Awesome Xmas Eve fun but he left the next morning [m/f]

A couple of days before Christmas, my gf and I play a sexual hazing/initiation game with my roommate. She's in love with it, it was awesome night. Christmas Eve, she dumps me to go back to her abusive husband. The day before that, my roommate left to go spend time with a girl he knows from high school. I have no plans, nothing to do, hardly any food.

This guy from class that I never went to starts talking to me on Facebook but nothing really happened with that. He was more interested in smoking out than anything plus I didn't really know him. That night I rode my bike to the local pizza place and had some beers and some food (had to get leftovers for XMAS). An older guy sits next to me at the bar and it's a TA from a class I have. Somehow he recognized me from the 5 times I went and we went start talking. It starts raining and he offers to bring me home. I won't say no to a free ride. When we got back to my apartment, he doesn't put his moves on me, we just BSed in his car. The rain gets worse but I want to go in, he doesn't have anywhere to go so I offer to let him come in. He knows what's up by now.

The Glorious Hustle Part 5: Gloria Looks Back by John Berand

The weed was almost tart, and clean, and Gloria wished she could handle it. She was easily addicted to things, and she worked hard not to smoke weed or tobacco. Debbie was more confident. Debbie had her feet up, and was watching some basketball game on silent. “Bitch it’s been a minute. How you been?” “Good. I been good. You ?” “Dibbling and dabbling. Just doing what I gotta do. What took you so long? I thought you got in last night?” “Well I had to make a stop.” Debbie raised her eyebrow. “You get paid?” “Well I did….my pussy is still sore.” Debbie burst into hysterical laughter, as did Gloria. “I meant did you get some money?” “He wants me to work for him.” “Makes no kind of sense. All you’re good for is pussy anyhow.” “Well thanks, friend..” “You don’t get it. All you actually want is to fuck. You don’t have some deeper goals in this thing. Don’t lead people along. Doesn’t work.” “So I give him back the money?” “Detail. Point is you need to know it’s not your plan to clock a 9 to 5.” “Ok. What do you do for bread?” “I still get my child support, and I still have that royalty money from the songs I did. And sometimes my friends are friendly.” “So you don’t stress?” “I make sure I’m focused on getting money, but sometimes you run out of fucks to give. You would be surprised how little people care about you. You have to do it. Make sure you get yours.” Debbie took another drag on her joint and stood up. She wore a golden silk sarong, wrapped under her armpits and over her breasts. She was bare footed. She went to the bathroom, brushed her teeth, swigged some mouthwash, took off the sarong and sat on the toilet. When she was finished she stepped into the shower. Looking at her Gloria marveled. Debbie was still the same. Thick mane of red hair, creamy complexion, still clear, tight waist, broad hips, big breasts, broad shoulders, long, jaunty stride. She was free. Or seemed that way. She never complained. But maybe Gloria complained first. Maybe. Debbie lived by herself, with her son, and in her earlier life she had been an effective songwriter, who had the good fortune to partner with a good man who sorted her out financially. That one decision had given her a degree of freedom which she took advantage of until today. In addition, she was good at keeping work and play separate. They had both played basketball together in high school, but Debbie was more point guard than a power forward like Gloria. She still maintained that thoughtful approach to life. Still careful, still plotting. Gloria always thought she could handle anything by hammering at it. Not true. “Do I have to ask?” Gloria walked over to the shower, and took her clothes off. She closed her eyes as they kissed. Debbie wasn’t as tall as her, but she was a great kisser, and she felt her head would explode. It had been a while, and somehow in this volatile world, a familiar tongue and body were sources of peace. It was going to be ok. For all Debbie’s brio, she was always gentle. Almost maternal, which was funny for the smaller woman. Gloria felt she could really relax. Like Debbie didn’t want anything from her but her affection. That affection was free. Her nipples hardened, and her pussy ached from the earlier ministrations of Tony and Jenny. After the shower they padded back into Debbie’s room, and lay on the bed, air drying. It was an old habit they had, of admiring each others bodies. Debbie still had a flat stomach, though her ass was a bit thicker than it used to be. Her pussy was waxed, and as she lay on her back Gloria came at her with some lotion, and started gently oiling her feet, then her shins, then her thighs. She opened her legs a crack, and Gloria started to work up, looking at her cleft, which slowly started glistening as Debbie got relaxed. Debbie pushed her legs all the way open. Her pussy was wine colored and thick, with a growing moisture as Gloria kept rubbing her inner thighs. “Ahhhh, keep sucking me there. Oh, keep that rough tongue on me. Oh God yes..” Gloria licked and sucked, lapping away at Debbie’s juices. “Tell me about your new man.” “I I I I don’t know why you assume I have a man.” Gloria reached into the bedside cabinet and pulled out a dark, polished wooden dildo. It was curved and lovingly oiled, with a rounded knob at the front, and a thicker body as one moved down from the front. She stroked it along Debbie’s left inner thigh. “I can tell you have a man, you’ve always loved dick.” She tapped Debbie’s clit with the dildo, first slowly, then faster. Debbie writhed. “This is torture, I mean… I have friends, I I have friends.” Debbie stuttered. This was the most fun. Trying to have a conversation when you wanted to just do anything other than talk. “ I try to stay in the flow of things, but I’ve….” She trailed off. Gloria had introduced the knob to Debbie’s pussy. She was slowly working it in and out of the pussy, an inch at a time. Debbie was writhing slowly, stroking her little red nipples. Her breasts were E cups, which on her 36 inch chest was a lot. They were firm but were true to gravity, and were a source of much attention for her. Gloria stroked the knob further inside, now stroking two inches at a time. “Bitch don’t torture me. Fuck me with that thing!” Gloria pulled it all the way out. “I’m just wondering what I’m missing out in Chicago. What would you do differently if you were me?” “Fuck.” Debbie sat up, reaching for the dildo. “No.” Gloria pushed her back down, and pushed it in again. Stroking her, rubbing its curved knob against the top of Debbie’s vagina. As she touched Debbie’s g spot Debbie froze, halfway sitting up. She lay back down again. Gloria sped up the pace, fucking her with the dildo. Debbie moaned. She writhed. She sat up and Gloria shoved her down. “Tell me you’ll never leave me.”

