November 16th, 2010, 11:56 AM
On the Prowl
Me and my boss.
Two years ago when I was 20 I worked at this huge office during my summer vacation. I really needed the money, because I wanted to buy a car when my school was beginning in September. I got hired at the financial department to do data entry and it was a nice place to work, because there were more students working there. We had so much fun during work and our boss was really chill, as long as we did our work well.
I never had a thing for older men, but my boss was this very good-looking man, always in nice suits. He knew how to dress himself. He was 38 I guess, married and has two children. I knew all that, but he was giving me strange vibes. Whenever he would speak to me, he always touched me on my shoulder. Sometimes as long as the conversation went on. He only did that with me and was complimenting my work every day. My colleagues were teasing me that I was his favorite,, but to be honest I always did my work better than the rest.
One day I went to the toilet and I was cleaning my hands when my boss came in. He smiled when he saw me and was just standing at the door, he didn't walk any further. We just talked and I wanted to leave when all of a sudden he grabbed my arms. He was taller and bigger than I was, he was about 6'1" and I am only 5'8". He pulled me close to him and started kissing me and grabbing my ass. At first I fought back, but he was really holding me tight. Than he stopped kissing me and asked if I was okay with him doing this. I told him not really and he stopped. He let me go and asked me why not, I told him I wasn't really comfortable doing this with my boss at work. He wasn't really upset, but he apologized and he left. That was the first time I got kissed by a man.
A week went by and he called me up to his office. I hadn't spoken to him the entire week and actually started to ignore him. My colleagues were wondering why I let them go to him, when I needed something from him. I just told them that he said something upsetting to me and I didn't wanted to see his face. I went to his office and I sat down. He said to me that he had the feeling that I was hurt by what he had done. I told him that I wasn't upset, but it was all just very uncomfortable. I asked him why he kissed me when he was married and that even to a woman. He told me that things with his wife weren't going well and he was thinking about divorcing her. He said that he always felt that we had this 'thing' when we looked into each other's eyes.
I didn't know what to think and asked him if he was in love with me. He started laughing and said no, just attracted to you I guess. I asked him if he was gay, he again said no. I wasn't out of the closet at the time but I always thought that he was very handsome, he looked a bit like Matthew McConaughey, but he had shorter hair. I was too young to get myself involved with an older married man who also happens to be my boss. We talked a bit and things cooled down. Then suddenly he walked towards the door and closed it..
Want to know what happens next..?
November 16th, 2010, 12:22 PM
Re: Me and my boss.
If he's hot I would probably fuck him lol. In all seriousness though, I sort of had a similar situation with this guy but he didn't really make a move. He had the hots for me though, I know that now. Problem was he has a wife and four kids. I think a lot of men get bored with their wives and want something different to be honest. Who knows?
November 16th, 2010, 03:40 PM
November 16th, 2010, 04:57 PM
November 17th, 2010, 12:00 AM
Re: Me and my boss.
Welcome to the JUB story board. You have made an interesting start, so please continue
November 17th, 2010, 12:09 PM
Re: Me and my boss.
Omg finish the story, I have a boner now!!
November 19th, 2010, 04:22 PM
On the Prowl
Re: Me and my boss.
After he closed the door and locked it I heard him walking towards me. He started touching my neck from behind. I looked at him and gave him a little smile, he came standing next to me. He kissed me on my lips and was holding my face with his two hands. While he kissed me I was feeling sad for him, but I was also very curious, so I wasn't stopping. Then he stopped and went sitting behind his desk, he said sorry to me. I said that he doesn’t need to feel sorry. He turned around on his chair and was looking outside the window.
I stood up and walked towards him, I climbed on top of him while he was sitting, pulled his tie to get him closer to me and started kissing him like crazy. His hands grabbed my ass immediately while we were kissing and I was feeling his cock getting hard. At first I was shocked, because it felt really big, but that kind of excited me even more. We kissed for like five minutes while he was touching me all over my back and ass.
I stopped kissing him and kneeled in front of him. I opened his pants and pulled out his big cock. It really was huge. I had never given a blowjob before, I did get them a few times from girls. I started kissing his dick and smelling it, it smelt great. I started to lick the top of his cock and he seemed to really enjoy it. Then I put my mouth around his cock and started to go up and down. He was really enjoying it, so I assumed I was doing a good job sucking his cock.
