Cindy's Boyfriend and Me

When I was 16-years-old, I met this group of friends that were older than me. They adopted me into their group. They had all known each other since elementary school and all came from privileged families. This group was about 10 people with tons of acquaintances from around town. Most of them were in college and had very liberal attitudes. Through the years, I've taken road trips with them, house sat for their parents, and spent plenty of time partying. They all new people that were exciting and fun. This is about two of the girls in particular, Sally and her bff Cindy. Sally was the first I'd met of this group. I'm still friends with her today.

By the time I'm 18, the group is taking me to restaurants where they had friends that were bartenders and I'd get to drink. I got into clubs with them and pretty much felt like I was their age. Cindy helped me get a job at her company which led her and I to really get to know one another. She was always off and one with this one guy, but I'd never met him, just knew of him. I'd heard about him from some of the others in the group. Seemed everyone thought he was an asshole.

Cindy and I worked together for a few years and had a lot of fun. We often did happy hours but then things started to change. She stopped dating and would bring up her ex-boyfriend more and more. She had got back together with him despite most in the group saying she shouldn't. They kept their relationship away from the group, so I never got to know him on my own. Apparently, he had known about me because I heard that he doesn't like me, so I approached Cindy about it. She said, "he's jealous of you, but don't worry about it because I'll fuck him up if he messes with you."

Fast forward to about 21-years-old. Cindy and I were at some mutual friend's house and we were all being playful in a naughty way. The two guys that lived there were crazy guys. I would later have an experience with one of them and his gf, and many years later the other showed up at my house wanting me to fuck him. More fucking stories OMG LMAO. While we're all messing around, I kissed Cindy on her neck and then gave it a quick suck. Well, she's so white she got a hicky right away. She yells and laughs that her boyfriend is going to be pissed. I forgot she had a boyfriend. Oopsie.

Later in the week, I had asked her if he got mad. She said he threated to come to work and stab my tires. Again, she said she had him in check and he should know we were only playing. So to make nice, she asks me to go have dinner with them. I was surprised to see what he looked like. He was rugged construction worker/hippy. Half white/Hispanic with a nice colored beard. Not bad looking at all. He gave me hateful eyes the whole night and I really couldn't even enjoy my Thai food. We call it a night and I figure he and I are just not going to like each other.

A few weeks later, Sally's boyfriend invited us over to his apartment. He's a good guy but was a smart ass like me. We were very, very tolerant of each other. We had a few drinks and smoked some pot. Sally is a beautiful blue-eyed blonde with a sexy body. Her boyfriend is completely secure about their relationship, and aware of how her and I play with each other. He's never given us any concern. Sally is tipsy and playful, so she gets me and throws me on the couch and starts riding me. I'm laughing my ass off and she's moaning telling me how to give it to her. Her boyfriend looks at us, smiles, and watches the show. Cindy's boyfriend is kind of shocked and just sitting there with a dumb look on his face holding on to the same beer he got when he arrived. They end up leaving, and I still can't shake the awkward feeling about him. Then Sally's boyfriend starts telling me how to make my load shoot farther with kegals lol.

Down the road in time, Sally and her boyfriend decide to shack up in an apartment near the mall. I helped them get some of the smaller furniture, but we waited on Cindy and her boyfriend to show up for the bigger stuff. Darkness came quickly, so we all just decide to sit around a drink. Cindy and I were talking and she said that her boyfriend isn't mad at me anymore because he saw how Sally and I are and figured that I'm just the gay guy having fun with the girls. I'm okay with this and we all have a good time joking and drinking. But I noticed Cindy's boyfriend hardly drank. I thought maybe he was a quick drunk or something.

Sally and her boyfriend leave to their room. I was too drunk to drive so I was just gonna stay. Cindy and her boyfriend decide the same. Cindy is wasted off her ass. They didn't have but a few blankets and we didn't know where the sheets where so the three of us made a makeshift bed on the floor. Cindy's boyfriend says, you sleep on the other side of my girlfriend, and we laughed. The other side would be next to him.

I had fallen asleep and woke up to the feeling of my pants being unzipped. I was intoxicated, so things were slow for me. Quite soon I feel my dick being played with and at that point I froze. My body responded and I got an erection. I could then feel my dick getting wet, and that's when I came to my senses of what was really happening. I felt my pants being opened and pulled down some. I remember settling my breathing to a slow and steady rate as if I were still asleep. I could feel him put the tip of my dick against his ass. He kept rubbing it and rubbing it, and soon I was leaking precum. I couldn't help but be turned on. My dick was rock hard. I was nervous over what would happen next.

