Milwaukee Cuckhold before the Cuckhold
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Milwaukee Cuckhold Vacation free porn video
I had a business meeting in Hawaii, whenever possible Judy would go with. While I attended my meetings she would arrange for sightseeing and other "fun things".
We had arranged to be there for 12 days. I had business meetings for 5 of those days. Judy was going to arrange her own fun. The fourth day I came home during the day from one of my meetings to change. Of course whenever I came home in the middle of the day I always hoped to catch her in action. Well that day when I got there the do not disturb sign was on the door and my hopes were up.
I go in and find no one there. We had a mini suite so I went into the bedroom and all I could find was her dirty clothes on the floor. I reached down for her panties and they were all gooey being filled with cum. Checked out the bed and there were cum stains all over. No signs of anyone though.
I took the Do not disturb sign off the door after changing and wwas heading back to my meeting when I see the maid in the hallway and she says, "you and Mrs. done now?" I told her she could go ahead and clean the room.
When I came back late that afternoon, Judy was in bed sound asleep. I found her clothes on the floor and looked for her panties again and found her new pair and they were again filled with cum. I was getting real excited wondering what I missed out on.
She never said a word when she woke up and carried on like she was kind of bored. The next day she knew I was done by noon and said tomorrow afternoon we can rest and then go sightseeing the couple of days after that.
The next day we were running late so I called Judy and she answered her phone huffing and puffing and a little out of breath, I asked if everything was ok and she said a little breathlessly that she ran t answer the phone, I knew she always had her phone with her so I new she was probably fucking someone. I told her I would be late and she sounded disappointed.
When I got back about 3pm she was back in bed taking a nap. I checked for her panties again and they were soaked more than ever. Since the meeting was over and this afternoon was supposed to be rest I stripped to my underwear and crawled in bed with her. She was gently snoring and I reached over to touch her privates and could feel she was soaking wet on her cunt and on her ass and her hair was matted and I was thinking I must have missed something good.
We woke up about an hour later and she took off her eye mask (which she uses when she sleeps to cover her eyes so no light bothers her.). I asked her how her day was and she said, "good, did a little shopping and that was it." I looked at her and laughed and said, "oh really". She said, "why do you find that surprising." I laughed and said, "well for a little shopping, your panties were awfully wet."
She got up and went over to the suitcase and rummaged for something which I couldn't see and came back to the bed. She slipped her eye mask on me and said, "well if you think you deserve to know, you have to do it my way." with that she proceeded to take one of my ties and tie each of my wrists to the bed board and the did the same to my ankles. I couldn't move much at that point and couldn't see.
She got a scissors and cut off my briefs and t-shirt. She laughed and said I see the inchworm is still an inchworm as she squeezed my less than endowed cock. She then proceeded to start pinching my nipples with one of her hands as she started playing with my cock with her other. I was getting very horny. She said, "just so you know I haven't gone sightseeing at all, I've been busy having other fun, but I am sure you figured that out by feeling my panties." I laughed and said, "I wouldn't do that" and she said the video camera that was set up shows differently." I stammered and she said, "don't worry, how much do you actually want to know?" With that she really pinched one of my nipples and as I squirmed in ectasy she said, "maybe I will tell you later." With that she stopped what she was doing and I could hear her getting dressed. She walked over and put my cell phone in my hand and said, "remember if it rings, just say answer or if you need to call me just say call Judy. It is already on speaker phone." With that she bent down and bit my nipple hard and said, "have fun, I know I will" and with that she left.
About 10 minutes later she called and said, "just so you know I took the do not disturb sign off the door, but I don't think housekeeping will come in anymore today, of course I could call them and ask them to." Before I could say anything she had hung up. Of course now I was horny as all hell and worried someone could come in. I lay there thinking of what she could be doing and time was passing since I couldn't see I didn't know what time it was. No one knocked or came in so I was happy about that. The phone rang sometime later. I figured it may have been about 4 hours. I said answer and Judy said, "having fun yet?" I said, hopefully not as much as you?" She laughed and asked, "have you ever seen a 10 inch cock close up?" "Well I'm looking at one now and it's a lot bigger than your two inches." In the background I hear someone say, 2 inches?" She hung up right after that. About twenty minutes later I hear a knock at the door and then someone saying, "housekeeping".
I was thinking "oh no" all of a sudden I hear Judy laughing and saying, "have you worried?" I heard her say something back to the living area, like come here. Someone else walked into the room and Judy said Damon this is the inchworm, inchworm this is Damon." The person with her said, "two inches may be generous."
