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Ten Illustrated Stories About First Time Sex

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I even felt bad about plotting to get into her pants. My First Cock - Chapter 3 Viewed: Just as hes about to cry, his neighbor Harley comes over. Trick or Treat [gay] Viewed: But I was a frequent masturbator, and figured I was so in touch with my own body and sexuality that as soon as I let someone else explore, all those years of pent-up sexual frustration would erupt out. I wanted to try all of the positions my friends had bragged about.

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The hammock swayed with his thrusts, making me dizzy, but I got used to it. Muscles Boys without Women [bi] Viewed: I needed to know what goes where, what to say to her, what or what not to wear. All I wanted to do was to go home, take a shower and put on the flannel PJs mommy got me for Christmas. We stayed together for three years.

Follow him on Facebook. Of course, this is not necessarily a bad thing. Less class equals more sex, and girls give sex out more freely than ever, though only to a handful of guys. San Diego is one of those cutthroat cities — where, if you have your shit together, getting laid can be as simple as shooting fish in a barrel. There are some 7 bases within 15 miles of each other in the actual city of San Diego, plus Camp Pendleton only 30 miles up the road in Oceanside.

This means that there are drunken Navy and Marine boys running around all the time. They often have quite a bit of money to blow because they live in the barracks and therefore have no living expenses. In addition to that, they are all in good shape. Be better than average. Many girls here are incapable of thoughtful conversation, iPhone-obsessed, and have the attention span of a child.

Yes, the numbers with other guys are shitty, but remember that the population of San Diego is well over a million people. Many girls are in good shape, athletic, and are in general, good-looking.

The city overall is very active due to the year-round gorgeous weather, which means that many people pride themselves on keeping themselves in top beach shape year round.

Do you have a great first-time story? My First Time runs every Tuesday on Nerve. I celebrated the end of my junior year of high school with my ultra-cool, apartment-renting, punk-rock-music-educating, twenty-one-year-old boyfriend dumping me.

So when I ended up at a local punk-rock show he was also attending a scant few months later, I decided jealousy was the best weapon. He was also shirtless, except for three pages torn from Hustler , adhered to him by his surprisingly sticky sweat. But what made him perfect, despite the fact he only topped a hundred pounds when holding his bass, was the fact that he was friends with my ex. Of course, his mother and still-elementary-school-aged sister could easily be heard moving through the rooms above us.

After making out moved us from recliner to mattress, we conveyed to each other through a series of head movements and meaningful glances that tonight was the night — no more V-card. While he fumbled around looking for a condom, I pulled my jeans and panties down, but left on my tank top, half because I was still so shy about my body and half because the chilly basement temperature.

Then he was on top of me… and then I think he was inside of me? My virginity, the last of its kind in my circle of friends, had been lost in under thirty seconds.

Still above me, Dan leaned back and whispered, "It gets better than this. I stumbled to the bathroom to clean myself. I came back to find Dan lounging in the recliner, staring blankly at the TV. We spent the rest of the night watching a marathon of the dating show Change of Heart. It would take weeks — weeks curiously void of any other attempt at intercourse — for the irony of that entertainment choice to sink in.

I was a girl-crazy junior in high school when I noticed a sophomore who was in two of my classes. She was a swimmer with a great toned body and sexy eyes. We started to hang out in the same group of friends and quickly it was clear there was a mutual attraction.

The first time we went out ended in handcuffs, a misdemeanor charge for criminal mischief, and our parents coming to the police station to pick us up. Not the ideal first date, but I guess it was foreshadowing things to come. Our parents did everything they could to keep us away from each other, which just fueled our determination to be together.

I finally bought some condoms and we agreed to meet in the parking lot around lunch and skip school that afternoon. Our options for privacy were limited. I parked the car and spread out a blanket on the rough field grass. We took off our pants, and I fumbled with the condom until I was finally in. In what felt like ten seconds later, we heard a car coming down the abandoned road — not just any car, but a police car coming to interrupt our little party in the middle of nowhere.

