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Pity fuck, have you?

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BubbleButtMan
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I was a bouncer in college. Lady came in and spent quite a while telling me how she had just found out her husband of eons had been having an affair. She eventually asked (short of begging) me take her home. Definitely wasn't someone I would have "picked up" but her story just kind of hit me, so, fuck it. All on all, she was great in bed and really knew how to suck a cock...
Guest
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No I haven't and I never will ...
Longredhair
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Yes, quite often. I've taken multiple virginity from multiple guys.

My fave kinds are seeing the incredibly shy guys who can barely talk to me... and the looks on their 'alpha' buddies faces when i drag this guy pff to the bedroom.
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Quote by BubbleButtMan
I was a bouncer in college. Lady came in and spent quite a while telling me how she had just found out her husband of eons had been having an affair. She eventually asked (short of begging) me take her home. Definitely wasn't someone I would have "picked up" but her story just kind of hit me, so, fuck it. All on all, she was great in bed and really knew how to suck a cock...


That's actually sounding quite kind of you, unless it was BS. IN which case she got to know you good ;)

Quote by Longredhair
Yes, quite often. I've taken multiple virginity from multiple guys.

Poor guys, what a bad girl!
dpw
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Quote by Hytherion

Poor guys, what a bad girl!

Multiple virginity has me confused.ySRAzRWyVoGM4fSm
oshkrozz
Advanced Wordsmith
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Quote by dpw

Multiple virginity has me confused.FYYThHrQgtsg5FxQ


Well you know first time for mouth ... vagina ... and


then she takes out the strap-on ...
HappyEndings
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I don't like to term it pity fuck because being kind and just giving a woman who has just been dumped a good toss in the sack to make her feel desireable again is fun for me and her or at least it has been in the past.

I think that sex is different for men or at least this man. It doesn't have to involve love or even liking someone. If the chemistry is good and if both people seem to want it then I'm not that particular about who I have sex with if they're clean and disease free.

Old women, not so beautiful women, overweight women.... It's all about sharing a beautiful experience and I enjoy it.

I'm not much of a head turner myself but I've had some encounters with women that some people might think was a "bad match" and if it was good for us then we didn't care. One in particular was somewhat famous and an absolute knockout and much younger than me but we had CHEMISTRY and she LOVED some of my particular talents and that I was patient enough to make sure she got to have a few orgasms and that was hard for her to relax enough to do.

I even had sex a few times with a woman who I really didn't like at all and she seemed to hate me but we had an undeniable chemistry and the sex was almost violent but it was very satisfying and we both enjoyed it although we always parted quickly after the sex was over.

Liking a woman or loving her isn't as important to me as chemistry and sharing and celebrating my manhood and her womanhood. It can be just for fun or just a release of sexual tensions or it can be for friendship and just having fun together.

Sex is a wonderful thing and I love to share it with women.

I didn't mean to ramble but I've always loved to talk about why I have sex and it's not about trophies or beautiful women for me. It's that chemistry and it comes in many forms.

I guess now I'm slightly embarrassed and some of you might think I'm a shameless slut but I had to say it anyway.... LOL
Great minds think alike but dirty minds work together.... ;)
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I've had plenty of pity dates, but it never came to sex. Once I was almost convinced to give a pity blow job, and now I regret not giving it. It was likely the largest cock I'd ever seen, and it frightened my young and impressionable self.
Kell
Rookie Scribe
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Quote by alison90
I have a few times and I'm not ashamed of it at all. Sometimes people just need a bit of comfort. If I can provide that for a friend, thats a good thing.


Take Pity on Me!!!!
dpw
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Quote by oshkrozz


Well you know first time for mouth ... vagina ... and


then she takes out the strap-on ...

Vagina? I haven't got one of those!
Guest
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I pity fucked an ex who would not leave me alone and I felt terribly guilty for leaving him. I regret it and I hate him for making me feel so bad that I would do that. It was crap as well smile
Robert0909
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I did when younger, and now Im slightly ashamed, because all I wanted was sex, and they were looking for more. Now I am the grateful one, if it happens
Rick_Valley
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No, it just never felt like the right thing to do.
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In the interest of honesty and balance...

