As most of you know I had been working at Mikes investment firm for over a year then. Mike was then 60 and I was 19. I have had so many great sexual experiences with Mike and or his clients in the last 16 months or so! I tell all about it in “My new Job” I have had some wild times everything from squirting my first time to anal,riding car shifters to interracial and group sex ! In my last story I tell about a interracial group encounter I had with Mike my Boss. One of his black clients and Mikes 45 year old brother in law Roy (who is married to Mikes younger sister) and who had been flirting with me for months had his first opportunity to have sex with me and we both really enjoyed it ! He has been really trying to get with me again ever since that night but Mike doesn’t want himself or Roy to get caught!
Well Mike had a family reunion he was going to attend with his sister Roy’s wife. Roy has a hunting trip the same weekend which he goes on every year. My boyfriend also goes hunting that same weekend ! Mike came up to me with Roy the Wednesday before and said he had a proposition for me. He told me of the circumstances and that Roy would like to take me out that weekend and what did I think about that? I said Roy you always go hunting with your brother I thought? Roy said Jenn my brother has a wedding to attend that weekend 2 1/2 hours in the opposite direction ! I said Mike has always been with me on any of these sexual escapades ! I said I wouldn’t do anything to jeopardize Mike and my situation. Mike said to me that I have his permission even though I didn’t need it but it was totally up to me ! Mike asked if I trusted Roy and when you and Roy were together at your special Birthday surprise did you have a good time? I said yes we had a Great time and Roy I would love to go with you ! Roy came over and gave me a huge hug. I asked Roy what are your plans? Roy asked if I would like to go to his hunting cabin for the weekend? He said we could leave Friday after work and come back some time Sunday what do you think about that Jenn? I thought for a second, mostly just to make him sweat a little and said Roy I would love to go with you this weekend ! Then I said Roy make sure you take your vitamins I want to make sure you can keep up with me! We all laughed ! Then Roy said you don’t need to worry about that Jenn!
Mike said Jenn would you like to get some new clothes for this weekend? I didn’t quite know what he meant? He then went to his money clip and took out $200 Here is a little bonus I know how hard you have been working lately! I said Mike you don’t need to do that ! But he insisted ! I said Roy what colors do you like ? He said Jenn I love red and also black ! I said well then Roy I’ll have to see what I can do for you ! Mike said Jenn if you would like to go shopping you can have the rest of the afternoon off ! I said well thank you Mike! Well when I left it was about 2pm and I usually work till 5. I decided to go to a town about 30 miles away to a shop where Mike had taken me shopping one time. I spent the entire afternoon picking out and trying on some very sexy outfits. I managed to spend most all of the $200.
Thursday about 3pm Mike asked me if I could stay a little late tonight that he had to go thru a portfolio and have it ready for the client first thing Friday morning I said I would be glad to Mike! He and I actually worked on it till 6 to get if all in order. Once we had everything done and put away Mike asked if I would like a drink and that he was going to have one. I said I sure would! He got some ice and poured us both a drink We were both sitting on his side of the desk when he asked what do you have in store for Roy this weekend kind of laughing. I said Mike are you a little jealous ? He said that he is and that he would really like to be there with us but he was sure I would have a Great time with Roy ! I said Mike I’m sure I will I always do? Right? He laughed and said Yes Jenn you always do! I rolled my chair over to Mikes and said I won’t tell you what I’m going to do with Roy but I will show you a couple of the things ok! He said Jenn yes please so I told him to pull his chair back a little. He did and I snuck under his desk and had him roll his chair up to me and I opened up his pants and said Mike let me show you how much I appreciate all you have done for me my Boss and number 1 lover! He said Jenn what would I do without you? I opened his pants and took his beautiful 8″ out. I licked it gently while caressing his balls He was now hard as hell and I said Lover let me out and now you can show me how much you appreciate me. I came out from under the desk. I took my heels,jeans and panties off then put my heels back on and we the started a very passionate kiss. He always was very passionate but this was more than ever and it went on forever I was on fire! When we broke I took my sweater off. I didn’t have a bra on and laid back on Mikes desk he followed me down and was kissing me just like before as he slid his beautiful cock in me. He never stopped kissing me while he was fucking me at such a nice pace. I was cumming every 15 seconds or so this went on for some time when I felt Mikes Cock twitching and then he came deep in me. All the while we never broke from our kiss. God it was the best! He said Jenn you are so special ! I said you are as well Mike. Thank you for everything! We kissed for quite a while then we got up and got dressed. He walked me to my car kissed me again and said see you in the morning.
