Confessions Diana's Ross

When I turned thirty, I decided to travel to the east coast. There was no particular reason except that I was restless. Katy had moved on, and really after her, not many stood a chance. So I figured I could use a holiday.

I had left bartending and become a manager at “sprawl mart.” There was an opportunity to transfer to Virginia. Not many wanted to leave Texas, but I was ready and very willing. So, I applied, and after two phone interviews, I was hired. I immediately quit my job, sublet my apartment and headed up to Blue Ridge Mountain territory.

Being a cheap bastard, I decided to drive and pocket the rest of the moving allowance. I could think of better things I could do with the relocation money besides buying a plane ticket. Besides, I would really miss my truck if I had left it behind.

Taking a week of vacation time, I planned on enjoying this ride. The route I chose took me to Atlanta, Georgia, and then cut up north. I got the cheapest motel room I could find and hit the best barbecue joint the locals could recommend. Because of the area I stayed in, it was easy to find some real “home town” folks who told me where to get some authentic BBQ and ice cold beer.

With only two wrong turns, I arrived at Fat Matt’s just in time for the band. They were still serving sandwiches and baked potatoes, along with beer from an iced down metal tub. I bought two sandwiches and two beers to start and found a corner table to hide at.

I’m a voyeur, and corner tables are my favorite spots, especially a dark corner in a smoked filled room. There’s something about that whole scene that makes beer and BBQ complete – well, that and the band.

Fat Back Deluxe churned the air with Mercy Me while I began to enjoy my evening in Atlanta. Ah, but the trick was to enjoy the evening and not miss Katy. You see, that lovely piece of God’s most beautiful handiwork introduced me to the blues.

The first time I heard Cleo’s Mood, I understood why sax and sex went hand in hand. People talk about the piano. They talk about the guitar. For me the sound that went down to my balls and woke up my soul came from that j-shaped horn. Ever notice how the sax looks like it’s got a hard on? Think about it.

I can’t do anything around the blues without thinking about Katy, so I drank my beer slowly, allowing each mouthful to wash over my tongue and then slide slowly down, hoping to wash her memory down as well. But I’ll be damned if her shadow didn’t linger, her fine ass seductively swaying to every note against the crotch of my jeans. God damn, I said aloud as I finished the first of two more beers.

While pressing the cold beer bottle to my lips, a voice broke the thick smoke and called towards me.

“You alone?”

I tried to see her, but all I could make out was her shape outlined by the dim bar lights and neon reflections off the stage.

She was about five seven, plenty of legs curving into shapely hips, a firm torso with about a mouthful of breasts and crowned with dark, shoulder length hair.

“Have a seat,” I half-yelled, standing up and pulling the stool out, trying to take note of the face that belonged to the body. Sun Shines Down made for a great background effect as she introduced herself. Diana.

As I took the lighter out of my pocket and lit the cigarette she held in between two beautifully manicured fingers, I caught a glimpse of her face. She did not disappoint, and I smiled, pulling my hand back and putting the lighter back in my pants. I adjusted myself quickly while my hand was in place – my cock’s attention had been aroused.

When Country Boy began, I asked Diana to dance, and we hit the floor. I held her close, our hips rolling to the bass. We turned corners quick and sharp, with a long slide away and then back into each other’s arms. She was damn good. Not as good as Katy, but she sure made the memories begin to fade, at least for a moment.

We danced a couple more numbers before the band took a break, and I retrieved more beer for us both. When I returned, we had a quick chance to talk a little. She lived in New Orleans but was in Atlanta for a business conference and had come out to blow off some steam. I was happy to oblige.

After the band finished their set, she invited me to her hotel room. The lounge was still open, so we went in and had another drink before going up. To be honest, I felt horny as hell, but there’s one thing you learn if you have any sense about you — you never rush a woman. Might as well say goodnight and give yourself a hand job. Ain’t gonna happen unless it’s in her own time, my friends.

She bullshitted through two martinis and now a glass of wine. The drunker Diana got, the more she talked, and we finally got to the topic of favorite sexual experiences.