I sucked his cock for ten minutes and licked his balls as well when he said that he was about to come. He stood up and shot his cum all over the window. He looked at me with a big smile and told me that this was his best blowjob ever. I felt really proud and smiled back. He took a little bit of his cum with his fingers and rubbed it on my lips. I licked it off, it tasted strange but I liked it. He pulled me up and kissed me and said thank you. He zipped his pants and told me I could go. When I unlocked the door I looked back at him and he winked at me, I smiled and went back to my place.
My colleagues were wondering why I was gone for so long. I told them that he asked me to do another project and that I declined it. They bought it and I went back to work. I couldn’t stop thinking about him the entire day. What had happened to me, I liked a man. One minute I was disgusted by myself and the other minute I was feeling really happy. The day went by and I went home. That evening the only thing I could think about was my boss. Was I in love?
Part 3 is coming up..
November 20th, 2010, 09:21 AM
On the Prowl
Re: Me and my boss.
It was Friday the next day when I went back to work. When I entered our floor I was looking for him, but I didn’t see him anywhere. It was twelve o’clock when I saw him walking in to his office. I tried to concentrate on my work, but I just couldn’t stop thinking about him. He was walking towards our desks, looking more handsome than ever. He was wearing a grey suit with a blue tie. I never really noticed it, but he was really buff. He also had an amazing ass, you could see that through his suit. I couldn’t believe it. I was actually checking him out. It actually made me laugh thinking about it. I didn’t know myself like this. I always checked out girls and their breast and asses, but now I was checking a man out.
When he was standing by our desks he greeted everyone, except me. It was very awkward, because I noticed that he ignored me deliberately. He went back to his office, I was shattered. I was wondering what I had done wrong and if he hated me for what happened the day before. I thought he enjoyed it. I felt really upset and just started working, just to take my mind of it. My co-worker told me that he had said to him that I had to work over hours that day and that he had to tell me that. That upset me even more, was he punishing me for it? It was five o’clock and everybody started to leave. When everybody left I looked towards his room, he was standing at the door and was staring at me with a smile. I looked away/
I wasn’t paying attention to him. He came walking to me. He was standing behind me, turned my chair and tried to kiss me. I told him no, he looked at me and asked me why not. I told him why not and he said that it was just a trick to keep me here alone. He could’ve just asked me, but he thought that would be more suspicious. He told me to grab my stuff and to come with him. I asked him why and he said just do it, he went back to grab his coat and bag. I was waiting outside his room for him. He walked out, took my hand and pulled me towards the elevator.
We went down to the parking lot where his car was. We stepped in and before I even sat down he pulled me towards him and started to kiss me. For the first time his hands went down to my crotch. He touched my cock and tried to make it hard, which he did. Then he started the car and we drove away. I didn’t know where we were going, but I didn’t care, I just wanted to be with him. After fifteen minutes we stopped and he parked the car. He stepped out and told me to come with him. He walked towards a door and opened it. I walked behind him. He told me that this was his house. I was shocked, but he immediately said that his wife and children were away to her parents for the weekend. I was relieved, but I also felt strange walking there. He asked me if I wanted something to eat and I said sure, so he ordered pizza.
When we were done eating he told me to take my clothes of. I did that, while he was looking at me. I got shy, but I was really aroused by him. He was still wearing his suit. He stood up while I was standing there naked and he lifted me up. I crossed my feet behind him and he started to kiss me. It was really intense, his tongue went everywhere in my mouth. He walked towards the bedroom while I was still holding him. He lied me down on bed and kissed my neck. Then he sucked on my nipples, it felt amazing. He went down even more and then he stopped at my cock. He went right to my balls and started to suck them. I never had anyone suck my balls and I was pleasantly surprised. He then put my cock in his mouth and gave me an amazing blow-job. While he was doing so he started touching my ass. His mouth started to go down as well and he grabbed my legs so he could lick my ass. It felt amazing, I was moaning really loud.
He then stood up and opened his zipper. There it was again, his huge cock. It must have been around 8.5". While I was giving him a blow-job, he unbuttoned his shirt. He was wearing a white t-shirt underneath it. He opened his belt and pulled down his pants. I was looking up to him, while he was touching my hair. He was really muscular, with a six pack and huge biceps. He had a little bit of chest hair. My cock stayed hard the entire time. I even touched his ass, he had a very round butt. He pulled me up and told me to go and lie on my back on bed.
