Milwaukee Cuckold’s Wife And The Crossdresser free porn video

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Judy 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 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.”

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 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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Jingle bells! Jingle bells! Jingle all the way! The sound of the holiday song hit Gunther's ears like an ice drift on the open sea. He tried to open his booze-laden eyes to see who was making the racket and saw it was the blasted elves again. Those holiday-enthused cretins were so full of Christmas spirit that they made a nuisance at this time of year as far back as he could remember. He wanted to shout out for them to cease and desist before he made them into little pieces of elves all...

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Milwaukee Cuckhold and her disabled husband

I had been having an issue with my foot and was stuck at home for most of two months and was going stir crazy and was still looking at another month at least. Judy felt bad for me but wouldn’t leave me alone and stayed at home with me. Finally, summer camp came up and the k**s were going to be gone for a month. Judy kept asking me if I wanted her to jerk me off. I kept telling her no that she should go out and have fun.She felt so bad for me that one day when I had a doctor’s appointment she...

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Andrew Running Part 1 of Andreas Stand

Andrew Running (part 1 of Andrea's Stand) Chapter 1: Running I called my Aunt Clara from the bus station. She didn't seem that surprised to hear from me and when I explained why I was there she told me to walk a couple of blocks to the local diner and get myself a cup of coffee. She'd pick me up in about half an hour. I sat and sipped chocolate milk and tried to eat a pastry while I glanced nervously out of the window waiting for my father to show up and force me into his...

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Candys Dandy

by Millie Dynamite Jaden and I meet a few weeks after he transferred to the Naval base just outside of town. I sat on a bar stool sipping my Pappy Van Winkle when this tall African-American man in full dress uniform sat next to me. He whore captain’s bars. He possessed an air of authority. I nodded to him when perched on the next stool. He returned my nod with his own acknowledgment, in a deep voice he said, “Yo.” He spoke without looking at me. “I’ll have bourbon, make it a shot of Evan...

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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

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Strange RelationshipsChapter 10 Armand Mixes in the Hernandezs Affairs

Armand Wilson sat in his home office/study sighing. From the office, things had looked pretty good; business was on track, and Sharon appeared to be handling her new situation well. But in the car on the way home, Armand began getting bad vibes, and when he arrived at his mansion, things were even worse. Everyone on staff was walking around as if on eggshells. It took Armand about twenty minutes' worth of snooping, but the situation resolved itself -- the Hernandez' quarters were an armed...

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Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

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CANDY FINDS HER SON HANDY AND DANDY

by Oediplex 8==3~ The sweetest mom discovers her boy is both convenient and delightful. [She also recounts when her dad fucked her at nineteen!] Like the name of Madame DeVille's moniker, Cruella, some names fit the personality they are bestowed upon. Disney came up with that evil woman's apropos handle. My mother's folks named their only child, a daughter, Candy. This was shortly before the infamous 1968 movie was out. Though there were aspects of mom that paralleled the...

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Confessions 5 Alessandra fools Father Peter

Father Peter of St. Johns Cathedral in Duketown has a fame for tolerance of sexual sinsHis virtual girlfriends from the net flock from everywhere to do their Confessions at himAlessandra is a local girl, attending mass at Sundays sometimes, when I lead the ceremonyAlessandra prefers private talks though, sometimes she gets a bit too friendly with FatherAlessandra plays a great girlish game with her beloved spiritual Father PeterAlessandra has confessed earlier at me, always being very honest,...

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Andersonville 21 Sins of the father Sins of the son

"Good morning, Miss Anderson," Crius said in a formal tone. "Please, call me, Linda," I replied. "Only if you call me, Crius," he answered. The Titan God smiled, but I detected no warmth to it. "Okay, Crius." I returned his smile with some reservation. I couldn't put my finger on it, but I didn't feel at ease with him. When he had asked me out to breakfast, I had been tempted to say 'no', but my curiosity had gotten the better of me. "So, what can I do for you?" "Nothing,...

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Androids of Evergreen pt3 Athena

Although Tom liked the quiet moments with her, today it was hard to resist his want to take Chloe there on the couch. He hadn’t fucked her in over 24 hours now. He was holding off and building up his cum for when his new daughter arrived. It was supposed to be any time now, but it was still frustrating having such a great piece right in front of him and having to hold off fucking her. He kept reminding himself that he would be blowing his load inside his new daughter very soon. Then, he would...

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My cheating wife Wanda went black

I came home from work unusually early, I made my way to the kitchen to get something to drink. I heard some weird noise coming from up stairs on the second floor where the bedrooms are and decided to go up and find out what it was. When I reached the top of the stairs I could hear the sounds coming from our bedroom, they sounded like sexual sounds. Quietly I approached our bedroom door that was left wide open and peeked inside to see what the fuck was going on. I was totally blown away when low...

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My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

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Old Mandingo Bosses Impregnate My White Teen Wife Part One

Many of us probably grow up believing in the fundamental goodwill of other people. I know that I was raised to think that most people are honest and could be trusted to do the right thing. However, this story describes a couple of situations in my life where I was taken advantage of by others, with very significant consequences.My name is Ed, and I was born and raised in an average, middle-class home just outside of Montgomery, Alabama. I am reasonably intelligent but was only a mediocre...

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Thangaiku Theriyaamal Amma Magalai Oothen

Indru tamil kama kathaiyil ilamaiyaana magalum pinbu vithavai ammavaiyum eppadi usar seithu matter poten endru ungaluku solugiren. Suvarasiyam athigam irukum kama kathaikul selalam vaarungal, en peyar karthik. En veethiiyil oru pen ilamaiyaaga sexiyaaga irupaal, avalai thinamum sight adithu kondu irupen. Thinamum aval kalluri sendru varum pozhuthu iru velaiyilum sight adika arambithu viduven. Aval peyar nandhini vayathu 21 irukum, avaluku veetil aan thunai kidaiyaathu. Veetil oru amma iru...

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From Candace to CandyChapter 7

Well, now it's time for school. Candace and I go to a small high school, not private, but because we are so rich, it is not exactly public either. The students have been screened by my fathers' security teams; they are all exceptionally bright, well mannered, not prone to causing trouble, and to add ice cream to the pie, all are very good looking. There are 40 students, 20 boys and 20 girls. When the school was larger it had state champion quality teams in boys basketball, girls volleyball...

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Milwaukee Cuckold and the Principal 2

Judy didn’t bother putting on her underwear and just put her skirt and blouse on. She went over and gave Principal Jefferson a kiss goodbye. It was no simple kiss they were virtually going at it again. When they finished Judy took my hand and lead me toward the door, she turned back and said, “we’ll see you tomorrow night” Principal Jefferson just smiled back.We got into the car and it was now dark out and there was only one other car in the lot, which I assume was the principals. Before we...

2 years ago
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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 family. 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...

4 years ago
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Milwaukee Cuckold and the Principal

My wife who had been working as a teacher’s assistant at the school for about 6 months was saying how much she enjoyed it. She was surprised though because she was getting mixed vibes from the principal. One evening she came home and said the principal had visited the classroom she was assisting in and rubbed her shoulders and told her how happy he was she was part of the team.I laughed and said, “maybe he is warm for your form.” She said, “I’m a 50 year old BBW and he is about 30 and sexy as...

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