Answer to DaneJutland’s: Your first experience
His full request or challenge was “Your first experience with a mature man or woman.” As I started writing a response to his post, I remembered the night as if it was now. So, decided to post here.
1960s, Indianapolis.
I was wearing my B..Sc..t uniform in a distant city while on a two weeks expedition through the western states for hiking and maturing. As the others went to sleep in the Y in their sleeping bags, I ventured out to explore. We were in the city center and there was an adult theater. Obviously I could not get in, but my cock got hard nonetheless. Then a mature woman, which I can now identify as a street walker, was walking slowly, looking for a new friend. She was full figured, not fat, just curvy with lots of stuffing in her ass, belly and her big breasts. She filled out a cheap light blue windbreaker and I could see her dark areola and spot her erect nipples. Her tight, very tight and very short white shorts, showed off her ass cheek bottoms and were tight on her cunt from the front. Her fake blond hair shined from the lamp lights as she sauntered slowly up the busy sidewalk. She crossed the street and walked toward the Y and I followed, probably looking ridiculous, like a starving puppy.
She walked past the Y and on into a neighborhood where the street lights were few and far between. In the middle of the block the shadows of the trees and limited lights made her harder to see. She sat on a house's three steps that went up to the lawn level, took out and lit a cigarette. I asked if I could sit there too. She looked at me and said why not. Her smoky, raspy voice was like an old B&W movie scene. We chatted, and I moved closer to her. Soon, it was cheek-to-cheek and I put my hand on her leg. She leaned forward and placed her big tit on my hand and rubbed it. I moved my hand under her nipple and enjoyed every second. She leaned back and spread her legs a little to open up her snatch. Her near arm was behind me for support on the house's sidewalk. I leaned into her full tit and she took the cigarette into her lips, dropping her left hand to guide my hand onto her crotch. She rubbed my hand up and down her tight shorts over her pussy. When I had the idea, she reached for her cigarette and leaned back as I rubbed her pussy. She responded, through pleasure or professional training and humped my hand for a few minutes. Suddenly she sat forward and her smoked cigarette went flying toward the street. She looked and me and kissed me. I was shocked and excited. Then she pushed her tongue inside my mouth and swirled and pumped. I was gone, clueless and happy. She took my hand and pressed into her breast, showing me how to knead and squeeze. Then she took my head and crammed my mouth on he r nipple. Now, this was I. The days of thick old fashioned bras, and she was big and needed the industrial type, but I felt her poking nipple and tried to suck on her. I asked if I could go with her, to do something…I was pretty clueless on techniques, but understood the main mechanics.
She had not touched my cock, or I would have cum for sure. Then she stood up, took my hand and walked further into the neighborhood. She turned right at the side street and then crossed into an alley half way down the block. She pushed me against a garage and leaned into me. Her big tits were about my mouth level and I did my best. She unzipped her jacket, unbuttoned her blouse and I tasted cleavage. Sweet, sweaty and amazing. “Are you quick?” She asked. I did not answer, since I was not sure what she meant. “Tell me before.” She fumbled at my belt, only to be confronted with a military sliding bar belt buckle. I helped her out. She unzipped my pants and pulled down my tighty-whites. He mouth swelled my stiff cock and I was stunned. So much better than my hand. What could ever top this? She slid over my cock and I felt her tongue swirling and caressing. I quickly erupted and suddenly heard choking as she pulled off. I looked down to see my angle spitting in disgust. “I told you…” I did not care. I looked down on a cheap whore, acne’s scarred face, great body, on her knees with my cum dripping from her lips. It was perfect.
“Can I go with you now.” I asked. She laughed and said I have more to do tonight, and you are done anyway. She stood, gave me a deep kiss and I tasted my cum on her tongue. Then she left as I pulled up my pants. I went back, crawled in my sleeping bag. But she was not quite correct…I came again before sleeping, sticky shorts to dry overnight.
1960s, Indianapolis.
I was wearing my B..Sc..t uniform in a distant city while on a two weeks expedition through the western states for hiking and maturing. As the others went to sleep in the Y in their sleeping bags, I ventured out to explore. We were in the city center and there was an adult theater. Obviously I could not get in, but my cock got hard nonetheless. Then a mature woman, which I can now identify as a street walker, was walking slowly, looking for a new friend. She was full figured, not fat, just curvy with lots of stuffing in her ass, belly and her big breasts. She filled out a cheap light blue windbreaker and I could see her dark areola and spot her erect nipples. Her tight, very tight and very short white shorts, showed off her ass cheek bottoms and were tight on her cunt from the front. Her fake blond hair shined from the lamp lights as she sauntered slowly up the busy sidewalk. She crossed the street and walked toward the Y and I followed, probably looking ridiculous, like a starving puppy.
She walked past the Y and on into a neighborhood where the street lights were few and far between. In the middle of the block the shadows of the trees and limited lights made her harder to see. She sat on a house's three steps that went up to the lawn level, took out and lit a cigarette. I asked if I could sit there too. She looked at me and said why not. Her smoky, raspy voice was like an old B&W movie scene. We chatted, and I moved closer to her. Soon, it was cheek-to-cheek and I put my hand on her leg. She leaned forward and placed her big tit on my hand and rubbed it. I moved my hand under her nipple and enjoyed every second. She leaned back and spread her legs a little to open up her snatch. Her near arm was behind me for support on the house's sidewalk. I leaned into her full tit and she took the cigarette into her lips, dropping her left hand to guide my hand onto her crotch. She rubbed my hand up and down her tight shorts over her pussy. When I had the idea, she reached for her cigarette and leaned back as I rubbed her pussy. She responded, through pleasure or professional training and humped my hand for a few minutes. Suddenly she sat forward and her smoked cigarette went flying toward the street. She looked and me and kissed me. I was shocked and excited. Then she pushed her tongue inside my mouth and swirled and pumped. I was gone, clueless and happy. She took my hand and pressed into her breast, showing me how to knead and squeeze. Then she took my head and crammed my mouth on he r nipple. Now, this was I. The days of thick old fashioned bras, and she was big and needed the industrial type, but I felt her poking nipple and tried to suck on her. I asked if I could go with her, to do something…I was pretty clueless on techniques, but understood the main mechanics.
She had not touched my cock, or I would have cum for sure. Then she stood up, took my hand and walked further into the neighborhood. She turned right at the side street and then crossed into an alley half way down the block. She pushed me against a garage and leaned into me. Her big tits were about my mouth level and I did my best. She unzipped her jacket, unbuttoned her blouse and I tasted cleavage. Sweet, sweaty and amazing. “Are you quick?” She asked. I did not answer, since I was not sure what she meant. “Tell me before.” She fumbled at my belt, only to be confronted with a military sliding bar belt buckle. I helped her out. She unzipped my pants and pulled down my tighty-whites. He mouth swelled my stiff cock and I was stunned. So much better than my hand. What could ever top this? She slid over my cock and I felt her tongue swirling and caressing. I quickly erupted and suddenly heard choking as she pulled off. I looked down to see my angle spitting in disgust. “I told you…” I did not care. I looked down on a cheap whore, acne’s scarred face, great body, on her knees with my cum dripping from her lips. It was perfect.
“Can I go with you now.” I asked. She laughed and said I have more to do tonight, and you are done anyway. She stood, gave me a deep kiss and I tasted my cum on her tongue. Then she left as I pulled up my pants. I went back, crawled in my sleeping bag. But she was not quite correct…I came again before sleeping, sticky shorts to dry overnight.
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