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It was about 10 on a Sunday morning and I was sitting on the hood of my wife's BMW in the Hilton parking lot, waiting for my loving wife to come out with her lover. I took a bunch of pictures as the couple came out and their passionate kiss goodbye. Jesse was still holding his hand when she spotted me, I could read her lips as she said, "Oh fuck, my husband." Joe, who had once been a very good friend of mine made eye contact with me. Jesse was pushing him away as she collapsed to her knees.
I nodded to the two process servers who were waiting and Jesse was served with divorce papers and a copy of the prenup her daddy had insisted on. Daddy had been wealthy at one point but the housing crisis wiped him out, I made out very well. All the text messages they sent to each other, with the dick and pussy pictures were included. I also sent a copy to her parents who thought their daughter was too good for me.
Joe was served with and "alienation of affection" suit. I didn't expect to get a lot of money but the lawyers to defend himself would cost him. His wife would be receiving a copy of the suit, both his and hers contained all the text messages Joe and my wife sent with the dick and pussy pictures included.
There were a few more errands I had to do before I left town hopefully for good. Since the house would be mine, I had already put it up for sale but I had to sign some paperwork before I left. The Saturday before was a very productive day, since Jesse had left Friday night to spend the weekend with her sister, I was able to gather all her shit and put it in a storage locker. The ashes from all our wedding stuff, like the photo album and her wedding dress were in a burn pit. A consignment shop had picked up all the furniture. I still had to pay and tip the cleaning crew that was in there. All the joint accounts had already been closed. Jesse was unaware but she was two months behind on her car payment.
There was also one more person I had to say goodbye to and that was Jesse's sister Jill. I had always thought we were close, nothing sexual but I thought of her as an honest friend. Yesterday evening I had called Jill and she said Jesse had run to the liquor store. Jesse's excuse for spending the weekend there was to watch her nephews while Jill went to a wedding. Fucking liars, and it wasn't the first time Jill covered for Jesse. I was disappointed in her so I dropped her off a copy of the divorce papers and text messages. I didn't say anything, handed her the packet and left.
Thank god Jesse couldn't bear me children. It was five years ago that we found out and I caught her cheating on me for the first time two months later. She promised it would never happen again and blamed it on her deep depression when she found out she was barren. Maybe she kept her promise or hid it better until a few months ago. I wasted ten years of my life with her, five of which I tried to be noble even though I knew she could never give me the children I wanted.
With my business in town completed, I headed to Denver. There's an old saying "when one door closes, another door opens." It was a couple of weeks after I realized Jesse was cheating on me that my boss called me into his office.
"Jack, you've been in a funk the last two weeks, is everything okay?"
"Yes, I'm blaming allergies but Jesse thinks I have a bug."
"Well, our operation in Denver is struggling, high staff turnover and shrinking profits. The board is considering shutting it down. There are some board members who don't want to put that many people out of work. I suggested that you take over. To be honest, they believe the problems are too ingrained. If you're successful, you'll be a hero, if not, they all thought it was impossible so you can come back here."
"The company will supply you with an extended stay hotel and cover your food expenses. We know this will be hard on you and Jesse so weekly flights back and forth will be covered for either you or Jesse, plus a significant bump in pay. What do you think?"
"I'm thinking I like it, but I need to discuss it with Jesse first. When will you expect me to leave?"
He gave me a date that sounded familiar. I went home and realized that Jesse had wrote that date on the calendar for babysitting her nephews. I called my boss and told him Jesse and I were thrilled with the opportunity both career wise and to spend some time in Denver.
So, on a beautiful Sunday after unleashing a shit storm, I was driving my Jeep stuffed with most of my belongings on a two day drive to Denver. My cell phone was turned off before I started the jeep. After making it to my overnight stay, I grabbed some dinner at a chain. Since all my meals were covered I ate well. I turned my cell back on and showered while the shit hit the fan. Feeling refreshed after the shower, I started with Jesse's voice mails.
The first was as expected, apologizing for cheating on me again and promising it would never happen again. I wanted to laugh because she couldn't cheat on me when we were divorced. The second was Jesse complaining because all our joint accounts were closed. Number three was her screaming about where was her stuff and what happened to our furniture and why I was selling the house. There were some other voice mails but she never asked me where I was and she never said she loved me.
In a moment of weakness, I called her, "Jesse, you need to read the information that you were served with today."
"I don't want to Jack, please come home. I'm so sorry and I know I haven't shown it but I do love you."
