Diana Learns Trombone

"Have you ever heard of a rusty trombone?" Diana asked.

"Have I ever heard of a rusty trombone? Sure, and yes, I'm up for it," I answered enthusiastically.

That was the first time I had ever been offered such an act and, more importantly, the woman offering the act was one that I had become smitten with and had just recently started to become very sexually adventurous with. A little background:

Diana and I had been seeing each other for about a year. We were both older (in our late 50's) and while I was still working, Diana had retired, the result of great business sense and her selling the marketing company she had founded. She created the business in New York and, with the sale, decided it was time to move back to her home in Chicago. I was on a dating web site when I ran across her profile and became intrigued. I had never seen a woman bold enough to include hilarious and candid photos of herself, dressed in a t-shirt, posing with her dog (both of them wearing glasses!) in addition to the traditional glamour shots.

We started dating and found we had many things in common -- we both enjoyed cooking, good food, good booze and a desire for more of a casual than a committed, traditional relationship.

Even though Diana was retired, she could not sit still, vacationing often at her place in New York or Maui and travelling whenever the urge hit her. We spent weekends together when we both were in town and formed a great relationship.

I learned that Diana was a widow and the last several years of her marriage had been rather sexless, due to her husband's illness. Once he passed, she had decided to loose her born again virginity and decided I would be the lucky man for the job.

I considered myself a capable, but average, lover, but one who considered himself to be very patient and sensitive to a woman's needs. Thankfully, Diana thought I was the world's greatest lover and could not get enough of me. Good for my ego! I also had a kinky streak and enjoyed sharing that with her, starting with eating her ass early on in our relationship. She found she quite enjoyed it, having never delved into the anal arts, and looked forward to me partaking of that frequently.

I never asked her to return the favor, figuring if she ever got a desire to, she would go for it or bring it up. And now she was.

"It would have to be at the right time. I'd be self-conscious and would have to use a garden hose or something to make sure I was all clean and cleaned out." I replied.

"I would appreciate that." Diana said. "While I want to do a rusty trombone, I don't want to do the rusty part," she said, frowning and crinkling her cute nose.

I hadn't said much about it but would occasionally tell her that it was still on the board and I was just waiting for the right time. In the meantime, I started putting some plans in place.

Diana would be returning from a three-week trip to Paris and I knew, from the texts she had been sending, that she was extremely horny. She would be flying in on Friday night, staying at my place for the weekend. I got the place cleaned up, stocked up with food and beverage and did my prep work for her arrival.

She took a car from O'Hare to my place where I greeted her warmly. We went to the bar, as we usually did, to start the evening. She was greeted with a menu I had printed out that foretold the activities of the evening:

Diana Comes to the Chicago House

The Rust Weekend

Curated Selections:

Beverage: The Rusty Nail. A classic cocktail combing scotch and Drambuie. Strong enough to lower the inhibitions and flavorful enough to accentuate your upcoming treat.

Music: Rust Never Sleeps. Neil Young and Crazy Horse. Another classic chosen, obviously, for the name.

Depraved sex act: Rusty Trombone. Diana's first foray into eating ass while jacking off my cock. Destined to be a classic.

Diana laughed a deep, hearty laugh and Neil Young began in the background. I mixed up a Rusty Nail and toasted to our upcoming adventure.

"To you eating my ass," I said.

"I can't wait," Diana quickly chimed in, "so why now?"

"Well, while we are relaxing I'll tell you about some of the prep work I've done and also an assignment you have."

"I took off work early today," I continued, "and came home and gave myself an enema. Yes, it was weird. But I really wanted to make sure I was super clean so you could enjoy this experience."

"And yesterday, I shaved my ass crack." Diana nearly spit out her drink with this revelation. While I'm not particularly hairy, according to Diana, I have an exceptionally hairy ass crack. "I wanted to make sure there wasn't anything that could cause any dingleberries. So, after we finish our drinks, we'll go shower together to make sure I'm freshly clean. We can lather each other up, then I'll lather your finger up and let you finger my ass a bit to make sure it's really clean, then we start the music!"

Diana's eyes bulged. She had been wanting to finger my asshole for a long time, claiming it was just because she thought I would like it, but I knew her well enough to know she really wanted to do it for her own enjoyment. I had always held her off, self-conscious about being dirty, but now that excuse was gone.

Diana quickly finished her drink and had a huge smile on her face.

I stood up and started to make a couple more Rusty Nails.

"There's a bit more, and I'm making this one a double. I mentioned you would have an assignment and here it is. After our shower I'm going to go to the bedroom and lay face down. From then on, you're in charge. This is your fantasy and the only thing that I'll be upset about is that, after we're all done, if there was something you wish we would have done that we did not do. So, anything you can think of, anything you want do to, this is your shot at it. At a minimum, you need to figure out what positions you want me in. You can have me laying on my side in bed, you can have me ass up with my head in the pillow, on all fours, squatting over you, standing up with you kneeling down behind me, whatever. Hell, I don't care if you bend me over the island in the kitchen and go to town. Whatever is going to get you off."

