Sharing Sherry with Strangers

The final of four parts. Warning for the haters, this story involves cuckolding.

Chapter Eleven

How did we progress from swinging with friends to this ... hanging out vicariously in a bar, admittedly an upmarket bar so my gorgeous wife Sherry can try to pick up a guy to invite back to our 5-star hotel room upstairs with the express intent of fucking his brains out while I watch? Could it be that we ran out of couples that we were close enough to that we could assume might swap and that were unlikely to take offence if our guess was wrong? We did enjoy two great nights, firstly with Cathy and Brian, then with Rebecca and Ben, although not enough to contemplate returning for seconds with either couple.

Can you believe that it was actually my darling Sherry that dreamed up this new plan and after spelling out some basic ground rules, I must admit that with such voyeuristic tendencies where my wife is concerned, I didn't take much convincing. I was beginning to wonder what dark thoughts lurk in her mind because although I was the one to start this by buying and playing that swingers DVD, pretending that my selection was purely accidental, it was Sherry who encouraged me to follow my fantasy and who made my voyeuristic dream a reality.

As I recall, this latest scheme came up out of the blue one lazy weeknight when we were luxuriating in the after-glow of joint orgasms from a frantic session of sex in bed. "Darling, have you given any thought to our next adventure?"

We were both laying on our backs, stark naked, our heavy breathing subsiding. I turned my head to look at my wife, "Adventure, what do you mean honey?"

"Well, swapping with Cathy and Brian and Rebecca and Ben was an adventure in sex for us, wasn't it?"

"Oh it sure was, two great nights."

"And we are both agreed that we wouldn't rush into any further sleepovers with those two couples ... right?"

"Sure honey, we both felt that having regular nights with the same couple carried a greater risk of infidelity on one or both sides."

"You wouldn't believe Mike; how difficult it's become already with Cathy and Brian. She's been at me for weeks for us to have another night with them. Now today, Brian called, applying more pressure."

"What did you tell him?"

"The same as I've said to Cathy, that we are not looking for ongoing nights, we want to keep it more as a special event. I don't think it will stop them calling."

"We went into this to pick up some pointers from hot sex sessions to rev up our own private times. You must admit after nights like tonight, it's working."

"That's not quite correct Mike, we did start because it had been your fantasy, but I do agree that we have enjoyed some hotter times in bed. I'd venture to say that your technique and your endurance just gets better and better darling. Do you think you learned some stuff off doing Cathy ... or even from Rebecca?"

"They both turned out to be very hot women, so maybe I did?"

"I'm so glad you got so much out of those nights ... you realise that either or both could have been a disaster?"

"So Sherry, you mentioned our next adventure, have you thought of another couple?"

My wife brought her hands up to cover her face, "No-o-o," she drew the word out. "Not another couple, but ... oh my God Mike, I'm embarrassed now that I would even think like this, see what you've done to me with your fantasy. You might think I'm really awful and become perverted. You may want to disown me."

"I never could, just try me."

"W-e-l-l darling, I've been thinking a lot about how all this started ... how you get a thrill out of watching me do it with another guy..."

"And a solid erection, not just a thrill."

"Yes, well I remember how you were disappointed when Rebecca insisted on separate rooms and you had to rely on me telling you everything that Ben and I did together." She removed her hands and turned her head around to look into my eyes, "I thought of somehow arranging a night where you weren't distracted by having to keep another woman happy, a night where you could just sit and watch me do it with another guy."

"Wow, you really have been thinking, haven't you? Hey, that could be exciting, but how would it work, how would we pick out a guy for you to do that with? Have you got anyone in mind?"

"No I don't darling ... oh my God, I am so nervous even suggesting this, I mean I don't want you to get the wrong idea. I'm not that into having sex with anyone else but you darling. But now you've explained your fantasy to me several times and I saw for myself how incredibly worked up you got watching Brian take me from behind on the kitchen table. I mean you banged it into Cathy so hard after watching us, she even commented to me next day how watching me and Brian had turned you into a wild man almost out of control."

"I hope I didn't scare her."

