I had been married for 18 years when my wife Ellen was killed in a car accident. That was February, 2002. Our two boys were 15 and 17 at the time. Ellen was out of town on business when a tractor trailer crossed the highway median and struck her car head-on. I was devastated even though my marriage had been on the rocks for years. We didn’t fight, Ellen and I had just drifted apart. I never measured up to her expectations. We had been talking openly about divorcing when our youngest son left for college.

Between Ellen's life insurance and the lawsuit against the trucking company of the negligent driver I was the beneficiary of over 4 million dollars. In addition, each of my boys got their own trust funds that would provide for college and well beyond.

I continued to live a modest life and other than a new pickup truck for me and a couple of nice used cars for the boys I invested the money and kept on working. For the next five years my priority was getting my boys raised.

I wasn't interested in getting into another committed relationship, I surely didn't want to live with anyone and there was no way in hell I ever wanted to be married again.

Every woman I dated had an agenda. They were all looking for some love-sick lonely dupe to marry them and pay their bills. Fuck that. I am extremely happy with my life. I love my low pressure job. No one tells me how to dress, how to decorate the house, what to watch on TV, nothing. I don't have to put up with a manipulative bitch who thinks I'm underpaid, getting pudgy, or that I need to start using Rogaine. I don't have to be played by a woman that thinks she can get me to do whatever she wants by occasionally laying down and spreading her legs and doing a poor imitation of a blowup doll.

Don't think get the wrong idea, I love women and I'm a total horn dog. I love pussy, I just love it on my terms.

For the next couple of years I got constant mercy fucks from women who wanted to take care of the poor widower and single dad. Women surrounded me like a wolf pack, all with the best of intentions of course. They wanted to cook for me and the boys, clean the house, be a shoulder to cry on, spread their pussy, suck my cock, lick my balls, and just about anything else you can imagine. Yeah, it's always good like that for a couple of weeks then their real agenda comes out.

As soon as I sensed my fuck toy wanted some kind of commitment or got nosey about where I was or what I was doing when I wasn't roto-rooting their throat with my cock, I ended it. That was easy enough for the fragile guy who's wife had died and who couldn't stop thinking about her.

“Goodbye“. Thanks for the memories. Sorry I don't have any parting gifts for you. I guess you'll have to find another pussy whipped fool to sink your claws into and suck the life out of.

Don’t worry about me though, the line of women wanting to be my therapist and fuck toy went around the block a couple of times.

When the boys left for college I sold my 4 bedroom house and moved into a 2 bedroom condo. It was the bachelor pad I had dreamed of my whole life.

After fucking half the women in Akron, the sympathy card wasn’t working anymore, so I started fucking strippers. Getting sex from a stripper isn‘t hard. It’s just a matter of how much it‘s going to cost you.
I’ll have to share my stripper fucking stories with you another time. This story is about a very sexy, very attractive young woman that came to work at my company last year. A woman named Holly.

Technically, I’m not Holly’s boss, but I am the senior artist at the firm, a small privately owned company that has grown steadily over the years. Although I have decent computer skills, my art skills are “old school”. I typically compose my work by hand and then convert it to digital. Today everything is done on computers from start to finish. Prior to Holly joining the firm, I was an art department of one.

Last year my workload got so heavy that I couldn’t keep up by myself anymore. The Marketing Director hired Holly, a 26 year old Kent State graduate and computer whiz-kid to help out. We work alone in a small well equipped office in the basement of an old building in downtown Akron. Holly is creative, well educated and I truly enjoy her company. She brings out the best in me. I think most people work better when they can collaborate with people they like and respect. I develop the basic concepts and Holly adds her touches and brings it to life on the computer.

One thing I noticed right away about Holly was that she had a lot of expensive clothes. During the first month at work she never wore the same outfit twice. She also had a lot of jewelry, designer handbags and shoes. Holly bragged that some of her handbags cost over $300. I figured her husband must be rich. A beautiful girl like Holly should be married to a rich guy. I knew she didn’t buy that all that stuff on a graphic designer’s salary.

I took Holly up on her offer to buy me lunch one day. I liked Holly but I had a daily routine that I didn't want to give up. Since I didn’t want her to think I was rude, we went out to lunch once a week and took turns picking up the check.

Holly assumed that I went home for lunch everyday. The truth is that I spent my long lunches at one of the handful strip clubs in the area. Day shift strippers are a lot less expensive to fuck than night shift strippers. The day shift strippers are a combination of single moms who have kids that they can’t leave alone at night, older strippers that are past their prime, girls with too many tattoos, stretch marks, scars, muffin tops or some combination of those things. You can think of these girls as the third string team. Maybe “Bush League” would be a better name. The big money at the strip club is made at night and on the weekends by the youngest and hottest girls. The clubs give the best shifts to their top earners. Like I said before, getting sex from a stripper is a matter of paying market price. A "first string" stripper making $2000 a week just by showing her pussy and giving lap dances isn’t going to fuck you for $200 no matter how much you remind her of her long lost daddy.

