I’m sure that we all remember our first time. We remember with fondness the guy that made us feel accepted and special. We remember our first love, so deep it hurt to be apart and nearly killed us when it ended. So many memories, tucked neatly in the files of our minds waiting to be savored like a fine wine in a passing moment. I shared the story of my first time with you awhile back and received so many wonderful comments.
After that, I shared a fantasy and again enjoyed your approval. Today, I want to share another memory. This one is from slightly later in life, Jeff and I have split and I have started to move on. I hope that everyone enjoys my tale, maybe it will trigger a memory for you.
I stepped out of the shower and began toweling myself dry. I had gotten home from work, gotten a bite to eat and was cleaning up to go out. My eyes traveled to the mirror and I looked at my naked body. My summer tan, bronze and dark, with no lines thanks to my nicely private balcony where I caught my sun. I quickly finished drying and moved to the bedroom to dress.
I stood in front of the closet for a minute before pulling out a pair of tan slacks and a black button down shirt. I thought about work as I slipped into a pair of skimpy yellow bikini briefs. Pulling on the slacks, I pushed that out of my mind and began to concentrate on the evening ahead. I had been so busy for the last few weeks that I hadn’t gone out at all. Work, my recent split with my lover and other things had been more important. Today at lunch I had decided that tonight, I was going to bust loose and enjoy life again. I slipped into a pair of black loafers, looked in the mirror and smiled. I looked good and I was on my way to dance and enjoy a night on the town, look out world.
I got to Ziggity’s about 30 minutes later and ordered an Absolute and tonic from the bar. A very cool place this is, lots of neon, plants and an art-deco kind of feel. There’s a large dance floor in the middle and several small seating areas spread around the room as well as a balcony area that circles above. I scanned the room and sipped my drink, beginning to relax at long last.
After awhile I started dancing, moving around the floor and letting the movement wash away my tension. Occasionally, someone would join me for a moment and then move on. Everyone was just warming up on a warm April evening. After quite a few songs, I went back to the bar and got another drink before finding a seat in a small alcove just off the dance floor that had a view of the fountains outside.
A few friends stopped by to say hello, a couple of them stayed to talk for a bit and went back to the dance floor or some other place. I sipped my drink and watched the room, my mood getting better all the time. I was looking out the window at the fountains, listening to the music when his voice startled me, “You looked thirsty over here”.
I turned, smiling as he sat a fresh drink on the table. I thanked him and invited him to join me. He told me that his name was Bill and that he was in town on business. We talked for a bit and I looked him over discreetly. He was older, maybe 35, with short, dark hair and deep brown eyes. His t-shirt wrapped around a tight waist and thick chest and his occasional smile was warm and inviting. We talked for a bit and I found myself enjoying his company. I had never been with anyone older than 22 or 23 before, so talking to someone who was wiser was refreshing, almost invigorating. He had a quick wit and….something else. He leaned in toward me and I took in the aroma of his cologne as he spoke. “I don’t dance and I’m not sure how you feel, but I have a hotel room up the street and would love to get to know you much better.” He said. Then I felt his lips brush my neck and I knew that I had to say yes.
We left the club and walked out into the warm spring night. Since his hotel was only a couple of blocks away, I decided to leave my car. We walked up the street, talking and laughing. We came to an art shop and I stopped to look at a picture. As I stood looking, Bill moved in behind me, wrapping his arms around my waist and pressing against me. I sighed softly as he kissed the back of my neck.
After that we, we quickly finished the walk to his hotel and got into the elevator to his room. I watched as he pushed the button for the 40’Th floor and felt the car start to rise. I smiled as he moved closer and placed his hands on my hips. I sensed that he was getting a bit nervous and I leaned forward, kissing him softly. I felt his hands tighten and we came together in a full embrace as our mouths moved roughly together. We pulled apart as the car stopped and a young couple entered. My mind raced, as I grappled with the fact that I was going to a hotel room with a guy that I had just met for the first time in my life.
Up to now, I had only been with friends. Jeff and I had occasionally invited a guy over to join us and on a few occasions, I had been with guys that I knew from the area alone. This was different. First, I had only known Bill for an hour or so and second, he was quite a bit older than I was. Both facts combined to send a rush of excitement through me. We got to his floor and quickly moved down the hall to the room.
