A Literary Connection Ch. 03

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Trent and Jessica finally connect, intimately.
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Part 3 of the 3 part series

Updated 03/16/2024
Created 03/09/2024
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Ollegio
Ollegio
59 Followers

Like? Hell, I loved what I saw! My average 6 1/2 inch cock sprung to attention instantly. I'm sure many younger folks don't think those of us in our 70s have, or are even interested in, sex but take it from me. There are plenty of sexually active seniors! We no longer have to worry about unplanned pregnancies and for guys who have trouble down there drugs can help. I'm among the lucky few who don't need chemical help to get it up yet and I'm eternally thankful for that.

Women in our age group often have difficulty with lubrication. I always keep a bottle of lube in my nightstand just in case. Just as with guys, it doesn't affect every woman. The dark spot on the front of her thong indicated to me that Jessica wasn't among those so afflicted.

"Jessica, I don't like what I see. I LOVE what I see! Are you sure this is where you want to go now?" I asked.

"No, dummy, I brought an overnight bag and sexy lingerie because I was hoping to sleep in your guest room," she replied, rolling her eyes but smiling at the same time.

I got up and met her halfway down the short hallway. "Sorry, babe. I just want to be sure we aren't rushing into things you might regret later."

"The only way I'll regret this is if you turn out to be lousy in bed. And that cannon I see in your pants is an indication that isn't going to happen." She grabbed me and kissed me hard and long, wrapping her tongue around mine.

My cock seemed to get even harder and was actually starting to hurt a little. I turned her around and led her back into my bedroom, and saw she had already turned down the quilt and sheet. Standing beside the bed, I removed her baby doll and then unclasped the front closure of her bra. She shrugged her shoulders to let the straps slide down her arms and then dropped it on the floor.

For the first time I saw her incredible breasts fully naked. Definitely small B cups, I thought. Age and gravity had caused some sagging but, thanks to being a small size to begin with, it was much less than some more well-endowed women of her age would have to contend with. Her areolae were darker, typical of a woman who had given birth, and displayed several enticing bumps I couldn't wait to explore with my tongue.

Her nipples were already erect. They were each about the diameter of the eraser on a wooden pencil, but erect, about twice the length. I imagined not only sucking but gently nibbling on each and somehow knew that would turn her on immensely.

I knelt down and hooked my fingers into the top of her panties. I slowly pulled them down over her hips, across her thighs, past her knees and along her calves until I reached her ankles. I tapped her left ankle with my right hand and she lifted her foot off the floor, allowing me to remove that side. I repeated my tapping on her right ankle and her panties were freed.

I stood up and gently eased her down, laying her on her back in the middle of the bed. As she watched me, I removed my t shirt and then kicked off my shoes. Sitting on the edge of the bed for a moment, I remove both socks and then stood again. Unbuckling my belt and unzipping my fly I slid my jeans down and kicked them off. My cock was tenting my boxer briefs and Jessica's eyes were glued to that view.

I smiled at her and teased just a bit by pulling out the waistband and then letting it go back. The next time I pulled it out to reveal just the head of my cock. She licked her lips at that view. I considered continuing the peep show but didn't want to be a total tease. I grabbed my shorts, lifted them past my erect cock, and slid them down over my hips. When they hit my ankles I stepped out of them and stood before her in all my modest glory.

"Oh my god!" she said, "Your cock is beautiful! It may be the largest I've ever seen in person!"

"Well thank you, hon, but it really is just average, or maybe on the upper end of the average range," I replied honestly.

"If that's true I guess I've been with a lot of under-average guys! Oops, I don't really mean a LOT...I'm not a hoe and I've only been with a few guys. My husband was my first and since the divorce there have only been a couple."

"Shhhhh. I don't care about your past. As the Goo Goo Dolls said,

I caught you burnin' photographs

Like that could save you from your past

History is like gravity

It holds you down away from me

You and me, we've both got sins

And I don't care about where you've been

Don't be sad and don't explain

This is where we start again"

"Hmmm, seems like we need to start for the first time before we can start again," Jessica said with a come hither look and gleam in her eyes.

I laid down on the bed next to her and wrapped my arm over her, pulling Jessica close. We kissed deeply and pressed our naked bodies together. I could feel her erect nipples on my chest and had no doubt she could feel my hard erection on her mound. My balls lay against her labia and I could feel her wetness.

I broke off our kiss and moved my lips to her neck. I could smell the faint fragrance of the perfume she had used sparingly. Something fresh, like an ocean breeze. I moved up and nibbled gently on her ear lobe and at the same time cupped her left breast with my hand. She moaned softly so I moved my hand up to rub my palm across her nipple. That elicited a stronger, deeper moan so I took it between my thumb and forefinger and rubbed and squeezed.

