hid the strap-on behind her back.

"I guess we are both busted browsing for sex toys."

"Not just toys it seems." she said looking at me icily.

"Oh, the condoms, no, they are not for me. They are for Jake. I told him I would pick some up for him, I didn't know what he wanted so I got a variety pack. You know, it would be awkward to ask, so what size are you, or do you prefer thins or lubricated? You know..." I realized I was rambling. "The jack off lube is for me." I showed her the jar.

She bust out laughing, and I followed.

"No seriously" I said calming down. "I don't want you to get the wrong impression about me. You caught me, I jerk off I admit that, but the condoms really are for Jake. I'll prove it." I pulled out my phone and showed her I was calling Jake's cell. I put the volume up so she could hear.

"Hi Pop, what's up?"

"Hi Jake, remember when I said I would pick up those condoms for you?"

"Yeah?"

"I wasn't sure what to get, so I thought I would pick up a variety pack, is that OK or were you looking for something specific?"

"No, that sounds good Pop, I appreciate it, thanks."

"OK, see you later."

"Bye."

"There see, they are for Jake."

"OK, I believe you" she said smiling, "Do you care to explain about the masturbation cream?"

"I don't, do you want to explain about the strap-on in your hand?"

"Not really, no."

"OK then." I said, knowing I had her.

"Actually, do you know anything about these?" she asked a little embarrassed.

"Not really. Do you want me to help you out?"

"How?"

I lifted up my hand and flagged over a clerk. "Excuse me miss, could you please give us a hand?"

"Yes, is there anything in particular you need?"

"Actually yes, this is a little embarrassing, but my wife and I are looking for a strap-on, and we don't know which one to get. Can you help us out with that?"

"Sure, will she be using it on you, or on a lady friend?" she asked. I was impressed at the professional nature in which she asked the question, pleasant and completely judgment free. I looked over at Peggy and she was very uncomfortable.

I smiled at the clerk and said "Both."

The clerk took it completely in stride. She walked us through the basics and showed ones that allowed us to change the dildo for different uses. She asked Peggy to pick out the dildo attachments. Peggy started to get into the role play and asked me what size I would like her to fuck me with, I played along and picked out a few for her to choose from. She said she would like to get one the size of my cock, and asked me which I thought was the closest. Again, I picked out a few for her to choose from. Peggy picked one that allowed for two attachments, one for her and one for the person she was going to use it on. Hers had a vibrator in it. She picked out two dildos for the front, one for anal use, so I was still unsure on whom she intended to use it. We walked up to the cash and paid for out items separately and left.

As we left Peggy said "Thanks Tom, I appreciate your help. You really are a sweet guy."

"Anytime Peggy" I said as I got in the car.

I got in and no one was home. I was a little charged from my encounter with Peggy, and I was still a little horny thinking about my afternoon with Gwen. I put my stuff in the office and put the box of condoms on Jake's nightstand. I went into the bedroom and got undressed. The house was still very warm. By the time I got back to my desk I was hard again. I didn't have much time before Sophie got home, so I thought I would rub one out quickly. I booted up my desktop and while it was starting I plugged in Gwen's clock. I searched for some videos with strap-ons I found two, one with a girl fucking a guy up the ass, and one with two lesbians. I couldn't decide so I opened both in separate windows and started them. I opened up my new jar of jack off lube and took out a dab, not sure how much to use. It didn't need much. I started jacking off to the two videos.

I tried to imagine that Peggy was in the videos, I was intrigued trying to figure out whether she was using it on a girl or a guy. She didn't mention that she was seeing anyone last time I saw her. I thought about asking Sophie, but that would be a difficult subject to bring up. I wondered what it would be like to have a woman fuck me up the ass. I imagined Peggy bending me over and sliding that dildo into my ass. I decided that it wasn't for me so I closed that video and concentrated on the two lesbians. I imagined Peggy fucking Sophie with that strap-on, and even though I had cum earlier this afternoon, within seconds felt my orgasm starting, I stood up quickly and I blew another load into a tissue. I could smell the cream a bit, but it wasn't overwhelming, the room smelt mostly of cum and pizza? I turned around and there was Sophie holding a pizza.
"So this is what you do when I am not home, huh?"