Unlike Seth Rogen in Superbad , the female police officer had no problem cock-blocking me, and after we got dressed she took the swimmer in for truancy because she was under sixteen. After her mom got the second call from the police to pick her up, we had to get even more careful about tricking our parents. But we were able to stay away from the police, and the extreme efforts turned out to be worth it.

In an admittedly self-righteous and rebellious moment, I decided to hop a train from the comfort of my seaside high-school town to visit a friend who was at a state university. I thought only about two things on the way up: But what I got was far more enthralling. At a college rager, amongst waves of red cups and cigarette butts, I met someone who would become the first love of my teenage life.

He was from Los Angeles, black-haired, clad in vintage specs and a white t-shirt. I was seventeen and indescribably smitten. But I was a frequent masturbator, and figured I was so in touch with my own body and sexuality that as soon as I let someone else explore, all those years of pent-up sexual frustration would erupt out. I started living for weekend trips, sneaking off to the city for heavy petting in the park and quiet time at the museum.

I was a little more creative than that. So, I devised a plan for spring break to fly on my own dime to L. My bohemian mother bought it, and soon I found myself flying across the country, alone, into the stardust city lights of Los Angeles, free and scared shitless.

We were staying at a pay-per-week motel in East Los Angeles, and no sooner had we checked in than I had him on the floor. We made out until our clothes were scattered about the room.

On our way to the bed, I made him turn off the lights. I wanted to try all of the positions my friends had bragged about. But they seemed pretty impossible for two chaste virgins in the dark. I wanted to be graceful, legs propped up like an umbrella, bent backward, sitting, standing, stretching. Instead, I had his body resting heavily on top of mine while he tore at my insides. The rest of my time in Los Angeles was a blur of moments captured in Polaroid memories.

That night, it was Nietzsche, and his barrage of two-bit words made it even less sexy than usual. We ran away and snuck up onto the roof to smoke a cigarette and talk about the sex neither of us would be having that night. We came down hours later, our friend passed out on the dorm couch, so I drove the girl to a diner, and eventually to the airport. She was quirky, odd, eccentric, but beautiful. It seemed too easy to connect with her, and admit our mutual physical attraction.

I thought she was crazy, but it only made me want her more. I even felt bad about plotting to get into her pants. I was supposed to be a nice guy, and a reliable friend. I met her at the airport in January. I drove her to her dorm, carried her bags into her room, and threw her up against a wall. We kissed, and fell into her bed. I awkwardly undressed her as she squirmed against me, trying to do the same. She had been a long-distance runner, and her body was spectacular.

As I dressed, she apologized repeatedly, crying and telling me to spend the night. When I declined, she started undressing me again, so I went back to bed. This would be a pattern for us over the next year and a half. I was her anchor, just as her sex was mine. I used to imagine that the gigantic breasts were some sort of extra bladder for pee. I know, I was a weird kid. By senior year of high school, I was known for my sweet face and dirty sense of humor.

With two kisses from two different guys, one boob touch, and half a blowjob, I was basically all talk, no walk. I started dating my boyfriend early second semester of twelfth grade. I knew everything there was to know, right? Thanks to our almost instantaneous emotional connection high school is good at creating those kinds of relationships and crazy chemistry, we progressed quickly from making out, to boob grabs, to handjobs, to blowjobs, to manual stimulation of my nether-regions.

We had to be careful not to get caught, so much of our time "watching TV" in the den with the lights out, or "talking" outside after dark was really put towards our sexy checklist. After two months of dating, and a ton of research on my part brands of condoms, the effectiveness of the "pull-out" method, careful observation of my cervical mucus for clues to my ovulation cycle, and the effects of low BMI on fertility , I felt suitably prepared to relinquish my V-card.

