July 1987 to March 1998.
Status: Married seven years, one kid (stepdaughter)
Occupation: CatererMeetings: Lost count
Age: 30 (today, 51)
The woman could even make a cheeseburger and fries a gourmet meal. Incredible. Cheri's plan was to specialize in catering business events. She already had some clients lined up and one night she dropped by with some food.
"For you. To thank you. I have my first official event set up for Thursday afternoon. You're a true friend. My husband isn't all that supportive. You are. I can't tell you how grateful I am."
"No big deal. I was glad to help."
"Can I ask you something?"
"Sure."
"Would you like to....uh.....maybe....to this to another level?"
"What?"
"Sleep with me? If not, that's cool."
Honestly, I didn't see that one coming at all. I know I'm usually running any kind of game to get a woman into bed, but that had been put on the shelf. This was all business for me. She was beautiful. She was funny. She was smart. And she was a client, whether I was being paid in money or food.
"Did I screw things up?", she asked.
"No.....but.....you do remember that you're married, don't you?"
"How could I forget? Are you really that surprised?"
"Yes."
"You're attractive...you're nice....and I've been here several times every week. Just to bring you food...just to say hello.....I like you. And I've thought it through. You interested?"
Of course I was. I reallllllllllllllllllly liked Cheri. But to be honest, I was wearing down a bit. I was 24 and starting to get tired of acting like a horny frat boy. How many married women could I fuck without getting a barrel full of buckshot pointed at my nads? How many Ashleys would I date just to get some hot ass? How much skulking around could one person do before it just got old? She knew I wanted her, but wasn't going to push.
She picked up her purse and stood up. "I won't apologize for asking. But I won't be upset if you say no. Take your time. Think about it. And I'll see you tomorrow night on my way home."
And she leaned down, kissed me, and left. Time to call my spiritual adviser.
"Jim, I need advice. Can you come over?"
"Okay. I shall come straight over. Need food?"
"No, I have some here that will make you cry with joy."
"In a few."
About a half hour later, my mentor arrived. I explained the whole thing as he ate Cheri's beef stroganoff.
"Fuck me in the ass, this is great."
"So what do I do?"
"Fuck her. You need me to tell you that?"
"She's a client."
"Not officially. You're working for her for free and she's gorgeous," he said, as he looked at her picture.
Jim hung out for awhile and then headed home. The next day, I called Cheri.
"Hey honey."
"You still coming over tonight?"
"See you at seven."
Soon the end of the day came, and I drove home. I showered, shaved again, and put on a pair of shorts and a t-shirt. And waited. Right at seven, Cheri arrived. She walked past me, put a casserole in the kitchen and walked over and wrapped her arms around me and we started kissing.
It was hot, it was passionate, and long overdue. I wished we had started this weeks ago once we were kissing. She grabbed my hand and said, "C'mon. Let's go to the bedroom."
We walked in and she stripped out of her blouse and skirt. I pulled off my shorts and shirt and reached around her and unhooked her bra. The straps slid down her arms and she let it fall to the floor.
"Yes?"
"Yes."
She leaned down and pulled off her panties and laid down on her back. I crawled up between her legs and spread her lips with my fingers and exposed her clit. She groaned softly and I started licking and sucking her clit. I took my time. There was no rush and I was enjoying how she tasted. I worked deliberately and worked her slowly toward an orgasm. Neither one of us were in a hurry; we just wanted to enjoy being together.
After about ten minutes of eating her out, Cheri moaned softly and said, "I'm cumming, honey...." and tensed up and came. I rested my head on her leg for a minute until I heard her say, "Come up here and lay down." I did as she ordered. Cheri then laid her head on my stomach and started slowly sucking my hard cock.
I took my hand and rubbed her back and shoulder. I relaxed and enjoyed having her warm mouth on me for several minutes. Finally, she got up and reached into her purse and pulled out a condom.
She smiled and said, "I thought we'd be using this last night....but tonight's just as good too, right?""Right."
She crawled on the bed and rolled the condom down my cock. She then smiled and said, "Which position would you like?" I told her to stay on her hands and knees. I needed to start off in the doggy position. It wasn't the most romantic sexual position (missionary is, due to the face to face proximity), but I wouldn't last more than thirty seconds in any other.