"Shut the fuck up Jesse, it's way too late for I'm sorry. Read the documents. Most importantly, I am exercising the prenup your father insisted we sign so you have no claim to any joint assets. Your personal belongings are in a storage facility, the paperwork and keys are in the envelope. I paid the first month's rent. The furniture is in a consignment shop, the address is in the envelope. You are free to buy back anything you're interested in. Also, in the envelope is a cash card representing half our checking and savings account because I was feeling generous. The joint cards are cancelled, your AmEx you use for your Hilton bill is still active. You're two months behind on the payments for the beamer you had to have. Thank god my name wasn't on that loan."
"This is our last direct communication so get a lawyer and we can talk through them. By the way, our cell phone plan expires at the end of the month."
I hung up and Jesse immediately tried calling me back so I blocked her. There were nasty voice mails and text messages from her parents, mostly about sharing the dick and pussy pictures with them. There was nasty voice mails and text messages from Joe because I told his wife and she was going to divorce him, all because my slut wife couldn't keep her legs closed. I forwarded that piece to Jesse. He also made a bunch of threats against my personal wellbeing, those I sent to my attorney. My sister-in-law Jill sent me a softer text message, telling me she told Jesse she was an idiot and was sorry she covered for her.
The following day, I was moving into the extended stay hotel. The view of the mountains from my windows was amazing.
Wednesday was my first visit to my new office. It took me minutes to realize the guy running the place was a dick. It started off bad when he showed me to a shoebox that would be my new office. Didn't he realize that he would be reporting to me? But I kept my mouth shut that first day, and he treated everyone like shit. No wonder there was such a high turnover rate. I called my old boss that night and gave him my first day impressions.
He said HR had done some exit interviews with former employees who all had the same impression of the guy. A team from HR will be there tomorrow morning to sever the employment relationship.
Once he was gone, I began the slow process of trying to heal the damage he had done, every morning I met with small groups finding out what they thought was going well and what wasn't. a few more people left, exercising offers they had already received. There were a couple of troublemakers that also had to be separated. But six months later we started doing well and had a decent quarter. The board was singing praises to my name.
Things on the Jesse front were dragging. Her father hired a bargain basement attorney to represent her who was unfit to be any kind of lawyer. My attorney said he was basically teaching the guy first year law stuff. The best one was when Jesse asked for counseling.
According to my lawyer, Jesse's lawyer explained to the judge that we had a loving relationship for the last ten years until Jesse's recent one time mistake in judgment.
My attorney shredded him, first by presenting evidence of her prior infidelity, then the months of text messages, dick and pussy pics Jesse and Joe had exchanged. The judge dismissed the request for counseling and ruled that Jesse was responsible for the court costs and my legal fees. The judge also sanctioned Jesse's attorney for wasting the courts time.
That was the last big roadblock and a year after Jesse's weekend in the Hilton we were divorced.
My mind was so focused on recovering that operating unit, I really didn't have time for a social life. My admin always organized different company functions like trips to ball games. Those were probably the extent of my social life that first year although my admin and several other women in the office were open to more. Especially as the white band on my wedding finger began to fade.
I would never have an affair with someone who worked for me. That was suicide today especially in my company. I had been living in the extended stay for a year, occasionally I met some female guests and enjoyed their company. Most of their stays were shorter than mine so the relationships were short lived. I wasn't complaining.
During one of my weekly status calls I mentioned to my boss that I was thinking of buying something permanent in the area. He asked me to wait. The board was so thrilled in how well the turnaround went that they were considering me for another position that would include a VP title, probably in a year. He wanted me to start grooming my successor.
Two or three year assignments were the norm and I was on my third move during that time. I still hadn't bought anything permanent. The longest relationship I had during that time was a year. I thought that relationship might lead to something permanent but I was transferred again and she didn't want to move.
Six years after Hilton night, I was back in my old town for a board meeting. Usually once or twice a year I had to attend these meetings. Being back there always put me in a funk as it dredged up bad memories. If being in town didn't suck enough, the board meetings were at that Hilton and we all had rooms there. I wondered if I was sleeping in the same room that Joe was fucking my wife. And then things got worse.
I was eating a late dinner in the hotel restaurant by myself when Jesse sat down across from me. She had put on a little weight and some wrinkles, I'm sure we both have but other than that she didn't look much different than she did six years ago.
"Hello Jack, I hope you don't mind if I sit here, I wanted to see how you were doing."
"I'm doing fine Jesse, how did you know I would be here?"
"I wasn't stalking you Jack, I'm the event coordinator here Jack so I knew you would be here. Someone and I'm pretty sure it wasn't you, sent the text messages to my old company, and since some of those were sent on company time, they allowed me to resign. I see you're doing well with a VP title."