“He was older, of course, but God, he was so good looking. Even at that age, I knew how to pick a man,” she began as she sipped her Merlot, leaving a shimmer of dark red lipstick on the edge of the glass. “I can’t tell you how much I miss him. The first time usually isn’t so great for a girl, but honey, let me tell you. He was the exception to the rule!”

Diana touched my shoulder as she laughed. She had a gorgeous smile, and her laugh was contagious. I couldn’t help but join in. We were having a hell of a good time, and I could hardly wait to hear the details. I wanted to hear all about what, and who, was coming, so I encouraged her to continue.

“Ross was a grease monkey and a friend of my brother’s. My favorite memory is of him visiting my grandparent’s house to play cards. This one night, I knew he was coming over, and I made sure to wear these shorts that cut just under my butt cheeks. I had a nice ass back in the day. You might not be able to tell now, but my ass cheeks were round and tight, Priest.”

“They’re holding up quite well if you ask me,” I coyly replied, lifting my glass in a toast to her ass before taking a sip of jack.

“You’re sweet, honey,” Diana smiled and reached over to pat my hand. I looked into her dark blue eyes and smiled back. Then, she took another sip of wine and left her hand on mine as she confessed more.

“I couldn’t help but feel so beautiful when he kissed me in the hallway on his way to the bathroom. I regretted feeling scared when he asked me to come to the bathroom with him, and I backed away and returned to the living room without saying another word. I wish I would have, but he turned out to be worth the wait.”

“So, just that one kiss and then what?”

“We’d been flirting around for a while. I’d find every excuse I could to sit on his lap, bring him a beer, for which he always hugged me and slid his hand discreetly down my waist and patted or playfully squeezed my butt. I often found excuses to go to the garage and see him, taking him a soda or a beer. One time I walked in on him when he was taking a piss. I backed out but not before looking straight down and catching a glimpse of his penis.”

I snickered. “Did you like what you saw?”

“What do you think?”

I pulled two of my fingers from under her palm and put them on top of her hand and stroked her soft skin. Diana seemed pleased, grinning seductively. I was liking where this was going. “So, then what,” I said, breaking the silence.

“Well, you know the old folks believed in fresh eggs. So, one morning Ross dropped by and said he’d go and pick up the eggs for breakfast and asked me if I wanted to go. Of course I didn’t say no. I was hoping he would make a move while we were out, and my heart beat harder and harder in anticipation until he did.

As we drove down the two lane highway, he told me to scoot over next to him, and when I did, he put his arm around me. Only a few minutes passed when he moved his hand down over my shoulder and reached for my breasts, putting his big strong hand over the one and massaging it until my little nipple stood way high.”

I licked my lips, trying to remain in control, but my dick was another story. I reached down and unzipped my pants slightly. I knew I’d end up with zipper burn if this kept up. Diana took another swallow of wine and then gave me more, not noticing, or pretending not to notice, my maneuver.

“I didn’t care if this was right or wrong, Priest. He made me feel so good. I enjoyed my breast being played with, even him pinching my nipple a little hard. The slight pain surprised me and excited me even more. Ross asked me if I liked what he was doing. Embarrassed, I whispered that I did, as he turned down a dirt road and started slowing down.”

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I smiled wickedly knowing what was coming as I took another sip of my drink. Hell, this was what I lived for, and I was ready to enjoy the ride. AND I was getting hornier and hornier by the minute.

“He asked me if he could pull over for a minute so we could talk. I knew what he meant, and I shook my head in agreement as he looked for a safe place to park.

While he maneuvered, I prayed he wouldn’t stop manipulating my breast, and he didn’t, but he put his hand under my shirt and bra and felt me up, pinching and rolling the nipple between his thick rough fingers harder and faster. I cried out a little, and he pulled me close to him.”

I attempted to look calm as my cock started testing the strength my partially open fly. I ran my fingers over her hand gently, indicating my ever increasing interest in what she had to say. I tried not to tip my hand, but I’m sure the twenty shades of red I was turning as I tried to control myself gave her come kind of clue.

“Ross was so protective. He found a cypress tree and parked behind the brush so we wouldn’t be seen. The way he looked at me melted my knees, and I thought I’d lose my breath as he leaned over and pulled my mouth to his.