She smiled. "Whatever you want." I got up behind her and slid in. Incredible. Nice, wet, and warm. And she laid her head on the bed, so there she was: gorgeous, wonderful woman with her ass in the air, her eyes shut, and a smile on her face. I was able to go in this position for five or so minutes. I alternated between sliding in and out and grinding my hips into hers.
Luckily, I was able to make her cum before I reached the point of no return. And I was really close when I heard her moan and cum. You know that little tingling you get before you shoot? I felt it and was able to pull out. I had her lay on her back.
"You need to cum, honey."
"Not yet."
Palm Pilot time. I got up and put some lube on my hand. Cheri was extremely wet at this point, but she also had a very hairy pussy. I love hairy pussies, but they present a bit of a challenge for the Pilot. They don't get as slick as shaved ones. So I went with the lube just to be safe. I started by fingering her clit and getting it hard. I could feel her tense a bit when it got too sensitive so I moved away.
"Sorry, baby."
"No, no....keep going....it's okay."
I kept some pressure on her clit with the palm of my hand and concentrated on her lips and fingering her pussy. After several minutes, she gripped my shoulder and squeezed hard and yelled out, "OH FUCK!", and came. She pulled me on top of her and I slid in again.
30 seconds later, I groaned and came hard. I guess that you can only delay the inevitable for so long. As I was cumming, I buried my head in her shoulder and heard her say, "Yeahhhh...that's it honey.....that's it...."
I pulled out and took my condom off and tossed it away. Cheri pulled me back onto her and we started kissing again. "As good as I thought it would be...better....." I laid on her and we kept kissing. My cock was resting on her pussy and started getting hard after only a few minutes (hey, I was only 24, the age of never-ending erections) and as we kissed, I started grinding it gently against her.
This had an immediate reaction. "Oh....yeah, that feels good....." So I kept doing it. She wrapped her legs around mine, I propped myself up on my arms, and kept sliding my cock up and down her lips. A few minutes later, she reached up and pulled my head down and kissed me as she came.
She reached over to the nightstand and unwrapped a condom. I took it and rolled it on and started fucking her in the missionary position for several minutes. She didn't cum, but was enjoying it quite a bit. We started kissing again as I slid in and out of her. Finally, I pulled out and had her roll onto her left side.
I got behind her and got on my left side and lifted up her right leg. She held it up and I slid into her again. Cherie then brought her leg down and I started fucking her in the spoon position. Spoon fucking is totally underrated. I reached around and started playing with her clit as I pumped her repeatedly.
Finally, I heard her say, "Cumming, honey....." and she groaned, tensed up, and relaxed again.
"C'mon...your turn......when you cum, cum on me."
That did it. I pulled out, took off the condom, and shot my load all over her side and stomach. I fell onto my back and Cheri snuggled up next to me. We kissed some more and then I put my arm around her and pulled her tight.
"That was......so nice...."
"Incredible....."
"I want to keep seeing you. I like this. I like you."
"I like you, too. A lot."
We talked for awhile. Cheri only had a few requests. She definitely needed discretion. And she emphasized that she wouldn't be able to leave her husband. I had already figured this out. Cheri had a stepdaughter named Ellen, who was nine years old.
Ellen was her husband's daughter from his first marriage, and her birth mother was no longer in the picture, having taken off when she was only two. Cheri loved her and was the only mom Ellen ever knew. So she was determined to stay.
Finally, Cheri looked at the time.
"Shit. Gotta go. Love you."
"You too."
"See you on Thursday, okay?"
"Okay."
I was happy that she didn't want to meet the next day. I had a date with Shay, another married lady. But a pattern of Cheri twice a week or so and the assorted married female here and there was a winning formula in my book. Cheri took a quick shower and went home.
I showered, had my dinner and passed out for a bit. I then worked on doing some rudimentary marketing of my freelance services to some of the local attorneys (and by rudimentary, I mean sending out writing samples, my resume, references, and a listing of what I could do for them).
Before I went to bed, the phone rang.
"Hey."
"Hey."
"I'm thinking of you. Wanted to thank you."
"Me too. I miss you."
"Me too. Until Thursday...."