"Yes, my company has been very good to me." I was trying to keep this conversation short.
"Relax Jack," as she ordered a drink. "No rings on your finger Jack, I thought some Denver honey would have roped you in by now."
"No rings and I'm in Atlanta now. No rings on your fingers either?" Jesse's smile cracked on that one, but she started this conversation.
"No rings Jack. I decided while our divorce played out that I didn't play well with men. Not to get too personal but I haven't gotten laid since that weekend."
A thousand sarcastic responses went through my mind, instead I said, "Your still young and very beautiful Jesse, you should find someone to share your life with."
Jesse smiled at the compliment, "Thank you Jack, that means a lot to me."
We continued to chat about her parents, her sister and her nephews, I was trying to end it but Jesse wasn't going to let it happen. She was fucking beautiful, maybe not to every guy but I found everything about her beautiful, especially that smile. She knew it and was flashing that smile a lot and then she kept reaching across the table and touching my hand.
Jesse was on her third glass of wine and I was nursing my third glass of scotch. Three drinks was usually her limit and it had been a long time since I had more than three. My mind was wondering how this was going to play out and my dick was reminding me how long he had been idle.
Jesse emptied her glass and grabbed my hand, "Jack, you can take me upstairs, no commitments, just two lonely people enjoying ourselves."
Her eyes were moist as she spoke and I could not say no, and that smile when I said 'let's go' was priceless.
Sex was Jesse was fantastic, easily the best sex I had since we split. After ten years of marriage, we knew what each other liked. There was blip when I realized that last man to fuck her was one of my best friends. Jesse was riding me, took a couple of extra grinds and had me hard again. After a second round, we fell asleep together.
In the morning, a porter was knocking on a door and he delivered a suitcase to Jesse. She saw the look on my face, "I'm the event coordinator Jack, and many of those events run late, most of the time it doesn't make sense to go home so I keep a bag here. Sometimes I wonder why I keep the apartment."
Jesse had to work and I had meetings to attend but we ate dinner and slept together the next three nights before I had to fly back to Atlanta. We had a good time together, almost too good. Sex between us had always been good, there's a line in a movie about a woman who could suck the ball from a trailer hitch through a garden hose and that described Jesse.
After returning to Atlanta, Jesse and I continued swapping texts back and forth. I had no doubt that Jesse hoped we would get back together. She already cheated on me twice, both were devastating.
Jesse wanted to visit Atlanta, she had a four day weekend coming up. There were no other women on my horizon so I invited her down and took a couple of days off. Whenever the company moved me they would set me up with a luxurious place to live and Jesse was blown away by the view from my windows.
I swore she was going to fuck me to death. When she said she wanted to come down for a visit, I thought she wanted to see the sights. Basically, we fucked the four days away and went out to eat. Jesse discovered she loved masturbating for me, that and flashing me. Anytime we were in the car, she would have her legs spread and her fingers in her pussy. She didn't bring a bra with her.
Toward her last day in Atlanta, Jesse began hinting about getting back together. I didn't comment one way or the other. For our last dinner, I took Jesse to my favorite restaurant in the area. I had become friendly with some of the waitstaff and my favorite waitress was taking care of us. Jesse outdid herself that night, a little black dress that showed lots of cleavage with her nipples poking through. She had bright blue panties on which I saw a lot of.
My favorite waitress took a picture of us which I posted on Facebook. Jesse was angry that I did that but couldn't give me a rationale reason why. The sex that night was fantastic, Jesse wouldn't let me come and kept taking me to the edge. She was doing the same thing to herself. Our mutual orgasm was probably the most intense of my life. As I drifted off to sleep I was wondering where she learned that trick considering she said she hadn't been with anyone since that night at the Hilton.
Jesse had an early flight the next morning and was quiet as she showered and dressed. On the way to the airport, she stopped hinting.
"Jack, what do you think about us getting back together. The sex has been fantastic."
"You're right Jesse, and your smile still thrills me. My current job has me bouncing around, moving every three years or less. So there's lots to think about and I will think about it. And you are fucking beautiful."
She smiled at that and I loved that smile, but she's already cheated on me twice.
A week later, I received a very long email from her sister Jill:
"Jack I saw the picture of you and Jesse down in Atlanta and it looks like you two are getting back together. I know I did you wrong by covering her liaison with Joe at the Hilton but you may not know I paid a price for that. My husband Jeff found out what I did when he saw the package you sent me."