He kissed me deeply, his tongue gently prying open my lips and dipping inside, exploring my own tongue and then retreating back into his mouth. He tasted like beer, and I loved it. And he smelled good. Ross always did. Chaps, I believe it was.

As we kissed, he took my hand and put it on his crotch, rubbing my fingers over the ever-swelling mound. I was a little startled ’cause I could feel it throbbing. Ross pulled me real close to him and then he put my hand on his thigh and unzipped his pants, pulling out his beautiful candy pink cock.

My eyes opened wide in amazement as Ross helped me massage his dick into full erection. The purple head matched perfectly with the now deep rose color of his hard flesh. I wasn’t sure what to do with it, but I knew I wanted it.”

So do I, the voice in my head responded.

“Ross kissed me again, and then guided my head downward. He told me not to be afraid as my mouth instinctively opened and his hot cock slipped inside. I tasted the salty-sweet pre-cum first and didn’t know quite what to make of it, but I closed my eyes and let my tongue explore the ridges and veins, the smooth sections in between and the crown of the ever-bulging head. I liked it.”

So do I, I thought trying to keep my composure and continue to look genuinely more interested in what she had to say than in the hard on that was getting harder to ignore. Jesus, I could have turned her over and fucked her on the table right then and there. Flashes of that scene kept creeping in, and I reached down and rubbed my crotch, trying to calm my throbbing dick down. I was having trouble, to tell you the truth, but her voice brought me back into our reality.

“Ross asked if I was okay, and I nodded yes as I continued to suck his cock deeper into my mouth. He helped me get a rhythm until he began to spew. The ejaculation surprised me, but I drank it in as best I could and continued to suck the hot cum out of his dick hole like trying to get a thick sip of milk shake out of a small straw.

When he told me how sweet I was, how good I made him feel, I knew I didn’t want to stop there. I raised my head from his crotch and looked at him, a little of his warm cum dripping down my chin. Ross smiled sweetly as wiped my mouth off and told me to take a sip of my coke, swirl it around and then spit it out the window like mouthwash. I did everything he told me to without hesitation.

Then he said, You like it, baby? Will you let me touch your panties? I wanna see if you’re wet. He made me melt with his soft, dark brown eyes and sexy lips, so I shook my head indicating that he could go right ahead!

Ross reached over and leaned the seat back. I followed the backward motion, breathing heavily as he then reached under the band of my shorts and felt the crotch of my underwear. He found out that not only was I wet, I was soaked.

Ross rubbed my crotch and then moved his hand under the material and touched my clit. I thought I’d shoot straight up out of the seat when I felt the tip of his finger rolling over my moistened hood, and I closed my eyes and moaned as he continued to excite me.

Leaning close, he pressed his lips tightly against mine, taking my breath as he worked his hands up and around the waistband of both my shorts and panties and tugged them down off my legs. I complied willingly, pulling my feet up as he freed the lower half of my body from its covering.

Ross took his time returning to my crotch, rubbing his rough hand slowly up my leg, stopping at my thighs and playing with spots that sent goose bumps all over my arms and legs. He laughed slightly as he felt my flesh reacting to his touch and then kissed me again while following the rest of my leg into the soft, moist flesh waiting for him. As his fingers slid up and down my slick cunt, I breathed heavily, my heart pounding harder and harder and my pussy getting wetter and wetter.

Soon, I found myself reaching down and pushing his hand towards my pussy hole. Ross obliged with an Are you sure, darlin’ in that sweet sexy Texas country boy drawl. I told him that I was as he reached down and pushed two fingers inside my pussy. I felt dizzy as he finger fucked me, a little pain and pleasure coming in waves.

Once when I opened my eyes, I looked down at his crotch and watched his hot pink cock dancing wildly while he fingered me. I quickly closed them again when he put in two more fingers and spread my hole out more and more. Slowly, I was getting used to his fingers and enjoying his strokes more than wincing from the pain.

