Jack wasn't sure where he was, the surroundings not looking familiar. He was outside, possibly in a park, but he wasn't sure. A man he did not know stood in front of Jack, he was a big man, approx. 6 foot 2 with a thick build, not fat but solid and void of any body hair. Jack didn't get a good look at his face; he could tell he had brown hair but nothing else caught his attention. What did catch Jacks attention was the very hard 9-inch cock that stood proudly out from this mystery man's crotch. It was glorious and Jack took hold of it with his left hand and gave it 5 good pulls. Jack felt compelled to suck this fine piece of meat, he opened his lips and relaxed his throat and took as much of it as he could into his mouth. Pressing his lips tight Jack moved his head back and forth, going as deep as he could on this stranger's wonderful cock. Clearly not content with how much Jack was indulging, he grabbed Jacks head and pulled him into his crotch, pushing this monster rod further down Jacks throat; Jack gagged, he eyes watery as he tried to relax and give his anonymous lover a terrific deep throat experience. Jack was having a wonderful time.... then all went blank..
Jack woke up sweating, he could also feel the moisture on the end of his penis and the sticky mess inside his boxer shorts. He looked over at Paige, these dreams were becoming more common, dreams of he and other men.
" You ok babe?" Paige mumbled in her sleepy daze.
" Yeah, just a bad dream" he replied.
"Do you want to talk about it?"
'Fuck no!' he thought. " No honey, go back to sleep"
Jack loved Paige, she could be pretty intense at times and challenge him mentally, but she was loyal and she clearly loved him. They did laugh together and have good times. The irony was, since Mandy came into Jacks life, his relationship with Paige was better than ever. The sex was better, she seemed to be making more of an effort to look sexy for him, amazingly even wearing her thong on several occasions and Jack himself finding himself being less snappy and more relaxed.
But was this all a charade? Mandy still had Jack in a trance, their relationship now going well beyond a manager and employee; the night in the hotel room after their work Christmas party changed that. And these dreams, they were taunting Jack to go back to a past life, a life he thought he had left behind. But could it ever be left behind? Jacks most impressionable years spent having sex with men, not women. He had only ever had sex with three women, one being Paige, yet he had slept with numerous men, too many to remember.
Jack laid there trying to go back to sleep, in his head was a voice, his voice, saying 'dude, you're all fucked up'....
Mandy laid in bed, it was mid-afternoon and she was horny. It was very rare for Mandy not to be horny; her sexual appetite was immense. Stopping short of calling herself a slut Mandy definitely conceded that she was a nympho. Nearly every guy Mandy walked past, she'd find hers wondering how big their cock was, she loved the dick.
Mandy walked over and opened her bottom draw, underneath a pile of clothes she hid her vibrator, she had to be careful where she kept it, as her mother, while being a lovely woman, was also a bit of a sticky beak. Mandy didn't think her mother would really care if she found the toy but she tried to avoid an awkward conversation.
Back on the bed, Mandy opened the web browser on her phone and searched up some gang bang porn, when she was horny like this the thought of being dominated by multiple men really turned her on. It was something she was yet to experience but it certainly made her hot.
Mandy licked her finger and started rubbing her clit, her pussy was smooth, freshly waxed the day before. Mandy hated body hair, being Maltese, her hair was dark and she really didn't like how dark her pubic hair was. But it wasn't just her own body hair she disliked, she preferred her men smooth as well, her worst blow jobs were on men with thick pubic hair, she just couldn't give them the attention they deserved, but on a cock that was smooth and hairless she could suck until her jaw became sore. She pressed the small vibrating wand on her clit. She was very wet, the sensation sent tingles through her entire body. She looked at her phone as this tiny blonde girl took a huge 10-inch black monster into her not so tight back door, the 5 muscular men taking turns at impaling her and filling all of her holes simultaneously. Mandy marvelled at how such a small petite girl could handle so much cock at once, each man rotating around her, destroying her openings and leaving her gasping for air. Finally, the men showered her in their huge loads of cum, soaking her head and hair with their thick cream, leaving her in a disgusting mess.
Mandy moaned in pleasure, she was approaching an orgasm herself, she changed her phone into camera mode and took some photos of the toy in her pussy, this would be good to send to some of her Snapchat guys. Mandy was flirting with several guys on Snapchat at the moment, 5 to be precise. She'd send them pictures of her naked body and her pleasuring herself and they reciprocate with multiple cock pics or videos of them cumming. She really was insatiable, her strict upbringing and living with such a controlling father made her worse as she lacked freedom.
