My Mothers Boyfriend Pt 01 02

**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.

I was already feeling more warmth in my body, and braver. I shifted my hips up and back down, sliding the hidden dildo in and out of me a bit causing a small moan to escape my lips. He tensed next to me, but didn't say anything.

"I just also think you deserve to be treated better." I finally said.

"What do you mean?" He asked me and took another swig, obviously wanting to keep his buzz for this convo.

"Well, I know how my mom is, and I know you aren't stupid. You know she's not happy, and I'm pretty sure you see a breakup coming, which is why you drink more." I said.

He got quiet and didn't say anything. So I continued, "I figure we're past awkward here, so..." I paused briefly and said fuck it in my head. "When was the last time you had sex?"

He didn't tense up this time, he just sighed and took another drink, which I also followed suit. "Fuck it. About 8 months ago. And even then, it was like I had to beg for it." He said.

I nodded and made sure to lift my hips a bit and slide the dildo inside me just enough to cause a small moan to come out after he said that. I could see the beginning of a tent in his flannel pants.

"So you're treated like crap, you're not getting laid. No wonder you've been unhappy and drinking." I said and took a drink. "I mean I'm a bit embarrassed that you caught me playing with myself, but I dunno, also kinda glad because I think you deserve to know you have someone who wants you, even if it is wrong. That you are desirable."

He just sighs and takes a drink again. I move my hips a bit and slide the dildo in me, making sure my moan is a bit louder, still higher pitched to emulate a woman's. He didn't say anything but I could see him straining his pants.

I turned and set my drink on my nightstand, careful, so nothing slipped out, moved over behind him. I put my hands on his shoulders.

He flinched and tried to turn, "What are you doing?"

"Relax!" I tell him and apply pressure to the muscles in his shoulders.

He's still tense, but he doesn't say anything. Now, he was about 46 at this time, about 5'10, dark gray hair cut short on top, full blooded Italian, but pale cause he usually worked nights. Gorgeous brown eyes. He had a soft body. Almost a "dad" bod type of appearance but he went running so he was slim, just soft. Although he had a little hair on his arms, his chest was bare of any hair anywhere, I think it was natural.

I started working his shoulders a bit and slowly but surely, he started to relax a bit. "See? You deserve to feel good like this. Just relax."

He didn't say anything, just kept taking a sip here and there. I massaged his shoulders, working my way around his muscles a bit, doing what I had learned from reading online. I made sure to press up against him as I did and knew he could feel my own boner pressing into him a bit. He just stayed quiet and took a drink.

"Take off your shirt, this will be easier." I said and started to lift the bottom of his shirt from behind.

He obliged, even if he hesitated at first. I knew he was drunk, I knew he was beyond horny, and I knew that I was taking advantage of him, but at that time, I didn't care. I had a goal in mind and I was going to get it.

I placed my hands back on his bare shoulders and resumed. He took smaller sips of his drink and I felt him relax in my hand. I occasionally pressed my lower half against his back and pressed my hard cock into him, but he never said anything. I'd rock back onto my dildo, and moan out a bit in a higher pitched voice, still he remained quiet.

So I got a bit braver, I slowed my massage and let my hands move over his shoulders and onto his bare chest. "See? You look amazing, man. Is it a wonder I did what I did?" And I briefly let one of my fingers glide across one of his nipples.

He tensed, but only a bit, and then relaxed again. "I mean," he trailed off and took another drink. "I guess not."

I massaged his soft pecs as best as I could from behind, and glided the tips of my fingers across his hardening nipples a couple more times.

"What are you doing?" He suddenly asked, in a moment of clarity.

"Nothing, just trying to give you what you deserve and what you need, a chance to relax and feel appreciated. The thing you're missing." I said.

"I'm not gay." He said, pretty firmly.

"I know you're not gay. I'm just trying to give you what you need. That's all." I said and lightly pinched his nipple.

He tensed up like he was going to pull away or say something and I got scared that I went too far too fast. But he stayed quiet, my hands still on his pecs, and he took another drink.

His back leaned into me a bit, allowing me more access from behind. I ran my hands along his pecs and over his soft belly a bit. I couldn't reach further yet. I lifted my hips a bit and moved the dildo a bit out and back into me, keeping my ass full, and I gently moaned into his ear in as feminine a voice as I could conjure asking him if it felt okay, and lightly pinched a nipple of his again before returning to massaging his soft pecs.

