Pity/Favor Sex
 

I'll just tell the short version but happy to share details of this weird encounter if anyone is interested.

I'm away for the weekend in a cabin with a group of people and been hitting on this girl I just met this trip. I'm pretty sure she's into me but I'm getting mixed signals. We end up in a hot tub together in our underwear and I put my hand on her leg and she does not resist. There's other people in the tub and I think it might be a bit of naughty fun to sneak in a little rubbing action right in front of everyone without them knowing. I move my hand higher, but she stops me. I'm only pretty sure that we're in fun flirt mode and she pushes back because of the people there, so I keep letting my hands wander. Just when I think I may have misread the situation and gone too far she reaches into my underwear and does this awesome slow hand job without anyone noticing. I try to reciprocate but she still pushes my hand away.

A couple hours later after the partying has died down I'm assuming that we are going change up the sleeping arrangements and find a bed together. To my surprise she says quite kindly and honestly' "Look, I'm just not interested in you in that way." I reminded her of the hot tub scene as if it was some sort of hallucination and she replies, "I was tired of you chasing me around with your erection all night so I thought if I just gave you what you needed then it would be best for both of us."

At first I felt a little rejected, but in retrospect I keep thinking what an awesome chick. Anyone else ever been given sex for pity or as a favor?

A related story...Not something that happened to me but it fits...

Recently we spent a weekend at a nude resort in Florida. The particular resort was basically taken over by swingers on weekends. FL nude resorts have varying tolerances for lifestyle activities. At this one, during the warmer months, there is activity by the pool after dark (otherwise at private homes on the property). Nothing happens on the dance floor or any other public area.
At many of them, any signs of PDA are grounds for immediate expulsion. Some are more accepting after dark on weekends.
We were having breakfast with some swingers (they were there together, but each was married to someone else). They were discussing another resort, where the problem was the owner. A very unpleasant guy. One of the issues they had that he forbade any swinging - UNLESS he was getting his. As they put it, one of the ladies had to "take one for the team" and do him, so the rest of them could play in peace.

DR

Pity Sex for a Widower
 

A friend of my wife and I recently loss his wife to cancer. Bill and his wife had been married forever, and he was taking her loss hard. We used to get together on a regular basis with Bill and his wife. I told my wife that Bill needed us now more than ever, and that we should have him over by himself. She readily agreed. So the big evening came, and Phil showed up with a bottle of wine. We all downed that in no time and started hitting the other booze that we had stocked. After some conversation with Bill talking mainly about missing his wife, we tried to turn the subject to happy times that we all had together. With the dinner hour closely approaching, I said that I had better go out and start the coals. Once outside, I realized that I was out of lighter fluid. I poked my head back in the door, and said that I was going down to the store to get some lighter fluid. Bill offered to come along, but I said to go ahead with his drink, and I would be back in about 30 minutes (the nearest store is 15 miles from our house). So off I went.

Upon returning, there was no one in sight -- not in the kitchen, not in the family room and not outside. As I was searching through the house, I heard a moan and then a groan from what sounded like Bill coming from the bedroom. I slowly opened the bedroom door just a little and saw Bill screwing my wife in the missionary position. I didn’t know what to do, and just shut the door back again to gather my thoughts. Here was one of my best friends fucking my wife. What in the hell? I just sat on the chair across the room from the bedroom door, and waited for them to come out. They did, and saw me immediately. Both looked guilty as hell. Bill said that my wife was only showing him a part of the house that he had never seen. I said, “What part of the house was that – her pussy?” Bill responded that it wasn’t what it looked like, and I replied, “Bull shit!!!” He then admitted it and said that he was so sorry. My wife said that she was sorry as well, and that she was only attempting to cheer Bill up. I asked Bill if he was cheered up. He took a few moments to respond, and then blurted out that he was or had been. Bill said that he didn’t want me to blame my wife. He initially said that maybe he should just leave, but then said, “Go ahead with whatever you want to do with me.” He told me that he would let me hit him or shoot him, and said that he is so miserable he just wished that I would shoot him. I just looked at them both and said that I needed to digest all this, and figure out what I was going to do. In the meantime, I told them just to stay put.

