I've been a wannabe cuckold for about 8 years through multiple relationships. Yesterday, or rather this morning M[29]y GF[28] finally made it happen.
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While my gf and I have had discussions about the fantasy and some interesting things to try along the way (glory holes, chastity cage, penis sleeves, etc.) We had not gone as far as discussing who would be a good partner for a first time. The furthest we had gone to this point was her sexting a friend of hers letting him know that it was for my cuckolding kink.
What happened yesterday was completely unplanned. We were winding down the night watching a Diary of a CEO discussion about porn, which led to us looking up Erika Lust's website and browsing some of those videos to watch together sometime down the line. However, when I suggested making love before bed, she mentioned being too tired.
Until she got a text from the same friend she had sexted 2 years ago. We had seriously considered him for a bull before, but he had began a relationship shortly after the sexting so nothing came of it. Last night though, he asked my gf through messenger if the offer was still on. He had just broken up with his gf and needed some release.
My GF came to ask me if I was okay going through with it tonight. It was just shy of midnight and I could not believe my ears. I told her yes, and started shaking from the excitement and nervousness. He replied that he would be over in 30 minutes. Those 30 minutes passed in a blur. I remember us taking out all the potential toys they would use, condoms, making the bed, picking out her lingerie, filling up a water bottle. Her asking me multiple times if I was sure, me asking her the same. The only other communication between her and the guy was that she asked him to be dominant and rough.
The "rules" were not fully fleshed out. Just a simple, if either of us want to stop it stops and otherwise, whatever she allowed would be allowed. I then "prepared her" by fingering her, kissing her, groping her and eating her out. Soon enough there was a knock at the door.
We introduced each other, but not many other words were exchanged. I told them I would be in the living room, and for them to have fun. They quickly moved to the bedroom. Almost instantly I heard them kissing, in the back of my head, there was a voice telling me that most women would have added a no kissing rule, but this was definitely way more exciting. I heard clothes drop and soon her moans echo down the hallway, they had started.
I decided to stay where I was, jerking off furiously while listening intently to what was happening. I think he was fingering her. After a bit, more clothing fell, I think I heard the jingle of his belt and a quiet gasp from her. A moment later, I heard the sounds of her deepthroating him, and gagging on it. A rush of jealousy and arousal overcame me. It was likely he was more well hung, since she could only gag a little bit on mine. I heard him throughout catch her up on his life, interspersed with grunts when she took him deep.
When he was done, they moved on, I think he offered to eat her out, but she blurted out "I need your dick" or something along those lines. I was a little too far to hear the finer points, I started creeping closer. When I got to the doorway, I knelt down, hand on dick, and saw him plowing her roughly and hard, with her legs on his shoulders, he had a hand between her legs, rubbing her clit I think. This was a favorite position of ours, but the sounds she was making were completely alien to me. Among other things, she mentioned how deep he was. And incredibly, her legs started to shake. She was having an orgasm from penetration. She had told me it was possible for her, but I've only ever managed it with a lot of effort and a lot of help from toys. And here she was, easily cumming on his dick. As the orgasm ran through her, it also triggered his, and he grunted, spewing his cum in the condom. They lay side by side as he rolled away.
As they began some pillow talk, I started to sneak away, but stopped when I heard her mention that she "really needed that orgasm." And he bragged that it wasn't the last one she would get tonight. Then walked around the bed, folded her up and started going at her vagina lips with his fingers. I don't know how long it took, but it felt short, as he brought her to orgasm again. I came on the floor, almost inadvertently, and panicked as I left to get some tissues to wipe it up. When I returned, he was propping her up, weak from the orgasms to eat her out. He told me after they were done that he wanted one orgasm each with dick, fingers and tongue. Sadly though she was a little too out of it for this third one.
After a bit, she wanted to repay the favor by, she got up unsteadily from his face and crawled to a better position, as he repositioned to prop himself up on the pillows. For the first time I saw what he was packing as he lazily stroked himself. His hand was replaced by both of hers as she wrung him out, he was sizeably longer and much much thicker. Their voices were lower now and he asked her something I didn't quite catch, but she replied that it "had been a while" (need to remind myself to ask about it).
I decided at this point to return to the couch, and stayed there until they were fully done. After which I walked over to give props and just banter a little.
Some of the details of that conversation:
It was the first time for him as a bull, and a first for me as a cuck, and the first for my gf as a hotwife(?) not sure what she just became.
She graded him a 9/10, and that it was "exactly the kind of sex she *needed* "
She also wished he could teach me about how to use my hands and tongue (I noted that she did not ask for dick skills, and glancing over at him and his soft package that was about the size of me at my hardest, I can't help but think that it was doing things I couldn't physically achieve)
After he left, she did mention that he was definitely bigger and better on almost everything, size, stamina, loads, skills with hands and fingers, physicality (manhandling)
She did mention that she was scared that she felt no guilt about it, and that sometime around the 1st to the 2nd orgasm, she forgot this was supposed to be cuckolding and that I was a part of it (though a passive part)
I haven't had time to talk to her properly as it ended at 2:15 in the morning and she had plans this morning, but all in all, it was an extremely positive experience for everyone, she's definitely interested in doing more, and from message to cuckolding, it was a whirlwind one hour.
We've re-confirmed our love for each other, and no regrets, so I'm just excited to see where this goes.