"Since I helped my sister coverup her infidelity, I must be okay with wives cheating on their husbands and he was convinced it would only be a matter of time before I cheated. Our divorce was finalized before you and Jesse's. My boys always worshipped their father and as soon as they were old enough, they chose to live with him. Thanks to helping my sister, I have been alone for the last two years."
"I have learned my lesson as far as my sister is concerned. Jesse said she told you some sad story about swearing off men and not having sex in six years. Nothing could be farther from the truth. First of all, she's been living with Joe in a one bedroom apartment since your divorce, neither could afford to live on their own so it started as a matter of convenience. Then she took the job at the Hilton where she's been fucking a bunch of different men. She has several regulars who visit the area frequently and accepts money from them. So instead of being celibate as she stated, she's been whoring her ass out."
"Jesse brags about her sex life with me, asking me to join her. Some of her friends would pay well for a threesome she said. Like I would participate in a threesome with my slut sister. I don't know what her number is but its way more than a hundred."
"This time I'm warning you Jack, run away and get yourself tested. Who knows what she's carrying."
Even before I finished the email I was vomiting in the bathroom. I sent Jill a thank you and told her that Jesse did want us to get back together but I didn't think I could ever trust her again. Your email helped me see things clearly.
Jill responded quickly, "Glad I could help and hopefully I have earned a little forgiveness for covering for her before. If you're ever back in the area, stop by and I'll fix you a nice dinner."
Jesse was bombarding me with text messages since she left Atlanta, most were sexual in nature, pictures of her pussy and tits. Pictures of her panties in public places and on most nights, videos of her masturbating with either her fingers or dildo. I had to end it so I sent her a text:
"I wanted to send you a present so I googled your address. I was surprised to see that you and Joe were sharing a one bedroom apartment. It must be hard to be celibate for six years sleeping next to your lover."
After that I blocked her had any emails sent to my spam folder. To be a dick, I sent all the pictures and videos she sent me to Joe but I wasn't sure that email address was valid.
Jill sent me another email a few days later. "Thanks for not revealing to my sister what I told you and you certainly started a shit storm. It seems Joe was okay with Jesse fucking other men as long as it was for money. He knew nothing about her trying to get back with you. But they are trapped together, neither can afford to live on their own. Jesse wanted to move in with me and I told her to fuck off."
Jill and I started emailing each other more frequently which turned into text messages. We were coming up to our annual board meeting which was going to be in the Hilton again. I was dreading going and Jill had remined me of her dinner invitation. Jill was as attractive as Jesse, some people thought they were twins but their personalities were completely different. I was already in love with Jesse when I met her sister but there were times I wondered if I married the right one. Jesse loved bars and getting drunk, Jill loved gardening and taking care of her kids. I don't think I ever saw Jill drunk.
I decided to take up Jill on her offer for dinner and it felt really weird walking up the sidewalk to her house. Her gardens were even more immaculate then I remembered. The Jill who answered the door looked tired, still beautiful like her sister and she seemed otherwise distracted. I kissed her cheek as I said hello wondering if I had been doing that for twenty years yet.
While the outside of the house showed off her gardening skills, the inside showed a lack of money. Her boys had been hard on furniture and most of their furniture was tattered that last time I was there and the carpeting was one big stain. I guess she tossed the worst of the furniture because there wasn't much left. She saw me looking at the couch with the cheap slipcover over it and lots of lumps underneath. Jill had always been an avid reader and there were piles of books everywhere.
There were only two chairs left at the kitchen table and Jill offered me a seat saying dinner will be done in fifteen. She talked about how well her boys were doing although she didn't see them very often as they were busy at college. She was still working the same job. Dinner was a simple stew, light on the meat but heavy on the vegetables she grew herself. It was delicious with an ample serving of homemade bread. There was no alcohol.
I teased her about the books, which pile was the books she read and which ones were waiting to be read. Jill gave me the first deep smile since I walked in.
"The piles on the left were ones I read, the piles on the right are waiting to be read, divided into sci-fi, romance and classics."
"It looks like my room when I was in high school, where my friends had layers of clothes scattered around their room, I had books."
"Sounds like me and Jesse, she had clothes everywhere growing up, I had books."
We talked about recent books we read, Jill had also read two of the last books I read. We shared a lot of our favorite authors. She put a homemade pie on the table for desert which was delicious.
I actually had a very pleasant time with Jill, so different than the time I spent with Jesse which was mostly fucking. But it was time to call it a night and on my way out I invited Jill out to dinner at the Hilton the next night. "My company is paying for it so you can feast on whatever you like," I said.