"And, just so you know, my expectation is that when you're done playing your trombone song, it will be my turn and I'll be eating your ass and making you come with my tongue buried as deep in your ass as I can get it."

I noticed she had become a bit flushed. She shivered a bit with the last revelation, finished her drink, stood up, took my hand and led me into the shower.

We showered quietly and quickly, both excited about the upcoming events. When I had gotten myself clean I took her hand and soaped up her middle finger. I held her finger as I turned around and slowly positioned it near my opening then slowly guided it in.

"It's all yours. Just be gentle."

Diana slowly rubbed my asshole, then quickened the pace a bit, gently exploring and fingering my asshole. I relaxed a bit, getting a bit more comfortable with the unusual sensation.

"Now it's my turn," I said as I reached around and took her hand away from my asshole. I turned her around, soaped up my finger and gently fingered her asshole.

"I can't wait to eat your asshole," I whispered in her ear as I rubbed her nipples. I heard her moan softly.

I finished us both with a thorough rinse, got dry and went into the bedroom, laying face down on the bed.

Diana got in next to me. "What a nice ass," she exclaimed. She started massaging my ass cheeks. As she massaged them, she separated them and I could tell she was looking directly at my asshole, starting to get excited about the upcoming activities. I felt her breath on the crack of my ass, then her tongue slowly licking me up and down.

"How is it?" I questioned.

"Delicious! And very clean! You can relax about being clean enough!"

"Get up on your knees keeping your head in the pillow," Diana commanded. I complied and as she massaged my ass I felt a sharp sting as she spanked my ass cheek firmly.

"You said I was in charge," she said, answering my question about the spanking before I even asked it.

She reached between my legs, grabbing my hard cock and started flicking her tongue across my asshole.

I quietly moaned in pleasure as her playing my trombone became more and more intense.

She took a break and told me to stand up and lay across the bed. She kneeled down behind me and resumed her concert. I was moaning louder now, her skills at both tonguing my ass and stroking my cock getting more proficient.

"My knees are starting to hurt, hold on," she said as she lay down in the bed.

"OK, come sit on my face and let me eat that ass." She didn't have to ask me twice as I climbed on the bed, straddling her face. She grabbed my ass cheeks and told me to bring my ass closer to her.

She was going to town on my ass but couldn't reach my cock very well. I was too excited to slow down so I began stroking my own cock. Her moans became more pronounced and vibrated my asshole. I knew I wasn't going to last long.

"That's it, eat my asshole," I exclaimed as I beat my meat, getting closer and going faster.

I felt the cum building up in both my balls and my ass at the same time. And I had a devilish thought.

"Keep eating my ass. Tongue fuck my asshole. Oh shit, that feels so good."

I knew I was close. I positioned my free hand under my cock.

"Yes, keep going," I muttered as I began spurting my hot cum into my open hand. Diana always said she loved the taste of my cum and I had a treat in store for her. I rose up off her face a bit and wiped my cum filled hand across my ass and lowered it back down.

"Eat my cum. Clean up that cum off my asshole. You deserve it, you worked hard for it!"

I felt her eagerly slurping and lapping up my sperm, anxious to get all she could.

When her licking slowed I rose off of her and looked down at her smiling face.

"You look so beautiful with my cum all over you face," I told her as I went down and kissed her passionately. I followed up my kisses with some tentative licks on her cheeks, tasting my cum.

"WOW! That was amazing," Diana exclaimed.

"Oh, we're not done yet. Roll over, it's time for me to do some serious ass eating."

As soon as Diana rolled over I was all over her ass, forcefully spreading her cheeks apart and licking away furiously at her asshole.

I could tell she was extremely excited as she got up on her knees, without being told and spread her ass cheeks apart. I probed my tongue into her asshole and she responded back, pushing her ass back on my tongue repeatedly, trying to get it further and further into her ass.

"It's my turn to lay down and enjoy myself," I said. I grabbed the Hitachi vibrator from the drawer, plugged it in and handed it to her as I was laying down in the bed.

"I want your asshole on my tongue and I want you to use the vibrator to cum with my tongue buried in your ass."

I didn't have to ask twice as Diana hopped on my face and awaited my tongue. I could smell her wet pussy and could tell she was really excited as she turned on the vibrator and held it against her clit. I spread her cheeks and started licking her asshole, waiting for it to open up a bit. Diana got in a good and comfortable position and my tongue slid up inside her. She moaned and started her a cadence that I would foretold her orgasm.

"Oh, Oh, Oh, I'm going to cum. Oh, Oh, Oh, your tongue feels so good up my ass. Oh, Oh, Oh, I'm cumming. I'm cumming. OHHHHH."

Diana rolled off of me, exhausted and very pleased.

"Oh my, that was so incredible!" she said, clearly basking in the afterglow of her orgasm.

We cuddled, both of us a bit stunned to say much, content to relax and be in the moment with each other.

After cuddling for a good long while, I was starting to feel a bit thirsty, thinking maybe another drink or a snack might be in order.

I looked at Diana and asked, "What do you want to do now?" thinking she would suggest either a drink or dinner.

She smiled at me with an evil smile and replied, "Have you ever heard of a prostate milking?"

To be continued...?