The Cheater - Cover

The Cheater

Copyright© 2020 by Pettybox

Chapter 16: The Unexpected

Erotica Sex Story: Chapter 16: The Unexpected - 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 spent almost 3 months making sure I worked on keeping myself clean, not putting myself to be in position to let things happen. Although I never frankly said “I Love You” to Janice, she knew and I knew I certainly meant it in the ways I acted, things I intimated in my words. That bothered me. To me, it was more “cheating” on Dory than any affair I had. The sexual deception was bad and I sluffed it off as nothing, but the implication of my words to Janice weighed on me.

I had been through my account visits and monthly duties 3 times since that night and the thought of being “with” any of my former partners never came up from any of them. Now, I had a new software upgrade to Medical Office, which the developer now called M.O. 9.0. It revamped a few minor details but added some tracking charts for follow ups and drug interaction information. The developer charged me $1000 for the license and suggested a $129.88 install price. Besides my 14 direct local users I had 20 other clients who used the program, so I stood to make 3K on installs and hoped word of mouth would get me more. I hated paying that much for my license, but it was a profitable venture for me anyway.

I had arranged with Esther at Experiat Medical to have time set aside for me for inventory and with June to do the install and a quick primer of the key changes. When I arrived at Experiat June was there with a lawyer type, it seemed, a guy with a briefcase with a smug look on his face. June looked spectacular, dressed to the nines, and made-up as pretty as I had seen her. Her tight skirt accented her figure greatly and her top showed just enough cleavage to show she was all woman. It was right after the visual assessment in my mind that I realized, she was not actually a woman. My mind had actually assessed a man, dressed as a woman. She had apparently had went through all the hormone treatments long ago, and she looked stunning. Whether she had augmented any physical parts of her body or not, by sheer looks, she was a good looking and desirable woman. If any man saw her on the street you would never believe she to be a he.

“Alex,” She said. “I’m glad I caught you before I left. I have your Purchase Order ready. I put the software on the first line so when Esther adds our supplies, you can do it all on one PO.”

“Thanks June, and if you don’t mind me saying, you look ready to take on the world today.”

“It’s not the world I’m taking on it’s the lawsuit you’ve been reading about, we and 3 other medical groups insurance suit. Just a mess, today is our testimony day. Wish us luck.” She said.

“Always, I’m sure you’ll knock it out.” I said with a smile, still shouting to myself, inside my head, “It’s a man!”

It seems there was a drug treatment they, and other clinics and hospitals administered that was fully approved by one particular insurance provider, and then after a side effect caused death in one patient, they pulled the approvals and denied payment, hoping to avoid lawsuit. Though the insurance provider claimed it had the right to back track, the judge on the case was hearing little of their protest. The daily testimonies were sinking the insurance provider deeper and deeper.

Just as June and their lawyer were leaving for court, June called me over.

“Uh Alex, if this goes the way the other firms went, I should be back by noon or 1 o’clock. Be sure you see me before you go, we have something to discuss.”

“Sure, June. Not a problem.” I assured her.

The rest of my morning, installing the software and then doing inventory with Esther went well, with no problems. There was always a little flirting from Esther, she loved bending over from the waist in front of me, and then add a little smile. She really wasn’t baiting a hook, and I really wasn’t fishing.

It got to be 11:45 and I was finishing up and hoping June would return soon so I could see her for some sort of discussion. Just as I checked her desk area to see if she had returned, I got a page for a phone call. I wasn’t accustomed to getting calls there, so I wondered who it might be.

“Hello?” I said.

“Alex, it’s June. It ends up, I’m not going back to the office today, but I do need to see you. I know you had lunches with Leidee and Esther, why don’t you meet me for lunch as well. I live in the Pottertown section, right on Decatur Ave, number 100.”

I was dumb-founded and didn’t know what to say and reading my hesitation she said, “Good then, I look forward to this afternoon, 100 Decatur Avenue, Pottertown section.” Click.

“Holy shit” was all I could think. Did she know, that I knew, she wasn’t, um . . . . . she? I was in freak out stage. The account was too good to just not show up. I had to speak to Leidee.

I went to reception where the woman, who knows I automatically, must see June said. “I’m sorry, June is gone for the day. Can someone else help you?”

“Yes, if I could see Leidee.” I said as she punched a few numbers in her console.

I heard her tell Leidee I wanted to see her.

“Let me show you to her office, once I get coverage.”

A minute later another man showed up so the receptionist could walk me to Leidee’s office.

“Hello Alex, how can I help you?” She said as I entered and closed the door.

“Leidee, I’m sort of in a panic here. Does June know that I know about her, um . . situation?”

“Yes, I thought it only fair. She knows you will be discreet.”

“She wants me to meet her at her place for lunch!” I told her in a panic.

“Oh dear, maybe Esther and my stories made her wish for the same.” She smiled.

“Did you put her up to this?” I said burning mad.