She was hesitating and I said she had to let me pay her back for the delicious meal. Jill finally relented and we made plans for me to pick her up at seven. I kissed her cheek again.
At about ten minutes to seven, I was only a few minutes away, Jill called me and said she had to cancel because something came up.
"I'm almost there Jill, let me stop by anyway." She hesitated before saying okay.
It was obvious that she had been crying when she answered the door and let me in. Jill sat on one end of the couch and I sat on the other. Then she offered me a cup of tea which I accepted. I followed her into the kitchen.
"What happened Jill, what came up?"
"A lot of things Jack, going out to dinner with my sister's ex-husband and I played a role in them not getting back together sparked some guilt."
"I'm thinking it's something else Jill, there is little difference between going out to dinner with your sister's ex-husband and inviting him to your house for dinner. One could say eating dinner in your house creates a worse optic, so please tell me what really came up."
Jill turned away from me and stared out the window, "This may sound so stupid to a man but I have nothing to wear to a place like the Hilton for dinner, especially if other people from your company will be there. The only thing I have left that fits me are jeans and shorts. Normally I would borrow a dress from Jesse if I needed one but I couldn't do that to go out with her ex."
"We could go to someplace more casual, Texas Roadhouse, Applebee's or anywhere else you would like to go."
We settled on a local joint serving ribs and got into a friendly debate about the hidden meaning in a classic we had both read. I had stated the lead character was a pedophile which was why he killed himself, he realized he was having trouble mentally restraining himself. We went through the short story, it had been years since I read it and finally Jill smacked her head and started laughing.
"I've read that story a dozen times over the last 30 years and was always confused why the guy killed himself. Maybe you're a pedophile and recognize the signs," she said laughing.
God she was beautiful when she laughed. She saw me staring at her and started apologizing.
"There's no need to apologize Jill, I was sitting here realizing how beautiful you are when you smiled."
Jill turned a deep shade of red and changed the subject. The ribs were fantastic and I drove Jill back to her house and walked her to her door. I went to kiss her cheek and she turned her head so that my kiss landed on her lips and soon the kiss was turning into more.
"I can't offer you a nightcap Jack, but I can offer you something else if you're okay with a 40 something woman."
"Jill, you're beautiful woman and would be happy if you're okay with this 40 something man."
Jill led me to her bedroom. The bed was a mattress and box spring sitting on the floor, there were no dressers, only cardboard boxes full of her clothes.
"What the fuck am I doing taking you into this slum," she said.
"I am here because a beautiful woman I had long admired invited me to her bed," I said and then took her into my arms and began kissing her. My hand creeped up between us and I toyed with her breast.
I must have hit the right button because Jill pushed me back on the bed and ordered me to strip while she started removing her clothes. The way she wiggled to get her jeans over her hips was enough to make me hard which became apparent when my slacks hit the floor. Jill climbed on top of me and guided my cock into her pussy. God she was beautiful. She pulled me over so I could drive for a while, I knew she came twice before I came inside her. I had the 'oh shit' look on my face.
"Don't worry Jack, I had my tubes tied after my second was born. You were pretty good there Jack, do you think two forty somethings could get a round two in. Unlike someone we know, it's really been over six years since I've had sex, at least with someone else. I have burned up a couple of vibrators though."
"I would pay to watch that," I said.
"Maybe while you all alone in Atlanta, I'll let you watch me over Facetime."
My cock wasn't hard but it was still inside her, and her talk of masturbating for me was beginning to revive me.
"And what would I be watching you do?"
"Well," she said, "I always like to start by playing with my tits, they are always a trigger for me, just like when you started caressing my breasts tonight." As she talked, she took both her tits in her hands and gave herself a massage.
"Then my nipples want some attention so I'll lick my fingers and start stroking my nipples, maybe imagining a 40 something year old man sucking on them."
Jill was rubbing wet fingers around her rock hard nipples which was making my cock hard enough to slowly move in and out of her pussy.
"And just recently, I was reading a porn story where a woman was talking about how much she loved when her lover pinched and pulled on her nipples, so I tried it. Oh my god it makes my pussy so wet. I'm 40 and still learning new things about my body."
Jill was pinching her nipples and yanking them in every direction.
"The harder I pinch or pull, the wetter my cunt. Your cock feels so much better than my vibrator. Fuck me Jack, fuck me hard."
My cock was certainly hard enough. I pushed her legs back and started fucking her hard. Jill was yelling she was coming, she was still pinching her nipples, she came again and I rolled us over. Jill was slowly bouncing up and down on my cock while she played with her tits.