"Yeah, it's okay." He said, and I knew I was getting closer to my goal. He leaned his bare back all the way into my, and I knew he felt my throbbing young cock pressing into him.

I ran my hands over his chest as he took another drink, and down to caress his belly. I could see over and saw a much bigger bulge in his flannel pants. I was able to lower on his body and let my rubbing hands glance across the waste-band of his pants and after a few more passes, even slide underneath, just a bit.

He didn't say anything, but I could see him straining his flannel pants. "You okay?" I asked softly with a slight feminine tone in my voice.

"No." He said hesitantly. "But yeah, I guess."

I reached behind me and slid the dildo out of me, I had to raise up a bit and I put it back and to the side of me. I started to move from behind him. "Lay back." Was all I said as I moved. He started to sit up as I moved from behind him, but I put a hand on his chest and gently pushed for him to lay down. He looked to the side and set his drink on my other night stand, sighed, and laid back.

"Good. Now close your eyes for me." He looked at me, I could see his drunkenness and horniness and repulsion play around and finally he closed his eyes.

He laid down for me, I was still kneeling at his side. I reached over and grabbed the dildo, it was still slick and wet and I leaned up and slid it back inside of me, not caring at this point if he opened his eyes and saw me do this. I sat back onto it, felt the silicone balls press against my cheeks and let out a small moan as I placed my hands back on his chest.

I massaged his pecs some more, lightly dragging the tips of my fingers across his hard nipples. He didn't say anything but I could clearly see the strain in his pajama pants. I leaned over a bit, knowing the big dildo would slide out of me about half way and rubbed my hands down his left arm, massaged his biceps, and gave a bit of a feminine moan as I sat back onto the dildo and moved my hands back to his chest. I know he heard me, but still he said nothing. I then ran my hands down his right arm, doing the same thing, and made sure to massage his bicep.

"You're so strong." I said to him as I moved back to his chest. "I love your arms."

I saw him about to say something and as he opened his mouth to speak, I lightly pinched his right nipple. A small, soft, and very quiet moan escaped him and he said "Thanks."

I knew that I had him. And I knew that I had manipulated him right where I wanted him. So I started rubbing his pecs again, and then his abdomen a bit. I watched his face as I neared his waste-band. I'd rub, and slightly slip a pinky underneath. Nothing. The next pass, I made sure I was obvious about sliding my pinky and right ring finger about an inch under the waste-band, and his eyes opened, we locked eyes, but he didn't say anything.

It felt like ages we stared at each other, but it was probably only a few seconds. He closed his eyes again and laid back. So I placed my hands on either side of his hips and massages there, knowing the dildo slid out of me a bit as I did. I'd work my fingers under the waste-band a bit, but not too far.

I started to slide back into my dildo, causing me to moan again. "Keep your eyes closed and just relax." I said as he moved his right arm up over his head to lay back. I reached between my legs to keep the silicone fuck stick inside me and turned a bit so I was facing more of the foot of the bed and more of my back was to him. Still resting on my knees I let go of the dildo. I'm sitting back on it, knowing he could see better if he opened his eyes and started massaging the outside of his hips over his pants. I'd occasionally rub my left hand back up the side of his body to his chest and tweak a nipple, getting a soft moan from him.

I return my hand and now both my hands are on his thighs, massaging, and I work them inwards. His legs spread slightly, giving me better access. I stop massaging for a second, unsure if I wanna go for it now. My heart thundered in my chest, I was afraid it would end the moment I touched him there and he would come to his senses.

But I swallowed down my suddenly dry throat and moved my right hand lightly over his bulging strain in his pants.

He tensed, very hard and quickly, so I brought my hand back over his bulging cock in his pants, a bit firmer this time. And again. He stayed tense, I knew he was reconsidering things again. So I went for it. I gripped his cock, which was angled upward in his pants toward his stomach, and gave him a couple firm strokes.

I heard a small moan from behind me, and slowly, as I gently stroked his covered cock, he relaxed again.

I knew this might fuck it up, but I asked anyway, nervous and horny as hell. "Are you okay?"

He was silent as I gently stroked him, until he finally responded. "I guess. Just weird."