The next work day was pretty uneventful. Mike left at 3:30 to pick up his sister for the family reunion. I stayed till 5pm then locked up and then went home to get ready. I met Roy at 7pm at the office I left my car in the garage there. I grabbed my bag and hopped into Roy’s truck. He was all smiles and said Jenn you don’t know how excited you have me! I said let me see Roy as I rubbed his crotch and could feel that he really was ! As soon as we got out of town he asked if I cared to sit next to him? I slid over and he put his arm around me. He asked me about how Mike and I ever ended up having sex? Well I told him and then we started talking about some of the experiences that Mike and I have had. He was all ears and had so many questions. Every once and a while I would brush my hand over his crotch. He was quite excited over the stories I had been telling him. In no time at all the hour and a half trip was over and we were pulling into his cabin. We pulled up and when Roy put the truck in park I pulled him to me and started kissing him. He broke the kiss and said Jenn let’s get inside!
I looked around once we got inside and was pleasantly surprised how nice it was ! He was all over me in a second. I said Roy slow down we have all weekend! I said Roy let’s have a drink and continue our chat we were having on the way up. He said yes Jenn I’ll make us a drink. He asked me what was my favorite experience? I told him it was my Birthday surprise that he was part of ! We talked about all the things I did that night. He told me that I was the perfect woman ! I said if my boyfriend ever found out about all the sex I had been having without him he may not think so! We both laughed really hard. I said Roy could I have a half hour or so I have something special for you. He said hell yes ! I grabbed my bag and asked where is the bathroom lover ? He pointed it out and turned the light on in it for me. Roy said you just take as long as you need! I can’t wait! I went in and got undressed. I put on my new black garter belt and then put on white thigh hi nylons and hooked them to the garter. I had 3″pumps I put on then my new shear bra! I thought about putting my red panties on but thought they would just get in the way ! I redid my hair and added more makeup and perfume! I looked in the full length mirror on the back of the door and thought the outfit looked very nice.
I could hear Roy had some music playing low. I asked Roy to meet me in the bedroom! He said ok Jenn. I waited about a minute and them headed to the bedroom. I cold see he had the lights turned low in the bedroom. I entered the room and Roy was laying on the bed with just his jeans on ! Roy said Oh My God Jenn you look amazing ! He went to get up to come to me and I told him you just stay put lover! He just kept saying Wow! I walked up to the bed and turned around very slowly Roy was then sitting up when I leaned over him and pushed him back crawling on him and kissing him all the way up till our lips met ! We kissed and then I started kissing my way back down ! I took his belt loose, opened his pants which was kind of hard because of his hard on and took out that very hard cock ! I went back up and kissed him while slowly stroking his cock. Then I went back down and put his cock in my mouth working my tongue around its head while holding his nuts in my left hand. He was moaning and telling me how much he loved it. I then said Roy now it’s my turn! I rolled over while Roy got up and took his pant off the rest of the way. I was on my back with my legs spread and my knees up! He immediately started licking my pussy then my Clit ! This was the first time I was to cum that night! He then put a finger in me and was massaging my G spot I came again He started kissing his way up to my mouth. I could taste my own pussy juice. I asked Roy put my legs up which he did and the eased his cock into me. He had my heels on his shoulders and was really fucking me good! He slowed down thats when I said Roy get on your back and let me on top. He turned over I got on top of him grabbed his cock and slid down on it! I was rocking back and forth on him he was deep in me! Roy had his hands on my breasts pinching my nipples while I was rocking at my own pace and cumming hard over and over! Roy said Jenn I’m going to cum and cum hard !!! I jumped off and got his cock in my mouth just in time. I sucked and sucked even after he came in my mouth he never went soft. I asked Roy do you have more for me lover? He said oh Jenn I do. I laid on my back and put my heels behind my head. I said Roy take me again! He said yes Jenn I will! He pounded me hard I could feel his balls slapping my ass He was in very deep that’s when I could feel him letting loose again ! We both collapsed and fell to sleep in each other’s arms !
