The Cheater - Cover

The Cheater

Copyright© 2020 by Pettybox

Chapter 7: Janice

Erotica Sex Story: Chapter 7: Janice - Alex finds his desires have not waned as he hit his 50's, but his wife feels old and dried up. He dealt with that for a long time until he gave into a sexual situation that fell in his lap. He still loves his wife, but has no regrets of the affair, and opens the door to other opportunities. He begins a journey to satisfy his wants and needs while still keeping his love for his wife alive, even when his conscience tells him to beware..

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Consensual   TransGender   Fiction   Cheating   Anal Sex   Analingus   Masturbation   Oral Sex  

I had cheated 4 times now and my guilt was little, if at all. If I had any thoughts that actual feelings were involved, I took solace in the fact I still ran into or worked directly with all those partners and little or nothing was said or implied. It was as if none of it happened. Man, did I love 21st Century women and how they dealt with their own pleasures.

I never considered myself flirtatious, but I never ignored a look my way, a wink, or a smile. I liked playing the game. Once I met my Dory, I never stopped appreciating those things, but never took step #2 in acting on them. Before I fell in love with her I was quite proficient on acting on little flirts, or instigating my own and I did what I consider “quite well” in the ladies department. If I was out in search of an interested party, I can think of but a few times I missed. Not that I bedded down all of them, but at least I had company for the day or night, and a phone number of a prospect. That may sound sexist, but I never had to force or coerce anyone to be with me, if even for a drink, or just a few intimate moments. I don’t think any female I was ever with, in any way, was not aware of what the end game might be, and all knew it was voluntary. Let’s face it, we are all sexual beings, we all enjoy the feeling of being in love, even if it’s just being acted out for the sake of release. I remember a Friday night into Saturday with a little redhead who seemed insatiable. When I finally delivered her back to her dorm Saturday evening I was worn out and she was trying to talk me into sneaking into her place. Fast forward a few weeks and I was at a post football game kegger on her campus. I saw her and was about to make a move her way when I saw she was with someone as she turned and ignored me. A friend told me to stand down, she was engaged to this football dude and he was a little possessive. Now, that situation didn’t happen since she was with me, she was out that night looking for some “strange” on her own, dropping her commitment and her morals for a wild fling. We all have our desires and act on things you don’t think you normally would. Sexual pleasure is a strange and wonderful thing, but it has brought down governments and world leaders. I knew I was playing with fire each time I strayed; no matter how I parsed it in my head.

It was probably 3 months since my last stray. I know I had been to Megan’s Man Cave at least 3 times since our last tryst and she never brought it up, or even flirted. We both remembered the nights we shared and those memories served as our basis of friendship, but never discussed them. It was all good.

Dealing real estate, I knew agents who have told tales of bedding down prospective buyers or sellers who hoped the agent might try extra hard to sell or find their dream house. One fellow, who once sat in our office (Larry Chisholm held the franchise for this national company) had to be let go because one particular lady was screwing the agent every time he showed her a house. It was found out when Larry made a cold call to the number provided and got her husband, who was not aware they were shopping for a new home. She had been shown 4 homes!

Unless I wanted to go back and attempt to talk one of the four women, Erin, Leidee, Lainey, or Meggy, into another round, I felt I had no prospects. I didn’t pursue any of them in the first place and all sort of fell into my lap. The fun had been basically, no chase, and that made things easier to accept, I guess. I figured my time for screwing around was done until Janice walked into our office. I did a double take and apologized, “I’m sorry, you look just like someone I knew from college, how can I help you?”

“Alex, it’s me, Janice, and you still know me.”

I double took again, I knew she was my age but only looked to be 35 or 40, and just as pretty as our college days. We dated for 6 months up until the end of my third year and we hit it off pretty good, until semester ended. I never came back for my last year, and finished nights at Community College. She still looked hot. I remembered feeling her up, fingering her, and her jerking me off a 100 times. Our last night she was going to “try” to put it in her mouth, but other cars came around and it was blowjob interruptus before her lips really sealed on me.

“Holy crap Janice, you still look great! How have you been?”

She proceeded to tell me of a career she had in investments and stock trading. She sounded quite successful and I asked her about husband and kids.

“Oh, I never married. I moved around so much, I never got to meet anyone who interested me that much.” She said quietly.

“You? Any kids?” She asked. “Yes, we have a Son who is a Jesuit Brother. He is estranged from us because of his vows. We only know he is a missionary, based in the Vatican, but usually in other countries. We hear from him at The Holidays. He’s happy and we’ve accepted it, and never talk about it.”

She nodded in acceptance and, I suppose, accepted my “never talk about it” respectfully.

“So why did you look me up?” I wondered.

“I hate to disappoint you, but my being here talking to you is sheer coincidence. I want to settle here, buy a house, instead of condo’s and apartments. Stay in one place. How long have you been in real estate?”

“It’s a sideline, I have investment opportunities I work at, some repping situations. I do quite OK, spreading myself around. One job, day to day, punch in, punch out, was never going to satisfy me. I’ve done well for myself.” I said proudly.

“I knew you married that Doris. When we were going out you said you might have a girl back home. I figured I was just something on the side.” She said snidely.

“Wait Janice, I was interested in Doris, but we didn’t have a relationship of any kind while I was at school. I DID NOT use you, if that was your reason for never answering my calls.” I protested.

“Alex, I went looking for you after I found you weren’t coming back to OS. It was apparent you didn’t miss me like I missed you. That’s 30 years of water under the bridge, our lives went different ways, let’s be friends like we started.” She said wanting to settle it.

We stood silently for a moment and then she dropped her guard a bit and spoke.

“I’ve had a few relationships and I’m not happy with my love life. I even tried women for a while and thought I was happy, but it was just an exciting experiment that blew up on me. I’ve had lots of men ask me to marry, or at least move in, but trust was always an issue. I missed being with someone, but there are ways to satisfy needs.” She said blushing and losing eye contact with me.

Janice was being totally frank with me, who, after thirty years was really a stranger. It was obvious she still felt the bond she and I had back at school, her talk being so personal and frank. We had become pretty fast friends and talked about life extensively. I guess I never knew how much she had cared for me. I wondered if taking her as a client was a good idea.

“Well, what’s past is passed. Let me tell you what I’m looking for and see if you can help me.” She said, quite decidedly, as I nodded.

“I don’t want to be in the city, no apartments, high rise condo’s, or like that. I’m looking for a home, a couple bedrooms, large kitchen, and a yard. I want to be goddam normal. I’m sort of retired, I have 20 really good portfolios I watch and move things around in. That, along with my own stuff, provides me with enough to keep a semi-retirement funded and me happy.”

I stroked my chin and wondered aloud, “What happens as these people die or move on to other investment advisors?”

“I don’t NEED any of them. The sheer volume of my own holdings is the anchor for them.”

“So, only if the market crashes are you in trouble.”

“Technically, but I have enough in things that can’t fail; or if they do the whole country is down the shitter.” She said, obviously annoyed and wanting to move on.

“Don’t get mad because I’m only asking because I could do something like that, and have considered it. I just don’t think I have the hustle, at this point, to look for business.” I apologized.

“My accounts were with other investment firms I worked with and culled for this intention. I had to pay them each a nice bonus. We can discuss this later. Let’s get started with WHY I’m here.” She said impatiently rattled.

I took my “Big Book” and went back to tell Larry I was leaving with a new client.

“Take the “logo van”, it makes us look sharp.” He said tossing me the keys.

The “logo van” was small Ford station wagon type van with our franchise decal all over it, both entire sides, the hood, roof and tail gate. I wasn’t in love with driving it, and usually shunned it, except when taking a client I intended to return with, rather than have them follow me. Since Janice was not familiar with the area, I would take her.

As we gathered things and went out to leave I noticed Janice was still very well taken care of, as she was back in college. She was dressed businesslike, but her shape was obvious, and nice. Of course I knew she was a 55 year old body underneath her clothes, but if it was as preserved as her beautiful face was, wow!

“I have an idea of where we might start, but if you lay the book on your lap and look at the green tabs, those are ideal for Dinks (double income-no kids) and family starters. In this area we are talking 150 to 200K for what you spoke of. If you want to expand on the price limits, we can, and if you want to stay on the low end, just speak up. You know what you like, what you want.”

