Sending [m]y girlfriend of[f] right

My girlfriend finished her bachelor’s degree yesterday. After years of working hard, she completed her last exam and is finally free. She already has a job lined up, but doesn’t start full time until June, so she decided to take a long vacation. She’ll be leaving today and I won’t be seeing her for a couple weeks. So naturally, being the horny fucker I am, I had to make the best of my last night with her.

It was almost midnight and I was already in bed, when she walked in wearing these tight black yoga pants and a tee shirt that fit her curves in the best way. A little about her, she’s 5′ 3″ with C cups and a hips that won’t quit. She’s got an amazing ass, and the yoga pants were making it that much hotter. I already knew I wanted to fuck her, but when she bent over to grab some stuff out of a drawer, my mind went blank and I knew I needed to have her now.

Surprise window sex with my wife in a hotel

This past weekend my wife Allison and I traveled a few states over for a family reunion. Her moms side of the family is quite large so it always turns into a circus trying to coordinate with so many people. She knows my disdain for events like this, but I put on a happy face and go because she enjoys them. The first day there was just as expected, tons of probing questions from the aunts and uncles, when we will have kids etc. That evening since we were tired from traveling we decided to skip out on the various groups of people going to different places to eat and head to the hotel. We went up to the room for a little bit to get settled in, and then I left to go grab us some food from down the street.

Bookworm hooks up with the jock [F/M]

So first off my name is Avery and all this happened like a year and a half ago. I’m 5 foot, half Mexican, but really tiny and petite, long dark hair that’s usually curly, glasses. I’ve always been called cute and adorable, but not really “sexy.” I was an ugly duckling until about junior year of highschool but really didn’t come into my own fully until college. I’ve always been the shy type and kind of a bookworm with a side of tomboy thanks to three older brothers.

Anyways so this all happened freshman year of college but I need to set the background first! So through high school I just kind of blended in with the crowd. I wasnt super popular and a pretty reserved person. I had my few close friends and had a boyfriend for awhile but in general just kind of blended in. I definitely WASNT on any of the popular guys radars or anything.

I took advantage of (m)y drunk (f)iance last night.

I’ve been with my girl for 4 years. Our sex life is great although we’re going thru a bit of a dry spell due to life stress and planning a wedding and money and all that crap. Lately I’ve been feeling sexually frustrated and so last night I decided to put an end to that spell.

So my lady is 5’5″, brunette, olive complexion, with perky B tits, hour glass figure and big booty that still drops my jaw. I mean this ass is so damn gorgeous, I can’t keep my hands off her. Maybe I can convince her to let me share a pic with you but she’s pretty self-conscious so probably not. For this story I’ll call her Bettie, after Bettie Page.

Last night we invited our couple-friends over for dinner, I was pretty tired from work but I put on my happy face because they put her at ease and temporarily relieve some stress… Plus we usually get drunk, smoke some weed, play cards and have a great time, so why not?

[M]y first anal, from the [f]riendliest stripper ever.

This all happened about five years ago. It was after my long-time girlfriend left me. We were in a new city, and she didn’t have any friends or family there. I can see why she left now. But back then, I still needed to get her off my mind. Other than that, it was a pretty good year for me. My new job was going well. I had lost one hundred pounds at that point in the year. Going from fat to average was a great accomplishment for me. I still felt fat in my head though. Undesired. Lonely. This is a story of the woman who got me over that.

She was sitting in a Starbucks when I first saw her. She had long black hair that went down to the small of her back. Almost ivory skin. I didn’t know what color her eyes were, but they were dark. Her face was held up by beautiful, full cheeks. She was wearing a t-shirt and sweatpants, almost like a Saturday morning at home, but at a Starbucks. She sat at a corner table listening to something on her phone and sipping her coffee. She had large tits that stretched out her t-shirt. Looking at her I could tell she was built for more comfort than speed. She wasn’t fat, but, plush almost. With a nice ass, that I could tell was big even though she was sitting, supported by strong legs that held everything up in a perfect display Maybe the best way to describe her was…squeezable.

Waterpark blowjob

I once took my (now ex) Jessica, her daughter and her bestfriend (Liz) to a local waterpark/amusement park. Jessica and I drove there together with her daughter, and Liz met us in the parking lot. We gathered our picnic lunch into a backpack, and then spent the next few hours playing in the park and riding the rides.

