This all happened around 2 years ago right after I had just turned 20 years old.
My name is Alex. I think I'm a good looking guy. I come from a well to do family and I have always lived in the same small town. At the time all of this occurred I had been in a 1 year relationship with my girlfriend, Sarah. I have always considered her to be out of my league. She was very active in her church and I was just as active because of her. She already had a good job at the local pharmacy and was working towards her degree in the same field. Her dad was CEO of a local packaging company and they were very well known in the area. Sarah and her parents were very good to me and I felt lucky. I could see myself settling down with her. I was as happy as I could be.
The reason I say that my girlfriend is out of my league is because I have always been a smaller guy. It's not just my height, but my frame. I have always felt as though I was behind all of the other guys when it came to physical development. I didn't have body hair, a strong jaw, or much muscle. At the time I attributed all of this to the fact that I was a swimmer. I was lucky enough to be on a team at a nearby junior college and competed in long distance events. The lack of development in my body couldn't have been more apparent than when our team was in the showers. The amount of muscle that some of the guys had along with the size of the cocks was enough to make me jealous. While they had to shave their body twice a week, I usually could go 2-3 weeks without any hair growing. I knew that I would never have that type of manly body.
This impression I had of myself affected me in the way I viewed women and men. As I said before, I considered myself lucky to be with my girlfriend and I never felt in charge. For example, she usually made decisions for us and this carried over to the bedroom where I would routinely go down on her with no reciprocation. If I was lucky, we would have sex, and I would be on bottom. Part of me knew this was due to my small dick, but I also knew that she was fairly dominant. With men, I knew I would never be considered an alpha male. When I was with my team I was friendly and didn't say a lot. I basically went with the flow.
While in college my porn consumption had grown out of control. It started with anal, then a2m, bdsm, shemales, sissy hypos, then gay porn with a lot of little fetishes in between. Finally, it became where porn wasn't enough, I needed interaction. Since it is incredibly difficult to find women willing to talk dirty or interact online I turned to men, specifically older men as this was my preference and still is today. They always seemed more confident and aggressive. Nothing turned me on more than an older man telling me what to do. I would go through craigslist or other sites and share pictures of myself and talk dirty. Over time I started to cam with older men and this raised the excitement even more. I loved making them cum! I ended up buying panties, bikinis, dildos; make up, a chastity cage, anything to make older men happier and more eager. Of course, all of this was anonymous. I would never share pictures of my face and when skyping I would have on sunglasses or some other type of disguise. I wrote all of this off as porn, even though it had clearly become something more. Almost every night I would write if off of my consciousness because of the guilt and shame that came over me after cumming. I would tell myself "never again", "this is dangerous, you could get caught", "what would Sarah think". Even with all of these thoughts I would end up at the same site night after night making older men cum. After months of this, I needed even more. I found myself wanting to meet an older man in person and satisfy him. I wanted to try it just once before I settled down too seriously with Sarah, so I started searching. It was odd to me that most of the time when I was around my team I wouldn't be turned on by them. I also wouldn't be turned on by an older man in everyday life, but as soon as one wanted me and gave me direction I instantly became attracted. I started talking to local men on "older men and admirer" sites. I would always search for the Dom Tops. They were the type that always made me horny. We would talk dirty, get worked up, set up a time to meet and then I would end up flaking out. I pissed some men off even though I really had intentions to meet, I could just never bring myself to go through with it. Then it happened.
It was Friday, I was camming again and I was extremely horny. I was completely shaven from a swim meet I had had that day and I completely cleaned myself inside and out twice so I could enjoy a whole night worth of fun. I even put my small dick in a chastity cage to be sure I wouldn’t cum to soon. I slid my panties on and then I went to my normal website that was specifically for older men and their admirers. It even had a chat room. My first chat was with a man named Henry. We had skyped a few times before. He was only 35 miles away so the excitement of possibly meeting made the session even more exciting.
H: Can you see me?
M: Yes sir.
H: Good, stand up and turn around so I can see your ass.
H: Damn, I love your ass boy! Spread those checks for me.
H: Now take those sunglasses off and show me your face.
M: I can’t sir, I will do anything else though.
H: You can’t trust me by now?
H: That-a-boy, you're good looking, now get down on your knees with your ass towards the camera.