He took off his shoes and pants and walked to his bathroom. He came back with a condom in his hands and put it on his cock. He told me not to be scared, he lifted my legs up. I actually was scared, I tried to have anal sex with girls before, but they all told me that it really hurts. He gently put his cock up my ass real slow. I felt it and it really hurt. I told him to stop, but he said it only hurts in the beginning. I was trying not to scream, I was biting my lips. He then stopped and said that his cock was all the way in my ass. I couldn’t believe it, it actually felt good. He then slowly pulled it out and then stuck it back in. We were looking into each others eyes, he was sensing that I had pain.
He pushed my legs down and came to close to kiss me. I couldn’t kiss back as much as I wanted to because of the pain, but he was holding me real tight. We were hugging while he was fucking me. He kissed my neck while I was grabbing on to his back. He was going faster and he was moaning real hard, he enjoyed it.
He stopped and told me he wanted to fuck me doggy style. So I stuck my ass in the air while he entered it. It felt amazing and he was pounding me real hard and fast, I liked it. He pulled me up so he could kiss me. He then lied on his back and I sat down on his cock facing him. He was touching me everywhere, touching my nipples, putting his finger in my mouth. I enjoyed every bit of it. I went down to kiss him and to kiss his neck and nipples. He whispered in my ears that he wanted to jerk me off while he was fucking me. So while I was sitting on top of him, he started to jerk me off. It took him about two minutes and I came all over his abs and chest. He then said it was his turn, so I took off his condom and put his cock in my mouth. He told me he was cumming, but I didn’t took my mouth of his cock. I wanted him to cum in my mouth, I liked that as well when a girl did that to me. He came and he was screaming real loud. I licked it all off and ate it, it felt amazing.
I kissed him and asked him if he liked it. He said yes and that he really needed this. He thanked me and walked to the shower. While he was in the shower he called me to join him. I walked towards the bathroom and went in the shower with him. We kissed and laughed and talked about how much we enjoyed it. He was soaping me and I liked it. Then we dried ourselves and he told me I could spend the night over. When we were in bed he told me all about his wife and how the love was gone between them. They were more parents than lovers. It was really sad and I hugged him. We kissed each other goodnight and I slept the entire night in his big arms with my head resting on his big chest.
The story isn’t over, Part 4 coming up...
November 20th, 2010, 10:09 AM
November 20th, 2010, 11:46 AM
November 20th, 2010, 04:50 PM
Re: Me and my boss.
son of a bitch, i hate TBC's! :P
November 20th, 2010, 05:30 PM
On the Prowl
Re: Me and my boss.
When I woke up Saturday morning in the bed of my boss I was in cloud nine. I was still naked and I looked beside me, he wasn’t there. He left a note that he was getting us breakfast. So I went to the toilet and brushed my teeth with a toothbrush he left me with the note. It was really thoughtful of him. After I showered I wondered what to wear, then I saw that he left me his sweatpants to wear. They were a few sizes to big, but I had nothing else to wear besides my jeans from the day before.
I walked to the living room and saw all these pictures of him and his family. I felt ashamed, but he was unhappy with his life and he made me happy. There were also lots of trophies, he used to play football. It was a big house and very nicely decorated. I heard someone open the door, he came walking in with a bag of sandwiches and coffee. I walked to him, he gave me a kiss and said good morning cutie. He asked me how I slept and if I found everything I needed. I told him yes. He looked so handsome, he was wearing jeans and a tight v-neck shirt. It was different seeing him wearing something else than his suits. We ate and watched television. We talked a bit about his football trophies and he was really proud of them. I picked up the plates and brought them to the kitchen. He followed me with the empty cups to throw away.
I was standing at the sink when he held me from behind and gave kisses in my neck. His hands were touching my chest and crotch. He said that last night was amazing and it felt good, I said the same. He was biting my ears and whispered sweet things in my ears. I turned around to face him and we kissed, he lifted me up and made me sit on the kitchen sink. It was really sensuous, he really knew how to kiss. He wanted to fuck me again, so I jumped of the kitchen sink, pulled my pants down and turned around. He went down and rimmed my ass, he was so good, I moaned like crazy. He took a condom from his pocket, pulled his jeans down and put it on his cock and started fucking me from behind. I was holding tight on the kitchen sink. He was smacking my ass and I told him to fuck me harder.
