Pity/Favor Sex

[Saddledrifter]

Bill did come over with a girlfriend to have a swapping opportunity with my wife and I. His girl was named Cindy. She had a pretty face, but was a little on the large side. However, she did have a nice set of jugs. As we had agreed with Bill, we would have group sex with he and a girlfriend. After a good hour or so of drinking straight shots of Jack and having dinner, and another hour of shots of Jack, we were all loosened up for the task at hand. We started by slow dancing with the other person's mate. Pretty soon, things got a little handsy with some groping and unbuttoning and unzipping. Then Cindy dropped down to her knees and began giving me a BJ. After a several minutes, I said that it was time for us all to retire to the bedroom. Everyone was half undressed by this time, so it was not long before each of us had fully undressed the other's partner. So with everyone nude, we all crawled into bed.

Cindy restarted the BJ on me, while Bill began a missionary fuck on my wife. I terminated the BJ, and pulled Cindy up and over to munch on her enormous boobs. Then we also began to indulge in a missionary style fuck. By now, Bill had me wife leaning over the bed while he was standing and screwing her doggy style. She was totally enjoying Bill's increasing rhythm. I didn't think I could reach Cindy's pussy from the backside due to her rather large derrière. So I continued with the missionary position. After a while with Bill's doggy style screw, my wife was back on the bed to cap Bill's fucking off with the missionary position. Bill was totally into feeling and kissing her boobs while fucking her. She seemed to be enjoying Bill's actions judging from the sounds she was emitting. Finally, we all managed to climax from our respective non-significant other's fuck. We all turned over and lay naked on our backs for awhile to regain our strength. After the ladies cleaned up, we went back to the great room for more drinks.

Several hours later with everyone still nude, we decided to call it a night. They dressed, while we stayed nude for bed. We walked Bill and Cindy out to their car. Everyone said that hey totally enjoyed the evening and their climaxes. With that, Cindy and Bill drove away with the promise that we would all do it again.

[hotsxysweet]

A friend of mine accompanied on a trip for a funeral. Nobody I was super close with but an old friend and since it was a few hour drive she asked if I wanted company. That night in the hotel we had separate beds so wasn't really planning anything. We had never done anything in the past or had an attraction to her other then a friend.

Before going to bed she came over to give me a hug and I went in for a kiss and she kinda pulled back. So I apologized and said I was sorry and it was just emotions or whatever. So i'm in bed and a few minutes later she gets in my bed and says she is sorry she acted that way and didn't mean to make me get embarrassed. She goes in and kisses me and we start to make out a bit, i go to reach down on her and she stops me and says sorry she is on her period. So I'm thinking thats the end but then she goes if you want I'll give you a blowjob. I say no its ok I was just upset and she was like really I don't mind.

So needless to say she went down and gave an incredible blowjob. Swallowed my load and then literally says I hope that made you feel better and she went back in bed. We never brought it up again and did anything after that. So I guess I count it as a pity blowjob lol

[Saddledrifter]

Well, here comes Ol' Bill again. You know the guy that loss his wife of a billion years. Last time he brought his new squeeze Cindy for a swap. But this time Bill was alone, because he broke up with Cindy. I think he just stopped in because he was horny and thought he might be able to do my wife. I was not very sympathetic, because I told Bill he needed to swap with me to continue doing my wife. The only thing Bill had with him was my favorite Gentleman Jack. He knew how to win me over. So we started drinking. I guess I was drinking faster and more heavily than my wife and Bill. I was pouring doubles all night.

We took turns dancing with my wife. She was braless, as usual, and Bill and I were both getting some pretty good feels as we slow danced with her. It seemed that I would dance with her and undo a button on her blouse, and Bill must have been doing the same thing, because pretty soon she only had the bottom button fastened, and during fast dances, you could see her boobs swaying back and forth and falling out of the relatively wide open blouse. Then I began to notice her short shorts were working down her body and were about three to four inches below her belly button. I had not touched them, so Bill must have been pulling them down to get some feels. After awhile, we were all pretty drunk. I saw a great opportunity to get some really good shots of my wife with her blouse totally open and her pants almost down around pussy level. I went back to the bedroom to get my camera, but when I returned, Bill had my wife stripped of her blouse and was slow dancing with her. He had her in such a tight embrace, I could not get a good picture of her boobs and front, so I went back to the bedroom to put my camera back and possibly get a later shot.

