It had been a week since the last time I heard from Dylan, but I knew that I would hear from her soon. Where previously she had a grainy security video of me sucking another man’s cock, I had given her much more to blackmail me with in our last encounter. I sucked six men off at the strip club thinking I would get to fuck one of her stripper friends, but Savannah had fucked me with a strap-on while I sucked her boyfriend. And with everything recorded, I knew Dylan would be in touch soon. The scary thing is how much I looked forward to her next contact with me.
I have only known Dylan for a short while, but am completely intoxicated by her. Not only is she extraordinarily beautiful with her long, sleek, sexy body, but the look in her beautiful eyes when she is making me do things I never thought I would do completely turns me on along with the smile she gives off while being cruel to me.
I didn’t have to wait long as Monday morning I opened my email and found a message from Dylan. I closed the door to my office before opening it. It read,
I hope you had as great a time as I did the other night. I could see from the look on your face just how much you love sucking cock for me. The videos picked up your love of cock too. You performed like a champion too when Savannah fucked your ass while you sucked Tony. I’m so glad I met a real whore like you. You make me so happy.
Until we meet again, I have an assignment for you. You are to suck at least one cock a day (but I wouldn’t be surprised if you sucked more) and send a picture of it to me. I expect to have at least one picture emailed to me each day by 10:00pm so I can show the girls in the club. I’m sure I don’t have to tell you the consequences of letting me down.
Hugs and Kisses,
My heart started racing as I immediately thought how I would go about this. I needed to find cocks to suck, but also needed to stay anonymous. I had trouble working that morning, so I decided to take the afternoon off. I started browsing online personals, but knew that wouldn’t give the anonymity I wanted. I was worried until I saw an ad from a man saying he was going to be at a glory hole at an adult book store about 30 miles away. I knew what I had to do.
I drove to the bookstore. Once inside, I browsed around for a little while and then snuck back into the video booths. I looked in a couple of the open ones, but saw no holes. Near the back of the booths, I finally saw a hole and entered that booth. I put a few dollars in the video machine and waited. A short while later, I heard the next booth open. My eyes went to the hole as my heart raced. The man next door started rubbing his crotch. I went down to my knees in front of the hole. I watched as the man took his cock from his pants and moved closer to the hole. My mouth moved closer to the hole and he stuck his cock through. I wrapped my lips around it and started to let him slide his cock into my mouth. As I felt it harden in my mouth, I thought about Dylan coaching me, telling me what I needed to do to get this man off. I moved his cock in and out of my mouth and took time to lick his balls. I thought I had him ready to cum and was about to finish him off when I remembered my assignment. I needed to have a picture of me sucking his cock to send Dylan. Taking my phone out, I quickly took a picture with it of me sucking his cock. Moments later I felt his cum flood my mouth. I swallowed every drop.
I watched him zip up and exit the booth, waited several minutes, and then left myself. As I exited the bookstore, the fat clerk smirked like he knew what I had just done. When I got home, I looked at the picture on my phone of me with my lips wrapped around a hard cock. I then sent it off to Dylan.
That night I scouted out other glory holes. I found two others less than an hour away. For the next week, I rotated bursa escort between the three not wanting to be known as a regular cocksucker to the clerks in the stores. Every night, I would send Dylan a picture of me sucking a cock. A few times, I even sent her pictures of me with cum all over my face and the other man’s cock still in the picture. I was surprised that I hadn’t heard from Dylan after I had sucked 10 cocks, but I knew I needed to keep going for her.
On Thursday night, I was getting ready to leave work and head to that night’s glory hole when my secretary, Tessa, alerted me to an emergency that needed to be taken care of immediately. This was something I had to take care of myself and couldn’t delegate to anyone else. I threw myself into solving the problem and finally fixed it. I was so into fixing the problem that I didn’t look at the clock and when I finally solved it, it was 10:30pm, 30 minutes past Dylan’s deadline for me. I was completely wiped out and knew it was already too late, so I just went home and to bed, fearing the worst.
The next morning, I was dreading the email I knew I would receive from Dylan, but I had been at work almost all day and not heard a single word. I thought I might try to suck two cocks for Dylan tonight to make up for last night and was planning to do so. My office door was closed as I planned my Friday night, but Tessa buzzed in saying that my 4:00pm appointment was here. I looked at my schedule and then told her that I didn’t have an appointment this afternoon. After a brief pause, Tessa said, “You were right, Steve. Dylan said her appointment wasn’t until next Friday and she and her partner are leaving.”