The next evening, Shay and I tore it up. I only saw her a few times. Shay was nice, but not somebody I wanted to have a long-term thing with, especially with Maria and Cheri handling my needs. Shay was great in bed though and will be my next entry.
Cheri and I continued to see each other over the next several months. The assignment I was on when I met her ended, and I started getting calls for freelance work in addition to several short-term assignments from my legal staffing agency. I was making some excellent money and enjoying my life quite a bit. I had no bills, a great apartment, great friends, lots of married women who wanted to fuck, the time to fuck them, and Cheri on top of it.
I could take off and spend the day with Jim drinking at Lake Elsinore (one time, we picked up two married women and banged them right on the beach). Life was good. It was incredibly self-indulgent, but good. Great, in fact. But there was one little problem: I was totally in love with Cheri. It sucked. The one woman I wanted to get serious about I had no chance of getting for my own.
Cheri confessed that she felt the same way. And it didn't help our relationship. Eventually, every time we got together, the fact that this could only be an affair stayed in our minds. In early December, she came over and we talked for awhile and finally called it quits. Well, for awhile at least.
All were fairly short-term hook ups. I met them by placing and answering ads in local fuck rags as well as the local paper, The Daily Bulletin (although my ads there were worded quite a bit differently than in the fuck rags). I always provided and required proof of clean health and always used condoms. I also didn't meet up with heavily experienced people. I had no use for hard-core swingers. I wanted women who had either never cheated or had only cheated once or twice.
It was easy as picking apples from a tree. There were plenty of ads to choose from and my ads generated quite a few responses. There were a lot of lonely wives in the area who wanted attention.
My total spiral in debauchery came to an end in the middle of August. I was fucking a married lady in her bedroom when her husband got home. I heard the door, pulled out, grabbed my clothes and bolted out the window. There's something about a screaming six foot, five inch guy chasing you through backyards and over fences until you put enough distance between you and him that makes you wonder if you're making the right choices.
Run naked through a backyard, through your clothes over a fence......run through another one.....clothes over the fence....etc.... Luckily, I was faster and a lot more nimble than the enraged husband. A nice head start didn't hurt either. Man, that guy was pissed. So was I. I forgot to grab my shoes on my way out. That was an eighty-dollar pair of Nunn Bush shoes I left behind. I still remember his loving words to me: "You motherfucker, I'm going to kick your bitch ass and beat you down like a dog, you piece of crap!"
Good thing the only info he had for me was a fake last name, an unlisted number (which I changed the next day) and a P.O. box for a mailing address.
Heh.
During this time, I knew that Cheri missed me as much as I missed her. A couple of times each week, a box of food mysteriously appeared on my doorstep. After my quick tour of that neighborhood's backyards, I decided to take some time off from having illicit sex (or any other kind of sex) with married women. Like the old saying goes, a good scare is better than good advice any day of the week.
A few weeks of abstinence was needed. But all bad things come to an end. One day in September, I heard a knock on the door. Still fearful of the large man who chased me, I made sure to check who it was through the peephole. I liked who I saw. I opened the door and Cheri walked in.
Without saying a word, she took some food and put it on my kitchen counter and walked over and grabbed my hand and led me to the bedroom. And we spent two hours fucking like crazy, making up for our eight-month drought.
Occupation: CatererMeetings: Lost count
Age: 30 (today, 51)
Cheri and I ran hot and cold and had several on-again, off-again periods. We broke up and got back together several times over those years. But I'm getting ahead of myself. This is an entry covering a long period of time, so I'm going to break it down into dates.
I liked this girl. And we chatted as she cleaned up. She was married and hoping to start her own catering service. Knowing a potential client when I saw one, I offered her my services.
I told her I would help her with the legal filings and forms, as well as related things like insurance and financing, etc. and that I'd do it just for a good reference. Remember, I hadn't been doing much freelance paralegal work at that point. So I was happy to bite the bullet so I could start a client base.
I remember her smile. "Wow. Nice...but I really wouldn't feel right taking advantage like that...." "Don't worry about it. I want to."
We kept chatting until the staff had finished cleaning up the kitchen and food serving areas. She smiled and said, "Well....I gotta take the van back in. Uh....really nice meeting you."
"You too." "So...I'll be calling you soon."
"Cool."
"Yeah," she laughed, "Cool."