"No, quite the contrary! In her own crude way of expressing things, she told me that was the hardest drilling she's ever had in her life. You can imagine what word she used instead of drilling Mike. It could be why they keep pressing for a second night. Anyway, I thought that it might be a special treat to watch me get done by some guy -- a total stranger this time - and then shove him out the door and you have me as often as you can afterward. Let me feel my wild and out of control man this time instead of Cathy. There, I've said it, what do you think, are you shocked?"

I took her hand and pulled it down to my groin. In spite of having just cum inside her, my cock had sprung up again simply from listening to her plan. "Does this tell you what I think about your idea?"

"Oh, that's amazing, so soon after cumming. You did cum before, didn't you?"

"I sure did and I was all shagged out until you just said what you did. Now I am ready to get inside your lovely body all over again."

"Oh goodie! I'm always ready for that."

"Before we do though, you haven't explained how we would find a guy to do this?"

"Oh no, I didn't did I? W-e-l-l, I hope this doesn't sound tacky, and we could be taking an awful risk, but I actually thought of us going into some upmarket bar ... maybe in a good hotel where the clientele might be businessmen staying in town overnight or something like that."

"If you think by doing that, you'll ensure somebody's clean, it's no guarantee. We could find a plumber or electrician who comes to the house and who looks after himself and is just as clean as some white-collar guy."

"Yes you're right darling, I shouldn't have limited the prospects to business guys. I guess I picked a hotel because we really wouldn't want to have some stranger come here to the house. I mean, he might like it so much that he'd become an ongoing nuisance. By moving this from friends to strangers, I guess we have to be much more careful, don't we?"

"Yes we do, how about we give it a lot more thought and combine our ideas to find the perfect situation. But overall honey, I love your plan and I'm so grateful to you for trying to find more ways to make me happy. Sherry, you're a special woman."

The time for words had finished, I pulled her into my arms and kissed her. When our lips parted, I had a suggestion to make, "Honey, I know you're all comfortable here in bed and we could be lazy and just enjoy one more slow fuck ... both cum again. But I've got an idea ... you reminded me of how turned on I was watching Brian fuck you from behind over the kitchen table. So how about we go repeat the kitchen table fuck ... I'm gonna do you from behind just like Brian did."

We had been so pleasantly relaxed that I anticipated that I might need to press her more to get out of bed, but she virtually crawled over me and was on her feet in no time, "Sounds great, let's do it."

I saw her grab something from off the bedside table and she led the way from our bedroom. Her telling me of the new fantasy was all I needed to get my erection back, but had I required more inspiration, just following her naked arse as she sashayed out to the kitchen would have done it.

She walked into our kitchen, directly to the table, spread her feet wide apart and bent forward over it, eagerly surrendering to a receptive position. I looked down as her arse cheeks naturally spread wide from the lewd position, saw a beautiful and tight anal ring wink at me. I reached for my erection and steered it to the appropriate part of her spread wet labia lips, knowing the top entry point was out of bounds with her.

Sherry half turned her head back toward me, "I'm fully wet, so no preliminaries, just get it in now," she urged and I pushed the head of my cock at her vaginal opening. "Umm! she purred, her head still half turned around. Although she was resting her upper body on both bent arms, she managed to open one hand to reveal her tube of KY-gel, "Here Mike, I want you to put some of this on your finger, and then I'd like you to stick that finger in my bottom."

Always the more delicate words from my Sherry. But whether she called it her bottom or her arse, I nearly fell over. She had never suggested any form of anal play with me since that first intimate night just after we met.

I almost dropped the KY tube on the floor, such was my haste to squeeze some gel onto two fingers. I was pleased I grabbed it before it fell because it would have been a distraction to have to pull my cock-head out of her vagina after just getting it pleasantly ensconced.

I brought the two lubed fingers up to her tight little pucker that was so openly displayed before my eyes. "Are you sure about this?" I checked even as I was running one finger around the outer rim, my digit spreading the gel all round her anal entrance.

"Really sure, it's only fair Mike, you watched Brian do it to me, I can't deny you, my husband."

