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Chicago Funland

My wife of 26 years Liza has come to her sexual apex. She has become very interested in sex and comes home with some interesting twists on things try. On the anniversary of when we met she asked if we could take a trip to Chicago and see if her college pal Wendy and her husband Mark would like to met us for a long weekend. I thought it was a great idea since we hadn’t seen them in about 5 years and they live just out side of Chicago in Rockford.
So Liza made arrangements with Wendy so that we could all meet up in Chicago. Once we had all the plans in place we headed to Chicago. Liza had made arrangements with Wendy that we would pick them up along the way since we had to go through Rockford on our way into Chicago. When we reached Wendy and Mark’s house we had been driving for about 2 1/2 hours so it was great to stop and take a break, while we loaded everything into the car. Wendy and Mark have known each other as long as Liza and I have known one another, but have only been married for 18 years. Mark was a little worried about losing his freedom and delayed getting married until he manned up. As for Wendy and Mark, Wendy is slightly shorter and a little thinner than Liza at 155 lbs and around 5 foot 4 inch tall. She does however have a lot bigger rack than Liza at 40 DD. As for Mark he is a lot taller than myself he is about 6 foot 2 inches and carries his 210 lbs a lot better then I carry my weight.
So as we left the ladies were in the back making plans for our days and evening activities. Unfortunately for me and Mark they weren’t planning any sporting events. They were talking about some really nice restaurants and going to some shows. The ones that I was looking forward to were the comedy club and the jazz club. I had heard that they are pretty entertaining.
We arrived a little later then I though we would. The hotel was on Michigan Ave and the ladies had reserved us a two bedroom suite, very nice place. A little more money then I thought we were going to spend, but not so bad split between the two of us. The room has this great common area with two large sofa’s and two large chairs that make a U around a big screen TV. Off to the side is a nice fully stocked bar and dining table. The bed rooms were great each had a king bed, full bathroom, big screen TV and a jacuzzi tube.
We were all tired from our trip so we ordered some room service and retired to our bedrooms. I was exhausted from the drive and Liza was a little horny and I knew that I wouldn’t be much use to her so I decide I would go down on her to satisfy her carnal want. She was so horny she wasn’t really interested in any fore play. So I slid down to her nicely shaved pussy.
I slid my tongue across the lips of her pussy and Liza let out a little moan. She said go to my bag I brought some thing along this trip. So I went to her over night bag and found her favorite a double headed vibrating dildo and lube. I returned to the bed and she was all smiles. I slid back down to her pussy and started sliding my tongue and the vibrator all over and in her pussy and on her clit. After a few minutes of this I took a small amount of lube and put it on the one head of the double headed dildo and slowly slid it down to her ass. As I was working her clit with my tongue and sliding one head of the dildo into her pussy Liza reached under herself and pulled her ass cheeks apart. She moaned and said fill my ass with that cock. Not wanting to upset her I did as she requested and slowly slid the second head into her ass. Liza let out a deep moan as soon as it entered her ass. She then pleaded with me to pump her pussy and ass. She pushed me away from tonguing her clit lifted her knees up around her head and said fuck both holes it feels great. So I kept pumping her pussy and ass with the double headed dildo. Liza’s puss was just dripping and she was loving it after about ten minutes she couldn’t handle it any more and just started rubbing her clit furiously and with in seconds her entire body was convulsing and she was panting.
I moved over to give her a kiss and asked how it was and she said great while trying to slow her breathing down. I should have known that watching all exposed and horny like that was going to get me horny as well. As we kissed Liza said what is that I feel against me, I looked at her and smiled. Liza said you are always horny I was wondering when you said you are too tired. Liza then said do you want me to see what I can do about that, I told her it would be okay but she wouldn’t have that. Liza slowly slid down to my swollen cock. First she just slid her hand over my and cupped my balls and that felt great. Then she slid her tongue over the head of my cock and the down to my balls nice and slowly. After this she alternated between just sucking on the head, sliding her tongue down my shaft and balls to taking the entire seven inches of cock in her mouth. She kept working this for about ten minutes and then I couldn’t handle it anymore so I blew my load deep into Liza’s throat. Liza kept working my cock and then said all gone do you feel better know and I said you always make me feel great and you did it again. To which we both laughed told each other how much we loved one another and passed out.
