Caitlin Cares

by Tony Tiger

Copyright© 2018 by Tony Tiger

Erotica Sex Story: Divided loyalty has pluses and minuses in bed. Man shows his young lover how it works.

Caution: This Erotica Sex Story contains strong sexual content, including Romantic   Sharing   MaleDom   .

A couple of big changes in my life happened very close together. I’d just been promoted to section manager in the big engineering project I was hired for. It was a lot more responsibility as well as pay and I was very pleased, being just a few years out of college. The second was the ending of an affair with an older married woman whose husband returned from a six-month overseas assignment. Relationships within the company were okay as long as there was no direct line of command.

She was only the second woman I had ever been intimate with and I learned a lot. She, on the other hand, had been down the road number of times before and was a hell of a good teacher.

Being now accustomed to a frequent and vigorous sex life, I was looking for a replacement. A young intern new with the company got my attention. Caitlin was a slender brunette who did an assortment of jobs on request throughout the project. She was fresh out of high school on her first job. I made an effort to visit with her and made a point to sit at her lunch table from time to time and visit.

Finally, I asked her out to an event that I thought she might enjoy. She was reluctant but when I insisted she acquiesced. We had a pleasant evening and when I asked her out again she accepted.

She seemed shy so I played it cool but also noticed that if I was assertive, she eventually agreed to my requests. My matronly tutor had taught me a bit about submissiveness and so I stepped up the game a little. The next time we went out and I returned her to her small apartment, I asked if I could come in. She looked embarrassed and said that her boyfriend was going to be there shortly. That was the first indication I had of any other relationships.

She agreed to go out with me again so I told her that next time I expected to be invited in. I also ordered her to have some vanilla ice cream.

I brought along a good liqueur to dress up the ice cream. She had several helpings which I had liberally dosed and seemed to be getting a little bit giddy. I had learned that she rarely drank. That night I got a little kiss and hug before I left.

Time to change up the game a little so I invited her to my place for dinner that I would prepare. I kept her wine glass full and it definitely affected her. When we moved to the couch and I started up a chick flick, I sat close to her and got no objection when putting my arm over her shoulder. During the sad part she snuggled up to me and finally during the romantically sexy part, I bent over and kissed her.

She seemed to be struggling with something but got right through it and started kissing me back harder and harder. My hands strayed to her chest and felt her pronounced nipples through her dress. Her small breasts didn’t need a brassiere. Her breathing deepened and her kissing got more intense so I took her hand and moved it down to my swelling. At first she pulled it back but I insisted and she began exploring the shape that she found.

She was breathing hard by now and pulled back to say, “No, I can’t!”

I was nuzzling and kissing her neck at that point and asked, “Why not? You’re old enough aren’t you?”

“Yes, but I was with my boyfriend this afternoon.”

I pulled back to look her straight in the eyes, “So? Did he wear you out or something?”

“What I mean was, uh, we had sex.”

“I figured that’s what you meant. But that was this afternoon and now is now.”

She just stared at me for a moment and I could see that her mind was whirling. I emphasized my point with a deep tongue kiss and she relaxed and got back into it. That was the turning point and I felt her avidly groping my bulge. I pulled off her top and her nipples felt my mouth on them. I’d learned how to make a woman orgasm just from that and she was soon shaking and squeaking with pleasure.

When she laid her head back on the couch I moved down to unfasten her slacks and pulled them off along with her shoes. She didn’t resist as I spread her legs and kissed my way from her knees up her thighs. When I followed the scent to its source in my tongue began probing, her moans steadily grew in intensity.

When she orgasmed the second time I let her rest for a moment and said, “How about me?”

She got the hint and pulled my pants off and explored what I later learned was only the second erection she had direct experience with. Her oral sex was pretty clumsy compared to the experienced partner I’d had recently had but I was not going to complain. Finally I ordered, “Ride me!”

Her slender body was pretty snug and it had been long enough I couldn’t tell that her boyfriend had been in there earlier. She was really wound up in her third orgasm which pulled my long pent up ejaculation out of me.

We snuggled for a while, got dressed and I took her home. She was very quiet during the drive and I only got a short kiss at her doorstep.

I didn’t see her for a few days at work but when I did I told her that “we” had plans for Friday evening. She protested, “But I already have some.”

“Change them. I’ll be there at seven.”

When I arrived she let me in and I put my arms around her and gave her a deep kiss. “It’s been a week and I want some more of the good loving we had last time. There is no rush to get where were going.” I silenced her slight objections with kisses and began taking her clothes off as we stood there. I could sense her struggling but I persisted and when my finger found her clit there was a lot of dampness.

When naked, I led her to her bed which was quite messed up with an evident wet spot not yet dried. “Go get a towel,” I ordered.

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