toothmedic's Blog

[Story] Milwaukee Cuckold and the Cleaning Lady

I still say I am one of the luckiest guys in the world. We have been married over 30 years and Judy my wife still has sex 3-4 times a week, with others. I am a cuckold and live vicariously through what my wife does.

Judy has a few regulars that she meets with while I am at work. One of these “friends” is actually an old friend of the f****y. Judy meets with him two times a week. He knows about our situation and the fact Judy fills me in on what they do.

Often times Judy will call while she is entertaining and leave me a message on my phone at the office. Once in a while I am lucky enoug... Continue»
Posted by toothmedic 1 month ago

[Story] Cuckold in Milwaukee Has Fun

After I exploded, Judy and her ther****t used their fingers to make me clean up all my cum. Judy then looked at her ther****t and said, “you really think it would humiliate him if I took him to get fitted for a bra?” Kris laughed and said, “he may cum on the spot.” Judy said that would be a great idea but not sure if I could walk in and do that to a store.

Kris said, “hang on a second, let me call Mary in and ask her where to go.” I laughed and said, you are going to call someone in and I am laying here naked?” Neither responded and Kris went to phone and asked Mary to come in. Mary came in... Continue»
Posted by toothmedic 1 month ago

[Story] Milwaukee cuckhold vacation 2

As the maid came in Judy came even harder. When the maid walked in far enough, she said, “Oh I can come back later.” Judy said, “No please stay and do what you need to do.” I could hear the maid going around the rom doing things. Judy kept pounding my face with her pussy and pinching and playing. I could hear the maid move into the room we were in and Judy started telling me about some of the things she had done.

It sounded like the maid was still milling close by and Judy said, “by the way this is the second time Susan has come to clean and walked in while I was having an orgasm.” I heard... Continue»
Posted by toothmedic 2 months ago

[Story] Milwaukee cuckhold vacation

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 min... Continue»
Posted by toothmedic 2 months ago

[Story] Cuckhold in Milwaukee 10

After watching Judy and her transgendered lover and his son have sex for hours they had fun jerking me off and talk about sissifying me.

After I came I figured Judy would get cleaned up and we would head home. She came over and placed my hand on her cum filled pussy and said let's stay the weekend. I looked at her and she said just think of all the sex we could have. That was all I needed to hear.

Jim came over by Judy and gave her a big deep kiss and said he was glad we were staying he can plan a lot of things. He said let's start with getting your hubby some proper clothes. Judy smil... Continue»
Posted by toothmedic 5 months ago

[Story] Milwaukee Cuckhold

One Saturday morning I got an emergency call for a patient that lost a filling. She was a long time patient who I thought was kind of cute but always thought she was a lesbian. I made arrangements to meet her at the office in an hour. As I got off the couch Judy asked where I was going. I said I was going to the office to see a patient as she broke a tooth. usually I do not got see a female patient alone after hours but since I have known her for 20 plus years and thought she was a lesbian I had no problems going alone. Judy looked at me and said, "you're not going to see a female patient alon... Continue»
Posted by toothmedic 5 months ago

[Story] Cuckhold in Milwaukee Part 9

I was cuckolded for over 20 years and considered myself one of the luckiest guys in the world. Though I got jerked off only once every couple of weeks I loved hearing about what my wife has done.

One night she was entertaining a friend, that is all she would tell me is that I was too stay downstairs. Of course I couldn't wait to hear what was happening. Well as the time creeped past midnight I was getting tired and dozing off. All of a sudden someone went by me and I open my eyes to see a woman dressed in stockings and a lace thong and a bra going by and I was thinking not a bad looking ass... Continue»
Posted by toothmedic 6 months ago

[Story] Cuckold in Milwaukee visits his wife's therap

Judy and Tammy were laying there after they had me lick out their cum filled pussies. They came a few more times and lay there talking after tying me back up

Tammy asked Judy if she had been getting much lately and Judy said she had been too busy and the only thing she had gotten was her ther****t when she was there complaining about my size. Tammy laughed and suggested they go out and see if they could arrange some fun. They got up naked and said they were going to go have more fun. I asked "what about me?" Judy told Tammy to dial her phone and Judy put her phone on speaker and laid it nex... Continue»
Posted by toothmedic 7 months ago

[Story] Cuckhold in Milwaukee & Craigslist

We had spent the last couple of weeks dropping off the k**s at their colleges. We were settling into an empty house when Judy asked me what I wanted to do for my birthday. I said, "whatever." She said, "Ok".

The day of my birthday I was wondering if she had cooked anything up. As the day wore on I was starting to wonder if maybe she didn't. Judy spent most of the afternoon on the computer and then at about 7pm stood up and said she was going to take a shower. While she went to take her shower I walked over to the computer to see what she had been looking at, since she left it on. When I wal... Continue»
Posted by toothmedic 8 months ago  |  1

[Story] Cuckhold in Milwaukee Part 7

I was able to lay there and relax for a while thinking about what has happened. I can't believe Judy was able to pull something like off.

I kept hearing the chime ding, but neither Sammy or Angie came back for a while. About an hour after my show for the bachelorette party, Angie came back and asked, "How are you doing." I looked at her and said "it has been an interesting morning." She said, "good, we'll try to keep it that way, Judy said you have sucked cock before." I said, "yes I have." She walked away smiling and I started to get a hard on.