I pushed her hands away and started pinching her nipples, "Who's hands feel better on your nipples Jill?"
"Your hands Jack, I'm coming again. Fuck me from behind Jack."
Jill and I were both on our knees on the floor, Jill's torso was on the bed as I started fucking her from behind. She had no place to move so I was fucking her as hard as I could. I gave her ass a slap and she moaned a yes as her body shuddered, three more times I did that with the same response before I came inside her. We both collapsed on the floor.
Jill laid her head on my chest, toying with my chest hair, "Jesse and I never spoke about sex with any of our boyfriends until she met you, she woke me up bragging about you. I was already engaged at the time and I couldn't get her to shut up about it. I thought she was exaggerating. She wasn't."
"Do you need to go to work tomorrow Jack?"
"Yes, tomorrow is the big reveal on my new duty assignment."
"What's that mean."
"Every few years they send me to a different plant, one that needs some help. I've been in Atlanta for three years now so I'm expecting another transfer, the rumor mill has me going to Seattle."
"Doesn't it suck on a personal level, no roots, no long term relationships?"
"Well, they pay me well, provide me with great places to live and all my meals and expenses are covered so most of my salary goes in the bank. There was a woman in Chicago I had hopes for but she refused to move to Atlanta."
"Is that the only reason you're still single?"
"Maybe, I was gun shy after your sister so that didn't help."
"And what about me Jack, do I get a chance to go to Seattle."
"I would love to discuss that with you when we have clothes on. But could I ask you a favor, there's a big dinner tomorrow night, an end of meeting dinner. Normally I'm the only solo guy there and I would love to have a date."
Jill sat up, "Jack I already told you I have nothing nice to wear and this sounds very formal."
"I know, I wasn't going to ask but I hate being the only solo guy there. The guy who couldn't get a date."
"Are you trying to make me feel sorry for you?"
"If it works, why not."
"But I still have nothing to wear."
"What if I gave you my credit card and you can buy whatever you need."
"The way to a man's heart is food, the way to a woman's is either jewelry or clothes, but I couldn't accept."
"Jill, do you know how much I was considering Jesse's request to get back together. You saved me, probably saved my life. I owe you more than you can imagine, I get to pay back that debt and have a beautiful woman on my arm at the dinner."
"I'll sleep on it Jack, can you send me some pictures from last year so I have an idea what I'm supposed to be shopping for."
I had to leave so I left her my Black card. The next morning my boss was teasing me if I was going to be solo again tonight. He was shocked when I told him I had a date and would need to leave a little early to pick her up. Nonsense he said, I'll have my limo pick her up. I gave him Jill's address and warned her about the limo.
Jill looked like a million dollars when she came in, I kissed her and told her she looked beautiful. The dress showed a lot of cleavage and a slit revealed an awful lot of Jill's leg.
"I hope you like it, it was one of the less expensive dresses in the store and cost more than everything else I own and that was before the shoes, lingerie and purse the woman insisted I buy. Plus getting my hair, nails and makeup done. And the limo, it was a block long. I couldn't believe it when the limo driver was knocking on my door, I said 'if you tell me your name is James, I'll shit myself.' So, he says, 'it's James but please don't shit yourself or we'll be late.' When we got in the car he told me it was really Charles."
Jill turned a bunch of heads as we entered the ballroom. My boss's wife snatched Jill's arm right away, 'Jack said you were beautiful but you are so much more.' And off they went.
My boss took my arm, he knew all about Jesse, "Jack why do I feel like I met your date before?"
"That is Jesse's sister Jill, we've been friends a long time and I talked her into being my date tonight so I didn't have to go stag again."
"I sense there's more to this story but we can discuss that at a later time, I am also certain I saw Jesse with you when we were here last year. But we should go gather our dates, it's almost time for dinner."
We sat down for dinner, Jill was very nervous, "I should have said no Jack, I am way out of my league here."
"Jill, everyone here is human in every way, they eat, piss and shit like all of us. But you are the most beautiful woman here. Relax and be you, the food will knock your socks off."
Dinner was pleasant and on the way to my room, Jill told me how welcoming my boss's wife was and knew right away she was related to Jesse.
But once in our room, I pulled Jill into my arms, god he was gorgeous. We ended it up in front of a hallway mirror and I turned Jill to face the mirror, nibbling on her neck, my hand slid up and cupped her breasts.
I gave her a gentle push on her shoulders, Jill dropped to her knees, pulled out my cock and started sucking. She was good but I had to pull her off my cock before I came.