I watched her walk away. I really wanted to try and get her into bed. Even if I hadn't been into married women (literally), I would've wanted her. But she was going to be a client.....and Jim had drummed the dangers of mixing business with pleasure. And at 24....I really needed to start a career. Girls I could get. A career was what I needed to focus on. And besides, I had already mixed business with pleasure a few hours earlier with Maria.
So I headed home and dealt with the mess my then-girlfriend, Ashley, had created (again, Maria entry) and got on with my life. Besides, the next day I had a date with a lovely married neighbor named Candace. A couple of weeks later, I still hadn't heard from Cheri.
Regardless, I was still hoping to do some work for her. I was still on my first signment for a legal temp agency, breaking down depositions for a large, pending civil lawsuit. So that definitely occupied my time (and brought in some nice cash as well).
One Monday, I came home and there was a message on my machine.
"Ryan? This is Cheri--we met at Maria's party--I'm ready for your help! Help me please!" and laughed. "Am I a sole proprietor or a corporation? I look like a person, so sole proprietor.....I'm a cook, not a business woman! Help!" and hung up.
It was easy to see that she had never taken a business class in her life. So I called her back.
"Hello. Is Cheri there?"
June to December, 1987
Cheri was the redheaded caterer that I met at Maria's party. Remember the caterers that I was joking around with when I was piling up the food to take home? Cheri was one of them. She was the one who mentioned that Maria let the staff take whatever food was left over from the party. I liked this girl. And we chatted as she cleaned up. She was married and hoping to start her own catering service. Knowing a potential client when I saw one, I offered her my services.
I told her I would help her with the legal filings and forms, as well as related things like insurance and financing, etc. and that I'd do it just for a good reference. Remember, I hadn't been doing much freelance paralegal work at that point. So I was happy to bite the bullet so I could start a client base.
I remember her smile. "Wow. Nice...but I really wouldn't feel right taking advantage like that...." "Don't worry about it. I want to."
We kept chatting until the staff had finished cleaning up the kitchen and food serving areas. She smiled and said, "Well....I gotta take the van back in. Uh....really nice meeting you."
"You too." "So...I'll be calling you soon."
"Cool."
"Yeah," she laughed, "Cool."
I watched her walk away. I really wanted to try and get her into bed. Even if I hadn't been into married women (literally), I would've wanted her. But she was going to be a client.....and Jim had drummed the dangers of mixing business with pleasure. And at 24....I really needed to start a career. Girls I could get. A career was what I needed to focus on. And besides, I had already mixed business with pleasure a few hours earlier with Maria.
So I headed home and dealt with the mess my then-girlfriend, Ashley, had created (again, Maria entry) and got on with my life. Besides, the next day I had a date with a lovely married neighbor named Candace. A couple of weeks later, I still hadn't heard from Cheri.
Regardless, I was still hoping to do some work for her. I was still on my first signment for a legal temp agency, breaking down depositions for a large, pending civil lawsuit. So that definitely occupied my time (and brought in some nice cash as well).
One Monday, I came home and there was a message on my machine.
"Ryan? This is Cheri--we met at Maria's party--I'm ready for your help! Help me please!" and laughed. "Am I a sole proprietor or a corporation? I look like a person, so sole proprietor.....I'm a cook, not a business woman! Help!" and hung up.
It was easy to see that she had never taken a business class in her life. So I called her back.
"Hello. Is Cheri there?"
A rather brusk voice replied, "Who may I ask is calling?"
"Ryan Callahan. I'm working with Cheri on her catering business."
"Oh, that. Yeah, hold on."
"That"? Dude either didn't want his wife starting her own business or he didn't like strange men help his wife start her own catering business.
"Hey Ryan, thanks for calling back."
"I call at a bad time?"
"No, I'm sorry. I'll explain when we meet."
"For the next few weeks, I can only meet at night or the weekends."
"Ryan Callahan. I'm working with Cheri on her catering business."
"Oh, that. Yeah, hold on."
"That"? Dude either didn't want his wife starting her own business or he didn't like strange men help his wife start her own catering business.
"Hey Ryan, thanks for calling back."
"I call at a bad time?"
"No, I'm sorry. I'll explain when we meet."
"For the next few weeks, I can only meet at night or the weekends."
"Okay....uh....Wednesday night? Is seven okay?"