She sent the picture to two of the guys that she thought would be most responsive, Bryan and Mitchell.
A reply came back within seconds from Bryan, it was a picture of his hard cock. He had a wonderful cock, approximately 9 inches in length and quite thick. He didn't have a large head but it stood very hard and straight when erect, they could have moulded a dildo from it. ' I want to bury this in you!' was the caption.
' Cum get it then!' Mandy replied
' There in 30' Was the response.
Mandy stopped playing with herself and got herself dressed. She put on a very short beige mini skirt and white singlet. Under neath she wore her favourite bra and panty set. It was a silky red set, the thong was very thin, just covering her pussy with a string back. She called these her ' Lucky' panties.
Bryan picked Mandy up and drove to his house, Mandy already had his cock out pulling it as he drove, she leant over and gave it a suck when they stopped at some traffic lights, in a way hoping she'd be caught by someone in a car next to them.
They arrived at Bryans house; he shared a house with some friends who were all out. They headed straight to the bedroom; clothes were off within seconds. Bryan was tall and lean; his body matched his cock. He laid on the bed, Mandy commenced working on his shaft, licking it up and down circling the head with her tongue. She opened her jaw wide and took as much as she could in her mouth, trying to take long breaths through her nose as Bryan's large rod filled her mouth. She loves sucking cock, Bryan was very well trimmed so that made it even more appealing to her. Bryan grabbed his cock and lifted it putting his balls on display, Mandy knew what to do and started licking his smooth balls taking them in her mouth one at a time. As Mandy kept giving Bryan's balls more attention, he bent his knees up and spread his legs further apart. Mandy knew what this meant from a previous session with him. Mandy placed a pillow under his lower back, Bryan pulled his knees up to his chest putting his ass on full display. He was shaven in the crack as well. Mandy moved her head into place and started rimming Bryan's tight hole with her tongue, licking it like she'd like her pussy licked. Bryan moaned in pleasure as she made his ass very wet. Using her index finger, Mandy pressed on his opening, firmly she pushed it into him, Bryan moaned again as she pushed herself in up to the knuckle. Slowly she started finger fucking him while licking his cock. The penetration was becoming easier, she pushed a second finger in. Mandy was unsure if Bryan was Bi or not, but he seemed to love having his ass fucked by her fingers. She pushed up on his prostate, giving it a firm push and started rubbing back and forth on it, this sensation caused some pre cum to eject from the tip of his rod, she licked it, it was sweet tasting.
" I want you in me now" she demanded moving herself over his body. Her pussy was saturated already, no need for lube as she lowered herself onto him, his 9 inches pushing deeper and deeper into her young pussy. ' Soooo good' she thought as Bryan pelvic thrusted into her harder and harder. It was a good long fucking he gave her, she turned and went reverse cowgirl, Mandy loves letting guys watch her ass bounce up and down on them, her tight asshole on display as her pussy is impaled.
Switching into doggie, Bryan continued pounding her and hearing the sound of his body slapping on her ass, he kept going, the speed increasing before he quickly withdrew and spirited streams of cum all over Mandy's ass, smothering it with his warm sticky load.
Boy did she love his cock.
"Good night" Jack said rolling over and kissing Paige. They not long finished having sex, it was good sex, she was being more adventurous now, tonight she made Jack cum while blowing him, she didn't swallow, she's not that adventurous yet.
" Night" she replied, and they went into slumber.
Jack had several dreams, nothing too memorable until he found himself in a strange room with old John. The same John that took Jacks virginity at 15 years old. Jack was wearing a schoolgirls skirt and black thong. He had no top on. John was behind him with his hard cock in hand. John was about 7 inches; Jack remembered the cock very well as it was his first. John pushed it into Jack, it slid into him with ease. Jack gasped as John furiously fucked his ass, then as with all dreams, it was over too quickly. Jack woke up, sweating again. ' I need to do something about this' he thought to himself.
Monday arrived; Jack's team had a meeting at 11am each Monday but Jack wanted to talk to Mandy first so he sent her a meeting invite for a one on one feedback session.
They went into a meeting room with frosted glass windows.
"So, I'm going to be telling the team this morning about an office move coming up in Melbourne and calling for volunteers. They'll be putting us up in hotels and flying us down. Are you interested?" Jack asked.
" Of course I fucking am!" She said excited.
"Awesome" he replied.
"Can we stay in the same room" she asked giggling.
" I'm sure we'll have a room each booked...but yes we can" he smiled.
The conversation shifted " Hey, I've been talking to these two new guys from Tinder. I think I want to meet up with them"
"Like at once?" Jack questioned.