The next morning we had a good breakfast. Liza and Wendy had our day planned we were to go to Millennium and Grant Parks. The ladies were dress very nicely. Liza wore a thigh length skirt that accentuated her bottom and form fitting top that did and even better job of top. As for Wendy she wore a sheer summer dress with spaghetti straps that came to just above her knees and since she had spaghetti straps she opted not to wear a bra. I must say that for a woman of 45 with 40 DD they seemed very firm in such a sheer dress. As for Mark and I we got away with shorts and golf shirts. Once we were all ready we headed off to Millennium Park spent some time there and then slowly made our way to Grant Park. Chicago is very beautiful on a summer day Mark and I took a rest at one of the park bench and made notice of all the young guys checking out our wives. I must admit that both ladies looked very delicious and we each commented to the other how attractive the others wife was. After our day at the parks we relaxed back to the hotel and got cleaned up for a night out on the town. Liza and I jumped into the shower and washed each other down she took her tits and wash down my cock until I came all over her tits and face. Once I was done I slid down to her pussy and worked her clit with my tongue until she came. In the end we were both clean and satisfied.
The ladies had chosen jazz club for us to spend the evening in and I was looking forward to the music and a little dancing with my lady. Both ladies looked exquisite they were both wearing form fitting dresses with plunging neck lines. Liza was in black number while Wendy was in a dark green color. Liza had 3 inch heels and when she faced me it was just the right height to hold on to her perfect ass. Wendy on the other hand was wearing 4 inch stilettos and she looked really hot. Mark and I had slacks and sport coats kind of looked bad compared to the ladies. The jazz club was only a couple of blocks from our hotel so we decided to walk, obliviously it wasn’t the first time Wendy had worn stilettos because she had no problem with the walk. The food, music and dancing were great. While we were there Mark and I both enjoyed a nice cigar and the ladies got asked to dance a couple of times. Seems the African American guys really liked our ladies and what’s not to like pretty faces, big tits, nice ass and beautiful legs. A couple of them to a real shine to Liza and Wendy and asked them to dance. The ladies seemed to enjoy the attention immensely. We left the club around 11:30 and had a nice leisurely walk back to our hotel.
Once back at the hotel Mark and Wendy decided that they wanted to watch the big screen in the common area and have a few drinks. Liza said that she and I were going to relax to our bedroom. I was a little upset I thought we would relax talk and have a few drinks. I took my time heading to the bedroom and got myself a drink from the bar. Liza said to me hurry up and get into our room and let these two have some privacy, I said they have there own room if they want privacy and as I said that Mark walked out in his boxers and a T-shirt and Wendy in this incredible thong and baby doll and she sure wasn’t shy about wearing it either. She came right over to Liza gave her a peck on the cheek and said goodnight and then immediately over to me and gave me a little peck and squeezed my leg. Liza looked at me sternly and said lets go to bed so I got up and headed to the bedroom.