I bolted from my office, right past Tessa. The elevator was already closed and on its way down so I ran down three flights of stairs. When I got to the bottom of the stairs, I could see Dylan and a man leaving the building. I shouted for them to wait, but they kept walking. I chased them out to the parking lot and finally got in front of them. I was breathing heavily, but couldn’t help but notice how absolutely stunning Dylan looked. In the strip club, she always looked sexy, but she came to my office today dressed like a professional businesswoman and she was absolutely stunning.
“Dylan, I’m sorry for” was all I got out before she slapped me across the face to shut me up.
“Listen to me, slut” Dylan said. “And listen to me well. You disappointed me last night when I couldn’t show my friends a picture of you sucking cock for me. That makes me look bad and I hate to look bad. I should have just sent all your cocksucking pictures to all your friends, your family, your co-workers, everyone. You are extremely lucky that I’m so nice. Maybe I should have you suck my friend, Bill, here off right in the parking lot in the middle of the day.”
I knew I had no other choice than to do what she demanded, but I had to beg her not to make me suck off this large, well-built man in the parking lot.
Bill smirked down at me. Dylan continued, “You have disappointed me and will have to pay a penalty. Let’s go up to your office and discuss how you are going to make this up to me.”
While relieved that I didn’t have to give Bill a blowjob in the parking lot, I still dreaded what was to come. We rode back up the elevator then walked past Tessa and into my office where I closed the door.
Dylan immediately commanded me to get nude. I moved to lock the office door, but when Dylan saw that she smirked and told me not to. I proceeded as ordered and stripped out of my suit to stand before her and her friend completely nude.
“First, as I’m sure you are aware of, you are going to suck Bill off in your office,” Dylan said before she broke into a big grin. “But Bill doesn’t let faggots suck him for free. I’m sure a bigwig like you has company checks to sign. You need to write a check bursa escort bayan to Bill Brown for $1,000.”
I went to my desk and pulled out a checkbook and did exactly as Dylan wanted and then handed him the check. I was thinking about how I what expense I could say it was for. Bill handed the check to Dylan and she said, “Something is missing here. You forgot one thing; you need to write in the memo line ‘For letting me suck your cock’.”
I knew I had no choice so I did exactly as she said. I thought it might go unnoticed by our accounting department, but knew I would have to do a huge cover up. I would have to worry about that later.
Dylan smiled and said, “Well you paid to suck his cock, you better do it.”
I got down on my knees in front of Bill, unzipped him and took his thick eight inch cock out of his pants. Nude, down on my knees, I started working on his cock. I used all the practice I had to perform for Dylan on her friend. After several minutes of attention to his cock, I knew he was getting close. Then Dylan told me to slow down. I continued to suck Bill’s cock very slowly, keeping him hard but not giving him release.
“I’m going to give you a choice today,” Dylan said with that lovely smirk on her face as she sat at my desk. “If I push this button, I can call your secretary in here to watch you suck Bill off. Your other option is to ask Bill to fuck your ass. I’ll give you 30 seconds to ask him that before I call your secretary in here.”
It didn’t take me two seconds to make the decision. I quickly asked Bill if he would fuck my ass. With no response, I started begging him to fuck me. Finally, he told me he would.
Dylan then interceded and quickly told Bill to cum on my face. Before I knew it hot ropes of his cum were spewing from his cock onto my face. As I went to wipe it away, Dylan told me not to. She then instructed me to give her my house key. I got up and did as she commanded. She then said that she would meet me at my house in an hour and that I was to keep his cum on my face until then. As she and Bill left, I looked at the clock. It was 4:45pm and everyone should be gone when I leave with cum on my face.
I stayed locked in my office until about 5:15. At that point, I was dressed in my business suit, but my face had Bill’s dried cum caked on. I slowly opened my door and didn’t see anyone. I made my way out of the building and all was clear. I had a sigh of relief as I got to my car and made it out of the parking lot.
I made it home five minutes ahead of the deadline and since I had given Dylan my house key had to right the doorbell. She smiled as she saw my still cum-covered face and let me in. Dylan had changed into lingerie and looked so incredibly beautiful as she led me into the bathroom and washed my face. She gave me a big hug and kiss, pressing her sexy body against me before telling me how much she was going to enjoy watching me take another man’s cock up my ass.