Then I told my wife that I needed to talk with her outside. While Bill waited, I asked her what in the hell led her to screw him. She apologized profusely, and said that there was no sexual attraction that led her to fuck him. She really just felt so sorry for him, she just wanted to give him some joy after all his sadness. She added that he wasn’t even that good in bed and had premature ejaculation. She really got no joy sexually from the screw. I began to feel some degree of remorse in my harshness toward her. I believed that she was really just doing it for him. She and I both have had other partners along the way. However, most of the time it has been swinging with other couples simultaneously. That was sex, but this was more of a humanitarian effort on her part. I thought for a few minutes and said that maybe this could work out. I always get off on watching her screw other people’s significant other while I am doing the same right alongside of her. I offered, what if I had her service Bill with a MFM approach with me being the other party. After awhile, maybe Bill could bring a willing partner along with him, and it could lead to MFMF. My wife said, “Are you really serious?” I nodded that I was. She said that she had to think about that one. I said that I wanted an answer within an hour, She agreed to supply one. Then I said that we had better get back into the house to Bill before he thought that I had done her in.

Upon returning to the kitchen, Bill was well on his way to becoming polluted on my Jack Daniels. I told them that we might as well eat those steaks that had been waiting for the grill. I went out and grilled the steaks. I don’t think any of us had a great time eating, but it helped break the ice. As we were cleaning up the dishes, my wife said that she had thought over my proposition, and she was game, if Bill was. Then over another Bourbon with my wife part of the conversation, I made the proposal to Bill. His mouth dropped open, and he said, “Are you really serious about this?” I agreed that we both were. He thought for a minute, and said that he was in need of being cheered up regularly and wanted to do it. We all shook on it, and Bill promised to find an additional female to participate as soon as possible for me to have as much enjoyment as him. With that, I said, “Well, is everyone ready to get started?” My wife said that Bill might need some time to recover. Bill responded that he thought that he might be good to go. So off to the bedroom the three of us went for a MFM. Amazingly, Bill was able to perform this time, and he and my wife said that he was much better the second time around. She managed to get two climaxes – one from each of us. While one was screwing her, the other was playing with her otherwise available parts. I think she really enjoyed the attention and variety. Then she also managed to get me excited enough while Bill was playing with her tits and pussy to give me a blow job as a grand conclusion to a really unique dinner party. As Bill departed, we all agreed to attempt to get together once a week to “Cheer Bill up.”

the instinct to take care of others -- Japanese style
 

I'd been off work sick with a cold and when I came back, one of my customers was concerned for me. She told me she'd cooked a meal for me and wanted to come over and basically make sure I was okay. I'm never one to say no to a free meal, so after the we closed up, we headed back to my place. We had dinner and then we chatted and watched something on TV. Nothing really happening and I wasn't expecting it to as. I certainly didn't want to kick her out straight away as she'd been kind enough to prepare a meal for me and come over and feed me. So as we were chatting she asked if I wanted a massage and of course I said yes. That went on for about 30 mins I started to fall asleep and she said it was probably best to take a shower or bath. She wasn't prepping to leave so I assumed she was just going to wait until I'd got myself to bed. I took my shower got dressed and then she asked me if I still felt some stress. I said I did and so she said for me to lie down, but this time on my back. She started to rub my chest and then my legs. And then before you know it, she was rubbing my cock. She just asked me if I was okay and I nodded. She then pulled down my pants and gave me a blowjob, swallowed, cleaned up, went to the toilet and said she had a good time and hoped she made me feel better and then left.

Pretty great way to get over a cold!

I guessed that this was her way to see me and it gave her a good excuse. We actually met quite a few times, but under healthier circumstances. Alas, she moved back to her hometown as uni had finished.

I'm glad you brought this up!

