Cuck Me One More Time

My partner, Jacqueline, is an attractive 50 year old business consultant with a secret life that few people know about. Around 4 years ago I encouraged her to be a Hotwife and we explored this lifestyle for some time although the frequency was relatively limited. She went to swinging clubs with a guy she met and I would be so excited watching her dress up in sexy underwear for another man. She would get home, rather drunk and completely fucked having had sex with three men and a woman. My heart would be beating so loudly as she would relay the stories of being spit roasted or the guy that fucked her so hard or the time another made her squirt for the first time in her life. All the men seemed to have much larger cocks than my 5 inch slim model and she would tell me how much she preferred a large cock. I loved this period of our lives together.

But overtime, she became more and more reluctant to play and I would just have to rely on my fantasies, reading stories on Literotica and sending her ideas on emails which she rarely read or responded to. I'd suggest loads of ways for her to play risk free without any reaction from me. I thought she could have a FWB or an affair but the emotional attachment worried her. I offered the option of meeting men and not telling me the details as long as I knew she was fucking, so she could keep the details secret. She really wasn't interested.

Having confided with her that I accepted her decision to put the Hotwife behind us, I asked if we could at least indulge this as a fantasy. She seemed so much more pleased with this outcome and so we embarked on a Hotwife / Cuckold fantasy world.

New Career, New Opportunities

In the very early days, before she ever had sex as a Hotwife, her first near miss liaison was with a friend called Andy. They had been friends for years but sometime before I met her, they had a brief kiss and cuddle on a night out. Nothing had happened and they remained as friends but she'd tell me about his mild flirting and innuendo when they'd meet.

Andy invited Jacqueline to a work function, as she was wonderful company, intelligent, very outgoing, bubbly and was a perfect plus one. Jacqueline agreed to go and over time I convinced her to dress for him with a view to getting off with him that night. Just another kiss and cuddle (that may possibly lead to more). Jacqueline dressed in black stockings, heels, basque and a sexy black dress that showed off her gorgeous figure. She has the most amazing breasts 36D with super sensitive nipples. I've always been a breast man and I love sucking on them and softly licking and flicking her nipples.

So Andy arrived and picked her up for the function and they left in a taxi. I spent the evening in a super state of excitement and arousal, hoping she would pull. A few hours later she arrived back and told me how she had been very flirtatious with Andy, giving him her complete attention and ,boy, had he noticed. She was a little tipsy at the end and was desperate to kiss him and have her breasts fondled. They got a taxi together and just as they were about to leave, a mutual friend asked to share the cab. Their unintentional chaperone had no idea and Jacqueline arrived home hugely disappointed. We fucked passionately that night and we always thought of Andy as the first experience of her hotwife life.

Having put the Hotwife life behind us, I was very interested and secretly excited to know that Jacqueline was considering working for the same company as Andy. My furtive imagination would consider the options: Christmas parties or drinks after work. I mentioned this to Jacqueline, but she laughed this off saying no chance.

They started working together and everything seemed to be going really well. Business was good and they enjoyed being mates working together and had a high level of mutual trust. Jacqueline would flirt a little as she always had but it was innocent enough. I never expected anything to happen.

Then came the opportunity I was looking forward to. They had to go away on a business trip together for 3 days. As part of our "fantasy-only" lifestyle, she had previously agreed to always take sexy underwear when she went away. It would never be used but provide some stimulus for my cuckold mind. I reminded her of the need to pack underwear and she reluctantly agreed, so in went the high heels bought by one of her fuckbuddies, stockings and basque. I pretended not to be so interested although the bulge in my trousers would have betrayed my true feelings.

Jacqueline left for her trip, looking as super as ever, lovely died red hair, sexy clothes and a secret case for a lucky man. The work was stressful and she texted me to say she was working late and would call. I replied that she need not worry. That evening Andy and Jacqueline had dinner at the Holiday Inn to discuss their day and tactics for the client for the forthcoming day. They drank wine and relaxed in each other's company as they laughed and talked about non work matters. Jacqueline made a mental note to tell me how well she was flirting and Andy seemed interested in her breasts.

At the end of the night, they parted with a small friendly kiss on the cheek and Jacqueline retired to her room. On her bed, she was aware she was feeling horny and had a little squeeze of her breasts through the material of her dress. Her phone bleeped and she assumed it was a text from me. It wasn't, it was from Andy.

"Fancy a nightcap in my room?"