Some years ago I dated, fell in love and eventually lived with a girl who rocked my world. Although we were very similar in terms of job, (both journalists), interests, (books, music etc.) and sense of humour, she was REALLY shy and lacking in confidence and if I am that, (the jury remains out...) I cover it up well...

Here's the thing. The sex was AWFUL, and I mean TERRIBLE... And, honestly, that hadn't ever been a previous problem for me. I think MAYBE her shyness led me to be too careful, too hesitant in fact, certainly not as confident or comfortable as I had been before, with other women, or indeed since. And I ADORED this girl. We were together for four years and I gotta be honest, it never really got any better in that department. In every other way than sexually we were ideal for each other. The oddest thing was that we BOTH knew this was a problem, but try as we did we couldn't get over it...

Did she 'pity-fuck' me? It pains me to admit that I guess she did. She eventually fell madly in love with a REALLY NICE (and YOUNGER!) jock-type guy who had none of my hang-ups concerning her. By then, she HAD become a lot more confident and self-assured, indeed, a lot more attractive, and I can say that I had a lot to do with that. But the sex thing never worked with us.

She's happily married now, a proud mother and still with her guy. Hand on heart, I am happy for her.

The funniest thing is that, knowing all I do in hindsight, I could NEVER have played it any other way with her. I just couldn't. By the time of her marriage, we had become more distant, my choice in the main, since I was still hopelessly in love with her. But our ships had passed in the night and sometimes you have to let it go. I sent her a congratulatory note at the time, and I meant it, containing the phrase, "It is not my fault I love you as I do, nor yours that you cannot..."

I have never seen her since. I dream of her sometimes, and in the dreams she is always married!

(See? I'm not a TOTAL shit!)

xx SF
WellMadeMale
Constant Gardener
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I first saw Debra in a nightclub standing next to a striking amazon blonde. The two of them were quite the pair. One stood nearly six foot tall, was lean and willowy with a sexy growling voice and some sort of British accent...she was from the UK but I never found out exactly where. The brunette's eyes came to the collarbone level of her taller friend.

Both were, simply put - the two best looking late thirty something women in that nightclub most every evening when I'd notice them standing court next to the bar side closest to the dance floor.

A constant stream of confident men would approach either one of them asking for a swirl to this song or that one. They were running a 90% shoot down rate, by my calculations.

Genna, the blonde, once stopped by my perch on her way back from the ladies room and brazenly inquired. "How come you and your friend have never approached either of us and asked for a dance or attempted to make small talk?"

I grinned and noticed my friend Brett smiling just to the left of me as I replied, "It's more fun to watch you two work, than it is to be worked."

Over the course of the next few years, I'd go on to dance with Genna perhaps a hundred times. Being closer to the same altitude and attitude, I felt we made better dance and drink partners.

Brett and Debra had one dance and I think he propositioned her while feeling up her nice little round firm ass during a slow ballad, and Deb let him get a cheap feel - but that was it for her and him ever again. Probably just as well, he always had a thing for honey blondes and Deb, to this day still owns a thick gorgeous mane of loose, chocolate curls.

Eventually I became trusted enough of each of them to gain their phone numbers and Genna and I even started working for the same corporation and would often take a lunch or meet on the smoking pavilion. I became pretty decent yet casual friends with both Genna and Deb over the following few years.

One Saturday afternoon in September of 2001, Debra called me and asked me what I'd had planned for that evening.

"Nothing special, the gal I've been seeing lately has girl's night out in her hometown of Topeka. I thought I might call Brett and see what's kicking with him."

"Come meet me at Fox & Hound in Overland Park. Don't bring that asshat with you. I'll be there by 6:30, it would be nice if you didn't treat me like my last two boyfriends and showed up at seven, if you catch my drift."

I agreed that I'd meet her there by 6:30 and I figured that would make for a decent jumping off point for the rest of the evening's prowlings. I'd toss back a few cocktails with a friend, grab some light dinner and be ready to hit the nightclub circuit around 8:30-9:00 pm.

On the drive to the sports bar, I called Brett to inquire what he might be up to and he had other plans with his wife that night anyway. Probably just as well, I was feeling hornier than usual and always had better luck with the women when I was flying solo as opposed to buddying around with another dude. Around 10 pm I'd be hitting the proper stride, I felt.

Fox & Hound was as dead as a whorehouse on Christmas when I walked in, which sort of surprised me...but it had been a pretty day and it was Saturday.

I strolled up to the nicely polished bar as I noticed what appeared to be what I hoped was a rum & coke in a tall glass, sitting on a wet napkin, in front of an empty bar chair. I took up residence one chair over in case it wasn't Deb's drink and she wasn't in the ladies room.

"Corona ... with the lime, please."

"Coming right up."

As I was paying the man and gathering the cold brew I felt a hand in the small of my back and turned to my right... "Hey Deb."

"I'll be damned. How long have you been waiting for me, Jeff?"

"Just got here."

That was not her drink, on the bar behind me. I'd arrived before even she had.

She seemed somewhat impressed by that.

"Can you get the first round, I just have plastic."

I agreed to and said - "What's your flavor tonight?"

She looked at the man behind the bar and said..."Can I have one of your large strawberry daiquiri's, with extra strawberries?"

He smiled and went about his business.

She wanted to shoot some pool so she walked back to the billiards room and I paid the bartender whatever the rate was back then for an hour of table time, purchased her drink, gave him a tip - and ordered a plate of appetizers as well.

We'd shot three quick games of 8-ball. She was always a pretty fair stick herself and she said, "You're not throwing these games are you, I've seen you and Brett play you know."

She had me two games to one at that point as I was racking the balls at the end of the table.

"I wouldn't do that to you, Deb."

"Wrong answer! It's my birthday and you should give me anything I want tonight!"

"Well...Happy Birthday Gorgeous...You're 30 again?"

She was 42 and could've passed for 32, but she laughed and said... "Yeap...again, I'll drink to that!

"Hey, I'm tired of making you my whipping boy on the pool table, let's get out of here and head back over to my place and let me put some meat on your bones with some of my birthday lasagna I made last night. I have a shit pile of it left and I won't ever eat it all before I have to throw it out."

I agreed - as that sounded like a good deal to me. She only lived five miles from here and that was five miles closer to where I wanted to be in another few hours. I'd tank up on some good grub and help keep a friend who obviously was a little lonely - some company on the evening of her birthday.

The thought of putting a move on Deb had never seriously crossed my mind in the previous almost four years that I'd known her. She might have thought at one time that I was playing hard to get, but seriously... I often thought that the girl was out of my league and after a year or so, I just enjoyed her company and scoping out her nice ass in tight blue jeans - more than I relished the idea of over-stepping the friendship some night and getting shot right the fuck down in flames.

As we walked to our cars in the parking lot she did mention, "Since I'm feeding you tonight - can you stop and pick up a six pack of Heineken, not any of that weak Corona piss...it'd go good with dinner."

I nodded agreement and I peeled off to the liquor store as she slid out onto the boulevard and head off to the South.

I got to her place with a two six packs of beer and she was right, it did go down great with her lasagna.

Afterwards, we sat on her screened in back porch, she lit up a fat joint of some prime skunk and we both just enjoyed each other's company for the next three beers apiece. I hadn't even been looking at my watch, but when she excused herself to use the bathroom on her second trip I did notice that it was right at 10:15 pm and I'd need to be heading out soon if I didn't want to end up hitting on the sevens or eights because any of the nines or tens were already encumbered.

I carried my empty bottle into her house and headed towards the kitchen to dispose of it, couldn't find her refuse container and just sat the bottle on her kitchen counter top.

I turned around and in the dim light of the dining room I saw her leaning against the side of the arched passageway between her living room and dining room - less than twenty feet away.

She was wearing a 1990s vintage Kansas City Chiefs 'Joe Montana' football jersey, and from what I could tell - maybe nothing else.

Deb raised the joint to her lips and as she did so, said, "Hey can you flick me your bic?"