My Step Sister [mf][oral][preg]

Our parents got married when I was 14 and she was 13. From that point on it was pure chaos. Although I spent most of my time at my mother's house most of my weekends were spent with my dad, my step mom and my step sister. We were like oil and water in the beginning, fighting with pretty much every breath we took. Though after awhile, as we started to grow up and the marriage stopped being so new things changed, albeit slowly at first.

At some point, although to tell you the truth I don't really remember when, I started to notice that she was becoming a woman, and that I was well on my way to becoming a man. Her mother was a very busty woman, and she took after her mother in this respect, starting to develop early and well. Although she used to sit in my lap and hang around my neck I had to put a stop to that as the side effects of close contact were… uncomfortable.

As the years went on we developed a strong relationship, and in fact became all but inseparable during our high school years. Although I still remember, with a strong twinge of jealousy, when she got her first boyfriend, though I was utterly confused by the emotions I felt.

[18F] Hottest night of my life. He [f]ucked [m]y brains out.

Three weeks ago, I recently turned 18 and lost my virginity to a stranger. The first time hurt a little when he entered me but I realized firsthand what amazing feelings my body can experience. The fullness is what made it enjoyable for me. Having a penis deep inside me is a much, much more satisfying experience than fingering myself. Constantly, thinking about my first time only made me more horny.

I want sex all the time. However, I haven't been fucked in three weeks. I think about sex during class and other situations. Being really horny is so frustrating. I can feel myself get wetter sometimes. Masturbating doesn't cut it for me anymore. I frequently dream about someone banging me really hard and pinching my nipples. I want to try everything once and twice if I like it. I never been a sexual person but now I'm the exact opposite.

In Her Hands [fmm][inc]

The two teenaged boys that had been so engrossed in playing their video game paused as they spied a young woman with wet, dirty blonde hair, wearing only a towel, saunter past the open bedroom door. Violet tossed the boys a wink on her way to her room, knowing full well the effect she had on the two high school seniors. She had only been home a week, having failed out of her second year of college, but she didn’t miss a chance to flirt with Gabe when their newlywed parents weren’t around. She didn’t have the hots for Gabe, it’s just that she liked the thrill of the tease.

