It all started when I had lunch by the lake, near where I work. I was in my truck parked in a parking area with a nice view of the lake enjoying a Sandwich, when a car pulled up next to me. I didn’t really think much about it, until after a few minutes I glanced over and noticed the guy next to me was looking at me, I just looked straight ahead and continued with my lunch, a few minutes later I look back and he had taken out his cock and was playing with it.
I was shocked but also mesmerized. I surprised myself by not driving away, I was married and very interested in women, but there I sat watching a stranger stroke himself. It was hypnotic. I continued to watch him stroke until he came all over his hand, then he put his cock into his pants and drove away. I am not sure why he picked me, or if he just liked having an audience, but this experience sent me down a road I never thought I would go down.
For some reason I like watching the guy by the lake jack off, so I began to take more of my lunches returning to same location hoping to see that happen again. I never saw the same guy again, but I was lucky enough to see a few others stroke themselves while I watched. I never took my cock out, I was always afraid of getting arrested, but I wanted to and I wanted them to see me stroking my cock as well.
I began looking at craigslist for others like me, and emailed back and forth but I was always to scared to meet. Then I got the idea of getting a webcam, my wife was a nurse, so she worked at 12 hour shifts at least three times a week. At first I just logged into yahoo chat and went to the chat rooms and watched other guys jack off it was arousing just to watch, however that was not enough, so I turned on my webcam, then I pulled my cock from my pants and began to stroke, I had a few people watch and it was a rush. I even had a couple of guys IM me and ask questions about me. I was beginning to look forward to my webcam time!
A few weeks later my wife had gone to work and I sat in front of the computer with my jeans unzipped allowing strangers to watch me stroke my cock.
When I started getting IM’s from a guy who was more telling me what to do than asking. First he asked if I like being watched, which I did. He told me to strip naked, which I did, then he told me to turn around and show him my ass, then bend over and spread my cheeks I don’t know why I was following his orders but I was. Other guys who were watching me began sending me lots of messages of encouragement and wanting to chat, I tried to respond but there was so many, Jimmy (the guy who had been giving the orders) saw I was responding to others and he told me to stop and that I should only be chatting with him.
I did as he asked, then he asked how many guys were watching me, it was 12 at the time, he told me to kick them all off except him. I did as he asked then he had me lean back in my chair, show him my balls and ass, I felt like I was being examined. He asked me a lot of questions if I was married, how many guys I had been with, he liked hearing that I had never been with a guy.
He then had me stroke my cock until I had came for him. He asked when the next time I would be online, I told him Friday, he told me in the next few days I was to go buy a 4 inch butt plug, some lubricant and a 7 inch dildo that looked like a real cock and have it all ready when I got online on Friday, Jimmy said not to turn on my cam until he said it was ok, and to not allow anyone to watch but him. I agreed and said goodbye….. I had my orders for my next webcam session.
The next day I went to an adult store and went in, I had been there before I was married and would buy magazines but I never went to the toy section, there were lots of dildos and vibrators some life like which was a turn on, I chose a nice dildo then I got to the butt plug section, I knew what they were for and I knew what Jimmy had in mind, I am just thankful he told me to buy a small one, as I looked at the larger ones, I didn’t think it would be possible to take something like that. I picked up the butt plug and paid for it and the dildo, I was embarrassed thinking that the cashier knows what I will be doing with these items later!
Friday got there very fast and I had my new butt plug and dildo out and lubricated, I logged into IM but did not turn on my cam. In about 5 minutes Jimmy sent me a message. He told me to turn my cam on, which I did. He told me no one else was allowed to watch. He told me to strip naked, he again had me turn around and show my ass and bend over and spread my cheeks for him. He asked if I had the toys and had me show them to him. He told me to start sucking on the dildo, as he watched, I put it my mouth and tried to suck it, he told me, that it looked like I needed to practice, so he told me from now on, once a day for 15 minutes straight I was to suck on that dildo to improve my blowjob skills.
He then had me move the webcam to my bed and told me to lay back and put my legs up in the air like a good little slut I did as he requested, a since of humiliation came over me, here I was naked with my legs in the air showing everything to a stranger that I had never even seen and was allowing him to order me around.
He told me to that we would not be using the butt plug today, because I needed to take care of some tasks before I start my anal training. I asked what training, Jimmy said, training so you can take me in your ass when I want! He told me the next time we chat, I was to be completely shaved around cock balls and ass that was the end of our conversation that day.