"Okay, let me know if I'm not doing it right?" and having made her tiny pucker wet and shiny, I stiffened one finger and gently pressed it in through the small opening. Her body tensed so I distracted her by pushing my cock forward a couple of inches, sinking some of my shaft into her vagina.

"Oh darling, you're sure doing it right!" she gasped as her body absorbed half of my erection.

"Yeah Sherry, I know I'm doing that part right, but it's this part..." and I pushed my finger firmly against her sphincter, it gave way surprisingly easily. I sunk in to the first knuckle, "...how's this going?"

"Oh God darling, it's going wonderfully, oh I love it!"

I pressed the rest of my cock up into the hot wet velvet lining of her passage, deliriously watching from above and behind the sight of the rest of my shaft disappearing inside her vagina. Then I stiffened that finger again and pushed the digit in to the second knuckle and my wife sighed in her contentment. 'How lucky am I to have such a woman,' I thought at this moment as I reflected on the new plan she had just proposed, taking our extra-marital activities to the next level.

I got into a rhythm, finger sliding into her anus as my cock withdrew and then cock pushing back all the way deep into her vagina as my finger withdrew until only the pad and the nail held tightly inside her tiny pucker. She was moaning with pleasure so I knew I was doing something right, but I had this overwhelming urge to not waste the gel I had gathered onto my second finger. With precision timing, I pushed the second finger in alongside the first on a given in-stroke and Sherry screamed out, "Oh God yes ... yes!"

We both came powerfully and as she did, I pushed my two fingers beyond the second knuckle, engulfing their complete length inside my wife's delectable arse.

When I ceased pumping any more cum into my wife's vagina, I looked down to watch the withdrawal of my two fingers from inside her anus. Then resting my free hand in the middle of her back to hold her body steady, I pulled my deflating cock out from the delicious sanctity of her velvety vagina.

My wife straightened her body up, turned and kissed me passionately, eventually breaking to tell me, "That was great darling, I loved it, especially you know what with your fingers. You can do that anytime you want from now on."

"How about we try my cock one day?"

"Err, how about we don't ... sorry, not for now."

Chapter Twelve

So here we were, Sherry and I in a very up-market bar at the Sheraton 5-star hotel in our city, apprehensive that we could run into somebody we knew. We had checked in around 3pm today, gone up to the room, contemplated christening the king-size bed with an afternoon delight fuck, but then Sherry talked me out of it. "I want you on the edge tonight darling, I want you to be hard all night as you watch me with some other guy. And you're not to masturbate while watching this man and me -- whoever he is -- doing it in front of you. You've got to wait until we kick him out of the room and then you're going to jump on top of me and do unspeakable things to me until you've cum at least twice."

"Sounds just great honey, for that I'm sure I can wait."

"I thought you might," she giggled and we settled for a coffee instead of sex.

It was now 10pm on a Wednesday night as we sat singly a couple of tables apart, not wanting to appear to be together as we each scanned the bar from a raised section, about 5 feet above the general floor area. There was quite a good crowd in tonight, but fortunately only one other couple had ventured up onto the raised section at which we sat. We were hoping to find an out-of-town businessman on whom we could try out Sherry's plan, which is why we chose midweek instead of a Friday night ... there could be more locals in the bar on Friday and we didn't want a man from around here. I was certain that if we saw the right one, Sherry would have no trouble in pulling him ... she looked a knockout tonight.

I have described her in a previous story part, but I will recap for the benefit of those who may have forgotten. She is 39 (I'm 42) and a ravishing redhead with shoulder-length hair and still a great body in spite of her having breast-fed our only child. Her boobs are good, about 35 inches and she works out at the gym at least twice a week to retain the narrow 24-inch waist that is more in keeping with a twenty-something. Yes, great bod and I've already indicated an arse to die for.

Tonight, Sherry had dressed to kill in a black number, halter style. Two pieces rose up from her waist in front, just barely covering each breast, continuing on to tie together around the back of her neck, creating a massive nude vee that dived down almost to her waist, exposing the inner slopes of each breast. There was equally massive exposure for the outer slopes too because this little black dress was backless to the waist. There was no way that a bra could be worn under this little number. The lower hem of the dress ended only halfway down her thighs, revealing more than 6 inches of naked flesh to the knees, even more if she sat and her dress rode up.

Nobody else was in earshot of us as I said softly, "What about the guy in the grey suit and tie at the end of the bar?" Sherry turned her head in the direction that I was looking.

"Yes, I've checked him out a couple of times already, he could be the one but I really need a closer look."

"Well, you can either walk right by him on the way to the ladies room or go stand near him to order a drink."

"Umm, I guess I could. I was actually trying to avoid having any more alcohol. I had a couple of wines to give me a buzz and try to wash away the nerves. But you know me, if I have too many more, I'll just become tired and we don't want that. I want to be awake to savour every moment. How are you holding up darling, are you still hard?"

"Honey, I've been rock hard since we checked in this afternoon, I think it's the anticipation of what's going to happen, what I'm going to see. When I lay on the bed watching you get dressed, I thought I was going to blow without even touching my cock. You are going to knock some lucky guy out tonight."

"I'm pleased you're excited about this darling ... no regrets, eh?"

"None at all, I am dying with anticipation."

"Shouldn't be too long now, I can't take the chance that an eligible guy might give up and go to bed on his own. Can you spot any other genuine prospects before I slip down to the bar and check this guy out?"

"No not really, I did think that guy in the blue suit, no tie, over at the table to the left looked promising, but he's got another guy with him and we don't want to take chances that you'd get stuck with two guys."

"Oh God no, look darling I'll cruise past that second one you suggested and just see if he looks interested. Maybe if he spots me and he is keen, he could tell his friend to get lost."

"Okay, I'll leave it to you ... you know the routine once you hook a live one. You bring him up here so that I can put the deal on the table?"

"Yes yes, we discussed all that, I'm good to go. Wish me luck darling, I've got an idea I'll be bringing one of them back with me."

I watched my wife with pride as she carefully navigated the five steps down from the raised section and crossed the floor toward the bar, slowly passing by the two guys at the table on the left. I could see her give the man that we targeted of that pairing a long lingering look and it was fun to watch the reaction of the two men, one nudging the other as she appeared to intentionally wiggle her arse walking away from them. Of course, they could also be reacting to seeing the limited back of Sherry's dress, bare to the waist.

Sherry walked right up to the far end of the bar and paused only 4 feet away from the man in the grey suit seated at the end of the bar. It looked like she might have said something to him or maybe he opened up a conversation. Anyway, my wife stared back down the bar attempting to catch the barman's attention. Then, holding only her purse in one hand, she moved away from the bar, passing close by the latest target, actually extending a hand out to touch his arm as she passed by him.

Wow, what was that about? Who hit on who? She had disappeared from the bar and I assumed that she had gone on to the Ladies Room. Just as the first pair of guys had done, the man in the grey suit turned his head to watch my Sherry until she disappeared from sight. Definitely some interest there.

Three minutes passed and Sherry came back into sight, walking around the end of the bar where the man in the grey suit sat, again touching his arm in an apparent come-on move. I saw her look up to where I was sitting at the table adjacent to where he would no doubt have spotted her earlier. 'What was she saying now?' I wondered.

She had caught the bartender's attention and a third glass of wine was delivered to her. Sherry opened her purse but got no further. The man in the grey suit threw a banknote at the barman. Was this mission accomplished? I watched her smile and say something to the man, maybe thanking him for the drink. She began to head back in my direction and I saw the man slip off his bar stool and follow her. Hey, it's reality time, it's gonna happen. I felt my palms starting to sweat. It was about to be my turn to talk to the man, just as soon as she got him back up here with her.

Sherry headed toward my table but then kept going, passing by me, smiling and winking. She didn't return to her table but continued on to a secluded booth and slid into it, sliding around to the inside end of the table, allowing the man to slip into whichever side he preferred and still leaving room for me to join them, sitting on the opposite side to the man.

He walked by me, drink in hand, a grin a mile wide on his face, already assuming he was on to a good thing. How would he take our proposition? I turned my head to see the man slide in on one side of the booth. I stood up and followed across, sliding in on the other side. The man looked up at me in surprise, "Hey buddy, get lost will you, this is a private party."