Jenny's Sigh
By RalphieG
January 29, 2025
Kneeling on the floor, facing that wagging hard big dick of the young strawberry-blonde guy Jenny had introduced as Bruce, the woman I knew as more than a casual date, but not yet a steady girlfriend, was surely amping up our sex play this night. I hadn’t exactly imagined this scenario, but keeping to the way the raven-haired beauty had kept me so far, Jenny had digested all we had done across our past three months (or more precisely what I had allowed) and sensed this would be a natural progression.
Which, it certainly was.
Not being exclusive, I didn’t know exactly what Jenny got up to and with whom, or she who I was with. But I found right then I was slightly more than obsessed with wondering how she had found Bruce, what she might have done with this guy who couldn’t be more than about twenty-five, and how she had not only introduced him to this possible future scenario but what he might have said when she had. Probably at least bi to be standing there raging hard bouncing over me (I am resolutely hetero, which made this all the more terrible/erotic…take your pick) or willing to at least experiment as much as us, he had obviously been taken in by my high-cheek-boned, even higher-assed friend, even though Jenny and I had to have a good two decades on the guy. I was intrigued, to say the least by this guy who had surprised me by walking into my condo only a half hour ago with Jenny not saying a word and dropping trou after she had simply said “Bruce, meet Carl, Carl meet Bruce. Bruce strip, Carl get on your knees.”
Surely, I could have refused. Surely, I could have explained that talking out a fantasy is altogether different than making it a reality. But then Jenny would have no way of knowing if I could execute a “good job,” as she called it (the thought of which she said had been storming her dreams) and she’d really have no reason for uncaging me and maybe, possibly, if she was moved enough by my sucking skills, letting me finally jerk off.
That I had been wearing a cock cage for the past few months, allowed only once-a-week prostate-coming massages and that two other dates had seen me caged, surely spoke to my submissive heart. Of course, this was a heart I had no idea beat so loudly until Jenny suggested the cage and promised all the fun we’d have with me being in chastity for her. One of the women who had seen the cage loved the idea and claimed she had never had her pussy eaten so fantastically across the three dates we had had so far. The last two times she had also taken a belt to my ass as I ate her. That I left sore, balls purple, complaining about the cage on me even, seemed to make her as happy as it did Jenny. The only other date I had over the course of ninety days lasted only slightly past a second dinner; when the petite black girl slipped my pants off, and saw the cage, she simply recoiled over something she said was just “too fucking weird, man.”
Regardless of these two, one positive and still going strong, the other negative ending quickly, the possibility of sweet bliss that possibly awaited me was worth the price I’d have to pay right then. As they had been for quite some time, but always grew more so when I was aroused, my balls pulled, the tip of my cock tingled and as I lean in to take Bruce between my lips, I heard Jenny sigh from over me.
That sigh was worth everything.
Which, it certainly was.
Not being exclusive, I didn’t know exactly what Jenny got up to and with whom, or she who I was with. But I found right then I was slightly more than obsessed with wondering how she had found Bruce, what she might have done with this guy who couldn’t be more than about twenty-five, and how she had not only introduced him to this possible future scenario but what he might have said when she had. Probably at least bi to be standing there raging hard bouncing over me (I am resolutely hetero, which made this all the more terrible/erotic…take your pick) or willing to at least experiment as much as us, he had obviously been taken in by my high-cheek-boned, even higher-assed friend, even though Jenny and I had to have a good two decades on the guy. I was intrigued, to say the least by this guy who had surprised me by walking into my condo only a half hour ago with Jenny not saying a word and dropping trou after she had simply said “Bruce, meet Carl, Carl meet Bruce. Bruce strip, Carl get on your knees.”
Surely, I could have refused. Surely, I could have explained that talking out a fantasy is altogether different than making it a reality. But then Jenny would have no way of knowing if I could execute a “good job,” as she called it (the thought of which she said had been storming her dreams) and she’d really have no reason for uncaging me and maybe, possibly, if she was moved enough by my sucking skills, letting me finally jerk off.
That I had been wearing a cock cage for the past few months, allowed only once-a-week prostate-coming massages and that two other dates had seen me caged, surely spoke to my submissive heart. Of course, this was a heart I had no idea beat so loudly until Jenny suggested the cage and promised all the fun we’d have with me being in chastity for her. One of the women who had seen the cage loved the idea and claimed she had never had her pussy eaten so fantastically across the three dates we had had so far. The last two times she had also taken a belt to my ass as I ate her. That I left sore, balls purple, complaining about the cage on me even, seemed to make her as happy as it did Jenny. The only other date I had over the course of ninety days lasted only slightly past a second dinner; when the petite black girl slipped my pants off, and saw the cage, she simply recoiled over something she said was just “too fucking weird, man.”
Regardless of these two, one positive and still going strong, the other negative ending quickly, the possibility of sweet bliss that possibly awaited me was worth the price I’d have to pay right then. As they had been for quite some time, but always grew more so when I was aroused, my balls pulled, the tip of my cock tingled and as I lean in to take Bruce between my lips, I heard Jenny sigh from over me.
That sigh was worth everything.