Milwaukee Cuckold's Wife and a New Adventure

We have been swinging for over 30 years. I am not well endowed and Judy likes bigger cocks so it has worked out well for us. Only a few people close to us know about the things we do. Two of Judy’s sisters and one of her best friends know. And one friend of mine knows or so I thought.

The reason my friend Sandy knew was that she confided in me that she cheated on her husband. She even gave me all of the horny details and I could tell she was getting horny telling me. She then went on to say that even though she hasn’t had sex with her husband for 15 years she didn’t enjoy this encounter. She said she enjoyed talking about it more than doing it. I laughed and said it made sense. She looked at me like I was nuts. I said I have been in that situation for years and proceeded to tell her Judy has had friends with benefits for a long time and I love hearing about what she has done. After asking why we did and finding out about my tiny penis she would occasionally ask about some of the things Judy had done. I had no problems filling her in and she seemed to enjoy hearing it. She once asked if I told Judy that I was telling others what she had done. I told her of course she could ask Judy anything she wanted.

Well she did. Judy started filling her in on some of the things she did as well as the things she did to me. Sandy never told me she went straight to the source. Judy never really mentioned it to me either. Well they started chatting 2 or 3 times a week. Judy mentioned once to Sandy that she even had videos and pictures of some of her escapade. Sandy asked her once if she would share some of them. Judy was enjoying the chats and had no problems sharing.

So, while they were face timing Judy would hold her phone up to catch the TV as the DVD was playing her escapades. Well as Judy was fucking on the DVD she started to hear moans that weren’t her own. She looked at her phone and Sandy had gotten naked and was busy playing with herself. She noticed Judy noticed her and Judy said, “don’t worry go on playing.” For the next couple of weeks Judy would play some of her videos and show Sandy some of her pictures. Eventually Judy started getting naked as well and the two of them would play with themselves while talking.

Sandy finally admitted she was telling her daughter the stories about swinging since her daughter was going through a divorce. She said she never told her daughter who she was chatting with and her daughter admitted to her she started swinging and doing some other kinky things. Eventually during one of these twice a week phone sex sessions as Judy and Sandy are both playing with themselves on Facetime Judy heard someone yell, “MOM, WHAT ARE YOU DOING?” Sandy didn’t miss a beat and came to two loud orgasms. Judy heard again, “MOM!” Judy recognized the voice of Sandy’s daughter Kelly. Judy then saw Kelly’s face on the phone and the video ended.

Judy admitted that she and Sandy had been having cybersex without actually having sex and that it had been kind of fun. While she was telling me everything that had gone on her phone rand and she said it was Sandy so she went out of the room to take it. When she came back in the room she said she was having lunch with Sandy and her daughter tomorrow. I asked if she knew why but she didn’t.

The next day while I working I got a text and all it said was “OMG”. Nothing else. Just as I was finishing for the day I got another cryptic “OMG”. I texted back and said, “what?” Twenty minutes later I get another message, “won’t be home for dinner, having fun, wait for more info.”

About 9pm I got another text from Judy, “won’t be home, it’s been a fun day, have some great pictures.” Still not sure what she was talking about, I just answered. “?” About 10pm I texted Sandy and asked if she had seen Judy today. Sandy texted back, “we spent the day together learning some things.” Nothing more. An hour later my phone started dinging with texts from a number I didn’t know. I look and the first picture I see is Judy’s gaping pussy filled with cum. I got about 15 pictures of Judy doing various things from fucking, to sucking to licking pussy, one had her with clothespins on her nipples and cunt lips. One of the pictures looked like Sandy was in it with her. About 5 minutes later I get a text that said, “your wife trains well, do you?” I wrote back, “who is this?” The answer is just “soon.” Overnight I received about twenty more pictures of Judy fucking, and sucking and even some really kinky stuff that amazed even me.

About 8am I get a text from Judy that says, “need to be cleaned, be there in 30 minutes, be ready.” I knew she wanted me to be in bed naked preferably tied to the head board but I could only do part of that. I got naked and got into bed. I heard the door chime and Judy came upstairs. She came into the bedroom and took off her coat and she wasn’t wearing anything underneath it. I said, “you are lucky you didn’t get stopped.” Her response was “might have been fun.”

As she walked toward the bed I could see she had been used and abused. She had wet and dry cum all over, she had gentle bruising over her tits and her ass and her pussy lips were so engorged it looked like she had a penis. I said, “so want to tell me what happened?” She put her fingers to her lips got on the bed and mounted my face and I started licking. Pretty soon she was moaning and groaning and grinding her pussy into my face. She had cum 3 times and started to say, “I have never had a night like that.” Before I could say anything, our phone rang, she moved aside so I could answer. I hear a voice and it says, “hey doc.” I know it is Sandy. She says, “I hate to bother you on a Saturday but Kelly just got back to town and she has a really bad toothache could you see her or give her some medication. Knowing Sandy and I are good friends I said I would go into the office to see her and I would meet them there in 30 minutes. She said she was busy but Kelly would be there.