Once inside, I looked around, taking in the king-size bed, a balcony looking out over the city and the smile on Bill’s face. I accepted his offer of a drink and excused myself to the bathroom. I came back into the room to find Bill on the balcony. I joined him and we talked while sipping our drinks and looking out over the city. I was feeling very relaxed and warm with him and was wondering if he was ever going to make a move.
Just then, he sat down his glass and turned toward me. I sat my glass next to his and looked into his eyes, smiling reassuringly. I gasped as he took me in his arms and began kissing my neck. Not in the soft, gentle way from the street, but more forcefully, almost desperately. My arms wrapped around him as his lips came down hard on mine and his tongue began to probe my mouth.
We broke our kiss and he began to take off my shirt, his fingers fumbling with the buttons as I pulled his shirt over his head, exposing his thick hairy chest. I moved my hands to help him with mine and slipped it off my shoulders, letting it fall to the ground. My hands moved to his belt and he started to lead me back into the room. I smiled as I un-did his slacks and knelt at his feet, wanting him right there on the balcony.
I helped him out of his shoes then returned to the slacks. Taking the zipper down and pushing them down. He stepped out of them and I moved my hands up his legs until I came to his boxers. I kissed a thigh and then moved higher. My nostrils took in his lovely aroma, a combination of him and a trace of cologne. My hands pushed up and stroked his very nice bulge through his boxers. I looked up and saw a smile on his face, “Do you like that Bill?” He nodded and I pulled the underwear down to expose his lovely cock.
I let my eyes travel slowly down his now naked body, taking in his oh so sexy masculinity. He was square-jawed and handsome in that rugged, 1950’s kind of way. He had short, dark hair and was clean-shaven although he did have the stubbly growth of the day. His chest was covered with a mat of hair that thinned as it grew down his flat belly before coming to the thick thatch at his crotch. His cock was nicely long and a bit thicker than most with a pair of large balls hanging beneath it.
I reached up and cupped his cock and balls in my hand for a moment, loving the heaviness of him. I heard his sigh as I gently kneaded him. I looked back into his eyes as I wrapped my hand around his cock and stroked it slowly from base to tip. I leaned forward and kissed his balls gently before sucking one into my mouth. I heard a deep groan as my tongue rolled it then sucked the other. I could feel his cock beginning to thicken and I left his balls to move on to more interesting things.
I let my tongue and lips slide up his shaft, going ever so slowly, relishing the feel of his flesh. “God, I love your cock.” I whispered as my lips came to his tapered head. “Mmmm, and I love your mouth…oh yeah.” he groaned as I kissed and then sucked the head between my lips. Slowly, I rolled my tongue around him, moving back and forth, as I sucked only the head of his sweet cock. “Nooooo.” I groaned as I felt his hands grabbing my shoulders and pulling me up into his arms.
I moaned as his lips found mine in a long gentle kiss. Our tongues played and we both ran our hands over the others bodies, his stopping to cup my ass. I was almost giddy at the feel of his body against mine, the hair of his chest rubbing against mine. We broke our kiss and he took my hand leading me back into the room. We came to the bed and I smiled as he gently guided me onto it. His hands removed my slacks and then slid my briefs over my hips. “Oh Jesus, you’re so hot.” He said as he slid onto the bed next to me and pulled me into his arms again.
We kissed and stroked for several minutes, enjoying the closeness. After a bit, he pushed me onto my back and began kissing down my body. I sighed and relaxed as his expert mouth teased me. He would kiss here and lick there, sometimes stroking a spot before his mouth got there. I felt him pull a nipple into his mouth and groaned in approval as he nibbled on it. He continued and I just spread out, giving him access to anything that he wanted.
I felt his mouth pass my erect cock and then he was kissing my thighs. He licked my balls and then began sucking my cock, taking the whole shaft deep into his mouth. A hand massaged my balls as he moved up and down on me. I flipped around on the bed so that I could suck him, quickly engulfing his cock in my mouth. I felt like I was in heaven with his rock hard shaft in my mouth as his fucked me. I was getting very close to shooting when he pulled back and flipped me over onto my belly.
