For my second story I'm going to talk about the quickie with my long term girlfriend at the time. Name changed for obvious reasons. Nicole was 5 years younger than me. I was able to meet her through my job and we immediately hit it off. She studies at the local university and we shared the same interests. In total we were together for a little over three years. We had the marriage talk, planned the future, etc. Things just didn't work out though. Nicole was the same height as me 5'10 and was around 145. Blonde hair, green eyes, an amazing round bottom, and B/small C cup boobs. She had really nice boobs even though she hated them. I went three years without and real nipple or boob play. Times were tough on that front. Anyways, she has (had?) amazingly tight and pretty pussy. I was her second BJ, and I took her virginity. She was the first woman I ever fucked bare and came inside of. She was on birth control of course. Getting off inside her only happened like three times because she didn't trust it, so those times were a treat for me. I could tell many stories about Nicole and myself but for the time being I'll tell the one thy sticks out in my mine the most. "The Work Break Quickie". After losing her virginity Nicole became very cock hungry. One time, over the course of a day we literally fucked like 5 or 6 times. She was by far one of the wettest pussies I have ever had the pleasure of being inside. It was like a faucet had turned on. I was off this particular spring/summer day and I received a text from Nicole that afternoon talking about how horny she was. I used this opportunity to sext things up and drive her crazy. She told me to stop since we wouldn't have time to do anything after she got off work. Being the good, mature boyfriend I listened. In turn I started using the thoughts of her turned on as one of those long, sensual masturbation session all of us men long for. Some time later, my phone does the double vibration signaling a text message. It read, "Going on break at 6. Pull around to the back of the parking lot and be ready to fuck." I don't know how long I had been peaking myself, but I was kinda pissed. I wasn't going to last long at all, (worked out perfectly since it was just a quickie though). I was pre-cumming everywhere, but I quickly threw on a shirt and some basketball shorts. I drive up and pull to the back of a parking lot. There are some trees and an embankment in front of the car, and to the right was the block walls that held trash dumpsters inside them. The problem came from the left side. There was a small distance and a a rise to another parking lot going into another retail store. At 6pm this retail store was busy too. Damn staggered retail set up! Cars were always circling behind her store too. Risky situation. So in my struggle to comprehend the very public situation I find myself in she comes up to the passenger door and gets inside. We have a quick kiss and she take my hand and puts it on her crotch, it's soaked. She says, "No foreplay, put it in me and let's do this." I needed no further encouragement as I slid my shorts down revealing my hard dick. She was doing the same with her pants when she reached over to give me a squeeze. My dick had that deep red/purple color that it gets when you are close to getting off. "Been playing with your self, huh?" She knew me well. She continues removing her standard black retail pants revealing her perfectly shaved and wet pussy. Nicole didn't wear underwear, she always said it allowed her "lady to breathe." I was worried about her taking them all of the way off in our present situation but she silenced my by removing them completely and spreading her legs revealing her glistening vagina. "Now" was all she said, and I quickly listened. I climbed over the console and in between her legs. I slid in like there was no resistance and started pumping away. Unfortunately, I couldn't look down at her. My eyes were scanning all over my right shoulder and out the back window. She used one of her hands and started playing with her clit. I do remember that she kept saying to concentrate on her because nobody was going to see us. She was probably right as the sun was now going down, but I was still l worried. She told me to speed up and I started thrusting faster and pushing deeper. Soon she started to wimper and her body convulsed as she got off. The heat from her orgasm was pulling me close to bursting. However, I'm still stupidly looking around when I spot a man leaving the store, looking our way while speaking to his wife. I'm my panic I drop right on top of her. Obviously, the man was just talking and concentrating on his wife, not us. Somehow that didn't piss Nicole of to the point to where she got up and left. She said, "Don't worry about anyone they can't see us." "Think about getting off and how hot this is". At this