There is a fine line between exciting a nipple and causing it pain, and that line is different for every woman. Some like it almost brutally hard while others scream in pain at anything beyond the lightest touch. I started gently and gradually increased the pressure, trying to learn what Jessica enjoyed.

As I squeezed harder Jessica's moan got louder and more urgent. When I was about half way between gentle and brutal she screamed out. I latched onto her other nipple with my lips, sucking it in and flicking the tip of my tongue over it and she immediately came in a crushing orgasm. Neither of us had touched her pussy at this point.

So, I thought to myself, she's very orgasmic and seems to like firm, but gentle, nipple play.

Later, Jessica told me that just then she was thinking, OMG, how does this guy know exactly what I like?

Jessica tried to rise from the bed and I instinctively knew she intended to go down on me, reciprocating for the orgasm I'd just given her. But I wasn't ready for that just yet. I pushed her back down and started kissing my way down her chest and abdomen.

Below her navel I discovered a nicely trimmed bush in the shape of a triangle pointing to her pussy. The tip of the bottom ended just above her clit and her labia below were completely bald. This is my favorite. I don't care for a fully bald woman as it seems too much like a prepubescent child. But I love going down on my woman and shaved labia reduce the chances of pube hairs between my teeth.

Taking full advantage of a playing field dressed as I prefer, I kissed down to her clit and teased it with my tongue. Just as my cock was fully erect, her clit stood proud beyond it's hood and proved just as sensitive as one would expect. Every flick of my tongue across it elicited a moan and when I took it into my lip and sucked and flicked she went crazy. I knew I should take it easy but she was enjoying my ministrations so much I couldn't help myself. I sucked and licked her to the second massive orgasm of our session.

"Oh geeze! Trent, stop teasing me! Fuck me, NOW! I need to feel you inside me!" Jessica screamed.

I slid up her body and kissed her, my face covered in her cum. She met my kiss with passion and when we broke apart she licked my face clean. Ahh, so she seems to like her own taste, I thought to myself. Good to know.

Positioned between her legs, I eased my hips up until the head of my cock felt her incredibly wet slit. I briefly regretted not running my tongue up it and into it but thought, another time. When she felt me at her entrance her need took over. Jessica grabbed my ass cheeks with both hands and pulled me into her.

Jessica's pussy felt fantastic. While no virgin, she we incredibly tight for a woman her age who had birthed two children. I later learned she'd had to have Caesarians for both and hadn't had sex in more than five years.

One of the benefits of being older is stamina, cum wise. At 18 it took about five strokes in a pussy for me to cum, although I could be ready for a repeat in just a few minutes. Those had reversed as I aged. I could now go as long as my hips and back could last before shooting off, but it was going to take at least 30-45 minutes before round two.

Jessica came twice more. I learned that picking up her butt would put the angle just right for my cock head to rub her G spot and that letting her down but moving up her body let the top of my cock to hit her clit. Both gave her great orgasms, although she later told me they were different. Both fantastic, but different.

After her second, I pulled out and turned her over. To be honest, I really just wanted to see how adventurous she was, sexually. Much to my delight I discovered she loves variety, but more about that later.

Pulling Jessica up onto her knees I took her doggy style. In my youth I could do this using mostly my leg muscles so my hands were free to play with my partner's clit and tits, but those days are behind me. For short spurts (no pun intended) I could free one hand to play with her, but most of the time I needed both on the bed beside her to keep pumping.

I am still able to alter my hip angles. If I raise them the top of my cock presses hard against her perineum, and whatever bone is behind that. The stimulation is intense and it wasn't long before I felt the heat in my loins and knew I didn't have long.

"Jessica, I'm going to cum!" I said.

"Yes, yes, yes! I want to feel you cum inside me, hon!"

That was all I needed as my cock began shooting into her pussy. I screamed out, the pleasure being almost more than I could take. I pumped a few more times until just the feel of her deliciously warm pussy was more than I could take.

Jessica dropped down flat onto the bed taking me with her. We lay together, sweaty, hot, and breathing hard, my cock still inside her. Eventually I softened and her pussy gently pushed me out. Or my shrinking cock withdrew - I've never been able to figure that out. I rolled off her and she rolled to face me.

"About time, stud," she smirked.

"Sorry, I guess 36 hours from meeting to orgasm is too long, huh?

Ollegio
Ollegio
59 Followers
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