Once we were in the privacy of our hotel room Emily started to make out with him. There was no need for the casual flirting anymore. It was clear where this was going. Clothes began to slowly come off and soon my wife was standing half naked, kissing another man, while he explored her body with his hands.
More than anything else the whole situation in those moments just seemed... surreal. Watching her remove her tank top. It had been selected earlier that night after much anxious fretting on Emily's part. She had tried on virtually every piece of clothing in her suitcase before settling on the top for its cleavage enhancing properties. She surmised that he had seemed to admire her breasts during their conversations by the pool over the previous few days. I couldn't deny her logic, and the red bra that she had selected to go underneath it had served to create a tantalizing canyon between her large breasts as it held them up and pushed them together.
This was the bra that I had just watched him remove. Unlike in the movies it did not just flick off and disappear like magic. The four clasps were responsible for a considerable task and he methodically undid them until they were released from their responsibilities. Her large boobs dropped down to hang naturally as she pulled the cups from her breasts and dropped the garment to the ground.
I had a momentary view of her spectacular chest before he wrapped his arms around her from behind, lifting, squeezing, and kneading her boobs. Something which I had done myself countless times over the years.
As they returned to kissing passionately my wife's panties were soon drawn down her legs until she was stood entirely nude in front of him. His tie was gone, shirt unbuttoned, and her hands had been exploring eagerly around the outside of his pants. Things appeared ready to progress further.
However, she broke from him and turned to me. She said nothing to him but held up a finger, silently asking him to wait and be patient for a moment. As she crossed the room slowly her eyes fixed on me and she gave me a knowing look.
I had been unsure that she would even go down this path. Just the sheer intensity of the evening so far had caused me to assume that perhaps she would skip this part of the encounter. It was her first time after all...
However, as she crossed the room towards me the look on her face made it very clear what she wanted me to do... and I wouldn't argue.
I walked over to my travel bag and reached for a small case in one of the inside pockets. I opened it and retrieved the contents. Running my hand over it I marvelled at the fact that
this
was ACTUALLY happening. Returning to my wife I passed the small plastic cage and lock into her outstretched hand. From across the room he watched in surprised curiosity. I reached down and unbuttoned my pants and allowed them to drop to the ground. I slid my underwear down to follow them. Watching my wife being stripped naked in front of me had caused my penis to begin to swell under my clothing. The sudden rush of cool air and the fact that he was watching me get naked served to undermine that and I felt it quickly decreasing in size. I pulled my shirt over my head in order to get it out of the way and provide unfettered access for my wife.
Emily reached to the bedside table and exchanged the cage for our bottle of lube and dripped some into her hands. I gritted my teeth and began to shrink some more as I felt one of her cold hands reach down, lift up my balls, and begin massaging the lube around them. Her other hand performed a similar task on my now flaccid dick. As she coated my penis in slick lube she held it up and pointed it towards her naked vagina, just a couple of inches away. The tuft of blonde pubic hair which traditionally adorned her mound was gone. It had been shaved off in the bath the prior evening as our fantasies of this happening started to feel more like a potential reality. Our lovemaking over the previous nights since she had met him had been spectacular. Each night became more exciting as we explored the fantasy further... and eventually considered it as an actual possibility. Despite how great our sex had been I knew that my efforts were surely about to be eclipsed by the eroticism of her being fucked by another man.
Emily's right hand left my balls and slowly rubbed it's way down her now bald and smooth pussy. The remaining lube was sexily, and slowly rubbed into it as I watched, entranced. She continued to hold my small penis between her two fingers and then lifted her gaze to catch my eye. "Uh uh" she murmured quietly shaking her head. As she did this she comically wiggled my dick back and forth in front of her entrance. So close! As she teased my penis in its smallest state I marvelled at how it could look quite serious when it was erect, but so... silly... when it was small.
Retrieving the cage Emily unlocked it and took the horseshoe shaped ring in her hand. Smiling slyly as she worked, she lifted my balls high and encircled the base with the ring. One by one she inserted the plastic pegs through base. Once complete she expertly fit the top closure onto it, completing the circle which now wrapped snug and tight around my balls and the base of my cock.
The fidgety work, made more difficult by lubricant and the pressure of someone else observing, did not seem to phase my wife. She completed it cooly and with ease, the result of many nights spent fooling around with it in our bedroom. Her locking my dick into the chastity cage. Fantasizing and roleplaying different scenarios. Ones that usually resembled something
quite similar
to what was actually transpiring in real life at the moment! I still struggled to compute that it was ACTUALLY happening. Thankfully my role in this required very little performance or activity. My nervousness would have surely shone through. In contrast, my wife was handling herself in a confident and seductive manner which far belied the fact that this was actually HER first time doing something like this as well.
