

Hello,
My girlfriend's name is Anna. We started dating in our mid twenties and we're now in our late twenties. Anna is incredibly sexy but also the type of girl who'd rather wear sweatpants than skirts and was more comfortable in a baggy t-shirt than a tube top. She doesn't show off her body too much but she is not prudish by any means. Her body count was around twenty at the time that I met her (while mine was just two). And almost all her hookups had been one night stand type events. She had only had a few longer term boyfriends before me.
Sexually, Anna is very open minded as well. Though I could never do it very well for her, she is actually very into bdsm and bondage type play. She likes being tied up, teased, and used thoroughly. Though her normal attitude is very confident and bold, she enjoys playing submissive and being dominated.
I told her about my cuckold fetish early on and she was generally receptive to it. It was during lockdowns so we didn't immediately seek out any bulls for her. But we did role-play a variety scenarios together that helped us determine our likes and dislikes. Anna recounting her previous sexual experiences while I licked her pussy was one of our favorites and we did it regularly. And when she ran out of stories from her past, she'd watch porn while I kneeled under her desk and licked her. Anna also tried to humiliate me in a variety of ways including comparing my cock size to previous men she'd been with, making me wear her panties, and giving me infrequent but quick ruined handjobs where I'd cum prematurely but she'd let go right when I started cumming and laugh at me. She even peed in my mouth once while I was licking her pussy in the shower and made me swallow some of her pee before letting me continue to lick her more.
Anna enjoyed this control that she had over me but it obviously wasn't fully satisfying for her sexually. And though I had never been able to fully ravage her, the fact that we stopped having penetrative sex after I first mentioned my cuckold desires didn't help. She had a dildo that was inches larger than me but that only could do so much for her. Seeing her frustration, I suggested that we finally move past role-play and find an actual guy for her. Anna was encouraged that I made suggestion and agreed to try.
In her search for a man, Anna wanted to try to kill two birds with one stone. The first bird was just achieving my cuckold fetish and having her hook up with another man. The second bird though was to find a guy with bdsm experience who could really dominate her. I was obviously game for both. The thought of her submitting herself to the sexual whims of another man was completely thrilling to me.
She started by putting up ads and profiles for herself on a few different websites. She didn't show her face in the pics but she included her body pics of herself in a few different outfits along with her first name and basic stats. She got tons of replies almost immediately but very few caught her interest.
Eventually though, one guy did stand out. His name was Mike. He was in his forties and had a big 8+ inch dick. That obviously stood out to Anna but what made Mike unique was his extensive bdsm experience. His response to Anna didn't include any face picture but he shared lots of pics of his body, dick, and of him conducting various bdsm activities on other women. The women were all gorgeous and bound in a variety of ropes, handcuffs, and other restraints. I could tell that Anna was immediately starting to imagine herself in those same situations.
Anna and Mike corresponded frequently over the next couple weeks as they got to know each other. Anna revealed that she was in another relationship but told Mike that I had a tiny dick and couldn't satisfy her at all. I was literally licking her pussy and jerking off as she wrote that part. She also talked about her submissive desires and need to be dominated and objectified thoroughly 'by a real man'. Mike's responses were always clear and confident. He shared stories of previous women he had played with and how he helped them achieve their desires. Anna was smitten with everything he said and even masturbated to some of the photos he shared. Eventually Anna told Mike that she wanted to meet and shared her face pic so he could see what she looked like. Mike responded with his own face pic and they agreed to meet at a coffee shop the next day.
The next morning, Anna took a long shower and completely shaved her legs and pussy. After her shower, she picked out a basic t-shirt and jeans to wear. Mike requested that she not wear a bra so her thin t-shirt would definitely be showing off her nipples. And another request from Mike was that she write SLUT on her chest under her shirt. Standing in front of me topless, I took a marker and wrote slut on her chest just above her boobs in large letters. Anna was giddy and admitted that she did in fact feel like a slut. She then threw her shirt on and told me to not masturbate until she came back. She said she'd text me updates as often as she could. I gave her a kiss and wished her luck and she smiled while quickly walking out the door.
A half hour later, I got a text from Anna saying she was at the coffee shop waiting for Mike. Then an hour later, she texted again saying that her coffee day with Mike went great. I asked what they talked about but she didn't respond immediately. Ten minutes later, she said she on her way home.
When Anna arrived back, she was still flustered by her meeting with Mike. She headed straight to the bedroom and took off her clothes. SLUT was still written clearly across her chest. She sat on the edge of the bed and asked me to lick her while she told me what happened. I eagerly followed her request and got on my knees in front of her. As I licked her, she said that Mike was very handsome and she was instantly attracted to him. After exchanging pleasantries, they had a very frank conversation about Anna's sexual experiences and desires.
Mike asked specifically what was lacking in her current relationship with me and Anna explained to him that there were both physical and skill based limitations to my lovemaking (not untrue). After they were done with their coffees, Mike walked her to her car. But before she got in, he pinned her against the side of the car and kissed her passionately. She reciprocated his tongue and they made out for a minute while softly groping each other. Then Mike backed away and asked Anna to show him that she had followed his commands. Anna then lifted up her shirt to show him her bare boobs in the middle of the parking lot with SLUT written across them. Mike was apparently pleased with her obedience. He then gave her one more homework assignment to complete before their next meeting. She had to take a photo of herself completely naked holding a ruler or tape measure extending up from her pussy to her belly button.
As she told me everything while I licked, she orgasmed at least twice. She eventually pushed my head back and started masturbating herself with her fingers and orgasmed a third time. After she had subsided, she looked down at me on my knees. She asked me to get a ruler and said we could take the picture for Mike immediately. I looked around and eventually found an old ruler we had. As I handed it to her, she told me to get naked. I quickly disrobed and stood naked in front of her with an already rock hard erection.
