My Turn to Ride

Mostly true.

Dee and I have been together since college days. We're retired now, but neither of us feels very old. We don't look the same as we did in our 20's, but when I see or feel her naked it's her look and feel from more than 40 years ago that comes to my mind. Our sex life remains satisfying and varied; we schedule time together several times a week, generally in the morning. We both feel very fortunate that we can still enjoy sex as often as we do. We can still have a lot of fun with it, even though our level of athleticism has decreased with age.

Not too long ago, we lay recovering from our orgasms after Dee had vigorously ridden my cock.

She said, "I'm so glad we can still do that -- it's one of my favorite positions, and it has been awhile since we've been so ambitious."

"I had plenty of fun too, you know," I replied.

"We don't have anything on the calendar two days from now. Maybe you would like to ride my cock to finish up our next party."

"Sounds great to me."

We both enjoy anal play in both directions; for me, a toy stretching my ass results in an intense, deluxe orgasm. It's particularly exciting to me when Dee suggests it -- when I ask for toy play, she generally consents readily, but even after all these years it's a bit hard for me to believe she really wants to do it. Like I said, I feel very fortunate.

When the day arrived, we were having our coffee while sitting in front of the picture window watching the birds, and she said

"You do remember what kind of party we're planning today, right?"

She knew perfectly well that I remembered, and that I had been thinking about it steadily for two days.

"I think that after you clean up, you should put in a good-sized plug." she said. "I want to use a significant dong to stretch you a bit, and I want you warmed up for it, and also thinking for the next couple hours about what I will be doing to you." Once again, she knew I wouldn't be thinking about much else in any case.

Given my level of excitement, it of course wasn't long before I was in the shower, cleaning up for our self-indulgent morning. I started with an enema; I find the sensations of anal play to be greatly enhanced when I'm clean inside, and easier cleanup afterward is a nice bonus. After I finished my shower and dried off, I opened my nightstand drawer to check out my butt plug collection.

I own a wide enough variety of plugs to suit almost any purpose or mood. Sizes range from cute and barely noticeable to nearly too big, materials from classic latex to rainbow silicon to handmade glass to mirrorlike stainless steel. Some are angled to tickle my prostate, others are just for feeling the weight or fullness in my bum as I move around during the day. All of them do a fine job at staying safely and securely inside me, no matter what (or whom) I am doing.

I chose my favorite stainless plug, just big enough for me to feel its weight at all times. I spread a touch of lube on its tip, felt its sweet coolness against my hole for a moment, and slowly pushed it in, feeling just a bit of a stretch as my butt expanded around the head, then the beautiful feeling inside along with the contact of the flange on the rim of my ass as it settled in place. I wiggled my hips a couple of times to savor the feeling, then headed back to the living room, where Dee was still on her laptop.

"Are you almost ready to get the party started?"

"I'd rather give you some more time to prepare mentally for your pounding," she said. "While I'm finishing a few more of my daily puzzles, why don't you read something to keep your mind on whatever plug you have up your bottom."

She didn't have to ask twice, and most readers of this story will have no trouble guessing where I found some appropriate reading matter online. I poured myself a little brandy to go with it.

I had gotten through a few stories from my favorite authors, along with my favorites' favorites, when I heard Dee in the shower. A few minutes later, she returned to the living room in her robe, with a bottle of sparkling wine and a vape pen. Our state has had legal cannabis for some time, and I grow a strain that we particularly enjoy before sex.

I don't remember what we started out talking about, but after a few puffs and a few sips, the conversation of course turned to our plans for the bedroom.

"You know I'll be wanting you to do more than just ride my big dildo," she reminded me.

"Of course, I expected that. Will you want some attention before my ride or after?"

"Before. As in before my pussy gets covered by the harness and the dong." Her favorite harness is a pair of well-fitting silken dildo shorts with a ring in front, so we don't get slowed by straps and buckles.

"Also before as in before you get to see the dong you will be riding. You can think about it while you eat me and while you still have the plug in your bum."

"Work work work," I lightly moaned as I pulled her to me for a kiss and a bit of a feel of her still-perky breast. "Finish your bubbly; I think it's time to get started."

In the bedroom, we laid a soft beach towel on the bed to keep lube and such off of our quilt, and Dee laid back comfortably on a couple of pillows. She pulled me in for a kiss, and I put my hand on her pussy, which already felt quite creamy as I gently stroked her.

