Late Evenings Pt. 1

Introduction:
My first attempt at this kind of thing. Please post feedback and let me know if you want more installments.
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Like other couples with kids, my wife Judy and I go out occasionally with the help of a sitter to watch the kids. We don’t usually go out more than once a month or so, and don’t tend to stay out very late, but the sitter was still part of the deal. On rare occasions we would actually stay out very late to watch some live music and the sitter was always very accommodating and never complained if we stumbled in around 2 in the morning.
The sitter – let’s call her Delia – is attractive and unusual only in the sense that she also has a good daytime job working downtown for a small business. Being 29 and more mature than some neighborhood kid came with a price premium for her services, but still affordable enough to make it worth our while. And, of course, she was trustworthy in our nice home with our kids for the evening. It also meant that since she had a real job and life of her own that she could hold a conversation, so my wife and I often ended up chatting with her whenever we got home even though it was usually past our normal times for bed. Usually, I would want to go straight to bed after a night out, but for some reason we would end up chatting with Delia for awhile before she split.
On one such night, we were all hanging out around midnight after my wife and I got home and Delia asked us if we might be interested in her new babysitting service. At first, I wasn’t paying close attention and figured she would explain to Judy about some scheme allowing us to check-in while we were out, or something along those lines. We weren’t the type to worry, so I started to tune out. But, then Delia caught my attention as she started speaking in a very roundabout way about this new ‘service.’ Delia said that she noticed how often married couples would return home after an evening of fun and seem like they were more interested in getting some sleep than any kind of romance.
In our case, she had us pegged exactly – on most nights (whether we went out or not) I would usually go to bed whenever I got tired and conk out before my wife even came to bed. That’s not because I wasn’t interested in fucking her brains out. No, I would love nothing more than fucking Judy silly any moment I got the chance. Judy keeps herself in great shape, still has a very trim and hot body, and always gets mistaken for someone 15 years younger. The problem is that Judy only ever had a vague interest in sex at the most, and after we had a family, that interest was gone forever. Whenever she was willing to fuck, it was clear that she wasn’t really interested and wanted me to just get it over with. A blowjob? Out of the question. Eating her pussy? Not in years. Doggie style? Nope. Just plain old missionary, and get it over with quickly. On a good night, I might be able to pull out and cum on her tits before she bolted to the bathroom to get cleaned off.
So, when Delia started talking about married couples and the lack of ‘romance,’ it hit home with a bullseye. This talk also caught our attention because it was not only unexpected, but generally the type of thing that is completely out of bounds for the situation. It’s just not everyday that your sitter starts remarking that you don’t look like you fuck very much. Did she say it like that? Of course not. Delia beat around the bush (no pun! turns out she doesn’t have a bush…) and I had no idea where she was going. My only thought (and hope!) was that Judy might get offended and defensive, and then after sending Delia home she would fuck me silly just to prove that she had it in her. Considering what my expectations had been for the remainder of the evening, even that was a very, very welcome thought.
But Delia got a little more to the point and said that we were nice and a good looking couple that deserved to enjoy each other a lot more. She explained that she wanted to ensure that she kept her sitting business going and didn’t want couples like us to stop going out if we weren’t having fun. This was the moment of truth, the moment where Judy could have prudishly responded with a curt ‘no, thank you” and sent Delia on her way for good. I could sense, however, that Judy was somewhat intrigued. Instead of blushing or putting on some bitchy face, she instead looked quizzical and said, “What do you have in mind?”
Delia casually, but confidently, moved over next to me on the couch and put her hand on my leg. She looked over to Judy, who was seated on a chair, and said, “how about if I get Tom in the mood for you?”
I was more than a little dumbfounded and was basically frozen and not sure what to do. Judy just continued to watch indifferently as Delia started massaging my leg and getting closer to my crotch. Judy looked on with the same type of curiosity she might have about a bug crawling on the outside of a window – only interested because she happened to notice it and not sure whether to continue watching.
As Delia softly massaged my leg, my hormones began to shake me from my stupor. I leaned back and didn’t try to hide the raging bulge inside my jeans. Her hands felt so, so good as they began to unbutton my fly. My mind, however, was beginning to enter an ongoing loop of “what the hell is happening” as my eyes darted from Judy, to Delia’s hands, to Delia’s hot little body, and back to Judy again over and over.
