The Cheater - Cover

The Cheater

Copyright© 2020 by Pettybox

Chapter 15: Janice, My Friend With Benefits

Erotica Sex Story: Chapter 15: Janice, My Friend With Benefits - 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  

After Esther, I really cooled my jets with the females in my universe. I was teased and propositioned a couple times based on reputation, and never acted on them hoping the ones who pursued me would think the stories were rumor, and I’m sure there were some of those as well.

One afternoon I had just finished showing a property and took my client for a quick lunch at Friendly’s, an ice cream and sandwich shop. As we sat in the booth discussing some details, a couple from a few booths away had my attention. They were sitting on just one side, their backs to me, and appeared to be necking furiously, then breaking, as the male looked around to see if they were being spied on, and then resume face sucking. A waitress interrupted them, probably sent by management, who asked in an indignant voice, “Is that going to be quite all?”

The man stood and handed her cash with the check she must have left earlier, and they quickly left. As they went by the table I was shocked to see, it was Janice!

She reacted to seeing me, looking embarrassed, but said nothing as they rushed out. I couldn’t wait to hear from her, and I knew she would call.

The next morning I was just about to enter one of my medical client facilities when my business cell rang, it was Janice.

Me: Hello hot stuff.

Janice: Funny, that’s what he called me too.

Me: Boyfriend?

Janice: Maybe, uh . . jealous?

Me: Why so catty? I thought we were friends.

Janice: I knew there would be smart-ass remarks.

Me: I’ve said nothing to joke or hurt you. You must have a guilty conscience.

Janice: Mmmmm, yes I do. I’ve never been like that on a first date. We clicked pretty loud.

Me: Is there a second date in sight?

Janice: We’ll see if he calls today.

Me: Is there something he needs to thank you for, and might want more of?

Janice: What are you, my Mother?

Me: You volunteered the information. I just want you to be happy, and be my friend.

Janice: Oh? Do you mean, friend with benefits?

Me: That’s up to you, but if you’re in a relationship, I would do nothing to hurt it.

Janice: Like I did to hurt yours?

Me: You did nothing to hurt my relationship, if anyone did anything, it was me, . . AND, there is nothing wrong with my relationship with my wife. We even had some sex at Christmas.

Janice: I bet you got a mercy fuck, or pity blowjob.

Me: Ouch! that hurts!

Janice: Because it’s true?

Me: Basically . . . yes.

Janice: I was struggling with a broken sprinkler and he stopped to rescue me. He showed me how to fix it and then set the timer as well. I had him come in for a cool drink and he asked me out. He’s nice, and just lives 5 or 6 houses up. He’s a widower; she’s been gone for 5 years.

Me: How did the sprinkler break?

Janice: THAT’S what you ask me? It didn’t retract and I didn’t see it when I ran over it with the mower.

Me: I hope he makes you happy.

Janice: He did, last night, a few times!

Me: Wow, you work fast!

Janice: Once you suck a guy’s dick, I guess they stick around. If I had known that long ago I may have kept a couple of the losers I hooked up with.

Me: Don’t sound so bitter. You’ve only followed your heart.

Janice: Oh, I know, but it worked like magic last night. He stayed all night and rocked my world again this morning. I should thank you for getting me to cum and learning to enjoy it.

Me: You always came with my hands.

Janice: But with a few dozen guys screwing me sore, I never came once. Your fat cock fixed all that.

Me: I was glad to help you. (chuckle)

Janice: I think the difference between you, is that Jared, that’s his name, and all the other losers I laid under, is that I really WANTED to be with you. The others, not so much, it was waiting for some sort of magic to happen, and I would fall uncontrollably in love.

Me: I’m glad you’re happy right now. Let me know how it works out.

Janice: Don’t run away from me! Just talking to you has me all flustered already. Let’s get together. Come over tomorrow?

Me: What if Jared calls and you end up busy tomorrow?

Janice: I’ll keep it open for you.

Me: You may change your tune tomorrow. Call me on this phone before noon, and we’ll talk.

My conversation with Janice had me confused as to her intentions. Did she want to start up with this guy, or just use him for a friend with benefits, as well?

I had a good day writing orders and even took an appointment off Larry’s hands, he double booked. I met a couple at one of our highest priced properties (the reason Larry let it go, we had shown it a dozen times, but it was overpriced) I met two men in their 60’s, dressed to the hilt, and a younger woman with lots of make-up at the property. They did a walk through, took a few photo’s and asked the price. They pow-wowed for a few minutes and contingent of getting permits to shoot a movie on the site, it was sold. They just had to head to City Hall. They were legitimate Hollywood directors and producers.

Late in the afternoon they called and said they got approvals and wanted to meet to give me a cashier’s check for 30 per cent down, and sign a contract for the sale. Never had one done so little to sell a $400K property. I was heading home, floating on the air of the sale when Janice called.

“So, do you want to come over tomorrow? I know it’s your realtor day when you go in for 4 o’clock. Come and see me around noon.” She said anxiously right on top of my hello.

“So Prince Charming didn’t call?” I asked.