I awoke about 7am to Roy eating me again ! I started moaning and cumming! He climbed on me again and in minutes he brought his cock to my mouth and came again ! He laid back along side of me and we both fell back to sleep till about 10:30. Roy asked if I cared to take a shower with him and I said by all means. We both got into the shower lathering each other up and kissing. I stroked his about 7″ cock for awhile and said maybe we should save a little for later, which he agreed ! We both got out and toweled each other off. We kissed again!
Roy asked me if I would like to go for lunch at a resort just down the road? I said sure lets get dressed. We were just pulling into the resort and I noticed a flashing sign that said “Girls Tonight” I asked Roy what’s that all about? He said they have strippers every night during hunting season. There are a lot of men out in the woods during hunting season and they like to spend a lot of money on pretty girls! I said laughing like me? He said yes like you! We went in and each of us ordered a drink. I asked Roy about his sex life with his wife? Oh he said it was ok. I asked if he ever had any other women besides me while he was married? He said no I was his first ! I said I must be pretty special. That’s when the waitress asked us for our order. When she left Roy told me that he almost had his wife talked into having sex with another man a few years ago but at the last minute she backed out. He said that really turned him on and he would love to watch her having sex with another man. He told me that’s one if the reasons that I turned him on so much ! That when he watched me with Mike and Jim at my Birthday Surprise he was so turned on! Well our lunch showed up and we ate it and had a couple more drinks talking about all kinds of sexual adventures we both had. Before we knew it, it was 5pm. I asked Roy what are your plans for this evening? He just started smiling! I laughed and asked him if he cared to go back to his cabin and have some sex? Then maybe later come back here and that way I could see what all the fuss was about with all of these hunting guys and the strippers ! He said that sounds like a great idea, let’s go!
We got back to Roy’s cabin as soon as we got into the living room I jumped up on him wrapping my arms around his neck and my legs around his waist kissing him! He laid me on the couch and we were tearing each other’s clothes off! He was so hard and in me in a seconds! We were both so excited from talking about sex all afternoon! God we fucked like we were both in heat! After about 5 minutes of that I said Roy please lay on your back and let me finish you off lover! He did and I passionately made love to his cock with my tongue and mouth till he came in my mouth swallowing all of his load. I went up and laid my head on his chest where we both fell to sleep.
Roy woke me up and it was almost 8pm. He asked if I still wanted to go back to the Resort where the strippers were tonight? I said yes by all means! Maybe I can learn a thing or two ! He said great ! I asked him if I could take a bath the get dressed? He said Jenn you can do what ever you would like! I will get ready, then start a fire in the fire place and watch TV till your ready. I said your great Lover! I soaked in the tub for about a half hour. When I was in there I shaved most of my pussy hair just leaving a small V above my pussy! Then I got out and did my hair. I thought what should I wear? I put on a pair of little red lacy panties with my new red garter belt hooked to black thigh hi stockings. Then my red shelf bra adjusting my breasts just right. Next my Gloria Vanderbilt blue jeans with a white blouse that buttoned up the front. I only buttoned it up to just below my bra so you could see it! You could also see my nipples thru the white blouse very easily ! I put my 3″ pumps on also. I added a little perfume in the right places. I put my stuff back in my bag and opened the door just a little and asked “Roy are you ready to see me?” He laughed and said you had me wait long enough laughing. I came out and asked him if I was worth the wait? He said Oh My God Jenn you look Fantastic !!! I said I’ll grab my coat and we will go! He said Yes by all means! It was almost 9pm.