M: Yes Sir
H: Scoot you ass as close to you camera as you can.
H: Mmm, fuck boy, you are smooth.
H: How long has it been since you got fucked?
M: A whole month sir, I need it! (Lie)
H: I bet you are craving a cock aren’t you?
M: Yes sir, I need a cock so bad.
H: Go ahead and slide a finger in that tight ass of yours.
H: Deeper, keep going.
H: Now, in and out.
H: Two fingers now.
H: That’s good, slap your ass for me
H: Harder!
H: Damn you are getting me worked up.
H: You like being used you little faggot?
M: Yes sir!
H: I bet you do. Add a third finger for me.
H: Damn boy, you have tight little ass!
H: Beg for daddy’s cock!
M: Please sir, give me your cock! I need your cum!
H: Turn around and open your mouth!
H: Oh fuck, ugh! Swallow my cum.
M: Mmmmm, thank you sir. I wish I was there to swallow every drop from that huge cock!
H: Do you really mean that?
M: Yes sir I do! I need it bad.
H: Why don’t you come over to my place? You’re only an hour or so away. We can have fun. I have a blue pill for myself.
M: Umm, my girlfriend is coming over an hour or so. I probably need to go.
H: Don’t be scared, you just told me in the chat room you plan to have a whole ni....
I cut off the chat, flaking out once again. I hopped back online, clicked on a sissy hypno, grabbed a smaller toy and started working my ass. After a few minutes of working my prostate I had a nice glob of precum at the tip of my penis. I used my finger to wipe it up off of my cage and taste it. I couldn’t have been more ready for cock. I kept my dick in its cage to keep the night going and logged on the chat again for more fun.....
After another hour of skype sessions I figured I would have one more go around before finally cumming and call it a night. Before I could start chatting a message popped up. “Hey Alex” was all it said. Blood rushed from my head and my stomach dropped. A cold sweat came over my entire body. I could barely swallow the spit in my mouth. How did he know my name?
H: Hey Alex
M: I think you have the wrong guy. My name is Chad.
H: No, it’s Alex
M: What makes you think that? My name is Chad.
H: Look on the floor behind you. You see that sweater?
Damn.... He had found out who I was! I was able to piece together exactly what happened within a few seconds. My sweater was on the ground behind me with our school logo and the words swim team under it. From there it would be a piece of cake to find me.
M: I guess you got me. My name is Alex.
H: I know, I looked up the swim team on the school website and there you were.
M: I must have put on quite a show for you to try and look me up haha
H: Yea, it was quite a show. I want you here in my house in 1 hour.
M: Sir, I can’t, my girlfriend is coming over.
H: Check your messages.
I opened up my inbox and clicked on his message. It had an attachment that I then opened. It was a video of our skype session that we just had...
M: You recorded that?!?
H: Yep, I want you over here in one hour, still in your cage and in a bikini or the video is going to be sent to your girlfriend Sarah through FB.
I quickly shut my laptop screen. I could hardly breathe. I was in a panic and I didn’t know what to do. I stood up pacing back and forth in my room trying to find a way out. I was on the verge of throwing up. Then my phone lights up. I received another message from him this time through FB. The message was screenshot of his phone showing him about to send the video to Sarah. I had to go over. I messaged him back. “What is your address?”
His house was in the next town over and in a good area. That didn’t help the fact that I was as nervous as I have ever been. I pulled up and parked on the street in front of his house. Just as I put it in park, another message popped up on my phone. “You just made it, come in”. I paused before getting out. It was a surreal moment. Sitting there, I finally noticed that my dick was still hard from before. I knew what was probably going to happen and that I had no choice. It was as if I had no thoughts except what I was feeling, which was a pressure around my small dick and a sick feeling in my stomach. Without thinking I opened the car door. I walked up to the door and knocked. The door opened and there was Henry. He was around 47, 6’2”, 250 lbs, overweight and hairy. He was scruffy but not bad looking. Truthfully, he was exactly my type. He had on a white shirt with a small logo. It was my girlfriend’s dad’s company. “Recognize the Logo?” My mind went blank. “Come on in Alex, make yourself at home.”