point we have probably been going at it for 4 or 5 minutes. I start thrusting once again with renewed vigor, since he scare has brought me down from the point of no return. She started saying things like how good my dick felt sliding inside her and how she could feel it swell, knowing I was getting close. I asked to get off inside her. She wouldn't let me though. I told her how hot it would be with my hot sticky cum inside and dripping out of her as she finished her shift. She continued to give a firm no. I then switched tactics to getting off in her mouth. She seemed to consider this, but her sensibilities took over and she realized that in our front seat situation I would likely miss her mouth and end up on her face or all over her clothes. This exchange lasted between 30-40 seconds. After she shut down the mouth idea she started unbuttoning the front of her button down shirt. One, two, three, then soon all of the buttons were off. She spread her shirt open revealing the blue and white polka dot bra she often wore. Her breast were swollen, even on her back they looked so nice and round. One of them (sorry can't remember which one) had slid up in the bra revealing just a little bit of the brown areola. "Shoot it all over my stomach.but doing get it on my face and neck." My mission was to reveal the rest of that beautiful boob. Like I stated before Nicole hated her boobs and never took her bra off during sex. I was going to thrust that damn nipple out! I started jack hammering as hard as I could. Unfortunately, 10 seconds in nature overtook determination and I felt it. I tried to hold as long as I could, but I couldn't last any longer. In my split second mind I thought about pushing deep and shooting the first shot inside her before pulling out Thankfully I didn't, (men who have unprotected sex without birth control, that thought us how you have children!) I pulled out and stroked myself on her stomach. One two, three, four shots came out. These weren't the big firing shot from my last story. They were the thick, gooey cumshots, they always feel so much better coming through and out of my shaft. I watched these shots land in her belly button, (she had an innie). Nicole made a statement about how purple my dick was. I disregarded that comment though. I had a new mission, fill that belly button as much as I could. I continued getting off. The earlier teasing, combined with the voyeurism resulted in the largest visible cumshot to date. I'm sure I've had one equal or larger but I couldn't physically see it. After the conclusion, I came to my senses and she was saying, "damn" and laughing. My legs were shaking and I was starting to cramp. I looked down and saw a puddle around her belly button. She continued laughing and said how good that must have felt for me. She ran her index finger through the goo and said it was "my lake." She pulled her finger out of it and in its thickness strung and and dripped off her finger. She said how she had never seen it that thick before. Then she dipped it back in and twirled her finger wrapping it in my cum. She brought it up to her mouth and closed her lips around the finger as she sucked it clean. Nicole paused for a second before she swallowed and said, "I don't like it thick, it feels weird." By this time I was back in the driver's seat getting my shorts on. She asked what I had to clean up the mess. I looked in the console but I was out of my trusty napkins. Thankfully my tennis bag was in my back seat. I unzipped the side zipper to took out one of my Nike bananas. She used that to clean up and put her pants back on. As she started buttoning up her shirt I took one last look at her bra. I hadn't succeeded, she scooted back up and her boob fell back into place as she finished buttoning it up. We chatted for a few minutes and then she kissed me goodbye and went back to work. I looked at the clock, the whole sex session lasted around 5-6 minutes. She text me when she got home and told me that she masturbated in the shower thinking about the quickie. Nicole was fascinated with his much I had shot but we never got that much volume before. Instead she turned her attention to how far she could get me to shoot. I'll tell some of those stories in the future.
Tag: Masturbation
[F/M] The time we got free Arby’s
…and then he grabbed my titty like I grab an Arby's roast beef, full palm and squeeze. I moaned and bucked against him.
"Harder… God please," I gasped desperately.
Speaking of Arby's roast beefs, we were on their premise. Specifically, in the woman's bathroom. Both us were just a little tipsy, a little full, and wholly horny.
My eyes lowered to his manhood, already full mast. I shuddered and grabbed him close, rubbing him between my lips the way I knew he liked. He moaned in my ear, louder this time. Heedless of the public indecency, I echoed his moans.