At this point I heard them start kissing. Judy said, "I hope you don't mind doing it in front of him." Damon said, not at all he can listen and learn." I heard clothes coming off and Judy came over and took my hand and said, "I just want you to feel what 10 inches feels like." I'll be honest it felt huge, I was thinking there is no way she will fit this in. Well for the next 2 hours they went at it like teenagers in heat. Judy kept begging for more and it sounded like she came numerous times. It even sounded like Damon had come a couple of times already.
I wasn't sure how long they could go when Judy said, "Damon have you ever had a useless cuckold suck on your cock?" He said, "no but there is always a first time." With that Judy came over and changed the restraints so I could do something. While she was doing that she took my hand and wiped it across her cunt and said it would never be the same. She was so full of come I was really excited. She then had Damon position himself in front of me and Judy helped guide his cock into my mouth. I almost gagged and Judy said, "go slow." I got into a rhythm and Judy said, "he's not doing bad for a sissy, hope it feels good for you Damon." Damon was grunting and said, "for a sissy cocksucker he's not bad he may be able to get a mouthful." Judy said, "oh please, fill is mouth."
After about 10 more minutes he started grunting and Judy told me to take him deeper. I heard a grunt and felt a hot stream going down my throat, I couldn't handle it all and Damon pulled out and finished all over my face. Judy laughed had me lie back down to restrain me again. Judy and Damon went back at it and for the next hour or two they kept cumming. It sounded like they kept changing positions and at one time Judy was taking it in the ass too.
I lay there with my face covered in cum and getting hornier. They finally finished and Damon said, "hey babe I gotta go, here's my number please call. We can even use the sissy cocksucker again."
Once he left, Judy came back and said, "I need to be cleaned out from the last 10 hours." I couldn't believe it had been that long. She straddled my face with her pussy and said, "get that tongue going." I started licking and could not believe how much cum was in her pussy. While I was licking she started playing with my nipples and my cock. She said no matter what, "You can't cum now."
She was grinding her pussy into my mouth and I could get a couple of different tastes and she said, "so how much of the last 5 days do you want to hear about." I couldn't say anything as she was grinding her pussy into my mouth and cumming. There was a knock at the door and a voice said, "housekeeping" and Judy in mid-orgasm said, "please cum in"......
We had arranged to be there for 12 days. I had business meetings for 5 of those days. Judy was going to arrange her own fun. The fourth day I came home during the day from one of my meetings to change. Of course whenever I came home in the middle of the day I always hoped to catch her in action. Well that day when I got there the do not disturb sign was on the door and my hopes were up.
I go in and find no one there. We had a mini suite so I went into the bedroom and all I could find was her dirty clothes on the floor. I reached down for her panties and they were all gooey being filled with cum. Checked out the bed and there were cum stains all over. No signs of anyone though.
I took the Do not disturb sign off the door after changing and wwas heading back to my meeting when I see the maid in the hallway and she says, "you and Mrs. done now?" I told her she could go ahead and clean the room.
When I came back late that afternoon, Judy was in bed sound asleep. I found her clothes on the floor and looked for her panties again and found her new pair and they were again filled with cum. I was getting real excited wondering what I missed out on.
She never said a word when she woke up and carried on like she was kind of bored. The next day she knew I was done by noon and said tomorrow afternoon we can rest and then go sightseeing the couple of days after that.
The next day we were running late so I called Judy and she answered her phone huffing and puffing and a little out of breath, I asked if everything was ok and she said a little breathlessly that she ran t answer the phone, I knew she always had her phone with her so I new she was probably fucking someone. I told her I would be late and she sounded disappointed.
When I got back about 3pm she was back in bed taking a nap. I checked for her panties again and they were soaked more than ever. Since the meeting was over and this afternoon was supposed to be rest I stripped to my underwear and crawled in bed with her. She was gently snoring and I reached over to touch her privates and could feel she was soaking wet on her cunt and on her ass and her hair was matted and I was thinking I must have missed something good.
We woke up about an hour later and she took off her eye mask (which she uses when she sleeps to cover her eyes so no light bothers her.). I asked her how her day was and she said, "good, did a little shopping and that was it." I looked at her and laughed and said, "oh really". She said, "why do you find that surprising." I laughed and said, "well for a little shopping, your panties were awfully wet."