In a cold sweat and blank mind I walked into his living room and he already had porn playing. The room was dark and he went before me to sit on the couch. He patted his hand beside him and I followed his instruction. On the screen was a good looking blonde. She was laying on her back with her head over the edge, she was being face fucked with saliva running down her face. “Do you like what you see?” “Yes sir”, I replied. “As horny as you were earlier, I figured we might as well start with something a little more hardcore. Relax a little Alex, we are just watching a little tv." Once the clip ended he turned on another video. This time it was a shemale and her male counterpart sucking each other. By this time I had started to relax only slightly, just enough to be turned on by what I was seeing despite the circumstances.
Henry slid his basketball shorts off and his big cock sprung up from the waistband and slapped his belly. He had big balls as well and they were hanging in between his hairy thighs. He turned his head to look at me and found me staring at it. His right arm raised and went around my back. "We both know what's about to happen. We both know you want it. You have no choice Alex, you can either run through it and get it over with or you can enjoy it. Either way you will be doing the same thing." It crossed my mind that he was right. "Why not enjoy it?”, I thought. I have wanted this for a while now. There is literally nothing that I can do short of beating this guy's ass and we both know that will never happen. I should just enjoy it and let it happen. If I don't like it at least I will finally know. He started squeezing my back down and I gave easily. I bent over across his thigh and took the head of his cock in my mouth. It was hard, warm, and fleshly. I wasn’t how I imagined it, but I liked it. I went down as deep as I could which wasn’t very far, then rolled my tongue around the head. He had a musky smell. He obviously didn't bother to shower before I came over. I guess he didn't have a reason too. Each time I went down my dick would strain against its cage. I was loving it! Like a newbie I focused on wrapping my lips around my teeth no to hurt him and didn't know how to keep from drooling all over him. Henry grabbed me by my hair, pulled me off and looked me in the eyes " I knew you were a faggot”, he said with a wink. "You want my cock boy!?" "Yes sir!" I replied. "Open your mouth you little bitch." I opened my mouth as wide as it would go. He leaned forward and spit right in my mouth. My head jumped back as soon as he spit. I didn’t even realize what was going on. I just loved that he was taking control. "Keep it open!” He demanded. I stayed there with my mouth open waiting for his direction with my throat closed. "You want to swallow my spit?" I nodded. He leaned over further and stuck his tongue in my mouth. We made out, rolling our tongues and swapping spit while his beard rubbed against my face. He grabbed my face and pulled me away again spitting in my mouth again. This time he smiled afterwards. He pushed my head down to his cock. I was so excited to get going again. "Put your hands behind your back." I didn't even hesitate and I planned on not hesitating for the rest of the night. I wanted to please him as much as possible. His left hand grabbed a handful of my hair and lowered me down. Then he rested his cock my face, he grabbed his cock in his right and then started slapping my face with his big cock. It hurt, but I liked it. "You like that faggot!?" He asked. "Yes sir!" Then he pulled his cock back and the left hand went from the side of my face to the top of my head. He pushed me down to his balls. He didn't even have to ask. I started sucking and licking. The smell was intense, but under the circumstances it was the hottest smell in the world. "That's a good boy. How bad do you want daddy's cock?" He asked. "I need it sir, please I need it so bad!" I was a bitch in heat. My dick hurt so badly! I only wanted more! "You are going to have to earn it slut. You are in no position to walk away. You are going to do everything I ask. If you do you'll end up with my cock in your hole. That's what you really want isn't it?" “Please” was the only word I could find. There was no denying it in my mind. Not after I had gotten this far and finally relaxed with another man. He scooted his ass forward on the couch and lifted his knees to his belly. His left hand took its place on my head again. "Time to earn it faggot" he stated. He pulled my head into his hairy ass as hard and he could. My face was buried and I couldn't hold my breath anymore. I inhaled and my lungs filled with an intense sent I had been getting all night. I started licking his hole. I ran my tongue around and around flicking his hole. Fuck, this was turning me on even more and I thanked the good lord he was clean. I dropped my head down lower and started at the bottom of his crack and licked my way up to his balls, giving them more attention. I came back down and started licking again. He grabbed my hair and pulled me up. He told me to open my mouth again. He spit in my mouth for a third time. I was ready for anything.