“Yes, he did. He came over and he spilled his guts about feeling guilty, like he cheated on his dead wife. A blowjob later he was all fixed up and we’re going out on his boat Friday. He says to pack a change of clothes as we can go down the coast and tie up for the night before coming back. My nosy neighbor Maria came over and told me that he was the catch of the neighborhood and many had tried to get him interested. She wondered what magic I used, hahaha.”

“So, you have no problem seeing me, while you’re seeing him?” I wondered.

“No, I have no commitment to him and he’s free to see who he wants. Two days ago I was a damsel in distress about to call you about a broken sprinkler head. The fact it looked like Old Faithful whenever I tried to test it drew his attention and he stopped to help. A cup of coffee with a lot of talk and a blowjob later we had a date, and after a couple fucks by morning, I had a new friend with benefits. I never used my sexuality like this before and it felt good, knowing I had that charm on my bracelet.” She spouted proudly.

“I guess I don’t understand why you never realized that. Your neighbor Maria wanted to know how you got to the neighborhood catch? Tell her to strip and look in the mirror. Janice, you look 25 or 30 clothed or naked. I’ve been trying to tell you, you have the goods!” I preached.

“Well, you got me out of my sexual shell. Maybe that’s why I want a little refresher. I love you in a way no one might understand. I certainly don’t want you for a steady guy, I’m not jealous of your wife, she can have you, but, we have something special as friends and spirits that we brewed in college. My want for you fucked up my life for a long time. When you fell back in my lap out of the blue, I guess I took it as a sign. We just had to do things to fix what I missed 30 years ago. If you think my reasoning is convoluted, I’m sorry. Your life is more complex than anything I could have ever put up with, but standing on the sidelines, knowing you can please me, teach me in so many ways, makes me glad I’m your friend...........................with benefits.” She finished grinning like a Cheshire knowing he couldn’t see her expression.

“A refresher, huh? I’ll have to check my records and manuals to see what we’ve missed. Maybe a little S&M, I’ll bring some ropes to tie you up.”

“Alex, we’ve done everything, and you even spanked my ass, if you want to call that S&M.”

“There are other things we can do on that end, and you have a nice end. Between your cheeks, where I’ve had a bird’s eye view, you have a pink and pouty little asshole that would just beg to get stretched and filled by my fat cock. Tut Tut, before you protest, it will be a little painful to begin, but I’ve never had a complaint once we were done.”

“Good Lord, what is it with guys and ladies assholes?” She asked as if disgusted.

“It’s just unchartered territory for some, a new way to create an orgasm, and quite satisfying for both, when done correctly.” I espoused.

“Oh, and I’m sure you’re the master?” She smart-alecked.

“No, but I’m willing to learn, (chuckle).”

“Not on me, you won’t.” She said, raising her voice.

“Relax Janice, I’ve never done it before being asked. There’s teasing and pleasing before it happens, and it’s not for everyone. I’ve known some who preferred it over vaginal sex, you can’t get pregnant and if you use a condom, there is no chance of getting a disease from someone.”

“Well, don’t try to talk me into it.” She said with a pout in her voice.

“I never would, it was you who commented that you needed a refresher, but we had done everything. Remember?” I reminded her.

“My words, but that was not my intention.” She admitted.

“I can come over around noon, or a little after. Shower and wait for me in bed. I’ll shower when I get there, leave a towel out.” I requested.

“In bed? Why in bed?” She asked.

“I haven’t seen you totally naked, felt your body next to mine and . . . “

“OK, I got it!” She interrupted, “You want it to be sexy, not slutty.”

“I guess you can put it that way. I’ll see you tomorrow.” I said hanging up.

Having finished my call in the Experiat parking lot I went to reception and asked for June, the manager, as always, so she knew where her people would be. Although I needed Esther, it wasn’t about inventories; it was about a damage claim on a shipment. The carrier had already seen it and was processing a damage check; they just needed me to extend it with actual billing losses.

“Good morning June, can I get Esther for a few minutes to review the damage claim and reorder the items?” I asked as I presented myself at her desk.

“Oh yes, she’s been waiting for you. Here, I’ll give you a new P.O., the old number will never get past receiving. First though, use that desk over there and I’ll get you through to Leidee. She’s working from home today, but she needs to talk to you. You’re listed as a reference on a new hire, well, possible new hire. Sit there; answer the flashing line when it rings.” June prattled on.

I sat, it rang, and I answered.

Me: Good morning Leidee.

Leidee: Hi, Alex. I have an applicant who used you as reference. We’re advertising for a go-fer with a clear license and driving record to shuttle everything from patients, records, pharmaceuticals, and etcetera, between our offices, clients, hospitals and clinics. Must be trustworthy and have knowledge of the area. Her name is Joyce Liptak.

Me: Oh God!

Leidee: That bad?

Me: No she would be good, but you actually sort of know her.

Leidee: I don’t know how.

Me: Your hemp oil delivery lady, she’s also my neighbor. She delivered for her ex-husbands business.

Leidee: Sort of a ditzy hippie chick?

Me: That’s her, but it gets worse. She knows about our lunch date.

Leidee: How? You didn’t tell her!!