When we got to the door of the Resort a guy stopped Roy and wanted a $5 cover for each of us. Roy said look at her! Really? He said no just go in and have fun!
When we walked in and there was a girl dancing on a stage to the right of the bar and it was packed with men! We went to the left and looked for a spot somewhere at the oval shaped bar. We walked around to the back when a bunch of guys said hey you can sit here ! Roy said Jenn have a chair! And I did. One guy immediately said what can I get you to drink? I said I will have a screw driver and my friend will have a beer as I winked at Roy! We all talked. We found out there where 4 guys in this group that were all hunting together and were certainly looking for a good time !!! I took off my jacket and the look on their faces was priceless ! I could feel my nipples were very hard to say the least!!! It could of been the cold outside, all the men on the inside or both! They were asking to buy me shots. I told them I would have 1 with them. They toasted Here’s to Jenn! We all slammed them ! I whispered to Roy are you enjoying this? He looked me in the eyes and nodded his head YES! I was now on my second screw driver and one of the guys said he had to use the Little Boys room ! The other 3 were rubbing my legs and arms all the time getting more brave. That’s when the guy that went to the bathroom came back with one of the dancers. He said we were all going to get our picture taken with her! I was giggling. She said they had to buy her a shot first! One of them said 2 shots and there was 2 shots on the bar. They said one for Saphire ( the dancer) and one for Jenn! Her and I each slammed them and put the glasses back on the bar! Then they bought Saphire and I each another screw driver! All the time these guys were rubbing us as much as they thought they could get away with. We each had 2 guys feeling us up! It was very Hott! While Roy was smiling and really enjoying watching me ! I could tell as I gently copped a feel of his crotch as the 2 guys that were feeling me up.
One of them said to Saphire could Jenn dance a set? She looked at me and said would you like to? If you do I’ll talk to the DJ. I looked at Roy and he had the biggest smile and the other 4 were egging me on as well as Diamond. I looked at her and shrugged my shoulders why not !!!! She took me by the hand and we walked up to the DJ. Diamond said she would like to dance a set is that ok? He said sure and he would play her music for me. He said what’s your name? I replied Jenn! I was so busy in the corner with the 4 guys I hadn’t realized it was past midnight already! The girl dancing just finished and now it was my turn! Wow! Saphire
took my hand and walked me up to the stage. The DJ announced we have a new girl for you guys here’s Jenn! The music started and I walked up on the stage. The place was going wild. I started dancing slowly. Guys had dollars in their hands wanting me to come over to them. I just kept dancing swaying back and forth moving all around the stage. When the second song started and I put my back to them swaying back and forth while unbuttoning my blouse buttons I turned around and had my blouse loose teasing them by pulling it open but not enough to see my nipples. I was pulling 1 side up the the other. The guys were going nuts! I turned back around and took it off. I turned around and they were screaming ! My tits sitting on that red shelf bra. My nipples almost breaking out of their skin! Then I started unbuttoning my pants and opened them up sliding them down first one side the the other. I took my pumps off and my pants all the way off then slipped my pumps back on! The place was going nuts ! I was strutting around the stage guys throwing money ! I was so wet and just on fire !!! Then before I knew it the third song was over and they wanted more! The guys were all yelling and whistling . Saphire took my hand and helped me pick up my clothes and all the money that was on the stage. Then she said come with me to the dressing room.
