18yo sex with my 34yo sister in-law
I've had a story I've not shared with anyone for fear of it getting back to my brother.
When I was 18, my father died suddenly the day after Christmas. As many families do, we all gathered together to comfort each other over the ensuing days. We found ourselves sitting around the house telling stories just like any family might.
My next door neighbor, to help with sleeping arrangements, gave us his house for a few days. We went over as a group to check the accomodations and, after some time most everyone went back to my house but my sister in-law (32) hung back to lay out her things and I was hanging out in the backyard. When I came back in and was heading to the kitchen, she came out from the bedroom wearing her pants and a bra. She turned away quickly and ran to the bedroom completely embarrassed, and I was left alone - shaky and with a typical raging 18 year old hard on.
Sheryl came back out dressed again and started to apologize. I have no idea what she was saying. Hers were the first tits I had ever seen up close. Yeah, she had a bra on but they were real and we were alone in the same room. All I could do was just stare at her chest. After a few minutes of apologizing, I think she finally noticed my erection through my pants. This and my staring changed her from saying sorry to getting offended about my looking at her.
She stepped closer to me and she put her hand under my chin to get me to raise my head away from the cause of my hard on. It was about this time that she started stuttering over her words. And the she finally stopped talking all together. Her hand that was under my chin slowly moved down from my chin to my neck. And then to my chest. To my stomach. And finally she had her hand firmly on my crotch. I almost came right there. She leaned to my ear and asked if I was a virgin. I told her I hadn't even kissed a girl. She then smiled and said, "Well, we're going to fix that." She put her lips to mine and had her tongue in my mouth. Again I almost came.
Sheryl lifted her hand away from my crotch for a moment and I thought we were done. But then she lifted my shirt up a little and thrust her hand down my pants and grabbed my shaft. My dick started to pulsate. She let go, reached further down my pants and then squeezed both my balls so hard that I almost collapsed. She just said, "Don't you dare." She then told me to make sure the front door was locked and to meet me back in the bedroom.
I secured the door and, by the time I got to the bedroom, she had the lights turned down and was lying on the bed. This was the second time I saw tits in person. They were still in that beautiful bra, but now her pants were off and she was wearing matching panties. My knees just about collapsed. She told me not to be afraid and to join her on the bed. I complied, climbing on the bed. She told me we wouldn't have much time but she was going to treat me like a man and get me caught up on things I should have experienced by now. Then, and I don't even remember it happening, she had me out of my clothes and had my cock down her throat. From that day till now, I have never had such amazing head. Within minutes I was exploding in her mouth. I thought I was spent for the night, but she left my limp cock and kissed her way back to my mouth and I tasted my cum on her breath. She then pulled away and told me it was my turn to make her cum. She straddled my face and had her dripping and hairy pussy on my mouth. After some coaching, it didn't take long before she was moaning. Her pussy juices started to taste different. Her back arched, she started to shudder and she finally let herself fall on the bed beside me.
By now, my cock had come back to life (ah, to be young). Sheryl looked at me and asked if I wanted fuck her. I swallowed hard and could barely get the words "fuck yeah" out of my mouth. She laid back, reached up and grabbed the rails on the headboard and told me to mount her. For what I lacked in technique, I made up for by having a young raging erection.
Sheryl's legs were wide open and, without any grace, I just thrust my cock into her. She screamed in pain for a second because she wasn't ready and made some adjustments. Then she looked in my eyes and just said, "Fuck me. As hard as you can." I started a little slower this time but within a few minutes, I was pushing in as hard as I could. I have no idea how long we did this, but eventually my cock exploded for the second time in 30 minutes. This time while I was balls deep inside a beautiful older woman.
As soon as we were done, she told me we could never speak of what we had done. She told me to get dressed and get over to the house. I got up, picked up my clothes and started putting my shirt on. While my shirt was going over my head, I felt Sheryl take my cock into her mouth one last time. I could feel it getting hard again and, just as it was fully erect she pulled away. Then she whispered "Always leave your lover wanting more. Now put your pants on and get out."
I don't know if what happened was a sympathy fuck or something else. All I know is, for the next six months, till I fucked the woman I would end up marrying, and then periodically through the rest of my life, I've thought of that night, I've never spoken about it again - even though I always wanted to when my friends would brag about their adventures, but I figured nobody would ever believe it happened. When I found this sub, I thought it would be just the place to finally share my secret.
Posted Jul 13, 2026, 10:30 AM UTC