"Get off your knees,” he demanded. I stood up, still in my street clothes. “Did you wear a bikini like I asked?” “Yes sir I did,” I replied. I took of my jeans and T-shirt and there I stood in front of him in a pink 2 piece bikini. He told me to remove my bottoms first. I untied the stings on the side and they fell to the floor. My small dick finally felt the air and that only increased the pain.
“Pick them up and put them in your mouth.” I followed his direction and stuffed them in my mouth. “Take off your top.” I was now naked in front of him. Turn around and look at the tv. There was now an older man fucking a younger guy in what looked like a hotel room. “Is that what you want boy?” “Yes sir it is,” I whimpered. He changed the setting on the tv and I saw myself. I couldn’t believe it, but at the same time I could. He had been filming the entire thing. I didn’t even care. In fact it made me even more ready to do whatever he wanted. “I hope you plan to watch this later.” I stated. “I won’t need to. You’ll be here whenever I want.”
“Now we have been camming together for a little while. I want you to give me a show right here,” Henry said with a smile. Bend over and spread your cheeks. I knelt to the ground with my face facing him and my face on the carpet and spread my cheeks. Mmm, you’re always so smooth. “You cleaned yourself out tonight didn’t you?” “Yes sir” I said. “Good boy” said my sir. Go ahead and slide a finger in your little hole. I then slid a finger inside myself and started working it in and out. Then he gets up off of the couch and gets behind me. “Keep going” he demanded. For a minute he sits there and watches, stroking his cock. His right hand starts he feel my ass and then he spanks me. Ugh! I moan into the carpet. He slaps me again in the same spot. I let out a slight whimper. He wasn’t holding anything back the next 5 licks he gave me. My ass was on fire. He grabbed my wrist and pulled my finger out, leads my finger to my mouth. “Spit out your bikini.” I did so and he shoved my finger in my mouth. His other hands circle my hole as a finger slides in. His knuckles were bigger than mine and I loved he sensation. It quickly became two and then three. My hole was stretching to meet his big fingers. I had only been stretched out like this a few times. A pain would run through my body each time his knuckles went in. I only wanted more. I started bouncing back against his hand to get all of his fingers. “Not enough for you slut?” He questioned. Finally, he added a fourth and it hurt! “Ahh fuck!”I cried around my finger. I stayed perfectly still and I could feel every single finger as it slid inside of me. Before he got to the knuckles, he stopped. “I don’t want to ruin your hole. My cock likes it right.” He slapped my ass one more good time as I jerked up. His hand pushed me back down and he let my hand go so I could take my finger out. It was replaced by some of his own. “Suck” was his only word. I bobbed my head and started to suck. I could only barely move because my head was still lying on the carpet. Then it hit me. Everything that I had done and was doing. I would never be able to come back from this. I liked it too much. I loved the dirtiness of the way he treated me and the taste of my ass and his. I would be coming back, I knew that. But I would never really know if it were myself or the circumstances that would drive me to him. That’s how I knew I was his.
Henry stands up. “Follow me.” I start to stand up. “Back on your knees!” he yells. “And stuff your bikini back in your mouth” He starts to walk away, I take my bikini bottom and stuff my mouth then I begin to crawl. We work our way down the hall. My thighs are grazing my caged dick. I’m about to cum from sensation. The hallway is so long that i don’t think I will be able to make it. Right before we get to his room I stop. I know what could happen if I go any further. My dick convulses just a little and a small amount of cum leaks from my cage. It was a ruined orgasm. I keep still and wait. Henry comes back in the hall to see if I had ran off. Then he sees what in between my knees on the ground. “Open your mouth” He grabs my bikini bottom and wipes up the mess. He crumples it up and stuffs it back in my mouth. We continue on with only a short ways to go. I can taste my cum, I have tasted it many times before. But now I wanted it to be his.