His hands grabbed my hips and pulled them from the bed and I gasped as I felt him kiss my exposed asshole. “Mmmmmm, such a sweet ass.” He said and then began to probe with his tongue. I pushed back toward him, moaning as he kissed, licked and slowly probed me with his tongue. I felt his hand move over my ass and then took in a deep breath as he slid a finger inside me. “Oh God yessssss.” I hissed as the thick digit slid deeper and then began to move in and out of me. He worked slowly and gently, taking his time to spread my tight anus.
I was tingling all over, my cock throbbing from his attention. His finger began thrusting in a bit faster and then he slowly inserted a second, spreading me even wider. He began thrusting in and out and then pulling out to tongue me. I moaned and groaned, loving every second. I was so hot, my cock throbbing and my ass tingling and I knew that I had to have him.
I rolled over onto my back and pulled him to me. I kissed him then took his face in my hands. “I want your cock Bill, fuck me please.” I said, my voice quivering with excitement. He smiled and then moved to kneel between my out-stretched legs. He took them in his hands and lifted them to his shoulders. I watched as he took his cock in hand and sighed as I felt the head press against me. Slowly he pushed forward, the head slipping easily into me.
I gasped as I felt him push another inch into me and he stopped. I saw a look of concern on his face and I could tell he was concerned about hurting me. I focused on his eyes and my hands grabbed his hips. I smiled and pulled on him, urging him to take me. “Take it baby, fuck my ass.” I growled. Then I stifled a cry as he gathered himself and buried his hard, fat shaft in my willing ass. “Oh my sweet God.” I whimpered as I felt his balls come to rest against my butt. He stayed there and I trembled beneath him, my ass slowly relaxing around the invading cock.
I felt him slowly pull back until just the head remained and then begin to thrust in and out of me. Again, he worked with a skill that I was not used to. One minute he was slowly moving in and out and then suddenly, thrusting into me hard, fast and deep. I moaned and groaned and whimpered beneath him. “You like that cock in your ass baby?” he asked as he thrust into me. I groaned deep in my throat, “Oh God yes, I love your cock,” I gasped, “Now fuck me, use me, fuck my sweet ass!”
I was quickly rewarded, as he began to slam his cock into me. His cock was like a piston, ramming deep into me with long, steady strokes. Then he pulled out and rolled me over. I quickly raised my hips and felt his cock slide in from the back. I cried out as he found bottom as the new position allowed him to go deeper. He started to thrust, driving himself into me with abandon and I groaned in approval, begging for more.
I lost track of everything except his shaft and I cussed and whimpered, more aroused than ever before. “Oh yessssss Bill, fuck me!” I cried, wanting him to know how much I loved it. I felt a hand wrap around my chest and he pinched a nipple…hard. That was all it took and I felt my cock swell and my balls tighten.
“Cumming! Oh God, yessssssss.” I cried and then groaned as I felt my cock explode, spraying a huge load of cum onto the bed below me. I could feel my ass clenching his thrusting cock as I came and each thrust pushed even more cum out of me. Then I heard him, a deep, throaty growl and his body tensed behind me. “Gonna cum…Oh yesss…gonna cum.” He said. I looked back, “In my mouth Bill, cum in my mouth.” He quickly pulled out and I rolled over. He was stroking his cock and I quickly took it in my mouth, wanting his load.
I felt him swell and then a huge blast of cum shot into my mouth. The force of it surprised me and I pulled back instinctively. I was rewarded by another, even larger shot splattering on my face as he grabbed his cock and stroked quickly. Two more streams coated my face and then he stopped stroking. I moved forward and took his cock in my mouth, feeling the sticky cum coating my face as I sucked the remaining drops.
Finally, he collapsed to the bed and I rolled next to him. I smiled at him and started rubbing his cum over my face, stopping occasionally to lick a finger. We kissed and caressed and at some point, I fell asleep in his arms.
I woke up in the morning to find a note lying on the pillow.
“Last night was wonderful. Sorry I had to go, but I had to get to a meeting. I’m flying out right after so this is good-bye. Thank you so much for a wonderful trip.”
I showered quickly and headed home. My thoughts were sweet as I remembered the night before. I only regret that I never saw him again.
Well, that’s my story. I hope you enjoyed. I hope that it will trigger a happy memory for you. Oh, and Bill? If you happen to read this and remember a night in Chicago, drop me an E-mail at this site.