I heard her husband mutter something in the background. "John, do you mind? Sorry, is that okay?"
"Sure. My place?"
"That's fine."
I gave her directions and we hung up. I tried not to imagine the argument that was taking place between those two. I really didn't want to know. I got home around 6:30 the following Wednesday and was beat. As glamorous as reading depositions sounds (note sarcasm, please), it can get old really fast.
I really wasn't looking forward to going over Cheri's plans for two hours, no matter how cute she was. But I had given her my word..... I quickly showered and changed. And sure enough, at 7:00 on the dot, I heard a knock on my door. I opened it and saw Cheri. "Hi! I brought a little something for you."
Just what I needed: food.
"Just some leftovers I made for dinner. Lasagna, some garlic bread."
"Wow. Thank you."
"I know a caterer bringing you lasagna is a bit of a cliche, but trust me, you'll like it." she laughed.
"Hey, I didn't say anything....besides, it looks great."
"Well, have some. Trust me, it ain't that frozen crap you can buy at the store," she smiled.
She was right. This was so good, my tongue nearly did back flips. And for good reason. The woman was a trained chef. She had graduated from The Culinary Institute of America several years earlier and had worked as cook in a couple of 4 star restaurants in Manhattan.
"So what brought you out here?"
"I was working as a sous chef at ***** when I met my husband at a party a few years ago. We dated and he proposed. Then he got a job out here--he's originally from San Diego--and I told him to take it. I was burned out on restaurant life. The hours, all that. I loved cooking, but just got tired of psychotic chefs yelling at everybody."
"Sounds stressful. But...you graduated from the CIA....not to sound snobby, but why work as a server for a caterer."
"No, that's okay. I took the job because it allows me to split my time serving a cooking. It's less stressful and honestly, I think there's more creativity involved. And it actually pays pretty well--I've been able to save up the money to start this business."
Made sense, especially the stress thing. It's one of the reasons I decided not to go to law school. As a paralegal, I had more flexibility in accepting assignments and taking jobs, and unlike law school graduates, I would never be at a loss for work. In the 80's, law schools were graduating lawyers at record numbers. There were a lot of law school graduates looking for any kind of law-related work.
Me? I could do a lot of the same work at lower rates. Who'd YOU hire? Anyway, I cleared up the whole sole proprietor/corporation question for Cheri, explaining the differences between the two (she actually had a general idea, but I broke it down even further for her), as well as insurance and accounting options (I recommended the accountant Jim used for his own business), and soon Cheri was on her way home.
Over the next couple of weeks, Cheri and I got all the necessary forms for her business license. I reviewed her lease on a small office/kitchen setup in Claremont and soon she was set to go. And every time she came over, I was fed a great meal.
I heard her husband mutter something in the background. "John, do you mind? Sorry, is that okay?"
"Sure. My place?"
"That's fine."
I gave her directions and we hung up. I tried not to imagine the argument that was taking place between those two. I really didn't want to know. I got home around 6:30 the following Wednesday and was beat. As glamorous as reading depositions sounds (note sarcasm, please), it can get old really fast.
I really wasn't looking forward to going over Cheri's plans for two hours, no matter how cute she was. But I had given her my word..... I quickly showered and changed. And sure enough, at 7:00 on the dot, I heard a knock on my door. I opened it and saw Cheri. "Hi! I brought a little something for you."
Just what I needed: food.
"Just some leftovers I made for dinner. Lasagna, some garlic bread."
"Wow. Thank you."
"I know a caterer bringing you lasagna is a bit of a cliche, but trust me, you'll like it." she laughed.
"Hey, I didn't say anything....besides, it looks great."
"Well, have some. Trust me, it ain't that frozen crap you can buy at the store," she smiled.
She was right. This was so good, my tongue nearly did back flips. And for good reason. The woman was a trained chef. She had graduated from The Culinary Institute of America several years earlier and had worked as cook in a couple of 4 star restaurants in Manhattan.
"So what brought you out here?"
"I was working as a sous chef at ***** when I met my husband at a party a few years ago. We dated and he proposed. Then he got a job out here--he's originally from San Diego--and I told him to take it. I was burned out on restaurant life. The hours, all that. I loved cooking, but just got tired of psychotic chefs yelling at everybody."