On our way I noticed a commotion over in the corner near Roy. We went into the dressing room and Diamond asked me if I enjoyed myself? I said I positively did! She asked if I ever did it before and I said only for 3 guys nothing like this! She said Jenn your a natural ! Really ! She just finished counting the money and said Jenn you have over a hundred dollars here! I said you can keep the money, I just was happy to have this experience and said thanks for helping me! I got dressed and went back out to find Roy. He was near the same spot but the other guys were all gone. I asked what happened to them? Roy said someone said they were going to take you home with them tonight and the 4 guys didn’t care for that and there was a fight and they all got kicked out! I said Roy I was hoping I could take a couple of them back to your cabin so you could watch like you said you liked! Ya Roy said that’s ok I still have you baby !!! Any way I said I need a drink! Roy said to the bartender I needed a screw driver. She said the gentleman over there is buying it for you. I looked and there was a guy across the bar waving to me. I looked again and I knew who he was ! He came walking over and I gave him a big hug! I said Roy I want you to meet Don! They shook hands. I told Roy that Don had gone out with my older sister for almost a year and we went to school together ! Don was 3 years older than me, he said my God Jenn you look Fantastic and all grown up too! I said I think you do as well Don and I haven’t seen you in it must be like 3 years. He said yes it’s been a long time. We had some small talk that’s when they called last call! I said Don that sucks I really wanted to catch up. He said he was hunting nearby. I said my friend Roy had a cabin near by. Roy said well Don the night is young would you like to come over with us and you guys can catch up? I said Hell yes Don come over! He said that sounded good. I will follow you guys over ok? We said yes let’s get out of here. It only took us about 5 minutes to get to the cabin and on the way over I asked Roy if he wanted me to do it ? He said yes Jenn I do ! I said this is going to be great! I would love to ask him who is better me or my sister! He said you are something Jenn !!! We arrived and went in. Don sat on the end of the couch. Roy got us all a drink and I sat right next to Don. Roy handed us our drinks and went and filled the the fireplace. The only light besides the fireplace was the light on in the kitchen! Then Roy sat on a chair across from the couch. Don asked how we met? I sad Roy let me handle this ! I said Don you have known me a long time how do remember me? He said a cute quiet k**. I said I was Don ! But when I graduated from high school I went to work for Roy’s brother in law. His name is Mike and he is 60. Roy is married to Mikes sister. I then put my hand on Dons thigh and looked him in the eye and said I have been having sex with Mike for over a year and Roy one other time before this weekend. Mike has taught me so much sexually ! What did you think when you saw me on that stage tonight Don? I thought it was you but wasn’t sure at first but once the third song was over I was almost positive! What else Don? He said that I wanted you! He started kissing me. Then he stopped and said what about him? I said if Roy wants some he can join us, is that ok Don? He just started kissing me again I was rubbing his cock and him my breasts. I said did you like my outfit that I had on on stage tonight Don? He said my god Jenn I loved it ! I said would you guys like to see it again? They both said “Yes” I said excuse me boys as I went to the bathroom to prepare. I came out of the bathroom with just what I had on when I got off the stage except I took the panties off and left them in the bathroom ! Don stood up as I came to the couch took my hand kissed me for some time and then seated me on the couch He then knelt down between my legs and started eating me ! I was leaning back really enjoying Don! I looked at Roy and he had a huge smile! Don then went up and was sucking my nipples god I couldn’t believe the best looking older guy in high school was eating me and now was sucking my breasts! I said Don stand up and I sat up and undid his pants. He slid them down and I pulled down his briefs and I was very pleasantly surprised to what I saw ! He was very hard and quite thick with a curve upward! I just looked at it admiring it for a minute then started stroking with one had and messaged his ball with the other! I couldn’t understand why my sister would of ever let him go! I then put my tongue under the tip and was teasingly flicking it back and