Maybe everyone has one of these stories, one of these memories? The one that makes you instantly hard or wet when you think about it, makes you re-live that experience like it happened yesterday. I don’t know about you, but I certainly have one.
When I was nineteen or twenty or so, I went on a dating website and answered an ad that an older woman had posted. She was looking for a younger man to go out with, to have sex with. There were no pictures on the site, there was no Tinder back then. We chatted for a bit and after a couple of days of that we agreed to meet at a bar, just to see what we looked like and if we wanted to take it further at a later date.
I can’t remember exactly, but I can guess that I was really nervous before the first meeting. I was quite young and inexperienced, at that point I had had sex with two girls, both my age and my “serious girlfriends”. The relationships didn’t last that long, the sex was quite nervous and experimental, we were trying to find out what we liked and how to act with another person, naked and vulnerable. I was a tall and skinny kid back then, not that sure about myself or confident in my physicality. I wasn’t awkward or anything, I was just young and inexperienced.
I don’t know what made me sign up for the dating site after these experiences or what made me message that older woman. I guess I wanted to know if I could do it, if I could have sex with someone I didn’t or care about on a deeper level. Maybe I wanted to find out who I was.
I was standing outside the bar a couple of minutes before our agreed upon time, when a woman walked up to me and said “Hi, are you Tom?” She was quite a bit shorter than me, a bit over 160 cm (what is that, 5’ 3” maybe?) and she had a round figure. Short hair, full cheeks and beautiful, beautiful lips. I nodded and replied “Yeah, and you must be Karen?” She said she was as she was checking me out. She smiled and said “Okay! Should we go in?” And in we went.
We had a pleasant enough time at the bar – a beer for me and a cognac for her – first making small talk and then getting to know each other a bit. She was 46 and married, working at an office somewhere nearby. She had short blonde hair and dark eyes. She kept leaning over the small table and I could see down her cleavage, white skin between her large round breasts. She only had time for that one drink, which was what we had agreed to beforehand, but I would have liked to take her to my place right then and there. I didn’t know what it was, but I really wanted to be with her. She wasn’t sexy or beautiful in a bombshell, film star, traditional way, but I was instantly smitten.
We parted ways after leaving the bar and almost immediately after she had left my eyesight, I received a text message about the next time we could meet. She wanted to come to my place a week from that night.
The week went by quickly. There was no texting or anything between us during that time, but the excitement was building up in me nonetheless. When the time came, I put on my best button down shirt and my one pair of nice pants and waited for her on the couch in my bedroom. I was living in a shared apartment, which I was glad to find empty of my flatmates. After a nervous fifteen minutes, the doorbell finally rang. She was here. I was actually going to do this!
I opened the door and invited her in. She looked the same as that night at the bar, same color of lipstick and same type of clothes: a tight pair of jeans, a smart blouse, nothing special. I gave her a quick tour of the small apartment and lead her to my room. I locked the door behind us.
We went straight for the couch, no awkward small talk or offerings of water or anything. We sat down next to each other and looked each other in the eyes. “Kiss me,” she said and I complied. She had beautiful, thick lips and a pinkish shade of lipstick that made her lips look like candy. I went in for the kiss and slid my hand on her thigh. We were both a bit cautious at first – she was married, I had kissed maybe four girls and never someone as old as her – but quickly found our rhythm, the way that we both liked kissing and to be kissed.
I slid my hand up to her breasts and started to open the buttons on her blouse. She helped, it seemed like she was eager to get my hands on her breats. Once her shirt was open, she put her hands in her bras and lifted her big, round breasts up from the cups. I’m not sure, but I think I actually stared at them before I could compose myself a bit and put my fingers on her nipples. I bent down and licked them and sucked them until they were hard on my tongue.
I lifted my head up to kiss her neck and up to her lips and she started unbuttoning my shirt in turn. Her hands were on my chest and my sides and then down on my lap. I was as hard as I could be, her hand finding her way to my shaft. We were kissing again, her hand stroking my cock through the cloth. Then she opened the buttons on my trousers and got my cock out into the air. Her hand was on it, she was holding it like it was something precious and valuable. “It’s so beautiful” she said and kissed me again.
Then she slid down on the floor, positioning herself on her knees between my legs. Without saying a word or waiting for my reaction, she grabbed her soft breasts and wrapped them around my cock. She was staring at it, engulfed between those big mounds and starting to move them up and down, up and down on my cock. She pressed them against it with her hands, applying pressure and moving them quickly along the shaft. She looked like she knew what she was doing, determined to give me pleasure with her hands and breasts.
I was in heaven. I had never had anyone do anything like that to me. The sight of that older, forty-year-old woman there on the floor and between my legs, rubbing her massive, beautiful, soft tits on my cock was something that I never could have even imagined. It was hot, it was sexy, it was deeply erotic and arousing. I grabbed the couch with my hands, gripping it when waves of pleasure washed over me as she continued to jerk me off with her breasts. I knew I couldn’t hang on for long.
“Please, I’m going to cum in a second if you keep doing that,” I whimpered and she just glanced up at my face and kept going. She was staring at my cock as it kept appearing and disappearing between her moving, bouncing tits. I could feel my body tensing, starting from my feet and going up to thighs, my ass and my back. The orgasm was building up inside me and I grabbed the couch tighter, moaned aloud and when she pressed those breasts against my cock even tighter, I came hard and fast. Sperm spurted out from my cock and onto my stomach in long, white streams. Still she kept pumping those breasts around it, slowing down and easing the pressure just a bit. My cock was still twitching with the aftershocks and I was breathing heavily. What an experience, what a feeling!
She let go of her breasts and put her fingers delicately on my cock. “What a beautiful thing you are,” she said to it and gave it a little kiss on the head. She put her breasts back in her bra and buttoned up her blouse as she stood. “Right, I think I’ll go now,” she said and started gathering her stuff. I sat there, my shirt open and my own cum covering my stomach. I grabbed for a paper towel to wipe myself off so I could escort her out of the apartment. I made some attempt to get her to stay, but she wanted to go. Maybe that was enough for her as the first step, making a young guy cum with her large breasts. I certainly could have done something else as well, I would have loved to enter her and make her cum as well, but I knew we could do it some other time.
But that other time never came. We were supposed to meet up a couple of times after that first one, but something always came up and then I think I met someone and, well, that’s the way life goes sometimes. You get to have something once and never again.
Now everytime I think of that night, I get instantly hard and excited. Just thinking about that feeling of having my cock stroked by her soft breasts gets me close to the edge in a second.
And the image of her pink, perfect lips on my cock head after the best orgasm of my life, well that has burned to my mind forever and will be with me until the day I die.
Source: reddit.com/r/eroticliterature/comments/ptuot3/mf_i_will_always_remember_my_first_time_with_an