This would continue until I would hiss with pain and smack him on the arm to "pull out, you dummy! I never worried about breaking my hymen because I had actually accomplished that in the first grade by falling out of a tree. I just wanted to make sure my vagina would be receptive to the whole "penetration process. It was one of those stand-alone hammocks — no trees necessary! My siblings were all asleep inside, and my mom had dozed off in front of the TV earlier. He wore regular clothes and threw his belt into the grass.

I lay back in the hammock and he carefully climbed on top of me. I took deep breaths of the jasmine-scented air and tried not to be nervous. I could see the moon over his shoulder and I remember thinking, "This is right. I helped him put on the condom being sure to pinch the tip , and kissed him over and over again.

With my hand guiding him in, we finally had real, complete sexual intercourse. The hammock swayed with his thrusts, making me dizzy, but I got used to it.

It started to feel really nice, like a foot-rub for my vagina. Afterwards, we declared it a success. I was no longer a virgin! I felt a little regretful, mostly because I had a residual childhood belief that unicorns existed and only appeared to virginal maidens. I told you I was a weird kid. I can totally come from intercourse like a pro. A moonlit night in spring, in a hammock, with a guy I loved? I think my first time was perfect.

I was fifteen and fighting with every ounce of my power not to be gay. There, I listened as my best friend and object of my every secret carnal desire, George, lost his virginity, quite loudly, with a German named Daisy, just opposite the wall to my right.

My heart could barely stand it. I thought he was like me. I was always hoping something would stir in my pants. I kept waiting for one to fix me. At a pool party, I pulled her aside for five minutes of carefully orchestrated "Oooo, this is so hot, we could get caught" time so I could fingerbang her and gauge just how I felt. Sad, and like I needed a Wet-Nap.

This was my last-ditch effort. Baby looked like Coco from Fame. I thought she was exquisite. She looked at me and smiled and I lifted her chin and kissed her. It was sweet, which I knew was probably wrong, so I pressed down hard with passion.

Nothing she did made a difference. My dick was a dismal wreck. There was nothing to do but roll off her, and crumble in a ball at her feet. There it was, no denial, in front of me, for the first time out loud, for someone else to judge and to mock me.

Baby was wise to the future. I heard taxis and laughter and night. George was finally quiet, I heard city and possibility, and I smiled.

Best money I ever spent. It was a blistering cold January night in , and The World nightclub was packed with drag queens, homeboys, and all sorts in between.

To seventeen-year-old me, he was as exotic as they came: Italian and Jewish from Bensonhurst, crazy green eyes bordered by Ken Wahl-esque brows and even crazier thick, full lips. But, mostly, I loved his scent, a blend of Obsession for Men, weed, alcohol, and sweat.

I turned back to my friends and grinned like an idiot, much to their irritation. None of them liked him. A few hours later, closing time was fast approaching and my friends wanted to go home. Leaving now was not an option. Just then, SJ surfaced from behind me and slipped his arms around my waist.

The bouncers made their final rounds, clearing out the club, ignoring the two of us as we sat on a couch — SJ had carte blanche with club management because he brought in so much business.

I started to shiver and he asked, "You cold? We gotta fix that. He fumbled to put the condom on and subsequently fumbled to put his penis in. When he did, I saw stars. I gasped and trembled in pain as my hands clutched onto the back of his neck. Nothing had ever hurt as much as this. Not really, I thought. After a few moments, he moaned and was still, then stepped backward.

I felt a hot liquid trickling down my leg. I feared the condom had broken, but in the dimness, I could see that it was blood. He grabbed napkins from behind a deserted bar. We pulled up our clothes. In the coat-check room, we discovered that my coat had been stolen.

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Getting His Apology - Chapter 01 Viewed: When he finally left, I slid the condoms gingerly onto the counter.

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My Disgusting Neighbor Viewed: Boating; An Ocean Discovery [gay] Viewed: My First Cock - Chapter 2 Viewed:

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First Day of College [bi] Viewed: I was seventeen and indescribably smitten. His gentle stroke, our eyes together, kissing fully. He abused the shit out of his accent, and enjoyed himself, to say the least. The Locker Room Viewed: