I’m not quite sure how to start off this story except to say I was in my early 20s, 22 or 23, and the woman would have been in her early 30s, either 32 or 33. She was about 10 years older anyway.
We met through mutual friends and there had always been a flirty relationship between us. She, we’ll call her Amy, would occasionally send me photos of her wearing a bra or of her body, showing off her curves. There was an instant attraction but both of us were too nervous to make the first move in person. Anyways, this changed when I went round to her house one day.
I knocked on the door and Amy answered. Amy was wearing a long flowing dress that went down to her ankles and showed off some of her cleavage. Amy was short, shorter than me, and had a slender body that had lovely curves. She had pointed facial features, but very attractive, and her boobs were probably B-cups.
She invites me in, we have a cup of coffee and all the rest of it. Amy suddenly stands up and invites me to look at something on her laptop. I follow her into another room and she sits down while I stand next to her. I think she knew exactly what she was doing because I had the perfect view of her breasts. Even if it was unintentional, she would have known but didn’t seem to mind. There had always been a flirty relationship between us but this shifted the mood in the room. I could feel my cock harden as I pretended to look at what was on Amy’s laptop but really I was checking out her boobs, thinking how much I wanted to see and touch them.
I can’t remember how this happened but we were suddenly laying on the floor on our stomachs, very close to each other. There was a heightened energy in the room now. Our conversation had begun to get more and more flirty, we both admitted we found each other ‘hot’ and suddenly we started making out. Passionately. It’s a bit cringe to think back now but we were literally rolling on the floor kissing each other. Because we were both had small frames, it was no effort to put the other on top.
I’m a bit ashamed and embarrassed by this next part, but I’m being as honest as I can be. This was the first time I had been in this situation (I had made out with one or two girls prior to this but nothing this passionate) and Amy’s dress had ridden up to her underwear. I was wearing denim shorts (don’t judge, this was a different time) but I could feel my cock rubbing against her pussy through her underwear. And I came. I could feel my sex drive waning a bit but I continued making out with Amy and I was curious to see where this was going to go.
After another minute or so of making out, Amy suggests we should go to the bedroom. The bed would be more comfortable than the floor. I nodded enthusiastically. She took me by the hand, led me to her room and closed the door behind us. She pushed me up against the door, kissed me on the lips, before making her way down. I knew what was coming and tried to remain calm. It had already been a big afternoon for this awkward virgin.
She sank to her knees, undid the fly on my highly fashionable denim shorts and reached in. I had no idea how the little fella was doing down there, if he was soft or hard but luckily, and much to my relief, he was standing to attention again. To be a 22/23 year old again.
Amy took my cock in her hands, admiring it. Not that I think it’s anything impressive. About six inches or so but she seemed to be happy with the size. After pumping it a couple of times, she took the tip just inside her mouth, started to slowly move her head up and down and played with it with her tongue. I very nearly went over the edge, especially when she looked up at me.
Not wanting a repeat explosion just yet, I reluctantly pulled her up to her feet and awkwardly guided her back to the bed where we lay next to each other kissing and rubbing our hands all over each other’s body. My hands were clumsily feeling up her boobs and I was trying to pull down her dress to get at them. She said she was thinking the same thing and suddenly got up off the bed, left the room and returned a few seconds later holding her dress in front of her. She then let her dress drop, revealing her naked body except for a black pair of underwear. I can’t remember my reaction, I was probably looking at her dumbly. This was the first woman I had seen naked – or near enough to – in person. And an attractive one at that. I tried to take in her naked body as much as I could. Her smiling, beautiful face, her shoulders, her perky breasts with pointy nipples, her toned stomach, her curves, black underwear and beautiful legs.
After a couple of seconds, Amy rejoined me on the bed. We began making out again, taking off my shirt, rubbing our hands over each other’s body, I squeezed her breasts and rubbed her nipples. I could feel her hand run down my chest and stomach to my cock where she slowly started jacking me off. I broke away to suck her nipples and to motorboat her (remember it was my first time seeing breasts in person) Which caused her to laugh.
She stopped me for a moment and settled down in the bed, looking up at me expectedly. This might have been my first time but I knew what she wanted. I got up onto my knees and shuffled round to her legs which she opened for me. I stayed there for a moment, trying to remember everything about her naked body. I looked up and saw her staring at my erect cock and balls. With a deep breath and shaking hands, I took off her underwear, revealing her wet pussy. I couldn’t restrain myself any more, I laid on top of Amy and with a shaking hand tried to direct my cock into her pussy.
Luckily Amy was patient and tried to calm me down. I finally found the entrance and pushed myself in. Probably way too quickly. Then, I froze. I literally could not move. I was worried if I even moved a little, I would cum again. Strangely, having cummed earlier might have helped with a longer build up during our earlier activities but now, the volcano threatened to erupt at any moment and there would be no survivors.
Amy asked if I was okay and I managed out a simple ‘yes’. Pretty lame. She suggested if she should go on top, which I agreed to. Amy rolled me over, straddled me, took my cock in one hand and slowly slid herself onto me. I could feel every inch inside her pussy. I breathe in sharply. Her pussy was warm and wet, I had never felt anything like it before.
Amy slowly started to move up and down. I reached up and play with her boobs and she leans down so I could suck on them some more. I automatically started to thrust but our sync was way out. It’s too late anyway. The flood gates were about to open.
“I’m going to cum,” I said to Amy but she didn’t seem to care. She stayed on me as my balls pumped what was left inside her. I was freaking out because you know, pregnancy reasons, but she assured me she was on the pill. Nine months later there was no baby so she must have been telling the truth.
In the post nut clarity, we awkwardly disentangle ourselves, got dressed and I left, embarrassed.
We never fucked again but there were some make out seshes but they aren’t worthwhile writing about here.
Anyways, if you’ve come to the end (sorry for such a long story) – thank you for reading!
Source: reddit.com/r/gonewildstories/comments/yivkul/losing_my_virginity_to_a_woman_older_than_me_mf