"Honey, that was the best you've given it to me in ages...I used to dream of sex as hot as that" Jen said.
I replied "sure, it's always my fantasy to see my cock in you when you're bent over".
Jen looked back at me, "it might turn you on, but that's not a fantasy, a fantasy is something you've never done but dream about doing". I looked at her breasts poised on the edge of the table, "of course, like having a threesome with you and another girl!".
She looked at me with a giggle "I know that's what you'd love to do, but this is a new era, men can only have their fantasy come true once the woman has had hers first".
I shot back "and what would yours be then?". Silence for a moment then she replied "oh, ah, well I don't really have one". It sounded guarded so I fired back "bullshit, everyone has one...what would you do, with who, if no-one would ever find out?".
She took a moment and hushly spoke up "I guess it would be curious to have sex with an older guy, someone with a hot smooth distinguished look like George Clooney".
With that the conversation drifted off and the topic to rest.
It was a month later when Jen came home and excitedly told me about her train ride home when a guy sat next to her and started talking to her. She noted he must have been in his 50's but he was a good looking guy and she got thinking about him and our conversation about her fantasy.
She cheekily added "maybe he can be the one I have my fantasy with?". Without really thinking it through I retorted "sure, as long as I get my fantasy next then you can give him a blowjob or something. Pity you can't find him again"
Her eyes widened, "he told me his name and the real estate company he owns, so I could track him down. Babe, I'm getting hot just thinking about touching his cock, you can watch me lick it".
We had a lot more discussion over the next couple of days before agreeing that she could at least call him and see if he was interested. It didn't take her long, a night later she told me she dropped into his office, put the proposition to him and suggested he come over Saturday night. He jumped at the chance, even kissing her cheek before she left.
Jen arrived back and told me his name was Sean and he was a grand 62 years old, owned his company and drove a Mercedes. Apparently he was also married to a younger woman. We discussed and agreed she could do what she was comfortable with on the night but she wouldn't have full sex with him, only with me.
The night arrived, and right on time his big car rolled up. Jen was nervous. She had a few drinks in the lead up to calm her nerves and I dropped a few hints to only mess around a bit with him until she was over the old guy fantasy.
Sean seemed extra confident, practically ignoring me as he dropped constant compliments on Jen, or "Jennifer", as he insisted on calling her. Sean told how his daughter was even several years older than Jennifer and that he had never had sex with someone so much younger than him. Jen was wearing a dress that wasn't too revealing but she did have some nice lingerie on underneath.
We had been in a nervous chatter for 20 minutes or so when Jen offered another drink to Sean.
He moved over to her, placing his hand on her bare shoulder and spoke "I think it's time to get to know you a lot better". As Jen sipped her drink, Sean brushed his hand downward, dropping the dress strap to dangle freely. He moved his other hand to place it on her butt.
Again, I couldn't believe he was moving in like this without even asking me for permission or acknowledge to me how this would go down.
Jen's top was now quite loose, she moved a few steps away, turned and pulled the dress down below her bra and looking at Sean, said "Follow me", as she walked into our bedroom. Sean removed his casual jacket and handed it to me, then headed into the dimly lit bedroom.
I took a few moments to settle my thoughts and walked toward the bedroom which now had the door almost closed. As I pushed it slowly open, I could see Jen had lit several of our candles. Sean was kneeling on the bed with his back to me, still clothed. Over to the side I could see several of our sex toys Jen had placed in line on the bedside table. Sean turned his head, the gray hair shining in the candlelight "You want to watch this little bud?" he asked as if I was the 3rd party here.
Moving over to a side chair I positioned myself down and now could see Jen....by this stage she was rubbing his pants over his cock, she looked at me, giddy with anticipation.
"How old are you again Sean" I asked, trying to put him in his place. He laughed, "62 years bud, but getting younger with each young girl like Jennifer". Then I heard a zipper, Jen was lying on her side, her g-string exposed and about to pull his old cock out. He reached one hand to her ass, while she fumbled with his belt till his pants dropped to his knees.
I was feeling uncomfortable, as the reality hit of seeing her in a sexual situation with someone else for the first time. She seemed to have gotten quite bold after her drinks earlier. "Honey, get my dress at the back" she barked at me, whilst removing the last of his boxer shorts leaving him now completely naked. I moved around the bed noticing his body was in decent shape but clearly that of an older man. Jen was holding his dick, stroking it making anxious noises usually reserved for me. As I lowered her zipper she immediately pulled the dress off with force, turned back to Sean and plunged his dick in her mouth.
Sean let out a moan, then boldly said "Back to your chair, bud....watch the show". He was moving his hips to force his dick deeper in Jen's throat each time she took more in. As she pulled her head back she looked up at Sean and proclaimed "such a big cock for an old man, it's harder than I could have imagined". Sean had moved his hand around to the front of her panties, stroking firstly on the tiny piece of fabric covering her pussy.
"My young Jennifer is a very wet girl tonight" Sean said in his lowered voice, and with that he pulled the panties aside and put two fingers over her bare skin. Jennifer giggled again "I had it waxed specially for you".
By now I felt like I was watching another couple altogether. I didn't even know Jen had just gotten waxed, she hadn't gone completely bald ever until now.
Sean was rubbing several fingers on her pussy and moved one finger inside her which she immediately responded to. He moved down to kiss her then whispered "let's have some fun", whilst reaching over to grab the silver dildo. That was the one Jen often said was too big to be comfortable so she generally wouldn't let me use it on her. Sean took his fingers off her pussy and swiftly inserted the silver dildo in half way. Jen let out a deep moan, her hand placed on his head, stroking through his gray hair. Sean then started pumping the dildo in and out her pussy with determination.
I looked to see if it was too much for Jen and thought of saying this was too far.
Jen then surprised me, "give it to me harder Sean, I love it", she leaned over again to suck his dick which he eagerly placed back in her mouth. The silver dildo was thrust into Jen repeatedly, Sean holding it tight in his fist, I could see the dildo glistening with her pussy juice. She kept going hard on his cock in her mouth, I could repeatedly hear her struggling as she took the entire length in her mouth, but as it pushed her ability to keep it in, Jen only was getting more into it.
My dick was hard watching them go at it, but I refrained from jerking off, it seemed weird to cum by myself in a chair, several feet from a 62 year old getting his dick sucked by my 27 year old girlfriend, who didn't realise I was there anymore. Then with one swift motion, Sean pulled his dick back, removed the dildo and grabbed Jen's hips. "Flip over Jennifer" he smoothly instructed.
Jen,with saliva dripping all out her mouth from the extended blow job, panted back "oh yeah baby, do it to me". It took me a moment to realise Sean was preparing to put his old dick into Jen's younger pussy. By this stage she was on all fours. Sean was sweaty and focused on guiding his cock toward her. It was an inch away as he lined up before plunging in, the tip slightly touched her protruded pussy lips.
I rose to my feet, "woah now guys, Jen...we agreed to hold back from sex!".
Sean turned back to me, his cock tip pressed firmly against the outside of her pussy but not yet inserted.
Jen, still panting, turned with frustration, "babe, get over it, I'm gonna fuck him, Sean is so hot, his cock is awesome, I wanna feel it inside me".
I wasn't ready for this, hearing him grunting as he used the dildo on her was getting too much.