The clinking ice cubes in his glass drew my attention. He had shifted to the bureau and retrieved his drink. He now seemingly understood the unexpected surprise and brief interlude and he leaned casually against the corner, giving Emily her space, but watching with curiosity.
With the ring in place Emily now retrieved the clear plastic tube and rubbed a generous amount of lube around the inside. She took a step back from me so that she could more easily asses her task and then pressed the base of the tube up against my lubed up dick. Even slick and in its smallest state my head was still larger than the entrance. Em and I both watched as she applied some pressure, relying on the sponginess of my head to give way which it soon did. It popped into the tube, smooshing out tightly against the clear plastic. With more pressure and the prodding encouragement of a couple of fingers she had soon shoved the entirety of my penis into the tight restraint. As my head pushed into the larger cavity at the end it began to regain its shape, albeit smaller. It rendered my endowment so that it appeared that I had very little shaft, mostly just my head which was restrained back tightly towards my encircled balls.
With the last couple adjustments complete my wife produced the lock. It was placed carefully through the small ring as I watched. She then took a step forward and her free arm wrapped around my back as she came in close to me. I felt her breath on my neck followed by a soft kiss. Another one close to my ear.
"I love you"
In that moment it sounded different, meant to carry several meanings.
Reassurance that everything would be ok and that the bond of our relationship and marriage was at no risk.
Appreciation that I was letting her do something like this. A fantasy that had been held unfulfilled for quite some time...
Confirmation that this was actually about to happen and in turn warning that I'd better get ready. My role for the rest of the night was to watch helplessly as my wife was bedded by another man. To watch her experience the lust of being pleasured by someone else... and to experience what would surely be the intense sexual and emotional frustration of not being able to stop her, fuck her myself, or even achieve an erection.
With that she clipped the lock shut.
"Go sit over there"
Different tone entirely. None of the previous empathy. A directive. It was happening. I could tell that she was trying to be serious and dominant now.
Watching as she returned to him I recognized that it was something that she clearly already knew. When they were kissing her hands had been active enough around his waistline that she would have had a pretty good idea of what he was working with.
It was not something we had discussed in the lead up to this. How would one even address it in a situation like this? Just four days ago he had been a stranger who she had started chatting with at one of the resort pools. The
attraction
that had developed over the last few days was what had drawn us to this point. Yes, the three large dildos in her bathroom drawer at home supported the notion that much of our fantasy and roleplay involved another partner who was 'larger' than me. But as she had gotten to know him over the past few days the topic of penis size certainly had not come up! In the dim light of our hotel room I knew that all of this had transpired due to her genuine attraction to him. Even if he'd been modestly endowed she would have still held the same excitement for this encounter.
As Emily drew down his underwear and her suspicions were confirmed her first reaction was to turn to me. Knelt on her knees she surely appreciated the look of
surprise
on my face as she revealed him to me. I appreciated the transparent look of excitement, anticipation, and blind lust on
hers.
She continued to look at me as she let her hand wrap around his thick shaft. Her smile was almost triumphant. Her first big cock.
Raising herself back up again she led him towards the bed and signalled for him to lay down. As he rested his head against the pillows Emily climbed up onto the bed and positioned herself leaning over him at waist level. Sitting in the chair I prepared myself for the first act of what would likely be the most erotic show of my life. Realizing that I was about to watch, and almost telepathically sensing my excitement, my wife rose up. With a sly smirk she twisted her body and repositioned herself so that she was now leaning over him... but facing away from me. I groaned inwardly as I realized she wasn't going to let me see. Instead, I was presented with a wondrous view of her bum as she slowly bent over in front of me and lowered her mouth to him.
The unmistakable sounds of oral sex could immediately be heard and I watched him considerately reach down and hold my wife's hair to the side as she sucked his large cock into her mouth. My view was of her ass, upturned and ready. The seductive curvature of her full bum was perfectly framed by the tanlines around the bottom of it. Several days in the sun had delivered a warm glow to much of her skin, but the areas protected by her one piece swimsuit remained a soft pale white. The same creamy color her whole body had been when we left the cold of Colorado close to a week prior.
The difference in skin tone almost served to accentuate the private nature of certain areas of her body. Anyone at the resort was welcome to view her sexy legs, softly sloped shoulders, or substantial cleavage. But the alabaster white of what was underneath her swimsuit was reserved for those who got to see her only in private settings. Tonight she had invited someone aside from me to see her in her most naked and exposed state. Of her 36 years we had been together for 11 of them. It had been
at least
that long since she had been completely nude in a bedroom with another man.
As Emily bent over him and allowed me to see her extraordinary bum it essentially served as the world's most tantalizing movie trailer. Preventing me from witnessing the opening scenes... but teasing me with what was to come/cum. I knew that in just a short period of time I would likely be witnessing that same view of her bent over, but with another man's penis plowing in and out of her.