"Sounds stressful. But...you graduated from the CIA....not to sound snobby, but why work as a server for a caterer."
"No, that's okay. I took the job because it allows me to split my time serving a cooking. It's less stressful and honestly, I think there's more creativity involved. And it actually pays pretty well--I've been able to save up the money to start this business."
Made sense, especially the stress thing. It's one of the reasons I decided not to go to law school. As a paralegal, I had more flexibility in accepting assignments and taking jobs, and unlike law school graduates, I would never be at a loss for work. In the 80's, law schools were graduating lawyers at record numbers. There were a lot of law school graduates looking for any kind of law-related work.
Me? I could do a lot of the same work at lower rates. Who'd YOU hire? Anyway, I cleared up the whole sole proprietor/corporation question for Cheri, explaining the differences between the two (she actually had a general idea, but I broke it down even further for her), as well as insurance and accounting options (I recommended the accountant Jim used for his own business), and soon Cheri was on her way home.
Over the next couple of weeks, Cheri and I got all the necessary forms for her business license. I reviewed her lease on a small office/kitchen setup in Claremont and soon she was set to go. And every time she came over, I was fed a great meal.
The woman could even make a cheeseburger and fries a gourmet meal. Incredible. Cheri's plan was to specialize in catering business events. She already had some clients lined up and one night she dropped by with some food.
"For you. To thank you. I have my first official event set up for Thursday afternoon. You're a true friend. My husband isn't all that supportive. You are. I can't tell you how grateful I am."
"No big deal. I was glad to help."
"Can I ask you something?"
"Sure."
"Would you like to....uh.....maybe....to this to another level?"
"What?"
"Sleep with me? If not, that's cool."
Honestly, I didn't see that one coming at all. I know I'm usually running any kind of game to get a woman into bed, but that had been put on the shelf. This was all business for me. She was beautiful. She was funny. She was smart. And she was a client, whether I was being paid in money or food.
"Did I screw things up?", she asked.
"No.....but.....you do remember that you're married, don't you?"
"How could I forget? Are you really that surprised?"
"Yes."
"You're attractive...you're nice....and I've been here several times every week. Just to bring you food...just to say hello.....I like you. And I've thought it through. You interested?"
Of course I was. I reallllllllllllllllllly liked Cheri. But to be honest, I was wearing down a bit. I was 24 and starting to get tired of acting like a horny frat boy. How many married women could I fuck without getting a barrel full of buckshot pointed at my nads? How many Ashleys would I date just to get some hot ass? How much skulking around could one person do before it just got old? She knew I wanted her, but wasn't going to push.
She picked up her purse and stood up. "I won't apologize for asking. But I won't be upset if you say no. Take your time. Think about it. And I'll see you tomorrow night on my way home."
And she leaned down, kissed me, and left. Time to call my spiritual adviser.
"Jim, I need advice. Can you come over?"
"Okay. I shall come straight over. Need food?"
"No, I have some here that will make you cry with joy."
"In a few."
About a half hour later, my mentor arrived. I explained the whole thing as he ate Cheri's beef stroganoff.
"Fuck me in the ass, this is great."
"So what do I do?"
"Fuck her. You need me to tell you that?"
"She's a client."
"Not officially. You're working for her for free and she's gorgeous," he said, as he looked at her picture.
Jim hung out for awhile and then headed home. The next day, I called Cheri.
"Hey honey."
"You still coming over tonight?"
"See you at seven."
Soon the end of the day came, and I drove home. I showered, shaved again, and put on a pair of shorts and a t-shirt. And waited. Right at seven, Cheri arrived. She walked past me, put a casserole in the kitchen and walked over and wrapped her arms around me and we started kissing.
It was hot, it was passionate, and long overdue. I wished we had started this weeks ago once we were kissing. She grabbed my hand and said, "C'mon. Let's go to the bedroom."
We walked in and she stripped out of her blouse and skirt. I pulled off my shorts and shirt and reached around her and unhooked her bra. The straps slid down her arms and she let it fall to the floor.
"Yes?"
"Yes."