Her heart jumped as he wasn't really offering a nightcap but she felt horny and maybe a little kiss or fondle would be OK.

"Yeah. That sounds good x"

She knocked quietly on the door and Andy opened it quickly still wearing his suit but having removed his tie. She felt nervous as she brushed past him smelling his aftershave. He got her a drink as she sat on the two seater sofa. He sat next to her and they were both quiet as the sexual tension grew. He placed a warm hand on her knee saying "Cheers" and she smiled that smile that could melt your heart. He leant in for a kiss and they embraced passionately as they had some years before. They both put their glasses down to free their hands for some caressing. Their tongues danced and Jacqueline told me afterwards she was instantly wet and horny. After several minutes of passionate interchange he got up and took her had to the bed. They lay together with legs entwined rubbing their bodies together feeling the temperature rise. He squeezed her bottom feeling the suspended strap as he kissed her. His hand squeezed her breast and she sighed in pleasure. She could feel an impressive erection through his trousers as they enjoyed their frottage.

Jacqueline, knowing I would be delighted at the unison, decided Andy probably needed some relief. She could give him a blow job without going all the way, so she massaged his cock through his trousers and he instinctively rolled onto his back to encourage her. She kissed him, rubbing her breasts on his chest as she felt his large member. She unzipped him and his fingers sort out his erect cock. It was much thicker than she was used to and the end was dripping precum. This wasn't going to take long. Expertly, she removed his cock from his underwear and wanked it slowly admiring its length and girth. She knelt between his legs as she licked the length and he stared in amazement. Smiling back, she licked the precum tasting his salty dew with her tongue. Andy removed his trousers and opened his legs allowing Jacqueline to lick his balls while wanking his superior member. His face gave away his near climax and she deftly placed the bulbous end in her eager mouth and gave him a deep blow job. Andy warned of his impending orgasm and she swallowed his cum moaning loudly at the tremendous volume. Slowly she kissed and sucked his cock as he moaned encouragement and gratitude.

She moved next to him to kiss some more and he kissed her with renewed passion, surprising her with a quick hand up her thigh. She parted her legs as the dress rode up and he could feel the heat from her wet pussy. His finger found her pussy and she moaned and pressed her tongue into his mouth. She needed to cum now. He finger fucked her and worked her closer to orgasm.

He removed his finger and asked her to take off her dress. Jacqueline wanted some breast attention and removed the dress quickly allowing Andy to admire the basque and prominent breasts. He seemed to read her mind and exposed both breasts before feasting on the soft flesh to her immediate delight. The nipples responded and were much larger than he had ever experienced. He marvelled at their shape and sucked each in turn as she thrived in ecstasy.

Andy removed her knickers and moved his face to her pussy entrance. The scent was delicious and he went to start kissing, sucking and probing her sweet pussy. She was in heaven as his hands reached up to simultaneously play with her nipples. Her orgasm was very apparent as she buckled, shook and moaned like never before. The sight of this beautiful lady in her moment of climax aroused him greatly and his cock twitched back to a full erection. He positioned his cock at her warm entrance and her eyes grew wide in amazement knowing she was going to get fucked. She raised her upper body off the bed with her arms to watch as the thicker cock slowly penetrated her warm pussy. She gasped at the size and he likewise was impressed that her pussy could be so tight. His cock was hard as steel again and he took his pleasure in her body, fucking her and kissing her at the same time. She enjoyed the excitement of the unexpected new cock, as he humped her skillfully.

There was true passion as the friends became lovers and she accepted his cock deep inside of her. With stamina, he maintained a steady motion and her pussy stretched to accept the bigger cock. He paused to ask her to ride him and she agreed. He dismounted and lay on the bed as she sucked his cock again, tasting her own juices. She placed the end at the entrance of her pussy and quivered as she slipped onto his erection. He tweaked her nipples as she rode him, enjoying being a whore again for the night. "Don't cum in me" she said as their bodies moved together as one.

He was getting close and decided to reposition himself and went behind her in doggy style. Jacqueline loves cock from behind and bunched her hair for him to hold. He fucked her from behind, holding her hair as his girl, the full length of his cock slipped in and out as she moaned loudly. He was becoming more urgent and she enjoyed feeling his balls slap against her. He grunted as he shot his load inside her pussy. She dropped her head to the bed leaving her ass for him to admire as he pulled his cock from her.

She knew his semen was inside her and he now had some ownership over her. He had taken her and made her his own. She would be his whore.