Unfortunately, I must have passed out on the bed, because I don't even remember the trip back down the hallway to the bedroom. I just remember waking up on the bed while lying on my camera. What woke me up? Well, the bed was shaking around pretty violently. I awoke slightly only to see Ol' Bill laying the wood to my wife. They were in sthe missionary position parallel to me. They were both nude, and she was really getting off on his screw job, and yelling don't stop. I was a little pissed off that he was screwing her while I was passed out. I arose and said, "No, I won't stop." Then I pushed him off of her. I told him I wasn't taking his cumy seconds. I then began pumping her instead of him. She climaxed as if there had never been an interruption in the sex act. Bill just sat there and watched as I pumped away and unloaded my load in her. I pulled out, and then said to Bill, "Now, you can have the seconds." He didn't hesitate one second and jumped back into gear. He pumped her and then turned her over and plunged in from behind. While he was nailing her from behind. I stuck my dick in her mouth and said, "Maybe you can get it hard again." She started giving me a blow job while getting her jollies from the back end screw. Pretty soon, she spit my dick out while she was screaming from the second climax of her evening. Then once she caught her breath, she went back to working on her BJ with my dick. It never got real hard, but she suck it and tongued it enough to get me a second climax.

I was still drunk as shit, and laid back down and passed out again. When I awoke the next morning, Ol' Bill was lying nude on top of my naked wife and in the missionary position. She had her legs spread wide open, and his dick may have still been inside of her for a second tryst or more that night. I got up and slapped Bill on his bare butt. He looked up, and asked what the hell. I said, "Did you get enough last night." He raise up off my wife and managed a "Well, I guess so." I went and peed while he was getting up. When I walked back in, he was kissing on my wife's tits and fondling her boobs. She was moaning in her sleep from the action. I asked him if he ever had enough. His reply was "not with your wife." I told him that in the future he was going to go without her if he didn't bring someone to swap. He agreed, and got dressed and left. A little later my wife got up with cum draining down her legs. She said, "What the hell?" i said that she had at least three loads in her. She grinned a little, and said, "I guess I did have a fun night." I said, "No more Bill unless he brings a swap." She agreed, but I think she always feels pity for Bill, and she will probably do him again with or without my permission. She is a sap for a sad story.

[GRITS]

Mrs. here,


I have a somewhat running affair w a friend of hubby who was badly injured in war.. his face is disfigured somewhat and went into deep depression.. He really has a very hard time meeting any women.


Hubby asked me a while ago if I would have sex w him?... I said yes, BUT we both agreed it should appear as an illecit affair to him... as if hubby doesn't know.


Reason:... because then he doesn't feel he can just stop by for sex because its ok w hubby.... also so there isn't any problem w him getting to attached.. which is not hard to do in his situation.... its all mental precautions..


So I do have an affair w him usually once a month at a hotel, not at his home by my choice.-- Actually he is very good in bed and I always have a good time w him.... But its still pity sex.... and I'm glad to do it for a brave nice guy.
Hubby always knows when we meet. Hes a fishing & drinking buddy of ours and comes to the house for friend visits and vanilla partys… nothing is said...

[jho]

My wife has a friend who’s wife is no longer interested in sex so she helps him out.
He lives several hours away so most of their encounters are on FaceTime but they have gotten together in person once ( so far)

I’m not sure if it counts as pity sex though because she thinks he is extremely hot and has always had a thing for him.

[piecenick]

My wife played some online word games with a guy on an oil rig in the North Sea. Then she told me she started having online sex with him and his friend, they would all masturbate together on cam. She said she felt sorry for them being away for 6 months at a time.

[guiltydawg]