She leaned down and pulled off her panties and laid down on her back. I crawled up between her legs and spread her lips with my fingers and exposed her clit. She groaned softly and I started licking and sucking her clit. I took my time. There was no rush and I was enjoying how she tasted. I worked deliberately and worked her slowly toward an orgasm. Neither one of us were in a hurry; we just wanted to enjoy being together.
After about ten minutes of eating her out, Cheri moaned softly and said, "I'm cumming, honey...." and tensed up and came. I rested my head on her leg for a minute until I heard her say, "Come up here and lay down." I did as she ordered. Cheri then laid her head on my stomach and started slowly sucking my hard cock.
I took my hand and rubbed her back and shoulder. I relaxed and enjoyed having her warm mouth on me for several minutes. Finally, she got up and reached into her purse and pulled out a condom.
She smiled and said, "I thought we'd be using this last night....but tonight's just as good too, right?""Right."
She crawled on the bed and rolled the condom down my cock. She then smiled and said, "Which position would you like?" I told her to stay on her hands and knees. I needed to start off in the doggy position. It wasn't the most romantic sexual position (missionary is, due to the face to face proximity), but I wouldn't last more than thirty seconds in any other.
She smiled. "Whatever you want." I got up behind her and slid in. Incredible. Nice, wet, and warm. And she laid her head on the bed, so there she was: gorgeous, wonderful woman with her ass in the air, her eyes shut, and a smile on her face. I was able to go in this position for five or so minutes. I alternated between sliding in and out and grinding my hips into hers.
Luckily, I was able to make her cum before I reached the point of no return. And I was really close when I heard her moan and cum. You know that little tingling you get before you shoot? I felt it and was able to pull out. I had her lay on her back.
"You need to cum, honey."
"Not yet."
Palm Pilot time. I got up and put some lube on my hand. Cheri was extremely wet at this point, but she also had a very hairy pussy. I love hairy pussies, but they present a bit of a challenge for the Pilot. They don't get as slick as shaved ones. So I went with the lube just to be safe. I started by fingering her clit and getting it hard. I could feel her tense a bit when it got too sensitive so I moved away.
"Sorry, baby."
"No, no....keep going....it's okay."
I kept some pressure on her clit with the palm of my hand and concentrated on her lips and fingering her pussy. After several minutes, she gripped my shoulder and squeezed hard and yelled out, "OH FUCK!", and came. She pulled me on top of her and I slid in again.
30 seconds later, I groaned and came hard. I guess that you can only delay the inevitable for so long. As I was cumming, I buried my head in her shoulder and heard her say, "Yeahhhh...that's it honey.....that's it...."
I pulled out and took my condom off and tossed it away. Cheri pulled me back onto her and we started kissing again. "As good as I thought it would be...better....." I laid on her and we kept kissing. My cock was resting on her pussy and started getting hard after only a few minutes (hey, I was only 24, the age of never-ending erections) and as we kissed, I started grinding it gently against her.
This had an immediate reaction. "Oh....yeah, that feels good....." So I kept doing it. She wrapped her legs around mine, I propped myself up on my arms, and kept sliding my cock up and down her lips. A few minutes later, she reached up and pulled my head down and kissed me as she came.
She reached over to the nightstand and unwrapped a condom. I took it and rolled it on and started fucking her in the missionary position for several minutes. She didn't cum, but was enjoying it quite a bit. We started kissing again as I slid in and out of her. Finally, I pulled out and had her roll onto her left side.
Finally, I heard her say, "Cumming, honey....." and she groaned, tensed up, and relaxed again.
"C'mon...your turn......when you cum, cum on me."
That did it. I pulled out, took off the condom, and shot my load all over her side and stomach. I fell onto my back and Cheri snuggled up next to me. We kissed some more and then I put my arm around her and pulled her tight.
"That was......so nice...."
"Incredible....."
"I want to keep seeing you. I like this. I like you."
"I like you, too. A lot."
We talked for awhile. Cheri only had a few requests. She definitely needed discretion. And she emphasized that she wouldn't be able to leave her husband. I had already figured this out. Cheri had a stepdaughter named Ellen, who was nine years old.
Ellen was her husband's daughter from his first marriage, and her birth mother was no longer in the picture, having taken off when she was only two. Cheri loved her and was the only mom Ellen ever knew. So she was determined to stay.
Finally, Cheri looked at the time.
"Shit. Gotta go. Love you."
"You too."