A few hours in and Liz needs to leave soon but we decide to stay longer. Before she leaves, Liz wants to ride a Rollercoaster that no one else wants to ride, but I finally agree so that Liz won’t have to go by herself. She wasn’t being as bitchy that day, so I didn’t mind so much.

The line was not long, but I had Liz’s ass damn near in my face (wearing her 2 piece) most of the stair climb up to the Rollercoaster. We rode the Rollercoaster without incident, and then met with Jessica again.

Liz said her goodbyes, and I walked away to check out other rides with Jessica and her daughter. About 15 minutes later, we see Liz walking towards us. Turns out she can’t find her keys, and thinks she left them in our car when we were loading the backpack. So I tell Jessica to keep doing rides with the kid, and I go with Liz to the parking lot.

Blowjob from the girlfriend of a total asshole

This story happened almost ten years ago, is one of the hottest stories of my life, and is absolutely true.

I had complicated friendship with a guy in college who, in the end, was a friend, but in spite of a lot of bad behavior on his part. He was an asshole by nature that patrolled college parties intimidating any non-aggressive personality-type males he could find. Total egomaniac, arrogant, good-looking, and, someone who believes in aggression as a virtue. We became friends early freshman year just because I was basically a bigger dude and didn’t take shit from someone like him, which I think he respected. Of course, he had a bunch of chicks around in the time I knew him, but our junior year he was with one for a while who was probably the best looking of the bunch. She was petite, maybe 5’6”, thin, blonde, C-cup, tight little ass, and your standard private school bitch personality, though innocently caught up in this guy’s whirlwind of a personality at an impressionable age. He cheats on her plenty, they fight, break up, get back together, and on and on. Eventually he cheats on her with this girl who was known to be able to deep-throat, and this gets back to the girlfriend who is furious.

A Friendly Blowjob [MF, oral]

I banged on the door. “Yo, Chris! Are you in there? Stop jerkin’ off! I need to borrow your printer!” I waited patiently for a few seconds. No response. I raised my hand to knock again when the door swung in, revealing Chris’s exasperated face, his brown eyes glaring at me. I held up my flash drive. “I just need to print out my essay, is that okay?”

He sighed. “Sure, come on. Make it quick.”

“What kind of a greeting is that?” I asked, as he shut the door behind me. “Is that any way to say hello to your beautiful neighbor?”

“Like you’re one to talk, Lisa. You nearly gave me a heart attack with that Verdun of a hello of yours. How do you knock so loud? You’re like, a hundred pounds.”

I flexed my arm and smiled. “You didn’t think I did all that taekwondo for nothing, did ya? Don’t tell me you need another demonstration…”

He winced. “I’m good. Just thinking about the last time makes me body ache…”

“I really didn’t mean to kick you in the balls. It was an accident!”

“It’s fine… Water under the bridge. Just…don’t do it again…”

How my mouth got used in a semi-public area [blowjob]

After writing the other story, I remembered that a similar thing actually happened a few years prior. This one happened in a somewhat public area so is probably better suited for this sub.

Anyways, here it goes:
There was this man I had a strange relationship with. We were close friends that also fucked a lot. A FWB. I am calling him a man instead of a guy because, being in his mid-thirties, he was also the oldest guy I ever fucked. We both always wanted more sex and would fuck as much as our available free time and location allowed – which ended up being about 3 times a day. I would give him everything he desired sexually and he would give me everything I desired sexually. We would cuddle closely all night and he would fill me with cum everyday.

Answered a craigslist ad from a guy willing to suck off straight guys, got more than I bargained for [M/M]

I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.

My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.

One day, on one of those nights when I was away from my girlfriend all my friends were out hooking up, I strayed from my normal porn appetite onto Craigslist’s casual encounters page. I wasn’t really planning to do anything there–I had never cheated on her–but I decided to browse and click a few ads. I started on the w4m section, but it soon became exceedingly clear that every one of the ads there was posted by a prostitute or a spammer. So I drifted over to the m4m section, mostly out of curiosity–and while most of the ads were not my style, one caught my eye. It was a guy a little older, 28 years old, who had posted a simple message offering a free, no-strings-attached blowjob to a straight/curious guy. His apartment would be dimmed with straight porn on the TV, and whoever answered the ad could walk in, get sucked off, and leave anonymously.