This story starts back in 2003 and is a true story. I was away at college and living in Peterborough, ON. I spent a lot of time on the computer doing school work and chatting with my friends from back home and girls that I was trying to hook up with.
Occasionally I would chat with a women from just outside of town. She was in her mid 40s and was apparently looking for someone to play with along with her husband. Being young and naïve I went a long with it.
After several months of chatting it seemed as though it was never going to happen. One night I received a message from her husband, he wanted to me just off campus. Sure I thought and got ready to go. My roommates and I were pretty tight and if I told them I was going somewhere they would likely want to come so I dressed like I was going jogging and set up. When I arrived at the plaza there was a grey van parked there. As I approached the back door opened and I jumped in. The husband was driving and the wife was sitting in the back seat. Her pictures were exactly the same (no bullshit here). I asked what we were going to do and she replied “get to know each other baby”. She then began to strip while her husband drove off. Once she was naked she motioned for me to take my clothes off. As I stripped she reached into a bag and pulled out a pair of neon green panties and matching bra. Once I was naked she looked me up and now and said to hubby “I feel dirty being attracted to this kid” he simply giggled and kept driving.
I was instructed to put the panties and bra on. Once I was dressed, she reclined my seat and began to rub my cock. At this point I was rock hard and completely OK with whatever we were going to do. About this time her husband pulled behind a grocery store and parked. He climbed into the back and his wife sat on his lap.
We chit chatted for a few minutes all while she was rubbing my balls and shaft. “Do you want to fuck my wife tonight?” he asked “Y-Y-yes” I replied. “Good” she said, “but first you have to suck his cock and let him cum on your ass”. I really wasn’t sure about this but agreed. He climbed onto my seat and dropped his tiny (maybe 5”) cock into my mouth. I sucked and sucked and sucked. Eventually he jumped off and yell for me to turn off. I quickly turned off and he ripped the panties down off my ass. He pushed me flat and his wife, using both hands spread my cheeks apart. Next thing I know I feel his warm cum filling my ass crack and my rose bud. The feeling of his cum in my ass was too much to handle, I started cuming. Filling the panties and spilling onto the seat.
The wife pulled my panties up and started massaging my ass, sqeezing my checks together so the cum had no where to go. I rolled off and they noticed the front of the panties were covered in cum. At this point she was angry, they both started raising their voices and demanded I take the panties and bra off. Once naked he opened the door and threw my clothes out and pushed me out of the van.
I never heard from them again. Or so I thought. About 8 months later a random guy added me to yahoo messenger. He claimed to be in his 50s and was a store manager at a local store. I asked how he got my contact info but he never really gave a compelling answer. We chatted for a few months and eventually he mentioned that he had heard from a friend that I sucked an excellent cock. He wanted to know if I would be willing to make an arrangement where I suck him for money on a weekly basis. I was floored. I didn’t even respond for a couple days because I really had no idea what I wanted to do. As a cash starved student any money is appreciated right? I thought… After a couple inquiries from him I decided what the hell.
We met every Friday at 5:15 at the same corner for 6 months. Each time I would hop in and he would drive off and I would suck him off. Once finished he would slip me a $50 and drive me back to the corner. Once school was over I moved back home. We continued to chat and anytime I was up in Peterborough I would stop by his store and blow him.
A couple years later I decided to return to school. I was out looking for work when I bumped into him on the street. We casually chatted and he mentioned that he was hiring for weekends and that I should drop by with a resume and him and the assistant manager would interview me.
That night I emailed him the resume. He called me at 10am the next morning to invite me that afternoon for an interview. I arrived and met the assistant manager. Seemed like a nice enough guy. We chatted and eventually he called the Manager (we’ll call him Peter) into the room. We chatted a bit more and then the assistant manager left. No sooner did the door close and Peter asked “how badly do you want this job?” “Badly” I replied. He then instructed me to suck him off. I obliged. Once we finished he took me out and introduced me to the staff.
I only worked Saturdays and Sundays. Occasionally, if I didn’t have school I would work a week day too. At the end of each shift I worked with Peter we would close together. Once the last person was gone he would drop his pants and I would blow him. I was then allowed to take $50 from the till and be on my way.
After a few weeks the Christmas rush was dying off and the store slowed down. All the seasonal staff were let me except me. Peter mentioned that I would stay on doing back room stuff until it picked up again in the spring. I didn’t care, I was just happy to keep getting a pay cheque so I didn’t ask to many questions.