Dylan took my hand and guided me down the hall to my bedroom where I saw Bill lying naked on my bed. I looked at his cock, knowing it would soon be fucking my ass as Dylan told me to get undressed. I quickly removed my clothing as I watched Bill stand up. Dylan told me to get him ready, so I went to my knees and started slowly sucking his cock. I felt his cock start to grow in my mouth when I heard the doorbell ring. I took his cock from my mouth and looked at Dylan who had a mischievous smile on her face.
“Don’t worry,” Dylan said. “I told a girlfriend that you were going to get fucked by Bill and she wanted to watch, so I invited her. Just keep sucking your stud. We’ll be right in.”
I went back to work on Bill, in front of him on my hands and knees with my mouth wrapped around his thick cock. Moments later, I heard “Oh my god, you were right. He is a faggot.” I immediately recognized the voice escort bursa and I stopped in complete shock. I took Bill’s cock from my mouth and turned around to see Tessa. I couldn’t believe that Dylan had invited my secretary. Although I never acted on my desires, I had long wanted to fuck Tessa. She is a 25 year old beautiful blonde with an incredibly fit body. Tessa just started laughing as Dylan took her hand and led her to a loveseat. Dylan commanded me to keep getting Bill ready. I sucked him as Dylan explained everything to Tessa.
After a few minutes, Bill was ready to fuck me. Dylan said that she wanted to watch my face as I took my first cock in the ass so I was to get on my hands and knees on the bed facing her and Tessa. As I crawled around, I saw Tessa’s face for the first time since she entered and she seemed to be very amused by my situation. My legs were spread and Bill started rubbing lube on my asshole. Dylan told Bill to go ahead and fuck me and then Tessa surprised me by saying the same thing. The two girls were snuggled next to one another on the loveseat when I felt Bill’s cock pressed against my asshole. Knowing it was coming, there was nothing to do but accept it. “Please, fuck me, Bill,” I said as he started to press inside me.
Inch by inch of Bill’s cock slid into my ass. He fucked me slowly letting me feel him getting deeper and deeper inside me until all eight inches were inside my ass. Then Bill picked up the pace, fucking me harder and harder. I moaned as I took it all in while watching Dylan and Tessa giggling and whispering to each other over on the loveseat. After several minutes of an increasingly harder fuck that Bill was giving me, he said he was ready. “Cum in his ass,” Dylan commanded followed by Tessa agreeing “Cum in his faggot ass.”
Bill thrust harder and harder and filled my ass with his cum. As he pulled out, I could feel it trickling out of my ass. Dylan told me to stay on my hands and knees as Bill got off the bed. Bill went to the bathroom to clean up and Dylan and Tessa moved behind me to see how Bill had spread my ass wide open. They moved back in front of me.
“I had to bring Tessa here because you let me down last night,” Dylan told me. “Tessa has promised me that she isn’t going to let anyone else in on your secret. Not yet anyways. Not unless you screw up again. Since I can’t trust you to go out and suck cock when I tell you to, I’m putting Tessa in charge of you. When I want to see you suck cock, I’ll just call Tessa up and she’ll make sure you do it. If you’re too busy to go out, she’ll find someone you can suck off in your office. Now that you’re taking it in the ass too, I’m sure she’ll be able to find guys for that too. And for all her hard work, I’m sure you’d agree that Tessa deserves a $10/hr raise.”
After a moment of silence, I looked up at Tessa and said, “Tessa, I’d like to give you a $10/hr raise for helping me find cocks to suck and men to fuck me.”
“Let’s seal it with a kiss,” Tessa said and bent down, her lips inches from mine. Then she moved back, turned around, lifted her skirt up and moved her ass to my face. I planted a kiss on each of her cheeks to seal the deal.
Dylan smiled and told me to throw on some clothes. I was getting dressed as she said, “Tessa and I have watched you with another man. Would you like to watch us with each other now?”
I couldn’t believe what I was hearing and quickly blurted out that I would.
“That’s too bad,” Tessa said. “You really disappointed Dylan earlier so you don’t deserve to watch us. Dylan and I are going to have a great time this weekend. But you’re going to have to spend it in a hotel. There is a bag packed for you. But don’t worry, I’ll send some company over for you. I’ll give you your house keys back at work on Monday.”
As I walked to the door, I picked up the bag. I looked back and saw Dylan and Tessa engaged in a deep kiss. I wanted to stay, but Bill was holding the door open for me. As I drove to the hotel, I worried more and more about what I had gotten myself into. But as much as it worried me, it excited me even more.