After our conversation, I got my electric razor and went into the bathroom and laid down a towel, I shaved and hair off my cock and balls and from around my ass, then I got into the shower with a razor and shaved everything smooth, the entire time my cock was hard thinking of my submissions to this stranger. I masturbated when I was done I was so turned on.
The next few days, I sucked on the dildo for 15 minutes everyday, I was getting better and taking more and more in my mouth and also able to do it for longer and longer periods of time. I kept myself clean shaven, and I did all this for a stranger and it excited me beyond belief.
Tuesday was my next webcam day, I got online and had an email, from Jimmy, he said he would be on at 11am and I was to already be naked on cam and allowing anyone who requested to see me. I did as he asked and at 11:00 I got an IM from Jimmy
he saw I had complied with his orders, he asked me how many men were watching me, it was 21. He told me to kick them all off, it was time for my anal training.
I got onto the bed and held my legs up, I took the lubricated butt plug and eased it into my ass, Jimmy was coaching me while I did it. It was uncomfortable at first but once it was in, it felt good. Once the bulb part was in my ass the plug was locked in. He told me to keep in inside me an hour a day. He asked about my blowjob skills and I told him I was getting better and continued to practice.
I asked him if I could jack off for him to watch, he said no more jacking off until I had sucked him to completion. Chills went up my spine, so far, it was all fantasy and some toy play but now he actually wanted to meet, and I had a choice, I could stay in my fantasy work or move into reality. Jimmy told me to meet him in a nearby mall parking lot in 30 minutes, he said he would be in a maroon explorer he asked me what I would be in, I told him black ford truck. He said see you soon and logged off.
My hands were shaking, I was torn on going through with this, I looked down and my cock was giving me the answer, it was standing straight up hard and straining to get even bigger. I put on some clothes and got in my truck and headed to the mall.
I drove into the parking lot, parking far away from the stores so I could be easily seen. I wished I had taken a beer with me or had a shot of something strong before I left the house. I didn’t have too much time to think about it because Jimmy pulled in beside me, he motioned for me to get into his SUV. I knew I was crossing a line that I could not go back over, but I took a deep breath got out of my truck and into his explorer.
Jimmy was around 6’2 red hair and had a little bit of a beer gut, his arms were muscular and defined. I didn’t know what to expect since I had never seen him so I was probably staring, He was wearing sweatpants and a short sleeved shirt. He chuckled as I got in and said you got here quick you must be hungry for my cock. All I could say was I didn’t know. Jimmy drove to another section of the mall parking lot and and parked between two larger trucks so that we could not be seen.
My adrenalin was pumping like crazy, I could feel my heart beating in my chest. Once he put his suv in park he pulled his sweatpants down and displayed his limp cock and told me to stroke him. Without hesitation I put my hand on it and stroked it for him. He leaned back in his seat with a smug look on his face. His cock was very soft and he was completely shaved as well, it didn’t take much time for his cock to harden to about 8 full inches. I could hear soft moans coming from Jimmy he was enjoying what I was doing to him, then he turned and looked and me and said ok slut its time for you to meet your first cock up close.
Jimmy then put his hand behind my head and pushed it down toward his cock, it was in slow motion as the head of his cock neared my lips, then it pressed up against my closed lips until with a small effort he pushed his cock into my mouth.
I opened and began sucking him like I had practiced. He had his hand on my head the entire time, guiding it and pushing it down when he wanted. He was saying some things to me, but my mind was racing with all that was going on, so I didn’t really hear anything, I was just enjoying the feeling of his cock sliding in and out of my mouth.
After a few minutes of sucking my mouth was getting tired so I took it out and licked his cock and balls, Jimmy seemed to like that. Then I put it back in my mouth and began sucking again. He began fucking my mouth, which I had a hard time keeping from gagging he took his other hand and lead my hand to his balls, so I played with his balls while he face fucked me, I felt them getting tighter and I heard his breathing getting more rapid, then he pushed down hard and I felt the pulses of his cum fill my mouth, it was incredible and frightening at the same moment, and before I could even thinking my options he told me to swallow his cum like a good little slut….. I did as I was told.
I raised up in the seat just like a slut who has just given a blowjob in the car, Jimmy told me I did ok for a first timer. He said go back home I will email you later. On the drive home I could not get over what I had just done Once home I checked my email to find Jimmy had already emailed me. He told me I needed to keep practicing on my blowjobs if I wanted to be a better slut. He told me, I was to meet him every Tuesday and Thursday at lunch in that same mall parking lot and I would be giving him a blowjob. I emailed back with a simple yes Sir.
