My First Time With A Man Pickup

It's been a while for me, and I haven't had it since I was in my mid-twenties. But if you've got time, you'll understand why I have fantasized by it for many, many solo sessions and more.

I'm 49 now, 6' tall blondish-brown hair, smooth skin, still very horny all the time. My tools aren't huge, but beautiful. I love to masturbate and edge for hours if possible. When my bulge is bulgier than most of my edging sessions, I can't help to think of the first time being with a man, the feelings that I've never felt before, the taboo thoughts, the energy of two cocks rubbing together and the act of submission was the best ever.

It felt so fucking good that every man, woman and or whomever you may be, should experience the same sex at least once in your life. That is what I remember of my first time with a beautiful muscled, bronzed skin, smooth Latin man.

As many woman I've had the pleasure of being with, there was nothing that more exciting- to this day. Here is my story of the first time I truly let go.

It was a hot July day. I was traveling to Chicago (Naperville). I got back to the hotel at 6:30, felt I needed a shower after a long day driving around the city on sales calls. Afterwards, I didn't want to lay around the room so went down for a cocktail at the Red Lion Hotel bar. A dark skinned man was sitting on one corner of the bar talking to the most beautiful woman I had ever seen. I sat down at the other corner to his left. He welcomed me with a big smile, white teeth, blue eyes, a beautiful tan and smooth skin. I ordered a drink, probably a rum and coke.

The lady departed and for some reason, I asked him what he was drinking. Something about the way he said, "Kamakazi" put a warm wave of energy that something good was going to happen.

We talked, gazed, and enjoyed each others time for about 2 hours or 4-5 cocktails. I recall somewhere down the line where he brushed my arm and put his hand on my shoulder when he excused himself to go to the bathroom.

Flooding with warm energy, I suggested we go to a bar nearby or grab some dinner. We never make it that far. When we got up, I felt his hand brushing my ill-positioned semi- hard cock.

He fixed it and whispered "I have drinks in my room." From that point, I was in his power and I knew what I could be in for.

In the elevator, we tried to maintain with other guests present. I couldn't help but to notice the outline of his pants sticking out. Even though there were 3 others in the elevator, I snuck a peek of his hard-on and could not get enough of the blood flowing through those veins around that silver dollar 8" beautiful piece pressing against his linen slacks. He couldn't of had underwear on and his bulge was obvious.

Getting off the elevator, I didn't care any longer. I was buzzed, and I would have sucked him right then and there if I could, I kept reaching for that outline in his pants on the way to the room, and every time I did, he would smack my ass just a little harder. This was escalating quickly. I was full of anxiety, and rushing with anticipation.

His room was all the way down the hall and I couldn't believe I was going to experience another man's touch, but I didn't care, I would worship this man tonight and feel whatever guilt I'm gonna feel tomorrow.

I felt warmth in my crotch so I reached in, and touched the tip of my cock and pulled a string of silky pre-cum to my finger and then put it on my lips like I do when I masturbate. The anticipation went from my cock to my head. This was lust, uncontrollable, meant to be, anticipation to the greatest degree with a nervous energy that could be described as butterflies.

With every passing second I could only imagine the things that I was gonna do with this clean laced Caribbean stud wearing linen pants and no underwear a white buttoned down shirt with a smooth hairless muscled chest. He must have been more than 6'2", taller than me, very masculine yet a sense of sensuality, and femininity.

I couldn't take this any longer.

We got to the door. At first the key card didn't work. Once, twice, yippee! Third time is a charm. Within seconds of the door closing we were in each others grip, his arm above my hip exploring, and grabbing my backside from my lower ass cheek to my neck- his hands were strong yet soft. I kept wanting to reach down and grab his beautiful tower of art that curved up so slightly to the right and felt like it had a mind of it's own. Uncontrollably we both were grinding our hips together. Kamikazee!

I wanted to touch his entire body, but I put my hand inside of the front of his pants, wrapped my fingers and slid down his entire shaft. It felt so much bigger than mine and it was a feeling of exhilaration. I felt the same silky, warm lube that I had just pulled from my own cock. I leaned down and kissed it noticing that it wasn't 8", it felt more like 10"- my forearm compared with girth that was larger than the head.

He was rock hard. I set his throbbing beautiful penis from his pants, it stood at attention, like a spring it pointed to the sky. The tip was dripping a warm soft liquid that I couldn't resist. I tasted it with the tip of my tongue, still a little nervous but very curious and so damn horny.