Pretty soon, Angie heads back and says, "... Continue»
Posted by toothmedic 8 months ago  |  1

[Story] Cuckhold in Milwaukee Part 6

Recently had to go away to a meeting. Drove 6 hours. Called my wife to tell her I wish she was with as I was passing all these adult toy stores and strip joints

Turns out there was one just a couple of exits away from my hotel. My wife asked about it and I filled her in that it looked kind of dead and empty. The few times I drove by it no one was there. The morning I was leaving at about 9am to go home. At 8:30 I get a text from my wife that she wanted me to stop and pick a few things at this particular place. I asked why this one it looks so dead. She said she called and they had what she ... Continue»
Posted by toothmedic 8 months ago  |  1

[Story] Cuckhold's wife has fun

There were many nights that my wife would have "friends" over and I could hear her in the other room having fun. She could become very loud and beg for more. She usually had me tied to a bed or chair so the most I could do was enjoy listening to her.

She even had me set up cameras so she could get things on tape. Sometimes she would use it to excite me and sometimes she would tape what she did to me just to embarrass me.

Of course a lot of this was easier before we had k**s. The funny thing was early on in our marriage we lived in apartments and no one ever questioned guys or couples sh... Continue»
Posted by toothmedic 1 year ago  |  1

[Story] Cuckhold in Milwaukee Part 5

I couldn't believe Bill was the patient. He suggested we go out for a drink that night so we did.

While at the bar, he told me he had been fucking her for 5 months now. He said he occasionally even brought his girlfriend over. He said one of the first times at the house he saw a picture of the two of us and asked Judy who the guy was. He was surprised when he heard I was her husband.

He told me because I wasn't a good enough husband to sustain my wife that he was going to give me a really good present while he did. He suggested we go to my house then.

When we got there we walked in ... Continue»
Posted by toothmedic 1 year ago  |  2

[Story] Cuckhold i Milwaukee Part 4

from Part 3
They started bantering back and forth about what they had done. Turns out they had been at it for over a year. I was so ready to cum. Judy turns to look at me and says, "wonder what he would think if he knew one of his patients was coming over again tomorrow."

At that point I exploded all over myself. Debbie goes, "wow for such a little cock he sure can cum." Judy said yeah but he made a mess so I think he needs to clean himself. So they both swoop in with their fingers to scoop up my cum and make me lick it. When they were done with that, Debbie says, "believe it or not that ... Continue»
Posted by toothmedic 1 year ago  |  2

[Story] Cuckhold in Milwaukee Part 3

I may have created a monster. My wife was horny all the time now.

She kept thanking me for introducing her into swinging and wanted to make sure I was cool with what she was doing. I told her no problem, just keep having fun and let me know what is happening. She gave me a big kiss and told me she will and tried to give my dick a squeeze but said oh well can't find it.

Later that night she gave me another kiss, I asked what was that for? She said, "to thank me again for all the fun she is having as she visited a of swinger sites and had a great week planned." I said what are you going to... Continue»
Posted by toothmedic 1 year ago  |  3

[Story] Becoming a cuckhold

How I became a cuckhold
February 15, 2013, 4:47 pm
My wife was amazed that I enjoyed watching and hearing about others having her. She said, "You really don't mind?" I said not a chance it makes me very horny! She said she's glad something makes my little cock horny.

She told me she wanted to keep fucking others, did I mind? I said whatever you want. She said I am glad you said that, from now I get my cock and pussy from others? I said what does that mean for me? she said I may let you watch and I may let you clean me after I fuck, and to be nice I will jerk you off once very couple of w... Continue»
Posted by toothmedic 1 year ago  |  4

[Story] Becoming a cuckhold part 2

Well my wife had a blast this afternoon. She had a couple over and came many many times. She had me clean her out and made me clean up the other couple which resulted in my sucking a cock for the first time.

When she was done she left me tied up. She wouldn't tell me why but proceeded to clean up. She attached a sheet to the open doorway to our bathroom and put a chair there with some restraints on it.

I kept begging her to tell me what was going to happen and she kept telling me I had to wait. Pretty soon I was begging her,"please tell me what's going to happen, I'll do anything yo want... Continue»
Posted by toothmedic 1 year ago

How I became a cuckhold part 2

Well my wife had a blast this afternoon. She had a couple over and came many many times. She had me clean her out and made me clean up the other couple which resulted in my sucking a cock for the first time.

When she was done she left me tied up. She wouldn't tell me why but proceeded to clean up. She attached a sheet to the open doorway to our bathroom and put a chair there with some restraints on it.

I kept begging her to tell me what was going to happen and she kept telling me I had to wait. Pretty soon I was begging her,"please tell me what's going to happen, I'll do anything yo want... Continue»
Posted by toothmedic 1 year ago  |  1

How I became a cuckhold

My wife was amazed that I enjoyed watching and hearing about others having her. She said, "You really don't mind?" I said not a chance it makes me very horny! She said she's glad something makes my little cock horny.

She told me she wanted to keep fucking others, did I mind? I said whatever you want. She said I am glad you said that, from now I get my cock and pussy from others? I said what does that mean for me? she said I may let you watch and I may let you clean me after I fuck, and to be nice I will jerk you off once very couple of weeks and fill you in on my exploits. I said ok just t... Continue»
Posted by toothmedic 1 year ago  |  2

[Story] How we started swinging (part 2)

Well I suggested swinging to my wife and wasn't sure how it would turn out. Well it turned out great from my wife's perspective.

She got fucked for a night and she wasn't even tired. We got into the car and she lifted her skirt and showed me her bald pussy filled with cum. She said, "oh well I forgot my underwear". I said I would turn around and go back to get it.

She said,"don't worry it's only a 90 minute ride and I won't need it". I looked at her and she just smiled and said let's go.

I asked her how she enjoyed our first try at swinging. She said she loved it an couldn't wait to d... Continue»
Posted by toothmedic 2 years ago