[MF] Trying to be good went bad.. but oh so good

I’ve been seeing alot of posts and questions about mutual masturbation on subs here last few days and that topic always beings me to one of my all time favorite experiences and wank bank moments. I’ve been hard for 2 days now and figure telling this one again will probably get me to finish the job and be done with it. So here it is.
This happened a few years ago, maybe more than a few. I had a very steady FWB who was a divorcee who’s ex was an alcoholic and a left her very much untouched for years, after they split she had an extreme awakening and new found interest in porn which all worked out great for me. For a year or so we were probably monthly fuck buddies, she was looking to try things that were new to her and she seemed to always have a great idea or two which made it great for me. But after a weekend of fun it would get a little klingy and the age gap was too much for me to take it all too seriously.. so we would have abrupt starts and stops, then she would call again and we’d be back at it. Anyway at one point I moved out of town and found a relationship. However I had business in the city in common with FWB so on occasions i’d be back int own for a few days at a time.
Onto the story.
She saw on FB I was in town and texted to have a drink, we agreed and met a place we used to hang out at. I’ll call her Sara here. Meet, drinks, cigs, chat chat chat and Sara gets up for another smoke and kinda stumbles.. weird but the bar tender shuts her off. She was a decent drinker in her own right and she was not even close to maxed out, but none the less we are done there. She has wine at home, we headed over. Now i told her throughout the night that i was in a thing and was really trying to be respectful. Truthfully I was very unsatisfied but still didnt want to be an asshole and also didnt want to start any drama that could get FB public in a hurry. She had that potential.
now we are on the couch drinking wine, watching TV more chat. First we are sitting normally but over time she has started to lean to her right with her legs up on the couch, leading to a had to be obvious look up her skirt at her thighs and bottom of her ample ass. Her feet make their way to my lap. I shot her a look as if to say dont go there, we laugh, but move on. I can see now that she is wearing black sheer panties.. I have a big thing for sheer. I dont think she even knew that at the time. I got up and when I came back to sit down she lifts her front leg and has shifted to her back more or less, with her other leg to the back of the couch, so as I sit I am now between her legs. This is a 3 seater couch too, so things are getting pretty snug. I am now looking down at her legs spread, skirt just hiked enough to get a panty view, i can see clearly the shape of the bottom have of her newly shaved pussy. Sara sees me looking, immediately conversation stops, she slides her skirt up slowly until her panties are fully exposed. She had always before been a manicured landing strip gal, she was full bald.
“i know, but i have been dying to show you.. its taken me all night to get the courage. i tried to slip it into conversation like 3 times but you didnt get the hint”. I really had not, still no idea what she meant by that, but who cares. I am loving the view. She begins tugging at the top of her panties and running a finger down under the hem to the sides, really modeling her new look thru the sheer.
“those panties are so sexy. they feel so nice” as I pinch an edge along the side of her pussy and pull them away from her mound and rub them between my finger.. wet.
“but how do I look” as she thrusts her hips forward a bit arches her back, trying to press her pussy to my fingers which are still holding the sheer fabric.
“so fucking good” I tell her as i slide my hand up, palm down to the top of her mound and use my thumb to press the skin above her slit up, causing her glistening soft lips to part just enough for her clit hood to pop free, and one more little pull to get her pink button to be exposed.
She gasped and arched, and ran her calf over my crotch pulling it back slow until her heel then toes had pressed my throbbing hard cock. My turn to gasp.
i mutter “fuckkkkk” as she hooks her panties and pulls them aside. I lowered my face to her, and gently pull her clit with a soft suck between my lips. I start sucking her clit in, firm and repeatedly like I am savoring the end a cocktail thru a straw. She is pressing up into my face and holding my head.
then i stop. My conscience kicked in… I could not, or should not, have sex with her. I dont know really what stopped me in truth, but I popped up. She groaned in anger or disappointment at the same time sliding her hand down to her wet, open and wanting pussy. We debated do’s and dont’s for a few seconds, She rubbing her pussy with mouth open and almost panting the whole time.
Plan was made, I went to her room, top drawer, new toy. It was one of those eggs with a little wire leading back to a remote.
