Bringing an older man fantasy to life

By prague2nyc

Original link:

Tags: older, man, fantasy, sex, threesome, mature, girlfriend

Added: 20 Feb 2010 Views: 38992 Avg Score: 4.87

Girlfriend always wanted to try out an older man, we found her one
We had just finished a sweaty sex session where I had Jenny bent over the couch.  It had been a damn hot day and the house was like a sauna.  When I finally came inside her, she collapsed on the ground relieved she could take a rest.  After a brief rest, we sat at the dining table with some drinks, still naked.
"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 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, 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. I lowered my pants and motioned to Sean to move out the way. He looked back "bud, she wants my dick, she wants it bad".
I spoke out again "Jen, you can have my cock to finish you off", her eyes lowered and she mumbled "just get it done then".

I moved onto the bed, Jen still on all fours as she had positioned herself for Sean's dick. But it would be me to finish the job.  I rubbed my cock a couple of times to make sure it was hard enough, then slided into Jen's pussy. I regained my power, Sean could do nothing but watch me fuck her and he was done for the night.  But strangely he seemed to ignore I was in control, he stood at the edge of the bed a mere 2 feet from us and put his hands onto Jen's breasts, circling her hard nipples.  She looked around to him, "I like that Sean".

I was now pumping her fast with my dick trying to get her attention back.  She had gotten so wet from the dildo I was starting to lose my ability to hold back. I fucked her for only a minute or two before I felt an eruption and came inside her. I couldn't stop it or go any longer, the last drop of cum I released as I pulled my dick from her pussy, I saw traces of my cum in a small trail leading out.
Sean held Jen's attention the whole time, still with one hand on her breast, tugging her nipple, with the other on her face, where she sucked 3 of his fingers.
He spoke as he looked me in the eye, "you done already bud? in a hurry to get somewhere else?".

I wasn't in the mood to hear from him, so I stood back up and walked out the room to go clean up in the bathroom. I was gone several minutes and had lost any thoughts of what might still be going on. I walked out assuming Jen and Sean would be putting their clothes back on and maybe out back in the lounge room, heading toward the end of the evening. 

No sign of them in the lounge or kitchen area.

The door to the bedroom was shut, but I saw no sign of them in the immediate other rooms.  I headed toward the bedroom door, by now I heard muffled noises, they sounded aggressive.  Jen was normally quiet during sex, certainly nothing loud or screaming.  The closer to the door I got, the louder the noise. I was still naked as I approached the door, grabbed the handle with anxiety and pushed the door open.

I couldn't believe my eyes.  Sean was standing with Jen pressed against the bedroom wall, her legs hooked around his waist, her arms flung over his shoulders.  I saw Sean's bare ass from behind, working hard to keep thrusting his dick inside Jen as she hung on.  There was no sound from Sean, the grunting noise was all coming from Jen.  She was getting fucked hard up against the wall, her mouth open, letting out deep moans...occasionally calling for more or repeating "oh yeah...oh yeah, yes, yes, baby".

She had been quiet to me while I was fucking her minutes ago but now used all her energy in holding Sean's 62 year old body as his cock pushed repeatedly in her pussy....the same pussy I came in after only a few minutes.

But he kept going, and going. I stood there in disbelief for a minute as he fucked her before me.  He didn't even turn around when he said "this is how you do it little buddy! She loves it a bit rough".
And with that he took one hand and slapped her firmly on the side of the face. Her face froze as it happened, tilting back a little before she yelled back "Sean, fuck me harder, fuck me harder" gritting her teeth and letting out another deep moaning sound.

Sean then grabbed Jen under her ass and carried her over toward the bed again, his dick still firmly inside her. He lowered her down on the edge of the bed so her remained standing, she lay across the bed, her legs in the air as he started again to pound her while holding onto Jen's ankles, keeping them high in the air and spread wide.  He didn't let up, still full of energy, this old guy was there fucking my girlfriend and getting reactions from her that I had rarely seen.

He crossed her legs in the air and kept fucking, exclaiming "that makes your pussy feel so tight around my cock", to which she started rocking her hips to ride his cock even more.  Her arms were thrown back, lifting her breasts in the air as they jiggled with each motion from Sean.  He would then reach forward with one hand to grab her tit, cupping it with a tight grip and flicking her nipple hard with a finger.  Jen would respond with another "ooww ooww" followed by a faster rocking against his dick.

I moved toward Jen, my cock stiffening up and asked in a weak voice "babe, you want to suck my cock...let me fuck you again or something?" hoping it could return to something more sensible than seeing her pounded by an older guy, with his sweaty, hairy and gray chest imposing over her.

She screamed back at me "Just get the fuck out of here, I just want to fuck Sean's thick cock, you had your chance but I need more".
I stood another minute or so, seeing her get worked over by this guy. He changed the pace of his strokes, letting me see side-on he did have a thick cock as he worked it into Jen with ease.  I started to pace back toward the door but still in the room as Jen spoke as her back arched high "Cum in me Sean, I want you to cum inside me...cum...cum".

Her voice trailed off as she was herself nearing climax.  The last sight I saw before leaving the room was Sean fucking her faster, nearing releasing his load inside Jen.  She had started her "I'm cuming" moans that seemed to keep going and going as her back arched tighter.

I went back out to the couch, lay down and blocked their shouts of ecstasy out of my mind.  Within minutes I was asleep.  I awoke early the next morning, around 6am.  I went back to the bedroom, it was empty.  "Jen?... Jen?"  No response.  I searched, but they had both gone, had Jen left with Sean I wondered?  Why?

It was another 7 hours later that there was a knock at the door, Jen stood there by herself, her hair in a complete mess and looking like she hadn't slept all night.
"Where have you been?" I asked.
"We went for a drive late last night" Jen replied. I looked at her wrists which had marks around them like they had been tied up, then asked "but it's after noon already, what did you do?".

Jen smiled back "he took me to meet his wife last night, she's got a hot body....then things got completely out of hand.  I guess I did my fantasy and your fantasy in one night."