" Haha, no..well not yet" she grinned.
" Who are they?
" One's name is Blake. He's so hot, big body builder and his cock is so thick. We've been sending each other Snapchats. The other is Max. He's Lebanese looking, not sure if he is, he's pretty fit as well. His cock is so fucking long." She told Jack.
Mandy's relationship with Jack had become very strong, Mandy had confided in Jack, telling him about the struggles she has with her father and how he restricts her lifestyle, she also told Jack about the guys she was talking to and fucking, she'd always send Jack a text with a map location where she was meeting a guy, Jack had become her security blanket, she trusted him, they had so much in common and he was a good strong influence on her. Some might say he was a bad influence.
" Show pics" he said
" I can't, it's all on Snapchat, the pictures don't save."
'Fuck' Jack though, he really wanted to see their cocks. " Fair enough, well when you going to see them? You know the drill, send me the map of where you are."
" Thanks honey" she said. When they spoke like this it was a totally different relationship to their work one. They both had the ability to switch it on and off at ease. " Max is pretty full on. He's already been saying how he's got some friends I'd like; I think he's trying to set me up for a threesome, or maybe more."
" How so you feel about that? Can you trust him?" Jack said trying to sound concerned. The thought of his little Maltese getting abused by multiple men turned him on, he'd love to be a fly on the wall while she was destroyed by several big dicks.
" Yeah, I've told him I just want to fuck him"
" Ok, anyway, just make sure I know where you are and when" he reiterated.
Jack thought to himself, is this my opportunity to tell her about my dreams, he wasn't sure how she'd react. He decided against it.
Two nights later Jack received a text from Mandy, ' I am here's it said with the map image of where. It wasn't that far from him; he could be there in 15 minutes.
' Who with?' he replied
' Blake' was her one-word response.
Mandy arrived home. The sex with Blake was quite disappointing. She messaged Jack, it was late, but he was up watching Game of Thrones on his own.
' I'm home' she typed.
' Excellent, was it good?'
' Not really, he's hot and his cock was amazing, he just didn't know how to use it, and he kept trying to put it in my butt.'
' Did he get it in?' Jack asked excited
' lol, no, I wouldn't' let him' she replied.
Jack thought ' I still need to train this girl don't I ?'
' Ok, I'm going to sleep, see you tomorrow x' he said
'xxx' She replied
Jack wakes up the following morning, while he's in the shower Paige walks in. " I think i'll come to Melbourne with you" she said inviting herself on the trip. "I can go see my sister"
'Oh for fuck sake!" Jack thought to himself, there goes my fun. "OK babe" was all he responded with.
After getting dressed Jack messaged Mandy ' We have a hurdle for Melbourne, Paige wants to come and see her sister. Lets chat when we get to work'
' Fuck!!' she replied with. Mandy wasn't happy.
Jack and Mandy had another 'One on one feedback session' that morning. They discussed the issue that was Paige coming with Jack to Melbourne, they had a plan. On the first night Paige had said she'd have dinner with her sister. Jack would say he was still working late but in reality, would be in Mandy's room watching 50 Shades of Grey with her. Mandy had never seen it and was very keep to. Jack knew the movie was on Netflix and would stream it from his laptop. They agreed on the plan.
That Friday Mandy told Jack that she was giving Blake a second chance.
"Really?" Jack said "wasn't he shit?"
"Yeah, but he's so hot" She replied.
"What if he tries to go in your ass again?"
"I'll stop him" she said
"Just let him get it do it for fuck sake, you'll be his hero forever" Jack said laughing, not really serious, but hopeful she would.
"Hmmm maybe" she almost agreed. 'Maybe i should give it a try' she thought to herself. Blake was thick though; she wasn't sure if she could take it.
"Well I expect a full report" Jack demanded
"Haha, you know I'll give you one" she said agreeingly.
It was Saturday night, Mandy sent Jack a text 'I'm here with Blake'
'Have fun, i hope you took lube, hahaha' Jack replied
Mandy was on top of Blake, riding him reverse cowgirl, her ass looked amazing as it bounced up and down on his thick cock, he was pumping really hard into her and she was bucking back and forth like she was riding a wild stallion. Blake could see her tight asshole each time she rose for another thrust, he reached forward rubbing it with his thumb. 'Here he goes' Mandy though to herself but she was in lust, Blake was performing a lot better this time, his pulsing rod highly satisfying her pussy. Mandy hopped off and got on all fours, Blake quickly in behind her and again burying his member in her cunt. He pounded with mass vigour, again his thumb finding it's way to her tight back door. Mandy didn't see to object as much as she did in their first encounter, the extra effort Blake was making had made her extremely horny. Blake noticed this and withdrew his cock from her pussy and placed it at the entrance to her virgin anus. 'Fuck, here we go' she thought to herself. Mandy had mentally prepared for this, she knew he'd try and her curiosity had given her the courage. Blake pushed; it was difficult to penetrate as she was so tight. Mandy pushed herself back towards him, his head pushed through opening, Mandy grimaced, it didn't hurt as bad as the thought, but she still felt it, Blake continued pushing in and was soon about 6 inches deep.
"Leave it there a second" Mandy said, trying to adjust and accommodate him in her other love passage.
Blake paused, he let his cock stay where it was for a moment, then he slowly retracted it and gave it another push. Mandy moaned when it went back into her, going slightly deeper again. The pace was slow as Blake let Mandy's body accept him. Gradually Blake increased the tempo and was soon pushing in and out of Mandy's ass at quite a pace. Mandy was now finding it quite comfortable as Blakes wide cock stretched her open. She reached down and started playing with her pussy. Blake was now really hitting her ass hard, each thrust knocking the air out of Mandy, she could feel his grip on her hips get tighter and knew he was close to exploding. Blake withdrew from her not so loose ass and exploded up her back. He let go of his cock and it rested on her ass crack.
"Was that good?" she asked. His heavy breathing and nod confirmed what he thought.
Mandy arrived home ' I'm home' she messaged Jack
'Fun?' Jack responded
'Yes, i let him do it!' She said
'The ass?' Jack asked
'Yes!' she replied
'How was it?'
'Not too bad actually, I'm amazed how easily it went in, lol'
'Awesome! another tick off the bucket list then ;)' Jack said.
'LOL, plenty more to go, night honey xx' She signed off with.
The following week was the Melbourne trip. The plane ride was uneventful, Paige caught different plane as her trip was self-funded. Jack and Mandy sat next to each other, careful not to get too close as Jai and Kurtis were in the row behind. The work component of the trip went well on the Saturday, the team all went out for dinner. It was getting late, Mandy texted Jack from the other side of the table ' Can we go soon?' she asked, clearly wanting to get back to her room with Jack and watch the soft porn 50 Shades with him.
'Soon' he responded.
Everyone left around 8pm to go back to the hotel. Jack knew Paige would still be out at her sister's house for a while longer. He didn't go to his room to get changed, he couldn't risk Paige coming home and knowing that he was no longer at work. Both he and Mandy snuck back into her room, luckily Mandy had been put in a room on another floor from he, Jai and Kurtis so they didn't have to worry about one of them seeing him enter or come from her room. Mandy went and showered, both were sweaty after a long day lifting and moving equipment. She came back out wearing her pyjamas, very similar ones to what she wore in the hotel after the Christmas party. The shorts were pink and very short and the singlet light blue. She wore no bra; Jack could easily see her nipples pressing through the fabric. 'What panties is she wearing he wondered' he knew it would be a thong of some sort.
" Do you mind if I jump in quicky?" he said
"Sure" Mandy responded.
Jack didn't have a change of clothes, he was wearing a T-shirt and shorts all day due to the nature of the work. He showered, when he got out he didn't put back on his underwear, he stuffed them in his pocket. He used some of her deodorant to spray himself and his clothes.
Jack set up his laptop on the table next to the bed, he'd downloaded 50 Shades of Grey as his laptop couldn't stream Netflix due to its firewall settings. The movie started, due to the positioning of the laptop on the table both laid on their side to watch it, Mandy in front and Jack behind her, they were close, almost spooning, as the movie progressed, they inched closer and closer, Jack soon having his arm around this tiny Maltese wonder. The move wasn't great but there were some scenes that turned them both on, Mandy was getting wet and Jack's cock rising. He was laying so close to her now, her ass pressing against his crotch, both were so horny. Jack knew that his hard on was pressing into Mandy's ass cheek, he didn't care, he wanted so badly to rip her pants off and bury his cock deep inside. Jack wasn't hugely endowed; he was around 6 inches but it got very hard with a slight upward bend just below the head.
Mandy could feel Jacks cock pressing hard against her ass 'Fuck, should i just jump on him?' she thought, similar thoughts to their last hotel sleepover together. She could feel as Jack pressed harder on her, was holding her quite tight in his arms now. Both were very horny.
Jacks phone buzzed. It was Paige, 'I'm staying at my sisters, have had too much wine' she said.
'Ok babe' Jack replied.
The message had broken the mood. Mandy thought to herself ' That's right, she exists...' and moved away from him slightly.
