Blackmail one, Get two

My 18th Birthday had just passed Monday, and on Friday my friends were planning to take me out to the club for the first time. I had been to teen clubs before but not one with people a lot older than me or where there would be drinks. I was anxious all week to go and many of my friends were thinking about getting me a VIP table and ordering bottles of Hennessy and Grey goose which were my favorite drinks. Friday morning came along and I went to all my classes at school and talked with everyone to coordinate at what time it was that we were going to leave.

My friends had known I was gay for about a year now, but I still hung out with the straight crowd about 99 percent of the time. We were going to go to a straight club that night and I had one of my girlfriends be my dance partner for that night. Because of the people whom I normally hung out with, I had yet to have any sexual experience with a guy. I was always really shy end extroverted and didn’t really feel comfortable meeting new people. I just enjoyed hanging out with the friends that I already had.

I have always been considered a really cute guy with a sexy body and face. My stomach was flat and just a tad bit toned and my legs are probably my best feature. I run about two miles every morning and stay on a well balanced diet. I had done a few photo shoots before and a lot of girls thought that I was gorgeous and would almost die when I said that I was gay. Im about 5’ 8” and weigh about 125, My hair is a silky brown color and my eyes are hazel. My butt is also a really nice feature that I love because it is so firm and round. My skin color is a natural tanned color and with lotion, it just seems to shine.

So anyways, after dinner we get in the cars and head out towards the clubs in downtown. We head to club Paris and get there within the next twenty to twenty five minutes. We go inside through the VIP entrance and get our table and a few bottles to begin with. We start the drinks and are having a blast and the time is going faster than I would have wished. I’m dancing with my friend Stephanie and as we are getting really into it, I notice that Jonathan, my sister’s boyfriend is about fifteen feet away and dancing with some chick. She was grinding all over him and I could tell that this girl wasn’t just a friend. Soon enough, they started kissing and he was grabbing her stomach, tits and even slid his hands around her pussy.

I was pissed at what I was seeing and felt like going over there and punching their lights out. Yet, I knew I couldn’t because deep down, I had always had a crush on Jonathan. He was in the same grade as me because he failed once, but was my sister’s age, about a year and a half older than I. At school, he knew better than to try and cheat on my sister, because he knew that I would find out. My sister was already in her first year of college and had me watch over him. He was really sexy and most girls at school wanted to get a piece of him. He played a whole bunch of sports and his body was amazing. If it wasn’t for the fact that I was looking over him, Im pretty sure he would have fucked half of the girls at school by now. He was a major showoff and always walked around with his shirt lifted on one side over his shoulder so that his abs would show. He would always flex and ask people how he looked and was always saying he was fat. He enjoyed the attention that he got from his body.

So back to the club; I finish dancing the song with Stephanie and head to get a drink. On my way back I head towards Jonathan and the chick that he is with and while he has his knees bent and grinding his crotch into her backside, I tap his shoulder and say, Hey Jonathan! He looks up and when he saw my face, he just froze and stayed in shock. I would have loved to take a picture of his face and print it out a thousand times. He really didn’t get to say much when I kept walking and went back to my friends.

At the end of the night, I make my way out to my car and when I look at my phone, I had about 30 missed calls from Jonathan. I call him back to see what his excuse was going to be and he told me that he was just down the road and wanted me to meet up with him. I drove to the parking lot where he told me he was located and got out of my car. He said that he was sorry and he didn’t want me to tell my sister. I told him that this was the only chance I was going to give him and that it better not happen again. We kept talking and he told me how he really liked my sister but that the girl was an ex that lives out of the state and wanted to spend a little bit of time with her. I told him to make sure to pick what he wanted and that if he was still in love with my sister that I wouldn’t tell her.

For the next few weeks, every time that Jonathan came to my house, he didn’t really want to look at me because he was ashamed of what happened. He knew that I could have blackmailed him and ruined his relationship. I guess that his conscience was getting the best of him and he started acting weird around my sister and they began to get into a whole bunch of arguments. After a month my sister started suspecting that he was cheating on her, but I hadn’t seen him with any chick at school. She wanted me to spy on him a bit and one day I took my dad’s Jaguar, which he had never seen and followed him around town.

This time was a Saturday night and I see Jonathan drive into a cheap motel with some blonde chick. I had my video camera with me this time and went to the door that he entered. To my surprise, the window which was right next to the door was a bit open and I could here them talking inside. After a few minutes, they headed into the bathroom together. Nobody was looking and I reached in through the window and was able to open the door from the inside. I closed the door silently and went inside the closet. I turned on the camera and waited for them to come back out. Sure enough within 10 minutes they came out, sharing the same towel and both jumped onto the bed. I was videotaping them through a slight opening in the closet door and since everything was pretty quiet, their noises could be heard on the tape.

Jonathan pushed his dick into her pussy and the girl let out a long but soft moan. He was really hard on her and as soon as his dick was inside her, he was pounding away at her pussy. I had never seen Jonathan’s dick up until that point and I loved the look of it. It sure matched his body and was just about as big as the rest of his muscles. He didn’t have a 10 inch monster but it was very thick and had a nice curve to it. The girl is breathing really heavily and he is just going at it like a rabbit. I kept video tapping and already, I had a major boner. I loved the sight of Jonathan penetrating her fully with that massive tool. I realized why it was that my sister loved going over to his house so much. I’m sure that he could please any ass or pussy without even having to move. He seemed like he was really into it and biting her neck and licking her tits. After a while he got off of the missionary position and she got on top of him. She bounced high on his dick and pushed back down. Her tits were flying all over the place and he just laid there with his hands behind his head. With his hands in that position, I could see his biceps and sexy shaved armpits. He really took care of his body and that girl was surely enjoying him.

The last thing for both of them that night was when he put her in doggy position on a chair and nailed her from behind. It didn’t take long for him to cum after that and when he did, he blew it into the condom he had on. They both put their clothes back on and left the room. I wasn’t sure if he was planning on returning and using the room, since he had already gotten use of it and I exited the closet. After about 10 minutes, I look out the window and his car is not there. I proceed to call him and he asks me whats up? I tell him to go back to the place he was just at with the blonde chick and he tries to pretend like he wasn’t just at a motel and like nothing happened. I told him that I had something really important to show him and that he should get there as soon as possible.

Another 10 minutes passed and Jonathan parked his black convertible mustang outside. He gets out of the car and I was waiting just outside the door to the room. He was pale as a ghost and I told him to open the door to the motel room. He did as he was told and we went inside. I had my camera in my hand and I told him that I wanted him to see something so that he could explain it to me. The video starts playing and he was in shock when he saw himself beating away at the girls pussy with his ass facing the camera. He could barely speak, but managed to ask how I was able to record him. I answered by telling him how I got inside the room after seeing him go inside with the blonde. He was shaking a bit from the nerves and he was pleading me again not to tell my sister. I told him that this was hundreds of times worse than at the club and that now, I had the proof. He asked me what it would cost him to get them tape and for me to stay quiet. I told him that he wasn’t getting the tape, but that didn’t mean I would show it to my sister if he paid up. He insisted that he would pay or do anything so that I didn’t show her because he still wanted the relationship with my sister.

I kept playing the video and told him to look exactly at the things he was doing to that chick. He looks at me and says, yea I see. I say to him, I want you to do the exact same thing to me. His eyes opened up even wider and asked, you want me to fuck you? I said, yeap, and just like you did it do her. He started shaking his head and saying that he couldn’t do that. I told him that it was ok but, that meant I would show my sister the tape. Again he said that he would do anything else as long as it wasn’t that. I didn’t let my guard down and exclaimed that the only way for me not to show her the tape was by nailing me in the same way he had just done that girl. He looked at me and said, fine then, I guess I will do it, but ive never fucked a guy and haven’t even fucked any chick in the ass. I didn’t feel bad for him at all at the moment and was actually pretty glad that I would be his first piece of ass. He then told me that we would have to wait since he had just came and wouldn’t be able to cum so fast. I said it was ok and that it could be later since I wanted to be ready for it as well. We left the motel and on our wait out I waved the tape and told him to not forget that he owed me.

During the next few days, Jonathan insisted that he didn’t want to fuck a dude and for me just to blow him off. I told him no, that I wanted to get fucked. He was pissed and knew that I wasn’t going to give up on getting nailed from behind and that time was running out. Saturday my entire family was going to go to the beach but since I had a couple of things to do in the morning, I wasn’t going. I had told him that he would have to come over that day around 3pm.
Friday night I get a call from Jonathan and he talks to me about a proposition that he has. Apparently, one of the guys from school owed him $1000 for a bike and Jonathan told him about the problem he was in. They came to an agreement that if the other guy fucked me, he wouldn’t have to pay the money. I asked him who the other guy was and he told me Xavier Ortiz and my jaw just about dropped. This was probably the guy I considered the hottest and best baseball player at school. I became exited the moment Jonathan said his name and I just about agreed. Still, I told Jonathan that He was the person who owed me and that Xavier could do the fucking but he still had to let me suck him off. He said that if I gave him the tape, which I had said I wouldn’t, that we had an agreement. I said ok and pretty much spent all night jumping around my room and of course calmed down and made a copy of the tape. LOL.