Judy asked what was going on and I told her. She offered to go with me. Normally I would have told her to rest but I didn’t like seeing female patients alone, even a friend’s daughter, so I told her sure. She said maybe she would just wear her coat. I told her she wouldn’t have the guts. She put her heals on and just her trench coat and I just laughed.

Got to the office and Kelly was there. Took Kelly into the operatory and told Judy we would be ready in a couple of minutes. Had Kelly get into the chair and as I ask every patient, “so what’s new and exciting besides your toothache?” She didn’t say anything and squirmed around on the chair. Finally, she said, “just got back from Chicago seeing my “friend”” and she made quotation marks when she said “friend”. She squirmed some more and I said “OH” realizing she meant fuck friend. She then said, “I didn’t even have time to put this on.” And she pulled a cum soaked thong out of her pocket. I had no idea what to say until Judy completely walked into the room and said, “good morning Mistress Kelly, thank you for last night.” I sat there looking flabbergasted and Kelly reached out and pulled up her skirt and took my hand and rubbed it against her bald cum soaked pussy.

Kelly laughed and said I guess we need to explain but why don’t we go back to my house. We got into my SUV with Judy and Kelly in the back and me driving. Kelly pulled her skirt up and directed Judy’s head down to lick her pussy. Kelly looked at me and said, “I have you to thank for all my fun.” She went on to explain that when she walked in on her mother and Judy having cybersex her mother explained to her how Judy told her about our cuckolding and swinging and everything Judy did. She then started watching her mother and Judy have cybersex and learning about everything we did. She then started swinging herself which kind of led to her divorce. Then to earn money she became a Madame/dominatrix. Last night it culminated she told me with Judy and her mother joining her for a party. During the ride, she managed to cum several times.

When we got to Kelly’s she had me park in the driveway. She led Judy who was still naked to the door. We went in and she suggested maybe that I should get undressed. Not sure what to do but intrigued I did so. While I was getting naked Kelly went into the other room and came out wearing 6 inch stilettos, a leather bustier with the nipples cut out and she had big tits and big pointy nipples, she was also wearing a very skimpy lace thong. Once I was naked, Kelly laughed and said, “wow you weren’t k**ding, this is one of the smallest cocks I have ever seen, it looks like a clit.” She took me by the nipple and lead me a room with a lock on the door.

I was amazed by what I saw. There were shackles on the wall, beds with restraints, ceiling swings, a variety of handcuffs, whips, vibrators, robo-sex machines. I had never seen so many toys in one place. Kelly said, “Welcome to Mistress Kelly’s Dungeon.” She took me by my nipple to some wall restraints. She shackled my arms and ankles so I was there until someone let me go. She then took what felt like clothespins and put them on my nipples and then she tightened them. Judy was playing with one of the big dildos and watching what Kelly was doing to me, she then put the same thing on my penis and turned to Judy and laughed and said, “you weren’t k**ding it’s small, it looks like my clit when I was 12.” Kelly then said, “I won’t blindfold you yet because I want to thank you.”

I was kind of dumbfounded and said, “huh?” Kelly said, “because you talked Judy into swinging and cuckolding you and because of that Judy and my mom exchanged ideas and had facetime sex that I walked in on. I eventually joined them and expanded it from there.” I heard door chimes and Kelly left, she came back with a middle-aged couple. She said, “Jim and Linda I know you are here to expand your sexual horizons, Linda is afraid to experiment or do too much and Jim is always horny, so I know just what we need to do. Why don’t the two of you go into the dressing room and strip and come back out.

While Jim and Linda were undressing, I noticed Sandy come into the room. She was completely naked with one of the hairiest bushes I’ve ever seen, her tits were big and sagging but she had some of the biggest nipples I have ever seen. She walked over to Judy and gave her a deep kiss with her tongue, she went up to her mother and did the same. Then she walked up to me pinched my nipple hard and kissed me and said, “thanks for changing my life with your teeny cock.”

Jim and Linda came out of the changing room. Linda was average looking, she had pert boobs and a little blond landing strip down by her pubes. Jim was rather well endowed with a 9-10-inch cock that was very thick. Kelly walked over and gently started pulling on his cock which sprang to attention. She said loudly, “since Linda is too frigid for fun, she needs to watch you have some fun Jim.” She got down on her knees and gently started licking his massive shaft. She eventually took the entire member in her mouth as Jim started moaning. Linda gasped and you could hear quietly say, “wow the whole thing.” Judy watching this walked over and disengaged Kelly and Jim and took Jim by the hand. She walked over by one of the swings hanging from the ceiling and she got on her knees and started massaging Jims cock with her tongue. Jim was slowly thrusting to meet her mouth with his cock. After 15 minutes Jim moaning Judy got into the sex swing and pulled Jim close and guided his cock into her soaking wet pussy. Each stroke worked its way a little deeper than the previous. Each time his cock penetrated to a new depth, another gasp came from Judy’s mouth.