Gently, Ross kissed me again, and then pulled his fingers out. I looked at him just in time to see that country grease monkey put them in his mouth and suck my juices down his throat. He told me, Mmmmm, you taste so good. Can I fuck you, baby?

I felt scared, but I liked him so much, and I wanted it to be him. I was so ready and willing, so I told him as sexy as I could, Sure, baby, we can fuck.

Ross grinned seductively while he reached down and flipped the knob that slid the seat back far enough so that he could climb over and position himself above me.

Gently, he helped me open my legs, putting one leg in the driver’s seat and hanging the other one out the passenger window. Ross looked at me and then whispered in my ear, You’re so sweet, honey. I’m gonna do my best not to hurt you, but you know it’s gonna hurt a little, right? Your pussy’s so small and tight. I’m sorry, but you’re so beautiful, and I have got to have you, darlin’.

I ran my hand up the front of Ross’ t-shirt, feeling the pounding beneath his muscular pecs. His hard body felt so good against my soft hand. I wanted him to do this to me so badly and didn’t care if it was going to hurt. I just wanted him to fuck me.

Reaching down, I petted his throbbing cock. It had ballooned and turned a bright reddish-purple, filled and ready to pop. Ross closed his eyes as he braced himself, allowing me to play with his big dick. His pre-cum was thick and made stroking the mushroom head feel like a slick, smooth pool ball in the palm of my hand. Taking a deep breath, I told him to put it in me.

Ross opened his eyes and looked at me while he reached down and took his dick in his hand. I pulled my legs up by the knees, determined to be as wide as possible for his entry.

He was right. It did hurt. It took a great deal of effort to get just the head in, and it was almost too much for me. With patience, though, he finally popped the tip of his cock in and stopped for a minute to let me get used to it.

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After a minute, Ross started rolling his hips slowly, working my pussy carefully while pushing his body up high so his torso could rub my clit. As I relaxed more, the pain soon gave way to pleasure, and I started rolling my hips in response.

Pressing slowly forward, he pushed more of his cock inside me. I could feel my virgin pussy stretching more and more, and he seemed to be going straight through my gut with each stroke. I closed my eyes and held my legs tight until I felt the tickle of his ball hair against my ass cheeks. I giggled knowing that finally all of Ross was inside me. I had all of him. I stretched my arms up around his neck as Ross kissed me again.

Yeah, that’s it, Ross breathed out while he fucked me slowly, with short thrusts at first and then long withdrawals and returns. He continued to rock back and forth, squeezing his tight round ass tighter and tighter. My pussy reacted quickly to pre-orgasm contractions as I rocked with him, matching every thrust and moving my body beneath him.”

Diana stopped to take a breath and take a look at me. My eyes felt like they were going to pop out as I tried to focus. I held on to my cock as hard as I could with one hand, trying to keep from blowing up in my pants. Diana noticed the sweat dripping down the side of my face. She was amused. The wicked smile erupting through her crimson lips assured me that the only one I was fooling was myself. Diana moved to the seat directly next to me, leaned close, and then continued her confession within inches of my ear.

“So Ross says, I’ve got to cum, baby. I’m gonna fuck you hard now, ’cause I’ve got to cum. Keep your eyes on me, darlin’. I want us to be looking right at each other when I shoot my load in your pretty pussy. Now, look at me.”

I turned towards Diana as if the command was meant for me and met her lips tenderly. While we kissed, Diana reached over and slid her hand up my chest and over my shoulder as I wrapped one arm around her shoulders and one around her waist. Our mouths melted into one another, and we teased each other expertly with slight tongue touches until we both retreated back into our drinks.

After a refreshing swallow, she again leaned over but this time she put her hand on my thigh and began stroking towards my crotch as she completed her tale.

“I forced myself to stare into Ross’s eyes. His passion roared like storm clouds, turning them so dark they almost appeared black. The intensity was overwhelming, and I quickly became lost in the way he looked at me, forgetting and relaxing as he began to hump me, fucking me hard, pressing an imprint of the seat into my back. I could feel the leather rubbing a burn into my ass as he continued until I felt the first hot bursts of his cum filling me.