I lifted up my hips so Delia could slide my jeans down to my knees. Her hand was warm on my cock and I’m sure she also noticed how hot my cock was. I felt like I was back in high school where you’re so shocked that a chick is actually working your cock that you’re not sure what to do next. All I knew is that I wanted a ‘next’ to happen very soon. Delia, however, was so casual about the handjob that you’d think she was just twirling her hair while sitting at a traffic light. She had a relaxed smile and was looking directly at Judy.
No one said a word, but as Delia continued to stroke me, I started to softly moan and Judy slowly shifted from a look of cold detachment to piqued interest. It was like she wanted to see what was going to happen, like she was watching a movie. I reached my right arm over to Delia and started to rub her back and run my fingers through her hair. She recognized this as the universal sign of “I want a blowjob” and immediately went down on me.
A blow job! An honest to God, real life blow job by a hottie who actually wanted to suck my dick! I thought those days were over! I couldn’t believe my luck. The last time I got a blow job from Judy, it was for hanging up a shelf and lasted about 45 seconds before saying she wanted me to fuck her (as if…!). Delia’s mouth and tongue incredibly warm and soft, and I could tell she was enjoying sucking my dick as much as I was having it in her cute little mouth. She wasn’t aggressive and clearly wasn’t trying to get me to cum. I looked over at Judy, and to my surprise she was relaxing back in her chair and enjoying the show. Her shock seemed to have had also worn off, and I could see her hands beginning to twitch a little bit.
Delia kept alternating between softly sucking the head of my cock and licking the shaft, and after a few minutes when she looked over at Judy, my sexless wife was beginning to lightly touch herself through her skirt. As Delia continued to gently and expertly suck my cock, Judy gently hiked up her own skirt so she could rub her panties. Delia just looked over at Judy and smiled, and then went back to work on me. Since I had never seen Judy stroke her own pussy, this was quite a new thrill for me.
Judy then pulled her panties to the side, and I could see her finger slowly sliding in and out of her pussy. At that point, Delia let go of my cock and turned to Judy, asking her, “Are you ready for him?” To my surprise, Judy responded, “No, keep going” as she started to rub her pussy a little more quickly. As Delia returned to my cock, I reached over and let my hand roam across Delia’s back and ass. I felt the back of her bra underneath her t-shirt, and as Judy watched me slide her shirt up and unfasten her bra, I could see she now had two fingers working her pussy.
Delia shifted her body so I could completely remove her shirt and bra, and my suspicions about her having a tone and taut body were confirmed. Her tits weren’t big, but their moderate size meant they had remained firm and the tan lines surrounding them once again took me back to my youth. Momentarily forgetting all about Judy, I reached over further and ran my hand inside Delia’s shorts so I could feel her smooth ass. I helped her scrunch up a little closer so I could reach over her shorts-clad ass and rub her pussy. The outside of her shorts were already beginning to feel damp and hot around her crotch.
I sat Delia up for a moment and started kissing her full on the mouth as I pawed at her tits. She kept rubbing my cock and I reached down to unzip her shorts and help her slide them off along with her panties. She had the ass we all dream of, and like her tits, it was cutely framed with tan lines. I slid a finger into her pussy. It was soaking wet and immediately covered my finger in her juice. As I pulled it out and licked my finger, Delia moved down to the floor with her ass facing Judy and once again started sucking my cock.
I looked back up at Judy and she now had her blouse unbuttoned with one large tit hanging out awkwardly from her bra. She still was sliding two fingers in and out of her pussy, but now her free hand was alternating between caressing her free tit and rubbing her clit. I could also see that not only was she intently watching the blowjob I was getting, she was also roaming her eyes all over Delia’s naked body.
Delia reached between her own legs and started to rub her own pussy. At this point, Judy’s eyes got a bit wider and she started to really finger fuck herself. Delia must have sensed Judy’s excitement and begin to pay more attention to her own pussy than to my cock. She was still holding it and mindlessly stroking me, but she was now enjoying the feeling of her own pussy getting some attention and kept glancing back at Judy.
Judy was getting hotter and hotter and had a wild look about her. She was intently focused on Delia’s fingers sliding in and out of her shaved pussy. Delia finally let go of my cock, put her head on the floor, arched her back even higher, and then started to really work her pussy while pulling her ass cheeks apart with her other hand so Judy could get an even better view. After about another minute of frenzied fingering, Judy began to shudder and then her entire body stiffened up. After a long moment she began to go limp, exhaled loudly, and sat motionless as Delia kept fingering herself.
