**This is a 100% true story. I swear on all the deities and whatever else that is out there. So some backstory, my mom had been with this guy for two years, and he was her 4th bf since she left my dad. She had a tendency, when she was done with the guy she was seeing but nothing was officially broken yet, to stop treating them well and stopped having sex, and avoided them at all costs. Also, I was freshly 18 when this happened, by about a month. This was about 15-16 years ago for me, and this is a trigger warning. As hot as this was for me, and it turned out okay in the end, I did force myself on someone who was not comfortable doing what we did. It was more manipulation and relentlessness to get what I wanted, and I did, but I learned as I got older that it was not okay and should not have happened, on a few different levels. I feel bad about it, but the gentleman in this story and I did remain in contact for years after this incident. So, in no way right in my part, but it thankfully turned out okay**
My moms ex-boyfriend caught me once. This was near the end of their relationship when she stopped fucking him and he drank a lot. He had been drinking that day while everyone was at work and came in to tell me dinner was here and caught me on all fours with my 8 inch dildo up my ass. He stood there for a couple minutes in baffled silence and I just moved it in and out a couple more times as he stared at me before he finally closed the door telling me to come eat.
I was a bit disappointed because I was insanely attracted to him. So I stopped and got dressed and joined him for pizza. He had a couple more drinks but he didn't really talk to me much as we sat on the couch next to one another, eating our food. I could see the remnants of a bulge in his lap. Me being freshly 18 and always horny, knew I had to try something. So I said I was gonna go back to my room.
I did, and left the door cracked a bit, stripped back down but left my jockstrap on, got on all fours again, this time with my ass pointed directly at my door. I lubed up my hole and started using my dildo again. I'd moan occasionally, and when I saw a shadow at my door, I moaned my moms bf's name, loud enough that I knew he heard me. It was like that for a few minutes, I could see his shadow in the slit of my door, watching my slide my dildo in and out of my young hole.
I moaned his name a few more times as I fucked myself. I pulled the dildo almost all the way out and pushed it in as hard and fast as I could, causing me to moan his name the loudest I dared. The door finally pushed in and he came in, upset and almost yelling, "What are you doing?!"
I was young and got a bit scared and just said "I don't know, it just felt good."
He asked me, "Why did you say my name?"
I was red in the face and terrified. My body was on fire, he was upset, I was still on all fours with the dildo buried inside me after that final push, too scared to move, but I said that I knew it wasn't exactly right, but I thought of him a lot when I did this, ever since the first time I caught him coming out of the shower.
"I'm with your mother though, it's not right to think that way." He said. "Take that thing out and talk to me."
I slid the dildo out of me and turned to sit up. My eyes looked at his, but I made a point to look lower on his body so he would see me do so. I could see his cock was hard in his pants though. So I asked him why not? It's not like she would ever know.
"Because it's just wrong." He said back to me.
Mind you I'm still in my jockstrap, my used dildo is laying next to me on the bed, and he's drunk and hard in front of me, fully clothed. A bit of my fear started to strip away and I finally asked him, "Maybe, but when was the last time you felt desired?"
He tried deflecting me, saying that wasn't the point he was making. So I redirected a bit because I was still scared, but also strangely brave and asked, "I'm a bit nervous about this, can I please have one of your beers, and maybe we can talk?"
He was silent for a few, the bulge in his pants went down a bit. "I'll give you a beer or two just because I hate drinking alone. But I don't want to talk about this."
He turned and left my room, I was going to get up and follow him but he said he'd be right back. So I decided to try something. I laid on my stomach, still in my jockstrap, so my ass was facing up and I repositioned the used dildo along my side near my hips and ass. My horny brain thought of keeping the two images connected in his head.
He came back with two new beers and a Jack and Coke for him. He stopped when he looked at me for a second when he came back in, didn't say anything, and walked around my bed and sat next to where I was laying down. He handed me a freshly open beer and took a drink of his Jack and Coke.
He sat there next to me, with me on my stomach, for a few minutes in extremely awkward silence while we each sipped our drinks until he finally spoke up. "Why would you do that while saying my name? You're still a kid."