We went into the bedroom, I undid the zipper on her dress and she let it fall to the floor revealing a half cup bra and a matching panty. I pushed her back on the bed, slid the panties off and started licking her lips. Jill was pinching her nipples. There was a thought in my head comparing the way Jill and Jesse tasted, there wasn't much difference I thought. Jill came twice and I wanted to be inside her. As I was working my cock in I noticed Jill was crying or at least had tears in her eyes.
"What's the matter Jill, did I hurt you?"
Jill rolled over, facing away from me. She was sobbing now.
"I'm sorry Jack, I really wanted the evening to be perfect for you but I'm really sore down there from last night. I can't believe I'm disappointing you after such a wonderful evening and that beautiful dress. Maybe in a few minutes we can try again."
"Stop that talk Jill, what if I didn't realize I was hurting you, would you have continued to let me fuck you?"
"Yes Jack, I wanted you inside me one more time before you have to leave tomorrow."
I pulled her to me and kissed her as her sobbing died down.
"Jill, don't ever let me hurt you like that again."
"Ok Jack, I'm sorry. I can suck you off instead."
"What if I said I just want to hold you, to feel your nakedness lying against me as we sleep."
"Are you sure you're not disappointed in me?"
"Jill you're beautiful and tonight in that dress you were absolutely stunning. Am I disappointed that I missed a chance to make love to you, yes. But I'm more disappointed you were going to allow me to physically hurt you and not in a fun way. We'll have other opportunities."
"When Jack, you're leaving tomorrow and I doubt if that monster your carrying isn't going to hurt any less before you leave."
"I guess we'll have to plan another get together."
"Do you expect me to fly to Atlanta like my sister did, to take her place and let you fuck me in the same bed you fucked her. I'm sorry, that came out harsher than I wanted."
"I'm leaving Atlanta in two weeks and heading to Seattle. Have you thought about coming with me?"
"Can we discuss this in the morning over breakfast."
I said okay and we were asleep in minutes.
We showered together in the morning, we were barely wet when Jill dropped to her knees and sucked me off. It didn't take me long to come. Jill held her mouth open, showing me, it was full of my come and swallowed.
Over breakfast, Jill said, "Jack, my world has grown very small and there's nothing for me here. Somehow my sister knows I ratted her out to you so that relationship is over. My boys barely speak to me. I have a few friends at the school where I teach but they're married. You've seen my house, with what I make I can barely keep the mortgage paid and the lights on. The few pieces of furniture I have left are about to crumble and every appliance is on its last leg."
"You whisking me off to Seattle is like a dream ending to a Cinderella like fairy tale. I don't know if my old life is sustainable but what happens if I'm in Seattle and you tire of me. How do I come back from that. I'm lonely here but at least I have a roof over my head."
"Those are good points Jill, I can offer you my promise that I would never leave you stranded but they could be empty. I don't think we know each other well enough right now to talk about marriage. I don't like the way it sounds but I could offer you money, like an insurance policy, if things go south between us for any reason, you'll have money in the bank to escape Seattle or wherever we end up."
"That almost sounds like I'm your prostitute Jack and that's not what I want to be."
"And I don't want a prostitute Jill, I want somebody to love, somebody to come home to and is happy to see me. What I don't want is for you to ever feel you're trapped. Neither one of us would want that."
"Let me think about it okay? I know I'm going to go home and look at me exhausted furniture and call myself an idiot for not saying yes right now. I would have to give notice at the school I'm teaching at, put the house up for sale so I can escape the mortgage, apply to jobs in Seattle and get all my books and clothes sent over. I'm sure there's a thousand other things."
"Keep the house Jill, I'll pay off the mortgage, then you'll at least have a place to escape to. Maybe you can rent it out. The company hires professional movers when they move me, they make it almost painless. I'll arrange to have them move you also. All you have to do is tell them what to pack and they'll box it up for you and when you get to Seattle, you tell them where you want it."
"Can I let you know tonight Jack?"
"Of course Jill. I should warn you, I never know what I'm walking into and the first few weeks are usually very busy for me. You'll be alone a lot during those weeks."
"I'm alone all the time now Jack. It will not be any different. At least I won't have to worry about the kitchen table collapsing on me. I don't want to be a leach but there will be a gap before I can find a job."
"Please don't worry about money Jill."
"Are you trying to make me a kept woman Jack," she said with a smile.
"I don't want to make you into anything, but I look forward to developing our relationship and I don't want something like money standing in the way."
I dropped Jill off at her house, I was under a time crunch so it was a quick kiss goodbye and her promise to call me that night and let me know her decision. Jill came running after me as I was backing out so she could give me back my Black card. I told her to keep it.
