I find the willingness of young women allowing themselves to be taken by older men fascinating. The allure for the guy is obvious, but the girl's attraction is what fascinates. My own occasion of being made a cuckold by a significantly older male:
As part of foreplay , I once asked my wife to describe a fantasy of having someone fuck her. What I failed to take into account in making that request was that she actually had very little in the way of sexual imagination. Since the “fantasy” she described lines up exactly with a guy (middle-aged, conference, bar, hotel) that she had taunted me about, I think what she really described was the time this guy triumphed in his efforts to take her into his bed.
There was this middle-aged guy in her line of work who was a fixture at their business conferences, probably about 50. This was a guy of significant prestige among his business associates. But she said he had a reputation for hanging out in the hotel bar and either getting ...... or hitting on the younger women at the conference, apparently with some success. And in line with the taunting she liked to do to make me uneasy about what was going on behind my back, she she always added that a number of times he had talked her up, too. On the occasion she related, she was hanging out in the hotel bar, uncharacteristic behavior since she didn’t drink much. But the guy was handsome enough, and she may have heard from other girls about his skills with his cock.
So, she said that since this middle-aged guy was persistent in hitting on her in the bar, she decided this time that she would take him up on his offer. She agreed to go up to his room. She did not mention anything about the elevator ride up, but presumably he started to kiss her and feel her up, because by the time they got to his room door, she claimed, he had already begun to get her clothes off. Since conference hotel rooms are not very big, the undressing of her took place quickly on the way to the bed. First her jacket, blouse and bra were opened up the front so he could fondle her breasts. And by that time they were at the bed, onto which he pushed her back, and as she described it “he had my panties and stockings off in a flash.” Things seemed to be going pretty fast for the both of them. His desire to start fucking my wife, and her willingness to take the cock on offer were apparently so urgent that he began plowing her with her jacket, blouse, and bra still on, though fully opened. Fortunately (for her, not me) his lust for taking my wife did not interfere with the quality of his performance: making my humiliation worse, she reported that “he fucked the hell out of me.”(!!)
It must have lasted some time, because she said that by the time he blew his load into her, her jacket, blouse and bra had long come off and she was under him taking his thrusts completely naked. After he had thoroughly fucked my wife in that first session, they lay together, she said with him continuing to fondle and kiss her breasts. She could of course have left at this point, but she apparently was willing to wait around to see what was next. And in short order she watched him begin to pop another erection. Fully erect, he rolled her over so she was face down on the bed, spread her legs apart, and kneeling between her legs thrust his erection into her again. (She never reported in her description of this whether she preferred taking his cock from the front or from behind.)
The detail in which she described this double fucking, and the fact that this second position, face down and legs spread, is not one that she and I used, leads me to conclude that this was not some imagined fucking, but a fairly accurate description of yet another occasion when I got cucked. The detail in which she recounted this fucking sure suggests to me a description rather than fantasy made up on the fly. I should add that apart from her enjoyment in taking another guy’s cock, she got a practical advantage out of being fucked by this guy. Though she never held a position under him (I mean employment, not lying beneath him, face up or face down with her legs spread open) he wrote her a recommendation which got her her first good job!
Entirely independent of this description of his triumph, a year or two later, my wife and I were invited to a dinner party at this guy’s house. I had never met him, and at the time still knew nothing about his cuckolding of me, as her description was some years later. Probably good luck for me, as I find it difficult to imagine enduring an entire evening with a guy who had twice plowed my wife’s pussy. I just assumed he was some big-wig in her line of work. The inuendoes or knowing glances between them were lost on me. Still, he must have taken some pleasure in meeting the husband he had successfully cuckolded. By way of illustration: her about the time he would have had her, so about 27; I would guess he was about 50: