I can’t believe I’m typing this but I recently had my first cuckolding experience. My girlfriend, Jessica, and I couldn’t be happier with the experience and both found it amazing!
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First off, Jessica is a tall blond (5’10” 170) with curves in all the right places. She always thinks she’s fat but I absolutely her phat ass and huge tits. We have a very active sex life but I’ve always felt like I had a hard time getting her off via conventional means……
What started the whole thing was she’d gotten a new dildo which is quite a bit larger than her others and I mentioned one night that she seemed to really like her new dildo and I couldn’t figure out what was so different about it lol. She blushed and tried to change the subject but when I pressed her on it she admitted that she “likes the way it stretches me, ok?” I found it super hot and couldn’t contain myself anymore so I asked her “have you ever taken a big cock?” She told me “no, but if I’m being honest I’ve always been curious about it.”
This piqued my interest so I asked “What makes you curious?”
She went on to tell me about her college roommate who constantly talked about the guys she was sleeping with and who raved about the big cocks she fucked, encouraging my girlfriend to try one out. She even showed Jessica pics of a couple big ones, which Jessica admitted turned her on at the time. I then asked her if she’d ever take a big one and she asked “what do you mean?” I explained my interest in the whole thing and after some questions she agreed to it and said “that actually sounds really hot.” We had amazing sex that night and couldn’t keep our hands off each other the rest of the week. She even teased me with her big dildo, pretending she was getting piped out by another man.
Jessica put up a tinder profile and got a lot of suitors (no surprise). After wading through them, she clicked with one guy in particular, Ben, who knew the whole situation and was cool with it. He sent her some dick pics eventually and neither of us could get over how big he was. It was literally almost the size of his forearm!
We arranged things over the following days and met up at a hotel and Jessica was super nervous as we were waiting. She was all dolled up in red lingerie and looked incredible. We went all out too, getting champagne and everything.
Ben arrived and honestly, it was kind of awkward at first. What eventually broke the ice, oddly enough, was Jessica ripping a huge belch lol. “Oh my god, that was the champagne!” We all laughed and he complimented her skills and she apologized and said “I forgot we had company haha.” She’s actually a really gassy person and burps insanely loud around the house all the time but tries to keep them quiet when we’re around new people.
After a little more chit chat, Jessica surprised me by saying “I’m so horny, can we get started?” I was taken aback how blunt she was but found it really sexy seeing a confident streak in her. She went over to Ben and began taking off his pants. Once she got them down, his massive bulge was on full display in his boxers. Jessica got his boxers down too and out popped his cock which swung down halfway to his knee, still limp. “Holy shit!” she exclaimed. He grinned and asked her to suck him. She proceeded to give him insanely sensual head (unlike anything she’d ever done for me) commenting repeatedly on his size as he grew to full size. She lovingly cupped and licked on his balls and up and down his shaft, trying her best to deep throat him. He got her bra off and caressed her tits. Then he got her on the bed and ate her pussy for a while, bringing her to her first orgasm. He asked her if she was ready for his big dick and she enthusiastically responded “Yes!”
She rolled a condom on his dick and remarked on how hard it was to get it on. The emotions flooding through me were crazy and was stomach was in knots but I was rock hard. She squirted some lube on him and sensually rubbed it over his shaft. As she prepared to mount him, she said “I don’t know if I can take all of this.” He gently ran his cock across her pussy then plunged in. Jessica immediately began moaning like I’d never heard before and started shaking. I didn’t know what was happening and asked if she was ok. She responded by crying out “I’m cumming!” and having a full body shaking orgasm. The mixture of emotions in the moment was crazy, knowing she was getting a level of pleasure I’d never given her, and I came in my pants right then. He grabbed her ass and started pounding her, keeping it up for ten minutes or so as she had a number of subsequent noisy orgasms.
They switched into missionary and he went back to pounding her. She went right back to cumming over and over, shouting out that he “was so deep!” I came in my pants again as she got caught up in the moment and told him “I’m in love with your cock.”
He moved her into doggystyle and unleashed a few huge queefs as he started going to town. Her ass cheeks clapped beautifully as he pounded away and she immediately began moaning in abject pleasure. She came so many times as he fucked her relentlessly and smacked her ass that she collapsed into a shuddering heap eventually and had to take a break. As she rested, he taunted me by stroking himself and saying “she’s never had a cock like this.” The humiliation was so hot but so palpable and I came in my pants for the third time.
After the break, he got her in prone bone and kept fucking her like crazy. He then dumped a huge load over her ass and told her to lap it up which she did gladly. They cuddled for a while and chatted afterwards. She thanked him for the fuck of her life and he got her to admit that size definitely mattered. She apologized to me but I told her it was ok, it’s obvious lol.
They had sex twice more that night lol!
After he left, I spooned with Jessica and we talked about the experience. I told her how hot I found it watching her get fucked and confessed that I’d cum in my pants multiple times. She told me that was hot to hear. I asked her if she wanted to do it again and she immediately blurted out “I have to. It was so good.”
I asked what was so good about it.
“I’ve never cum like that. I didn’t know it was humanly possible haha.”
I was so turned on in that moment I had to fuck her and was greeted to a beautifully stretched out pussy as I entered. She told me should could barely feel me as I pounded her as hard as I could and came in two or three minutes.
We’ve already scheduled another meet with Ben….
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