My Boss Was a Prick! Part 1

Lisa_Steve

Well-Known Member
I, Lisa, worked for an asshole several years ago. He was fat, not really ugly, and a total prick. I work in an industry that is primarily blue collar men so I’m used to the crude comments and jokesfrom them...and even joke back with them regularly. My boss though regularly took things to another level. He once refused to approve my vacation unless I showed him my tits. Now, I’m sure everyone will point out that I could file sexual harassment against him, and you’re right. But the industry I’m in is an extremely close knit community. I discussed it with Steve and we decided to let it go. Anyway, a bunch of us would regularly go out to a nearby bar after work, we called it having a “staff meeting” though it was really about drinking and having fun. “Bradley”, our boss, rarely came but would on occasion. No one really liked him, but we treated him nicely because he was the boss.

One night, we were drinking and I was talking to one of the only other ladies that worked there, Lynn. We discussed what an asshole Brad is and then Lynn asked me if I’d ever sucked his dick? I nearly choked and said hell no and asked why she would ask that. She said there was a rumor that we had hooked up a few times. She then admitted that she had given him head on more than 1 occasion and said that his cock was short and fat. And by short she meant about 5” long. And by fat she meant EXTREMELY fat. Steve has a great dick, approximately 8 1/2” long and average thickness. I’ve always enjoyed sex with him and felt it was the perfect size. It was around 8:00 at the time, Brad wasn’t there but he did arrive a couple of minutes later. Lynn and I had been drinking since 6:30 and I was pretty buzzed. I strangely found it interesting what she was saying about the dickhead’s penis and wanted to get a peek at it for myself. I told Lynn this and she came up with a plan to get him to show it to me.

She announced we were moving the “meeting” to her house and gave everyone the address. She stopped and spoke to Brad in private before we left. It was 8:30 when we walked out the door, I rode with her because I was already too drunk to drive. Steve was working until around 2:00 am so he couldn’t pick me up. I called and left him a message telling him where I’d be, and then we left. She had invited about 10 people over but 30 minutes after we got there no one had shown up. We’d decided they weren’t coming so I put on a pair of her shorts and a T-shirt so we could get in her hot tub. She. Is very flat chested so she didn’t have a swim suit I could wear. She turned on some music, grabbed a six pack of beer and we went out and got in the tub. We were only in the hot tub for about 10 minutes when the back gate opened and Brad walked in. He had a bottle of Patron in 1 hand and a 12 pack of beer in the other. He said he had stopped by the liquor store for tequila and the grocery store for beer. He asked where everyone was and we explained no one showed up. Lynn told him to hop in, knowing he would have to strip at least to his underwear, but he refused.

We drank a couple of shots and a beer and Lynn tried again to get him to join us in the hot tub, he refused again. I got an idea and asked him if he still wanted to see my tits? He stammered a bit before saying hell yes, so I told him “I’ll show you my tits on 2 conditions. First, you approve my vacation request and Lynn will be my witness. Second, you strip down and get in this hot tub!” He said he would definitely approve my vacation, but said I’d have to show him my tits before he’d would do part 2. I stood up and lifted the T-shirt over my head and tossed it onto a chair and stood there with tits on display. I then sat down and told him “Now you!” He was still in his work clothes but quickly removed his shirt, shoes, and socks. Finally he turned around with his back to us and took his pants off. He then quickly turned around and stepped into the hot tub. He was only out of the water for about 10:seconds so I didn’t get a good look at his bulge. I looked at Lynn and she shrugged. She suggested we all get naked but Brad seemed uncomfortable with it, which we both found strange.

We continued drinking, we had nearly finished the Patron and Brad’s 12 pack was gone, when he got up to go ********. Lynn got out a minute later and waited for him to return. When he walked up, she grabbed his underwear and yanked them down, ripping them when she did. I was standing and about a foot from my face was the fattest cock I’ve ever seen! It was easily twice as big in diameter as Steve’s, maybe more. He was sporting a woody and, even hard, it was less than 6” long. His fat stomach hung down and nearly covered it, and might have had he not been hard. His balls were very large as well, they would have filled my hand completely. I stood there speechless, kind of in shock. Lynn slid the torn underwear down and told him he might as well take them off. As he stepped out of them he said “If I’m gonna be butt ass naked, you have to be as well!” Lynn didn’t hesitate and immediately stripped out of her swimsuit. I quickly sat down and said “I can’t! I’m married! Steve will kill both of us! Then I corrected it and said “All of us!” I couldn’t explain that He hated Brad so much that he’d go nuts if he found out I was naked with him. Lynn laughed and said “Bullshit, if anything he’ll be upset that he wasn’t here!” Brad stepped into the tub and repeated my words from a few minutes earlier “Now you!” When I just sat there he got on his knees in front of me and Lynn sat down behind me and grabbed my arms. Brad then started trying to pull my pants off. He got the shorts off but I locked my legs together so he couldn’t get my panties down. Unfortunately, they were small panties and were just strings on the sides so he ripped them and pulled them between my legs! Lynn got back in the hot tub and we were now naked in the hot tub with a boss we both hated!