She was going to cum, I had started it, its only the polite thing to do right? She turns it on and sets the initial pace, positions it over her clit still at first.. then smaller but growing circles covering the length of her soaked lips, ultimately popping it in and out about 3/4 of the egg into her hungry pussy. Staring at me intensely the whole time, either with a very aggressive I’m going to cum face, or a very pissed I am not fucking her face… either way she meant business.
while she is control and i am aching, I pull out my cock. Much to her approval, she lets out a long “mmmmm uh ha uh ha” like a moan with a yes at the end. She hands me the remote, lets me handle the pace while she continue to work the positioning. “turn it up, turn it up, up,… ” shes losing the ability to speak for a second. Her eyes still burning into me, alternating between my cock and face. As i am getting used to the remote I let my cock go, as it flopped down a string of precum landed on her thigh. She moaned and shook, she loved that, and pressed the egg full in. As she did her mouth flung open and she arched and came, she stopped breathing and closed her eyes. when she landed back she ordered me “come closer, i need it close to me.” I stood and got in front of her on the couch, she is laying sideways legs wide open. Her routine has resarted, egg on her clit but starting to circle, she is building a new orgasm. She now starts sucking her fingers furiously and closed her eyes. I had never seen her do this before. As she is building I see a change in her. Sara’s body relaxes a bit, she opens her eyes and mouth wide. She grabbed the remote from me and drops it besides her. She is now pumping the egg in and out and with a focused rhythm. Her mouth is wide open tongue extended. She pushed the egg in all the was, just the wire exposed and halfway closes her legs, getting i suspect a tight deep grip on her pulsating orb.
“just cum in my mouth, its ok I’m not touching you” she says. Never before and never since heard an invitation/demand quite like that. I mean I had been kinda good under difficult circumstances so far, right?
I get closer, she gets closer, we are closing the distance quickly.. i had already been on edge for awhile but since she took the remote i had taken the chance to rub precum all down the length of shaft and I too was now a glistening mess. With the head of my cock now withing the basin of her mouth, her breath hot on me, I took one final full length, base to ridge pull and unloaded. I shook and rocked front to back, almost fell on top of her, hand landing on the wall above the couch to brace myself. Which left me in a position so that I was basically right on top of her shooting stream after stream directly into her throat. She didnt gag, didnt complain, also couldnt make a sound. She did pop up sensing my final pulse had exited, and take me in fully for a once up and once down clean off. It was a deep, thorough suck. In my position I could not object or avoid, doubt i would have anyway. By the time her head hit the couch again, She has swallowed me away. She grabbed the back of my thigh to keep me still and close and hummed her way thru a long but seemingly relaxed, legs still closed, orgasm.
I collapsed next to her as we finished our wine as i casually watched her remove the egg and remain displayed for me. Her pussy was flushed and just a little open, I like to think it was smiling at me for the rest of the night.

[M] F Waxed on a dare

My then GF and I took a cruise together as our first real “couple” vacation and in preparation we went on a big shopping spree to pick out bathing suits and what we figured to be cool “cruise” clothes.. of course the boat ended up being full of retirees or children.. little in between. But not the point here. We also went tanning in preparation, and the GF decided to go a step further and got a Brazilian wax. She had shaved before, but this was a much bigger deal in her view anyway.. must say I loved it, was smoother and stayed that way stubble free for the entire trip. But she was looking i think for a medal of some sort for bravery and pain tolerance… after day 2-3 i had heard enough. She then dared me to go to the salon onboard and put my bravery to the test.
During one of the Port days I slipped in… during the conversation leading up to my appointment with there was lots of bravado and “if you can take i can take it” talk.. but the walk in was somewhere between shame and terror. I wasnt even sure how to ask for this “treatment”. Luckily I met an angel of mercy for my embarrassment, and later for a bit more.
