Cuckolded by Vacation Pics

My Dominatrix has been cuckolding me. Our dungeon sessions go like this… I strip nude. She binds me to a chair with expensive silk ropes. She teases me by tracing her nails around my nipples and chest, then down to my thighs, while my cock desperately twitches. She tells me I have to pay for yet another vacation for her and her boyfriend, buy her more bikinis from Reef or Billabong or Wicked Weasel websites. She will show me pics from the vacation during the the session I schedule after her trip. The pics are on her phone. She won’t send me any of them. She will show them to me up close, so close I want to cry. I feel weak looking at her with her perfect muscular manly boyfriend. My cock starts dripping, my balls aching. I know I can never have her. I am a skinny wimp who works in Tech. I make a lot of money. Even escorts I book for sex come over to my place, hang by my pool, text their friends, take my money and tell me to masturbate. My dick is average length, but very skinny, like a finger. My Mistress told me when she looked at my dick, that all it would need is a fingernail to fulfill its true form.

I don’t like physical pain, but psychic pain is what my Domme deals out. I have to take it. Her boyfriend works at a surf shop and is an avid surfer. So most of the vacations I pay for are to surfing destinations. Sometimes my Mistress will sing “Surfing Safari” by the Beach Boys to torment me into paying for another vacation. She sings the song in a slowed down tempo in her sexy alto voice. She’ll change lyrics around to sing things like, “Pay for another surfing safari for my boyfriend and me!!” And laugh at me. Because she knows I will. I haven’t had a girlfriend in years. My Dominatrix cuckolds me and nothing else excites me sexually as much as being cuckolded by her. I am so desperate that I am going to ask her to Snapchat the cuckolding pics during the vacation so I can masturbate to them while she is away. Perhaps she has a premium price in mind for this privilege.

Cuckolded at the Glory Hole

Cuckold Mistress Sara, Let me add a humiliating write-up to your cuckold blog about what happened to me at the glory hole. Well this glory hole is actually an adult bookstore with booths in the back for gay sex. I’m not even sure why people call these places adult bookstores, because I’ve never seen one where books are sold. So at this place there are discount bins for adult dvd’s since everyone streams porn online instead. There are some shelves with magazines, lots of sex toys, cheap lingerie, lube and condoms. Well I happened to hit the ABS when it was deader than a doornail. No one was even in the back. I asked the clerk, a black chick with a huge weave, if it was a slow night. She said yeah whiteboi then went back to texting on her phone with her super long talons. Then this black guy walked in, huge dredlocks, smelled like he had been smoking weed. Bae he said then he and the girl locked into a slow grind. What time you get off this place he asked her. Two more hours she answered. Fuck he said. I need this job bae I can’t just lock up and go even if it’s slow as a motherfucker the girl lamented.

Then the black guy said whiteboi watch the counter here while me and my girl go in the back. He don’t know how to use the register or the credit card machine the girl protested. They have to pay in cash, the guy ordered. Don’t let anyone in the back she said, tell them the back is closed for cleanup. They went into the back and I went behind the counter. This place has cctv surveillance of the booths! OMG! That meant any clerk could see all of the booth action. So I watched them fuck, omg, his cock was so huge. My reverie was ruined when the store’s front door opened and a little bell chimed. It was some older fat white dude. I acted like the clerk and greeted him and asked him what he was interested in tonite. He said he was going to the back. I told him it was closed for cleaning. I told him it had been super slow and someone was cleaning it. What the fuck, place never gets cleaned he said. At least buy something I said. Are you that desperate the guy asked. It’s cash only I added. The credit card machine is down. He bought some condoms for cash and left.

I then decided to jack off to the black chick and her bull having sex in the back. I came quick because that’s one of my humiliating weaknesses besides having a small dick. I licked up the cum.