I was pretty high but I knew a come'on when I heard one and I was digging my lighter out of my shirt pocket as I walked towards her...I went to hand her the lighter but she handed me the roach instead and turned in a graceful pirouette and started sashaying - but not overtly, down her hard wood floored hallway towards her bedroom across the hall from the bathroom I'd used a few times already.

"Light that puppy up and bring it with you, Mister."

Did I pity Debra in that moment?

Not one fucking bit. My dick immediately became so hard I could probably have cut steel plate with it...but yet I held back. Flicked my bic and took a couple of short pulls and then with the flame extinguished I inhaled one slow, long drag.

"It's my birthday, Jeffie... Aren't you supposed to give the birthday girl anything she wants on her special night?" I heard her voice from 25-30 feet away as I also suddenly heard my heartbeat pulsing in my ears.

Exhaling I tried, as casually as I could, to meter my steps down her hallway so as not to sound like a breakneck gallop.

All the lights were off, a handful of candles lit on her mirrored dresser and some light from her neighbor's backyard lamp cast a faint glow through some southerly facing windows and blinds upon her bed. She always kept most of the lights in her home either off or at a low setting so I could quickly see pretty well in that darkened room.

I just walked to the bedside and asked if she wanted another hit, and she took the evil weed from my fingertips. I backed away a step and immediately started disrobing.

"I like it when a man knows how to buy a clue," she said, laughing.

I slid onto her queen sized mattress and watched as she placed the joint into an empty coffee cup then turned back to me and said..."Give me your best shot Jeff, show me what I've been missing."

There was the usual clumsiness involved as with any new lover as the timings and position play was being established...the kisses learned, the moans heard and noted.

I began to slide my torso down the length of her petite frame as she laid on her back, and I shifted to where I was between those succulent legs...it was apparent to her where my tongue was heading and she exclaimed, "Wait...I don't do that. At least not on the first date, come back up here...

"Do you have any condoms?"

"Yeah, yeah I have one in my..."

"That's alright, I got one right here - we don't need you to go digging through your wallet for three month old rubbers!"

She'd pulled a packet out of her nightstand drawer and then laid back again atop three plush pillows, had her legs spread invitingly and I think she was rubbing her clit. In the dark it was a bit hard to discern.

I ripped open the packet and pulled out a condom that felt to my touch like it was made from balloon latex. It felt rigid and thick..and as I rolled it down my shaft, it was also somewhat constricting - and not in a pleasant, barely noticeable way.

By the time I managed to get myself sheathed, Debra had removed the football jersey and...damn, she had a marvelous set of real, firm, tig ole bitties! I could almost not wait to mount her, yet I tried to regain my composure and we kissed a bit again to establish the mood once more...

When I sunk myself into her - missionary style, I couldn't feel her warmth, I could not feel her wetness. It felt like I was wearing industrial grade pvc pool liner material wrapped tightly around my throbbing cock. She was moving her hips perfectly and her pussy felt like it was alternately trying to milk me and also grab and wrench my skinny ass around between her legs.

It felt GREAT! If only I could have really felt more. After what seemed like ten minutes of mutual thrusting where we'd established a nice rhythm but was probably only four or five, I slowly pulled out and attempted to maneuver her atop me, so she could ride cowgirl style and take some control. I could tell that a few of my thrusts had gone perhaps too deeply as her body seemed to tense up a bit too much.

"What are you doing, Jeff? You're ruining a perfectly good orgasm here."

"Just trying to add a little spice to the night, babe."

"I'm sorry I can't do that position, I've got weak knees and it aches after just a few moments...just climb back in and keep doing what you've been doing."

I dutifully obeyed - even though I seriously couldn't feel a damned thing myself.

Another ten or twenty or hell maybe thirty minutes passed. My thighs and hips and stomach were beyond aching...she finally came and I thrusted a few more times myself and gave out a low moaning, groaning grunt. I'd never faked an orgasm before, but by that time I really was more worn out and had very little adrenalin or testosterone to fuel my body as in similar other circumstances.

