Truth or Dare in a hot tub [MF] [FF] [MM]

The folks over at /r/gaystoriesgonewild thought some of you guys might appreciate this, so here goes:

A while back, I wrote a story about back in the early ’00s and a truth or dare game. Those games are always good for a chuckle or two..and I haven’t played one since…well, since back before the wife and I were married. But as it turns out, you’re never too old for kid games.

My wife is on one of those ‘deal of the week’ email things for vacations. Usually, they’re kind of shit-shows, due to the travel dates being some of the worst times possible. She’d actually found one that ended up being a pretty good deal, a pretty good destination, and pretty good timing.

Things were going to work out very well, until she let me know that we’d be going down at the same time as one of her friends and her husband.

Confessions of a Retail Manager [MF] [cheating]

It all started in Dallas.

We were both managers for a very popular retail chain, and we were at the annual company-wide conference. While her store and mine were very close, we never really talked outside of the occasional district meeting. I had noticed her, though.

Anna was about 5 feet 4 inches, with straight blonde hair and an attractive face. What really caught my attention was her breasts. To say she was “blessed” would be an insult to blessings. They were huge (I would come to find out she was a 44J). The rest of her body was attractive as well, but it was hard to look past her enormous chest. As a breast-man myself, I would often find myself inadvertently staring, across the meeting table, watching the buttons on her shirt straining to keep her chest contained. At least I was never caught doing so, and I would be able to look away before embarrassing myself.

[MM] A straight boy on vacation makes his first trip to a gay bar and a gloryhole.

On a trip to Spain with a group of friends on a guys holiday I decide to finally do something I’d always wanted to do get dirty with another guy.
At the time I was in my early 20’s and had a sex drive that I could never satisfy. I had had all kinds of sex with plenty of girls up to this point, I had a dirty mind and a good sized cock so I had no problem getting pussy and owning it but I wanted to play a different part tonight.
My friends the typical jock crowd were drinking heavy and passed out early, I had taken it easy that night so to be able to sneak away. I got a taxi to the well known gay centre of town, my cock was straining at my shorts already I could believe the open sexuality everywhere it turned me on so much.
I had a drink in a few bars but didn’t like the crowd in them so I finally settled on one, a dark bar with mostly leather wearing older guys inside and a sign about anything goes gloryhole’s in the back. I didn’t want to waste any time anymore so I drank a shot at the bar for courage and made my way to the back.
Behind the curtain was a single urinal and two empty booths with three different sized holes in each I made my way into one and locked the door.
As soon as I got in I started wanking my cock, I was alone but couldn’t take it any longer the dirty feeling of being here, the horny looks from the men outside and the smell in the booths drive me crazy. Just as I thought I was going to cum the door to the next booth opened. I was so nervous I had no experience with guys and I was in the deep end now.
I knelt at the middle hole and so did he, he was a Middle aged English guy with a beard, he kissed me hard through the whole and his rough beard pressed hard to my soft young face. Then he stood up and slid his semi hard cock through the whole. I had never given a blowjob before but I knew what made a good one and i was pretty drunk at this stage, so I straight away took his cock in my mouth sucking on it covering it with my spit and letting it grow hard in my mouth. His size shocked me as it grew thicker and longer than my cock until I had less than half in my mouth. This scared and excited me so much that I just kept going bobbing my head and moaning loudly and slobbering all over his cock. He tried to pump into my throats but I couldn’t take more than half I tried to deep throat but had no chance he responded my forcing and extra half inch down every time I reached my limit. After about 8 minutes he got vocal and encouraged me to make him cum with some of the nastiest shit I’ve ever been called, “suck that cock bitch boy, get ready to be my cum whore, moan you cunt, deeper slut deeper fucking gag!” Before he finally came, shooting two streams straight down my throat before I could react, he then pulled back and shouted for me to catch the rest and hold it, with a puddle of cum in my mouth he knelt down again looking me in the eyes and told me, “now swallow and say thank you”. With a gulp I swallowed his salty load and thanked him honestly, he kissed me hard again and left. I stood in the booth still holding my own load and hard cock.

The Cabo Maid [mf]

My freshman year in college my family took a vacation to Cabo. The resort we stayed at was really nice, it had villas at one end and a separate hotel at the other. Being a family of 5, we were in one of the villas which didn’t have maid service, which who knows why my mom would be a fan of cleaning for everyone even while on vacation.

So the hotel was a couple minute walk down the boardwalk. There they had the big pool with the swim up bar, the slide, and the rest of the fun stuff. So for the week we were there, we spent most of our time at that pool or down at the beach.

Sleeping on a sofa bed in a two bedroom room with 4 of your family members leaves you absolutely no privacy, so a couple days in I was getting really horny, and spending days at the pool watching women walk by makes it no easier. Nor does having only a few girls my age either.

[M]e and my sisters [F]riend part 2 (long)

Please read part one for context (find it in my posted).
After me and E’s first encounter we kept our public contact at a minimum. She created a second Snapchat account where we would exchange nudes once in a while.

It was around a month after my first time with E when her family troubles became so bad she started permanently staying at our house for comfort for my older sister.

This was when our love story really heated up. One the 2nd night of her staying in our spare bedroom (which we made hers) I received nearly 20 snapchats of her masturbating and her lying completely naked on her bed. She was evidently wet and I could see patches where she had already orgasmed. I quietly left my room and approached the door on the other side of the room. I could hear her soft moans through the door. As I opened the door I knew she was expecting me as she had dressed up into full lacy underwear, hardly covering much.