A few minutes later the black couple came out, looking all high and like they’d just had sex. Did anyone come in whiteboi? Yes a guy bought condoms and I showed her the ten dollar bill he paid with. She slid the bill into her jeans pocket. Smells like cum out here. Derron does it smell like cum she asked? Fuck if I know he said I put enough cum in you to flood out this joint. I asked if I could leave and they said yeah get the fuck out whiteboi. And started making out. I got to my car and jacked off again feeling like such a cuckold.

College Cuckoldress

Mistress,

Here is another pathetic confession for your blog. Back in college I had one of the hottest girls on campus as my girlfriend. Well I thought I did. Early evenings after dinner in the cafeteria, we would do our homework, well I would do hers and then finish mine later. I was so horny I tried to have sex with her and she refused saying that she was a virgin, she wasn’t ready for sex and that we needed to wait. After that, she would let me lick her pussy, but I had to keep my clothes on and I couldn’t jerk off in front of her. And then she would tell me to go back to my dorm room and do it there, I wasn’t allowed to masturbate in front of her. She thought that was rude. I was willing to wait for Tamara to be ready for sex. I respected that she was a virgin. In fact I thought it was good that she didn’t have any sexual experience. Because I knew my dick wasn’t big compared to guys I saw in the locker room in HS and in college. But I had a great body, was an athlete (lacrosse), girls told me I was cute etc.

The college I was going to is a huge university. But no matter how huge a university is, it’s a small world after all as the Disney song goes. Word soon word got back to me that my beautiful girlfriend Tamara was fucking black guys. I couldn’t believe it. I thought it was a cruel joke played on me by guys who were jealous I had such a beautiful girlfriend. But then I stalked her one night after we were done studying, following her from her dorm and saw her meet up with a black stud football player. OMG I went back to my dorm room and jacked off to that. I had no clue I was a cuckold. I kept acting like Tamara was my girlfriend, I kept doing her homework, I kept licking her pussy that black guys were fucking. She kept telling me no sex, and how she might stay a virgin till she got married and I just pretended it was the truth. I could have let her go and found another girlfriend but I was so into this girl and the powerful and exciting sexual feelings I felt.

I didn’t know I was a cuckold. I didn’t even know the word existed. Then one night about seven years ago I saw this video of Shane Diesel fucking some hot blonde while they both laughed at and humiliated the blonde’s husband. The video was a cuckold video. I began watching cuckold videos all the time. And I looked up cuckolding online, which was how I originally found you on your Cuckoldress.com blog. OK you probably think I am naive, but I was only 23 then. As for my college cuckoldress girlfriend, Tamara broke off with me at the end of the semester and got herself another white boy cuckold for the next semester. Luckily I graduated ahead of her so I didn’t have to continue to bear the humiliation of what she did to me in front of my friends, but I still jerk off to the cuckold humiliation to this day. And now I can follow her on social media. Her twitter has so many links to rapper videos and references to hot black rappers and athletes. And she is always hash-tagging black cock related or attention whore hash tags on twitter like #eggplantfriday (pics of big black dicks) or #whitegirlwednesday (pics of hot white girls who love BBCs).

Cuckold Bitch

My cuckold confession is unbearable. Many cucks are not allowed to have sex with their hot wives or girlfriends at all. This is only natural. However, on the flip side, having sex with your hot wife when you are a cucky might be worse than no sex at all. My wife will occasionally have sex with me as her cuckold husband, but she only gives me pity fucks or humiliation fucks. This means I can only fuck her when she lets me, and this is how it happens… After she has been fucked by one of her two BBC boyfriends, and if she’s in the mood to humiliate me, she will let me fuck her. She doesn’t make her black bulls use condoms, so her pussy is always filled with their cum and it’s stretched out from their massive cocks. When I put my little 4.5 inch dick inside her, my tiny dick feels like it’s swimming in her creamy pussy. I can’t really get off and she knows it and she laughs at me and tells me to just use their superior sperm to stroke with and finish up. Then she makes me lick up her creampie with my tongue. She will often text one of them while I’m cleaning her pussy to advise them what I’m doing. One time she showed me the text response from her black stud named Romulus who texted her back: Good bitch.