After blinking a moment of at the empty doorway, Josh asked, “Have you tagged that yet?”

“Not yet”, Gabe smirked, jabbing his elbow into his friend’s side as they sat on the end of his bed. He always pretended to be more sexually active than he was. He was still technically a virgin since he’s only had blowjobs and handjobs. Coming to his senses he shook his head. “Wait… no. I gotta get used to having a sister.”

“A hot step-sister”, Josh corrected. “It’s totally cool for you two to hook up.”

Indiscretions of [m]y youth: [F]irst time trying anal.

As with all of my tales of the transgressions of my past, I'd like to start off with a little bit about me. At this point in my life I was 18 years old and was probably in the best shape I'll ever be in. I had just finished playing football, and was still weightlifting and playing other sports for fun. At 5'10 and 170 lbs. I was solid and muscular. For those who care about cock size, I was nothing impressive, just an average 5.5". I didn't get a lot of girls while in high school, random hook-ups mostly and a few relationships that lasted about 2 years combined. However, as I was getting into my final year of school things started to pick up, a bit. This particular story is about the first time that I got to have anal sex. Bit long, but I have broken it up for you.

The beginning…

My First Experience Pegging [F/M]

Background: We were both eighteen at the time. Me a high school junior (adopted and changed schools during the middle of the year) and him a high school senior. I'm Asian, 5'2, long black hair, green eyes, athletic toned petite body, thick ass, 34a tits, and a shaved pussy. He's white, about 6'2, shorter brown hair, blue eyes, muscley toned body, 7 inch uncut cock, shaved.

At the beginning of the school year in one of my classes I ended up meeting this guy who seemed pretty cool. We sat next to eachother and ended up talking quite a bit and got eachothers number. We started exchanging texts and became more flirtatious. I hadn't known him before that year so I started talking to my friends about him. Most of them were jealous because he was pretty attractive and also just a very nice guy. I took this as a sign to go ahead and try to start something more with him. We went on a few dates which were fun and usually ended with some making out which didn't bother me but after a while of this happening I really just wanted to fuck him.

[M4F] Why I want to indulge in my voyeuristic side

All my life I have been fascinated with voyeuristic tendencies. Recently I have begun to explore them and have also looked into myself, to see why it is such a big fantasy of mine. Some of the events written here may or may not be true, as my mind has reshaped and forgotten things over the years. But here is my story..

Ever since I was a young boy, let's say about 8 years old, I've been excited by the idea of watching girls, unseen. I had found my first nudie mag, at a construction site. My much older sister knew about it, and told me "that's what the girls look like in the locker room at school." She would tease me from time to time with stories of seeing so-and-so naked there (neighbors, her friends, etc.).

I’m back: Sex with a church girl on a church ski trip [m/f]

Some of you might remember me. I posted under a different ironman name up until recently. I deleted my account, because it got hacked. Some of the stories I posted over the last couple of years are gone forever from reddit, so I figured I would come back and start posting some old ones to make sure they aren't lost. I will post new stories as well when I have a chance. (New stories will come I promise). Here is an old one. Hope you enjoy:

Like I've said in previous posts. I figured it would be fun to go back to my promiscuous (man-whore) days and recall some of the stories from back then. I'm generally considered a good-looking guy (used to model, 6’3”, dark hair, blue eyes, swimmers build, workout regularly), so that enabled me to have quite a fun sex life. These stories are 100% true and not embellished in any way. I think that a straight honest story even if not as exciting at times is a bigger turn on, so that is what I will continue to try to give.

The virgin and his friend [MM/F]

My roommates were away: Selene went to Cancun for Spring Break; Caroline was building houses for Habitat for Humanity in Atlanta. I had planned to go back home to the parents' place, but decided in the end to stay where I was and catch up on school work. Cold weather lingered in the midwest through the end of March. I remember it being a productive several days, but by the end of the week, I had a severe case of cabin fever.

A pair of high school students accosted me on my way in to the liquor store. They claimed that they were 18 and needed someone to buy them beer. I was only 20; bearing a driver's license that my older sister had "lost," I agreed to help them. We made conversation at my car afterwards, and I invited the pair back to my place to drink with me.