Older man.

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:
 

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We've lived in Europe for about a year now and made friends from our new country, and also within a group of mainly American ex-pats. A new kink has started with May. We're younger than a lot of the ex-pats and we've met a few older men who have lost their wives.

The first time May provided sympathy sex for one of these men happened a couple of months ago. We were talking with Bob, who is in his 70s, at a bar in town and he was talking about his deceased wife. May asked him if he's met anyone since then and he said no. She decided to take him back with us for more drinks. After a bit May was sitting on the sofa next to Bob and took her top off and asked him to play with her tits. Eventually she undid his pants and worked on his cock, which finally got hard and she asked him to fuck her. He hesitated, since I was there, but finally took advantage of my wife!

I write this because just tonight another older guy who has only been in our city for a short time got a shot at May. We'd seen him in the bar 3 nights in a row and he and May hit it off. I'll call him Dick. I simply asked him if he wanted to fuck my wife. He wasn't sure, but gladly accepted the offer to come back to our apartment.

We'd had a few drinks already and May started flirting with him some more. I asked him what he thought of May and he answered that he loved the look of her tits. May asked him if he wanted a better look and took off her top. He mentioned he had a hard time getting an erection and she asked if she could help him with that. He stood up to take off his shorts and she got on her knees and started sucking his cock. Again, it took some effort, but he got hard in May's mouth. She asked him if he wanted to fuck her. He said he didn't feel comfortable with that yet, but he felt comfortable enough with his cock in my wife's mouth to grab her head and fuck her face!

She gave me this look as she was performing her community servicing work.
 

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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:
Ur wife sure is sexy, i see why he wanted her and Bravely hit on her,. U didnt know at that time that U would get eXcited telling in depth how she made U a cuckold. How active is she now? are U involved in her eXtra cock adventures??
 
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We've lived in Europe for about a year now and made friends from our new country, and also within a group of mainly American ex-pats. A new kink has started with May. We're younger than a lot of the ex-pats and we've met a few older men who have lost their wives.

The first time May provided sympathy sex for one of these men happened a couple of months ago. We were talking with Bob, who is in his 70s, at a bar in town and he was talking about his deceased wife. May asked him if he's met anyone since then and he said no. She decided to take him back with us for more drinks. After a bit May was sitting on the sofa next to Bob and took her top off and asked him to play with her tits. Eventually she undid his pants and worked on his cock, which finally got hard and she asked him to fuck her. He hesitated, since I was there, but finally took advantage of my wife!

I write this because just tonight another older guy who has only been in our city for a short time got a shot at May. We'd seen him in the bar 3 nights in a row and he and May hit it off. I simply asked him if he wanted to fuck my wife. He wasn't sure, but gladly accepted the offer to come back to our apartment.

We'd had a few drinks already and May started flirting with him some more. I asked him what he thought of May and he answered that he loved the look of her tits. May asked him if he wanted a better look and took off her top. He mentioned he had a hard time getting an erection and she asked if she could help him with that. He stood up to take off his shorts and she got on her knees and started sucking his cock. Again, it took some effort, but he got hard in May's mouth. She asked him if he wanted to fuck her. He said he didn't feel comfortable with that yet, but he felt comfortable enough with his cock in my wife's mouth to grab her head and fuck her face!

She gave me this look as she was performing her community servicing work.

Went back to the same bar last night for a beer, and who walks in but Dick!! He sat down next to me at the bar and the first thing he asked was "Where is May?" Told him she stayed home. He thanked me for having May give him a blowjob the previous night and I told him it wasn't a problem, she was happy to do it.

He was kind enough to buy me beers all night!
 
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