“No, that’s a good starting spot. For that range they should be 2 bedroom and maybe an office, decent neighborhoods?” She asked.

“Mmm, for the most part, I’m trying to keep the yard factor in there too. As we go uptown you’ll be in the high 100’s and low 2’s. But you’ll have more of a development situation, bigger yards, bigger homes, but many alike; however you’ll have manicured yards, walkways, and boulevards.”

“Look, Alex I can afford a lot more than the parameters I gave you, I just don’t want more house than I need, and I want to be where I can be part of a neighborhood.”

As she spoke my eyes raced over her. I remembered how good her breasts felt in my hand so many years ago. They were perfect handfuls, and felt just delicious in your hand. She loved when I played with them. As she spoke I remembered her voice as she cooed and groaned as I played with those boobs. She was speaking business to me, and all I could think of were the times in my car, or alone in my dorm. I never fucked her, but I fingered her to orgasm so many times, and she jerked me off for each time I fingered her. The last night we were together I had just finished fingering her to ecstasy and she was jerking me off. She was bent over me watching her hand intently as I was encouraging her to take me in her mouth. She lowered her head and I felt her hot breath as her mouth was closing over me. Suddenly a car pulled in beside us, a couple setting out to do what we were, but Janice spooked and sat up, never finishing the hand or blow job. We promised to meet up over the summer, but I never returned to classes and finished by degree at Community College.

“ALEX, are you listening to me? You seem to be in another world.” She shouted.

“Yes, I’m trying to think if there’s any home for you in my head that I might be missing.” I feigned.

Finally we got to the green tabbed home I wanted to start with. It was vacant with a realtors lock box on the door. We sat in the car as I fumbled for the skeleton key that opened the box and she seemed to pick up my vibe.

“Do you remember the last time we were in a car together?” She giggled and then looked at me seriously. “If we had a house to hide away in that night, we might be married now.” She said as my mouth dropped open.

“Don’t look so surprised! If I had sucked your dick that night I’m not sure you would have went home for the summer. I know you would have come back in the fall. You pleaded with me for 2 whole weeks for oral, and I was ready to give in to that to convince you to stay. If that didn’t convince you, you could have taken my virginity.”

I sat in stunned silence and tried to swallow everything she just said.

“For God’s sake BREATHE! You don’t believe me? Think about it; think about us at that time.” She shouted.

“Alex, this wasn’t planned. You were the LAST person I thought I might run into today. If I were to think about where I might look for you, it would have been back in Colorado. Right now I know we STILL have a connection.”

“Don’t get any crazy ideas Janice.” I warned her.

“I’m not crazy, and I know I lost you to another woman, and I don’t want to change that. But, I do want to finish something that has haunted me from all those years ago. I barely got a taste of you then, and I’ve never tasted any man since then.” She swore, suddenly the horny student she was then.

“I’m supposed to believe that?” I laughed.

“Believe what you like, but I never felt that way about anyone since you. To me, that’s more personal, more showing of love, than even fucking. I have only been with a few men, ones I felt strongly enough about to sleep with. All of them either left me or cheated on me because of my refusal to do that. When I lived with a woman I had no problem with oral with her, but after 2 years I was just not happy and realized I like men.”

“Janice, you have problems.” I said wanting to end our meeting, our conversation.

Her eyes welled up and she implored me, reaching and taking my hand.

“Is it a problem that I have truly loved only ONE man? Is it a problem that I have given myself to 4 other men who I slept with, lived with, shared life with, in some cases, and never got you out of my head? Don’t you think there was a reason why I walked into that office today? Kismet? Maybe, but probably just dumb luck.”

“Janice, if I ever thought you felt this strongly, I would have pursued you then. But now, I just don’t understand. First off, I’m no prize. I cheat on my wife. She’s turned cold to my advances and has no interest in intimacy. I haven’t sought out the women I’ve been with, they’ve come on to me and I’ve been too needy, and I suppose weak, to turn them down, and I feel no remorse.”

She sat back and looked both ways to check for peering eyes and then pulled her top up, revealing the two perfect breasts I had dreamed of groping again just a few minutes before.

“We can be alone in this house Alex, finish what we started all those years ago, and maybe then I can move on or maybe we can start a regular affair.”

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