"That feels great, but I've been thinking about your tongue and I want it now."

"Who am I to argue?" I murmured as I nibbled my way down to my favorite position between her legs, and locked eyes with her as I slowly ran my tongue the length of her vulva to her clit tip. I saw her eyes roll back a bit as she sighed deeply.

I was in an excellent position as well -- my hardon was pressed against the soft towel, and I could feel the heavy buttplug against my prostate as I moved my body while licking her pussy.

Dee had clearly been indulging in some mental foreplay before entering the bedroom. Her clit was fully erect, and growing as I licked from her moist vagina up to the tip with long strokes. While my tongue was covering her clit, I gently teased her labia and vagina with my fingers. Her fingers wandered to her breasts, and lightly stroked her nipples. As I continued my licking, she began to rock her hips in a slow rhythm, and I knew she was getting close. She began to come as I gently slid two fingers into her. She grabbed my head and pressed my tongue hard against the shaft of her clit as her pussy pulsations slowly faded. We held one another tightly as she caught her breath.

"That was just what the doctor ordered," she said as she slowly sat up. "You've been so patient, I think it's time to show you the toy that will be stretching your tush today."

She reached behind her stack of pillows and pulled out the dildo shorts. Already set in the front ring was the dildo we call Big Blue; not our biggest one, but one that definitely needs to go in slowly and carefully. It's a twenty-first century silicone reissue of an old favorite from the latex era, with a big smooth head and a lot of veins on the shaft; I think of its style as semi-realistic. A large pair of balls makes it work well in a harness, and keeps me safe.

Dee slipped into the shorts, with a little help from me, and reclined on her pillows against the headboard. I held the dildo and pressed its flat end against her pussy, asking "Are you comfortable?"

"I make a living."

"No you don't; you're retired."

"Thank goodness for that. Now turn around, and let me get you ready."

I complied, and she took hold of the plug's end. She of course did not just pull it straight out. She rotated it back and forth just a tad, knowing that it was sitting right against my prostate, and then pulled on it very gently, stretching my anus a little before pushing the plug back in. She repeated it a few more times with a few little comments:

"There's a nice-looking stretch."

"I'll be seeing that bum stretched a lot more in a few minutes."

"Such a pretty plug to look at while I push it in."

All the while as I felt her working the plug, I faced Big Blue, protruding from her crotch. I grabbed the dildo to steady myself as she slowly removed the metal plug with a hearty "Hi-yo, Silver!" She reached for the lube, and added a bit to my hole with a finger or three.

"Time for you to use some more of this," she said while handing me the lube.

I applied lube liberally to the dildo, turned around, and carefully straddled her belly, with the dong comfortably nestled in my butt crack. I positioned the head of the toy against my hole and just held it there for a moment, savoring the contact and knowing that it would soon be spreading my butt wide.

Slowly I sat back on the shaft, savoring the pressure and then the stretch at my anus, while Dee took hold of my boner, which was quickly becoming harder from the blend of sensation both fore and aft. I settled all the way down on the shaft, and Dee, still gripping my penis in one hand, pulled my head down with the other for a deep kiss. As I sat back up to start moving, I steadied myself with my hands on her breasts.

While I slowly moved up and down on the dildo, I could feel the veins stimulating my stretched anal canal, and the head lightly caressing my prostate. It was my turn to feel softly transported, as my eyes began to close while I reveled in the fucking I was getting. Dee gave my erection an extra squeeze, and said,

"How about you lean back for a moment so I can get a good look at your bum with Big Blue stretching it?"

I did so, and she gently ran a fingertip around my rim against the dildo. It of course made me moan. As I sat up, I grabbed the lube and added a generous dollop to Dee's hand and my erection. She knew just what to do. While I rode the dildo a bit more rapidly and with longer strokes, she gripped my penis more tightly and began to move her lubed hand up and down the shaft. My orgasm came on slowly, spreading out from my anus and prostate. Its gradual crescendo radiated through my pelvis and took over my consciousness, as semen began hitting the pillow near Dee's face, then her neck, then her breast and belly. I must have been crying out a bit, but I barely heard it. I stayed on top of her with the toy still in me, and we embraced; I was in no hurry to climb off of Big Blue and return to real life.

After I caught my breath, drifted back to earth, and climbed off of Big Blue, I asked, "So what snack shall we have with the rest of the bubbly?" As I said, we feel very fortunate.