“Alex, I swear to you, I DID NOT! She thinks for herself, and I think she may have been a little envious for the same. You know, a mouth is a mouth, she knows that was only as far we would go.”

“You think I should just go!” I almost shouted to her.

“You’re the one who wanted to play. Now, play.” She said sitting back in her desk looking at me smugly.

“Keep in mind, YOU came on to me, Esther came on to me. I did not initiate either of those situations. I gladly played along, but don’t make it sound like I coerced either of you.” I said, still in a panic.

“SIT!” Leidee demanded, pointing to the chair before her desk, and I complied.

“I’m going to speak of things that no one knows but the 3 of us “girls”. We are 3 great friends, we know we are all attractive and can have most any man we pursue. June dresses down, somewhat, here at work, but she is every bit as feminine as Esther or I. Her situation may seem freaky to many, but Esther and I know otherwise. We have each been with her, not like you think. (in the threesome Esther mentioned?) We swing both ways from time to time and have been with women before, usually in a threesome. Don’t let this talk shock you, you KNOW we are open sexually. Except for the fact she has little balls and a limp dick, she is as sexy a woman as you have ever seen. She won’t want you to reciprocate, she can’t. She can make herself cum, and does not want anyone else to try. She chose her lifestyle and is happy with it. She has never elaborated about what goes on when she is with another of her kind. That is her business, but we do know she likes to be, and perform as, a WOMAN in the ways she can. Except for her sex parts, you will see an incredible woman, great body, tits and ass like a model. I suggest you go and let things happen, remembering, she is a woman and doesn’t want to be treated otherwise. If you go and try to be with her and it doesn’t work for you, she will understand. Two nights ago we had a little get together and we told her about our lunch hours with you and she was visibly flustered. That probably brought this on. She won’t make demands of you, she is not like that. This all I’m going to say.”

I sat for a moment thinking and was calming down, somehow, her words had me see things differently.

“I’m going to go and let things happen at her pace. If I freak out, she won’t hold that against me?” I asked.

“Not the June I know. She knows her situation is not for everyone, and that is why she is so protective of her secret. The fact she has invited you to lunch, and referencing mine and Esther lunch hours, you know what you’re going for. Play along as much as you can, stop when you’re uncomfortable. She’ll understand.” Leidee assured me.

I finished my work at Experiat and said nothing of where I was going to anyone. I suspect Leidee told Esther at one point, but I was convinced they had NOT put her up to this. There simply was no reason why they would.

It was just after the noon hour I drove to the subdivision of Pottertown and easily found 100 Decatur. I pulled in the drive and sat for a minute or two before going to the door.

June answered in a dressing gown, still with her make-up from this morning, I thought at first, but she smelled a little flowery and definitely soapy, as if fresh from the bath or shower. She did look every bit the part of a beautiful woman.

“Good afternoon Alex, I’m so glad you decided to come by. I knew there was a chance you might stand me up, and I would have understood. What does or does not happen here today has no effect on our business relationship. Do you understand that? I do not work that way.”

I just nodded and said, “I understand.”

She showed me to the sofa in her living room and asked me if I wanted a drink, offering me coffee, soda, beer, or drink. I asked if she had a bottle of water, and she brought me one, sitting next to me.

As she sat I couldn’t help but notice through the somewhat sheer gown, her breasts and the darkened aereole and nipples. She did look great and as she spoke I noticed her voice was definitely not manly or forced to sound differently, she spoke softly in a sexy woman voice.

She turned to me on the sofa and we spoke about business at first and slowly the conversation changed to Leidee and Esther. She told of what great friends they were and how they met out many times.

“They look for guys to bring home and if someone should flirt with me, I might carefully choose to leave with them, as long as the ground rules are understood. Obviously I don’t leave with strong sexual guys like you.” She said moving her hand to my arm.

“You can’t be too careful in todays world. I can handle myself, but against a man like you, I might be over powered and that would be fine until my secret is discovered, and then it turns violent. Do you understand?”

“Yes, I do June. It won’t happen like that today. I am aware of the situation and will see what happens.” I said nervously, but she WAS putting me at ease.

She turned and leaned into my space and whispered “Relax” and pressed her lips to mine. Just before her lips met mine I saw the top tie and her gown was undone and I got a full glimpse of one of her breasts and it was perfect.

Our kiss continued and I knew what I had to do once she got things started. If she was a woman, she would enjoy having her breasts handled, I reached up with my left hand and slipping inside her gown I held one of her perfect boobs and felt the nipple react as she swooned in my mouth. At that moment, the inner cheating dog that I was shouted out to me, “This was going to be easy!”

When this story gets more text, you will need to Log In to read it

Close
 

WARNING! ADULT CONTENT...

Storiesonline is for adult entertainment only. By accessing this site you declare that you are of legal age and that you agree with our Terms of Service and Privacy Policy.