Here I am, I was with a girl a few nights before and now I'm on my knees, his pants were now at his ankles and I couldn't wait to taste more. The slightly salty skin that attaches to the head was my next move. His cock flinched and felt a little bigger and harder. He wanted this as much as me.

The uncircumsized skin moved so effortlessly as I stroked it. I couldn't let go. My lips couldn't stop kissing and lapping up that warm silkiness of his soft and sweet pre-cum. I wrapped my other hand around the base of his cock, stretching his skin back and forth for what ended too quickly. I needed to lick and to feel his freshly manicured balls which were supple and full.

Instead, he pulled me up and sucked on my neck, turned my head and kissed me and bit my chin softly as if to say "lets do this." He knew what he liked, he'd done this before.

Both of our cocks rubbed together at some point and both of our hips pushed towards each other. I could have grinded him for eternity. The energy of two cocks touching was like we were connected. Both of us were dripping lube and it made the sliding and grinding perfectly slippery.

He smelled of an expensive cologne, woodsy, combined with a citrus smell. His cheeks, and chin had stubble that felt like soft bristles. I kept kissing his neck, and ears.

I squeezed his nipples, and he pulled me up by the bottom of my ass. For some reason, I wrapped my legs around him and said, let's lay down. I pulled his pants the rest of the way off. and couldn't believe his ass was so round, so hard, so tanned and so perfect. He unbuttoned his shirt and revealed he smoothest chest and abs. I put my hand down his lower back and felt the his sculpted cheeks, wandering, warm, inviting and grinding on me as if wanting me to pull it closer down his ass. I took the chance and rubbed my middle finger so softly around his hole that he grunted ever so slightly in my ear with a deep breath, spread his legs and started slowly stroking his beautiful piece.

I was a different man that night, I could have taken 5 hard cocks and loads of cum. I'm not sure if it was the alcohol or what but I became a submissive toy for whatever he wanted.

We rubbed our cocks together with just a little oil. I turned him over, lifted him up so he was doggy style in front of me. I spread his cheeks and tongued the back of his balls (I really like when it's done to me and I know he felt the same). I ran my tongue over his ass, and instinctively put a little pressure. There was soft peach fuzz that felt so incredible. His anus was soft, puffy and slightly rosy pink.

I stood up, put my cock in my hands and dry humped his backside as I kissed the side of his neck and shoulders. He played with his cock with one hand, moved his hands around to my ass and put a finger just inside and pulled the side as if to say he's ready.

I don't know who liked it more. Me grinding my pre-cum silky cock and touching his anus with the tip of my cock all the way down to the balls, or him loving the smooth grinding and my hands and nails softly down his back. I felt like he wanted me in him, but I couldn't yet, although I could think of nothing hotter. I didn't want this to end.

I wanted him in my mouth as deep as I could go. I've practiced with things before and I couldn't wait. I put it in my mouth and couldn't believe how wide it was, how pulsated the veins were, how big his mushroom head was, and how salty and delicious it tasted. I went deeper, I went faster, gripping my lips every time he pulled back and I could feel the texture of a soft skin of his head, followed up by a hard mash to the back of my throat. The bottom of his cock slid on my tongue as he pushed in. His vein was enormous. I could feel the pressure building. I couldn't breathe but I didn't care.

After 5 minutes, I felt him tightening up. My eyes watered, and I softly tickled and stroked the back side of his balls, carefully squeezing each testicle, pushing one finger in his hole.

Instantly, I felt his hands on the back of my head, pulled me close, his tool going deeper in my throat, faster. He flinched, quivered, groaned and shook. I took his load, all of it. He continued to convulse, and pulled me closer to deposit his warm juices. His dick was so far down my throat I thought I would choke.

I never tasted a thing but I know it was there as I could feel it shooting deep down my throat, his dick pushing more and more cum in my mouth. He pulled out, wiping the tip of his head onto my cheeks, I took a deep breath, tried to clean it up but just wanted that cock even more so I pulled it back into my mouth and tried to lick as much of the cum out as I could before he went soft.

Even though I had never done anything like this, I fantasized about it and I wanted to prove to myself and him that I am an incredible cock sucker and it is as sexy as it sounds.

After he came and I licked every drop, he giggled, we laid down for a few minutes, I tickled his back, and grinded my unspent cock just inside of his ass cheeks softly so that I wouldn't cum yet, although I needed to cum. I couldn't control the thrusting of my hips.