Me: NO! She was out front waiting, sorting her deliveries when we pulled up. She saw it was me and watched. She knew what we were up to, you know, in your house for an hour. She confronted me a few weeks later.

Leidee: She threatened to tell your wife?

Me: Not exactly. They are friends, but that was never a threat.

Leidee: Oh my God, you’re fucking HER now!

Me: Not any more, I have things to hold over her head now, we have an understanding.

Leidee: I can’t even call her for an interview, she’ll recognize me.

Me: For sure.

Leidee: Gee, I was going to tell you about a woman here who has hot panties for you, but I guess I better not. Too bad, she was a 2nd runner up Miss America from Washington State, 20 years ago, but she still looks great.

Me: No! Screwing around with customers is going to go off my plate.

Leidee: That’s why I’m always one and done, no messes to clean up later. Too bad, Esther has you on her radar.

Me: Esther? The gal who took your place in purchasing?

Leidee: One in the same.

Me: She was watching your place, taking in mail, watering, when you were gone.

Leidee: On my God, you horny toad, you did her at my place?

Me: Play by play like you and I. YOU do kiss and tell.

Leidee: WE CONFIDE! Women confide.

Me: Sounded like more than that, but neither here nor there, who am I to judge.

Leidee: You can’t keep talking on the phone like this, someone might hear you. Can you meet me at The Golddust sometime so we can talk?

Me: Why The Golddust?

Leidee: Because it’s not my place and I don’t want to give you ideas.

Me: You seduced me, remember? I can’t do it today, I have appointments the rest of the day.

Leidee: They open for coffee and doughnuts from 6:30 til 9:00. It’s mostly to go, but we can get a booth.

Me: see you there tomorrow at 7:30, OK?

Leidee: OK, thanks Alex.

Shit! My life was becoming about getting laid and I was self diagnosing myself as being in denial about getting older. But, the more I thought about it, I still blamed Dory. Why did she feel so cold about intimacy? We HAD a great active sex life and she loved it and was usually the instigator. Should I have her consult a doctor? The way I was going, I was going to get caught, either physically, or in a lie. Then, I stood to lose everything. I really did like the sex though. I felt younger and more alive when I knew that I was desirable, even at my age. I mean, I wasn’t fooling myself; I know half the reason some of these women came on to me was because I was safe. IE: Not bad looking, in good shape, married, NOT looking for a girlfriend, and not one to puppy dog them. I knew, and they knew the reason WHY we got together. The only exception to that was Janice, who would take up with me, probably even marry me, if pressed, but she knew the real me. I suppose Lainey would have me too, but in her case, its security. She wants a man to come home to, and sleep with every night. The only thing she wants is to be kept. Love would be nice, but not necessary.

I made busy the afternoon, for tomorrow I had coffee with Leidee, a lunch appointment with Janice, and the evening at the realty office. All in all, a hectic, satisfying, day on tap.

Dory was a little surprised to see me getting going so early on a Wednesday since I work the Realty office that night, but I just told her “breakfast meeting” with an account and she kissed me goodbye.

The Golddust was a casual lunch and dinner spot that actually became a pretty hot night spot once the dinner crowd moved on. They usually featured a folk singer, or the like, beginning at 9. It always set the mood for some drinks and late night snacking. But mostly the evening hours were for couples, and those who wished to be coupled for the night. It was not unusual to ride by early and see a few cars that were there all night, their owners leaving with a mate the evening before.

Opening for coffee and doughnuts, mostly to go, was a great move by management. They had a cleanup crew there anyway, lights on, A/C or heat going, and only needed one person to keep coffee brewed and lay out the morning delivery from Presto’s Bakery.

Leidee and I walked in together and she motioned to one of the crew, who obviously knew her that she was taking a spot inside. We sat and she got right to the point.

“I hadn’t talked to Esther in a few weeks and I’d only been back from out of state a few days, and YES, we talk about who and what we’ve done. June too, she’s usually in that mix too. Be assured there are no jealousies or any of that stuff. We are 3 women who find themselves in the same boat, middle aged out of bad marriages or bad relationships and we make the best of it all together. We are all careful who we are with and we always know where any of us should be. You became the subject of a late night chat we had and that’s where I got the idea to bring you home and Esther was jealous once I gave her the play by play. You shouldn’t have a problem with that, you got your dick sucked again. I just want you to know that nothing goes beyond the 3 of us. I’m not worried about you; I have lots to hold over your head.”

“You have no need to worry about me anyway. I’m a firm believer in “whatever two people agree to do behind closed doors that doesn’t hurt anyone else, is their business” and I’ve always felt that way.

“Where does June fit into any of this?” I wondered aloud.

As far as attractiveness, June wasn’t as much of the total package like Leidee or Esther, but she was a pretty fair looking woman. Not homely, plain, or ugly in any sense, just not a stone head turner. She rarely wore make-up and that might make the change she needed.

“Let’s begin with Esther’s big mouth. She told you we were in a threesome once, and I respect your comment to her about having your own sins to hide. We trust you to keep things private. Now I’m going to tell you something that should it ever get out, you will lose the account. June has 2 brothers on the Board and can swing a big hammer.”

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