'Babe please,' I wanted him to give me a milkshake so bad. God, I wanted him to shake my milk…shakes. Maybe I already did, there was definitely a boy in my yard.
Well, time to make milkshakes out of my God-given shaker. Luke looked at me curiously as I dislodged myself from our tangle on the ground and pushed him against the wall with tipsy legs, right next to the automatic hand dryer. I grabbed his thick meat again with my palm, and this time began pumping away in earnest. My tongue flicked on his tip tantalizing the way I knew him. But I was drunk, he was full on tipsy, and it was time to get kinky.
A Retired Police Officer Paid Me to Strip for His Wife for Their Anniversay [M/F]
This is my first post, so here's a little introduction:
My name is Dion, and I'm a male stripper. I started stripping as a college student in 2003, and continue to do so today. I'm also one of the only male stripper bloggers around: http://malestripping.blogspot.com
Anyway, this story took place in 2004 when I was still a college student at the University of Florida in Gainesville, Florida. My company at the time was French Addiction (no longer in business), a lingerie store that also booked male strippers for customers in the surrounding area.
Most of my parties were bachelorette or birthday parties, along with the occasional sorority party. And most of the customers were female… Except this one time.
French Addiction booked a gig at a bar for me on a weeknight, and I was told to call the customer for extra instructions. The customer was an older man named Terry. “It’s our 20th anniversary,” he explained. “I bought a ring and I want you to give it to her.”
“Does she know I’m coming?”
Terry laughed. “Oh, no! She doesn’t know anything about this at all!”
[M]y first [T]ime with a trans woman
So, it was a half-assed sort of bachelor party.
I've been in a few weddings, and the thing is, bachelor parties are off the hook these days. Movies always just have guys go to a strip club or whatever, but nowadays people are getting creative, going on paintballing excursions, hunting trips, indoor skydiving, you know… crazy, awesome, memorable shit.
This was not that. This was not even going to a strip club.
This was going to some bars and getting drunk. I'd flown in from out of town for this, and I was in Chicago – one of the coolest, craziest cities in the world – and I was drinking beers with the fellas, something I could have done for a lot cheaper back home.
The one upside was that one dude in our group had the hookup at this club we were at – friends with the DJ or something – and so we were drinking for free.
It was a decent club, too, I'll say that – expensive, and kinda full of douchebags (we were near Wrigley, the douchebag capitol of Chicago), but it also had good music, cute bartenders, and loads of college-age folks on the dance floor.
I wake up a girl [fantasy] [gender-swap] Help me finish or give me feedback?
I was gorgeous, a gorgeous girl. My first thought was "If I'm as sexy a girl as I was a boy, I was a lot better looking than I thought". But then maybe its easier for a girl to be attractive.
I had average sized breasts, but they were well shaped and round and the the nipples were the perfect size. My legs were long and shapely, but thick thighs met a thick ass. My ass was amazing, I would have fucked my own ass if I could.
My dark hair reached below my shoulders, and it framed my attractive but not stunning face well. Brown eyes, brown skin. I was a gorgeous Indian girl, the type I would have lusted over in a second.
I touched myself all over, but it was unsatisfying. I was sexy, but I couldn't access it. I wanted to fuck myself, but even masturbation felt unfulfilling. I wasn't great at finding the sweet spots on my vagina. "I must have been terrible in bed" I thought to myself, wondering if my fingers were as clumsy with the girls I had played with.
Party Hook-Up [F]ucked on [M]y balcony
I guess I'm an average looking guy. Just a hair under 6 foot, average build, not lean but not fat either, with some muscle shining through in leaner spots. The thing that sets me apart is I have a 7.5 inch dick that is proportionally thick.
My friend is in a Frat and he talked me into going to their party last night, I was reluctant at first, but we got there about 11 and the party was going strong and I started to loosen up.