A little experiment with some new toys with the new boy. [MF][Kink]

I pulled into the driveway and killed the engine. I finished my cigarette by taking one long drag, feeling my nerves slowly getting the best of me. I reached for my purse, which was housing a few toys for us to play with. But he was completely unaware that I was bringing anything except myself. Not only that, but in a neighboring pocket were some sexy thigh highs. He may have thought I didn’t catch him say how sexy he thought they were, but I ran out and bought a pair the day after his comment.

What was is about him, I don’t know. Pheromones, perhaps. How perfect I thought his body was. The feelings I got around him. The fact that he makes me feel just as sexy as I view him. We had only been seen each other about three weeks at this point. Which seems like nothing, but has felt like everything. We were already emotionally bonded on a number of levels, but the sex… The sex was the best I’d ever had in my life. And the communication and openness we had toward it only made it that much better. We had already slept together numerous times, I recalled as I got out of my car and made my way to his front door. Each time different than the last. Different rooms, different positions, different amounts of foreplay. Sometimes gentle, sometimes rough. We mentioned our deepest desires and fantasies already. And one he mentioned got me soaking wet. I knew that one fantasy just had to come first because of how kinky it was, and it had to happen now. He didn’t know just how badly I really wanted it, too.

Gonna be one of those days…

It was a warm morning, the sun breaking through the crack in the curtains lighting up the room as she slowly opened her eyes trying to focus them when a thought popped into her to head “7:30….I have to be at work at 8…..shit”. Jumping out of bed she reached for her clothes throwing anything on she could grab, quick bit of make up applied and no time for breakfast. Flying out the door and down the stairs just as the bus she was was suppose to be on flew past her “it’s gonna be a long day” she muttered to herself. Eventually after waiting and getting on the next bus she arrived at work, ok so it was a little bit later than planned but at least she made it, When suddenly a deep voice boomed across the office, “LOUISE…..”, she knew this wasn’t going to be good, her boss comes flying down the hall way like a bat out of hell, face red and seething, her stomach started churning like a washing machine on fast spin, until suddenly he was there standing right in front of her, he looks her up and down and calmly says without breaking his deep stare “late again, third time this week and I don’t want any excuses this time, because your late, you will take this and get on with it” he handed her a piece of paper with a time and address on it, “guess I better get to work then” she whispered, before turning sharply on her heels and heading out the door before her boss could say anything else.

Office Goodbye (MF) [NSFW] snowballing

Office Goodbye

One evening late at work you came by my office to say goodbye. You had just accepted a new job at another company. I stood up from behind my desk to give you a congratulatory hug. Our embrace turned into a full body hug, not one of those polite and prude cheek and shoulder things, but you breasts pressed firmly against my chest and my arm tightly wrapped around you holding you close.
Our eyes met in this intimate moment and then our lips met as well. We shared a deep passionate kiss, a kiss filled with all of the pent up angst and sexual desire that we mutually shared but never acted on due to our shared employer. My tongue parting your soft sweet lips and intertwining with yours. Our hands starting to migrate and explore each others body. Amusingly we both grabbed each others ass, firmly kneading and caressing.
I placed a hand on each cheek and pulled you up off the floor and held you against me as our tongues continued to dance together. I felt the dizziness and butterflies of all the fantasies and desires that I harbored for you. Our kissing and touching, your body and soul were all that I was aware of in that everlasting moment of time.
Some noise down the hallway outside my office broke our passionate connection. I freed my grip on your sumptuous rump and gently let you down to the floor. You backed away and kicked the door stop away from the door, right as someone walked by, and the door closed with a slam, as if it knew the urgency of our need for privacy. With a flick of the light switch, our only illumination came from the music player visulizer on my computer screen, on which I increased the volume.

Sticking my dick in Princess [MF]

This short chapter will have more backstory than sexy parts, so feel free to skip it if that’s what you’re here for.

Princess was a girl I dated for a couple of years. She was 5’3″ straight blonde hair brown eyes curvy figure with DD cups and a bubble butt. She’s referred to as Princess because that’s how she saw herself and expected others to treat her as such. I should have broken it off early if not for the fact that she lived by the old adage of “Keep your man’s stomach full and his balls empty”. This translating to sucking my dick literally every single day we were together. Once she decided to lose her virginity (which took us four attempts until success), sex was on the menu in addition to the daily blowjob.

She would go down on me almost on command, anywhere I asked. Any trip that was going to take 10 minutes or more was an opportunity for road head, and there were several movies that I had to watch twice because she wanted to go down on me in the theater. She liked to try out things she saw in porn, so I got to give her facials and cum on her huge tits.

Helped turn my buddy’s GF into a slut last night. Pics coming soon! [MFM]

TL:DR – Buddy’s GF wanted to try two cocks at the same time, I obliged. Got drinks at a bar, got a blowjob in the backseat while he drove us home and then we fucked her hard. She’s now his slut in training and is eager for more!

This story is about both how it came to be AND what went down when it finally happened. Skip ahead to the marker if you just want to read the sexy part.

Met my buddy a couple years back in a sports league where we played on the same team, and we’d usually end up at the bar afterwards for some drinks. He’s a total horndog just like I am, so lots of times our convos would turn to sex and sexual conquests or fantasies. Over time, he & I got closer and I let him in on our little secret that my wife & I are in the lifestyle, and his reply was that he figured as much and he & his ex had done some stuff in the past but never really got too into it.
(They actually talked about inviting us over for drinks and making a move on us cause they thought we’d be into it, which we would have been, haha. Never ended up happening though)