My wife finds it weird because when she's sick, she just wants to be left alone to wallow in her misery...But when I'm sick, I absolutely love to just lay there and have her rub me down with light, fingertip caresses (a kind of wimpy massage), followed by a long, teasing blowjob/handjob. That makes me being sick almost worth it! In fact, this my favorite time for a little non-reciprocated attention!

What do you all think? When you're sick, would you rather be left alone or does my wife's treatment sound like a good idea to you?

Helping out a friend
 

A couple years ago we were hanging out with another couple playing card games and drinking. The other wife got a little over served and fell asleep. We played on for a while expecting she would rejoin us, but after a while it was clear she wad down for the night.

Before she had passed out we had been playing games that had occasional dares like flashing tits or mooning, and when she first passed out we had stopped the dares, but after a while they started up again. Every time my wife showed her tits our friend would comment about how great they looked (his wife has much smaller boobs) and my wife really enjoyed the compliments.

After a while I finally said to my wife that since he admires them so much, she should let him have a good feel of her boobs. She resisted at first saying that her friend wouldn’t like it, but after a while we wore her down and she let him have a good groping of her boobs.

Then after that I suggested that he can’t really get the full experience of her tits unless he sucks on her nipples. My wife said that she felt bad for him because his wife had crashed and for the rest of the night that became her reason for everything we did.

At the end of the evening I mentioned that I felt bad about our friend going to bed all worked up, and she agreed that was unfair, so she got on her knees and gave us a double blow job.

Then we all went to bed.

The next morning I asked her about it and she said she felt genuinely bad about getting him aroused, and thought it was only fair to finish what she had started.

I had just graduated high school and I was barely 18 years old when this happened. One of my best friends in school was a guy. We had practically grown up together. We went to a small high school where everyone basically knew everyone and we had been in school together since grade school.

I will call him Aaron for this. He was dating a girl from a neighboring town and they had dated for 2 years. She was a year younger than us. He had caught her cheating a few days after our senior prom and right before graduation. She actually thought she could go to another town and go to a prom there with a guy and not get caught. Of course someone from our school was there and saw her. So anyway he was really tore up about it and forgave her at first until some of our other guy friends rode him hard for being a pushover.

We had each other on speed dial on our cell phones and I had been his shoulder to cry on several nights. My bf knew of our friendship and the way it was between us so he had no problems with me hanging out with him and talking to him. I hate jealousy anyway and had never given him a reason to be jealous.

My bf wanted to go with a bunch of his friends to a MMA match in Tulsa. Aaron knew they were going and asked me if we could hang out that night. I told my bf and he was like no problem. So Aaron and I went out to eat an early supper and then we went back to his house to watch TV and talk in his room.

His folks weren't home.

I was like where are your folks and they were in Oklahoma City at Bricktown. So we went to his room and we did not turn on the TV. We talked about a lot of stuff we had already talked about over the phone. He kept telling me I was his best friend and we had been hugging each other.


He got some wine out of his folks fridge and we drank some. He seemed nervous and I was like what? He said, "Rachel you know you are my absolute closest friend?"

I said, "Yes. I know."

He said, "I am just going to come out and ask you this so don't get mad." I just shrugged my shoulders a little bewildered.

He said, "Would you let me have sex with you?"

I was like Whah? Are you serious?!

He says, "Rachel I wouldn't ask you if I didn't really need to do this."

I said Why would you need to do this other than being horny?

He took a long deep breath and he says, "Confidence. I feel like I have been punched in the gut. I need to get this over with."

"What about my bf?" I said. "You know I asked him if he was okay with me hanging out with you!"

He said, "I would never tell a soul." He looks at me in my eyes and he says, "I really need this and you are the only person I trust enough to ask to do this."

I said, "Dude you know it would be too weird to kiss!"

He said, "We don't have to kiss if you don't want to."

I felt weird and I was surprised when I realized I was turned on some from our conversation. "So you just want to fuck me?"

He said,"Honestly that is what it would be but it would be more than that between you and me."

I sit there and I know I looked shocked. I said, "If I did it you could never tell."