Now my wife will tell me “good bitch” when I’ve done things that please her like cook steaks for her and one of her bulls on the grill, buy her a spa certificate, lick her pussy for hours or buy another bottle of her favorite perfume, Tom Ford Black Orchid. It’s almost $200 a bottle and she only wears it for her bulls, not for me.

Sugar Daddy Cuckold

From the Mistress Cuckold…

I recently met up with a cuckold who told me he was on Seeking Arrangement and wanted to speak with me in person about cuckolding, since we only lived an hour apart. He was in a critical situation, he said. We arranged to have coffee at an upscale cafe and he paid me for my cockold consultation time. He told me he signed up for Seeking Arrangement (a sugar daddy website) as some type of revenge against his wife, who was cuckholding him. She was no longer having sex with him at all. She was only having sex with well hung men she met on Tinder or Adult Friend Finder. He informed me that younger girls in college, 19 – 22, were at first interested in a sugar daddy relationship with him when he would email and chat with them on the site. He showed me the listing for one girl, a cute blonde Barbie type who, at first, wanted $1K a week from him. Her terms were that she would have sex with him twice a week for $1K. He negotiated it to $500 a week for a one time hook up. After a few hook ups, she laughed and told him that having sex with him was easy, because his dick was so small and he only lasted a few minutes. I also had to laugh at that. I said: “Did you really think you’d be able to escape being a cuckold? Even girls in college are going to cuckold you and take your money and laugh at you. Your dick is small and you cum quick. You’re a Sugar Daddy Cuckold.”

He had to hang his head and admit that this was true. He had met with other sugar babies from the site who didn’t even want to have sex with him, they wanted him to take them shopping. He said maybe they’d give him a hand job after or watch him jerk off after the shopping spree. Another sugar baby was too afraid to meet him alone the first time and brought her girlfriend to the hotel bar and then they went up to a hotel room for sex. Once she saw how small his dick was she called for her friend to come out of the bathroom to see his tiny dick and they both laughed at it. I told him he should continue being cuckolded by these college girls, since it was what he deserved anyway!

Cuckold Faggot

Sara, I’m mortally embarrassed about my cuckold situation. I broke up with my girlfriend I found out she was cheating on me. She had also been borrowing a lot of money from me and would laugh when I asked her to repay it. She also laughed when I broke up with her and told me good luck with finding another girlfriend, ever! And she even gave me the small pinky wave. I thought she had picked up all her stuff that was at my place, but turns out she had forgotten some lingerie. I was planning to throw out her slutty bras and panties and garter belt and stockings, but she texted me that she was going to be picking up the lingerie to wear for her man. I put everything in a shopping bag and hooked it around the outside doorknob of my condo so I wouldn’t have to deal with her. I’ll call her Jessica in this letter to you. When Jessica came by she rang the doorbell anyway, but I didn’t answer. What kind of wimp am I? I peeped through my mini-blinds and saw her leave in a car driven I assume by her new boyfriend. She then texted me a photo of a huge dick in her mouth. I assume that was her new boyfriend’s cock. I jerked off to that pic immediately. A few minutes later, she texted, so did you cum yet faggot? She told me to Google Wallet her some money and she would send me more pics of his cock. She wanted $100. So I sent her the money. Was she doing this in front of her new boyfriend while they were driving back to his place? Was her boyfriend laughing at me? Why did Jessica even date me except I would buy her things, mostly clothes, heels and lingerie and she would borrow money for her bills that she didn’t pay back?

Now I’m such a cuckold faggot loser. All I jerk off to are pics of her boyfriend’s cock. I’m worried that if I’m becoming a faggot, I won’t be able to go back to just being a wimp. His cock is so amazing I can’t help it.

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