I was just fucking glad that she had climaxed and given me an excuse to roll over and off of her. I lay there panting along with my friend who lit up the roach and we both laid there recuperating and passing it back and forth for the next ten minutes before she took it one last time and got up and disappeared into her bathroom across the hallway.

I took that as my cue to get up, get dressed and attempt to gracefully get the fuck out of there.I was standing in the hallway by her living room, not fifteen feet from her front door when she came out of the bathroom wearing a plush, pink velour robe...She'd turned to come towards her kitchen when she noticed me in the dim light...and she smiled.

"So you're one of those guys who comes over and knocks off a piece and then leaves, are ya?"

Before I could say jackshit, she cracked her infectious belly laugh, gave me a hug and a kiss to my chest and dreamily said... "Thank you for my birthday present."

"The pleasure was almost all mine," I chuckled.

"Now you get out of here and be careful driving around tonight."

Awkward? No, not particularly. We had been friends, we'd only just had sex - couldn't we still be friends? She seemed comfortable and that chilled me out too.

Pity fuck? That much, I still don't know. But I have sometimes thought that was as close to one as I'd ever come before or since.

All I knew then as I was backing out of her driveway was that it was already nearly fucking midnight and I was already pitying the last-call-for-alcohol bar skanks at whichever nightclub I was going to hit first about twenty minutes from then. I had a backed up load and I meant to unfuck myself for the night.


(damn, is this long enough for a submittable story)
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
adele
Weaver of Words
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Quote by WellMadeMale


(damn, is this long enough for a submittable story)



Nearly 2600 words... so yes!
Sluttyredhead
Active Ink Slinger
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The closest I've done was a pity handjob . We were dating about a week and I have a habit of being mischievous in boring movies , well when he was maybe three and a half or four inches and a slender as a pencil I felt like I had to be nice and follow through.
Magical_felix
Wild at Heart
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Quote by WellMadeMale
I first saw Debra in a nightclub standing next to a striking amazon blonde. The two of them were quite the pair...

(damn, is this long enough for a submittable story) d'oh!



That's how far I was able to get. So I guess it would be up to your regular standards for a submittable story.
Verbal
Gravelly-Voiced Fucker
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The one time I gave a pity fuck was to a girl I just broken up with. It was really nice. It provided a real sense of closure.
WellMadeMale
Constant Gardener
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Quote by Magical_felix


That's how far I was able to get. So I guess it would be up to your regular standards for a submittable story.


If only I'd included some lengthy sock and huge dripping cock pictures to keep your interest up. But I can't please everyone.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
curvygalore
Bonnet Flaunter
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Yep. Because I was not in a good enough place in myself to tell the guy concerned to sod the hell off. Irony being he was in a much stronger position in life than me at the time. No regrets, but never again.
stridepower
Advanced Wordsmith
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Quote by BethanyFrasier
Mea culpa. Nice girl that I am, I was suckered into a pity-fuck! lol I was working as a server in a restaurant over the summer after my freshman year of college. There was your usual share of pretty girls and hot guys among the staff, and most of us were dating, or having sex with each other. But there was this one nerdy Jewish kid who was really sweet, but very shy and awkward with girls, so he never got up the courage to ask any of us out, especially after being shot-down by a couple of girls already, but he and I got to be friend-zone type friends, and he kind of hung around me like a puppy. Then, a little past the middle of summer, he had to have an operation to remove one of his nuts, and when he came back to work, he was mortified about losing part of his manhood, and just to ask him about how he was doing after the surgery, we really had to coax him to open up about it, but he was afraid everyone but me would make fun of him. So some of the guys kept pushing me to go out with him, since I was the main object of his dreams, and pretty soon even the other girls were telling me I was the one who should have sex with him, to convince him he was still able to function, and get a girl in bed with him. I finally gave in and agreed to 'take one for the team'! lol I asked him to come home with me to help me move some furniture around in my apartment after he had healed enough, and after we got done, I cooked dinner for him and let him hang around all evening, and finally let him spend the night with me.



Well Bethany. Did he perform well as far as getting you there - was it worth it? And did he appreciate the assistance?
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Yes I have had a pity fuck with of all people my loser husband