When we had completely finished the Patron, Lynn went inside and brought more beer and some peppermint schnapps our. I hate peppermint so I drank the beer and they started drinking the schnapps from the bottle. We were all shitfaced by now so I no longer hesitated to get out to go ********. When I came back outside and got in the hot tub again , Brad said it was his turn, and went inside to ********. Lynn asked me if I needed to call Steve again, it was well after midnight by now, to tell him I was spending the night with her. I said no, he’d come and get me after work. She then got out and went inside as Brad staggered back out. When he got in the tub he sat down so close to me that our arms and legs were touching. He told me I was making him horny and said “I know you hate me, but I’ve wanted to fuck your brains out since the day I hired you! That’s really the only reason I DID hire you since you had no experience!” I could only assume he was being honest because I hadn’t had any experience and the job paid 4 or 5 times more than what I had ever made before. But I also knew that I was very good at my job now and he knew it too. I told him that I knew he wanted me to fuck him but that I couldn’t do it. He then said, “I bet if you ever fuck me once you’ll want to fuck me again! As a matter of fact, I’ll bet you. You let me fuck you tonight and if you don’t come to me by next weekend to fuck you again, I’ll pay you for your vacation and I won’t count it against your time!” I laughed, partially because I didn’t believe him and partially because I was drunk and considering it! But Lynn came back out at that time and sat down beside us.
 
Part 2!

We sat there talking and flirting for a while longer until I got out to ******** again. When I walked toward the patio door, I saw Brad sitting on the side of the hot tub. Lynn was in the tub facing him giving him a blowjob. I was surprised to find I was a bit jealous, but I turned and took a shower then went to bed in Lynn’s guest bedroom. The guest room was on the opposite side of the house from the master bedroom, and right beside her son’s room. He wasn’t home thank god, although he was 18 I certainly didn’t want to embarrass myself in front of her kid. I pulled the covers down and climbed in bed covering myself with the sheet. I figured I fall asleep immediately but I found myself awake, lying there thinking about the evening. Brad had actually been a fun person to party with, and I did find his cock fascinating! I eventually dozed off but not for long. I woke to someone whispering in my ear. I was lying on my back, completely naked, and Brad was lying beside me also completely naked! I don’t know what he said at first, but when I was awake enough to comprehend I heard him ask “Did you get mad at me for letting Lynn suck my dick?” I told him no, of course not. He then asked “Then why did you go to bed when you saw us? You looked like you were upset.” I told him I was just tired and needed sleep. I was very drunk at that point and certainly didn’t want him to know I was jealous. He kept questioning me about it and I realized after a few minutes that he was playing with my pussy as he’d talked..and I was enjoying it. I felt my pussy getting wetter and a familiar tingling in my clit. I knew I should stop him but frankly, I didn’t want to. I remember telling him we really shouldn’t, but I knew I was pushing my crotch into his hand so he didn’t care. He started caressing my breasts, licking my nipples and gently biting them. I was ready to fuck and told him something like “Ok... I give in. I really want to feel you inside me!” He kissed me on the lips. And whispered “Not yet!”

He then slid between my legs and sucked my clit into his mouth and I shook all over with my first orgasm. He got me off with his mouth 2 more times before climbing on top of me and asking “Are you ready now?” I could only respond with a loud “Oh yes!” I felt the head of his cock at my opening and remember thinking that he shouldn’t have any problem entering me because I was soaking wet, I could even feel where my pussy had soaked the bed sheet! As he began to enter me he said “I’ll go slow so I don’t hurt you. I know Steve’s cock isn’t like mine”. He started pushing into me and that’s when I really knew he was right! At first, I thought he would tear my vagina open. But he moved slowly and gently, easing in a bit and back out going a little deeper each time. I had my legs spread as far apart as I could trying to accommodate his girth. Finally he was all the way in. All I can say is thank GOD his dick is short or I wouldn’t have been able to handle it. I’ve slept with some fairly large cocks before, but never have I been stretched like this. Once he was all the way in, he lay still for a moment, then started moving slowly. He whispered “I have to go slow, I don’t want to cum too soon. But your body is so fucking hot!” I said “Please go easy, and don’t cum inside me!” I hadn’t been on the pill in over a year and did not want to get pregnant. Steve had a vasectomy 2 years earlier so it wasn’t a problem with him.