I wasn’t surprised when Holly started telling me about the big fights she was having with her husband about bills and her over-spending. I guess they had a lot of credit cards and a mountain of debt. A few weeks later her husband cut all their credit cards in half and put Holly on a budget. She was really pissed . She started packing a lunch.

When Holly brought a brown bag lunch to work the first time, she looked like a kid who just had her lunch money stolen. I felt sorry for her and told her to join me for lunch. Holly declined at first, reminding me that it was her turn to buy and she didn‘t have any money. It didn’t take much arm twisting for me to convince her to throw her cold sandwich away and let me buy lunch.

At lunch, Holly asked me where I went when I didn‘t have lunch with her. During a long pause, I considered a number of different plausible lies I could tell her. Something made me tell her the truth, but the minute the words came out of my mouth I worried she would think I was a dirty, degenerate perv and our friendship would be ruined. Of course I didn’t tell her my reason for going to the strip clubs was to scout desperate needy women that I could fuck for cheap.

Holly seemed a little uncomfortable after my dirty confession and changed the subject to trashing her “tight-wad” husband which had become her favorite thing to talk about. On the drive back to the office I asked her if she was offended by what I had told her. Holly took a deep breath and said, “You would be more surprised by my secret than I was with yours.”

I didn’t press her, figuring she would tell me her secret if she wanted me to know. Later, as I was tidying my work space preparing to leave for the day Holly approached my desk and asked, “Would you like to guess how I paid my way through college?”

“Drawing $5 caricatures at carnivals?”, I joked.

Holly slapped my arm. “I was a D A N C E R ”, she said.

“Oh, a dancer….. At the ballet?” I joked again.

“Fuck you Todd”, she laughed and slapped my arm again. “You better not ever tell anyone”, she said. I stuck my hand out to shake and promised her she could trust me.

The next day we carried on like nothing had happened. I was anxious to know more but I’ve learned the best way to get a woman do what you want is to play it cool. I knew she was dying to spill her guts about her shady past.

When I took my lunch break that day, Holly joked that she was going to inspect me for glitter when I got back. I told her to enjoy her leftover meatloaf. We teased each other like that for the next few days. Neither asking the other anything too personal.

The following Tuesday, I told Holly not to pack a lunch the next day because I was taking her out to lunch. Holly said she didn’t think it was fair that she couldn’t pay, but admitted that she enjoyed our lunches and didn’t want to give that up.

After a couple of minutes she perked up and said she had an idea. “You skip the strip club tomorrow, buy me lunch and I’ll show you MY tits”.

“Sounds like one helluva good idea”, I replied.

“You want to see them now or tomorrow?, Holly stood up and grabbed the bottom of her top as if she was ready to expose herself.
My smile was so big that she didn’t wait for an answer, she pulled her top up grabbing her bra on the way up. Out plopped her perfectly shaped 34 D cup boobs. Holly stood there exposing them in their full glory, letting me take my time to admire them. “Very very nice”, I said.

They looked too perfect to be real, I would have bet money they were implants, but there were no visible scars. I was curious, but asking would be rude. I would find out soon enough that they were all natural.

The next day at lunch Holly spilled her guts to me. She told me about her childhood and family and growing up in Cleveland. Holly didn’t fit the profile of the typical stripper. Believe me, I know that sad story by heart. Holly came from a big Catholic family with loving parents that were still together. She started stripping during her Junior year at Kent State to avoid going into any further debt with student loans. Holly said she made over $500 a night stripping. She said she continued stripping for two years after graduating, making over $80,000 a year.

Holly said she managed to avoid becoming a drunk or drug addict but did develop a bit of a shopping problem. She said she pissed through all that money, blowing it on designer clothes, jewelry and vacations.

Holly said her parents never had a clue that she was stripping and her husband has no idea about her past either. Holly said walking away from stripping and the money was a hard decision. She now makes less than half what she used to make. I told her that a long career in stripping always has a sad ending and that she made the right choice.

The conversation switched to me. Holly asked me why I spend so much time in strip clubs. I told her that I enjoyed the company of attractive nude women. I liked getting to know the girls, and that I had become something of a Sugar Daddy to a couple of them.

“I used to have a Sugar Daddy before I got married”, Holly blurted out.

“Really? What did you do for your Sugar Daddy”, I asked.

“Hmmm, we’ll have to continue this conversation another time”, she said. “But I’ll bet you have a pretty good idea how that works Big Daddy.”

All of a sudden, my favorite strippers weren’t as appealing as they were before. They seemed dirty and stupid. I had been planning to hookup with Cheyenne that night but thinking about her saggy deflated tits and various gang tattoos made me nauseous so I cancelled our rendezvous.

If Cheyenne and Holly were steaks, Cheyenne would be ground round and Holly would be fillet mignon. If they were cars, Cheyenne was a Kia and Holly was a Ferrari.