I can hear him pull up spit and then I could feel his spit on my dick. He did this several times making the tip of my dick really sensitive. Then he starts pushing his ass against my body, my dick starts to slide between his cheeks with more and more precum. He grabs my dick and tries to put it in him - nature told me to thrust forward, but I just froze. My dick had trouble getting into his tight hole. I thought he was going to stop trying and it would all be over.

He got up and I got scared. He grabbed his drink that was on an end table and sipped up the liquid in his mouth slowly moving it to his hand, then to my dick, then to his ass. He was lubing everything up. He did this a few times until all my precum was mixed with his drink making his ass and my dick slippery. I think it was mostly watered down tonic.

He lays his body as close as he can to mine, my heart is racing, and I can't help but feeling turned on. I know this is wrong, I know he shouldn't be doing this, and I know I should stop, but I can't. I'm frozen. I'm intoxicated from the alcohol. Slow.

He grabs my dick and starts rubbing it against his hole. I can feel how hairy his ass is. My ex was hairy like that and I know the sensation. It tickles my dick good. He keeps backing into my body and trying to align my dick to his asshole. Finally, he opens himself up, and then he pushes himself back on me and my dick slides right inside him. It felt amazing. He didn't even flinch, he just accepted it just as much as he wanted it. He grabs my hand and puts it on his dick trying to get me to jack him off, but I can't. My hand falls limp. He starts fucking my dick. His ass was tight and gripping my dick. I could hear him breathing heavily with each push back. I could feel my heart beat reach my dick, it was throbbing and so hard it felt like it would break off. I think adrenaline combined with everything else of the situation just made my blood pump faster and make my dick harder. And being a hormonal young man at the time, I couldn't help but keep responding sexually, over and over with the precum.

By this time, his ass is soaking wet with my precum. He stops to pull my dick out and feel if I've cum. I can feel him pull the precum to the tip of my dick and then push back into me, my dick sliding into his wet hairy hole again. He's really into it. He slows down and pushed back real slow until all of my cock can slide in, and then all the way out. He wanted to feel my dick penetrate him over and over. I could tell he wanted me. He was like a bitch in heat, wanting me to fuck him good. I'm getting close to an orgasm, but I hold it in because I was afraid to nut inside of him.

He keeps the movement going but starts to slow down and leave my dick inside him for longer periods. I can feel my dick throbbing and I keep trying to hold my cum. He's jacking himself off, still trying to get my hand to jack him off. His dick felt thick and was very hard. He pushes all the way back and grabs my ass with one hand and pulls me into him. I'm as far as I can be up inside of him. I'm conflicted with physical and mental components of this sexual act. I like it, but also, I'm being taken advantage of.

He grips my dick with his ass. I can't take anymore and I start to cum just barely pulling out in time. I just lay there with no further movement. He grabs my dick and starts feeling my cum. He plays with it for a while and grabs some with his fingers. I'm not sure if he tasted it. I can't lie and say the orgasm wasn't good, because it was really good, but... yikes.

I woke up the next morning with his face next to mine... and his finger up my asshole. I felt so awful of what had happened and wondered how else he touched me while I was out. I went and sat on the chair. Sally comes in and she notices right away the look on my face and she says, what's the matter babe? I told her I had to go but will call her once I get home. Cindy's boyfriend was there sleeping with a smile on his face I kid you not.

Later, I told Sally what happened and she said she believed me 100%, no doubt. I confronted him over the phone asking what happened last night and he said nothing happened. It put me and Cindy in an awkward place because she believed me but said he was too drunk.... and she actually said this "maybe he thought you were me." Yeah, because she grew a dick LMAO. He went back to his asshole self and we only ever hung out once or twice after. They threw me a big party for my 22nd birthday, and that was the last time I associated with them together. They went on to get married. A few years later, someone I know dies... guess who that person's half brother is? Cindy's husband. What a small world. You know, they were pretty open minded and had he just come clear to me that he wanted me to fuck him, I would have. But crazy way to go about it. If I ever see him again, I'm gonna ask if he liked my cock and cum inside him lol. They're divorced now, I'm sure he's still in the closet looking at gay porn fantasizing about the one time he wanted his exwife's friend's dick. lol.

How crazy to have been turned on by something like this. It really messed with my mind for a long time. But now, meh, I should have fucked the hell outta him and said nothing. How we grow lol.