She got up and went over to the suitcase and rummaged for something which I couldn't see and came back to the bed. She slipped her eye mask on me and said, "well if you think you deserve to know, you have to do it my way." with that she proceeded to take one of my ties and tie each of my wrists to the bed board and the did the same to my ankles. I couldn't move much at that point and couldn't see.
She got a scissors and cut off my briefs and t-shirt. She laughed and said I see the inchworm is still an inchworm as she squeezed my less than endowed cock. She then proceeded to start pinching my nipples with one of her hands as she started playing with my cock with her other. I was getting very horny. She said, "just so you know I haven't gone sightseeing at all, I've been busy having other fun, but I am sure you figured that out by feeling my panties." I laughed and said, "I wouldn't do that" and she said the video camera that was set up shows differently." I stammered and she said, "don't worry, how much do you actually want to know?" With that she really pinched one of my nipples and as I squirmed in ectasy she said, "maybe I will tell you later." With that she stopped what she was doing and I could hear her getting dressed. She walked over and put my cell phone in my hand and said, "remember if it rings, just say answer or if you need to call me just say call Judy. It is already on speaker phone." With that she bent down and bit my nipple hard and said, "have fun, I know I will" and with that she left.
About 10 minutes later she called and said, "just so you know I took the do not disturb sign off the door, but I don't think housekeeping will come in anymore today, of course I could call them and ask them to." Before I could say anything she had hung up. Of course now I was horny as all hell and worried someone could come in. I lay there thinking of what she could be doing and time was passing since I couldn't see I didn't know what time it was. No one knocked or came in so I was happy about that. The phone rang sometime later. I figured it may have been about 4 hours. I said answer and Judy said, "having fun yet?" I said, hopefully not as much as you?" She laughed and asked, "have you ever seen a 10 inch cock close up?" "Well I'm looking at one now and it's a lot bigger than your two inches." In the background I hear someone say, 2 inches?" She hung up right after that. About twenty minutes later I hear a knock at the door and then someone saying, "housekeeping".
I was thinking "oh no" all of a sudden I hear Judy laughing and saying, "have you worried?" I heard her say something back to the living area, like come here. Someone else walked into the room and Judy said Damon this is the inchworm, inchworm this is Damon." The person with her said, "two inches may be generous."
At this point I heard them start kissing. Judy said, "I hope you don't mind doing it in front of him." Damon said, not at all he can listen and learn." I heard clothes coming off and Judy came over and took my hand and said, "I just want you to feel what 10 inches feels like." I'll be honest it felt huge, I was thinking there is no way she will fit this in. Well for the next 2 hours they went at it like teenagers in heat. Judy kept begging for more and it sounded like she came numerous times. It even sounded like Damon had come a couple of times already.
I wasn't sure how long they could go when Judy said, "Damon have you ever had a useless cuckold suck on your cock?" He said, "no but there is always a first time." With that Judy came over and changed the restraints so I could do something. While she was doing that she took my hand and wiped it across her cunt and said it would never be the same. She was so full of come I was really excited. She then had Damon position himself in front of me and Judy helped guide his cock into my mouth. I almost gagged and Judy said, "go slow." I got into a rhythm and Judy said, "he's not doing bad for a sissy, hope it feels good for you Damon." Damon was grunting and said, "for a sissy cocksucker he's not bad he may be able to get a mouthful." Judy said, "oh please, fill is mouth."
After about 10 more minutes he started grunting and Judy told me to take him deeper. I heard a grunt and felt a hot stream going down my throat, I couldn't handle it all and Damon pulled out and finished all over my face. Judy laughed had me lie back down to restrain me again. Judy and Damon went back at it and for the next hour or two they kept cumming. It sounded like they kept changing positions and at one time Judy was taking it in the ass too.
I lay there with my face covered in cum and getting hornier. They finally finished and Damon said, "hey babe I gotta go, here's my number please call. We can even use the sissy cocksucker again."
Once he left, Judy came back and said, "I need to be cleaned out from the last 10 hours." I couldn't believe it had been that long. She straddled my face with her pussy and said, "get that tongue going." I started licking and could not believe how much cum was in her pussy. While I was licking she started playing with my nipples and my cock. She said no matter what, "You can't cum now."
She was grinding her pussy into my mouth and I could get a couple of different tastes and she said, "so how much of the last 5 days do you want to hear about." I couldn't say anything as she was grinding her pussy into my mouth and cumming. There was a knock at the door and a voice said, "housekeeping" and Judy in mid-orgasm said, "please cum in"......
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