Jack had been deliberating for weeks about telling Mandy about his life before Paige and how he was having these dreams about men.
"Hey, can I tell you something? it's been on my mind for a while" Jack asked
"Sure, what is it? Mandy replied. Mandy's brain started ticking, 'is he going to tell me he loves me or something?' she thought to herself.
" I'm a bit nervous, I've never told anyone I know this. Before Paige I had never had a proper girlfriend. I actually thought I used to be gay when I was much younger. I finally broke my virginity with a girl when I was 24. She was fat and ugly, it was atter one of our football matches, she was one of the guy's sisters. As I got older, I always felt I wasn't gay as I would always be perving on girls, but I'd never been with one." He said almost ashamed.
" You'd never kissed one" She asked
"Well, I did kiss a girl from school on the Gold Coast at schoolies week, but that was it. But here's the thing I'm nervous about. I actually lost my virginity fully when i was 15, and it was with a man."
Her eyes opened very wide, as though she had just snorted a line of coke. " Oh my fucking god!!" she exclaimed " that is so fucking hot!! Tell me more!!"
Jack sighed in relief, she hadn't kicked him out from her room, that was a positive.
"Well, I was 15, obviously living with my parents. We lived in a small block of apartments near the beach. the man that lived in the tiny apartment out back's name was John. He was pretty old, I'd say in his 50's. One night I found him looking at me through my bedroom window. He ran away when I saw him. I found him doing it again a few nights later, I could see him in my TV reflection. I didn't turn to face him instead i started playing with my cock. When I did turn, he didn't run this time. It happened again a few times, my bedroom window was just off the walkway the led to our front door, so it was easily accessible. One night when he was there, I moved closer to the window, and he had his cock ut pulling it. I reached through and grabbed it, pulling it as well. I made him cum. It kept going until one night he motioned to me to follow him so i climbed out the window and went into his apartment. I gave my first blow job. It escalated from there, a few nights later he fucked me for the first time, fuck it hurt, he was pretty big, bigger than me. But that was the beginning. From that time I'd fuck him a few times a week, he introduced me to some of his friends, I fucked them too. I had a threesome with him and his friend for my 16th birthday. They spit roasted the fuck out of me.
"Oh my fucking god!!" she said in delight. Jack continued telling her some stories about guys he had been with, it has clearly turning her on as she rubbed her pussy through her pants without even realizing she was doing it.
"Then I met Paige, I thought I had to stop, it was time for me to be hetro, but fuck it's been tough."
"So you haven't fucked any guys since being with her?" Mandy asked
"None" he replied "But lately I've been having these dreams, all about me and other guys. It started just after I met you haha, I think you've woken my inner beast"
"Wow, you have to fuck a guy!" she demanded
"I'm not sure i could at the moment, I've probably tightened up too much" He said
"Oh get fucked, if I could take Blakes cock in my butt the other week you can start again"
"I used to have a lot of toys, dildo's butt plugs etc. They'd keep me trained, I got rid of them all when I met Paige. I had a favourite, it was 12 inches, a John Holmes replica. I loved it, it was so big and thick."
" Do you think you can cheat on Paige with guys?" she asked "I'm guessing Paige wouldn't be into it?"
" I'm not sure, in a weird way I'm quite loyal, yet you make me do things I didn't think I'd do" he explained.
" I know how you feel, I've been wanting to fuck you for months, but i wont, because i know your girlfriend, there's no way I could be at work seeing her knowing that I've fucked her boyfriend." she said. It was good that she said that it gave him clarity why they hadn't fucked yet. "OMG, let's go buy you a dildo, I'll buy it!" Mandy was so excited.
He hesitated briefly, "OK"
Mandy searched on her phone for sex toy shops nearby. There was one two blocks away. She quickly changed into some jeans and a jacket, and they headed out. They arrived and walked up the stairs into the store. There were a few men in the shop, two of them creepy looking old guys but one younger businessman in a suit.
Jack and Mandy started looking at toys "how big do you want?" she asked
"I think 6 or 7 would be the max at the moment" he replied
They found a black 7-inch dong on the rack, it was quite thick, just wider than two fingers. It had the suction base that Jack liked, he loved sticking them to a table and riding them. "This one" he said.
The younger guy was staring at them, actually so were the creepers, Mandy smiled at him thinking he was looking at her, but she could quickly tell that his eyes were on Jack.
"He wants you" she whispered to Jack.