The next Saturday I showed up for my first back room shift. I was instructed to ensure the washrooms were sparkling and keep the storage room clean. “No problem” I said and set out to clean the mens room. I was about half way through cleaning when there was a knock at the door. “Sorry, I’m cleaning you’ll have to come back” I said. I looked up and a man in his 40’s was closing the door and locking it. “Can I help you?” “Yes, actually you can” said the man. “Peter mentioned I would find you in here, says you’re a good suck” as he pulled out one of the biggest cocks I had ever seen. I was still on my knees as he held it out to my mouth. I started licking it. He was enormous, filled my entire mouth and constantly caused me to gag. I eventually sucked him dry. Without saying a word he left a $50 bill on the counter and left. I sat there dazed for a few minutes. “What the hell just happened” I wondered. Before long Peter appeared. “You’re doing some fantastic work! Keep it up” and he left. Once I finished the mens room I went into the storage room to have a break. A couple minutes later another man appeared. “Hi, I’m here for the blowjob” “uhhh, yes, you’re in the right spot I said” He nervously pulled his cock out. I started sucking but he wasn’t getting hard. I asked if there was a problem? “Well I’ve never had a guy suck my cock before, would you mind putting those on” He said as he motioned to the bag he brought in.
Strange I thought but sure. I got dressed. In it was black 3” heels, pantyhose, a thong, mini skirt and blouse, bra and a redheaded wig. Once I was dressed I went back to sucking. It didn’t take long for him to swell and blow… maybe a minute. He slipped a $50 in my skirt and left.
Peter came right in. “Wow, you are doing great work today!” I said “Since when did I become a blowjob machine Peter?” He mentioned that he didn’t have the work to keep me but he could supply a steady stream of customers. I could see him eying me up in my outfit. “Keep the outfit handy, lots of guys will want you in that” he then proceeded to give some more instructions for store tasks and left.
This continued every Saturday and Sunday right through until April. On my last Sunday shift I was so busy. Usually I made $250-$350 a day but that day I made close to $600. Around 4:45 I sat on a bed and just sighed. I was so tired and just wanted to go home. I laid there until almost 5pm hoping/praying no one else would come through the door. Peter announced that the store was now closed and all customers should proceed to the check out. I hurried to the front eager to get out. “Whoa, Tiger” said Peter “You can’t leave on your last day that quickly. We have a going away present for you” “oh ok, awesome. I’ll just wait in the back I guess?”
“Yes, but make sure you are dressed” I hurried and go dressed and sat at the desk waiting… and waiting… and waiting. After about 15 minutes Peter called out “Can you come to the back please”
I nervously walked out into the store looking around. I didn’t see anyone so I headed to the back of the store. At the back were two beds that were for sale. Laying on the beds were a man and women and Peter was sitting on the other bed.
“For all the hard work you have put in here, this is my thank you to you” He said as he motioned for me to join the couple on the bed. Immediately the women started caressing me. We locked eyes. “holy shit” I blurted out, “you guys are from the van” “Yes sweetie, we are” she replied as we began to kiss. Her husband didn’t do much. He just chatted with Peter and watched us fool around.
I laid her on her back and began to make my way down to her pussy. I really wanted to eat her out. As a began to lick I felt to hands on my hips. My ass was pointing in the air while I ate her pussy. He husband took this as an invitation to try and fuck me.
I initially resisted but peter came over and convinced me to do it. He fucked me until I was almost in tears. I could barely play with his wife. I could feel his cock swelling and knew he was about to cum. He gripped by hips and shoved his cock deep in my ass as he squirted more and more hot cum into my ass. When he was finished he pulled out and climbed on to the other bed. I lay there panting. I was sore and exhausted and the feeling of cum flowing out of ass was very weird. Within seconds Peter was motioning me to get back in position. No sooner was on my knees was his cock sliding into my ass. He was WAY bigger than the other guy, I could feel the size difference. He started fast right away. At this point the women rolled over and put her ass in my face. I started licking her anus as I was getting pumped. After maybe 3 minutes Peter was filling my ass with cum. It was the weirdest feeling ever as my ass was completely full of two men’s liquids.
I collapsed. Dead from the fuckings and all the bj’s I had dished out that day. The women climbed on top of my face and instructed me to finish her off. I obliged. Once she was done she kissed me and tucked an envelop into my bra as he and her hubby left. Peter showed them out while I lay on the bed. While he was gone I counted out the money in the envelop. $1000. Jesus I thought, how on earth could they part with that much money. When Peter returned we chatted for another 30 minutes before walking out. As we passed his office he said “Just a second, I have one last thing for you” He came back with another envelop. “This is for you, its 10% of all the fees I collected from the guys he saw over the last few months.”
I was speechless. He opened the door and motioned for me to leave. As he was closing the door behind me he whispered, “If you’re ever in the area, let me know. You know the money is good” and with that he shut the door and I was on my own