"See you on Thursday, okay?"
"Okay."
I was happy that she didn't want to meet the next day. I had a date with Shay, another married lady. But a pattern of Cheri twice a week or so and the assorted married female here and there was a winning formula in my book. Cheri took a quick shower and went home.
I showered, had my dinner and passed out for a bit. I then worked on doing some rudimentary marketing of my freelance services to some of the local attorneys (and by rudimentary, I mean sending out writing samples, my resume, references, and a listing of what I could do for them).
Before I went to bed, the phone rang.
"Hey."
"Hey."
"I'm thinking of you. Wanted to thank you."
"Me too. I miss you."
"Me too. Until Thursday...."
The next evening, Shay and I tore it up. I only saw her a few times. Shay was nice, but not somebody I wanted to have a long-term thing with, especially with Maria and Cheri handling my needs. Shay was great in bed though and will be my next entry.
Cheri and I continued to see each other over the next several months. The assignment I was on when I met her ended, and I started getting calls for freelance work in addition to several short-term assignments from my legal staffing agency. I was making some excellent money and enjoying my life quite a bit. I had no bills, a great apartment, great friends, lots of married women who wanted to fuck, the time to fuck them, and Cheri on top of it.
I could take off and spend the day with Jim drinking at Lake Elsinore (one time, we picked up two married women and banged them right on the beach). Life was good. It was incredibly self-indulgent, but good. Great, in fact. But there was one little problem: I was totally in love with Cheri. It sucked. The one woman I wanted to get serious about I had no chance of getting for my own.
Cheri confessed that she felt the same way. And it didn't help our relationship. Eventually, every time we got together, the fact that this could only be an affair stayed in our minds. In early December, she came over and we talked for awhile and finally called it quits. Well, for awhile at least.
December 1987 to September 1988
It was tough when Cheri left. The physical part was secondary; it was her I missed and her friendship, smile, and company. So I compensated the only way I knew how. I worked, made a ton of money, and fucked every married woman I could get my hands on, as well as a few single ones. I had no interest in a girlfriend; I just wanted to run up the score. And I did.All were fairly short-term hook ups. I met them by placing and answering ads in local fuck rags as well as the local paper, The Daily Bulletin (although my ads there were worded quite a bit differently than in the fuck rags). I always provided and required proof of clean health and always used condoms. I also didn't meet up with heavily experienced people. I had no use for hard-core swingers. I wanted women who had either never cheated or had only cheated once or twice.
It was easy as picking apples from a tree. There were plenty of ads to choose from and my ads generated quite a few responses. There were a lot of lonely wives in the area who wanted attention.
My total spiral in debauchery came to an end in the middle of August. I was fucking a married lady in her bedroom when her husband got home. I heard the door, pulled out, grabbed my clothes and bolted out the window. There's something about a screaming six foot, five inch guy chasing you through backyards and over fences until you put enough distance between you and him that makes you wonder if you're making the right choices.
Run naked through a backyard, through your clothes over a fence......run through another one.....clothes over the fence....etc.... Luckily, I was faster and a lot more nimble than the enraged husband. A nice head start didn't hurt either. Man, that guy was pissed. So was I. I forgot to grab my shoes on my way out. That was an eighty-dollar pair of Nunn Bush shoes I left behind. I still remember his loving words to me: "You motherfucker, I'm going to kick your bitch ass and beat you down like a dog, you piece of crap!"
Good thing the only info he had for me was a fake last name, an unlisted number (which I changed the next day) and a P.O. box for a mailing address.
Heh.
During this time, I knew that Cheri missed me as much as I missed her. A couple of times each week, a box of food mysteriously appeared on my doorstep. After my quick tour of that neighborhood's backyards, I decided to take some time off from having illicit sex (or any other kind of sex) with married women. Like the old saying goes, a good scare is better than good advice any day of the week.
A few weeks of abstinence was needed. But all bad things come to an end. One day in September, I heard a knock on the door. Still fearful of the large man who chased me, I made sure to check who it was through the peephole. I liked who I saw. I opened the door and Cheri walked in.
Without saying a word, she took some food and put it on my kitchen counter and walked over and grabbed my hand and led me to the bedroom. And we spent two hours fucking like crazy, making up for our eight-month drought.