Too long without any attention on my cock, I reached down and pulled Delia’s face back up from the floor and positioned it over my waiting dick. As she abandoned her pussy and went back to work on my cock, Judy got up slowly and stumbled out of the room. I wasn’t sure if that meant anything, but I figured at this point there was no sense to stop having fun with Delia. I leaned back again and continued to enjoy Delia’s mouth on my cock. After a few minutes, I decided that I wanted a whole bunch of that hot pussy she had been fingering.
I helped Delia stand up and lay back on the couch, and then dived head first into that beautiful pink slit of hers. She was wet inside and out, and I did my best to lick up every drop. I nibbled on her clit and sucked on it, and then went back to trying to suck out every drop from the inside of her pussy. I kept going back and forth between her slit and her clit, and sometimes I worked her wet asshole with my tongue. She was completely shaved and I was like a kid in a candy store. Well, much better than that. I was a grown man with my faced stuffed in a beautiful pussy and ass, and if the world was coming to an end I would have been the last to know. Or care.
I finally decided that I really needed to fuck this gorgeous chick, so I flipped her over and started to bang her doggie style. She felt better than I remember any chick feeling, but I wanted to take my time and enjoy it. Too much recent history of “hurry up and cum” in my past. My trance was broken as Judy walked up, but before I could worry or even wonder what to do, she sat down right next to us. She had gotten up to get a glass of wine, and I was surprised to see her return, and especially to have her sit down right next to her husband while he was fucking someone else!
As I was fucking Delia, I looked at Judy who was just lying back a bit with a content look on her face. I was surprised to see that although she still had her blouse on, it was completely unbuttoned and she had removed her bra. She was still wearing her skirt as well, but I could see that she had taken her panties off. I kept fucking Delia as Judy just sat there watching us. Delia noticed Judy right next to her and reached over and grabbed one of Judy’s tits once in a while, but she seemed to be enjoying the fucking too much to make much of an effort to grope Judy. I kept looking down at her beautifully shaped ass and tanned body, and then over at Judy with her own gorgeous body that had all the right places exposed.
Judy parted her legs slightly and once again started gently touching her own pussy, and this was starting to really drive me crazy. She slipped a finger in and was watching me pound the shit out of Judy from behind. I could see that her pussy was getting wet again, so I reached down and stuck my own finger in her hole. We both had fingers in her pussy and I could feel how incredibly hot it was. Delia started bucking backwards really hard and I knew I wasn’t going to last much longer. I grabbed Delia’s hips and thrust as hard as I could while looking at Judy rubbing her pussy. Judy seemed like she wanted to get off again, but there was no way in hell I was gonna last long enough to do anything about it.
Realizing that I was going to cum soon, she started really fingering herself. I looked down at her glistening fingers and knew I would blow any moment now. After giving Delia one last thrust, I pulled out my cock and aimed it at Judy. I guess she thought I would blow my load in Delia and looked a bit startled. She pulled her hand way reflexively and then I started cumming. The first burst hit her tits and blouse, and the next landed near her navel and on her skirt. The last couple of bursts I aimed right at her pussy and hit the inside of her thigh and finally just above her swollen clit.
Just as I was finishing my orgasm, Delia spun around and was looking at Judy’s cum covered tits and pussy. She quickly knelt over her and gently tasted a drop of cum that had fallen between Judy’s tits. Liking what she tasted, she began moving her mouth all over Judy’s tits and started slurping up the cum and sucking on her nipples, swallowing everything she could find. Delia then moved down and licked some cum off of Judy’s skirt before getting onto the floor between Judy’s legs. From there, she gobbled up the big gob of cum dangling from Judy’s inner thigh.
I looked up at Judy’s face and her eye’s were screwed tightly shut but she was squeezing one of her own tits and pulling on the nipple. I looked back down at Delia who proceeded to lick the cum off the area around Judy’s pussy. Delia then stuck her tongue in her pussy and started to eat Judy’s juices the same way I had eaten hers. Instantly, Judy started bucking her pussy up into Delia’s face and Delia had to slip her arms under Judy’s spread legs in order to hang on. As Judy started cumming over and over at the touch of Delia’s experienced tongue, I reached over and started squeezing Judy’s tits.
After Judy’s orgasms subsided and we all caught our breath, Delia said “well, I guess I should be going” and slipped quickly back into her shorts and t-shirt, not bothering with her panties and bra. Judy stood up and fastened a couple buttons on her blouse and straightened her skirt before going over to the table to get her purse so she could pay Delia. Judy said “thanks for watching the kids” and Delia told us that she hoped we enjoyed the rest of our weekend. I didn’t say anything, and after closing the door behind Delia, I followed Judy to bed as if nothing unusual at all had happened.

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