I'm not shy, but I'm not the kinda guy who really knows how to walk up to a woman and get her into my bed the same night. I've had FWBs and GFs but only 1 real hook-up before this. That being said, I was pretty surprised that I was getting a lot of attention from this one girl. My friend pointed her out, and her girlfriends kept talking into her ears over the music and gesturing our way. She was at least part Asian, Chinese if I had to guess, she had a pretty face and you could see that she had some Caucasian in her too, making her Asian features less pronounced, but still noticeable. Her body was great about 5'5", lean but with just the right amount of fat to give her gentle curves and keep it soft to the touch. She had B cups that looked bigger than they were thanks to her petite frame. Her ass fit her body and was very shapely in the black skirt she painted on.
I’m a 42 year-old virgin [M] who regularly hosts and watches a young couple [21m/19f] have sex.
(I posted this a year ago and then quickly deleted it. Feeling brave enough to repost now. I will write a follow up if there's interest.)
This isn't your usual sexy tale, but I thought if anyone would appreciate it, it would be you guys! Totally odd, totally true.
About me: I'm a 42 y/o heterosexual single man, living on my own. I'm well kept, have a good job, and most people would have no idea I'm still a virgin. (In before Steve Carrell jokes.) It just never happened for me and for the most part I'm comfortable and happy living on my own.
Sometimes as part of my masturbation routine I'll browse Casual Encounters on craigslist, mostly just to see the pictures. This time I saw an interesting post right at the top of the page: it was a young couple (him 21, her 19) asking for an older man (age: 40-45) to provide a safe place for them to have sex and who could watch them.
Sexy Scrabble: part 3 [f] [mast] [orgasm]
I am sitting in my old red Honda Civic in the parking lot of my school. Gahhh! Normally, I would be excited to leave my piece of shit car and make my way to the school’s courtyard to gossip with my friends before dreaded school started. But this Monday morning, I am dreading seeing Ethan. I know he’ll be there in the courtyard…with my best friends/his girlfriend Rachel.
I hit my head back against my car’s headrest. Why does life have to be so complicated? After I cummed all over Ethan’s basement floor and the haze of lust had cleared my mind, I then realized I had just tried to fuck my best friend’s boyfriend. In a blushing red panic I had grabbed my purse and ran out of his house, forgetting that there was even a scrabble game to finish.
That was Saturday, and we still haven’t spoken about it yet.
Do I tell Rachel? Should he tell Rachel? Or should we pretend this never happened? With a sigh I exit my car; I can’t avoid my friends forever.
I make my way over to the courtyard, and I see Rachel give me a huge grin. Great…she still has no idea.
The Good Girl [M/F]
[Names and superfluous events tweaked in the interest of anonymity]
I know this story is a lot longer than most here, and I thought about cutting it down. But to tell the truth our entire encounter was meant to be slow and teasing, so I have kept our story of it the same.
I knew from the first time we talked I was into her. She was young, pale, and skinny with long red hair and gorgeous blue eyes behind a pair of horn-rimmed glasses, beautiful legs and perky breasts, if there was ever a "Sexy Librarian" look, she was the embodiment of it. She was at the end of her teens, I was at the end of my twenties. We talked for hours on the phone the same day we met, going over everything from relationships, to fears, to desires. She wanted to make sure we were as compatible sexually as we were mentally before she wasted any time.
The One Who Got Away, Pt. 1 [mf]
This is largely just an introduction, told from the perspective of a typical high school/college kid. Naturally, there's less sex in this part. Other chapters, I promise, will have much more satisfactory material. Comments and suggestions are always welcome.
It wasn’t meant to last, right? Do such things really ever last? He placed his classmates into two categories. There were those, like himself, who found a love, or, more accurately, an infatuation early — coinciding neatly with that period in life in which one sheds their innocence of sex. And then there were what he now called the realists, who outwardly showed no signs of romance, but eagerly embraced the pleasures that came with high school. He supposed there was possibly a third group, the unlucky. But given all the heartache their more “lucky” classmates experienced, he didn’t know if that was the right term. Late bloomers, might be more precise.