Once we were in the room I said what is up and all I got was a shhh! So we got changed and ready for bed Liza shut off the lights and then got out of bed and started peeking out our bedroom door. I slowly went up to see what she was doing and she motioned for me to be quite. Once at the door I could see what she was peeking at Wendy and Mark were getting hot and heavy out on the sofa. Wendy worked her self down on Mark as he sat on the sofa and started to go to work sucking on his cock. She seemed very diligent in her work. Next thing I know Mark basically leaned forward picked Wendy up and placed her on his cock. I must say pretty impressive. Once she was on his lap she started pumping him slowly and then progressively started going faster. As she was doing this Liza opened our door more and started to go out into the common area heading to the bar that was just outside our door. I started to follow her and she pushed as if to say stay in the room, so I did. Liza sat herself up on one of the bar stools and proceed to unbutton her pajama shirt to expose her tits. Once she had done this she started tweking and twisting her nipples. This always gets Liza wet. After a short period of time Wendy noticed Liza sitting at the bar and just smiled at her, it almost looked like they had it planned. At this point my cock was rock hard and I motioned to Liza to get back into the room and she motioned to me just a minute. The next thing I know Liza has her pussy uncovered and she starts slid her fingers in to her sopping wet pussy and then rubs her clit. Once Wendy saw this she slid off Marks lap and lay across the arm of the sofa facing towards the bar. As soon as Wendy did this Mark jumped up behind Wendy and started pumping her pussy with all of his might. Then the two of them looked up to see Liza pulling on her tits and rubbing her pussy feverishly. The sight of Liza seem to push both Wendy and Mark into over drive and before you know it Mark had filled Wendy with a massive load and Wendy was screaming and moaning it pleasure. Liza unfortunately had not came so she slid from her chair proceeded into our bedroom closed the door bent over on the bed and told me to come quick. I got behind Liza and slid my cock up to her pussy, she said no way so I placed the head of my cock up to her ass and her tight little hole seem to kiss the end of my cock. I pushed the end of my cock in just enough to push open her ass a little and she moaned. I pulled my cock back from her ass and Liza let out a louder moan. She said I want your cock in my ass. So again I pushed the end of my cock in just enough to push open her ass a little and she moaned. I pulled my cock back from her ass and Liza let out a louder moan and said I want that cock. I asked why and she yelled I want my ass fucked I love a cock in my ass. That is when I decided she had waited enough. I placed the head of my cock at the entrance to her tight ass and then slid it in with one slow smooth motion to which Liza let out a very deep moan. This was followed by the command to pump her ass hard and fill it full of cum. So not wanting to displease my horny wife I did as she asked and filled her up.
The next morning over breakfast we all sort of looked around the table a little curiously at each other and then all let out a laugh. Liza and Wendy laughed at Mark and said hopefully we didn’t make you to uncomfortable with our plan to you horny and he said no not at all. He then looked at me and said I guess tonight is your turn to which I looked at Liza and said I guess it is and she let out a laugh and said we’ll see how I feel.
After breakfast we headed to the Navy Pier and had a great day. We came back to the hotel just long enough to get ready and go out for diner to a wonderful restaurant on Michigan Ave. We all had a great meal on the way back to the hotel we found a little shop that sold ice cream so we all got a cone for the walk back to the hotel. Once we got back to the room we turned on the big screen TV. Mark and I were watching some sports highlights with Mark and Wendy on one sofa and Liza and I on the other sofa. After about 15 minutes Wendy said I am tired and heading to bed Mark said while I am coming as well. Liza and I said good night and once they were in the room Liza picked up the TV remote and brought up the pay per view channels. She started scrolling through the movies and eventually made it to the X-rated section. She started scrolling through the titles and picked this one called Amateur Threesomes, so we started watching. She snuggled up to me and said this reminds me of Jamaica and I just smiled at her. After a little while I started massaging her tits and tweeking and twisting her nipples. I could tell this was getting Liza hot because her breathing was getting heavier. A little time after I started this I noticed that Mark and Wendy’s bedroom door was slightly open enough so that they could see us on the couch. The next thing I know Liza slowly slid down to my swollen cock. First she just slid her hand over my and cupped my balls and that felt great. Then she slid her tongue over the head of my cock and the down to my balls nice and slowly. After this she alternated between just sucking on the head, sliding her tongue down my shaft and balls to taking the entire seven inches of cock