Anna then took the ruler and held it against my dick. Measuring me up, she then laughed while just saying '4 inches!'. I was humiliated. She then held the ruler against her stomach while handing me her phone. I then got into position to take the photo. Anna posed with her finger pointing to the 4 inch mark on the ruler as I snapped the shot. The 8 inch mark was nearly to her belly button and I was already imagining Mike's dick going twice as far inside of her than I ever had. I then asked Anna if I could masturbate. She said yes but acted impatient and told me to make it quick. I started stroking myself while Anna took her phone and messaged the photo to Mike. And by she hit send, I already came.
When I got home from work the next evening, Anna was almost ready to head over to Mike's house. She said she didn't know when she would be home but would text when she got there and when she was leaving. She reminded me not to masturbate until she got home and I promised I wouldn't.
By the time I got her text that she had arrived, I was already a bit of a wreck imaging all the things that Mike would soon do to her. I responded wishing her luck (not being sure what else to say) and then waited for the next couple hours. Around midnight, I got a text from Anna telling me that she headed home. She told me to naked and ready for her in the bedroom. I stripped off my clothes and waited in the bedroom for her. It felt like forever but eventually she unlocked the door and walked in to find me.
She told me to lay down on my back on the ground and I complied. She took off her clothes and then proceeded to walk around me. I could see that her body had more writing on it. SLUT was still vaguely visible across her chest from the previous day but she now had MIKE'S PUSSY written below her belly button with an arrow down to her vagina. But her pussy was covered completely with a piece of tape. And on her lower back, another caption and arrow claiming that her asshole was his as well. Before I could say anything, Anna proceeded to tell me about all the things that Mike did with her.
First, Mike had her strip completely in his doorway before letting her into his house. She had to fold and leave all her clothes on his door step. Once inside, he then guided her to her knees and put a collar and leash around her neck. He then led her around his house on her hands and knees, pulling her by the leash the entire time. They eventually arrived at a bdsm room in the back corner of the house. He sat her on her knees in the middle of the room and then handcuffed her hands behind her back. He inspected her body closely before taking his cock out right in front of her face. Anna tried to take it into her mouth but he told her to beg for it first. She begged for minutes before he eventually moved forward and let his dick into her lips. She said he was huge and tried to suck him as best as she could but he eventually took control and held the back of her head while fucking her mouth aggressively.
Eventually Mike pulled his dick out of her mouth. He put a blindfold over her eyes and a ball gag in her mouth before pushing her forward onto her chest. Her hands were still cuffed behind her back and her ass was sticking straight up in the air. He then took a spreader bar and attached it to both of her ankles while forcing her legs to be spread apart. Anna felt completely exposed and vulnerable. She felt him drip lube into her asshole before sticking a butt plug in it. Anna had never used a butt plug before. She said it hurt at first but then felt incredible once she was use to the size of it. Unexpectedly, Mike then spanked Anna several times across both cheeks. She yelped each time. Then she felt him kneel behind her and insert his dick into her pussy. He grabbed both her hips and pulled her violently back against his crotch and sinking his cock deep inside of her. She said he felt incredible and she orgasmed continuously nearly the entire time but the ball gag muffled her screams of pleasure.
After he was done with her pussy, he then pulled the butt plug out of her ass and positioned the head of his cock against her asshole. He pushed in slowly as she moaned. Anna had done anal with other guys before but never with me and not for several years (and definitely not with a dick of MIke's size). He was gentle at first but eventually worked his way all the way in. Then he started fucking her with steadily increasing pace. As he fucked her ass, he undid her handcuffs and removed her ball gag and blindfold. He then used the leash to pull Anna up so she could kneel on both her hands and knees. Anna started to moan in pleasure and then surprisingly had her first anal orgasm ever.
Mike then pulled out and flipped Anna around onto her back. Her legs were still bound by the spreader bar which he pushed up so that her ankles were close to her head. He put his cock back into her pussy and started to fuck her once again. Anna orgasmed a couple more times before starting to beg for his cum. Mike obliged and shot his load deep into her pussy. And once he pulled out, he took a piece of tape and covered Anna pussy so that no cum could drip out. He unhooked the spread bar and collar and stood Anna up. She said she felt drunk and could barely stand after the experience. He took a marker and claimed his pussy and asshole on both sides of her body before leading her to his front door. Holding her against the door, he kissed her passionately for a minute before opening the door and pushing her out into the cold. Anna then gathered her clothing and put it on hastily before driving home.
As Anna completed her story, she was standing right above my head. She then got down and straddled my face with her knees. Her pussy was inches from my face as she peeled the tape off her pussy and then quickly pressed it down against my mouth. I momentarily tried to resist but she grabbed my hair and commanded me to lick her clean. I did and then quickly tasted a flood of Mike's cum and Anna's pussy juices flow into my mouth. It was simultaneously the most humiliating and exhilarating thing that had ever happened to me. I swallowed as quickly as I could and then licked Anna's well used pussy until she was satisfied. She then got back up and used her foot to press my boner down against my stomach. She pushed it forward and back a few times and then I erupted across my entire stomach and chest. Anna just laughed and then went to the bathroom to clean up.
Anna plans to continue meeting Mike. I'm both excited and scared for what will happen next.
Cuck - mahmiss@tutanota.com
Other Couples' Blog Submissions:
My Girlfriend thinks I don't Know
The Origin of my Cuckold Fetish
My Wife at a Conference with a Built Man












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