Saturday morning, everyone leaves the house and I go and do everything that I have to. When I return, I placed my video camera underneath some clothes with a small opening and planned to tape the whole ordeal. About five minutes past three, there’s a knock at the door. To my surprise, both guys are here together and I let them in. We go to my room and Xavier, whom I had never talked to, was awestruck at the size and décor of our house. As soon as we get inside the room, Jonathan says, lets hurry up and get this over with and unzips his pants and pulls them down. I kneeled in front of him and Xavier stands just to his left and does the same. I started with Jonathan and I was laughing inside because I had never seen anyone elses dick when it was soft. It was way smaller than I had seen at the hotel. I started to suck on it and within the minute it was growing to full size. The curve in his cock was becoming apparent and it was getting harder for me to fit it in my mouth. I slobbered all over his dick and in no time it got rock hard. I loved the taste of cock in my mouth and I felt as if it was natural to have it inside me. I had never felt anything so good in my mouth and loved the texture and warmness to it. I look to my left and I see that Xavier’s dick is getting bigger and I move to him. I put his dick and my mouth while still jacking Jonathan off. While im sucking on it, he moans and loves when I swirl my tongue around the head. He placed his hand on the back on my head and pushed it down onto him. The tip of his cock hit the back of my throat and I gagged. Even though gagging didn’t feel so great, I loved the experience. He tried to get me to go faster but I went back to Jonathan’s dick. As I’m sucking on Jonathan I keep my left hand on Xavier and while I’m jacking him off, he takes of his shirt. We all moved to my bed and I sat them both down. Every time I went back to Xavier’s dick, I could tell that he was enjoying it and wasn’t bothered at all by what was happening. After about 4 times of switching from one guy to the other, Xavier gets up and says, I was supposed to fuck him right? He puts a condom on and lubes his dick up. His dick wasn’t as thick as Jonathans but it was about 3 inches longer which I knew was still to going to cause me some pain. He bent his knees a little to accommodate himself and found my hole and rubbed on it with his finger. He played with my hot and waiting hole for a little while, teasing me and then shoving his finger inside me. The feeling was amazing and I loved having him back there. He then kneeled even more and started to rim me. I had never even thought about getting my ass eaten out, but I wasn’t going to tell him to stop. While Xavier is playing with my ass, I keep sucking on Jonathan’s dick and it was all wet and slippery by now. He must always take a long time to cum, like at the motel, because the way I was sucking at him would have made any guy cum by now.

Xavier puts the head of his cock at the entrance to my ass and slowly pushes in. As soon as his head starts to spread my sphincter open, I feel a sharp pain all over my body and wasn’t even able to concentrate on the dick that was in my mouth. I let out a hard moan and he stopped. When I eased up a bit, he kept pushing in and got to hit my anal wall. It hurt like hell when that happened and he hadn’t even gotten all the way in. I got accustomed to his girth and he started to rock back and forth. I was so happy to finally be getting fucked and I was in such pleasure with two of the hottest guys at school. I couldn’t believe my luck to be having my fantasy of being with two guys come true on the day I lost my virginity. I go back to sucking Jonathan off and he was so hard at that point that I knew that he was going to erupt. His dick began to get really red and really warm and his breathing was getting real intense. I keep my head bobbing up and down and in an instant, I feel a huge burst of cum fly to the back of my mouth. I keep working on him and a few more streams of cum came out, filling me up quickly. I kept sucking and swallowed it all and waited till he was all done. When he seemed finish I let go and Jonathan just got up and put his clothes on and left.

Xavier stayed in the room and kept working at my ass. He was already going with a faster rhythm and my ass was filled with ecstasy. The feeling of being fucked was so great, that my entire body tingled. I had been on my knees the whole time and felt like I wanted to switch to a different position. I pushed Xavier off of me with my right hand and he made a weird smirk as if wondering if he was doing it all right. I told him “damn you fuck real good, but let me lead now,” and he agreed. I lay him on the bed, climb on top of him and kneel on the bed. I ease back and down slowly and let his rock hard dick enter me slowly. Being on top of him made me go wild and I couldn’t resist grinding all over his crotch and feeling his shaved pubes on my buttocks. I started to bounce up and down while grabbing on to his shoulders and pecs. Being in control eased the pain a lot for me and now I was able to control my sphincter and squeeze real hard on his dick. As I bounced my dick would keep hitting Xavier’s abs and from the pleasure in my ass, I couldn’t stop the oozing precum. His stomach was all wet and shiny and I thought he might be pissed but what he did next was my biggest surprise of not only that day or week, but maybe even my life. Xavier took his left hand, wet two of his fingers with my precum and placed them into his mouth. I had never ever thought about him being gay and I was in such shock that I stopped rocking on his cock.

After a few seconds of just staring at him, he moves his head close to mine and kisses me on the lips and asks, what? Still I was frozen and he proceeded to get me off of him and he threw me stomach down onto the bed. He climbed on top of me and thrust his long dick into my ass again. I finally came back down to reality and I turned my head around and asked him if he was gay. I think he liked the question and he pushed his cock into me, the hardest he had that day and started pounding and beating away. He just smiled and answered, you can call me what you want, I just like sex. I didn’t respond back and just let him keep working at my now swollen ass. I was feeling so tired and beaten up that I didn’t know if I could take much more. I began to moan and pant and would tell Xavier to stop. He pushed my head into a pillow and held it there and went faster and faster. I could feel my ass hugging onto his cock even more and he was definitely going deeper into me. His breathing got heavier and he penetrated me slowly and deeply and I could feel that he was spent inside the condom. He fell on top of me and slowly retreated his beautiful cock.

I showed Xavier to the bathroom and when he finished cleaning his dick he hopped into the shower. He gave me a nice look which meant I could join him and that’s when he said it was my turn to do the fucking. I smiled and joined him, but That story will come later.