in her mouth. While Liza was doing this I noticed Wendy slid out the bedroom door and sit down on the couch across from us, Liza didn’t notice her as she was to busy working on my cock. Liza then got up from her knees and straddled me and slowly lowered herself over my cock. Once she was on it she started to slide her self up and down alternating between fast and slow and rotating her hips on my cock. All the time I was working a finger into her ass. The entire time we were are doing this I assumed Wendy was diligently working her pussy like Liza had done the previous night, because I couldn’t really see her while I had Liza’s beautiful tits pressed up to my face. The next thing I know Liza says to me take you finger out of my ass and I did. The next thing she leans forward pushing her tits into my face while she pushed her shoulders back. Then I hear Mark’s voice saying to Liza you want it in your ass and Liza moaning out Yessss! Then I can see Mark up over top of Liza and I can tell from being inside her pussy that she has a cock in her ass. Liza looked down at me and had this extreme look of ecstasy on her face. Liza said in a moaning voice I love having two cocks. I love my ass and pussy being filled. She said feels so good having a cock in her pussy while getting her ass pumped. I said you like getting your tight ass pumped. Liza moaned out again Yesss! I said is it as good as you remember, she said panting its better! Liza said it feels so good to get double fucked by two big cocks. Liza kept pumping her pussy on to my cock and Mark kept pumping his cock hard into her ass. I could hear her sopping wet pussy sucking my cock deep inside. I said what do you like and she let out a moan I love to get double fucked I love having two big cocks fuck me. She screamed out she loved two cocks in her and she yelled at us to keep fucking her. She screamed fill me up, fill me up, fill me up, I love this double fuck. This was followed by the command to pump her pussy and ass hard and fill it full of cum. So not wanting to disappoint my horny wife, Mark and I did as she asked and filled her up. Almost at the same time we all came she let out a moaning scream and Mark dropped a massive load deep in her ass and I let go a huge load up her pussy. Mark climbed off Liza and laid down on the other sofa were Wendy was lying spent from working her pussy until she came. Liza lay limp on top of me I asked her if she was okay and she said I am great that was so intense and she slid off my cock and sat on the sofa.
I had my eyes closed for a minute when all of a sudden I could feel this tongue on my cock. I opened my eyes to find Wendy on her knees teasing at the end of my cock with her tongue. Wendy slowly started taking my cock into her mouth and before I knew it I was hard. Then Liza slid down off the sofa and started kissing Wendy and they alternated sucking on my cock. Then Mark started showing signs of reviving so Wendy crawled over to Mark and started sucking on his cock after a short time Wendy climbed up onto Marks hard cock and slowly slide her wet pussy down and started working on his cock. Liza stopped sucking on my cock and said look at that little tight ass on Wendy doesn’t it look nice and I said yes it sure does. Liza looked up at me with her bottom lip on my cock and said why not go over there and give it a good fuck. I said are you sure and Liza said yeah I want to see you pumping her tight little ass. So I got up and started walking towards Wendy as I got closer Wendy placed her hands on her as and pulled her ass cheeks apart and said Joe slide your cock into my ass. I got behind Wendy and slid my cock up to her tight little ass and her tight little hole was kissing the end of my cock. I pushed the end of my cock in just enough to push open her tight little ass and Wendy let out this loud moan. I pulled my cock back from her ass and Wendy said I want your cock in my ass. So I pushed the end of my cock in just enough to push open her tight little ass a little more and pulled my cock back from her ass and Wendy said sternly I want that cock in my ass. I placed the head of my cock at the entrance to her tight little ass and then slid it in with one quick smooth motion to which Wendy let out a very loud deep moan. This was followed by the order to pump her ass hard and fill it full of cum. So not wanting to displease Liza’s horny friend I did as she asked and filled her up. I was pumping away on her ass and I could hear Wendy’s wet pussy slapping against Mark. Mark called out to Wendy and asked if she liked her first double fuck and she said just don’t stop keep fucking me. I looked back and Liza and she had gotten her double headed dildo from our bedroom and was working her pussy and ass while Mark and I double stuffed Wendy. Before long we all came Wendy let out a loud moaning scream and Mark dropped a massive load in her pussy and I let go a massive load deep in her ass. The four of us carried on alternating up until morning.
At breakfast we were all smiles and told each other we had a great weekend. Liza and Wendy said they were a little tired and Mark and I were a little week in the knees, but we all agreed that the Chicago trip would have to happen again and we made arrangements to get together twice a year for some erotic fun.

End of Story