Introducing Denise To Anal Sex
by Master Jonathan
Copyright© 2022 by Master Jonathan
Erotica Sex Story: Denise was an associate with another company whom he had befriended. After a trip back home so she could care for a sick relative, he learns that she hooked up with her old boyfriend while she was there...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Anal Sex Oral Sex .
I met Denise one day while I was delivering some paperwork from my company to hers. Denise worked as a secretary for a company looking to buy a property to expand their operation locally, and I was an agent for the realty company they chose to find the property. Our companies had worked together before, but I hadn’t run across Denise until the one day when our usual courier service was swamped with other deliveries.
This sale her company was working on was time sensitive and very lucrative for both parties, so I decided I would hand carry the paperwork to the company myself. It’s not something I usually do, but like I said this was a special case.
That day I walked into the office expecting to see Margaret, the regular receptionist, who I often chatted and even did a little innocent flirting with. But when I rang the little bell, a new and quite spectacular face emerged from behind a file cabinet. She smoothed out her dress (she had been kneeling to get something out of a bottom file drawer) and approached me.
“Can I help you, Sir?” The sparkle in her kind hazel eyes was only surpassed by her dazzling smile. She was very attractive and it took me a long moment to gather my wits about me to continue our conversation.
“Um, yes, Denise (I read her nametag), I’m from the realty agency your company is working with. These papers need Mr. Andrew’s signature and returned to our office as soon as possible so we can move ahead with the purchase process.”
“Oh okay, I will see that he gets them as soon as he gets back to the office.”
“Thanks. By the way, where is Margaret, the regular receptionist? I kind of expected to see her here.”
“She got transferred to our office in Denver.”
“Oh really? She didn’t mention anything about it to me. She and I had gotten to be good friends.”
“Yeah, I guess it was a spur of the moment thing ... a personal issue, I understand. Anyway, if you and I are going to be seeing each other like this, perhaps we can become friends as well. I’m still kind of new here in town and I could always use a friendly face. The company kind of frowns on fraternization. So I don’t have any real friends here, only business associates, and then only the secretaries and such.”
“I’d like that, Denise. This sale is going to take awhile to come together and our companies will be working together closely until then. Afterward, hopefully, we can continue the relationship.”
“Relationship?”
“I meant our companies! Our two companies relationship!” I blushed, realizing my meaning had been misconstrued.
Denise giggled at my discomfort. “Well, who knows how long our ‘relationship’ might last. But it’s off to a good start!”
I knew right then that this accidental meeting could be the start of something very interesting. I wanted to see if I could push my luck a bit more. “Say, Denise, you said you are new to Springfield, why don’t you let me take you to dinner and maybe show you around a bit? Unless you have someone – a husband or boyfriend or something?”
“No, no husband and only an ex-boyfriend. But I left him back in Bloomington where I’m from.”
“Really! I’m from Terre Haute! We’re practically neighbors!”
“That’s pretty wild! So how about you? I’m assuming your asking me out means you don’t have a special someone either?”
“No, I haven’t had anyone ‘special’ for several years – since college. Just never found anyone that could put up with me I guess.”
“Oh I don’t know ... you don’t seem like the ax-murderer type. And judging from my past, I can put up with just about anything but!”
“Well, this has been fun, Denise, and it was really nice meeting you. But unfortunately, I have to get back to the office. How about I call you tonight and we can discuss that dinner some more? Here’s my business card.” I handed her a card from my shirt pocket.
“That would be fine.” She wrote down her number on the back of one of her companies business cards. “Here’s my number. I hope you do call – I’m sorry, you know my name from my name badge, but I didn’t get yours!”
“Oh! It’s John ... John Davidson. Duh!” I gave myself a mental kick in the pants for my stupidity.
“Well I hope you do call, John Davidson, I am looking forward to talking with you some more. And dinner sounds nice.”