"Surely he wants you?" Jack queried. Jack pointed to Mandy as if to say 'her?' The man shook his head, motioning towards the video booths. As the stranger made his way into one of the booths Jack said to Mandy "let's go"
"No fucking way, get in there and suck him" she said assertively. How cold Jack deny such a command and he made his way into the adjacent booth.
Mandy went over to the counter and said to the shop assistant. "Can i just wait here a minute?" she asked
"Your boyfriend?" he asked in his very queer voice.
"No, my boss" she said laughing.
Jack put in a two-dollar coin to get the video playing. The booths had a glory hole for sucking your neighbour. Within seconds through came this hard long penis. It was approximately 6 to 7 inches, but it was rock hard. Jack grabbed it, 'here we go again' he thought to himself. It had been over two years since his last cock. Jack got on his knees and took it in his mouth. It was just like riding a bike and Jack worked his shaft, head and balls with his tongue. The movie stopped playing, Jack moved away and put another coin in. He knew how this worked; the shop didn't mind people using the booths for lewd behaviour as long as they kept the coins going in. Jack pressed his lips tightly around this strange man's cock and sucked harder and faster. It was tiring as it had been a while and he was out of practice, suddenly without warning his mouth filled with warm fluid, this man was pumping his load into Jacks mouth. Jack struggled to keep up with the load gulping as fast as he could trying to avoid getting his t shirt dirtied. The man pulled his cock back, they were done.
Jack walked out to find Mandy waiting, the smile on her face was from ear to ear. "So???"
"It was great" he replied "Lets go" Mandy had already paid for the toy and they left the store.
"Was he big?" she asked as they walked own the stairs, Mandy wanted all the details, so he told her everything. "You slut!" she said.
"I sure am, you aint seen nothing yet" He winked at her. They were both so excited, Mandy as she could live certain fantasies through Jack, and Jack as the beast had been released from the cage.
They walked back to the hotel "Can you take it back on the plane for me? I cant have that in my bag with Paige here" Jack asked
"Haha, of course" she agreed "Hey, Jai and I have been flirting a bit, I think I might fuck him"
" Cool, go for it!" he said giving her permission. If he couldn't fuck her, he wanted her to be like him when he was single, he wanted her to experience all the sexual experience that single people should go through.
Jack awoke the next morning and messaged Mandy 'going to have some breakfast, you cum with?'
She replied 'lol, yes I cum, meet you in 10 mins downstairs'
As they walked out of the foyer, Paige was coming in the door. She gave him a hug and kissed his lips. 'Hahahaha, those lips sucked dick and swallowed cum last night you stupid bitch' Mandy chuckled to herself.
"How was last night?" Paige asked
"We just went for dinner with the guys then came back here. I was in bed by 10pm" he lied.
Mandy chuckled to herself again 'this is going to be sooo much fun' she thought.
"Ok, he said, we have to go, will talk to you later" Jack said kissing Paige again. Again, Mandy laughed to herself.
"You're so bad" Mandy said as they walk out. Jack just looked and smiled.
The rest of the trip passed by. Mandy and Jai sent pictures to each other but o some reason didn't fuck while they both had a hotel room available! Jack and Paige fucked on the last night, they started in the shower with Jack punishing her from behind before finishing on the bed where Jack shot his load up into her while she rode him. He really hoped he hadn't just made her pregnant. I think she hoped he had as she didn't get off in a hurry.
It was the following Thursday. 'Hey, are you going to staff drinks tomorrow night' flashed the message on Skype.
"Yeah" he replied to Mandy. "You?"
"Yes!" she said. "So Jai and I have ben chatting, he wants to get a hotel room tomorrow night, thoughts?"
"I think you and Jai should get a hotel room tomorrow night ; )' he responded.
"LOL, OK, thanks boss"
Conversations on Skype were not recorded, it was decided that backing up everyone's conversations used up too much back up space. Some of the conversations that must have been had on Skype would be truly intriguing.
It was Friday night, there was a large crowd up on the deck for drinks, lots of beer and wine being consumed. Only about an hour in Mandy came over to Jack "I'm going"
"Have fun" he smiled as Mandy made her way to her rendezvous point. Jai had already left before.
The drinks continued, there were several people now well and truly drunk, such a person was Mary. Mary worked in the IT team as an administrator. She was a lovely lady, always happy and smiling, she also had her own fashion. Mary loved to wear big elaborate hats to work. This would usually be matched by a similar coloured women's suit jacket and skirt. She was dressed like this now, her hat, suit and skirt sky blue. She came over to Jack, she was clearly feeling the effects of several wines. Jack also feeling the effects of multiple beers. Mary's hands began wandering, she was touching Jack on the arm, the lower back and one blatant time on the butt. Jack didn't care, he was playing along thinking she'd go home soon. Mary was a middle-aged woman, Jack guessed that she'd be in her late 40's. Jack knew that she was married with a teenage daughter. They had spoken before while Jack assisted her with IT issues. She was quite curvy, not in a fat way but she had hips that reflected a mother and quite large bosoms. Her hair was just past shoulder length and light brown, and she had a tendency to wear very bright red lipstick that really made her lips stick out.