While Judy and Jim were making use of the swing Linda’s hand slid down to just below her landing strip and she started to massage her cunt lips as her love juices ran down her leg. Sandy noticed this and walked over by Linda and reached her hand down to her pussy and started massaging Linda’s snatch with Linda. Linda said I’ve never liked sucking his cock and now two women have swallowed the entire thing.” Sandy laughed and said, “I think you just prefer someone without a penis. She leaned up and started kissing Linda who was kissing back.

I was getting the show of a lifetime. My wife is fucking and sucking someone with a huge cock and a good friend I got to see naked for the first time and she’s making out with another woman. All of this while Mistress Kelly came up to me and said because of you this couple is paying me $1500 for 4 hours of fun. How can I thank you?” I just smiled and said, “do whatever you want.” She smiled and said, “gladly.” At that moment I heard Judy scream, “I’m cuuummmming.” As Judy was bucking and moaning Jim continued thrusting and you could see just as he came Judy moaned loudly once more and laid back in the swing. Linda stopped to watch and then pulled Sandy’s tongue back down to her crotch.

Kelly took my restraints off and told me to be good, she took me by the hand over by the swing and said it’s time for the dickless wonder to clean up. Kelly had me get down and start cleaning Judy. Judy grabbed my head and pulled me closer to her cunt to clean out all of the cum that Jim left. Pretty soon Judy was writhing and cumming again. After she was spent Kelly took me by the hand and said, “remember you said anything?” She took me over by Jim and said, “go ahead and make him cum again.” I looked at her and she said, “remember you said anything.”

I got down on my knees and grabbed Jim’s massive cock with my hand and slowly started licking up and down his shaft. Slowly I started to take his cock in my mouth. I gagged a little but eventually got most of it in my mouth. Jim Started moaning and Kelly laughed and said, “wow Judy, we got us a new cocksucker.” She then turned to Linda and said, “Linda did you know your hubby was bi? Or did he know you were gay.” That must have excited Linda because she grabbed Sandy’s head and buried it in her crotch and she yelled that she was cumming. When she did that I felt Jim’s shaft really stiffen in my mouth and felt spurts of hot liquid shooting into my mouth. I could barely swallow fast enough to prevent myself from gagging.

Once I was done, Kelly took me by the nipple again and led me back to the shackles. For the next 4 hours, she continued to have Judy and Sandy service Jim and Linda. They kept switching. Kelly would occasionally come over by me and ask if I was enjoying? I said yes but it was hard to believe her mom who was such a good friend and her daughter who I knew since she was 10 were as slutty as my wife. She smiled and said, “Judy said you were content with your worthless cock and you like to be humiliated.” I said, “true on all counts.” She laughed and said, “good!”

After Jim and Linda were done with their four hours Kelly took them out. When she came back and held up this 8-inch strap-on and said, “who wants to use this?” Sandy raised her hand and said, “I do.” Kelly gave it to her and said, “have fun.” Sandy came over by me and released the restraints and led me over to the couch. She had me lean over the ottoman and lubed up my ass and put on the strap-on.

While this was happening, Kelly looked at Judy and said, “ok do you want Jake or your husband to lick your cunt.” Judy didn’t hesitate as she got down on all fours and said Jake. Kelly smiled and went to the door and yelled, “Jake.” In bounded this large German Shepard who seemed to know exactly what to do and mounted Judy who let out a gasp. Just as I heard that I felt Sandy slide into my ass and grab my titties and say, “I always wanted to do this.” I have to say as she kept thrusting it felt good. As Judy started to moan Jake thrusted faster. Kelly cam over by me and laid down and had me bury my head into her bald pussy and, said, “work your tongue on my twat and just wait for the humiliation later. “With that Jake came and knotted himself in Judy who looked at me contently and just smiled.
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toothmedic
toothmedic Άτομο δημοσίευσης Πριν από 2 έτη
σε Spooky1451 : They have
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Spooky1451
Spooky1451 Πριν από 2 έτη
wow, very hot story, I hope all the friendships have continued.
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toothmedic
toothmedic Άτομο δημοσίευσης Πριν από 3 έτη
σε chiguy_38 : They keep going
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chiguy_38
chiguy_38 Πριν από 3 έτη
Very hot story.  I'm sure the adventures did stop there.
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dirtyoldbiman
wow, lot of activity for 1 day or weekend
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toothmedic
toothmedic Άτομο δημοσίευσης Πριν από 6 έτη
σε nickandnicole1 : thanks
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toothmedic
toothmedic Άτομο δημοσίευσης Πριν από 6 έτη
σε maturehungmale : It was exciting and I never expected it considering how it happened!
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maturehungmale
maturehungmale Πριν από 6 έτη
fucking hot story, agree that it was awesome
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nickandnicole1 Πριν από 6 έτη
Awesome
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