She was older (40’s) and curvy, but quite Milfish and very easy to talk too considering. So it started slow with getting onto the table, and some warning type conversation about what was about to happen and what she would be using etc. Although i am not overly hairy it is more or less all a continuous head to toe flow of body hair, so we had to discuss exactly what i wanted to have go. So for purposes of proving myself to the GF I opted for a reasonable clearing zone. So fast forward thru small talk, told her why i was there (the dare), she started the process and i turned many shades of red for many less than enjoyable reasons. Did the lower belly portion down around thighs, to under the junk (ouch), and balls, (quick, more trim pluck than pull thankfully) and started in on the central parts. We are probably 15 minutes in now so i have gotten used to the sensations, coolish wipe, warmer application, yank, sooth.
now where it got good.. very light flirting, mostly about the lonely life on the boat, most of her customers are old/mean woman or old fat European men. She rarely gets a man for this task, but when she does it is of that sort. Now shes working just above my cock and in positioning herself has me pointed full down and resting her hand/forearm on my cock and also offering a decent amount of cleavage in plain view. She would also get her face in low and close enough to inspect i could feel her breath on occasion. sooo things start happening… she would shift, i would rise, she would reposition to get me back down. This went of for a brief while, then she got up and gave me a break, half bare above my cock and of course it sprang up. i was trying not to look, she was moving around behind me with my embarrassment and arousal obvious. She kinda laughed and smiled as she sat, and tells me “its ok this makes it easier for the last part” (hair on base of my shaft) and grabbed a hold with one had as she soothed the bare spot where she had just torn my hair out from the roots. BTW it had already been decided 1) GF is tougher than me 2) i would never again get waxed.
From this point however she never didnt have a grip on me. Never an overt stroke really, but much squeezing, thumb caresses in all the right spots, moving from side to side, brushes with fingers, the back of a hand, clealry much more contact and gentle feeling than the task required. Then things really slowed down. she smiled all the way and was not at all shy about long looks and careful positioning me seeminlgy for her enjoyment only. AT one point she was looking down around the balls and pushed my cock down flat to my belly and held it there with her open handed palm, just so subtly moving her hand in a circular pattern.. i thought that was it, I was about to cum in the grips of a woman just doing her job.. a strange position to be in, I wanted so bad the release but had this feeling I would feel so terrible immediately after. I tensed, toes straight up… help my breath and maybe even a slight moan. She sensed an saw all this and straightened up in her chair. she laughed and again reassured me, this was all ok, she released my cock from its pinned position but held it upright. she slid her hand up and aimed it at her, and with her other hand used one of the damp warm toilette’s to swipe off precum that had formed and begun to leak down. she let out a sound of approval.. not sure how to describe the sound. From there she cleared and soothed the remainder above and wet to work on my base. That HURT again… to the point i began to loose my excited state, she disapproved. Took a short break and said “stay with me honey” and gave my a good up and down with a towelette before holding me still in a tight embrace while chatting. The final phase was the bottom base, and she returned me to the pressed to the belly open palm position. She said as she was ending up, “i know this was your favorite part” she then slid her chair up to mid chest on me and let go, just long enough to pour the finishing lotion and give me a good long application. my squirming was intense, precum likely hidden in the mess but i was flowing and twitching which i know she felt and when she let go i was like one of those 20 ft used car lot inflatables flapping all over.. it was to much to bear. She asked if i wanted to go see the GF like this. I was comfortable enough at this point to jokingly say i cant make it down the hall, i hope the boat is empty. She said, well dont bother, just relax here for a minute. She gave me a pump of lotion onto the shaft and top of my cock but then sat back and put her elbows on the table. staring me in the eye, then looking down at me, my hands seemed to follow her eyes and i grabbed myself. still a little unsure until she started to massage my thigh. I began to stroke and imitate the squeeze technique she had been using on me”thats it, make your trip to the room so much more comfortable” she stood, one hand on my thigh the other on my chest looking straight down. she grabbed a towelette once again and held it flat in her open hand above the head of my cock. “in here honey” before her sentence was done I was spurting and bucking, she laughed out loud, a prideful laugh i think. I shot clear over her napkin and hand onto my chest. She grabbed another as i lad back and wiped my brow with one hand as she cleaned up the pools of cum with her other. GF is braver, but she didnt get that.