Mary asked Jack to help her get to a taxi so Jack being the gentleman that he is took her to the lift. In the lift Mary was leaning on Jack, her hips and round ass pressing on Jacks thigh. Out front a taxi arrived. Jack heled Mary in, she wouldn't let go of his hand, insistent that he took her home as she didn't feel comfortable being in a taxi on her own while this drunk. 'OK' he thought, 'she lives on the way to my place, I'll make her pay to get me home.' He told the taxi driver to wait and went back up to get his bag. Paige had not come tonight; she had the day off work due to a toenail infection.
Jack came back down and hopped in the back with Mary. He sat on the opposite window to her. The taxi started driving, every soon Mary started sliding over towards jack, soon she was sitting right next to him, both their thighs rubbing together.
"Why do you make me so horny Jack?" she asked as her hand found it's way onto his thigh. Jack wasn't really sure what to say. Her hand started making it's way up his leg and was soon unzipping his jeans.
"Whoah! there tiger" Jack burst out. "Aren't you married"
"I don't care, i just want to suck your cock" she said, pulling his hardening shaft from his pants.
Jack was a bit dumbstruck on what to do, this older woman had his rod in her hand stroking it up and down, the taxi driver very aware of what was happening. He leaned back in the seat and went with the flow. Mary leaned over and took his stiff wand into her mouth, it actually felt really good Jack thought. He moved his hand down her back and rubber her ass. ' What's she got under there?' he thought to himself. Jack always wondered what sort of panties women were wearing. He could feel that it wasn't a thong but full briefs, not unexpected for a woman her age. Mary sucked for longer, she then reached up her thigh and started lowering her panties.
"Mary, we can't fuck in the taxi" Jack said quietly.
"Of course, we can sweetie" she whispered back.
"No, i can't" Jack demanded, stopping her hand.
Mary sat back up, she seemed angry, and she moved back over to the other side of the back seat. Jack breathed a sigh of relief as the taxi approached her house. The driver pulled over. Mary handed him her credit card to pay the fee.
"Get out" she ordered Jack "I'll get Ron to drive you home from here" she said referring to her husband.
'Ok' Jack thought and he got out of the taxi. Mary led Jack to the front door and fumbled her keys as she opened it.
"Shhh, be quiet noisy" came another man's voice from around the corner, "Claire's asleep" he said referring to their teenage daughter.
Mary grabbed Jacks hand and dragged him down the hall entering the third door on the right. It was their master bedroom, Mary literally shoved Jack onto the bed and began undressing.
"Ron, can you get us a drink" she quite loudly yelled to her husband while now down to her bra and panties.
"OK, this is weird" Jack said alarmingly
"Not at all sweetie" she responded as Ron walked into the room holding two glasses of Scotch on the rocks. "Jack, this is my husband Ron"
The men said hello, where was this going Jack thought. Mary's intentions were very clear as she was soon pulling down Jacks jeans and underwear. Ron sat on a chair in the corner.
"It's ok sweetie, he likes to watch" she whispered in Jacks ear, grabbing his erect penis again and giving it a tug.
Jack had been in some interesting sexual scenarios over the years but this was a first, it was kinky and he liked it. He wasn't really attracted to Mary but what could he do, this older woman was insisting on raping him. She climbed on him and placed his cock between her thighs, lowering herself down on his younger rod. Jack grabbed her hips and pushed up into her. She was so warm and wet inside, it was the first time Jack had fucked a child bearing pussy In fact, Mary was only the 4th woman that Jack had fucked, ever!!. The first being Suzette, the fat girl that he lost his hetro virginity to, then Amber that he worked with at a previous job, followed by Paige and now Mary. Jack felt guilt but he also felt ecstasy as he proceeded to roger this old cougar, soon thrusting up into her with venom. Her large tits bouncing as she pounded up and down on him like a sledgehammer. Ron sat in the corner, his cock now in his hand. It was quite a big cock, likely 8 inches and quite thick. He was a fit man, apparently a boy scouts' leader so was often away hiking on weekends. Maybe this was why Mary liked to play around.