Brad began moving faster and in no time I had an unbelievable orgasm! The first one quickly became another one. I have never really been multi orgasmic, and never before from intercourse. Usually it requires oral sex for a very long time for me to cum twice. Sometimes, I cum during intercourse if I play with my clit while Steve fucks me. But I had already cum multiple times and could tell I was about to have the biggest one yet. He continued to fuck me, he was fucking me so hard I’m sure the slapping noise could be heard all over the house. Once again I felt the orgasm building and then I began shaking. I heard myself moan loudly and I asked him not to stop. I began shaking harder and heard him say “My turn now!” The next thing I kne I was lying limp underneath him, unable to move. I was sweating profusely and Brad was telling me “Sorry babe, but I totally filled your pussy with my cum!” I just held on to him shuddering every now and then. He finally pulled out of me and I felt it pop as he did. He wasted no time getting up so I asked him where he was going. He said “To clean up.” He then stood by the bed and pulled me to him and said “You should be able to fit it in your mouth now.” And he turned my head toward his cock and had me clean him up. He then said “I knew you could do it. I have to go now. See you at work! Oh, tell Steve hello.” He turned to leave and I rolled over and went to sleep. I woke up around 9:30 feeling thoroughly fucked and used. When I opened my eyes I lay there trying to process what had happened the night before. I heard a noise and looked over. Brad had left the bedroom door open and Lynn’s son, Cabe, was standing there looking at me. I looked for a blanket but they’d all been knocked on the floor. Cabe stood there for a moment than said “And all this time I thought you were married. How is Steve anyway?” He then grinned at me and went into the bathroom.

I got up and looked for something to wear. There was a small towel in the closet, not enough to completely cover me, but something. I had Brads cum dried on my thighs and I desperately wanted a shower, but Cabe was in there and I wanted to leave even more, so I grabbed the shorts and T-shirt from last night and put them on. I then gathered my things and went to leave before remembering that I left my car at the fucking bar I tried to wake Lynn up, but she was still out. I had no choice but to wait for Cabe to come out of the shower and ask him to drive me. He agreed so I decided to shower first. I didn’t want to ride in his car covered in cum. When I got out of the shower we left, at least I was wearing my own clothes now. We didn’t speak at first then Cabe asked “Won’t Steve be pissed off at you?” I asked him “For What?” He was grinning when he looked back at me and said “We both know for what!” and he laughed. I asked what time he got home this morning and he said “Around 2:45” he was grinning again. I told him to please not tell his mother he had seen anything and he agreed he wouldn’t. He didn’t say anything else about it, but I had a feeling he would soon...I was right.

He dropped me off at my car and I drove home. Steve was up and said he was about to cake me and let me know he was on his way to get me. He told me I looked like I’d had a rough night and asked what happened. I told him I had drank way too much but he knew there was more to it than that. He then asked who was at Lynn’s house. When I told him he looked surprised then asked “Which one of you fucked Brad?” I asked why he thought anyone had and he said “Because Brad is a whore and he wouldn’t have stayed more than 10 minutes if he wasn’t getting into someone’s pants!” When I didn’t answer he got angry and said he couldn’t believe I would fuck that asshole! He gave me hell for more than an hour telling me I’ve always had permission to fuck who I wanted, but Brad is out of the question! He finally calmed down and eventually asked me about his cock. I laughed and said it’s about 5” long! We both laughed at that and he seemed to calm down. I wanted to take a longer shower so I went to the bathroom and locked the door. I sat on the toilet and felt Brads cum still coming out of me. I looked down and nearly screamed! My thighs from my pussy 1/2 way to my knees were black and blue! I put my hand between my legs and the opening to my pussy was gaping wide. When I wiped myself I found I had been bleeding just a bit. For the next few days I hurt to walk. I actually considered calling in sick on Monday but decided I better not. All day at work Brad kept giving me a weird grin. I couldn’t wait for the day to be over.

Brad quickly went from being a nice guy and lover to being a prick again. He called me into his office and told me he was ready for a repeat performance this weekend. I told him that wasn’t going to happen, though it might have if he’d been polite. He played a recording on his phone for me. It was the 2 of us having sex, with me saying things I didn’t even know I had said. I had promised to fuck him again and repeatedly moaned about how great he was. I apparently even gave him permission to cum inside me! I could tell he was playing it as a threat, hinting that Steve would hear it if I refused to fuck him again. I laughed and told him “Steve already knows, I told him!” The look on his face was priceless, part disappointment, part fear. He knows Steve could easily kick the shit out of him. But I actually think he was more unhappy that he couldn’t blackmail me. What a douche!