Then he stopped, and he lifted me up. He was holding me in his hands like a child and he kissed me. He walked towards the couch and he sat down. He told me to come and sit on top of him. I climbed on top of him and put his cock in my ass. I was facing him and while I went up and down on him we were hugging and kissing. I took of his shirt and we were in this position for a few minutes. Then he lifted me and put me on my back on the couch. He was fucking and told me he wanted to come inside my ass. I told him he could do that. He was sweating and I looked at him while he was fucking me, I smiled and moaned at the same time. So he went faster and faster and then he said he was coming. I felt him coming in my ass, it was really intense. He kissed me and told me that it was my turn to come.
He jerked me off while I was lying on the couch and I came all over my chest and stomach. I asked him if he wanted to taste it and he started to lick it of my stomach, it tickled a bit. He said it tasted amazing and better than he expected, so he licked it all off my chest and cock as well. He even made me taste it, but I thought his tasted better. We laughed and he went lying on the other side of the couch. I went over to him and kissed him. I was lying in his arms and we stayed like this for an hour, it felt so good. We then showered and he drove me home. During the car drive he told that we had to keep things professional at work and I agreed.
When I went back to work on Monday we kept it professional. We only talked about work related stuff. Sometimes he winked at me and I smiled back or we both checked each other out from head to toe. The week went by and it was Friday. I would’ve thought to hear something from him, but nothing. It was four o’clock when I saw him leaving his room to leave the office. I didn’t understand it, so I texted him asking if we would meet up. He didn’t respond, so I just went home. My buddy called and asked me if I would join him to get a drink with a group of friends. I was feeling a little bit down, so I said yes, only not to think about him. We went to a club, where a few girls were trying to hit on me. I wasn’t interesting, but after a few drinks I kissed this really hot girl. She was actually turning me on.
I danced with this girl and then I saw my boss inside the club with this woman. They were sitting in the lounge area of the vlub. They were talking and it looked serious. I assumed that it was his wife who he was with. She looked really hot and beautiful, I was actually getting jealous of her. He spotted me and I looked away. I began to kiss this girl again whom I was dancing with. I saw him looking at me, he looked even more upset. He stood up and he and his wife left the club, without looking back to me. I stopped kissing immediately. I wasn’t in the mood anymore and told my buddies that I was going home. When I was home I got a text message from him that he wanted to meet me the next day. I responded and said that he could pick me up around three o’clock in the afternoon.
He came at exactly three o’clock and I stepped in his car. He didn’t say a word and we drove away, it was really awkward. I looked out of the window and sometimes I looked at him, but he was just looking at the road. He parked the car in a remote industrial area. There was no one here. He started talking to me and asking me who that girl was. He asked me if she was my girlfriend, I denied it, but he didn’t believe it. I asked him if that was his wife who he was with last night, he said she was. He told me that she needed a break from the children, but I didn’t believe it as well. I though they were in a fight and thinking about breaking up. He said that last night they spoke about divorcing and they both agreed that it was the best solution for them and their children. He started to get emotional. I stepped out of the car, walked towards his side and hugged him. I couldn’t hug him with him standing up, because he was taller and he couldn’t put his head on my shoulder. I told him I was there for him and gave him a kiss on the lips. It was a strange moment that I had with my boss, but I really liked him.
We talked a bit inside the car and he started to laugh again. After a while he started touching his cock and I was also getting horny. He put on some music and I climbed on top of him. I started to move a little on top of him and giving him kisses and touching his body. We then moved to the backseat of the car and I lied on my back while he was on top of me. We were just kissing. I could lie on my back, but he was too tall to do the same, so his feet were on the ground. Then his phone rang and it was his wife. She told him that he needed to pick up his four year old son from his playdate. He said he would do it, so we went to the front seat and he dropped me off telling me he wanted to see me in the evening. I said he could call me, I also wanted to be with him that evening..
Part 5 coming up as well..
November 21st, 2010, 04:24 PM
On the Prowl
Re: Me and my boss.