forth. Don said Wow Jenn you are good,very good! That’s when I put as much of it in my mouth as I could! My tongue was racing around the head of that Beautiful cock of his! He just kept saying Jenn,Jenn,Jenn you are an amazing girl! He then really started to pump his cock in and out of my mouth! I stopped and laid down on the couch. He laid on top of me kissing me then he positioned me and slid his curved Cock deep in me! In one quick stroke he was all the way up in me! OMG he felt amazing ! He took a few strokes and I said Don pull out ! He did and I squirted all over! Don yelled Oh My God Jenn that’s amazing! I heard about girls that could do that but I never figured I would see it ! He put his cock back in me and was really Fucking me like I have never felt before! I said his cock was thick and it was the upward curve that was rubbing my G spot and I was coming over over and over!!! That’s when Don said Jenn I’m going to cum ! I said please Donnie cum in my mouth ! Once again he said Oh My God Jenn you are amazing as he was cumming in my mouth! Once he stopped cumming I kept sucking him to make sure I got every drop ! I have had a few cocks but none curved up like his was and it was the best by far! He sat back down along side of me and cuddled me close to him! He said Jenn you are the absolute best I have ever had! Roy then said thank you both for the show! I got up and walked over to Roy I told him Stand up ! He did and we kissed while I rubbed his cock through his pants I then pulled his pants down pushed him back to his chair and started sucking his cock ! In a minute I stopped and looked over at Don and he was hard ! I said Donnie,Roy I want you both ! Are you both ok with that??? I said Donnie lay down here in front of the fireplace Which he did! I straddled his cock and slid it up in me. Wow he felt good ! I was kissing him and he was kissing me back! Then I asked Roy you know what to do right? He said yes I do lover. He spit on his cock and then put the head of his cock in my ass. He went slowly as Don held still. Once he was in all the way he started pumping his cock in and out of me ass. I then started a rhythm that they all 3 of us where enjoying and I again was coming nonstop!!! Roy was kissing the back of my neck and Don and I had our tongues deep in each other’s mouths. The fireplace had a beautiful glow and they felt sooo good ! This was the absolute best sex I have ever had! Soon Roy said Jenn I’m cumming baby. In your ass ! I said oh yes Roy fill me ! When he was done he kissed me on the side of my cheek and went and sat back on his chair ! Donnie rolled me over and now was on top and kissing me and fucking me so good! I was cumming and cumming because of Donnie’s cock ! The girth and it’s curve! My god he was magic! I could feel him tighten and let loose in me and never stopped kissing me ! Then we rolled onto our sides looking into each other’s eyes. Just looking not saying anything for a few minutes. Donnie said Jenn I have never experienced anyone like you You are amazing. Don told me he still lived very near me and why hasn’t he seen me out before? I said I have a boyfriend we didn’t go out to bars much and when I go out with my boss Mike we usually go to different towns. I said Roy is married. I said Donnie do I really turn you on this much? He said yes you do Jenn and I would love to see you again! That is if it’s ok with you and Roy and your boss! I kissed him and said Donnie I want you too! The light was now starting to shine in the windows Don said he didn’t want leave but had to. Could we go out Wednesday night ? I said yes I would love to! We exchanged numbers Then he said Jenn I’m so happy I got to do this with you tonight.! He got dressed we kissed and neither of us wanted to let go! He left then I went to Roy and asked him what he thought? My god girl you are insatiable. I then started sucking his cock again. We went to bed and he fucked the hell out of me! Again!
Monday at work Mike was full of questions ! We talked about what had happened over the weekend ! I said Mike you really missed out on this one! My boyfriend was off of work Monday and came home from hunting Monday afternoon. He came over to my house and confronted me saying he heard some things about me with other guys? And what did I have to say about that? I was quiet for a bit and all I said was I think we need to break up !
I kept a journal about all my adventures while it was all happening. I am having so much fun reading and reliving all of those great times! I do have more to share and will soon! I sure hope you enjoyed this. Please comment and let me know your thoughts! Luv Jenn