He said, "I won't." And he stood up and started taking off his clothes. I was wearing a light blouse and jeans. I had on comfy cotton panties and a bra that did not match. I was not here to be sexy. I got up and took my clothes off and I was feeling really warm inside. I had just gotten my tattoo on my hip a few weeks before and he leaned forward and kissed it. He guided me down to the bed and pushed my legs apart and ate my pussy.

He knew what he was doing and I put my hand down to rub his head as he licked me and sucked on my pussy. I felt his tongue inside and I was breathing hard. It was really feeling good and he got up and he jumped out of bed and ran to the bathroom. He came back with baby oil and put some on his penis. He was very hard. He got on the bed between my legs and he made the connection and it slid up inside of me.

His face hovered over mine as he fucked me, moving in and out slow but hard, pushing hard against me as he thrust. He moved in and out as we looked in each other's eyes and I opened my mouth to moan some. He kissed me gently on the lips once, not much more than a peck and then he told me I was so tight he was going to cum.

He barely got the word out of his mouth and he started grunting and throbbing inside of me. His orgasm brought on mine and we came together though not exactly together. I was breathing hard as he pushed it inside of me and he told me about their prom night and he told me something I didn't know. He talked to her about marriage some and she had said she wanted that after he got out of college.

He is telling me all of this while he is inside of me. I can feel his sperm running down between my butt cheeks and never seemed to get real soft. About the time his story ended he was hard again and we started round two. It was much harder, passionate and he sucked my titties a lot (Yes the same titties in my avatar picture) and he made me cum again long before he came the second time.

When he emptied himself inside of me he asked me how I felt. I said, "Aaron, I feel like you got me to do to my bf what your gf did to you."

His eyes got wide like he had never thought of that. He said, "Rachel I am sorry."

I said, "Don't start being sorry now. We are best friends, right?"

He said most definitely.

I asked him if we were through and he said no, not yet.

We went down stairs and he had me to get on my hands and knees in the living room floor (Carpet) and he put a pillow down for my knees. He got behind me and fucked me doggy style for a long time. I didn't cum that time but he did. I swear he shot almost as much sperm inside of me the third time as he did the second time but it was real watery and ran out of me when I got up.

He told me I could take a shower before I went home. I checked my watch and it was close to the time I told my folks and my bf I would be home. I told him no, I better not show up at home showered.

I got a pantyliner out of my purse and put it in my panties and got dressed. He knew I was feeling weird and he took my hand and he smiled and said, "Thanks for the pity pussy Rachel."

We both started laughing so hard. It was like it totally broke the awkward tension. I said, "You are freaking pathetic."

He said he knew.

That was the only sexual encounter he and I ever had. My bf and I did not stay together long once college started anyway. I don't feel it was right to cheat but I did. Sometimes you do the wrong thing for the right reasons. That is my contribution for what it is worth.

Happened in a swing club
 

I was hanging out in a club one night while away on business. It was kind of a slow night, but there was a good mix of couples and singles. There wasn't a whole lot of action going on, but enough that most had fun. This guy came in by himself and if you looked up nerd in the dictionary you would see his picture.

Small, mousy guy, homely, and quiet as could be. I and others would say something to him, but all we got back was one-word responses. The group I was socializing with at the bar started to talk about him. Whenever a gal went in "the back" to have fun he would discretely follow them. He was able to watch some action and when he did he would fondle himself, but be covered by his towel.

Our social group at he bar were now making jokes of him when he would go to"the back". Our group included two women who were "players". Some of us guys started teasing the gals about how they should mercy fuck this nerd. Neither wanted to have anything to do with that. We egged them on more and more especially with dirty talk.

We finally convinced them to roll a dice game and the loser had to have sex with him. Game over and this forty y o MILF lost. She was a brunette, big boobs and a fine ass. Usually very socially and sexually aggressive. She waited until the guy had followed the this couple (The gal (Kelsey) was the one that didn't lose the dice game.) to "the back".