Jill did come to Seattle, first for a weekend and then she moved in a month after the Hilton. We settled into a comfortable life, Jill got a job reading to kids at one of the big bookstores. I had put ten grand into a checking account in her name as an escape fund.
There was always a thought in my head that Jill was here more for my money than for me. It was never spoken out loud but Jill refused to accept any extravagant gifts from me. It was a challenge to get her to buy a nice dress when we had to attend a formal function. She refused any jewelry I bought her. After some serious discussions, she would accept the vacations I planned.
It was a few months after she moved in that she told me she loved me as she fell asleep. Two weeks later I said the same to her. It was still hard for me to say that to someone but Jill seemed to relax after that.
Jill and I had been living together for almost two years and she still had the black card but usually only used it for groceries. I knew she was using the escape fund for the property taxes on the house. I rarely looked at either the card or the escape fund and the one time I looked at the escape fund I saw some unusual transactions, Jill just happened to be walking by so I asked her about them. I was more concerned with fraud than anything else.
Jill sat down across from me looking like a scared kitten
"I am sorry Jack, I know I should have told you but I was afraid you would be angry. Jesse moved into my old house after Joe threw her out. I think he found out she was cheating on him. I think I told you before that all of my appliances were on their last legs before I moved here. They have been dying one after another. I used the escape fund to replace them. I'm sorry I didn't tell you, I'm living in luxury and couldn't let my sister freeze to death."
She was crying as I came around the table and hugged her. "Jill, I am not angry about the money, I am concerned that you didn't feel you could tell me. Jesse isn't my favorite person but I wouldn't want her to freeze to death either."
"I'm sorry Jack, there's so much history between you and Jesse, I wouldn't blame you for wanting to let her freeze. Some of it is the guilt trips she puts me on, she sees us on Facebook cruising the Med or flying off in the company jet to spend a long weekend in the Caribbean and reminds me that it could have been her if I hadn't interfered."
"But Jill, she was the one who lied about being celibate for six years and I did have an STI. Jesse would have been informed that I had an STI and listed her as a my only recent sex partner. If you hadn't informed me of Jesse's lies I still would have figured it out."
"I love you Jesse and I want you to feel comfortable telling me anything."
We sat there staring at each other, there was something else on her mind.
"What is your biggest fear Jill," I asked.
"That you would tire of me and discard me, or a fight between us that escalated to the same end point. I know I have the escape fund but it would be hard to return to that life. What's your biggest fear Jack?"
"That you're only here for the money or it was the money that got you here."
"Jack, never in my life have I wanted to slap a man as much as I want to right now, I can see how you could think that, but to think that of me is so fucking insulting. You may have just started our first fight."
"Slow down Jill, we started talking about being comfortable telling each other anything, I never said it was a rational fear and I assumed that I might discard you was not a rational fear. Or I could respond in kind and say, 'to think that of me is so fucking insulting.'"
"So, how do we make this better Jill?"
"What if I told you I wanted to be your wife? And I wanted to sign a prenup like you had with Jesse. We both address our irrational fears."
"I don't know about the prenup thing, you're father drove that when I wanted to marry Jesse. As far as marriage, you would have to let me buy you some expensive jewelry first, like an engagement ring and maybe some matching earrings and necklace, and of course a matching tennis bracelet."
"Does that mean you'll marry me Jack?"
"Of course but let's go out to dinner to a really nice restaurant to discuss what that would look like."
Jill turned a lot of heads as we entered the restaurant. God he was so beautiful. After dinner and before desert, I dropped to my knee and offered her the engagement ring I bought months earlier. She pulled me into her arms whispering yes. We exchanged 'I Love You and kisses. I sat back in my chair, Jill took a picture of the ring and posted it on Facebook.
The maître d came over to us, "Excuse me sir, but I have been informed that you have just asked this beautiful woman to marry you and she said yes."
I nodded, "Congratulations to both of you," he said as he snapped his fingers and two waiters came over with a very expensive bottle of champagne and flutes.
"Compliments of one of our guest who wishes to remain anonymous."
"Please tell him we said thank you."
"He knows," said the maître d as he bowed and stepped away.
When we got home, Jill and I made gentle love, it was perfect end of the day.
Looking at our phones over morning coffee I was surprised that number of congratulations we received didn't break Facebook. All Jill posted was a picture of the ring and a caption that read, "I said yes!"
"You know Jesse is going to see that."
"I hope so, that's why I posted it, well not the only reason. Jesse has been guilting me into shit since I was in diapers I think. I'm done with that."
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