Once he felt that I was rock hard, he turned around, laid me face down, ass up and gave me the massage of my life. He put a pillow under my belly, my ass slightly up, he oiled me with warm oil that he prepared in his hands. He spread my cheeks, rubbed everywhere around my inner thighs with both hands. Eventually he slid his finger in my ass. It was a feeling I had never felt before.

He knew where to press, where to explore. He pulled my cock back from under me and worked it like a pro, barely touching and kissing the most sensitive part of my shaft with his tongue and lips sliding up and down my shaft like he was playing the flute.

Oil covering his hands he wrapped them around my tool- that was harder than usual- and pulled on it keeping pressure on the sensitive area. He stopped, stood up, pulled me closer to the edge of the bed, spread my legs apart and I felt the tip of his cock and balls sliding up and down the lower back and upper part of my ass cheeks. He was rock hard again.

He turned me over, spread my legs and again ran his oiled finger softly inside my tight hole.

I felt a tickle. His finger was softly pressing on the front inside of my ass. I grabbed my legs and submissively pulled them towards me. I looked at him as if I was saying. "yes." I felt the hardest yet softest, warmest cock exploring around my ass pushing inside ever so slightly, pulling back, and then back in as if to train and prepare me.

I felt that nervousness of anticipation. I needed it harder and deeper. I wanted to feel him deep inside me. I wanted to be submissive and feel what it felt like to be fucked. I wanted to watch him enjoy me, use me, and I was ready to serve.

It was painful at first, that involuntary clinch. I gave in, relaxed and let it happen. When his giant cock was 2-3 inches inside of me, I knew I wanted the whole thing. I knew I could and the day came. I felt warm coconut oil being put generously on my ass, he looked at me in the eyes and it slid in, further, wider. We were connected and for that moment I was his and he was mine.

Ecstacy was all I felt, he pushed hard and slow. I felt the head, I felt the veins, and after 5 minutes of pure ecstasy with him pumping hard, I felt his cum for the second time. For 4 seconds I couldn't move. He was gushing in me, he went deeper with every push, and I had mini-orgasms every time he did.

I'd never felt an orgasm like this without stroking my cock, which was somehow semi- flacid. I felt him squeeze, he pulled out slowly and dripped more on cock, ass and balls.

The warm liquid leaked from my ass down to the bed. I could feel him pulling me closer to him, he grabbed the back of my neck, and my lower back and he pulled with everything he had and he grinded as close to me so I could now cum on his slightly soft spent cock, his balls rolling alongside both sides of my shaft.

I laid back again, he straddled me, put his cock on top of mine and slid back and forth. It felt so good. He knew exactly I wanted him to feel my cum, to push our cocks together and lather in each others juice. I closed my eyes and had the absolute best orgasm, shooting multiple loads of cum between our bodies and onto his sculpted tan belly. The roller coaster feeling lasted at least what seemed like eternity. We laid together, again, he looked in my eyes and both of us laughed. Our cum still between us and our semi-soft cocks still grinding together softly. Our legs were intertwined and it felt like heaven. Zero guilt.

He knew what he was doing. He'd done this before and I don't blame him. I was temporarily spent. I slept for a few minutes and then felt I needed to put my hand on his ass cheeks. Before I knew it, I was cumming on the backside of his ass. What cum I had left seeping down in his cheeks. I kept grinding deep into his spread ass cheeks. He too was hard as he'd been 4 hours earlier. He came with me, rubbing his own dick. He had a huge load in his hand, that he fed to me and I don't know if I loved his fingers being in my mouth or the taste and feel of his warm cum.

We played all night. We ordered room service, and beverages, fed each other and flirted. The room was trashed, our clothes were everywhere, the smell of musty sex lingered. He joined me in the shower and I left him in the morning, I had a spring in my step. I had just done something that they say is so wrong but feels so fucking good. No guilt, no remorse. I have visualized this story for years and it is still as sexy as the day it happened. If I see him again, we'll grin, and maybe even grind. He told me he went by Dino, and he played one year Major league baseball. From the DR, but living in Florida.

I Hope some of you have met Dino in passing.

P.S. Thank You again for reading! I had the biggest hard-on writing this story. I'm glad I did and the orgasm to follow was a deep relaxed roller coaster ride as it always is, full of cum pumping and dripping down into my hand. It's now been 4 hours since I wrote it, and I just re-read it once again, I have my beautiful cock in my hands as I hope you do too. I regret not entering him, and I have never had an opportunity to do this again, although I wished maybe someday it would present itself. I hope you enjoyed my story.