I waited the entire evening for him to call me up. It was nine o’clock when my phone went off. It was my boss, he said that he was outside waiting in his car and that I should pack some things for the night. I walked towards the car and got inside. He pinched my leg and greeted me with a smile. I asked him where we were going and he told me that it was a surprise. My excitement was getting bigger. He parked the car in front of a very luxurious hotel. I smiled and said that I liked it. He stepped out of the car and grabbed his bag from the trunk. We walked towards the entrance of the hotel and he said that I had to wait in the lobby. He went to the reception, I looked at his ass from behind and smiled. He walked back and told me to follow him. We took the elevator to the seventh floor and we walked towards a room. He opened the door and let me walk in first.
It was a nice room, it had a separate bedroom and sitting area. I put my bag on the king-sized bed and he came over, touched my chin and kissed me full on my mouth. I was of course kissing him back and stroking and pinching his ass. He said he would be right back, he went to the bathroom. I sat down on the bed, he came walking back to me and started to undress me. He first began to take my shoes and socks off. He started licking and sucking my feet and toes, I didn’t know that it felt so good. He then opened my pants and pulled them down. He took my shirt off and told me to lie on bed. He opened his bag and took out a bottle of whipped cream. He took off his clothes and came lying next to me.
He took the bottle of whipped cream and shook it. He put some on his nipples and abs, he said that to lick it off. I started with his nipples, I licked it of very gently and I went down to his abs and ate it all. He then put some on his mouth and I licked it of with my tongue. He pushed me on my back and sprayed whipped cream all over my stomach and chest. He licked it and I started to giggle, it tickled. He gave me a kiss and went lying on his stomach beside me. He wanted me to lick whipped cream from his ass. I sprayed it on his butt cheeks and in between as well. I licked it all and widened his butt cheeks so I could lick his hole. I went down on his ass and started to lick it with my tongue and kissing it. I also used my fingers, he said that I was doing a good job. I could hear that that he liked it, he was moaning very loudly.
He reached for his bag and took out a condom and told me to put it on my own cock. I was surprised, was I really about to fuck my boss. I put the condom on and he said that he wanted me to do it very gently, just the way he had done to me. This was also his first time getting fucked. I wasn’t as well endowed as he was, but I started very gently. He moaned and said that I could go further inside. When I was all the way inside his ass he said that it felt good. I began to fuck him very slow, he had a very tight ass. It felt amazing. I fucked him harder and harder and he told me how good it felt. He then came up a little with his ass and legs so I could fuck him doggy style. I couldn’t hold it any longer and I came in his ass, what an amazing feeling. He took my cock out of his ass and he turned around on his back.
He pulled me towards him and kissed me, I was really sweaty and he liked that. I was lying on top of him and started to jerk him off while kissing him. It was so romantic, he was grabbing and stroking my ass the entire time. After a few minutes he came all over his chest and my face as well. I touched his cum and licked it of my hands, he was smiling, he liked me doing that. He told me he wanted to take a bath with me, so we went to the bathroom. He turned on the water and sat in the bath and I sat in between his arms and legs. He cleaned me and we talked and laughed and kissed. He told me that he really liked spending time with me, not just for the sex. I said that I felt the same way. After a good bath we brushed our teeth and went to bed, naked of course.
When I woke up we were curled into each others bodies. I was lying on top of him in his arms, he was still asleep. I was feeling up his big chest and stomach and went down with my hand, his cock wasn’t hard. Even soft he had a big cock. I put his soft cock in my mouth, trying to make it hard. He moved a little, but I continued sucking his cock. Slowly it grew and after a few minutes it was rock hard. I was going up and down real fast. Then he woke up and pulled the covers away. He said it what a nice way to wake up. He told me to turn over, so he could do the same to me. We were 69ing each other and we both moaned and sucked at the same time. As always I came real fast and he let me come in his mouth. A few minutes after I came he came as well in my mouth.
We each took a quick shower and packed our stuff to go downstairs and eat something. We were sitting to order breakfast when his phone went off, it was his wife. She was crying on the phone. He asked if something was wrong, she asked him to come back home to talk. He said he was coming right away. He told me he had to go home and asked me if I could go home myself. I said sure and he went to the reception to check out. I ate my breakfast en took the bus home.
