Background Reading Chapters 1 -9 first.
I am cuckolded by my wife Angela, and it's been a lifestyle for a couple of years now. I am compressive and we both get so much pleasure out of this fact.
We wanted to celebrate the easing of lockdown by meeting a couple of guy's for sex as soon as restrictions changed. There was only one week to wait when the news broke, the remaining restrictions would be in place for another four weeks. It was disappointing but we discussed it and we went ahead as planned.
To make the event memorable and celebrate a return to wife sharing freedom we decided to arrange an evening of group fun. It was a compromise, my wife particularly enjoys the attention of two men. I was hoping for a larger group to make it a truly memorable party. Angela said that was not going to happen and she would be more comfortable with just a couple of guy's, however, after some persuasion we settled on three to make it amazing for both of us. We decided to stay over at a nice hotel instead of using our house.
We booked a small suite so to have enough space for a few mini bar drinks and Champagne to get us in the mood and lighten any tension.
We carefully selected the three men who would be most suited as a group. I was more than happy to sit and watch Angela enjoy herself as she entertained them all.
The men we had chosen were all known to us and were previous lovers who have had sex with her numerous times in the past.
Ben was one of the first experienced 'Bulls' my wife had been with. He is caucasian, 36, good looking, a fit body, strong build and a dominant alpha male. Ben is single and will eternally stay as such, he is very skilled in the bedroom for pleasuring any cuckolding wife and enjoys proving it. Ben takes delight in making the husband uncomfortable and enjoys showing he is better equipped in size and technique to satisfy his wife. Ben was also the first guy to introduce my wife to anal sex.
The second guy, Tyler is black, also younger than my wife, solid in his build and generally a mountain of a man. Angela has had plenty of sexy fun with him and there is a real connection between them. Tyler understands her and he knows which buttons to press to fulfill her needs. Tyler also introduced her to several of his friends at a New Year's Eve party which went from an innocent gathering and then turned into flirting, sexy talk and heavy petting. We don't recall much from that night at all, but we know several of the guy's made out with Angela. Tyler is very tender and he too loves sex with other men's wives.
The third guy was Paul, whom has only recently made our acquaintance as a lodger, he is three years older than Angela. It has since turned out to be much more than a room for the night. When someone lives under the same roof you soon build a rapport with them, but this went much deeper with Paul. In an instant Paul made an impression on my wife and she often spent the night in his bed. Paul is also black and he is in a relationship with the ever suffering Becky.
We were bending the rules for the meet to go ahead as six people are allowed to meet inside, however that means social distancing should take place. It just won't be happening when we are in the hotel room though, quite the opposite as my wife will be very close.
The week leading up to our hotel date was difficult to deal with, it had been several months since we played last. We discussed all kinds of scenarios, ordinarily we turned up, one thing led to another and Angela would end up in bed having sex while I watched.
Unusually we were very apprehensive, this time felt different though, it took us back to our earlier meets when we hurriedly bumbled our way, almost blind. It was often rushed and functional, but eventually we learned to savour it more and slowed the pace to make the most of it.
This was back to the beginning, a nervousness which would be over turned by excitement and passion by the end. I reassured my wife she would be fine, as soon as we met the guy's she would relax more. I tried to ease her worries by the fact that if it didn't feel right at any point we could back out and call it off. Angela said she didn't want to do that and it would be fine when the time comes she will definitely feel in the mood for sex.
"I'm being silly love, we can take it slowly, after all, it will be the same as making love three times in a row," she smiled.
I smiled too, "we can ease into it, we will be fine love, afterwards we will be wondering why we were so worried." I guess we were convincing each other.
Unable to recall all the exact details of conversations I have tried to keep the content as close as I can so you can get the gist of it.
This is my memory of the events of that evening on Friday June 25th 2021.
We arranged to meet in the bar of the hotel late afternoon, all the guy's arrived separately. Angela and I had checked in as early as possible to explore the suite and mini bar. We wanted to celebrate properly, after all it wasn't cheap, so an early arrival was important to us. The health suite was real classy and we spent a few hours relaxing. I was already thinking about the evening and possibly the night ahead too. Angela and I felt the same, we were both nervous, apprehensive, and excited at the same time as it had been a while since our last encounter.
All through the day we were very 'touchy, feely' to reassure each other. Angela loves to please me by going through with this very intimate act of sharing her with others and I want to watch my wife enjoy the pleasure and freedom it gives to her.
While we were in the steam room she mentioned that Ben had text her earlier in the week.
"I assume he is still coming love?" I asked.
"Yes, he is, no doubt about that, he did have a special request though," Angela said with a grin.
"Which was...?"
"I'm to ensure you are wearing the cock cage he sent us that very first time the three of us hooked up together."
"Why? Did he say why love?"
"Yes, he likes to see a cuckold know his place, anyway I want you in it too. Three men are plenty enough for one night and you get off just by watching, don't you dear?" she said, smiling at me. "We can make love anytime, let's just see how it goes, we can wait until I'm in the mood for sex again in the next day or so."
"I'm fully aware you enjoy the restriction chastity brings, you cannot hide the secret from me, I know you too well, you love it. Anyway I have packed it in our bags, so it's decided, and we can't disappoint Ben so I will fit it before we meet him." Angela's tone sounded abrupt, it was clearly non negotiable.
Quietly though, my cock was feeling a twinge of excitement to be honest, my wife certainly knows me so well.
Whilst at the hotel Angela enjoyed some beauty treatments, she wanted to look and feel her best for our long awaited return to wife sharing. After an afternoon of her body being pampered she would be very relaxed and ready for a sexually charged evening.
Angela was getting ready after her spa sessions, I had just stepped from the shower to see her in newly purchased bra and panties, she looked lovely. I could smell her perfume, her hair and makeup was perfect, my anxiety was becoming excitement now. In an hour or so my eyes would not be alone seeing my wife in just her underwear. A brand new dress was waiting on the hanger.
"I've been waiting for you love, we don't want to be late. I have something for you."
The chastity cage was in her hand, already opened and ready to fit on me. I could feel myself getting harder under my towel, I dropped it and stood naked and waiting. Angela tried to ease my cock into the device but I was already swelling, impatiently she tried to ease it in. I yelped out as her nails cut into my foreskin.
"For fuck sake Alan, I've got to get it in."