Me being the fresh "adult" that I was, shot back that I was an adult now.
"You know what I mean. And plus I'm in my mid 40's, way too big of an age gap and I don't like men. I love your mother." He said.
I drank quickly and downed my beer, I could feel it working a little magic already and I got a little extra courage.
I remember most of this like it was yesterday and I remember saying "I know you do. But I can't help what I fantasize about or who, and I know you and my mom haven't done anything for months. That isn't fair to you."
I readjusted my position a bit on the bed and caught his side glance at my ass. "But don't you see how sick it is? To lust after someone who's with your mother?"
"Maybe." I remember saying. "But I can't help how I feel." I paused for a second. "Can I have that second beer?"
He takes a swig of his big glass and hands me the beer after he opens it for me. He hasn't said anything yet.
I take a big drink, which as anyone who's tried drinking while laying on their stomach knows, it's not the most comfortable position. But I'm feeling a bit braver and still have a horny brain.
"I mean, it didn't really start until the first time I saw you getting out of the shower. You just had such a nice body. And I couldn't believe my eyes at how big you looked soft. It was a huge turn on for me." I said. I knowingly lifted up my hips a bit, lifting my ass. I reached back to scratch one of my cheeks, and dragged a couple fingers across my hole as I brought my arm back up, letting a small, higher pitched moan escape my lips.
He blushed a little at that and said, "Well, thanks I guess."
I moved a bit to sit up and sat on my knees next to him. I made a motion, which he watched, of me reaching back and moving my dildo over to sit it behind us.
"I don't know what I expected. I didn't even know you heard me. I've just always sort of fantasized about you that way after that. Stories online didn't help." I said.
He was quiet for a few, took another drink and asked, "What kind of stories?"
I blushed and drank my beer. "You know? Like dad and son or step dad and son stories. I always liked those."
"Really?" He asked. "But don't you see how those are wrong?"
"Yeah, but that's the best part I guess." I said. "How wrong they are."
We were quiet for a bit and drank. But I scooted a bit closer to him so my bare thigh and shoulder were touching him. He didn't say anything about that, just took another drink.
"How big is that thing?" He asked suddenly.
I was a bit caught off guard, but the beer and a half in my inexperienced self got brave. "About 8 inches. I had heard mom mention on the phone one time to one of her girlfriends when you first started dating that that was about as big as you were, so I got one the same size. I wanted to get as close as I could to imagining it was you fucking me, and not a piece of rubber."
"See? Just not right." Was all he said and had another swig from his big cup. His other hand reached over to adjust his crotch.
I noticed the bulge returned to his pants a bit so I decided to down my second beer and toss the can into the trash can in my room.
"Can I have a drink of yours?" I asked as I reached for his cup intentionally, making sure our fingers touched. He flinched a bit, but he let me take his cup and have a drink of liquor. I made sure our fingers touched again when I handed it back to him and let mine linger, my index finger stroking his lightly before I let go completely.
I sort of let my hand fall slowly and grazed the top and outside of his thigh before coming back into my lap. He didn't flinch.
"Why me though?" He finally asked, his drink almost empty. "Actually, wait here. I need a refill."
He got up and left my room. So I had another thought after he left. Since I was sitting on my knees on my bed, I lifted myself up, reached for the lube, lubed up my dildo and slipped it back inside me. I sat back down onto it back into the same sitting position I was in before, just this time with the dildo buried inside me.
I rocked my hips back and forth a few times, enjoying the sensation of being filled up before my moms boyfriend came back and I stopped. He had two glasses of Jack and Coke, and he had changed out of his jeans and into his flannel sleep pants.
"Here. Don't tell your mother about this." He said and handed me a glass. I saw his eyes looking at the bed. I couldn't be sure if he noticed the dildo was missing or not, but he came and sat back down next to me on the bed, shoulders touching. If he had any idea the dildo was inside me, he didn't say anything. He took a long drink and after, he again asked me, "Why me?"
I took a drink from what I assumed was my bribe, and said, "Well, you're hot first of all. You have a great body. But you're also sweet and nice, caring."
"Well thanks." He said and took a drink.