In all honesty this story isn’t one of my finest moments but sexually I loved it. This story deals with me cheating on a boyfriend when we were having a rough time and I know that doesn’t excuse it or make it alright but like I said I feel as though it is a good erotic story.
When I started high school my brother was beginning his junior year. We always got along but when I got to high school we actually started to become pretty good friends and I started being friends with a lot of his friends as well. One particular friend was a guy named Dustin and he and I actually began dating as my freshman year came to an end.
Dustin and I actually had a really good relationship through high school. We shared a lot of first and just like a lot of relationships had our ups and downs. When he graduated he left for college and we had our first experience with a long distance relationship. We fought a little more while he was away but I think we still did pretty well.
Well I guess when Dustin was at college he hit some money problems and maxed out a couple of credit cards and ended up leaving after a year and coming back to town. When he got back he didn’t have a job and spent any money he had trying to pay off some bills he had racked up. He did some work for his parents but till he had a job his parents didn’t want him driving around or going out a lot.
So when I started my senior year Dustin was back in town but I had to drive to his house five miles out of town to see him most of the time. I also had started my first job and was working as a cook for a local restaurant and most nights this meant I worked till ten or eleven. Afterwards I would make the drive to his house but we only had an hour or so together before I needed to get home and go to bed. Also by the time I got out there both of us were usually tired so we tended to put in a movie and fall asleep.
At this time my brother was still living at home and working part-time for a local news station as a camera man. One of our other friends Stewart was kind of a party guy and still trying to figure out what he wanted to do but his family wasn’t really enjoying him taking his time. They ended up having a huge fight and kicking him out of their house. He went to my brother and asked if he wanted to get an apartment together but neither really had the money. My brother came up with the alternate suggestion that maybe he could stay at our house for a little bit in the extra bedroom we had. He asked our parents and they said they were fine with it.
Well when I’d get home from seeing Dustin, Stewart would often be up as he was a night owl. He and I were friends so he’d often ask me how my day went and we’d just sit down and talk for a little bit. My brother and he worked opposite schedules so I think he was just happy to have someone to talk with. So it became pretty common for us to talk for a little bit after I get home from work or from seeing Dustin.
Well as you can imagine with Dustin we weren’t exactly having a lot of sex. Not that we had tons before because I didn’t want to get pregnant. Here we were though only getting together after both having long days so were both tired. His parents are either out in the living room or in their bedroom and usually I just got done with work so I smell like a restaurant and that doesn’t exactly set the mood for me. We messed around here and there but nothing like full out and out sex.
So one night I came home after seeing Dustin and Stewart says hello to me and I go in and start talking to him. He was showing me some funny videos on his computer and when I look at his lap I notice the head of his penis sticking out. At this point he was just in his boxer shorts. I was kind of amazed because mentally I measured the length and soft he was longer than Dustin was hard. Well he caught me looking and apologized saying that it happened sometimes and then he adjusted himself so it was hidden. I apologized for staring and felt I needed to explain that I just hadn’t seen one that was that big in real life. He smiled at me and said that he had been gifted in that area.
We watched a couple more videos and then I noticed he was smiling at me again. I asked him what he was smiling at and he asked me if I wanted to see his full penis since I said I hadn’t seen one that big. I can’t even claim to have been having deep thoughts as it took me just a couple of seconds to say yes. Stewart then reached into the fly of his boxers and pulled out a soft penis that was between eight and ten inches. I literally was amazed at the size of it. I had heard stories of Stewart being a lady’s man but I never really got it until this point as I didn’t think he was an attractive man.
Well in my staring at it Stewart said I could touch it if I wanted to. I’d be lying to say that I didn’t want to touch it and unfortunately I only know one way to really touch a dick. So I reached over and wrap my hand around it. I could feel the girth of it and I could even feel the slight pulsing beginning to start. I wondered how much bigger it got when he got hard. So in just natural habit I started slowly stroking him and running my hand over the head of it. As was expected he started getting excited and very hard. In just a minute I was fully stroking him and amazed at what looked to be close to twelve inches of super hard cock that I couldn’t my fingers completely wrapped around.
At this point I had gone a lot further than I should have and I’ll admit that being that hindsight is 20/20. To be completely honest though someone could have come in and said what about your boyfriend and I probably wouldn’t have heard them or understand them.
I’d been so focused on watching his dick grow I’d hadn’t looked Stewart in the face to see just how much enjoyment he was getting out of this. This is when it occurred to me that show and tell had turned into me jacking him off. As I looked Stewart in the eyes all he said to me was “suck on it.” If I had been smart I would have let go and gone to my room right then. Unfortunately not my smartest moment and I crawled onto the bed all the way and laid down putting my head into his lap. I brushed my hair behind my ears and took the head of his penis into my mouth and I had always done.