I did call her that night and we talked for a couple hours about home, about our pasts, and about our jobs and living in Springfield. Before we said goodnight, we set up a dinner date for that Friday night. I asked her what kind of foods she liked and found a suitable restaurant for us and made the reservation.
That was about three years ago now and since then we have grown quite fond of each other, even sharing the “L” word more than once. We still haven’t taken the leap of living together quite yet but we have talked about it a little.
Sex with Denise is amazing – she is up for anything fun and with a smoking hot body like hers, that pretty much means no limits! The only thing we hadn’t tried was anal sex – for whatever reason, Denise had a hang-up about that. But with everything else on the table, I could overlook her opposition to anal sex.
Yeah, things were great between Denise and I and we looked to the future with bright promise. That is up until a couple months ago. Our relationship hit a bit of a “speed bump” and we had to take a step back and regroup.
You see, last July, Denise’s mother got sick and Denise took some of her vacation time to go back to Bloomington to see her. Denise had always been very close to her mother and she was getting up there in age so Denise wanted to see her. Since she was expected to make a full recovery, I went ahead and stayed in Springfield and let her go back home by herself. I had some work that I needed to get out anyway, and she would only be gone for a week or so.
Or so the plan was initially. But four or five days after she got there, her mother was better and was released from the hospital and sent home. I got a call from Denise that night and she told me that Mom was home again but that she wanted to spend a few more days there to help her until she was stronger and able to take care of herself. Of course, I agreed, happy that things had worked out so good.
Due to the severity of Mom’s illness, it took her a little longer to get back to where she could look after herself without help. Denise was gone for three weeks and when she got back she told me all about her trip. She told me that while she was there her ex-boyfriend, Tommy Martin, came by.
Apparently, while they were going together he had spent a lot of time at her house and got to know her mother well. So when he heard she was sick, he thought it would be a good way to see Denise again.
She had told me that her family had a swimming pool and when she was younger, she loved swimming in it and lounging around on the deck around it. While she was out soaking up some of the Indiana sun, her ex showed up and they sat out on the deck “just talking” according to her.
I knew that she and Tommy had been pretty close, even talking at one point about marriage. I also knew Denise, she was a very playful and flirtatious woman. I pressed her further on what she and Tommy had been doing and finally, she admitted that one night after having a few drinks (a few too many) she and Tommy began doing a little heavy petting and making out.
Denise and I hadn’t had sex for two or three days before the trip and she had been gone for a couple weeks I guess, so the need was there. She caved and before she knew it, she was kneeling down giving her ex-boyfriend a blowjob on her mother’s deck.
I’d heard enough. I jumped up grabbed her by the arm.
“I’m glad that your mother is better and is back home. But I am more than pissed off with this news that you sucked off your ex-boyfriend!”
“But John, Tommy wanted to sleep with me at first. I told him I couldn’t, and finally, he settled on a blowjob instead. He said he missed the sex we used to have and wanted me to come back home to be with him!”
“Well, it’s good to know you had enough sense to realize that you are my girl now. Tommy had his chance and he blew it. You know, I sent you back to Bloomington to be with your mother – to take care of her and help her as she recovered. I didn’t send you home so you could satisfy your ex-boyfriend’s sexual urges.
“I have needs as well, you know, and I haven’t seen you in three weeks. I have been sitting here at home, patiently waiting for you to come back and thinking you were caring for your sick mother. Now I find out you were ‘caring’ for someone just not her!”
“John, please...”
“QUIET! I want you to get in that bedroom and get out of those clothes right now. Make it quick – I have already lost my patience with you!”
She gave me a little smile and quickly padded off to the bedroom. I guess she thought this was all part of some sexual domination game or something. But I was serious ... she had royally fucked up and she needed to be punished.
I gave her a five or ten minutes to get ready, not only be naked but also be waiting and wanting to see what kind of “game” I had in mind. I knew that her curiosity and her imagination would work on her and she would be on pins and needles waiting to see what I was going to do with her.
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