Milwaukee Cuckold’s Wife and the Crossdresser

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Milwaukee Cuckold’s Wife and the CrossdresserJudy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her thigh high stockings with garter and a sexy negligee and 3 inch heels, which she never wore. She went to the front hall and put on her coat and said she would be back soon. She told me to get undressed and go lay on the couch.About 45 minutes later I heard the garage door go up and the backdoor open. I heard laughing and talking. No one came back to the family room but all of a sudden I heard footsteps upstairs in our bedroom. Thirty minutes later Judy came into the family room and said, “oh good, you listened and stayed there. I have someone I want you to meet.” She came back and said, “This is Terri, and Terri, this is the dickless wonder.” In walked a very nice looking 55-year-old woman wearing a very sexy bra that had the nipples cut out. When I looked down it looked like her panties had a huge bulge.She looked at me and giggled and turned around to walk out. Judy came over to me and handed me the iPad set up to our video camera in our bedroom. She said I should stay right where I am and she may let me watch something. With that she flashed her bald pussy at me which was soaking wet. Before I could ask about the panties with the bulge she was out of the room.I could hear the footsteps in our bedroom again, so I turned on the iPad. I could see them kissing and their hands roaming. All of a sudden in a voice huskier than illegal bahis I expected Terri said, “wow you weren’t k**ding about him being a dickless wonder, it looks more like a little clit than a dick.” With that Judy took Terri by the hand toward the camera in our bedroom and said, “I think we should show him.” With that she reached around Terri’s waste and pulled down her panties to expose a very nice 9-inch cock. I was looking at Terri completely nude and she had these real nice B cup boobs with nice pointy nipples and a rather nice looking thick nine-inch cock. Judy and Terri went over to the bed and engaged in fore play for the next 45 minutes. Judy shut the video off for part of the time and I was left wondering what they were doing. She eventually turned its back on as she got on to the end of the bed and stuck her ass in the air. Terri walked up to her and started fucking Judy doggie style. Judy started moaning and said, “oh yes, please fuck me with that big dick. Stick it in deeper.” Her breathing got shallower and she was moaning more and then she started yelling, “yes, yes, I’m going to cuuuummmmm.” After watching Judy cum, they moved back onto the bed and spent the next 10 minutes kissing and making out. Terri then said, “did you tell him we are expecting more company.” Judy said, “I forgot, let me go down and tell him.” Terri said, “don’t worry, I will.”Terri came walking into the room and stood in front of me. She said, “were you surprised?” I said, “very much so.” She said, “we’ve been seeing each other for the past 12 months, I’m the first crossdresser Judy has been with.” She then walked up to me with her cock about 12 inches in front of my face and said, “bet you would love to taste this.” Before I could answer she said, we’re going to have company soon, please make sure you answer the door just like that and send them upstairs.” illegal bahis siteleri She got back upstairs and Judy said, “well what did he say?” Terri said, “I told him he has to answer the door just like that.” Judy laughed and said, “I hope no one else comes, there’s no peep hole.” They went back to their love making. It was amazing to watch this crossdresser, totally enthrall Judy as they fucked doggie style and in a missionary position and anally. Eventually they got into a 69 position when I heard the doorbell. I walked cautiously to the door and I heard Judy say, “I wish we could watch him open the door.”Got to the door and opened it carefully so as to not being seen and there stood a nice looking 25-year-old guy. He said, “are Jim and Judy here? I mean Terri and Judy?” I said, “Please come in.” I tried to modestly cover myself up and this young man goes, “don’t worry, I’ve seen lots of pictures of you.” Not knowing what to say, I pointed up the stairs and said to go in the first door on the left.I hurried back to the family room and watched him enter the room, Judy said, “hi Brad.” The young man gave Judy a kiss and hugged Terri and said, “Hello, Judy, hi dad, I see you guys started without me. With that they helped him undress and they all got on the bed.Judy took Terri in her mouth and Brad doggie style. After about 15 minutes Terri started to grunt a little bit and Brad said, “pull out as you cum.” Judy started to moan faster and started thrusting her hips more and just as Terri pulled out and filled her face with cum, she yelled, “I’m cumming.” Over the next two hours they did just about everything and Judy had so much cum all over her and in her I, was wondering what she was going to do about it. Just then the live feed cut. I heard footsteps coming toward me and Judy walked in to the room. She saw my little 2inch dick spring up and canlı bahis siteleri she says “Someone liked what he saw.” Before I can answer she takes my hand and says, “come with me there is a lot of cleanup that needs to be done.”She took me upstairs and she got into the middle of the bed and said, “Please clean me and let Terri and Brad watch and enjoy.” With that she had me start with her face and had me work down to her pussy. I slowly worked down while the three of them watched. When I got to her cum filled pussy she told me there was a lot to clean and I better make her cum. Pretty soon as I was making sure I got all of the cum and pretty soon her hips were gyrating as she was getting close. Another 10 minutes I had gotten it all and she was on the verge of cumming and all of a sudden, she just let go and came all over my face. She got done and just laid there for a few moments and got up and said we now have two cocks to clean I took Terri’s first and managed to get most of it in. With Judy encouraging me and not gagging I managed to get Terri to cum in about 10 minutes and he shot a load of jism that just dripped down my throat. When done with Terri, Judy pointed to Brad and said, “Ok one more to go.” Brad’s penis was a little bit bigger than his dads. I gagged on it but managed to finish him as he shot a massive load down my throat. After he finished I just lay there. Brad said he needed to take off. He thanked us all and Judy and Terri walked him to the door telling me to stay where I was which I did.Judy and Terri came back into the room and said to Terri, “want to see how his little clit cums.” She had me lay down and tied my ankles and wrists and put a blindfold on me. As I felt two sets of hands start to pinch and knead my nipples and play with my little dicklet Judy said, “were you surprised when you heard Terri and I have been seeing each other for over a year?” Before I could answer Terri said, “I suppose you haven’t told him you were thinking about hormone creams to make his man boobs grow or taking him for a bra.” Hearing say that I deposited a huge load of cum over everything.

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