To this point my experience with deep throating had only been one accident that had gagged me. So I did what I had always done which was suck on the head and go down a little bit so he was at the back of my mouth. Stewart was bigger so my mouth was pretty full and my motions were pretty small. That’s when I felt his hand on the back of my head and when I would go to go down he would put a small amount of pressure on the back of my head and push me a little further. I would start to kind of gag and he would release. Once when I took a moment to take a deep breath I looked and his penis had saliva on it further down than I thought I would be able to take. This really turned me on so I started pushing myself and trying to take him deeper and deeper. I would push myself close to gagging and then Stewart would push me a little further. There were a couple of times I gagged but I was too excited to car.
During this point Stewart took his hand off of the back of my head and started touching my ass. He was rubbing it and slightly spanking it. Then he slid his hand underneath them and grabbed my pink thong and pulled on it. As my thong pulled tighter against my now very sensitive vagina it felt great pulling between my two lips. I let out a small moan but obviously he heard it. He said “oh you like that?” and began pulling harder which did feel great. I actually heard my thong ripping but I didn’t care.
At this point I was literally trying to gag myself on his dick. I would push down till I was choking if I could because I could actually feel my throat beginning to stretch. Stewart stopped pulling on my thong and his hand was back in my pants. I was kind of surprised when I felt his fingers push between my cheeks and apply pressure to my ass. I stopped sucking for just a moment to tell him that it was my ass he was at and all he replied with was that he knew and then he pushed his finger into it. At this point I had had anal sex but I had never had my ass fingered. It actually felt really good as he slowly guided the single finger in and out of my ass.
Stewart all of the sudden grabbed my shoulder and slightly pulled me away from sucking on him. As I sat up he told me to lay back. I laid down on the bed as he stood up. I felt him undoing the buttons to my pants and then grabbed the waist and pulling them down and off. I pulled my legs up as he got on the bed and started rubbing my vagina. It felt good and I could definitely tell I was swollen and really sensitive. He told me my thong was soaked and buried in between the lips of my vagina. He then leaned his head down and gave my slit a long slow lick. Okay, orgasm on the way. Then he grabbed my thong and just tore it and went back to rubbing my sopping wet vagina.
At this point I was on cloud nine and loving it. Stewart then looked at me and asked if I was ready. I didn’t know what exactly he was talking about but I was ready for anything. This would be the first time anyone had used the shocker on me. The only thing I can really say about it was that it was really intense. Whereas Stewart had been slow and gentle before with fingering my ass he now went fast and hard sliding two fingers in and out of my vagina and one in and out of my ass. He also was trying to push them as deep as possible. It felt great and my body responded as I could hear the wetness as his fingers and hand drove as far as possible.
At this point I was done waiting for the grand show and I started chanting fuck me. Stewart heard me and his hand stopped. I looked up and saw him go over to his dresser and reach in one of the drawers. He pulled out a condom tearing the package open. He then dropped his boxers to the floor and he pulled the condom over the huge member that was coming for me. I was so excited that I was shaking. He came back over and got on the bed as I pulled up my legs again. There was no asking if I was ready this time as I felt the head push between my lips and go further. The first time he pushed into me was slow but sent waves through my body. I was pretty sure I was going to last about ten seconds. As he started pushing in further and further it seemed like it just didn’t stop going in. He got into position and then reached behind my head locking his hands together. Then he started going for it. I’m not talking slow love making for passion but quick and hard fucking. His movements were quick and deep and with him locking us together it gave him a perfect position. I actually started squinting in pain as I was not used to something this large but after about thirty seconds the pleasure outweighed the pain. This is also the point where I started to orgasm. All my muscles tightened as hard as they could and warmth shot through my body. I honestly couldn’t tell if I was peeing or not it just all felt great and I didn’t care. Stewart showed no signs of stopping or giving up as he just continued to fuck me with everything he had. I was doing a mix of trying to catch my breath and moan while trying to keep quiet as best I could. I’m sure it sounded like I was choking or something. This is when orgasm number two started and again warmth shot through my body as all my muscles tightened down. As I was coming down slightly Stewart thrust into me and pushed as hard as he could. It hurt but it was a good hurt if that makes sense.
It felt like a minute or so before both of us relaxed our bodies. Stewart was still inside me as he looked down at me. My legs dropped to the side and both of us were breathing heavy. He asked if it had been what I was hoping for and all I could do is smile in return. Stewart stood up and took his condom off walking over to put back on his boxers. I grabbed my pants off of the floor and put them back on. I looked at my torn thong next to them and I just left them there. I told him I should probably go to bed and he smiled in return to me.
As I started walking down the hall to my bedroom it clicked at what I had just done. Suddenly I remembered that I had a boyfriend that hadn’t been able to do anything more than kiss and finger me in the last little bit and one of our friends had just latterly fucked the Hell out of me. Sleep did not come well that night and being super sore the next day just reminded me of what I had done. The next day I told Dustin what I had done and as to be expected it did not go well and we took a break. Two weeks later Stewart and my cousin started dating.