That evening he texted me to say that he was joining his wife on a holiday she had planned. She was going alone with the children, but he thought it would be wise to go for the sake of the children. Two weeks went by and I was wondering when he would come back to the office. Nobody knew when and he didn’t respond to my messages either. I felt hurt and assumed he must have made things right with his wife.
Part 6 coming up..
November 28th, 2010, 03:52 PM
On the Prowl
Re: Me and my boss.
It was three weeks ago that I last saw him, I started to miss him. I couldn’t stop thinking about him. I think I was in love with my boss. My colleagues wondered why I was so quiet and distant. I just told them I was stressed out about school, they believed it. College was about to begin in two weeks, so I would stop working at the office by then. While I was working I heard people telling each other that the he was back. I didn’t think a second and walked towards his office. He was indeed sitting there looking at his computer screen. I closed the door behind me and walked to him. I asked him what his problem was and why he ignored me all this time he was away. He told me that he patched things up with his wife and they renewed their vows on their holiday. He then said that he didn’t have time for this and if I could go back to work. He didn’t even look at me. I was upset and shocked at the same time and asked him again if he meant that. He said yes and that I should just forget what had happened between us. I told him that I didn’t want to work here anymore and that I resigned. I marched out of his office to get my stuff and went home.
At home I started to get emotional, but I didn’t want to cry. I never cried. I went to bed and just slept the rest of the day. When I woke up the next morning I checked my phone to see if I received a message from him, but noting. I went to the gym that morning, when I came home I got a message from him asking me if he could pick me up. I was hesitant at first, but I was curious to know what he wanted from me.
When he showed up in his car I stepped in. He didn’t say a thing. We drove to the forest and he parked the car at this empty place. He took something out of the drawer. He stepped out, walked towards my side and gave me a gift. I asked him what it was, but he said just open it. It was a watch, it looked very expensive. He said that he never saw me wear one and thought this one would look good on me. He took it out, kneeled in front of me and helped me wear it. Then he stood up, held my hand and pulled me up as well. He gave me a hug and told me that he missed me. I pushed him away and asked him why he treated me like crap at work. He said that this morning he believed that things with his wife were going fine, but when he came home they had a fight and she left him for good. I said I didn’t know what to think about it.
He said I didn’t have to think and he held my head and kissed me. My feelings took control over me and I kissed him back. He grabbed my legs and lifted me up. He was holding me while we were kissing. I told him that I missed him as well. He walked with me towards the car hood and lied me down on my back. I had my legs wrapped around his waist while he was still kissing me. He stroked my cheek and gave kisses in my neck. We were hugging and kissing.
Then he started to touch my cock, it was rock hard. Before I knew it, he pulled my pants down and removed my shirt. There I was naked in the forest with him kissing me all over my body. He began to suck my cock, it felt so good. We were looking in each others eyes the entire time and I was smiling and moaning at the same time. He pulled my legs up and licked my ass. The he held my hand and I stood up, he kissed me and I pulled his cock out of his jeans trough his zipper. I started to lick it and suck it. I stroked his ass and he enjoyed it. He took a condom from his jacket and I put it on his cock.
He turned me around and he fucked me from behind. I was screaming so loud, it felt really good. I had my hands on the hood of the car. He pulled my hair and put his fingers in my mouth. He fucked me so hard that the car was shaking as well. Then he turned me around on my back and fucked me. I pulled his tie so that I could kiss him. He was whispering sweet things in my ear and he told me that he was coming. After he came we lied there for a few good minutes.
I wore my clothes again and we sat in the car. He told me that he really liked me, but there was no future between us. I agreed and told him that I felt the same. He gave me a kiss and he drove me back home. I didn’t go back working for him. He started dating other women and I did the same, but with men. I’m more attracted to men now. When we feel lonely we have an occasional fuck.
November 28th, 2010, 05:47 PM
Re: Me and my boss.
This is the best story ever!!!!!!!!!!!!!
December 1st, 2010, 11:14 PM
Re: Me and my boss.
I would have loved them ending up together! :3
December 5th, 2010, 07:39 PM
Re: Me and my boss.
I wish this were a true story!
December 9th, 2010, 10:58 AM
November 13th, 2012, 06:05 AM
August 4th, 2014, 04:12 PM