Mary climbed off Jack and got on all fours, Jack kneeled in behind her and pushed into her again. Hard thrusts making her body shake. He soon felt a hand on his ass, pushing him forward into Mary's love chamber. 'Well, what do we have here?' he thought as Ron moved onto the bed next to Jack, his hard cock pressing on Jack's leg. Without asking Ron leaned in and kissed Jack on the mouth. 'How the fuck did he know I was bi?' Jack thought. He reciprocated and opened his mouth slightly, allowing Ron to explore his mouth with his tongue. Jack in the meantime continuing to forcefully fuck Ron's wife from behind. While kissing Jack grabbed Ron's cock and pulled it, Ron soon standing on the bed placing his tool in front of Jacks face. Jack didn't need and invite as he took it in his mouth, devouring as much of it as he could, sucking it with all his might, making it so wet and slippery with his sliver.
Jack continued pushing into Mary, Ron moved around behind him, his cock rubbing all over Jacks chubby ass. 'Fuck, can i take this?' Jack thought. he was yet to use the toy he bought down in Melbourne with Mandy. Jack leaned forward a bit, his cock sliding out of Mary's cunt, his stomach resting on Mary's back. Ron pushed the tip in between Jacks cheeks. Mary slid out from under Jack, kneeling next to him, she placed her hands on his ass cheeks pulling them apart, she spat into his ass crack, rubbing her saliva over his man hole. Ron moved back in again and pressed his head against Jack's ass. He pushed, Jack grimaced as it popped in though the opening, 'Ok, not so bad' Jack thought. Ron commenced giving Jack a slow fucking, gradually increasing the pace as Jack's ass become more accommodating. This was nothing compared to what Jack could take in his heyday, Jack had fit much more than this in him before, he was just out of match practice. Soon Ron was really belting into Jack, the wind being knocked out of the younger lad. Mary stayed kneeling next to him, stroking his back and ass cheeks as her husband had her way with her work colleague.
Ron moved out from behind and hopped on the bed. It had been a long time since Jack had been a cowboy but he loved it. He stretched his groin out and placed a knee on each side of Ron, he was soon riding the horse, bouncing up and down on the older stallion. Mary moved in front of Jack and put a knee to each side of Ron's head, her position forcing Ron to eat her wet pussy. She reached out with her hands and pinched Jacks nipples, fuck he loved when people played with his tits, it drove him wild, and this was evident as Jack nearly crushed Ron with his dramatic bucking.
"Fuck, I'm cumming!" Ron belched, Jack jumped off Ron quickly grabbing Ron's cock pumping it with his hand, Mary placing her head next to the imminent explosion, Ron shooting his load at her waiting face, smothering her white skin with this even whiter juices.
It was Jacks turn to finish, Mary laid on her back, Jack repositioning between her legs, he went straight in and pumped hard and fast. Within minutes he knew he was about to go, he pulled out, Ron grabbing Jacks cock in his hand and pumped Jack's load all over Mary's stomach. Mary rubbed it in and licked it from her fingers. They were done.
Ron was driving Jack home, they had a little bit of a chat, Ron advising that their open marriage is what keeps them going, Jack wondering if the daughter had heard them. Jack got out of the car thanking Ron for the lift. Ron hoped to see Jack again soon. Jack said he hoped so too.
Paige was in bed asleep, Jack went straight to the shower, his ass was burning after it's first penetration in a couple of years. He washed himself thoroughly and gave his mouth a good rinse. Grabbing his phone he messaged Mandy ' Fuck do I have a story for you!'
Mandy felt her phone vibrate. her and Jai had finished having sex and were now readying for sleep. He asked who it was. "Just mum seeing if I'm ok" she lied. She typed, 'I Can't wait!!'. Mandy and Jai's first time was ok. Jai was quite young and inexperienced, he didnt have a huge cock, about 5 and a half to 6 inches. Luckily Mandy knew how to make a smaller cock please her, she'd had plenty of practice, she once fucked an Asian man with a small dick ad still got herself to cum. Jai had fucked her doggie and she rode him, his cock not filling her pussy totally, but her hip movement still got her across the line. She had made Jai spend a considerable time eating her pussy, if he wasn't that well-endowed he could let his tongue to the work or a while.
"Have you ever used sex toys?" she asked Jai. He replied that he hadn't. "OK then, I think we need to go shopping" she said with an evil smile.
Jai didn't know what he was in for.....
The end of chapter two.
We hope you enjoyed chapter two of our story. Please watch out for chapter three for more adventures. We love feedback, please feel free to send any to jacki_j@rocketmail.com and mandy_z22@yahoo.com