When they got in "the back" the couple started getting on in the open area. Sure enough the nerd started fondling himself under the towel. The rest of us including the dice game loser (Sandy) quietly went into the back. The rest of us kept our distance, but Sandy quietly walked up behind him.

She whispered something in his ear and he jumped like he was shocked. She reached her hand under his towel and grabbed his cock and told him in a sexy voice that she had to have some of his cock. I don't think he could even speak a word he was so shook up. She took his arm and led him onto a mattress.

She took his towel and had him lay on his back. When she moved away a bit we all could see that this nerdy guy had a huge fat cock. Sandy leaned down and kissed the head and looked at Kelsey and said that it looks like she had actually won the dice game. The rest of us watched her ravish his body until he got aggressive and started pleasuring Sandy.

He ate that pussy of hers like there was no tomorrow. Of course she sucked him well and they fucked like rabbits. Kelsey ended up joining them for s while then the rest of us joined in the festivities. You wouldn't believe how this guy "came out of his shell". Talkative, social, laughing, but still looked like the nerd. He ended up having sex with three women. We never saw him again, but I bet he won't ever forget that night.

I've posted this before, likely years ago. When were married about 4 years we lived in an apartment complex, one of the first people we met was a bachelor who lived upstairs. He was from the Midwest, a CPA who worked for one of the big accounting firms. The term wasn't used yet, but today John would be called a nerd, tall, glasses, skinny and shy. He was a great friend, he was a sports nut like me, we went hunting, fishing, my wife liked that I didn't bother her to go to football games, which she hated.

John didn't date that we could see, my wife set him up with her hot sister and we double dated. It was an awkward evening to say the least, John barely said a word, he was so uncomfortable around an attractive woman he couldn't talk. My wife was likely the only woman, besides his distant mother and sister, that he spoke to.

One night we invited him over, I made a big batch of spaghetti and we knew he would appreciate company. John brought some wine, a surprise since he rarely even had a beer. We had dinner, finished the wine, my wife was nursing, so she only had a sip. The three of us started watching a movie, at some point there was a brief nude scene, some actress was topless for a few minutes. I made a big "wow" deal out of it, my wife elbowed me, John said something about the only breasts he had ever seen were in movies or magazines.

The movie ended, we were finishing up the wine and my wife surprised me by asking John if he was serious that he had never seen a woman's breasts, he assured her he had not. Now I know the way my wife thinks, so I knew what was next, we had a baby girl and my wife had been very modest about nursing her, only me, my mother and sister-in-law, had seen more than a cover-up. Like on cue, I hear the baby waking up, my wife goes and get her, usually she excuses herself and nurses the baby in her room. This time she came out with the baby, sat down in the rocker, unbuttoned her blouse, unhooked her bra in front, and bared her breasts to John. Her very sexy, huge since she was nursing, ripe, pink breasts. Johns eyes were as big as saucers, my wife said "I don't mind you watching, it's a natural part of being a person."

She even invited him to come watch closer, he was staring, but I could tell he was also enjoying the beauty of the moment. I didn't expect to be so turned on by having another guy look at my wife's breasts, but I couldn't wait for him to leave so I could have fun with her. Discovering my fetish gave us a lot of fun times later.

Years ago, my girlfriend was studying in America for a year. We had a 6 week tour of the States planned but things had changed in her mind in the time she'd been away and she broke up with me the day I got there. Being British and stubborn we stiffened our upper lips and carried on with the trip. I was still totally in love with her, she had moved on (a few times as it turned out) but I guess she still had her sexual needs. We had sex every few days, most of it passionless, but she gave me a few pity hand/blow jobs over the course of the trip too.

I've given a few pity shags over the years too - been set up with a few friends of friends and whether I was attracted to them or not I usually slept with them at the end of the night

This is a follow-up to "Pity Sex" (Frame 3 of this string)
 

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.

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

Pity Sex Again
 

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.

Yes
 

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.

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.

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.

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

But does that actually qualify? :D

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.