“Stand up, sit down at the computer and log in to our website” I did as he asked. He goes into the chat room and types" Check out my cam, about to suck a cock!” The messages roll in. The chat room has a public cam setting and he chooses that option. We were now streaming to everyone. He lowers the camera to his crotch. “Get up and get on your knees”. Henry hops on the seat and turn the chair 90 degrease so our viewers can see everything. “Go ahead slut” I take his cock into my mouth and start working it. I was so hungry for what I was receiving. The messages continue to roll in. Each time a new one came in a “bing” sounds would be made. The amount of messages was overwhelming because I knew that they could see me. He grabbed my head and pushed me down until a I gagged. Saliva started running down his cock. We did this repeatedly. His warn cock was so hard and the way it fucked my mouth was amazing. “We have 87 viewers. I want 100. Make it happen” He took his hands off of my head and I started throat fucking myself, doing what a I could to take more of his cock. His cock was too big to go all the way down and his girth was taking a toll on my throat and jaws. I kept going, making sure to leave as much saliva as I could. Then I dropped down lower and worked his balls. They were covered in my spit. "93 boy."
I raised my head back up and started sucking his cock again. Going down as far as possible, gagging each time. This time I was going much further. I could feel him in my throat and my reflex was starting to subside. Oh fuck boy, keep going. He was as hard as a rock. His hips started thrusting a little taking his cock deeper. Both his hands jerked my head off before he came. "107 boy, good job." I smiled. Saliva was running down my chin and chest. Henry picks up my bikini bottom and without him asking I open my mouth the receive them.
He walks toward the bed. “Crawl over here.” I make my way over, a bikini bottom string hanging out of my mouth. My dick is numb from the straining and pain. I arrive at his feet. “It’s time to make you all mine. Hop on the bed with your ass facing me.” I hop up, knees on the edge, raising my ass as I as it could go. Your ready aren’t you slut. "Yes sir! I want it all." Both hands grabbed a cheek and spread my ass. I could feel his beard first and then the rest of his face, finally his tongue worked my hole. Each hand squeezed a cheek and he moaned. Damn, I love a smooth ass. He bent over and started again, eventually darting is tongue inside of me. His large hand reached under and pulled at my cage. "Oh fuck," I screamed. Pain and pleasure were fighting each other and I could tell which one was winning. He stood up. "Stay where you are” He walked over to his bedside table and pulled out a tube of lube along with a small brown bottle. He arrived back behind me and I heard he cap flip open. He squeezed and the cold lube landed right on my hole. I knew better than to ask if he was going to wear a condom. His finger worked the lube inside of me. I was ready. He reached around a showed me his brown bottle. "This is a popper. Ever had one?" "No sir," I replied. He put the bottle under my nose, “Sniff.” I couldn’t do it. I had no idea what it was. “Breathe in, you'll love it” I gave in and inhaled. What other option did I have?
He places the tip of his cock on my hole and starts the push. I The head popped through and a little pain shot through me. He pushed further and his cock slid deeper stretching me apart the further it went. The poppers then started to take effect. That pain became a very intense pleasure. He kept pushing, trying to get balls deep. "Oh my god," came out of my mouth. He pushed a little more and I could feel his balls graze my ass. After a couple of seconds he grabbed my waist and pulled me to him while he pushed his cock and inched forward. The pleasure was intense. It felt like I was being split into two but it felt so good. His balls were resting on mine and he slapped my ass. My hole clinched around his dick. He pulled his cock all the way out. The whole process started again. This time much more pleasure and less pain. I could feel every inch of his cock spreading me. The stress against my insides as he pushed in and the insane pleasure along my prostate was a feeling that you can't describe. I couldn't tell if it was the poppers or the size of his cock but my mind was in ecstasy. You’re in the moment and all you can do is feel and the feelings are so overwhelming that you can’t think, your brain is simply processing to much. As he started fucking me harder without stopping I could feel the precum dripping from my dick. It was wiggling around underneath me in pain. For the first time I wasn’t receiving pleasure from my dick but from my ass and it was so incredible I knew I wanted more. Pumping harder and harder his thighs slapped against me. I couldn't help but moan. He finally grabbed my hips and pulled me in while thrusting as hard as he could. He pressed against my insides. The extreme felling of being full made me leak even more. Henry pulled out and went to his drawer again. He was still rock hard and his cock was pointing up in the air. He grabbed a band out of the drawer and wrapped it around his cock and balls. I knew I was in for more.