My sister and I bought a house together in the early 80s when interest rates we're crazy and we were both starting out in our 20s. We had a succession of roommates live with us, some guys and some girls. We had 2 girls plus my sister at times, or 2 guys plus me at times. Different combinations.
Anyway, at one point we had Deb and Kathy living upstairs with my sister while I lived in the basement. I was watching TV upstairs with Kathy one night. Kathy was a friend of Debbie's who was a friend of my sisters.
I don't remember what we were watching, or why I thought I could get away with it. But out of the blue I said to Debbie "How about giving me a blowjob?"
She looks over at me and give me a look like something came over her and said 'Sure'.
Wow.
So we went downstairs and to my room. I had never even kissed Kathy before. She wasn't beautiful, she was kinda chunky. It was probably awful of me at the time, but looking back, I can't believe how horny I was, constantly. I was in really, really good shape but I wasn't seeing anyone at the time. Kathy was a really good friend and we had fun together. But she wasn't sexy to me at the time.
I took off my clothes but she kept hers on. I laid down on my bed and she laid next to me. She couldn't get over how big my cock was. I don't think it's huge, but over the years, I've had many comments from women who've seen a few in their days and they say I'm from big to huge. I know I wouldn't trade it, I'm happy with it.
Anyway, Kathy loved my dick. She gave me a fantastic blowjob, and I played with her tits.
Over the months, she and I kept meeting for blowjobs.
Kathy asked me to fuck her, and I said no, that if we fucked, it would change our friendship. I really thought that. I wasn't that attracted to her, but she was a good friend to me. Looking back of course, I know I should have fucked her. If I could go back I would. She looked forward to our sessions more than me, I think.
When I asked for a blowjob from her, I was asking for me, of course. I wouldn't say it was 'pity' but we both got something we wanted, me more than her at the time.

We also had Bev living with us for a time. Bev was a southern belle who was really nice looking with a nice thin, firm body. I don't remember how we started having sex, but we did, and it was great. I remember one time I came home and she came home at the same time from a Jazzercise type class. That was right about the time of Olivia Newton John and the "Get Physical" video was going around, and all the women were wearing spandex outfits and tights with those thigh stockings. Bev was wearing a all black outfit with those tall thigh stockings and we ended up in the laundry room. I wasn't really in the mood, but boy, she was, and she wasn't letting me go. I fucked her standing while she was on top of the dryer. I think she was one of the first women who was just unabashedly looking for sex when she wanted it. I was glad to help out when I could. Bev loved my dick but she didn't love sucking dick. But we fucked long and hard when she was in the mood. Not sure if that was pity sex....probably more convenience sex than pity sex.

[VXCguy]

I've had some of the best pity sex of my life with my sex partner............ MY HAND LOL!

But does that actually qualify?

[karlhein]

I was on a visit to my sister, between finishing college and heading to professional school. One of my sisters friends had just finished 1st year,at universuty and had a,bad breakup with the bf. She wasn't the most attractive girl, sort of too round, a bit pimply with boobs that didn't attract attention. But, she was pretty smart and very pleasant, but not kind of girl that you chase after right away.
The 2nd afternoon I was there, my sister was off at wirk, so we were alone by the pool. I was,a bit of jock, so she kept looking at me. Turns out the bf was a bit if a tool, had really taken advantage of her as,someone to fuck every couple of weeks.without ever making he feel all that good. He had taken her cherry and made her choke while giving him bjs, but she had nerver cum with him, indeed from what she said, I'm not sure if she had ever cum at all.
After talkng we had gone for a swim, which led to some splashing and a bit of contact. One thing led to another abd we woubd up pressed together and kissing. I wasn't lookibg for a relationship, but my dick told me that it might be fun to be the teacher.
As it turned out, she liked being kissed slow and deep, didn't object when I pulled the top of her swimsuit down, and seemed to like it as I teased her nipples, and really like it when I sucked her nipples. Befire long, her hand was in my trunks, exploring my cock. In due course we were out of the pool with out suits off. Her mouth was on my cock and my finger in her very slippery pussy, rubbing her clitty and makubg her back arch.i was getting worked up and soon was cumming in her mouth.
As I calmed down, I stretched her out and began to lick her pussy. Her old bf had bever done that for her, and she really liked it. Over the bext 20 minutes, I explored her pussy with my mouth, fingers and eyes. As some point, her breeathing changed and she began chenching up, abd had her first orgasm. Her smile afterwards was priceless.
We stayed on the pool deck the rest of the the afternoon, doing lots of fun stuff. I guess I was better endowed than her bf, and thought that sex ought to be mutually pleasureable. That afternoon, we fucked 3 different times, and she got the orgasm thing down.
I stayed at my sisters place for the rest of the week, and we had a lot if sex, in almost every position you could imagine. My sister was laughing at the transformation of her plain Jane friend. I think I taught her that she was beautuful and wasn't just a cum bag for some dorky guy. I even got her to masturbate while I watched, then jerked off for her.
I was never with her again, but heard via my sister that she had a succession of pretty good bfs afterwards, so I guess she just needed to see that sex is mutual affection and pleasure.