The intense heat pouring into my cunt together with the piston-like action of his fucking pushed my senses into places I had never gone before. I wasn’t sure if I had a vaginal orgasm, but it sure felt like I had. When Ross was finished, he lay his body against mine, sweat dripping from his forehead down his neck and rolling over my wet skin. He smelled like spices and leather. I enjoyed smelling him as much as I enjoyed his fucking me.

Before he got up, Ross kissed me again, his tongue darting playfully in and out of my mouth. When he asked if I had cum, I looked at him and didn’t know what to say. I still did not understand all the sexual dynamics, but evidently my silence told him I needed a little help. Ross rolled over to the driver’s seat, taking his soaked dick out of me and putting it back behind a closed zipper.
Then he asked, Do you play with yourself, put your fingers on your pussy and rub it ’til it feels good? I thought for a minute and then told him how I liked to lay underneath the water faucet in the bathtub and let the water tickle me. I told him how good it felt, and he informed me that I had been having orgasms already.

I blushed at the news. I felt rather stupid, but he hugged me and told me it was okay. He said he’d help me out and took my hand, putting it in between my cunt lips and pushing my fingers onto my clit.

Then he told me to lay back, close my eyes, and keep rubbing my pussy ’cause he was gonna do something that he knew would make me feel real good. Ross then reached down and put his fingers in my freshly deflowered hole. I winced a little, but he was gentle, and his touch soon felt soothing. I leaned back, allowing myself to trust him while I stroked my clit. Slowly, Ross pulled his fingers out and slid them down to between my ass cheeks. I jerked as he touched my puckered hole.

Ross patted my ass playfully and continued circling the entrance with the tip of his middle finger as he asked if I’d ever play with my butt hole. Yeah, I answered gleefully ashamed. Ross laughed and then kissed me, pressing his finger harder against my hole until the tip slipped in.

At his urging, I leaned back again and breathed deeply as he pushed his finger all the way in. I gasped slightly at the wonderful feeling I got. Soon he was pulling it in and out real slow as I rubbed my clit again.

While he fingered my ass, Ross pursed his lips and leaned down. Pressing his tongue on my clit, he licked up and down, dowsing my pussy with gobs of spit while he ate my cunt and fingered my ass. I smiled as I felt myself rush with the wonderful sensations he was giving me, and just when I was heading towards that tickle I got under the water faucet, he raised his head and told me to finish playing with myself.

Obediently, I put my hand back over my clit. Soaked in spit and pussy juice, it was slick enough to glide over without discomfort. Soon, I felt the rush building again, an almost burning sensation right before I gasped and twitched with the wave pounding between my legs. Ross slid another finger in at the same time and fucked me quickly in rhythm with the pulse he felt in my ass. Over and over, he followed my body’s rhythm until I lay still, sweating, panting, and smiling like never before.

After my orgasm, he told me to pull up my pants so we could get the eggs and get back home. We finished driving up to the Gardner house, picking up the fresh eggs waiting for us. All the way back to my grandparent’s house, I sat right next to Ross, leaning my head against him with my arms wrapped around his hard bicep. He kept his hand on my leg, rubbing it tenderly. From time to time I would reach over and pat his crotch, rubbing his bulge teasingly.

When we got near my grandparents’ place, he pulled over, and we kissed one last time, at least for that day. It’d be another month before I got to see him again, and I felt so sad about that. Until then, he gave me his phone number and told me to call him. Ross promised we could still have fun even when we weren’t together, and he would be glad to teach me how, and I could hardly wait to get back home and call him.”

“He was your first phone sex, too, then huh,” I inquired, trying to concentrate even though I was ready to blow my load.

“Yes, but it’s late, and that’s another long story, Priest,” Diana told me with a smile as she patted my inflated half-zipped jeans, tipped the last of the wine down her throat, and stood up.


“Well, what, ma’am?”

“You wanna go up to my room?”

“Thought you’d never ask.” I stood up, pulled my zipper up carefully, and took her by the hand, walking over to the elevators. Pulling her close as we waited for the doors to open, I kissed her just as the doors closed, taking us where we both would get some much needed relief.

Updated: December 20, 2016 — 7:00 PM

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