During our next personal conversation at work the following day, things got even more interesting. Holly asked me how much it cost to be a Sugar Daddy these days. She was shocked to find out I spend around $600 a week on my “friends”.

Holly told me about her Sugar Daddy. An older guy named Roger. Roger was a businessman who owned a bunch of rental properties in Kent. He provided Holly with a nice furnished apartment, paid all her utilities and took her on a “shopping spree” in Cleveland once a month. He occasionally left envelopes of extra cash on her kitchen table when he spent the night. Holly says they still keep in touch by email but she hasn’t seen Roger since she got married last year.

Like most days, the hours had flown by at work and it was quitting time. “Interesting conversation”, I said. “It’s a good thing you’re a happily married and faithful woman”.

Holly shut down her computer and collected her things while I waited to walk out with her. “I’ll think about how to reply to that tonight and you think about these”, she said as she flashed her spectacular tits again.

I had a lot of things on my mind as I drove home that day. Was I on the verge of fucking up a great friendship and work relationship? Holly and I would have to do some serious talking before we took this Sugar Daddy game any farther. But I knew I had to have her. At that moment, I wanted her more than I ever wanted any woman in my life. I drove right past one of my favorite strip clubs without a glance. “What the fuck is wrong with me?”, I wondered. My bank balance grows at the rate of $15,000 a month, yet I choose to fuck those dirty hustling sluts. I realized that if I fucked Holly, I would never be able to go back to fucking Bush League whores again.

What was I saving all that money for? I wasn’t getting any younger. Holly had already brightened my life, but she was about to brighten it a whole lot more, and I was going to make her life a lot easier too.

When I took Holly to my apartment for the first time, I told her I wanted to take our time. This was going to be something really special and I wanted to savor every second of it. Holly didn’t disappoint either. She told me to put on some music. She did a slow strip tease to the music of Harry Connick Jr. while I watched in my favorite chair. She tossed her blouse and bra across the room and moved toward me seductively. She told me I couldn't touch. I kept my hands folded in my lap, enjoying the show.

Holly bent over letting her breasts glide against my face and lips. When I tried to kiss and suck her nipple she backed away and reminded me that we were taking it slow. Holly grabbed my face and planted a wet kiss on my lips. I was surprised by the kiss. I wasn’t sure that she would even let me kiss her. She moved in for another kiss, this a deep open mouth kiss. Our tongues entwined and explored each other‘s mouths. Holly placed my hands on her tits as we continued to kiss like 15 year old kids who had just discovered French kissing. I couldn’t remember the last time I had kissed anyone like this. The room was getting hot, I was getting dizzy with lust and I had an enormous erection.

Holly stepped back long enough to remove her skirt, leaving her lavender thong panties on for now. She unzipped my pants and pulled my stiff cock out then she sat on my lap grinding on my cock to the slow rhythm of the music while I played with her tits and hard nipples and kissed her mouth. I could feel Holly’s wetness with the head of my cock. A thin layer of material was the only thing preventing me from sliding inside her. Small beads of sweat began to form on Holly’s breasts, neck and the small of her back. She moaned as she pushed my face toward her breasts, telling me it was time to suck them.

I sucked softy alternating between each breast. At Holly’s request I began to suck harder, then nibble, then bite. Holly moaned and ground her pussy against me even harder. Her breathing quickened and she yelled “bite harder baby, I’m cumming. Holly collapsed on me panting hard. I could smell the heavenly scent of her pussy and I wanted to lick it. I hugged her softly and held onto her while she kissed my neck. I could feel her pelvic muscles flexing against my cock. “Did you know I have a snapper?”, she whispered in my ear. We both giggled. I admitted that I was impressed.

Holly slid down between my knees and helped me wiggle out of my jeans and briefs. Then she stepped out of her soaked panties giving me a glimpse of her pretty shaved pussy for the first time. She handed the panties to me, telling me, “play with these while I suck your cock”. I pressed the panties to my face and took a slow deep breath as Holly gripped the shaft of my cock firmly and begin to lick the swollen head. Her tongue flicked the sensitive sweet spot causing jolts of electricity to shoot through my body. I leaned back and closed my eyes while Holly did amazing things to my cock with her hand and mouth.

“These balls seem heavy with cum”, she said as she slowly and gently sucked each testicle. “You want to cum in my mouth don’t you?”

“Uh huh”, I mumbled.

“Watch me”, she demanded.

I opened my eyes in time to see Holly take all 8 inches of my cock to the back of her throat. Who could have ever imagined that the bright sweet sexy innocent newlywed I had been working with for the last couple of months was such an incredible sexpot? A few minutes of steady deep throating had me blowing a huge load into Holly’s mouth. She stroked and milked the last drops of my cum onto her tongue before licking my cock clean and swallowing every drop.

Holly pulled me up. “Take me to your bedroom and fuck me”, she said.