Henry grabs my hips and spins me around. I’m now facing him on my knees. "Lay on your back." I quickly obliged. He reached in the drawer again and pulled out a toy that looked like a plastic plug with a tube running from it into a plastic ball. Henry crawled on the bed and told me to lay on my back, head near the edge, and pull my knees towards my chest. I pulled them all the way until my ass was slightly in the air. He took his left hand and took the panties out of my mouth. By this point they were soaked. He put them in his right hand and placed them at my hole. He took one finger and started shoving them in. He shoved them in as deep as they would go and then grabbed his toy. He applied lube to the plug and slid it in my ass, shoving my panties deeper inside. "Make sure it doesn’t fall out." I reached down and make sure it stayed where it was. I felt around and could tell my hole had been fucked. Henry got off the bed and stood at the edge of the bed where my head was. He pulled me towards him and my head started hanging over the edge of the bed just like the pornstar we saw before. He grabbed my head and shoved my face in his balls and rubbed his sack up and down my face. Open your mouth slut. He took his cock and shoved it in my mouth. From this angle he was able to slide it pretty far down my throat. He started thrusting and going deeper and deeper. Spit was rolling down my face into my hair. Henry went a little further down and held it there while I gagged, then I felt the toy inside of me expand. He pulled his cock all the way out as stands of my spit rolled over my face. He grabbed me by the hair, lifting my head to the ceiling and showed me his pump handle. He held the brown bottle back up to my nose and I inhaled without being asked. I knew from before that I needed it. Henry pumped two more times expanding me further. Henry's cock was basically resting on my neck and my mouth was near his balls as I moaned in pleasure. "This feels so fucking good". Two more pumps and the felling was pain mixed with pleasure. Mr. Danny reached down and pulled out the plug then showed me how much of a slut I was. It was enormous. It was only around 9 inches long but as big around as the top of a red solo cup. Henry put the toy back near my ass and wiggled it back in. I yelled in pain. Ow, fuck! The feeling was too intense. I felt as though I was about to pass out. Henry slowly removed it once again. I felt completely empty. With my head over the edge of the bed Henry grabbed the panties and put them back in my mouth.
Henry crawled to my legs and his finger entered my gaping hole. He fished out the panties and showed them back in my mouth. He kept my knees pushed up to my chest and shoved his cock inside of me and started fucking me as hard as he could. The only feeling I had was pleasure. I could still feel every inch of him inside of me. The drugs I was given were making this incredible. He started fucking me relentlessly again wrapping his hand around my throat and choking me. His balls slapping my ass and his cock putting pressure on my prostate, giving me a constant sensation of being close to an orgasm. "You want my cum boy!?'' I spit out the panties. "Yes sir! Please, cum inside of me! "I need it so bad, cum deep in me sir, please! He continued to plow me until he started to tighten up and his grunts became louder. Finally, I could feel it. His spurts of cum shot inside of me filling me up with warm cum. He was deep inside when he let go and his small thrusts in and out were to round of his pleasure. He slowly slid his cock out and I could feel cum follow him out and run down my ass. "You are one good slut" I see Henry reach down and feel him wipe up the cum rolling out of my ass with the panties and shoves them back in my mouth.
"I can't wait for next time," he said with his back turned to me and him looking at the computer screen. "Me neither sir, that was incredible," I replied. "Come over here and check out the recording of us," Henry stated. It didn’t even faze me that he had recorded everything. What more could he have over my head. I leaned over his shoulder and watched myself getting fucked. It was insanely hot. I looked good getting fucked! "What did you think Sarah!?" Henry said looking at the computer. The sound of my girlfriend’s voice came over the speakers. "That was all I hoped it would be Henry!" My stomach dropped just as it did before, blood rushed from my face and the incredible pressure against my cage went down as a result. Mr. Henry minimized the screen and there was my girlfriend. She had been watching through the camera the entire time. "Hey baby, did you have fun tonight?" I couldn't think of anything to say. "Don't worry; we have been setting this up for around a month, I have always known." "It turns me on so much to see you get manhandled. I came twice watching." "I can't believe this!" was my only reply. "You liked it didn't you? I just heard you," Sarah stated. "Yea, I guess so, I said softly" Sarah laughed. "We all know there is no more guessing. You'll continue being my boyfriend and servicing me like you have. Next time I will be in the room watching and helping. Then we will add a few more guys from the company into the mix.
And that’s exactly what happened. Two years later, I'm married to Sarah, writing this story on a Saturday afternoon and already know what happens tonight.