From then on I continued my daily blow job practice so I could be a better cocksucker for Jimmy, why I was so obsessed with serving this stranger? I would meet Jimmy in the mall parking lot and not many words were exchanged, I would get in his SUV, he would drive to a private location and pull down his sweatpants and I would go to work on his cock.
After a week Jimmy told me to come to our meetings with my butt plug so he could see how I was doing. That next meeting after he filled my mouth with cum, he held me in place and ran his hand down the back of my pants into my underwear, he felt the butt plug lodged in my ass, and told me to unbuckle my pants, this allowed him to work the but plug in and out of my ass a little. He told me I was getting close to losing my ass cherry to him and I told him I was ready, I could feel my dick getting hard, knowing I would be getting fucked very soon, I had become a complete slut to this man. It must have turned him on too because he pulled my head back down to his cock and told me to get it hard again. It took a little while but I soon received my second load of cum for the day.
On the drive home my cock was still hard thinking about what was ahead for me. Once home there was an email waiting from Jimmy he had new orders for me, I was to continue my oral practice but I was to buy a bigger butt plug so I could be ready for him. Also everyday I was to lube my asshole before I left the house, in case I was needed to service him.
The next day I went to buy the larger plug and yes my ass was lubed and ready for action, I even stopped at a gas station restroom and inserted the butt plug, I was too excited to wait until I was home.
Thursday I went to meet Jimmy and while I was sucking him, he checked my ass to see if I was lubed, he started fingering me as I sucked him which caused him to shoot very quickly. He then took my face in his hands and wiped his dick off with my face, he told me not to wash my face until after my wife kissed me on the cheek tonight.
I got into my truck and headed home and later that night my wife went to kiss me and I turned my head slightly so her lips landed on my cheek where Jimmy’s dick and cum had been earlier that day.
The next morning’s email from Jimmy was short and to the point, I was to be lubed and ready and be and an address at 3pm. I was to strip naked as soon as I walked in the door. I was shaking with anticipation all day, I wore the larger butt plug all day so I would be ready to serve. I took a shower before heading to Jimmy’s house, once there I stripped naked right in the entry hall, he told me to go get him a beer, when I returned to the living room, he had sat on the couch and turned on some porn, he told me to get on my knees on the floor while he drank his beer.
I sat and waited as he drank his beer, the movies must have been getting him excited because he unbuttoned his jeans and slid them down, I helped him finished removing his pants and then saw the beautiful cock I had been servicing for the last few months. Jimmy spread his legs and told me to lick his balls, so I began licking and sucking his big balls, it was much easier doing this in a living room and not in a car, then Jimmy leaned back farther and pulled his legs up showing me his ass, I knew what he wanted, but a paused for a second until Jimmy reminded me what a slut I was, and this is what sluts do, and with that I began licking his asshole.
Jimmy was fully erect when he put me on my back, he felt my ass to see if I was properly lubricated, which I made sure I was before I left, he then put his cock head at the entrance to my ass, and told me to beg him to fuck me.
My cock was rock hard and I was so ready to be fucked by this man, but he was teasing me, so I began begging almost pleading with him to fuck me, he asked me if I was his slave and I said yes, and would I do anything he asked, and I said yes.
With that his cock began slowly entering me, nothing could have prepared me for the feelings and size that Jimmy putting inside me, inch after inch, I felt completely full but he kept sliding further and further, then he began to steadily fuck me, until I became used to the size, that’s when he put my legs over his shoulders and began pounding me ass calling me a bitch, and telling me how easy I was. He was amazed I sucked his dick twice a week and was now giving up my ass to him when he was a stranger to me. He started fucking me faster and fast it was uncomfortable and borderline painful
I didn’t know if I could go much longer when he pulled out and came on my chest and face. Then he got up, threw me some towels and told me to clean him up and then myself.
After I had done my cleaning, I was back on my knees while he watched more Tv, he had me suck him and swallow another load before I left.
After I got home I had another email from Jimmy, I would continue meeting him for his twice a week blowjob and once a week for me to give my ass to him.
I had become a total slut to this man, willing to do whatever he asked I didn’t know what the future held, but the fact my cock was getting hard thinking about it, made me think I was headed in the right direction.